NP-MRD: Showing NP-Card for Rubrocashmeriquinone (NP0008795)

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Record Information

Version

2.0

Created at

2020-12-09 06:17:51 UTC

Updated at

2021-07-15 17:01:26 UTC

NP-MRD ID

NP0008795

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rubrocashmeriquinone

Provided By

NPAtlas

Description

6,8-Dihydroxy-2-methyl-4H,4aH,5H,9H,10aH-cyclohexa[g]chromene-4,5,9-trione 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. Rubrocashmeriquinone is found in Lethariella sernanderi. Rubrocashmeriquinone was first documented in 2010 (PMID: 19802654). Based on a literature review very few articles have been published on 6,8-dihydroxy-2-methyl-4H,4aH,5H,9H,10aH-cyclohexa[g]chromene-4,5,9-trione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106303D          

 30 32  0  0  0  0            999 V2000
    4.6487    0.9215   -0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3373    0.2455   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3109   -1.0828   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175   -1.7065   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170   -2.9081    0.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163   -0.8547   -0.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3887   -1.4316    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -2.4893    1.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6010   -0.5987    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -1.1283    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9431   -2.5015    0.3439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121   -0.3147    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8594    1.0132   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9826    1.8222   -0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598    1.6701   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    2.9166   -0.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3606    0.8384    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1560    1.3557    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    0.5183    0.3007 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1950    1.0424   -0.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050    1.3844   -1.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373    1.6708    0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4776    0.1846   -0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381   -1.6416   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180   -0.7500   -1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7384   -3.0512   -0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049   -0.7458    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    2.7936    0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0856    2.4517    0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741    0.3758    1.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20  2  1  0  0  0  0
 19  6  1  0  0  0  0
 17  9  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
  3 24  1  0  0  0  0
  6 25  1  6  0  0  0
 11 26  1  0  0  0  0
 12 27  1  0  0  0  0
 14 28  1  0  0  0  0
 18 29  1  0  0  0  0
 19 30  1  1  0  0  0
M  END

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    4.6487    0.9215   -0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3373    0.2455   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3109   -1.0828   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175   -1.7065   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170   -2.9081    0.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163   -0.8547   -0.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3887   -1.4316    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -2.4893    1.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6010   -0.5987    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -1.1283    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9431   -2.5015    0.3439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121   -0.3147    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8594    1.0132   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9826    1.8222   -0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598    1.6701   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    2.9166   -0.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3606    0.8384    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1560    1.3557    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    0.5183    0.3007 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1950    1.0424   -0.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050    1.3844   -1.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373    1.6708    0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4776    0.1846   -0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381   -1.6416   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180   -0.7500   -1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7384   -3.0512   -0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049   -0.7458    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    2.7936    0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0856    2.4517    0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741    0.3758    1.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 19  6  1  0
 17  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  6
 11 26  1  0
 12 27  1  0
 14 28  1  0
 18 29  1  0
 19 30  1  1
M  END


  Mrv1652306242106303D          

 30 32  0  0  0  0            999 V2000
    4.6487    0.9215   -0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3373    0.2455   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3109   -1.0828   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175   -1.7065   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170   -2.9081    0.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163   -0.8547   -0.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3887   -1.4316    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -2.4893    1.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6010   -0.5987    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -1.1283    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9431   -2.5015    0.3439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121   -0.3147    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8594    1.0132   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9826    1.8222   -0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598    1.6701   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    2.9166   -0.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3606    0.8384    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1560    1.3557    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    0.5183    0.3007 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1950    1.0424   -0.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050    1.3844   -1.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373    1.6708    0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4776    0.1846   -0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381   -1.6416   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180   -0.7500   -1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7384   -3.0512   -0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049   -0.7458    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    2.7936    0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0856    2.4517    0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741    0.3758    1.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20  2  1  0  0  0  0
 19  6  1  0  0  0  0
 17  9  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
  3 24  1  0  0  0  0
  6 25  1  6  0  0  0
 11 26  1  0  0  0  0
 12 27  1  0  0  0  0
 14 28  1  0  0  0  0
 18 29  1  0  0  0  0
 19 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0008795

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)[C@]3([H])C(=O)C([H])=C(O[C@@]3([H])C([H])=C2C1=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O6/c1-5-2-7(15)12-10(20-5)3-6-11(14(12)19)8(16)4-9(17)13(6)18/h2-4,10,12,16-17H,1H3/t10-,12+/m0/s1

> <INCHI_KEY>
FFDDYPNVBJUCAM-UHFFFAOYSA-N

> <FORMULA>
C14H10O6

> <MOLECULAR_WEIGHT>
274.228

> <EXACT_MASS>
274.047738042

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.11412749428648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,10aS)-6,8-dihydroxy-2-methyl-4H,4aH,5H,9H,10aH-cyclohexa[g]chromene-4,5,9-trione

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
0.18847999766666673

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.093625742556346

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.259237487357519

> <JCHEM_PKA_STRONGEST_BASIC>
-4.086738336610016

> <JCHEM_POLAR_SURFACE_AREA>
100.90000000000002

> <JCHEM_REFRACTIVITY>
72.28110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,10aS)-6,8-dihydroxy-2-methyl-4aH,10aH-cyclohexa[g]chromene-4,5,9-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    4.6487    0.9215   -0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3373    0.2455   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3109   -1.0828   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175   -1.7065   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170   -2.9081    0.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163   -0.8547   -0.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3887   -1.4316    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -2.4893    1.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6010   -0.5987    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -1.1283    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9431   -2.5015    0.3439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121   -0.3147    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8594    1.0132   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9826    1.8222   -0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598    1.6701   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    2.9166   -0.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3606    0.8384    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1560    1.3557    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    0.5183    0.3007 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1950    1.0424   -0.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050    1.3844   -1.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373    1.6708    0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4776    0.1846   -0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381   -1.6416   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180   -0.7500   -1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7384   -3.0512   -0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049   -0.7458    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    2.7936    0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0856    2.4517    0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741    0.3758    1.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 19  6  1  0
 17  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  6
 11 26  1  0
 12 27  1  0
 14 28  1  0
 18 29  1  0
 19 30  1  1
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       4.649   0.922  -0.631  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.337   0.246  -0.427  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.311  -1.083  -0.338  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.018  -1.706  -0.141  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.917  -2.908   0.105  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.816  -0.855  -0.243  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.389  -1.432   0.393  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.478  -2.489   1.019  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.601  -0.599   0.223  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.813  -1.128   0.203  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.943  -2.502   0.344  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.012  -0.315   0.037  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.859   1.013  -0.096  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.983   1.822  -0.256  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.560   1.670  -0.080  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.489   2.917  -0.209  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.361   0.838   0.087  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.156   1.356   0.119  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.040   0.518   0.301  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.195   1.042  -0.340  0.00  0.00           O+0
HETATM   21  H   UNK     0       4.705   1.384  -1.635  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.837   1.671   0.173  0.00  0.00           H+0
HETATM   23  H   UNK     0       5.478   0.185  -0.558  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.238  -1.642  -0.415  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.618  -0.750  -1.336  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.738  -3.051  -0.497  0.00  0.00           H+0
HETATM   27  H   UNK     0      -5.005  -0.746   0.019  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.961   2.794   0.060  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.086   2.452   0.003  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.274   0.376   1.403  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    1    3   20                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   19   25                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   17                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   26                                                       
CONECT   12   10   13   27                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   28                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18    9                                                  
CONECT   18   17   19   29                                                  
CONECT   19   18   20    6   30                                             
CONECT   20   19    2                                                       
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    3                                                            
CONECT   25    6                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   14                                                            
CONECT   29   18                                                            
CONECT   30   19                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

RDKit          3D

30 32  0  0  0  0  0  0  0  0999 V2000
    4.6487    0.9215   -0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3373    0.2455   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3109   -1.0828   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175   -1.7065   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170   -2.9081    0.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8163   -0.8547   -0.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3887   -1.4316    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -2.4893    1.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6010   -0.5987    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -1.1283    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9431   -2.5015    0.3439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121   -0.3147    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8594    1.0132   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9826    1.8222   -0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598    1.6701   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    2.9166   -0.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3606    0.8384    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1560    1.3557    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    0.5183    0.3007 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1950    1.0424   -0.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050    1.3844   -1.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373    1.6708    0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4776    0.1846   -0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381   -1.6416   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180   -0.7500   -1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7384   -3.0512   -0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049   -0.7458    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    2.7936    0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0856    2.4517    0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741    0.3758    1.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 19  6  1  0
 17  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  6
 11 26  1  0
 12 27  1  0
 14 28  1  0
 18 29  1  0
 19 30  1  1
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₄H₁₀O₆

Average Mass

274.2280 Da

Monoisotopic Mass

274.04774 Da

IUPAC Name

(4aS,10aS)-6,8-dihydroxy-2-methyl-4H,4aH,5H,9H,10aH-cyclohexa[g]chromene-4,5,9-trione

Traditional Name

(4aS,10aS)-6,8-dihydroxy-2-methyl-4aH,10aH-cyclohexa[g]chromene-4,5,9-trione

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2C(O1)C=C1C(=O)C(O)=CC(O)=C1C2=O

InChI Identifier

InChI=1S/C14H10O6/c1-5-2-7(15)12-10(20-5)3-6-11(14(12)19)8(16)4-9(17)13(6)18/h2-4,10,12,16-17H,1H3

InChI Key

FFDDYPNVBJUCAM-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
Lethariella sernanderi	NPAtlas	19802654

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
Naphthalene
Cyclohexenone
1,3-diketone
Pyranone
Dihydropyranone
1,3-dicarbonyl compound
Pyran
Vinylogous ester
Vinylogous acid
Ketone
Oxacycle
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.88	ALOGPS
logP	0.19	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.26	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.28 m³·mol⁻¹	ChemAxon
Polarizability	26.11 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

NPA002155

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435926

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583700

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kinoshita K, Togawa T, Hiraishi A, Nakajima Y, Koyama K, Narui T, Wang LS, Takahashi K: Antioxidant activity of red pigments from the lichens Lethariella sernanderi, L. cashmeriana, and L. sinensis. J Nat Med. 2010 Jan;64(1):85-8. doi: 10.1007/s11418-009-0364-2. Epub 2009 Oct 3. [PubMed:19802654 ]

Showing NP-Card for Rubrocashmeriquinone (NP0008795)

MOL for NP0008795 (Rubrocashmeriquinone)

3D MOL for NP0008795 (Rubrocashmeriquinone)

3D SDF for NP0008795 (Rubrocashmeriquinone)

3D-SDF for NP0008795 (Rubrocashmeriquinone)

PDB for NP0008795 (Rubrocashmeriquinone)

3D PDB for NP0008795 (Rubrocashmeriquinone)

SMILES for NP0008795 (Rubrocashmeriquinone)

INCHI for NP0008795 (Rubrocashmeriquinone)

Structure for NP0008795 (Rubrocashmeriquinone)

3D Structure for NP0008795 (Rubrocashmeriquinone)