NP-MRD: Showing NP-Card for 25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside (NP0071925)

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Record Information

Version

2.0

Created at

2022-04-28 17:18:46 UTC

Updated at

2022-04-28 17:18:46 UTC

NP-MRD ID

NP0071925

Secondary Accession Numbers

None

Natural Product Identification

Common Name

25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside

Description

2-[(1S,2S,3S,4R,7R,9S,12R,14S,17R,18R,19R,21S,22S)-2-hydroxy-3,8,8,17,19-pentamethyl-9-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-23,24-dioxaheptacyclo[19.2.1.0¹,¹⁸.0³,¹⁷.0⁴,¹⁴.0⁷,¹².0¹²,¹⁴]Tetracosan-22-yl]propan-2-yl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside is found in Souliea vaginata. Based on a literature review very few articles have been published on 2-[(1S,2S,3S,4R,7R,9S,12R,14S,17R,18R,19R,21S,22S)-2-hydroxy-3,8,8,17,19-pentamethyl-9-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-23,24-dioxaheptacyclo[19.2.1.0¹,¹⁸.0³,¹⁷.0⁴,¹⁴.0⁷,¹².0¹²,¹⁴]Tetracosan-22-yl]propan-2-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282219182D          

 47 54  0  0  1  0            999 V2000
    7.8316    1.0010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5288    1.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6846    1.9426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1824    1.2332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5069    0.4067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1363    0.7334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8032   -0.0681    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1180    0.4047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3499    1.2004    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7784    1.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9770    1.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7461    0.8046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3166    0.2087    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0857   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2844   -0.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7139   -0.1835    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9448    0.6086    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3743    1.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5729    1.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3420    0.2164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9125   -0.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3368   -0.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0805   -1.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407    0.0204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098   -0.7717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8803   -1.3676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6494   -2.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -2.3557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7225   -1.7598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4916   -0.9677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0620   -0.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5238   -1.9558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -3.1478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757    1.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574    1.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9686   -0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7989   -0.8931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1483   -0.2239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411    0.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6635   -0.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2652   -0.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3860   -0.6515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4022   -1.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1247   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6960   -1.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0619    0.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3646    2.7030    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  1  0  0  0
  1  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  1  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 29 32  1  6  0  0  0
 28 33  1  1  0  0  0
 17 34  1  1  0  0  0
 12 34  1  1  0  0  0
  9 35  1  1  0  0  0
  8 36  1  6  0  0  0
  7 37  1  1  0  0  0
  5 38  1  0  0  0  0
 38 39  1  0  0  0  0
  1 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 40 46  1  0  0  0  0
  3 47  1  6  0  0  0
M  END


  Mrv1652304282219182D          

 47 54  0  0  1  0            999 V2000
    7.8316    1.0010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5288    1.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6846    1.9426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1824    1.2332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5069    0.4067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1363    0.7334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8032   -0.0681    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1180    0.4047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3499    1.2004    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7784    1.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9770    1.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7461    0.8046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3166    0.2087    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0857   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2844   -0.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7139   -0.1835    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9448    0.6086    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3743    1.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5729    1.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3420    0.2164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9125   -0.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3368   -0.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0805   -1.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407    0.0204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098   -0.7717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8803   -1.3676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6494   -2.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -2.3557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7225   -1.7598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4916   -0.9677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0620   -0.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5238   -1.9558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -3.1478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757    1.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574    1.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9686   -0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7989   -0.8931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1483   -0.2239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411    0.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6635   -0.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2652   -0.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3860   -0.6515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4022   -1.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1247   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6960   -1.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0619    0.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3646    2.7030    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  1  0  0  0
  1  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  1  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 29 32  1  6  0  0  0
 28 33  1  1  0  0  0
 17 34  1  1  0  0  0
 12 34  1  1  0  0  0
  9 35  1  1  0  0  0
  8 36  1  6  0  0  0
  7 37  1  1  0  0  0
  5 38  1  0  0  0  0
 38 39  1  0  0  0  0
  1 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 40 46  1  0  0  0  0
  3 47  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0071925

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H]2O[C@@]3(O[C@@H]2C(C)(C)OC(C)=O)[C@@H](O)[C@@]2(C)[C@@H]4CC[C@@H]5[C@]6(C[C@@]46CC[C@]2(C)[C@@H]13)CC[C@H](O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O)C5(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C37H58O10/c1-18-15-21-28(32(5,6)45-19(2)38)47-37(46-21)27(18)33(7)13-14-36-17-35(36)12-11-24(44-29-26(41)25(40)20(39)16-43-29)31(3,4)22(35)9-10-23(36)34(33,8)30(37)42/h18,20-30,39-42H,9-17H2,1-8H3/t18-,20-,21+,22+,23+,24+,25+,26-,27-,28+,29+,30+,33-,34-,35-,36+,37+/m1/s1

> <INCHI_KEY>
NNFJPOSVDKIWPO-ZASJFUDRSA-N

> <FORMULA>
C37H58O10

> <MOLECULAR_WEIGHT>
662.861

> <EXACT_MASS>
662.402998068

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
27.132018309521953

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1S,2S,3S,4R,7R,9S,12R,14S,17R,18R,19R,21S,22S)-2-hydroxy-3,8,8,17,19-pentamethyl-9-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-23,24-dioxaheptacyclo[19.2.1.0^{1,18}.0^{3,17}.0^{4,14}.0^{7,12}.0^{12,14}]tetracosan-22-yl]propan-2-yl acetate

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
3.4245560943333317

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.842644272196601

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.150778763317401

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265806236668267

> <JCHEM_POLAR_SURFACE_AREA>
144.14000000000001

> <JCHEM_REFRACTIVITY>
168.64690000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S,2S,3S,4R,7R,9S,12R,14S,17R,18R,19R,21S,22S)-2-hydroxy-3,8,8,17,19-pentamethyl-9-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-23,24-dioxaheptacyclo[19.2.1.0^{1,18}.0^{3,17}.0^{4,14}.0^{7,12}.0^{12,14}]tetracosan-22-yl]propan-2-yl acetate

> <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      14.619   1.869   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.054   3.375   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.478   3.626   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.540   2.302   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.146   0.759   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.321   1.369   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.833  -0.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.554   0.755   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.987   2.241   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.920   3.346   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.424   2.980   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.993   1.502   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.058   0.389   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.627  -1.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.131  -1.455   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.066  -0.342   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.497   1.136   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.432   2.248   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.936   1.882   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.505   0.404   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.570  -0.708   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.495  -1.812   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.884  -2.216   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.009   0.038   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.578  -1.440   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.643  -2.553   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.212  -4.031   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.284  -4.397   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.349  -3.285   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.918  -1.806   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.982  -0.694   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.844  -3.651   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.715  -5.876   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.928   2.614   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.561   3.670   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.275  -0.759   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.825  -1.667   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      13.344  -0.418   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      14.823   0.271   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.172  -0.472   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.428  -1.821   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      17.520  -1.216   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      17.551  -2.756   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      18.899  -3.499   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      16.233  -3.552   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      16.915   0.876   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      11.881   5.046   0.000  0.00  0.00           C+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   47                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7   38                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   37                                                  
CONECT    8    7    9   13   36                                             
CONECT    9    8    4   10   35                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17   34                                             
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   12   18   34                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   16   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   25   31                                                  
CONECT   31   30                                                            
CONECT   32   29                                                            
CONECT   33   28                                                            
CONECT   34   17   12                                                       
CONECT   35    9                                                            
CONECT   36    8                                                            
CONECT   37    7                                                            
CONECT   38    5   39                                                       
CONECT   39   38    1   40                                                  
CONECT   40   39   41   42   46                                             
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   40                                                            
CONECT   47    3                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  108    0
END

View in JSmol

Synonyms

Value	Source
2-[(1S,2S,3S,4R,7R,9S,12R,14S,17R,18R,19R,21S,22S)-2-Hydroxy-3,8,8,17,19-pentamethyl-9-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-23,24-dioxaheptacyclo[19.2.1.0,.0,.0,.0,.0,]tetracosan-22-yl]propan-2-yl acetic acid	Generator

Chemical Formula

C₃₇H₅₈O₁₀

Average Mass

662.8610 Da

Monoisotopic Mass

662.40300 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H]2O[C@@]3(O[C@@H]2C(C)(C)OC(C)=O)[C@@H](O)[C@@]2(C)[C@@H]4CC[C@@H]5[C@]6(C[C@@]46CC[C@]2(C)[C@@H]13)CC[C@H](O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O)C5(C)C

InChI Identifier

InChI=1S/C37H58O10/c1-18-15-21-28(32(5,6)45-19(2)38)47-37(46-21)27(18)33(7)13-14-36-17-35(36)12-11-24(44-29-26(41)25(40)20(39)16-43-29)31(3,4)22(35)9-10-23(36)34(33,8)30(37)42/h18,20-30,39-42H,9-17H2,1-8H3/t18-,20-,21+,22+,23+,24+,25+,26-,27-,28+,29+,30+,33-,34-,35-,36+,37+/m1/s1

InChI Key

NNFJPOSVDKIWPO-ZASJFUDRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actaea vaginata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Cycloartanol-skeleton
Triterpenoid
Cycloartane-skeleton
9b,19-cyclo-lanostane-skeleton
Hydroxysteroid
15-hydroxysteroid
O-glycosyl compound
Glycosyl compound
Ketal
Oxepane
Oxane
Monosaccharide
Cyclic alcohol
Meta-dioxolane
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.04	ALOGPS
logP	3.42	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	12.15	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	144.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	168.65 m³·mol⁻¹	ChemAxon
Polarizability	27.13 Å³	ChemAxon
Number of Rings	8	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

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

162903021

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside (NP0071925)

MOL for NP0071925 (25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside)

3D MOL for NP0071925 (25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside)

3D SDF for NP0071925 (25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside)

3D-SDF for NP0071925 (25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside)

PDB for NP0071925 (25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside)

3D PDB for NP0071925 (25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside)

SMILES for NP0071925 (25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside)

INCHI for NP0071925 (25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside)

Structure for NP0071925 (25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside)

3D Structure for NP0071925 (25-O-Acetylcimigenol-3-O-beta-D-xylopyranoside)