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1-Methyl-4-(1-methylvinyl)cyclohexan-1-ol

PubChem CID: 8748

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Compound Synonyms BETA-TERPINEOL, 138-87-4, cis-beta-Terpineol, trans-beta-Terpineol, p-Menth-8-en-1-ol, Cyclohexanol, 1-methyl-4-(1-methylethenyl)-, trans-, A-Terpineol, 1-Methyl-4-(1-methylethenyl)cyclohexanol, cis-.beta.-Terpineol, 1-Methyl-4-(1-methylvinyl)cyclohexan-1-ol, trans-.beta.-terpineol, 1-Methyl-4-isopropenylcyclohexan-1-ol, 4-Isopropenyl-1-methyl-1-cyclohexanol, 1-methyl-4-(prop-1-en-2-yl)cyclohexan-1-ol, 7299-40-3, 4-Isopropenyl-1-methylcyclohexanol, cis-, A-Terpineol, (E)-beta-Terpineol, 7299-41-4, Cyclohexanol, 1-methyl-4-(1-methylethenyl)-, trans-, 1-methyl-4-prop-1-en-2-ylcyclohexan-1-ol, Terpineol, cis-.beta.-, Cyclohexanol, 1-methyl-4-(1-methylethenyl)-, cis-, S00R85C5ER, DTXSID7041209, 55258Z4SCW, p-Menth-8-en-1-ol, stereoisomer, Terpinol, beta-, t-Menth-1-en-8-ol, b-terpineol, FEMA No. 3564, beta-Terpineol, cis-, beta-Terpineol, trans-, EINECS 205-342-6, UNII-XS86XKC2VT, BRN 2205072, UNII-S00R85C5ER, beta-Terpinol, UNII-55258Z4SCW, beta -terpineol, AI3-00731, 4-isopropenyl-1-methyl-cyclohexanol, cis-I(2)-Terpineol, trans-I(2)-Terpineol, (E)-.beta.-terpineol, (Z)-.beta.-Terpineol, XS86XKC2VT, cis-p-Menth-8-en-1-ol, trans-p-Menth-8-en-1-ol, P-menth-8-en-1-ol, cis, 4-06-00-00254 (Beilstein Handbook Reference), SCHEMBL1245775, .BETA.-TERPINEOL, CIS-, CHEMBL3184678, DTXCID5021209, SCHEMBL13895789, SCHEMBL14278527, SCHEMBL22882350, FEMA 3564, .BETA.-TERPINEOL, TRANS-, CHEBI:132899, DTXSID201317014, DTXSID301316364, Tox21_302378, MFCD00037724, AKOS006282035, HY-119963A, HY-119963B, 4-Isopropenyl-1-methylcyclohexanol, cis, NCGC00255487-01, CAS-138-87-4, DA-69594, DA-78581, 1-methyl-4-(prop-1-en-2-yl)cyclohexanol, 1-Methyl-4-(1-Methylethenyl)-cyclohexanol, 4-Isopropenyl-1-methylcyclohexanol, trans-, DB-243107, CS-0089116, CS-0089118, NS00012934, C17517, 1-Methyl-4-(1-methylethenyl)-trans-Cyclohexanol, 1beta-Methyl-4alpha-(1-methylethenyl)cyclohexanol, TERPIN MONOHYDRATE IMPURITY B [EP IMPURITY], Q27261256, Q27288363, Q67880219, Rel-(1r,4r)-1-methyl-4-(prop-1-en-2-yl)cyclohexan-1-ol, (1S,4S)-1-METHYL-4-(PROP-1-EN-2-YL)CYCLOHEXAN-1-OL, 844-907-7
Ghose Rule False
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 20.2
Hydrogen Bond Donor Count 1.0
Pfizer 3 75 Rule False
Scaffold Graph Level C1CCCCC1
Np Classifier Class Menthane monoterpenoids, Monocyclic monoterpenoids
Deep Smiles CC=C)CCCCCC6))C)O
Heavy Atom Count 11.0
Classyfire Class Prenol lipids
Description Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. trans-beta-Terpineol is found in rosemary.
Scaffold Graph Node Level C1CCCCC1
Classyfire Subclass Monoterpenoids
Isotope Atom Count 0.0
Molecular Complexity 152.0
Database Name cmaup_ingredients;fooddb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Uniprot Id Q03181
Iupac Name 1-methyl-4-prop-1-en-2-ylcyclohexan-1-ol
Prediction Hob 1.0
Class Prenol lipids
Veber Rule True
Classyfire Superclass Lipids and lipid-like molecules
Xlogp 2.5
Superclass Lipids and lipid-like molecules
Subclass Monoterpenoids
Gsk 4 400 Rule True
Molecular Formula C10H18O
Scaffold Graph Node Bond Level C1CCCCC1
Prediction Swissadme 1.0
Inchi Key RUJPNZNXGCHGID-UHFFFAOYSA-N
Silicos It Class Soluble
Fcsp3 0.8
Logs -2.033
Rotatable Bond Count 1.0
Logd 2.044
Synonyms (E)-beta-Terpineol, 1-Methyl-4-(1-methylethenyl)-trans-cyclohexanol, Cyclohexanol, 1-methyl-4-(1-methylethenyl)-, trans-, p-Menth-8-en-1-ol, trans-form, trans-beta-Terpineol, trans-P-Menth-8-en-1-ol, &beta, -terpineol, 1-Methyl-4-(1-Methylethenyl)-cyclohexanol, 1-Methyl-4-(1-methylethenyl)cyclohexanol, 1-Methyl-4-(1-methylvinyl)cyclohexan-1-ol, 1-Methyl-4-isopropenylcyclohexan-1-ol, 4-Isopropenyl-1-methyl-1-cyclohexanol, 4-Isopropenyl-1-methylcyclohexanol, b-Terpineol, beta -Terpineol, beta-Terpineol, Cyclohexanol, 1-methyl-4-(1-methylethenyl)-, FEMA 3564, (Z)-&beta, -Terpineol, (Z)-beta-Terpineol, cis-&beta, -Tterpineol, cis-beta-Tterpineol, cis-p-Menth-8-en-1-ol, p-Menth-8-en-1-ol, cis-form, Terpineol, cis-&beta, -, (e)-beta-terpineol, beta terpineol, beta-terpineol, beta-terpineol*, cis- β -terpineol, cis-beta-terpineol, cis-β-terpineol, p -menth-8-en-1-ol, terpineol, beta, terpineol, beta, cis, terpineol<cis-beta->, trans-beta-terpineol, z-beta-terpineol, β- terpineol, β-terpineol, β-terpineol *
Substituent Name Menthane monoterpenoid, Monocyclic monoterpenoid, Cyclohexanol, Tertiary alcohol, Cyclic alcohol, Hydrocarbon derivative, Organooxygen compound, Alcohol, Aliphatic homomonocyclic compound
Esol Class Soluble
Functional Groups C=C(C)C, CO
Compound Name 1-Methyl-4-(1-methylvinyl)cyclohexan-1-ol
Kingdom Organic compounds
Prediction Hob Swissadme 1.0
Exact Mass 154.136
Formal Charge 0.0
Monoisotopic Mass 154.136
Hydrogen Bond Acceptor Count 1.0
Molecular Weight 154.25
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 0.0
Total Bond Stereocenter Count 0.0
Lipinski Rule Of 5 True
Esol -2.3179686000000004
Inchi InChI=1S/C10H18O/c1-8(2)9-4-6-10(3,11)7-5-9/h9,11H,1,4-7H2,2-3H3
Smiles CC(=C)C1CCC(CC1)(C)O
Nring 1.0
Np Classifier Biosynthetic Pathway Terpenoids
Defined Bond Stereocenter Count 0.0
Egan Rule True
Np Classifier Superclass Monoterpenoids

  • 1. Outgoing r'ship FOUND_IN to/from Abies Balsamea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 2. Outgoing r'ship FOUND_IN to/from Achillea Millefolium (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2001.9699697
  • 3. Outgoing r'ship FOUND_IN to/from Alpinia Calcarata (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2005.9698877
  • 4. Outgoing r'ship FOUND_IN to/from Alpinia Galanga (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699900
  • 5. Outgoing r'ship FOUND_IN to/from Alpinia Malaccensis (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2017.1374216
  • 6. Outgoing r'ship FOUND_IN to/from Alpinia Zerumbet (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2010.9700264
  • 7. Outgoing r'ship FOUND_IN to/from Amomum Longiligulare (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 8. Outgoing r'ship FOUND_IN to/from Amomum Subulatum (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2003.9712138
  • 9. Outgoing r'ship FOUND_IN to/from Amomum Villosum (Plant) Rel Props:Source_db:npass_chem_all
  • 10. Outgoing r'ship FOUND_IN to/from Amomum Xanthioides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 11. Outgoing r'ship FOUND_IN to/from Anacardium Occidentale (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2007.9699302
  • 12. Outgoing r'ship FOUND_IN to/from Anethum Graveolens (Plant) Rel Props:Source_db:fooddb_chem_all
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  • 14. Outgoing r'ship FOUND_IN to/from Argania Spinosa (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2014.977563
  • 15. Outgoing r'ship FOUND_IN to/from Artemisia Absinthium (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2016.1257370
  • 16. Outgoing r'ship FOUND_IN to/from Artemisia Persica (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2006.9699162
  • 17. Outgoing r'ship FOUND_IN to/from Bupleurum Scorzonerifolium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 18. Outgoing r'ship FOUND_IN to/from Bursera Graveolens (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.1563
  • 19. Outgoing r'ship FOUND_IN to/from Carissa Carandas (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2004.9698764
  • 20. Outgoing r'ship FOUND_IN to/from Carum Carvi (Plant) Rel Props:Source_db:fooddb_chem_all
  • 21. Outgoing r'ship FOUND_IN to/from Chamaecyparis Lawsoniana (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2000.9712032
  • 22. Outgoing r'ship FOUND_IN to/from Chrysanthemum Morifolium (Plant) Rel Props:Source_db:npass_chem_all
  • 23. Outgoing r'ship FOUND_IN to/from Cinnamomum Verum (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2015.1004120
  • 24. Outgoing r'ship FOUND_IN to/from Citrus Aurantiifolia (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 25. Outgoing r'ship FOUND_IN to/from Citrus Aurantium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 26. Outgoing r'ship FOUND_IN to/from Citrus Japonica (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.1996.9700651
  • 27. Outgoing r'ship FOUND_IN to/from Citrus Limon (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.1992.9698150
  • 28. Outgoing r'ship FOUND_IN to/from Citrus Natsudaidai (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 29. Outgoing r'ship FOUND_IN to/from Citrus Paradisi (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.1995.9698477
  • 30. Outgoing r'ship FOUND_IN to/from Citrus Reticulata (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 31. Outgoing r'ship FOUND_IN to/from Citrus Sinensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 32. Outgoing r'ship FOUND_IN to/from Citrus Trifoliata (Plant) Rel Props:Source_db:cmaup_ingredients
  • 33. Outgoing r'ship FOUND_IN to/from Citrus Unshiu (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 34. Outgoing r'ship FOUND_IN to/from Clinopodium Bolivianum (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.1996.9700621
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  • 38. Outgoing r'ship FOUND_IN to/from Coriandrum Sativum (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2008.10643676
  • 39. Outgoing r'ship FOUND_IN to/from Corymbia Citriodora (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699894
  • 40. Outgoing r'ship FOUND_IN to/from Curcuma Amada (Plant) Rel Props:Reference:ISBN:9788172362133
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  • 45. Outgoing r'ship FOUND_IN to/from Daucus Carota (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2001.9699720
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  • 47. Outgoing r'ship FOUND_IN to/from Elettaria Cardamomum (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 48. Outgoing r'ship FOUND_IN to/from Ephedra Sinica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 49. Outgoing r'ship FOUND_IN to/from Eucalyptus Alba (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699894
  • 50. Outgoing r'ship FOUND_IN to/from Eucalyptus Camaldulensis (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699894
  • 51. Outgoing r'ship FOUND_IN to/from Eucalyptus Deglupta (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699894
  • 52. Outgoing r'ship FOUND_IN to/from Eucalyptus Globulus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 53. Outgoing r'ship FOUND_IN to/from Eucalyptus Robusta (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699894
  • 54. Outgoing r'ship FOUND_IN to/from Eucalyptus Saligna (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699894
  • 55. Outgoing r'ship FOUND_IN to/from Eucalyptus Urophylla (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699894
  • 56. Outgoing r'ship FOUND_IN to/from Garcinia Dulcis (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.1187
  • 57. Outgoing r'ship FOUND_IN to/from Hedychium Spicatum (Plant) Rel Props:Reference:https://doi.org/10.1002/minf.201000163
  • 58. Outgoing r'ship FOUND_IN to/from Houttuynia Cordata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 59. Outgoing r'ship FOUND_IN to/from Hyptis Suaveolens (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2014.935019
  • 60. Outgoing r'ship FOUND_IN to/from Illicium Griffithii (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.1995.9698561
  • 61. Outgoing r'ship FOUND_IN to/from Isodon Melissoides (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2005.9698895
  • 62. Outgoing r'ship FOUND_IN to/from Juniperus Communis (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2005.10643434
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  • 65. Outgoing r'ship FOUND_IN to/from Lavandula Stoechas (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2009.10643750
  • 66. Outgoing r'ship FOUND_IN to/from Leonurus Japonicus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 67. Outgoing r'ship FOUND_IN to/from Ligusticum Sinense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 68. Outgoing r'ship FOUND_IN to/from Limonia Acidissima (Plant) Rel Props:Reference:ISBN:9770972795006
  • 69. Outgoing r'ship FOUND_IN to/from Lippia Alba (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2010.9700253
  • 70. Outgoing r'ship FOUND_IN to/from Litsea Cubeba (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 71. Outgoing r'ship FOUND_IN to/from Mentha Arvensis (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.1417
  • 72. Outgoing r'ship FOUND_IN to/from Murraya Koenigii (Plant) Rel Props:Reference:ISBN:9770972795006
  • 73. Outgoing r'ship FOUND_IN to/from Myristica Fragrans (Plant) Rel Props:Source_db:fooddb_chem_all
  • 74. Outgoing r'ship FOUND_IN to/from Ocimum Americanum (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699894
  • 75. Outgoing r'ship FOUND_IN to/from Ocimum Basilicum (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2016.1197801
  • 76. Outgoing r'ship FOUND_IN to/from Ocimum Filamentosum (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2015.1076742
  • 77. Outgoing r'ship FOUND_IN to/from Ocimum Gratissimum (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699894
  • 78. Outgoing r'ship FOUND_IN to/from Ocimum Kilimandscharicum (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2016.1232607
  • 79. Outgoing r'ship FOUND_IN to/from Ocimum Tenuiflorum (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2016.1232607
  • 80. Outgoing r'ship FOUND_IN to/from Origanum Majorana (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2006.9699210
  • 81. Outgoing r'ship FOUND_IN to/from Origanum Onites (Plant) Rel Props:Source_db:fooddb_chem_all;npass_chem_all
  • 82. Outgoing r'ship FOUND_IN to/from Origanum Vulgare (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2011.10643917
  • 83. Outgoing r'ship FOUND_IN to/from Paeonia Veitchii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 84. Outgoing r'ship FOUND_IN to/from Pelargonium Graveolens (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2006.12067128
  • 85. Outgoing r'ship FOUND_IN to/from Piper Attenuatum (Plant) Rel Props:Reference:https://doi.org/10.1002/(sici)1099-1026(199909/10)14:5&lt;279::aid-ffj821&gt;3.0.co;2-0
  • 86. Outgoing r'ship FOUND_IN to/from Piper Cubeba (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 87. Outgoing r'ship FOUND_IN to/from Piper Nigrum (Plant) Rel Props:Source_db:fooddb_chem_all
  • 88. Outgoing r'ship FOUND_IN to/from Pistacia Chinensis (Plant) Rel Props:Reference:ISBN:9788171360536; ISBN:9788172362461
  • 89. Outgoing r'ship FOUND_IN to/from Pistacia Lentiscus (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.2730060406
  • 90. Outgoing r'ship FOUND_IN to/from Prunella Vulgaris (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2012.10644102
  • 91. Outgoing r'ship FOUND_IN to/from Punica Granatum (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.2035
  • 92. Outgoing r'ship FOUND_IN to/from Rosa Damascena (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2016.1153985
  • 93. Outgoing r'ship FOUND_IN to/from Rosmarinus Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all;npass_chem_all
  • 94. Outgoing r'ship FOUND_IN to/from Salvia Officinalis (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all
  • 95. Outgoing r'ship FOUND_IN to/from Santolina Chamaecyparissus (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.2730070109
  • 96. Outgoing r'ship FOUND_IN to/from Spondias Mombin (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2005.9698933
  • 97. Outgoing r'ship FOUND_IN to/from Stachys Byzantina (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.1594
  • 98. Outgoing r'ship FOUND_IN to/from Stachys Lavandulifolia (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.1594
  • 99. Outgoing r'ship FOUND_IN to/from Syzygium Aromaticum (Plant) Rel Props:Source_db:fooddb_chem_all
  • 100. Outgoing r'ship FOUND_IN to/from Taraxacum Campylodes (Plant) Rel Props:Reference:ISBN:9788172363093
  • 101. Outgoing r'ship FOUND_IN to/from Thymus Kotschyanus (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.3333
  • 102. Outgoing r'ship FOUND_IN to/from Thymus Linearis (Plant) Rel Props:Reference:ISBN:9788185042114
  • 103. Outgoing r'ship FOUND_IN to/from Thymus Quinquecostatus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 104. Outgoing r'ship FOUND_IN to/from Thymus Vulgaris (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 105. Outgoing r'ship FOUND_IN to/from Trachyspermum Ammi (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2017.1383193
  • 106. Outgoing r'ship FOUND_IN to/from Trianthema Portulacastrum (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2016.1205523
  • 107. Outgoing r'ship FOUND_IN to/from Zanthoxylum Bungeanum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 108. Outgoing r'ship FOUND_IN to/from Zanthoxylum Piperitum (Plant) Rel Props:Source_db:npass_chem_all
  • 109. Outgoing r'ship FOUND_IN to/from Zanthoxylum Schinifolium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 110. Outgoing r'ship FOUND_IN to/from Zingiber Officinale (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2017.1417747