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Sipholenol L
- Family: Animalia - Callyspongiidae
- Kingdom: Animalia
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | CC1=CC[C@H]2[C@@H]([C@@H]1CC[C@@H]1[C@@](C)(O)CC[C@H]3[C@@]1(C)CC[C@@H](C(O3)(C)C)O)C(C)(C)CC[C@]2(C)O |
|---|---|
| InChI | InChI=1S/C30H52O4/c1-19-9-11-21-25(26(2,3)17-18-29(21,7)32)20(19)10-12-22-28(6)15-13-23(31)27(4,5)34-24(28)14-16-30(22,8)33/h9,20-25,31-33H,10-18H2,1-8H3/t20-,21+,22+,23+,24+,25-,28+,29+,30+/m1/s1 |
| InChIKey | KNWLCYSMHRPQLC-ZWULGDALSA-N |
| Formula | C30H52O4 |
| HBA | 4 |
| HBD | 3 |
| MW | 476.74 |
| Rotatable Bonds | 3 |
| TPSA | 69.92 |
| LogP | 6.02 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.93 |
| Exact Mass | 476.39 |
| 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
Sipholenol L
(3S,5aS,6S,7S,9aS)-6-(2-((1S,4aS,5S,8aR)-5-hydroxy-2,5,8,8-tetramethyl-1,4,4a,6,7,8a-hexahydronaphthalen-1-yl)ethyl)-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo(b)oxepine-3,7-diol
(3S,5aS,6S,7S,9aS)-6-[2-[(1S,4aS,5S,8aR)-5-hydroxy-2,5,8,8-tetramethyl-1,4,4a,6,7,8a-hexahydronaphthalen-1-yl]ethyl]-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepine-3,7-diol
CHEMBL562568
- 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, Abraham I, et al. (2009). Sipholane triterpenoids: Chemistry, reversal of ABCB1/P-glycoprotein-mediated multidrug resistance, and pharmacophore modeling.. Journal of Natural Products,2009,72(7),1291-1298. [View] [PubMed]
No compound-protein relationship available.
SMILES: C1CCCC(C12)CC=CC2CCC3CCCC(C34)OCCCC4
Level: 1
Mol. Weight: 476.74 g/mol
SMILES: C1CCCC(C12)OCCCC2
Level: 0
Mol. Weight: 476.74 g/mol
SMILES: C1C=CCC(C12)CCCC2
Level: 0
Mol. Weight: 476.74 g/mol
Antiproliferative
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.77
- 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
- -2.6
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.03
- Plasma Protein Binding
- 79.66
- 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
- 7.99
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.22
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.71
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.77
- 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
- Toxic
- T. Pyriformis
- -90.55
- Rat (Acute)
- 3.29
- Rat (Chronic Oral)
- 1.51
- 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
- 472.1
- Hydration Free Energy
- -3.17
- Log(D) at pH=7.4
- 4.8
- Log(P)
- 6.54
- Log S
- -6.2
- Log(Vapor Pressure)
- -8.24
- Melting Point
- 189.36
- pKa Acid
- 11.16
- pKa Basic
- 8.25
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7989 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7989 |