NP-MRD: Showing NP-Card for β,β-carotene (NP0256916)

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Record Information

Version

1.0

Created at

2022-09-07 21:53:58 UTC

Updated at

2022-09-07 21:53:58 UTC

NP-MRD ID

NP0256916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

β,β-carotene

Description

13-Cis-beta-Carotene belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. 13-Cis-beta-Carotene is possibly neutral. Outside of the human body, 13-cis-beta-Carotene is found, on average, in the highest concentration within mango. 13-Cis-beta-Carotene has also been detected, but not quantified in, several different foods, such as pepper (c. Frutescens), common pea, pepper (c. Annuum), root vegetables, and sweet oranges. β,β-carotene is found in Cucurbita moschata, Diospyros kaki, Prunus persica and Psidium guajava. It was first documented in 1992 (PMID: 1416048). This could make 13-cis-beta-carotene a potential biomarker for the consumption of these foods (PMID: 9164160) (PMID: 15003396).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307301919572D          

 40 41  0  0  0  0            999 V2000
    9.2881    9.4875    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


  Mrv1652307301919572D          

 40 41  0  0  0  0            999 V2000
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    6.8625    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 20 14  2  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 27 25  2  0  0  0  0
 28 26  2  0  0  0  0
 29 15  1  0  0  0  0
 30 16  1  0  0  0  0
 31  1  1  0  0  0  0
 31 17  2  0  0  0  0
 31 19  1  0  0  0  0
 32  2  1  0  0  0  0
 32 18  2  0  0  0  0
 32 20  1  0  0  0  0
 33  3  1  0  0  0  0
 33 21  2  0  0  0  0
 33 25  1  0  0  0  0
 34  4  1  0  0  0  0
 34 22  2  0  0  0  0
 34 26  1  0  0  0  0
 35  5  1  0  0  0  0
 35 23  1  0  0  0  0
 36  6  1  0  0  0  0
 36 24  1  0  0  0  0
 37 27  1  0  0  0  0
 37 35  2  0  0  0  0
 38 28  1  0  0  0  0
 38 36  2  0  0  0  0
 39  7  1  0  0  0  0
 39  8  1  0  0  0  0
 39 29  1  0  0  0  0
 39 37  1  0  0  0  0
 40  9  1  0  0  0  0
 40 10  1  0  0  0  0
 40 30  1  0  0  0  0
 40 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256916

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17-,32-18+,33-21+,34-22+

> <INCHI_KEY>
OENHQHLEOONYIE-MZMZTKINSA-N

> <FORMULA>
C40H56

> <MOLECULAR_WEIGHT>
536.888

> <EXACT_MASS>
536.438201803

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
71.48544221092571

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3,3-trimethyl-2-[(1E,3E,5E,7Z,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene

> <JCHEM_LOGP>
11.124081100000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
191.6118

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
β,β-carotene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0      17.338  17.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.671  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003  17.710   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.012  15.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.992  15.040   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.820   1.273   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.810   2.987   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.672  13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.338  13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.671  16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.671   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.671  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.672  15.400   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338  11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.004  15.400   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.004   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  15.400   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.671   6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  15.400   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.338  16.170   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.004  10.780   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.003  16.170   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
CONECT    1   31                                                            
CONECT    2   32                                                            
CONECT    3   33                                                            
CONECT    4   34                                                            
CONECT    5   35                                                            
CONECT    6   36                                                            
CONECT    7   39                                                            
CONECT    8   39                                                            
CONECT    9   40                                                            
CONECT   10   40                                                            
CONECT   11   12   17                                                       
CONECT   12   11   18                                                       
CONECT   13   19   21                                                       
CONECT   14   20   22                                                       
CONECT   15   23   29                                                       
CONECT   16   24   30                                                       
CONECT   17   11   31                                                       
CONECT   18   12   32                                                       
CONECT   19   13   31                                                       
CONECT   20   14   32                                                       
CONECT   21   13   33                                                       
CONECT   22   14   34                                                       
CONECT   23   15   35                                                       
CONECT   24   16   36                                                       
CONECT   25   27   33                                                       
CONECT   26   28   34                                                       
CONECT   27   25   37                                                       
CONECT   28   26   38                                                       
CONECT   29   15   39                                                       
CONECT   30   16   40                                                       
CONECT   31    1   17   19                                                  
CONECT   32    2   18   20                                                  
CONECT   33    3   21   25                                                  
CONECT   34    4   22   26                                                  
CONECT   35    5   23   37                                                  
CONECT   36    6   24   38                                                  
CONECT   37   27   35   39                                                  
CONECT   38   28   36   40                                                  
CONECT   39    7    8   29   37                                             
CONECT   40    9   10   30   38                                             
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

View in JSmol

Synonyms

Value	Source
13-cis-b-Carotene	Generator
13-cis-Β-carotene	Generator
13-cis-beta-carotene	SMPDB
(13Z)-b-Carotene	Generator
(13Z)-Β-carotene	Generator

Chemical Formula

C₄₀H₅₆

Average Mass

536.8880 Da

Monoisotopic Mass

536.43820 Da

IUPAC Name

1,3,3-trimethyl-2-[(1E,3E,5E,7Z,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene

Traditional Name

β,β-carotene

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17-,32-18+,33-21+,34-22+

InChI Key

OENHQHLEOONYIE-MZMZTKINSA-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
Cucurbita moschata	LOTUS Database	35616633
Diospyros kaki	LOTUS Database	35616633
Prunus persica	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Carotenes

Alternative Parents

Substituents

Carotene
Branched unsaturated hydrocarbon
Cycloalkene
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	11.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	191.61 m³·mol⁻¹	ChemAxon
Polarizability	71.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0112265

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019124

KNApSAcK ID

Not Available

Chemspider ID

8432151

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10256668

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Khachik F, Spangler CJ, Smith JC Jr, Canfield LM, Steck A, Pfander H: Identification, quantification, and relative concentrations of carotenoids and their metabolites in human milk and serum. Anal Chem. 1997 May 15;69(10):1873-81. doi: 10.1021/ac961085i. [PubMed:9164160 ]
Khachik F, Beecher GR, Goli MB, Lusby WR, Smith JC Jr: Separation and identification of carotenoids and their oxidation products in the extracts of human plasma. Anal Chem. 1992 Sep 15;64(18):2111-22. doi: 10.1021/ac00042a016. [PubMed:1416048 ]
Fraser PD, Bramley PM: The biosynthesis and nutritional uses of carotenoids. Prog Lipid Res. 2004 May;43(3):228-65. doi: 10.1016/j.plipres.2003.10.002. [PubMed:15003396 ]
LOTUS database [Link]

Showing NP-Card for β,β-carotene (NP0256916)

MOL for NP0256916 (β,β-carotene)

3D MOL for NP0256916 (β,β-carotene)

3D SDF for NP0256916 (β,β-carotene)

3D-SDF for NP0256916 (β,β-carotene)

PDB for NP0256916 (β,β-carotene)

3D PDB for NP0256916 (β,β-carotene)

SMILES for NP0256916 (β,β-carotene)

INCHI for NP0256916 (β,β-carotene)

Structure for NP0256916 (β,β-carotene)

3D Structure for NP0256916 (β,β-carotene)