NP-MRD: Showing NP-Card for sterigmatocystin Q (NP0351048)

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Record Information

Version

2.0

Created at

2025-05-25 09:47:45 UTC

Updated at

2026-02-08 05:11:14 UTC

NP-MRD ID

NP0351048

Natural Product DOI

https://doi.org/10.57994/4037

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sterigmatocystin Q

Description

sterigmatocystin Q was first documented in 2025 (PMID: 40560068).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03072312122D          

 28 32  0  0  1  0            999 V2000
    5.4751    1.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0938    1.0348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4616    0.2963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8728   -0.2816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1412    0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2778    0.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6044   -0.6629    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7363   -1.0952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203   -1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525   -0.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7291   -0.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2734   -1.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6412   -1.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.5415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532   -3.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4646   -1.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500   -1.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -0.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588   -0.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969   -0.9630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1709   -1.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    0.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467    1.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1702    1.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6258    1.7880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379    0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613    0.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -1.7522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  4  7  1  6  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
  9 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 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
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 11 27  1  0  0  0  0
 17 28  2  0  0  0  0
M  END


  Mrv2104 03072312122D          

 28 32  0  0  1  0            999 V2000
    5.4751    1.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0938    1.0348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4616    0.2963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8728   -0.2816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1412    0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2778    0.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6044   -0.6629    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7363   -1.0952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203   -1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525   -0.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7291   -0.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2734   -1.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6412   -1.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.5415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532   -3.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4646   -1.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500   -1.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -0.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588   -0.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969   -0.9630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1709   -1.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    0.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467    1.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1702    1.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6258    1.7880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5379    0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613    0.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -1.7522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  4  7  1  6  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
  9 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 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
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 11 27  1  0  0  0  0
 17 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0351048

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12O[C@@H](O)C=C1C1=C(O2)C=C(OC)C2=C1OC1=C(O)C=CC(OC)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H14O8/c1-23-9-4-3-8(20)17-14(9)16(22)15-10(24-2)6-11-13(18(15)27-17)7-5-12(21)26-19(7)25-11/h3-6,12,19-21H,1-2H3/t12-,19-/m1/s1

> <INCHI_KEY>
MHQROIAAKDIZPY-CWTRNNRKSA-N

> <FORMULA>
C19H14O8

> <MOLECULAR_WEIGHT>
370.313

> <EXACT_MASS>
370.068867411

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
36.25476910253569

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,7R)-5,18-dihydroxy-11,15-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),3,10,14,16,18-heptaen-13-one

> <JCHEM_LOGP>
1.9960832136666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.97674705315497

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.38337145299389

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6788816607903603

> <JCHEM_POLAR_SURFACE_AREA>
103.68

> <JCHEM_REFRACTIVITY>
91.66640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R,7R)-5,18-dihydroxy-11,15-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),3,10,14,16,18-heptaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-MAR-23         0                                  
HETATM    1  O   UNK     0      10.220   3.297   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.508   1.932   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.195   0.553   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.096  -0.526   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.730   0.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.985   1.705   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0      10.462  -1.237   0.000  0.00  0.00           H+0
HETATM    8  O   UNK     0       8.841  -2.044   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.318  -2.271   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.631  -0.893   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.094  -0.798   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.244  -2.082   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.930  -3.460   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.080  -4.744   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.766  -6.123   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.467  -3.555   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.707  -1.987   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.020  -0.609   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.483  -0.514   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.368  -1.798   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.319  -3.176   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.203   0.865   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.647   2.149   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.184   2.054   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.035   3.338   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.871   0.675   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.408   0.580   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.856  -3.271   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7    8                                             
CONECT    5    4    6   10                                                  
CONECT    6    5    2                                                       
CONECT    7    4                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13    9                                                       
CONECT   17   12   18   28                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   18   27                                                  
CONECT   27   26   11                                                       
CONECT   28   17                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₄O₈

Average Mass

370.3130 Da

Monoisotopic Mass

370.06887 Da

IUPAC Name

(5R,7R)-5,18-dihydroxy-11,15-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),3,10,14,16,18-heptaen-13-one

Traditional Name

(5R,7R)-5,18-dihydroxy-11,15-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),3,10,14,16,18-heptaen-13-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12O[C@@H](O)C=C1C1=C(O2)C=C(OC)C2=C1OC1=C(O)C=CC(OC)=C1C2=O

InChI Identifier

InChI=1S/C19H14O8/c1-23-9-4-3-8(20)17-14(9)16(22)15-10(24-2)6-11-13(18(15)27-17)7-5-12(21)26-19(7)25-11/h3-6,12,19-21H,1-2H3/t12-,19-/m1/s1

InChI Key

MHQROIAAKDIZPY-CWTRNNRKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C2D6OS, experimental)	1452982612@qq.com	Hainan Normal University	Wenxing Li	2025-05-25	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.0, , simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.0, , simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-08	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2	ChemAxon
pKa (Strongest Acidic)	8.38	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.67 m³·mol⁻¹	ChemAxon
Polarizability	36.25 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li WX, Chen ZX, Jiang CJ, Li XZ, Li XR, Lu HY, Hui Y, Chen WH: Discovery of Aflatoxins and Sterigmatocystins with Antitumor Activity from Aspergillus sp. PQJ-1 of Sphagneticola trilobata. J Nat Prod. 2025 Jul 25;88(7):1616-1630. doi: 10.1021/acs.jnatprod.5c00391. Epub 2025 Jun 25. [PubMed:40560068 ]
DOI: 10.1021/acs.jnatprod.5c00391
PMID: 40560068

Showing NP-Card for sterigmatocystin Q (NP0351048)

MOL for NP0351048 (sterigmatocystin Q)

3D MOL for NP0351048 (sterigmatocystin Q)

3D SDF for NP0351048 (sterigmatocystin Q)

3D-SDF for NP0351048 (sterigmatocystin Q)

PDB for NP0351048 (sterigmatocystin Q)

3D PDB for NP0351048 (sterigmatocystin Q)

SMILES for NP0351048 (sterigmatocystin Q)

INCHI for NP0351048 (sterigmatocystin Q)

Structure for NP0351048 (sterigmatocystin Q)

3D Structure for NP0351048 (sterigmatocystin Q)