2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid

C15H18O5 — CID 163045963

IUPAC2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid
SMILESC=C[C@]1(C)C[C@]2(O)OC(=O)C(C)=C2C[C@H]1C(=C)C(=O)O
InChIInChI=1S/C15H18O5/c1-5-14(4)7-15(19)11(9(3)13(18)20-15)6-10(14)8(2)12(16)17/h5,10,19H,1-2,6-7H2,3-4H3,(H,16,17)/t10-,14+,15-/m0/s1
InChIKeyLCYXSLKTAYHKQA-VQISRLSMSA-N
MW278.30 g/mol
LogP1.79
Rot. Bonds3

About 2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid

2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid (PubChem CID 163045963) has the molecular formula C15H18O5 and a molecular weight of 278.30 g/mol. Its IUPAC name is 2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid.

Molecular Properties

Compound Name2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid
PubChem CID163045963
Molecular FormulaC15H18O5
Molecular Weight278.30 g/mol
Exact Mass278.12
IUPAC Name2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid
SMILESC=C[C@]1(C)C[C@]2(O)OC(=O)C(C)=C2C[C@H]1C(=C)C(=O)O
InChIInChI=1S/C15H18O5/c1-5-14(4)7-15(19)11(9(3)13(18)20-15)6-10(14)8(2)12(16)17/h5,10,19H,1-2,6-7H2,3-4H3,(H,16,17)/t10-,14+,15-/m0/s1
InChIKeyLCYXSLKTAYHKQA-VQISRLSMSA-N
XLogP1.79
TPSA83.83 Ų
H-Bond Donors2
H-Bond Acceptors4
Rotatable Bonds3
Heavy Atoms20
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500278.30
LogP ≤ 51.79
H-Bond Donors ≤ 52
H-Bond Acceptors ≤ 104

Computed Properties (RDKit)

Structural Alerts{'alert_name': 'isolated_alkene', 'substructure': 'N/A'}, {'alert_name': 'Michael_acceptor_1', 'substructure': 'N/A'}

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Related Compounds

methyl 2-[(5S,6R,7aR)-6-ethenyl-7a-methoxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoate
CID 162930058
(4aS,8aR)-9a-hydroxy-3,8a-dimethyl-5-methylidene-4,4a,6,9-tetrahydrobenzo[f][1]benzofuran-2-one
CID 163189392
(8aS,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-4,4a,6,9-tetrahydrobenzo[f][1]benzofuran-2-one
CID 171669711
[(4aS,8R,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-2-oxo-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-8-yl] acetate
CID 14258972
(9a-hydroxy-3,5,8a-trimethyl-2-oxo-4a,7,8,9-tetrahydro-4H-benzo[f][1]benzofuran-8-yl) acetate
CID 78173140
methyl 2-[(5S,6S,7aR)-6-ethenyl-3,6-dimethyl-2-oxo-4,5,7,7a-tetrahydro-1-benzofuran-5-yl]prop-2-enoate
CID 163066280
4a,9a-dihydroxy-3,5,8a-trimethyl-8,9-dihydro-4H-benzo[f][1]benzofuran-2,7-dione
CID 163139763
[(4aR,8aS,9aS)-9a-hydroxy-3,8a-dimethyl-2-oxo-4a,9-dihydro-4H-benzo[f][1]benzofuran-5-yl]methyl acetate
CID 163099903
2-[(1R,2R,3R,4S,6S)-3-(1-carboxyethenyl)-4-ethenyl-2,6-dihydroxy-4-methylcyclohexyl]propanoic acid
CID 23241291
2-[(3aR,4R,6S,7R,7aR)-6-ethenyl-6-methyl-4-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-4,5,7,7a-tetrahydro-3aH-1-benzofuran-7-yl]prop-2-enoic acid
CID 162984485
8,9a-dihydroxy-3,4a,5-trimethyl-7,8,8a,9-tetrahydro-4H-benzo[f][1]benzofuran-2-one
CID 162912462
(5R,7S,7aR)-5-tert-butyl-7,7a-dihydroxy-3-methyl-4,5,6,7-tetrahydro-1-benzofuran-2-one
CID 135045154

Frequently Asked Questions

What is the IUPAC name of 2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid?
The IUPAC name of 2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid (CID 163045963) is 2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid.
What is the SMILES notation for 2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid?
The canonical SMILES for 2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid is C=C[C@]1(C)C[C@]2(O)OC(=O)C(C)=C2C[C@H]1C(=C)C(=O)O.
What is the InChIKey of 2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid?
The InChIKey is LCYXSLKTAYHKQA-VQISRLSMSA-N. The full InChI is InChI=1S/C15H18O5/c1-5-14(4)7-15(19)11(9(3)13(18)20-15)6-10(14)8(2)12(16)17/h5,10,19H,1-2,6-7H2,3-4H3,(H,16,17)/t10-,14+,15-/m0/s1.
What are the key properties of 2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid?
2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid has a molecular weight of 278.30 g/mol, XLogP of 1.79, 3 rotatable bonds, 2 hydrogen bond donors, and 4 hydrogen bond acceptors.
Where does this data come from?
All data for 2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid is sourced from PubChem (CID 163045963), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).