NP-MRD: Showing NP-Card for (2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid (NP0298957)

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Record Information

Version

2.0

Created at

2022-09-10 10:31:34 UTC

Updated at

2022-09-10 10:31:34 UTC

NP-MRD ID

NP0298957

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid

Description

Momordin Ic 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. (2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid is found in Anredera baselloides. (2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid was first documented in 2021 (PMID: 34326883). Based on a literature review a small amount of articles have been published on Momordin Ic (PMID: 35640567) (PMID: 34049792) (PMID: 33795649).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102212312D          

 54 60  0  0  1  0            999 V2000
   -0.4733   -3.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -3.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -3.8230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -2.3941    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145   -1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -0.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -2.3941    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9645   -1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -3.1086    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7895   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020   -3.8230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7895   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0270   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4395   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2645   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0270   -3.8230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4395   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -3.8230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9645   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337   -6.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6882   -6.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 26 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
 34 33  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 34 41  1  0  0  0  0
 41 42  1  6  0  0  0
 32 43  1  0  0  0  0
 24 43  1  0  0  0  0
 43 44  1  1  0  0  0
 22 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 45 48  1  0  0  0  0
 18 48  1  0  0  0  0
 48 49  1  6  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 17 51  1  0  0  0  0
 12 51  1  0  0  0  0
 51 52  1  6  0  0  0
 53 14  1  1  0  0  0
  6 53  1  0  0  0  0
 53 54  1  0  0  0  0
  2 54  1  0  0  0  0
M  END

     RDKit          3D

118124  0  0  0  0  0  0  0  0999 V2000
   -7.4249    1.6769   -2.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6235    2.2381   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.6876    1.4749   -0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0875    0.8557    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9037   -0.0348    0.1074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4746   -1.2353   -0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7121   -1.3934   -0.5802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6927   -2.2030   -1.1368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3773   -0.5378    1.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0672   -1.2275    1.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0214   -0.2748    0.8603 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6956    0.6923    1.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4902    0.5218   -0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5429    1.1021   -1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0952    1.0434   -0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6955    0.0769    0.2517 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2896   -0.4209    0.1980 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1784   -0.9465   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971    0.7845    0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2301    0.6495    1.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1066   -0.5773    1.8998 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0708   -0.3871    0.9187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3556   -0.2806    1.4256 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9145    0.9846    1.1757 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8210    1.2058    2.2220 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3271    2.5909    2.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9190    3.3184    1.1833 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2506    3.0768    3.0544 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9421    0.2235    2.0273 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.2841    1.6062   -2.6629 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3092    2.6880   -3.5429 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3204   -0.8603   -2.4856 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1806   -1.8346   -2.9870 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3026   -1.2932    0.8844 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3149   -2.4439    1.6702 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2405   -1.7779    1.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8517   -2.8261    0.8109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1264   -2.4411    3.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1425   -1.3924    1.3374 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0368   -2.5982    1.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619   -2.0847    1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7544   -0.9873    0.3620 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0953   -1.5988   -0.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7896    1.5802    1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7541   -3.1716   -0.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1218   -1.3257    1.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4743    0.2592    2.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7933   -1.5898    2.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1867   -2.1166    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9958    0.2691    2.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6350    0.8752    2.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4180    1.7067    1.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8704    1.6996   -1.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774    2.0902   -0.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6291    0.8871   -1.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403    0.6647    1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2793   -1.0996   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2260   -1.9282   -1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0769   -0.1600   -1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9354    1.5274    1.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472    0.7361    2.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6557   -0.5864    2.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907   -0.3911    2.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2957    1.0449    3.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7794    2.4266    3.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8726    0.7968    1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0163   -0.5610    3.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4188   -1.5405    0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0298957

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@@H]([C@@H](O)[C@H](O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)C(O)=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C41H64O13/c1-36(2)14-16-41(35(49)50)17-15-39(6)20(21(41)18-36)8-9-24-38(5)12-11-25(37(3,4)23(38)10-13-40(24,39)7)52-34-29(46)30(28(45)31(54-34)32(47)48)53-33-27(44)26(43)22(42)19-51-33/h8,21-31,33-34,42-46H,9-19H2,1-7H3,(H,47,48)(H,49,50)/t21-,22+,23-,24+,25-,26-,27+,28-,29+,30-,31-,33-,34+,38-,39+,40+,41-/m0/s1

> <INCHI_KEY>
HWYBGIDROCYPOE-WEAQAMGWSA-N

> <FORMULA>
C41H64O13

> <MOLECULAR_WEIGHT>
764.95

> <EXACT_MASS>
764.434692121

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
118

> <JCHEM_AVERAGE_POLARIZABILITY>
84.43398422708742

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_LOGP>
4.003771621999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.767162605012912

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4549741748076737

> <JCHEM_PKA_STRONGEST_BASIC>
-3.52658066213482

> <JCHEM_POLAR_SURFACE_AREA>
212.67

> <JCHEM_REFRACTIVITY>
192.35600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.883  -6.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.831  -5.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.424  -7.136   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.654  -5.803   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.424  -4.469   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.654  -3.135   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.424  -1.802   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      12.114  -3.135   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.964  -4.469   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      16.734  -3.135   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      16.734  -5.803   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      18.274  -5.803   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      19.044  -7.136   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      18.274  -8.470   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      19.044  -9.804   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      20.584  -9.804   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      21.354 -11.137   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      21.354  -8.470   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      22.894  -8.470   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      20.584  -7.136   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      21.354  -5.803   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      15.964  -7.136   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      16.734  -8.470   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.885 -11.335   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   54                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10   53                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   51                                             
CONECT   13   12                                                            
CONECT   14   12   15   53                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   51                                                  
CONECT   18   17   19   20   48                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   45                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   43                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   43                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   41                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   34   42                                                  
CONECT   42   41                                                            
CONECT   43   32   24   44                                                  
CONECT   44   43                                                            
CONECT   45   22   46   47   48                                             
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   45   18   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   17   12   52                                             
CONECT   52   51                                                            
CONECT   53   14    6   54                                                  
CONECT   54   53    2                                                       
MASTER        0    0    0    0    0    0    0    0   54    0  120    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₁H₆₄O₁₃

Average Mass

764.9500 Da

Monoisotopic Mass

764.43469 Da

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@@H]([C@@H](O)[C@H](O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)C(O)=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=O

InChI Identifier

InChI=1S/C41H64O13/c1-36(2)14-16-41(35(49)50)17-15-39(6)20(21(41)18-36)8-9-24-38(5)12-11-25(37(3,4)23(38)10-13-40(24,39)7)52-34-29(46)30(28(45)31(54-34)32(47)48)53-33-27(44)26(43)22(42)19-51-33/h8,21-31,33-34,42-46H,9-19H2,1-7H3,(H,47,48)(H,49,50)/t21-,22+,23-,24+,25-,26-,27+,28-,29+,30-,31-,33-,34+,38-,39+,40+,41-/m0/s1

InChI Key

HWYBGIDROCYPOE-WEAQAMGWSA-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
Anredera baselloides	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
Triterpenoid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Pyran
Oxane
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	4	ChemAxon
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	192.36 m³·mol⁻¹	ChemAxon
Polarizability	84.43 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00057711

Chemspider ID

153797

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

176596

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Senggunprai L, Kukongviriyapan V, Prawan A, Kongpetch S: Epidermal growth factor receptor as a potential target of momordin Ic to promote apoptosis of cholangiocarcinoma cells. J Pharm Pharmacol. 2022 Jul 15;74(7):996-1005. doi: 10.1093/jpp/rgac033. [PubMed:35640567 ]
Luo M, Zeng B, Wang H, Yang Z, Peng Y, Zhang Y, Wang C: Kochia scoparia Saponin Momordin Ic Modulates HaCaT Cell Proliferation and Apoptosis via the Wnt/beta-Catenin Pathway. Evid Based Complement Alternat Med. 2021 Jul 16;2021:5522164. doi: 10.1155/2021/5522164. eCollection 2021. [PubMed:34326883 ]
Xianjun F, Xirui X, Jie T, Huiwen M, Shaojun Z, Qiaoyun L, Yunxin L, Xuqun S: Momordin Ic induces G0/1 phase arrest and apoptosis in colon cancer cells by suppressing SENP1/c-MYC signaling pathway. J Pharmacol Sci. 2021 Aug;146(4):249-258. doi: 10.1016/j.jphs.2021.04.007. Epub 2021 May 11. [PubMed:34049792 ]
Li J, Wu R, Yung MMH, Sun J, Li Z, Yang H, Zhang Y, Liu SS, Cheung ANY, Ngan HYS, Braisted JC, Zheng W, Wei H, Gao Y, Nemes P, Pei H, Chan DW, Li Y, Zhu W: SENP1-mediated deSUMOylation of JAK2 regulates its kinase activity and platinum drug resistance. Cell Death Dis. 2021 Apr 1;12(4):341. doi: 10.1038/s41419-021-03635-6. [PubMed:33795649 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid (NP0298957)

MOL for NP0298957 ((2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid)

3D MOL for NP0298957 ((2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid)

3D SDF for NP0298957 ((2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for NP0298957 ((2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid)

PDB for NP0298957 ((2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid)

3D PDB for NP0298957 ((2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid)

SMILES for NP0298957 ((2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid)

INCHI for NP0298957 ((2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid)

Structure for NP0298957 ((2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid)

3D Structure for NP0298957 ((2s,3s,4s,5r,6r)-6-{[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxane-2-carboxylic acid)