NP-MRD: Showing NP-Card for Asclepin (NP0052127)

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Record Information

Version

2.0

Created at

2022-04-27 23:17:41 UTC

Updated at

2022-04-27 23:17:41 UTC

NP-MRD ID

NP0052127

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asclepin

Description

Asclepin belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. Thus, asclepin is considered to be a sterol. Asclepin is found in Asclepias curassavica L. , Gomphocarpus fruticosus, Asclepias fruticosa R.Br. , Asclepias spp. and Asclepias vestita. Based on a literature review very few articles have been published on Asclepin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201172D          

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M  END

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M  END


  Mrv1652304282201172D          

 41 47  0  0  1  0            999 V2000
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    6.4080    1.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4586   -0.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -0.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571    1.4981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3358    0.9553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4952    0.1458    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2759   -0.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8739   -0.3970    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0932   -0.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0662    0.6792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5551    1.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8470    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -1.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140   -1.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4353   -0.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734   -2.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546   -0.6636    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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 15 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 12 24  1  6  0  0  0
 11 25  1  6  0  0  0
  5 26  1  6  0  0  0
 26 27  2  0  0  0  0
  2 28  1  6  0  0  0
 29 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  1 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 35  1  0  0  0  0
 34 36  1  1  0  0  0
 32 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 30 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052127

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](OC(C)=O)[C@]2(O)O[C@@H]3C[C@@]4(C=O)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@H](CC[C@]54O)C4=CC(=O)OC4)C[C@H]3O[C@@H]2O1

> <INCHI_IDENTIFIER>
InChI=1S/C31H42O10/c1-16-10-25(39-17(2)33)31(36)27(38-16)40-23-12-19-4-5-22-21(29(19,15-32)13-24(23)41-31)6-8-28(3)20(7-9-30(22,28)35)18-11-26(34)37-14-18/h11,15-16,19-25,27,35-36H,4-10,12-14H2,1-3H3/t16-,19+,20-,21+,22-,23-,24-,25+,27+,28-,29-,30+,31+/m1/s1

> <INCHI_KEY>
OXKMZIABKYHLAR-SVDYBJNLSA-N

> <FORMULA>
C31H42O10

> <MOLECULAR_WEIGHT>
574.667

> <EXACT_MASS>
574.277797552

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
60.88166181594901

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-14-formyl-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-9-yl acetate

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
2.405041269666666

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.428618461498136

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.180164253002987

> <JCHEM_PKA_STRONGEST_BASIC>
0.26903894433302056

> <JCHEM_POLAR_SURFACE_AREA>
137.82

> <JCHEM_REFRACTIVITY>
142.6751

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-14-formyl-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-9-yl acetate

> <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       5.408   0.788   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.111   2.299   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.270   3.312   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.728   2.814   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.025   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.865   0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.483   0.805   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.642   1.818   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.345   3.329   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.887   3.827   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.100   1.321   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.397  -0.190   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.237  -1.203   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.780  -0.706   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.926  -0.374   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.574   1.023   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.445   2.071   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.676  -1.719   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.205  -1.903   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.503  -3.414   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      17.900  -4.062   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      15.158  -4.164   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.029  -3.117   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.851  -1.662   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.962   2.855   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.323  -0.208   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.163  -1.221   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.653   2.796   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.493   1.783   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.791   0.272   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.248  -0.226   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.631  -0.741   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.174  -0.243   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.124   1.268   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.036   2.281   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.581   1.766   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.929  -2.252   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.386  -2.750   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.546  -1.737   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.684  -4.261   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.089  -1.239   0.000  0.00  0.00           O+0
CONECT    1    2    6   31                                                  
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   26                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   17   25                                             
CONECT   12   11   13   15   24                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11                                                       
CONECT   18   15   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   18                                                       
CONECT   24   12                                                            
CONECT   25   11                                                            
CONECT   26    5   27                                                       
CONECT   27   26                                                            
CONECT   28    2   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31   32   41                                             
CONECT   31   30    1                                                       
CONECT   32   30   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34   29                                                       
CONECT   36   34                                                            
CONECT   37   32   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   30                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Value	Source
3'-O-Acetylcalotropin	Kegg

Chemical Formula

C₃₁H₄₂O₁₀

Average Mass

574.6670 Da

Monoisotopic Mass

574.27780 Da

IUPAC Name

(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-14-formyl-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-9-yl acetate

Traditional Name

(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-14-formyl-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-9-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](OC(C)=O)[C@]2(O)O[C@@H]3C[C@@]4(C=O)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@H](CC[C@]54O)C4=CC(=O)OC4)C[C@H]3O[C@@H]2O1

InChI Identifier

InChI=1S/C31H42O10/c1-16-10-25(39-17(2)33)31(36)27(38-16)40-23-12-19-4-5-22-21(29(19,15-32)13-24(23)41-31)6-8-28(3)20(7-9-30(22,28)35)18-11-26(34)37-14-18/h11,15-16,19-25,27,35-36H,4-10,12-14H2,1-3H3/t16-,19+,20-,21+,22-,23-,24-,25+,27+,28-,29-,30+,31+/m1/s1

InChI Key

OXKMZIABKYHLAR-SVDYBJNLSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Asclepias curassavica	Plant	KNApSAcK
Asclepias fruticosa	LOTUS Database	35616633
Asclepias fruticosa R.Br.	Plant	KNApSAcK
Asclepias spp.	Plant	KNApSAcK
Asclepias vestita	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
19-oxosteroid
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
2-furanone
Dicarboxylic acid or derivatives
Para-dioxane
Oxane
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Enoate ester
Dihydrofuran
Tertiary alcohol
Hemiacetal
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxide
Aldehyde
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cardenolide glycoside (CHEBI:2867 )
cardanolide (C08849 )

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	1.66	ALOGPS
logP	2.41	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	137.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	142.68 m³·mol⁻¹	ChemAxon
Polarizability	60.88 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00003603

Chemspider ID

390421

KEGG Compound ID

C08849

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441844

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Asclepin (NP0052127)

MOL for NP0052127 (Asclepin)

3D MOL for NP0052127 (Asclepin)

3D SDF for NP0052127 (Asclepin)

3D-SDF for NP0052127 (Asclepin)

PDB for NP0052127 (Asclepin)

3D PDB for NP0052127 (Asclepin)

SMILES for NP0052127 (Asclepin)

INCHI for NP0052127 (Asclepin)

Structure for NP0052127 (Asclepin)

3D Structure for NP0052127 (Asclepin)