NP-MRD: Showing NP-Card for Calpurmenine (NP0055121)

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Record Information

Version

2.0

Created at

2022-04-28 01:15:26 UTC

Updated at

2022-04-28 01:15:26 UTC

NP-MRD ID

NP0055121

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calpurmenine

Description

(1S,2R,9R,10R,11S,12S)-11,12-dihydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]Heptadecan-6-one belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems. Calpurmenine is found in Calpurnia aurea subsp. aurea . Based on a literature review very few articles have been published on (1S,2R,9R,10R,11S,12S)-11,12-dihydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]Heptadecan-6-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.6536   -1.7377    2.5677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277   -0.8263    1.7387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9748   -0.0360    1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2407   -0.2886   -0.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0713    0.1031   -0.8779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8229    0.4521   -0.1552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5729    0.2480   -0.8315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5196   -1.2812   -0.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4972   -1.5378    0.1380 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2245   -0.9272    1.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6078   -0.4638    1.0014 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6612   -0.8117   -0.4691 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7086   -0.3375    0.4858 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4957   -0.9534    1.7376 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8367    1.1491    0.6523 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1087    1.4841    1.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5813    1.9068   -0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5724    0.9109   -1.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5081   -0.0310   -1.6594 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2398    0.7066   -1.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7391    1.0272    1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7819   -0.4185    2.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1779    0.1991   -0.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4467   -1.3943   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979    1.0153   -1.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8541   -0.6468   -1.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860    1.4687    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821    0.6742    0.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501   -1.8009   -0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1054   -1.6390   -1.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5699   -2.6187    0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3142   -0.1594    1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3998   -1.7601    2.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2033   -1.7097   -0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7600   -0.6734    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3472   -1.0426    2.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133    1.4879    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7584    0.9743    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6764    2.5207   -0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4224    2.6228   -0.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    1.5199   -2.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697    0.4790   -1.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0994    0.3558   -2.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4318    1.7901   -1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 12 19  1  0
  6  7  1  0
  2 11  1  0
 16 38  1  0
 15 37  1  1
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 20 43  1  0
 20 44  1  0
  7 28  1  1
  8 29  1  0
  8 30  1  0
  9 31  1  1
 10 32  1  0
 10 33  1  0
  6 27  1  1
  5 25  1  0
  5 26  1  0
  4 23  1  0
  4 24  1  0
  3 21  1  0
  3 22  1  0
 12 34  1  6
 13 35  1  6
 14 36  1  0
M  END


  Mrv1652304282203152D          

 20 23  0  0  1  0            999 V2000
    6.3404    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -0.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    1.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114    2.0344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6259    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281    2.6178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1646    1.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.6260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3281    0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197    1.2094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9197    2.0344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    2.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    1.2094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2053    0.7969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2053   -0.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7763    0.7969    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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  6  0  0  0
 17 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0055121

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CCN2C[C@@H]3C[C@H](CN4[C@@H]3CCCC4=O)[C@@H]2[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O3/c18-12-4-5-16-7-9-6-10(14(16)15(12)20)8-17-11(9)2-1-3-13(17)19/h9-12,14-15,18,20H,1-8H2/t9-,10+,11+,12-,14+,15+/m0/s1

> <INCHI_KEY>
UTXHASMILNXHNR-YYQHBFALSA-N

> <FORMULA>
C15H24N2O3

> <MOLECULAR_WEIGHT>
280.368

> <EXACT_MASS>
280.178692641

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
30.43443875514175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,9R,10R,11S,12S)-11,12-dihydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

> <ALOGPS_LOGP>
-0.06

> <JCHEM_LOGP>
-1.1466739080000008

> <ALOGPS_LOGS>
-0.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.070612083847188

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.486236916314724

> <JCHEM_PKA_STRONGEST_BASIC>
8.825692359525828

> <JCHEM_POLAR_SURFACE_AREA>
64.01

> <JCHEM_REFRACTIVITY>
74.12790000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.84e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,9R,10R,11S,12S)-11,12-dihydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-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      11.835   3.798   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.835   2.258   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.502   1.488   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.502  -0.052   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.168   2.258   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.168   3.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.502   4.568   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.079   4.886   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.774   2.835   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.539   1.169   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.079   1.169   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.450   2.258   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.450   3.798   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.539   4.886   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.116   4.568   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.783   3.798   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.783   2.258   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.116   1.488   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.116  -0.052   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.449   1.488   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    8                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18                                                            
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄N₂O₃

Average Mass

280.3680 Da

Monoisotopic Mass

280.17869 Da

IUPAC Name

(1S,2R,9R,10R,11S,12S)-11,12-dihydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

Traditional Name

(1S,2R,9R,10R,11S,12S)-11,12-dihydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

CAS Registry Number

Not Available

SMILES

O[C@H]1CCN2C[C@@H]3C[C@H](CN4[C@@H]3CCCC4=O)[C@@H]2[C@@H]1O

InChI Identifier

InChI=1S/C15H24N2O3/c18-12-4-5-16-7-9-6-10(14(16)15(12)20)8-17-11(9)2-1-3-13(17)19/h9-12,14-15,18,20H,1-8H2/t9-,10+,11+,12-,14+,15+/m0/s1

InChI Key

UTXHASMILNXHNR-YYQHBFALSA-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
Calpurnia aurea subsp. aurea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Sparteine, lupanine, and related alkaloids

Direct Parent

Sparteine, lupanine, and related alkaloids

Alternative Parents

Substituents

Sparteine-lupanine skeleton
Quinolizidinone
Quinolizidine
Piperidinone
Delta-lactam
Piperidine
Tertiary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Lactam
Carboxamide group
Amino acid or derivatives
1,2-diol
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	-0.06	ALOGPS
logP	-1.1	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Acidic)	13.49	ChemAxon
pKa (Strongest Basic)	8.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.01 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	74.13 m³·mol⁻¹	ChemAxon
Polarizability	30.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

162972648

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Calpurmenine (NP0055121)

MOL for NP0055121 (Calpurmenine)

3D MOL for NP0055121 (Calpurmenine)

3D SDF for NP0055121 (Calpurmenine)

3D-SDF for NP0055121 (Calpurmenine)

PDB for NP0055121 (Calpurmenine)

3D PDB for NP0055121 (Calpurmenine)

SMILES for NP0055121 (Calpurmenine)

INCHI for NP0055121 (Calpurmenine)

Structure for NP0055121 (Calpurmenine)

3D Structure for NP0055121 (Calpurmenine)