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Sipholenol I
- Family: Animalia - Callyspongiidae
- Kingdom: Animalia
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | O[C@@H]1CC[C@]2([C@H](OC1(C)C)CC[C@]([C@@H]2CC[C@]12O[C@]2(C)[C@H](O)CC2C(C1(C)C)CC[C@@]2(C)O)(C)O)C |
|---|---|
| InChI | InChI=1S/C30H52O6/c1-24(2)18-9-14-27(6,33)19(18)17-22(32)29(8)30(24,36-29)16-10-20-26(5)13-11-21(31)25(3,4)35-23(26)12-15-28(20,7)34/h18-23,31-34H,9-17H2,1-8H3/t18?,19?,20-,21-,22-,23-,26-,27-,28+,29-,30+/m1/s1 |
| InChIKey | WWWZOBMNBOEYTA-NYKFADQYSA-N |
| Formula | C30H52O6 |
| HBA | 6 |
| HBD | 4 |
| MW | 508.74 |
| Rotatable Bonds | 3 |
| TPSA | 102.68 |
| LogP | 4.35 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 36 |
| Formal Charge | 0 |
| Fraction CSP3 | 1.0 |
| Exact Mass | 508.38 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Callyspongia siphonella | Callyspongiidae | Animalia | 469330 |
| 2 | Callyspongia siphonella | Callyspongiidae | Animalia | 469330 |
Showing of synonyms
Sipholenol I
14beta,15beta-epoxysipholenol E
(1aS,5R,7R,7aR)-1a-(2-((3R,5aR,6R,7S,9aR)-3,7-dihydroxy-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo(b)oxepin-6-yl)ethyl)-2,2,5,7a-tetramethyl-2a,3,4,5a,6,7-hexahydroazuleno(5,6-b)oxirene-5,7-diol
(1aS,5R,7R,7aR)-1a-[2-[(3R,5aR,6R,7S,9aR)-3,7-dihydroxy-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepin-6-yl]ethyl]-2,2,5,7a-tetramethyl-2a,3,4,5a,6,7-hexahydroazuleno[5,6-b]oxirene-5,7-diol
(3S,5aS,6S,7S,9aS)-6-(2-((1aS,2S,3aS,4S,7aR,7bR)-4-hydroxy-1a,2,4,7,7-pentamethyl-2,3,3a,5,6,7a-hexahydronaphtho(1,2-b)oxiren-7b-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-[(1aS,2S,3aS,4S,7aR,7bR)-4-hydroxy-1a,2,4,7,7-pentamethyl-2,3,3a,5,6,7a-hexahydronaphtho[1,2-b]oxiren-7b-yl]ethyl]-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepine-3,7-diol
CHEMBL388090
- 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]
Pubchem:
16737095
Chembl:
CHEMBL388090
No compound-protein relationship available.
SMILES: C1CCC(C2)C1CCC(O3)C23CCC4CCCC(C45)OCCCC5
Level: 1
Mol. Weight: 508.74 g/mol
SMILES: C1CCCC(C12)OCCCC2
Level: 0
Mol. Weight: 508.74 g/mol
SMILES: C12C(O2)CCC3C(C1)CCC3
Level: 0
Mol. Weight: 508.74 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -5.21
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.89
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.35
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.17
- Plasma Protein Binding
- 65.03
- 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
- 10.89
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.05
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.01
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 6.1
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -304.71
- Rat (Acute)
- 4.42
- Rat (Chronic Oral)
- 1.94
- Fathead Minnow
- 3.59
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 461.17
- Hydration Free Energy
- -3.03
- Log(D) at pH=7.4
- 3.51
- Log(P)
- 3.99
- Log S
- -4.67
- Log(Vapor Pressure)
- -8.11
- Melting Point
- 188.02
- pKa Acid
- 6.96
- pKa Basic
- 6.85
| 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 | 0.7770 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7770 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7382 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7382 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7379 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7379 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7309 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7309 |