NP-MRD: Showing NP-Card for peneciraistin C (NP0041192)

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Record Information

Version

2.0

Created at

2021-06-20 23:09:49 UTC

Updated at

2021-06-30 00:15:33 UTC

NP-MRD ID

NP0041192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

peneciraistin C

Provided By

JEOL Database JEOL Logo

Description

(3S,3'S,4S,6S,6'S,7R)-3'-(acetyloxy)-6,7-dihydroxy-6',7-dimethyl-8-oxo-1,4,5,6,7,8-hexahydrospiro[2-benzopyran-3,2'-oxane]-4-yl acetate belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center. peneciraistin C is found in Penicillium raistrickii. peneciraistin C was first documented in 2012 (Ma, L.-Y., et al.). Based on a literature review very few articles have been published on (3S,3'S,4S,6S,6'S,7R)-3'-(acetyloxy)-6,7-dihydroxy-6',7-dimethyl-8-oxo-1,4,5,6,7,8-hexahydrospiro[2-benzopyran-3,2'-oxane]-4-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101093D          

 54 56  0  0  0  0            999 V2000
    2.5676   -4.1529    4.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8743   -3.6343    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9895   -3.6166    2.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7315   -3.2005    2.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9006   -2.5950    1.0062 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9200   -3.6789   -0.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0487   -3.0297   -1.4443 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9586   -1.9783   -1.6454 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1615   -1.2269   -2.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9629   -1.0080   -0.5907 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5165   -2.2255    0.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6188   -1.3646    0.4985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5312   -0.0150    1.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4244    0.4588    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    1.8075    2.4270 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5014    2.7375    2.0190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5165    3.8789    2.8832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8617    2.0293    2.0358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3311    1.6101    3.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8360    2.9560    1.5279 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1158    1.1578    2.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9001   -5.0152    4.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
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 14 13  1  0  0  0  0
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  2  1  1  0  0  0  0
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M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
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    0.9586   -1.9783   -1.6454 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.5165   -2.2255    0.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3311    1.6101    3.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8360    2.9560    1.5279 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306212101093D          

 54 56  0  0  0  0            999 V2000
    2.5676   -4.1529    4.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8743   -3.6343    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9895   -3.6166    2.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7315   -3.2005    2.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9006   -2.5950    1.0062 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9200   -3.6789   -0.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0487   -3.0297   -1.4443 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9586   -1.9783   -1.6454 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.1513   -1.9080   -3.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1110   -0.6801   -2.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706   -0.4814   -3.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910   -1.2591   -0.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5195   -1.8887    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    2.3204    2.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3400    1.6693    3.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3059    3.1217    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    4.3697    2.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3179    1.1347    3.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6497    0.8973    3.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4438    2.4783    4.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5585    2.4083    1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7863   -0.8769    2.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8957    1.0555    2.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7820    2.1983    2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319    0.8691    1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 24  1  0  0  0  0
 14 13  1  0  0  0  0
 13 12  1  0  0  0  0
 11 12  1  6  0  0  0
 11 24  1  0  0  0  0
 17 19  1  0  0  0  0
 17 18  1  0  0  0  0
 11  5  1  0  0  0  0
 19 20  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 14  1  0  0  0  0
  5  4  1  0  0  0  0
 10  8  1  0  0  0  0
  8  9  1  0  0  0  0
 15 16  1  0  0  0  0
 24 25  1  0  0  0  0
 16 17  1  0  0  0  0
 19 21  1  6  0  0  0
 15 14  2  0  0  0  0
  4  2  1  0  0  0  0
  8  7  1  0  0  0  0
  2  1  1  0  0  0  0
  7  6  1  0  0  0  0
  2  3  2  0  0  0  0
  6  5  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 11 10  1  0  0  0  0
 26 28  2  0  0  0  0
  8 37  1  6  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
  6 33  1  0  0  0  0
  6 34  1  0  0  0  0
  5 32  1  1  0  0  0
 17 45  1  6  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
 24 51  1  1  0  0  0
 18 46  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
  9 40  1  0  0  0  0
 21 50  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 27 52  1  0  0  0  0
 27 53  1  0  0  0  0
 27 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C2=C(C(=O)[C@@]1(O[H])C([H])([H])[H])C([H])([H])O[C@@]1(O[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])OC(=O)C([H])([H])[H])[C@@]2([H])OC(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O9/c1-9-5-6-15(26-10(2)20)19(28-9)17(27-11(3)21)12-7-14(22)18(4,24)16(23)13(12)8-25-19/h9,14-15,17,22,24H,5-8H2,1-4H3/t9-,14-,15-,17-,18+,19-/m0/s1

> <INCHI_KEY>
MPVZXVXIZMIJFZ-NVBYNIPGSA-N

> <FORMULA>
C19H26O9

> <MOLECULAR_WEIGHT>
398.408

> <EXACT_MASS>
398.157682417

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.90408335065969

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3'S,4S,6S,6'S,7R)-3'-(acetyloxy)-6,7-dihydroxy-6',7-dimethyl-8-oxo-1,4,5,6,7,8-hexahydrospiro[2-benzopyran-3,2'-oxane]-4-yl acetate

> <ALOGPS_LOGP>
-0.35

> <JCHEM_LOGP>
0.1690500926666666

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.550493939353778

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.288359230810707

> <JCHEM_PKA_STRONGEST_BASIC>
-3.345685879914985

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
93.66259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3'S,4S,6S,6'S,7R)-3'-(acetyloxy)-6,7-dihydroxy-6',7-dimethyl-8-oxo-1,4,5,6-tetrahydrospiro[2-benzopyran-3,2'-oxane]-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
    2.5676   -4.1529    4.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8743   -3.6343    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9895   -3.6166    2.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7315   -3.2005    2.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9006   -2.5950    1.0062 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9200   -3.6789   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0487   -3.0297   -1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9586   -1.9783   -1.6454 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1615   -1.2269   -2.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9629   -1.0080   -0.5907 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628   -1.5689    0.7265 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5165   -2.2255    0.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6188   -1.3646    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5312   -0.0150    1.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4244    0.4588    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    1.8075    2.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    2.7375    2.0190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5165    3.8789    2.8832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8617    2.0293    2.0358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3311    1.6101    3.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8360    2.9560    1.5279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7823    0.7958    1.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7417    0.4537    0.4385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114   -0.4283    1.8102 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9828    0.3888    1.6177 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9664    0.2621    2.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1158    1.1578    2.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305   -0.4739    3.5220 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128   -3.3621    4.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4963   -4.4672    4.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9001   -5.0152    4.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -2.0581    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084   -4.2868   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517   -4.3732    0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9958   -3.7934   -2.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0369   -2.5571   -1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0213   -2.4680   -1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513   -1.9080   -3.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1110   -0.6801   -2.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706   -0.4814   -3.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910   -1.2591   -0.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5195   -1.8887    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    2.3204    2.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3400    1.6693    3.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3059    3.1217    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    4.3697    2.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3179    1.1347    3.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6497    0.8973    3.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4438    2.4783    4.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5585    2.4083    1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7863   -0.8769    2.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8957    1.0555    2.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7820    2.1983    2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319    0.8691    1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 24  1  0
 14 13  1  0
 13 12  1  0
 11 12  1  6
 11 24  1  0
 17 19  1  0
 17 18  1  0
 11  5  1  0
 19 20  1  0
 19 22  1  0
 22 23  2  0
 22 14  1  0
  5  4  1  0
 10  8  1  0
  8  9  1  0
 15 16  1  0
 24 25  1  0
 16 17  1  0
 19 21  1  6
 15 14  2  0
  4  2  1  0
  8  7  1  0
  2  1  1  0
  7  6  1  0
  2  3  2  0
  6  5  1  0
 25 26  1  0
 26 27  1  0
 11 10  1  0
 26 28  2  0
  8 37  1  6
  7 35  1  0
  7 36  1  0
  6 33  1  0
  6 34  1  0
  5 32  1  1
 17 45  1  6
 16 43  1  0
 16 44  1  0
 13 41  1  0
 13 42  1  0
 24 51  1  1
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
 21 50  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       2.568  -4.153   4.273  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.874  -3.634   2.902  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.990  -3.617   2.401  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.732  -3.200   2.302  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.901  -2.595   1.006  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.920  -3.679  -0.074  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.049  -3.030  -1.444  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.959  -1.978  -1.645  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.161  -1.227  -2.955  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.963  -1.008  -0.591  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.763  -1.569   0.727  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.517  -2.225   0.819  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.619  -1.365   0.499  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.531  -0.015   1.148  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.424   0.459   1.753  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.357   1.808   2.427  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.501   2.737   2.019  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.517   3.879   2.883  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.862   2.029   2.036  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.331   1.610   3.430  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.836   2.956   1.528  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.782   0.796   1.132  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.742   0.454   0.439  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.811  -0.428   1.810  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.983   0.389   1.618  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.966   0.262   2.547  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.116   1.158   2.202  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.930  -0.474   3.522  0.00  0.00           O+0
HETATM   29  H   UNK     0       2.113  -3.362   4.875  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.496  -4.467   4.758  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.900  -5.015   4.202  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.858  -2.058   0.961  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.008  -4.287  -0.019  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.752  -4.373   0.091  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.996  -3.793  -2.228  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.037  -2.557  -1.514  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.021  -2.468  -1.683  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.151  -1.908  -3.811  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.111  -0.680  -2.951  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.371  -0.481  -3.092  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.691  -1.259  -0.589  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.519  -1.889   0.836  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.580   2.320   2.180  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.340   1.669   3.515  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.306   3.122   1.009  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.329   4.370   2.646  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.318   1.135   3.375  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.650   0.897   3.904  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.444   2.478   4.088  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.559   2.408   1.157  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.786  -0.877   2.812  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.896   1.056   2.962  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.782   2.198   2.184  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.532   0.869   1.234  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5   11    4    6   32                                             
CONECT    6    7    5   33   34                                             
CONECT    7    8    6   35   36                                             
CONECT    8   10    9    7   37                                             
CONECT    9    8   38   39   40                                             
CONECT   10    8   11                                                       
CONECT   11   12   24    5   10                                             
CONECT   12   13   11                                                       
CONECT   13   14   12   41   42                                             
CONECT   14   13   22   15                                                  
CONECT   15   24   16   14                                                  
CONECT   16   15   17   43   44                                             
CONECT   17   19   18   16   45                                             
CONECT   18   17   46                                                       
CONECT   19   17   20   22   21                                             
CONECT   20   19   47   48   49                                             
CONECT   21   19   50                                                       
CONECT   22   19   23   14                                                  
CONECT   23   22                                                            
CONECT   24   15   11   25   51                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   52   53   54                                             
CONECT   28   26                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41   13                                                            
CONECT   42   13                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   24                                                            
CONECT   52   27                                                            
CONECT   53   27                                                            
CONECT   54   27                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

RDKit          3D

54 56  0  0  0  0  0  0  0  0999 V2000
    2.5676   -4.1529    4.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8743   -3.6343    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9895   -3.6166    2.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7315   -3.2005    2.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9006   -2.5950    1.0062 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9200   -3.6789   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0487   -3.0297   -1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9586   -1.9783   -1.6454 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1615   -1.2269   -2.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9629   -1.0080   -0.5907 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628   -1.5689    0.7265 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5165   -2.2255    0.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6188   -1.3646    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5312   -0.0150    1.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4244    0.4588    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    1.8075    2.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    2.7375    2.0190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5165    3.8789    2.8832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8617    2.0293    2.0358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3311    1.6101    3.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8360    2.9560    1.5279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7823    0.7958    1.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7417    0.4537    0.4385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114   -0.4283    1.8102 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9828    0.3888    1.6177 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9664    0.2621    2.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1158    1.1578    2.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305   -0.4739    3.5220 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128   -3.3621    4.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4963   -4.4672    4.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9001   -5.0152    4.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -2.0581    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084   -4.2868   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517   -4.3732    0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9958   -3.7934   -2.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0369   -2.5571   -1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0213   -2.4680   -1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513   -1.9080   -3.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1110   -0.6801   -2.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706   -0.4814   -3.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910   -1.2591   -0.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5195   -1.8887    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    2.3204    2.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3400    1.6693    3.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3059    3.1217    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    4.3697    2.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3179    1.1347    3.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6497    0.8973    3.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4438    2.4783    4.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5585    2.4083    1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7863   -0.8769    2.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8957    1.0555    2.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7820    2.1983    2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319    0.8691    1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 24  1  0
 14 13  1  0
 13 12  1  0
 11 12  1  6
 11 24  1  0
 17 19  1  0
 17 18  1  0
 11  5  1  0
 19 20  1  0
 19 22  1  0
 22 23  2  0
 22 14  1  0
  5  4  1  0
 10  8  1  0
  8  9  1  0
 15 16  1  0
 24 25  1  0
 16 17  1  0
 19 21  1  6
 15 14  2  0
  4  2  1  0
  8  7  1  0
  2  1  1  0
  7  6  1  0
  2  3  2  0
  6  5  1  0
 25 26  1  0
 26 27  1  0
 11 10  1  0
 26 28  2  0
  8 37  1  6
  7 35  1  0
  7 36  1  0
  6 33  1  0
  6 34  1  0
  5 32  1  1
 17 45  1  6
 16 43  1  0
 16 44  1  0
 13 41  1  0
 13 42  1  0
 24 51  1  1
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
 21 50  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
M  END

View in JSmol

Synonyms

Value	Source
(3S,3's,4S,6S,6's,7R)-3'-(Acetyloxy)-6,7-dihydroxy-6',7-dimethyl-8-oxo-1,4,5,6,7,8-hexahydrospiro[2-benzopyran-3,2'-oxane]-4-yl acetic acid	Generator

Chemical Formula

C₁₉H₂₆O₉

Average Mass

398.4080 Da

Monoisotopic Mass

398.15768 Da

IUPAC Name

(3S,3'S,4S,6S,6'S,7R)-3'-(acetyloxy)-6,7-dihydroxy-6',7-dimethyl-8-oxo-1,4,5,6,7,8-hexahydrospiro[2-benzopyran-3,2'-oxane]-4-yl acetate

Traditional Name

(3S,3'S,4S,6S,6'S,7R)-3'-(acetyloxy)-6,7-dihydroxy-6',7-dimethyl-8-oxo-1,4,5,6-tetrahydrospiro[2-benzopyran-3,2'-oxane]-4-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])C2=C(C(=O)[C@@]1(O[H])C([H])([H])[H])C([H])([H])O[C@@]1(O[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])OC(=O)C([H])([H])[H])[C@@]2([H])OC(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C19H26O9/c1-9-5-6-15(26-10(2)20)19(28-9)17(27-11(3)21)12-7-14(22)18(4,24)16(23)13(12)8-25-19/h9,14-15,17,22,24H,5-8H2,1-4H3/t9-,14-,15-,17-,18+,19-/m0/s1

InChI Key

MPVZXVXIZMIJFZ-NVBYNIPGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Penicillium raistrickii	JEOL database	Ma, L.-Y., et al, Tetrahedron 68, 2276 (2012)

Species Where Detected

Species Name	Source	Reference
Penicillium raistrickii HQ717799	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaphilones

Sub Class

Not Available

Direct Parent

Azaphilones

Alternative Parents

Substituents

Azaphilone
Benzopyran
Ketal
Cyclohexenone
Acyloin
Dicarboxylic acid or derivatives
Oxane
Pyran
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Ketone
Secondary alcohol
Oxacycle
Acetal
Carboxylic acid derivative
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	-0.35	ALOGPS
logP	0.17	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.66 m³·mol⁻¹	ChemAxon
Polarizability	38.9 Å³	ChemAxon
Number of Rings	3	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

C00053645

Chemspider ID

34982015

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101564886

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ma, L.-Y., et al. (2012). Ma, L.-Y., et al, Tetrahedron 68, 2276 (2012). Tetrahedron.

Showing NP-Card for peneciraistin C (NP0041192)

MOL for NP0041192 (peneciraistin C)

3D MOL for NP0041192 (peneciraistin C)

3D SDF for NP0041192 (peneciraistin C)

3D-SDF for NP0041192 (peneciraistin C)

PDB for NP0041192 (peneciraistin C)

3D PDB for NP0041192 (peneciraistin C)

SMILES for NP0041192 (peneciraistin C)

INCHI for NP0041192 (peneciraistin C)

Structure for NP0041192 (peneciraistin C)

3D Structure for NP0041192 (peneciraistin C)