NP-MRD: Showing NP-Card for Flavadine (NP0067182)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 11:28:09 UTC

Updated at

2022-04-28 11:28:09 UTC

NP-MRD ID

NP0067182

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Flavadine

Description

(1S,2R,4S,5R,7R,8S,9S,10S,13S,16S,17R)-11-ethyl-4,16-dihydroxy-13-methyl-6-methylidene-11-oxo-11λ⁵-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]Nonadecan-7-yl acetate belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Flavadine is found in Aconitum flavum. Based on a literature review very few articles have been published on (1S,2R,4S,5R,7R,8S,9S,10S,13S,16S,17R)-11-ethyl-4,16-dihydroxy-13-methyl-6-methylidene-11-oxo-11λ⁵-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]Nonadecan-7-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282213282D          

 30 35  0  0  1  0            999 V2000
    0.9778    0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7495   -0.3516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4299   -1.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348   -1.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679   -1.6576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1355   -0.8277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3833    0.1948    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9307   -0.0464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8812    0.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4996   -0.5643    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4706   -0.7374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9211   -1.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4630   -1.8127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8733   -2.4406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0537   -2.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369   -1.3373    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0959   -3.2350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8925   -1.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7133   -0.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107   -0.4213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5078    0.3798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3001    0.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4972    1.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8953    0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618    0.8361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2929    1.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032    1.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954    1.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2875   -2.2984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0330   -0.0901    0.0000 C   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
  6  7  1  6  0  0  0
  7  8  1  1  0  0  0
  8  9  1  1  0  0  0
 10  9  1  1  0  0  0
  2 10  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
  6 16  1  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  1  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  7 25  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 29  1  1  0  0  0
  2 30  1  1  0  0  0
M  END


  Mrv1652304282213282D          

 30 35  0  0  1  0            999 V2000
    0.9778    0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7495   -0.3516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4299   -1.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348   -1.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679   -1.6576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1355   -0.8277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3833    0.1948    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9307   -0.0464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8812    0.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4996   -0.5643    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4706   -0.7374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9211   -1.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4630   -1.8127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8733   -2.4406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0537   -2.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369   -1.3373    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0959   -3.2350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8925   -1.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7133   -0.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107   -0.4213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5078    0.3798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3001    0.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4972    1.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8953    0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618    0.8361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2929    1.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032    1.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954    1.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2875   -2.2984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0330   -0.0901    0.0000 C   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
  6  7  1  6  0  0  0
  7  8  1  1  0  0  0
  8  9  1  1  0  0  0
 10  9  1  1  0  0  0
  2 10  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
  6 16  1  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  1  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  7 25  1  0  0  0  0
  1 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 29  1  1  0  0  0
  2 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0067182

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1(=O)C[C@@]2(C)CC[C@H](O)[C@]34[C@@H]2C[C@H]([C@H]13)[C@]12C[C@@H]([C@@H](O)C[C@@H]41)C(=C)[C@H]2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H35NO5/c1-5-25(29)11-22(4)7-6-19(28)24-17(22)8-15(20(24)25)23-10-14(16(27)9-18(23)24)12(2)21(23)30-13(3)26/h14-21,27-28H,2,5-11H2,1,3-4H3/t14-,15-,16+,17-,18-,19+,20+,21-,22-,23-,24-,25?/m1/s1

> <INCHI_KEY>
CVKNHZTVQWAOMK-WEVPJGPBSA-N

> <FORMULA>
C24H35NO5

> <MOLECULAR_WEIGHT>
417.546

> <EXACT_MASS>
417.251523231

$$$$

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       1.825   0.906   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.399  -0.656   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.803  -2.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.745  -3.424   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.300  -3.094   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.986  -1.545   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.449   0.364   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.471  -0.087   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.512   0.336   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.799  -1.053   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.478  -1.376   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.319  -2.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.331  -3.384   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.230  -4.556   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.700  -4.132   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.296  -2.496   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.646  -6.039   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.133  -2.004   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.665  -1.848   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.047  -0.787   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.415   0.709   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.894   1.138   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.261   2.633   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.005   0.072   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       3.289   1.561   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0       4.280   2.739   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.806   3.023   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.298   3.336   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.270  -4.290   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.062  -0.168   0.000  0.00  0.00           C+0
CONECT    1    2   25                                                       
CONECT    2    1    3   10   30                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7   10   16                                             
CONECT    7    6    8   25                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    2    6                                                  
CONECT   11    8   12   16   20                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    6   11                                                  
CONECT   17   14                                                            
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    7    1   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29    5                                                            
CONECT   30    2                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,4S,5R,7R,8S,9S,10S,13S,16S,17R)-11-Ethyl-4,16-dihydroxy-13-methyl-6-methylidene-11-oxo-11-azahexacyclo[7.7.2.1,.0,.0,.0,]nonadecan-7-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₅NO₅

Average Mass

417.5460 Da

Monoisotopic Mass

417.25152 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCN1(=O)C[C@@]2(C)CC[C@H](O)[C@]34[C@@H]2C[C@H]([C@H]13)[C@]12C[C@@H]([C@@H](O)C[C@@H]41)C(=C)[C@H]2OC(C)=O

InChI Identifier

InChI=1S/C24H35NO5/c1-5-25(29)11-22(4)7-6-19(28)24-17(22)8-15(20(24)25)23-10-14(16(27)9-18(23)24)12(2)21(23)30-13(3)26/h14-21,27-28H,2,5-11H2,1,3-4H3/t14-,15-,16+,17-,18-,19+,20+,21-,22-,23-,24-,25?/m1/s1

InChI Key

CVKNHZTVQWAOMK-WEVPJGPBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aconitum flavum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Azepane
Piperidine
Trialkyl amine oxide
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
Monocarboxylic acid or derivatives
Carboxylic acid derivative
N-oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
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

163184428

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Flavadine (NP0067182)

MOL for NP0067182 (Flavadine)

3D MOL for NP0067182 (Flavadine)

3D SDF for NP0067182 (Flavadine)

3D-SDF for NP0067182 (Flavadine)

PDB for NP0067182 (Flavadine)

3D PDB for NP0067182 (Flavadine)

SMILES for NP0067182 (Flavadine)

INCHI for NP0067182 (Flavadine)

Structure for NP0067182 (Flavadine)

3D Structure for NP0067182 (Flavadine)