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Proanthocyanidin B-2

Family: Plantae - Hypericaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2c1c(O)cc(c2c1O[C@@H]([C@@H](C2)O)c1ccc(c(c1)O)O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26?,27-,28-,29-/m1/s1
InChIKey	XFZJEEAOWLFHDH-ATEOAPGCSA-N
Formula	C₃₀H₂₆O₁₂
HBA	12
HBD	10
MW	578.53
Rotatable Bonds	3
TPSA	220.76
LogP	3.0
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.2
Exact Mass	578.14
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Psorospermum densipunctatum	Hypericaceae	Plantae	999533

Showing of synonyms

Tanemossu S, Franke K, et al. (2015). Chemical constituents of Psorospermum densipunctatum (Hypericaceae). Biochemical Systematics and Ecology, 2015, 59, 174-176. [View]

Pubchem: 5320711

Nmrshiftdb2: 60025049

No compound-protein relationship available.

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CC(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 578.53 g/mol

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CCOc(c45)cccc5

Level: 2

Mol. Weight: 578.53 g/mol

SMILES: O1CCCc(c12)cccc2C3CC(c4ccccc4)Oc(c35)cccc5

Level: 2

Mol. Weight: 578.53 g/mol

SMILES: O1CCCc(c12)cccc2C3CCOc(c34)cccc4

Level: 1

Mol. Weight: 578.53 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 578.53 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 578.53 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 578.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.62
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.63
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 9.07

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.81
Plasma Protein Binding: 74.63
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-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: Non-Inhibitor

Excretion

Clearance: 11.81
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.72
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.13
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.21
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: -11809.87
Rat (Acute): 2.39
Rat (Chronic Oral): 4.23
Fathead Minnow: 27.54
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: 531.52
Hydration Free Energy: -3.17
Log(D) at pH=7.4: 1.3
Log(P): 1.74
Log S: -4.33
Log(Vapor Pressure): -12.5
Melting Point: 278.82
pKa Acid: 6.61
pKa Basic: 7.26

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9053
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.9013
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8923
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8840
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8816
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8643
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.8568
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8510
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8506
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8421
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8396
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8360
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8319
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.8315
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8313
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8235
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8208
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8188
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	4	0.8155
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8121
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8099
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8007
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8006
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7880
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7863
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7821
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7820
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7771
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7768
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7748
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7657
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7623
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7610
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7594
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7551
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7477
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7423
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7366
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7352
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7296
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7267
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	4	0.7249
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7230
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	4	0.7215
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7214
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7211
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7211
Prostaglandin reductase 3	Q8N4Q0	PTGR3_HUMAN	Homo sapiens	5	0.7152
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7139
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	4	0.7137
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7094
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.7093
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	5	0.7026
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7019
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7009

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