NP-MRD: Showing NP-Card for gamma-Crocetin (NP0048151)

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Record Information

Version

2.0

Created at

2022-03-17 20:51:54 UTC

Updated at

2022-03-17 20:51:55 UTC

NP-MRD ID

NP0048151

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-Crocetin

Description

Gamma-Crocetin, also known as γ-crocetin, 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. Gamma-Crocetin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, gamma-Crocetin has been detected, but not quantified in, herbs and spices and saffrons. gamma-Crocetin is found in Aristolochia cymbifera. This could make gamma-crocetin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308142D          

 26 25  0  0  0  0            999 V2000
    2.4750   -5.7158    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
    4.9500   -4.2868    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
    6.1875   -2.1434    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
    0.8250   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -4.2868    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
    1.2375   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.8579    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
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    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
    2.0625   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -3.5724    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
    4.9500   -2.8579    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
    4.5375   -2.1434    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
    5.7750   -2.8579    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
  8  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17  1  1  0  0  0  0
 17 11  2  0  0  0  0
 17 13  1  0  0  0  0
 18  2  1  0  0  0  0
 18 12  2  0  0  0  0
 18 14  1  0  0  0  0
 19  3  1  0  0  0  0
 19 15  2  0  0  0  0
 20  4  1  0  0  0  0
 20 16  2  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  2  0  0  0  0
 24 22  2  0  0  0  0
 25  5  1  0  0  0  0
 25 21  1  0  0  0  0
 26  6  1  0  0  0  0
 26 22  1  0  0  0  0
M  END


  Mrv0541 05061308142D          

 26 25  0  0  0  0            999 V2000
    2.4750   -5.7158    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
    4.9500   -4.2868    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
    6.1875   -2.1434    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
    0.8250   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -4.2868    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
    1.2375   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.8579    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
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    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
    2.0625   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -3.5724    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
    4.9500   -2.8579    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
    4.5375   -2.1434    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
    5.7750   -2.8579    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
  8  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17  1  1  0  0  0  0
 17 11  2  0  0  0  0
 17 13  1  0  0  0  0
 18  2  1  0  0  0  0
 18 12  2  0  0  0  0
 18 14  1  0  0  0  0
 19  3  1  0  0  0  0
 19 15  2  0  0  0  0
 20  4  1  0  0  0  0
 20 16  2  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  2  0  0  0  0
 24 22  2  0  0  0  0
 25  5  1  0  0  0  0
 25 21  1  0  0  0  0
 26  6  1  0  0  0  0
 26 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048151

> <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)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O4/c1-17(13-9-15-19(3)21(23)25-5)11-7-8-12-18(2)14-10-16-20(4)22(24)26-6/h7-16H,1-6H3/b8-7+,13-9+,14-10+,17-11-,18-12+,19-15+,20-16-

> <INCHI_KEY>
OXNHRKGZZFWUQZ-KYBHHSLLSA-N

> <FORMULA>
C22H28O4

> <MOLECULAR_WEIGHT>
356.4553

> <EXACT_MASS>
356.198759384

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
42.589235276130246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,16-dimethyl (2Z,4E,6E,8E,10Z,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

> <ALOGPS_LOGP>
5.49

> <JCHEM_LOGP>
5.158658009333333

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.549657400058861

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
113.335

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,16-dimethyl (2Z,4E,6E,8E,10Z,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

> <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       4.620 -10.669   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.240  -8.002   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.550  -4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540  -8.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.310  -6.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.160  -8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.310  -9.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.540  -5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.620  -8.002   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.930  -6.668   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.850  -9.336   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.310  -4.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.470  -6.668   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.240  -5.335   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.470  -4.001   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.780  -5.335   0.000  0.00  0.00           O+0
HETATM   26  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   20                                                            
CONECT    5   25                                                            
CONECT    6   26                                                            
CONECT    7    8   11                                                       
CONECT    8    7   12                                                       
CONECT    9   13   15                                                       
CONECT   10   14   16                                                       
CONECT   11    7   17                                                       
CONECT   12    8   18                                                       
CONECT   13    9   17                                                       
CONECT   14   10   18                                                       
CONECT   15    9   19                                                       
CONECT   16   10   20                                                       
CONECT   17    1   11   13                                                  
CONECT   18    2   12   14                                                  
CONECT   19    3   15   21                                                  
CONECT   20    4   16   22                                                  
CONECT   21   19   23   25                                                  
CONECT   22   20   24   26                                                  
CONECT   23   21                                                            
CONECT   24   22                                                            
CONECT   25    5   21                                                       
CONECT   26    6   22                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

View in JSmol

Synonyms

Value	Source
g-Crocetin	Generator
Γ-crocetin	Generator
8,8'-Diapo-psi,psi-carotenedioic acid dimethyl ester	HMDB
Crocetine dimethyl ester	HMDB
1,16-Dimethyl (2Z,6E,8E,10Z,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid	Generator

Chemical Formula

C₂₂H₂₈O₄

Average Mass

356.4553 Da

Monoisotopic Mass

356.19876 Da

IUPAC Name

1,16-dimethyl (2Z,4E,6E,8E,10Z,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

Traditional Name

1,16-dimethyl (2Z,4E,6E,8E,10Z,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

CAS Registry Number

5892-54-6

SMILES

COC(=O)C(\C)=C/C=C/C(/C)=C/C=C/C=C(/C)\C=C\C=C(/C)C(=O)OC

InChI Identifier

InChI=1S/C22H28O4/c1-17(13-9-15-19(3)21(23)25-5)11-7-8-12-18(2)14-10-16-20(4)22(24)26-6/h7-16H,1-6H3/b8-7+,13-9+,14-10+,17-11-,18-12+,19-15+,20-16-

InChI Key

OXNHRKGZZFWUQZ-KYBHHSLLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aristolochia cymbifera	Plant	KNApSAcK
Crocus sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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 acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	5.49	ALOGPS
logP	5.16	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	113.34 m³·mol⁻¹	ChemAxon
Polarizability	42.59 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

HMDB0035099

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013728

KNApSAcK ID

C00023154

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

131751665

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for gamma-Crocetin (NP0048151)

MOL for NP0048151 (gamma-Crocetin)

3D MOL for NP0048151 (gamma-Crocetin)

3D SDF for NP0048151 (gamma-Crocetin)

3D-SDF for NP0048151 (gamma-Crocetin)

PDB for NP0048151 (gamma-Crocetin)

3D PDB for NP0048151 (gamma-Crocetin)

SMILES for NP0048151 (gamma-Crocetin)

INCHI for NP0048151 (gamma-Crocetin)

Structure for NP0048151 (gamma-Crocetin)

3D Structure for NP0048151 (gamma-Crocetin)