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28-hydroxysipholenol A
- Family: Animalia - Callyspongiidae
- Kingdom: Animalia
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | OCC1=CCC2C(C(C1CC[C@H]1[C@@](C)(O)CC[C@@H]3[C@]1(C)CC[C@H](C(O3)(C)C)O)(C)C)CC[C@@]2(C)O |
|---|---|
| InChI | InChI=1S/C30H52O5/c1-26(2)20(19(18-31)8-9-22-21(26)12-16-29(22,6)33)10-11-23-28(5)15-13-24(32)27(3,4)35-25(28)14-17-30(23,7)34/h8,20-25,31-34H,9-18H2,1-7H3/t20?,21?,22?,23-,24-,25-,28-,29-,30+/m1/s1 |
| InChIKey | WWNUXCFWCRMYCN-NXHAIPTASA-N |
| Formula | C30H52O5 |
| HBA | 5 |
| HBD | 4 |
| MW | 492.74 |
| Rotatable Bonds | 4 |
| TPSA | 90.15 |
| LogP | 4.99 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.93 |
| Exact Mass | 492.38 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Callyspongia siphonella | Callyspongiidae | Animalia | 469330 |
Showing of synonyms
28-hydroxysipholenol A
(3R,5aR,6R,7S,9aR)-6-(2-((1R)-1-hydroxy-6-(hydroxymethyl)-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulen-5-yl)ethyl)-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo(b)oxepine-3,7-diol
(3R,5aR,6R,7S,9aR)-6-[2-[(1R)-1-hydroxy-6-(hydroxymethyl)-1,4,4-trimethyl-2,3,3a,5,8,8a-hexahydroazulen-5-yl]ethyl]-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepine-3,7-diol
CHEMBL388091
Pubchem:
16738312
Chembl:
CHEMBL388091
No compound-protein relationship available.
SMILES: C1CCC(C12)CC(C=CC2)CCC3CCCC(C34)OCCCC4
Level: 1
Mol. Weight: 492.74 g/mol
SMILES: C1CCCC(C12)OCCCC2
Level: 0
Mol. Weight: 492.74 g/mol
SMILES: C1CCC(C12)CCC=CC2
Level: 0
Mol. Weight: 492.74 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.84
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.87
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.5
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.85
- Plasma Protein Binding
- 68.12
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.04
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.29
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.09
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.67
- 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
- -154.44
- Rat (Acute)
- 3.8
- Rat (Chronic Oral)
- 1.74
- Fathead Minnow
- 3.82
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 486.83
- Hydration Free Energy
- -3.06
- Log(D) at pH=7.4
- 3.87
- Log(P)
- 4.88
- Log S
- -5.42
- Log(Vapor Pressure)
- -8.65
- Melting Point
- 183.41
- pKa Acid
- 10.63
- pKa Basic
- 8.46
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8757 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8757 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7688 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7688 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7617 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7617 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7540 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7540 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7440 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7440 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7216 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7216 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7186 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7186 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7160 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7160 |