NP-MRD: Showing NP-Card for (3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate (NP0264337)

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Record Information

Version

2.0

Created at

2022-09-08 07:49:27 UTC

Updated at

2022-09-08 07:49:27 UTC

NP-MRD ID

NP0264337

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

Description

Linichlorin A 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. (3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate is found in Rhaponticum repens, Centaurea glastifolia, Centaurea hermannii, Cousinia piptocephala and Saussurea elegans. (3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate was first documented in 2013 (PMID: 23910095). Based on a literature review very few articles have been published on Linichlorin A (PMID: 33371413).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082209492D          

 26 28  0  0  1  0            999 V2000
    0.5751    2.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660    3.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4218   -1.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881   -1.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511   -2.0667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 18  1  0  0  0  0
 19 15  1  6  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  6  0  0  0
  7 26  1  0  0  0  0
 20 26  1  0  0  0  0
M  END

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
    4.3598    0.7401    1.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6188    0.1956    0.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210    0.0365    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5514   -0.2597   -0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8045   -0.7838   -1.4293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2311   -0.1243    0.0683 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1303   -0.5453   -0.7332 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5023   -1.7022    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631   -1.2435    1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5411   -1.3091    2.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5233   -0.7207    1.3797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5928   -1.5979    0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6886   -0.6629    0.2539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7675   -0.7408   -1.1300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2185    0.6832    0.7273 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4566    0.6903    2.1261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866    1.8445    0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6524    1.7813    0.4575 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7424    0.5727    0.5670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2402    0.2656   -0.7987 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8544    0.9854   -1.8447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660    1.1419   -2.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3046    1.2845   -4.1016 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3518    1.1034   -2.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875    1.4424   -2.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2055    0.6150   -0.9199 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3406    0.8559    2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630    1.0688    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6436    0.8572    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0447    0.0063   -0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3832   -0.9320    0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5511   -0.9654   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1196   -2.3522   -0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3665   -2.3601    0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5458   -1.6821    2.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -0.9921    3.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7973   -0.4797    2.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0554   -2.2077    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2370   -2.2942    0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6590   -0.8854    0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2355   -1.5613   -1.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3399    0.2525    2.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7369    2.0037   -0.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5304    2.7675    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1699    1.3694    1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663   -0.8126   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389    1.3876   -2.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4329    1.7814   -3.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705    1.4822   -0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  3
 24 26  1  0
 26  7  1  0
 19 11  1  0
 26 20  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  1 27  1  0
  1 28  1  0
  7 32  1  6
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  1
 12 38  1  0
 12 39  1  0
 13 40  1  1
 14 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  1
 20 46  1  6
 25 47  1  0
 25 48  1  0
 26 49  1  1
M  END


  Mrv1652309082209492D          

 26 28  0  0  1  0            999 V2000
    0.5751    2.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660    3.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4218   -1.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881   -1.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511   -2.0667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 18  1  0  0  0  0
 19 15  1  6  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  6  0  0  0
  7 26  1  0  0  0  0
 20 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0264337

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)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/C19H23ClO6/c1-8(2)17(22)25-12-5-9(3)11-6-13(21)19(24,7-20)15(11)16-14(12)10(4)18(23)26-16/h11-16,21,24H,1,3-7H2,2H3/t11-,12-,13-,14+,15-,16-,19+/m0/s1

> <INCHI_KEY>
ONMAQPPVCANFPB-URUZQALBSA-N

> <FORMULA>
C19H23ClO6

> <MOLECULAR_WEIGHT>
382.84

> <EXACT_MASS>
382.1183162

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
38.51741728810868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

> <JCHEM_LOGP>
1.7852155226666657

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.750061204320708

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.797944327077428

> <JCHEM_PKA_STRONGEST_BASIC>
-3.266584119533176

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
93.5374

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       1.073   5.261   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.507   5.824   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.737   7.347   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.145   5.426   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.665   3.341   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.254  -3.044   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.325  -2.319   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       6.255  -3.858   0.000  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.343   0.879   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   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   19                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   15   11   20                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    7   20                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₃ClO₆

Average Mass

382.8400 Da

Monoisotopic Mass

382.11832 Da

IUPAC Name

(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

Traditional Name

(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=C)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/C19H23ClO6/c1-8(2)17(22)25-12-5-9(3)11-6-13(21)19(24,7-20)15(11)16-14(12)10(4)18(23)26-16/h11-16,21,24H,1,3-7H2,2H3/t11-,12-,13-,14+,15-,16-,19+/m0/s1

InChI Key

ONMAQPPVCANFPB-URUZQALBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acroptilon repens	LOTUS Database	35616633
Centaurea glastifolia	LOTUS Database	35616633
Centaurea hermannii	LOTUS Database	35616633
Cousinia piptocephala	LOTUS Database	35616633
Saussurea elegans	LOTUS Database	35616633

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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Chlorohydrin
Halohydrin
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Alkyl chloride
Alkyl halide
Organohalogen compound
Organochloride
Organooxygen compound
Carbonyl group
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	1.79	ChemAxon
pKa (Strongest Acidic)	12.8	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.54 m³·mol⁻¹	ChemAxon
Polarizability	38.52 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

C00020443

Chemspider ID

158587

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182337

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Estevez-Sarmiento F, Saavedra E, Ruiz-Estevez M, Leon F, Quintana J, Brouard I, Estevez F: Chlorinated Guaiane-Type Sesquiterpene Lactones as Cytotoxic Agents against Human Tumor Cells. Int J Mol Sci. 2020 Dec 21;21(24):9767. doi: 10.3390/ijms21249767. [PubMed:33371413 ]
Ooi LC, Watanabe N, Futamura Y, Sulaiman SF, Darah I, Osada H: Identification of small molecule inhibitors of p27(Kip1) ubiquitination by high-throughput screening. Cancer Sci. 2013 Nov;104(11):1461-7. doi: 10.1111/cas.12246. Epub 2013 Sep 6. [PubMed:23910095 ]
LOTUS database [Link]

Showing NP-Card for (3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate (NP0264337)

MOL for NP0264337 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate)

3D MOL for NP0264337 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate)

3D SDF for NP0264337 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate)

3D-SDF for NP0264337 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate)

PDB for NP0264337 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate)

3D PDB for NP0264337 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate)

SMILES for NP0264337 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate)

INCHI for NP0264337 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate)

Structure for NP0264337 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate)

3D Structure for NP0264337 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate)