NP-MRD: Showing NP-Card for narbonolide (NP0187132)

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Record Information

Version

2.0

Created at

2022-09-04 03:11:53 UTC

Updated at

2022-09-04 03:11:54 UTC

NP-MRD ID

NP0187132

Secondary Accession Numbers

None

Natural Product Identification

Common Name

narbonolide

Description

Narbonolide belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Narbonolide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. narbonolide is found in Streptomyces venezuelae. narbonolide was first documented in 2008 (PMID: 18512859). Based on a literature review a small amount of articles have been published on narbonolide (PMID: 22168449) (PMID: 18427928) (PMID: 18245260) (PMID: 18239422).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 57 57  0  0  0  0  0  0  0  0999 V2000
    4.3353    0.2909    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348    0.4976    1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8232    0.1103    0.4888 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5992    0.8451   -0.6714 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5131    2.1806   -0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2318    2.7156   -1.7917 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6408    3.1120   -0.1011 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4574    3.9137    0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253    2.4697    0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6412    2.4463    1.7146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    1.8562   -0.3269 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3069    3.0211   -0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4965    0.9376    0.3394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7010    0.8431   -0.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -0.4283    0.6409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1932   -1.1636    1.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7483   -1.2196   -0.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855   -2.6740   -0.3752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7075   -3.5253   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453   -3.2160   -1.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995   -4.5001   -1.1888 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267   -2.4980   -1.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6109   -1.6927   -1.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6842   -1.3587    0.2358 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8264   -2.1869    0.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0364   -0.3815    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9326    1.2388    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1510   -0.0498   -0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2318    0.0083    2.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1009    1.5943    1.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497    0.3424    1.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2823    3.9275   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121    4.8599    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589    3.3794    1.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    4.1913    0.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0849    1.3141   -1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2800    3.9035   -0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3527    2.7424   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7806    3.3536   -1.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7871    1.4213    1.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4671    0.7185   -1.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1936   -0.4954    1.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8528   -2.0606    1.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5212   -0.4481    2.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0527   -1.2810    0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6659   -1.1529   -1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333   -0.7139   -1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3528   -2.8404    0.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4551   -4.2679   -1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -4.1093    0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4990   -2.8805   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238   -2.6482   -2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3832   -1.1970   -1.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7560   -1.7854    0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7058   -2.2263    0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0346   -1.9813    1.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363   -3.2521    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24  3  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  1
  7 32  1  6
  8 33  1  0
  8 34  1  0
  8 35  1  0
 11 36  1  6
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  1
 14 41  1  0
 15 42  1  1
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  1
 19 49  1  0
 19 50  1  0
 19 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  1
 25 55  1  0
 25 56  1  0
 25 57  1  0
M  END


  Mrv1652309042205112D          

 25 25  0  0  1  0            999 V2000
    2.0562    2.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161    1.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.8851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3263    1.5088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765    1.9765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4064    0.5733    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2166    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664   -0.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562    0.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364   -0.8299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9465   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5963   -1.4535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8664   -2.2331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.2976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0562   -2.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461   -1.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360   -1.7654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1041   -2.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6442   -0.8299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7060   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9760    1.0410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7060    1.8206    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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  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  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  2  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
  3 24  1  0  0  0  0
 24 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0187132

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)C[C@@H](C)C(=O)\C=C\[C@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/c1-7-17-11(2)8-9-16(21)12(3)10-13(4)18(22)14(5)19(23)15(6)20(24)25-17/h8-9,11-15,17-18,22H,7,10H2,1-6H3/b9-8+/t11-,12-,13+,14-,15-,17-,18+/m1/s1

> <INCHI_KEY>
YFFOFFWSBYZSOI-HQWJGCFGSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.471

> <EXACT_MASS>
352.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.186912898875946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,5R,6S,7S,9R,11E,13R,14R)-14-ethyl-6-hydroxy-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11-ene-2,4,10-trione

> <JCHEM_LOGP>
4.369182534

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.595200151036575

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.499174442175379

> <JCHEM_PKA_STRONGEST_BASIC>
-3.002328309545227

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
97.27

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
narbonolide

> <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       3.838   4.272   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.830   3.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.334   1.652   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.342   2.816   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.855   2.525   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.863   3.689   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.359   1.070   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.871   0.779   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.351  -0.094   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.838   0.197   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.855  -1.549   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.367  -1.840   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.846  -2.713   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.351  -4.168   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.334  -2.422   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.838  -3.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.326  -3.586   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.814  -3.295   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.194  -4.459   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.310  -1.840   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.203  -1.549   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.318  -0.676   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.814   0.779   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.822   1.943   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.318   3.398   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    3   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₅

Average Mass

352.4710 Da

Monoisotopic Mass

352.22497 Da

IUPAC Name

(3R,5R,6S,7S,9R,11E,13R,14R)-14-ethyl-6-hydroxy-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11-ene-2,4,10-trione

Traditional Name

narbonolide

CAS Registry Number

Not Available

SMILES

CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)C[C@@H](C)C(=O)\C=C\[C@H]1C

InChI Identifier

InChI=1S/C20H32O5/c1-7-17-11(2)8-9-16(21)12(3)10-13(4)18(22)14(5)19(23)15(6)20(24)25-17/h8-9,11-15,17-18,22H,7,10H2,1-6H3/b9-8+/t11-,12-,13+,14-,15-,17-,18+/m1/s1

InChI Key

YFFOFFWSBYZSOI-HQWJGCFGSA-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 venezuelae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
1,3-dicarbonyl compound
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Cyclic ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

enone (CHEBI:29650 )
macrolide (CHEBI:29650 )

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	4.37	ChemAxon
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	97.27 m³·mol⁻¹	ChemAxon
Polarizability	39.19 Å³	ChemAxon
Number of Rings	1	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4445265

KEGG Compound ID

C11997

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282035

PDB ID

Not Available

ChEBI ID

29650

Good Scents ID

Not Available

References

General References

Oh HS, Kang HY: Total synthesis of pikromycin. J Org Chem. 2012 Jan 20;77(2):1125-30. doi: 10.1021/jo201158q. Epub 2011 Dec 30. [PubMed:22168449 ]
Gupta S, Lakshmanan V, Kim BS, Fecik R, Reynolds KA: Generation of novel pikromycin antibiotic products through mutasynthesis. Chembiochem. 2008 Jul 2;9(10):1609-16. doi: 10.1002/cbic.200700635. [PubMed:18512859 ]
Pageni BB, Oh TJ, Lee HC, Sohng JK: Metabolic engineering of noviose: heterologous expression of novWUS and generation of a new hybrid antibiotic, noviosylated 10-deoxymethynolide/narbonolide, from Streptomyces venezuelae YJ003-OTBP1. Biotechnol Lett. 2008 Sep;30(9):1609-15. doi: 10.1007/s10529-008-9733-2. Epub 2008 Apr 22. [PubMed:18427928 ]
Jung WS, Jeong SJ, Park SR, Choi CY, Park BC, Park JW, Yoon YJ: Enhanced heterologous production of desosaminyl macrolides and their hydroxylated derivatives by overexpression of the pikD regulatory gene in Streptomyces venezuelae. Appl Environ Microbiol. 2008 Apr;74(7):1972-9. doi: 10.1128/AEM.02296-07. Epub 2008 Feb 1. [PubMed:18245260 ]
Pageni BB, Oh TJ, Liou K, Yoon YJ, Sohng JK: Genetically engineered biosynthesis of macrolide derivatives including 4-amino-4,6-dideoxy-L-glucose from Streptomyces venezuelae YJ003-OTBP3. J Microbiol Biotechnol. 2008 Jan;18(1):88-94. [PubMed:18239422 ]
LOTUS database [Link]

Showing NP-Card for narbonolide (NP0187132)

MOL for NP0187132 (narbonolide)

3D MOL for NP0187132 (narbonolide)

3D SDF for NP0187132 (narbonolide)

3D-SDF for NP0187132 (narbonolide)

PDB for NP0187132 (narbonolide)

3D PDB for NP0187132 (narbonolide)

SMILES for NP0187132 (narbonolide)

INCHI for NP0187132 (narbonolide)

Structure for NP0187132 (narbonolide)

3D Structure for NP0187132 (narbonolide)