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13189-98-5 molecular structure
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(2R)-2-amino-3-[(3-hydroxypropyl)sulfanyl]propanoic acid

ChemBase ID: 72844
Molecular Formular: C6H13NO3S
Molecular Mass: 179.23732
Monoisotopic Mass: 179.06161428
SMILES and InChIs

SMILES:
[C@@H](C(=O)O)(CSCCCO)N
Canonical SMILES:
OCCCSC[C@@H](C(=O)O)N
InChI:
InChI=1S/C6H13NO3S/c7-5(6(9)10)4-11-3-1-2-8/h5,8H,1-4,7H2,(H,9,10)/t5-/m0/s1
InChIKey:
KINWYTAUPKOPCQ-YFKPBYRVSA-N

Cite this record

CBID:72844 http://www.chembase.cn/molecule-72844.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R)-2-amino-3-[(3-hydroxypropyl)sulfanyl]propanoic acid
IUPAC Traditional name
fudosteine
Synonyms
Fudosteine
3-[(3-Hydroxypropyl)thio]alanine
(-)-3-[(3-Hydroxypropyl)thio]-L-alanine
Cleanal
Fudosteine
SS 320A
Spelear
S-(3-Hydroxypropyl)-L-cysteine
CAS Number
13189-98-5
MDL Number
MFCD00899873
PubChem SID
162037765
PubChem CID
134669

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 134669 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 2.3556938  H Acceptors
H Donor LogD (pH = 5.5) -3.1388693 
LogD (pH = 7.4) -3.1458898  Log P -3.1388948 
Molar Refractivity 44.0815 cm3 Polarizability 17.567696 Å3
Polar Surface Area 83.55 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
>190°C (dec.) expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Purity
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals TRC TRC
Selleck Chemicals - S2129 external link
Research Area: Respiratory Diseases
Biological Activity:
Fudosteine is a novel mucoactive agent and a MUC5AC mucin hypersecretion inhibitor. MUC5AC mucin synthesis and the expression of the MUC5AC gene were increased by LPS in rats or TNF-α in NCI-H292 cells; these effects were inhibited by fudosteine treatment. Fudosteine inhibits MUC5AC mucin hypersecretion by reducing MUC5AC gene expression and the effects of fudosteine are associated with the inhibition of extracellular signal-related kinase and p38 mitogen-activated protein kinase in vivo and extracellular signal-related kinase in vitro. [1]
Toronto Research Chemicals - H952575 external link
An antiinflammatory expectorant used in the treatment of MUC5 mucin obstructive pulmonary disease.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  Antonela Antoniu S. Expert Opin Investig Drugs
  • • Takeyama, K., et al.: J. Immunol.,164, 1546 (2000)
  • • Komatsu, H., et al.: Pulm. Pharmacol. Ther., 18, 121 (2000)
  • • Rhee, C., et al.: Eur. Respir. J., 32, 1195 (2000)
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PATENTS

PATENTS

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INTERNET

INTERNET

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