NP-MRD: Showing NP-Card for Apo-10'-bixinal (NP0065890)

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Record Information

Version

2.0

Created at

2022-04-28 10:04:50 UTC

Updated at

2022-04-28 10:04:50 UTC

NP-MRD ID

NP0065890

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apo-10'-bixinal

Description

Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate, also known as apo-10'-bixinal, belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms. Apo-10'-bixinal is found in Bixa orellana . Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 46  0  0  0  0  0  0  0  0999 V2000
   -3.2265    5.1895    1.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3298    3.7471    1.7468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7094    3.3017    1.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4234    4.3380    1.8904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1254    1.9857    1.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3139    0.9889    1.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8531   -0.4364    1.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1324   -0.7582    2.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8389   -1.0954    1.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928   -1.7824    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7049   -1.1428    0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404   -1.6044    0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4456   -0.4729   -1.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6306   -1.9540   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394   -2.4458   -0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7603   -1.4957   -0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0656   -1.8060   -1.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9400   -0.9533   -1.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6957    0.5374   -1.7939 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2860   -1.2881   -2.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1858   -0.4420   -2.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5009   -1.0083   -3.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3345   -0.2170   -3.5641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6542    5.5635    2.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9688    5.6197    0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597    5.5928    1.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2029    1.7508    2.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069    1.1915    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0041   -1.4821    3.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8035   -1.2016    1.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5885    0.1553    3.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6188   -2.2632    1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7103   -2.8528    1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796   -0.0443    0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5201   -0.7917   -1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5967    0.3743   -0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2594   -1.0406   -1.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244   -3.2978    0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403   -3.4366   -0.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -0.4664   -0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3561   -2.8762   -1.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0468    1.0346   -2.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2985    0.8974   -0.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6342    0.7002   -1.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5077   -2.3780   -2.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0074    0.5814   -2.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6666   -2.0579   -3.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
M  END


  Mrv0541 05061306162D          

 23 22  0  0  0  0            999 V2000
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -7.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 15 14  2  0  0  0  0
 16  8  1  0  0  0  0
 17  1  1  0  0  0  0
 17  9  2  0  0  0  0
 17 11  1  0  0  0  0
 18  2  1  0  0  0  0
 18 10  2  0  0  0  0
 18 13  1  0  0  0  0
 19  3  1  0  0  0  0
 19 12  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  2  0  0  0  0
 22 20  2  0  0  0  0
 23  4  1  0  0  0  0
 23 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0065890

> <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=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O3/c1-17(9-5-6-10-18(2)13-8-16-21)11-7-12-19(3)14-15-20(22)23-4/h5-16H,1-4H3/b6-5+,11-7+,13-8+,15-14+,17-9+,18-10+,19-12-

> <INCHI_KEY>
NXZZZYUALZNGOO-OKMAZBOSSA-N

> <FORMULA>
C20H24O3

> <MOLECULAR_WEIGHT>
312.4028

> <EXACT_MASS>
312.172544634

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.49241848418512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E,4Z,6E,8E,10E,12E,14E)-4,8,13-trimethyl-16-oxohexadeca-2,4,6,8,10,12,14-heptaenoate

> <ALOGPS_LOGP>
5.09

> <JCHEM_LOGP>
4.073074660666666

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.30181485109397

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
103.2083

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E,4Z,6E,8E,10E,12E,14E)-4,8,13-trimethyl-16-oxohexadeca-2,4,6,8,10,12,14-heptaenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.160  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -9.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.620  -5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.850  -6.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850 -12.003   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.620  -8.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.620 -10.669   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.620 -13.337   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.850  -9.336   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.160 -13.337   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   23                                                            
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7   11   12                                                       
CONECT    8   13   16                                                       
CONECT    9    5   17                                                       
CONECT   10    6   18                                                       
CONECT   11    7   17                                                       
CONECT   12    7   19                                                       
CONECT   13    8   18                                                       
CONECT   14   15   19                                                       
CONECT   15   14   20                                                       
CONECT   16    8   21                                                       
CONECT   17    1    9   11                                                  
CONECT   18    2   10   13                                                  
CONECT   19    3   12   14                                                  
CONECT   20   15   22   23                                                  
CONECT   21   16                                                            
CONECT   22   20                                                            
CONECT   23    4   20                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

View in JSmol

Synonyms

Value	Source
Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoic acid	Generator
Apo-10'-bixinal	HMDB
Methyl (4Z,6E,8E,10E,12E,14E)-4,8,13-trimethyl-16-oxohexadeca-2,4,6,8,10,12,14-heptaenoic acid	Generator

Chemical Formula

C₂₀H₂₄O₃

Average Mass

312.4028 Da

Monoisotopic Mass

312.17254 Da

IUPAC Name

methyl (2E,4Z,6E,8E,10E,12E,14E)-4,8,13-trimethyl-16-oxohexadeca-2,4,6,8,10,12,14-heptaenoate

Traditional Name

methyl (2E,4Z,6E,8E,10E,12E,14E)-4,8,13-trimethyl-16-oxohexadeca-2,4,6,8,10,12,14-heptaenoate

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=O

InChI Identifier

InChI=1S/C20H24O3/c1-17(9-5-6-10-18(2)13-8-16-21)11-7-12-19(3)14-15-20(22)23-4/h5-16H,1-4H3/b6-5+,11-7+,13-8+,15-14+,17-9+,18-10+,19-12-

InChI Key

NXZZZYUALZNGOO-OKMAZBOSSA-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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty aldehydes

Direct Parent

Fatty aldehydes

Alternative Parents

Substituents

Fatty aldehyde
Acyclic monoterpenoid
Monoterpenoid
Fatty acid ester
Alpha,beta-unsaturated aldehyde
Enal
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Aldehyde
Organooxygen compound
Organic oxygen 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	5.09	ALOGPS
logP	4.07	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	103.21 m³·mol⁻¹	ChemAxon
Polarizability	37.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031976

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008669

KNApSAcK ID

C00023151

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

131751234

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Apo-10'-bixinal (NP0065890)

MOL for NP0065890 (Apo-10'-bixinal)

3D MOL for NP0065890 (Apo-10'-bixinal)

3D SDF for NP0065890 (Apo-10'-bixinal)

3D-SDF for NP0065890 (Apo-10'-bixinal)

PDB for NP0065890 (Apo-10'-bixinal)

3D PDB for NP0065890 (Apo-10'-bixinal)

SMILES for NP0065890 (Apo-10'-bixinal)

INCHI for NP0065890 (Apo-10'-bixinal)

Structure for NP0065890 (Apo-10'-bixinal)

3D Structure for NP0065890 (Apo-10'-bixinal)