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Kihadalactone A
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: A-Seco-Limonoid
| Canonical Smiles | CC(=O)OC1CC2C(C)(C)OC(=O)CC([C@@]2(C2[C@]1(C)C1=CCC(C1(CC2)C)c1ccoc1)C)OC(=O)C |
|---|---|
| InChI | InChI=1S/C30H40O7/c1-17(31)35-24-14-23-27(3,4)37-26(33)15-25(36-18(2)32)30(23,7)22-10-12-28(5)20(19-11-13-34-16-19)8-9-21(28)29(22,24)6/h9,11,13,16,20,22-25H,8,10,12,14-15H2,1-7H3/t20?,22?,23?,24?,25?,28?,29-,30+/m0/s1 |
| InChIKey | ONWYJKOVGIGNQN-UOXTVKHISA-N |
| Formula | C30H40O7 |
| HBA | 7 |
| HBD | 0 |
| MW | 512.64 |
| Rotatable Bonds | 3 |
| TPSA | 92.04 |
| LogP | 5.73 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 37 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 512.28 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Vepris uguenensis | Rutaceae | Plantae | 2695421 |
| 2 | Vepris uguenensis | Rutaceae | Plantae | 2695421 |
Showing of synonyms
Kihadalactone A
NSC653154
NSC-653154
NCI60_018592
- Kiplimo JJ, Shahidul Islam M, et al. (2012). Ring A-seco limonoids and flavonoids from the Kenyan Vepris uguenensis Engl. and their antioxidant activity. Phytochemistry,2012,83(2012),136-143. [View] [PubMed]
- Kiplimo JJ, Koorbanally NA. (2012). The phytochemistry and biological activity of secondary metabolites from Kenyan Vernonia and Vepris species. PhD Thesis, University of Kwazulu-Natal, South Africa,2012. [View] [PubMed]
Pubchem:
374817
No compound-protein relationship available.
SMILES: c1occc1C(CC2)C(C=23)CCC4C3CCC5C4CCC(=O)OC5
Level: 1
Mol. Weight: 512.64 g/mol
SMILES: C1CCC(C=12)CCC3C2CCC4C3CCC(=O)OC4
Level: 0
Mol. Weight: 512.64 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 512.64 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.9
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.89
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.73
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.38
- Plasma Protein Binding
- 60.51
- 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
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 10.06
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.08
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.21
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.39
- 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
- -743.17
- Rat (Acute)
- 3.6
- Rat (Chronic Oral)
- 2.21
- Fathead Minnow
- 6.38
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 458.52
- Hydration Free Energy
- -2.84
- Log(D) at pH=7.4
- 3.82
- Log(P)
- 5.0
- Log S
- -6.4
- Log(Vapor Pressure)
- -7.93
- Melting Point
- 170.78
- pKa Acid
- 10.12
- pKa Basic
- 5.21
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8571 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8571 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8116 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8116 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8069 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8069 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8041 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8041 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7922 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7922 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7837 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7837 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7672 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7672 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7669 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7669 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7589 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7589 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7585 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7585 |
| AGAP003309-PA | A0A1U7F4W2 | A0A1U7F4W2_ANOGA | Anopheles gambiae | 2 | 0.7577 |
| AGAP003309-PA | A0A1U7F4W2 | A0A1U7F4W2_ANOGA | Anopheles gambiae | 2 | 0.7577 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7552 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7552 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7542 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7542 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7539 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7539 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 3 | 0.7462 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 3 | 0.7462 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7447 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7447 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 2 | 0.7444 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 2 | 0.7444 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7421 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7421 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 2 | 0.7398 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 2 | 0.7398 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7392 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7392 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7308 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7308 |
| Metapyrocatechase | Q7WYF5 | Q7WYF5_9PSED | Pseudomonas alkylphenolica | 2 | 0.7307 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7307 |
| Metapyrocatechase | Q7WYF5 | Q7WYF5_9PSED | Pseudomonas alkylphenolica | 2 | 0.7307 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7307 |
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 2 | 0.7261 |
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 2 | 0.7261 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7227 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7227 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7134 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7134 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7118 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7118 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7103 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7103 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7084 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7084 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7041 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7041 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7023 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7023 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7007 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7007 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7001 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7001 |