(4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

C22H27N3O8S — CID 18657797

IUPAC(4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
SMILESC=CCOC(=O)N1C[C@@H](SC2=C(C(=O)O)N3C(=O)[C@H]([C@@H](C)O)[C@H]3[C@H]2C)C[C@H]1C1CC(=O)NC1=O
InChIInChI=1S/C22H27N3O8S/c1-4-5-33-22(32)24-8-11(6-13(24)12-7-14(27)23-19(12)28)34-18-9(2)16-15(10(3)26)20(29)25(16)17(18)21(30)31/h4,9-13,15-16,26H,1,5-8H2,2-3H3,(H,30,31)(H,23,27,28)/t9-,10-,11+,12?,13+,15-,16-/m1/s1
InChIKeyBZHWGVMWOQAIAU-YCAINXAZSA-N
MW493.54 g/mol
LogP0.30
Rot. Bonds7

About (4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

(4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (PubChem CID 18657797) has the molecular formula C22H27N3O8S and a molecular weight of 493.54 g/mol. Its IUPAC name is (4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid.

Molecular Properties

Compound Name(4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
PubChem CID18657797
Molecular FormulaC22H27N3O8S
Molecular Weight493.54 g/mol
Exact Mass493.15
IUPAC Name(4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
SMILESC=CCOC(=O)N1C[C@@H](SC2=C(C(=O)O)N3C(=O)[C@H]([C@@H](C)O)[C@H]3[C@H]2C)C[C@H]1C1CC(=O)NC1=O
InChIInChI=1S/C22H27N3O8S/c1-4-5-33-22(32)24-8-11(6-13(24)12-7-14(27)23-19(12)28)34-18-9(2)16-15(10(3)26)20(29)25(16)17(18)21(30)31/h4,9-13,15-16,26H,1,5-8H2,2-3H3,(H,30,31)(H,23,27,28)/t9-,10-,11+,12?,13+,15-,16-/m1/s1
InChIKeyBZHWGVMWOQAIAU-YCAINXAZSA-N
XLogP0.30
TPSA153.55 Ų
H-Bond Donors3
H-Bond Acceptors8
Rotatable Bonds7
Heavy Atoms34
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500493.54
LogP ≤ 50.30
H-Bond Donors ≤ 53
H-Bond Acceptors ≤ 108

Computed Properties (RDKit)

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

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Related Compounds

(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5R)-1-prop-2-enoxycarbonyl-5-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CID 67705582
(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5R)-1-prop-2-enoxycarbonyl-5-[1-(1H-pyrazol-4-yl)ethyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CID 67705468
(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(3S,5S)-5-(5-oxo-2-prop-2-enoxycarbonylpyrazolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CID 18657936
prop-2-enyl 6-(1-hydroxyethyl)-4-methyl-7-oxo-3-[1-prop-2-enoxycarbonyl-5-(1-prop-2-enoxycarbonyl-4,5-dihydroimidazol-2-yl)pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
CID 142648844
(4R,5S,6S)-3-[(3S,5R)-5-[2-[2-(2-amino-2-oxoethyl)imidazol-1-yl]ethyl]-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CID 67705537
(4R,5S,6S)-3-[(3S,5S)-5-[(Z)-3-amino-3-oxoprop-1-enyl]-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-6-[(1R)-1-prop-2-enoxycarbonyloxyethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CID 67794229
prop-2-enyl (4R,5S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[[(4-hydroxypiperidine-1-carbothioyl)amino]methyl]-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
CID 11548957
(4R,5S,6S)-3-[(3S,5R)-5-[2-[5-(3-amino-3-oxoprop-1-enyl)imidazol-1-yl]ethyl]-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CID 67705757
(4R,5S,6S)-3-[(3S,5S)-5-[2-[5-(3-amino-3-oxoprop-1-enyl)imidazol-1-yl]ethyl]-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CID 67873214
(4R,5S,6S)-3-[(3S,5R)-5-[(2,5-dioxopyrrolidin-3-yl)methyl]-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CID 18657768
prop-2-enyl (4R)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-1-prop-2-enoxycarbonyl-5-(2-thiomorpholin-4-ylethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
CID 11786808
(4R,5S,6S)-3-(3-aminocyclobutyl)sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CID 170261328

Frequently Asked Questions

What is the IUPAC name of (4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid?
The IUPAC name of (4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (CID 18657797) is (4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid.
What is the SMILES notation for (4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid?
The canonical SMILES for (4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid is C=CCOC(=O)N1C[C@@H](SC2=C(C(=O)O)N3C(=O)[C@H]([C@@H](C)O)[C@H]3[C@H]2C)C[C@H]1C1CC(=O)NC1=O.
What is the InChIKey of (4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid?
The InChIKey is BZHWGVMWOQAIAU-YCAINXAZSA-N. The full InChI is InChI=1S/C22H27N3O8S/c1-4-5-33-22(32)24-8-11(6-13(24)12-7-14(27)23-19(12)28)34-18-9(2)16-15(10(3)26)20(29)25(16)17(18)21(30)31/h4,9-13,15-16,26H,1,5-8H2,2-3H3,(H,30,31)(H,23,27,28)/t9-,10-,11+,12?,13+,15-,16-/m1/s1.
What are the key properties of (4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid?
(4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid has a molecular weight of 493.54 g/mol, XLogP of 0.30, 7 rotatable bonds, 3 hydrogen bond donors, and 8 hydrogen bond acceptors.
Where does this data come from?
All data for (4R,5S,6S)-3-[(3S,5S)-5-(2,5-dioxopyrrolidin-3-yl)-1-prop-2-enoxycarbonylpyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid is sourced from PubChem (CID 18657797), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).