NP-MRD: Showing NP-Card for trans-Bixin (NP0336855)

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Record Information

Version

2.0

Created at

2024-09-11 08:08:56 UTC

Updated at

2024-09-11 08:08:56 UTC

NP-MRD ID

NP0336855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans-Bixin

Description

Beta-Bixin, also known as b-bixin or labile bixin, belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, beta-bixin is considered to be an isoprenoid lipid molecule. Beta-Bixin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Beta-Bixin is a constituent of the pigment annatto found in Bixa orellana (achiote). trans-Bixin was first documented in 2009 (PMID: 19891958). ; It is a major ingredient in the popular spice blend "Sazón" made by Goya Foods (PMID: 21111424) (PMID: 20723662) (PMID: 20924658) (PMID: 21381747).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10291204352D          

 29 28  0  0  0  0            999 V2000
   -7.4471    3.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7327    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0182    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3037    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5893    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8748    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1603    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7314    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3024    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4120    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1265    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5555    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9844    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7327    1.7679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5893    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7314    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410    1.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6989    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4133    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6989    1.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1278    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8422    3.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5567    2.5930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2712    3.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8422    3.8305    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
  3  4  2  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
  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
 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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  2 18  2  0  0  0  0
  5 19  1  0  0  0  0
  9 20  1  0  0  0  0
 14 21  1  0  0  0  0
 17 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
M  END


  Mrv0541 10291204352D          

 29 28  0  0  0  0            999 V2000
   -7.4471    3.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7327    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0182    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3037    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5893    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8748    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1603    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7314    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3024    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4120    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1265    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5555    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2699    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9844    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7327    1.7679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5893    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7314    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410    1.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6989    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4133    3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6989    1.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1278    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8422    3.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5567    2.5930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2712    3.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8422    3.8305    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
  3  4  2  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
  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
 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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  2 18  2  0  0  0  0
  5 19  1  0  0  0  0
  9 20  1  0  0  0  0
 14 21  1  0  0  0  0
 17 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0336855

> <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(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15+

> <INCHI_KEY>
RAFGELQLHMBRHD-IFNPSABLSA-N

> <FORMULA>
C25H30O4

> <MOLECULAR_WEIGHT>
394.5033

> <EXACT_MASS>
394.214409448

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
47.526811168768646

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E,10E,12E,14E,16E,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid

> <ALOGPS_LOGP>
6.00

> <JCHEM_LOGP>
5.529483531333334

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.006181302265473

> <JCHEM_PKA_STRONGEST_BASIC>
-6.799704490920508

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
129.0529

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bixin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-OCT-12         0                                  
HETATM    1  O   UNK     0     -13.901   5.610   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0     -12.568   4.840   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.234   5.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.900   4.840   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.567   5.610   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.233   4.840   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.899   5.610   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.565   4.840   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.232   5.610   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.898   4.840   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.564   5.610   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.769   4.840   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.103   5.610   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.437   4.840   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.770   5.610   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.104   4.840   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.438   5.610   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -12.568   3.300   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -8.567   7.150   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.232   7.150   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.437   3.300   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.771   4.840   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.105   5.610   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.771   3.300   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.439   4.840   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.772   5.610   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.106   4.840   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      15.440   5.610   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.772   7.150   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   22                                                       
CONECT   18    2                                                            
CONECT   19    5                                                            
CONECT   20    9                                                            
CONECT   21   14                                                            
CONECT   22   17   23   24                                                  
CONECT   23   22   25                                                       
CONECT   24   22                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

View in JSmol

Synonyms

Value	Source
6'-Methyl hydrogen 9'-cis-6,6'-diapocarotene-6,6'-dioate	ChEBI
6'-Methyl hydrogen 9'-Z-6,6'-diapocarotene-6,6'-dioate	ChEBI
Methyl (9-cis)-hydrogen-6,6'-diapo-psi,psi-carotenedioate	ChEBI
6'-Methyl hydrogen 9'-cis-6,6'-diapocarotene-6,6'-dioic acid	Generator
6'-Methyl hydrogen 9'-Z-6,6'-diapocarotene-6,6'-dioic acid	Generator
Methyl (9-cis)-hydrogen-6,6'-diapo-psi,psi-carotenedioic acid	Generator
b-Bixin	Generator
Β-bixin	Generator
Bixin	HMDB
Labile bixin	HMDB

Chemical Formula

C₂₅H₃₀O₄

Average Mass

394.5033 Da

Monoisotopic Mass

394.21441 Da

IUPAC Name

(2E,4E,6E,8E,10E,12E,14E,16E,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid

Traditional Name

bixin

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(O)=O

InChI Identifier

InChI=1S/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15+

InChI Key

RAFGELQLHMBRHD-IFNPSABLSA-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 acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Long-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Unsaturated fatty acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

C40 isoprenoids (tetraterpenes) (LMPR01070210 )

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	6	ALOGPS
logP	5.53	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	5.01	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	129.05 m³·mol⁻¹	ChemAxon
Polarizability	47.53 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035074

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013698

KNApSAcK ID

C00003762

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bixin

METLIN ID

Not Available

PubChem Compound

6376436

PDB ID

Not Available

ChEBI ID

3136

Good Scents ID

Not Available

References

General References

Chiste RC, Yamashita F, Gozzo FC, Mercadante AZ: Simultaneous extraction and analysis by high performance liquid chromatography coupled to diode array and mass spectrometric detectors of bixin and phenolic compounds from annatto seeds. J Chromatogr A. 2011 Jan 7;1218(1):57-63. doi: 10.1016/j.chroma.2010.10.094. Epub 2010 Oct 30. [PubMed:21111424 ]
Takahashi N, Goto T, Taimatsu A, Egawa K, Katoh S, Kusudo T, Sakamoto T, Ohyane C, Lee JY, Kim YI, Uemura T, Hirai S, Kawada T: Bixin regulates mRNA expression involved in adipogenesis and enhances insulin sensitivity in 3T3-L1 adipocytes through PPARgamma activation. Biochem Biophys Res Commun. 2009 Dec 25;390(4):1372-6. doi: 10.1016/j.bbrc.2009.10.162. Epub 2009 Nov 3. [PubMed:19891958 ]
Kang EJ, Campbell RE, Bastian E, Drake MA: Invited review: Annatto usage and bleaching in dairy foods. J Dairy Sci. 2010 Sep;93(9):3891-901. doi: 10.3168/jds.2010-3190. [PubMed:20723662 ]
Dias VM, Pilla V, Alves LP, Oliveira HP, Munin E: Optical characterization in annatto and commercial colorific. J Fluoresc. 2011 Jan;21(1):415-21. doi: 10.1007/s10895-010-0730-1. Epub 2010 Oct 6. [PubMed:20924658 ]
Marcolino VA, Zanin GM, Durrant LR, Benassi Mde T, Matioli G: Interaction of curcumin and bixin with beta-cyclodextrin: complexation methods, stability, and applications in food. J Agric Food Chem. 2011 Apr 13;59(7):3348-57. doi: 10.1021/jf104223k. Epub 2011 Mar 7. [PubMed:21381747 ]

Showing NP-Card for trans-Bixin (NP0336855)

MOL for NP0336855 (trans-Bixin)

3D MOL for NP0336855 (trans-Bixin)

3D SDF for NP0336855 (trans-Bixin)

3D-SDF for NP0336855 (trans-Bixin)

PDB for NP0336855 (trans-Bixin)

3D PDB for NP0336855 (trans-Bixin)

SMILES for NP0336855 (trans-Bixin)

INCHI for NP0336855 (trans-Bixin)

Structure for NP0336855 (trans-Bixin)

3D Structure for NP0336855 (trans-Bixin)