NP-MRD: Showing NP-Card for 8,8'-Diapo-psi,psi-carotenedial (NP0065891)

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Record Information

Version

2.0

Created at

2022-04-28 10:04:52 UTC

Updated at

2022-04-28 10:04:52 UTC

NP-MRD ID

NP0065891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8,8'-Diapo-psi,psi-carotenedial

Description

Crocetin dialdehyde 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, crocetin dialdehyde is considered to be an isoprenoid. 8,8'-Diapo-psi,psi-carotenedial is found in Gardenia jasminoides , Jacquinia angustifolia and Plectranthus barbatus. Based on a literature review very few articles have been published on crocetin dialdehyde.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 45  0  0  0  0  0  0  0  0999 V2000
   -7.9872   -0.0919   -0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7885    0.7015    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9181    1.2310    1.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0757    1.0207    0.8049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5435    0.8969    0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4264    0.3377    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1743    0.5134    0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0174    0.0066   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1093   -0.7863   -1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8061    0.2716    0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998   -0.2174   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5985    0.0499    0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236   -0.4192   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947   -0.1166    0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796    0.6917    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2422   -0.5654   -0.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4477   -0.3499   -0.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6530   -0.8388   -0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8433   -0.5745   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9013    0.2329    0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0798   -1.0585   -0.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2096   -0.8208   -0.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5128   -1.0917   -0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0496   -0.2640   -0.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4801    0.3370   -1.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7542    1.8014    2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3486    1.4683    1.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6282   -0.2320   -0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0528    1.1060    1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0933   -0.7335   -1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3798   -0.3912   -2.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8998   -1.8493   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7597    0.8568    1.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6463   -0.8024   -1.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6024    0.6363    1.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931   -1.0058   -1.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9687    1.0548    1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642    1.6238    1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614    0.0687    2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1680   -1.1622   -1.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5671    0.2271    0.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6076   -1.4251   -1.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9203    0.3345    1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2920   -0.2801    1.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4582    1.2471    0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9757   -1.6392   -1.8138 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
  2  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
M  END


  Mrv1652304282212042D          

 22 21  0  0  0  0            999 V2000
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    5.0013    0.0000 O   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    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
    0.0000   -1.4289    0.0000 O   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
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    3.5724    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
  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
 17 18  2  0  0  0  0
 16 19  1  0  0  0  0
 12 20  1  0  0  0  0
  7 21  1  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0065891

> <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=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O2/c1-17(11-7-13-19(3)15-21)9-5-6-10-18(2)12-8-14-20(4)16-22/h5-16H,1-4H3/b6-5+,11-7+,12-8+,17-9+,18-10+,19-13+,20-14+

> <INCHI_KEY>
YHCIKUXPWFLCFN-QHUUTLAPSA-N

> <FORMULA>
C20H24O2

> <MOLECULAR_WEIGHT>
296.41

> <EXACT_MASS>
296.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
36.048012690310244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedial

> <ALOGPS_LOGP>
5.13

> <JCHEM_LOGP>
4.082970726

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8678175916950566

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
101.946

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
crocetindial

> <JCHEM_VEBER_RULE>
1

$$$$

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      16.170   9.336   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.710   9.336   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.400   8.002   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.090   6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.780   5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.550   4.001   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.170   6.668   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1                                                            
CONECT    3    1    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   12                                                            
CONECT   21    7                                                            
CONECT   22    3                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
Crocetindial	ChEBI
8,8'-Diapocarotene-8,8'-dial	Kegg

Chemical Formula

C₂₀H₂₄O₂

Average Mass

296.4100 Da

Monoisotopic Mass

296.17763 Da

IUPAC Name

(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedial

Traditional Name

crocetindial

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=O

InChI Identifier

InChI=1S/C20H24O2/c1-17(11-7-13-19(3)15-21)9-5-6-10-18(2)12-8-14-20(4)16-22/h5-16H,1-4H3/b6-5+,11-7+,12-8+,17-9+,18-10+,19-13+,20-14+

InChI Key

YHCIKUXPWFLCFN-QHUUTLAPSA-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
Gardenia jasminoides	Plant	KNApSAcK
Jacquinia angustifolia	Plant	KNApSAcK
Plectranthus barbatus	LOTUS Database	35616633

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
Fatty aldehyde
Fatty acyl
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enal (CHEBI:53166 )
dialdehyde (CHEBI:53166 )
apo carotenoid diterpenoid (CHEBI:53166 )
Acyclic diterpenoids (LMPR0104010021 )

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	5.13	ALOGPS
logP	4.08	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	101.95 m³·mol⁻¹	ChemAxon
Polarizability	36.05 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00023152

Chemspider ID

9284374

KEGG Compound ID

C19730

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11109238

PDB ID

Not Available

ChEBI ID

53166

Good Scents ID

Not Available

References

General References

Showing NP-Card for 8,8'-Diapo-psi,psi-carotenedial (NP0065891)

MOL for NP0065891 (8,8'-Diapo-psi,psi-carotenedial)

3D MOL for NP0065891 (8,8'-Diapo-psi,psi-carotenedial)

3D SDF for NP0065891 (8,8'-Diapo-psi,psi-carotenedial)

3D-SDF for NP0065891 (8,8'-Diapo-psi,psi-carotenedial)

PDB for NP0065891 (8,8'-Diapo-psi,psi-carotenedial)

3D PDB for NP0065891 (8,8'-Diapo-psi,psi-carotenedial)

SMILES for NP0065891 (8,8'-Diapo-psi,psi-carotenedial)

INCHI for NP0065891 (8,8'-Diapo-psi,psi-carotenedial)

Structure for NP0065891 (8,8'-Diapo-psi,psi-carotenedial)

3D Structure for NP0065891 (8,8'-Diapo-psi,psi-carotenedial)