3-hydroxy-2-methoxy-8,9-methylenedioxypterocarpene - Compound Card

3-hydroxy-2-methoxy-8,9-methylenedioxypterocarpene

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3-hydroxy-2-methoxy-8,9-methylenedioxypterocarpene

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Pterocarpin
Canonical Smiles COc1c(O)ccc2c1OCc1c2oc2c1cc1c(c2)OCO1
InChI InChI=1S/C17H12O6/c1-19-17-11(18)3-2-8-15-10(6-20-16(8)17)9-4-13-14(22-7-21-13)5-12(9)23-15/h2-5,18H,6-7H2,1H3
InChIKey GCMNUBMUFAKPBL-UHFFFAOYSA-N
Formula C17H12O6
HBA 6
HBD 1
MW 312.28
Rotatable Bonds 1
TPSA 70.29
LogP 3.44
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 312.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia rhodesica Leguminosae/Fabaceae Plantae 556521

Showing of synonyms

  • Atilaw Y, Muiva-Mutisya L, et al. (2020). Prenylated Flavonoids from the Roots of Tephrosia rhodesica. Journal of natural products, 2020, 83(8), 2390–2398. [View]
Pubchem: 44257500

No compound-protein relationship available.

Structure

SMILES: c1cccc(OC2)c1c(c2c34)oc3cc5c(c4)OCO5

Level: 0

Mol. Weight: 312.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.570
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.370
Plasma Protein Binding
81.71
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
Non-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
10.690
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.810
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.700
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.090
Micronucleos
Toxic
NR-AhR
Toxic
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
Toxic
T. Pyriformis
2.410
Rat (Acute)
2.260
Rat (Chronic Oral)
1.870
Fathead Minnow
5.170
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
430.620
Hydration Free Energy
-8.620
Log(D) at pH=7.4
2.790
Log(P)
3.19
Log S
-4.79
Log(Vapor Pressure)
-8.95
Melting Point
227.7
pKa Acid
8.46
pKa Basic
1.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9517
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9463
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.9361
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9343
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9241
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9239
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.9198
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.9197
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9169
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9123
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9092
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9081
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9074
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9073
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9071
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8992
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8952
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8936
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8921
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.8907
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8907
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.8891
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8818
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8689
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8663
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8580
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8560
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8450
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8440
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8418
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8406
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8400
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8389
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8387
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8383
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8363
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8317
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8295
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.8281
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.8264
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8218
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8137
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8087
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.8084
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8047
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8043
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8034
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8026
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8018
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8008
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7981
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7968
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7968
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7963
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7961
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7935
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7859
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7857
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7847
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7835
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7829
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7766
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7754
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7742
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7733
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7714
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7710
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7710
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7688
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7678
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7664
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7664
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7659
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7656
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7647
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7645
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7628
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 4 0.7625
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7624
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7620
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7610
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7597
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7595
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7580
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7522
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7515
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7511
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7499
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7491
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7490
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7480
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7476
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7474
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7465
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7454
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7434
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7424
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7420
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7419
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7418
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7398
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7392
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7389
Farnesyl pyrophosphate synthase P14324 FPPS_HUMAN Homo sapiens 2 0.7377
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7376
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7364
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7363
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7352
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7341
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7341
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7325
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7321
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7305
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7296
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7291
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7286
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7278
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7263
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7259
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7259
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 3 0.7245
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7242
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7241
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7235
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7231
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7228
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.7220
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7208
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7196
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7180
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7160
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7158
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7154
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7148
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7147
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7146
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7133
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7130
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7125
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7110
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7105
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7103
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7100
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7097
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7075
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7075
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7070
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7060
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7059
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7057
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7053
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7052
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7042
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7041
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7037
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7033
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7015
Rho family GTPase C4M4W4 C4M4W4_ENTHI Entamoeba histolytica 4 0.7008
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7005

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