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Procyanidin trimer C2

Family: Plantae - Rosaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Hydroxybenzoic Derivative

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+/m0/s1
InChIKey	MOJZMWJRUKIQGL-WNCKYJNFSA-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 monogyna	Rosaceae	Plantae	140997

Showing of synonyms

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: 11182062

Cas: 37064-31-6

Gnps: CCMSLIB00000209707

Zinc: ZINC000096095373

Chebi: 75644

Nmrshiftdb2: 60028431

Metabolights: MTBLC75644

CPRiL: 422597

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

No bioactivities available.

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: 214098.86

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.68
Plasma Protein Binding: 71.52
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: 10.39
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -4970.83
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: 490492.34
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: 43694118.92
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -9.95
Log(P): 2.73
Log S: -5.34
Log(Vapor Pressure): -1438722.33
Melting Point: 314.07
pKa Acid: -10439.7
pKa Basic: -52.55

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.9005
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8313
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	3	0.8275
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8211
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8210
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7826
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7716
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7571
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7195
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7172
Primosomal protein N'	A6TGC5	A6TGC5_KLEP7	Klebsiella pneumoniae subsp. pneumoniae	4	0.7166
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7135
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7075

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