NP-MRD: Showing NP-Card for (2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid (NP0196100)

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Record Information

Version

2.0

Created at

2022-09-04 14:06:32 UTC

Updated at

2022-09-04 14:06:32 UTC

NP-MRD ID

NP0196100

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid

Description

Dorrigocin B belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. (2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid is found in Streptomyces platensis. (2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid was first documented in 2005 (PMID: 16117518). Based on a literature review very few articles have been published on Dorrigocin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042216062D          

 36 36  0  0  1  0            999 V2000
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042216062D          

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    7.1447   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 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
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 29 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196100

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H](\C=C\CC\C=C\C(O)=O)[C@@H](O)[C@H](C)[C@@H](O)C(\C)=C\[C@H](C)C(=O)CCCC1CC(O)=NC(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H41NO8/c1-17(21(29)11-9-10-20-15-23(30)28-24(31)16-20)14-18(2)26(34)19(3)27(35)22(36-4)12-7-5-6-8-13-25(32)33/h7-8,12-14,17,19-20,22,26-27,34-35H,5-6,9-11,15-16H2,1-4H3,(H,32,33)(H,28,30,31)/b12-7+,13-8+,18-14+/t17-,19+,22-,26-,27-/m0/s1

> <INCHI_KEY>
YQDJUXPUIRGKNV-NRWIMSPQSA-N

> <FORMULA>
C27H41NO8

> <MOLECULAR_WEIGHT>
507.624

> <EXACT_MASS>
507.283217284

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.878175824606046

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,6E,8S,9S,10R,11R,12E,14S)-9,11-dihydroxy-18-(6-hydroxy-2-oxo-2,3,4,5-tetrahydropyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid

> <JCHEM_LOGP>
2.737282861666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.365055594272874

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4597172441775546

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1110322863318727

> <JCHEM_POLAR_SURFACE_AREA>
153.72

> <JCHEM_REFRACTIVITY>
137.976

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6E,8S,9S,10R,11R,12E,14S)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3H-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668 -20.790   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.002 -18.480   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0      13.337  -9.240   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    3   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₁NO₈

Average Mass

507.6240 Da

Monoisotopic Mass

507.28322 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@@H](\C=C\CC\C=C\C(O)=O)[C@@H](O)[C@H](C)[C@@H](O)C(\C)=C\[C@H](C)C(=O)CCCC1CC(O)=NC(=O)C1

InChI Identifier

InChI=1S/C27H41NO8/c1-17(21(29)11-9-10-20-15-23(30)28-24(31)16-20)14-18(2)26(34)19(3)27(35)22(36-4)12-7-5-6-8-13-25(32)33/h7-8,12-14,17,19-20,22,26-27,34-35H,5-6,9-11,15-16H2,1-4H3,(H,32,33)(H,28,30,31)/b12-7+,13-8+,18-14+/t17-,19+,22-,26-,27-/m0/s1

InChI Key

YQDJUXPUIRGKNV-NRWIMSPQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 platensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Piperidinedione
Amino fatty acid
Branched fatty acid
Delta-lactam
Heterocyclic fatty acid
Hydroxy fatty acid
Piperidinone
Methyl-branched fatty acid
Fatty acid
Piperidine
Unsaturated fatty acid
Carboxylic acid imide
Carboxylic acid imide, n-unsubstituted
Dicarboximide
Secondary alcohol
Ketone
Lactam
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Carboxylic acid
Dialkyl ether
Monocarboxylic acid or derivatives
Ether
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24604151

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44543727

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ju J, Lim SK, Jiang H, Seo JW, Shen B: Iso-migrastatin congeners from Streptomyces platensis and generation of a glutarimide polyketide library featuring the dorrigocin, lactimidomycin, migrastatin, and NK30424 scaffolds. J Am Chem Soc. 2005 Aug 31;127(34):11930-1. doi: 10.1021/ja053118u. [PubMed:16117518 ]
LOTUS database [Link]

Showing NP-Card for (2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid (NP0196100)

MOL for NP0196100 ((2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid)

3D MOL for NP0196100 ((2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid)

3D SDF for NP0196100 ((2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid)

3D-SDF for NP0196100 ((2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid)

PDB for NP0196100 ((2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid)

3D PDB for NP0196100 ((2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid)

SMILES for NP0196100 ((2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid)

INCHI for NP0196100 ((2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid)

Structure for NP0196100 ((2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid)

3D Structure for NP0196100 ((2e,6e,8s,9s,10r,11r,12e,14s)-9,11-dihydroxy-18-(2-hydroxy-6-oxo-4,5-dihydro-3h-pyridin-4-yl)-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,12-trienoic acid)