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Kirkinine
- Family: Plantae - Thymelaeaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Daphnane Diterpene Ester
| Canonical Smiles | CCCCCCCCCCCCC/C=C/[C@@]12O[C@H]3[C@](O1)(C(=C)C)[C@@H]([C@H]([C@@]1(O2)[C@H]3[C@@H]2O[C@@]2([C@H]([C@]2([C@H]1C=C(C2=O)C)O)O)CO)C)OC(=O)C |
|---|---|
| InChI | InChI=1S/C38H56O10/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-35-46-32-28-31-34(22-39,45-31)33(42)36(43)27(21-24(4)29(36)41)38(28,48-35)25(5)30(44-26(6)40)37(32,47-35)23(2)3/h19-21,25,27-28,30-33,39,42-43H,2,7-18,22H2,1,3-6H3/b20-19+/t25-,27-,28+,30-,31+,32-,33-,34+,35-,36-,37+,38+/m1/s1 |
| InChIKey | MDZJGGUQWHZDTA-UELJRACISA-N |
| Formula | C38H56O10 |
| HBA | 10 |
| HBD | 3 |
| MW | 672.86 |
| Rotatable Bonds | 16 |
| TPSA | 144.28 |
| LogP | 4.98 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 48 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.79 |
| Exact Mass | 672.39 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Synaptolepis kirkii | Thymelaeaceae | Plantae | 2896602 |
| 2 | Synaptolepis kirkii | Thymelaeaceae | Plantae | 2896602 |
| 3 | Synaptolepis kirkii | Thymelaeaceae | Plantae | 2896602 |
Showing of synonyms
Kirkinine
[(1R,2R,6S,7S,8R,10S,11S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-[(E)-pentadec-1-enyl]-16-prop-1-en-2-yl-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl] acetate
((1R,2R,6S,7S,8R,10S,11S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-((E)-pentadec-1-enyl)-16-prop-1-en-2-yl-9,13,15,19-tetraoxahexacyclo(12.4.1.01,11.02,6.08,10.012,16)nonadec-3-en-17-yl) acetate
300691-92-3
CHEMBL502037
- He W, Cik M, et al. (2000). Kirkinine, a new daphnane orthoester with potent neurotrophic activity from Synaptolepis kirkii. Journal of Natural Products,2000,63(9),1185-1187. [View] [PubMed]
- He W, Cik M, et al. (2002). Neurotrophic and antileukemic daphnane diterpenoids from Synaptolepis kirkii. Bioorganic and Medicinal Chemistry,2002,10(10),3245-3255. [View] [PubMed]
- He W, De Kimpe N. (2000). Study of biological active principles from Kenyan medicinal plants. PhD Thesis, University of Ghent, Belgium, 2000-2001. [View]
No compound-protein relationship available.
SMILES: O1C(O2)OC(CC3)C1C4C(O5)C5CC(C6C234)C(=O)C=C6
Level: 0
Mol. Weight: 672.86 g/mol
Antitumor
Neurotrophic
Absorption
- Caco-2 (logPapp)
- -5.03
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.14
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 117.48
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.99
- Plasma Protein Binding
- 91.21
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-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
- Non-Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 8.03
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.45
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.3
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 8.04
- Micronucleos
- Safe
- 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
- Toxic
- T. Pyriformis
- -218670.74
- Rat (Acute)
- 4.41
- Rat (Chronic Oral)
- 3.12
- Fathead Minnow
- 288.82
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 21422.73
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 4.13
- Log(P)
- 7.5
- Log S
- -5.61
- Log(Vapor Pressure)
- -662.83
- Melting Point
- 125.34
- pKa Acid
- 3.9
- pKa Basic
- 1.93
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7591 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7591 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7238 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7238 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7159 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7159 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7050 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7050 |