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Sipholenone A
- Family: Animalia - Callyspongiidae
- Kingdom: Animalia
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | CC1=CCC2C(C(C1CC[C@H]1[C@@](C)(O)CC[C@@H]3[C@]1(C)CCC(=O)C(O3)(C)C)(C)C)CC[C@@]2(C)O |
|---|---|
| InChI | InChI=1S/C30H50O4/c1-19-9-10-22-21(13-17-29(22,7)32)26(2,3)20(19)11-12-23-28(6)16-14-24(31)27(4,5)34-25(28)15-18-30(23,8)33/h9,20-23,25,32-33H,10-18H2,1-8H3/t20?,21?,22?,23-,25-,28-,29-,30+/m1/s1 |
| InChIKey | LKZQMXLIWZQEEU-GGRPBLHXSA-N |
| Formula | C30H50O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 474.73 |
| Rotatable Bonds | 3 |
| TPSA | 66.76 |
| LogP | 6.23 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 474.37 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Callyspongia siphonella | Callyspongiidae | Animalia | 469330 |
| 2 | Siphonochalina species | Callyspongiidae | Animalia | 412817 |
| 3 | Siphonochalina siphonella | Callyspongiidae | Animalia | 469330 |
Showing of synonyms
Sipholenone A
(5aR,6R,7S,9aR)-7-hydroxy-6-(2-((1R)-1-hydroxy-1,4,4,6-tetramethyl-2,3,3a,5,8,8a-hexahydroazulen-5-yl)ethyl)-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydrobenzo(b)oxepin-3-one
(5aR,6R,7S,9aR)-7-hydroxy-6-[2-[(1R)-1-hydroxy-1,4,4,6-tetramethyl-2,3,3a,5,8,8a-hexahydroazulen-5-yl]ethyl]-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydrobenzo[b]oxepin-3-one
CHEMBL226142
- Abdel-Lateff A, Al-Abd AM, et al. (2016). Antiproliferative effects of triterpenoidal derivatives, obtained from the marine sponge Siphonochalina sp., on human hepatic and colorectal cancer cells.. Zeitschrift für Naturforschung C,2016,71(1-2),29-35. [View] [PubMed]
- Ayyad SEN, Angawi RF, et al. (2014). Cytotoxic neviotane triterpene-type from the red sea sponge Siphonochalina siphonella.. Pharmacognosy Magazine,2014,Supplement-2,1-7. [View] [PubMed]
- Jain S, Laphookhieo S, et al. (2007). Reversal of P-glycoprotein-mediated multidrug resistance by sipholane triterpenoids.. Journal of Natural Products,2007,70(6),928-931. [View] [PubMed]
CPRiL:
291846
SMILES: C1CCC(C12)CC(C=CC2)CCC3CCCC(C34)OCC(=O)CC4
Level: 1
Mol. Weight: 474.73 g/mol
SMILES: C1CCCC(C12)OCC(=O)CC2
Level: 0
Mol. Weight: 474.73 g/mol
SMILES: C1CCC(C12)CCC=CC2
Level: 0
Mol. Weight: 474.73 g/mol
Anticancer
Antiproliferative
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.68
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.74
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.13
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.2
- Plasma Protein Binding
- 81.45
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.41
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.43
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.19
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.14
- 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
- -91.36
- Rat (Acute)
- 2.81
- Rat (Chronic Oral)
- 1.43
- Fathead Minnow
- 3.92
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 459.05
- Hydration Free Energy
- -2.95
- Log(D) at pH=7.4
- 4.84
- Log(P)
- 6.3
- Log S
- -6.13
- Log(Vapor Pressure)
- -7.82
- Melting Point
- 177.08
- pKa Acid
- 9.94
- pKa Basic
- 6.84
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7474 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7474 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7434 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7434 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7403 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7403 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7244 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7244 |