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Loganin
- Family: Plantae - Dipsacaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Iridoid Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@@H](C)[C@H](C3)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1 |
| InChIKey | AMBQHHVBBHTQBF-UOUCRYGSSA-N |
| Formula | C17H26O10 |
| HBA | 10 |
| HBD | 5 |
| MW | 390.39 |
| Rotatable Bonds | 4 |
| TPSA | 155.14 |
| LogP | -2.15 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.82 |
| Exact Mass | 390.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Dipsacus laciniatus | Dipsacaceae | Plantae | 398307 |
Showing of synonyms
Loganin
Loganoside
7-Hydroxy-6-desoxyverbenalin
CHEBI:15771
UNII-H7WJ16Q93C
H7WJ16Q93C
EINECS 242-398-0
NSC 606403
LOGANIN, (-)-
NSC-606403
1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta(c)pyran-4-carboxylic acid methyl ester
1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid methyl ester
Methyl (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta(c)pyran-4-carboxylate
Methyl (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, methyl ester, (1S, 4aS, 6S, 7R, 7aS)-
Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, methyl ester, (1S-(1alpha,4aalpha,6alpha,7alpha,7aalpha))-
(1S)-1alpha-(beta-D-GLUCOPYRANOSYLOXY)-1,4Aalpha,5,6,7,7Aalpha-HEXAHYDRO-6alpha-HYDROXY-7alpha-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID METHYL ESTER
242-398-0
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(beta-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(beta-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, (1S,4AS,6S,7R,7AS)-
18524-94-2
Cyclopenta[c]pyran-4-carboxylic acid,1-(b-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, methyl ester, (1S,4aS,6S,7R,7aS)-
Methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
MFCD00075645
(1S,4aS,6S,7R,7aS)-Methyl 6-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
Methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate
(-)-Loganin
C17H26O10
Loganin (Standard)
Spectrum_001503
SpecPlus_000563
LOGANIN [MI]
Spectrum2_001637
Spectrum3_001875
Spectrum4_001914
Spectrum5_000628
Loganin, analytical standard
BSPBio_003350
KBioGR_002535
KBioSS_001983
DivK1c_006659
SCHEMBL307017
SPECTRUM1504066
SPBio_001733
MEGxp0_000723
CHEMBL1081584
ACon1_001749
HY-N0512R
KBio1_001603
KBio2_001983
KBio2_004551
KBio2_007119
KBio3_002852
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, (1S-(1.ALPHA.,4A.ALPHA.,6.ALPHA.,7.ALPHA.,7A.ALPHA.))-
HY-N0512
BDBM50279529
CCG-38757
MSK158033
S3835
AKOS022190418
CS-5019
LMPR0102070001
ML11578
SDCCGMLS-0066747.P001
NCGC00178124-01
NCGC00178124-02
NCGC00178124-03
NCGC00178124-04
NCGC00178124-08
AC-34479
AS-75232
C01433
5A5AFFBA-93AB-4635-A071-FC87B9DC023D
Q15426222
(1S)-1.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A.ALPHA.,5,6,7,7A.ALPHA.-HEXAHYDRO-6.ALPHA.-HYDROXY-7.ALPHA.-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID METHYL ESTER
(1S,4aS,6S,7R,7aS)-Methyl6-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
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, (1S,4AS,6S,7R,7AS)-
Methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
METHYL (1S-(1.ALPHA.,4A.ALPHA.,6.ALPHA.,7.ALPHA.,7A.ALPHA.))-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLATE
Methyl (1S-(1alpha,4aalpha,6alpha,7alpha,7aalpha))-1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta(c)pyran-4-carboxylate
Methyl 6-hydroxy-7-methyl-1-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5
- Abdallah OM (1991). Phenolic glucoside and other constituents of Dipsacus laciniatus. Phytochemistry,1991,30(8),2805-2806. [View]
Pubchem:
87691
Cas:
18524-94-2
Gnps:
CCMSLIB00006479813
Zinc:
ZINC000003978792
Kegg Ligand:
C01433
Chebi:
15771
Metabolights:
MTBLC15771
Chembl:
CHEMBL1081584
Bindingdb:
50279529
CPRiL:
55828
SMILES: C1CCC(C12)C(OC=C2)OC3CCCCO3
Level: 1
Mol. Weight: 390.39 g/mol
SMILES: C1CCC(C12)COC=C2
Level: 0
Mol. Weight: 390.39 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 390.39 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.51
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.080
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.84
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.560
- Plasma Protein Binding
- 54.78
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.610
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.150
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.660
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.770
- Micronucleos
- Safe
- 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
- -9.670
- Rat (Acute)
- 2.590
- Rat (Chronic Oral)
- 3.260
- Fathead Minnow
- 3.470
- 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
- 447.290
- Hydration Free Energy
- -13.800
- Log(D) at pH=7.4
- 0.010
- Log(P)
- -1.26
- Log S
- -1.02
- Log(Vapor Pressure)
- -11.8
- Melting Point
- 158.49
- pKa Acid
- 5.56
- pKa Basic
- 3.75
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7504 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7504 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7194 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7194 |
| Periplasmic pH-dependent serine endoprotease DegQ | P39099 | DEGQ_ECOLI | Escherichia coli | 3 | 0.7001 |
| Periplasmic pH-dependent serine endoprotease DegQ | P39099 | DEGQ_ECOLI | Escherichia coli | 3 | 0.7001 |