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(7S,8R)-8‐hydroxy-sydowic acid
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
-
Class: Terpenoid
- Subclass: Meroterpenoid
| Canonical Smiles | O[C@@H]1CCC(O[C@@]1(C)c1ccc(cc1O)C(=O)O)(C)C |
|---|---|
| InChI | InChI=1S/C15H20O5/c1-14(2)7-6-12(17)15(3,20-14)10-5-4-9(13(18)19)8-11(10)16/h4-5,8,12,16-17H,6-7H2,1-3H3,(H,18,19)/t12-,15+/m1/s1 |
| InChIKey | SSBNXPFUYGSWLX-DOMZBBRYSA-N |
| Formula | C15H20O5 |
| HBA | 4 |
| HBD | 3 |
| MW | 280.32 |
| Rotatable Bonds | 2 |
| TPSA | 86.99 |
| LogP | 2.26 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 280.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus versicolor | Trichocomaceae | Fungi | 46472 |
Showing of synonyms
(7S,8R)-8‐hydroxy-sydowic acid
(-)-(7S,8R)-8-hydroxysydowic acid
3-hydroxy-4-[(2S,3R)-3-hydroxy-2,6,6-trimethyloxan-2-yl]benzoic acid
3-Hydroxy-4-((2S,3R)-3-hydroxy-2,6,6-trimethyloxan-2-yl)benzoate
3-hydroxy-4-((2S,3R)-3-hydroxy-2,6,6-trimethyloxan-2-yl)benzoic acid
3-Hydroxy-4-[(2S,3R)-3-hydroxy-2,6,6-trimethyloxan-2-yl]benzoate
(-)-(7S,8R)-8-Hydroxysydowate
CHEBI:211836
- Elsbaey M, Tanaka C, et al. (2019). New secondary metabolites from the mangrove endophytic fungus Aspergillus versicolor. Phytochemistry Letters,2019,32,70-76. [View]
No compound-protein relationship available.
SMILES: c1ccccc1C2CCCCO2
Level: 1
Mol. Weight: 280.32 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 280.32 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 280.32 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.03
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.91
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.85
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.39
- Plasma Protein Binding
- 64.81
- 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
- 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
- 11.72
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.14
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.74
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 2.93
- Micronucleos
- Toxic
- 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
- 1.19
- Rat (Acute)
- 2.21
- Rat (Chronic Oral)
- 2.69
- Fathead Minnow
- 3.88
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 356.01
- Hydration Free Energy
- -10.91
- Log(D) at pH=7.4
- 0.24
- Log(P)
- 2.49
- Log S
- -2.57
- Log(Vapor Pressure)
- -7.1
- Melting Point
- 190.9
- pKa Acid
- 5.35
- pKa Basic
- 5.69
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.9156 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.9006 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8626 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8488 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8247 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8083 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7861 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7734 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7675 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7566 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7523 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7475 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7456 |
| Transcriptional regulator URE2 | P23202 | URE2_YEAST | Saccharomyces cerevisiae | 3 | 0.7344 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7222 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7194 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7194 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7187 |
| Angiotensin-converting enzyme | Q10714 | ACE_DROME | Drosophila melanogaster | 2 | 0.7171 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7166 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7117 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7047 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7023 |