12-deoxo-12a-hydroxyelliptone - Compound Card

12-deoxo-12a-hydroxyelliptone

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12-deoxo-12a-hydroxyelliptone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Rotenoid
Canonical Smiles COc1cc2c(cc1OC)OCC1C2[C@H](O)c2c(O1)c1ccoc1cc2
InChI InChI=1S/C20H18O6/c1-22-15-7-12-14(8-16(15)23-2)25-9-17-18(12)19(21)11-3-4-13-10(5-6-24-13)20(11)26-17/h3-8,17-19,21H,9H2,1-2H3/t17?,18?,19-/m1/s1
InChIKey ZVEDKPGZOXEGTK-CTWPCTMYSA-N
Formula C20H18O6
HBA 6
HBD 1
MW 354.36
Rotatable Bonds 2
TPSA 70.29
LogP 3.42
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 354.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia duchesnei Leguminosae/Fabaceae Plantae 2708899

Showing of synonyms

  • Ngandeu F, Bezabih M, et al. (2008). Rotenoid derivatives and other constituents of the twigs of Millettia duchesnei.. Phytochemistry,2008, 69(1), 258-263. [View] [PubMed]
Pubchem: 23238582

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)ccc3c2OC4C(C3)c5c(OC4)cccc5

Level: 0

Mol. Weight: 354.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.570
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.280
Plasma Protein Binding
66.75
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.750
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.220
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.430
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.620
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
Safe
T. Pyriformis
-8.050
Rat (Acute)
2.660
Rat (Chronic Oral)
2.210
Fathead Minnow
5.090
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
453.430
Hydration Free Energy
-6.960
Log(D) at pH=7.4
2.690
Log(P)
2.56
Log S
-4.03
Log(Vapor Pressure)
-8.84
Melting Point
178.6
pKa Acid
10.77
pKa Basic
3.82
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9262
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8983
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8978
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8960
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8883
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8851
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8834
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8805
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8761
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8704
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8633
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8587
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.8547
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8511
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8497
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8443
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8435
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8424
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8423
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8400
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8267
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8252
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8240
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8157
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8115
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8019
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.8013
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7966
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7953
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7952
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7938
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7905
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7864
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 4 0.7812
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7794
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7790
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7763
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7740
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7735
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7722
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7702
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7681
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7664
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7641
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7616
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7583
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.7573
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7553
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7522
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7492
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7482
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7480
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7478
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7470
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7467
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7462
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7461
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7451
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7448
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7439
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7428
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7425
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7418
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7416
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7403
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7401
Enoyl-acyl carrier reductase C6KSZ2 C6KSZ2_PLAF7 Plasmodium falciparum 4 0.7396
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7391
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7386
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7369
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7368
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7355
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7348
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7348
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7339
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7335
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7334
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7325
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7321
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7303
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7288
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7284
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7281
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7274
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7271
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7253
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7241
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7232
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7228
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7226
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7224
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7217
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7204
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7199
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7162
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7158
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7158
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7153
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7142
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7125
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7120
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7112
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7100
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 2 0.7100
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7096
Inorganic pyrophosphatase Q3JUV5 Q3JUV5_BURP1 Burkholderia pseudomallei 3 0.7084
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7084
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7080
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7071
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 4 0.7065
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7053
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7052
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7043
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7038
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7035
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7031
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7021
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7013
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7012
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7008
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7000

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