NP-MRD: Showing NP-Card for (2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid (NP0245524)

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Record Information

Version

2.0

Created at

2022-09-07 06:38:11 UTC

Updated at

2022-09-07 06:38:12 UTC

NP-MRD ID

NP0245524

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid

Description

(2S)-3-{[(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review very few articles have been published on (2S)-3-{[(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208382D          

 28 30  0  0  1  0            999 V2000
   -0.4082    3.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125    3.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961    2.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    1.9557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1394    1.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249    0.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -0.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105    1.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7105    1.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040    0.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040   -0.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7185    1.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8827    2.3137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5909    1.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    1.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122    2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0165    2.2497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880    3.1919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663    3.1180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5519    3.7630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7269    3.7630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4720    4.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    5.0325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1394    5.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069    4.5476    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3653    5.1549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6156    4.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612    5.0034    0.0000 Cl  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
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  0  0  0
 13 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -0.2598   -2.6205    1.6044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6846   -1.8893    0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2983   -1.7075   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9903   -0.3762   -0.4439 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0112   -0.4525    0.5622 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3670   -0.3171    0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6451   -0.1273   -0.9809 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411   -0.3889    1.2220 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7695   -0.1965    0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2940    0.6513    2.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3281    1.4459    2.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897    0.7799    3.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0913    0.7804   -0.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4641    1.9985   -0.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6071    2.6822   -0.8702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6608    2.3552   -1.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6267    3.1179   -2.8004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731    1.6868   -1.2644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493    0.5274   -0.6103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1245    0.1606    0.6068 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0513   -1.3711    0.7267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9769   -1.7775   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9987   -0.6421   -0.5379 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9232   -0.0544   -1.7874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5985    0.3390    0.5282 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1345   -0.1394    1.7343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1004    1.7167    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5164    2.7177    1.6994 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7325   -3.0367    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9004   -2.7994    2.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -1.9269   -1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125   -2.4836   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4990   -0.2048   -1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5026   -1.3876    1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8023   -0.9207   -0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7571    0.8637    0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6191   -0.2955    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1454    0.4507    3.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1348    1.0559    0.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782    3.5659   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4144    2.3836   -0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599   -0.3026   -1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6832    0.5752    1.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4720   -1.6053    1.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5304   -2.6767   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4749   -2.0099   -1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229   -0.9949   -0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8238   -0.0325   -2.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6257   -0.9734    1.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9554    2.1805   -0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2220    1.6763    0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
 10 12  1  0
 10 11  2  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  1
 25 27  1  0
 27 28  1  0
 25 20  1  0
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 16 14  1  0
 14 15  2  3
 14 13  1  0
 13  4  1  0
 20 21  1  0
 13 19  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
  8 34  1  1
 12 38  1  0
  4 33  1  6
  3 31  1  0
  3 32  1  0
  1 29  1  0
  1 30  1  0
 21 44  1  1
 22 45  1  0
 22 46  1  0
 23 47  1  1
 24 48  1  0
 26 49  1  0
 27 50  1  0
 27 51  1  0
 20 43  1  1
 19 42  1  6
 15 40  1  0
 15 41  1  0
 13 39  1  1
M  END


  Mrv1652309072208382D          

 28 30  0  0  1  0            999 V2000
   -0.4082    3.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125    3.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961    2.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    1.9557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1394    1.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249    0.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -0.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105    1.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7105    1.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040    0.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040   -0.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7185    1.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8827    2.3137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5909    1.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    1.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2122    2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0165    2.2497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880    3.1919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663    3.1180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5519    3.7630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7269    3.7630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4720    4.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    5.0325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1394    5.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069    4.5476    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3653    5.1549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6156    4.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612    5.0034    0.0000 Cl  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
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  0  0  0
 13 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245524

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](C(O)=O)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)[C@](O)(CCl)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C19H23ClO8/c1-7-4-11(27-18(25)9(3)16(22)23)13-8(2)17(24)28-15(13)14-10(7)5-12(21)19(14,26)6-20/h9-15,21,26H,1-2,4-6H2,3H3,(H,22,23)/t9-,10-,11-,12-,13+,14-,15-,19+/m0/s1

> <INCHI_KEY>
KCCZVNWVTKPUHZ-IKYBHFBFSA-N

> <FORMULA>
C19H23ClO8

> <MOLECULAR_WEIGHT>
414.84

> <EXACT_MASS>
414.1081454

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.60764499098357

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-3-{[(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid

> <JCHEM_LOGP>
0.835253417333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.79794432913408

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7918146444645475

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2665841195282406

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
95.4512

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-{[(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.762   6.163   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.263   5.820   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.606   4.319   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.994   3.651   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.994   2.111   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.660   1.341   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.660  -0.199   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.326   2.111   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.326   3.651   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.007   1.341   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.007  -0.199   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.341   2.111   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.381   4.319   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.703   3.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.841   1.995   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.863   4.542   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.364   4.200   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -7.258   5.958   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.724   5.820   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.764   7.024   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.224   7.024   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.748   8.489   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.994   9.394   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.994  10.934   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.239   8.489   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.282   9.622   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.749   8.184   0.000  0.00  0.00           C+0
HETATM   28 Cl   UNK     0      -7.768   9.340   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    4   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20    2   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   20   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
(2S)-3-{[(3ar,4S,6ar,8S,9S,9as,9BS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoate	Generator

Chemical Formula

C₁₉H₂₃ClO₈

Average Mass

414.8400 Da

Monoisotopic Mass

414.10815 Da

IUPAC Name

(2S)-3-{[(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid

Traditional Name

(2S)-3-{[(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](C(O)=O)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)[C@](O)(CCl)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C19H23ClO8/c1-7-4-11(27-18(25)9(3)16(22)23)13-8(2)17(24)28-15(13)14-10(7)5-12(21)19(14,26)6-20/h9-15,21,26H,1-2,4-6H2,3H3,(H,22,23)/t9-,10-,11-,12-,13+,14-,15-,19+/m0/s1

InChI Key

KCCZVNWVTKPUHZ-IKYBHFBFSA-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 guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
1,3-dicarbonyl compound
Gamma butyrolactone
Enoate ester
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Lactone
Chlorohydrin
Secondary alcohol
Carboxylic acid ester
1,2-diol
Halohydrin
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Organooxygen compound
Organochloride
Organohalogen 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	0.84	ChemAxon
pKa (Strongest Acidic)	3.79	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.45 m³·mol⁻¹	ChemAxon
Polarizability	39.61 Å³	ChemAxon
Number of Rings	3	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

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

163007346

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid (NP0245524)

MOL for NP0245524 ((2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid)

3D MOL for NP0245524 ((2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid)

3D SDF for NP0245524 ((2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid)

3D-SDF for NP0245524 ((2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid)

PDB for NP0245524 ((2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid)

3D PDB for NP0245524 ((2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid)

SMILES for NP0245524 ((2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid)

INCHI for NP0245524 ((2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid)

Structure for NP0245524 ((2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid)

3D Structure for NP0245524 ((2s)-3-{[(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]oxy}-2-methyl-3-oxopropanoic acid)