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12a-hydroxyrotenone
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Isoflavone
| Canonical Smiles | COc1cc2c(cc1OC)OC[C@@H]1[C@@]2(O)C(=O)c2c(O1)c1C[C@@H](Oc1cc2)C(=C)C |
|---|---|
| InChI | InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1 |
| InChIKey | JFVKWCYZKMUTLH-AYPBNUJASA-N |
| Formula | C23H22O7 |
| HBA | 7 |
| HBD | 1 |
| MW | 410.42 |
| Rotatable Bonds | 3 |
| TPSA | 83.45 |
| LogP | 2.81 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.35 |
| Exact Mass | 410.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tephrosia rhodesica | Leguminosae/Fabaceae | Plantae | 556521 |
Showing of synonyms
12a-hydroxyrotenone
Rotenolone
509-96-6
12alpha-Hydroxyrotenone
(-)-cis-Rotenolone
6ab,12ab-Rotenolone
(-)-cis-12a-Hydroxyrotenone
(1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6ah)-one, 1,2,12,12a-alpha-tetrahydro-6a-alpha-hydroxy-2-alpha-isopropenyl-8,9-dimethoxy-
[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aR,12aR)-
(1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one
1,2,12,12a-Tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-(2R,6aR,12aR)-[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
DTXSID301019530
6alpha(beta),12alpha(beta)-Rotenolone
(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aR,12aR)-
(1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo(11.8.0.0^(3,11).0^(4,8).0^(14,19))henicosa-3,8,10,14(19),15,17-hexaen-12-one
(1R,6R,13R)-13-hydroxy-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo(11.8.0.03,11.04,8.014,19)henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
1,2,12,12a-Tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-(2R,6ar,12ar)-(1)benzopyrano(3,4-b)furo(2,3-H)(1)benzopyran-6(6ah)-one
545-76-6
DTXCID201477490
(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-, (2R-(2alpha,6abeta,12abeta))-
6 alpha(beta),12 alpha(beta)-Rotenolone
Rotenalone
Rotenolone I
Rotenolon I
6a-beta,12a-beta-Rotenolone
CHEBI:68051
12-Hydroxyrotenone
12-alpha-Hydroxyrotenone
HN2R8MKH6Y
UNII-HN2R8MKH6Y
(-)-12alpha-Hydroxyrotenone
CHEMBL240545
BDBM50480247
Hydroxy-isopropenyl-dimethoxy-[?]one
AKOS040753816
DA-77539
FH137905
FS-10634
HY-119694
C10464
Q27104952
(2R,6aR,12aR)-1,2,12,12a-Tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
- Atilaw Y, Muiva-Mutisya L, et al. (2020). Prenylated Flavonoids from the Roots of Tephrosia rhodesica. Journal of natural products, 2020, 83(8), 2390–2398. [View]
Pubchem:
68184
Cas:
509-96-6
Zinc:
ZINC000004098734
Kegg Ligand:
C10464
Chebi:
68051
Nmrshiftdb2:
60026042
Metabolights:
MTBLC68051
Chembl:
CHEMBL240545
Bindingdb:
50480247
CPRiL:
294781
SMILES: C1COc(c12)ccc3c2OC4C(C3=O)c5c(OC4)cccc5
Level: 0
Mol. Weight: 410.42 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.87
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.670
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.99
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.280
- Plasma Protein Binding
- 83.2
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-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
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.060
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.050
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.510
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.810
- 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
- -50.910
- Rat (Acute)
- 3.010
- Rat (Chronic Oral)
- 1.970
- Fathead Minnow
- 4.810
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 455.030
- Hydration Free Energy
- -4.090
- Log(D) at pH=7.4
- 2.750
- Log(P)
- 3.36
- Log S
- -4.02
- Log(Vapor Pressure)
- -8.87
- Melting Point
- 211.17
- pKa Acid
- 8.32
- pKa Basic
- 1.78
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9507 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8953 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.8271 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8165 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8150 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8109 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.8012 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7965 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7945 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7831 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7755 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7598 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7577 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7530 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7488 |
| Beta-elicitin cinnamomin | P15569 | ELIB_PHYCI | Phytophthora cinnamomi | 3 | 0.7480 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7370 |
| Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.7269 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 3 | 0.7252 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7250 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7242 |
| Isoflavone-7-O-methyltransferase 8 | O24529 | 7OMT8_MEDSA | Medicago sativa | 4 | 0.7206 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7189 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7171 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7166 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.7153 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7107 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7102 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7052 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.7048 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7042 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7036 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7007 |