MiMeDB: Showing metabocard for Dihydrosterigmatocystin (MMDBc0015068)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 05:58:28 UTC

Update Date

2022-12-15 22:51:45 UTC

Metabolite ID

MMDBc0015068

Metabolite Identification

Common Name

Dihydrosterigmatocystin

Description

Dihydrosterigmatocystin, also known as DHST, 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. Dihydrosterigmatocystin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Dihydrosterigmatocystin.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652305152107582D          

 26 30  0  0  1  0            999 V2000
    3.1579    6.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1732    2.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6289    3.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3498    2.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2421    2.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5739    2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0553    5.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3787    3.5351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2611    3.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9820    3.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8788    5.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996    4.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9674    4.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4377    3.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2465    4.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529    3.9164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7168    4.5978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5256    5.3870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344    6.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9416    3.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1586    3.3238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164    4.7300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103    3.1538    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845    4.2977    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21 11  1  0  0  0  0
 22  6  1  0  0  0  0
 22 18  1  0  0  0  0
 23 10  1  0  0  0  0
 23 17  1  0  0  0  0
 24 12  1  0  0  0  0
 24 18  1  0  0  0  0
  8 25  1  1  0  0  0
 18 26  1  1  0  0  0
M  END

  Mrv1652305152107582D          

 26 30  0  0  1  0            999 V2000
    3.1579    6.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1732    2.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6289    3.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3498    2.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2421    2.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5739    2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0553    5.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3787    3.5351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2611    3.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9820    3.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8788    5.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996    4.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9674    4.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4377    3.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2465    4.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529    3.9164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7168    4.5978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5256    5.3870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344    6.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9416    3.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1586    3.3238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164    4.7300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103    3.1538    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845    4.2977    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  2  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21 11  1  0  0  0  0
 22  6  1  0  0  0  0
 22 18  1  0  0  0  0
 23 10  1  0  0  0  0
 23 17  1  0  0  0  0
 24 12  1  0  0  0  0
 24 18  1  0  0  0  0
  8 25  1  1  0  0  0
 18 26  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0015068

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]12OCC[C@@]1([H])C1=C(O2)C=C(OC)C2=C1OC1=CC=CC(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O6/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/h2-4,7-8,18-19H,5-6H2,1H3/t8-,18+/m0/s1

> <INCHI_KEY>
RHGQIWVTIHZRLI-DCXZOGHSSA-N

> <FORMULA>
C18H14O6

> <MOLECULAR_WEIGHT>
326.304

> <EXACT_MASS>
326.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.46099202888788

> <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[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),10,14,16,18-hexaen-13-one

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
3.086612646

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.3829743852684

> <JCHEM_PKA_STRONGEST_BASIC>
-3.628616632158748

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
83.6095

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),10,14,16,18-hexaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       5.895  11.434   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.790   4.636   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.641   5.920   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.253   4.731   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.452   5.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.071   4.853   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.970  10.340   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.707   6.599   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.954   7.299   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.566   6.110   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.507  10.245   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.119   9.056   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.806   7.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.417   7.393   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.194   8.867   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.731   8.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.343   7.583   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.659   7.311   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.805   8.582   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.581  10.056   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.358  11.529   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.758   6.232   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.029   6.204   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.404   8.829   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       2.073   5.887   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.024   8.022   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2    3    4                                                       
CONECT    3    2    9                                                       
CONECT    4    2   10                                                       
CONECT    5    6    8                                                       
CONECT    6    5   22                                                       
CONECT    7   11   12                                                       
CONECT    8    5   13   18   25                                             
CONECT    9    3   14   19                                                  
CONECT   10    4   14   23                                                  
CONECT   11    7   15   21                                                  
CONECT   12    7   13   24                                                  
CONECT   13    8   12   17                                                  
CONECT   14    9   10   16                                                  
CONECT   15   11   16   17                                                  
CONECT   16   14   15   20                                                  
CONECT   17   13   15   23                                                  
CONECT   18    8   22   24   26                                             
CONECT   19    9                                                            
CONECT   20   16                                                            
CONECT   21    1   11                                                       
CONECT   22    6   18                                                       
CONECT   23   10   17                                                       
CONECT   24   12   18                                                       
CONECT   25    8                                                            
CONECT   26   18                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

Synonyms

Value	Source
2',3'-Dihydrosterigmatocystin	ChEBI
8-Hydroxy-6-methoxy-1,2,3ar,12CS-tetrahydro-7H-furo(3',2':4,5)furo(2,3-c)xanthen-7-one	ChEBI
DHST	ChEBI

Molecular Formula

C₁₈H₁₄O₆

Average Mass

326.304

Monoisotopic Mass

326.079038171

IUPAC Name

(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),10,14,16,18-hexaen-13-one

Traditional Name

(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),10,14,16,18-hexaen-13-one

CAS Registry Number

Not Available

SMILES

[H][C@]12OCC[C@@]1([H])C1=C(O2)C=C(OC)C2=C1OC1=CC=CC(O)=C1C2=O

InChI Identifier

InChI=1S/C18H14O6/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/h2-4,7-8,18-19H,5-6H2,1H3/t8-,18+/m0/s1

InChI Key

RHGQIWVTIHZRLI-DCXZOGHSSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for Dihydrosterigmatocystin (MMDBc0015068)

MOL for #<Metabolite:0x00007fb7a0f33ec8>

3D MOL for #<Metabolite:0x00007fb7a0f33ec8>

3D SDF for #<Metabolite:0x00007fb7a0f33ec8>

3D-SDF for #<Metabolite:0x00007fb7a0f33ec8>

PDB for #<Metabolite:0x00007fb7a0f33ec8>

3D PDB for #<Metabolite:0x00007fb7a0f33ec8>

SMILES for #<Metabolite:0x00007fb7a0f33ec8>

INCHI for #<Metabolite:0x00007fb7a0f33ec8>

Structure for #<Metabolite:0x00007fb7a0f33ec8>

3D Structure for #<Metabolite:0x00007fb7a0f33ec8>