NP-MRD: Showing NP-Card for methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate (NP0192671)

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Record Information

Version

2.0

Created at

2022-09-04 09:56:39 UTC

Updated at

2022-09-04 09:56:39 UTC

NP-MRD ID

NP0192671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate

Description

Daphnezomine K belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate is found in Daphniphyllum macropodum. Based on a literature review very few articles have been published on Daphnezomine K.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042211562D          

 29 34  0  0  1  0            999 V2000
   -0.0309   -2.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0902   -1.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927   -1.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3350   -1.7922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5333   -0.6094    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1175   -0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9630    0.8549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1209    0.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401    1.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023    0.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540   -0.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284   -0.1269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4749    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122    2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0481    2.3513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8105    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1168    1.0275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027   -0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029   -0.0760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4206   -0.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6512    0.7527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7600    1.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819    2.1477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3523    2.9549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361    1.7737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4112    1.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0080    1.0433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6662    0.5296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5796   -0.2908    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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
  8 12  1  0  0  0  0
  5 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  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
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 15 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 21 28  1  0  0  0  0
 17 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END


  Mrv1652309042211562D          

 29 34  0  0  1  0            999 V2000
   -0.0309   -2.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0902   -1.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927   -1.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3350   -1.7922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5333   -0.6094    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1175   -0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9630    0.8549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1209    0.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401    1.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023    0.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540   -0.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284   -0.1269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4749    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122    2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0481    2.3513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8105    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1168    1.0275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027   -0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029   -0.0760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4206   -0.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6512    0.7527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7600    1.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819    2.1477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3523    2.9549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361    1.7737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4112    1.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0080    1.0433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6662    0.5296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5796   -0.2908    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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
  8 12  1  0  0  0  0
  5 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  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
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 15 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 21 28  1  0  0  0  0
 17 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0192671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1C[C@@]23C4=C(CC[C@H]14)CC[C@H]1CN4C[C@H](C)[C@@H](C[C@@H](O)[C@]21CO)[C@@]34O

> <INCHI_IDENTIFIER>
InChI=1S/C23H33NO5/c1-12-9-24-10-14-5-3-13-4-6-15-16(20(27)29-2)8-22(19(13)15)21(14,11-25)18(26)7-17(12)23(22,24)28/h12,14-18,25-26,28H,3-11H2,1-2H3/t12-,14-,15+,16+,17+,18+,21+,22+,23+/m0/s1

> <INCHI_KEY>
AALIZCQLLBKATA-LNOKRELDSA-N

> <FORMULA>
C23H33NO5

> <MOLECULAR_WEIGHT>
403.519

> <EXACT_MASS>
403.235873167

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.98631566110115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,3R,4R,10R,14R,15R,17R,18S,19R)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icos-7(20)-ene-3-carboxylate

> <JCHEM_LOGP>
0.3747024439999989

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.445649313102574

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.584242065852607

> <JCHEM_PKA_STRONGEST_BASIC>
10.05176245783713

> <JCHEM_POLAR_SURFACE_AREA>
90.23

> <JCHEM_REFRACTIVITY>
107.2946

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,3R,4R,10R,14R,15R,17R,18S,19R)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1^{1,4}.0^{10,18}.0^{15,19}.0^{7,20}]icos-7(20)-ene-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.058  -5.073   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.168  -3.537   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.106  -2.673   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.492  -3.346   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.996  -1.137   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.086  -0.072   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.798   1.596   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.226   1.293   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.008   2.204   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.244   1.173   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.781  -0.315   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.240  -0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.887   3.795   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.396   4.752   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.956   4.389   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.380   3.539   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.951   1.918   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.738  -0.053   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.232  -0.142   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.385  -1.163   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.949   1.405   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.152   2.914   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.073   4.009   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.391   5.516   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.307   3.311   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.768   3.291   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.015   1.948   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.110   0.989   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.949  -0.543   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   25   28                                             
CONECT    8    7    9   12                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8    5                                                  
CONECT   13    9   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   15    7   26                                             
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   21   17    7   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   68    0
END

View in JSmol

Synonyms

Not Available

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

COC(=O)[C@@H]1C[C@@]23C4=C(CC[C@H]14)CC[C@H]1CN4C[C@H](C)[C@@H](C[C@@H](O)[C@]21CO)[C@@]34O

InChI Identifier

InChI=1S/C23H33NO5/c1-12-9-24-10-14-5-3-13-4-6-15-16(20(27)29-2)8-22(19(13)15)21(14,11-25)18(26)7-17(12)23(22,24)28/h12,14-18,25-26,28H,3-11H2,1-2H3/t12-,14-,15+,16+,17+,18+,21+,22+,23+/m0/s1

InChI Key

AALIZCQLLBKATA-LNOKRELDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Daphniphyllum macropodum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
Indolizidine
Indole or derivatives
N-alkylpyrrolidine
Piperidine
Methyl ester
Pyrrolidine
Cyclic alcohol
Secondary alcohol
Hemiaminal
Carboxylic acid ester
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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

101026198

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate (NP0192671)

MOL for NP0192671 (methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate)

3D MOL for NP0192671 (methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate)

3D SDF for NP0192671 (methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate)

3D-SDF for NP0192671 (methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate)

PDB for NP0192671 (methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate)

3D PDB for NP0192671 (methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate)

SMILES for NP0192671 (methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate)

INCHI for NP0192671 (methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate)

Structure for NP0192671 (methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate)

3D Structure for NP0192671 (methyl (1r,3r,4r,10r,14r,15r,17r,18s,19r)-17,19-dihydroxy-18-(hydroxymethyl)-14-methyl-12-azahexacyclo[10.6.1.1¹,⁴.0¹⁰,¹⁸.0¹⁵,¹⁹.0⁷,²⁰]icos-7(20)-ene-3-carboxylate)