[(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate

C22H26O8 — CID 162984626

IUPAC[(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
SMILESC=C1C(=O)O[C@H]2[C@H]1[C@@H](OC(=O)[C@@]1(C)O[C@H]1C)[C@H](OC(C)=O)C(=C)[C@]1(O)CC=C(C)[C@H]21
InChIInChI=1S/C22H26O8/c1-9-7-8-22(26)11(3)16(27-13(5)23)18(29-20(25)21(6)12(4)30-21)14-10(2)19(24)28-17(14)15(9)22/h7,12,14-18,26H,2-3,8H2,1,4-6H3/t12-,14-,15+,16+,17-,18+,21-,22+/m0/s1
InChIKeyXDWMWDMIPCSQNB-NKDHHQRPSA-N
MW418.44 g/mol
LogP1.37
Rot. Bonds3

About [(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate

[(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate (PubChem CID 162984626) has the molecular formula C22H26O8 and a molecular weight of 418.44 g/mol. Its IUPAC name is [(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate.

Molecular Properties

Compound Name[(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
PubChem CID162984626
Molecular FormulaC22H26O8
Molecular Weight418.44 g/mol
Exact Mass418.16
IUPAC Name[(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
SMILESC=C1C(=O)O[C@H]2[C@H]1[C@@H](OC(=O)[C@@]1(C)O[C@H]1C)[C@H](OC(C)=O)C(=C)[C@]1(O)CC=C(C)[C@H]21
InChIInChI=1S/C22H26O8/c1-9-7-8-22(26)11(3)16(27-13(5)23)18(29-20(25)21(6)12(4)30-21)14-10(2)19(24)28-17(14)15(9)22/h7,12,14-18,26H,2-3,8H2,1,4-6H3/t12-,14-,15+,16+,17-,18+,21-,22+/m0/s1
InChIKeyXDWMWDMIPCSQNB-NKDHHQRPSA-N
XLogP1.37
TPSA111.66 Ų
H-Bond Donors1
H-Bond Acceptors8
Rotatable Bonds3
Heavy Atoms30
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500418.44
LogP ≤ 51.37
H-Bond Donors ≤ 51
H-Bond Acceptors ≤ 108

Computed Properties (RDKit)

Structural Alerts{'alert_name': '>_2_ester_groups', 'substructure': 'N/A'}, {'alert_name': 'isolated_alkene', 'substructure': 'N/A'}, {'alert_name': 'Michael_acceptor_1', 'substructure': 'N/A'}, {'alert_name': 'Three-membered_heterocycle', 'substructure': 'N/A'}

Analyze [(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate with MolForge

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Related Compounds

methyl (1S,2S,4R,7E,9S,10S,11R)-9-acetyloxy-10-[(2S,3R)-2,3-dimethyloxirane-2-carbonyl]oxy-4-methyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-ene-8-carboxylate
CID 95400936
methyl (1S,2R,4S,5R,7E,9R,10S,11R)-9-acetyloxy-10-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-5-hydroxy-4-methyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-ene-8-carboxylate
CID 122178697
(6-hydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl) 2,3-dimethyloxirane-2-carboxylate
CID 14191409
[(3aS,4S,5S,5aR,6S,7S,9aS,9bS)-6,7-dihydroxy-5a,9-dimethyl-5-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate
CID 162976898
methyl 10-acetyloxy-11-(2,3-dimethyloxirane-2-carbonyl)oxy-4-methyl-13-methylidene-14-oxo-3,6,15-trioxatetracyclo[10.3.0.02,4.05,7]pentadec-8-ene-9-carboxylate
CID 85041601
[(3aR,4R,5R,9aR,9bS)-4-acetyloxy-9a-hydroxy-6,9-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,9b-tetrahydroazuleno[4,5-b]furan-5-yl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate
CID 163014678
methyl (3aR,4R,5R,6E,10E,11aR)-5-acetyloxy-4-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
CID 146014776
methyl 5-acetyloxy-4-(2,3-dimethyloxirane-2-carbonyl)oxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
CID 74155557
[(1R,3S,5S,6R,10S,11R)-3,12-dimethyl-7-methylidene-8-oxo-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradec-12-en-5-yl] acetate
CID 14466131
[(1R,3S,5S,6R,10S)-3,12-dimethyl-7-methylidene-8-oxo-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradec-12-en-5-yl] acetate
CID 76764519
methyl (1S,2S,4R,7E,9S,10S,11R)-10-acetyloxy-9-[(2R,3R)-2,3-dimethyloxirane-2-carbonyl]oxy-4-methyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-ene-8-carboxylate
CID 162980497
methyl (1R,2Z,4S,6R,7E,9R,10S,11S)-9-acetyloxy-10-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.04,6]tetradeca-2,7-diene-8-carboxylate
CID 122178696

Frequently Asked Questions

What is the IUPAC name of [(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate?
The IUPAC name of [(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate (CID 162984626) is [(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate.
What is the SMILES notation for [(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate?
The canonical SMILES for [(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate is C=C1C(=O)O[C@H]2[C@H]1[C@@H](OC(=O)[C@@]1(C)O[C@H]1C)[C@H](OC(C)=O)C(=C)[C@]1(O)CC=C(C)[C@H]21.
What is the InChIKey of [(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate?
The InChIKey is XDWMWDMIPCSQNB-NKDHHQRPSA-N. The full InChI is InChI=1S/C22H26O8/c1-9-7-8-22(26)11(3)16(27-13(5)23)18(29-20(25)21(6)12(4)30-21)14-10(2)19(24)28-17(14)15(9)22/h7,12,14-18,26H,2-3,8H2,1,4-6H3/t12-,14-,15+,16+,17-,18+,21-,22+/m0/s1.
What are the key properties of [(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate?
[(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate has a molecular weight of 418.44 g/mol, XLogP of 1.37, 3 rotatable bonds, 1 hydrogen bond donors, and 8 hydrogen bond acceptors.
Where does this data come from?
All data for [(3aS,4R,5R,6aS,9aR,9bS)-5-acetyloxy-6a-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,7,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate is sourced from PubChem (CID 162984626), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).