NP-MRD: Showing NP-Card for Uscharidin (NP0052160)

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Record Information

Version

2.0

Created at

2022-04-27 23:19:05 UTC

Updated at

2022-04-27 23:19:05 UTC

NP-MRD ID

NP0052160

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Uscharidin

Description

Uscharidin 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, uscharidin is considered to be a sterol. Uscharidin is found in Asclepias curassavica L. , Gomphocarpus fruticosus, Asclepias fruticosa R.Br. , Asclepias subulata, Calotropis procera and Thymus vulgaris. Uscharidin was first documented in 2003 (PMID: 14627515). Based on a literature review a small amount of articles have been published on Uscharidin (PMID: 33572107) (PMID: 34563976) (PMID: 19251412) (PMID: 15313684).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304282201192D          

 38 44  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END

  Mrv1652304282201192D          

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    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
    1.6546   -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  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 35 37  1  1  0  0  0
 30 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052160

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC(=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/C29H38O9/c1-15-9-23(31)29(34)25(36-15)37-21-11-17-3-4-20-19(27(17,14-30)12-22(21)38-29)5-7-26(2)18(6-8-28(20,26)33)16-10-24(32)35-13-16/h10,14-15,17-22,25,33-34H,3-9,11-13H2,1-2H3/t15-,17+,18-,19+,20-,21-,22-,25+,26-,27-,28+,29+/m1/s1

> <INCHI_KEY>
YOCULAYFPPWLRI-OLEQQPCLSA-N

> <FORMULA>
C29H38O9

> <MOLECULAR_WEIGHT>
530.614

> <EXACT_MASS>
530.251582804

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
56.053324297874134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,5S,7R,10R,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-7,18-dimethyl-9-oxo-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}]pentacosane-14-carbaldehyde

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.756145030999999

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.67234103160317

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.168340415106215

> <JCHEM_PKA_STRONGEST_BASIC>
0.2690382455064799

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
132.59089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,5S,7R,10R,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-7,18-dimethyl-9-oxo-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}]pentacosane-14-carbaldehyde

> <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  O   UNK     0       1.929  -2.252   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.174  -0.243   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.124   1.268   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.036   2.281   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.581   1.766   0.000  0.00  0.00           C+0
HETATM   38  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   36                                                  
CONECT   30   29   31   32   38                                             
CONECT   31   30    1                                                       
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35   29                                                       
CONECT   37   35                                                            
CONECT   38   30                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₈O₉

Average Mass

530.6140 Da

Monoisotopic Mass

530.25158 Da

IUPAC Name

(1S,3R,5S,7R,10R,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-7,18-dimethyl-9-oxo-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}]pentacosane-14-carbaldehyde

Traditional Name

(1S,3R,5S,7R,10R,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-7,18-dimethyl-9-oxo-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}]pentacosane-14-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC(=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/C29H38O9/c1-15-9-23(31)29(34)25(36-15)37-21-11-17-3-4-20-19(27(17,14-30)12-22(21)38-29)5-7-26(2)18(6-8-28(20,26)33)16-10-24(32)35-13-16/h10,14-15,17-22,25,33-34H,3-9,11-13H2,1-2H3/t15-,17+,18-,19+,20-,21-,22-,25+,26-,27-,28+,29+/m1/s1

InChI Key

YOCULAYFPPWLRI-OLEQQPCLSA-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 subulata	LOTUS Database	35616633
Calotropis procera	Plant	KNApSAcK
Thymus vulgaris	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
Oxosteroid
14-hydroxysteroid
Hydroxysteroid
Para-dioxane
2-furanone
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Alcohol
Aldehyde
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cardenolide glycoside (CHEBI:9913 )
cardanolide (C08883 )

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	2.26	ALOGPS
logP	2.76	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.17	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.59 m³·mol⁻¹	ChemAxon
Polarizability	56.05 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

C00003640

Chemspider ID

390450

KEGG Compound ID

C08883

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441874

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bader A, Omran Z, Al-Asmari AI, Santoro V, De Tommasi N, D'Ambola M, Dal Piaz F, Conti B, Bedini S, Halwani M: Systematic Phytochemical Screening of Different Organs of Calotropis procera and the Ovicidal Effect of Their Extracts to the Foodstuff Pest Cadra cautella. Molecules. 2021 Feb 9;26(4). pii: molecules26040905. doi: 10.3390/molecules26040905. [PubMed:33572107 ]
He YL, Yang HY, Huang PZ, Feng WJ, Gao K: Cytotoxic cardenolides from Calotropis gigantea. Phytochemistry. 2021 Dec;192:112951. doi: 10.1016/j.phytochem.2021.112951. Epub 2021 Sep 24. [PubMed:34563976 ]
Li JZ, Qing C, Chen CX, Hao XJ, Liu HY: Cytotoxicity of cardenolides and cardenolide glycosides from Asclepias curassavica. Bioorg Med Chem Lett. 2009 Apr 1;19(7):1956-9. doi: 10.1016/j.bmcl.2009.02.045. Epub 2009 Feb 14. [PubMed:19251412 ]
Fang CH, Zhang GQ, Zhu XY, Gong JQ: Distribution of oval cells and c-myc mRNA expression in mouse hepatocarcinogenesis. Hepatobiliary Pancreat Dis Int. 2004 Aug;3(3):433-9. [PubMed:15313684 ]
Fang CH, Zhang W, Zhu XY, Gong JQ, Zhang GQ: The expression of c-kit and proliferating cell nuclear antigen in oval cells of rats with hepatocellular carcinoma. Hepatobiliary Pancreat Dis Int. 2003 Nov;2(4):537-44. [PubMed:14627515 ]

Showing NP-Card for Uscharidin (NP0052160)

MOL for NP0052160 (Uscharidin)

3D MOL for NP0052160 (Uscharidin)

3D SDF for NP0052160 (Uscharidin)

3D-SDF for NP0052160 (Uscharidin)

PDB for NP0052160 (Uscharidin)

3D PDB for NP0052160 (Uscharidin)

SMILES for NP0052160 (Uscharidin)

INCHI for NP0052160 (Uscharidin)

Structure for NP0052160 (Uscharidin)

3D Structure for NP0052160 (Uscharidin)