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Barlerin
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Monoterpene
| Canonical Smiles | CC(=O)O[C@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)C |
|---|---|
| InChI | InChI=1S/C19H28O12/c1-7(21)31-19(2)4-9(22)11-8(16(26)27-3)6-28-17(12(11)19)30-18-15(25)14(24)13(23)10(5-20)29-18/h6,9-15,17-18,20,22-25H,4-5H2,1-3H3/t9-,10-,11+,12-,13-,14+,15-,17+,18+,19+/m1/s1 |
| InChIKey | ARFRZOLTIRQFCI-NGQYDJQZSA-N |
| Formula | C19H28O12 |
| HBA | 12 |
| HBD | 5 |
| MW | 448.42 |
| Rotatable Bonds | 5 |
| TPSA | 181.44 |
| LogP | -2.47 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.79 |
| Exact Mass | 448.16 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Morinda asteroscepa | Rubiaceae | Plantae | 43521 |
Showing of synonyms
Barlerin
57420-46-9
8-O-Acetyl shanzhiside methyl ester
8-O-Acetylshanzhiside methyl ester
Methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
5beta-Dihydro Finasteride
Cyclopenta[c]pyran-4-carboxylic acid,7-(acetyloxy)-1-(b-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-5-hydroxy-7-methyl-, methyl ester, (1S,4aS,5R,7S,7aS)-
Umbroside
172922-52-0
Ac-Shanz-ME
Barlerin (Standard)
MFCD15071141
CHEMBL463751
SCHEMBL3244727
8-O-Acetylshanzhisidemethylester
HY-N0758R
DTXSID80206008
HY-N0758
S9244
AKOS030573654
CCG-269219
CS-6504
AC-34946
AS-76883
F17723
(4aR,4bS,6aS,7S,9aS,9bS,11aS)-N-(1,1-Dimethylethyl)hexadecahydro-4a,6a-dimethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxamide
(5ss,17ss)-N-(1,1-dimethylethyl)-3-oxo-4-azaandrostane-17-carboxamide
[4aR-(4aa,4bss,6aa,7a,9ass,9ba,11aa)]-N-(1,1-Dimethylethyl)hexadecahydro-4a,6a-dimethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxamide
Cyclopenta(c)pyran-4-carboxylic acid, 7-(acetyloxy)-1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-5-hydroxy-7-methyl-, methyl ester, (1S-(1alpha,4aalpha,5alpha,7alpha,7aalpha))-
InChI=1/C19H28O12/c1-7(21)31-19(2)4-9(22)11-8(16(26)27-3)6-28-17(12(11)19)30-18-15(25)14(24)13(23)10(5-20)29-18/h6,9-15,17-18,20,22-25H,4-5H2,1-3H3/t9-,10-,11+,12-,13-,14+,15-,17+,18+,19+/m1/s
METHYL (1S,4AS,5R,7S,7AS)-7-(ACETYLOXY)-5-HYDROXY-7-METHYL-1-{[(2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}-1H,4AH,5H,6H,7AH-CYCLOPENTA[C]PYRAN-4-CARBOXYLATE
Methyl (1S,4aS,5R,7S,7aS)-7-acetoxy-5-hydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Pubchem:
162823
Cas:
57420-46-9
Gnps:
CCMSLIB00006481772
Zinc:
ZINC000031475539
Nmrshiftdb2:
20108976
Chembl:
CHEMBL463751
Comptox:
DTXSID80206008
CPRiL:
100518
SMILES: C1CCC(C12)C(OC=C2)OC3CCCCO3
Level: 1
Mol. Weight: 448.42 g/mol
SMILES: C1CCC(C12)COC=C2
Level: 0
Mol. Weight: 448.42 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 448.42 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.67
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.88
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.7
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.62
- Plasma Protein Binding
- 58.3
- 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
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.14
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.36
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.0
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.32
- 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
- Safe
- T. Pyriformis
- -35.16
- Rat (Acute)
- 2.85
- Rat (Chronic Oral)
- 3.38
- Fathead Minnow
- 3.88
- 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
- 473.49
- Hydration Free Energy
- -7.05
- Log(D) at pH=7.4
- -0.27
- Log(P)
- -1.44
- Log S
- -0.89
- Log(Vapor Pressure)
- -12.26
- Melting Point
- 152.1
- pKa Acid
- 5.58
- pKa Basic
- 2.46
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.9174 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8071 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7847 |