NP-MRD: Showing NP-Card for Macaridine (NP0075539)

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Record Information

Version

2.0

Created at

2022-04-28 20:48:51 UTC

Updated at

2022-04-28 20:48:51 UTC

NP-MRD ID

NP0075539

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Macaridine

Description

Macaridine belongs to the class of organic compounds known as dihydropyridines. Dihydropyridines are compounds containing a dihydropyridine moiety, which is a semi-saturated pyridine derivative with two double bonds. Macaridine is a moderately basic compound (based on its pKa). Outside of the human body, Macaridine has been detected, but not quantified in, root vegetables. Macaridine is found in Lepidium meyenii . This could make macaridine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.6714    0.4271   -3.3035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7955   -0.1101   -2.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838    0.0556   -1.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0138   -0.4725   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1207   -1.2792   -0.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4366   -0.6769   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0321   -1.0011    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2391   -0.4551    1.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112    0.4374    0.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3278    0.7697   -0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1077    0.2171   -1.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1678   -0.2606    1.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723    0.5146    1.5917 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4697    0.7426    2.9448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1920    1.0704    0.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0204    0.8616   -0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368   -0.6619   -3.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0950   -2.3136   -0.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1840   -1.4821   -1.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884   -1.7052    1.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -0.7145    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8649    0.8713    0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8394    1.4726   -1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629    0.4821   -2.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2948   -1.2861    1.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2478    0.1608    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1566    1.6728    3.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0330    1.6654    1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7459    1.3036   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  3 16  1  0
 16 15  2  0
 15 13  1  0
 11  6  1  0
 14 27  1  0
 12 25  1  0
 12 26  1  0
  5 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
  2 17  1  0
 16 29  1  0
 15 28  1  0
M  END


  Mrv0541 05061311092D          

 16 17  0  0  0  0            999 V2000
    2.1434    2.0625    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
    1.4289    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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    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
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    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
    0.0000    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14  7  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075539

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ON1CC(CC2=CC=CC=C2)=C(C=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H13NO2/c15-10-12-6-7-14(16)9-13(12)8-11-4-2-1-3-5-11/h1-7,10,16H,8-9H2

> <INCHI_KEY>
PHSAQLJHWJOCBJ-UHFFFAOYSA-N

> <FORMULA>
C13H13NO2

> <MOLECULAR_WEIGHT>
215.2478

> <EXACT_MASS>
215.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.66677432254366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-benzyl-1-hydroxy-1,2-dihydropyridine-4-carbaldehyde

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
1.1797762779999998

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.207032557035589

> <JCHEM_PKA_STRONGEST_BASIC>
1.8653098678629216

> <JCHEM_POLAR_SURFACE_AREA>
40.540000000000006

> <JCHEM_REFRACTIVITY>
63.7075

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-benzyl-1-hydroxy-2H-pyridine-4-carbaldehyde

> <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       4.001   3.850   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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.000   9.240   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       5.335  10.780   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   11                                                       
CONECT    5    3   11                                                       
CONECT    6    7   12                                                       
CONECT    7    6   14                                                       
CONECT    8   11   13                                                       
CONECT    9   13   14                                                       
CONECT   10   12   15                                                       
CONECT   11    4    5    8                                                  
CONECT   12    6   10   13                                                  
CONECT   13    8    9   12                                                  
CONECT   14    7    9   16                                                  
CONECT   15   10                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
3-Benzyl-1,2-dihydro-1-hydroxy-4-pyridinecarboxaldehyde	HMDB
3-Benzyl-1,2-dihydro-N-hydroxypyridine-4-carbaldehyde	HMDB
3-Benzyl-1-hydroxy-1,2-dihydro-pyridine-4-carbaldehyde	HMDB
3-Benzyl-1-hydroxy-1,2-dihydropyridine-4-carbaldehyde	HMDB
3-Benzyl-4-formyl-1,2-dihydro-1-hydroxypyridine	HMDB
3-Benzyl-1,2-dihydro-N-hydroxypyridine	HMDB
Macaridine	MeSH

Chemical Formula

C₁₃H₁₃NO₂

Average Mass

215.2478 Da

Monoisotopic Mass

215.09463 Da

IUPAC Name

3-benzyl-1-hydroxy-1,2-dihydropyridine-4-carbaldehyde

Traditional Name

3-benzyl-1-hydroxy-2H-pyridine-4-carbaldehyde

CAS Registry Number

Not Available

SMILES

ON1CC(CC2=CC=CC=C2)=C(C=O)C=C1

InChI Identifier

InChI=1S/C13H13NO2/c15-10-12-6-7-14(16)9-13(12)8-11-4-2-1-3-5-11/h1-7,10,16H,8-9H2

InChI Key

PHSAQLJHWJOCBJ-UHFFFAOYSA-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
Lepidium meyenii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyridines. Dihydropyridines are compounds containing a dihydropyridine moiety, which is a semi-saturated pyridine derivative with two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Dihydropyridines

Alternative Parents

Substituents

Dihydropyridine
Benzenoid
Monocyclic benzene moiety
Azacycle
N-organohydroxylamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aldehyde
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.21	ALOGPS
logP	1.18	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	15.21	ChemAxon
pKa (Strongest Basic)	1.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.71 m³·mol⁻¹	ChemAxon
Polarizability	22.67 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0039455

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019054

KNApSAcK ID

C00037457

Chemspider ID

552337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Macaridine (NP0075539)

MOL for NP0075539 (Macaridine)

3D MOL for NP0075539 (Macaridine)

3D SDF for NP0075539 (Macaridine)

3D-SDF for NP0075539 (Macaridine)

PDB for NP0075539 (Macaridine)

3D PDB for NP0075539 (Macaridine)

SMILES for NP0075539 (Macaridine)

INCHI for NP0075539 (Macaridine)

Structure for NP0075539 (Macaridine)

3D Structure for NP0075539 (Macaridine)