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Methyl (1S,4As,6S,7R,7As)-6-Hydroxy-7-Methyl-1-(3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl)Oxy-1,4A,5,6,7,7A-Hexahydrocyclopenta(C)Pyran-4-Carboxylate

HCID 354446
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Basic information

CAS
18524-94-2
Standard SMILES
COC(=O)C1=CO[C@@H](OC2OC(CO)C(O)C(O)C2O)[C@@H]2[C@@H](C)[C@@H](O)C[C@H]12
InChIKey
AMBQHHVBBHTQBF-PTGPOGFDSA-N
Molecular formula
C17H26O10
Average molar mass
390.4 g/mol
Monoisotopic mass
390.15259702

Names & identifiers

Preferred name
Methyl (1S,4As,6S,7R,7As)-6-Hydroxy-7-Methyl-1-(3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl)Oxy-1,4A,5,6,7,7A-Hexahydrocyclopenta(C)Pyran-4-Carboxylate
IUPAC
methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
English name
Loganin
Molecular formula
C17H26O10
Molecular weight
390.38

Names & synonyms

methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylateMethyl (1S,4As,6S,7R,7As)-6-Hydroxy-7-Methyl-1-(3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl)Oxy-1,4A,5,6,7,7A-Hexahydrocyclopenta(C)Pyran-4-CarboxylateRefChem:1089170MLS000728659CHEMBL2135791SCHEMBL23805434DTXSID60939948HMS2267G06NSC606403SMR000470832L0268SR-01000760596
Show more names
LoganosideLoganicCuchiloside7-HYDROXY-6-DESOXYVERBENALINMethyl 6-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[d]pyran-4-carboxylateLOGANINMeliatinLoganinlLOGANINENSC 606403
SR-01000760596-2Methyl (1S,4aS,6S,7R,7aS)-1-(hexopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylateMethyl 1-(hexopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Database identifiers

CAS
18524-94-2
PubChem CID
354446
DTXSID
DTXSID60939948
ChEMBL
CHEMBL2135791

Properties

Computed structural properties

XLogP
-1.4
Topological polar surface area
155 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
10
Rotatable bonds
5
Heavy atoms
27
Formal charge
0
Complexity
580

Physicochemical properties

Melting point
222 °C · 222°C
alpha
20 · D20 -82.1° (water)
Boiling point
608.8 · 608.8±55.0 °C(Predicted)
Density
1.5 · 1.50±0.1 g/cm3(Predicted)
storage temp.
Sealed in dry,Room Temperature
Water Solubility
Completely soluble in water
solubility
15 mg/ml; · DMF: 15 mg/ml; DMSO: 10 mg/ml; PBS (pH 7.2): 10 mg/ml
form
Solid
pka
12.8 · 12.80±0.70(Predicted)
color
White to Almost white
λmax
240 nm · 240nm(MeOH)(lit.)
Merck
14 · 14,5560
BRN
55724 · 55724
Major Application
food and beverages
InChIKey
AMBQHHVBBHTQBF-UHFFFAOYSA-N
SMILES
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]3[C@@H](C)[C@@H](O)C[C@H]13
LogP
-2.73 · -2.730 (est)
CAS DataBase Reference
18524 · 18524-94-2(CAS DataBase Reference)
FDA UNII
7 WJ16Q93C · H7WJ16Q93C
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319
Precautionary statements
264 · P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
PPE
95 · Eyeshields, Gloves, type N95 (US)
Risk Statements
22 · 22
Safety Statements
22 · 22-45-24/25
RIDADR
1544 · 1544
WGK Germany
3 · 3
F
3 · 3-10-23
HS Code
29389090 · 29389090
Storage Class
11 · 11 - Combustible Solids

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
3-10-23
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
ridadr
1544
hs_code
29389090
risk_code
22
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
22-45-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319
Precautionary statements
P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Chemistry & industry

Applications · 1 item

UsesLoganin is an iridoid glycoside that exhibits protective effects against hepatic injury and other diabetic complications associated with abnormal metabolic states and inflammation caused by oxidative stress and advanced glycation endproduct formation.

Additional notes

DefinitionChEBI: An iridoid monoterpenoid isolated from the plant species of the genus Cornus.

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