NP-MRD: Showing NP-Card for 4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one (NP0146534)

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Record Information

Version

2.0

Created at

2022-09-02 01:56:57 UTC

Updated at

2022-09-02 01:56:57 UTC

NP-MRD ID

NP0146534

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one

Description

40950-57-0 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. 4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one is found in Erysimum marshallii. Based on a literature review very few articles have been published on 40950-57-0.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203562D          

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M  END

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M  END


  Mrv1652309022203562D          

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    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850   -3.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582   -3.7596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1539   -3.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385   -4.5355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4067   -5.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7507   -4.6807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0310   -5.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 30 29  1  6  0  0  0
  9 30  1  0  0  0  0
 30 31  1  0  0  0  0
  6 31  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0146534

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H](CC[C@]43O)C3=CC(=O)OC3)C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O8/c1-15-23(31)24(32)25(33)26(36-15)37-18-6-9-27(2)17(13-18)4-5-21-20(27)7-10-28(3)19(8-11-29(21,28)34)16-12-22(30)35-14-16/h12,15,17-21,23-26,31-34H,4-11,13-14H2,1-3H3/t15-,17-,18+,19-,20+,21-,23-,24+,25-,26+,27+,28-,29+/m1/s1

> <INCHI_KEY>
WQMLFJWIKARBFW-QYLLKCSRSA-N

> <FORMULA>
C29H44O8

> <MOLECULAR_WEIGHT>
520.663

> <EXACT_MASS>
520.303618377

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.92179838684257

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1S,2S,5S,7R,10R,11S,14R,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
2.3434289080000013

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.22438311998636

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182632278127244

> <JCHEM_PKA_STRONGEST_BASIC>
0.2422282932905614

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
134.5102

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,2S,5S,7R,10R,11S,14R,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.777  -7.831   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.261  -7.560   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.737  -6.112   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.221  -5.841   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.728   0.744   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.779   2.283   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      11.944  -0.202   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.505  -5.709   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.229  -7.018   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.287  -6.747   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.752  -8.466   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.759  -9.644   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -3.268  -8.737   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.791 -10.186   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   30                                             
CONECT   10    9                                                            
CONECT   11    9   12   27                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   25                                             
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   17                                                       
CONECT   23   16   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   14   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   11   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    9   31                                                  
CONECT   31   30    6                                                       
CONECT   32    4   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    2   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₄O₈

Average Mass

520.6630 Da

Monoisotopic Mass

520.30362 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H](CC[C@]43O)C3=CC(=O)OC3)C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C29H44O8/c1-15-23(31)24(32)25(33)26(36-15)37-18-6-9-27(2)17(13-18)4-5-21-20(27)7-10-28(3)19(8-11-29(21,28)34)16-12-22(30)35-14-16/h12,15,17-21,23-26,31-34H,4-11,13-14H2,1-3H3/t15-,17-,18+,19-,20+,21-,23-,24+,25-,26+,27+,28-,29+/m1/s1

InChI Key

WQMLFJWIKARBFW-QYLLKCSRSA-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
Erysimum marshallii	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
Steroidal glycoside
14-hydroxysteroid
Hydroxysteroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
2-furanone
Oxane
Monosaccharide
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
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
logP	1.75	ALOGPS
logS	-4	ALOGPS

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

20147879

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20841608

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one (NP0146534)

MOL for NP0146534 (4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D MOL for NP0146534 (4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D SDF for NP0146534 (4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D-SDF for NP0146534 (4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

PDB for NP0146534 (4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D PDB for NP0146534 (4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

SMILES for NP0146534 (4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

INCHI for NP0146534 (4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

Structure for NP0146534 (4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D Structure for NP0146534 (4-[(1r,3as,3br,5ar,7s,9as,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)