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201608-14-2 molecular structure
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(4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-carboxy-2-acetamidopropanamido]butanoic acid

ChemBase ID: 106349
Molecular Formular: C30H34F3N5O13
Molecular Mass: 729.6118696
Monoisotopic Mass: 729.21052083
SMILES and InChIs

SMILES:
CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)C)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
Canonical SMILES:
OC(=O)C[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(=O)O)CCC(=O)O
InChI:
InChI=1S/C30H34F3N5O13/c1-12(2)25(38-26(47)17(6-7-21(40)41)36-28(49)18(10-22(42)43)34-13(3)39)29(50)37-19(11-23(44)45)27(48)35-14-4-5-15-16(30(31,32)33)9-24(46)51-20(15)8-14/h4-5,8-9,12,17-19,25H,6-7,10-11H2,1-3H3,(H,34,39)(H,35,48)(H,36,49)(H,37,50)(H,38,47)(H,40,41)(H,42,43)(H,44,45)/t17-,18-,19-,25-/m0/s1
InChIKey:
GZDRODOYEFEHGG-NUDCOPPTSA-N

Cite this record

CBID:106349 http://www.chembase.cn/molecule-106349.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-carboxy-2-acetamidopropanamido]butanoic acid
IUPAC Traditional name
(4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-carboxy-2-acetamidopropanamido]butanoic acid
Synonyms
Ac-Asp-Glu-Val-Asp-AFC
Ac-DEVD-AFC
Ac-Asp-Glu-Val-Asp-7-Amino-4-trifluoromethylcoumarin
N-Acetyl-Asp-Glu-Val-Asp-7-amido-4-trifluoromethylcoumarin
CAS Number
201608-14-2
MDL Number
MFCD01310970
PubChem SID
162087205
PubChem CID
644234

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 644234 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.3861065  H Acceptors 12 
H Donor LogD (pH = 5.5) -6.030276 
LogD (pH = 7.4) -10.821213  Log P -1.2104636 
Molar Refractivity 162.6725 cm3 Polarizability 61.966278 Å3
Polar Surface Area 283.7 Å2 Rotatable Bonds 18 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
H2O: soluble1 mg/mL expand Show data source
Apperance
white powder expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... CASP3(836) expand Show data source
Purity
≥90% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich
MP Biomedicals - 03AFC138 external link
A fluorogenic substrate for Caspase-3 (CPP32, YAMA). Also acts as a substrate for granzyme B-processed caspase-6, caspase-7, caspase-8, and caspase-10.
Excitation max.: ~400 nm, Emission max.: ~505 nm
Sigma Aldrich - A0466 external link
Amino Acid Sequence
NAc-Asp-Glu-Val-Asp-AFC
Biochem/physiol Actions
A fluorogenic substrate for caspase 3, a protease that is rapidly activated when cells are exposed to apoptotic conditions and that cleaves poly(ADP-ribose) polymerase. The 7-amido-4-trifluoromethylcoumarin derivative has better membrane permeability than the 7-amido-4-methylcoumarin derivative (A1086).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Thornberry, N.A. et al., Science, 281:1312 (1998).
  • • Nicholson, D.W. et al., Nature, 376:37 (1995).
  • • Keramaris, E., et al. 2000. Mol. Cell Neurosci. 15, 368.
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PATENTS

PATENTS

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INTERNET

INTERNET

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