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3beta-hydroxyisoiphion-11(13)-en-12-oic acid
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpenoid
| Canonical Smiles | C=C([C@@H]1CC[C@@]2([C@@](C1)(C(=O)C)[C@@H](O)CC2)C)C(=O)O |
|---|---|
| InChI | InChI=1S/C15H22O4/c1-9(13(18)19)11-4-6-14(3)7-5-12(17)15(14,8-11)10(2)16/h11-12,17H,1,4-8H2,2-3H3,(H,18,19)/t11-,12+,14+,15+/m1/s1 |
| InChIKey | QHMVDJGMBDTIEY-DHMWGJHJSA-N |
| Formula | C15H22O4 |
| HBA | 3 |
| HBD | 2 |
| MW | 266.34 |
| Rotatable Bonds | 3 |
| TPSA | 74.6 |
| LogP | 2.16 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 266.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Jasonia montana | Asteraceae | Plantae | 441235 |
Showing of synonyms
3beta-hydroxyisoiphion-11(13)-en-12-oic acid
Cyperanic acid
117869-89-3
2-[(3S,3aR,5R,7aS)-3a-acetyl-3-hydroxy-7a-methyl-2,3,4,5,6,7-hexahydro-1H-inden-5-yl]prop-2-enoic acid
1H-Indene-5-aceticacid, 3a-acetyloctahydro-3-hydroxy-7a-methyl-a-methylene-, (3S,3aR,5R,7aS)-
SCHEMBL19419905
ACon1_001588
DTXSID30922569
CHEBI:181357
AKOS040736208
NCGC00180350-01
NCGC00180350-02
BRD-K30690667-001-01-9
2-(3a-Acetyl-3-hydroxy-7a-methyloctahydro-1H-inden-5-yl)prop-2-enoic acid
1H-Indene-5-acetic acid, 3a-acetyloctahydro-3-hydroxy-7a-methyl-alpha-methylene-, (3S,3aR,5R,7aS)-
NCGC00180350-02_C15H22O4_2-[(3S,3aR,5R,7aS)-3a-Acetyl-3-hydroxy-7a-methyloctahydro-1H-inden-5-yl]acrylic acid
- Ahmed AA, Jakupovic J (1990). Sesqui- and monoterpenes from Jasonia montana. Phytochemistry,1990,29(11),3658-3661. [View]
Pubchem:
189528
Cas:
117869-89-3
Gnps:
CCMSLIB00000855023
Zinc:
ZINC000005167277
Chebi:
181357
Nmrshiftdb2:
70015113
No compound-protein relationship available.
SMILES: C1CCC(C12)CCCC2
Level: 0
Mol. Weight: 266.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.78
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.62
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.36
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.48
- Plasma Protein Binding
- 56.9
- 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
- Inhibitor
- CYP 2C9 Substrate
- 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
- -1.12
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.41
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 2.75
- 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
- -0.56
- Rat (Acute)
- 2.33
- Rat (Chronic Oral)
- 2.38
- Fathead Minnow
- 3.94
- 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
- 346.16
- Hydration Free Energy
- -9.18
- Log(D) at pH=7.4
- -0.69
- Log(P)
- 2.01
- Log S
- -2.33
- Log(Vapor Pressure)
- -6.48
- Melting Point
- 155.31
- pKa Acid
- 4.03
- pKa Basic
- 7.63
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8789 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8789 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 3 | 0.8766 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 3 | 0.8766 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8676 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8676 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 3 | 0.8584 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 3 | 0.8584 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8520 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8520 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8485 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8485 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8317 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8317 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 3 | 0.8150 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 3 | 0.8150 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8138 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8138 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 3 | 0.7806 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 3 | 0.7806 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7692 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7692 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7523 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7523 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7318 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7318 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7270 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7270 |
| Lactaldehyde dehydrogenase | P25553 | ALDA_ECOLI | Escherichia coli | 3 | 0.7214 |
| Lactaldehyde dehydrogenase | P25553 | ALDA_ECOLI | Escherichia coli | 3 | 0.7214 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7199 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7199 |