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Sipholenol A
- Family: Animalia - Callyspongiidae
- Kingdom: Animalia
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | CC1=CC[C@@H]2[C@H](C([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)CC[C@@]2(C)O |
|---|---|
| InChI | InChI=1S/C30H52O4/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/h9,20-25,31-33H,10-18H2,1-8H3/t20-,21+,22+,23+,24+,25+,28+,29+,30-/m0/s1 |
| InChIKey | LVWWPNAIMBYRKG-KOHQYJKCSA-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 | Callyspongia siphonella | Callyspongiidae | Animalia | 469330 |
| 3 | Siphonochalina species | Callyspongiidae | Animalia | 412817 |
| 4 | Siphonochalina siphonella | Callyspongiidae | Animalia | 469330 |
Showing of synonyms
Sipholenol A
SIPHOLENOL-A
78518-73-7
(3R,5aR,6R,7S,9aR)-6-[2-[(1R,3aR,5S,8aR)-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-hexahydro-3H-benzo[b]oxepine-3,7-diol
(3R,5aR,6R,7S,9aR)-6-(2-((1R,3aR,5S,8aR)-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-hexahydro-3H-benzo(b)oxepine-3,7-diol
NSC378977
CHEMBL1965248
SCHEMBL20591098
NSC-378977
NCI60_003571
(3R,5aR,6R,7S,9aR)-6-[2-[(1R,3aR,5S,8aR)-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-hexahydro-3H-benzo[b]oxepine-3,7-diol
(3R,5aR,6R,7S,9aR)-6-{2-[(1R,3aR,5S,8aR)-1-hydroxy-1,4,4,6-tetramethyl-2,3,3a,5,8,8a-hexahydroazulen-5-yl]ethyl}-2,2,5a,7-tetramethyl-hexahydro-3H-1-benzoxepine-3,7-diol
- 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]
- 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]
CPRiL:
193375
SMILES: C1CCC(C12)CC(C=CC2)CCC3CCCC(C34)OCCCC4
Level: 1
Mol. Weight: 476.74 g/mol
SMILES: C1CCCC(C12)OCCCC2
Level: 0
Mol. Weight: 476.74 g/mol
SMILES: C1CCC(C12)CCC=CC2
Level: 0
Mol. Weight: 476.74 g/mol
Anticancer
Antiproliferative
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.73
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.73
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.47
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.99
- Plasma Protein Binding
- 80.45
- 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
- 8.1
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.19
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.52
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.79
- 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
- -94.47
- Rat (Acute)
- 3.28
- Rat (Chronic Oral)
- 1.53
- 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
- 463.24
- Hydration Free Energy
- -3.04
- Log(D) at pH=7.4
- 4.83
- Log(P)
- 6.71
- Log S
- -6.24
- Log(Vapor Pressure)
- -8.29
- Melting Point
- 191.36
- pKa Acid
- 11.3
- pKa Basic
- 8.28
| 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 | 0.7463 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7463 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7298 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7298 |