6a,12a-dehydrodeguelin - Compound Card

6a,12a-dehydrodeguelin

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6a,12a-dehydrodeguelin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1cc2Oc3c(COc2cc1OC)oc1c(c3=O)ccc2c1C=CC(O2)(C)C
InChI InChI=1S/C23H20O7/c1-23(2)8-7-12-14(30-23)6-5-13-20(24)22-19(29-21(12)13)11-27-17-9-15(25-3)16(26-4)10-18(17)28-22/h5-10H,11H2,1-4H3
InChIKey CKHVKQDEOBZNIX-UHFFFAOYSA-N
Formula C23H20O7
HBA 7
HBD 0
MW 408.41
Rotatable Bonds 2
TPSA 76.36
LogP 4.68
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 408.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia dura Leguminosae/Fabaceae Plantae 62119

Showing of synonyms

  • Yenesew A, Derese S, et al. (2003). Effect of rotenoids from the seeds of Millettia dura on larvae of Aedes aegypti.. Pest Management Science,2003,59(10),1159-1161. [View] [PubMed]
Pubchem: 10092854
Nmrshiftdb2: 89601

No compound-protein relationship available.

Structure

SMILES: C1=CCOc(cc2)c1c(c23)oc4c(c3=O)Oc5c(OC4)cccc5

Level: 0

Mol. Weight: 408.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.97
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.500
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.520
Plasma Protein Binding
85.55
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
Non-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
10.210
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.930
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.990
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.860
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
-39.430
Rat (Acute)
3.760
Rat (Chronic Oral)
0.980
Fathead Minnow
5.670
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
506.930
Hydration Free Energy
-4.690
Log(D) at pH=7.4
3.090
Log(P)
4.29
Log S
-5.17
Log(Vapor Pressure)
-9.07
Melting Point
213.77
pKa Acid
9.07
pKa Basic
0.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9224
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9224
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9185
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9185
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8879
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8879
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8747
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8747
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8649
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8649
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8502
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8502
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8482
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8482
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8475
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8475
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8278
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8278
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.8269
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.8269
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8127
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8127
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8040
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8040
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8000
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8000
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7950
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7950
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7944
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7944
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7884
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7884
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7841
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7841
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7777
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7777
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7718
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7718
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7700
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7700
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7687
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7687
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7652
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7652
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7647
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7647
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7646
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7646
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7642
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7642
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7625
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7625
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7604
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7604
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7582
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7582
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7562
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7562
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7540
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7540
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7522
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7522
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 4 0.7499
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 4 0.7499
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7494
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7494
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7316
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7316
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7312
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7312
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7306
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7306
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7249
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7249
2-Hydroxyacid oxidase 1 Q9UJM8 HAOX1_HUMAN Homo sapiens 3 0.7225
2-Hydroxyacid oxidase 1 Q9UJM8 HAOX1_HUMAN Homo sapiens 3 0.7225
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7200
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7200
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7191
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7191
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7189
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7189
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7180
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7180
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7129
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7129
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7118
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7118
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7110
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7110
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7107
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7107
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7106
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7106
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7099
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7099
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7079
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7079
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7078
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7078
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7071
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7071
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7047
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7047
A disintegrin and metalloproteinase with thrombospondin motifs 5 Q9UNA0 ATS5_HUMAN Homo sapiens 3 0.7030
A disintegrin and metalloproteinase with thrombospondin motifs 5 Q9UNA0 ATS5_HUMAN Homo sapiens 3 0.7030
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7030
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7030
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7029
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7029
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7018
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7018
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7018
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7018
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7007
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7007
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7004
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7004

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