NP-MRD: Showing NP-Card for apocarotenal (NP0242004)

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Record Information

Version

2.0

Created at

2022-09-07 02:12:45 UTC

Updated at

2022-09-07 02:12:46 UTC

NP-MRD ID

NP0242004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

apocarotenal

Description

8'-Apo-beta,psi-caroten-8'-al, also known as apocarotenal or all-trans-beta-apo-8'-carotenal, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. apocarotenal is found in Averrhoa carambola, Citrus reticulata, Dracaena draco and Palisota barteri. apocarotenal was first documented in 2000 (PMID: 10917914). 8'-Apo-beta,psi-caroten-8'-al is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 15686550).

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1533006051505192D          
 
 31 31  0  0  0  0            999 V2000
    8.8058  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8058  -11.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0880  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5161  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0880  -11.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5161  -11.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3732  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4880   -9.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6621   -9.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2303  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3732  -11.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9440  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6576  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9440   -9.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3761  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0897  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8075  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5210  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8075   -9.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2313  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9491  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6626  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3748  -10.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1044  -10.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8106  -10.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5200  -10.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2190  -10.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9320  -10.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6291  -10.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3703  -11.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2144  -11.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  2  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  7 11  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 30  1  0  0  0  0
 27 31  1  0  0  0  0
M  END

     RDKit          3D

 71 71  0  0  0  0  0  0  0  0999 V2000
   -7.4707    4.2392    0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5136    3.6207   -0.6918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4718    2.8893   -1.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3719    2.7729   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3072    2.0937   -0.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1453    1.9294    0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2207    2.5847    1.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0978    1.2310    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131    1.0121    0.9348 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3181   -0.0302    1.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5597    0.4797    2.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345   -0.7906    0.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4501   -1.1386    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -1.9211    0.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919   -2.2449    1.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5424   -3.0109    0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -3.4883   -0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7560   -3.3421    1.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7247   -4.0866    1.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9345   -4.3699    1.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9056   -5.1198    1.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7252   -5.6649    0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0907   -5.4095    2.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2651   -4.9632    3.4445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4087    2.2358   -2.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3030    0.7306   -2.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2625    2.7003   -3.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6708    2.4695   -3.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8927    2.6717   -2.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7220    3.8492   -1.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5761    4.9169    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3518    4.8604    0.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3857    3.4904    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3937    3.2562    0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1847    1.5933   -1.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4480    2.1736    2.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9988    3.6857    1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2371    2.5080    2.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238    0.7705   -0.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977    1.4234    1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -0.1407   -0.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2284   -0.2323    3.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6293    0.7414    2.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    1.4229    2.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725   -1.1732   -0.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7282   -0.8256    2.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1562   -2.2804   -0.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7935   -1.8901    2.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9044   -2.6675   -1.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2829   -3.7314   -0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6756   -4.3864   -0.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8583   -2.9211    2.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6640   -4.5126    0.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9996   -3.9423    2.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6304   -4.7629   -0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5954   -6.2554   -0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8030   -6.2558    0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8818   -6.0445    1.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2422    0.4330   -1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4727    0.3612   -2.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2238    0.2353   -2.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6338    3.4830   -2.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6415    1.8506   -3.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7032    3.2413   -4.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8574    1.6082   -3.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5506    3.3569   -3.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0549    1.7457   -1.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7294    2.9003   -3.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6418    3.9080   -0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6624    4.7938   -2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 24  1  0
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 22 21  2  0
 21 20  1  0
 20 19  2  0
 19 17  1  0
 17 18  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  6  2  0
  6  7  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 31  1  0
 31 30  1  0
 30 29  1  0
 29 26  1  0
 26 27  1  0
 26 28  1  0
 26  3  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 21 55  1  0
 20 54  1  0
 19 53  1  0
 18 50  1  0
 18 51  1  0
 18 52  1  0
 16 49  1  0
 15 48  1  0
 14 47  1  0
 13 46  1  0
 12 43  1  0
 12 44  1  0
 12 45  1  0
 10 42  1  0
  9 41  1  0
  8 40  1  0
  7 37  1  0
  7 38  1  0
  7 39  1  0
  5 36  1  0
  4 35  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 31 70  1  0
 31 71  1  0
 30 68  1  0
 30 69  1  0
 29 66  1  0
 29 67  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
M  END

 
  Mrv1533006051505192D          
 
 31 31  0  0  0  0            999 V2000
    8.8058  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8058  -11.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0880  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5161  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0880  -11.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5161  -11.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3732  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4880   -9.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6621   -9.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2303  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3732  -11.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9440  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6576  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9440   -9.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3761  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0897  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8075  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5210  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8075   -9.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2313  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9491  -10.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6626  -10.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3748  -10.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1044  -10.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8106  -10.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5200  -10.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2190  -10.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9320  -10.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6291  -10.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3703  -11.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2144  -11.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  2  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
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 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  7 11  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 30  1  0  0  0  0
 27 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(C=O)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O/c1-24(13-8-9-14-25(2)16-11-18-27(4)23-31)15-10-17-26(3)20-21-29-28(5)19-12-22-30(29,6)7/h8-11,13-18,20-21,23H,12,19,22H2,1-7H3/b9-8+,15-10+,16-11+,21-20+,24-13+,25-14+,26-17+,27-18+

> <INCHI_KEY>
DFMMVLFMMAQXHZ-DOKBYWHISA-N

> <FORMULA>
C30H40O

> <MOLECULAR_WEIGHT>
416.649

> <EXACT_MASS>
416.307915908

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.06391305763613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohex-1-en-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenal

> <ALOGPS_LOGP>
7.97

> <JCHEM_LOGP>
7.603525913

> <ALOGPS_LOGS>
-5.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.168847587359038

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
146.77890000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.33e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
apocarotenal

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JUN-15         0                                  
HETATM    1  C   UNK     0      16.438 -19.580   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.438 -21.136   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.098 -18.821   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.763 -18.821   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.098 -21.909   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.763 -21.909   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.763 -19.580   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.844 -17.313   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.303 -17.389   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.097 -19.580   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.763 -21.129   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.429 -18.821   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.761 -19.580   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.429 -17.280   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.102 -18.821   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.434 -19.580   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.774 -18.821   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.106 -19.580   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.774 -17.280   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.432 -18.821   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.772 -19.580   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.104 -18.821   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.433 -19.598   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.795 -18.822   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      35.113 -19.593   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      36.437 -18.838   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      37.742 -19.601   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      39.073 -18.842   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      40.374 -19.602   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      32.425 -21.145   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      37.734 -21.145   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8    9                                             
CONECT    4    1   10                                                       
CONECT    5    2   11                                                       
CONECT    6    2                                                            
CONECT    7    3   11                                                       
CONECT    8    3                                                            
CONECT    9    3                                                            
CONECT   10    4   12                                                       
CONECT   11    5    7                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   23                                                            
CONECT   31   27                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

View in JSmol

Synonyms

Value	Source
8'-Apo-beta-caroten-8'-al	ChEBI
8'-Apo-beta-carotenal	ChEBI
8'Apo-beta,psi-carotenal	ChEBI
all-trans-8'-Apo-beta-carotenal	ChEBI
all-trans-beta-Apo-8'-carotenal	ChEBI
Apocarotenal	ChEBI
beta-Apo-8'-carotenal (C30)	ChEBI
beta-Apo-carotenal	ChEBI
beta-Apocarotenal	ChEBI
C Orange 16	ChEBI
C.I. FOOD orange 6	ChEBI
FOOD Orange 6	ChEBI
8'-Apo-b-caroten-8'-al	Generator
8'-Apo-β-caroten-8'-al	Generator
8'-Apo-b-carotenal	Generator
8'-Apo-β-carotenal	Generator
8'Apo-b,psi-carotenal	Generator
8'Apo-β,psi-carotenal	Generator
all-trans-8'-Apo-b-carotenal	Generator
all-trans-8'-Apo-β-carotenal	Generator
all-trans-b-Apo-8'-carotenal	Generator
all-trans-Β-apo-8'-carotenal	Generator
b-Apo-8'-carotenal (C30)	Generator
Β-apo-8'-carotenal (C30)	Generator
b-Apo-carotenal	Generator
Β-apo-carotenal	Generator
b-Apocarotenal	Generator
Β-apocarotenal	Generator
8'-Apo-b,psi-caroten-8'-al	Generator
8'-Apo-β,psi-caroten-8'-al	Generator
FOOD Dye e160E	MeSH
beta-Apo-8'-carotenal	MeSH

Chemical Formula

C₃₀H₄₀O

Average Mass

416.6490 Da

Monoisotopic Mass

416.30792 Da

IUPAC Name

(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohex-1-en-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenal

Traditional Name

apocarotenal

CAS Registry Number

Not Available

SMILES

C\C(C=O)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C30H40O/c1-24(13-8-9-14-25(2)16-11-18-27(4)23-31)15-10-17-26(3)20-21-29-28(5)19-12-22-30(29,6)7/h8-11,13-18,20-21,23H,12,19,22H2,1-7H3/b9-8+,15-10+,16-11+,21-20+,24-13+,25-14+,26-17+,27-18+

InChI Key

DFMMVLFMMAQXHZ-DOKBYWHISA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Averrhoa carambola	LOTUS Database	35616633
Citrus reticulata	LOTUS Database	35616633
Dracaena draco	LOTUS Database	35616633
Palisota barteri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

enal (CHEBI:53154 )
apo carotenoid triterpenoid (CHEBI:53154 )

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	7.97	ALOGPS
logP	7.6	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	146.78 m³·mol⁻¹	ChemAxon
Polarizability	54.06 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

C00045115

Chemspider ID

Not Available

KEGG Compound ID

C19728

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5478003

PDB ID

Not Available

ChEBI ID

53154

Good Scents ID

Not Available

References

General References

Ruch S, Beyer P, Ernst H, Al-Babili S: Retinal biosynthesis in Eubacteria: in vitro characterization of a novel carotenoid oxygenase from Synechocystis sp. PCC 6803. Mol Microbiol. 2005 Feb;55(4):1015-24. doi: 10.1111/j.1365-2958.2004.04460.x. [PubMed:15686550 ]
Barua AB, Olson JA: beta-carotene is converted primarily to retinoids in rats in vivo. J Nutr. 2000 Aug;130(8):1996-2001. doi: 10.1093/jn/130.8.1996. [PubMed:10917914 ]
LOTUS database [Link]

Showing NP-Card for apocarotenal (NP0242004)

MOL for NP0242004 (apocarotenal)

3D MOL for NP0242004 (apocarotenal)

3D SDF for NP0242004 (apocarotenal)

3D-SDF for NP0242004 (apocarotenal)

PDB for NP0242004 (apocarotenal)

3D PDB for NP0242004 (apocarotenal)

SMILES for NP0242004 (apocarotenal)

INCHI for NP0242004 (apocarotenal)

Structure for NP0242004 (apocarotenal)

3D Structure for NP0242004 (apocarotenal)