NP-MRD: Showing NP-Card for 5'-Carboxy-alpha-chromanol (NP0339093)

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Record Information

Version

2.0

Created at

2024-09-11 19:39:02 UTC

Updated at

2024-09-11 19:39:03 UTC

NP-MRD ID

NP0339093

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5'-Carboxy-alpha-chromanol

Description

5'-Carboxy-alpha-chromanol, also known as alpha-CMBHC, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. The metabolites a-tocopheronic acid and its lactone, known as the Simon metabolites, are generally believed to be artefacts. 5'-Carboxy-alpha-chromanol is an extremely weak basic (essentially neutral) compound (based on its pKa). These remnants are taken up by the liver. The tocopherols ( a-tocopherol , b-tocopherol ,r-tocopherol and d-tocopherol ) and their corresponding tocotrienols are synthesized by plants and have vitamin E antixoidant activity (see pathway vitamin E biosynthesis ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016462D          

 23 24  0  0  1  0            999 V2000
   11.5055  -11.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6805  -11.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2681  -12.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6805  -13.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2681  -13.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6805  -14.6324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8555  -14.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6805  -15.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3950  -15.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1096  -15.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8242  -15.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8242  -16.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5381  -15.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2527  -15.8699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5381  -14.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2527  -14.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8242  -14.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8242  -13.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1096  -14.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3950  -14.2199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2681  -11.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6805  -10.3457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4431  -11.0602    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 21  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  6 20  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 19  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339093

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O4/c1-11(18(21)22)7-6-9-19(5)10-8-15-14(4)16(20)12(2)13(3)17(15)23-19/h11,20H,6-10H2,1-5H3,(H,21,22)/t11?,19-/m1/s1

> <INCHI_KEY>
QWPNLVBAEZJBMI-IMFVZPHKSA-N

> <FORMULA>
C19H28O4

> <MOLECULAR_WEIGHT>
320.4232

> <EXACT_MASS>
320.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.96262790886203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2-methylpentanoic acid

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
5.312855164333332

> <ALOGPS_LOGS>
-3.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.802178268699103

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.295285814500001

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852614909520738

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
91.16019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2-methylpentanoic 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      21.477 -21.980   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.937 -21.980   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.167 -23.314   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.937 -24.646   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.167 -25.980   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.937 -27.314   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.397 -27.314   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.937 -28.854   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.271 -29.624   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.605 -28.854   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.939 -29.624   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.939 -31.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.271 -28.854   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      26.605 -29.624   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      25.271 -27.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.605 -26.544   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.939 -26.544   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.939 -25.004   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.605 -27.314   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      21.271 -26.544   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      19.167 -20.646   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      19.937 -19.312   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      17.627 -20.646   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   20                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   10   17   20                                                  
CONECT   20    6   19                                                       
CONECT   21    2   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
5'-Carboxy-alpha-tocopherol	HMDB
alpha-CMBHC	HMDB
5-[(2R)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2-methylpentanoate	Generator

Chemical Formula

C₁₉H₂₈O₄

Average Mass

320.4232 Da

Monoisotopic Mass

320.19876 Da

IUPAC Name

5-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2-methylpentanoic acid

Traditional Name

5-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)C(O)=O

InChI Identifier

InChI=1S/C19H28O4/c1-11(18(21)22)7-6-9-19(5)10-8-15-14(4)16(20)12(2)13(3)17(15)23-19/h11,20H,6-10H2,1-5H3,(H,21,22)/t11?,19-/m1/s1

InChI Key

QWPNLVBAEZJBMI-IMFVZPHKSA-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 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Medium-chain fatty acid
Alkyl aryl ether
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	4.16	ALOGPS
logP	5.31	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.3	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	5	ChemAxon
Refractivity	91.16 m³·mol⁻¹	ChemAxon
Polarizability	36.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012798

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029177

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

53481524

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5'-Carboxy-alpha-chromanol (NP0339093)

MOL for NP0339093 (5'-Carboxy-alpha-chromanol)

3D MOL for NP0339093 (5'-Carboxy-alpha-chromanol)

3D SDF for NP0339093 (5'-Carboxy-alpha-chromanol)

3D-SDF for NP0339093 (5'-Carboxy-alpha-chromanol)

PDB for NP0339093 (5'-Carboxy-alpha-chromanol)

3D PDB for NP0339093 (5'-Carboxy-alpha-chromanol)

SMILES for NP0339093 (5'-Carboxy-alpha-chromanol)

INCHI for NP0339093 (5'-Carboxy-alpha-chromanol)

Structure for NP0339093 (5'-Carboxy-alpha-chromanol)

3D Structure for NP0339093 (5'-Carboxy-alpha-chromanol)