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7-deacetoxy-7-oxogedunin
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | O=C1OC(c2ccoc2)C2(C3(C1O3)C1(C)C(=O)CC3C(C1CC2)(C)C=CC(=O)C3(C)C)C |
|---|---|
| InChI | InChI=1S/C26H30O6/c1-22(2)16-12-18(28)25(5)15(23(16,3)9-7-17(22)27)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)32-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3 |
| InChIKey | PMISPNORJONCHB-UHFFFAOYSA-N |
| Formula | C26H30O6 |
| HBA | 6 |
| HBD | 0 |
| MW | 438.52 |
| Rotatable Bonds | 1 |
| TPSA | 86.11 |
| LogP | 4.2 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 438.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Khaya ivorensis | Meliaceae | Plantae | 486173 |
| 2 | Pseudocedrela kotschyi | Meliaceae | Plantae | 356281 |
Showing of synonyms
7-deacetoxy-7-oxogedunin
7-Deacetyl-7-oxogedunin
13072-74-7
Desacetoxy-oxo-7-gedunine
7-Desacetoxy-7-oxogedunin
NSC 309908
7-(furan-3-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.02,4.02,8.012,17]nonadec-13-ene-5,15,19-trione
16,17-Seco-24-nor-5.alpha.,13.alpha.,14.beta.,17.alpha.-chola-1,20,22-trien-16-oic acid, 14,15.beta.:21,23-diepoxy-17-hydroxy-4,4,8-trimethyl-3,7-dioxo-, .delta.-lactone
D-Homo-24-nor-17-oxachola-1,20,22-triene-3,7,16-dione, 14,15:21,23-diepoxy-4,4,8-trimethyl-, (5.alpha.,13.alpha.,14.beta.,15.beta.,17a.alpha.)-
7-(furan-3-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo(9.8.0.02,4.02,8.012,17)nonadec-13-ene-5,15,19-trione
16,17-Seco-24-nor-5alpha,13alpha,14beta,17alpha-chola-1,20,22-trien-16-oic acid, 14,15beta:21,23-diepoxy-17-hydroxy-4,4,8-trimethyl-3,7-dioxo-, delta-lactone
D-Homo-24-nor-17-oxachola-1,20,22-triene-3,7,16-dione, 14,15:21,23-diepoxy-4,4,8-trimethyl-, (5alpha,13alpha,14beta,15beta,17aalpha)-
16,17-Seco-24-nor-5alpha,13alpha,14beta,17alpha-chola-1,20,22-trien-16-oic acid, 14,15beta:21,23-diepoxy-17-hydroxy-4,4,8-trimethyl-3,7-dioxo-, delta-lactone (8CI)
Pmispnorjonchb-uhfffaoysa-n
7-Oxo-7-deacetoxygedunin
NSC309908
7-Oxodeacetoxydihydro-..-gedunol
GEDUNIN, 7-KETO
SCHEMBL20639417
DTXSID70926869
7-Oxodeacetoxydihydro-.alpha.-gedunol
NSC-309908
(1S,3aS,41R,4a1R,10aS,12aS)-1-(furan-3-yl)-5-methoxy-4a1,7,7,10a,12a-pentamethyl-6,6a,7,10a,10b,11,12,12a-octahydronaphtho[2,1-f]oxireno[2,3-d]isochromene-3,5,8(1H,3aH,4a1H)-trione
1-(3-Furyl)-4b,7,7,10a,12a-pentamethyl-1,6a,7,10a,10b,11,12,12a-octahydronaphtho[2,1-f]oxireno[2,3-d]isochromene-3,5,8(3ah,4bh,6H)-trione #
10-(Furan-3-yl)-4,4,6a,10a,12b-pentamethyl-4a,6a,10,10a,11,12,12a,12b-octahydrooxireno[c]phenanthro[1,2-d]pyran-3,6,8(4H,5H,7aH)-trione
16,13.alpha.,14.beta.,17.alpha.-chola-1,20,22-trien-16-oic acid, 14,15.beta.:21,23-diepoxy-17-hydroxy-4,4,8-trimethyl-3,7-dioxo-, .delta.-lactone
D-Homo-24-nor-17-oxachola-1,22-triene-3,7,16-dione, 14,15:21,23-diepoxy-4,4,8-trimethyl-, (5.alpha.,13.alpha.,14.beta.,15.beta.,17a.alpha.)-
- Abdelgaleil S, El-Aswad AF (2005). Antifeedant and Growth Inhibitory Effects of Tetranortriterpenoids Isolated from Three Meliaceous Species on the Cotton Leafworm, Spodoptera littoralis (Boisd.). Journal of Applied Sciences Research, 2005, 1(2). [View]
- Sidjui LS, Nganso YOD, et al. (2018). Kostchyienones A and B, new antiplasmodial and cytotoxicity of limonoids from the roots of Pseudocedrela kotschyi (Schweinf.) Harms.. Zeitschrift fur Naturforschung. C, Journal of biosciences,2018, 73(3-4), 153-160. [View] [PubMed]
CPRiL:
415930
SMILES: c1occc1C(OC(=O)C(C234)O4)C3CCC5C2C(=O)CC6C5C=CC(=O)C6
Level: 1
Mol. Weight: 438.52 g/mol
SMILES: C123C(O3)C(=O)OCC2CCC4C1C(=O)CC5C4C=CC(=O)C5
Level: 0
Mol. Weight: 438.52 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 438.52 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.18
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.78
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.27
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.75
- Plasma Protein Binding
- 17.03
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 15.54
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.05
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.2
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 6.67
- Micronucleos
- Toxic
- NR-AhR
- Safe
- 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
- -109.1
- Rat (Acute)
- 3.18
- Rat (Chronic Oral)
- 1.82
- Fathead Minnow
- 4.92
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 458.05
- Hydration Free Energy
- -2.74
- Log(D) at pH=7.4
- 3.3
- Log(P)
- 2.72
- Log S
- -4.99
- Log(Vapor Pressure)
- -7.99
- Melting Point
- 223.24
- pKa Acid
- 4.4
- pKa Basic
- 3.25
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.9545 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.9504 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.9320 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.9154 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.8933 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.8907 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 3 | 0.8804 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8597 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.8467 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8356 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8266 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8254 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 | O88703 | HCN2_MOUSE | Mus musculus | 3 | 0.8196 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 3 | 0.8165 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.8129 |
| AcsD | Q93AT8 | Q93AT8_DICCH | Dickeya chrysanthemi | 3 | 0.7907 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7847 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7818 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7768 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7766 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7755 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7718 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7665 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7637 |
| cAMP-dependent protein kinase type II-beta regulatory subunit | P12369 | KAP3_RAT | Rattus norvegicus | 3 | 0.7578 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7568 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7486 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7478 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7467 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7465 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7411 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7405 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7380 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7363 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7355 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7337 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7332 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7301 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7275 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7268 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7250 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7246 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7243 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7231 |
| DNA-binding transcriptional dual regulator CRP | P0ACJ8 | CRP_ECOLI | Escherichia coli | 3 | 0.7223 |
| Ras-related protein Rap-1b | P61224 | RAP1B_HUMAN | Homo sapiens | 3 | 0.7212 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7204 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7199 |
| Casein kinase II subunit alpha' | P19784 | CSK22_HUMAN | Homo sapiens | 3 | 0.7198 |
| Probable esterase KAI2 | Q9SZU7 | KAI2_ARATH | Arabidopsis thaliana | 3 | 0.7189 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7188 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7176 |
| Adenosine kinase | Q9TVW2 | ADK_TOXGO | Toxoplasma gondii | 3 | 0.7100 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7096 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7084 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.7054 |
| Cyclic nucleotide-gated potassium channel mll3241 | Q98GN8 | CNGK1_RHILO | Mesorhizobium japonicum) | 3 | 0.7039 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 2 | 0.7011 |