NP-MRD: Showing NP-Card for Cammaconine (NP0050773)

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Record Information

Version

2.0

Created at

2022-04-27 22:06:20 UTC

Updated at

2022-04-27 22:06:20 UTC

NP-MRD ID

NP0050773

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cammaconine

Description

32152-70-8, Also known as columbiananine, belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. Cammaconine is found in Aconitum columbianum, Aconitum contortum, Aconitum forrestii, Aconitum karakolicum, Aconitum liljestrandii, Aconitum orientale, Aconitum talassicum, Aconitum variegatum, Aconitum varigatum, Delphinium linearilobum and Hansenia weberbaueriana. Based on a literature review very few articles have been published on 32152-70-8.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200062D          

 29 34  0  0  1  0            999 V2000
   -1.4203   -1.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138   -1.7742    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2009   -1.7085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8077   -1.4449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4745   -0.5800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3558   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9140   -0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0296    0.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786    0.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4476   -0.7834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0963   -1.1216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3031   -1.9438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5610   -2.4846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5081   -2.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9650   -2.4748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1926   -3.0339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5578   -2.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436   -3.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4440   -4.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1388   -1.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372   -1.1688    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9980   -0.4617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5019   -0.2213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2205    0.5543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961   -0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3596   -1.1031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5736   -2.7232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -2.7335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  6  0  0  0
  8  9  1  0  0  0  0
  4 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
  3 14  1  6  0  0  0
 13 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  1  0  0  0
 22 25  1  6  0  0  0
 10 25  1  6  0  0  0
 21 26  1  1  0  0  0
 26 27  1  0  0  0  0
 12 28  1  1  0  0  0
  1 29  1  0  0  0  0
M  END


  Mrv1652304282200062D          

 29 34  0  0  1  0            999 V2000
   -1.4203   -1.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138   -1.7742    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2009   -1.7085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8077   -1.4449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4745   -0.5800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3558   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9140   -0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0296    0.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786    0.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4476   -0.7834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0963   -1.1216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3031   -1.9438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5610   -2.4846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5081   -2.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9650   -2.4748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1926   -3.0339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5578   -2.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436   -3.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4440   -4.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1388   -1.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372   -1.1688    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9980   -0.4617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5019   -0.2213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2205    0.5543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961   -0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3596   -1.1031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5736   -2.7232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729   -2.7335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  6  0  0  0
  8  9  1  0  0  0  0
  4 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
  3 14  1  6  0  0  0
 13 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  1  0  0  0
 22 25  1  6  0  0  0
 10 25  1  6  0  0  0
 21 26  1  1  0  0  0
 26 27  1  0  0  0  0
 12 28  1  1  0  0  0
  1 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050773

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(CO)CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@H](C[C@H]23)[C@@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C23H37NO5/c1-4-24-10-21(11-25)6-5-17(29-3)23-13-7-12-15(28-2)9-22(27,18(13)19(12)26)14(20(23)24)8-16(21)23/h12-20,25-27H,4-11H2,1-3H3/t12-,13-,14+,15+,16-,17+,18-,19+,20-,21+,22+,23-/m1/s1

> <INCHI_KEY>
WCEASIFXIDFWHE-VHNKBEDGSA-N

> <FORMULA>
C23H37NO5

> <MOLECULAR_WEIGHT>
407.551

> <EXACT_MASS>
407.267173295

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
45.34763829753619

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4S,5S,6S,8S,9S,10R,13S,16S,17R)-11-ethyl-13-(hydroxymethyl)-6,16-dimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8-diol

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
-0.9132254113333347

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.618395292235157

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.942479907185017

> <JCHEM_PKA_STRONGEST_BASIC>
9.842197654305751

> <JCHEM_POLAR_SURFACE_AREA>
82.39000000000001

> <JCHEM_REFRACTIVITY>
108.28620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4S,5S,6S,8S,9S,10R,13S,16S,17R)-11-ethyl-13-(hydroxymethyl)-6,16-dimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8-diol

> <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      -2.651  -3.636   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.146  -3.312   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.375  -3.189   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.508  -2.697   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.886  -1.083   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.664  -0.649   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.706  -1.817   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.922   0.057   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.453   1.524   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.702  -1.462   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.913  -2.094   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.299  -3.628   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.914  -4.638   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.949  -4.777   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.801  -4.620   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.360  -5.663   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.041  -4.893   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.455  -7.200   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.829  -8.051   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.859  -3.569   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.603  -2.182   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.596  -0.862   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.670  -0.413   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.145   1.035   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.726  -0.065   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.138  -2.059   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.799  -0.668   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.804  -5.083   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -3.123  -5.103   0.000  0.00  0.00           O+0
CONECT    1    2   29                                                       
CONECT    2    1    3    7   17                                             
CONECT    3    2    4   14                                                  
CONECT    4    3    5   10   15                                             
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9                                                       
CONECT    9    8                                                            
CONECT   10    4   11   25                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13   20   28                                             
CONECT   13   12   14   15                                                  
CONECT   14   13    3                                                       
CONECT   15   13    4   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16    2                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   12   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   11   24                                                  
CONECT   24   23                                                            
CONECT   25   22   10                                                       
CONECT   26   21   27                                                       
CONECT   27   26                                                            
CONECT   28   12                                                            
CONECT   29    1                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   68    0
END

View in JSmol

Synonyms

Value	Source
Columbiananine	MeSH

Chemical Formula

C₂₃H₃₇NO₅

Average Mass

407.5510 Da

Monoisotopic Mass

407.26717 Da

IUPAC Name

(1S,2R,3R,4S,5S,6S,8S,9S,10R,13S,16S,17R)-11-ethyl-13-(hydroxymethyl)-6,16-dimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8-diol

Traditional Name

(1S,2R,3R,4S,5S,6S,8S,9S,10R,13S,16S,17R)-11-ethyl-13-(hydroxymethyl)-6,16-dimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,8-diol

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(CO)CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@H](C[C@H]23)[C@@H]14

InChI Identifier

InChI=1S/C23H37NO5/c1-4-24-10-21(11-25)6-5-17(29-3)23-13-7-12-15(28-2)9-22(27,18(13)19(12)26)14(20(23)24)8-16(21)23/h12-20,25-27H,4-11H2,1-3H3/t12-,13-,14+,15+,16-,17+,18-,19+,20-,21+,22+,23-/m1/s1

InChI Key

WCEASIFXIDFWHE-VHNKBEDGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aconitum columbianum	LOTUS Database	35616633
Aconitum contortum	LOTUS Database	35616633
Aconitum forrestii	LOTUS Database	35616633
Aconitum karakolicum	LOTUS Database	35616633
Aconitum liljestrandii	LOTUS Database	35616633
Aconitum orientale	LOTUS Database	35616633
Aconitum talassicum	LOTUS Database	35616633
Aconitum variegatum	Plant	KNApSAcK
Aconitum varigatum	Plant	KNApSAcK
Delphinium linearilobum	Plant	KNApSAcK
Hansenia weberbaueriana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Aconitane-type diterpenoid alkaloids

Alternative Parents

Substituents

Aconitane-type diterpenoid alkaloid
Quinolidine
Alkaloid or derivatives
Azepane
Piperidine
1,3-aminoalcohol
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Amine
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	0.4	ALOGPS
logP	-0.91	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.94	ChemAxon
pKa (Strongest Basic)	9.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.39 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.29 m³·mol⁻¹	ChemAxon
Polarizability	45.35 Å³	ChemAxon
Number of Rings	6	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

C00001622

Chemspider ID

78315882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101600197

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cammaconine (NP0050773)

MOL for NP0050773 (Cammaconine)

3D MOL for NP0050773 (Cammaconine)

3D SDF for NP0050773 (Cammaconine)

3D-SDF for NP0050773 (Cammaconine)

PDB for NP0050773 (Cammaconine)

3D PDB for NP0050773 (Cammaconine)

SMILES for NP0050773 (Cammaconine)

INCHI for NP0050773 (Cammaconine)

Structure for NP0050773 (Cammaconine)

3D Structure for NP0050773 (Cammaconine)