NP-MRD: Showing NP-Card for Dipsacoside B (NP0137241)

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Record Information

Version

2.0

Created at

2022-05-30 16:46:19 UTC

Updated at

2022-05-30 16:46:19 UTC

NP-MRD ID

NP0137241

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dipsacoside B

Description

3,4,5-Trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 10-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate 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. Dipsacoside B is found in Anemone cernua, Clematis tibetana, Decaisnea fargesii, Hedera helix, Kalopanax septemlobus, Lonicera japonica, Lonicera macranthoides, Medicago polymorpha and Nigella damascena. 3,4,5-Trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 10-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121516542D          

 75 83  0  0  0  0            999 V2000
   11.4395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7605    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8230    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2355    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5230    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7766    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8342    2.3388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2645    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
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 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
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 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
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 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
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 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
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 27 28  2  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
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 23 39  1  0  0  0  0
 28 39  1  0  0  0  0
 39 40  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
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 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
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 51 52  1  0  0  0  0
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 46 60  1  0  0  0  0
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 62 63  1  0  0  0  0
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 44 64  1  0  0  0  0
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 20 66  1  0  0  0  0
 15 66  1  0  0  0  0
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  4 70  1  0  0  0  0
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 72 73  1  0  0  0  0
 72 74  1  0  0  0  0
  2 74  1  0  0  0  0
 74 75  1  0  0  0  0
M  END

     RDKit          3D

161169  0  0  0  0  0  0  0  0999 V2000
  -12.9317    1.4656    2.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5243    1.4578    2.3063 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.2255    0.3407    1.5432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8943    0.2318    1.1819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.6856   -0.3679   -0.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9947   -1.5566   -0.0288 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8300   -1.5578   -1.0423 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7054   -1.2136   -0.7103 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0594    0.5263   -0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682    0.4736   -0.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0752   -0.1337   -1.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3905    0.2507   -1.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -0.0755   -0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6811    1.4894   -1.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8676    2.3655   -1.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3761    3.8253   -1.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6561    2.2889   -2.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8095    2.1748   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7764    0.3937    1.1416 C   0  0  2  0  0  0  0  0  0  0  0  0
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   11.5398   -1.8070    0.3971 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9166   -1.5206   -2.3537 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8019   -0.7739   -2.7352 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5241   -2.8993   -1.8739 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.6204    0.4766    2.4226 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.5548   -0.9167   -2.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0700   -2.2598   -2.0706 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.4514   -2.2539   -2.3791 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.2098   -2.3330    0.0451 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 04121516542D          

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    6.7766    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8342    2.3388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2645    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  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
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  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  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  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
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 23 39  1  0  0  0  0
 28 39  1  0  0  0  0
 39 40  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 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
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 51 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 58  1  0  0  0  0
 49 58  1  0  0  0  0
 58 59  1  0  0  0  0
 46 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  1  0  0  0  0
 44 64  1  0  0  0  0
 64 65  1  0  0  0  0
 20 66  1  0  0  0  0
 15 66  1  0  0  0  0
 66 67  1  0  0  0  0
 66 68  1  0  0  0  0
 68 69  1  0  0  0  0
  4 70  1  0  0  0  0
 70 71  1  0  0  0  0
 70 72  1  0  0  0  0
 72 73  1  0  0  0  0
 72 74  1  0  0  0  0
  2 74  1  0  0  0  0
 74 75  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137241

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2C(O)C(O)COC2OC2CCC3(C)C(CCC4(C)C3CC=C3C5CC(C)(C)CCC5(CCC43C)C(=O)OC3OC(COC4OC(CO)C(O)C(O)C4O)C(O)C(O)C3O)C2(C)CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C53H86O22/c1-23-32(57)36(61)40(65)44(70-23)74-42-33(58)26(56)20-68-46(42)73-31-11-12-49(4)29(50(31,5)22-55)10-13-52(7)30(49)9-8-24-25-18-48(2,3)14-16-53(25,17-15-51(24,52)6)47(67)75-45-41(66)38(63)35(60)28(72-45)21-69-43-39(64)37(62)34(59)27(19-54)71-43/h8,23,25-46,54-66H,9-22H2,1-7H3

> <INCHI_KEY>
GFPLPBCJRRNZHM-UHFFFAOYSA-N

> <FORMULA>
C53H86O22

> <MOLECULAR_WEIGHT>
1075.249

> <EXACT_MASS>
1074.561074409

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
161

> <JCHEM_AVERAGE_POLARIZABILITY>
113.1914318580047

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 10-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
-0.5892678450000011

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.185047614267752

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.747827176191878

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648688400147722

> <JCHEM_POLAR_SURFACE_AREA>
353.90000000000003

> <JCHEM_REFRACTIVITY>
257.56410000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 10-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

> <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      21.354  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.584  -0.564   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      19.044  -0.564   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      18.274   0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      16.734   0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      15.964  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.734  -1.897   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      18.274  -1.897   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.964  -3.231   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.734  -4.565   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.424  -3.231   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.654  -1.897   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.424  -0.564   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.023   3.635   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -0.976   4.771   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -2.516   4.771   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -3.286   6.105   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -4.826   6.105   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -5.596   7.438   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -7.136   7.438   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -7.906   6.105   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -9.446   6.105   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -10.216   4.771   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0     -11.756   4.771   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0     -10.216   7.438   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0     -11.756   7.438   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      -9.446   8.772   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0     -10.216  10.106   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      -7.906   8.772   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -7.136  10.106   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -2.516   7.438   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      -3.286   8.772   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      -0.976   7.438   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -0.206   8.772   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      -0.206   6.105   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0       1.334   6.105   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      12.650   2.920   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      11.397   3.643   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      12.757   4.366   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0      19.044   2.104   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0      18.274   3.437   0.000  0.00  0.00           O+0
HETATM   72  C   UNK     0      20.584   2.104   0.000  0.00  0.00           C+0
HETATM   73  O   UNK     0      21.354   3.437   0.000  0.00  0.00           O+0
HETATM   74  C   UNK     0      21.354   0.770   0.000  0.00  0.00           C+0
HETATM   75  O   UNK     0      22.894   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   74                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   70                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   66                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   25                                             
CONECT   19   18                                                            
CONECT   20   18   21   66                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   39                                             
CONECT   24   23                                                            
CONECT   25   23   18   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   39                                                  
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   29   37   41                                             
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   23   28   40                                             
CONECT   40   39                                                            
CONECT   41   36   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45   64                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   60                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   58                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   54                                                  
CONECT   52   51   53                                                       
CONECT   53   52                                                            
CONECT   54   51   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   49   59                                                  
CONECT   59   58                                                            
CONECT   60   46   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   44   65                                                  
CONECT   65   64                                                            
CONECT   66   20   15   67   68                                             
CONECT   67   66                                                            
CONECT   68   66   69                                                       
CONECT   69   68                                                            
CONECT   70    4   71   72                                                  
CONECT   71   70                                                            
CONECT   72   70   73   74                                                  
CONECT   73   72                                                            
CONECT   74   72    2   75                                                  
CONECT   75   74                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  166    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 10-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid	Generator
3-O-alpha-L-Rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl hederagenin 28-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl ester	MeSH

Chemical Formula

C₅₃H₈₆O₂₂

Average Mass

1075.2490 Da

Monoisotopic Mass

1074.56107 Da

IUPAC Name

3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 10-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Traditional Name

3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 10-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

CAS Registry Number

Not Available

SMILES

CC1OC(OC2C(O)C(O)COC2OC2CCC3(C)C(CCC4(C)C3CC=C3C5CC(C)(C)CCC5(CCC43C)C(=O)OC3OC(COC4OC(CO)C(O)C(O)C4O)C(O)C(O)C3O)C2(C)CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C53H86O22/c1-23-32(57)36(61)40(65)44(70-23)74-42-33(58)26(56)20-68-46(42)73-31-11-12-49(4)29(50(31,5)22-55)10-13-52(7)30(49)9-8-24-25-18-48(2,3)14-16-53(25,17-15-51(24,52)6)47(67)75-45-41(66)38(63)35(60)28(72-45)21-69-43-39(64)37(62)34(59)27(19-54)71-43/h8,23,25-46,54-66H,9-22H2,1-7H3

InChI Key

GFPLPBCJRRNZHM-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
Anemone cernua	LOTUS Database	35616633
Clematis tibetana	LOTUS Database	35616633
Decaisnea fargesii	LOTUS Database	35616633
Hedera helix	LOTUS Database	35616633
Kalopanax septemlobus	LOTUS Database	35616633
Lonicera japonica	LOTUS Database	35616633
Lonicera macranthoides	LOTUS Database	35616633
Medicago polymorpha	LOTUS Database	35616633
Nigella damascena	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
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.61	ALOGPS
logP	-0.59	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	353.9 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	257.56 m³·mol⁻¹	ChemAxon
Polarizability	113.19 Å³	ChemAxon
Number of Rings	9	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

14284443

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dipsacoside B (NP0137241)

MOL for NP0137241 (Dipsacoside B)

3D MOL for NP0137241 (Dipsacoside B)

3D SDF for NP0137241 (Dipsacoside B)

3D-SDF for NP0137241 (Dipsacoside B)

PDB for NP0137241 (Dipsacoside B)

3D PDB for NP0137241 (Dipsacoside B)

SMILES for NP0137241 (Dipsacoside B)

INCHI for NP0137241 (Dipsacoside B)

Structure for NP0137241 (Dipsacoside B)

3D Structure for NP0137241 (Dipsacoside B)