ANPDB

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Procyanidin dimer B

Family: Plantae - Sterculiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol

Canonical Smiles	Oc1cc(O)c2c(c1)O[C@@H]([C@@H]([C@H]2c1c(O)cc2c(c1O)CC([C@@H](O2)c1ccc(c(c1)O)O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21?,26-,28-,29+,30-/m1/s1
InChIKey	GMISZFQPFDAPGI-WXXMRKNTSA-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	Sterculia setigera	Sterculiaceae	Plantae	66667

Showing of synonyms

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]

Pubchem: 131752343

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(c3ccccc3)CC2c(c4)ccc(c45)OC(CC5)c6ccccc6

Level: 3

Mol. Weight: 578.53 g/mol

SMILES: c1cccc(c12)OCCC2c(c3)ccc(c34)OC(CC4)c5ccccc5

Level: 2

Mol. Weight: 578.53 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)CC2c(c4)ccc(c45)OCCC5

Level: 2

Mol. Weight: 578.53 g/mol

SMILES: c1cccc(c12)OCCC2c(c3)ccc(c34)OCCC4

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): -6.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.65
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 9.06

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.79
Plasma Protein Binding: 80.8
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: 11.69
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.71
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.09
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.29
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: -11868.89
Rat (Acute): 2.4
Rat (Chronic Oral): 4.28
Fathead Minnow: 27.55
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: 525.35
Hydration Free Energy: -3.17
Log(D) at pH=7.4: 1.23
Log(P): 2.16
Log S: -4.16
Log(Vapor Pressure): -12.77
Melting Point: 297.06
pKa Acid: 6.46
pKa Basic: 7.45

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	0.9182
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9008
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8971
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8803
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8781
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8746
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8742
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.8724
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8644
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8612
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8602
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8543
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8503
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	4	0.8456
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8432
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8415
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8409
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8391
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8323
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8319
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8296
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	4	0.8260
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8229
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8180
Beta-glucosidase 1A	Q25BW5	BGL1A_PHACH	Phanerodontia chrysosporium	3	0.8171
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8151
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8093
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8021
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8016
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7993
Polymerase basic protein 2	Q2LG68	Q2LG68_9INFA	Influenza A virus)	6	0.7964
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7953
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.7925
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7887
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7835
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7833
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7809
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7792
chitinase	B0Y2Y2	B0Y2Y2_ASPFC	Aspergillus fumigatus	4	0.7785
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7776
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7744
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7721
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7719
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7719
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7710
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7705
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7685
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	4	0.7679
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7601
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7577
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7552
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.7537
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7537
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	4	0.7523
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7508
Leucine--tRNA ligase	P07813	SYL_ECOLI	Escherichia coli	4	0.7504
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7501
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7500
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7495
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7487
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7461
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7413
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	4	0.7390
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7384
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	4	0.7364
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7362
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7359
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	4	0.7345
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7345
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7300
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7298
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7274
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7222
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7219
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7216
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7180
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.7164
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7162
Enoyl-[acyl-carrier-protein] reductase [NADH]	Q2GKM8	Q2GKM8_ANAPZ	Anaplasma phagocytophilum	4	0.7160
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7150
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7144
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.7138
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7130
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7123
Histidinol dehydrogenase	Q8G2R2	HISX_BRUSU	Brucella suis biovar 1	4	0.7122
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7122
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	5	0.7120
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7103
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7088
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7084
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7080
mRNA-capping enzyme subunit alpha	P78587	MCE1_CANAX	Candida albicans	3	0.7067
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.7025
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7023
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.7023
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7001

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