NP-MRD: Showing NP-Card for Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside (NP0331635)

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Record Information

Version

2.0

Created at

2023-05-18 04:04:37 UTC

Updated at

2024-09-03 04:16:20 UTC

NP-MRD ID

NP0331635

Natural Product DOI

https://doi.org/10.57994/0623

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside

Description

Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside was first documented in 2023 (PMID: 37178131). Based on a literature review very few articles have been published on Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305182306042D          

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M  END


  Mrv1652305182306042D          

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 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
 63 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  2  0  0  0  0
 61 66  1  0  0  0  0
 58 67  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@H](O[C@@H]2[C@H](C)O[C@H](C[C@@H]2OC)O[C@@H]2[C@@H](C)O[C@H](C[C@@H]2OC)O[C@H]2CC[C@]3(C)C4C[C@@H](OC(=O)\C=C\C5=CC=CC=C5)[C@]5(C)[C@@](O)(CC[C@]5(O)[C@]4(O)CC=C3C2)C(C)=O)O[C@H](C)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C51H74O16/c1-28-44(54)35(58-7)24-42(61-28)66-46-30(3)63-43(26-37(46)60-9)67-45-29(2)62-41(25-36(45)59-8)64-34-18-19-47(5)33(23-34)17-20-50(56)38(47)27-39(65-40(53)16-15-32-13-11-10-12-14-32)48(6)49(55,31(4)52)21-22-51(48,50)57/h10-17,28-30,34-39,41-46,54-57H,18-27H2,1-9H3/b16-15+/t28-,29-,30+,34+,35+,36+,37+,38?,39-,41+,42+,43+,44-,45-,46-,47+,48-,49-,50+,51-/m1/s1

> <INCHI_KEY>
QYHZBUGINHXFOL-FTIKASFPSA-N

> <FORMULA>
C51H74O16

> <MOLECULAR_WEIGHT>
943.137

> <EXACT_MASS>
942.497686303

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
141

> <JCHEM_AVERAGE_POLARIZABILITY>
102.60275473538486

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5S,10S,11R,14S,15S,16R)-14-acetyl-10,11,14-trihydroxy-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6S)-5-{[(2S,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
5.011791303666669

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.941186494479727

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.331715862469366

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5080226034341653

> <JCHEM_POLAR_SURFACE_AREA>
207.35999999999996

> <JCHEM_REFRACTIVITY>
241.39539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5S,10S,11R,14S,15S,16R)-14-acetyl-10,11,14-trihydroxy-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6S)-5-{[(2S,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAY-23         0                                  
HETATM    1  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.307  -5.242   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.081  -4.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.112  -6.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.501  -6.170   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.725  -1.551   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      18.871  -3.977   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.380  -4.883   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      20.333  -7.780   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      19.810  -9.228   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.803 -10.406   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.294  -9.499   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.771 -10.948   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.255 -11.219   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.764 -12.125   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      18.240 -13.574   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      19.233 -14.751   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      20.749 -14.480   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      21.742 -15.657   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      23.258 -15.386   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      21.219 -17.106   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      22.211 -18.283   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      19.703 -17.377   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      19.179 -18.825   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      17.663 -19.096   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      18.710 -16.199   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      20.280 -11.854   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      21.272 -13.031   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      22.788 -12.760   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      17.825  -6.874   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      17.301  -8.322   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      15.785  -8.593   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      16.832  -5.696   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       8.729  -8.500   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       8.206  -9.949   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       9.198 -11.126   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       8.675 -12.574   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       9.668 -13.752   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       9.145 -15.200   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       7.629 -15.471   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       6.636 -14.294   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       7.159 -12.845   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      10.245  -8.229   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6   56                                             
CONECT    3    2    4   11   12                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7   10                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6                                                            
CONECT   11    3                                                            
CONECT   12    3   13   14   54                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   52                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   50                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   49                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   46                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   43                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   43                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   42                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   39   33                                                       
CONECT   43   31   27   44                                                  
CONECT   44   43   45                                                       
CONECT   45   44                                                            
CONECT   46   24   47   49                                                  
CONECT   47   46   48                                                       
CONECT   48   47                                                            
CONECT   49   46   20                                                       
CONECT   50   18   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   16   53   54                                             
CONECT   53   52                                                            
CONECT   54   52   12   55                                                  
CONECT   55   54   56                                                       
CONECT   56   55    2   57                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59   67                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62   66                                                  
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   61                                                       
CONECT   67   58                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  148    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₁H₇₄O₁₆

Average Mass

943.1370 Da

Monoisotopic Mass

942.49769 Da

IUPAC Name

(2R,5S,10S,11R,14S,15S,16R)-14-acetyl-10,11,14-trihydroxy-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6S)-5-{[(2S,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-3-phenylprop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@H](O[C@@H]2[C@H](C)O[C@H](C[C@@H]2OC)O[C@@H]2[C@@H](C)O[C@H](C[C@@H]2OC)O[C@H]2CC[C@]3(C)C4C[C@@H](OC(=O)\C=C\C5=CC=CC=C5)[C@]5(C)[C@@](O)(CC[C@]5(O)[C@]4(O)CC=C3C2)C(C)=O)O[C@H](C)[C@H]1O

InChI Identifier

InChI=1S/C51H74O16/c1-28-44(54)35(58-7)24-42(61-28)66-46-30(3)63-43(26-37(46)60-9)67-45-29(2)62-41(25-36(45)59-8)64-34-18-19-47(5)33(23-34)17-20-50(56)38(47)27-39(65-40(53)16-15-32-13-11-10-12-14-32)48(6)49(55,31(4)52)21-22-51(48,50)57/h10-17,28-30,34-39,41-46,54-57H,18-27H2,1-9H3/b16-15+/t28-,29-,30+,34+,35+,36+,37+,38?,39-,41+,42+,43+,44-,45-,46-,47+,48-,49-,50+,51-/m1/s1

InChI Key

QYHZBUGINHXFOL-FTIKASFPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C5D5N, experimental)	1458407846@qq.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C5D5N, experimental)	1458407846@qq.com	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.035880294, C5D5deposition_typeN, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
auriculatum		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Triterpenoid
Steroidal glycoside
Steroid ester
20-oxosteroid
Androstane-skeleton
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
14-hydroxysteroid
Delta-5-steroid
Cinnamic acid ester
Fatty alcohol ester
Cinnamic acid or derivatives
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Acyloin
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	5.01	ChemAxon
pKa (Strongest Acidic)	12.33	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	207.36 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	241.4 m³·mol⁻¹	ChemAxon
Polarizability	102.6 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside (NP0331635)

MOL for NP0331635 (Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside)

3D MOL for NP0331635 (Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside)

3D SDF for NP0331635 (Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside)

3D-SDF for NP0331635 (Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside)

PDB for NP0331635 (Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside)

3D PDB for NP0331635 (Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside)

SMILES for NP0331635 (Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside)

INCHI for NP0331635 (Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside)

Structure for NP0331635 (Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside)

3D Structure for NP0331635 (Kidjoranin 3-O-β-D-cymaropyranosyl-(1 →4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside)