NP-MRD: Showing NP-Card for Dehydrocitreaglycon A (NP0011305)

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Record Information

Version

2.0

Created at

2021-01-05 21:02:37 UTC

Updated at

2021-07-15 17:08:32 UTC

NP-MRD ID

NP0011305

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dehydrocitreaglycon A

Provided By

NPAtlas

Description

13,15,16-Trihydroxy-3-methoxy-3-methyl-1,14-dioxo-1,3,4,6,7,14-hexahydro-2,9-dioxahexaphene-12-carboxylic acid belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Dehydrocitreaglycon A is found in Streptomyces caelestis. Dehydrocitreaglycon A was first documented in 2012 (PMID: 23203278). Based on a literature review very few articles have been published on 13,15,16-trihydroxy-3-methoxy-3-methyl-1,14-dioxo-1,3,4,6,7,14-hexahydro-2,9-dioxahexaphene-12-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242116553D          

 57 62  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242116553D          

 57 62  0  0  0  0            999 V2000
    6.3002   -0.7814   -1.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4962    0.2929   -0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    1.2557   -1.3881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5380   -0.3657    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815    0.0515    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9204    1.0840   -0.7681 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3189   -2.4693    2.4674 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7065   -2.0851    2.4195 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0923   -1.4043   -2.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8763   -1.3518   -0.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3813   -0.6502   -1.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3141    2.7017   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7818    0.9907    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5824    1.6567   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5019    1.5122    1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8590   -0.1861    1.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061   -1.1848    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859    2.3251   -1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -2.9023    2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6047   -2.4528    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4125   -1.3275   -0.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6524    2.6015   -2.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0195    2.0799   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271    1.6664   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -3.5503    2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0695   -2.3917    3.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3373   -2.9564    2.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -1.8393    3.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 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
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 17 36  1  0  0  0  0
 36 37  1  0  0  0  0
 15  3  1  0  0  0  0
 34 16  1  0  0  0  0
 12  6  1  0  0  0  0
 33 19  1  0  0  0  0
 37  8  1  0  0  0  0
 30 21  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  4 41  1  0  0  0  0
  4 42  1  0  0  0  0
  4 43  1  0  0  0  0
  5 44  1  0  0  0  0
  5 45  1  0  0  0  0
  7 46  1  0  0  0  0
 11 47  1  0  0  0  0
 18 48  1  0  0  0  0
 22 49  1  0  0  0  0
 23 50  1  0  0  0  0
 27 51  1  0  0  0  0
 29 52  1  0  0  0  0
 35 53  1  0  0  0  0
 36 54  1  0  0  0  0
 36 55  1  0  0  0  0
 37 56  1  0  0  0  0
 37 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011305

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C2OC3=C([H])C4=C(C(O[H])=C3C(=O)C2=C1O[H])C1=C(C([H])=C2C(C(=O)O[C@@](OC([H])([H])[H])(C([H])([H])[H])C2([H])[H])=C1O[H])C([H])([H])C4([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H20O10/c1-27(35-2)9-12-7-10-3-4-11-8-15-20(23(30)17(11)16(10)22(29)18(12)26(34)37-27)24(31)19-14(36-15)6-5-13(21(19)28)25(32)33/h5-8,28-30H,3-4,9H2,1-2H3,(H,32,33)/t27-/m0/s1

> <INCHI_KEY>
VMTRONAGVWJCNB-UHFFFAOYSA-N

> <FORMULA>
C27H20O10

> <MOLECULAR_WEIGHT>
504.447

> <EXACT_MASS>
504.105646844

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
51.63143543228212

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-13,15,16-trihydroxy-3-methoxy-3-methyl-1,14-dioxo-1,3,4,6,7,14-hexahydro-2,9-dioxahexaphene-12-carboxylic acid

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
6.658498693333334

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.918242711497026

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.861890729893138

> <JCHEM_PKA_STRONGEST_BASIC>
-3.671607093995776

> <JCHEM_POLAR_SURFACE_AREA>
159.82

> <JCHEM_REFRACTIVITY>
129.67979999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-13,15,16-trihydroxy-3-methoxy-3-methyl-1,14-dioxo-6,7-dihydro-4H-2,9-dioxahexaphene-12-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
    6.3002   -0.7814   -1.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5897    0.3837   -1.5633 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7517    1.2573   -0.5205 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2112    1.6772   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2990    0.7301    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529    0.4081    0.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3800   -0.6349    1.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409   -0.9582    1.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1655   -0.2238    0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5982    0.8057   -0.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498    1.5673   -0.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9706    1.1150   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5568    2.1746   -0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8607    2.8791   -1.5554 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474    2.4168   -0.7882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462   -0.6099    0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017   -1.6835    1.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208   -2.0692    1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8709   -1.4131    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1319   -1.7881    0.9951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0759   -1.1974    0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3963   -1.6177    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3813   -0.9931   -0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1393    0.0891   -1.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2480    0.6702   -1.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3970    0.1951   -1.7345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1463    1.7245   -2.7663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8277    0.5027   -1.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4417    1.5435   -2.0678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8223   -0.1456   -0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4962    0.2929   -0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    1.2557   -1.3881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5380   -0.3657    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815    0.0515    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9204    1.0840   -0.7681 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3189   -2.4693    2.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065   -2.0851    2.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0923   -1.4043   -2.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8763   -1.3518   -0.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3813   -0.6502   -1.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3141    2.7017   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7818    0.9907    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5824    1.6567   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5019    1.5122    1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8590   -0.1861    1.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061   -1.1848    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859    2.3251   -1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -2.9023    2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6047   -2.4528    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4125   -1.3275   -0.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6524    2.6015   -2.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0195    2.0799   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271    1.6664   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -3.5503    2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0695   -2.3917    3.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3373   -2.9564    2.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -1.8393    3.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 24 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 17 36  1  0
 36 37  1  0
 15  3  1  0
 34 16  1  0
 12  6  1  0
 33 19  1  0
 37  8  1  0
 30 21  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  7 46  1  0
 11 47  1  0
 18 48  1  0
 22 49  1  0
 23 50  1  0
 27 51  1  0
 29 52  1  0
 35 53  1  0
 36 54  1  0
 36 55  1  0
 37 56  1  0
 37 57  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.300  -0.781  -1.453  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.590   0.384  -1.563  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.752   1.257  -0.521  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.211   1.677  -0.492  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.299   0.730   0.811  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.853   0.408   0.756  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.380  -0.635   1.537  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.041  -0.958   1.541  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.165  -0.224   0.749  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.598   0.806  -0.029  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.850   1.567  -0.817  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.971   1.115  -0.015  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.557   2.175  -0.825  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.861   2.879  -1.555  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.947   2.417  -0.788  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.246  -0.610   0.791  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.602  -1.684   1.621  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.921  -2.069   1.678  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.871  -1.413   0.935  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.132  -1.788   0.995  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.076  -1.197   0.308  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.396  -1.618   0.394  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.381  -0.993  -0.329  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.139   0.089  -1.189  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.248   0.670  -1.901  0.00  0.00           C+0
HETATM   26  O   UNK     0      -9.397   0.195  -1.734  0.00  0.00           O+0
HETATM   27  O   UNK     0      -8.146   1.724  -2.766  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.828   0.503  -1.272  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.442   1.544  -2.068  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.822  -0.146  -0.524  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.496   0.293  -0.624  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.275   1.256  -1.388  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.538  -0.366   0.123  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.182   0.052   0.046  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.920   1.084  -0.768  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.319  -2.469   2.467  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.706  -2.085   2.420  0.00  0.00           C+0
HETATM   38  H   UNK     0       6.092  -1.404  -2.346  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.876  -1.352  -0.576  0.00  0.00           H+0
HETATM   40  H   UNK     0       7.381  -0.650  -1.262  0.00  0.00           H+0
HETATM   41  H   UNK     0       7.314   2.702  -0.045  0.00  0.00           H+0
HETATM   42  H   UNK     0       7.782   0.991   0.135  0.00  0.00           H+0
HETATM   43  H   UNK     0       7.582   1.657  -1.536  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.502   1.512   1.572  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.859  -0.186   1.113  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.106  -1.185   2.144  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.986   2.325  -1.424  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.251  -2.902   2.311  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.605  -2.453   1.054  0.00  0.00           H+0
HETATM   50  H   UNK     0      -8.412  -1.327  -0.257  0.00  0.00           H+0
HETATM   51  H   UNK     0      -8.652   2.602  -2.672  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.019   2.080  -2.635  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.427   1.666  -1.360  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.138  -3.550   2.201  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.070  -2.392   3.526  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.337  -2.956   2.073  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.139  -1.839   3.432  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5   15                                             
CONECT    4    3   41   42   43                                             
CONECT    5    3    6   44   45                                             
CONECT    6    5    7   12                                                  
CONECT    7    6    8   46                                                  
CONECT    8    7    9   37                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   47                                                       
CONECT   12   10   13    6                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    3                                                       
CONECT   16    9   17   34                                                  
CONECT   17   16   18   36                                                  
CONECT   18   17   19   48                                                  
CONECT   19   18   20   33                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23   49                                                  
CONECT   23   22   24   50                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   51                                                       
CONECT   28   24   29   30                                                  
CONECT   29   28   52                                                       
CONECT   30   28   31   21                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   19                                                  
CONECT   34   33   35   16                                                  
CONECT   35   34   53                                                       
CONECT   36   17   37   54   55                                             
CONECT   37   36    8   56   57                                             
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    4                                                            
CONECT   42    4                                                            
CONECT   43    4                                                            
CONECT   44    5                                                            
CONECT   45    5                                                            
CONECT   46    7                                                            
CONECT   47   11                                                            
CONECT   48   18                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   27                                                            
CONECT   52   29                                                            
CONECT   53   35                                                            
CONECT   54   36                                                            
CONECT   55   36                                                            
CONECT   56   37                                                            
CONECT   57   37                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

RDKit          3D

57 62  0  0  0  0  0  0  0  0999 V2000
    6.3002   -0.7814   -1.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5897    0.3837   -1.5633 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7517    1.2573   -0.5205 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2112    1.6772   -0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2990    0.7301    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529    0.4081    0.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3800   -0.6349    1.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409   -0.9582    1.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1655   -0.2238    0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5982    0.8057   -0.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498    1.5673   -0.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9706    1.1150   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5568    2.1746   -0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8607    2.8791   -1.5554 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474    2.4168   -0.7882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462   -0.6099    0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017   -1.6835    1.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208   -2.0692    1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8709   -1.4131    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1319   -1.7881    0.9951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0759   -1.1974    0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3963   -1.6177    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3813   -0.9931   -0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1393    0.0891   -1.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2480    0.6702   -1.9013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3970    0.1951   -1.7345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1463    1.7245   -2.7663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8277    0.5027   -1.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4417    1.5435   -2.0678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8223   -0.1456   -0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4962    0.2929   -0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    1.2557   -1.3881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5380   -0.3657    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815    0.0515    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9204    1.0840   -0.7681 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3189   -2.4693    2.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065   -2.0851    2.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0923   -1.4043   -2.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8763   -1.3518   -0.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3813   -0.6502   -1.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3141    2.7017   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7818    0.9907    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5824    1.6567   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5019    1.5122    1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8590   -0.1861    1.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061   -1.1848    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859    2.3251   -1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -2.9023    2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6047   -2.4528    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4125   -1.3275   -0.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6524    2.6015   -2.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0195    2.0799   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271    1.6664   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -3.5503    2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0695   -2.3917    3.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3373   -2.9564    2.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -1.8393    3.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 24 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 17 36  1  0
 36 37  1  0
 15  3  1  0
 34 16  1  0
 12  6  1  0
 33 19  1  0
 37  8  1  0
 30 21  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  7 46  1  0
 11 47  1  0
 18 48  1  0
 22 49  1  0
 23 50  1  0
 27 51  1  0
 29 52  1  0
 35 53  1  0
 36 54  1  0
 36 55  1  0
 37 56  1  0
 37 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
13,15,16-Trihydroxy-3-methoxy-3-methyl-1,14-dioxo-1,3,4,6,7,14-hexahydro-2,9-dioxahexaphene-12-carboxylate	Generator

Chemical Formula

C₂₇H₂₀O₁₀

Average Mass

504.4470 Da

Monoisotopic Mass

504.10565 Da

IUPAC Name

(3S)-13,15,16-trihydroxy-3-methoxy-3-methyl-1,14-dioxo-1,3,4,6,7,14-hexahydro-2,9-dioxahexaphene-12-carboxylic acid

Traditional Name

(3S)-13,15,16-trihydroxy-3-methoxy-3-methyl-1,14-dioxo-6,7-dihydro-4H-2,9-dioxahexaphene-12-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1(C)CC2=C(C(=O)O1)C(O)=C1C(CCC3=CC4=C(C(O)=C13)C(=O)C1=C(O4)C=CC(C(O)=O)=C1O)=C2

InChI Identifier

InChI=1S/C27H20O10/c1-27(35-2)9-12-7-10-3-4-11-8-15-20(23(30)17(11)16(10)22(29)18(12)26(34)37-27)24(31)19-14(36-15)6-5-13(21(19)28)25(32)33/h5-8,28-30H,3-4,9H2,1-2H3,(H,32,33)

InChI Key

VMTRONAGVWJCNB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces caelestis	NPAtlas	23203278

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Macrolide lactam
Alpha-amino acid ester
Macrolactam
Macrolide
Alpha-amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Secondary alcohol
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	3.36	ALOGPS
logP	6.66	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	2.86	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	159.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	129.68 m³·mol⁻¹	ChemAxon
Polarizability	51.63 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA011869

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29215279

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586401

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu LL, Xu Y, Han Z, Li YX, Lu L, Lai PY, Zhong JL, Guo XR, Zhang XX, Qian PY: Four new antibacterial xanthones from the marine-derived actinomycetes Streptomyces caelestis. Mar Drugs. 2012 Nov 20;10(11):2571-83. doi: 10.3390/md10112571. [PubMed:23203278 ]

Showing NP-Card for Dehydrocitreaglycon A (NP0011305)

MOL for NP0011305 (Dehydrocitreaglycon A)

3D MOL for NP0011305 (Dehydrocitreaglycon A)

3D SDF for NP0011305 (Dehydrocitreaglycon A)

3D-SDF for NP0011305 (Dehydrocitreaglycon A)

PDB for NP0011305 (Dehydrocitreaglycon A)

3D PDB for NP0011305 (Dehydrocitreaglycon A)

SMILES for NP0011305 (Dehydrocitreaglycon A)

INCHI for NP0011305 (Dehydrocitreaglycon A)

Structure for NP0011305 (Dehydrocitreaglycon A)

3D Structure for NP0011305 (Dehydrocitreaglycon A)