7a-O-methyl-12a-hydroxydeguelol - Compound Card

7a-O-methyl-12a-hydroxydeguelol

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7a-O-methyl-12a-hydroxydeguelol

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Rotenoid
Canonical Smiles COc1c(ccc2c1C=CC(O2)(C)C)C(=O)C1(O)CCOc2c1cc(OC)c(c2)OC
InChI InChI=1S/C24H26O7/c1-23(2)9-8-14-17(31-23)7-6-15(21(14)29-5)22(25)24(26)10-11-30-18-13-20(28-4)19(27-3)12-16(18)24/h6-9,12-13,26H,10-11H2,1-5H3
InChIKey ZBBONRPQJAKJAQ-UHFFFAOYSA-N
Formula C24H26O7
HBA 7
HBD 1
MW 426.47
Rotatable Bonds 5
TPSA 83.45
LogP 3.75
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 426.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Derris trifoliata Leguminosae/Fabaceae Plantae 185716
2 Derris trifoliata Leguminosae/Fabaceae Plantae 185716

Showing of synonyms

  • Yenesew A, Kiplagat JT Mushibe EK Derese S, et al. (2005). Rotenoid derivatives from Kenyan Millettia and Derris species as larvicidal agents. Natural products and drug discovery, Proceedings of the 11th NAPRECA Symposium August 9-12, 2005, Hôtel Panorama, Antananarivo, Madagascar. [View] [PubMed]
  • Yenesew A1, Kiplagat JT, et al. (2006). Two unusual rotenoid derivatives, 7a-O-methyl-12a-hydroxydeguelol and spiro-13-homo-13-oxaelliptone, from the seeds of Derris trifoliata.. Phytochemistry,2006,67(10):988-991. [View] [PubMed]
Pubchem: 102188214
Nmrshiftdb2: 80017056

No compound-protein relationship available.

Structure

SMILES: C1=CCOc(c12)ccc(c2)C(=O)C3CCOc(c34)cccc4

Level: 1

Mol. Weight: 426.47 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 426.47 g/mol

Structure

SMILES: C1=CCOc(c12)cccc2

Level: 0

Mol. Weight: 426.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.090
Plasma Protein Binding
47.69
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.770
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.670
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.480
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.650
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
Toxic
T. Pyriformis
-43.050
Rat (Acute)
2.780
Rat (Chronic Oral)
2.120
Fathead Minnow
5.140
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
454.590
Hydration Free Energy
-3.760
Log(D) at pH=7.4
3.290
Log(P)
3.37
Log S
-3.85
Log(Vapor Pressure)
-7.85
Melting Point
137.22
pKa Acid
8.27
pKa Basic
2.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9637
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9637
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.9309
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.9309
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9287
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9287
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9091
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9091
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8895
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8895
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8818
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8818
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8720
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8720
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8527
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8527
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8467
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8467
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8467
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8467
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8401
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8401
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8351
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8351
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8294
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8294
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8167
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8167
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8160
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8160
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8142
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8142
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8122
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8122
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8106
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8106
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8067
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8067
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8029
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8029
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8010
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8010
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7931
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7931
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7928
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7928
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7899
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7899
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7883
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7883
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7752
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7752
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7727
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7727
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7718
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7718
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7717
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7717
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7680
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7680
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7665
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7665
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7658
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7658
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7592
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7592
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7548
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7548
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7543
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7543
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7534
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7534
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7508
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7508
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7494
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7494
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7490
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7490
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7487
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7487
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 5 0.7477
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 5 0.7477
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7460
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7460
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7421
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7421
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7415
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7415
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7406
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7406
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7393
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7393
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7368
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7368
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7361
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7361
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7354
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7354
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7335
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7335
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7326
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7326
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7315
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7315
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7313
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7313
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7299
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7299
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7294
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7294
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7256
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7256
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7233
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7233
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7213
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7213
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7206
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7206
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7201
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7201
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7188
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7188
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7170
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7170
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7166
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7166
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7160
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7160
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7155
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7155
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.7152
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.7152
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7139
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7139
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7137
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7137
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7131
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7131
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7088
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7088
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7084
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7084
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7027
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7027

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