NP-MRD: Showing NP-Card for Methyl apo-6'-lycopenoate (NP0065857)

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Record Information

Version

2.0

Created at

2022-04-28 10:03:22 UTC

Updated at

2022-04-28 10:03:23 UTC

NP-MRD ID

NP0065857

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl apo-6'-lycopenoate

Description

Methyl (7Z,9Z,9'Z)-6'-apo-y-caroten-6'-oate, also known as methyl 6'-apo-9'z-lycopen-6'-Oate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Methyl apo-6'-lycopenoate is found in Bixa orellana and Shepherdia canadensis . Methyl (7Z,9Z,9'Z)-6'-apo-y-caroten-6'-oate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241210022D          

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M  END

     RDKit          3D

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  Mrv0541 02241210022D          

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 13 14  1  0  0  0  0
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 14 31  1  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
 19 32  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 33  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0065857

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\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/C33H44O2/c1-27(2)15-11-18-30(5)21-13-23-31(6)22-12-19-28(3)16-9-10-17-29(4)20-14-24-32(7)25-26-33(34)35-8/h9-10,12-17,19-26H,11,18H2,1-8H3/b10-9+,19-12+,20-14+,23-13+,26-25+,28-16+,29-17+,30-21+,31-22+,32-24+

> <INCHI_KEY>
SLFLEAITCHGGJK-VCZKBJCCSA-N

> <FORMULA>
C33H44O2

> <MOLECULAR_WEIGHT>
472.7013

> <EXACT_MASS>
472.334130652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
61.107845964341934

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2E,4E,6E,8E,10E,12E,14E,16E,18E,20E)-4,8,13,17,21,25-hexamethylhexacosa-2,4,6,8,10,12,14,16,18,20,24-undecaenoate

> <ALOGPS_LOGP>
8.12

> <JCHEM_LOGP>
8.920271370000002

> <ALOGPS_LOGS>
-5.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.799704490919829

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
165.81400000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.31e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E,4E,6E,8E,10E,12E,14E,16E,18E,20E)-4,8,13,17,21,25-hexamethylhexacosa-2,4,6,8,10,12,14,16,18,20,24-undecaenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -17.349  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -16.014  -0.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.680  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.345  -0.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.011  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.676  -0.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.342  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.007  -0.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.672  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.338  -0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.004  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.669  -0.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.669  -0.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.004  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.338  -0.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.673  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.007  -0.001   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.342  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.676  -0.001   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.011  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.345  -0.001   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.680  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.014  -0.001   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      17.349  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -16.014   1.541   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -10.676   1.541   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.338   1.541   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   1.541   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.673  -2.313   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.011  -2.313   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      16.014   1.541   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      14.677   2.313   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   31                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   33                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26                                                            
CONECT   28    2                                                            
CONECT   29    6                                                            
CONECT   30   10                                                            
CONECT   31   14                                                            
CONECT   32   19                                                            
CONECT   33   23                                                            
CONECT   34   26   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   68    0
END

View in JSmol

Synonyms

Value	Source
Methyl (7Z,9Z,9'z)-6'-apo-y-caroten-6'-Oic acid	Generator
Methyl 6'-apo-9'z-lycopen-6'-Oate	HMDB
Methyl (2E,4E,6E,8E,10E,12E,14E,16E,18E,20E)-4,8,13,17,21,25-hexamethylhexacosa-2,4,6,8,10,12,14,16,18,20,24-undecaenoic acid	Generator
Methyl 6'-apo-9'z-lycopen-6'-Oic acid	Generator

Chemical Formula

C₃₃H₄₄O₂

Average Mass

472.7013 Da

Monoisotopic Mass

472.33413 Da

IUPAC Name

methyl (2E,4E,6E,8E,10E,12E,14E,16E,18E,20E)-4,8,13,17,21,25-hexamethylhexacosa-2,4,6,8,10,12,14,16,18,20,24-undecaenoate

Traditional Name

methyl (2E,4E,6E,8E,10E,12E,14E,16E,18E,20E)-4,8,13,17,21,25-hexamethylhexacosa-2,4,6,8,10,12,14,16,18,20,24-undecaenoate

CAS Registry Number

Not Available

SMILES

COC(=O)\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/C33H44O2/c1-27(2)15-11-18-30(5)21-13-23-31(6)22-12-19-28(3)16-9-10-17-29(4)20-14-24-32(7)25-26-33(34)35-8/h9-10,12-17,19-26H,11,18H2,1-8H3/b10-9+,19-12+,20-14+,23-13+,26-25+,28-16+,29-17+,30-21+,31-22+,32-24+

InChI Key

SLFLEAITCHGGJK-VCZKBJCCSA-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
Bixa orellana	Plant	KNApSAcK
Shepherdia canadensis	Plant	KNApSAcK

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
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	8.12	ALOGPS
logP	8.92	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	165.81 m³·mol⁻¹	ChemAxon
Polarizability	61.11 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

HMDB0031381

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003448

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

15285539

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Methyl apo-6'-lycopenoate (NP0065857)

MOL for NP0065857 (Methyl apo-6'-lycopenoate)

3D MOL for NP0065857 (Methyl apo-6'-lycopenoate)

3D SDF for NP0065857 (Methyl apo-6'-lycopenoate)

3D-SDF for NP0065857 (Methyl apo-6'-lycopenoate)

PDB for NP0065857 (Methyl apo-6'-lycopenoate)

3D PDB for NP0065857 (Methyl apo-6'-lycopenoate)

SMILES for NP0065857 (Methyl apo-6'-lycopenoate)

INCHI for NP0065857 (Methyl apo-6'-lycopenoate)

Structure for NP0065857 (Methyl apo-6'-lycopenoate)

3D Structure for NP0065857 (Methyl apo-6'-lycopenoate)