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12a-hydroxyrotenone
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Rotenoid
| Canonical Smiles | COc1cc2c(cc1OC)OC(C1C2C(=O)c2c(O1)c1CC(Oc1cc2)C(=C)C)O |
|---|---|
| InChI | InChI=1S/C23H22O7/c1-10(2)15-8-13-14(28-15)6-5-11-20(24)19-12-7-17(26-3)18(27-4)9-16(12)29-23(25)22(19)30-21(11)13/h5-7,9,15,19,22-23,25H,1,8H2,2-4H3 |
| InChIKey | OFLJOIFZMITSOL-UHFFFAOYSA-N |
| Formula | C23H22O7 |
| HBA | 7 |
| HBD | 1 |
| MW | 410.42 |
| Rotatable Bonds | 3 |
| TPSA | 83.45 |
| LogP | 3.02 |
| 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 | Millettia ferruginea | Leguminosae/Fabaceae | Plantae | 1096003 |
| 2 | Tephrosia rhodesica | Leguminosae/Fabaceae | Plantae | 556521 |
Showing of synonyms
12a-hydroxyrotenone
6-Hydroxyrotenone
LMPK12060030
NS00097341
- Buyinza D, Chalo DM, et al. (2020). Flavonoids and Isoflavonoids of Millettia dura and Millettia ferruginea: Phytochemical review and chemotaxonomic values. Biochemical Systematics and Ecology, 2020, 91, 104053. [View]
- 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:
14427381
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)
- -4.89
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.600
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.3
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.190
- Plasma Protein Binding
- 39.31
- 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
- 12.240
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.060
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.020
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.780
- 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
- -49.780
- Rat (Acute)
- 3.480
- Rat (Chronic Oral)
- 1.950
- Fathead Minnow
- 5.200
- 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
- 467.320
- Hydration Free Energy
- -3.750
- Log(D) at pH=7.4
- 2.710
- Log(P)
- 3.35
- Log S
- -4.26
- Log(Vapor Pressure)
- -8.85
- Melting Point
- 187.87
- pKa Acid
- 8.05
- pKa Basic
- 1.66
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9157 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8637 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.8563 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8474 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8333 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8261 |
| 17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 3 | 0.8233 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7923 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 3 | 0.7730 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7444 |
| Beta-elicitin cinnamomin | P15569 | ELIB_PHYCI | Phytophthora cinnamomi | 3 | 0.7388 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7384 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7337 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7280 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7263 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7200 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7146 |
| Cytochrome P450 1A1 | P04798 | CP1A1_HUMAN | Homo sapiens | 3 | 0.7097 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7092 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7050 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7033 |
| Diphtheria toxin | P00588 | DTX_CORBE | Corynephage beta | 3 | 0.7027 |
| Type IV pilus retractation ATPase PilT | P24559 | PILT_PSEAE | Pseudomonas aeruginosa | 3 | 0.7008 |