NP-MRD: Showing NP-Card for sterigmatocystin (NP0034325)

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Record Information

Version

2.0

Created at

2021-06-20 18:05:12 UTC

Updated at

2021-08-20 00:00:29 UTC

NP-MRD ID

NP0034325

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sterigmatocystin

Provided By

JEOL Database JEOL Logo

Description

sterigmatocystin is found in Collariella virescens, Aspergillus variecolor, Aspergillus versicolor, Emericella nidulans var.acristata, Aspergillus striatus and Monocillium nordinii. sterigmatocystin was first documented in 2001 (PMID: 11727790). Based on a literature review a small amount of articles have been published on Sterigmatocystin (PMID: 12739707) (PMID: 15283159) (PMID: 15968996) (PMID: 17540384).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120053D          

 36 40  0  0  0  0            999 V2000
    2.8431   -0.9210    3.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5471   -0.7378    3.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2705   -1.3028    2.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -1.9945    1.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8463   -2.5269    0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -2.3997   -0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -1.7149    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -1.6277   -0.1163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315   -0.9684    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8832   -0.9156   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9483   -0.2632    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7638    0.3378    1.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5162    0.2844    2.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072    0.8960    3.6515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -0.3697    1.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1159   -0.4436    2.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589    0.0914    3.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496   -1.1634    1.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4579   -3.0670   -1.5892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3277   -4.3225   -1.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -5.3443   -1.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432   -5.0421   -1.8840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -3.6000   -1.7454 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7001   -3.2195   -0.5961 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6075   -0.4456    3.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609   -1.9828    4.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8610   -0.4319    4.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486   -2.1318    1.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0315   -1.3826   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9220   -0.2223    0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5886    0.8476    2.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4783    0.7777    3.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913   -2.3737   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004   -4.3927   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2703   -6.3949   -1.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -3.1946   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  2  0  0  0  0
 10  9  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
 18 16  1  0  0  0  0
 16 15  1  0  0  0  0
  6 19  1  0  0  0  0
 23 24  1  0  0  0  0
 24  5  1  0  0  0  0
 23 19  1  0  0  0  0
  9  8  1  0  0  0  0
  7  6  1  0  0  0  0
  7 18  2  0  0  0  0
  9 15  2  0  0  0  0
  5  4  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 13  1  0  0  0  0
 13 14  1  0  0  0  0
 16 17  2  0  0  0  0
 13 12  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  2  1  1  0  0  0  0
 12 11  1  0  0  0  0
 23 36  1  6  0  0  0
  3 18  1  0  0  0  0
 19 33  1  6  0  0  0
  4 28  1  0  0  0  0
 12 31  1  0  0  0  0
 11 30  1  0  0  0  0
 10 29  1  0  0  0  0
 20 34  1  0  0  0  0
 21 35  1  0  0  0  0
 14 32  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END

     RDKit          3D

 36 40  0  0  0  0  0  0  0  0999 V2000
    2.8431   -0.9210    3.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5471   -0.7378    3.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2705   -1.3028    2.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -1.9945    1.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8463   -2.5269    0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -2.3997   -0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -1.7149    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -1.6277   -0.1163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315   -0.9684    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8832   -0.9156   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9483   -0.2632    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7638    0.3378    1.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5162    0.2844    2.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072    0.8960    3.6515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -0.3697    1.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1159   -0.4436    2.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589    0.0914    3.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496   -1.1634    1.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4579   -3.0670   -1.5892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3277   -4.3225   -1.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -5.3443   -1.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432   -5.0421   -1.8840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -3.6000   -1.7454 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7001   -3.2195   -0.5961 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6075   -0.4456    3.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609   -1.9828    4.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8610   -0.4319    4.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486   -2.1318    1.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0315   -1.3826   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9220   -0.2223    0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5886    0.8476    2.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4783    0.7777    3.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913   -2.3737   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004   -4.3927   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2703   -6.3949   -1.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -3.1946   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  2  0
 10  9  1  0
  5  6  2  0
  7  8  1  0
 18 16  1  0
 16 15  1  0
  6 19  1  0
 23 24  1  0
 24  5  1  0
 23 19  1  0
  9  8  1  0
  7  6  1  0
  7 18  2  0
  9 15  2  0
  5  4  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 15 13  1  0
 13 14  1  0
 16 17  2  0
 13 12  2  0
  3  2  1  0
  4  3  2  0
  2  1  1  0
 12 11  1  0
 23 36  1  6
  3 18  1  0
 19 33  1  6
  4 28  1  0
 12 31  1  0
 11 30  1  0
 10 29  1  0
 20 34  1  0
 21 35  1  0
 14 32  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END


  Mrv1652306202120053D          

 36 40  0  0  0  0            999 V2000
    2.8431   -0.9210    3.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5471   -0.7378    3.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2705   -1.3028    2.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -1.9945    1.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8463   -2.5269    0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -2.3997   -0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -1.7149    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -1.6277   -0.1163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315   -0.9684    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8832   -0.9156   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9483   -0.2632    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7638    0.3378    1.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5162    0.2844    2.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072    0.8960    3.6515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -0.3697    1.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1159   -0.4436    2.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589    0.0914    3.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496   -1.1634    1.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4579   -3.0670   -1.5892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3277   -4.3225   -1.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -5.3443   -1.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432   -5.0421   -1.8840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -3.6000   -1.7454 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7001   -3.2195   -0.5961 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6075   -0.4456    3.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609   -1.9828    4.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8610   -0.4319    4.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486   -2.1318    1.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0315   -1.3826   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9220   -0.2223    0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5886    0.8476    2.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4783    0.7777    3.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913   -2.3737   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004   -4.3927   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2703   -6.3949   -1.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -3.1946   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  2  0  0  0  0
 10  9  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
 18 16  1  0  0  0  0
 16 15  1  0  0  0  0
  6 19  1  0  0  0  0
 23 24  1  0  0  0  0
 24  5  1  0  0  0  0
 23 19  1  0  0  0  0
  9  8  1  0  0  0  0
  7  6  1  0  0  0  0
  7 18  2  0  0  0  0
  9 15  2  0  0  0  0
  5  4  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 13  1  0  0  0  0
 13 14  1  0  0  0  0
 16 17  2  0  0  0  0
 13 12  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  2  1  1  0  0  0  0
 12 11  1  0  0  0  0
 23 36  1  6  0  0  0
  3 18  1  0  0  0  0
 19 33  1  6  0  0  0
  4 28  1  0  0  0  0
 12 31  1  0  0  0  0
 11 30  1  0  0  0  0
 10 29  1  0  0  0  0
 20 34  1  0  0  0  0
 21 35  1  0  0  0  0
 14 32  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034325

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C([H])C2=C1C(=O)C1=C(O2)C2=C(O[C@@]3([H])OC([H])=C([H])[C@@]23[H])C([H])=C1OC([H])([H])[H]

> <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>
32.11754704883042

> <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),4,10,14(19),15,17-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>
74.22

> <JCHEM_REFRACTIVITY>
83.7026

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e-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),4,10,14(19),15,17-heptaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 40  0  0  0  0  0  0  0  0999 V2000
    2.8431   -0.9210    3.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5471   -0.7378    3.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2705   -1.3028    2.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -1.9945    1.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8463   -2.5269    0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -2.3997   -0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -1.7149    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -1.6277   -0.1163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315   -0.9684    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8832   -0.9156   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9483   -0.2632    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7638    0.3378    1.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5162    0.2844    2.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072    0.8960    3.6515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -0.3697    1.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1159   -0.4436    2.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589    0.0914    3.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496   -1.1634    1.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4579   -3.0670   -1.5892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3277   -4.3225   -1.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -5.3443   -1.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432   -5.0421   -1.8840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -3.6000   -1.7454 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7001   -3.2195   -0.5961 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6075   -0.4456    3.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609   -1.9828    4.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8610   -0.4319    4.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486   -2.1318    1.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0315   -1.3826   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9220   -0.2223    0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5886    0.8476    2.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4783    0.7777    3.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913   -2.3737   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004   -4.3927   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2703   -6.3949   -1.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -3.1946   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  2  0
 10  9  1  0
  5  6  2  0
  7  8  1  0
 18 16  1  0
 16 15  1  0
  6 19  1  0
 23 24  1  0
 24  5  1  0
 23 19  1  0
  9  8  1  0
  7  6  1  0
  7 18  2  0
  9 15  2  0
  5  4  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 15 13  1  0
 13 14  1  0
 16 17  2  0
 13 12  2  0
  3  2  1  0
  4  3  2  0
  2  1  1  0
 12 11  1  0
 23 36  1  6
  3 18  1  0
 19 33  1  6
  4 28  1  0
 12 31  1  0
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 10 29  1  0
 20 34  1  0
 21 35  1  0
 14 32  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       2.843  -0.921   3.964  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.547  -0.738   3.411  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.270  -1.303   2.195  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.224  -1.994   1.436  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.846  -2.527   0.218  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.561  -2.400  -0.270  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.402  -1.715   0.454  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.645  -1.628  -0.116  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.632  -0.968   0.567  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.883  -0.916  -0.053  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.948  -0.263   0.571  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.764   0.338   1.816  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.516   0.284   2.432  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.407   0.896   3.652  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.446  -0.370   1.809  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.116  -0.444   2.433  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.959   0.091   3.525  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.050  -1.163   1.694  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.458  -3.067  -1.589  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.328  -4.322  -1.616  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.502  -5.344  -1.790  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.843  -5.042  -1.884  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.902  -3.600  -1.745  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.700  -3.220  -0.596  0.00  0.00           O+0
HETATM   25  H   UNK     0       3.607  -0.446   3.341  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.061  -1.983   4.119  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.861  -0.432   4.943  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.249  -2.132   1.763  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.032  -1.383  -1.024  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.922  -0.222   0.089  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.589   0.848   2.307  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.478   0.778   3.960  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.191  -2.374  -2.392  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.400  -4.393  -1.520  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.270  -6.395  -1.860  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.384  -3.195  -2.644  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3    2    4   18                                                  
CONECT    4    5    3   28                                                  
CONECT    5    6   24    4                                                  
CONECT    6    5   19    7                                                  
CONECT    7    8    6   18                                                  
CONECT    8    7    9                                                       
CONECT    9   10    8   15                                                  
CONECT   10   11    9   29                                                  
CONECT   11   10   12   30                                                  
CONECT   12   13   11   31                                                  
CONECT   13   15   14   12                                                  
CONECT   14   13   32                                                       
CONECT   15   16    9   13                                                  
CONECT   16   18   15   17                                                  
CONECT   17   16                                                            
CONECT   18   16    7    3                                                  
CONECT   19    6   23   20   33                                             
CONECT   20   19   21   34                                                  
CONECT   21   20   22   35                                                  
CONECT   22   21   23                                                       
CONECT   23   24   19   22   36                                             
CONECT   24   23    5                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    4                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   14                                                            
CONECT   33   19                                                            
CONECT   34   20                                                            
CONECT   35   21                                                            
CONECT   36   23                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

RDKit          3D

36 40  0  0  0  0  0  0  0  0999 V2000
    2.8431   -0.9210    3.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5471   -0.7378    3.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2705   -1.3028    2.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -1.9945    1.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8463   -2.5269    0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -2.3997   -0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -1.7149    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -1.6277   -0.1163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315   -0.9684    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8832   -0.9156   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9483   -0.2632    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7638    0.3378    1.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5162    0.2844    2.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072    0.8960    3.6515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -0.3697    1.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1159   -0.4436    2.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589    0.0914    3.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496   -1.1634    1.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4579   -3.0670   -1.5892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3277   -4.3225   -1.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -5.3443   -1.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432   -5.0421   -1.8840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -3.6000   -1.7454 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7001   -3.2195   -0.5961 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6075   -0.4456    3.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609   -1.9828    4.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8610   -0.4319    4.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486   -2.1318    1.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0315   -1.3826   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9220   -0.2223    0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5886    0.8476    2.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4783    0.7777    3.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913   -2.3737   -2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004   -4.3927   -1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2703   -6.3949   -1.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -3.1946   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  2  0
 10  9  1  0
  5  6  2  0
  7  8  1  0
 18 16  1  0
 16 15  1  0
  6 19  1  0
 23 24  1  0
 24  5  1  0
 23 19  1  0
  9  8  1  0
  7  6  1  0
  7 18  2  0
  9 15  2  0
  5  4  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 15 13  1  0
 13 14  1  0
 16 17  2  0
 13 12  2  0
  3  2  1  0
  4  3  2  0
  2  1  1  0
 12 11  1  0
 23 36  1  6
  3 18  1  0
 19 33  1  6
  4 28  1  0
 12 31  1  0
 11 30  1  0
 10 29  1  0
 20 34  1  0
 21 35  1  0
 14 32  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END

View in JSmol

Synonyms

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

Chemical Formula

C₁₈H₁₂O₆

Average Mass

324.2880 Da

Monoisotopic Mass

324.06339 Da

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),4,10,14(19),15,17-heptaen-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),4,10,14(19),15,17-heptaen-13-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C([H])C2=C1C(=O)C1=C(O2)C2=C(O[C@@]3([H])OC([H])=C([H])[C@@]23[H])C([H])=C1OC([H])([H])[H]

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achaetomiella virescens	LOTUS Database	35616633
Aspergillus stellatus	Fungi	KNApSAcK
Aspergillus versicolor	JEOL database	Fremlin, L. J., et al, J. Nat. Prod. 72, 666 (2009)
Emericella nidulans var.acristata	-	KNApSAcK
Emericella striata	LOTUS Database	35616633
Monocillium nordinii	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Aspergillus amstelodami	KNApSAcK Database	22123792
Aspergillus chevalieri	KNApSAcK Database	22123792
Aspergillus flavus	KNApSAcK Database	22123792
Aspergillus multicolor	KNApSAcK Database	22123792
Aspergillus nidulans	KNApSAcK Database	22123792
Aspergillus nomius	KNApSAcK Database	22123792
Aspergillus parasiticus	KNApSAcK Database	22123792
Aspergillus quadrilineatus	KNApSAcK Database	22123792
Aspergillus ruber	KNApSAcK Database	22123792
Aspergillus unguis	KNApSAcK Database	22123792
Aspergillus ustus Bainier	KNApSAcK Database	22123792
Aspergillus variecolor	KNApSAcK Database	22123792
Bipolaris sorokiniana	KNApSAcK Database	22123792
Chaetomium spp.	KNApSAcK Database	22123792
Chaetomium thielavioideum	KNApSAcK Database	22123792
Farrowia sp.	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound 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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	246.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Boiling Point	569.75 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1.44 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.169 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
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	32.12 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000563

Chemspider ID

4444077

KEGG Compound ID

C00961

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sterigmatocystin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18227

Good Scents ID

rw1284441

References

General References

Sivakumar V, Thanislass J, Niranjali S, Devaraj H: Lipid peroxidation as a possible secondary mechanism of sterigmatocystin toxicity. Hum Exp Toxicol. 2001 Aug;20(8):398-403. doi: 10.1191/096032701682692955. [PubMed:11727790 ]
Ma F, Misumi J, Zhao W, Aoki K, Kudo M: Long-term treatment with sterigmatocystin, a fungus toxin, enhances the development of intestinal metaplasia of gastric mucosa in Helicobacter pylori-infected Mongolian gerbils. Scand J Gastroenterol. 2003 Apr;38(4):360-9. [PubMed:12739707 ]
Misumi J: [The mechanisms of gastric cancer development produced by the combination of Helicobacter pylori with Sterigmatocystin, a mycotoxin]. Nihon Rinsho. 2004 Jul;62(7):1377-86. [PubMed:15283159 ]
Yao DS, Wen SM, Liu DL, Xie CF, Bai Y, Ran YH: [The primary study on the detection of sterigmatocystin by biologic enzyme electrode modified with the multiwall carbon nanotubes]. Sheng Wu Gong Cheng Xue Bao. 2004 Jul;20(4):601-6. [PubMed:15968996 ]
Versilovskis A, Bartkevics V, Mikelsone V: Analytical method for the determination of sterigmatocystin in grains using high-performance liquid chromatography-tandem mass spectrometry with electrospray positive ionization. J Chromatogr A. 2007 Jul 20;1157(1-2):467-71. doi: 10.1016/j.chroma.2007.05.022. Epub 2007 May 13. [PubMed:17540384 ]
Fremlin, L. J., et al. (2009). Fremlin, L. J., et al, J. Nat. Prod. 72, 666 (2009). J. Nat. Prod..

Showing NP-Card for sterigmatocystin (NP0034325)

MOL for NP0034325 (sterigmatocystin)

3D MOL for NP0034325 (sterigmatocystin)

3D SDF for NP0034325 (sterigmatocystin)

3D-SDF for NP0034325 (sterigmatocystin)

PDB for NP0034325 (sterigmatocystin)

3D PDB for NP0034325 (sterigmatocystin)

SMILES for NP0034325 (sterigmatocystin)

INCHI for NP0034325 (sterigmatocystin)

Structure for NP0034325 (sterigmatocystin)

3D Structure for NP0034325 (sterigmatocystin)