NP-MRD: Showing NP-Card for phomonaphthalenone A (NP0042168)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-20 23:53:58 UTC

Updated at

2021-06-30 00:17:06 UTC

NP-MRD ID

NP0042168

Secondary Accession Numbers

None

Natural Product Identification

Common Name

phomonaphthalenone A

Provided By

JEOL Database JEOL Logo

Description

(1S,9S,12R,14S)-3,6-dihydroxy-4-methoxy-12-methyl-11,15-dioxatetracyclo[10.2.1.0²,⁷.0⁹,¹⁴]Pentadeca-2(7),3,5-trien-8-one belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. phomonaphthalenone A is found in Phomopsis sp. HCCB04730. phomonaphthalenone A was first documented in 2013 (Yang, Z., et al.). Based on a literature review very few articles have been published on (1S,9S,12R,14S)-3,6-dihydroxy-4-methoxy-12-methyl-11,15-dioxatetracyclo[10.2.1.0²,⁷.0⁹,¹⁴]Pentadeca-2(7),3,5-trien-8-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101533D          

 37 40  0  0  0  0            999 V2000
   -4.9625   -2.4883    1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712   -1.4548    0.8515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250   -0.8895    1.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -1.2611    2.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4048   -0.5941    2.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8190   -1.0245    4.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852    0.4544    2.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    0.8389    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914    0.1498    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263    0.4846   -0.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9825    1.9340    0.0598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6691    3.1847    0.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758    4.2274    0.2316 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1908    5.4101   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5789    3.6031   -0.3604 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4858    2.2583    0.3272 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7198    2.4409    1.8362 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0806    3.6009    2.4544 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3474    4.6720    1.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3383    1.1739    2.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9648    0.7660    3.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694   -2.8183    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2569   -2.1178    2.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2934   -3.3510    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9311   -2.0604    3.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0045   -0.5039    4.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1279   -0.0750   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996    1.6610   -0.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4684    5.1146   -1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    5.8256   -0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4473    6.2125   -0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4977    4.1467   -0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    3.4824   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615    1.5036   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916    2.6206    1.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705    4.0165    3.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435    3.2677    2.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0  0  0  0
  3  4  2  0  0  0  0
 16 15  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 13  1  0  0  0  0
 13 15  1  0  0  0  0
 13 12  1  0  0  0  0
 11 12  1  0  0  0  0
  8 11  1  0  0  0  0
 13 14  1  6  0  0  0
  7 20  1  0  0  0  0
 11 28  1  6  0  0  0
 20 17  1  0  0  0  0
 16 34  1  6  0  0  0
 16 11  1  0  0  0  0
 20 21  2  0  0  0  0
 16 17  1  0  0  0  0
  5  6  1  0  0  0  0
  4  5  1  0  0  0  0
  3  2  1  0  0  0  0
  5  7  2  0  0  0  0
  9 10  1  0  0  0  0
  8  7  1  0  0  0  0
  2  1  1  0  0  0  0
  9  3  1  0  0  0  0
 17 35  1  6  0  0  0
  4 25  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 14 29  1  0  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
  6 26  1  0  0  0  0
 10 27  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -4.9625   -2.4883    1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712   -1.4548    0.8515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250   -0.8895    1.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -1.2611    2.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4048   -0.5941    2.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8190   -1.0245    4.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852    0.4544    2.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    0.8389    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914    0.1498    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263    0.4846   -0.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9825    1.9340    0.0598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6691    3.1847    0.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758    4.2274    0.2316 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1908    5.4101   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5789    3.6031   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858    2.2583    0.3272 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7198    2.4409    1.8362 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0806    3.6009    2.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3474    4.6720    1.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3383    1.1739    2.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9648    0.7660    3.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694   -2.8183    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2569   -2.1178    2.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2934   -3.3510    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9311   -2.0604    3.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0045   -0.5039    4.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1279   -0.0750   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996    1.6610   -0.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4684    5.1146   -1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    5.8256   -0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4473    6.2125   -0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4977    4.1467   -0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    3.4824   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615    1.5036   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916    2.6206    1.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705    4.0165    3.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435    3.2677    2.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  3  4  2  0
 16 15  1  0
 17 18  1  0
 18 19  1  0
 19 13  1  0
 13 15  1  0
 13 12  1  0
 11 12  1  0
  8 11  1  0
 13 14  1  6
  7 20  1  0
 11 28  1  6
 20 17  1  0
 16 34  1  6
 16 11  1  0
 20 21  2  0
 16 17  1  0
  5  6  1  0
  4  5  1  0
  3  2  1  0
  5  7  2  0
  9 10  1  0
  8  7  1  0
  2  1  1  0
  9  3  1  0
 17 35  1  6
  4 25  1  0
 18 36  1  0
 18 37  1  0
 15 32  1  0
 15 33  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
  6 26  1  0
 10 27  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652306212101533D          

 37 40  0  0  0  0            999 V2000
   -4.9625   -2.4883    1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712   -1.4548    0.8515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250   -0.8895    1.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -1.2611    2.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4048   -0.5941    2.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8190   -1.0245    4.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852    0.4544    2.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    0.8389    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914    0.1498    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263    0.4846   -0.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9825    1.9340    0.0598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6691    3.1847    0.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758    4.2274    0.2316 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1908    5.4101   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5789    3.6031   -0.3604 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4858    2.2583    0.3272 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7198    2.4409    1.8362 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0806    3.6009    2.4544 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3474    4.6720    1.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3383    1.1739    2.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9648    0.7660    3.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694   -2.8183    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2569   -2.1178    2.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2934   -3.3510    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9311   -2.0604    3.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0045   -0.5039    4.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1279   -0.0750   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996    1.6610   -0.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4684    5.1146   -1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    5.8256   -0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4473    6.2125   -0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4977    4.1467   -0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    3.4824   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615    1.5036   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916    2.6206    1.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705    4.0165    3.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435    3.2677    2.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0  0  0  0
  3  4  2  0  0  0  0
 16 15  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 13  1  0  0  0  0
 13 15  1  0  0  0  0
 13 12  1  0  0  0  0
 11 12  1  0  0  0  0
  8 11  1  0  0  0  0
 13 14  1  6  0  0  0
  7 20  1  0  0  0  0
 11 28  1  6  0  0  0
 20 17  1  0  0  0  0
 16 34  1  6  0  0  0
 16 11  1  0  0  0  0
 20 21  2  0  0  0  0
 16 17  1  0  0  0  0
  5  6  1  0  0  0  0
  4  5  1  0  0  0  0
  3  2  1  0  0  0  0
  5  7  2  0  0  0  0
  9 10  1  0  0  0  0
  8  7  1  0  0  0  0
  2  1  1  0  0  0  0
  9  3  1  0  0  0  0
 17 35  1  6  0  0  0
  4 25  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 14 29  1  0  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
  6 26  1  0  0  0  0
 10 27  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042168

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)[C@]3([H])C([H])([H])O[C@@]4(O[C@]([H])(C2=C(O[H])C(OC([H])([H])[H])=C1[H])[C@@]3([H])C4([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O6/c1-15-4-6-7(5-20-15)12(17)10-8(16)3-9(19-2)13(18)11(10)14(6)21-15/h3,6-7,14,16,18H,4-5H2,1-2H3/t6-,7+,14-,15+/m0/s1

> <INCHI_KEY>
JSFXOJVYQRUNET-XOEPVMSWSA-N

> <FORMULA>
C15H16O6

> <MOLECULAR_WEIGHT>
292.287

> <EXACT_MASS>
292.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.53697832064333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S,12R,14S)-3,6-dihydroxy-4-methoxy-12-methyl-11,15-dioxatetracyclo[10.2.1.0^{2,7}.0^{9,14}]pentadeca-2(7),3,5-trien-8-one

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
1.5491341513333325

> <ALOGPS_LOGS>
-1.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.826968865900906

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.866095181683193

> <JCHEM_PKA_STRONGEST_BASIC>
-4.005968429922674

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
72.75960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S,12R,14S)-3,6-dihydroxy-4-methoxy-12-methyl-11,15-dioxatetracyclo[10.2.1.0^{2,7}.0^{9,14}]pentadeca-2(7),3,5-trien-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -4.9625   -2.4883    1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712   -1.4548    0.8515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250   -0.8895    1.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -1.2611    2.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4048   -0.5941    2.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8190   -1.0245    4.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852    0.4544    2.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    0.8389    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914    0.1498    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263    0.4846   -0.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9825    1.9340    0.0598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6691    3.1847    0.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758    4.2274    0.2316 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1908    5.4101   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5789    3.6031   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858    2.2583    0.3272 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7198    2.4409    1.8362 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0806    3.6009    2.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3474    4.6720    1.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3383    1.1739    2.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9648    0.7660    3.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694   -2.8183    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2569   -2.1178    2.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2934   -3.3510    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9311   -2.0604    3.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0045   -0.5039    4.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1279   -0.0750   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996    1.6610   -0.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4684    5.1146   -1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    5.8256   -0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4473    6.2125   -0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4977    4.1467   -0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    3.4824   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615    1.5036   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916    2.6206    1.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705    4.0165    3.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435    3.2677    2.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  3  4  2  0
 16 15  1  0
 17 18  1  0
 18 19  1  0
 19 13  1  0
 13 15  1  0
 13 12  1  0
 11 12  1  0
  8 11  1  0
 13 14  1  6
  7 20  1  0
 11 28  1  6
 20 17  1  0
 16 34  1  6
 16 11  1  0
 20 21  2  0
 16 17  1  0
  5  6  1  0
  4  5  1  0
  3  2  1  0
  5  7  2  0
  9 10  1  0
  8  7  1  0
  2  1  1  0
  9  3  1  0
 17 35  1  6
  4 25  1  0
 18 36  1  0
 18 37  1  0
 15 32  1  0
 15 33  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
  6 26  1  0
 10 27  1  0
  1 22  1  0
  1 23  1  0
  1 24  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      -4.963  -2.488   1.633  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.371  -1.455   0.852  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.225  -0.890   1.350  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.570  -1.261   2.520  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.405  -0.594   2.898  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.819  -1.024   4.060  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.885   0.454   2.121  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.527   0.839   0.933  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.691   0.150   0.571  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.326   0.485  -0.599  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.983   1.934   0.060  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.669   3.185   0.266  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.676   4.227   0.232  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.191   5.410  -0.566  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.579   3.603  -0.360  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.486   2.258   0.327  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.720   2.441   1.836  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.081   3.601   2.454  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.347   4.672   1.550  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.338   1.174   2.565  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.965   0.766   3.541  0.00  0.00           O+0
HETATM   22  H   UNK     0      -5.869  -2.818   1.117  0.00  0.00           H+0
HETATM   23  H   UNK     0      -5.257  -2.118   2.620  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.293  -3.351   1.715  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.931  -2.060   3.158  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.005  -0.504   4.202  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.128  -0.075  -0.628  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.100   1.661  -0.998  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.468   5.115  -1.583  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.088   5.826  -0.093  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.447   6.213  -0.614  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.498   4.147  -0.119  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.504   3.482  -1.448  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.161   1.504  -0.089  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.792   2.621   1.988  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.471   4.016   3.306  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.044   3.268   2.861  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    3    1                                                       
CONECT    3    4    2    9                                                  
CONECT    4    3    5   25                                                  
CONECT    5    6    4    7                                                  
CONECT    6    5   26                                                       
CONECT    7   20    5    8                                                  
CONECT    8    9   11    7                                                  
CONECT    9    8   10    3                                                  
CONECT   10    9   27                                                       
CONECT   11   12    8   28   16                                             
CONECT   12   13   11                                                       
CONECT   13   19   15   12   14                                             
CONECT   14   13   29   30   31                                             
CONECT   15   16   13   32   33                                             
CONECT   16   15   34   11   17                                             
CONECT   17   18   20   16   35                                             
CONECT   18   17   19   36   37                                             
CONECT   19   18   13                                                       
CONECT   20    7   17   21                                                  
CONECT   21   20                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27   10                                                            
CONECT   28   11                                                            
CONECT   29   14                                                            
CONECT   30   14                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   18                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

RDKit          3D

37 40  0  0  0  0  0  0  0  0999 V2000
   -4.9625   -2.4883    1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3712   -1.4548    0.8515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250   -0.8895    1.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -1.2611    2.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4048   -0.5941    2.8977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8190   -1.0245    4.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852    0.4544    2.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    0.8389    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914    0.1498    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263    0.4846   -0.5990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9825    1.9340    0.0598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6691    3.1847    0.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6758    4.2274    0.2316 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1908    5.4101   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5789    3.6031   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858    2.2583    0.3272 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7198    2.4409    1.8362 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0806    3.6009    2.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3474    4.6720    1.5495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3383    1.1739    2.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9648    0.7660    3.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694   -2.8183    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2569   -2.1178    2.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2934   -3.3510    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9311   -2.0604    3.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0045   -0.5039    4.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1279   -0.0750   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996    1.6610   -0.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4684    5.1146   -1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    5.8256   -0.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4473    6.2125   -0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4977    4.1467   -0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    3.4824   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615    1.5036   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916    2.6206    1.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705    4.0165    3.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435    3.2677    2.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  3  4  2  0
 16 15  1  0
 17 18  1  0
 18 19  1  0
 19 13  1  0
 13 15  1  0
 13 12  1  0
 11 12  1  0
  8 11  1  0
 13 14  1  6
  7 20  1  0
 11 28  1  6
 20 17  1  0
 16 34  1  6
 16 11  1  0
 20 21  2  0
 16 17  1  0
  5  6  1  0
  4  5  1  0
  3  2  1  0
  5  7  2  0
  9 10  1  0
  8  7  1  0
  2  1  1  0
  9  3  1  0
 17 35  1  6
  4 25  1  0
 18 36  1  0
 18 37  1  0
 15 32  1  0
 15 33  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
  6 26  1  0
 10 27  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₆

Average Mass

292.2870 Da

Monoisotopic Mass

292.09469 Da

IUPAC Name

(1S,9S,12R,14S)-3,6-dihydroxy-4-methoxy-12-methyl-11,15-dioxatetracyclo[10.2.1.0^{2,7}.0^{9,14}]pentadeca-2(7),3,5-trien-8-one

Traditional Name

(1S,9S,12R,14S)-3,6-dihydroxy-4-methoxy-12-methyl-11,15-dioxatetracyclo[10.2.1.0^{2,7}.0^{9,14}]pentadeca-2(7),3,5-trien-8-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(=O)[C@]3([H])C([H])([H])O[C@@]4(O[C@]([H])(C2=C(O[H])C(OC([H])([H])[H])=C1[H])[C@@]3([H])C4([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H16O6/c1-15-4-6-7(5-20-15)12(17)10-8(16)3-9(19-2)13(18)11(10)14(6)21-15/h3,6-7,14,16,18H,4-5H2,1-2H3/t6-,7+,14-,15+/m0/s1

InChI Key

JSFXOJVYQRUNET-XOEPVMSWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Phomopsis sp. HCCB04730	JEOL database	Yang, Z., et al, Phytochem. Lett. 6, 257 (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
Naphthofuran
Tetralin
Naphthalene
Aryl alkyl ketone
Aryl ketone
Anisole
1-hydroxy-2-unsubstituted benzenoid
Ketal
Pyranone
Dioxepane
Alkyl aryl ether
1,3-dioxepane
Benzenoid
Pyran
Oxane
Vinylogous acid
Tetrahydrofuran
Ketone
Oxacycle
Ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.33	ALOGPS
logP	1.55	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	8.87	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.76 m³·mol⁻¹	ChemAxon
Polarizability	28.54 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583689

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang, Z., et al. (2013). Yang, Z., et al, Phytochem. Lett. 6, 257 (2013) . Phytochem..

Showing NP-Card for phomonaphthalenone A (NP0042168)

MOL for NP0042168 (phomonaphthalenone A)

3D MOL for NP0042168 (phomonaphthalenone A)

3D SDF for NP0042168 (phomonaphthalenone A)

3D-SDF for NP0042168 (phomonaphthalenone A)

PDB for NP0042168 (phomonaphthalenone A)

3D PDB for NP0042168 (phomonaphthalenone A)

SMILES for NP0042168 (phomonaphthalenone A)

INCHI for NP0042168 (phomonaphthalenone A)

Structure for NP0042168 (phomonaphthalenone A)

3D Structure for NP0042168 (phomonaphthalenone A)