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12-O-butenyl-5-hydroxy-6,7-epoxy-resiniferonol-9,13-14-orthobenzoate
- Family: Plantae - Thymelaeaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: 12-Hydroxy-Daphnane Ester
| Canonical Smiles | CC/C=C/C(=O)O[C@@H]1[C@@H](C)[C@@]23O[C@]4(O[C@]1(C(=C)C)[C@@H]([C@@H]2[C@@H]1O[C@@]1([C@H]([C@]1([C@H]3C=C(C1=O)C)O)O)CO)O4)c1ccccc1 |
|---|---|
| InChI | InChI=1S/C32H36O10/c1-6-7-13-21(34)38-24-18(5)31-20-14-17(4)23(35)29(20,37)27(36)28(15-33)25(39-28)22(31)26-30(24,16(2)3)41-32(40-26,42-31)19-11-9-8-10-12-19/h7-14,18,20,22,24-27,33,36-37H,2,6,15H2,1,3-5H3/b13-7+/t18-,20-,22+,24-,25+,26-,27-,28+,29-,30+,31+,32-/m1/s1 |
| InChIKey | GMGZRLUWSNMNKB-NEGGUVPJSA-N |
| Formula | C32H36O10 |
| HBA | 10 |
| HBD | 3 |
| MW | 580.63 |
| Rotatable Bonds | 6 |
| TPSA | 144.28 |
| LogP | 1.82 |
| Number Rings | 7 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 42 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.56 |
| Exact Mass | 580.23 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Thymelaea hirsuta | Thymelaeaceae | Plantae | 69845 |
Showing of synonyms
12-O-butenyl-5-hydroxy-6,7-epoxy-resiniferonol-9,13-14-orthobenzoate
- Brooks G, Evans AT, et al. (1990). Daphnane diterpenes of Thymelaea hirsuta. Phytochemistry,1990,29(7),2235-2237. [View]
Pubchem:
163012668
No compound-protein relationship available.
SMILES: C1=CC(=O)C(C1C234)CC5C(O5)C2C6C(CC3)OC(O6)(O4)c7ccccc7
Level: 1
Mol. Weight: 580.63 g/mol
SMILES: O1C(O2)OC(CC3)C1C4C(O5)C5CC(C6C234)C(=O)C=C6
Level: 0
Mol. Weight: 580.63 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 580.63 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.23
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.57
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 7.85
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.81
- Plasma Protein Binding
- 76.83
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 9.91
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.09
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.31
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.9
- Micronucleos
- Toxic
- 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
- -18210.57
- Rat (Acute)
- 5.06
- Rat (Chronic Oral)
- 3.23
- Fathead Minnow
- 40.12
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 318.15
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 2.16
- Log(P)
- 3.17
- Log S
- -4.07
- Log(Vapor Pressure)
- -10.03
- Melting Point
- 170.36
- pKa Acid
- 4.03
- pKa Basic
- 0.13
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8925 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8925 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7215 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7215 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7146 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7146 |
| Protein LlR18A | P52778 | L18A_LUPLU | Lupinus luteus | 3 | 0.7004 |
| Protein LlR18A | P52778 | L18A_LUPLU | Lupinus luteus | 3 | 0.7004 |