NP-MRD: Showing NP-Card for Gomandonine 13-O-acetate (NP0067190)

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Record Information

Version

2.0

Created at

2022-04-28 11:29:28 UTC

Updated at

2022-04-28 11:29:28 UTC

NP-MRD ID

NP0067190

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gomandonine 13-O-acetate

Description

(1R,2S,5S,8R,9R,10S,11S,12S,13R,15R,16R,18S)-2,11-dihydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]Nonadecane-12,2'-oxirane]-18-yl acetate belongs to the class of organic compounds known as danudatine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the danudatine skeleton, which is a hexacyclic compound with an additional C-20-C7 bond in the atisine skeleton. Gomandonine 13-O-acetate is found in Aconitum delphinifolium. Based on a literature review very few articles have been published on (1R,2S,5S,8R,9R,10S,11S,12S,13R,15R,16R,18S)-2,11-dihydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]Nonadecane-12,2'-oxirane]-18-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282213292D          

 29 35  0  0  1  0            999 V2000
    2.4832   -0.3163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6355   -0.1764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7306    0.8317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0458    0.3838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2330    0.1251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0762    0.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4019    1.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2462    1.5607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4601    2.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790   -0.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1952   -0.9208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926   -1.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965   -0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9382    0.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271    0.9843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1418    0.2385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1126    0.1585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6361    0.8441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9647    1.3664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1652    1.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7022    0.5702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6661   -0.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1313    1.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5828    1.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7634    1.7839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096    2.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882    1.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3998    0.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6597   -0.5685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  1  0  0  0
 11 12  1  0  0  0  0
  5 13  1  6  0  0  0
  4 14  1  6  0  0  0
  1 14  1  1  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
  1 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 15 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 18 27  1  1  0  0  0
 27 28  1  0  0  0  0
 18 28  1  0  0  0  0
 17 29  1  1  0  0  0
M  END


  Mrv1652304282213292D          

 29 35  0  0  1  0            999 V2000
    2.4832   -0.3163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6355   -0.1764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7306    0.8317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0458    0.3838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2330    0.1251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0762    0.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4019    1.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2462    1.5607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4601    2.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790   -0.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1952   -0.9208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926   -1.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965   -0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9382    0.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271    0.9843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1418    0.2385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1126    0.1585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6361    0.8441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9647    1.3664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1652    1.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7022    0.5702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6661   -0.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1313    1.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5828    1.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7634    1.7839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096    2.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882    1.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3998    0.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6597   -0.5685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  1  0  0  0
 11 12  1  0  0  0  0
  5 13  1  6  0  0  0
  4 14  1  6  0  0  0
  1 14  1  1  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
  1 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 15 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 18 27  1  1  0  0  0
 27 28  1  0  0  0  0
 18 28  1  0  0  0  0
 17 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0067190

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C[C@@]2(C)CC[C@H](O)[C@@]34[C@@H]5C[C@@H]6[C@H](C[C@]5([C@@H](C[C@H]23)[C@@H]14)[C@H](O)[C@@]61CO1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H33NO5/c1-11(25)29-14-8-21-13-7-15-20(2)5-4-17(26)23(15,18(13)24(3)9-20)16(21)6-12(14)22(10-28-22)19(21)27/h12-19,26-27H,4-10H2,1-3H3/t12-,13+,14+,15-,16-,17+,18-,19+,20-,21-,22-,23+/m1/s1

> <INCHI_KEY>
SNJXXMIUXNTITL-JLISYNOWSA-N

> <FORMULA>
C23H33NO5

> <MOLECULAR_WEIGHT>
403.519

> <EXACT_MASS>
403.235873167

$$$$

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       4.635  -0.590   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.053  -0.329   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.230   1.553   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.952   0.716   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.435   0.234   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.142   1.723   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.750   3.037   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.326   2.913   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.725   4.501   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.708  -1.339   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.231  -1.719   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.786  -3.211   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.114  -0.212   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.618   0.542   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.904   1.837   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.865   0.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.677   0.296   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.654   1.576   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.401   2.551   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.908   3.102   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.911   1.064   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.843  -0.655   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.845   2.133   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.821   3.509   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.292   3.330   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.431   4.922   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.871   2.519   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.080   0.993   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.698  -1.061   0.000  0.00  0.00           O+0
CONECT    1    2   14   16                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4    8   15                                             
CONECT    4    3    5   14                                                  
CONECT    5    4    6   10   13                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11                                                            
CONECT   13    5                                                            
CONECT   14    4    1                                                       
CONECT   15    3   16   20                                                  
CONECT   16   15    1   17   22                                             
CONECT   17   16   18   29                                                  
CONECT   18   17   19   27   28                                             
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19   22   23                                                  
CONECT   22   21   16                                                       
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   18   28                                                       
CONECT   28   27   18                                                       
CONECT   29   17                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,5S,8R,9R,10S,11S,12S,13R,15R,16R,18S)-2,11-Dihydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2,.0,.0,.0,]nonadecane-12,2'-oxirane]-18-yl acetic acid	Generator

Chemical Formula

C₂₃H₃₃NO₅

Average Mass

403.5190 Da

Monoisotopic Mass

403.23587 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CN1C[C@@]2(C)CC[C@H](O)[C@@]34[C@@H]5C[C@@H]6[C@H](C[C@]5([C@@H](C[C@H]23)[C@@H]14)[C@H](O)[C@@]61CO1)OC(C)=O

InChI Identifier

InChI=1S/C23H33NO5/c1-11(25)29-14-8-21-13-7-15-20(2)5-4-17(26)23(15,18(13)24(3)9-20)16(21)6-12(14)22(10-28-22)19(21)27/h12-19,26-27H,4-10H2,1-3H3/t12-,13+,14+,15-,16-,17+,18-,19+,20-,21-,22-,23+/m1/s1

InChI Key

SNJXXMIUXNTITL-JLISYNOWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aconitum delphinifolium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as danudatine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the danudatine skeleton, which is a hexacyclic compound with an additional C-20-C7 bond in the atisine skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Danudatine-type diterpenoid alkaloids

Alternative Parents

Substituents

Danudatine-type diterpenoid alkaloid
Alkaloid or derivatives
Azepane
Piperidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
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

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

163106000

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gomandonine 13-O-acetate (NP0067190)

MOL for NP0067190 (Gomandonine 13-O-acetate)

3D MOL for NP0067190 (Gomandonine 13-O-acetate)

3D SDF for NP0067190 (Gomandonine 13-O-acetate)

3D-SDF for NP0067190 (Gomandonine 13-O-acetate)

PDB for NP0067190 (Gomandonine 13-O-acetate)

3D PDB for NP0067190 (Gomandonine 13-O-acetate)

SMILES for NP0067190 (Gomandonine 13-O-acetate)

INCHI for NP0067190 (Gomandonine 13-O-acetate)

Structure for NP0067190 (Gomandonine 13-O-acetate)

3D Structure for NP0067190 (Gomandonine 13-O-acetate)