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14,15-dihydro-ajugapitin
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Epimeric Clerodane Diterpenoid
| Canonical Smiles | CCC(C(=O)O[C@H]1[C@H](O)C[C@H]2[C@@]([C@]31CO3)(COC(=O)C)[C@@H](OC(=O)C)C[C@H]([C@]2(C)[C@@H]1C[C@@H]2[C@H](O1)OCC2)C)C |
|---|---|
| InChI | InChI=1S/C29H44O10/c1-7-15(2)25(33)39-24-20(32)12-21-27(6,22-11-19-8-9-34-26(19)38-22)16(3)10-23(37-18(5)31)28(21,13-35-17(4)30)29(24)14-36-29/h15-16,19-24,26,32H,7-14H2,1-6H3/t15?,16-,19-,20-,21-,22+,23+,24+,26+,27+,28+,29-/m1/s1 |
| InChIKey | XMVULWKEVGKECE-DBNYLVSFSA-N |
| Formula | C29H44O10 |
| HBA | 10 |
| HBD | 1 |
| MW | 552.66 |
| Rotatable Bonds | 7 |
| TPSA | 130.12 |
| LogP | 2.77 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 39 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 552.29 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ajuga pseudoiva | Lamiaceae | Plantae | 2026104 |
Showing of synonyms
14,15-dihydro-ajugapitin
Dihydroajugapitin
14,15-DIHYDROAJUGAPITIN
87480-84-0
CHEBI:67467
Q27135934
(1R,2S,3R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-[(2S,3aR,6aS)-hexahydrofuro[2,3-b]furan-2-yl]-3-hydroxy-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylbutanoate
Caryoptinol, 14,15-dihydro-2-hydroxy-, 3-(2-methylbutanoate), (2,3)-
- Ben Jannet H, Chaari A, et al. (1999). Neo-clerodane diterpenoids from Ajuga pseudoiva leaves. Phytochemistry,1999,52(8),1541-1545. [View]
No compound-protein relationship available.
SMILES: O1CC12C3C(CCC2)C(CCC3)C(C4)OC(C45)OCC5
Level: 1
Mol. Weight: 552.66 g/mol
SMILES: O1CC12C3C(CCC2)CCCC3
Level: 0
Mol. Weight: 552.66 g/mol
SMILES: C1COC(C12)OCC2
Level: 0
Mol. Weight: 552.66 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.03
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.81
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.22
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.44
- Plasma Protein Binding
- 54.83
- 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
- Non-Inhibitor
Excretion
- Clearance
- 11.01
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.23
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.41
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.69
- Micronucleos
- Toxic
- 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
- Safe
- T. Pyriformis
- -2284.12
- Rat (Acute)
- 5.33
- Rat (Chronic Oral)
- 1.94
- Fathead Minnow
- 8.06
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 417.91
- Hydration Free Energy
- -2.89
- Log(D) at pH=7.4
- 2.16
- Log(P)
- 2.42
- Log S
- -4.62
- Log(Vapor Pressure)
- -9.01
- Melting Point
- 118.51
- pKa Acid
- 5.89
- pKa Basic
- 2.36
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.9731 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.9731 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8001 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8001 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7591 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7591 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7438 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7438 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7276 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7276 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7106 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7106 |
| Sodium-dependent dopamine transporter | Q7K4Y6 | DAT_DROME | Drosophila melanogaster | 2 | 0.7097 |
| Sodium-dependent dopamine transporter | Q7K4Y6 | DAT_DROME | Drosophila melanogaster | 2 | 0.7097 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7079 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7079 |