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Apiole (parsley)

PubChem CID: 10659

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Compound Synonyms Apiole, 523-80-8, Apioline, Apiol, Apiole (parsley), Parsley apiole, Parsley camphor, Parsley apiol, Petersiliencampher, 5-Allyl-4,7-dimethoxy-1,3-benzodioxole, 4,7-DIMETHOXY-5-(2-PROPANYL)-1,3-BENZODIOXOLE, 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propenyl)-, NSC 9070, 5-Allyl-4,7-dimethoxybenzo[d][1,3]dioxole, 1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene, APIOLUM, QQ67504PXO, 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 5-Allyl-4,7-dimethoxy-1,3-benzodioxol, APIOLE, PARSLEY, NSC-9070, EINECS 208-349-2, BRN 0195747, UNII-QQ67504PXO, 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propen-1-yl)-, AI3-14843, BENZENE, 1-ALLYL-2,5-DIMETHOXY-3,4-(METHYLENEDIOXY)-, CHEBI:70353, NSC9070, 4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-Benzodioxole, 1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)benzene, 4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole, Camphre de Persil, Apiol1503, Spectrum_000400, APIOLE [VANDF], APIOLUM [HPUS], Spectrum2_000419, Spectrum3_001283, Spectrum4_001643, Spectrum5_001718, 4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole, BSPBio_002885, KBioGR_002105, KBioSS_000880, SPECTRUM390001, SCHEMBL497412, SPBio_000378, APIOLE (PARSLEY) [MI], CHEMBL1560118, DTXSID4041236, KBio2_000880, KBio2_003448, KBio2_006016, KBio3_002105, CCG-39582, MFCD00047270, MSK179657, STK664284, 1-Allyl-2,4-(methylenedioxy)benzene, AKOS003398564, 1, 4,7-dimethoxy-5-(2-propenyl)-, ApiolineApiole (parsley), Parsley apiole, NCGC00094551-01, NCGC00094551-02, NCGC00094551-03, FS-10667, 5-allyl-4,7-dimethoxy-benzo-1,3-dioxole, Benzene,5-dimethoxy-3,4-(methylenedioxy)-, DB-052116, HY-135217, 5-Allyl-4,7-dimethoxy-1,3-benzodioxole #, CS-0109902, NS00032497, WLN: T56 BO DO CHJ FO1 H2U1 IO1, G88932, Apioline, Apiol, Parsley apiole, Parsley camphor, SR-05000002460, SR-05000002460-1, 1-Allyl-2,5-dimethoxy-3, 4-(methylenedioxy)benzene, 1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)-Benzene, 4,7-dimethoxy-5-(prop-2-en-1-yl)-1,3-benzodioxole, Q21071561, 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9CI
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 36.9
Hydrogen Bond Donor Count 0.0
Pfizer 3 75 Rule False
Scaffold Graph Level C1CCC2CCCC2C1
Np Classifier Class Cinnamic acids and derivatives
Deep Smiles C=CCcccOC))ccc6OC)))OCO5
Heavy Atom Count 16.0
Classyfire Class Benzodioxoles
Description Occurs in Sassafras albidum (sassafras) and Anethum graveolens (dill) Apiol is an organic chemical compound, also known as parsley apiol, apiole or parsley camphor. It is found in celery, parsley seeds, and the essential oil of parsley. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation., In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders. It is an irritant and in high doses it is toxic and can cause liver and kidney damage.
Scaffold Graph Node Level C1CCC2OCOC2C1
Isotope Atom Count 0.0
Molecular Complexity 243.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Uniprot Id P51450, P16050, P08684, O94782, Q9NPD5, Q9Y6L6, Q7BGE6, n.a.
Iupac Name 4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole
Prediction Hob 1.0
Class Benzodioxoles
Veber Rule True
Classyfire Superclass Organoheterocyclic compounds
Target Id NPT792, NPT109
Xlogp 2.7
Superclass Organoheterocyclic compounds
Gsk 4 400 Rule True
Molecular Formula C12H14O4
Scaffold Graph Node Bond Level c1ccc2c(c1)OCO2
Prediction Swissadme 1.0
Inchi Key QQRSPHJOOXUALR-UHFFFAOYSA-N
Silicos It Class Soluble
Fcsp3 0.3333333333333333
Logs -2.885
Rotatable Bond Count 4.0
State Solid
Logd 2.605
Synonyms 1-Allyl-2,5-dimethoxy-3, 4-(methylenedioxy)benzene, 1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)-benzene, 1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)benzene, 1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene, 1,3-Benzodioxole, 4, 7-dimethoxy-5-(2-propenyl)-, 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propen-1-yl)-, 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propenyl)-, 4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole, 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9CI, 5-Allyl-4,7-dimethoxy-1,3-benzodioxol, 5-Allyl-4,7-dimethoxy-1,3-benzodioxole, Apiol, Apiole (parsley), Apioline, Benzene, 1-allyl-2,5-dimethoxy-3, 4-(methylenedioxy)-, Benzene, 1-allyl-2,5-dimethoxy-3,4-(methylenedioxy)-, Camphre de persil, Parsley apiol, Parsley apiole, Parsley camphor, Petersiliencampher, 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9ci, apiol, apiole, parsley apiole
Substituent Name Benzodioxole, Anisole, Alkyl aryl ether, Benzenoid, Oxacycle, Ether, Acetal, Hydrocarbon derivative, Organooxygen compound, Aromatic heteropolycyclic compound
Esol Class Soluble
Functional Groups C=CC, c1cOCO1, cOC
Compound Name Apiole (parsley)
Kingdom Organic compounds
Prediction Hob Swissadme 1.0
Exact Mass 222.089
Formal Charge 0.0
Monoisotopic Mass 222.089
Hydrogen Bond Acceptor Count 4.0
Molecular Weight 222.24
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 0.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteropolycyclic compounds
Lipinski Rule Of 5 True
Esol -2.963887999999999
Inchi InChI=1S/C12H14O4/c1-4-5-8-6-9(13-2)11-12(10(8)14-3)16-7-15-11/h4,6H,1,5,7H2,2-3H3
Smiles COC1=C2C(=C(C(=C1)CC=C)OC)OCO2
Nring 2.0
Np Classifier Biosynthetic Pathway Shikimates and Phenylpropanoids
Defined Bond Stereocenter Count 0.0
Egan Rule True
Taxonomy Direct Parent Benzodioxoles
Np Classifier Superclass Phenylpropanoids (C6-C3)

  • 1. Outgoing r'ship FOUND_IN to/from Acacia Caven (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699797
  • 2. Outgoing r'ship FOUND_IN to/from Acalypha Hispida (Plant) Rel Props:Reference:https://doi.org/10.3923/ip.2011.144.148
  • 3. Outgoing r'ship FOUND_IN to/from Anethum Graveolens (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 4. Outgoing r'ship FOUND_IN to/from Anethum Sowa (Plant) Rel Props:Reference:ISBN:9788172361150
  • 5. Outgoing r'ship FOUND_IN to/from Anthriscus Sylvestris (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2015.1060176
  • 6. Outgoing r'ship FOUND_IN to/from Apium Graveolens (Plant) Rel Props:Source_db:fooddb_chem_all
  • 7. Outgoing r'ship FOUND_IN to/from Artemisia Dracunculus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 8. Outgoing r'ship FOUND_IN to/from Artemisia Scoparia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 9. Outgoing r'ship FOUND_IN to/from Asarum Heterotropoides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 10. Outgoing r'ship FOUND_IN to/from Astilbe Koreana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 11. Outgoing r'ship FOUND_IN to/from Atroxima Liberica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 12. Outgoing r'ship FOUND_IN to/from Bergenia Crassifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 13. Outgoing r'ship FOUND_IN to/from Boronia Muelleri (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 14. Outgoing r'ship FOUND_IN to/from Brassica Oleracea (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2002.9699748
  • 15. Outgoing r'ship FOUND_IN to/from Brucea Javanica (Plant) Rel Props:Reference:ISBN:9770972795006; ISBN:9788172362089
  • 16. Outgoing r'ship FOUND_IN to/from Bunium Persicum (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2015.1137240
  • 17. Outgoing r'ship FOUND_IN to/from Carum Carvi (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2000.9712206
  • 18. Outgoing r'ship FOUND_IN to/from Cassia Carnaval (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 19. Outgoing r'ship FOUND_IN to/from Christisonia Bicolor (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 20. Outgoing r'ship FOUND_IN to/from Cinnamomum Camphora (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 21. Outgoing r'ship FOUND_IN to/from Colchicum Macedonicum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 22. Outgoing r'ship FOUND_IN to/from Convallaria Majalis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 23. Outgoing r'ship FOUND_IN to/from Coprosma Acerosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 24. Outgoing r'ship FOUND_IN to/from Coptis Deltoidea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 25. Outgoing r'ship FOUND_IN to/from Coriandrum Sativum (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2016.1256234
  • 26. Outgoing r'ship FOUND_IN to/from Cranfillia Vulcanica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 27. Outgoing r'ship FOUND_IN to/from Crithmum Maritimum (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.2730060205
  • 28. Outgoing r'ship FOUND_IN to/from Crotalaria Orixensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 29. Outgoing r'ship FOUND_IN to/from Cullen Corylifolium (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2015.1024890
  • 30. Outgoing r'ship FOUND_IN to/from Cymbopogon Winterianus (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2010.10643885
  • 31. Outgoing r'ship FOUND_IN to/from Dalbergia Frutescens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 32. Outgoing r'ship FOUND_IN to/from Daucus Carota (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 33. Outgoing r'ship FOUND_IN to/from Dicliptera Riparia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 34. Outgoing r'ship FOUND_IN to/from Dillenia Papuana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 35. Outgoing r'ship FOUND_IN to/from Dracocephalum Moldavica (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2000.9712206
  • 36. Outgoing r'ship FOUND_IN to/from Euphorbia Caducifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 37. Outgoing r'ship FOUND_IN to/from Ferula Persica (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.1496
  • 38. Outgoing r'ship FOUND_IN to/from Ficus Elastica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 39. Outgoing r'ship FOUND_IN to/from Foeniculum Vulgare (Plant) Rel Props:Source_db:fooddb_chem_all;npass_chem_all
  • 40. Outgoing r'ship FOUND_IN to/from Hansenia Weberbaueriana (Plant) Rel Props:Source_db:cmaup_ingredients
  • 41. Outgoing r'ship FOUND_IN to/from Hypericum Papuanum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 42. Outgoing r'ship FOUND_IN to/from Ilex Kaushue (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 43. Outgoing r'ship FOUND_IN to/from Illicium Verum (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2012.10644074
  • 44. Outgoing r'ship FOUND_IN to/from Inula Thapsoides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 45. Outgoing r'ship FOUND_IN to/from Kaunia Arbuscularis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 46. Outgoing r'ship FOUND_IN to/from Laggera Aurita (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2009.10643715
  • 47. Outgoing r'ship FOUND_IN to/from Laurus Nobilis (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2000.9712206
  • 48. Outgoing r'ship FOUND_IN to/from Lawsonia Inermis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 49. Outgoing r'ship FOUND_IN to/from Levisticum Officinale (Plant) Rel Props:Source_db:fooddb_chem_all
  • 50. Outgoing r'ship FOUND_IN to/from Licaria Brasiliensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 51. Outgoing r'ship FOUND_IN to/from Limeum Pterocarpum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 52. Outgoing r'ship FOUND_IN to/from Linum Crispum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 53. Outgoing r'ship FOUND_IN to/from Lupinus Formosus (Plant) Rel Props:Source_db:npass_chem_all
  • 54. Outgoing r'ship FOUND_IN to/from Mentha Piperita (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2017.1423247
  • 55. Outgoing r'ship FOUND_IN to/from Nigella Sativa (Plant) Rel Props:Reference:ISBN:9770972795006
  • 56. Outgoing r'ship FOUND_IN to/from Ocimum Basilicum (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2000.9712206
  • 57. Outgoing r'ship FOUND_IN to/from Oxandra Xylopioides (Plant) Rel Props:Source_db:npass_chem_all
  • 58. Outgoing r'ship FOUND_IN to/from Palafoxia Texana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 59. Outgoing r'ship FOUND_IN to/from Palicourea Alpina (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 60. Outgoing r'ship FOUND_IN to/from Passiflora Foetida (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2009.10643715
  • 61. Outgoing r'ship FOUND_IN to/from Perilla Frutescens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 62. Outgoing r'ship FOUND_IN to/from Persicaria Thunbergii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 63. Outgoing r'ship FOUND_IN to/from Petroselinum Crispum (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 64. Outgoing r'ship FOUND_IN to/from Pimpinella Acuminata (Plant) Rel Props:Reference:ISBN:9788185042114
  • 65. Outgoing r'ship FOUND_IN to/from Piper Aduncum (Plant) Rel Props:Reference:https://doi.org/10.1002/(sici)1099-1026(1998070)13:4<269::aid-ffj744>3.0.co;2-a
  • 66. Outgoing r'ship FOUND_IN to/from Piper Angustifolium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 67. Outgoing r'ship FOUND_IN to/from Piper Betle (Plant) Rel Props:Reference:https://doi.org/10.1002/ffj.2730090611
  • 68. Outgoing r'ship FOUND_IN to/from Piper Sarmentosum (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2017.1303405
  • 69. Outgoing r'ship FOUND_IN to/from Posoqueria Latifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 70. Outgoing r'ship FOUND_IN to/from Pseudocinchona Pachyceras (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 71. Outgoing r'ship FOUND_IN to/from Rabdosia Angustifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 72. Outgoing r'ship FOUND_IN to/from Rhodomyrtus Tomentosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 73. Outgoing r'ship FOUND_IN to/from Rosa Canina (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2019.1604167
  • 74. Outgoing r'ship FOUND_IN to/from Rosmarinus Officinalis (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2007.10643580
  • 75. Outgoing r'ship FOUND_IN to/from Salix Sieboldiana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 76. Outgoing r'ship FOUND_IN to/from Salvia Hians (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2011.10643987
  • 77. Outgoing r'ship FOUND_IN to/from Salvia Xalapensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 78. Outgoing r'ship FOUND_IN to/from Sambucus Ebulus (Plant) Rel Props:Source_db:npass_chem_all
  • 79. Outgoing r'ship FOUND_IN to/from Sanguisorba Officinalis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 80. Outgoing r'ship FOUND_IN to/from Satureja Hortensis (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2000.9712206
  • 81. Outgoing r'ship FOUND_IN to/from Scrophularia Smithii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 82. Outgoing r'ship FOUND_IN to/from Scutellaria Sieberi (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 83. Outgoing r'ship FOUND_IN to/from Smilax Bracteata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 84. Outgoing r'ship FOUND_IN to/from Solanum Torvum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 85. Outgoing r'ship FOUND_IN to/from Tanacetum Santolinoides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 86. Outgoing r'ship FOUND_IN to/from Thymus Quinquecostatus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 87. Outgoing r'ship FOUND_IN to/from Thymus Vulgaris (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 88. Outgoing r'ship FOUND_IN to/from Torilis Leptophylla (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2012.10662596
  • 89. Outgoing r'ship FOUND_IN to/from Trifolium Alexandrium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 90. Outgoing r'ship FOUND_IN to/from Trifolium Pratense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 91. Outgoing r'ship FOUND_IN to/from Tylophora Flava (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 92. Outgoing r'ship FOUND_IN to/from Tynanthus Panurensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 93. Outgoing r'ship FOUND_IN to/from Vepris Nobilis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 94. Outgoing r'ship FOUND_IN to/from Wunderlichia Mirabilis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 95. Outgoing r'ship FOUND_IN to/from Zilla Spinosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all