NP-MRD: Showing NP-Card for (+)-cochlearol A (NP0013465)

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Record Information

Version

2.0

Created at

2021-01-05 22:49:12 UTC

Updated at

2021-07-15 17:14:33 UTC

NP-MRD ID

NP0013465

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-cochlearol A

Provided By

NPAtlas

Description

(1S,10S,13R)-3,6-dihydroxy-8-oxo-14,16-dioxatetracyclo[11.2.1.0¹,¹⁰.0²,⁷]Hexadeca-2,4,6-triene-10-carboxylic acid belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (+)-cochlearol A is found in Ganoderma. It was first documented in 2012 (PMID: 34383397). Based on a literature review very few articles have been published on (1S,10S,13R)-3,6-dihydroxy-8-oxo-14,16-dioxatetracyclo[11.2.1.0¹,¹⁰.0²,⁷]Hexadeca-2,4,6-triene-10-carboxylic acid (PMID: 25402560) (PMID: 34383398) (PMID: 33749282) (PMID: 31433660).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119363D          

 36 39  0  0  0  0            999 V2000
    0.5354    3.0453   -1.3240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4193    1.8285   -1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802    1.0168   -1.6174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2667    0.4322   -0.2877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6647    1.5584    0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5640    2.7505    0.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739    1.4926    1.8429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078   -0.4037   -0.6823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6791   -1.5448    0.3169 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4186   -2.3389    0.2813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7566   -2.3362    1.5070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -0.9841    1.6069 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2544   -0.5082    0.2050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4420   -1.7283   -0.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1675   -0.1194    0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1931   -0.9023    0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9529   -2.0558    1.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180   -0.5299    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    0.6016   -0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391    1.4093   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437    2.5475   -1.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287    1.0376   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5350    0.2313   -2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5620    1.7206   -1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    2.1021    2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979    0.2205   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241   -0.8849   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616   -2.1324   -0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9737   -1.1188    1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6434   -3.3607   -0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760   -0.5311    2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4377   -0.8838    2.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7192   -2.6045    1.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305   -1.1419    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725    0.9400   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5364    3.1750   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22  2  1  0  0  0  0
 13  4  1  0  0  0  0
 22 15  1  0  0  0  0
 14 10  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  7 25  1  0  0  0  0
  8 26  1  0  0  0  0
  8 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  6  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 17 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  0  0  0  0
 21 36  1  0  0  0  0
M  END

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
    0.5354    3.0453   -1.3240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4193    1.8285   -1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802    1.0168   -1.6174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667    0.4322   -0.2877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6647    1.5584    0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5640    2.7505    0.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739    1.4926    1.8429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078   -0.4037   -0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791   -1.5448    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186   -2.3389    0.2813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7566   -2.3362    1.5070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -0.9841    1.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2544   -0.5082    0.2050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4420   -1.7283   -0.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1675   -0.1194    0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1931   -0.9023    0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9529   -2.0558    1.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180   -0.5299    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    0.6016   -0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391    1.4093   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437    2.5475   -1.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287    1.0376   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5350    0.2313   -2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5620    1.7206   -1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    2.1021    2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979    0.2205   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241   -0.8849   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616   -2.1324   -0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9737   -1.1188    1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6434   -3.3607   -0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760   -0.5311    2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4377   -0.8838    2.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7192   -2.6045    1.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305   -1.1419    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725    0.9400   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5364    3.1750   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  1
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  1  1
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 13  4  1  0
 22 15  1  0
 14 10  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  6
 12 31  1  0
 12 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
M  END


  Mrv1652306242119363D          

 36 39  0  0  0  0            999 V2000
    0.5354    3.0453   -1.3240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4193    1.8285   -1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802    1.0168   -1.6174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2667    0.4322   -0.2877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6647    1.5584    0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5640    2.7505    0.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739    1.4926    1.8429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078   -0.4037   -0.6823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6791   -1.5448    0.3169 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4186   -2.3389    0.2813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7566   -2.3362    1.5070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -0.9841    1.6069 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2544   -0.5082    0.2050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4420   -1.7283   -0.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1675   -0.1194    0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1931   -0.9023    0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9529   -2.0558    1.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180   -0.5299    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    0.6016   -0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391    1.4093   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437    2.5475   -1.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287    1.0376   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5350    0.2313   -2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5620    1.7206   -1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    2.1021    2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979    0.2205   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241   -0.8849   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616   -2.1324   -0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9737   -1.1188    1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6434   -3.3607   -0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760   -0.5311    2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4377   -0.8838    2.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7192   -2.6045    1.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305   -1.1419    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725    0.9400   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5364    3.1750   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22  2  1  0  0  0  0
 13  4  1  0  0  0  0
 22 15  1  0  0  0  0
 14 10  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  7 25  1  0  0  0  0
  8 26  1  0  0  0  0
  8 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  6  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 17 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  0  0  0  0
 21 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0013465

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]12C([H])([H])C(=O)C3=C(O[H])C([H])=C([H])C(O[H])=C3[C@]11O[C@@]([H])(OC1([H])[H])C([H])([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O7/c16-7-1-2-8(17)12-11(7)9(18)5-14(13(19)20)4-3-10-21-6-15(12,14)22-10/h1-2,10,16-17H,3-6H2,(H,19,20)/t10-,14-,15+/m1/s1

> <INCHI_KEY>
APQUUNCMRUQJLX-KMUNFCNLSA-N

> <FORMULA>
C15H14O7

> <MOLECULAR_WEIGHT>
306.27

> <EXACT_MASS>
306.073952791

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.109389711728433

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10S,13R)-3,6-dihydroxy-8-oxo-14,16-dioxatetracyclo[11.2.1.0^{1,10}.0^{2,7}]hexadeca-2,4,6-triene-10-carboxylic acid

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
1.4444563853333332

> <ALOGPS_LOGS>
-1.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.700923900640065

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.323611654053809

> <JCHEM_PKA_STRONGEST_BASIC>
-4.075898965815121

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
71.8236

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10S,13R)-3,6-dihydroxy-8-oxo-14,16-dioxatetracyclo[11.2.1.0^{1,10}.0^{2,7}]hexadeca-2,4,6-triene-10-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
    0.5354    3.0453   -1.3240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4193    1.8285   -1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802    1.0168   -1.6174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667    0.4322   -0.2877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6647    1.5584    0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5640    2.7505    0.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739    1.4926    1.8429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078   -0.4037   -0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791   -1.5448    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186   -2.3389    0.2813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7566   -2.3362    1.5070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -0.9841    1.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2544   -0.5082    0.2050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4420   -1.7283   -0.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1675   -0.1194    0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1931   -0.9023    0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9529   -2.0558    1.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180   -0.5299    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    0.6016   -0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391    1.4093   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437    2.5475   -1.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287    1.0376   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5350    0.2313   -2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5620    1.7206   -1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    2.1021    2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979    0.2205   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241   -0.8849   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616   -2.1324   -0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9737   -1.1188    1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6434   -3.3607   -0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760   -0.5311    2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4377   -0.8838    2.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7192   -2.6045    1.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305   -1.1419    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725    0.9400   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5364    3.1750   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  1
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  1  1
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 13  4  1  0
 22 15  1  0
 14 10  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  6
 12 31  1  0
 12 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  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  O   UNK     0       0.535   3.045  -1.324  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.419   1.829  -1.230  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.780   1.017  -1.617  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.267   0.432  -0.288  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.665   1.558   0.554  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.564   2.751   0.130  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.174   1.493   1.843  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.508  -0.404  -0.682  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.679  -1.545   0.317  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.419  -2.339   0.281  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.757  -2.336   1.507  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.432  -0.984   1.607  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.254  -0.508   0.205  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.442  -1.728  -0.519  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.167  -0.119   0.001  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.193  -0.902   0.502  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.953  -2.056   1.191  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.518  -0.530   0.310  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.876   0.602  -0.369  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.839   1.409  -0.887  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.144   2.547  -1.577  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.529   1.038  -0.694  0.00  0.00           C+0
HETATM   23  H   UNK     0      -0.535   0.231  -2.355  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.562   1.721  -1.963  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.856   2.102   2.226  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.398   0.221  -0.774  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.324  -0.885  -1.665  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.562  -2.132  -0.052  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.974  -1.119   1.268  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.643  -3.361  -0.079  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.276  -0.531   2.164  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.438  -0.884   2.272  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.719  -2.604   1.543  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.330  -1.142   0.703  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.872   0.940  -0.548  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.536   3.175  -1.998  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   23   24                                             
CONECT    4    3    5    8   13                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5   25                                                       
CONECT    8    4    9   26   27                                             
CONECT    9    8   10   28   29                                             
CONECT   10    9   11   14   30                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   31   32                                             
CONECT   13   12   14   15    4                                             
CONECT   14   13   10                                                       
CONECT   15   13   16   22                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   33                                                       
CONECT   18   16   19   34                                                  
CONECT   19   18   20   35                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   36                                                       
CONECT   22   20    2   15                                                  
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    7                                                            
CONECT   26    8                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   17                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   21                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

RDKit          3D

36 39  0  0  0  0  0  0  0  0999 V2000
    0.5354    3.0453   -1.3240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4193    1.8285   -1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802    1.0168   -1.6174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667    0.4322   -0.2877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6647    1.5584    0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5640    2.7505    0.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739    1.4926    1.8429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078   -0.4037   -0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791   -1.5448    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186   -2.3389    0.2813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7566   -2.3362    1.5070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -0.9841    1.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2544   -0.5082    0.2050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4420   -1.7283   -0.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1675   -0.1194    0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1931   -0.9023    0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9529   -2.0558    1.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180   -0.5299    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    0.6016   -0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391    1.4093   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437    2.5475   -1.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287    1.0376   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5350    0.2313   -2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5620    1.7206   -1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    2.1021    2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979    0.2205   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241   -0.8849   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616   -2.1324   -0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9737   -1.1188    1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6434   -3.3607   -0.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760   -0.5311    2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4377   -0.8838    2.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7192   -2.6045    1.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305   -1.1419    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725    0.9400   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5364    3.1750   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  1
  5  6  2  0
  5  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  1  1
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 13  4  1  0
 22 15  1  0
 14 10  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  6
 12 31  1  0
 12 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1S,10S,13R)-3,6-Dihydroxy-8-oxo-14,16-dioxatetracyclo[11.2.1.0,.0,]hexadeca-2,4,6-triene-10-carboxylate	Generator

Chemical Formula

C₁₅H₁₄O₇

Average Mass

306.2700 Da

Monoisotopic Mass

306.07395 Da

IUPAC Name

(1S,10S,13R)-3,6-dihydroxy-8-oxo-14,16-dioxatetracyclo[11.2.1.0^{1,10}.0^{2,7}]hexadeca-2,4,6-triene-10-carboxylic acid

Traditional Name

(1S,10S,13R)-3,6-dihydroxy-8-oxo-14,16-dioxatetracyclo[11.2.1.0^{1,10}.0^{2,7}]hexadeca-2,4,6-triene-10-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)[C@]12CC[C@@H]3OC[C@]1(O3)C1=C(O)C=CC(O)=C1C(=O)C2

InChI Identifier

InChI=1S/C15H14O7/c16-7-1-2-8(17)12-11(7)9(18)5-14(13(19)20)4-3-10-21-6-15(12,14)22-10/h1-2,10,16-17H,3-6H2,(H,19,20)/t10-,14-,15+/m1/s1

InChI Key

APQUUNCMRUQJLX-KMUNFCNLSA-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
Ganoderma	NPAtlas	25402560

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
2-naphthalenecarboxylic acid or derivatives
2-naphthalenecarboxylic acid
Tetralin
Naphthalene
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Oxepane
Benzenoid
Pyran
Oxane
Vinylogous acid
Meta-dioxolane
Ketone
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	0.75	ALOGPS
logP	1.44	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.82 m³·mol⁻¹	ChemAxon
Polarizability	28.11 Å³	ChemAxon
Number of Rings	4	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

NPA001268

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78440741

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583439

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dou M, Di L, Zhou LL, Yan YM, Wang XL, Zhou FJ, Yang ZL, Li RT, Hou FF, Cheng YX: Cochlearols A and B, polycyclic meroterpenoids from the fungus Ganoderma cochlear that have renoprotective activities. Org Lett. 2014 Dec 5;16(23):6064-7. doi: 10.1021/ol502806j. Epub 2014 Nov 17. [PubMed:25402560 ]
Mitchell PM: The cost-effectiveness of what in health and care?. 2021 Feb. [PubMed:34383398 ]
Authors unspecified: Ozanimod. 2012. [PubMed:34383397 ]
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Showing NP-Card for (+)-cochlearol A (NP0013465)

MOL for NP0013465 ((+)-cochlearol A)

3D MOL for NP0013465 ((+)-cochlearol A)

3D SDF for NP0013465 ((+)-cochlearol A)

3D-SDF for NP0013465 ((+)-cochlearol A)

PDB for NP0013465 ((+)-cochlearol A)

3D PDB for NP0013465 ((+)-cochlearol A)

SMILES for NP0013465 ((+)-cochlearol A)

INCHI for NP0013465 ((+)-cochlearol A)

Structure for NP0013465 ((+)-cochlearol A)

3D Structure for NP0013465 ((+)-cochlearol A)