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129-46-4 molecular structure
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hexasodium 8-{4-methyl-3-[3-({[3-({2-methyl-5-[(4,6,8-trisulfonatonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzamido]benzamido}naphthalene-1,3,5-trisulfonate

ChemBase ID: 105193
Molecular Formular: C51H34N6Na6O23S6
Molecular Mass: 1429.17068
Monoisotopic Mass: 1427.93857306
SMILES and InChIs

SMILES:
[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].Cc1c(NC(=O)c2cccc(NC(=O)Nc3cccc(c3)C(=O)Nc3c(C)ccc(c3)C(=O)Nc3ccc(c4c3c(cc(c4)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-])c2)cc(cc1)C(=O)Nc1ccc(c2c1c(cc(c2)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-]
Canonical SMILES:
O=C(Nc1cccc(c1)C(=O)Nc1cc(ccc1C)C(=O)Nc1ccc(c2c1c(cc(c2)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-])Nc1cccc(c1)C(=O)Nc1cc(ccc1C)C(=O)Nc1ccc(c2c1c(cc(c2)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
InChI:
InChI=1S/C51H40N6O23S6.6Na/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80;;;;;;/h3-24H,1-2H3,(H,54,60)(H,55,61)(H,56,58)(H,57,59)(H2,52,53,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80);;;;;;/q;6*+1/p-6
InChIKey:
VAPNKLKDKUDFHK-UHFFFAOYSA-H

Cite this record

CBID:105193 http://www.chembase.cn/molecule-105193.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
hexasodium 8-{4-methyl-3-[3-({[3-({2-methyl-5-[(4,6,8-trisulfonatonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzamido]benzamido}naphthalene-1,3,5-trisulfonate
IUPAC Traditional name
hexasodium 8-{4-methyl-3-[3-({[3-({2-methyl-5-[(4,6,8-trisulfonatonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzamido]benzamido}naphthalene-1,3,5-trisulfonate
hexapotassium 8-{4-methyl-3-[3-({[3-({2-methyl-5-[(4,6,8-trisulfonatonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzamido]benzamido}naphthalene-1,3,5-trisulfonate
Synonyms
Suramine sodium salt
Suramin sodium salt
SURAMIN SODIUM SALT
CAS Number
129-46-4
EC Number
204-949-3
MDL Number
MFCD00210217
Beilstein Number
3694087
PubChem SID
24277738
162092285
PubChem CID
8514

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 8514 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa -3.4551167  H Acceptors 23 
H Donor LogD (pH = 5.5) -8.680967 
LogD (pH = 7.4) -8.681957  Log P 5.577431 
Molar Refractivity 308.1744 cm3 Polarizability 120.47429 Å3
Polar Surface Area 500.73 Å2 Rotatable Bonds 16 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
H2O: >10 mg/mL expand Show data source
Storage Condition
2-8°C expand Show data source
RTECS
QM7000000 expand Show data source
MSDS Link
Download expand Show data source
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
Gene Information
human ... EGF(1950), P2RX1(5023), P2RY1(5028), PDGFA(5154), PLD1(5337) expand Show data source
Purity
≥95% expand Show data source
≥99.0% (TLC) expand Show data source
98% expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C51H34N6Na6O23S6 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02159021 external link
Sodium Salt
Purity: 98%
Various growth factor inhibitor. Protein G uncoupler from receptors through interaction with intracellular domains. A strong competitive reverse transcriptase inhibitor. Also demonstrates T-lymphocyte protection against HIV infection. Strongly inhibits melanoma heparanase and tumor cell metastasis.
Sigma Aldrich - S2671 external link
Biochem/physiol Actions
Suramin is a polysulfonated naphthylurea anticancer agent that inhibits tumor cell proliferation. It inhibits the activity of topoisomerase II by blocking the binding of the enzyme to DNA. It′s antiangiogenic activity may be related to its ability to bind to and inhibit the activity of several growth factors, including FGFa, FGFb, and PGDF. It uncouples G-proteins from receptors. It is an broad spectrum antagonist at P2X and P2Y purinergic receptors. Suramin has well documented antiprotozoal and anthelmintic activity.
Sigma Aldrich - 86203 external link
Biochem/physiol Actions
Suramin is a polysulfonated naphthylurea anticancer agent that inhibits tumor cell proliferation. It inhibits the activity of topoisomerase II by blocking the binding of the enzyme to DNA. It′s antiangiogenic activity may be related to its ability to bind to and inhibit the activity of several growth factors, including FGFa, FGFb, and PGDF. It uncouples G-proteins from receptors. It is an broad spectrum antagonist at P2X and P2Y purinergic receptors. Suramin has well documented antiprotozoal and anthelmintic activity.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Huang, R.-R.C., et al., Mol. Pharmacol. , 37 : 304, (1990).
  • • Hosang, M., J. Cell Biochem. , 29 : 265, (1985).
  • • Nakajima, M., et al., J. Biol. Chem. , 266 : 9661, (1991).
  • • Mitsuya, H., et al., Science , 226 : 172, (1984).
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PATENTS

PATENTS

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INTERNET

INTERNET

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