3,9-dihydroxy-4-prenyl-[6aR:11aR]pterocarpan - Compound Card

3,9-dihydroxy-4-prenyl-[6aR:11aR]pterocarpan

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3,9-dihydroxy-4-prenyl-[6aR:11aR]pterocarpan

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Pterocarpan
Canonical Smiles CC(=CCc1c(O)ccc2c1OC[C@@H]1[C@H]2Oc2c1ccc(c2)O)C
InChI InChI=1S/C20H20O4/c1-11(2)3-5-14-17(22)8-7-15-19(14)23-10-16-13-6-4-12(21)9-18(13)24-20(15)16/h3-4,6-9,16,20-22H,5,10H2,1-2H3/t16-,20-/m0/s1
InChIKey QKYUTKLCEVEMIE-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: 46880035
Nmrshiftdb2: 60065837
Bindingdb: 50311578

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC3C2COc4c3cccc4

Level: 0

Mol. Weight: 324.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.9
Plasma Protein Binding
82.45
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
6.35
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.49
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.09
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.17
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
1.84
Rat (Acute)
1.75
Rat (Chronic Oral)
2.05
Fathead Minnow
4.72
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
436.83
Hydration Free Energy
-8.7
Log(D) at pH=7.4
3.67
Log(P)
4.39
Log S
-4.72
Log(Vapor Pressure)
-8.38
Melting Point
191.09
pKa Acid
9.91
pKa Basic
7.03
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9704
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9571
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9187
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.9109
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8934
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8889
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8776
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.8522
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8499
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8492
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8434
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8384
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8335
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8254
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8207
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8204
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.8132
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8131
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8020
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8010
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7990
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7943
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7941
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7938
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7905
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7866
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7835
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7823
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7823
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7818
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7815
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7803
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7797
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7755
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7748
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7747
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7746
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7733
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7714
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7708
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7705
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7646
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7643
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7636
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7631
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7628
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7623
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7623
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7615
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7597
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7580
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7545
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7539
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7531
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7518
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7503
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7495
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7493
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7492
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7470
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7440
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7418
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7413
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7410
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7402
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7396
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7340
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7328
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7325
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7319
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7307
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7305
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7299
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7289
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 3 0.7282
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7280
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7278
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7272
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7254
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7246
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7245
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7228
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7219
Cytidylate kinase Q5SL35 KCY_THET8 Thermus thermophilus 3 0.7215
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7213
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7198
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7187
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7181
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7173
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7173
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7172
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7156
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7154
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7154
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7142
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7140
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7129
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7126
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7112
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7100
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7097
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7092
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7082
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7071
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7068
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7059
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7054
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7052
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7045
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7038
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7034
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 2 0.7031
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7029
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7026
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7021
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7006
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7000

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