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Versiol
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
-
Class: Pyrone
- Subclass: Naphthopyrone
| Canonical Smiles | C[C@H]1C[C@H](O)[C@H]2C(=C1)C=C[C@]1([C@]2(C)C(=O)CCO1)C |
|---|---|
| InChI | InChI=1S/C16H22O3/c1-10-8-11-4-6-15(2)16(3,13(18)5-7-19-15)14(11)12(17)9-10/h4,6,8,10,12,14,17H,5,7,9H2,1-3H3/t10-,12+,14-,15+,16-/m1/s1 |
| InChIKey | SXHZNZFKZCCMFJ-ZZIHQOKHSA-N |
| Formula | C16H22O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 262.35 |
| Rotatable Bonds | 0 |
| TPSA | 46.53 |
| LogP | 2.25 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.69 |
| Exact Mass | 262.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus versicolor | Trichocomaceae | Fungi | 46472 |
Showing of synonyms
Versiol
UNII-50TPF0MD67
50TPF0MD67
59684-36-5
VERSIOL, (+)-
1H-Naphtho(2,1-b)pyran-1-one, 2,3,4a,8,9,10,10a,10b-octahydro-10-hydroxy-4a,8,10b-trimethyl-, (4aR,8R,10R,10aR,10bS)-rel-(-)-
1H-NAPHTHO(2,1-B)PYRAN-1-ONE, 2,3,4A,8,9,10,10A,10B-OCTAHYDRO-10-HYDROXY-4A,8,10B-TRIMETHYL-, (4AS,8S,10S,10AS,10BR)-
DTXSID90208376
(4aS,8S,10S,10aS,10bR)-10-hydroxy-4a,8,10b-trimethyl-2,3,8,9,10,10a-hexahydrobenzo(f)chromen-1-one
(4aS,8S,10S,10aS,10bR)-10-hydroxy-4a,8,10b-trimethyl-2,3,8,9,10,10a-hexahydrobenzo[f]chromen-1-one
DTXCID10130867
CHEMBL5418127
Q27260821
- Abdelwahab M, Kurtán T, et al. (2018). Induced secondary metabolites from the endophytic fungus Aspergillus versicolor through bacterial co-culture and OSMAC approaches. Tetrahedron Letters,2018,59(27),2647-2652. [View]
Pubchem:
101042985
Cas:
59684-36-5
Zinc:
ZINC000085555469
Nmrshiftdb2:
70012211
Chembl:
CHEMBL5418127
No compound-protein relationship available.
SMILES: C1CCCC(C=12)C3C(C=C2)OCCC3=O
Level: 0
Mol. Weight: 262.35 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.66
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.36
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.4
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.57
- Plasma Protein Binding
- 46.44
- 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
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.6
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.12
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.13
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.61
- 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
- Toxic
- T. Pyriformis
- -1.39
- Rat (Acute)
- 2.61
- Rat (Chronic Oral)
- 1.5
- Fathead Minnow
- 3.69
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 348.7
- Hydration Free Energy
- -8.45
- Log(D) at pH=7.4
- 1.43
- Log(P)
- 1.81
- Log S
- -2.33
- Log(Vapor Pressure)
- -5.26
- Melting Point
- 153.98
- pKa Acid
- 10.01
- pKa Basic
- 4.59
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.9262 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8375 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8370 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8166 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8150 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7887 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7662 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.7586 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7565 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7546 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7540 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7390 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7366 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7354 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7229 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7165 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7163 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7154 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7147 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7130 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7113 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7098 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7097 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7092 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7079 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7007 |