NP-MRD: Showing NP-Card for (-)-Andrachcinine (NP0081232)

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Record Information

Version

2.0

Created at

2022-04-29 02:11:50 UTC

Updated at

2022-04-29 02:11:50 UTC

NP-MRD ID

NP0081232

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Andrachcinine

Description

Andrachcinine belongs to the class of organic compounds known as hydropyridines. Hydropyridines are compounds containing a hydrogenated pyridine ring (i.E. Containing less than the maximum number of double bonds.). (-)-Andrachcinine is found in Andrachne aspera. (-)-Andrachcinine was first documented in 2000 (PMID: 10869196). Based on a literature review very few articles have been published on Andrachcinine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 45  0  0  0  0  0  0  0  0999 V2000
   -6.2709    1.1829   -0.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0783    0.5073   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8635    0.6899   -0.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6576   -0.0242   -0.3070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1094   -1.3676   -0.2271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626    0.1047   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1811   -0.4855   -0.7320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1568   -1.9778   -0.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975   -2.3925    0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9086   -1.5790    0.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8686   -0.1278    0.5180 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8709    0.2986   -0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2539   -0.0495   -0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5170   -1.1976    0.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2754    1.0267   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6131    0.4910    0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5268    0.2679    0.2517 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1412    0.6301    1.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1234    1.2225    0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6347    0.6744   -1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0648    2.2509   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2761   -0.5495    0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8841    0.9968    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0901    0.3153   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6455    1.7584   -0.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6611    0.3389    0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5061   -1.5711    0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2863    1.2061   -1.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -0.2437   -2.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897   -0.3607   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0744   -2.4111   -0.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -2.5357   -1.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831   -3.4466    0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7033   -1.9915    1.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1739    0.4606    1.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447    1.3769   -0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6270   -0.2452   -1.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9067    1.8362    0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3488    1.4590   -1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7099    0.7733    1.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4053    0.9335   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6035   -0.6136    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7277   -0.1307    1.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7372    1.5507    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605    0.9482    2.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 11 17  1  0
 17 18  1  0
 17  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  1
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  6
  8 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  1
 12 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
M  END


  Mrv1652304292204112D          

 18 18  0  0  1  0            999 V2000
   -1.4289    1.6500    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
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  2  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
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 O   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
   -2.1434   -1.2375    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
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    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
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
  4 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 14 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081232

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@@H](O)C[C@@H]1CC=C[C@@H](CC(=O)CC)N1C

> <INCHI_IDENTIFIER>
InChI=1S/C15H27NO2/c1-4-7-15(18)11-13-9-6-8-12(16(13)3)10-14(17)5-2/h6,8,12-13,15,18H,4-5,7,9-11H2,1-3H3/t12-,13-,15+/m0/s1

> <INCHI_KEY>
YXZGFTYVZJDUDK-KCQAQPDRSA-N

> <FORMULA>
C15H27NO2

> <MOLECULAR_WEIGHT>
253.386

> <EXACT_MASS>
253.204179113

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
30.215856896682528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2R,6S)-6-[(2R)-2-hydroxypentyl]-1-methyl-1,2,5,6-tetrahydropyridin-2-yl]butan-2-one

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
2.4527367666666673

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.77063235289646

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.211304106044228

> <JCHEM_PKA_STRONGEST_BASIC>
8.598452913746556

> <JCHEM_POLAR_SURFACE_AREA>
40.540000000000006

> <JCHEM_REFRACTIVITY>
76.0966

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,6S)-6-[(2R)-2-hydroxypentyl]-1-methyl-5,6-dihydro-2H-pyridin-2-yl]butan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.000   3.080   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    5                                                            
CONECT   13    4   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₇NO₂

Average Mass

253.3860 Da

Monoisotopic Mass

253.20418 Da

IUPAC Name

1-[(2R,6S)-6-[(2R)-2-hydroxypentyl]-1-methyl-1,2,5,6-tetrahydropyridin-2-yl]butan-2-one

Traditional Name

1-[(2R,6S)-6-[(2R)-2-hydroxypentyl]-1-methyl-5,6-dihydro-2H-pyridin-2-yl]butan-2-one

CAS Registry Number

Not Available

SMILES

CCC[C@@H](O)C[C@@H]1CC=C[C@@H](CC(=O)CC)N1C

InChI Identifier

InChI=1S/C15H27NO2/c1-4-7-15(18)11-13-9-6-8-12(16(13)3)10-14(17)5-2/h6,8,12-13,15,18H,4-5,7,9-11H2,1-3H3/t12-,13-,15+/m0/s1

InChI Key

YXZGFTYVZJDUDK-KCQAQPDRSA-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
Andrachne aspera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydropyridines. Hydropyridines are compounds containing a hydrogenated pyridine ring (i.E. Containing less than the maximum number of double bonds.).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Hydropyridines

Alternative Parents

Substituents

Beta-aminoketone
Hydropyridine
1,3-aminoalcohol
Ketone
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Amine
Alcohol
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	2.42	ALOGPS
logP	2.45	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	15.21	ChemAxon
pKa (Strongest Basic)	8.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	76.1 m³·mol⁻¹	ChemAxon
Polarizability	30.22 Å³	ChemAxon
Number of Rings	1	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00047004

Chemspider ID

8952596

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10777283

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mill S, Hootele C: Alkaloids of Andrachne aspera. J Nat Prod. 2000 Jun;63(6):762-4. doi: 10.1021/np9905214. [PubMed:10869196 ]

Showing NP-Card for (-)-Andrachcinine (NP0081232)

MOL for NP0081232 ((-)-Andrachcinine)

3D MOL for NP0081232 ((-)-Andrachcinine)

3D SDF for NP0081232 ((-)-Andrachcinine)

3D-SDF for NP0081232 ((-)-Andrachcinine)

PDB for NP0081232 ((-)-Andrachcinine)

3D PDB for NP0081232 ((-)-Andrachcinine)

SMILES for NP0081232 ((-)-Andrachcinine)

INCHI for NP0081232 ((-)-Andrachcinine)

Structure for NP0081232 ((-)-Andrachcinine)

3D Structure for NP0081232 ((-)-Andrachcinine)