methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

C17H20O9 — CID 162893503

IUPACmethyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
SMILESCOC(=O)C1=CO[C@@H](OC(C)=O)[C@@H]2C(COC(C)=O)=C[C@@H](OC(C)=O)[C@H]12
InChIInChI=1S/C17H20O9/c1-8(18)23-6-11-5-13(25-9(2)19)15-12(16(21)22-4)7-24-17(14(11)15)26-10(3)20/h5,7,13-15,17H,6H2,1-4H3/t13-,14-,15+,17+/m1/s1
InChIKeyCNYKDWSMWFETDQ-AIANPOQGSA-N
MW368.34 g/mol
LogP0.63
Rot. Bonds5

About methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate (PubChem CID 162893503) has the molecular formula C17H20O9 and a molecular weight of 368.34 g/mol. Its IUPAC name is methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate.

Molecular Properties

Compound Namemethyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
PubChem CID162893503
Molecular FormulaC17H20O9
Molecular Weight368.34 g/mol
Exact Mass368.11
IUPAC Namemethyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
SMILESCOC(=O)C1=CO[C@@H](OC(C)=O)[C@@H]2C(COC(C)=O)=C[C@@H](OC(C)=O)[C@H]12
InChIInChI=1S/C17H20O9/c1-8(18)23-6-11-5-13(25-9(2)19)15-12(16(21)22-4)7-24-17(14(11)15)26-10(3)20/h5,7,13-15,17H,6H2,1-4H3/t13-,14-,15+,17+/m1/s1
InChIKeyCNYKDWSMWFETDQ-AIANPOQGSA-N
XLogP0.63
TPSA114.43 Ų
H-Bond Donors
H-Bond Acceptors9
Rotatable Bonds5
Heavy Atoms26
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500368.34
LogP ≤ 50.63
H-Bond Donors ≤ 50
H-Bond Acceptors ≤ 109

Computed Properties (RDKit)

Structural Alerts{'alert_name': '>_2_ester_groups', 'substructure': 'N/A'}, {'alert_name': 'isolated_alkene', 'substructure': 'N/A'}

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Related Compounds

Asperuloside
CID 84298
Geniposide
CID 107848
Asperulosidic Acid
CID 11968867
Daphylloside
CID 21602024
Scandoside, methyl ester
CID 442433
Deacetyl asperulosidic acid methyl ester
CID 6325021
Methyl (1S,4aS,7aS)-7-((acetyloxy)methyl)-1,4a,5,7a-tetrahydro-1-((2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy)cyclopenta(c)pyran-4-carboxylate
CID 162083
10-O-Acetylgeniposide
CID 6324916
6'-O-acetylgeniposide
CID 44253991
4-[[(1S,4aS,7aS)-4-methoxycarbonyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methoxy]-4-oxobutanoic acid
CID 44255239
Methyl 7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
CID 3515873
(5-(hexopyranosyloxy)-1-oxo-2a,4a,5,7b-tetrahydro-1H-2,6-dioxacyclopenta(cd)inden-4-yl)methyl acetate
CID 233330

Frequently Asked Questions

What is the IUPAC name of methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate?
The IUPAC name of methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate (CID 162893503) is methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate.
What is the SMILES notation for methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate?
The canonical SMILES for methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate is COC(=O)C1=CO[C@@H](OC(C)=O)[C@@H]2C(COC(C)=O)=C[C@@H](OC(C)=O)[C@H]12.
What is the InChIKey of methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate?
The InChIKey is CNYKDWSMWFETDQ-AIANPOQGSA-N. The full InChI is InChI=1S/C17H20O9/c1-8(18)23-6-11-5-13(25-9(2)19)15-12(16(21)22-4)7-24-17(14(11)15)26-10(3)20/h5,7,13-15,17H,6H2,1-4H3/t13-,14-,15+,17+/m1/s1.
What are the key properties of methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate?
methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate has a molecular weight of 368.34 g/mol, XLogP of 0.63, 5 rotatable bonds, 0 hydrogen bond donors, and 9 hydrogen bond acceptors.
Where does this data come from?
All data for methyl (1S,4aS,5R,7aS)-1,5-diacetyloxy-7-(acetyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate is sourced from PubChem (CID 162893503), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).