NP-MRD: Showing NP-Card for (-)-semivioxanthin (NP0003645)

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Record Information

Version

1.0

Created at

2020-12-09 00:50:11 UTC

Updated at

2021-07-15 16:46:59 UTC

NP-MRD ID

NP0003645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-semivioxanthin

Provided By

NPAtlas

Description

(3S)-9,10-dihydroxy-7-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-1-one belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. (-)-semivioxanthin is found in Cryptosporiopsis and Pezicula livida. It was first documented in 2001 (PMID: 11302197). Based on a literature review very few articles have been published on (3S)-9,10-dihydroxy-7-methoxy-3-methyl-1H,3H,4H-naphtho[2,3-c]pyran-1-one (PMID: 34380192) (PMID: 34380191) (PMID: 34380190) (PMID: 34380189).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117493D          

 34 36  0  0  0  0            999 V2000
   -5.6767    0.5373   -0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4821    1.0871   -0.8328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    0.5093   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635   -0.5416    0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0843   -1.1177    0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535   -2.1698    1.8056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8906   -0.6247    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3043   -1.1829    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067   -2.2130    1.7294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987   -0.6319    0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119    0.4038   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243    0.9597   -0.9370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8556    0.4426   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674    0.9716   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010    0.9464   -1.0363 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9281    0.6831   -0.0948 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2510    0.9522   -0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9313   -0.6839    0.2907 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7531   -1.2331    0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8282   -2.1825    1.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369   -0.5620   -0.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5734    0.9616   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7177    0.6457    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2028   -0.9587    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0205   -2.5369    2.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1701   -2.7691    2.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    1.7930   -1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807    1.8097   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981    2.0153   -1.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0028    0.4198   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058    1.2865    0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909    2.0242   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490    0.6670   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3716    0.2920   -1.6274 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  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14  3  1  0  0  0  0
 13  7  1  0  0  0  0
 19 10  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  4 24  1  0  0  0  0
  6 25  1  0  0  0  0
  9 26  1  0  0  0  0
 12 27  1  0  0  0  0
 14 28  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  1  0  0  0
 17 32  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
M  END

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.6767    0.5373   -0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4821    1.0871   -0.8328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    0.5093   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635   -0.5416    0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0843   -1.1177    0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535   -2.1698    1.8056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8906   -0.6247    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3043   -1.1829    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067   -2.2130    1.7294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987   -0.6319    0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119    0.4038   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243    0.9597   -0.9370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8556    0.4426   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674    0.9716   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010    0.9464   -1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281    0.6831   -0.0948 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2510    0.9522   -0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9313   -0.6839    0.2907 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7531   -1.2331    0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8282   -2.1825    1.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369   -0.5620   -0.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5734    0.9616   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7177    0.6457    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2028   -0.9587    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0205   -2.5369    2.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1701   -2.7691    2.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    1.7930   -1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807    1.8097   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981    2.0153   -1.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0028    0.4198   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058    1.2865    0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909    2.0242   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490    0.6670   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3716    0.2920   -1.6274 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  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 14  3  1  0
 13  7  1  0
 19 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  1
 17 32  1  0
 17 33  1  0
 17 34  1  0
M  END


  Mrv1652306242117493D          

 34 36  0  0  0  0            999 V2000
   -5.6767    0.5373   -0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4821    1.0871   -0.8328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    0.5093   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635   -0.5416    0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0843   -1.1177    0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535   -2.1698    1.8056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8906   -0.6247    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3043   -1.1829    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067   -2.2130    1.7294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987   -0.6319    0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119    0.4038   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243    0.9597   -0.9370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8556    0.4426   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674    0.9716   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010    0.9464   -1.0363 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9281    0.6831   -0.0948 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2510    0.9522   -0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9313   -0.6839    0.2907 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7531   -1.2331    0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8282   -2.1825    1.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369   -0.5620   -0.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5734    0.9616   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7177    0.6457    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2028   -0.9587    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0205   -2.5369    2.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1701   -2.7691    2.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    1.7930   -1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807    1.8097   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981    2.0153   -1.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0028    0.4198   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058    1.2865    0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909    2.0242   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490    0.6670   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3716    0.2920   -1.6274 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  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14  3  1  0  0  0  0
 13  7  1  0  0  0  0
 19 10  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  4 24  1  0  0  0  0
  6 25  1  0  0  0  0
  9 26  1  0  0  0  0
 12 27  1  0  0  0  0
 14 28  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
 16 31  1  1  0  0  0
 17 32  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003645

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(O[H])=C3C(=O)O[C@@]([H])(C([H])([H])[H])C([H])([H])C3=C([H])C2=C([H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-7-3-8-4-9-5-10(19-2)6-11(16)12(9)14(17)13(8)15(18)20-7/h4-7,16-17H,3H2,1-2H3/t7-/m0/s1

> <INCHI_KEY>
BWNCKEBBYADFPQ-ZETCQYMHSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.272

> <EXACT_MASS>
274.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.47279378562031

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
3.1078611586666662

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.716545277078671

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.460773501088157

> <JCHEM_PKA_STRONGEST_BASIC>
-4.471777320323214

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
72.6869

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.6767    0.5373   -0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4821    1.0871   -0.8328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    0.5093   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635   -0.5416    0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0843   -1.1177    0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535   -2.1698    1.8056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8906   -0.6247    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3043   -1.1829    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067   -2.2130    1.7294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987   -0.6319    0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119    0.4038   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243    0.9597   -0.9370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8556    0.4426   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674    0.9716   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010    0.9464   -1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281    0.6831   -0.0948 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2510    0.9522   -0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9313   -0.6839    0.2907 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7531   -1.2331    0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8282   -2.1825    1.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369   -0.5620   -0.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5734    0.9616   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7177    0.6457    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2028   -0.9587    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0205   -2.5369    2.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1701   -2.7691    2.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    1.7930   -1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807    1.8097   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981    2.0153   -1.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0028    0.4198   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058    1.2865    0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909    2.0242   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490    0.6670   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3716    0.2920   -1.6274 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  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 14  3  1  0
 13  7  1  0
 19 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  1
 17 32  1  0
 17 33  1  0
 17 34  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      -5.677   0.537  -0.318  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.482   1.087  -0.833  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.279   0.509  -0.399  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.264  -0.542   0.484  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.084  -1.118   0.917  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.154  -2.170   1.806  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.891  -0.625   0.450  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.304  -1.183   0.867  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.407  -2.213   1.729  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.499  -0.632   0.351  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.512   0.404  -0.521  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.324   0.960  -0.937  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.856   0.443  -0.450  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.067   0.972  -0.842  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.801   0.946  -1.036  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.928   0.683  -0.095  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.251   0.952  -0.766  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.931  -0.684   0.291  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.753  -1.233   0.803  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.828  -2.183   1.599  0.00  0.00           O+0
HETATM   21  H   UNK     0      -5.637  -0.562  -0.524  0.00  0.00           H+0
HETATM   22  H   UNK     0      -6.573   0.962  -0.767  0.00  0.00           H+0
HETATM   23  H   UNK     0      -5.718   0.646   0.792  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.203  -0.959   0.877  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.021  -2.537   2.153  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.170  -2.769   2.223  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.298   1.793  -1.637  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.081   1.810  -1.547  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.698   2.015  -1.255  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.003   0.420  -1.989  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.806   1.287   0.816  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.391   2.024  -1.011  0.00  0.00           H+0
HETATM   33  H   UNK     0       6.049   0.667  -0.026  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.372   0.292  -1.627  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   24                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   25                                                       
CONECT    7    5    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   26                                                       
CONECT   10    8   11   19                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14    7                                                  
CONECT   14   13    3   28                                                  
CONECT   15   11   16   29   30                                             
CONECT   16   15   17   18   31                                             
CONECT   17   16   32   33   34                                             
CONECT   18   16   19                                                       
CONECT   19   18   20   10                                                  
CONECT   20   19                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    4                                                            
CONECT   25    6                                                            
CONECT   26    9                                                            
CONECT   27   12                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   17                                                            
CONECT   33   17                                                            
CONECT   34   17                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
   -5.6767    0.5373   -0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4821    1.0871   -0.8328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2791    0.5093   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2635   -0.5416    0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0843   -1.1177    0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535   -2.1698    1.8056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8906   -0.6247    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3043   -1.1829    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067   -2.2130    1.7294 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987   -0.6319    0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5119    0.4038   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243    0.9597   -0.9370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8556    0.4426   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674    0.9716   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010    0.9464   -1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281    0.6831   -0.0948 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2510    0.9522   -0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9313   -0.6839    0.2907 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7531   -1.2331    0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8282   -2.1825    1.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369   -0.5620   -0.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5734    0.9616   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7177    0.6457    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2028   -0.9587    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0205   -2.5369    2.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1701   -2.7691    2.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    1.7930   -1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807    1.8097   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981    2.0153   -1.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0028    0.4198   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058    1.2865    0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3909    2.0242   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0490    0.6670   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3716    0.2920   -1.6274 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  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 14  3  1  0
 13  7  1  0
 19 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  1
 17 32  1  0
 17 33  1  0
 17 34  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2720 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC2=CC3=C(C(=O)O[C@@H](C)C3)C(O)=C2C(O)=C1

InChI Identifier

InChI=1S/C15H14O5/c1-7-3-8-4-9-5-10(19-2)6-11(16)12(9)14(17)13(8)15(18)20-7/h4-7,16-17H,3H2,1-2H3/t7-/m0/s1

InChI Key

BWNCKEBBYADFPQ-ZETCQYMHSA-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
Cryptosporiopsis	NPAtlas	11302197
Pezicula livida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
1-naphthol
Benzopyran
Isochromane
Naphthalene
2-benzopyran
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Benzenoid
Pyran
Vinylogous acid
Lactone
Carboxylic acid ester
Ether
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	2.55	ALOGPS
logP	3.11	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.46	ChemAxon
pKa (Strongest Basic)	-4.5	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	1	ChemAxon
Refractivity	72.69 m³·mol⁻¹	ChemAxon
Polarizability	28.47 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

NPA012574

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8835262

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10659908

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yada H, Sato H, Toshima H, Deura M, Ichihara A: (-)-Semivioxanthin, a new abscisic active compound against Hinoki cypress leaves isolated from Cryptosporiopsis abietina. Biosci Biotechnol Biochem. 2001 Feb;65(2):484-6. doi: 10.1271/bbb.65.484. [PubMed:11302197 ]
Kim S, Park KY, Chung J, Kim YB, Lee JW, Huh SK: Comparative Analysis of Feasibility of the Retrograde Suction Decompression Technique for Microsurgical Treatment of Large and Giant Internal Carotid Artery Aneurysms. J Korean Neurosurg Soc. 2021 Aug 12. pii: jkns.2021.0066. doi: 10.3340/jkns.2021.0066. [PubMed:34380192 ]
Bahloul M, Kharrat S, Chtara K, Hafdhi M, Turki O, Baccouche N, Ammar R, Kallel N, Hsairi M, Chakroun-Walha O, Hamida CB, Chelly H, Mahfoudh KB, Karoui A, Karray H, Rekik N, Bouaziz M: Clinical characteristics and outcomes of critically ill COVID-19 patients in Sfax, Tunisia. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00129. doi: 10.4266/acc.2021.00129. [PubMed:34380191 ]
Yi J, Kim KH: Identification and infection control of carbapenem-resistant Enterobacterales in intensive care units. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00409. doi: 10.4266/acc.2021.00409. [PubMed:34380190 ]
Lee Y, Kim SH, Hwang HY, Sohn SH, Choi JW, Kim KH: Perfusion parameters during cardiopulmonary bypass as a predictor of acute kidney injury after aortic valve replacement. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00094. doi: 10.4266/acc.2021.00094. [PubMed:34380189 ]

Showing NP-Card for (-)-semivioxanthin (NP0003645)

MOL for NP0003645 ((-)-semivioxanthin)

3D MOL for NP0003645 ((-)-semivioxanthin)

3D SDF for NP0003645 ((-)-semivioxanthin)

3D-SDF for NP0003645 ((-)-semivioxanthin)

PDB for NP0003645 ((-)-semivioxanthin)

3D PDB for NP0003645 ((-)-semivioxanthin)

SMILES for NP0003645 ((-)-semivioxanthin)

INCHI for NP0003645 ((-)-semivioxanthin)

Structure for NP0003645 ((-)-semivioxanthin)

3D Structure for NP0003645 ((-)-semivioxanthin)