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Vomifoliol
- Family: Plantae - Boraginaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpenoid
| Canonical Smiles | C[C@H](/C=C/[C@@]1(O)C(=CC(=O)CC1(C)C)C)O |
|---|---|
| InChI | InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10-,13-/m1/s1 |
| InChIKey | KPQMCAKZRXOZLB-KOIHBYQTSA-N |
| Formula | C13H20O3 |
| HBA | 3 |
| HBD | 2 |
| MW | 224.3 |
| Rotatable Bonds | 2 |
| TPSA | 57.53 |
| LogP | 1.6 |
| Number Rings | 1 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 16 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 224.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cynara sibthorpiana | Asteraceae | Plantae | 935151 |
| 2 | Conyza bonariensis | Asteraceae | Plantae | 91242 |
| 3 | Otanthus maritimus | Asteraceae | Plantae | 1155244 |
| 4 | Xanthium pungens | Asteraceae | Plantae | 1979456 |
| 5 | Heliotropium bacciferum | Boraginaceae | Plantae | 244092 |
Showing of synonyms
Vomifoliol
23526-45-6
(6S,9R)-vomifoliol
(6S,9R)-6-hydroxy-3-oxo-alpha-ionol
(+)-Vomifoliol
Vomifoliol, (+)-
CHEBI:49164
(4S)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one
P86438KC5J
DTXSID601009964
(4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one
(6S,9R)-6-HYDROXY-3-OXO-.ALPHA.-IONOL
(4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
2-CYCLOHEXEN-1-ONE, 4-HYDROXY-4-(3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-, (+)-
CHEBI:28258
(4S)-4-hydroxy-4-((1E,3R)-3-hydroxybut-1-en-1-yl)-3,5,5-trimethylcyclohex-2-en-1-one
(4S)-4-hydroxy-4-((1E,3R)-3-hydroxybut-1-enyl)-3,5,5-trimethylcyclohex-2-en-1-one
(4S)-4-hydroxy-4-((E,3R)-3-hydroxybut-1-enyl)-3,5,5-trimethylcyclohex-2-en-1-one
DTXCID101436388
4-hydroxy-4-((1e)-3-hydroxybut-1-en-1-yl)-3,5,5-trimethylcyclohex-2-en-1-one
4-hydroxy-4-[(1e)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one
BLUMENOL A
Roseoside aglycon
(+/-)-Volifoliol
(+/-)-Blumenol-A
B7QV234K84
(6S,7E,9R)-6,9-dihydroxy-4,7-megastigmadien-3-one
50763-73-0
FEMA no. 4661, (4S,3R)-(E)-(+/-)-
2-Cyclohexen-1-one, 4-hydroxy-4-((1E,3R)-3-hydroxy-1-buten-1-yl)-3,5,5-trimethyl-, (4S)-
2-Cyclohexen-1-one, 4-hydroxy-4-((1E,3R)-3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (4S)-
2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (R*,S*-(E))-
2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (S-(R*,S*-(E)))-
4-Hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-2-cyclohexen-1-one, (4S,3R)-(E)-(+/-)-
2-Cyclohexen-1-one, 4-hydroxy-4-((1E,3R)-3-hydroxy-1-buten-1-yl)-3,5,5-trimethyl-, (4S)-rel-
2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (R*,S*-(E))-(+/-)-
(+-)-Vomifoliol
(+-)-Blumenol A
Vomifoliol, (+-)-
UNII-B7QV234K84
UNII-P86438KC5J
(+)-BLUMENOL A
CHEMBL463088
SCHEMBL1243896
HY-N1077
(+-)-6-hydroxy-3-oxo-alpha-ionol
BDBM50463336
NSC805019
AKOS032948398
FS-9636
NSC-805019
2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (+-)-
DA-59041
FV177947
CS-0016364
NS00122932
C01760
G14079
Q22911785
(S)-4-Hydroxy-4-((R,E)-3-hydroxybut-1-en-1-yl)-3,5,5-trimethylcyclohex-2-en-1-one
- Mabrouk S, Elaissi A, et al. (2011). Chemical composition of essential oils from leaves, stems, flower heads and roots of Conyza bonariensis L. from Tunisia. Natural Product Research,2011,5(1),77-84. [View] [PubMed]
- Omar A, Sarg TA, et al. (1984). Guaianolides from Cynara sibthorpiana. Phytochemistry,1984,23(10),2381-2382. [View]
- Aïssaoui H, Mencherini T, et al. (2019). Heliotropium bacciferum Forssk. (Boraginaceae) extracts: chemical constituents, antioxidant activity and cytotoxic effect in human cancer cell lines. Natural product research, 2019, 33(12), 1813-1818. [View] [PubMed]
- Jakupovic J, Boeker R, et al. (1988). Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry,1988,27(4),1135-1140. [View]
- Ahmed AA, Jakupovic J, et al. (1990). Sesquiterpene lactones from Xanthium pungens. Phytochemistry,1990,29(7),2211-2215. [View]
Pubchem:
5280462
Cas:
23526-45-6
Zinc:
ZINC000004095719
Kegg Ligand:
C01760
Chebi:
49164
Nmrshiftdb2:
60019478
Metabolights:
MTBLC49164
Chembl:
CHEMBL463088
Bindingdb:
50463336
CPRiL:
83172
SMILES: O=C1C=CCCC1
Level: 0
Mol. Weight: 224.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.68
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.0
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.65
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.18
- Plasma Protein Binding
- 36.62
- 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
- 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
- 4.56
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.19
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.86
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.07
- 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
- -1.33
- Rat (Acute)
- 2.23
- Rat (Chronic Oral)
- 1.65
- Fathead Minnow
- 3.97
- 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
- 294.1
- Hydration Free Energy
- -11.45
- Log(D) at pH=7.4
- 0.56
- Log(P)
- 0.48
- Log S
- -0.99
- Log(Vapor Pressure)
- -4.68
- Melting Point
- 115.53
- pKa Acid
- 8.46
- pKa Basic
- 4.78
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8828 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8828 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8680 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8680 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8526 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.8526 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8471 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8471 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8349 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8349 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7975 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7975 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7786 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7786 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7636 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7636 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7610 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7610 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7511 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7511 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7414 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7414 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7406 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7406 |
| FKBP-type peptidyl-prolyl cis-trans isomerase FkpA | P45523 | FKBA_ECOLI | Escherichia coli | 4 | 0.7333 |
| FKBP-type peptidyl-prolyl cis-trans isomerase FkpA | P45523 | FKBA_ECOLI | Escherichia coli | 4 | 0.7333 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7220 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7220 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7192 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7192 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7037 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7037 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7030 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7030 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7008 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7008 |