NP-MRD: Showing NP-Card for 6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0228830)

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Record Information

Version

2.0

Created at

2022-09-06 08:38:32 UTC

Updated at

2022-09-06 08:38:32 UTC

NP-MRD ID

NP0228830

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Description

AC1NAVQQ 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. 6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid is found in Gymnema sylvestre. AC1NAVQQ is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121517042D          

 57 62  0  0  0  0            999 V2000
   -2.1730   -6.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -4.5375    0.0000 O   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
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  0  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
    0.7145   -7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -8.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -7.3954    0.0000 C   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
    1.6257   -6.7869    0.0000 O   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  0  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  0  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  0  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  0  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  0  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  0  0  0  0  0  0  0  0  0  0
    8.5520   -2.3941    0.0000 C   0  0  0  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  0  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
    8.5520   -3.8230    0.0000 C   0  0  0  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
    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
    6.0770   -5.2520    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
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955   -6.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  0  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  0  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  0  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
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -2.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -3.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  0  0  0  0
 34 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 30 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 44 48  1  0  0  0  0
 26 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 20 51  1  0  0  0  0
 25 51  1  0  0  0  0
 51 52  1  0  0  0  0
 22 53  1  0  0  0  0
 11 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
  8 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  1  0  0  0  0
M  END

     RDKit          3D

123128  0  0  0  0  0  0  0  0999 V2000
   -9.4851   -2.9159    1.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7972   -3.4492    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6780   -2.9468   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0544   -3.5303   -1.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0229   -1.8102    0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5330   -1.2831    1.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8535   -1.2597   -0.1191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2257   -0.1315    0.5461 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8586   -0.5390    0.8974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2826   -1.2301   -0.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9967    0.5870    1.3871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5964    1.0563    2.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9034    1.5491    2.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5059    1.9939    3.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9105    2.5345    3.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8884    1.9502    4.8658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412    0.0247    1.6814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5577   -1.2509    1.0602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176    0.8250    1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4674    1.8955    0.4054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6901    3.1881    1.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6834    1.5390   -0.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5605    1.0025   -1.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3023    0.6862   -2.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1751   -0.6090   -2.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7217   -0.8121    2.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2095    0.0342    2.9082 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0811   -1.0503    2.2023 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9312   -2.9976    1.4536 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8767   -3.1754    2.8436 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9142   -3.8114    0.7188 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3456   -3.9030   -0.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5397   -3.1378    0.6880 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9474   -3.1447    1.9278 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6611    0.8588   -1.6232 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6991    1.5115   -0.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2276    1.0224   -3.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5327    0.4442   -3.0829 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3291    1.3763   -1.3490 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -7.7811   -3.9332   -2.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2664   -4.2748   -1.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9110    0.0572    1.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9343   -1.2656    1.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6464   -2.1486   -0.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917    1.8853    3.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5174    0.2516    3.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9614    3.1967    2.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1263    3.1338    4.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5644    1.6776    3.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633   -0.3030    2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7540   -1.7228    1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4037    0.0913    1.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3783   -2.3087   -1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4648   -1.7968   -0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2625   -1.3112    0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 04121517042D          

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M  END
> <DATABASE_ID>
NP0228830

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1C(O)C2(COC(C)=O)C(O)CC3(C)C(=CCC4C5(C)CCC(OC6OC(C(O)C(O)C6O)C(O)=O)C(C)(CO)C5CCC34C)C2CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C43H66O14/c1-10-21(2)36(53)57-34-33(50)43(20-54-22(3)45)24(17-38(34,4)5)23-11-12-26-39(6)15-14-28(55-37-31(49)29(47)30(48)32(56-37)35(51)52)40(7,19-44)25(39)13-16-41(26,8)42(23,9)18-27(43)46/h10-11,24-34,37,44,46-50H,12-20H2,1-9H3,(H,51,52)

> <INCHI_KEY>
VEFSVJGWJQPWFS-UHFFFAOYSA-N

> <FORMULA>
C43H66O14

> <MOLECULAR_WEIGHT>
806.987

> <EXACT_MASS>
806.445256805

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
88.91247980510764

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
2.664481777333336

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.204319728332118

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5182148378040545

> <JCHEM_PKA_STRONGEST_BASIC>
-2.785723760002405

> <JCHEM_POLAR_SURFACE_AREA>
229.73999999999998

> <JCHEM_REFRACTIVITY>
204.9572000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      -4.056 -12.471   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.826 -11.137   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.056  -9.804   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.826  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.516  -9.804   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.746 -11.137   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334 -13.805   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.104 -15.138   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.206 -13.805   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.035 -12.669   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.424  -7.136   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.654  -5.803   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.424  -4.469   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.964  -4.469   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      16.734  -3.135   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      16.734  -5.803   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      18.274  -5.803   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      15.964  -7.136   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      16.734  -8.470   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      13.654  -3.135   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      14.424  -1.802   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      12.114  -3.135   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      11.076 -11.320   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  O   UNK     0      13.058 -11.847   0.000  0.00  0.00           O+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
HETATM   55  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.510  -5.597   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -0.742  -6.320   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   55                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17   53                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   11   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   51                                             
CONECT   21   20                                                            
CONECT   22   20   23   53                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   51                                                  
CONECT   26   25   27   28   48                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   44                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   41                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32   40                                                  
CONECT   40   39                                                            
CONECT   41   34   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   30   45   46   48                                             
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46                                                            
CONECT   48   44   26   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   20   25   52                                             
CONECT   52   51                                                            
CONECT   53   22   11   54                                                  
CONECT   54   53   55                                                       
CONECT   55   54    8   56   57                                             
CONECT   56   55                                                            
CONECT   57   55                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

View in JSmol

Synonyms

Value	Source
6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₄₃H₆₆O₁₄

Average Mass

806.9870 Da

Monoisotopic Mass

806.44526 Da

IUPAC Name

6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1C(O)C2(COC(C)=O)C(O)CC3(C)C(=CCC4C5(C)CCC(OC6OC(C(O)C(O)C6O)C(O)=O)C(C)(CO)C5CCC34C)C2CC1(C)C

InChI Identifier

InChI=1S/C43H66O14/c1-10-21(2)36(53)57-34-33(50)43(20-54-22(3)45)24(17-38(34,4)5)23-11-12-26-39(6)15-14-28(55-37-31(49)29(47)30(48)32(56-37)35(51)52)40(7,19-44)25(39)13-16-41(26,8)42(23,9)18-27(43)46/h10-11,24-34,37,44,46-50H,12-20H2,1-9H3,(H,51,52)

InChI Key

VEFSVJGWJQPWFS-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
Gymnema sylvestre	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
Steroid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Pyran
Oxane
Fatty acyl
Monosaccharide
Hydroxy acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Carboxylic acid
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
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	3.43	ALOGPS
logP	2.66	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	229.74 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	204.96 m³·mol⁻¹	ChemAxon
Polarizability	88.91 Å³	ChemAxon
Number of Rings	6	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

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

4483444

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0228830)

MOL for NP0228830 (6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for NP0228830 (6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for NP0228830 (6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for NP0228830 (6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for NP0228830 (6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for NP0228830 (6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for NP0228830 (6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for NP0228830 (6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for NP0228830 (6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for NP0228830 (6-({8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)