(3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid

C16H16O8 — CID 10131826

IUPAC(3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid
SMILESO=C(/C=C/c1ccc(O)c(O)c1)O[C@@H]1C=C(C(=O)O)C[C@@H](O)[C@@H]1O
InChIInChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-5,7,12-13,15,17-19,21H,6H2,(H,22,23)/b4-2+/t12-,13-,15+/m1/s1
InChIKeyMRDAXWGGWWDUKL-VKJPNVGWSA-N
MW336.30 g/mol
LogP0.16
Rot. Bonds4

About (3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid

(3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid (PubChem CID 10131826) has the molecular formula C16H16O8 and a molecular weight of 336.30 g/mol. Its IUPAC name is (3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid.

Molecular Properties

Compound Name(3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid
PubChem CID10131826
Molecular FormulaC16H16O8
Molecular Weight336.30 g/mol
Exact Mass336.08
IUPAC Name(3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid
SMILESO=C(/C=C/c1ccc(O)c(O)c1)O[C@@H]1C=C(C(=O)O)C[C@@H](O)[C@@H]1O
InChIInChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-5,7,12-13,15,17-19,21H,6H2,(H,22,23)/b4-2+/t12-,13-,15+/m1/s1
InChIKeyMRDAXWGGWWDUKL-VKJPNVGWSA-N
XLogP0.16
TPSA144.52 Ų
H-Bond Donors5
H-Bond Acceptors7
Rotatable Bonds4
Heavy Atoms24
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500336.30
LogP ≤ 50.16
H-Bond Donors ≤ 55
H-Bond Acceptors ≤ 107

Computed Properties (RDKit)

Structural Alerts{'alert_name': 'catechol_A(92)', 'substructure': 'N/A'}, {'alert_name': 'catechol', 'substructure': 'N/A'}, {'alert_name': 'Michael_acceptor_1', 'substructure': 'N/A'}

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Related Compounds

(3R,4S,5R)-4,5-dihydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexene-1-carboxylic acid
CID 71447328
(5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxycyclohexene-1-carboxylic acid
CID 5315602
(2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid
CID 163182420
trans-(3S,5S)-3,5-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
CID 162954739
5-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-2,3,4-trihydroxycyclohexane-1-carboxylic acid
CID 162852427
(3S,4R,5S)-4-hydroxy-5-(3-phenylprop-2-enoyloxy)-3-(3,4,5-trihydroxybenzoyl)oxycyclohexene-1-carboxylic acid
CID 163157271
[(1R,2R,3R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxycyclopentyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CID 53496254
(2S,3R,4R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-2,4-dihydroxycyclohexane-1-carboxylic acid
CID 134458277
[(3S,4S)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxyoxolan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CID 6476076
(1S,3R,4R,5S)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
CID 7067333
(1S,3R,4R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexane-1-carboxylic acid
CID 139557019
(1S,3R,4S)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
CID 5318529

Frequently Asked Questions

What is the IUPAC name of (3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid?
The IUPAC name of (3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid (CID 10131826) is (3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid.
What is the SMILES notation for (3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid?
The canonical SMILES for (3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid is O=C(/C=C/c1ccc(O)c(O)c1)O[C@@H]1C=C(C(=O)O)C[C@@H](O)[C@@H]1O.
What is the InChIKey of (3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid?
The InChIKey is MRDAXWGGWWDUKL-VKJPNVGWSA-N. The full InChI is InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-5,7,12-13,15,17-19,21H,6H2,(H,22,23)/b4-2+/t12-,13-,15+/m1/s1.
What are the key properties of (3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid?
(3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid has a molecular weight of 336.30 g/mol, XLogP of 0.16, 4 rotatable bonds, 5 hydrogen bond donors, and 7 hydrogen bond acceptors.
Where does this data come from?
All data for (3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid is sourced from PubChem (CID 10131826), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).