NP-MRD: Showing NP-Card for 15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one (NP0180101)

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Record Information

Version

2.0

Created at

2022-09-03 18:25:01 UTC

Updated at

2022-09-03 18:25:01 UTC

NP-MRD ID

NP0180101

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one

Description

5,6-Dimethoxysterigmatocystin 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. 5,6-Dimethoxysterigmatocystin is an extremely weak basic (essentially neutral) compound (based on its pKa). 15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one is found in Aspergillus multicolor. Mycotoxin production by Aspergillus multicolor.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305222D          

 28 32  0  0  0  0            999 V2000
    4.8820    6.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2798    1.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860    1.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1575    2.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3415    2.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5443    2.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9707    4.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2940    2.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1765    3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7941    4.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5150    4.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0886    1.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8828    3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3531    3.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1619    4.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9853    4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2651    1.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7062    3.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8974    2.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624    3.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6322    4.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4410    4.8170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2498    5.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4563    1.1752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095    1.2768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9737    2.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6990    4.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0739    2.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  2  0  0  0  0
 18 13  1  0  0  0  0
 18 15  2  0  0  0  0
 19 14  2  0  0  0  0
 19 17  1  0  0  0  0
 20  8  1  0  0  0  0
 21  9  1  0  0  0  0
 22 16  2  0  0  0  0
 23  1  1  0  0  0  0
 23 10  1  0  0  0  0
 24  2  1  0  0  0  0
 24 12  1  0  0  0  0
 25  3  1  0  0  0  0
 25 17  1  0  0  0  0
 26  5  1  0  0  0  0
 26 20  1  0  0  0  0
 27 11  1  0  0  0  0
 27 20  1  0  0  0  0
 28 18  1  0  0  0  0
 28 19  1  0  0  0  0
M  END

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
    5.9943   -1.2461   -0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6624   -1.6764    0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6395   -0.7394    0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9225    0.5887   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8649    1.5099   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2240    2.8089   -0.3548 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5612    1.0761   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5003    1.9490   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596    3.1734   -0.2523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7920    1.4464    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8403    2.3413   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5889    3.7001   -0.1869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5846    4.6739   -0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1122    1.8248    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    0.4632    0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2914   -0.4160    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0070    0.0804    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0351   -0.7163    0.2427 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2749   -0.2611    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3182   -1.1622    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1096   -2.5211    0.3382 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -3.3636   -0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8466   -1.7791    0.5319 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1299   -2.4595   -0.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3798   -2.8880   -0.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0110   -2.5528    0.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2687   -1.5157    1.0321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5353   -0.2585    0.4480 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2774   -0.4942    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1997   -0.8395   -1.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6466   -2.1515    0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    0.9484   -0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7737    3.6491   -0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0154    4.8226   -1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298    5.6467    0.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555    4.4350    0.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9414    2.5218    0.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5766   -3.0204   -1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -3.2692   -1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1621   -4.3977   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2812   -2.3881    1.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4318   -2.5919   -1.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8967   -3.4251   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3395   -1.5264    2.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 16 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 16 17  1  0
 17 10  2  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7 19  2  0
 19 18  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
 10 11  1  0
  5  7  1  0
 28 15  1  0
 18 17  1  0
 27 23  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 23 41  1  1
 24 42  1  0
 25 43  1  0
 27 44  1  1
 22 38  1  0
 22 39  1  0
 22 40  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
M  END


  Mrv0541 05061305222D          

 28 32  0  0  0  0            999 V2000
    4.8820    6.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2798    1.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860    1.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1575    2.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3415    2.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5443    2.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9707    4.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2940    2.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1765    3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7941    4.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5150    4.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0886    1.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8828    3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3531    3.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1619    4.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9853    4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2651    1.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7062    3.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8974    2.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624    3.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6322    4.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4410    4.8170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2498    5.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4563    1.1752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095    1.2768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9737    2.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6990    4.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0739    2.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  2  0  0  0  0
 18 13  1  0  0  0  0
 18 15  2  0  0  0  0
 19 14  2  0  0  0  0
 19 17  1  0  0  0  0
 20  8  1  0  0  0  0
 21  9  1  0  0  0  0
 22 16  2  0  0  0  0
 23  1  1  0  0  0  0
 23 10  1  0  0  0  0
 24  2  1  0  0  0  0
 24 12  1  0  0  0  0
 25  3  1  0  0  0  0
 25 17  1  0  0  0  0
 26  5  1  0  0  0  0
 26 20  1  0  0  0  0
 27 11  1  0  0  0  0
 27 20  1  0  0  0  0
 28 18  1  0  0  0  0
 28 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0180101

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O2)C(OC)=C(OC)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O8/c1-23-10-7-11-13(8-4-5-26-20(8)27-11)18-15(10)16(22)14-9(21)6-12(24-2)17(25-3)19(14)28-18/h4-8,20-21H,1-3H3

> <INCHI_KEY>
RSPJLZQIZABVSE-UHFFFAOYSA-N

> <FORMULA>
C20H16O8

> <MOLECULAR_WEIGHT>
384.3362

> <EXACT_MASS>
384.084517488

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
37.433613356752645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14(19),15,17-heptaen-13-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.783249159666666

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.01257877642427

> <JCHEM_PKA_STRONGEST_BASIC>
-4.157713549521234

> <JCHEM_POLAR_SURFACE_AREA>
92.68000000000002

> <JCHEM_REFRACTIVITY>
96.62899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14(19),15,17-heptaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.113  11.843   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.456   2.099   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.307   2.478   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.894   4.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.371   3.789   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.083   4.856   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.412   9.276   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.149   5.535   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.396   6.235   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.949   9.181   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.561   7.992   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.232   3.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.248   6.614   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.859   6.329   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.636   7.803   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.173   7.708   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.695   3.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.785   6.519   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.008   5.046   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.783   6.247   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.247   7.518   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.023   8.992   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.800  10.465   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      13.918   2.194   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.844   2.383   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.684   5.168   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.038   7.765   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       9.471   5.140   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4    5    8                                                       
CONECT    5    4   26                                                       
CONECT    6    9   12                                                       
CONECT    7   10   11                                                       
CONECT    8    4   13   20                                                  
CONECT    9    6   14   21                                                  
CONECT   10    7   15   23                                                  
CONECT   11    7   13   27                                                  
CONECT   12    6   17   24                                                  
CONECT   13    8   11   18                                                  
CONECT   14    9   16   19                                                  
CONECT   15   10   16   18                                                  
CONECT   16   14   15   22                                                  
CONECT   17   12   19   25                                                  
CONECT   18   13   15   28                                                  
CONECT   19   14   17   28                                                  
CONECT   20    8   26   27                                                  
CONECT   21    9                                                            
CONECT   22   16                                                            
CONECT   23    1   10                                                       
CONECT   24    2   12                                                       
CONECT   25    3   17                                                       
CONECT   26    5   20                                                       
CONECT   27   11   20                                                       
CONECT   28   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Value	Source
10,11-Dimethoxysterigmatocystin	HMDB
Dimethoxysterigmatocystin	HMDB
5,6-Dimethoxysterigmatocystin	MeSH

Chemical Formula

C₂₀H₁₆O₈

Average Mass

384.3362 Da

Monoisotopic Mass

384.08452 Da

IUPAC Name

15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14(19),15,17-heptaen-13-one

Traditional Name

15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14(19),15,17-heptaen-13-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O2)C(OC)=C(OC)C=C1O

InChI Identifier

InChI=1S/C20H16O8/c1-23-10-7-11-13(8-4-5-26-20(8)27-11)18-15(10)16(22)14-9(21)6-12(24-2)17(25-3)19(14)28-18/h4-8,20-21H,1-3H3

InChI Key

RSPJLZQIZABVSE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus multicolor	LOTUS Database	35616633

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
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyran
Benzenoid
Vinylogous acid
Vinylogous ester
Dihydrofuran
Heteroaromatic compound
Ether
Acetal
Organoheterocyclic compound
Oxacycle
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-4591 )

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	2.78	ALOGPS
logP	2.78	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.63 m³·mol⁻¹	ChemAxon
Polarizability	37.43 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

HMDB0030592

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002485

KNApSAcK ID

Not Available

Chemspider ID

4447461

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5284386

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one (NP0180101)

MOL for NP0180101 (15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

3D MOL for NP0180101 (15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

3D SDF for NP0180101 (15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

3D-SDF for NP0180101 (15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

PDB for NP0180101 (15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

3D PDB for NP0180101 (15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

SMILES for NP0180101 (15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

INCHI for NP0180101 (15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

Structure for NP0180101 (15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)

3D Structure for NP0180101 (15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,4,9,11,14,16,18-heptaen-13-one)