NP-MRD: Showing NP-Card for 9'-Carboxy-gamma-tocotrienol (NP0339106)

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Record Information

Version

2.0

Created at

2024-09-11 19:42:48 UTC

Updated at

2024-09-11 19:42:49 UTC

NP-MRD ID

NP0339106

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9'-Carboxy-gamma-tocotrienol

Description

9'-Carboxy-gamma-tocotrienol, also known as gamma-cdmoenhc, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 9'-Carboxy-gamma-tocotrienol is an extremely weak basic (essentially neutral) compound (based on its pKa). This mechanism was also observed in separate prostate cancer and melanoma cell line studies. 9'-Carboxy-r-tocotrienol is a dehydrogenation carboxylate product of 9'-hydroxy-r-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016462D          

 27 28  0  0  1  0            999 V2000
   13.6423  -12.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174  -12.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4049  -11.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174  -10.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4049   -9.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174   -9.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6423   -9.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4049   -8.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174   -7.7152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5799   -8.4297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4049  -12.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174  -13.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4049  -14.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174  -14.8593    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9924  -14.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174  -15.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5319  -16.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2464  -15.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9609  -16.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6749  -15.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3894  -16.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6749  -14.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3894  -14.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9609  -14.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9609  -13.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2464  -14.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5319  -14.4469    0.0000 O   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
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 14 27  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 26  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  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
M  END


  Mrv1652303102016462D          

 27 28  0  0  1  0            999 V2000
   13.6423  -12.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174  -12.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4049  -11.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174  -10.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4049   -9.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174   -9.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6423   -9.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4049   -8.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174   -7.7152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5799   -8.4297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4049  -12.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174  -13.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4049  -14.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174  -14.8593    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9924  -14.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8174  -15.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5319  -16.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2464  -15.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9609  -16.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6749  -15.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3894  -16.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6749  -14.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3894  -14.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9609  -14.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9609  -13.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2464  -14.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5319  -14.4469    0.0000 O   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
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 14 27  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 26  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  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
M  END
> <DATABASE_ID>
NP0339106

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CC\C=C(/C)C(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O4/c1-15(8-6-10-16(2)22(25)26)9-7-12-23(5)13-11-19-14-20(24)17(3)18(4)21(19)27-23/h9-10,14,24H,6-8,11-13H2,1-5H3,(H,25,26)/b15-9+,16-10+/t23-/m1/s1

> <INCHI_KEY>
QSRURDPJEKTSFH-ODPFLYRHSA-N

> <FORMULA>
C23H32O4

> <MOLECULAR_WEIGHT>
372.4978

> <EXACT_MASS>
372.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.136882748045856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,6E)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
6.309535750666667

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.470423824805662

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.011795647351914

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852470626714918

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
110.79749999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6E)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      25.466 -22.403   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.926 -22.403   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.156 -21.069   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.926 -19.736   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.156 -18.402   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.926 -17.068   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.466 -17.068   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.156 -15.735   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      23.926 -14.402   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      21.616 -15.735   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      23.156 -23.737   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.926 -25.070   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.156 -26.404   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.926 -27.737   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.386 -27.737   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.926 -29.277   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.260 -30.047   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.593 -29.277   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.927 -30.047   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.260 -29.277   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      30.594 -30.047   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      29.260 -27.737   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      30.594 -26.968   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.927 -26.968   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.927 -25.428   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      26.593 -27.737   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      25.260 -26.968   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   27                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   18   24   27                                                  
CONECT   27   14   26                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
9'-Carboxy-g-tocotrienol	Generator
9'-Carboxy-γ-tocotrienol	Generator
gamma-CDMOenHC	HMDB
(2E,6E)-9-[(2R)-6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoate	Generator

Chemical Formula

C₂₃H₃₂O₄

Average Mass

372.4978 Da

Monoisotopic Mass

372.23006 Da

IUPAC Name

(2E,6E)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid

Traditional Name

(2E,6E)-9-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnona-2,6-dienoic acid

CAS Registry Number

Not Available

SMILES

C\C(CC\C=C(/C)C(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2

InChI Identifier

InChI=1S/C23H32O4/c1-15(8-6-10-16(2)22(25)26)9-7-12-23(5)13-11-19-14-20(24)17(3)18(4)21(19)27-23/h9-10,14,24H,6-8,11-13H2,1-5H3,(H,25,26)/b15-9+,16-10+/t23-/m1/s1

InChI Key

QSRURDPJEKTSFH-ODPFLYRHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Benzopyran
Aromatic monoterpenoid
Chromane
1-benzopyran
Medium-chain fatty acid
Branched fatty acid
1-hydroxy-2-unsubstituted benzenoid
Heterocyclic fatty acid
Hydroxy fatty acid
Alkyl aryl ether
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Benzenoid
Fatty acid
Ether
Monocarboxylic acid or derivatives
Carboxylic acid
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	5.4	ALOGPS
logP	6.31	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	5.01	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	110.8 m³·mol⁻¹	ChemAxon
Polarizability	44.14 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

HMDB0012869

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029193

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

53481537

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 9'-Carboxy-gamma-tocotrienol (NP0339106)

MOL for NP0339106 (9'-Carboxy-gamma-tocotrienol)

3D MOL for NP0339106 (9'-Carboxy-gamma-tocotrienol)

3D SDF for NP0339106 (9'-Carboxy-gamma-tocotrienol)

3D-SDF for NP0339106 (9'-Carboxy-gamma-tocotrienol)

PDB for NP0339106 (9'-Carboxy-gamma-tocotrienol)

3D PDB for NP0339106 (9'-Carboxy-gamma-tocotrienol)

SMILES for NP0339106 (9'-Carboxy-gamma-tocotrienol)

INCHI for NP0339106 (9'-Carboxy-gamma-tocotrienol)

Structure for NP0339106 (9'-Carboxy-gamma-tocotrienol)

3D Structure for NP0339106 (9'-Carboxy-gamma-tocotrienol)