NP-MRD: Showing NP-Card for (-)-Andrachcinidine (NP0081231)

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Record Information

Version

2.0

Created at

2022-04-29 02:11:47 UTC

Updated at

2022-04-29 02:11:47 UTC

NP-MRD ID

NP0081231

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Andrachcinidine

Description

(?)-Andrachcinidine belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. (-)-Andrachcinidine is found in Andrachne aspera. (-)-Andrachcinidine was first documented in 2003 (PMID: 12617646). Based on a literature review very few articles have been published on (?)-Andrachcinidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
    5.3900   -1.4772    0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554   -1.0089   -0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062   -0.4192    0.7243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603    0.0471    0.1757 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1739    1.0134   -0.7862 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812    0.5822    1.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2844    1.0990    1.0077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3656    2.2176    0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9510    1.9136   -1.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1048    0.9410   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934    0.6050    0.1614 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6240   -0.1970    0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6505   -1.5122   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8485   -2.3745   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7276   -1.9137   -0.9506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1972   -0.0124    0.7045 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2144   -0.8002   -0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6646   -2.4843   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4492   -1.4816    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -0.2868   -1.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5291   -1.9053   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780    0.4574    1.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1001   -1.1182    1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -0.8343   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490    1.6301   -0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9359   -0.2733    2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7123    1.3060    1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792    1.4847    1.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    2.6662   -0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9414    3.0979    0.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1828    1.6079   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3721    2.8678   -1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9996    1.3141   -1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7684    0.0335   -1.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5415    1.5775    0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4781    0.3953   -0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8340   -0.3032    1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6440   -3.4274   -0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2262   -2.3841    0.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6557   -1.9648   -0.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611   -0.6787    0.0306 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 11 16  1  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  6
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  1
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  1
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
M  END


  Mrv1652304292204112D          

 16 16  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  1  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
   -1.4289   -0.8250    0.0000 O   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
    0.7145    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  2  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  1  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
  4 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081231

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@H](O)C[C@H]1CCC[C@@H](CC(C)=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C13H25NO2/c1-3-5-13(16)9-12-7-4-6-11(14-12)8-10(2)15/h11-14,16H,3-9H2,1-2H3/t11-,12+,13-/m0/s1

> <INCHI_KEY>
GFVMHSQLCIEXNG-XQQFMLRXSA-N

> <FORMULA>
C13H25NO2

> <MOLECULAR_WEIGHT>
227.348

> <EXACT_MASS>
227.188529049

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.32675213054162

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2S,6R)-6-[(2S)-2-hydroxypentyl]piperidin-2-yl]propan-2-one

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
1.5751671790000001

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.50149404216825

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.212167658108001

> <JCHEM_PKA_STRONGEST_BASIC>
9.654704357423391

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
65.2124

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2S,6R)-6-[(2S)-2-hydroxypentyl]piperidin-2-yl]propan-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      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   16  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   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₅NO₂

Average Mass

227.3480 Da

Monoisotopic Mass

227.18853 Da

IUPAC Name

1-[(2S,6R)-6-[(2S)-2-hydroxypentyl]piperidin-2-yl]propan-2-one

Traditional Name

1-[(2S,6R)-6-[(2S)-2-hydroxypentyl]piperidin-2-yl]propan-2-one

CAS Registry Number

Not Available

SMILES

CCC[C@H](O)C[C@H]1CCC[C@@H](CC(C)=O)N1

InChI Identifier

InChI=1S/C13H25NO2/c1-3-5-13(16)9-12-7-4-6-11(14-12)8-10(2)15/h11-14,16H,3-9H2,1-2H3/t11-,12+,13-/m0/s1

InChI Key

GFVMHSQLCIEXNG-XQQFMLRXSA-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 piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Not Available

Direct Parent

Piperidines

Alternative Parents

Substituents

Beta-aminoketone
Piperidine
1,3-aminoalcohol
Ketone
Secondary alcohol
Secondary aliphatic amine
Azacycle
Secondary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Hydrocarbon derivative
Alcohol
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	1.61	ALOGPS
logP	1.58	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	15.21	ChemAxon
pKa (Strongest Basic)	9.65	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	65.21 m³·mol⁻¹	ChemAxon
Polarizability	27.33 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

C00047003

Chemspider ID

9022228

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

10846934

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shu C, Liebeskind LS: Enantiocontrolled synthesis of 2,6-disubstituted piperidines by desymmetrization of meso-eta-(3,4,5)-dihydropyridinylmolybdenum complexes. application to the total synthesis of (-)-dihydropinidine and (-)-andrachcinidine. J Am Chem Soc. 2003 Mar 12;125(10):2878-9. doi: 10.1021/ja029537y. [PubMed:12617646 ]

Showing NP-Card for (-)-Andrachcinidine (NP0081231)

MOL for NP0081231 ((-)-Andrachcinidine)

3D MOL for NP0081231 ((-)-Andrachcinidine)

3D SDF for NP0081231 ((-)-Andrachcinidine)

3D-SDF for NP0081231 ((-)-Andrachcinidine)

PDB for NP0081231 ((-)-Andrachcinidine)

3D PDB for NP0081231 ((-)-Andrachcinidine)

SMILES for NP0081231 ((-)-Andrachcinidine)

INCHI for NP0081231 ((-)-Andrachcinidine)

Structure for NP0081231 ((-)-Andrachcinidine)

3D Structure for NP0081231 ((-)-Andrachcinidine)