Np mrd loader

Showing NP-Card for 11'-Carboxy-gamma-tocotrienol (NP0339029)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-11 19:20:16 UTC
Updated at2024-09-11 19:20:17 UTC
NP-MRD IDNP0339029
Secondary Accession NumbersNone
Natural Product Identification
Common Name11'-Carboxy-gamma-tocotrienol
Description11'-Carboxy-gamma-tocotrienol, also known as gamma-CDMD(en)(2)HC, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 11'-Carboxy-gamma-tocotrienol is an extremely weak basic (essentially neutral) compound (based on its pKa). 11'-Carboxy-r-tocotrienol is a dehydrogenation carboxylate product of 11'-hydroxy-r-tocotrienol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. This mechanism was also observed in separate prostate cancer and melanoma cell line studies.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0339029 (11'-Carboxy-gamma-tocotrienol)


  Mrv1652303102016452D          

 29 30  0  0  1  0            999 V2000
   12.7770  -13.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -13.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396  -12.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -11.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396  -10.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -10.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7770  -10.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396   -9.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521   -8.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396   -8.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521   -7.3399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7147   -8.0544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396  -13.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -14.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396  -15.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -15.9127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1272  -15.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -16.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6666  -17.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3811  -16.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0956  -17.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8095  -16.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5240  -17.1501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8095  -15.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5240  -15.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0956  -15.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0956  -14.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3811  -15.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6666  -15.5003    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 13  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 16 29  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 28  2  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
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
Download

3D MOL for NP0339029 (11'-Carboxy-gamma-tocotrienol)

Download
3D SDF for NP0339029 (11'-Carboxy-gamma-tocotrienol)

  Mrv1652303102016452D          

 29 30  0  0  1  0            999 V2000
   12.7770  -13.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -13.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396  -12.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -11.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396  -10.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -10.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7770  -10.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396   -9.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521   -8.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396   -8.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521   -7.3399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7147   -8.0544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396  -13.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -14.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5396  -15.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -15.9127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1272  -15.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9521  -16.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6666  -17.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3811  -16.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0956  -17.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8095  -16.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5240  -17.1501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8095  -15.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5240  -15.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0956  -15.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0956  -14.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3811  -15.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6666  -15.5003    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 13  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 16 29  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 28  2  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
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339029

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O4/c1-17(8-6-9-18(2)11-12-23(27)28)10-7-14-25(5)15-13-21-16-22(26)19(3)20(4)24(21)29-25/h9-10,16,26H,6-8,11-15H2,1-5H3,(H,27,28)/b17-10+,18-9+/t25-/m1/s1

> <INCHI_KEY>
QRIWRFHSVDRBRJ-LNRRRGPJSA-N

> <FORMULA>
C25H36O4

> <MOLECULAR_WEIGHT>
400.5509

> <EXACT_MASS>
400.26135964

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.230933728180794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4E,8E)-11-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundeca-4,8-dienoic acid

> <ALOGPS_LOGP>
5.54

> <JCHEM_LOGP>
6.686738716666667

> <ALOGPS_LOGS>
-5.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.470423562225404

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.928869630455024

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852470626727407

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
119.94769999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.58e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E,8E)-11-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-4,8-dimethylundeca-4,8-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339029 (11'-Carboxy-gamma-tocotrienol)
Download
PDB for NP0339029 (11'-Carboxy-gamma-tocotrienol)
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      23.850 -24.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.311 -24.370   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.541 -23.036   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.311 -21.702   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.541 -20.369   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.311 -19.035   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.850 -19.035   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.541 -17.702   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.311 -16.369   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.541 -15.035   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.311 -13.701   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      20.001 -15.035   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      21.541 -25.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.311 -27.036   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.541 -28.370   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.311 -29.704   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.771 -29.704   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.311 -31.244   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.644 -32.014   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.978 -31.244   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.312 -32.014   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.644 -31.244   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      28.978 -32.014   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      27.644 -29.704   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.978 -28.934   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      26.312 -28.934   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      26.312 -27.394   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.978 -29.704   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      23.644 -28.934   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   29                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   20   26   29                                                  
CONECT   29   16   28                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

Download
3D PDB for NP0339029 (11'-Carboxy-gamma-tocotrienol)
Download
SMILES for NP0339029 (11'-Carboxy-gamma-tocotrienol)
C\C(CC\C=C(/C)CCC(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2
Download
INCHI for NP0339029 (11'-Carboxy-gamma-tocotrienol)
InChI=1S/C25H36O4/c1-17(8-6-9-18(2)11-12-23(27)28)10-7-14-25(5)15-13-21-16-22(26)19(3)20(4)24(21)29-25/h9-10,16,26H,6-8,11-15H2,1-5H3,(H,27,28)/b17-10+,18-9+/t25-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
11'-Carboxy-g-tocotrienolGenerator
11'-Carboxy-γ-tocotrienolGenerator
gamma-CDMD(En)(2)HCHMDB
(4E,8E)-11-[(2R)-6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundeca-4,8-dienoateGenerator
Chemical FormulaC25H36O4
Average Mass400.5509 Da
Monoisotopic Mass400.26136 Da
IUPAC Name(4E,8E)-11-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-4,8-dimethylundeca-4,8-dienoic acid
Traditional Name(4E,8E)-11-[(2R)-6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl]-4,8-dimethylundeca-4,8-dienoic acid
CAS Registry NumberNot Available
SMILES
C\C(CC\C=C(/C)CCC(O)=O)=C/CC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2
InChI Identifier
InChI=1S/C25H36O4/c1-17(8-6-9-18(2)11-12-23(27)28)10-7-14-25(5)15-13-21-16-22(26)19(3)20(4)24(21)29-25/h9-10,16,26H,6-8,11-15H2,1-5H3,(H,27,28)/b17-10+,18-9+/t25-/m1/s1
InChI KeyQRIWRFHSVDRBRJ-LNRRRGPJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Sesquiterpenoid
    • 

  • Long-chain fatty acid
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Branched fatty acid
    • 

  • Heterocyclic fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Benzenoid
    • 

  • Unsaturated fatty acid
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.54ALOGPS
logP6.69ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)4.93ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity119.95 m³·mol⁻¹ChemAxon
Polarizability48.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012518  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029111  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481454  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References