NP-MRD: Showing NP-Card for sarmentoic acid (NP0032865)

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Record Information

Version

2.0

Created at

2021-06-19 23:33:59 UTC

Updated at

2021-06-30 00:02:18 UTC

NP-MRD ID

NP0032865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sarmentoic acid

Provided By

JEOL Database JEOL Logo

Description

Sarmentoic acid, also known as sarmentoate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. sarmentoic acid is found in Sedum sarmentosum. sarmentoic acid was first documented in 2007 (PMID: 17291046). Based on a literature review very few articles have been published on Sarmentoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101343D          

 41 41  0  0  0  0            999 V2000
   -0.8465   -1.1521   -2.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433   -1.3681   -1.0683 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1423   -2.5263   -1.5351 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2762   -2.8260   -0.5642 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2252   -1.7668   -0.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502   -3.0573    0.8488 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8153   -1.9419    1.3977 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6335   -0.6805    1.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2102   -2.4895    2.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -1.6400    0.3599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2746   -0.4937    0.8235 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7611   -0.8615    0.6680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7143    0.2715    1.0516 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4371    0.7485    2.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194    1.4483    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799    1.3781   -1.1319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3312    2.6043    0.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029   -1.0342   -3.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.2450   -1.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354   -2.0023   -2.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467   -0.4523   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5335   -3.4306   -1.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -2.2782   -2.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085   -3.7252   -0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5334   -1.6447   -1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6001   -3.1874    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2009   -4.0089    0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5082   -0.9402    2.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458    0.0351    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9920   -0.1489    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999   -1.7465    3.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231   -3.3635    2.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008   -2.7985    3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9277   -2.5607    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0476    0.4269    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -0.2501    1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632   -1.7190    1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9738   -1.1843   -0.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7538   -0.0735    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4924   -0.0256    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2435    2.3765    1.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  4  3  1  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
 11 12  1  0  0  0  0
 10  7  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4  5  1  0  0  0  0
 13 15  1  0  0  0  0
  6  4  1  0  0  0  0
 15 17  1  0  0  0  0
 10 11  1  0  0  0  0
 15 16  2  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  4 24  1  6  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  2 21  1  1  0  0  0
 10 34  1  6  0  0  0
  5 25  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 13 39  1  1  0  0  0
 14 40  1  0  0  0  0
 17 41  1  0  0  0  0
M  END

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
   -0.8465   -1.1521   -2.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433   -1.3681   -1.0683 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1423   -2.5263   -1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2762   -2.8260   -0.5642 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2252   -1.7668   -0.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502   -3.0573    0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8153   -1.9419    1.3977 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6335   -0.6805    1.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2102   -2.4895    2.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -1.6400    0.3599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2746   -0.4937    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611   -0.8615    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7143    0.2715    1.0516 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4371    0.7485    2.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194    1.4483    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799    1.3781   -1.1319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3312    2.6043    0.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029   -1.0342   -3.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.2450   -1.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354   -2.0023   -2.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467   -0.4523   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5335   -3.4306   -1.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -2.2782   -2.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085   -3.7252   -0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5334   -1.6447   -1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6001   -3.1874    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2009   -4.0089    0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5082   -0.9402    2.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458    0.0351    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9920   -0.1489    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999   -1.7465    3.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231   -3.3635    2.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008   -2.7985    3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9277   -2.5607    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0476    0.4269    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -0.2501    1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632   -1.7190    1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9738   -1.1843   -0.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7538   -0.0735    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4924   -0.0256    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2435    2.3765    1.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  1
  4  3  1  0
  2  1  1  0
  3  2  1  0
  7  9  1  0
  2 10  1  0
 11 12  1  0
 10  7  1  0
 12 13  1  0
 13 14  1  0
  4  5  1  0
 13 15  1  0
  6  4  1  0
 15 17  1  0
 10 11  1  0
 15 16  2  0
  6 26  1  0
  6 27  1  0
  4 24  1  6
  3 22  1  0
  3 23  1  0
  2 21  1  1
 10 34  1  6
  5 25  1  0
 11 35  1  0
 11 36  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  1
 14 40  1  0
 17 41  1  0
M  END


  Mrv1652306202101343D          

 41 41  0  0  0  0            999 V2000
   -0.8465   -1.1521   -2.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433   -1.3681   -1.0683 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1423   -2.5263   -1.5351 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2762   -2.8260   -0.5642 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2252   -1.7668   -0.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502   -3.0573    0.8488 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8153   -1.9419    1.3977 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6335   -0.6805    1.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2102   -2.4895    2.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -1.6400    0.3599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2746   -0.4937    0.8235 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7611   -0.8615    0.6680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7143    0.2715    1.0516 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4371    0.7485    2.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194    1.4483    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799    1.3781   -1.1319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3312    2.6043    0.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029   -1.0342   -3.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.2450   -1.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354   -2.0023   -2.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467   -0.4523   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5335   -3.4306   -1.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -2.2782   -2.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085   -3.7252   -0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5334   -1.6447   -1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6001   -3.1874    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2009   -4.0089    0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5082   -0.9402    2.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458    0.0351    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9920   -0.1489    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999   -1.7465    3.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231   -3.3635    2.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008   -2.7985    3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9277   -2.5607    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0476    0.4269    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -0.2501    1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632   -1.7190    1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9738   -1.1843   -0.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7538   -0.0735    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4924   -0.0256    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2435    2.3765    1.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  4  3  1  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
 11 12  1  0  0  0  0
 10  7  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4  5  1  0  0  0  0
 13 15  1  0  0  0  0
  6  4  1  0  0  0  0
 15 17  1  0  0  0  0
 10 11  1  0  0  0  0
 15 16  2  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  4 24  1  6  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  2 21  1  1  0  0  0
 10 34  1  6  0  0  0
  5 25  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 13 39  1  1  0  0  0
 14 40  1  0  0  0  0
 17 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(O[H])C([H])([H])C([H])([H])[C@@]1([H])[C@]([H])(C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H24O4/c1-8-6-9(14)7-13(2,3)10(8)4-5-11(15)12(16)17/h8-11,14-15H,4-7H2,1-3H3,(H,16,17)/t8-,9-,10+,11-/m1/s1

> <INCHI_KEY>
HJEKFWBWYCIINK-CHWFTXMASA-N

> <FORMULA>
C13H24O4

> <MOLECULAR_WEIGHT>
244.331

> <EXACT_MASS>
244.167459253

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
26.568902499801155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-hydroxy-4-[(1S,4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexyl]butanoic acid

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.584196181333333

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.283612074488467

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.314905745565401

> <JCHEM_PKA_STRONGEST_BASIC>
-1.074502779502235

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
64.357

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-hydroxy-4-[(1S,4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
   -0.8465   -1.1521   -2.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433   -1.3681   -1.0683 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1423   -2.5263   -1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2762   -2.8260   -0.5642 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2252   -1.7668   -0.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502   -3.0573    0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8153   -1.9419    1.3977 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6335   -0.6805    1.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2102   -2.4895    2.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -1.6400    0.3599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2746   -0.4937    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611   -0.8615    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7143    0.2715    1.0516 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4371    0.7485    2.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194    1.4483    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799    1.3781   -1.1319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3312    2.6043    0.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029   -1.0342   -3.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.2450   -1.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354   -2.0023   -2.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467   -0.4523   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5335   -3.4306   -1.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -2.2782   -2.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085   -3.7252   -0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5334   -1.6447   -1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6001   -3.1874    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2009   -4.0089    0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5082   -0.9402    2.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458    0.0351    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9920   -0.1489    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999   -1.7465    3.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231   -3.3635    2.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008   -2.7985    3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9277   -2.5607    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0476    0.4269    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -0.2501    1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632   -1.7190    1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9738   -1.1843   -0.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7538   -0.0735    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4924   -0.0256    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2435    2.3765    1.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  1
  4  3  1  0
  2  1  1  0
  3  2  1  0
  7  9  1  0
  2 10  1  0
 11 12  1  0
 10  7  1  0
 12 13  1  0
 13 14  1  0
  4  5  1  0
 13 15  1  0
  6  4  1  0
 15 17  1  0
 10 11  1  0
 15 16  2  0
  6 26  1  0
  6 27  1  0
  4 24  1  6
  3 22  1  0
  3 23  1  0
  2 21  1  1
 10 34  1  6
  5 25  1  0
 11 35  1  0
 11 36  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  1
 14 40  1  0
 17 41  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.847  -1.152  -2.126  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.243  -1.368  -1.068  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.142  -2.526  -1.535  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.276  -2.826  -0.564  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.225  -1.767  -0.563  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.750  -3.057   0.849  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.815  -1.942   1.398  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.634  -0.681   1.752  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.210  -2.490   2.715  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.329  -1.640   0.360  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.275  -0.494   0.824  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.761  -0.862   0.668  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.714   0.272   1.052  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.437   0.749   2.379  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.619   1.448   0.076  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.780   1.378  -1.132  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.331   2.604   0.729  0.00  0.00           O+0
HETATM   18  H   UNK     0      -0.403  -1.034  -3.121  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.425  -0.245  -1.930  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.535  -2.002  -2.166  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.847  -0.452  -1.042  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.534  -3.431  -1.665  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.564  -2.278  -2.517  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.809  -3.725  -0.895  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.533  -1.645  -1.478  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.600  -3.187   1.532  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.201  -4.009   0.848  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.508  -0.940   2.360  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.046   0.035   2.336  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.992  -0.149   0.867  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.400  -1.746   3.237  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.423  -3.364   2.525  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.001  -2.799   3.409  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.928  -2.561   0.287  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.048   0.427   0.274  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.111  -0.250   1.877  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.963  -1.719   1.323  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.974  -1.184  -0.356  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.754  -0.074   1.042  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.492  -0.026   2.971  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.244   2.377   1.687  0.00  0.00           H+0
CONECT    1    2   18   19   20                                             
CONECT    2    1    3   10   21                                             
CONECT    3    4    2   22   23                                             
CONECT    4    3    5    6   24                                             
CONECT    5    4   25                                                       
CONECT    6    7    4   26   27                                             
CONECT    7    6    8    9   10                                             
CONECT    8    7   28   29   30                                             
CONECT    9    7   31   32   33                                             
CONECT   10    2    7   11   34                                             
CONECT   11   12   10   35   36                                             
CONECT   12   11   13   37   38                                             
CONECT   13   12   14   15   39                                             
CONECT   14   13   40                                                       
CONECT   15   13   17   16                                                  
CONECT   16   15                                                            
CONECT   17   15   41                                                       
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    2                                                            
CONECT   22    3                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    6                                                            
CONECT   28    8                                                            
CONECT   29    8                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32    9                                                            
CONECT   33    9                                                            
CONECT   34   10                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   17                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   82    0
END

RDKit          3D

41 41  0  0  0  0  0  0  0  0999 V2000
   -0.8465   -1.1521   -2.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433   -1.3681   -1.0683 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1423   -2.5263   -1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2762   -2.8260   -0.5642 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2252   -1.7668   -0.5634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502   -3.0573    0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8153   -1.9419    1.3977 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6335   -0.6805    1.7518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2102   -2.4895    2.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -1.6400    0.3599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2746   -0.4937    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611   -0.8615    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7143    0.2715    1.0516 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4371    0.7485    2.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194    1.4483    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799    1.3781   -1.1319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3312    2.6043    0.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029   -1.0342   -3.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -0.2450   -1.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354   -2.0023   -2.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467   -0.4523   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5335   -3.4306   -1.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -2.2782   -2.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085   -3.7252   -0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5334   -1.6447   -1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6001   -3.1874    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2009   -4.0089    0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5082   -0.9402    2.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458    0.0351    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9920   -0.1489    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999   -1.7465    3.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231   -3.3635    2.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008   -2.7985    3.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9277   -2.5607    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0476    0.4269    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -0.2501    1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632   -1.7190    1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9738   -1.1843   -0.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7538   -0.0735    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4924   -0.0256    2.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2435    2.3765    1.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  1
  4  3  1  0
  2  1  1  0
  3  2  1  0
  7  9  1  0
  2 10  1  0
 11 12  1  0
 10  7  1  0
 12 13  1  0
 13 14  1  0
  4  5  1  0
 13 15  1  0
  6  4  1  0
 15 17  1  0
 10 11  1  0
 15 16  2  0
  6 26  1  0
  6 27  1  0
  4 24  1  6
  3 22  1  0
  3 23  1  0
  2 21  1  1
 10 34  1  6
  5 25  1  0
 11 35  1  0
 11 36  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  1
 14 40  1  0
 17 41  1  0
M  END

View in JSmol

Synonyms

Value	Source
Sarmentoate	Generator

Chemical Formula

C₁₃H₂₄O₄

Average Mass

244.3310 Da

Monoisotopic Mass

244.16746 Da

IUPAC Name

(2R)-2-hydroxy-4-[(1S,4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexyl]butanoic acid

Traditional Name

(2R)-2-hydroxy-4-[(1S,4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexyl]butanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]([H])(O[H])C([H])([H])C([H])([H])[C@@]1([H])[C@]([H])(C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C13H24O4/c1-8-6-9(14)7-13(2,3)10(8)4-5-11(15)12(16)17/h8-11,14-15H,4-7H2,1-3H3,(H,16,17)/t8-,9-,10+,11-/m1/s1

InChI Key

HJEKFWBWYCIINK-CHWFTXMASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sedum sarmentosum	JEOL database	Yoshikawa, M., et al, J. Nat. Prod. 70, 575 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Megastigmane sesquiterpenoid
Sesquiterpenoid
Cyclohexanol
Alpha-hydroxy acid
Fatty acid
Hydroxy acid
Monosaccharide
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	1.47	ALOGPS
logP	1.58	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	4.31	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	64.36 m³·mol⁻¹	ChemAxon
Polarizability	26.57 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

17344290

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16216665

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yoshikawa M, Morikawa T, Zhang Y, Nakamura S, Muraoka O, Matsuda H: Megastigmanes and their glucosides from the whole plant of Sedum sarmentosum. J Nat Prod. 2007 Apr;70(4):575-83. doi: 10.1021/np068059s. Epub 2007 Feb 10. [PubMed:17291046 ]
Yoshikawa, M., et al. (2007). Yoshikawa, M., et al, J. Nat. Prod. 70, 575 (2007) . J. Nat. Prod..

Showing NP-Card for sarmentoic acid (NP0032865)

MOL for NP0032865 (sarmentoic acid)

3D MOL for NP0032865 (sarmentoic acid)

3D SDF for NP0032865 (sarmentoic acid)

3D-SDF for NP0032865 (sarmentoic acid)

PDB for NP0032865 (sarmentoic acid)

3D PDB for NP0032865 (sarmentoic acid)

SMILES for NP0032865 (sarmentoic acid)

INCHI for NP0032865 (sarmentoic acid)

Structure for NP0032865 (sarmentoic acid)

3D Structure for NP0032865 (sarmentoic acid)