NP-MRD: Showing NP-Card for (2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid (NP0308902)

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Record Information

Version

2.0

Created at

2022-09-11 03:02:59 UTC

Updated at

2022-09-11 03:02:59 UTC

NP-MRD ID

NP0308902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid

Description

24-Epiquadrangularic acid G belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. (2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid was first documented in 2000 (PMID: 10650080). Based on a literature review very few articles have been published on 24-epiquadrangularic acid G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205032D          

 38 42  0  0  1  0            999 V2000
    2.2494   -1.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9639   -2.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9639   -3.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6783   -1.9424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6783   -1.1174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3928   -2.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073   -1.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217   -2.3549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5362   -1.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5362   -1.1174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2507   -2.3549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217   -3.1799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4892   -3.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2342   -4.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4092   -4.4494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7448   -5.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8572   -5.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1121   -5.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5601   -6.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7531   -6.2887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2011   -6.9018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9008   -7.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8921   -7.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000   -8.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0751   -7.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7660   -8.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -6.7303    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8421   -7.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -5.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6912   -5.3326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4363   -4.5479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4982   -5.5041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2433   -4.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0502   -4.8910    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7953   -4.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3473   -3.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1543   -3.6648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9828   -2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12  8  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  1  1  0  0  0
 34 33  1  1  0  0  0
 17 34  1  0  0  0  0
 32 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
 12 37  1  0  0  0  0
 15 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END

     RDKit          3D

 86 90  0  0  0  0  0  0  0  0999 V2000
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   -4.7876    1.1000   -0.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4043   -0.2288   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9136   -2.5849   -0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0914   -3.4998   -0.4215 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5880   -0.7372    0.4679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2636   -1.6311    1.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7672   -1.9299    1.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921   -0.6486    0.8963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3350    0.4282    1.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0890   -0.7474    0.3321 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.2825   -0.1214   -1.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0554    2.3798   -0.7526 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7766    3.0553    0.4582 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3821    0.3852   -0.5406 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2928    1.3542   -0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060    0.9354   -0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3398   -0.4626   -0.2186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0575   -1.4051   -1.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0194    2.6026    0.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1745    1.2283   -0.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5321   -0.9682   -0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6302   -0.7581   -1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8409   -1.4550    0.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5341    0.6786    1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2967    2.6693    1.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8963    1.6515   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1627    1.7022   -1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2912   -0.7398   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7471   -0.0409   -2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6046   -1.1136    0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9074    0.2655    0.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7320   -1.8777    2.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -1.7992    0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1578   -1.1737    1.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144    1.0781    1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0393   -1.2001   -1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3923   -0.0882   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7502    0.4399   -2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4183    2.3612   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6974    1.1012   -1.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3444   -0.9641   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6689   -2.3982   -1.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709   -1.5535   -1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 23  1  0
 23 24  2  0
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 21 22  1  0
 21 27  1  0
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 29 30  1  0
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 36 37  1  0
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 19 20  1  0
 12  8  1  0
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  7  6  1  0
  6  4  1  0
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  4  2  1  0
  2  3  1  0
  2  1  2  3
  8  9  1  0
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  1 39  1  0
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 11 51  1  0
M  END


  Mrv1652309112205032D          

 38 42  0  0  1  0            999 V2000
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    7.2507   -2.3549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1121   -5.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5601   -6.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7531   -6.2887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2011   -6.9018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9008   -7.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8921   -7.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000   -8.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0751   -7.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7660   -8.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -6.7303    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8421   -7.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -5.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6912   -5.3326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4363   -4.5479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4982   -5.5041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2433   -4.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0502   -4.8910    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7953   -4.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3473   -3.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1543   -3.6648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9828   -2.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12  8  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  1  1  0  0  0
 34 33  1  1  0  0  0
 17 34  1  0  0  0  0
 32 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
 12 37  1  0  0  0  0
 15 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0308902

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(C)[C@@H](O)C[C@H](O)[C@]23C[C@]22CC[C@]4(C)[C@H](CC[C@@]4(C)[C@@H]2CC[C@@H]13)[C@@H](CC[C@@H](O)C(C)=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H48O7/c1-17(2)20(32)8-7-18(25(35)36)19-11-12-28(4)21-9-10-22-29(5,26(37)38-6)23(33)15-24(34)31(22)16-30(21,31)14-13-27(19,28)3/h18-24,32-34H,1,7-16H2,2-6H3,(H,35,36)/t18-,19-,20-,21+,22+,23+,24+,27-,28+,29+,30+,31-/m1/s1

> <INCHI_KEY>
KALMVCDXDQYBPA-WQXOJWCKSA-N

> <FORMULA>
C31H48O7

> <MOLECULAR_WEIGHT>
532.718

> <EXACT_MASS>
532.340003886

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
60.546970906501976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5R)-2-[(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid

> <JCHEM_LOGP>
3.344491981666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.164577731463485

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.568865711482195

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4574444510441338

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
142.12569999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5R)-2-[(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       4.199  -3.626   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.533  -4.396   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.533  -5.936   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.866  -3.626   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.866  -2.086   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.200  -4.396   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.534  -3.626   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.867  -4.396   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.201  -3.626   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.201  -2.086   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      13.535  -4.396   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.867  -5.936   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.113  -6.841   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.637  -8.306   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.097  -8.306   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.724  -9.712   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.067  -9.450   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.543 -10.915   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.512 -12.059   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.006 -11.739   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.975 -12.883   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.281 -13.699   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.399 -14.311   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.347 -15.525   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.874 -14.526   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.297 -15.953   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.469 -12.563   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.439 -13.708   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.993 -11.099   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.024  -9.954   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.548  -8.490   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.530 -10.274   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.054  -8.810   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.560  -9.130   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.085  -7.665   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.115  -6.521   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.621  -6.841   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.301  -5.335   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   37                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   37                                             
CONECT   16   15                                                            
CONECT   17   15   18   34                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   20   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   21   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   20   33   34                                             
CONECT   33   32   34                                                       
CONECT   34   33   17   32   35                                             
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   12   15   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
24-Epiquadrangularate g	Generator

Chemical Formula

C₃₁H₄₈O₇

Average Mass

532.7180 Da

Monoisotopic Mass

532.34000 Da

IUPAC Name

(2R,5R)-2-[(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid

Traditional Name

(2R,5R)-2-[(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(C)[C@@H](O)C[C@H](O)[C@]23C[C@]22CC[C@]4(C)[C@H](CC[C@@]4(C)[C@@H]2CC[C@@H]13)[C@@H](CC[C@@H](O)C(C)=C)C(O)=O

InChI Identifier

InChI=1S/C31H48O7/c1-17(2)20(32)8-7-18(25(35)36)19-11-12-28(4)21-9-10-22-29(5,26(37)38-6)23(33)15-24(34)31(22)16-30(21,31)14-13-27(19,28)3/h18-24,32-34H,1,7-16H2,2-6H3,(H,35,36)/t18-,19-,20-,21+,22+,23+,24+,27-,28+,29+,30+,31-/m1/s1

InChI Key

KALMVCDXDQYBPA-WQXOJWCKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
Tetrahydroxy bile acid, alcohol, or derivatives
24-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid acid
3-hydroxysteroid
1-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
11-beta-hydroxysteroid
11-hydroxysteroid
Medium-chain fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Unsaturated fatty acid
Fatty acid
Fatty acyl
Hydroxy acid
Dicarboxylic acid or derivatives
Methyl ester
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.34	ChemAxon
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	142.13 m³·mol⁻¹	ChemAxon
Polarizability	60.55 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

C00046573

Chemspider ID

8872900

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10697557

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Banskota AH, Tezuka Y, Tran KQ, Tanaka K, Saiki I, Kadota S: Thirteen novel cycloartane-type triterpenes from Combretum quadrangulare. J Nat Prod. 2000 Jan;63(1):57-64. doi: 10.1021/np990336q. [PubMed:10650080 ]
LOTUS database [Link]

Showing NP-Card for (2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid (NP0308902)

MOL for NP0308902 ((2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid)

3D MOL for NP0308902 ((2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid)

3D SDF for NP0308902 ((2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid)

3D-SDF for NP0308902 ((2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid)

PDB for NP0308902 ((2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid)

3D PDB for NP0308902 ((2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid)

SMILES for NP0308902 ((2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid)

INCHI for NP0308902 ((2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid)

Structure for NP0308902 ((2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid)

3D Structure for NP0308902 ((2r,5r)-2-[(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7-(methoxycarbonyl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl]-5-hydroxy-6-methylhept-6-enoic acid)