MiMeDB: Showing metabocard for Sterigmatocystin (MMDBc0006553)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 23:42:32 UTC

Update Date

2022-12-15 22:51:43 UTC

Metabolite ID

MMDBc0006553

Metabolite Identification

Common Name

Sterigmatocystin

Description

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1533006081517262D          
 
 26 30  0  0  1  0            999 V2000
    9.6113   -9.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6113  -10.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3257  -10.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0402  -10.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0402   -9.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3257   -8.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7547  -10.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4691  -10.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4691   -9.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7547   -8.8688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1836  -10.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8981  -10.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8981   -9.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1836   -8.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7547  -11.3438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1836  -11.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3257  -11.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6014  -11.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1542   -8.0618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2924   -8.0581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9982   -8.7705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4484   -7.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7941   -6.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0384   -7.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9792   -8.0618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5087   -7.9756    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
  7 15  2  0  0  0  0
 11 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 19 25  1  6  0  0  0
 20 26  1  6  0  0  0
M  END

 
  Mrv1533006081517262D          
 
 26 30  0  0  1  0            999 V2000
    9.6113   -9.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6113  -10.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3257  -10.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0402  -10.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0402   -9.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3257   -8.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7547  -10.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4691  -10.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4691   -9.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7547   -8.8688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1836  -10.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8981  -10.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8981   -9.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1836   -8.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7547  -11.3438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1836  -11.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3257  -11.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6014  -11.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1542   -8.0618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2924   -8.0581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9982   -8.7705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4484   -7.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7941   -6.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0384   -7.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9792   -8.0618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5087   -7.9756    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
  7 15  2  0  0  0  0
 11 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 19 25  1  6  0  0  0
 20 26  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0006553

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]12OC=C[C@@]1([H])C1=C3OC4=CC=CC(O)=C4C(=O)C3=C(OC)C=C1O2

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
UTSVPXMQSFGQTM-DCXZOGHSSA-N

> <FORMULA>
C18H12O6

> <MOLECULAR_WEIGHT>
324.288

> <EXACT_MASS>
324.063388106

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.484915386697015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
3.0985916909999993

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.382688883759405

> <JCHEM_PKA_STRONGEST_BASIC>
-3.701431358515738

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
83.70260000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sterigmatocystin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUN-15         0                                  
HETATM    1  C   UNK     0      17.941 -17.325   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.941 -18.865   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.275 -19.635   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.608 -18.865   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.608 -17.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.275 -16.555   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.942 -19.635   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.276 -18.865   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.276 -17.325   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      21.942 -16.555   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      24.609 -19.635   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.943 -18.865   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.943 -17.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.609 -16.555   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      21.942 -21.175   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      24.609 -21.175   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      19.275 -21.175   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      17.923 -21.956   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.954 -15.049   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.346 -15.042   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.797 -16.372   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      19.504 -13.642   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.282 -12.611   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.872 -13.535   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      20.494 -15.049   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      15.883 -14.888   0.000  0.00  0.00           H+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1   19                                                  
CONECT    7    4    8   15                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9    5                                                       
CONECT   11    8   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    7                                                            
CONECT   16   11                                                            
CONECT   17    3   18                                                       
CONECT   18   17                                                            
CONECT   19    6   20   22   25                                             
CONECT   20   19   21   24   26                                             
CONECT   21   20    1                                                       
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   20                                                       
CONECT   25   19                                                            
CONECT   26   20                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

Synonyms

Value	Source
8-Hydroxy-6-methoxy-3a,12C-dihydro-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one	ChEBI

Molecular Formula

C₁₈H₁₂O₆

Average Mass

324.288

Monoisotopic Mass

324.063388106

IUPAC Name

(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one

Traditional Name

sterigmatocystin

CAS Registry Number

Not Available

SMILES

[H][C@]12OC=C[C@@]1([H])C1=C3OC4=CC=CC(O)=C4C(=O)C3=C(OC)C=C1O2

InChI Identifier

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

InChI Key

UTSVPXMQSFGQTM-DCXZOGHSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. And Bipolaris spp.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Sterigmatocystins

Sub Class

Not Available

Direct Parent

Sterigmatocystins

Alternative Parents

Substituents

Sterigmatocystin backbone
Xanthone
Dibenzopyran
Xanthene
Chromone
Benzopyran
1-benzopyran
Coumaran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Dihydrofuran
Vinylogous ester
Vinylogous acid
Ether
Oxacycle
Acetal
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sterigmatocystins (CHEBI:18227 )
Aflatoxins and related substances (C00961 )
Mycotoxins (C00961 )
Aflatoxins and related substances (LMPK10000001 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2.73	ALOGPS
logP	3.1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.38	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.7 m³·mol⁻¹	ChemAxon
Polarizability	31.48 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	19	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00000563

Chemspider ID

Not Available

KEGG Compound ID

C00961

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sterigmatocystin

METLIN ID

Not Available

PubChem Compound

5280389

PDB ID

Not Available

ChEBI ID

18227

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Sterigmatocystin (MMDBc0006553)

MOL for #<Metabolite:0x00007f921e453348>

3D MOL for #<Metabolite:0x00007f921e453348>

3D SDF for #<Metabolite:0x00007f921e453348>

3D-SDF for #<Metabolite:0x00007f921e453348>

PDB for #<Metabolite:0x00007f921e453348>

3D PDB for #<Metabolite:0x00007f921e453348>

SMILES for #<Metabolite:0x00007f921e453348>

INCHI for #<Metabolite:0x00007f921e453348>

Structure for #<Metabolite:0x00007f921e453348>

3D Structure for #<Metabolite:0x00007f921e453348>