NP-MRD: Showing NP-Card for Azafrin (NP0052225)

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Record Information

Version

2.0

Created at

2022-04-27 23:21:47 UTC

Updated at

2022-04-27 23:21:47 UTC

NP-MRD ID

NP0052225

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Azafrin

Description

Azafrin belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. Azafrin is found in Alectra parasitica var. chitrakutensis, Christisonia bicolor and Escobedia scabrofolia. Azafrin was first documented in 2014 (PMID: 24627973). Based on a literature review a small amount of articles have been published on Azafrin (PMID: 31795510) (PMID: 30166096).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201212D          

 31 31  0  0  1  0            999 V2000
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    0.0000    0.8250    0.0000 C   0  0  2  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
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0363    1.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4236    2.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481    2.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6354    3.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5 29  1  6  0  0  0
  4 30  1  6  0  0  0
  4 31  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282201212D          

 31 31  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0052225

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\[C@@]1(O)C(C)(C)CCC[C@@]1(C)O)=C/C=C/C=C(\C)/C=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O4/c1-21(11-7-8-12-22(2)15-16-24(28)29)13-9-14-23(3)17-20-27(31)25(4,5)18-10-19-26(27,6)30/h7-9,11-17,20,30-31H,10,18-19H2,1-6H3,(H,28,29)/b8-7+,13-9+,16-15+,20-17+,21-11+,22-12+,23-14+/t26-,27-/m1/s1

> <INCHI_KEY>
NYWCITDWPAZNBU-DYISAODMSA-N

> <FORMULA>
C27H38O4

> <MOLECULAR_WEIGHT>
426.597

> <EXACT_MASS>
426.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.03487936220527

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E,8E,10E,12E,14E)-15-[(1R,2R)-1,2-dihydroxy-2,6,6-trimethylcyclohexyl]-4,9,13-trimethylpentadeca-2,4,6,8,10,12,14-heptaenoic acid

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
5.203874968666668

> <ALOGPS_LOGS>
-5.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.92873453765121

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.744392025091597

> <JCHEM_PKA_STRONGEST_BASIC>
-3.322440457479063

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
135.27040000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azafrin

> <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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.539   1.594   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.262   2.953   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.801   3.007   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.524   4.367   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.063   4.421   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.786   5.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.325   5.834   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.048   7.194   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.587   7.248   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -11.310   8.607   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.849   8.661   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -13.572  10.021   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -15.111  10.075   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -15.834  11.434   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -17.373  11.488   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -18.189  10.182   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0     -18.096  12.848   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -12.756  11.327   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.141   4.528   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.617   1.701   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.816   2.846   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.816  -1.306   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.539  -0.054   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   30   31                                             
CONECT    5    4    6    9   29                                             
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   20                                                            
CONECT   27   15                                                            
CONECT   28   11                                                            
CONECT   29    5                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

View in JSmol

Synonyms

Value	Source
5,6-Dihydro,5,6-dihydroxy-10'-apo-beta,psi-carotenoic acid	MeSH

Chemical Formula

C₂₇H₃₈O₄

Average Mass

426.5970 Da

Monoisotopic Mass

426.27701 Da

IUPAC Name

(2E,4E,6E,8E,10E,12E,14E)-15-[(1R,2R)-1,2-dihydroxy-2,6,6-trimethylcyclohexyl]-4,9,13-trimethylpentadeca-2,4,6,8,10,12,14-heptaenoic acid

Traditional Name

azafrin

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C=C(/C)\C=C\[C@@]1(O)C(C)(C)CCC[C@@]1(C)O)=C/C=C/C=C(\C)/C=C/C(O)=O

InChI Identifier

InChI=1S/C27H38O4/c1-21(11-7-8-12-22(2)15-16-24(28)29)13-9-14-23(3)17-20-27(31)25(4,5)18-10-19-26(27,6)30/h7-9,11-17,20,30-31H,10,18-19H2,1-6H3,(H,28,29)/b8-7+,13-9+,16-15+,20-17+,21-11+,22-12+,23-14+/t26-,27-/m1/s1

InChI Key

NYWCITDWPAZNBU-DYISAODMSA-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
Alectra parasitica var. chitrakutensis	Plant	KNApSAcK
Christisonia bicolor	Plant	KNApSAcK
Escobedia scabrofolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Long-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Cyclohexanol
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Tertiary alcohol
1,2-diol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

sesterterpenoid (CHEBI:2944 )

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	5.4	ALOGPS
logP	5.2	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	135.27 m³·mol⁻¹	ChemAxon
Polarizability	51.03 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00003761

Chemspider ID

4444637

KEGG Compound ID

C08581

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang X, Li C, Wang L, Fei Y, Qin W: Analysis of Centranthera grandiflora Benth Transcriptome Explores Genes of Catalpol, Acteoside and Azafrin Biosynthesis. Int J Mol Sci. 2019 Nov 29;20(23). pii: ijms20236034. doi: 10.3390/ijms20236034. [PubMed:31795510 ]
Yang S, Chou G, Li Q: Cardioprotective role of azafrin in against myocardial injury in rats via activation of the Nrf2-ARE pathway. Phytomedicine. 2018 Aug 1;47:12-22. doi: 10.1016/j.phymed.2018.04.042. Epub 2018 Apr 18. [PubMed:30166096 ]
Agrawal P, Laddha K, Tiwari A: Isolation and HPLC method development of azafrin from Alectra parasitica var. chitrakutensis. Nat Prod Res. 2014;28(13):940-4. doi: 10.1080/14786419.2014.896009. Epub 2014 Mar 17. [PubMed:24627973 ]

Showing NP-Card for Azafrin (NP0052225)

MOL for NP0052225 (Azafrin)

3D MOL for NP0052225 (Azafrin)

3D SDF for NP0052225 (Azafrin)

3D-SDF for NP0052225 (Azafrin)

PDB for NP0052225 (Azafrin)

3D PDB for NP0052225 (Azafrin)

SMILES for NP0052225 (Azafrin)

INCHI for NP0052225 (Azafrin)

Structure for NP0052225 (Azafrin)

3D Structure for NP0052225 (Azafrin)