NP-MRD: Showing NP-Card for diapocarotene-6,6'-dioic acid (NP0052229)

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Record Information

Version

2.0

Created at

2022-04-27 23:21:58 UTC

Updated at

2022-04-27 23:21:58 UTC

NP-MRD ID

NP0052229

Secondary Accession Numbers

None

Natural Product Identification

Common Name

diapocarotene-6,6'-dioic acid

Description

Norbixin, also known as alpha-norbixin or beta-norbixin, 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, norbixin is considered to be an isoprenoid. diapocarotene-6,6'-dioic acid is found in Bixa orellana . diapocarotene-6,6'-dioic acid was first documented in 2020 (PMID: 33520083). Based on a literature review a significant number of articles have been published on Norbixin (PMID: 35453480) (PMID: 35408535) (PMID: 35222486) (PMID: 35133226) (PMID: 35075680) (PMID: 34632693).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201212D          

 28 27  0  0  0  0            999 V2000
   10.7250    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    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    0.7145    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
    0.8250    1.4289    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
   -0.4125   -0.7145    0.0000 C   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
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    7.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9625    6.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 12 23  1  0  0  0  0
  7 24  1  0  0  0  0
  3 25  1  0  0  0  0
  1 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END

     RDKit          3D

 56 55  0  0  0  0  0  0  0  0999 V2000
   -2.6305   -0.8435   -2.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0490    0.1166   -0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4041    0.1368   -0.9806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3081    0.6560   -0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7029    0.6781   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6972    1.1373    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3021    1.6851    1.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0761    1.0996   -0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0883    1.5485    0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4271    1.4752   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3880    1.8941    0.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6314    0.9427   -1.2716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8793    0.0992   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -0.3565   -0.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4861   -0.0389    0.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8173   -0.4322   -0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9565   -0.3030    0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3020    0.7566    1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2170   -0.1458    0.6101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3135   -0.8026    0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6277   -0.6018    0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7183   -1.1920    0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6275   -2.1162   -1.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0380   -0.8715    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1638   -1.3963    0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4576   -1.0034    0.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4023   -0.1501    1.7852 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6427   -1.5705    0.4429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525   -1.6885   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6141   -0.8800   -2.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9848   -0.0975   -2.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8486   -0.1975   -1.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9332    1.0259    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0068    0.2720   -1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6271    0.9225    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1020    1.8645    2.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7056    2.6137    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2898    0.6780   -1.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9112    1.9757    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5074    0.6241   -1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8521    0.7060    0.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874   -0.9533   -1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2650    0.5629    0.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432   -1.1243   -1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375    1.0081    1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9651    1.4834    0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566   -0.0277    1.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308    0.4852    1.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589   -1.4327   -0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7924    0.0675    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9338   -1.5793   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2959   -3.0169   -0.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6224   -2.5017   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0995   -0.1322    1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1365   -2.1279   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7901   -2.5647    0.3723 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  2 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 28  1  0
 26 27  2  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
 28 56  1  0
M  END


  Mrv1652304282201212D          

 28 27  0  0  0  0            999 V2000
   10.7250    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    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    0.7145    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
    0.8250    1.4289    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
   -0.4125   -0.7145    0.0000 C   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
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    7.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9625    6.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 12 23  1  0  0  0  0
  7 24  1  0  0  0  0
  3 25  1  0  0  0  0
  1 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052229

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C(O)=O)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O4/c1-19(11-7-13-21(3)15-17-23(25)26)9-5-6-10-20(2)12-8-14-22(4)16-18-24(27)28/h5-18H,1-4H3,(H,25,26)(H,27,28)/b6-5+,11-7+,12-8+,17-15+,18-16+,19-9+,20-10+,21-13+,22-14+

> <INCHI_KEY>
ZVKOASAVGLETCT-UOGKPENDSA-N

> <FORMULA>
C24H28O4

> <MOLECULAR_WEIGHT>
380.484

> <EXACT_MASS>
380.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
45.91567365821665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E,10E,12E,14E,16E,18E)-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaenedioic acid

> <ALOGPS_LOGP>
5.52

> <JCHEM_LOGP>
5.150256142

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.307211297928775

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.705151306600813

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
124.28379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.09e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
norbixin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      20.020  10.669   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.710   9.336   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.400   8.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.090   6.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.780   5.335   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   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      -2.310  -1.334   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  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.860   5.335   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.480   8.002   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.790  12.003   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      20.020  13.337   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      22.330  12.003   0.000  0.00  0.00           O+0
CONECT    1    2   26                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   12                                                            
CONECT   24    7                                                            
CONECT   25    3                                                            
CONECT   26    1   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

View in JSmol

Synonyms

Value	Source
alpha-Norbixin	MeSH
beta-Norbixin	MeSH
Norbixin, (9-cis)-isomer	MeSH
Norbixin, potassium salt	MeSH
Norbixin, sodium salt	MeSH

Chemical Formula

C₂₄H₂₈O₄

Average Mass

380.4840 Da

Monoisotopic Mass

380.19876 Da

IUPAC Name

(2E,4E,6E,8E,10E,12E,14E,16E,18E)-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaenedioic acid

Traditional Name

norbixin

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C=C(/C)\C=C\C(O)=O)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(O)=O

InChI Identifier

InChI=1S/C24H28O4/c1-19(11-7-13-21(3)15-17-23(25)26)9-5-6-10-20(2)12-8-14-22(4)16-18-24(27)28/h5-18H,1-4H3,(H,25,26)(H,27,28)/b6-5+,11-7+,12-8+,17-15+,18-16+,19-9+,20-10+,21-13+,22-14+

InChI Key

ZVKOASAVGLETCT-UOGKPENDSA-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 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
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Unsaturated fatty acid
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

diterpenoid (CHEBI:7623 )
C40 isoprenoids (tetraterpenes) (C08608 )
C40 isoprenoids (tetraterpenes) (LMPR01070209 )

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	5.52	ALOGPS
logP	5.15	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	124.28 m³·mol⁻¹	ChemAxon
Polarizability	45.92 Å³	ChemAxon
Number of Rings	0	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003782

Chemspider ID

4444661

KEGG Compound ID

C08608

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bixin

METLIN ID

Not Available

PubChem Compound

5281249

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1416301

References

General References

Saini RK, Prasad P, Lokesh V, Shang X, Shin J, Keum YS, Lee JH: Carotenoids: Dietary Sources, Extraction, Encapsulation, Bioavailability, and Health Benefits-A Review of Recent Advancements. Antioxidants (Basel). 2022 Apr 18;11(4). pii: antiox11040795. doi: 10.3390/antiox11040795. [PubMed:35453480 ]
Lima IT, da Silva Crispim J, de Sa Neto OP, de Sousa Junior RT, Ribeiro Junior LA, da Silva Filho DA: Organic Electronics from Nature: Computational Investigation of the Electronic and Optical Properties of the Isomers of Bixin and Norbixin Present in the Achiote Seeds. Molecules. 2022 Mar 25;27(7). pii: molecules27072138. doi: 10.3390/molecules27072138. [PubMed:35408535 ]
Us-Camas R, Aguilar-Espinosa M, Rodriguez-Campos J, Vallejo-Cardona AA, Carballo-Uicab VM, Serrano-Posada H, Rivera-Madrid R: Identifying Bixa orellana L. New Carotenoid Cleavage Dioxygenases 1 and 4 Potentially Involved in Bixin Biosynthesis. Front Plant Sci. 2022 Feb 11;13:829089. doi: 10.3389/fpls.2022.829089. eCollection 2022. [PubMed:35222486 ]
Kusmita L, Franyoto YD, Mutmainah M, Puspitaningrum I, Nurcahyanti ADR: Bixa orellana L. carotenoids: antiproliferative activity on human lung cancer, breast cancer, and cervical cancer cells in vitro. Nat Prod Res. 2022 Feb 8:1-7. doi: 10.1080/14786419.2022.2036144. [PubMed:35133226 ]
Bertho G, Oumezziane IE, Caradeuc C, Guibout L, Balducci C, Dinan L, Dilda PJ, Camelo S, Lafont R, Giraud N: Structural analysis of unstable norbixin isomers guided by pure shift nuclear magnetic resonance. Magn Reson Chem. 2022 May;60(5):504-514. doi: 10.1002/mrc.5252. Epub 2022 Feb 7. [PubMed:35075680 ]
Sousa RC, Viana VGF, Meneses LFC, Maia Filho ALM, Santos FEP, Azevedo MMF, Nascimento HMS, Pinto LSS, Vasconcelos DFP: In vivo evaluation of bone repair guided with biological membrane based on polyhydroxybutyrate and norbixin. J Biomed Mater Res B Appl Biomater. 2022 Apr;110(4):743-754. doi: 10.1002/jbm.b.34953. Epub 2021 Oct 10. [PubMed:34632693 ]
Liu H, Zhang J, Xiong Y, Peng S, McClements DJ, Zou L, Liang R, Liu W: Improving norbixin dispersibility and stability by liposomal encapsulation using the pH-driven method. J Sci Food Agric. 2022 Mar 30;102(5):2070-2079. doi: 10.1002/jsfa.11546. Epub 2021 Oct 7. [PubMed:34569077 ]
Fontaine V, Fournie M, Monteiro E, Boumedine T, Balducci C, Guibout L, Latil M, Sahel JA, Veillet S, Dilda PJ, Lafont R, Camelo S: A2E-induced inflammation and angiogenesis in RPE cells in vitro are modulated by PPAR-alpha, -beta/delta, -gamma, and RXR antagonists and by norbixin. Aging (Albany NY). 2021 Sep 20;13(18):22040-22058. doi: 10.18632/aging.203558. Epub 2021 Sep 20. [PubMed:34544906 ]
Assis RQ, Pagno CH, Stoll L, Rios PD, Rios AO, Olivera FC: Active food packaging of cellulose acetate: Storage stability, protective effect on oxidation of riboflavin and release in food simulants. Food Chem. 2021 Jul 1;349:129140. doi: 10.1016/j.foodchem.2021.129140. Epub 2021 Feb 4. [PubMed:33582545 ]
Camelo S, Latil M, Veillet S, Dilda PJ, Lafont R: Beyond AREDS Formulations, What Is Next for Intermediate Age-Related Macular Degeneration (iAMD) Treatment? Potential Benefits of Antioxidant and Anti-inflammatory Apocarotenoids as Neuroprotectors. Oxid Med Cell Longev. 2020 Dec 8;2020:4984927. doi: 10.1155/2020/4984927. eCollection 2020. [PubMed:33520083 ]

Showing NP-Card for diapocarotene-6,6'-dioic acid (NP0052229)

MOL for NP0052229 (diapocarotene-6,6'-dioic acid)

3D MOL for NP0052229 (diapocarotene-6,6'-dioic acid)

3D SDF for NP0052229 (diapocarotene-6,6'-dioic acid)

3D-SDF for NP0052229 (diapocarotene-6,6'-dioic acid)

PDB for NP0052229 (diapocarotene-6,6'-dioic acid)

3D PDB for NP0052229 (diapocarotene-6,6'-dioic acid)

SMILES for NP0052229 (diapocarotene-6,6'-dioic acid)

INCHI for NP0052229 (diapocarotene-6,6'-dioic acid)

Structure for NP0052229 (diapocarotene-6,6'-dioic acid)

3D Structure for NP0052229 (diapocarotene-6,6'-dioic acid)