NP-MRD: Showing NP-Card for fimbricalyx anhydride A (NP0043558)

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Record Information

Version

1.0

Created at

2021-06-21 00:55:59 UTC

Updated at

2021-06-30 00:19:18 UTC

NP-MRD ID

NP0043558

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fimbricalyx anhydride A

Provided By

JEOL Database JEOL Logo

Description

CHEMBL2409523 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. fimbricalyx anhydride A is found in Strophioblachia fimbricalyx. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on CHEMBL2409523 (PMID: 27466641) (PMID: 27253005) (PMID: 26389468) (PMID: 26389426).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102563D          

 38 40  0  0  0  0            999 V2000
   -0.0599    5.5819   -0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5796    4.8397   -1.8268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818    3.4740   -1.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306    2.7474   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909    1.3271   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946    0.5409    0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -0.8639    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0354   -1.5058   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7449   -0.7579   -1.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132   -1.4117   -2.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897    0.6482   -1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    1.3895   -2.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3530    2.7885   -2.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277    3.5281   -3.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784   -1.6106    1.3140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0393   -3.0007    0.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7576   -1.8023    2.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296   -0.7968    1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -1.3147    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747    0.5345    1.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5528    1.1661    1.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2078    2.2244    1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1083    6.6444   -0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732    5.3567    0.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411    5.4104   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    3.2926   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -2.5884   -0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4525   -2.3710   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993    0.8592   -3.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4479    4.1067   -4.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819    2.8416   -4.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8541    4.2022   -3.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6988   -3.4876    1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1972   -3.6837    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -2.9240   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4271   -0.8480    3.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -2.3084    3.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397   -2.4040    2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  5  2  0  0  0  0
  3  4  2  0  0  0  0
  7 15  1  0  0  0  0
  6 21  1  0  0  0  0
 18 15  1  0  0  0  0
  4  5  1  0  0  0  0
 13 14  1  0  0  0  0
 13  3  1  0  0  0  0
  3  2  1  0  0  0  0
 11  9  1  0  0  0  0
  2  1  1  0  0  0  0
  5  6  1  0  0  0  0
  9 10  1  0  0  0  0
  7  8  1  0  0  0  0
 18 19  2  0  0  0  0
  8  9  2  0  0  0  0
 15 16  1  0  0  0  0
  7  6  2  0  0  0  0
 21 22  2  0  0  0  0
 11 12  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 13  2  0  0  0  0
 15 17  1  0  0  0  0
  4 26  1  0  0  0  0
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  8 27  1  0  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
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  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 10 28  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
M  END

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.0599    5.5819   -0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5796    4.8397   -1.8268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818    3.4740   -1.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306    2.7474   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909    1.3271   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946    0.5409    0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -0.8639    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0354   -1.5058   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7449   -0.7579   -1.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132   -1.4117   -2.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897    0.6482   -1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    1.3895   -2.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3530    2.7885   -2.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277    3.5281   -3.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784   -1.6106    1.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393   -3.0007    0.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7576   -1.8023    2.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296   -0.7968    1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -1.3147    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747    0.5345    1.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5528    1.1661    1.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2078    2.2244    1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1083    6.6444   -0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732    5.3567    0.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411    5.4104   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    3.2926   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -2.5884   -0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4525   -2.3710   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993    0.8592   -3.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4479    4.1067   -4.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819    2.8416   -4.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8541    4.2022   -3.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6988   -3.4876    1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1972   -3.6837    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -2.9240   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4271   -0.8480    3.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -2.3084    3.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397   -2.4040    2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  5  2  0
  3  4  2  0
  7 15  1  0
  6 21  1  0
 18 15  1  0
  4  5  1  0
 13 14  1  0
 13  3  1  0
  3  2  1  0
 11  9  1  0
  2  1  1  0
  5  6  1  0
  9 10  1  0
  7  8  1  0
 18 19  2  0
  8  9  2  0
 15 16  1  0
  7  6  2  0
 21 22  2  0
 11 12  1  0
 18 20  1  0
 20 21  1  0
 12 13  2  0
 15 17  1  0
  4 26  1  0
 12 29  1  0
  8 27  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 10 28  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  END


  Mrv1652306212102563D          

 38 40  0  0  0  0            999 V2000
   -0.0599    5.5819   -0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5796    4.8397   -1.8268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818    3.4740   -1.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306    2.7474   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909    1.3271   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946    0.5409    0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -0.8639    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0354   -1.5058   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7449   -0.7579   -1.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132   -1.4117   -2.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897    0.6482   -1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    1.3895   -2.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3530    2.7885   -2.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277    3.5281   -3.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784   -1.6106    1.3140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0393   -3.0007    0.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7576   -1.8023    2.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296   -0.7968    1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -1.3147    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747    0.5345    1.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5528    1.1661    1.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2078    2.2244    1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1083    6.6444   -0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732    5.3567    0.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411    5.4104   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    3.2926   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -2.5884   -0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4525   -2.3710   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993    0.8592   -3.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4479    4.1067   -4.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819    2.8416   -4.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8541    4.2022   -3.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6988   -3.4876    1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1972   -3.6837    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -2.9240   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4271   -0.8480    3.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -2.3084    3.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397   -2.4040    2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  5  2  0  0  0  0
  3  4  2  0  0  0  0
  7 15  1  0  0  0  0
  6 21  1  0  0  0  0
 18 15  1  0  0  0  0
  4  5  1  0  0  0  0
 13 14  1  0  0  0  0
 13  3  1  0  0  0  0
  3  2  1  0  0  0  0
 11  9  1  0  0  0  0
  2  1  1  0  0  0  0
  5  6  1  0  0  0  0
  9 10  1  0  0  0  0
  7  8  1  0  0  0  0
 18 19  2  0  0  0  0
  8  9  2  0  0  0  0
 15 16  1  0  0  0  0
  7  6  2  0  0  0  0
 21 22  2  0  0  0  0
 11 12  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 13  2  0  0  0  0
 15 17  1  0  0  0  0
  4 26  1  0  0  0  0
 12 29  1  0  0  0  0
  8 27  1  0  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 10 28  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043558

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(=O)OC(=O)C2(C([H])([H])[H])C([H])([H])[H])C2=C1C([H])=C(C(OC([H])([H])[H])=C2[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O5/c1-8-5-9-10(6-13(8)21-4)14-11(7-12(9)18)17(2,3)16(20)22-15(14)19/h5-7,18H,1-4H3

> <INCHI_KEY>
HTIPWCMGJSDMSU-UHFFFAOYSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.31

> <EXACT_MASS>
300.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.113832035449068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-9-methoxy-4,4,8-trimethyl-1H,3H,4H-naphtho[1,2-c]pyran-1,3-dione

> <ALOGPS_LOGP>
3.45

> <JCHEM_LOGP>
3.5434111626666667

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.087900278079337

> <JCHEM_PKA_STRONGEST_BASIC>
-4.823460736775334

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
80.42739999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-9-methoxy-4,4,8-trimethylnaphtho[1,2-c]pyran-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.0599    5.5819   -0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5796    4.8397   -1.8268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818    3.4740   -1.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306    2.7474   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909    1.3271   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946    0.5409    0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -0.8639    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0354   -1.5058   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7449   -0.7579   -1.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132   -1.4117   -2.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897    0.6482   -1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    1.3895   -2.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3530    2.7885   -2.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277    3.5281   -3.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784   -1.6106    1.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393   -3.0007    0.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7576   -1.8023    2.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296   -0.7968    1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -1.3147    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747    0.5345    1.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5528    1.1661    1.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2078    2.2244    1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1083    6.6444   -0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732    5.3567    0.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411    5.4104   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    3.2926   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -2.5884   -0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4525   -2.3710   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993    0.8592   -3.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4479    4.1067   -4.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819    2.8416   -4.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8541    4.2022   -3.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6988   -3.4876    1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1972   -3.6837    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -2.9240   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4271   -0.8480    3.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -2.3084    3.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397   -2.4040    2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  5  2  0
  3  4  2  0
  7 15  1  0
  6 21  1  0
 18 15  1  0
  4  5  1  0
 13 14  1  0
 13  3  1  0
  3  2  1  0
 11  9  1  0
  2  1  1  0
  5  6  1  0
  9 10  1  0
  7  8  1  0
 18 19  2  0
  8  9  2  0
 15 16  1  0
  7  6  2  0
 21 22  2  0
 11 12  1  0
 18 20  1  0
 20 21  1  0
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 15 17  1  0
  4 26  1  0
 12 29  1  0
  8 27  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 10 28  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.060   5.582  -0.796  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.580   4.840  -1.827  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.582   3.474  -1.714  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.131   2.747  -0.752  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.091   1.327  -0.674  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.795   0.541   0.292  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.761  -0.864   0.276  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.035  -1.506  -0.678  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.745  -0.758  -1.615  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.513  -1.412  -2.545  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.690   0.648  -1.639  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.398   1.389  -2.608  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.353   2.789  -2.655  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.128   3.528  -3.710  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.578  -1.611   1.314  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.039  -3.001   0.819  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.758  -1.802   2.601  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.830  -0.797   1.653  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.926  -1.315   1.849  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.675   0.535   1.817  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.553   1.166   1.408  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.208   2.224   1.915  0.00  0.00           O+0
HETATM   23  H   UNK     0       0.108   6.644  -0.996  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.373   5.357   0.185  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.141   5.410  -0.802  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.747   3.293  -0.045  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.112  -2.588  -0.699  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.452  -2.371  -2.409  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.999   0.859  -3.346  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.448   4.107  -4.344  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.682   2.842  -4.359  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.854   4.202  -3.245  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.699  -3.488   1.548  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.197  -3.684   0.663  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.595  -2.924  -0.123  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.427  -0.848   3.027  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.349  -2.308   3.373  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.140  -2.404   2.415  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    3    1                                                       
CONECT    3    4   13    2                                                  
CONECT    4    3    5   26                                                  
CONECT    5   11    4    6                                                  
CONECT    6   21    5    7                                                  
CONECT    7   15    8    6                                                  
CONECT    8    7    9   27                                                  
CONECT    9   11   10    8                                                  
CONECT   10    9   28                                                       
CONECT   11    5    9   12                                                  
CONECT   12   11   13   29                                                  
CONECT   13   14    3   12                                                  
CONECT   14   13   30   31   32                                             
CONECT   15    7   18   16   17                                             
CONECT   16   15   33   34   35                                             
CONECT   17   15   36   37   38                                             
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21    6   22   20                                                  
CONECT   22   21                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    4                                                            
CONECT   27    8                                                            
CONECT   28   10                                                            
CONECT   29   12                                                            
CONECT   30   14                                                            
CONECT   31   14                                                            
CONECT   32   14                                                            
CONECT   33   16                                                            
CONECT   34   16                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   17                                                            
CONECT   38   17                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

RDKit          3D

38 40  0  0  0  0  0  0  0  0999 V2000
   -0.0599    5.5819   -0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5796    4.8397   -1.8268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818    3.4740   -1.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306    2.7474   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909    1.3271   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946    0.5409    0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -0.8639    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0354   -1.5058   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7449   -0.7579   -1.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5132   -1.4117   -2.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897    0.6482   -1.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    1.3895   -2.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3530    2.7885   -2.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277    3.5281   -3.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784   -1.6106    1.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393   -3.0007    0.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7576   -1.8023    2.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296   -0.7968    1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -1.3147    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747    0.5345    1.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5528    1.1661    1.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2078    2.2244    1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1083    6.6444   -0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732    5.3567    0.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411    5.4104   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    3.2926   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -2.5884   -0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4525   -2.3710   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993    0.8592   -3.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4479    4.1067   -4.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819    2.8416   -4.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8541    4.2022   -3.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6988   -3.4876    1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1972   -3.6837    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -2.9240   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4271   -0.8480    3.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -2.3084    3.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397   -2.4040    2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  5  2  0
  3  4  2  0
  7 15  1  0
  6 21  1  0
 18 15  1  0
  4  5  1  0
 13 14  1  0
 13  3  1  0
  3  2  1  0
 11  9  1  0
  2  1  1  0
  5  6  1  0
  9 10  1  0
  7  8  1  0
 18 19  2  0
  8  9  2  0
 15 16  1  0
  7  6  2  0
 21 22  2  0
 11 12  1  0
 18 20  1  0
 20 21  1  0
 12 13  2  0
 15 17  1  0
  4 26  1  0
 12 29  1  0
  8 27  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 10 28  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₅

Average Mass

300.3100 Da

Monoisotopic Mass

300.09977 Da

IUPAC Name

6-hydroxy-9-methoxy-4,4,8-trimethyl-1H,3H,4H-naphtho[1,2-c]pyran-1,3-dione

Traditional Name

6-hydroxy-9-methoxy-4,4,8-trimethylnaphtho[1,2-c]pyran-1,3-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C(=O)OC(=O)C2(C([H])([H])[H])C([H])([H])[H])C2=C1C([H])=C(C(OC([H])([H])[H])=C2[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C17H16O5/c1-8-5-9-10(6-13(8)21-4)14-11(7-12(9)18)17(2,3)16(20)22-15(14)19/h5-7,18H,1-4H3

InChI Key

HTIPWCMGJSDMSU-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Strophioblachia fimbricalyx	JEOL database	Seephonkai, P., et al, J. Nat. Prod. 76, 1358 (2013)

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-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Pyran
Carboxylic acid anhydride
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Carbonyl group
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	3.45	ALOGPS
logP	3.54	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.09	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.43 m³·mol⁻¹	ChemAxon
Polarizability	31.11 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30820781

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71746809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Stomach (Gastric) Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389468 ]
Authors unspecified: Childhood Central Nervous System Atypical Teratoid/Rhabdoid Tumor Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389426 ]
Seephonkai, P., et al. (2013). Seephonkai, P., et al, J. Nat. Prod. 76, 1358 (2013). J. Nat. Prod..

Showing NP-Card for fimbricalyx anhydride A (NP0043558)

MOL for NP0043558 (fimbricalyx anhydride A)

3D MOL for NP0043558 (fimbricalyx anhydride A)

3D SDF for NP0043558 (fimbricalyx anhydride A)

3D-SDF for NP0043558 (fimbricalyx anhydride A)

PDB for NP0043558 (fimbricalyx anhydride A)

3D PDB for NP0043558 (fimbricalyx anhydride A)

SMILES for NP0043558 (fimbricalyx anhydride A)

INCHI for NP0043558 (fimbricalyx anhydride A)

Structure for NP0043558 (fimbricalyx anhydride A)

3D Structure for NP0043558 (fimbricalyx anhydride A)