NP-MRD: Showing NP-Card for (9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one (NP0206099)

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Record Information

Version

2.0

Created at

2022-09-05 02:12:58 UTC

Updated at

2022-09-05 02:12:58 UTC

NP-MRD ID

NP0206099

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one

Description

Pladienolide G belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one is found in Streptomyces platensis. Based on a literature review very few articles have been published on Pladienolide G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204122D          

 36 37  0  0  0  0            999 V2000
   -3.9849    1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5243   -0.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8743   -0.5868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2868   -2.1263    0.0000 O   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


  Mrv1652309052204122D          

 36 37  0  0  0  0            999 V2000
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  -12.2565   -4.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5387   -5.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0690   -4.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2565   -3.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9710   -3.3638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5421   -3.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5421   -2.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8276   -2.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8276   -1.3013    0.0000 C   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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 10  1  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
 12 14  1  0  0  0  0
 14 15  2  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  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  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
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  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
 19 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206099

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(O)C(C)(O)C1OC1CC(C)\C=C\C=C(/C)C1OC(=O)CC(O)CCC(C)(O)C(O)\C=C\C1C

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O8/c1-7-22(30)28(6,34)26-21(35-26)15-17(2)9-8-10-18(3)25-19(4)11-12-23(31)27(5,33)14-13-20(29)16-24(32)36-25/h8-12,17,19-23,25-26,29-31,33-34H,7,13-16H2,1-6H3/b9-8+,12-11+,18-10+

> <INCHI_KEY>
GOQNOCIWFDQNEZ-AEXVIOBPSA-N

> <FORMULA>
C28H46O8

> <MOLECULAR_WEIGHT>
510.668

> <EXACT_MASS>
510.319268441

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.19506948757562

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9E)-12-[(2E,4E)-6-{[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]methyl}hepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one

> <JCHEM_LOGP>
2.186713534666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.563102606395567

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.862987182193944

> <JCHEM_PKA_STRONGEST_BASIC>
-2.801081156274676

> <JCHEM_POLAR_SURFACE_AREA>
139.98

> <JCHEM_REFRACTIVITY>
139.8787

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9E)-12-[(2E,4E)-6-{[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]methyl}hepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.438   2.755   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.438   1.215   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.772   0.445   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0     -10.106   1.215   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -8.772  -1.095   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.312  -1.095   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.232  -1.095   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.772  -2.635   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -8.002  -3.969   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -9.542  -3.969   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -10.876  -4.739   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.209  -3.969   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -12.209  -2.429   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -13.543  -4.739   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -14.877  -3.969   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -16.210  -4.739   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -17.544  -3.969   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -17.544  -2.429   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -18.878  -4.739   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -18.878  -6.279   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -17.544  -7.049   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -16.210  -6.279   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -17.544  -8.589   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -18.878  -9.359   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -18.878 -10.899   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -20.212  -8.589   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -21.545  -9.359   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -22.879  -8.589   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -23.406 -10.036   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -24.395  -8.322   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -22.879  -7.049   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -24.213  -6.279   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -21.545  -6.279   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -21.545  -4.739   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -20.212  -3.969   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -20.212  -2.429   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8   10                                                       
CONECT   10    9    8   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   35                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   19   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₆O₈

Average Mass

510.6680 Da

Monoisotopic Mass

510.31927 Da

IUPAC Name

(9E)-12-[(2E,4E)-6-{[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]methyl}hepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one

Traditional Name

(9E)-12-[(2E,4E)-6-{[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]methyl}hepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one

CAS Registry Number

Not Available

SMILES

CCC(O)C(C)(O)C1OC1CC(C)\C=C\C=C(/C)C1OC(=O)CC(O)CCC(C)(O)C(O)\C=C\C1C

InChI Identifier

InChI=1S/C28H46O8/c1-7-22(30)28(6,34)26-21(35-26)15-17(2)9-8-10-18(3)25-19(4)11-12-23(31)27(5,33)14-13-20(29)16-24(32)36-25/h8-12,17,19-23,25-26,29-31,33-34H,7,13-16H2,1-6H3/b9-8+,12-11+,18-10+

InChI Key

GOQNOCIWFDQNEZ-AEXVIOBPSA-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 diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Macrolide
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Polyol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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
logP	2.19	ChemAxon
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	139.98 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	139.88 m³·mol⁻¹	ChemAxon
Polarizability	57.2 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8567060

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10391618

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one (NP0206099)

MOL for NP0206099 ((9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one)

3D MOL for NP0206099 ((9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one)

3D SDF for NP0206099 ((9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one)

3D-SDF for NP0206099 ((9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one)

PDB for NP0206099 ((9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one)

3D PDB for NP0206099 ((9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one)

SMILES for NP0206099 ((9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one)

INCHI for NP0206099 ((9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one)

Structure for NP0206099 ((9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one)

3D Structure for NP0206099 ((9e)-12-[(2e,4e)-7-[3-(2,3-dihydroxypentan-2-yl)oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-4,7,8-trihydroxy-7,11-dimethyl-1-oxacyclododec-9-en-2-one)