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Sterigmatocystin - Compound Summary (CID 5280389)

A carcinogenic mycotoxin produced in high yields by strains of the common molds, Aspergillus versicolor, A. nidulans, and an unidentified species of Bipolaris. It causes necrosis of the liver and kidney and has an inhibitory effect on orotic acid incorporation into nuclear RNA.


Drug and Chemical Information: (Total:1)         

  Chemical Classification
Biological Factors
      Toxins, Biological
            Mycotoxins
                  Sterigmatocystin
Heterocyclic Compounds
      Heterocyclic Compounds, 3-Ring
            Xanthenes
                  Xanthones
                        Sterigmatocystin


Safety and Toxicology

HSDB - Peer-reviewed summary of toxicity and biomedical effects

CCRIS - Carcinogenicity, tumor promotion, tumor inhibition, and mutagenicity tests

EINECS - European Inventory of Existing Commercial Chemical Substances

GENETOX - Genetic toxicology information

TOXLINE - Citations to the toxicological literature


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BioActivity Results:
Tested in BioAssays: All: 72   Active: 10   Inactive: 60
BioActivity Summary:
This Compound   with Similar Compounds

AID: 330 Source: DTP/NCI
NCI In Vivo Anticancer Drug Screen. Data for tumor model P388 Leukemia (intraperitoneal) in CD2F1 (CDF1) mice

AID: 328 Source: DTP/NCI
NCI In Vivo Anticancer Drug Screen. Data for tumor model P388 Leukemia (intraperitoneal) in B6D2F1 (BDF1) mice

AID: 248 Source: DTP/NCI
NCI In Vivo Anticancer Drug Screen. Data for tumor model L1210 Leukemia (intraperitoneal) in B6D2F1 (BDF1) mice

AID: 117 Source: DTP/NCI
NCI human tumor cell line growth inhibition assay. Data for the P388/ADR Leukemia cell line

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Depositor-Supplied Synonyms: (Total: 30)
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Properties Computed from Structure:
Molecular Weight324.28428 [g/mol]
Molecular FormulaC18H12O6
XLogP3-AA3.4
H-Bond Donor1
H-Bond Acceptor6
Rotatable Bond Count1
Tautomer Count5
Exact Mass324.063388
MonoIsotopic Mass324.063388
Topological Polar Surface Area74.2
Heavy Atom Count24
Formal Charge0
Complexity562
Isotope Atom Count0
Defined Atom StereoCenter Count2
Undefined Atom StereoCenter Count0
Defined Bond StereoCenter Count0
Undefined Bond StereoCenter Count0
Covalently-Bonded Unit Count1


Descriptors Computed from Structure:
Canonical SMILES: COC1=C2C(=C3C4C=COC4OC3=C1)OC5=C(C2=O)C(=CC=C5)O
Isomeric SMILES: COC1=C2C(=C3[C@@H]4C=CO[C@@H]4OC3=C1)OC5=C(C2=O)C(=CC=C5)O
InChI: InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)
14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1

InChIKey: UTSVPXMQSFGQTM-DCXZOGHSSA-N


Compound Information:
CID 5280389   
Create Date: 2004-09-16

Related Compounds:
Same, Connectivity: 3 Links

Similar Compounds: 200 Links
Similar Conformers: 88 Links    View Conformers


Substance Information:
Substances: 15 Links

Category: [for same structure substances]
Biological Properties: 10 Links
   ChEBI ( 1 )
SID 8143844 - External ID: CHEBI:18227
   ChemBank ( 2 )
SID 11406116 - External ID: NCI60_001723
SID 11447279 - External ID: NCIMech_000632
   DiscoveryGate ( 1 )
SID 24583175 - External ID: 5280389
   DTP/NCI ( 2 )
SID 450614 - External ID: 201423
SID 124690 - External ID: 204985
   LeadScope ( 1 )
SID 49857152 - External ID: LS-7165
   LipidMAPS ( 1 )
SID 24701550 - External ID: LMPK02000002
   MTDP ( 1 )
SID 8137229 - External ID: NSC204985
   NextBio ( 1 )
SID 51432309 - External ID: 5280389

Metabolic Pathways: 1 Link
   KEGG ( 1 )
SID 4212 - External ID: C00961

Physical Properties: 1 Link
   ChemExper Chemical Directory ( 1 )

Substance Vendors: 3 Links
   ChemExper Chemical Directory ( 1 )
   ChemSpider ( 1 )
SID 39289543 - External ID: 4444077
   ZINC ( 1 )
SID 12157635 - External ID: ZINC03861783

Theoretical Properties: 1 Link
   ZINC ( 1 )
SID 12157635 - External ID: ZINC03861783

Toxicology: 1 Link
   ChemIDplus ( 1 )
SID 167666 - External ID: 010048132

     

2D

3D

Compound ID5280389
Molecular Weight324.28428 [g/mol]
Molecular FormulaC18H12O6
XLogP3-AA3.4
H-Bond Donor1
H-Bond Acceptor6


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