NP-MRD: Showing NP-Card for (1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate (NP0203658)

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Record Information

Version

2.0

Created at

2022-09-04 23:10:26 UTC

Updated at

2022-09-04 23:10:26 UTC

NP-MRD ID

NP0203658

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate

Description

(1S,2S,5S,9S,11S,12R,13R,15R,16R,18S)-2-(acetyloxy)-11-hydroxy-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. (1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate is found in Aconitum sachalinense. Based on a literature review very few articles have been published on (1S,2S,5S,9S,11S,12R,13R,15R,16R,18S)-2-(acetyloxy)-11-hydroxy-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 3D MOL SDF PDB SMILES InChI


  Mrv1652309052201102D          

 32 38  0  0  1  0            999 V2000
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M  END

     RDKit          2D

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M  END


  Mrv1652309052201102D          

 32 38  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0203658

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C[C@@]2(C)CC[C@H](OC(C)=O)[C@]34[C@@H]5C[C@@H]6[C@H](CC5([C@H](C[C@H]23)C14)[C@H](O)[C@]61CO1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H35NO6/c1-12(27)31-16-9-23-15-8-17-22(3)6-5-19(32-13(2)28)25(17,20(15)26(4)10-22)18(23)7-14(16)24(11-30-24)21(23)29/h14-21,29H,5-11H2,1-4H3/t14-,15-,16+,17-,18-,19+,20?,21+,22-,23?,24+,25-/m1/s1

> <INCHI_KEY>
SVJXZSAPSHPUSE-VTVJAWNTSA-N

> <FORMULA>
C25H35NO6

> <MOLECULAR_WEIGHT>
445.556

> <EXACT_MASS>
445.246437851

> <ALOGPS_LOGP>
1.36

> <ALOGPS_LOGS>
-2.87

> <ALOGPS_SOLUBILITY>
5.99e-01 g/l

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      15.416  -0.985   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.849   0.493   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      17.346   0.857   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      14.786   1.607   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      13.289   1.243   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.495  -0.144   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.689  -0.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.583  -1.503   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.442  -0.505   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.758  -0.561   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.266  -1.148   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.830  -1.703   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.520   0.251   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.248   1.647   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.833   1.652   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.466   3.056   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.568   4.306   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.035   4.153   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.202   5.710   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.903   0.430   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.971  -1.432   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       7.221  -2.843   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       7.951  -4.199   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.657  -2.694   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.515   0.897   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.392   2.250   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.969   2.095   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.624   0.553   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.118   0.228   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.590   1.694   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.853  -1.173   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.632  -2.502   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   25   31                                             
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12   13   24                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   10   21   25                                             
CONECT   21   20    8   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   11                                                       
CONECT   25   20    7   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26    5   28                                                  
CONECT   28   27   29   30   31                                             
CONECT   29   28   30                                                       
CONECT   30   29   28                                                       
CONECT   31   28    7   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   76    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₅H₃₅NO₆

Average Mass

445.5560 Da

Monoisotopic Mass

445.24644 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CN1C[C@@]2(C)CC[C@H](OC(C)=O)[C@]34[C@@H]5C[C@@H]6[C@H](CC5([C@H](C[C@H]23)C14)[C@H](O)[C@]61CO1)OC(C)=O

InChI Identifier

InChI=1S/C25H35NO6/c1-12(27)31-16-9-23-15-8-17-22(3)6-5-19(32-13(2)28)25(17,20(15)26(4)10-22)18(23)7-14(16)24(11-30-24)21(23)29/h14-21,29H,5-11H2,1-4H3/t14-,15-,16+,17-,18-,19+,20?,21+,22-,23?,24+,25-/m1/s1

InChI Key

SVJXZSAPSHPUSE-VTVJAWNTSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Aconitum sachalinense	LOTUS Database	35616633

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
Dicarboxylic acid or derivatives
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
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

163189958

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate (NP0203658)

MOL for NP0203658 ((1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate)

3D MOL for NP0203658 ((1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate)

3D SDF for NP0203658 ((1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate)

3D-SDF for NP0203658 ((1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate)

PDB for NP0203658 ((1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate)

3D PDB for NP0203658 ((1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate)

SMILES for NP0203658 ((1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate)

INCHI for NP0203658 ((1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate)

Structure for NP0203658 ((1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate)

3D Structure for NP0203658 ((1s,2s,5s,9s,11s,12r,13r,15r,16r,18s)-18-(acetyloxy)-11-hydroxy-5,7-dimethyl-7-azaspiro[hexacyclo[7.6.2.2¹⁰,¹³.0¹,⁸.0⁵,¹⁶.0¹⁰,¹⁵]nonadecane-12,2'-oxiran]-2-yl acetate)