NP-MRD: Showing NP-Card for Platensimycin (NP0006551)

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Record Information

Version

2.0

Created at

2020-12-09 03:32:06 UTC

Updated at

2021-07-15 16:55:08 UTC

NP-MRD ID

NP0006551

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Platensimycin

Provided By

NPAtlas

Description

Platensimycin belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. Platensimycin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Platensimycin is found in Streptomyces and Streptomyces aureus. Platensimycin was first documented in 2006 (PMID: 16953632). Based on a literature review a small amount of articles have been published on Platensimycin (PMID: 21214253) (PMID: 21915133) (PMID: 20158476) (PMID: 21808805).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118283D          

 59 63  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118283D          

 59 63  0  0  0  0            999 V2000
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   -2.4400    0.2907   -0.2253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2237    1.0815    1.0114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9668    0.5970    2.2299 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4054    0.7399    1.7156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6098   -0.4812    0.8204 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9358    2.3003    0.8080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7810    2.7700    2.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9719    3.1149    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463    3.9951    1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0623    1.8830   -1.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6566    1.1920   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1097   -1.1336   -1.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3055   -2.0551   -3.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010   -2.8414   -0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7293   -2.5734   -0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693   -2.0826    1.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929    0.6137   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -0.2584    0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -1.7691   -1.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049   -2.2603    0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4742   -2.4407   -0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462   -1.9861    3.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553   -0.6495    2.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0492    0.6910    1.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9038    2.4917   -2.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714    0.4999   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    1.0317   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1937    1.3756    1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7689    1.3125    3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191   -0.4390    2.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1332    0.8259    2.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2519   -1.3752    1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6931   -0.4914    0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  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  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 21 25  2  0  0  0  0
 25 26  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 28 32  1  0  0  0  0
 30  2  1  0  0  0  0
 32  2  1  0  0  0  0
 27  4  1  0  0  0  0
 31  4  1  0  0  0  0
 25 16  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  5 38  1  0  0  0  0
  6 39  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
 10 42  1  0  0  0  0
 11 43  1  0  0  0  0
 11 44  1  0  0  0  0
 12 45  1  0  0  0  0
 12 46  1  0  0  0  0
 15 47  1  0  0  0  0
 18 48  1  0  0  0  0
 19 49  1  0  0  0  0
 20 50  1  0  0  0  0
 24 51  1  0  0  0  0
 26 52  1  0  0  0  0
 27 53  1  6  0  0  0
 28 54  1  1  0  0  0
 29 55  1  0  0  0  0
 29 56  1  0  0  0  0
 30 57  1  1  0  0  0
 31 58  1  0  0  0  0
 31 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006551

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(O[H])C(N([H])C(=O)C([H])([H])C([H])([H])[C@@]2(C(=O)C([H])=C([H])[C@]34C([H])([H])[C@@]5([H])C([H])([H])[C@]([H])(O[C@@]5(C([H])([H])[H])C3([H])[H])[C@@]24[H])C([H])([H])[H])=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H27NO7/c1-22(7-6-17(28)25-18-14(26)4-3-13(19(18)29)21(30)31)16(27)5-8-24-10-12-9-15(20(22)24)32-23(12,2)11-24/h3-5,8,12,15,20,26,29H,6-7,9-11H2,1-2H3,(H,25,28)(H,30,31)/t12-,15+,20+,22-,23+,24+/m1/s1

> <INCHI_KEY>
CSOMAHTTWTVBFL-OFBLZTNGSA-N

> <FORMULA>
C24H27NO7

> <MOLECULAR_WEIGHT>
441.4737

> <EXACT_MASS>
441.178752223

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.65081135001755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{3-[(1S,5S,6R,7S,9S,10S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1^{7,10}.0^{1,6}]tridec-2-en-5-yl]propanamido}-2,4-dihydroxybenzoic acid

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
3.2362086423333336

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.149922452000974

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9567831906943804

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3995074083452637

> <JCHEM_POLAR_SURFACE_AREA>
133.16

> <JCHEM_REFRACTIVITY>
116.81049999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{3-[(1S,5S,6R,7S,9S,10S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1^{7,10}.0^{1,6}]tridec-2-en-5-yl]propanamido}-2,4-dihydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
   -5.2034    3.0399    1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2924    1.9024    0.7860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5742    1.3309   -0.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833   -0.0434   -0.4198 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1022   -0.8988   -1.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950   -1.4185   -2.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7082   -1.1422   -1.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8098   -1.1811   -2.8039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -0.8187   -0.5161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7512   -2.1020    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0945   -0.3800   -0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842   -1.3712   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2966   -0.7458   -0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3389    0.4103    0.3732 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002   -1.4724   -0.2964 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7344   -0.8791    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2090   -1.0521    1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4586   -1.8153    2.2308 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4097   -0.4891    1.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1110    0.2504    0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6688    0.4614   -0.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4830    1.2597   -1.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5760    1.7380   -0.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1621    1.5356   -2.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4720   -0.1162   -0.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9478    0.0279   -2.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4400    0.2907   -0.2253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2237    1.0815    1.0114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9668    0.5970    2.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    0.7399    1.7156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6098   -0.4812    0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358    2.3003    0.8080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7810    2.7700    2.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9719    3.1149    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463    3.9951    1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0623    1.8830   -1.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6566    1.1920   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1097   -1.1336   -1.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3055   -2.0551   -3.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010   -2.8414   -0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7293   -2.5734   -0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693   -2.0826    1.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929    0.6137   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -0.2584    0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -1.7691   -1.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049   -2.2603    0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4742   -2.4407   -0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462   -1.9861    3.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553   -0.6495    2.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0492    0.6910    1.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9038    2.4917   -2.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714    0.4999   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    1.0317   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1937    1.3756    1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7689    1.3125    3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191   -0.4390    2.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1332    0.8259    2.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2519   -1.3752    1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6931   -0.4914    0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  6
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  2  0
 25 26  1  0
  9 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 28 32  1  0
 30  2  1  0
 32  2  1  0
 27  4  1  0
 31  4  1  0
 25 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  5 38  1  0
  6 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 15 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 24 51  1  0
 26 52  1  0
 27 53  1  6
 28 54  1  1
 29 55  1  0
 29 56  1  0
 30 57  1  1
 31 58  1  0
 31 59  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      -5.203   3.040   1.128  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.292   1.902   0.786  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.574   1.331  -0.600  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.883  -0.043  -0.420  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.102  -0.899  -1.577  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.095  -1.419  -2.301  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.708  -1.142  -1.950  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.810  -1.181  -2.804  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.480  -0.819  -0.516  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.751  -2.102   0.220  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.095  -0.380  -0.195  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.984  -1.371  -0.501  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.297  -0.746  -0.112  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.339   0.410   0.373  0.00  0.00           O+0
HETATM   15  N   UNK     0       3.500  -1.472  -0.296  0.00  0.00           N+0
HETATM   16  C   UNK     0       4.734  -0.879   0.072  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.209  -1.052   1.332  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.459  -1.815   2.231  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.410  -0.489   1.730  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.111   0.250   0.817  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.669   0.461  -0.497  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.483   1.260  -1.389  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.576   1.738  -0.931  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.162   1.536  -2.684  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.472  -0.116  -0.847  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.948   0.028  -2.108  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.440   0.291  -0.225  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.224   1.081   1.011  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.967   0.597   2.230  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.405   0.740   1.716  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.610  -0.481   0.820  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.936   2.300   0.808  0.00  0.00           O+0
HETATM   33  H   UNK     0      -5.781   2.770   2.046  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.972   3.115   0.318  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.646   3.995   1.248  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.062   1.883  -1.391  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.657   1.192  -0.752  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.110  -1.134  -1.877  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.305  -2.055  -3.163  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.001  -2.841  -0.200  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.729  -2.573  -0.081  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.569  -2.083   1.291  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.093   0.614  -0.641  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.071  -0.258   0.933  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.007  -1.769  -1.511  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.905  -2.260   0.190  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.474  -2.441  -0.702  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.746  -1.986   3.178  0.00  0.00           H+0
HETATM   49  H   UNK     0       6.755  -0.650   2.744  0.00  0.00           H+0
HETATM   50  H   UNK     0       8.049   0.691   1.126  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.904   2.492  -2.929  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.271   0.500  -2.894  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.218   1.032  -1.068  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.194   1.376   1.216  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.769   1.313   3.042  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.819  -0.439   2.497  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.133   0.826   2.506  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.252  -1.375   1.309  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.693  -0.491   0.576  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3   30   32                                             
CONECT    3    2    4   36   37                                             
CONECT    4    3    5   27   31                                             
CONECT    5    4    6   38                                                  
CONECT    6    5    7   39                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   27                                             
CONECT   10    9   40   41   42                                             
CONECT   11    9   12   43   44                                             
CONECT   12   11   13   45   46                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   47                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   48                                                       
CONECT   19   17   20   49                                                  
CONECT   20   19   21   50                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   51                                                       
CONECT   25   21   26   16                                                  
CONECT   26   25   52                                                       
CONECT   27    9   28    4   53                                             
CONECT   28   27   29   32   54                                             
CONECT   29   28   30   55   56                                             
CONECT   30   29   31    2   57                                             
CONECT   31   30    4   58   59                                             
CONECT   32   28    2                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   15                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   24                                                            
CONECT   52   26                                                            
CONECT   53   27                                                            
CONECT   54   28                                                            
CONECT   55   29                                                            
CONECT   56   29                                                            
CONECT   57   30                                                            
CONECT   58   31                                                            
CONECT   59   31                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  126    0
END

RDKit          3D

59 63  0  0  0  0  0  0  0  0999 V2000
   -5.2034    3.0399    1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2924    1.9024    0.7860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5742    1.3309   -0.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833   -0.0434   -0.4198 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1022   -0.8988   -1.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950   -1.4185   -2.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7082   -1.1422   -1.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8098   -1.1811   -2.8039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -0.8187   -0.5161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7512   -2.1020    0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0945   -0.3800   -0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842   -1.3712   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2966   -0.7458   -0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3389    0.4103    0.3732 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002   -1.4724   -0.2964 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7344   -0.8791    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2090   -1.0521    1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4586   -1.8153    2.2308 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4097   -0.4891    1.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1110    0.2504    0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6688    0.4614   -0.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4830    1.2597   -1.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5760    1.7380   -0.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1621    1.5356   -2.6839 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4720   -0.1162   -0.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9478    0.0279   -2.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4400    0.2907   -0.2253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2237    1.0815    1.0114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9668    0.5970    2.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    0.7399    1.7156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6098   -0.4812    0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358    2.3003    0.8080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7810    2.7700    2.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9719    3.1149    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6463    3.9951    1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0623    1.8830   -1.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6566    1.1920   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1097   -1.1336   -1.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3055   -2.0551   -3.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010   -2.8414   -0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7293   -2.5734   -0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693   -2.0826    1.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929    0.6137   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -0.2584    0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -1.7691   -1.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049   -2.2603    0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4742   -2.4407   -0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462   -1.9861    3.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553   -0.6495    2.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0492    0.6910    1.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9038    2.4917   -2.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714    0.4999   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    1.0317   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1937    1.3756    1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7689    1.3125    3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191   -0.4390    2.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1332    0.8259    2.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2519   -1.3752    1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6931   -0.4914    0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  6
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  2  0
 25 26  1  0
  9 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 28 32  1  0
 30  2  1  0
 32  2  1  0
 27  4  1  0
 31  4  1  0
 25 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  5 38  1  0
  6 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 15 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 24 51  1  0
 26 52  1  0
 27 53  1  6
 28 54  1  1
 29 55  1  0
 29 56  1  0
 30 57  1  1
 31 58  1  0
 31 59  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-Platensimycin	ChEBI
3-[[3-[(1S,3S,4S,5AS,9S,9ar)-1,4,5,8,9,9a-hexahydro-3,9-dimethyl-8-oxo-3H-1,4:3,5a-dimethano-2-benzoxepin-9-yl]-1-oxopropyl]amino]-2,4-dihydroxybenzoic acid	ChEBI
3-[[3-[(1S,3S,4S,5AS,9S,9ar)-1,4,5,8,9,9a-hexahydro-3,9-dimethyl-8-oxo-3H-1,4:3,5a-dimethano-2-benzoxepin-9-yl]-1-oxopropyl]amino]-2,4-dihydroxybenzoate	Generator

Chemical Formula

C₂₄H₂₇NO₇

Average Mass

441.4737 Da

Monoisotopic Mass

441.17875 Da

IUPAC Name

3-{3-[(1S,5S,6R,7S,9S,10S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1^{7,10}.0^{1,6}]tridec-2-en-5-yl]propanamido}-2,4-dihydroxybenzoic acid

Traditional Name

3-{3-[(1S,5S,6R,7S,9S,10S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1^{7,10}.0^{1,6}]tridec-2-en-5-yl]propanamido}-2,4-dihydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@]34C[C@H]1C[C@H](O2)[C@H]3[C@](C)(CCC(=O)NC1=C(O)C=CC(C(O)=O)=C1O)C(=O)C=C4

InChI Identifier

InChI=1S/C24H27NO7/c1-22(7-6-17(28)25-18-14(26)4-3-13(19(18)29)21(30)31)16(27)5-8-24-10-12-9-15(20(22)24)32-23(12,2)11-24/h3-5,8,12,15,20,26,29H,6-7,9-11H2,1-2H3,(H,25,28)(H,30,31)/t12-,15+,20+,22-,23+,24+/m1/s1

InChI Key

CSOMAHTTWTVBFL-OFBLZTNGSA-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	16953632
Streptomyces aureus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces platensis	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Dihydroxybenzoic acid
Salicylic acid or derivatives
Salicylic acid
Hydroxybenzoic acid
Benzoic acid
Resorcinol
Benzoyl
Oxepane
Phenol
1-hydroxy-4-unsubstituted benzenoid
Cyclohexenone
1-hydroxy-2-unsubstituted benzenoid
Oxane
Vinylogous acid
Tetrahydrofuran
Ketone
Cyclic ketone
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:68236 )
monocarboxylic acid amide (CHEBI:68236 )
aromatic amide (CHEBI:68236 )
cyclic ether (CHEBI:68236 )
dihydroxybenzoic acid (CHEBI:68236 )
polycyclic cage (CHEBI:68236 )

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	2.6	ALOGPS
logP	3.24	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.16 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	116.81 m³·mol⁻¹	ChemAxon
Polarizability	45.65 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA017180

HMDB ID

Not Available

DrugBank ID

DB08407

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00048823

Chemspider ID

5257055

KEGG Compound ID

C20132

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Platensimycin

METLIN ID

Not Available

PubChem Compound

6857724

PDB ID

Not Available

ChEBI ID

68236

Good Scents ID

Not Available

References

General References

Singh SB, Jayasuriya H, Ondeyka JG, Herath KB, Zhang C, Zink DL, Tsou NN, Ball RG, Basilio A, Genilloud O, Diez MT, Vicente F, Pelaez F, Young K, Wang J: Isolation, structure, and absolute stereochemistry of platensimycin, a broad spectrum antibiotic discovered using an antisense differential sensitivity strategy. J Am Chem Soc. 2006 Sep 13;128(36):11916-20. doi: 10.1021/ja062232p. [PubMed:16953632 ]
Zhang C, Ondeyka J, Herath K, Jayasuriya H, Guan Z, Zink DL, Dietrich L, Burgess B, Ha SN, Wang J, Singh SB: Platensimycin and platencin congeners from Streptomyces platensis. J Nat Prod. 2011 Mar 25;74(3):329-40. doi: 10.1021/np100635f. Epub 2011 Jan 7. [PubMed:21214253 ]
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Showing NP-Card for Platensimycin (NP0006551)

MOL for NP0006551 (Platensimycin)

3D MOL for NP0006551 (Platensimycin)

3D SDF for NP0006551 (Platensimycin)

3D-SDF for NP0006551 (Platensimycin)

PDB for NP0006551 (Platensimycin)

3D PDB for NP0006551 (Platensimycin)

SMILES for NP0006551 (Platensimycin)

INCHI for NP0006551 (Platensimycin)

Structure for NP0006551 (Platensimycin)

3D Structure for NP0006551 (Platensimycin)