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37682-72-7 molecular structure
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2-({[(1S)-4-carbamimidamido-1-{[(1S)-1-[(5-carbamimidamido-1-oxopentan-2-yl)carbamoyl]-2-methylpropyl]carbamoyl}butyl]carbamoyl}amino)-3-phenylpropanoic acid dihydrochloride

ChemBase ID: 133234
Molecular Formular: C27H46Cl2N10O6
Molecular Mass: 677.62354
Monoisotopic Mass: 676.2978846
SMILES and InChIs

SMILES:
CC(C)[C@@H](C(=O)NC(CCCNC(=N)N)C=O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)NC(Cc1ccccc1)C(=O)O.Cl.Cl
Canonical SMILES:
O=CC(NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)NC(C(=O)O)Cc1ccccc1)CCCNC(=N)N)CCCNC(=N)N.Cl.Cl
InChI:
InChI=1S/C27H44N10O6.2ClH/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17;;/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43);2*1H/t18?,19-,20?,21-;;/m0../s1
InChIKey:
YAHXZYICKJUJEO-BXLPLHKWSA-N

Cite this record

CBID:133234 http://www.chembase.cn/molecule-133234.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-({[(1S)-4-carbamimidamido-1-{[(1S)-1-[(5-carbamimidamido-1-oxopentan-2-yl)carbamoyl]-2-methylpropyl]carbamoyl}butyl]carbamoyl}amino)-3-phenylpropanoic acid dihydrochloride
IUPAC Traditional name
2-({[(1S)-4-carbamimidamido-1-{[(1S)-1-[(5-carbamimidamido-1-oxopentan-2-yl)carbamoyl]-2-methylpropyl]carbamoyl}butyl]carbamoyl}amino)-3-phenylpropanoic acid dihydrochloride
Synonyms
N-(Nα-Carbonyl-Arg-Val-Arg-al)-Phe
Antipain dihydrochloride from microbial source
CAS Number
37682-72-7
MDL Number
MFCD00135957
PubChem SID
24891067
162227511
PubChem CID
16218941

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
A6191 external link Add to cart Please log in.
Data Source Data ID
PubChem 16218941 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.433761  H Acceptors 12 
H Donor 11  LogD (pH = 5.5) -5.394688 
LogD (pH = 7.4) -5.3856344  Log P -3.4464593 
Molar Refractivity 178.2286 cm3 Polarizability 60.508217 Å3
Polar Surface Area 277.5 Å2 Rotatable Bonds 19 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
1-butanol: soluble expand Show data source
1-propanol: soluble expand Show data source
DMSO: soluble expand Show data source
ethanol: soluble expand Show data source
H2O: soluble50 mg/mL expand Show data source
methanol: soluble expand Show data source
RTECS
YV9350800 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
Quality Level
PREMIUM expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - A6191 external link
Application
Concentrations for 50% inhibition (μg/ml): papain, 0.16trypsin, 0.26cathepsin A, 1.19cathepsin B, 0.59cathepsin D, 125plasmin, >93chymotrypsin and pepsin, >250It also has been reported to inhibit calpain I, (porcine) with Ki = 1.4 μM
Preparation Note
Solubility testing at 50 mg/ml in water yields a clear to slightly hazy yellow solution. It is reportedly soluble in methanol, water, and DMSO; less soluble in ethanol, butanol, and propanol; insoluble in benzene, hexane, and chloroform.8 A stock solution in water or buffer is stable for about a month at -20 °C.Dilute solutions should be stored on ice and kept for only a day because of the terminal aldehyde, which is subject to oxidation and racemization.
Stock solutions in water or buffer stable for 1 week at 4 °C, 1 month at -20 °C.
Biochem/physiol Actions
Reversible inhibitor of serine/cysteine proteases and some trypsin-like serine proteases. Its action resembles leupeptin; however, its plasmin inhibition is less and its cathepsin A inhibition is more than that observed with leupeptin. Chronic administration of antipain can reduce the frequency of chemically induced transformation in BALB/c-/3T3 cells.1

REFERENCES

REFERENCES

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PATENTS

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