NP-MRD: Showing NP-Card for (21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside (NP0331785)

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Record Information

Version

2.0

Created at

2023-08-30 12:01:01 UTC

Updated at

2024-09-03 04:16:55 UTC

NP-MRD ID

NP0331785

Natural Product DOI

https://doi.org/10.57994/0858

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside

Description

(21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside was first documented in 2023 (PMID: 37611978).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 08302312012D          

 64 71  0  0  1  0            999 V2000
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  1  2  1  0  0  0  0
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  7  8  1  1  0  0  0
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M  END


  Mrv2104 08302312012D          

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   11.2019   -1.2094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0331785

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1O[C@@H](C[C@]1(O)[C@H]1CC[C@]2(C)C1CCC1[C@@]2(C)CCC2C(C)(C)[C@H](CC[C@]12C=O)O[C@@H]1OC[C@H](O)[C@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C47H76O17/c1-22(2)17-24-18-47(56,42(57-8)61-24)26-11-14-44(6)25(26)9-10-30-45(44,7)15-12-29-43(4,5)31(13-16-46(29,30)21-48)62-41-38(64-40-36(55)34(53)32(51)23(3)60-40)37(28(50)20-59-41)63-39-35(54)33(52)27(49)19-58-39/h17,21,23-42,49-56H,9-16,18-20H2,1-8H3/t23-,24+,25?,26-,27+,28-,29?,30?,31-,32-,33-,34+,35+,36+,37-,38+,39-,40-,41-,42-,44+,45+,46+,47-/m0/s1

> <INCHI_KEY>
ZFVRCXKMVFZMJZ-XUACVWTGSA-N

> <FORMULA>
C47H76O17

> <MOLECULAR_WEIGHT>
913.108

> <EXACT_MASS>
912.508250987

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
140

> <JCHEM_AVERAGE_POLARIZABILITY>
99.11331046215284

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3aR,3bR,7S,9aS)-1-[(2S,3S,5S)-3-hydroxy-2-methoxy-5-(2-methylprop-1-en-1-yl)oxolan-3-yl]-7-{[(2S,3R,4S,5S)-5-hydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-3a,3b,6,6-tetramethyl-hexadecahydro-1H-cyclopenta[a]phenanthrene-9a-carbaldehyde

> <JCHEM_LOGP>
1.9589429569999994

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.325657298202172

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.860154643243474

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265806621235742

> <JCHEM_POLAR_SURFACE_AREA>
252.74999999999994

> <JCHEM_REFRACTIVITY>
225.49300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3aR,3bR,7S,9aS)-1-[(2S,3S,5S)-3-hydroxy-2-methoxy-5-(2-methylprop-1-en-1-yl)oxolan-3-yl]-7-{[(2S,3R,4S,5S)-5-hydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-3a,3b,6,6-tetramethyl-dodecahydro-1H-cyclopenta[a]phenanthrene-9a-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-AUG-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-AUG-23         0                                  
HETATM    1  C   UNK     0       0.023  -9.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.102  -8.808   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.689  -7.324   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.593  -9.193   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.672  -8.094   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.195  -8.320   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.881  -6.942   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.400  -6.686   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.380  -7.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.417  -6.575   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.232  -4.425   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.725  -1.551   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      16.832  -5.696   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      17.825  -6.874   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      20.333  -7.780   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      21.380  -4.883   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      21.903  -3.435   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      20.910  -2.257   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      21.433  -0.809   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      22.949  -0.538   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      23.473   0.910   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      23.942  -1.715   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      25.458  -1.444   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      23.419  -3.164   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      24.412  -4.341   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      18.871  -3.977   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      19.394  -2.529   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      18.402  -1.351   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      16.886  -1.622   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      15.893  -0.445   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      14.377  -0.716   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      16.416   1.003   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      15.423   2.181   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      17.932   1.274   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      18.455   2.723   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      18.925   0.097   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      20.441   0.368   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      12.284  -6.510   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10    7   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   64                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   64                                             
CONECT   17   16                                                            
CONECT   18   16   19   20   61                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   58                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27   56                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   44                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   44                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   42                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   35   43                                                  
CONECT   43   42                                                            
CONECT   44   33   28   45                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   54                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   46   55                                                  
CONECT   55   54                                                            
CONECT   56   26   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   22   59   61                                             
CONECT   59   58   60                                                       
CONECT   60   59                                                            
CONECT   61   58   18   62                                                  
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   16   13                                                  
MASTER        0    0    0    0    0    0    0    0   64    0  142    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₇₆O₁₇

Average Mass

913.1080 Da

Monoisotopic Mass

912.50825 Da

IUPAC Name

(1S,3aR,3bR,7S,9aS)-1-[(2S,3S,5S)-3-hydroxy-2-methoxy-5-(2-methylprop-1-en-1-yl)oxolan-3-yl]-7-{[(2S,3R,4S,5S)-5-hydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-3a,3b,6,6-tetramethyl-hexadecahydro-1H-cyclopenta[a]phenanthrene-9a-carbaldehyde

Traditional Name

(1S,3aR,3bR,7S,9aS)-1-[(2S,3S,5S)-3-hydroxy-2-methoxy-5-(2-methylprop-1-en-1-yl)oxolan-3-yl]-7-{[(2S,3R,4S,5S)-5-hydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-3a,3b,6,6-tetramethyl-dodecahydro-1H-cyclopenta[a]phenanthrene-9a-carbaldehyde

CAS Registry Number

Not Available

SMILES

CO[C@H]1O[C@@H](C[C@]1(O)[C@H]1CC[C@]2(C)C1CCC1[C@@]2(C)CCC2C(C)(C)[C@H](CC[C@]12C=O)O[C@@H]1OC[C@H](O)[C@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)C=C(C)C

InChI Identifier

InChI=1S/C47H76O17/c1-22(2)17-24-18-47(56,42(57-8)61-24)26-11-14-44(6)25(26)9-10-30-45(44,7)15-12-29-43(4,5)31(13-16-46(29,30)21-48)62-41-38(64-40-36(55)34(53)32(51)23(3)60-40)37(28(50)20-59-41)63-39-35(54)33(52)27(49)19-58-39/h17,21,23-42,49-56H,9-16,18-20H2,1-8H3/t23-,24+,25?,26-,27+,28-,29?,30?,31-,32-,33-,34+,35+,36+,37-,38+,39-,40-,41-,42-,44+,45+,46+,47-/m0/s1

InChI Key

ZFVRCXKMVFZMJZ-XUACVWTGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)	yinanzhang@njucm.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C5D5N, experimental)	yinanzhang@njucm.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)	yinanzhang@njucm.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)	yinanzhang@njucm.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C5D5N, experimental)	yinanzhang@njucm.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)	yinanzhang@njucm.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C5D5N, experimental)	yinanzhang@njucm.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
pentaphyllum		Not Available

Chemical Taxonomy

Classification

Not classified

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	1.96	ChemAxon
pKa (Strongest Acidic)	11.86	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	252.75 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	225.49 m³·mol⁻¹	ChemAxon
Polarizability	99.11 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

Not Available

References

General References

Not Available

Showing NP-Card for (21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside (NP0331785)

MOL for NP0331785 ((21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside)

3D MOL for NP0331785 ((21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside)

3D SDF for NP0331785 ((21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside)

3D-SDF for NP0331785 ((21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside)

PDB for NP0331785 ((21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside)

3D PDB for NP0331785 ((21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside)

SMILES for NP0331785 ((21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside)

INCHI for NP0331785 ((21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside)

Structure for NP0331785 ((21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside)

3D Structure for NP0331785 ((21S)-(23S)-Dimethoxyl-3β,(20S)-dihydroxy-19-oxo- 21,23-epoxydammar-24-ene-3-O-[α-L-rhamnopyranosyl (1→2)][β-D-xylopyranosyl(1→3)]-α-L-arabinopyranoside)