NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate (NP0263420)

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Record Information

Version

2.0

Created at

2022-09-08 06:35:53 UTC

Updated at

2022-09-08 06:35:53 UTC

NP-MRD ID

NP0263420

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate

Description

Cyclotricuspidoside C, also known as cyclopassifloside XI, belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. Cyclotricuspidoside C is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cyclotricuspidoside C has been detected, but not quantified in, fruits. 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate is found in Passiflora edulis and Trichosanthes tricuspidata. This could make cyclotricuspidoside C a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307152D          

 60 66  0  0  0  0            999 V2000
    9.2327    3.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9182    5.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4539    3.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0631    2.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0937    0.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377   -1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2983   -0.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5890   -0.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8184    3.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0635    4.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2675    2.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582    2.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303    0.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7850    0.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7761    1.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9571   -4.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8489    1.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0498    3.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6730    4.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0135    3.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2616    1.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9884    1.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2296   -3.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2880    0.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8694   -0.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4406   -0.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1396    1.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7684    2.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3822    0.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0403   -3.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5945    1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3127   -2.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4129    1.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7745   -2.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0191    2.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9639   -2.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6982   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9870    2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9973    1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1601   -0.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5685    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8683    4.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8591    0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9576    0.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4953   -5.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0865    1.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313   -0.4658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1294    2.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5638   -0.0035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5784   -4.3534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9884    0.4868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1233   -2.7959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6252    2.0963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0470   -1.5453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5089   -0.9201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6867    5.0703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8375    3.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8068    2.1657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915   -3.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4258   -1.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 19  1  1  0  0  0  0
 19  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20  9  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 16  1  0  0  0  0
 24  7  1  0  0  0  0
 25  8  1  0  0  0  0
 26 13  1  0  0  0  0
 27 13  1  0  0  0  0
 28 20  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  1  0  0  0  0
 30 23  1  0  0  0  0
 31 29  1  0  0  0  0
 32 30  1  0  0  0  0
 33 31  1  0  0  0  0
 34 32  1  0  0  0  0
 35 33  1  0  0  0  0
 36 34  1  0  0  0  0
 38  4  1  0  0  0  0
 38 11  1  0  0  0  0
 38 28  1  0  0  0  0
 39  5  1  0  0  0  0
 39 14  1  0  0  0  0
 39 24  1  0  0  0  0
 39 38  1  0  0  0  0
 40  6  1  0  0  0  0
 40 25  1  0  0  0  0
 40 26  1  0  0  0  0
 40 37  1  0  0  0  0
 41 12  1  0  0  0  0
 41 17  1  0  0  0  0
 41 24  1  0  0  0  0
 42 10  1  0  0  0  0
 42 18  1  0  0  0  0
 42 19  1  0  0  0  0
 43 17  1  0  0  0  0
 43 25  1  0  0  0  0
 43 27  1  0  0  0  0
 43 41  1  0  0  0  0
 44 15  1  0  0  0  0
 45 16  1  0  0  0  0
 46 21  1  0  0  0  0
 47 26  1  0  0  0  0
 48 27  1  0  0  0  0
 49 29  1  0  0  0  0
 50 30  1  0  0  0  0
 51 31  1  0  0  0  0
 52 32  1  0  0  0  0
 53 33  1  0  0  0  0
 54 34  1  0  0  0  0
 55 37  2  0  0  0  0
 56 42  1  0  0  0  0
 57 18  1  0  0  0  0
 57 35  1  0  0  0  0
 58 22  1  0  0  0  0
 58 35  1  0  0  0  0
 59 23  1  0  0  0  0
 59 36  1  0  0  0  0
 60 36  1  0  0  0  0
 60 37  1  0  0  0  0
M  END

     RDKit          3D

132138  0  0  0  0  0  0  0  0999 V2000
   -7.1008   -2.8115   -2.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2744   -1.5560   -2.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0527   -0.4535   -2.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6966   -1.2130   -0.8190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9786   -0.0385   -0.9799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6389   -2.2963   -0.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9207   -2.2204    0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8916   -3.3237    0.8215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6588   -4.6247    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7126   -3.2294   -0.0538 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7560   -4.4029    0.1073 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6755   -4.9351    1.3546 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -3.9238   -0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3620   -2.4995   -0.8309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0422   -2.6019   -2.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5591   -1.6270   -0.5780 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3742   -1.5915   -1.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7948   -1.1679   -1.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6639   -0.1056   -0.4093 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8745    0.7668   -0.4071 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6607    0.7199   -1.6982 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7242    1.9077   -2.3730 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5681    0.5607    0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1833   -0.1920   -0.3263 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1557    0.0983   -0.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8178   -2.8256   -3.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061307152D          

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M  END
> <DATABASE_ID>
NP0263420

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(O)(CCC(C)C1C(O)CC2(C)C3CCC4C5(CC35CCC12C)C(O)CC(O)C4(C)C(=O)OC1OC(CO)C(O)C(O)C1O)COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C43H72O17/c1-19(2)42(56,18-57-35-33(53)31(51)29(49)22(15-44)58-35)10-9-20(3)28-21(46)14-39(5)24-7-8-25-40(6,37(55)60-36-34(54)32(52)30(50)23(16-45)59-36)26(47)13-27(48)43(25)17-41(24,43)12-11-38(28,39)4/h19-36,44-54,56H,7-18H2,1-6H3

> <INCHI_KEY>
JRBZRACFBGYSHE-UHFFFAOYSA-N

> <FORMULA>
C43H72O17

> <MOLECULAR_WEIGHT>
861.0216

> <EXACT_MASS>
860.476950878

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
93.99722723239458

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate

> <ALOGPS_LOGP>
-0.40

> <JCHEM_LOGP>
-1.581437244666663

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.4127720327781

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.897354947669003

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0745761337603374

> <JCHEM_POLAR_SURFACE_AREA>
296.75000000000006

> <JCHEM_REFRACTIVITY>
208.58370000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      17.234   7.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.647   9.772   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.181   6.946   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.451   5.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.508   0.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.057  -2.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.023  -0.017   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.699  -0.803   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.728   6.153   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.185   7.623   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.966   4.603   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.642   3.817   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.670   1.457   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.799   1.852   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.115   2.083   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.520  -8.699   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.318   3.030   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.026   6.460   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.190   8.301   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.225   5.814   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.688   3.109   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.645   2.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.029  -7.245   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.004   1.523   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.356  -0.050   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.689  -0.083   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.994   2.243   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.768   4.344   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.513   1.496   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.542  -6.959   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.043   1.953   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.050  -5.506   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.704   3.456   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.046  -4.338   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.836   4.500   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.533  -4.624   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.037  -2.004   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.309   3.850   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.328   2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.032  -0.836   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.661   2.276   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.687   7.962   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.337   1.490   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      20.454   0.581   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       6.525  -9.866   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      13.228   3.128   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       1.365  -0.869   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       3.975   3.783   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      17.852  -0.007   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       8.546  -8.126   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      14.912   0.909   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       9.563  -5.219   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      14.234   3.913   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       7.554  -2.885   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       6.550  -1.718   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      14.349   9.465   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      16.497   6.002   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      18.306   4.043   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       5.024  -6.078   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       4.528  -3.457   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   38                                                            
CONECT    5   39                                                            
CONECT    6   40                                                            
CONECT    7    8   24                                                       
CONECT    8    7   25                                                       
CONECT    9   10   20                                                       
CONECT   10    9   42                                                       
CONECT   11   12   38                                                       
CONECT   12   11   41                                                       
CONECT   13   26   27                                                       
CONECT   14   21   39                                                       
CONECT   15   22   44                                                       
CONECT   16   23   45                                                       
CONECT   17   41   43                                                       
CONECT   18   42   57                                                       
CONECT   19    1    2   42                                                  
CONECT   20    3    9   28                                                  
CONECT   21   14   28   46                                                  
CONECT   22   15   29   58                                                  
CONECT   23   16   30   59                                                  
CONECT   24    7   39   41                                                  
CONECT   25    8   40   43                                                  
CONECT   26   13   40   47                                                  
CONECT   27   13   43   48                                                  
CONECT   28   20   21   38                                                  
CONECT   29   22   31   49                                                  
CONECT   30   23   32   50                                                  
CONECT   31   29   33   51                                                  
CONECT   32   30   34   52                                                  
CONECT   33   31   35   53                                                  
CONECT   34   32   36   54                                                  
CONECT   35   33   57   58                                                  
CONECT   36   34   59   60                                                  
CONECT   37   40   55   60                                                  
CONECT   38    4   11   28   39                                             
CONECT   39    5   14   24   38                                             
CONECT   40    6   25   26   37                                             
CONECT   41   12   17   24   43                                             
CONECT   42   10   18   19   56                                             
CONECT   43   17   25   27   41                                             
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   21                                                            
CONECT   47   26                                                            
CONECT   48   27                                                            
CONECT   49   29                                                            
CONECT   50   30                                                            
CONECT   51   31                                                            
CONECT   52   32                                                            
CONECT   53   33                                                            
CONECT   54   34                                                            
CONECT   55   37                                                            
CONECT   56   42                                                            
CONECT   57   18   35                                                       
CONECT   58   22   35                                                       
CONECT   59   23   36                                                       
CONECT   60   36   37                                                       
MASTER        0    0    0    0    0    0    0    0   60    0  132    0
END

View in JSmol

Synonyms

Value	Source
Cyclopassifloside XI	HMDB
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid	Generator

Chemical Formula

C₄₃H₇₂O₁₇

Average Mass

861.0216 Da

Monoisotopic Mass

860.47695 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)C(O)(CCC(C)C1C(O)CC2(C)C3CCC4C5(CC35CCC12C)C(O)CC(O)C4(C)C(=O)OC1OC(CO)C(O)C(O)C1O)COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C43H72O17/c1-19(2)42(56,18-57-35-33(53)31(51)29(49)22(15-44)58-35)10-9-20(3)28-21(46)14-39(5)24-7-8-25-40(6,37(55)60-36-34(54)32(52)30(50)23(16-45)59-36)26(47)13-27(48)43(25)17-41(24,43)12-11-38(28,39)4/h19-36,44-54,56H,7-18H2,1-6H3

InChI Key

JRBZRACFBGYSHE-UHFFFAOYSA-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
Passiflora edulis	LOTUS Database	35616633
Trichosanthes tricuspidata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
Pentahydroxy bile acid, alcohol, or derivatives
24-hydroxysteroid
Cholane-skeleton
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
1-hydroxysteroid
16-hydroxysteroid
11-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Steroid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Beta-hydroxy acid
Oxane
Hydroxy acid
Monosaccharide
Fatty acyl
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Acetal
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
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	-0.4	ALOGPS
logP	-1.6	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	296.75 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	208.58 m³·mol⁻¹	ChemAxon
Polarizability	94 Å³	ChemAxon
Number of Rings	7	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

HMDB0033636

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011735

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

73801618

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate (NP0263420)

MOL for NP0263420 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate)

3D MOL for NP0263420 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate)

3D SDF for NP0263420 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate)

3D-SDF for NP0263420 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate)

PDB for NP0263420 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate)

3D PDB for NP0263420 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate)

SMILES for NP0263420 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate)

INCHI for NP0263420 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate)

Structure for NP0263420 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate)

3D Structure for NP0263420 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4,6,14-trihydroxy-15-[5-hydroxy-6-methyl-5-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)heptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylate)