NP-MRD: Showing NP-Card for 4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate (NP0314559)

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Record Information

Version

2.0

Created at

2022-09-11 12:42:57 UTC

Updated at

2022-09-11 12:42:58 UTC

NP-MRD ID

NP0314559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate

Description

4,8A-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate is found in Amaranthus caudatus. 4,8A-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171519322D          

 57 63  0  0  0  0            999 V2000
    4.4270   -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
    5.2520   -0.3020    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
    6.4895   -1.0164    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
    7.3145    0.4125    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
    5.9337    1.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907    1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    6.8522    1.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4842    0.8788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955    2.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7707    2.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9140    3.3162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6892    3.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8325    4.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6077    4.6930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3212    3.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0965    3.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1780    2.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8099    1.7253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4027    1.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2595    1.1610    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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 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
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 33 42  1  0  0  0  0
 42 43  1  0  0  0  0
  8 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 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
 49 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 47 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  END

     RDKit          3D

119125  0  0  0  0  0  0  0  0999 V2000
    1.3600   -3.4632    3.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4879   -2.8326    2.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -3.5518    2.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6397   -2.5615    1.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740   -1.3269    1.1419 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2123   -0.5204    0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3804    0.6334    1.1374 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1444   -0.9407   -0.2627 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2422   -0.1070   -0.6826 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1483    0.1241   -2.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2373    0.7628   -2.5498 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2359    2.2629   -2.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2039    2.7199   -1.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5661    0.1586   -2.1571 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2171    0.8992   -1.1702 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2552   -1.1995   -1.5153 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3609   -1.8879   -2.3374 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4817   -0.8432   -0.2418 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2295   -1.9704    0.5053 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157   -1.8534    0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265   -0.8324   -0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8054    0.2477    0.0982 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3957    1.5739   -0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.2317    1.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3190    1.8253    1.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1038    1.7051    0.4592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5585    2.0507    0.3363 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8381    2.6289   -1.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9695    3.1471    1.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4011    0.7977    2.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6684    0.1688   -0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2509   -0.5355   -0.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8751   -0.7881   -0.6316 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9070   -0.0228   -1.1445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7843   -0.7290   -1.9434 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.7322    0.3013   -2.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4108    0.9749   -1.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5694   -1.6731   -1.0419 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.8773   -1.2081   -0.9249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9816   -1.7080    0.3507 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.4557   -2.8635    1.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4811   -1.8034    0.3305 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0745   -3.1010   -0.0291 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2091    0.8643   -0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1745    0.5937   -3.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1510    2.6684   -2.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3483    2.6616   -2.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0597    3.0155   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2261   -0.0609   -3.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8439    0.2678   -0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1573   -1.7700   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3871   -2.8575   -2.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1594   -0.1951    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1240   -2.7907   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4953   -2.5859    0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -2.4100   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4962    1.5655    2.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7229    3.0044    2.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894    4.0648    0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8357    3.6655    2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
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 50108  1  0
M  END


  Mrv1533004171519322D          

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M  END
> <DATABASE_ID>
NP0314559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(O)C(O)C(C)(C1CCC1(C)C2CC=C2C3CC(=C)CCC3(CCC12C)C(=O)OC1OC(CO)C(O)C(O)C1O)C(=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C41H62O16/c1-18-8-11-41(36(53)57-34-31(50)29(48)27(46)23(17-43)55-34)13-12-38(3)19(20(41)14-18)6-7-24-37(2)15-21(44)32(51)40(5,25(37)9-10-39(24,38)4)35(52)56-33-30(49)28(47)26(45)22(16-42)54-33/h6,20-34,42-51H,1,7-17H2,2-5H3

> <INCHI_KEY>
HFXIXQIJWYYSGD-UHFFFAOYSA-N

> <FORMULA>
C41H62O16

> <MOLECULAR_WEIGHT>
810.931

> <EXACT_MASS>
810.403785916

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
119

> <JCHEM_AVERAGE_POLARIZABILITY>
86.01497384553575

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylate

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
-0.4722066923333341

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.393261296212952

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.884161788647047

> <JCHEM_PKA_STRONGEST_BASIC>
-3.169406055656494

> <JCHEM_POLAR_SURFACE_AREA>
273.35999999999996

> <JCHEM_REFRACTIVITY>
196.86800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.114  -1.897   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.076   3.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.023   3.635   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.976   4.771   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.516   4.771   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.286   6.105   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.826   6.105   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -5.596   7.438   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.516   7.438   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.286   8.772   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.976   7.438   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -0.206   8.772   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.206   6.105   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.334   6.105   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      12.791   2.630   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      13.971   1.640   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      13.058   4.147   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      14.505   4.674   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      14.773   6.190   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      16.220   6.717   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      16.487   8.234   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      17.934   8.760   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      17.400   5.727   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      18.847   6.254   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      17.132   4.211   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      18.312   3.221   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      15.685   3.684   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      15.418   2.167   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10   15                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   44                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   28                                             
CONECT   14   13                                                            
CONECT   15   13    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19   26   30                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   13   18   29                                             
CONECT   29   28                                                            
CONECT   30   25   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   42                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   33   43                                                  
CONECT   43   42                                                            
CONECT   44    8   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48   56                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   52                                                  
CONECT   50   49   51                                                       
CONECT   51   50                                                            
CONECT   52   49   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   47   57                                                  
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  126    0
END

View in JSmol

Synonyms

Value	Source
4,8a-Bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylic acid	Generator

Chemical Formula

C₄₁H₆₂O₁₆

Average Mass

810.9310 Da

Monoisotopic Mass

810.40379 Da

IUPAC Name

4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylate

Traditional Name

4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate

CAS Registry Number

Not Available

SMILES

CC12CC(O)C(O)C(C)(C1CCC1(C)C2CC=C2C3CC(=C)CCC3(CCC12C)C(=O)OC1OC(CO)C(O)C(O)C1O)C(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C41H62O16/c1-18-8-11-41(36(53)57-34-31(50)29(48)27(46)23(17-43)55-34)13-12-38(3)19(20(41)14-18)6-7-24-37(2)15-21(44)32(51)40(5,25(37)9-10-39(24,38)4)35(52)56-33-30(49)28(47)26(45)22(16-42)54-33/h6,20-34,42-51H,1,7-17H2,2-5H3

InChI Key

HFXIXQIJWYYSGD-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
Amaranthus caudatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
12-hydroxysteroid
Hydroxysteroid
Steroid
Hexose monosaccharide
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Oxane
Monosaccharide
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.78	ALOGPS
logP	-0.47	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	273.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	196.87 m³·mol⁻¹	ChemAxon
Polarizability	86.01 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate (NP0314559)

MOL for NP0314559 (4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

3D MOL for NP0314559 (4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

3D SDF for NP0314559 (4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

3D-SDF for NP0314559 (4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

PDB for NP0314559 (4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

3D PDB for NP0314559 (4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

SMILES for NP0314559 (4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

INCHI for NP0314559 (4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

Structure for NP0314559 (4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

3D Structure for NP0314559 (4,8a-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)