NP-MRD: Showing NP-Card for beta-Carotinal (NP0048628)

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Record Information

Version

2.0

Created at

2022-03-17 20:59:30 UTC

Updated at

2022-03-17 20:59:31 UTC

NP-MRD ID

NP0048628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Carotinal

Description

Beta-Carotinal, also known as apocarotenal or β-carotinal, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Beta-Carotinal is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, beta-Carotinal has been detected, but not quantified in, several different foods, such as citrus, eggs, green vegetables, and sweet oranges. beta-Carotinal is found in Dracaena draco , Lavandula angustifolia and Pandanous amryllifolius. This could make beta-carotinal a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309232D          

 31 31  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 16 11  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 21 20  2  0  0  0  0
 22 12  1  0  0  0  0
 24  1  1  0  0  0  0
 24 13  2  0  0  0  0
 24 15  1  0  0  0  0
 25  2  1  0  0  0  0
 25 14  2  0  0  0  0
 25 16  1  0  0  0  0
 26  3  1  0  0  0  0
 26 17  2  0  0  0  0
 26 20  1  0  0  0  0
 27  4  1  0  0  0  0
 27 18  2  0  0  0  0
 27 23  1  0  0  0  0
 28  5  1  0  0  0  0
 28 19  1  0  0  0  0
 29 21  1  0  0  0  0
 29 28  2  0  0  0  0
 30  6  1  0  0  0  0
 30  7  1  0  0  0  0
 30 22  1  0  0  0  0
 30 29  1  0  0  0  0
 31 23  2  0  0  0  0
M  END


  Mrv0541 05061309232D          

 31 31  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 16 11  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 21 20  2  0  0  0  0
 22 12  1  0  0  0  0
 24  1  1  0  0  0  0
 24 13  2  0  0  0  0
 24 15  1  0  0  0  0
 25  2  1  0  0  0  0
 25 14  2  0  0  0  0
 25 16  1  0  0  0  0
 26  3  1  0  0  0  0
 26 17  2  0  0  0  0
 26 20  1  0  0  0  0
 27  4  1  0  0  0  0
 27 18  2  0  0  0  0
 27 23  1  0  0  0  0
 28  5  1  0  0  0  0
 28 19  1  0  0  0  0
 29 21  1  0  0  0  0
 29 28  2  0  0  0  0
 30  6  1  0  0  0  0
 30  7  1  0  0  0  0
 30 22  1  0  0  0  0
 30 29  1  0  0  0  0
 31 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048628

> <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-IPIGPKAOSA-N

> <FORMULA>
C30H40O

> <MOLECULAR_WEIGHT>
416.638

> <EXACT_MASS>
416.307915902

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
53.87393157303923

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E,8E,10E,12E,14Z,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>
146.77890000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.33e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E,10E,12E,14Z,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

> <JCHEM_VEBER_RULE>
1

$$$$

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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   30                                                            
CONECT    7   30                                                            
CONECT    8    9   13                                                       
CONECT    9    8   14                                                       
CONECT   10   15   17                                                       
CONECT   11   16   18                                                       
CONECT   12   19   22                                                       
CONECT   13    8   24                                                       
CONECT   14    9   25                                                       
CONECT   15   10   24                                                       
CONECT   16   11   25                                                       
CONECT   17   10   26                                                       
CONECT   18   11   27                                                       
CONECT   19   12   28                                                       
CONECT   20   21   26                                                       
CONECT   21   20   29                                                       
CONECT   22   12   30                                                       
CONECT   23   27   31                                                       
CONECT   24    1   13   15                                                  
CONECT   25    2   14   16                                                  
CONECT   26    3   17   20                                                  
CONECT   27    4   18   23                                                  
CONECT   28    5   19   29                                                  
CONECT   29   21   28   30                                                  
CONECT   30    6    7   22   29                                             
CONECT   31   23                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

View in JSmol

Synonyms

Value	Source
b-Carotinal	Generator
Β-carotinal	Generator
8'-Apo-beta,psi-carotenal	HMDB
8'-Apo-beta-caroten-8'-al	HMDB
8'-Apo-beta-carotenal	HMDB
8'Apo-beta,psi-carotenal	HMDB
all-trans-8'-Apo-beta-carotenal	HMDB
all-trans-beta-Apo-8'-carotenal	HMDB
Apocarotenal	HMDB
b-Apo-2-carotinal	HMDB
beta -Apo-8'-carotenal	HMDB
beta-Apo-8'-carotenal	HMDB
beta-Apo-8'-carotenal (C30)	HMDB
beta-Apo-carotenal	HMDB
beta-Apocarotenal	HMDB
C Orange 16	HMDB
C.I. FOOD orange 6	HMDB
FOOD Orange 6	HMDB
trans-beta-Apo-8'-carotenal	HMDB

Chemical Formula

C₃₀H₄₀O

Average Mass

416.6380 Da

Monoisotopic Mass

416.30792 Da

IUPAC Name

(2E,4E,6E,8E,10E,12E,14Z,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

(2E,4E,6E,8E,10E,12E,14Z,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

CAS Registry Number

1107-26-2

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-IPIGPKAOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dracaena draco	Plant	KNApSAcK
Lavandula angustifolia	Plant	KNApSAcK
Pandanous amryllifolius	-	KNApSAcK

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

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	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	53.87 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

HMDB0036886

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015844

KNApSAcK ID

Not Available

Chemspider ID

30777173

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101701200

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for beta-Carotinal (NP0048628)

MOL for NP0048628 (beta-Carotinal)

3D MOL for NP0048628 (beta-Carotinal)

3D SDF for NP0048628 (beta-Carotinal)

3D-SDF for NP0048628 (beta-Carotinal)

PDB for NP0048628 (beta-Carotinal)

3D PDB for NP0048628 (beta-Carotinal)

SMILES for NP0048628 (beta-Carotinal)

INCHI for NP0048628 (beta-Carotinal)

Structure for NP0048628 (beta-Carotinal)

3D Structure for NP0048628 (beta-Carotinal)