12-deoxo-12alpha-methoxyelliptone - Compound Card

12-deoxo-12alpha-methoxyelliptone

Select a section from the left sidebar

12-deoxo-12alpha-methoxyelliptone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles CO[C@H]1C2C(COc3c2cc(OC)c(c3)OC)Oc2c1ccc1c2cco1
InChI InChI=1S/C21H20O6/c1-22-16-8-13-15(9-17(16)23-2)26-10-18-19(13)21(24-3)12-4-5-14-11(6-7-25-14)20(12)27-18/h4-9,18-19,21H,10H2,1-3H3/t18?,19?,21-/m1/s1
InChIKey LGJWBTKCQLVCIA-GZNCHQMQSA-N
Formula C21H20O6
HBA 6
HBD 0
MW 368.39
Rotatable Bonds 3
TPSA 59.29
LogP 4.07
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 368.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia duchesnei Leguminosae/Fabaceae Plantae 2708899
2 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 De Wild. Planta Med. 2008, 74-PB76. [View]
  • 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: 101837046

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 368.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.11
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.510
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.380
Plasma Protein Binding
64.54
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
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.330
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.330
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.160
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.990
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
Safe
T. Pyriformis
-15.890
Rat (Acute)
2.930
Rat (Chronic Oral)
1.930
Fathead Minnow
5.450
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
460.710
Hydration Free Energy
-6.420
Log(D) at pH=7.4
2.950
Log(P)
3.53
Log S
-4.38
Log(Vapor Pressure)
-8.08
Melting Point
140.41
pKa Acid
11.45
pKa Basic
5.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9249
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9238
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9127
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9069
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9054
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8999
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8917
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8863
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8770
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.8607
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8581
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8563
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8520
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8518
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8481
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8357
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8217
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8178
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8167
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8162
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8141
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8129
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8104
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8071
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8055
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.8045
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8035
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8034
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8007
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7988
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7941
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7920
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7902
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7814
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7788
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7784
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7781
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7755
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7736
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7730
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7729
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7706
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7693
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7692
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7602
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7580
Amine oxidase [flavin-containing] B P27338 AOFB_HUMAN Homo sapiens 3 0.7576
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7567
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7564
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7543
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7506
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7506
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7492
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7487
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7477
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7476
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7472
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7463
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7445
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7415
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7414
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7410
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7401
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7390
Enoyl-acyl carrier reductase C6KSZ2 C6KSZ2_PLAF7 Plasmodium falciparum 4 0.7382
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7374
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7372
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7362
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7359
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7358
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7356
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7342
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7318
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7312
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7306
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7300
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7299
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7289
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7289
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7276
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7263
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7262
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7251
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7238
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 2 0.7237
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7236
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7229
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7227
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7224
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7213
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7207
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7201
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7167
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7156
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7156
Mu-type opioid receptor P42866 OPRM_MOUSE Mus musculus 3 0.7136
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7129
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7125
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7123
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7110
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7105
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7084
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7076
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7075
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7068
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7060
Lanosterol 14-alpha demethylase A6ZSR0 A6ZSR0_YEAS7 Saccharomyces cerevisiae 3 0.7053
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7029
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7028
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7019
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7015
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7011
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7011
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7001

Download SDF