NP-MRD: Showing NP-Card for (3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate (NP0144995)

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Record Information

Version

2.0

Created at

2022-09-02 00:05:42 UTC

Updated at

2022-09-02 00:05:42 UTC

NP-MRD ID

NP0144995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(3AR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl benzoate 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)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate is found in Centaurea scoparia. Based on a literature review very few articles have been published on (3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202052D          

 29 32  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  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  2  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  1  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
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  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 O   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  2  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  1  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
    1.5912   -0.6430    0.0000 C   0  0  2  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
    1.0691   -1.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371   -2.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241   -2.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -3.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -3.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8659   -3.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9889   -2.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3439   -2.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2598   -1.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -1.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -2.2055    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
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
  6 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 16 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -2.4309    0.0864    2.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099   -0.7376    1.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8494   -0.8647    1.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0887    0.2017    0.0829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3321   -0.0445   -0.4880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636    0.1222   -1.0170 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1348    1.2993   -1.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2085    1.7231   -2.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967    1.8728   -1.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    3.0176   -2.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9063    0.9456   -1.3373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344    0.1715   -0.4498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1756   -1.1938   -0.1935 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2804   -1.4294    1.3262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0201   -0.6891    1.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858   -1.1906    0.8117 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0864   -0.3873    0.5793 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3955   -0.6550    0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6726   -1.7569    1.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3996    0.3507    0.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0351    1.5554   -0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446    2.5347   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2894    2.3174   -0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6653    1.1158    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7469    0.1508    0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2230   -1.5716   -0.4452 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2240   -2.9871   -0.6101 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8712   -1.0618   -1.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1127   -1.5682   -3.0770 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.3246    0.5986    3.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5177    0.2536    3.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5995   -0.7910    1.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -1.8510    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0996    1.1694    0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3648   -0.8587   -1.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2237   -0.7863   -1.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1620    1.2197   -2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868    2.5981   -3.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7524    0.7916    0.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8960   -1.9519   -0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477   -2.4950    1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1662   -1.0343    2.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2248    0.3681    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3820   -2.1344    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9738    1.7705   -0.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6551    3.4850   -0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9912    3.0984   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7327    0.9395    0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0323   -0.8152    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1710   -3.2319   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1736   -0.0228   -1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376   -1.6473   -1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 16 26  1  0
 26 27  1  6
 26 28  1  0
 28 29  1  0
 26 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  7  1  0
  7  8  2  3
  7  6  1  0
  6  4  1  0
 13 14  1  0
  6 12  1  0
 25 20  1  0
  5 35  1  0
  4 34  1  1
  3 32  1  0
  3 33  1  0
  1 30  1  0
  1 31  1  0
 14 41  1  6
 15 42  1  0
 15 43  1  0
 16 44  1  1
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 27 50  1  0
 28 51  1  0
 28 52  1  0
 13 40  1  6
 12 39  1  1
  8 37  1  0
  8 38  1  0
  6 36  1  6
M  END


  Mrv1652309022202052D          

 29 32  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  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  2  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  1  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
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  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 O   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  2  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  1  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
    1.5912   -0.6430    0.0000 C   0  0  2  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
    1.0691   -1.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371   -2.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241   -2.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -3.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -3.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8659   -3.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9889   -2.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3439   -2.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2598   -1.6778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -1.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -2.2055    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
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  6  0  0  0
  6 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 16 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0144995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC(=C)[C@@H]2C[C@H](OC(=O)C3=CC=CC=C3)[C@](O)(CCl)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C22H23ClO6/c1-11-8-15(24)17-12(2)20(25)29-19(17)18-14(11)9-16(22(18,27)10-23)28-21(26)13-6-4-3-5-7-13/h3-7,14-19,24,27H,1-2,8-10H2/t14-,15-,16-,17+,18-,19-,22+/m0/s1

> <INCHI_KEY>
FKRRWLGLGLGHLD-BZKPKAPTSA-N

> <FORMULA>
C22H23ClO6

> <MOLECULAR_WEIGHT>
418.87

> <EXACT_MASS>
418.1183162

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.25034741861414

> <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)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl benzoate

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
2.454213131333333

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.718873120629961

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.791675512479067

> <JCHEM_PKA_STRONGEST_BASIC>
-2.924139504050693

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
105.2031

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       3.482   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.665   3.341   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.530   1.186   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.996  -3.683   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.429  -4.246   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.792  -4.644   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.021  -6.166   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.183  -7.126   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.616  -6.564   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.846  -5.041   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.642  -4.081   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.218  -3.132   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.634  -2.601   0.000  0.00  0.00           C+0
HETATM   29 Cl   UNK     0       5.366  -4.117   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12   14   26                                                  
CONECT   14   13    2   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   16   13   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(3AR,4S,6ar,8S,9S,9as,9BS)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl benzoic acid	Generator

Chemical Formula

C₂₂H₂₃ClO₆

Average Mass

418.8700 Da

Monoisotopic Mass

418.11832 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@H]1CC(=C)[C@@H]2C[C@H](OC(=O)C3=CC=CC=C3)[C@](O)(CCl)[C@@H]2[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C22H23ClO6/c1-11-8-15(24)17-12(2)20(25)29-19(17)18-14(11)9-16(22(18,27)10-23)28-21(26)13-6-4-3-5-7-13/h3-7,14-19,24,27H,1-2,8-10H2/t14-,15-,16-,17+,18-,19-,22+/m0/s1

InChI Key

FKRRWLGLGLGHLD-BZKPKAPTSA-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
Centaurea scoparia	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
Sesquiterpenoid
Guaiane sesquiterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Chlorohydrin
Secondary alcohol
Halohydrin
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Alkyl halide
Alkyl chloride
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.07	ALOGPS
logP	2.45	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.79	ChemAxon
pKa (Strongest Basic)	-2.9	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	105.2 m³·mol⁻¹	ChemAxon
Polarizability	42.25 Å³	ChemAxon
Number of Rings	4	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

162916868

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate (NP0144995)

MOL for NP0144995 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate)

3D MOL for NP0144995 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate)

3D SDF for NP0144995 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate)

3D-SDF for NP0144995 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate)

PDB for NP0144995 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate)

3D PDB for NP0144995 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate)

SMILES for NP0144995 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate)

INCHI for NP0144995 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate)

Structure for NP0144995 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate)

3D Structure for NP0144995 ((3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate)