NP-MRD: Showing NP-Card for 7-desmethylherbarin (NP0009256)

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Record Information

Version

2.0

Created at

2020-12-09 06:39:54 UTC

Updated at

2021-07-15 17:02:45 UTC

NP-MRD ID

NP0009256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-desmethylherbarin

Provided By

NPAtlas

Description

7-desmethylherbarin is found in Corynespora. 7-desmethylherbarin was first documented in 2010 (PMID: 20521776). Based on a literature review very few articles have been published on 3,7-dihydroxy-9-methoxy-3-methyl-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-5,10-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106343D          

 35 37  0  0  0  0            999 V2000
   -4.6086    1.7622   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2611    1.4677   -0.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    0.2420   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.7825    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -2.0074    0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1672   -3.0005    0.8999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -2.1605    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737   -1.1572    0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4567    0.0553    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    1.1146   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742    2.2316   -0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    0.8863    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073   -0.2649    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8780   -0.3838    0.6348 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6098    0.2912   -0.4724 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0616    0.4559   -0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566   -0.6189   -1.5539 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646    1.4474   -0.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840    1.9385   -0.2663 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4693   -1.3376    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9187   -2.4329    1.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1434    2.0239    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714    2.5882   -1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1594    0.9015   -1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7537   -0.6509    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508   -3.6701    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256   -3.1100    1.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1331    0.1376    1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -1.4415    0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1923    1.3845    0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3473   -0.3783    0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7622    0.4031   -0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8006   -1.1054   -1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2478    2.4806    0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834    2.6905   -0.9103 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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  6  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
  9  3  1  0  0  0  0
 19 12  1  0  0  0  0
 20  8  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
  4 25  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
 16 30  1  0  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 17 33  1  0  0  0  0
 19 34  1  0  0  0  0
 19 35  1  0  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.6086    1.7622   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2611    1.4677   -0.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    0.2420   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.7825    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -2.0074    0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1672   -3.0005    0.8999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -2.1605    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737   -1.1572    0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4567    0.0553    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    1.1146   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742    2.2316   -0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    0.8863    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073   -0.2649    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8780   -0.3838    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098    0.2912   -0.4724 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0616    0.4559   -0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566   -0.6189   -1.5539 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646    1.4474   -0.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840    1.9385   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693   -1.3376    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9187   -2.4329    1.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1434    2.0239    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714    2.5882   -1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1594    0.9015   -1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7537   -0.6509    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508   -3.6701    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256   -3.1100    1.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1331    0.1376    1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -1.4415    0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1923    1.3845    0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3473   -0.3783    0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7622    0.4031   -0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8006   -1.1054   -1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2478    2.4806    0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834    2.6905   -0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  6
 15 18  1  0
 18 19  1  0
 13 20  1  0
 20 21  2  0
  9  3  1  0
 19 12  1  0
 20  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 14 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  1  0
M  END


  Mrv1652306242106343D          

 35 37  0  0  0  0            999 V2000
   -4.6086    1.7622   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2611    1.4677   -0.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    0.2420   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.7825    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -2.0074    0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1672   -3.0005    0.8999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -2.1605    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737   -1.1572    0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4567    0.0553    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    1.1146   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742    2.2316   -0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    0.8863    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073   -0.2649    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8780   -0.3838    0.6348 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6098    0.2912   -0.4724 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0616    0.4559   -0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566   -0.6189   -1.5539 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646    1.4474   -0.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840    1.9385   -0.2663 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4693   -1.3376    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9187   -2.4329    1.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1434    2.0239    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714    2.5882   -1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1594    0.9015   -1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7537   -0.6509    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508   -3.6701    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256   -3.1100    1.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1331    0.1376    1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -1.4415    0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1923    1.3845    0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3473   -0.3783    0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7622    0.4031   -0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8006   -1.1054   -1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2478    2.4806    0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834    2.6905   -0.9103 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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  6  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
  9  3  1  0  0  0  0
 19 12  1  0  0  0  0
 20  8  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
  4 25  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
 16 30  1  0  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 17 33  1  0  0  0  0
 19 34  1  0  0  0  0
 19 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(=O)C3=C(C2=O)C([H])([H])[C@@](O[H])(OC3([H])[H])C([H])([H])[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O6/c1-15(19)5-9-10(6-21-15)14(18)12-8(13(9)17)3-7(16)4-11(12)20-2/h3-4,16,19H,5-6H2,1-2H3/t15-/m0/s1

> <INCHI_KEY>
OHQMZDGELJCFFD-UHFFFAOYSA-N

> <FORMULA>
C15H14O6

> <MOLECULAR_WEIGHT>
290.271

> <EXACT_MASS>
290.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.882548183986533

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3,7-dihydroxy-9-methoxy-3-methyl-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-5,10-dione

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
0.368142124

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.377267054377336

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.367532983159445

> <JCHEM_PKA_STRONGEST_BASIC>
-4.009576334206362

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
74.29789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3,7-dihydroxy-9-methoxy-3-methyl-1H,4H-naphtho[2,3-c]pyran-5,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.6086    1.7622   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2611    1.4677   -0.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    0.2420   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.7825    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -2.0074    0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1672   -3.0005    0.8999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -2.1605    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737   -1.1572    0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4567    0.0553    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    1.1146   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742    2.2316   -0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    0.8863    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073   -0.2649    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8780   -0.3838    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098    0.2912   -0.4724 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0616    0.4559   -0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566   -0.6189   -1.5539 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646    1.4474   -0.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840    1.9385   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693   -1.3376    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9187   -2.4329    1.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1434    2.0239    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714    2.5882   -1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1594    0.9015   -1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7537   -0.6509    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508   -3.6701    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256   -3.1100    1.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1331    0.1376    1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -1.4415    0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1923    1.3845    0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3473   -0.3783    0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7622    0.4031   -0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8006   -1.1054   -1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2478    2.4806    0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834    2.6905   -0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  6
 15 18  1  0
 18 19  1  0
 13 20  1  0
 20 21  2  0
  9  3  1  0
 19 12  1  0
 20  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 14 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  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      -4.609   1.762  -0.818  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.261   1.468  -0.589  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.810   0.242  -0.115  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.690  -0.783   0.164  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.240  -2.007   0.637  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.167  -3.001   0.900  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.884  -2.160   0.817  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.974  -1.157   0.548  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.457   0.055   0.077  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.473   1.115  -0.205  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.874   2.232  -0.636  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.951   0.886   0.008  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.407  -0.265   0.456  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.878  -0.384   0.635  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.610   0.291  -0.472  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.062   0.456  -0.030  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.657  -0.619  -1.554  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.065   1.447  -0.939  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.984   1.938  -0.266  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.469  -1.338   0.746  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.919  -2.433   1.174  0.00  0.00           O+0
HETATM   22  H   UNK     0      -5.143   2.024   0.132  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.671   2.588  -1.557  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.159   0.902  -1.265  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.754  -0.651   0.018  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.451  -3.670   0.193  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.526  -3.110   1.185  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.133   0.138   1.583  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.175  -1.442   0.720  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.192   1.385   0.564  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.347  -0.378   0.656  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.762   0.403  -0.888  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.801  -1.105  -1.641  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.248   2.481   0.674  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.483   2.691  -0.910  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   26                                                       
CONECT    7    5    8   27                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10    3                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   28   29                                             
CONECT   15   14   16   17   18                                             
CONECT   16   15   30   31   32                                             
CONECT   17   15   33                                                       
CONECT   18   15   19                                                       
CONECT   19   18   12   34   35                                             
CONECT   20   13   21    8                                                  
CONECT   21   20                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28   14                                                            
CONECT   29   14                                                            
CONECT   30   16                                                            
CONECT   31   16                                                            
CONECT   32   16                                                            
CONECT   33   17                                                            
CONECT   34   19                                                            
CONECT   35   19                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

RDKit          3D

35 37  0  0  0  0  0  0  0  0999 V2000
   -4.6086    1.7622   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2611    1.4677   -0.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    0.2420   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898   -0.7825    0.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -2.0074    0.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1672   -3.0005    0.8999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -2.1605    0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737   -1.1572    0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4567    0.0553    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    1.1146   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742    2.2316   -0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    0.8863    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073   -0.2649    0.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8780   -0.3838    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098    0.2912   -0.4724 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0616    0.4559   -0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566   -0.6189   -1.5539 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646    1.4474   -0.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840    1.9385   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693   -1.3376    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9187   -2.4329    1.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1434    2.0239    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714    2.5882   -1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1594    0.9015   -1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7537   -0.6509    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508   -3.6701    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256   -3.1100    1.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1331    0.1376    1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -1.4415    0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1923    1.3845    0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3473   -0.3783    0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7622    0.4031   -0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8006   -1.1054   -1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2478    2.4806    0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834    2.6905   -0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  6
 15 18  1  0
 18 19  1  0
 13 20  1  0
 20 21  2  0
  9  3  1  0
 19 12  1  0
 20  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
 14 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₆

Average Mass

290.2710 Da

Monoisotopic Mass

290.07904 Da

IUPAC Name

(3S)-3,7-dihydroxy-9-methoxy-3-methyl-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-5,10-dione

Traditional Name

(3S)-3,7-dihydroxy-9-methoxy-3-methyl-1H,4H-naphtho[2,3-c]pyran-5,10-dione

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)C3=C(CC(C)(O)OC3)C(=O)C2=CC(O)=C1

InChI Identifier

InChI=1S/C15H14O6/c1-15(19)5-9-10(6-21-15)14(18)12-8(13(9)17)3-7(16)4-11(12)20-2/h3-4,16,19H,5-6H2,1-2H3

InChI Key

OHQMZDGELJCFFD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, 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
Corynespora	NPAtlas	20521776

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Benzoisochromanequinones

Direct Parent

Benzoisochromanequinones

Alternative Parents

Substituents

Benzoisochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Naphthalene
Aryl ketone
Quinone
Anisole
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Ketone
Hemiacetal
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.65	ALOGPS
logP	0.37	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	5.37	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.3 m³·mol⁻¹	ChemAxon
Polarizability	28.88 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

NPA016881

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78436006

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46850691

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wijeratne EM, Bashyal BP, Gunatilaka MK, Arnold AE, Gunatilaka AA: Maximizing chemical diversity of fungal metabolites: biogenetically related Heptaketides of the endolichenic fungus Corynespora sp. (1). J Nat Prod. 2010 Jun 25;73(6):1156-9. doi: 10.1021/np900684v. [PubMed:20521776 ]

Showing NP-Card for 7-desmethylherbarin (NP0009256)

MOL for NP0009256 (7-desmethylherbarin)

3D MOL for NP0009256 (7-desmethylherbarin)

3D SDF for NP0009256 (7-desmethylherbarin)

3D-SDF for NP0009256 (7-desmethylherbarin)

PDB for NP0009256 (7-desmethylherbarin)

3D PDB for NP0009256 (7-desmethylherbarin)

SMILES for NP0009256 (7-desmethylherbarin)

INCHI for NP0009256 (7-desmethylherbarin)

Structure for NP0009256 (7-desmethylherbarin)

3D Structure for NP0009256 (7-desmethylherbarin)