(2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid

C22H20O10 — CID 138532986

IUPAC(2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid
SMILESC[C@@H](OC(=O)/C=C/c1ccc(O)c(O)c1)[C@H](OC(=O)/C=C/c1ccc(O)c(O)c1)C(=O)O
InChIInChI=1S/C22H20O10/c1-12(31-19(27)8-4-13-2-6-15(23)17(25)10-13)21(22(29)30)32-20(28)9-5-14-3-7-16(24)18(26)11-14/h2-12,21,23-26H,1H3,(H,29,30)/b8-4+,9-5+/t12-,21+/m1/s1
InChIKeyISUNQDCGPVUMLK-ISOZMGBCSA-N
MW444.39 g/mol
LogP2.16
Rot. Bonds8

About (2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid

(2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid (PubChem CID 138532986) has the molecular formula C22H20O10 and a molecular weight of 444.39 g/mol. Its IUPAC name is (2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid.

Molecular Properties

Compound Name(2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid
PubChem CID138532986
Molecular FormulaC22H20O10
Molecular Weight444.39 g/mol
Exact Mass444.11
IUPAC Name(2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid
SMILESC[C@@H](OC(=O)/C=C/c1ccc(O)c(O)c1)[C@H](OC(=O)/C=C/c1ccc(O)c(O)c1)C(=O)O
InChIInChI=1S/C22H20O10/c1-12(31-19(27)8-4-13-2-6-15(23)17(25)10-13)21(22(29)30)32-20(28)9-5-14-3-7-16(24)18(26)11-14/h2-12,21,23-26H,1H3,(H,29,30)/b8-4+,9-5+/t12-,21+/m1/s1
InChIKeyISUNQDCGPVUMLK-ISOZMGBCSA-N
XLogP2.16
TPSA170.82 Ų
H-Bond Donors5
H-Bond Acceptors9
Rotatable Bonds8
Heavy Atoms32
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500444.39
LogP ≤ 52.16
H-Bond Donors ≤ 55
H-Bond Acceptors ≤ 109

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

(2S,3S,4R,5R)-2,3,4-tris[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-5-(2-methylpropanoyloxy)hexanedioic acid
CID 99649705
(2S,3R,4S,5S)-2,3,5-tris[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4-hydroxyhexanedioic acid
CID 101227453
2-[(Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanedioic acid
CID 132917520
(1R,2S)-1-[(Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropane-1,2,3-tricarboxylic acid
CID 163194056
(1R,2S)-1-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propane-1,2,3-tricarboxylic acid
CID 162889953
2,3-bis[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy]butanedioic acid
CID 46202731
acetic acid;3-(3,4-dihydroxyphenyl)prop-2-enoic acid
CID 159549195
(E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
CID 689043
(2S,3S)-2-acetyloxy-3-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxybutanedioic acid
CID 162919789
3-(3,4-dihydroxyphenyl)prop-2-enoic acid;formic acid
CID 175480823
tert-butyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CID 44571369
[1-(3,4-dihydroxyphenyl)-2-methoxy-2-oxoethyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CID 57344911

Frequently Asked Questions

What is the IUPAC name of (2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid?
The IUPAC name of (2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid (CID 138532986) is (2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid.
What is the SMILES notation for (2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid?
The canonical SMILES for (2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid is C[C@@H](OC(=O)/C=C/c1ccc(O)c(O)c1)[C@H](OC(=O)/C=C/c1ccc(O)c(O)c1)C(=O)O.
What is the InChIKey of (2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid?
The InChIKey is ISUNQDCGPVUMLK-ISOZMGBCSA-N. The full InChI is InChI=1S/C22H20O10/c1-12(31-19(27)8-4-13-2-6-15(23)17(25)10-13)21(22(29)30)32-20(28)9-5-14-3-7-16(24)18(26)11-14/h2-12,21,23-26H,1H3,(H,29,30)/b8-4+,9-5+/t12-,21+/m1/s1.
What are the key properties of (2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid?
(2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid has a molecular weight of 444.39 g/mol, XLogP of 2.16, 8 rotatable bonds, 5 hydrogen bond donors, and 9 hydrogen bond acceptors.
Where does this data come from?
All data for (2S,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanoic acid is sourced from PubChem (CID 138532986), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).