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Melitensin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | OCC(=C)[C@@H]1[C@H]2OC(=O)[C@H]([C@@H]2[C@H](C[C@@]1(C)C=C)O)C |
|---|---|
| InChI | InChI=1S/C15H22O4/c1-5-15(4)6-10(17)11-9(3)14(18)19-13(11)12(15)8(2)7-16/h5,9-13,16-17H,1-2,6-7H2,3-4H3/t9-,10-,11+,12+,13-,15+/m0/s1 |
| InChIKey | BJNRYKWHTCAVLA-JSXSYOHWSA-N |
| Formula | C15H22O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 266.34 |
| Rotatable Bonds | 3 |
| TPSA | 66.76 |
| LogP | 1.29 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 266.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Centaurea pullata | Asteraceae | Plantae | 347528 |
| 2 | Centaurea nicaeensis | Asteraceae | Plantae | 41503 |
Showing of synonyms
Melitensin
CHEMBL513441
MEGxp0_000791
ACon1_000762
NCGC00169384-01
(3S,3aR,4S,6S,7R,7aR)-4-hydroxy-7-[1-(hydroxymethyl)vinyl]-3,6-dimethyl-6-vinyl-3,3a,4,5,7,7a-hexahydrobenzofuran-2-one
- Hammoud L, Seghiri R, et al. (2012). A new flavonoid and other constituents from Centaurea nicaeensis All. var. walliana M.. Natural Product Research,2012,26(3),203-208. [View] [PubMed]
- Djeddi S, Karioti A, et al. (2008). A novel sesquiterpene lactone from Centaurea pullata: Structure elucidation, antimicrobial activity, and prediction of pharmacokinetic properties. Bioorganic and Medicinal Chemistry,2008,16,3725-3731. [View] [PubMed]
No compound-protein relationship available.
SMILES: C1C(=O)OC(C12)CCCC2
Level: 0
Mol. Weight: 266.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.81
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.340
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.43
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.440
- Plasma Protein Binding
- 49.9
- 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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.150
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.100
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.690
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.140
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -0.510
- Rat (Acute)
- 3.480
- Rat (Chronic Oral)
- 1.850
- Fathead Minnow
- 3.920
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 338.370
- Hydration Free Energy
- -9.730
- Log(D) at pH=7.4
- 0.550
- Log(P)
- 1.22
- Log S
- -1.95
- Log(Vapor Pressure)
- -6.42
- Melting Point
- 120.59
- pKa Acid
- 7.97
- pKa Basic
- 4.98
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8666 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8666 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.8279 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.8279 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8233 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8233 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7582 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7582 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7120 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7120 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.7012 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.7012 |