NP-MRD: Showing NP-Card for (2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate (NP0191486)

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Record Information

Version

2.0

Created at

2022-09-04 08:28:18 UTC

Updated at

2022-09-04 08:28:18 UTC

NP-MRD ID

NP0191486

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate

Description

(2S)-4-[(3aS,4R,6aR,8S,9aR,9bR)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate 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)-4-[(3aS,4R,6aR,8S,9aR,9bR)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042210282D          

 32 34  0  0  1  0            999 V2000
    5.6412   -1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1803   -0.8820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9967   -1.6863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6417   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188   -3.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1638   -3.5308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508   -3.3179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0522   -4.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4494   -2.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -2.4269    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9828   -3.6193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599   -4.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049   -4.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0919   -4.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -0.8820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5541   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.2321    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9461    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691    1.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    1.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241    2.0766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.2370    0.0000 C   0  0  2  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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  8 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  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
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 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  2  0  0  0  0
 32 30  1  6  0  0  0
 23 32  1  0  0  0  0
  6 32  1  0  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
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   -0.9621   -0.9590   -2.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459    0.4648   -2.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912    1.1118   -3.3547 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385    1.0161   -2.1793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6918    0.2120   -1.1421 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1594   -1.0731   -1.1863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7284   -1.2704    0.1323 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1001   -1.6976    0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5470   -0.8945    1.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9618    0.9442    1.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9819    1.9019    2.8587 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.9502    0.7912    0.3548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8497    1.7261   -0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0581    2.4340   -1.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7005    1.9692   -1.0967 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -2.0359    0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6314   -2.1237    0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9348   -3.4248    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5927   -1.1553   -0.2311 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3945   -0.4696    0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588    0.6311    0.0449 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7601    1.5380    0.8260 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1342    1.6553    0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9996    2.5711    1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6903    0.9371   -0.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490    1.1656   -0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290    2.4397   -0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469   -0.0618   -1.1324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4925   -2.9669   -2.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4799    0.7851   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6431   -1.8816   -1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3144   -2.7536    0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4937   -0.4439    2.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9016   -0.9999    2.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7844   -1.8665    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3537    1.5834    1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    0.2906    2.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9515    2.1986   -0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8629    3.5125   -1.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1832    2.2327   -2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4969   -1.5668    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1393   -3.0073    1.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784   -3.6136   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2837   -4.2385    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4026   -1.7083   -0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1515   -1.1359    1.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6874   -0.0269    1.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7151    0.0912   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0420    2.1477    1.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6224    2.8051    2.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0868    3.5117    0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686    3.1922   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6369    2.8086   -1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066   -0.2108   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
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 32  6  1  0
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 30 25  1  0
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 28 56  1  0
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 31 59  1  0
 31 60  1  0
M  END


  Mrv1652309042210282D          

 32 34  0  0  1  0            999 V2000
    5.6412   -1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1803   -0.8820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9967   -1.6863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6417   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188   -3.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1638   -3.5308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508   -3.3179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0522   -4.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4494   -2.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -2.4269    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    3.2534   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -0.8820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5541   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.2321    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9461    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691    1.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    1.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241    2.0766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.2370    0.0000 C   0  0  2  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  2  0  0  0  0
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  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0191486

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@H]2[C@@H]([C@H]3OC(=O)C(=C)[C@@H]3[C@@H](CC(=O)[C@@](C)(CCl)OC(C)=O)CC2=C)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C24H29ClO7/c1-11-7-16(8-19(28)24(6,10-25)32-15(5)27)20-13(3)23(29)31-22(20)21-12(2)18(9-17(11)21)30-14(4)26/h16-18,20-22H,1-3,7-10H2,4-6H3/t16-,17+,18+,20-,21+,22+,24-/m1/s1

> <INCHI_KEY>
ZUJROUFLVVXBEN-RAMSZUDPSA-N

> <FORMULA>
C24H29ClO7

> <MOLECULAR_WEIGHT>
464.94

> <EXACT_MASS>
464.160181

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
47.68903802269277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-4-[(3aS,4R,6aR,8S,9aR,9bR)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate

> <JCHEM_LOGP>
2.9596304616666655

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.03291779959297

> <JCHEM_PKA_STRONGEST_BASIC>
-6.475479432059466

> <JCHEM_POLAR_SURFACE_AREA>
95.97000000000003

> <JCHEM_REFRACTIVITY>
115.66009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-4-[(3aS,4R,6aR,8S,9aR,9bR)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      10.530  -1.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.245  -1.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.176   0.433   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.380   1.393   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.691   0.843   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.843  -0.442   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.803  -1.646   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.461  -3.148   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.665  -4.108   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.435  -5.631   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.639  -6.591   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.001  -6.193   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.564  -7.627   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.439  -4.760   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       4.916  -4.530   0.000  0.00  0.00          Cl+0
HETATM   16  O   UNK     0       5.568  -6.756   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.338  -8.279   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.542  -9.239   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.905  -8.841   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.073  -3.816   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.686  -3.148   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.482  -4.108   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.343  -1.646   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.901  -1.105   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.970   0.433   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.766   1.393   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.996   2.916   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.429   3.479   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.792   3.876   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.455   0.843   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.996   2.285   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.303  -0.442   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   16                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    8   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23    6                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
(2S)-4-[(3AS,4R,6ar,8S,9ar,9BR)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetic acid	Generator

Chemical Formula

C₂₄H₂₉ClO₇

Average Mass

464.9400 Da

Monoisotopic Mass

464.16018 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@H]2[C@@H]([C@H]3OC(=O)C(=C)[C@@H]3[C@@H](CC(=O)[C@@](C)(CCl)OC(C)=O)CC2=C)C1=C

InChI Identifier

InChI=1S/C24H29ClO7/c1-11-7-16(8-19(28)24(6,10-25)32-15(5)27)20-13(3)23(29)31-22(20)21-12(2)18(9-17(11)21)30-14(4)26/h16-18,20-22H,1-3,7-10H2,4-6H3/t16-,17+,18+,20-,21+,22+,24-/m1/s1

InChI Key

ZUJROUFLVVXBEN-RAMSZUDPSA-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
Sesquiterpenoid
Guaiane sesquiterpenoid
Tricarboxylic acid or derivatives
Alpha-acyloxy ketone
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
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	2.96	ChemAxon
pKa (Strongest Acidic)	18.03	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Rotatable Bond Count	8	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

162816951

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate (NP0191486)

MOL for NP0191486 ((2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate)

3D MOL for NP0191486 ((2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate)

3D SDF for NP0191486 ((2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate)

3D-SDF for NP0191486 ((2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate)

PDB for NP0191486 ((2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate)

3D PDB for NP0191486 ((2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate)

SMILES for NP0191486 ((2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate)

INCHI for NP0191486 ((2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate)

Structure for NP0191486 ((2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate)

3D Structure for NP0191486 ((2s)-4-[(3as,4r,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl]-1-chloro-2-methyl-3-oxobutan-2-yl acetate)