NP-MRD: Showing NP-Card for A80915D (NP0006565)

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Record Information

Version

2.0

Created at

2020-12-09 03:32:44 UTC

Updated at

2021-07-15 16:55:10 UTC

NP-MRD ID

NP0006565

Secondary Accession Numbers

None

Natural Product Identification

Common Name

A80915D

Provided By

NPAtlas

Description

Antibiotic A 80915D 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. A80915D is found in Streptomyces and Streptomyces aculeolatus. Based on a literature review very few articles have been published on Antibiotic A 80915D.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118293D          

 68 71  0  0  0  0            999 V2000
    4.8848    3.9833   -0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9631    2.9202   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6230    1.8797   -0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627    1.8183   -2.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259    0.8269   -0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1796    0.8449    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -0.2240    1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2297   -0.4692    2.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4683   -0.9888    0.1309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4690   -0.1330   -0.6261 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.3949    2.9871    1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6301   -1.7558   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
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  9 22  1  0  0  0  0
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  6 33  1  0  0  0  0
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 31  5  1  0  0  0  0
 29  9  1  0  0  0  0
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  4 41  1  0  0  0  0
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 17 52  1  0  0  0  0
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 21 59  1  0  0  0  0
 24 60  1  0  0  0  0
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 25 63  1  0  0  0  0
 25 64  1  0  0  0  0
 25 65  1  0  0  0  0
 26 66  1  6  0  0  0
 28 67  1  0  0  0  0
 28 68  1  0  0  0  0
M  CHG  2  34   1  35  -1
M  END

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
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  2  3  2  0
  3  4  1  0
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  5  6  2  0
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 19 20  1  0
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 31  5  1  0
 29  9  1  0
 19 11  1  0
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 25 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  6
 28 67  1  0
 28 68  1  0
M  CHG  2  34   1  35  -1
M  END


  Mrv1652306242118293D          

 68 71  0  0  0  0            999 V2000
    4.8848    3.9833   -0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9631    2.9202   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6230    1.8797   -0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627    1.8183   -2.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259    0.8269   -0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1796    0.8449    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -0.2240    1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2297   -0.4692    2.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4683   -0.9888    0.1309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4690   -0.1330   -0.6261 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.4991   -0.0026    0.9204 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.2763   -3.2197    0.8380 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9038   -4.1914    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8256   -3.4680    2.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3207   -3.6978   -0.1129 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2429   -5.0924    0.5425 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3284   -2.5951   -0.3569 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5333   -1.4489   -0.8891 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6279   -2.0313   -2.3026 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3553   -0.3123   -1.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4955    1.9499    1.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9898    1.9668    2.7369 N   0  3  0  0  0  4  0  0  0  0  0  0
    1.3149    2.2803    3.7227 N   0  5  0  0  0  2  0  0  0  0  0  0
    3.3949    2.9871    1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679    3.9367    1.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4273    2.5424   -1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2882    3.2230    0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4812    2.8196    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8907    1.6885   -0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6295    0.2003    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6369    1.2679    2.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5237   -5.2291    0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4605   -4.1677    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264   -3.9351   -0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7266   -4.5580    2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777   -2.9392    2.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8623   -3.1436    2.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -4.0208   -1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0226   -2.9178   -1.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784   -2.3269    0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  1  0  0  0
  9 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
  6 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  2  0  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36  2  1  0  0  0  0
 31  5  1  0  0  0  0
 29  9  1  0  0  0  0
 19 11  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
 10 42  1  0  0  0  0
 10 43  1  0  0  0  0
 11 44  1  1  0  0  0
 13 45  1  0  0  0  0
 13 46  1  0  0  0  0
 13 47  1  0  0  0  0
 14 48  1  0  0  0  0
 14 49  1  0  0  0  0
 14 50  1  0  0  0  0
 15 51  1  1  0  0  0
 17 52  1  0  0  0  0
 17 53  1  0  0  0  0
 18 54  1  0  0  0  0
 18 55  1  0  0  0  0
 20 56  1  0  0  0  0
 20 57  1  0  0  0  0
 20 58  1  0  0  0  0
 21 59  1  0  0  0  0
 24 60  1  0  0  0  0
 24 61  1  0  0  0  0
 24 62  1  0  0  0  0
 25 63  1  0  0  0  0
 25 64  1  0  0  0  0
 25 65  1  0  0  0  0
 26 66  1  6  0  0  0
 28 67  1  0  0  0  0
 28 68  1  0  0  0  0
M  CHG  2  34   1  35  -1
M  END
> <DATABASE_ID>
NP0006565

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(=O)C(=[N+]=[N-])C2=C1C(=O)[C@@]1(Cl)C([H])([H])[C@@]([H])(Cl)C(O[C@]1(C2=O)C([H])([H])[C@]1([H])[C@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(Cl)C1(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H31Cl3N2O6/c1-11-18(32)16-15(17(31-30)19(11)33)21(35)26(9-12-22(2,3)13(27)7-8-24(12,6)36)25(29,20(16)34)10-14(28)23(4,5)37-26/h12-14,32,36H,7-10H2,1-6H3/t12-,13-,14+,24-,25-,26-/m0/s1

> <INCHI_KEY>
DTXSUAICQAUGGW-GIXVMFRNSA-N

> <FORMULA>
C26H31Cl3N2O6

> <MOLECULAR_WEIGHT>
573.89

> <EXACT_MASS>
572.1247698

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.8127936702911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4aR,10aS)-3,4a-dichloro-10a-{[(1S,3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-6-hydroxy-9-(-lambda4,-lambda2-diazynylidene)-2,2,7-trimethyl-2H,3H,4H,4aH,5H,8H,9H,10H,10aH-naphtho[2,3-b]pyran-5,8,10-trione

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.4673294541240542

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.918646023463738

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2665309914746525

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9023984249988493

> <JCHEM_POLAR_SURFACE_AREA>
117.97000000000001

> <JCHEM_REFRACTIVITY>
139.1725

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.50e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4aR,10aS)-3,4a-dichloro-10a-{[(1S,3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-6-hydroxy-9-(-lambda4,-lambda2-diazynylidene)-2,2,7-trimethyl-3H,4H-naphtho[2,3-b]pyran-5,8,10-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
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  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
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  9 10  1  6
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 11 12  1  0
 12 13  1  6
 12 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  1
  9 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  6
 29 31  1  0
 31 32  2  0
  6 33  1  0
 33 34  2  0
 34 35  2  0
 33 36  1  0
 36 37  2  0
 36  2  1  0
 31  5  1  0
 29  9  1  0
 19 11  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  1
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 20 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  6
 28 67  1  0
 28 68  1  0
M  CHG  2  34   1  35  -1
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.885   3.983  -0.749  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.963   2.920  -0.244  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.623   1.880  -0.988  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.163   1.818  -2.267  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.726   0.827  -0.523  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.180   0.845   0.707  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.285  -0.224   1.144  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.230  -0.469   2.371  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.468  -0.989   0.131  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.469  -0.133  -0.626  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.519   0.637   0.022  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.240   1.391  -1.114  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.179   0.530  -1.882  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.230   1.990  -2.066  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.955   2.530  -0.461  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      -3.737   3.476  -1.778  0.00  0.00          Cl+0
HETATM   17  C   UNK     0      -4.039   1.950   0.370  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.694   0.839   1.274  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.499  -0.003   0.920  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.996  -1.365   0.534  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.818  -0.185   2.158  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.157  -1.978   0.761  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.276  -3.220   0.838  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.904  -4.191   0.707  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.826  -3.468   2.246  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.321  -3.698  -0.113  0.00  0.00           C+0
HETATM   27 Cl   UNK     0       2.243  -5.092   0.543  0.00  0.00          Cl+0
HETATM   28  C   UNK     0       2.328  -2.595  -0.357  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.533  -1.449  -0.889  0.00  0.00           C+0
HETATM   30 Cl   UNK     0       0.628  -2.031  -2.303  0.00  0.00          Cl+0
HETATM   31  C   UNK     0       2.355  -0.312  -1.342  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.781  -0.311  -2.534  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.495   1.950   1.598  0.00  0.00           C+0
HETATM   34  N   UNK     0       1.990   1.967   2.737  0.00  0.00           N+1
HETATM   35  N   UNK     0       1.315   2.280   3.723  0.00  0.00           N-1
HETATM   36  C   UNK     0       3.395   2.987   1.105  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.668   3.937   1.867  0.00  0.00           O+0
HETATM   38  H   UNK     0       5.921   3.647  -0.562  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.705   4.203  -1.816  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.706   4.888  -0.139  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.138   1.496  -2.334  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.184   0.631  -1.163  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.819  -0.762  -1.502  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.023   1.474   0.603  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.612  -0.326  -2.327  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.547   1.127  -2.745  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.049   0.151  -1.350  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.427   2.542  -1.560  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.794   2.746  -2.676  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.862   1.242  -2.805  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.288   3.223   0.074  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.481   2.820   0.948  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.891   1.688  -0.329  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.630   0.200   1.344  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.637   1.268   2.322  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.630  -1.756  -0.405  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.828  -2.139   1.343  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.129  -1.391   0.456  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.316  -0.759   2.760  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.524  -5.229   0.529  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.460  -4.168   1.658  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.526  -3.935  -0.172  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.727  -4.558   2.498  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.178  -2.939   2.960  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.862  -3.144   2.328  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.911  -4.021  -1.080  0.00  0.00           H+0
HETATM   67  H   UNK     0       3.023  -2.918  -1.150  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.878  -2.327   0.566  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    1    3   36                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3   41                                                       
CONECT    5    3    6   31                                                  
CONECT    6    5    7   33                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   22   29                                             
CONECT   10    9   11   42   43                                             
CONECT   11   10   12   19   44                                             
CONECT   12   11   13   14   15                                             
CONECT   13   12   45   46   47                                             
CONECT   14   12   48   49   50                                             
CONECT   15   12   16   17   51                                             
CONECT   16   15                                                            
CONECT   17   15   18   52   53                                             
CONECT   18   17   19   54   55                                             
CONECT   19   18   20   21   11                                             
CONECT   20   19   56   57   58                                             
CONECT   21   19   59                                                       
CONECT   22    9   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23   60   61   62                                             
CONECT   25   23   63   64   65                                             
CONECT   26   23   27   28   66                                             
CONECT   27   26                                                            
CONECT   28   26   29   67   68                                             
CONECT   29   28   30   31    9                                             
CONECT   30   29                                                            
CONECT   31   29   32    5                                                  
CONECT   32   31                                                            
CONECT   33    6   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37    2                                                  
CONECT   37   36                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    4                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   17                                                            
CONECT   53   17                                                            
CONECT   54   18                                                            
CONECT   55   18                                                            
CONECT   56   20                                                            
CONECT   57   20                                                            
CONECT   58   20                                                            
CONECT   59   21                                                            
CONECT   60   24                                                            
CONECT   61   24                                                            
CONECT   62   24                                                            
CONECT   63   25                                                            
CONECT   64   25                                                            
CONECT   65   25                                                            
CONECT   66   26                                                            
CONECT   67   28                                                            
CONECT   68   28                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  142    0
END

RDKit          3D

68 71  0  0  0  0  0  0  0  0999 V2000
    4.8848    3.9833   -0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9631    2.9202   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6230    1.8797   -0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1627    1.8183   -2.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259    0.8269   -0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1796    0.8449    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -0.2240    1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2297   -0.4692    2.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4683   -0.9888    0.1309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4690   -0.1330   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5191    0.6371    0.0218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2400    1.3905   -1.1142 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1793    0.5297   -1.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2296    1.9903   -2.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9553    2.5299   -0.4614 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7375    3.4757   -1.7776 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0387    1.9498    0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6938    0.8388    1.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4991   -0.0026    0.9204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9960   -1.3645    0.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178   -0.1845    2.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1572   -1.9785    0.7608 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763   -3.2197    0.8380 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9038   -4.1914    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8256   -3.4680    2.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3207   -3.6978   -0.1129 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2429   -5.0924    0.5425 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3284   -2.5951   -0.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5333   -1.4489   -0.8891 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6279   -2.0313   -2.3026 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3553   -0.3123   -1.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7809   -0.3107   -2.5339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955    1.9499    1.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9898    1.9668    2.7369 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.3149    2.2803    3.7227 N   0  0  0  0  0  2  0  0  0  0  0  0
    3.3949    2.9871    1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679    3.9367    1.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9213    3.6467   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7052    4.2032   -1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7060    4.8884   -0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381    1.4959   -2.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1841    0.6306   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -0.7621   -1.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226    1.4745    0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -0.3258   -2.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5468    1.1272   -2.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0492    0.1511   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273    2.5424   -1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7936    2.7456   -2.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8616    1.2424   -2.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2882    3.2230    0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4812    2.8196    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8907    1.6885   -0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6295    0.2003    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6369    1.2679    2.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6301   -1.7558   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8284   -2.1385    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1291   -1.3912    0.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3164   -0.7591    2.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237   -5.2291    0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4605   -4.1677    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264   -3.9351   -0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7266   -4.5580    2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777   -2.9392    2.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8623   -3.1436    2.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -4.0208   -1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0226   -2.9178   -1.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784   -2.3269    0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  1
  9 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  6
 29 31  1  0
 31 32  2  0
  6 33  1  0
 33 34  2  0
 34 35  2  0
 33 36  1  0
 36 37  2  0
 36  2  1  0
 31  5  1  0
 29  9  1  0
 19 11  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  1
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 20 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  6
 28 67  1  0
 28 68  1  0
M  CHG  2  34   1  35  -1
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₆H₃₁Cl₃N₂O₆

Average Mass

573.8900 Da

Monoisotopic Mass

572.12477 Da

IUPAC Name

(3R,4aR,10aS)-3,4a-dichloro-10a-{[(1S,3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-6-hydroxy-9-(-lambda4,-lambda2-diazynylidene)-2,2,7-trimethyl-2H,3H,4H,4aH,5H,8H,9H,10H,10aH-naphtho[2,3-b]pyran-5,8,10-trione

Traditional Name

(3R,4aR,10aS)-3,4a-dichloro-10a-{[(1S,3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-6-hydroxy-9-(-lambda4,-lambda2-diazynylidene)-2,2,7-trimethyl-3H,4H-naphtho[2,3-b]pyran-5,8,10-trione

CAS Registry Number

Not Available

SMILES

CC1=C(O)C2=C(C(=O)[C@]3(C[C@@H]4[C@@](C)(O)CC[C@H](Cl)C4(C)C)OC(C)(C)[C@H](Cl)C[C@]3(Cl)C2=O)C(=[N+]=[N-])C1=O

InChI Identifier

InChI=1S/C26H31Cl3N2O6/c1-11-18(32)16-15(17(31-30)19(11)33)21(35)26(9-12-22(2,3)13(27)7-8-24(12,6)36)25(29,20(16)34)10-14(28)23(4,5)37-26/h12-14,32,36H,7-10H2,1-6H3/t12-,13-,14+,24-,25-,26-/m0/s1

InChI Key

DTXSUAICQAUGGW-GIXVMFRNSA-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	NPAtlas	1696251
Streptomyces aculeolatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthalene
Cyclohexanol
Cyclohexyl halide
Cyclohexenone
Pyranone
Oxane
Pyran
Alpha-haloketone
Alpha-chloroketone
Cyclic alcohol
Vinylogous acid
Tertiary alcohol
Ketone
Diazo compound
Cyclic ketone
Dialkyl ether
Enol
Ether
Oxacycle
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alkyl chloride
Alcohol
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Alkyl halide
Organic zwitterion
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.57	ALOGPS
logP	3.47	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	2.27	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	117.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	139.17 m³·mol⁻¹	ChemAxon
Polarizability	55.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA004191

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31128551

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

136249370

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for A80915D (NP0006565)

MOL for NP0006565 (A80915D)

3D MOL for NP0006565 (A80915D)

3D SDF for NP0006565 (A80915D)

3D-SDF for NP0006565 (A80915D)

PDB for NP0006565 (A80915D)

3D PDB for NP0006565 (A80915D)

SMILES for NP0006565 (A80915D)

INCHI for NP0006565 (A80915D)

Structure for NP0006565 (A80915D)

3D Structure for NP0006565 (A80915D)