12-hydroxyerosone - Compound Card

12-hydroxyerosone

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12-hydroxyerosone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1cc2c(cc1OC)CC[C@@H]1[C@@]2(O)C(=O)c2c(O1)cc1c(c2)cco1
InChI InChI=1S/C21H18O6/c1-24-17-8-11-3-4-19-21(23,14(11)9-18(17)25-2)20(22)13-7-12-5-6-26-15(12)10-16(13)27-19/h5-10,19,23H,3-4H2,1-2H3/t19-,21-/m1/s1
InChIKey OQUXSJDSDHAMOY-TZIWHRDSSA-N
Formula C21H18O6
HBA 6
HBD 1
MW 366.37
Rotatable Bonds 2
TPSA 78.13
LogP 3.23
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 366.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Neorautanenia mitis Leguminosae/Fabaceae Plantae 167620

Showing of synonyms

  • Sakurai Y, Sakurai N, et al. (2006). Rautandiols A and B, pterocarpans and cytotoxic constituents from Neorautanenia mitis.. Journal of Natural Products,2006,69(3),397-399. [View] [PubMed]
Pubchem: 44575274
Nmrshiftdb2: 70043356

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)cc3c(c2)C(=O)C4c5c(CCC4O3)cccc5

Level: 0

Mol. Weight: 366.37 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.650
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.410
Plasma Protein Binding
79.04
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
5.900
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.610
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.130
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.250
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
-11.930
Rat (Acute)
3.180
Rat (Chronic Oral)
2.130
Fathead Minnow
4.880
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
449.690
Hydration Free Energy
-6.650
Log(D) at pH=7.4
2.890
Log(P)
2.84
Log S
-4.15
Log(Vapor Pressure)
-8.89
Melting Point
218.61
pKa Acid
8.07
pKa Basic
2.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9294
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9294
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.9183
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.9183
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.9048
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.9048
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8846
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8846
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8812
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8812
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8764
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8764
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8758
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8758
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8453
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8453
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8433
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8433
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8423
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8423
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8394
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8394
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8306
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8306
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8248
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8248
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.8235
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.8235
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8208
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8208
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8191
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8191
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 4 0.8075
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 4 0.8075
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8037
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8037
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8028
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8028
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7915
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7915
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7898
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7898
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7811
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7811
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7792
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7792
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.7766
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.7766
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7761
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7761
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7748
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7748
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7722
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7722
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7710
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7710
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7709
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7709
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7665
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7665
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7657
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7657
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7651
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7651
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 3 0.7639
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 3 0.7639
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7619
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7619
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7615
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7615
Enoyl-acyl carrier reductase C6KSZ2 C6KSZ2_PLAF7 Plasmodium falciparum 4 0.7601
Enoyl-acyl carrier reductase C6KSZ2 C6KSZ2_PLAF7 Plasmodium falciparum 4 0.7601
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7589
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7589
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7572
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7572
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7564
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7564
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7557
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7557
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7522
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7522
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7520
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7520
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7510
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7510
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7504
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7504
AGAP001556-PA Q7PXT9 Q7PXT9_ANOGA Anopheles gambiae 3 0.7480
AGAP001556-PA Q7PXT9 Q7PXT9_ANOGA Anopheles gambiae 3 0.7480
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7460
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7460
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7458
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7458
Orf1ab polyprotein Q6T1E9 Q6T1E9_CVHSA SARS coronavirus CUHK-L2 3 0.7443
Orf1ab polyprotein Q6T1E9 Q6T1E9_CVHSA SARS coronavirus CUHK-L2 3 0.7443
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7427
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7427
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7417
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7417
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7401
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7401
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7380
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7380
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7350
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7350
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7331
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7331
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7327
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7327
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7307
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7307
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7297
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7297
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7297
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7297
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7291
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7291
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7241
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7241
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7241
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7241
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7235
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7235
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7225
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7225
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7217
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7217
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7184
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7184
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7175
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7175
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7170
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7170
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7161
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7161
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7153
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7153
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7145
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7145
Mu-type opioid receptor P42866 OPRM_MOUSE Mus musculus 3 0.7144
Mu-type opioid receptor P42866 OPRM_MOUSE Mus musculus 3 0.7144
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7142
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7142
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7136
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7136
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7136
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7136
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7107
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7107
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7100
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7100
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7089
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7089
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7079
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7079
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7075
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7075
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7074
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7074
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7071
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7071
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7069
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7069
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7050
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7050
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7046
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7046
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7038
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7038
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7013
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7013
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7008
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7008

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