NP-MRD: Showing NP-Card for Aurachin RE (NP0008243)

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Record Information

Version

2.0

Created at

2020-12-09 05:53:09 UTC

Updated at

2021-07-15 16:59:51 UTC

NP-MRD ID

NP0008243

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aurachin RE

Provided By

NPAtlas

Description

Aurachin RE is found in Rhodococcus. Aurachin RE was first documented in 2008 (PMID: 19168983). Based on a literature review a small amount of articles have been published on Aurachin Re (PMID: 25301659) (PMID: 24269679) (PMID: 23677853) (PMID: 22449052).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106083D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242106083D          

 62 63  0  0  0  0            999 V2000
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   -7.8396    1.2380   -0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0808    0.6515   -0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1871   -0.6532   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0672   -1.3460   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8145   -0.7329    0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6935   -1.4147    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449   -2.6157    0.7608 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7338    2.5142    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6611    2.1292   -0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5811    0.9196    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4570   -0.9752   -0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4906   -0.3414   -1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9968   -0.5670   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6316    2.7740    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523    0.5265   -1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0328    3.1353   -1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2778   -0.3403    0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4674    1.2165    1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705   -2.0285   -0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1213   -0.7256   -2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523   -1.4061   -1.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456    1.1061    1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -0.9200   -1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3939    0.6295   -0.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0478   -1.6311    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263   -0.0999    1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8105   -2.3510   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4582   -3.5575   -0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0939   -2.8356   -0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230   -0.2785    1.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7124   -2.1106    1.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2498   -2.5051    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    2.1942   -0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2535    0.7519   -0.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043    1.6998    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5704    3.2177   -0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7601    2.2698   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9826    1.1874   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1554   -1.1377   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1681   -2.3673    0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 17  1  0  0  0  0
 27 22  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  4 36  1  0  0  0  0
  5 37  1  6  0  0  0
  6 38  1  0  0  0  0
  7 39  1  0  0  0  0
  7 40  1  0  0  0  0
  9 41  1  0  0  0  0
  9 42  1  0  0  0  0
  9 43  1  0  0  0  0
 10 44  1  0  0  0  0
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 11 46  1  0  0  0  0
 12 47  1  0  0  0  0
 12 48  1  0  0  0  0
 14 49  1  0  0  0  0
 14 50  1  0  0  0  0
 14 51  1  0  0  0  0
 15 52  1  0  0  0  0
 16 53  1  0  0  0  0
 16 54  1  0  0  0  0
 19 55  1  0  0  0  0
 19 56  1  0  0  0  0
 19 57  1  0  0  0  0
 21 58  1  0  0  0  0
 23 59  1  0  0  0  0
 24 60  1  0  0  0  0
 25 61  1  0  0  0  0
 26 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008243

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]ON1C2=C([H])C([H])=C([H])C([H])=C2C(=O)C(=C1C([H])([H])[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H33NO3/c1-17(2)15-21(27)16-19(4)10-8-9-18(3)13-14-22-20(5)26(29)24-12-7-6-11-23(24)25(22)28/h6-7,10-13,15,21,27,29H,8-9,14,16H2,1-5H3/b18-13+,19-10+/t21-/m0/s1

> <INCHI_KEY>
CHMBGHGLJJOOSO-VAKGXLRMSA-N

> <FORMULA>
C25H33NO3

> <MOLECULAR_WEIGHT>
395.543

> <EXACT_MASS>
395.246043927

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.71246176938318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-hydroxy-3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2-methyl-1,4-dihydroquinolin-4-one

> <ALOGPS_LOGP>
4.94

> <JCHEM_LOGP>
5.460390849666666

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.238812159446812

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.928640352249552

> <JCHEM_PKA_STRONGEST_BASIC>
-1.316994042215399

> <JCHEM_POLAR_SURFACE_AREA>
60.77

> <JCHEM_REFRACTIVITY>
134.1159

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2-methylquinolin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 63  0  0  0  0  0  0  0  0999 V2000
    9.0315    1.7307    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8117    1.1029   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6911    1.7841   -0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6805    0.5226    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4371   -0.0633   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4834   -1.0839   -1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2794    0.3474    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0219   -0.2228   -0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3413   -0.8911    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9576   -1.5212    0.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0702   -2.5973   -0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0515   -1.0592    1.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3465   -1.6269    0.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4343   -0.7848    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3551    0.5211    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0595    1.2654    0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4959    1.1454   -0.3257 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4042    2.4623   -0.7111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7042    0.5719   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8396    1.2380   -0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0808    0.6515   -0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1871   -0.6532   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0672   -1.3460   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8145   -0.7329    0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6935   -1.4147    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449   -2.6157    0.7608 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7338    2.5142    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6611    2.1292   -0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5811    0.9196    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4570   -0.9752   -0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4906   -0.3414   -1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9968   -0.5670   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6316    2.7740    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523    0.5265   -1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0328    3.1353   -1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2778   -0.3403    0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4674    1.2165    1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705   -2.0285   -0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1213   -0.7256   -2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523   -1.4061   -1.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456    1.1061    1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -0.9200   -1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3939    0.6295   -0.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0478   -1.6311    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263   -0.0999    1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8105   -2.3510   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4582   -3.5575   -0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0939   -2.8356   -0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230   -0.2785    1.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7124   -2.1106    1.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2498   -2.5051    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    2.1942   -0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2535    0.7519   -0.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043    1.6998    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5704    3.2177   -0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7601    2.2698   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9826    1.1874   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1554   -1.1377   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1681   -2.3673    0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 28 17  1  0
 27 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  6
  6 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 14 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 19 55  1  0
 19 56  1  0
 19 57  1  0
 21 58  1  0
 23 59  1  0
 24 60  1  0
 25 61  1  0
 26 62  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       9.031   1.731   0.438  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.812   1.103  -0.166  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.916  -0.267  -0.719  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.691   1.784  -0.186  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.444   1.205  -0.776  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.639   2.239  -1.251  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.681   0.523   0.332  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.437  -0.063  -0.224  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.483  -1.084  -1.293  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.279   0.347   0.259  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.022  -0.223  -0.279  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.341  -0.891   0.905  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.958  -1.521   0.547  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.070  -2.597  -0.466  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.051  -1.059   1.200  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.346  -1.627   0.902  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.434  -0.785   0.447  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.355   0.521   0.062  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.059   1.265   0.056  0.00  0.00           C+0
HETATM   20  N   UNK     0      -5.496   1.145  -0.326  0.00  0.00           N+0
HETATM   21  O   UNK     0      -5.404   2.462  -0.711  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.704   0.572  -0.361  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.840   1.238  -0.761  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.081   0.652  -0.798  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.187  -0.653  -0.418  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.067  -1.346  -0.012  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.814  -0.733   0.018  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.694  -1.415   0.421  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.845  -2.616   0.761  0.00  0.00           O+0
HETATM   30  H   UNK     0       8.734   2.514   1.154  0.00  0.00           H+0
HETATM   31  H   UNK     0       9.661   2.129  -0.383  0.00  0.00           H+0
HETATM   32  H   UNK     0       9.581   0.920   0.950  0.00  0.00           H+0
HETATM   33  H   UNK     0       7.457  -0.975  -0.020  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.491  -0.341  -1.744  0.00  0.00           H+0
HETATM   35  H   UNK     0       8.997  -0.567  -0.787  0.00  0.00           H+0
HETATM   36  H   UNK     0       6.632   2.774   0.217  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.652   0.527  -1.624  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.033   3.135  -1.009  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.278  -0.340   0.748  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.467   1.216   1.157  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.970  -2.029  -0.975  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.121  -0.726  -2.278  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.552  -1.406  -1.457  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.246   1.106   1.055  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.271  -0.920  -1.086  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.394   0.630  -0.642  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.048  -1.631   1.337  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.226  -0.100   1.672  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.811  -2.351  -1.262  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.458  -3.558  -0.017  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.094  -2.836  -0.903  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.923  -0.279   1.939  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.712  -2.111   1.869  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.250  -2.505   0.210  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.239   2.194  -0.581  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.253   0.752  -0.466  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.804   1.700   1.042  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.570   3.218  -0.059  0.00  0.00           H+0
HETATM   59  H   UNK     0      -7.760   2.270  -1.063  0.00  0.00           H+0
HETATM   60  H   UNK     0      -9.983   1.187  -1.118  0.00  0.00           H+0
HETATM   61  H   UNK     0     -10.155  -1.138  -0.438  0.00  0.00           H+0
HETATM   62  H   UNK     0      -8.168  -2.367   0.282  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   33   34   35                                             
CONECT    4    2    5   36                                                  
CONECT    5    4    6    7   37                                             
CONECT    6    5   38                                                       
CONECT    7    5    8   39   40                                             
CONECT    8    7    9   10                                                  
CONECT    9    8   41   42   43                                             
CONECT   10    8   11   44                                                  
CONECT   11   10   12   45   46                                             
CONECT   12   11   13   47   48                                             
CONECT   13   12   14   15                                                  
CONECT   14   13   49   50   51                                             
CONECT   15   13   16   52                                                  
CONECT   16   15   17   53   54                                             
CONECT   17   16   18   28                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   55   56   57                                             
CONECT   20   18   21   22                                                  
CONECT   21   20   58                                                       
CONECT   22   20   23   27                                                  
CONECT   23   22   24   59                                                  
CONECT   24   23   25   60                                                  
CONECT   25   24   26   61                                                  
CONECT   26   25   27   62                                                  
CONECT   27   26   28   22                                                  
CONECT   28   27   29   17                                                  
CONECT   29   28                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   14                                                            
CONECT   50   14                                                            
CONECT   51   14                                                            
CONECT   52   15                                                            
CONECT   53   16                                                            
CONECT   54   16                                                            
CONECT   55   19                                                            
CONECT   56   19                                                            
CONECT   57   19                                                            
CONECT   58   21                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
CONECT   62   26                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  126    0
END

RDKit          3D

62 63  0  0  0  0  0  0  0  0999 V2000
    9.0315    1.7307    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8117    1.1029   -0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9162   -0.2672   -0.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6911    1.7841   -0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4444    1.2052   -0.7762 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6390    2.2390   -1.2512 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6805    0.5226    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4371   -0.0633   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4834   -1.0839   -1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2794    0.3474    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0219   -0.2228   -0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3413   -0.8911    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9576   -1.5212    0.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0702   -2.5973   -0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0515   -1.0592    1.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3465   -1.6269    0.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4343   -0.7848    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3551    0.5211    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0595    1.2654    0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4959    1.1454   -0.3257 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4042    2.4623   -0.7111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7042    0.5719   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8396    1.2380   -0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0808    0.6515   -0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1871   -0.6532   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0672   -1.3460   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8145   -0.7329    0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6935   -1.4147    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449   -2.6157    0.7608 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7338    2.5142    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6611    2.1292   -0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5811    0.9196    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4570   -0.9752   -0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4906   -0.3414   -1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9968   -0.5670   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6316    2.7740    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523    0.5265   -1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0328    3.1353   -1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2778   -0.3403    0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4674    1.2165    1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705   -2.0285   -0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1213   -0.7256   -2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523   -1.4061   -1.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456    1.1061    1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -0.9200   -1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3939    0.6295   -0.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0478   -1.6311    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263   -0.0999    1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8105   -2.3510   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4582   -3.5575   -0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0939   -2.8356   -0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230   -0.2785    1.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7124   -2.1106    1.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2498   -2.5051    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392    2.1942   -0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2535    0.7519   -0.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043    1.6998    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5704    3.2177   -0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7601    2.2698   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9826    1.1874   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1554   -1.1377   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1681   -2.3673    0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 28 17  1  0
 27 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  6
  6 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 14 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 19 55  1  0
 19 56  1  0
 19 57  1  0
 21 58  1  0
 23 59  1  0
 24 60  1  0
 25 61  1  0
 26 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₅H₃₃NO₃

Average Mass

395.5430 Da

Monoisotopic Mass

395.24604 Da

IUPAC Name

1-hydroxy-3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2-methyl-1,4-dihydroquinolin-4-one

Traditional Name

1-hydroxy-3-[(2E,6E,9R)-9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2-methylquinolin-4-one

CAS Registry Number

Not Available

SMILES

CC(C)=CC(O)C\C(C)=C\CC\C(C)=C\CC1=C(C)N(O)C2=CC=CC=C2C1=O

InChI Identifier

InChI=1S/C25H33NO3/c1-17(2)15-21(27)16-19(4)10-8-9-18(3)13-14-22-20(5)26(29)24-12-7-6-11-23(24)25(22)28/h6-7,10-13,15,21,27,29H,8-9,14,16H2,1-5H3/b18-13+,19-10+

InChI Key

CHMBGHGLJJOOSO-VAKGXLRMSA-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
Rhodococcus	NPAtlas	19168983

Chemical Taxonomy

Classification

Not classified

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	4.94	ALOGPS
logP	5.46	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.93	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.77 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.12 m³·mol⁻¹	ChemAxon
Polarizability	47.71 Å³	ChemAxon
Number of Rings	2	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

NPA000904

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28286034

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25188767

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kitagawa W, Tamura T: A quinoline antibiotic from Rhodococcus erythropolis JCM 6824. J Antibiot (Tokyo). 2008 Nov;61(11):680-2. doi: 10.1038/ja.2008.96. [PubMed:19168983 ]
Kitagawa W, Hata M, Sekizuka T, Kuroda M, Ishikawa J: Draft Genome Sequence of Rhodococcus erythropolis JCM 6824, an Aurachin RE Antibiotic Producer. Genome Announc. 2014 Oct 9;2(5). pii: 2/5/e01026-14. doi: 10.1128/genomeA.01026-14. [PubMed:25301659 ]
Yasutake Y, Kitagawa W, Hata M, Nishioka T, Ozaki T, Nishiyama M, Kuzuyama T, Tamura T: Structure of the quinoline N-hydroxylating cytochrome P450 RauA, an essential enzyme that confers antibiotic activity on aurachin alkaloids. FEBS Lett. 2014 Jan 3;588(1):105-10. doi: 10.1016/j.febslet.2013.11.016. Epub 2013 Nov 20. [PubMed:24269679 ]
Kitagawa W, Ozaki T, Nishioka T, Yasutake Y, Hata M, Nishiyama M, Kuzuyama T, Tamura T: Cloning and heterologous expression of the aurachin RE biosynthesis gene cluster afford a new cytochrome P450 for quinoline N-hydroxylation. Chembiochem. 2013 Jun 17;14(9):1085-93. doi: 10.1002/cbic.201300167. Epub 2013 May 15. [PubMed:23677853 ]
Debnath J, Siricilla S, Wan B, Crick DC, Lenaerts AJ, Franzblau SG, Kurosu M: Discovery of selective menaquinone biosynthesis inhibitors against Mycobacterium tuberculosis. J Med Chem. 2012 Apr 26;55(8):3739-55. doi: 10.1021/jm201608g. Epub 2012 Apr 6. [PubMed:22449052 ]

Showing NP-Card for Aurachin RE (NP0008243)

MOL for NP0008243 (Aurachin RE)

3D MOL for NP0008243 (Aurachin RE)

3D SDF for NP0008243 (Aurachin RE)

3D-SDF for NP0008243 (Aurachin RE)

PDB for NP0008243 (Aurachin RE)

3D PDB for NP0008243 (Aurachin RE)

SMILES for NP0008243 (Aurachin RE)

INCHI for NP0008243 (Aurachin RE)

Structure for NP0008243 (Aurachin RE)

3D Structure for NP0008243 (Aurachin RE)