NP-MRD: Showing NP-Card for (-)-Pohakuline (NP0068366)

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Record Information

Version

2.0

Created at

2022-04-28 13:32:07 UTC

Updated at

2022-04-28 13:32:07 UTC

NP-MRD ID

NP0068366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Pohakuline

Description

(6S)-6-[(1S,3R,9aR)-1-(hydroxymethyl)-octahydro-1H-quinolizin-3-yl]-3,4,5,6-tetrahydropyridin-2-ol belongs to the class of organic compounds known as lupinine-type alkaloids. These are lupin alkaloids with a structure based on the lupinine skeleton, which is a bicyclic compound consisting of a quinolizidine. (-)-Pohakuline is found in Sophora chrysophylla Seem., Ulex australis, Ulex densus, Ulex minor and Ulex jussiaei. Based on a literature review very few articles have been published on (6S)-6-[(1S,3R,9aR)-1-(hydroxymethyl)-octahydro-1H-quinolizin-3-yl]-3,4,5,6-tetrahydropyridin-2-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
    5.1577    0.0306    1.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0807   -0.1173    0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763   -1.2700   -0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4824   -0.7709   -1.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6380    0.4287   -1.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619    1.0164   -0.3719 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7189    0.6933   -0.1230 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1749    1.2658    1.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    1.2388    0.9952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0524    1.9603    2.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261    3.3086    2.0348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7505   -0.1912    0.8408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2311   -0.1667    0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6765   -1.5283   -0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8647   -2.0757   -1.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6763   -1.1363   -1.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469   -0.9373   -0.1131 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3725   -0.7585   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0089    0.8041    0.7590 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8536   -1.8155   -0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1573   -1.9722    0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959   -1.6460   -2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4413   -0.6440   -2.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7203    0.1948   -2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654    1.1970   -2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671    2.1451   -0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410    1.1843   -0.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4085    0.5377    1.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696    2.2644    1.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5471    1.7483    0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1274    1.9920    1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9305    1.5213    3.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7523    3.6255    1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122   -0.6965    1.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3763    0.5405   -0.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8114    0.1067    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7268   -1.4263   -0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098   -2.2554    0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4332   -3.0699   -0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4650   -2.1922   -2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721   -1.7147   -2.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9624   -0.2238   -1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7308   -1.1758   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900   -1.3340    0.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8638    1.3143    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 19  1  0
 12  9  1  0
 19  6  1  0
 12 17  1  0
 11 33  1  0
 10 31  1  0
 10 32  1  0
  9 30  1  6
  8 28  1  0
  8 29  1  0
  7 27  1  6
 18 43  1  0
 18 44  1  0
 16 41  1  0
 16 42  1  0
 15 39  1  0
 15 40  1  0
 14 37  1  0
 14 38  1  0
 13 35  1  0
 13 36  1  0
 12 34  1  1
  6 26  1  6
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
  3 20  1  0
  3 21  1  0
 19 45  1  0
M  END


  Mrv1652304282215322D          

 19 21  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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
    1.4289   -0.0000    0.0000 C   0  0  2  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
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 N   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 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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  1  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
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  6  0  0  0
  7 18  1  1  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1C[C@H](CN2CCCC[C@H]12)[C@@H]1CCCC(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C15H26N2O2/c18-10-12-8-11(13-4-3-6-15(19)16-13)9-17-7-2-1-5-14(12)17/h11-14,18H,1-10H2,(H,16,19)/t11-,12-,13+,14-/m1/s1

> <INCHI_KEY>
ZZHSEFNKICJBHK-YIYPIFLZSA-N

> <FORMULA>
C15H26N2O2

> <MOLECULAR_WEIGHT>
266.385

> <EXACT_MASS>
266.199428085

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
30.477086332662445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6S)-6-[(1S,3R,9aR)-1-(hydroxymethyl)-octahydro-1H-quinolizin-3-yl]piperidin-2-one

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
0.33367417766666646

> <ALOGPS_LOGS>
-1.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.503416767471034

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.654883855191677

> <JCHEM_PKA_STRONGEST_BASIC>
9.504218918276393

> <JCHEM_POLAR_SURFACE_AREA>
52.57000000000001

> <JCHEM_REFRACTIVITY>
74.81309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-6-[(1S,3R,9aR)-1-(hydroxymethyl)-octahydro-1H-quinolizin-3-yl]piperidin-2-one

> <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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -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       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       5.335  -4.620   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11                                                       
CONECT   18    7   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆N₂O₂

Average Mass

266.3850 Da

Monoisotopic Mass

266.19943 Da

IUPAC Name

(6S)-6-[(1S,3R,9aR)-1-(hydroxymethyl)-octahydro-1H-quinolizin-3-yl]piperidin-2-one

Traditional Name

(6S)-6-[(1S,3R,9aR)-1-(hydroxymethyl)-octahydro-1H-quinolizin-3-yl]piperidin-2-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1C[C@H](CN2CCCC[C@H]12)[C@@H]1CCCC(=O)N1

InChI Identifier

InChI=1S/C15H26N2O2/c18-10-12-8-11(13-4-3-6-15(19)16-13)9-17-7-2-1-5-14(12)17/h11-14,18H,1-10H2,(H,16,19)/t11-,12-,13+,14-/m1/s1

InChI Key

ZZHSEFNKICJBHK-YIYPIFLZSA-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
Sophora chrysophylla	Plant	KNApSAcK
Ulex australis	Plant	KNApSAcK
Ulex densus	Plant	KNApSAcK
Ulex minor	Plant	KNApSAcK
Ulex parviflorus subsp. jussiaei	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lupinine-type alkaloids. These are lupin alkaloids with a structure based on the lupinine skeleton, which is a bicyclic compound consisting of a quinolizidine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Lupinine-type alkaloids

Direct Parent

Lupinine-type alkaloids

Alternative Parents

Substituents

Lupinine
Quinolizidine
Quinolizine
Tetrahydropyridine
Hydropyridine
Piperidine
1,3-aminoalcohol
Cyclic carboximidic acid
Tertiary amine
Tertiary aliphatic amine
Lactim
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.29	ALOGPS
logP	0.33	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	14.65	ChemAxon
pKa (Strongest Basic)	9.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.57 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.81 m³·mol⁻¹	ChemAxon
Polarizability	30.48 Å³	ChemAxon
Number of Rings	3	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

Not Available

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

163035603

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

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References

General References

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Showing NP-Card for (-)-Pohakuline (NP0068366)

MOL for NP0068366 ((-)-Pohakuline)

3D MOL for NP0068366 ((-)-Pohakuline)

3D SDF for NP0068366 ((-)-Pohakuline)

3D-SDF for NP0068366 ((-)-Pohakuline)

PDB for NP0068366 ((-)-Pohakuline)

3D PDB for NP0068366 ((-)-Pohakuline)

SMILES for NP0068366 ((-)-Pohakuline)

INCHI for NP0068366 ((-)-Pohakuline)

Structure for NP0068366 ((-)-Pohakuline)

3D Structure for NP0068366 ((-)-Pohakuline)