NP-MRD: Showing NP-Card for Chlorobactene (NP0065655)

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Record Information

Version

2.0

Created at

2022-04-28 09:51:21 UTC

Updated at

2022-04-28 09:51:21 UTC

NP-MRD ID

NP0065655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chlorobactene

Description

Chlorobactene belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, chlorobactene is considered to be an isoprenoid lipid molecule. Chlorobactene is found in Chlorobium limicola and Chlorobium phaeobacteroides. Chlorobactene was first documented in 1973 (PMID: 4774401). Chlorobactene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 16923888) (PMID: 18365725) (PMID: 25920497) (PMID: 526104).

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1533006051505192D          
 
 40 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END

 
  Mrv1533006051505192D          
 
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   21.5557  -11.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2703  -11.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9849  -11.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6995  -11.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4141  -11.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1287  -11.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8433  -11.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5579  -11.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2726  -11.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9597  -11.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2657  -10.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1241  -10.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5557  -12.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4141  -12.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2726  -12.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4066  -11.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6916  -11.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6891  -12.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4043  -13.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1194  -12.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8317  -13.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6939  -12.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4066  -10.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9768  -11.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  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  2  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 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
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  4 27  1  0  0  0  0
  8 28  1  0  0  0  0
 17 29  1  0  0  0  0
 21 30  1  0  0  0  0
 25 31  1  0  0  0  0
  1 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
  1 36  2  0  0  0  0
 36 37  1  0  0  0  0
 13 38  1  0  0  0  0
 32 39  1  0  0  0  0
 33 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0065655

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C=CC(C)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C40H52/c1-31(2)17-13-20-34(5)23-15-25-35(6)24-14-21-32(3)18-11-12-19-33(4)22-16-26-36(7)27-30-40-38(9)29-28-37(8)39(40)10/h11-12,14-19,21-30H,13,20H2,1-10H3/b12-11+,21-14+,22-16+,25-15+,30-27+,32-18+,33-19+,34-23+,35-24+,36-26+

> <INCHI_KEY>
VJASLAGEYVTOGS-IQAIWTHGSA-N

> <FORMULA>
C40H52

> <MOLECULAR_WEIGHT>
532.856

> <EXACT_MASS>
532.406901674

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
72.04377662805308

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaen-1-yl]-1,3,4-trimethylbenzene

> <ALOGPS_LOGP>
9.34

> <JCHEM_LOGP>
12.25830874

> <ALOGPS_LOGS>
-6.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
194.62140000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.19e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorobactene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JUN-15         0                                  
HETATM    1  C   UNK     0      18.894 -22.165   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.228 -21.396   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.562 -22.165   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.896 -21.396   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.230 -22.165   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.564 -21.396   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.898 -22.165   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.232 -21.396   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.566 -22.165   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.900 -21.396   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.234 -22.165   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.568 -21.396   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.901 -22.165   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.235 -21.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.569 -22.165   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.903 -21.396   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      40.237 -22.165   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.571 -21.396   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      42.905 -22.165   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.239 -21.396   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      45.573 -22.165   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      46.907 -21.396   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      48.241 -22.165   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      49.575 -21.396   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      50.909 -22.165   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      52.191 -21.396   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.896 -19.857   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.232 -19.857   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      40.237 -23.705   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      45.573 -23.705   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      50.909 -23.705   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.559 -21.389   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.224 -22.155   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.220 -23.693   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      17.555 -24.470   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      18.890 -23.704   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      20.219 -24.477   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      34.895 -23.697   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      17.559 -19.851   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.890 -21.379   0.000  0.00  0.00           C+0
CONECT    1    2   32   36                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   38                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25                                                            
CONECT   27    4                                                            
CONECT   28    8                                                            
CONECT   29   17                                                            
CONECT   30   21                                                            
CONECT   31   25                                                            
CONECT   32    1   33   39                                                  
CONECT   33   32   34   40                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    1   37                                                  
CONECT   37   36                                                            
CONECT   38   13                                                            
CONECT   39   32                                                            
CONECT   40   33                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   80    0
END

View in JSmol

Synonyms

Value	Source
trans-Chlorobactene	ChEBI

Chemical Formula

C₄₀H₅₂

Average Mass

532.8560 Da

Monoisotopic Mass

532.40690 Da

IUPAC Name

2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaen-1-yl]-1,3,4-trimethylbenzene

Traditional Name

chlorobactene

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C=CC(C)=C1C

InChI Identifier

InChI=1S/C40H52/c1-31(2)17-13-20-34(5)23-15-25-35(6)24-14-21-32(3)18-11-12-19-33(4)22-16-26-36(7)27-30-40-38(9)29-28-37(8)39(40)10/h11-12,14-19,21-30H,13,20H2,1-10H3/b12-11+,21-14+,22-16+,25-15+,30-27+,32-18+,33-19+,34-23+,35-24+,36-26+

InChI Key

VJASLAGEYVTOGS-IQAIWTHGSA-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
Chlorobium limicola	Bacteria	KNApSAcK
Chlorobium phaeobacteroides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Styrene
Benzenoid
Monocyclic benzene moiety
Aromatic hydrocarbon
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

triterpenoid (CHEBI:80167 )
C40 isoprenoids (tetraterpenes) (C15908 )
C40 isoprenoids (tetraterpenes) (LMPR01070163 )

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	9.34	ALOGPS
logP	12.26	ChemAxon
logS	-6.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	194.62 m³·mol⁻¹	ChemAxon
Polarizability	72.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	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

C00022819

Chemspider ID

Not Available

KEGG Compound ID

C15908

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10098570

PDB ID

Not Available

ChEBI ID

80167

Good Scents ID

Not Available

References

General References

Maresca JA, Bryant DA: Two genes encoding new carotenoid-modifying enzymes in the green sulfur bacterium Chlorobium tepidum. J Bacteriol. 2006 Sep;188(17):6217-23. doi: 10.1128/JB.00766-06. [PubMed:16923888 ]
Koppen OI, Berg IA, Lebedeva NV, Taisova AS, Kolganova TV, Slobodova NV, Bulygina ES, Turova TP, Ivanovskii RN: [Chlorobaculum macestae sp. nov., a new green sulfur bacterium]. Mikrobiologiia. 2008 Jan-Feb;77(1):79-88. [PubMed:18365725 ]
Niedzwiedzki DM, Cranston L: Excited state lifetimes and energies of okenone and chlorobactene, exemplary keto and non-keto aryl carotenoids. Phys Chem Chem Phys. 2015 May 28;17(20):13245-56. doi: 10.1039/c5cp00836k. [PubMed:25920497 ]
Moshier SE, Chapman DJ: Biosynthetic studies on aromatic carotenoids. Biosynthesis of chlorobactene. Biochem J. 1973 Oct;136(2):395-404. doi: 10.1042/bj1360395. [PubMed:4774401 ]
Leutwiler LS, Chapman DJ: Biosynthesis of aryl carotenoids: inhibitor studies of chlorobactene biosynthesis in Chlorobium limicola f. thiosulfatophilum. Arch Microbiol. 1979;123(3):267-73. doi: 10.1007/BF00406660. [PubMed:526104 ]

Showing NP-Card for Chlorobactene (NP0065655)

MOL for NP0065655 (Chlorobactene)

3D MOL for NP0065655 (Chlorobactene)

3D SDF for NP0065655 (Chlorobactene)

3D-SDF for NP0065655 (Chlorobactene)

PDB for NP0065655 (Chlorobactene)

3D PDB for NP0065655 (Chlorobactene)

SMILES for NP0065655 (Chlorobactene)

INCHI for NP0065655 (Chlorobactene)

Structure for NP0065655 (Chlorobactene)

3D Structure for NP0065655 (Chlorobactene)