(2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid

C16H14O10 — CID 163182420

IUPAC(2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid
SMILESO=C(C=Cc1ccc(O)c(O)c1)O[C@@H]1C=C(C(=O)O)O[C@@H](C(=O)O)[C@@H]1O
InChIInChI=1S/C16H14O10/c17-8-3-1-7(5-9(8)18)2-4-12(19)25-10-6-11(15(21)22)26-14(13(10)20)16(23)24/h1-6,10,13-14,17-18,20H,(H,21,22)(H,23,24)/t10-,13-,14-/m1/s1
InChIKeyZQFOLQKZDARIIB-LERXQTSPSA-N
MW366.28 g/mol
LogP-0.16
Rot. Bonds5

About (2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid

(2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid (PubChem CID 163182420) has the molecular formula C16H14O10 and a molecular weight of 366.28 g/mol. Its IUPAC name is (2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid.

Molecular Properties

Compound Name(2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid
PubChem CID163182420
Molecular FormulaC16H14O10
Molecular Weight366.28 g/mol
Exact Mass366.06
IUPAC Name(2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid
SMILESO=C(C=Cc1ccc(O)c(O)c1)O[C@@H]1C=C(C(=O)O)O[C@@H](C(=O)O)[C@@H]1O
InChIInChI=1S/C16H14O10/c17-8-3-1-7(5-9(8)18)2-4-12(19)25-10-6-11(15(21)22)26-14(13(10)20)16(23)24/h1-6,10,13-14,17-18,20H,(H,21,22)(H,23,24)/t10-,13-,14-/m1/s1
InChIKeyZQFOLQKZDARIIB-LERXQTSPSA-N
XLogP-0.16
TPSA170.82 Ų
H-Bond Donors5
H-Bond Acceptors8
Rotatable Bonds5
Heavy Atoms26
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500366.28
LogP ≤ 5-0.16
H-Bond Donors ≤ 55
H-Bond Acceptors ≤ 108

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)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-4,5-dihydroxycyclohexene-1-carboxylic acid
CID 10131826
5-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-2,3,4-trihydroxycyclohexane-1-carboxylic acid
CID 162852427
(5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxycyclohexene-1-carboxylic acid
CID 5315602
[(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
trans-(3S,5S)-3,5-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
CID 162954739
[(3R,4S,5S,6R)-4,5,6-trihydroxy-6-(hydroxymethyl)oxan-3-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate
CID 175511269
[(3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CID 57337917
(2S)-2-[(2R,3R,4R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-4-hydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid
CID 162960322
[(1R,3R,4R,5R)-1,4-dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CID 102210472
(1R,3R,4S)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3-dihydroxycyclohexane-1-carboxylic acid
CID 166464398

Frequently Asked Questions

What is the IUPAC name of (2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid?
The IUPAC name of (2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid (CID 163182420) is (2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid.
What is the SMILES notation for (2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid?
The canonical SMILES for (2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid is O=C(C=Cc1ccc(O)c(O)c1)O[C@@H]1C=C(C(=O)O)O[C@@H](C(=O)O)[C@@H]1O.
What is the InChIKey of (2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid?
The InChIKey is ZQFOLQKZDARIIB-LERXQTSPSA-N. The full InChI is InChI=1S/C16H14O10/c17-8-3-1-7(5-9(8)18)2-4-12(19)25-10-6-11(15(21)22)26-14(13(10)20)16(23)24/h1-6,10,13-14,17-18,20H,(H,21,22)(H,23,24)/t10-,13-,14-/m1/s1.
What are the key properties of (2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid?
(2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid has a molecular weight of 366.28 g/mol, XLogP of -0.16, 5 rotatable bonds, 5 hydrogen bond donors, and 8 hydrogen bond acceptors.
Where does this data come from?
All data for (2R,3R,4R)-4-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid is sourced from PubChem (CID 163182420), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).