NP-MRD: Showing NP-Card for (15z)-lycopene (NP0186955)

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Record Information

Version

2.0

Created at

2022-09-04 02:58:00 UTC

Updated at

2022-09-04 02:58:00 UTC

NP-MRD ID

NP0186955

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(15z)-lycopene

Description

15-Cis-Lycopene, also known as (15Z)-lycopene, 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. 15-Cis-Lycopene is a carotenoid found in human fluids. 15-Cis-Lycopene is possibly neutral. Outside of the human body, 15-cis-Lycopene has been detected, but not quantified in, guava. This could make 15-cis-lycopene a potential biomarker for the consumption of these foods. Studies have shown an inverse relationship between the consumption of certain fruits and vegetables and the risk of epithelial cancer. Animals are unable to synthesise carotenoids de novo, and rely upon the diet as a source of these compounds. Carotenoids are isoprenoid molecules that are widespread in nature and are typically seen as pigments in fruits, flowers, birds and crustacea. Since carotenoids are among the micronutrients found in cancer preventive foods, detailed qualitative and quantitative determination of these compounds, particularly in fruits and vegetables and in human plasma, have recently become increasingly important (PMID: 15003396 ). Over recent years there has been considerable interest in dietary carotenoids with respect to their potential in alleviating age-related diseases in humans. (15z)-lycopene is found in Psidium guajava. This attention has been mirrored by significant advances in cloning most of the carotenoid genes and in the genetic manipulation of crop plants with the intention of increasing levels in the diet.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306111918572D          

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M  END

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M  END


  Mrv1652306111918572D          

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10003.480610005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.765910005.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.051110005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.336210005.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.621510005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.906710005.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.191910005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.477010005.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.762210005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.047510005.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.332810005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.618110005.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.903110005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.618110006.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.477010006.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.336210006.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.195310006.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.881210006.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.454910005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.170510005.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.886010005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.599510005.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.315110005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.030710005.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.744110005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.459810005.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.175310005.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.459810006.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.599510006.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.741410006.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 29  1  0  0  0  0
  1 40  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 28  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 27  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 26  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 25  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
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 39  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186955

> <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/C=C(\C)CCC=C(C)C

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

> <INCHI_KEY>
OAIJSZIZWZSQBC-XKKDEUFYSA-N

> <FORMULA>
C40H56

> <MOLECULAR_WEIGHT>
536.8726

> <EXACT_MASS>
536.438201792

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
72.6006241079647

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6E,8E,10E,12E,14E,16Z,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene

> <ALOGPS_LOGP>
9.16

> <JCHEM_LOGP>
11.931831819333333

> <ALOGPS_LOGS>
-6.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
197.8060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.97e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6E,8E,10E,12E,14E,16Z,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-JUN-19         0                                  
HETATM    1  C   UNK     0    8686.7178677.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8685.3828676.841   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8684.0508677.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8682.7148676.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8681.3788677.610   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8680.0468676.841   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8678.7118677.610   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8677.1718677.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8675.8368676.841   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8674.4988677.610   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8673.1648676.841   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8671.8308677.610   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8670.4958676.841   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8669.1618677.610   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8667.8278676.841   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.4938677.610   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.1588676.841   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.8248677.610   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8662.4908676.841   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.1558677.610   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8659.8218676.841   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8658.4878677.610   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8657.1528676.841   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8658.4878679.150   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8663.8248679.150   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8669.1618679.150   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8674.4988679.150   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8681.3788679.150   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8688.0498676.841   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8689.3858677.610   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8690.7218676.841   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8692.0528677.610   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8693.3888676.841   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8694.7248677.610   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8696.0568676.841   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8697.3928677.610   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8698.7278676.841   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0    8697.3928679.150   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0    8692.0528679.150   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0    8686.7178679.150   0.000  0.00  0.00           C+0
CONECT    1    2   29   40                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   18                                                            
CONECT   26   14                                                            
CONECT   27   10                                                            
CONECT   28    5                                                            
CONECT   29    1   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   32                                                            
CONECT   40    1                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   78    0
END

View in JSmol

Synonyms

Value	Source
(15Z)-Lycopene	HMDB
15-cis-Psi,psi-carotene	HMDB
15-cis-Ψ,ψ-carotene	HMDB
15-cis-Lycopene	HMDB

Chemical Formula

C₄₀H₅₆

Average Mass

536.8726 Da

Monoisotopic Mass

536.43820 Da

IUPAC Name

(6E,8E,10E,12E,14E,16Z,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene

Traditional Name

(6E,8E,10E,12E,14E,16Z,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene

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/C=C(\C)CCC=C(C)C

InChI Identifier

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

InChI Key

OAIJSZIZWZSQBC-XKKDEUFYSA-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
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
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Acyclic olefin
Hydrocarbon
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	9.16	ALOGPS
logP	11.93	ChemAxon
logS	-6.1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	197.81 m³·mol⁻¹	ChemAxon
Polarizability	72.6 Å³	ChemAxon
Number of Rings	0	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

HMDB0240367

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001775

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440363

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (15z)-lycopene (NP0186955)

MOL for NP0186955 ((15z)-lycopene)

3D MOL for NP0186955 ((15z)-lycopene)

3D SDF for NP0186955 ((15z)-lycopene)

3D-SDF for NP0186955 ((15z)-lycopene)

PDB for NP0186955 ((15z)-lycopene)

3D PDB for NP0186955 ((15z)-lycopene)

SMILES for NP0186955 ((15z)-lycopene)

INCHI for NP0186955 ((15z)-lycopene)

Structure for NP0186955 ((15z)-lycopene)

3D Structure for NP0186955 ((15z)-lycopene)