NP-MRD: Showing NP-Card for Cladosporin (NP0021576)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2021-01-06 06:51:52 UTC

Updated at

2021-07-15 17:36:43 UTC

NP-MRD ID

NP0021576

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cladosporin

Provided By

NPAtlas

Description

Cladosporin is found in Alternaria alternata, Cladosporium cladosporioides and Polysiphonia urceolata. It was first documented in 1971 (PMID: 5169000). Based on a literature review very few articles have been published on (3R)-6,8-dihydroxy-3-{[(2R,6S)-6-methyloxan-2-yl]methyl}-3,4-dihydro-1H-2-benzopyran-1-one (PMID: 33969584) (PMID: 33843204) (PMID: 33084231) (PMID: 32195573) (PMID: 31961156) (PMID: 31401763).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105163D          

 41 43  0  0  0  0            999 V2000
   -4.2462   -0.9653   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762    0.4909   -0.9526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3925    0.6784    0.5583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3730   -0.1912    1.2095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9680   -0.0288    0.6649 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8556    0.4620   -0.7114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7173    1.3974   -0.9354 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6450    0.8791   -0.7014 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0390    0.4057    0.6374 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5363    0.1298    0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652    0.3702    1.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116    0.0747    1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3492    0.3170    2.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2137   -0.4451    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -0.6722   -0.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919   -1.1898   -1.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0836   -0.3825   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.5729   -1.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -1.0515   -2.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268   -0.2043   -1.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863    1.0935   -1.2305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3463   -1.1068   -2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897   -1.3674   -0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4299   -1.5717   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9664    1.0207   -1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1585    1.7360    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3888    0.3556    0.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7230   -1.2538    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372   -0.0214    2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3976    0.5899    1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5592   -1.0839    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716   -0.3931   -1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    2.3472   -0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7340    1.7227   -2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205    1.6739   -0.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8624    1.1776    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6251   -0.5381    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7744    0.7822    2.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4059   -0.4614    3.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2771   -0.6693    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9726   -1.4036   -1.6975 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  1  0  0  0  0
  9 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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  6 21  1  0  0  0  0
 21  2  1  0  0  0  0
 20  8  1  0  0  0  0
 17 10  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  2 25  1  6  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  6 32  1  6  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  8 35  1  6  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 11 38  1  0  0  0  0
 13 39  1  0  0  0  0
 14 40  1  0  0  0  0
 16 41  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.2462   -0.9653   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762    0.4909   -0.9526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3925    0.6784    0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3730   -0.1912    1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9680   -0.0288    0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    0.4620   -0.7114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7173    1.3974   -0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    0.8791   -0.7014 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0390    0.4057    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5363    0.1298    0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652    0.3702    1.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116    0.0747    1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3492    0.3170    2.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2137   -0.4451    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -0.6722   -0.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919   -1.1898   -1.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0836   -0.3825   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.5729   -1.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -1.0515   -2.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268   -0.2043   -1.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863    1.0935   -1.2305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3463   -1.1068   -2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897   -1.3674   -0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4299   -1.5717   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9664    1.0207   -1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1585    1.7360    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3888    0.3556    0.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7230   -1.2538    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372   -0.0214    2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3976    0.5899    1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5592   -1.0839    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716   -0.3931   -1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    2.3472   -0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7340    1.7227   -2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205    1.6739   -0.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8624    1.1776    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6251   -0.5381    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7744    0.7822    2.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4059   -0.4614    3.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2771   -0.6693    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9726   -1.4036   -1.6975 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  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  6 21  1  0
 21  2  1  0
 20  8  1  0
 17 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  6
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  6
  7 33  1  0
  7 34  1  0
  8 35  1  6
  9 36  1  0
  9 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  0
M  END


  Mrv1652306242105163D          

 41 43  0  0  0  0            999 V2000
   -4.2462   -0.9653   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762    0.4909   -0.9526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3925    0.6784    0.5583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3730   -0.1912    1.2095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9680   -0.0288    0.6649 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8556    0.4620   -0.7114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7173    1.3974   -0.9354 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6450    0.8791   -0.7014 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0390    0.4057    0.6374 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5363    0.1298    0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652    0.3702    1.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116    0.0747    1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3492    0.3170    2.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2137   -0.4451    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -0.6722   -0.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919   -1.1898   -1.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0836   -0.3825   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.5729   -1.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -1.0515   -2.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268   -0.2043   -1.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863    1.0935   -1.2305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3463   -1.1068   -2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897   -1.3674   -0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4299   -1.5717   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9664    1.0207   -1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1585    1.7360    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3888    0.3556    0.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7230   -1.2538    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372   -0.0214    2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3976    0.5899    1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5592   -1.0839    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716   -0.3931   -1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    2.3472   -0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7340    1.7227   -2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205    1.6739   -0.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8624    1.1776    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6251   -0.5381    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7744    0.7822    2.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4059   -0.4614    3.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2771   -0.6693    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9726   -1.4036   -1.6975 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  1  0  0  0  0
  9 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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  6 21  1  0  0  0  0
 21  2  1  0  0  0  0
 20  8  1  0  0  0  0
 17 10  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  2 25  1  6  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  6 32  1  6  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  8 35  1  6  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 11 38  1  0  0  0  0
 13 39  1  0  0  0  0
 14 40  1  0  0  0  0
 16 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021576

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)O[C@@]([H])(C([H])([H])[C@]3([H])O[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C3([H])[H])C([H])([H])C2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O5/c1-9-3-2-4-12(20-9)8-13-6-10-5-11(17)7-14(18)15(10)16(19)21-13/h5,7,9,12-13,17-18H,2-4,6,8H2,1H3/t9-,12+,13+/m0/s1

> <INCHI_KEY>
WOMKDMUZNBFXKG-ZWKOPEQDSA-N

> <FORMULA>
C16H20O5

> <MOLECULAR_WEIGHT>
292.331

> <EXACT_MASS>
292.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.14239171695815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-6,8-dihydroxy-3-{[(2R,6S)-6-methyloxan-2-yl]methyl}-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
3.25894017

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.35801693365849

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.50958170683555

> <JCHEM_PKA_STRONGEST_BASIC>
-4.010522392333969

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
77.1648

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-6,8-dihydroxy-3-{[(2R,6S)-6-methyloxan-2-yl]methyl}-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.2462   -0.9653   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762    0.4909   -0.9526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3925    0.6784    0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3730   -0.1912    1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9680   -0.0288    0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    0.4620   -0.7114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7173    1.3974   -0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    0.8791   -0.7014 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0390    0.4057    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5363    0.1298    0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652    0.3702    1.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116    0.0747    1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3492    0.3170    2.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2137   -0.4451    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -0.6722   -0.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919   -1.1898   -1.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0836   -0.3825   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.5729   -1.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -1.0515   -2.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268   -0.2043   -1.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863    1.0935   -1.2305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3463   -1.1068   -2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897   -1.3674   -0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4299   -1.5717   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9664    1.0207   -1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1585    1.7360    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3888    0.3556    0.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7230   -1.2538    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372   -0.0214    2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3976    0.5899    1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5592   -1.0839    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716   -0.3931   -1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    2.3472   -0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7340    1.7227   -2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205    1.6739   -0.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8624    1.1776    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6251   -0.5381    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7744    0.7822    2.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4059   -0.4614    3.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2771   -0.6693    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9726   -1.4036   -1.6975 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  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  6 21  1  0
 21  2  1  0
 20  8  1  0
 17 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  6
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  6
  7 33  1  0
  7 34  1  0
  8 35  1  6
  9 36  1  0
  9 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  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      -4.246  -0.965  -1.305  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.176   0.491  -0.953  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.393   0.678   0.558  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.373  -0.191   1.210  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.968  -0.029   0.665  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.856   0.462  -0.711  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.717   1.397  -0.935  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.645   0.879  -0.701  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.039   0.406   0.637  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.536   0.130   0.605  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.265   0.370   1.741  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.612   0.075   1.716  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.349   0.317   2.862  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.214  -0.445   0.591  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.438  -0.672  -0.538  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.992  -1.190  -1.685  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.084  -0.383  -0.537  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.265  -0.573  -1.724  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.752  -1.052  -2.785  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.927  -0.204  -1.627  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.986   1.093  -1.230  0.00  0.00           O+0
HETATM   22  H   UNK     0      -4.346  -1.107  -2.381  0.00  0.00           H+0
HETATM   23  H   UNK     0      -5.190  -1.367  -0.833  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.430  -1.572  -0.916  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.966   1.021  -1.512  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.159   1.736   0.785  0.00  0.00           H+0
HETATM   27  H   UNK     0      -5.389   0.356   0.857  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.723  -1.254   1.101  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.337  -0.021   2.304  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.398   0.590   1.380  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.559  -1.084   0.681  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.672  -0.393  -1.448  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.836   2.347  -0.336  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.734   1.723  -2.034  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.421   1.674  -0.986  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.862   1.178   1.430  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.625  -0.538   0.995  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.774   0.782   2.623  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.406  -0.461   3.533  0.00  0.00           H+0
HETATM   40  H   UNK     0       6.277  -0.669   0.600  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.973  -1.404  -1.698  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3   21   25                                             
CONECT    3    2    4   26   27                                             
CONECT    4    3    5   28   29                                             
CONECT    5    4    6   30   31                                             
CONECT    6    5    7   21   32                                             
CONECT    7    6    8   33   34                                             
CONECT    8    7    9   20   35                                             
CONECT    9    8   10   36   37                                             
CONECT   10    9   11   17                                                  
CONECT   11   10   12   38                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   39                                                       
CONECT   14   12   15   40                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   41                                                       
CONECT   17   15   18   10                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    8                                                       
CONECT   21    6    2                                                       
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    2                                                            
CONECT   26    3                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31    5                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   11                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   16                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
   -4.2462   -0.9653   -1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762    0.4909   -0.9526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3925    0.6784    0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3730   -0.1912    1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9680   -0.0288    0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    0.4620   -0.7114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7173    1.3974   -0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450    0.8791   -0.7014 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0390    0.4057    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5363    0.1298    0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652    0.3702    1.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116    0.0747    1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3492    0.3170    2.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2137   -0.4451    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375   -0.6722   -0.5377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919   -1.1898   -1.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0836   -0.3825   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.5729   -1.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -1.0515   -2.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268   -0.2043   -1.6265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863    1.0935   -1.2305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3463   -1.1068   -2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1897   -1.3674   -0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4299   -1.5717   -0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9664    1.0207   -1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1585    1.7360    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3888    0.3556    0.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7230   -1.2538    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372   -0.0214    2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3976    0.5899    1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5592   -1.0839    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6716   -0.3931   -1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    2.3472   -0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7340    1.7227   -2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205    1.6739   -0.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8624    1.1776    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6251   -0.5381    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7744    0.7822    2.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4059   -0.4614    3.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2771   -0.6693    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9726   -1.4036   -1.6975 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  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  6 21  1  0
 21  2  1  0
 20  8  1  0
 17 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  6
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  6
  7 33  1  0
  7 34  1  0
  8 35  1  6
  9 36  1  0
  9 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Isocladosporin	MeSH
3,4-Dihydro-6,8-dihydroxy-3-(6-methyltetrahydropyran- 2-ylmethyl)isocoumarin	MeSH
Asperentin	MeSH

Chemical Formula

C₁₆H₂₀O₅

Average Mass

292.3310 Da

Monoisotopic Mass

292.13107 Da

IUPAC Name

(3R)-6,8-dihydroxy-3-{[(2R,6S)-6-methyloxan-2-yl]methyl}-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

(3R)-6,8-dihydroxy-3-{[(2R,6S)-6-methyloxan-2-yl]methyl}-3,4-dihydro-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC[C@H](C[C@H]2CC3=CC(O)=CC(O)=C3C(=O)O2)O1

InChI Identifier

InChI=1S/C16H20O5/c1-9-3-2-4-12(20-9)8-13-6-10-5-11(17)7-14(18)15(10)16(19)21-13/h5,7,9,12-13,17-18H,2-4,6,8H2,1H3/t9-,12+,13+/m0/s1

InChI Key

WOMKDMUZNBFXKG-ZWKOPEQDSA-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
Alternaria alternata	LOTUS Database	35616633
Cladosporium cladosporioides	NPAtlas	5169000
Polysiphonia urceolata	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Chaetomium globasum	KNApSAcK Database	22123792
Microascus tardifaciens	KNApSAcK Database	22123792

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	2.4	ALOGPS
logP	3.26	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.51	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.16 m³·mol⁻¹	ChemAxon
Polarizability	31.14 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

NPAtlas ID

NPA019737

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23327352

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13990016

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Scott PM, Van Walbeek W, MacLean WM: Cladosporin, a new antifungal metabolite from Cladosporium cladosporioides. J Antibiot (Tokyo). 1971 Nov;24(11):747-55. doi: 10.7164/antibiotics.24.747. [PubMed:5169000 ]
Babbar P, Sato M, Manickam Y, Mishra S, Harlos K, Gupta S, Parvez S, Kikuchi H, Sharma A: Inhibition of Plasmodium falciparum Lysyl-tRNA Synthetase via a Piperidine-Ring Scaffold Inspired Cladosporin Analogues. Chembiochem. 2021 Jul 15;22(14):2468-2477. doi: 10.1002/cbic.202100212. Epub 2021 May 28. [PubMed:33969584 ]
Babbar P, Das P, Manickam Y, Mankad Y, Yadav S, Parvez S, Sharma A, Reddy DS: Design, Synthesis, and Structural Analysis of Cladosporin-Based Inhibitors of Malaria Parasites. ACS Infect Dis. 2021 Jun 11;7(6):1777-1794. doi: 10.1021/acsinfecdis.1c00092. Epub 2021 Apr 12. [PubMed:33843204 ]
Zhang R, Noordam L, Ou X, Ma B, Li Y, Das P, Shi S, Liu J, Wang L, Li P, Verstegen MMA, Reddy DS, van der Laan LJW, Peppelenbosch MP, Kwekkeboom J, Smits R, Pan Q: The biological process of lysine-tRNA charging is therapeutically targetable in liver cancer. Liver Int. 2021 Jan;41(1):206-219. doi: 10.1111/liv.14692. Epub 2020 Oct 20. [PubMed:33084231 ]
Zhou J, Zheng L, Hei Z, Li W, Wang J, Yu B, Fang P: Atomic Resolution Analyses of Isocoumarin Derivatives for Inhibition of Lysyl-tRNA Synthetase. ACS Chem Biol. 2020 Apr 17;15(4):1016-1025. doi: 10.1021/acschembio.0c00032. Epub 2020 Mar 26. [PubMed:32195573 ]
Lauro G, Das P, Riccio R, Reddy DS, Bifulco G: DFT/NMR Approach for the Configuration Assignment of Groups of Stereoisomers by the Combination and Comparison of Experimental and Predicted Sets of Data. J Org Chem. 2020 Mar 6;85(5):3297-3306. doi: 10.1021/acs.joc.9b03129. Epub 2020 Feb 4. [PubMed:31961156 ]
Savi DC, Noriler SA, Ponomareva LV, Thorson JS, Rohr J, Glienke C, Shaaban KA: Dihydroisocoumarins produced by Diaporthe cf. heveae LGMF1631 inhibiting citrus pathogens. Folia Microbiol (Praha). 2020 Apr;65(2):381-392. doi: 10.1007/s12223-019-00746-8. Epub 2019 Aug 10. [PubMed:31401763 ]
Goel P, Parvez S, Sharma A: Genomic analyses of aminoacyl tRNA synthetases from human-infecting helminths. BMC Genomics. 2019 May 2;20(1):333. doi: 10.1186/s12864-019-5679-0. [PubMed:31046663 ]
Chhibber-Goel J, Sharma A: Side chain rotameric changes and backbone dynamics enable specific cladosporin binding in Plasmodium falciparum lysyl-tRNA synthetase. Proteins. 2019 Sep;87(9):730-737. doi: 10.1002/prot.25699. Epub 2019 May 9. [PubMed:31017332 ]

Showing NP-Card for Cladosporin (NP0021576)

MOL for NP0021576 (Cladosporin)

3D MOL for NP0021576 (Cladosporin)

3D SDF for NP0021576 (Cladosporin)

3D-SDF for NP0021576 (Cladosporin)

PDB for NP0021576 (Cladosporin)

3D PDB for NP0021576 (Cladosporin)

SMILES for NP0021576 (Cladosporin)

INCHI for NP0021576 (Cladosporin)

Structure for NP0021576 (Cladosporin)

3D Structure for NP0021576 (Cladosporin)