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12-O-heptadecenoyl-5-hydroxy-6,7-epoxy-resiniferonol-9,13,14-orthobenzoate
- Family: Plantae - Thymelaeaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: 12-Hydroxy-Daphnane Ester
| Canonical Smiles | CCCCCCCCCCCCCC/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/C44H60O10/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-22-25-33(46)50-36-30(5)43-32-26-29(4)35(47)41(32,49)39(48)40(27-45)37(51-40)34(43)38-42(36,28(2)3)53-44(52-38,54-43)31-23-20-19-21-24-31/h19-26,30,32,34,36-39,45,48-49H,2,6-18,27H2,1,3-5H3/b25-22+/t30-,32-,34+,36-,37+,38-,39-,40+,41-,42+,43+,44-/m1/s1 |
| InChIKey | PPQADCYEUBNTIO-ZQEBQFCLSA-N |
| Formula | C44H60O10 |
| HBA | 10 |
| HBD | 3 |
| MW | 748.95 |
| Rotatable Bonds | 18 |
| TPSA | 144.28 |
| LogP | 6.5 |
| Number Rings | 7 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 54 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.68 |
| Exact Mass | 748.42 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Thymelaea hirsuta | Thymelaeaceae | Plantae | 69845 |
Showing of synonyms
12-O-heptadecenoyl-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:
163069578
Zinc:
ZINC000255259677
No compound-protein relationship available.
SMILES: C1=CC(=O)C(C1C234)CC5C(O5)C2C6C(CC3)OC(O6)(O4)c7ccccc7
Level: 1
Mol. Weight: 748.95 g/mol
SMILES: O1C(O2)OC(CC3)C1C4C(O5)C5CC(C6C234)C(=O)C=C6
Level: 0
Mol. Weight: 748.95 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 748.95 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.89
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 20.82
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 3385.36
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.12
- Plasma Protein Binding
- 101.4
- 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
- 9.26
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -82.57
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.4
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.21
- 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
- -6149514.15
- Rat (Acute)
- 4.17
- Rat (Chronic Oral)
- 3.7
- Fathead Minnow
- 7768.07
- 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
- 688684.42
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 5.15
- Log(P)
- 9.07
- Log S
- -5.85
- Log(Vapor Pressure)
- -22587.37
- Melting Point
- 141.7
- pKa Acid
- -126.52
- pKa Basic
- 1.33
| 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 | 0.8570 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8570 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7784 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7784 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7674 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7674 |
| Protein LlR18A | P52778 | L18A_LUPLU | Lupinus luteus | 3 | 0.7666 |
| Protein LlR18A | P52778 | L18A_LUPLU | Lupinus luteus | 3 | 0.7666 |
| Sodium-dependent dopamine transporter | Q7K4Y6 | DAT_DROME | Drosophila melanogaster | 2 | 0.7472 |
| Sodium-dependent dopamine transporter | Q7K4Y6 | DAT_DROME | Drosophila melanogaster | 2 | 0.7472 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7230 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7230 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7226 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7226 |
| Phenazine biosynthesis protein A/B | Q396C9 | Q396C9_BURL3 | Burkholderia lata | 2 | 0.7208 |
| Phenazine biosynthesis protein A/B | Q396C9 | Q396C9_BURL3 | Burkholderia lata | 2 | 0.7208 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7126 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7126 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7052 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7052 |