4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid

C18H20O15 — CID 91449850

IUPAC4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid
SMILESO=C(O)C=CC(=O)OC[C@H](OC(=O)C=CC(=O)O)[C@@H](OC(=O)C=CC(=O)O)[C@H](O)[C@H](O)CO
InChIInChI=1S/C18H20O15/c19-7-9(20)17(30)18(33-16(29)6-3-13(25)26)10(32-15(28)5-2-12(23)24)8-31-14(27)4-1-11(21)22/h1-6,9-10,17-20,30H,7-8H2,(H,21,22)(H,23,24)(H,25,26)/t9-,10+,17-,18-/m1/s1
InChIKeyZDFYJIPVEKNDHA-AYBUMKCRSA-N
MW476.34 g/mol
LogP-3.01
Rot. Bonds14

About 4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid

4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid (PubChem CID 91449850) has the molecular formula C18H20O15 and a molecular weight of 476.34 g/mol. Its IUPAC name is 4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid.

Molecular Properties

Compound Name4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid
PubChem CID91449850
Molecular FormulaC18H20O15
Molecular Weight476.34 g/mol
Exact Mass476.08
IUPAC Name4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid
SMILESO=C(O)C=CC(=O)OC[C@H](OC(=O)C=CC(=O)O)[C@@H](OC(=O)C=CC(=O)O)[C@H](O)[C@H](O)CO
InChIInChI=1S/C18H20O15/c19-7-9(20)17(30)18(33-16(29)6-3-13(25)26)10(32-15(28)5-2-12(23)24)8-31-14(27)4-1-11(21)22/h1-6,9-10,17-20,30H,7-8H2,(H,21,22)(H,23,24)(H,25,26)/t9-,10+,17-,18-/m1/s1
InChIKeyZDFYJIPVEKNDHA-AYBUMKCRSA-N
XLogP-3.01
TPSA251.49 Ų
H-Bond Donors6
H-Bond Acceptors12
Rotatable Bonds14
Heavy Atoms33
Complexity—

Lipinski Rule of Five

2 violations

RuleValue
MW ≤ 500476.34
LogP ≤ 5-3.01
H-Bond Donors ≤ 56
H-Bond Acceptors ≤ 1012

Computed Properties (RDKit)

Structural Alerts{'alert_name': '>_2_ester_groups', 'substructure': 'N/A'}, {'alert_name': 'Michael_acceptor_1', 'substructure': 'N/A'}

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Related Compounds

(Z)-4-[(2R,3S,4R,5R)-1,2,3,4,5,6-hexahydroxyhexoxy]-4-oxobut-2-enoic acid
CID 88724547
[(2S,3S,4R,5R)-1,2-dicarboxyoxy-4,5,6-trihydroxyhexan-3-yl] hydrogen carbonate
CID 54363619
4-(2,3-dihydroxypropoxy)-4-oxobut-2-enoic acid
CID 54038335
(E)-4-[2-[(E)-3-carboxyprop-2-enoyl]oxypropoxy]-4-oxobut-2-enoic acid
CID 6446969
pentakis((2S,3R)-butane-1,2,3,4-tetrol);bis((Z)-but-2-enedioic acid)
CID 157481940
(Z)-4-(2-hydroxy-3-prop-2-enoyloxypropoxy)-4-oxobut-2-enoic acid
CID 90382332
(Z)-4-[2-hydroxy-3-[(Z)-4-oxobut-2-enoyl]oxypropoxy]-4-oxobut-2-enoic acid
CID 89216787
[(2R,3S,4S,5S)-6-hydroxy-2,3,4,5-tetra(prop-2-enoyloxy)hexyl] prop-2-enoate
CID 133126600
2-[2-[[2-[(2S,3S,4R,5R)-2,3-bis[[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetyl]oxy]-4,5,6-trihydroxyhexoxy]-2-oxoethyl]-(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid
CID 57259658
(E)-4-(2-ethylbutoxy)-4-oxobut-2-enoic acid
CID 88825906
(Z)-but-2-enedioic acid;(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
CID 155146644
but-2-enedioic acid;(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
CID 159896498

Frequently Asked Questions

What is the IUPAC name of 4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid?
The IUPAC name of 4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid (CID 91449850) is 4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid.
What is the SMILES notation for 4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid?
The canonical SMILES for 4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid is O=C(O)C=CC(=O)OC[C@H](OC(=O)C=CC(=O)O)[C@@H](OC(=O)C=CC(=O)O)[C@H](O)[C@H](O)CO.
What is the InChIKey of 4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid?
The InChIKey is ZDFYJIPVEKNDHA-AYBUMKCRSA-N. The full InChI is InChI=1S/C18H20O15/c19-7-9(20)17(30)18(33-16(29)6-3-13(25)26)10(32-15(28)5-2-12(23)24)8-31-14(27)4-1-11(21)22/h1-6,9-10,17-20,30H,7-8H2,(H,21,22)(H,23,24)(H,25,26)/t9-,10+,17-,18-/m1/s1.
What are the key properties of 4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid?
4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid has a molecular weight of 476.34 g/mol, XLogP of -3.01, 14 rotatable bonds, 6 hydrogen bond donors, and 12 hydrogen bond acceptors.
Where does this data come from?
All data for 4-[(2S,3S,4R,5R)-2,3-bis(3-carboxyprop-2-enoyloxy)-4,5,6-trihydroxyhexoxy]-4-oxobut-2-enoic acid is sourced from PubChem (CID 91449850), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).