NP-MRD: Showing NP-Card for Acremoside A (NP0332598)

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Record Information

Version

1.0

Created at

2024-03-06 20:01:06 UTC

Updated at

2024-05-02 18:16:30 UTC

NP-MRD ID

NP0332598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acremoside A

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03062420012D          

 39 39  0  0  1  0            999 V2000
    7.9697    4.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822    3.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2072    3.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697    3.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822    2.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2072    2.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197    1.8118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9052    1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342    2.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322    1.0974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6197    0.3829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697    0.3829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0947    0.3829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5072   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7447   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9822   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7947   -1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822   -1.7605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5572   -1.7605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5572   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7947   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3822   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322   -3.1895    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  7  9  1  1  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 15 23  2  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END


  Mrv2104 03062420012D          

 39 39  0  0  1  0            999 V2000
    7.9697    4.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822    3.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2072    3.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697    3.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822    2.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2072    2.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197    1.8118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9052    1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342    2.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322    1.0974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6197    0.3829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697    0.3829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0947    0.3829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5072   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7447   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9822   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7947   -1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822   -1.7605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5572   -1.7605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5572   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7947   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3822   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322   -3.1895    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  7  9  1  1  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 15 23  2  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332598

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC[C@](C)(O)[C@H](O)C[C@@H](OC(=O)CC1=CC=CC=C1)C(\C)=C\CO[C@H]([C@H](O)CO)[C@H](O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O10/c1-19(2)9-8-13-29(4,37)25(34)16-24(39-26(35)15-21-10-6-5-7-11-21)20(3)12-14-38-28(23(33)18-31)27(36)22(32)17-30/h5-7,9-12,22-25,27-28,30-34,36-37H,8,13-18H2,1-4H3/b20-12+/t22-,23-,24-,25-,27-,28-,29+/m1/s1

> <INCHI_KEY>
KAGJKNNSLQUVHD-VWRBAWPUSA-N

> <FORMULA>
C29H46O10

> <MOLECULAR_WEIGHT>
554.677

> <EXACT_MASS>
554.309097681

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
60.50666643027401

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4R,6R,7S)-6,7-dihydroxy-3,7,11-trimethyl-1-{[(2R,3R,4R,5R)-1,2,4,5,6-pentahydroxyhexan-3-yl]oxy}dodeca-2,10-dien-4-yl 2-phenylacetate

> <JCHEM_LOGP>
0.5031573709999992

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.30229057583274

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.697590745025034

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9742178449927836

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
147.49410000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4R,6R,7S)-6,7-dihydroxy-3,7,11-trimethyl-1-{[(2R,3R,4R,5R)-1,2,4,5,6-pentahydroxyhexan-3-yl]oxy}dodeca-2,10-dien-4-yl 2-phenylacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAR-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-24         0                                  
HETATM    1  C   UNK     0      14.877   8.717   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.647   7.383   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.187   7.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.877   6.049   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.647   4.716   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.187   4.716   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.957   3.382   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.623   2.612   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      19.290   4.152   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      18.727   2.048   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      17.957   0.715   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      20.267   2.048   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.037   0.715   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      22.577   0.715   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      23.347  -0.619   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.887  -0.619   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.657  -1.953   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.197  -1.953   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.967  -3.286   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.197  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.657  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.887  -3.286   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.577  -1.953   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.267  -0.619   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.037  -1.953   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.727  -0.619   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.957  -1.953   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.417  -1.953   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.647  -3.286   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.107  -3.286   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.337  -1.953   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      14.107  -5.954   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.797  -4.620   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      11.027  -5.954   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      16.417  -4.620   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      15.647  -5.954   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      17.957  -4.620   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      18.727  -5.954   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   15                                                            
CONECT   24   13   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   29   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₆O₁₀

Average Mass

554.6770 Da

Monoisotopic Mass

554.30910 Da

IUPAC Name

(2E,4R,6R,7S)-6,7-dihydroxy-3,7,11-trimethyl-1-{[(2R,3R,4R,5R)-1,2,4,5,6-pentahydroxyhexan-3-yl]oxy}dodeca-2,10-dien-4-yl 2-phenylacetate

Traditional Name

(2E,4R,6R,7S)-6,7-dihydroxy-3,7,11-trimethyl-1-{[(2R,3R,4R,5R)-1,2,4,5,6-pentahydroxyhexan-3-yl]oxy}dodeca-2,10-dien-4-yl 2-phenylacetate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@](C)(O)[C@H](O)C[C@@H](OC(=O)CC1=CC=CC=C1)C(\C)=C\CO[C@H]([C@H](O)CO)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C29H46O10/c1-19(2)9-8-13-29(4,37)25(34)16-24(39-26(35)15-21-10-6-5-7-11-21)20(3)12-14-38-28(23(33)18-31)27(36)22(32)17-30/h5-7,9-12,22-25,27-28,30-34,36-37H,8,13-18H2,1-4H3/b20-12+/t22-,23-,24-,25-,27-,28-,29+/m1/s1

InChI Key

KAGJKNNSLQUVHD-VWRBAWPUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	ganml@imb.pumc.edu.cn	Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College	Maoluo Gan	2024-05-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	ganml@imb.pumc.edu.cn	Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College	Maoluo Gan	2024-05-02	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
sp. IMB18-086		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	0.5	ChemAxon
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	147.49 m³·mol⁻¹	ChemAxon
Polarizability	60.51 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for Acremoside A (NP0332598)

MOL for NP0332598 (Acremoside A)

3D MOL for NP0332598 (Acremoside A)

3D SDF for NP0332598 (Acremoside A)

3D-SDF for NP0332598 (Acremoside A)

PDB for NP0332598 (Acremoside A)

3D PDB for NP0332598 (Acremoside A)

SMILES for NP0332598 (Acremoside A)

INCHI for NP0332598 (Acremoside A)

Structure for NP0332598 (Acremoside A)

3D Structure for NP0332598 (Acremoside A)