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Sophorapterocarpan A

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Pterocarpan

Canonical Smiles	CC(=CCc1cc2c(cc1O)O[C@@H]1[C@H]2COc2c1ccc(c2)O)C
InChI	InChI=1S/C20H20O4/c1-11(2)3-4-12-7-15-16-10-23-18-8-13(21)5-6-14(18)20(16)24-19(15)9-17(12)22/h3,5-9,16,20-22H,4,10H2,1-2H3/t16-,20-/m0/s1
InChIKey	AZLNYSCXKUKIRV-JXFKEZNVSA-N
Formula	C₂₀H₂₀O₄
HBA	4
HBD	2
MW	324.38
Rotatable Bonds	2
TPSA	58.92
LogP	4.22
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	324.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Erythrina abyssinica	Leguminosae/Fabaceae	Plantae	1237573

Showing of synonyms

Nguyen PH, Le TV, et al. (2009). Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica. Bioorganic & medicinal chemistry letters,2009, 19(23), 6745-9. [View] [PubMed]

Pubchem: 14017299

Cas: 77369-92-7

Zinc: ZINC000015115206

Nmrshiftdb2: 60060532

Chembl: CHEMBL1088321

Bindingdb: 50311584

No compound-protein relationship available.

SMILES: c1cccc(c12)OC3C2COc4c3cccc4

Level: 0

Mol. Weight: 324.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.77
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.64
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.7

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.81
Plasma Protein Binding: 85.41
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.88
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.68
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.82
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.16
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: 1.75
Rat (Acute): 1.72
Rat (Chronic Oral): 1.99
Fathead Minnow: 4.74
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 439.04
Hydration Free Energy: -9.2
Log(D) at pH=7.4: 3.96
Log(P): 4.18
Log S: -4.69
Log(Vapor Pressure): -8.98
Melting Point: 207.34
pKa Acid: 10.3
pKa Basic: 7.24

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9544
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9528
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9402
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.9202
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	4	0.9143
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	4	0.9122
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.9049
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8978
Isoflavone 4'-O-methyltransferase	Q29U70	I4OMT_MEDTR	Medicago truncatula	4	0.8953
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8944
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8934
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8837
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8763
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8756
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8736
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8717
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8707
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.8661
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8585
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8569
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8545
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8524
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8493
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8490
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	4	0.8425
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	4	0.8415
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8415
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8370
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8367
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8357
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.8351
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8350
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8340
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8336
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.8274
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8159
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.8140
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8136
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8112
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8106
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8092
Cytochrome P450 130	P9WPN5	CP130_MYCTU	Mycobacterium tuberculosis	3	0.8073
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8067
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8025
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8019
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	4	0.7987
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7975
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7952
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7939
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7915
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7908
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7906
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7903
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7889
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7863
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7842
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7831
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7748
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7711
Beta-adrenergic receptor kinase 1	P25098	ARBK1_HUMAN	Homo sapiens	3	0.7689
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7679
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7679
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	4	0.7676
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7671
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7669
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7668
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7629
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7619
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7605
Putative cytochrome P450	Q70AS3	Q70AS3_STRPE	Streptomyces peucetius	4	0.7596
Isoflavone 4'-O-methyltransferase	Q29U70	I4OMT_MEDTR	Medicago truncatula	4	0.7586
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7581
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7575
Japanin	M1MR49	M1MR49_RHIAP	Rhipicephalus appendiculatus	3	0.7565
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7565
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7497
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7492
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7487
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7469
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7448
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7442
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7440
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7416
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7413
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7408
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7394
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7352
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7348
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7338
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7313
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7312
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	3	0.7311
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7307
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7295
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7268
Uridine phosphorylase	P0A1F6	UDP_SALTY	Salmonella typhimurium	3	0.7259
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7251
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7224
orotidine-5'-phosphate decarboxylase	Q8T6J6	Q8T6J6_PLAFA	Plasmodium falciparum	4	0.7222
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7220
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7216
Cellular retinol-binding protein type II	Q8UVG6	Q8UVG6_DANRE	Danio rerio	3	0.7208
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7199
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7190
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7183
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7178
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7169
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.7156
O-GlcNAcase NagJ	Q0TR53	OGA_CLOP1	Clostridium perfringens	3	0.7149
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7142
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7114
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7111
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7095
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7090
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7089
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7078
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7073
Uridine phosphorylase 2	O95045	UPP2_HUMAN	Homo sapiens	3	0.7073
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7070
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7061
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7061
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7055
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7045
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7040
L-methionine gamma-lyase	P13254	MEGL_PSEPU	Pseudomonas putida	3	0.7029
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7021
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7015
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7012
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7010
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7008
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7005

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