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Procyanidin C-1
- Family: Plantae - Rosaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Proanthocyanidin
| Canonical Smiles | Oc1cc(O)c2c(c1)O[C@@H]([C@@H]([C@H]2c1c(O)cc(c2c1O[C@H](c1ccc(c(c1)O)O)[C@@H]([C@H]2c1c(O)cc(c2c1O[C@@H]([C@@H](C2)O)c1ccc(c(c1)O)O)O)O)O)O)c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1 |
| InChIKey | MOJZMWJRUKIQGL-XILRTYJMSA-N |
| Formula | C45H38O18 |
| HBA | 18 |
| HBD | 15 |
| MW | 866.78 |
| Rotatable Bonds | 5 |
| TPSA | 331.14 |
| LogP | 4.44 |
| Number Rings | 9 |
| Number Aromatic Rings | 6 |
| Heavy Atom Count | 63 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.2 |
| Exact Mass | 866.21 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Crataegus sinaica | Rosaceae | Plantae | 298646 |
| 2 | Psorospermum densipunctatum | Hypericaceae | Plantae | 999533 |
| 3 | Sterculia setigera | Sterculiaceae | Plantae | 66667 |
| 4 | Crataegus monogyna | Rosaceae | Plantae | 140997 |
Showing of synonyms
Procyanidin C-1
Procyanidin C1
37064-30-5
Procyanidol C1
Proanthocyanidin C1
Cinnamtannin A1
UNII-33516LCW4F
CHEBI:75643
33516LCW4F
EC-(4b,8)-EC-(4b,8)-EC
(2r,2'r,2''r,3r,3'r,3''r,4r,4's)-2,2',2''-tris(3,4-dihydroxyphenyl)-3,3',3'',4,4',4''-hexahydro-2h,2'h,2''h-4,8':4',8''-terchromene-3,3',3'',5,5',5'',7,7',7''-nonol
Epicatechin-(4beta->8)-epicatechin-(4beta->8)-epicatechin
PROCYANIDIN C1, (+)-
DTXSID10190562
[Epicatechin(4b->8)]2-epicatechin
(4,8':4',8''-Ter-2H-1-benzopyran)-3,3',3'',5,5',5'',7,7',7''-nonol, 2,2',2''-tris(3,4-dihydroxyphenyl)-3,3',3'',4,4',4''-hexahydro-, stereoisomer
[Epicatechin-(4beta->8)]2-epicatechin
(Epicatechin(4b->8))2-epicatechin
(Epicatechin-(4beta->8))2-epicatechin
DTXCID50113053
PROCYANIDIN C1 (CONSTITUENT OF MARITIME PINE)
(2R,2'R,2''R,3R,3'R,3''R,4R,4'S)-2,2',2''-Tris(3,4-dihydroxyphenyl)-[4,8':4',8''-terchroman]-3,3',3'',5,5',5'',7,7',7''-nonaol
Procyanidin trimer C1
CHEMBL290632
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
C45H38O18
PCC1
Procyanidin C1 (Standard)
SCHEMBL678609
HY-N2342R
HY-N2342
BDBM50240460
MSK166802
AKOS027321198
AC-35069
DA-77079
MS-31600
1ST166802
CS-0021304
C17624
Q7247556
Epicatechin-(4beta-8)-epicatechin-(4beta-8)-epicatechin
PROCYANIDIN C1 (CONSTITUENT OF MARITIME PINE) [DSC]
Epicatechin-(4.beta.-->8)epicatechin-(4.beta.-->8)epicatechin
EPICATECHIN-(4.BETA.->8)-EPICATECHIN-(4.BETA.->8)-EPICATECHIN
(2R,3R,4R,2''R,3''R,4''S,2''''R,3''''R)-2,2'',2''''-Tris-(3,4-dihydroxy-phenyl)-3,4,3'',4'',3'''',4''''-hexahydro-2H,2''H,2''''H-[4,8''
4'',8'''']terchromene-3,5,7,3'',5'',7'',3'''',5'''',7''''-nonaol
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-4-yl]chromane-3,5,7-triol
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
- Shahat AA, Ismail SI, et al. (1998). Anti-HIV activity of flavonoids and proanthocyanidins from Crataegus sinaica. Phytomedicine,1998,5(2),133-136. [View] [PubMed]
- Andima M, Coghi P, et al. (2021). Chemical constituents and biological activities of African medicinal tree Sterculia setigera Delile stem bark. South African Journal of Botany, 2021, 143, 274-281. [View]
- Tanemossu S, Franke K, et al. (2015). Chemical constituents of Psorospermum densipunctatum (Hypericaceae). Biochemical Systematics and Ecology, 2015, 59, 174-176. [View]
- Mraihi F, Hidalgo M, et al. (2015). Wild grown red and yellow hawthorn fruits from Tunisia as source of antioxidants. Arabian Journal of Chemistry, 2015, 8(4), 570-578. [View]
Pubchem:
169853
Cas:
37064-30-5
Gnps:
CCMSLIB00005756138
Zinc:
ZINC000096095372
Kegg Ligand:
C17624
Chebi:
75643
Nmrshiftdb2:
60027098
Metabolights:
MTBLC75643
Chembl:
CHEMBL290632
Comptox:
DTXSID10190562
Bindingdb:
50240460
CPRiL:
413375
SMILES: c1cccc(c12)OC(c3ccccc3)CC2c4cccc(c45)C(CC(O5)c6ccccc6)c7cccc(c78)CCC(O8)c9ccccc9
Level: 5
Mol. Weight: 866.78 g/mol
SMILES: c1cccc(c12)OCCC2c3cccc(c34)C(CC(O4)c5ccccc5)c6cccc(c67)CCC(O7)c8ccccc8
Level: 4
Mol. Weight: 866.78 g/mol
SMILES: c1cccc(c12)OC(c3ccccc3)CC2c4cccc(c45)C(CCO5)c6cccc(c67)CCC(O7)c8ccccc8
Level: 4
Mol. Weight: 866.78 g/mol
SMILES: O1CCCc(c12)cccc2C(CC(O3)c4ccccc4)c(c35)cccc5C6CC(c7ccccc7)Oc(c68)cccc8
Level: 4
Mol. Weight: 866.78 g/mol
SMILES: c1cccc(c12)OCCC2c3cccc(c34)C(CCO4)c5cccc(c56)CCC(O6)c7ccccc7
Level: 3
Mol. Weight: 866.78 g/mol
SMILES: O1CCCc(c12)cccc2C(CCO3)c(c34)cccc4C5CC(c6ccccc6)Oc(c57)cccc7
Level: 3
Mol. Weight: 866.78 g/mol
SMILES: O1CCCc(c12)cccc2C(CC(O3)c4ccccc4)c(c35)cccc5C6CCOc(c67)cccc7
Level: 3
Mol. Weight: 866.78 g/mol
SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CC(c5ccccc5)Oc(c46)cccc6
Level: 3
Mol. Weight: 866.78 g/mol
SMILES: O1CCCc(c12)cccc2C(CCO3)c(c34)cccc4C5CCOc(c56)cccc6
Level: 2
Mol. Weight: 866.78 g/mol
SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CCOc(c45)cccc5
Level: 2
Mol. Weight: 866.78 g/mol
SMILES: O1CCCc(c12)cccc2C3CC(c4ccccc4)Oc(c35)cccc5
Level: 2
Mol. Weight: 866.78 g/mol
SMILES: O1CCCc(c12)cccc2C3CCOc(c34)cccc4
Level: 1
Mol. Weight: 866.78 g/mol
SMILES: c1cccc(c12)OC(CC2)c3ccccc3
Level: 1
Mol. Weight: 866.78 g/mol
SMILES: C1CCOc(c12)cccc2
Level: 0
Mol. Weight: 866.78 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 866.78 g/mol
Anti-hiv
Absorption
- Caco-2 (logPapp)
- -6.18
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 1630.78
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 214098.82
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.68
- Plasma Protein Binding
- 72.28
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 10.38
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -4970.21
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.26
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.12
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -388567011.86
- Rat (Acute)
- 2.27
- Rat (Chronic Oral)
- 4.93
- Fathead Minnow
- 490492.19
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 43694066.05
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -10.43
- Log(P)
- 2.78
- Log S
- -5.34
- Log(Vapor Pressure)
- -1438724.11
- Melting Point
- 315.98
- pKa Acid
- -10439.05
- pKa Basic
- -52.25
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8788 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8788 |
| Multidrug-efflux transporter 1 regulator | P39075 | BMRR_BACSU | Bacillus subtilis | 3 | 0.8567 |
| Multidrug-efflux transporter 1 regulator | P39075 | BMRR_BACSU | Bacillus subtilis | 3 | 0.8567 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8365 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8365 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8333 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8333 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.8295 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.8295 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8214 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8214 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8189 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8189 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7804 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7804 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7281 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7281 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7256 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7256 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7235 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7235 |
| UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7163 |
| UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7163 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7162 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7162 |
| 5-formyltetrahydrofolate cyclo-ligase | P75430 | MTHFS_MYCPN | Mycoplasma pneumoniae | 2 | 0.7025 |
| 5-formyltetrahydrofolate cyclo-ligase | P75430 | MTHFS_MYCPN | Mycoplasma pneumoniae | 2 | 0.7025 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7007 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7007 |