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Proanthocyanidin A1

PubChem CID: 9872976

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Compound Synonyms Proanthocyanidin A1, Procyanidin A1, 103883-03-0, (1R,5R,6S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol, C30H24O12, (1R,5R,6S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol, (2R,3S,8S,14R,15R)-2,8-Bis(3,4-dihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol, Proanthocyanidin A-1, (+)-Proanthocyanidin A2, (1R,5R,6S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo(11.7.1.0^(2,11).0^(3,8).0^(15,20))henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol, (1R,5R,6S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo(11.7.1.02,11.03,8.015,20)henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol, 12798-56-0, Procyanidin A1 (Standard), LX492GRN5W, CHEMBL450916, SCHEMBL1689429, HY-N2344R, (+)-PROANTHOCYANIDIN A1, CHEBI:169780, HY-N2344, BDBM50428821, EC-(4b,8)(2b,7)-C, AKOS037515001, Epicatechin-(2b->7,4b->8)-catechin, AC-35020, DA-57053, CS-0021306, (2R,3S,8S,14R,15R)-2,8-BIS(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-8,14-METHANO-2H,14H-1-BENZOPYRANO(7,8-D)(1,3)BENZODIOXOCIN-3,5,11,13,15-PENTOL, 2,8-Bis(3,4-dihydroxyphenyl)-3,4-dihydro-8,14-methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, Procyanidol A1, 8,14-METHANO-2H,14H-1-BENZOPYRANO(7,8-D)(1,3)BENZODIOXOCIN-3,5,11,13,15-PENTOL, 2,8-BIS(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, (2R,3S,8S,14R,15R)-, 8,14-METHANO-2H,14H-1-BENZOPYRANO(7,8-D)(1,3)BENZODIOXOCIN-3,5,11,13,15-PENTOL, 2,8-BIS(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, (2R-(2.ALPHA.,3.BETA.,8.BETA.,14.BETA.,15R*))-
Topological Polar Surface Area 210.0
Hydrogen Bond Donor Count 9.0
Heavy Atom Count 42.0
Description Isolated from cassia bark (Cinnamomum aromaticum). Proanthocyanidin A1 is found in many foods, some of which are lingonberry, peanut, cinnamon, and cocoa bean.
Isotope Atom Count 0.0
Molecular Complexity 986.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;npass_chem_all;pubchem
Defined Atom Stereocenter Count 5.0
Uniprot Id n.a., P15692, P49763
Iupac Name (1R,5R,6S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
Prediction Hob 0.0
Class Flavonoids
Xlogp 2.4
Superclass Phenylpropanoids and polyketides
Subclass Biflavonoids and polyflavonoids
Molecular Formula C30H24O12
Prediction Swissadme 0.0
Inchi Key NSEWTSAADLNHNH-TXZJYACMSA-N
Fcsp3 0.2
Logs -3.913
Rotatable Bond Count 2.0
State Solid
Logd 1.742
Synonyms EC-(4b,8)(2b,7)-C, Epicatechin-(2b->7,4b->8)-catechin, Proanthocyanidin A1, Proanthocyanidin a-1, Proanthocyanidin a1
Compound Name Proanthocyanidin A1
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 576.127
Formal Charge 0.0
Monoisotopic Mass 576.127
Hydrogen Bond Acceptor Count 12.0
Molecular Weight 576.5
Covalent Unit Count 1.0
Total Atom Stereocenter Count 5.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteropolycyclic compounds
Esol -5.210919142857145
Inchi InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26+,27+,29+,30-/m0/s1
Smiles C1[C@@H]([C@H](OC2=C1C(=CC3=C2[C@@H]4[C@H]([C@](O3)(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O)C7=CC(=C(C=C7)O)O)O
Nring 7.0
Defined Bond Stereocenter Count 0.0
Taxonomy Direct Parent Biflavonoids and polyflavonoids

  • 1. Outgoing r'ship FOUND_IN to/from Aconitum Pseudohuiliense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 2. Outgoing r'ship FOUND_IN to/from Aconitum Sachalinense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 3. Outgoing r'ship FOUND_IN to/from Alangium Premnifolium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 4. Outgoing r'ship FOUND_IN to/from Alstonia Deplanchei (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 5. Outgoing r'ship FOUND_IN to/from Angelica Tarokoensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 6. Outgoing r'ship FOUND_IN to/from Arachis Hypogaea (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 7. Outgoing r'ship FOUND_IN to/from Aster Bellidiastrum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 8. Outgoing r'ship FOUND_IN to/from Asteriscus Graveolens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 9. Outgoing r'ship FOUND_IN to/from Baccharis Megapotamica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 10. Outgoing r'ship FOUND_IN to/from Bombax Ceiba (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 11. Outgoing r'ship FOUND_IN to/from Bragantia Wallichii (Plant) Rel Props:Source_db:npass_chem_all
  • 12. Outgoing r'ship FOUND_IN to/from Cacalia Bicolor (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 13. Outgoing r'ship FOUND_IN to/from Centrosema Pascuorum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 14. Outgoing r'ship FOUND_IN to/from Ceratozamia Fuscoviridis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 15. Outgoing r'ship FOUND_IN to/from Citrus Glauca (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 16. Outgoing r'ship FOUND_IN to/from Codium Decorticatum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 17. Outgoing r'ship FOUND_IN to/from Critonia Quadrangularis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 18. Outgoing r'ship FOUND_IN to/from Delphinium Andersoni (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 19. Outgoing r'ship FOUND_IN to/from Diphasia Angolensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 20. Outgoing r'ship FOUND_IN to/from Dolomiaea Souliei (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 21. Outgoing r'ship FOUND_IN to/from Epimedium Davidii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 22. Outgoing r'ship FOUND_IN to/from Erigeron Crispus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 23. Outgoing r'ship FOUND_IN to/from Erysimum Odoratum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 24. Outgoing r'ship FOUND_IN to/from Eucalyptus Camaldulensis (Plant) Rel Props:Source_db:npass_chem_all
  • 25. Outgoing r'ship FOUND_IN to/from Eupatorium Gracile (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 26. Outgoing r'ship FOUND_IN to/from Ficus Simplicissima (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 27. Outgoing r'ship FOUND_IN to/from Flemingia Congesta (Plant) Rel Props:Source_db:npass_chem_all
  • 28. Outgoing r'ship FOUND_IN to/from Frullania Tamarisci (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 29. Outgoing r'ship FOUND_IN to/from Galenia Africana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 30. Outgoing r'ship FOUND_IN to/from Garcinia Mangostana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 31. Outgoing r'ship FOUND_IN to/from Globba Malaccensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 32. Outgoing r'ship FOUND_IN to/from Gnidia Lamprantha (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 33. Outgoing r'ship FOUND_IN to/from Halimodendron Halodendron (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 34. Outgoing r'ship FOUND_IN to/from Haplophyllum Dauricum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 35. Outgoing r'ship FOUND_IN to/from Heterotheca Inuloides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 36. Outgoing r'ship FOUND_IN to/from Ilex Amara (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 37. Outgoing r'ship FOUND_IN to/from Isodon Japonicus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 38. Outgoing r'ship FOUND_IN to/from Knightia Excelsa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 39. Outgoing r'ship FOUND_IN to/from Leonurus Glaucescens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 40. Outgoing r'ship FOUND_IN to/from Lepidium Draba (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 41. Outgoing r'ship FOUND_IN to/from Lonicera Hypoleuca (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 42. Outgoing r'ship FOUND_IN to/from Maba Buxifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 43. Outgoing r'ship FOUND_IN to/from Marrubium Supinum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 44. Outgoing r'ship FOUND_IN to/from Metalasia Bolusii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 45. Outgoing r'ship FOUND_IN to/from Micromeria Pineolens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 46. Outgoing r'ship FOUND_IN to/from Nicotiana Sylvestris (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 47. Outgoing r'ship FOUND_IN to/from Orthosphenia Mexicana (Plant) Rel Props:Source_db:npass_chem_all
  • 48. Outgoing r'ship FOUND_IN to/from Oxyanthus Speciosus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 49. Outgoing r'ship FOUND_IN to/from Pterospermum Heyneanum (Plant) Rel Props:Source_db:npass_chem_all
  • 50. Outgoing r'ship FOUND_IN to/from Quercus Dentata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 51. Outgoing r'ship FOUND_IN to/from Quercus Sessiliflora (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 52. Outgoing r'ship FOUND_IN to/from Relhania Pumila (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 53. Outgoing r'ship FOUND_IN to/from Rheum Tanguticum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 54. Outgoing r'ship FOUND_IN to/from Salacia Madagascariensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 55. Outgoing r'ship FOUND_IN to/from Saussurea Carthamoides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 56. Outgoing r'ship FOUND_IN to/from Senecio Latifolius (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 57. Outgoing r'ship FOUND_IN to/from Senecio Rivularis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 58. Outgoing r'ship FOUND_IN to/from Senecio Vellereus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 59. Outgoing r'ship FOUND_IN to/from Serpocaulon Triseriale (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 60. Outgoing r'ship FOUND_IN to/from Solanum Acaule (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 61. Outgoing r'ship FOUND_IN to/from Solanum Elaeagnifolium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 62. Outgoing r'ship FOUND_IN to/from Stevia Mercedensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 63. Outgoing r'ship FOUND_IN to/from Strychnos Tabascana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 64. Outgoing r'ship FOUND_IN to/from Styrax Perkinsiae (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 65. Outgoing r'ship FOUND_IN to/from Swertia Delavayi (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 66. Outgoing r'ship FOUND_IN to/from Swinglea Glutinosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 67. Outgoing r'ship FOUND_IN to/from Theobroma Cacao (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 68. Outgoing r'ship FOUND_IN to/from Thuja Standishii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 69. Outgoing r'ship FOUND_IN to/from Verbesina Rupestris (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 70. Outgoing r'ship FOUND_IN to/from Vismia Jefensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 71. Outgoing r'ship FOUND_IN to/from Wibelia Divaricata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all