NP-MRD: Showing NP-Card for Sch 642305 (NP0005012)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 02:22:53 UTC

Updated at

2021-07-15 16:50:48 UTC

NP-MRD ID

NP0005012

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sch 642305

Provided By

NPAtlas

Description

Sch 642305 is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Sch 642305 is found in Penicillium verrucosum. Sch 642305 was first documented in 2003 (PMID: 14695789). Based on a literature review a small amount of articles have been published on sch 642305 (PMID: 17429757) (PMID: 19420701) (PMID: 32999145).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118163D          

 38 39  0  0  0  0            999 V2000
   -3.8022    0.7995   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8223    0.8637    0.5814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3203   -0.5288    0.7865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8637   -1.2017   -0.4845 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8189   -2.2243   -0.0947 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5586   -1.8695   -0.5864 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2830   -0.9015    0.2803 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6551   -1.4171    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -2.6380    0.3581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6743   -0.4773    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609    0.7370    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6308    1.0681   -0.5497 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5316    2.4767   -0.5861 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2621    0.5083   -0.2372 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4834    1.4266    0.7138 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6739    2.0357   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272    2.6656   -1.0457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132    1.8696    0.4909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116    0.5251   -0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160    1.8465   -1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4334    0.1470   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4930    1.0807    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -1.1315    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5957   -0.6328    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003   -1.7166   -1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.4503   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -3.1929   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356   -2.4269    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -1.4813   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1587   -2.7946   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -0.9169    1.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -0.7929    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    1.4326    0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9825    0.7745   -1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9961    2.8910    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300    0.4648   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064    2.2473    1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141    0.9345    1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18  2  1  0  0  0  0
 14  7  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  1  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  7 31  1  1  0  0  0
 10 32  1  0  0  0  0
 11 33  1  0  0  0  0
 12 34  1  6  0  0  0
 13 35  1  0  0  0  0
 14 36  1  6  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
M  END

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.8022    0.7995   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8223    0.8637    0.5814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3203   -0.5288    0.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637   -1.2017   -0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8189   -2.2243   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586   -1.8695   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2830   -0.9015    0.2803 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6551   -1.4171    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -2.6380    0.3581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6743   -0.4773    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609    0.7370    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6308    1.0681   -0.5497 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5316    2.4767   -0.5861 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2621    0.5083   -0.2372 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4834    1.4266    0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    2.0357   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272    2.6656   -1.0457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132    1.8696    0.4909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116    0.5251   -0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160    1.8465   -1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4334    0.1470   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4930    1.0807    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -1.1315    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5957   -0.6328    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003   -1.7166   -1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.4503   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -3.1929   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356   -2.4269    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -1.4813   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1587   -2.7946   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -0.9169    1.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -0.7929    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    1.4326    0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9825    0.7745   -1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9961    2.8910    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300    0.4648   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064    2.2473    1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141    0.9345    1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  1
 10 32  1  0
 11 33  1  0
 12 34  1  6
 13 35  1  0
 14 36  1  6
 15 37  1  0
 15 38  1  0
M  END


  Mrv1652306242118163D          

 38 39  0  0  0  0            999 V2000
   -3.8022    0.7995   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8223    0.8637    0.5814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3203   -0.5288    0.7865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8637   -1.2017   -0.4845 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8189   -2.2243   -0.0947 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5586   -1.8695   -0.5864 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2830   -0.9015    0.2803 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6551   -1.4171    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -2.6380    0.3581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6743   -0.4773    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609    0.7370    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6308    1.0681   -0.5497 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5316    2.4767   -0.5861 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2621    0.5083   -0.2372 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4834    1.4266    0.7138 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6739    2.0357   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272    2.6656   -1.0457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132    1.8696    0.4909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116    0.5251   -0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160    1.8465   -1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4334    0.1470   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4930    1.0807    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -1.1315    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5957   -0.6328    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003   -1.7166   -1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.4503   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -3.1929   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356   -2.4269    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -1.4813   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1587   -2.7946   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -0.9169    1.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -0.7929    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    1.4326    0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9825    0.7745   -1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9961    2.8910    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300    0.4648   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064    2.2473    1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141    0.9345    1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18  2  1  0  0  0  0
 14  7  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  1  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  7 31  1  1  0  0  0
 10 32  1  0  0  0  0
 11 33  1  0  0  0  0
 12 34  1  6  0  0  0
 13 35  1  0  0  0  0
 14 36  1  6  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005012

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])=C([H])C(=O)[C@]2([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[C@@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O4/c1-9-4-2-3-5-10-11(8-14(17)18-9)13(16)7-6-12(10)15/h6-7,9-11,13,16H,2-5,8H2,1H3/t9-,10+,11+,13-/m0/s1

> <INCHI_KEY>
WTQWDNIIFGEBSZ-WGBDABJCSA-N

> <FORMULA>
C14H20O4

> <MOLECULAR_WEIGHT>
252.31

> <EXACT_MASS>
252.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.5937623272524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,8aR,12S,12aR)-12-hydroxy-4-methyl-2,4,5,6,7,8,8a,9,12,12a-decahydro-1H-3-benzoxecine-2,9-dione

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
1.7101348846666666

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.07377256642904

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.489863387026475

> <JCHEM_PKA_STRONGEST_BASIC>
-3.021849918964624

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
67.42800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,8aR,12S,12aR)-12-hydroxy-4-methyl-4,5,6,7,8,8a,12,12a-octahydro-1H-3-benzoxecine-2,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.8022    0.7995   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8223    0.8637    0.5814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3203   -0.5288    0.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637   -1.2017   -0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8189   -2.2243   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586   -1.8695   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2830   -0.9015    0.2803 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6551   -1.4171    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -2.6380    0.3581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6743   -0.4773    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609    0.7370    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6308    1.0681   -0.5497 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5316    2.4767   -0.5861 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2621    0.5083   -0.2372 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4834    1.4266    0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    2.0357   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272    2.6656   -1.0457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132    1.8696    0.4909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116    0.5251   -0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160    1.8465   -1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4334    0.1470   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4930    1.0807    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -1.1315    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5957   -0.6328    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003   -1.7166   -1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.4503   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -3.1929   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356   -2.4269    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -1.4813   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1587   -2.7946   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -0.9169    1.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -0.7929    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    1.4326    0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9825    0.7745   -1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9961    2.8910    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300    0.4648   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064    2.2473    1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141    0.9345    1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  1
 10 32  1  0
 11 33  1  0
 12 34  1  6
 13 35  1  0
 14 36  1  6
 15 37  1  0
 15 38  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.802   0.800  -0.599  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.822   0.864   0.581  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.320  -0.529   0.787  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.864  -1.202  -0.485  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.819  -2.224  -0.095  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.559  -1.869  -0.586  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.283  -0.902   0.280  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.655  -1.417   0.523  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.953  -2.638   0.358  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.674  -0.477   0.964  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.661   0.737   0.438  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.631   1.068  -0.550  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.532   2.477  -0.586  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.262   0.508  -0.237  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.483   1.427   0.714  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.674   2.036  -0.005  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.327   2.666  -1.046  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.913   1.870   0.491  0.00  0.00           O+0
HETATM   19  H   UNK     0      -4.812   0.525  -0.283  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.816   1.847  -1.006  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.433   0.147  -1.399  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.493   1.081   1.469  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.216  -1.131   1.131  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.596  -0.633   1.620  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.700  -1.717  -1.004  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.485  -0.450  -1.204  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.085  -3.193  -0.569  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.836  -2.427   1.005  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.438  -1.481  -1.631  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.159  -2.795  -0.681  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.762  -0.917   1.281  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.408  -0.793   1.697  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.425   1.433   0.773  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.982   0.775  -1.559  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.996   2.891   0.160  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.730   0.465  -1.233  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.206   2.247   1.006  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.214   0.935   1.645  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3   18   22                                             
CONECT    3    2    4   23   24                                             
CONECT    4    3    5   25   26                                             
CONECT    5    4    6   27   28                                             
CONECT    6    5    7   29   30                                             
CONECT    7    6    8   14   31                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   32                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13   14   34                                             
CONECT   13   12   35                                                       
CONECT   14   12   15    7   36                                             
CONECT   15   14   16   37   38                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2                                                       
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    4                                                            
CONECT   27    5                                                            
CONECT   28    5                                                            
CONECT   29    6                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   15                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

RDKit          3D

38 39  0  0  0  0  0  0  0  0999 V2000
   -3.8022    0.7995   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8223    0.8637    0.5814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3203   -0.5288    0.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637   -1.2017   -0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8189   -2.2243   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586   -1.8695   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2830   -0.9015    0.2803 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6551   -1.4171    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -2.6380    0.3581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6743   -0.4773    0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609    0.7370    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6308    1.0681   -0.5497 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5316    2.4767   -0.5861 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2621    0.5083   -0.2372 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4834    1.4266    0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    2.0357   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272    2.6656   -1.0457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132    1.8696    0.4909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116    0.5251   -0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160    1.8465   -1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4334    0.1470   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4930    1.0807    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -1.1315    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5957   -0.6328    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003   -1.7166   -1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.4503   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -3.1929   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356   -2.4269    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -1.4813   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1587   -2.7946   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -0.9169    1.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -0.7929    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    1.4326    0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9825    0.7745   -1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9961    2.8910    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300    0.4648   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2064    2.2473    1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141    0.9345    1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  1
 10 32  1  0
 11 33  1  0
 12 34  1  6
 13 35  1  0
 14 36  1  6
 15 37  1  0
 15 38  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(+)-SCH 642305	ChEBI

Chemical Formula

C₁₄H₂₀O₄

Average Mass

252.3100 Da

Monoisotopic Mass

252.13616 Da

IUPAC Name

(4S,8aR,12S,12aR)-12-hydroxy-4-methyl-2,4,5,6,7,8,8a,9,12,12a-decahydro-1H-3-benzoxecine-2,9-dione

Traditional Name

(4S,8aR,12S,12aR)-12-hydroxy-4-methyl-4,5,6,7,8,8a,12,12a-octahydro-1H-3-benzoxecine-2,9-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1CCCC[C@@H]2[C@@H](CC(=O)O1)[C@@H](O)C=CC2=O

InChI Identifier

InChI=1S/C14H20O4/c1-9-4-2-3-5-10-11(8-14(17)18-9)13(16)7-6-12(10)15/h6-7,9-11,13,16H,2-5,8H2,1H3/t9-,10+,11+,13-/m0/s1

InChI Key

WTQWDNIIFGEBSZ-WGBDABJCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Penicillium verrucosum	NPAtlas	14695789

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	1.06	ALOGPS
logP	1.71	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.49	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.43 m³·mol⁻¹	ChemAxon
Polarizability	26.59 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA012507

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045061

Chemspider ID

552951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sch 642305

METLIN ID

Not Available

PubChem Compound

637324

PDB ID

Not Available

ChEBI ID

66181

Good Scents ID

Not Available

References

General References

Chu M, Mierzwa R, Xu L, He L, Terracciano J, Patel M, Gullo V, Black T, Zhao W, Chan TM, McPhail AT: Isolation and structure elucidation of Sch 642305, a novel bacterial DNA primase inhibitor produced by Penicillium verrucosum. J Nat Prod. 2003 Dec;66(12):1527-30. doi: 10.1021/np0302302. [PubMed:14695789 ]
Nicoletti R, Lopez-Gresa MP, Manzo E, Carella A, Ciavatta ML: Production and fungitoxic activity of Sch 642305, a secondary metabolite of Penicillium canescens. Mycopathologia. 2007 May;163(5):295-301. doi: 10.1007/s11046-007-9015-x. Epub 2007 Apr 12. [PubMed:17429757 ]
Ishigami K: Synthetic studies of natural 10-membered lactones, mueggelone, microcarpalide, and sch 642305, which have interesting bioactivities. Biosci Biotechnol Biochem. 2009 May;73(5):971-9. doi: 10.1271/bbb.80877. Epub 2009 May 7. [PubMed:19420701 ]
Fujioka H: Development of New Innovative Synthetic Organic Chemistry Using Lone Pairs of Oxygen Atoms. Chem Pharm Bull (Tokyo). 2020;68(10):907-945. doi: 10.1248/cpb.c20-00178. [PubMed:32999145 ]

Showing NP-Card for Sch 642305 (NP0005012)

MOL for NP0005012 (Sch 642305)

3D MOL for NP0005012 (Sch 642305)

3D SDF for NP0005012 (Sch 642305)

3D-SDF for NP0005012 (Sch 642305)

PDB for NP0005012 (Sch 642305)

3D PDB for NP0005012 (Sch 642305)

SMILES for NP0005012 (Sch 642305)

INCHI for NP0005012 (Sch 642305)

Structure for NP0005012 (Sch 642305)

3D Structure for NP0005012 (Sch 642305)