NP-MRD: Showing NP-Card for Clementein C (NP0064069)

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Record Information

Version

2.0

Created at

2022-04-28 08:21:50 UTC

Updated at

2022-04-28 08:21:50 UTC

NP-MRD ID

NP0064069

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Clementein C

Description

(3S,3aS,4S,4'R,6aR,8S,9S,9aR,9bS)-8-hydroxy-4',9-dimethyl-6-methylidene-2-oxo-decahydro-2H-spiro[azuleno[4,5-b]furan-3,2'-oxetane]-4-yl 2-(hydroxymethyl)prop-2-enoate 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. Clementein C is found in Centaurea clementei. Based on a literature review very few articles have been published on (3S,3aS,4S,4'R,6aR,8S,9S,9aR,9bS)-8-hydroxy-4',9-dimethyl-6-methylidene-2-oxo-decahydro-2H-spiro[azuleno[4,5-b]furan-3,2'-oxetane]-4-yl 2-(hydroxymethyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282210212D          

 28 31  0  0  1  0            999 V2000
    3.7268    3.2209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3592    2.4823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5526    2.3093    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9143    2.8320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9251    3.6569    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5768    4.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786    3.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9014    4.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865    4.0246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356    4.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8233    5.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970    5.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2906    4.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    6.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924    6.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2199    2.3865    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4290    1.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9063    0.9502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.5407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644    2.0552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1331    2.8107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8886    3.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6355    3.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480    1.9045    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6796    2.2859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5429    3.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4181    1.9183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8266    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  5  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  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  3 19  1  6  0  0  0
 16 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 21 23  1  6  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  1 26  1  6  0  0  0
 25 27  1  6  0  0  0
 24 28  1  1  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    5.3856    0.0530    0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1873   -0.4758    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9716   -1.5562    1.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1354   -1.8414    2.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218    0.0366   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3333    0.9637   -1.2039 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279   -0.4645   -0.3217 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8357    0.0685   -1.1782 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4305   -1.0292   -2.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9494   -1.4812   -1.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9153   -1.1752   -2.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987   -2.1821   -0.4451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4165   -3.0564   -0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4779   -2.4642    0.3097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6336   -2.1905   -0.4090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9251   -1.1708    0.8760 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3448   -1.1030    2.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4007   -1.3206    0.7545 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6907   -0.0470    0.8203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4754    0.9208    1.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2192    2.1929    0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7980    3.2839    1.2435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1063    2.0528    0.0442 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0238    3.0928   -1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1595    3.5087   -0.1424 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8143    4.7111    0.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    2.2956    0.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304    0.6320   -0.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1992   -0.2862    0.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6106    0.8513   -0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220   -1.3175    2.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7062   -2.4748    0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3431   -1.0582    2.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2756    0.8822   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027   -1.9167   -2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4171   -0.7105   -3.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658   -0.6499   -3.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -1.3935   -2.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397   -2.8858   -0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7687   -3.2118   -1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2267   -4.0922   -0.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7817   -3.1631    1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6807   -1.2441   -0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925   -0.2777    0.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1860   -0.0875    2.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4317   -1.3122    2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8018   -1.8605    2.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1119   -1.9367    1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2607   -0.1253    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683    2.7400   -2.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8293    3.7952   -1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1501    3.6057   -0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6538    5.4531    0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0817    5.2565    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6675    4.4845    1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2046    0.6817   -1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 27  1  1
 23 28  1  0
 28 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 19 18  1  0
 18 16  1  0
 16 17  1  0
 16 14  1  0
 14 15  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  2  3
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
 27 25  1  0
  8 28  1  0
 21 23  1  0
 12 18  1  0
 26 53  1  0
 26 54  1  0
 26 55  1  0
 25 52  1  6
 24 50  1  0
 24 51  1  0
 28 56  1  6
 19 49  1  1
 18 48  1  1
 16 44  1  6
 17 45  1  0
 17 46  1  0
 17 47  1  0
 14 42  1  1
 15 43  1  0
 13 40  1  0
 13 41  1  0
 12 39  1  1
 11 37  1  0
 11 38  1  0
  9 35  1  0
  9 36  1  0
  8 34  1  6
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
M  END


  Mrv1652304282210212D          

 28 31  0  0  1  0            999 V2000
    3.7268    3.2209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3592    2.4823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5526    2.3093    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9143    2.8320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9251    3.6569    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5768    4.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786    3.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9014    4.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865    4.0246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356    4.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8233    5.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970    5.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2906    4.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    6.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924    6.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2199    2.3865    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4290    1.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9063    0.9502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.5407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644    2.0552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1331    2.8107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8886    3.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6355    3.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480    1.9045    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6796    2.2859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5429    3.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4181    1.9183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8266    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  5  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  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  3 19  1  6  0  0  0
 16 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 21 23  1  6  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  1 26  1  6  0  0  0
 25 27  1  6  0  0  0
 24 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0064069

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@]2(O1)[C@@H]1[C@@H](OC2=O)[C@H]2[C@H](C)[C@@H](O)C[C@H]2C(=C)C[C@@H]1OC(=O)C(=C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O7/c1-9-5-15(26-19(24)10(2)8-22)17-18(16-12(4)14(23)6-13(9)16)27-20(25)21(17)7-11(3)28-21/h11-18,22-23H,1-2,5-8H2,3-4H3/t11-,12-,13+,14+,15+,16+,17+,18+,21+/m1/s1

> <INCHI_KEY>
ASHNISLKCRABOJ-JDNQVCSQSA-N

> <FORMULA>
C21H28O7

> <MOLECULAR_WEIGHT>
392.448

> <EXACT_MASS>
392.183503242

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.47228214885896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aS,4S,4'R,6aR,8S,9S,9aR,9bS)-8-hydroxy-4',9-dimethyl-6-methylidene-2-oxo-decahydro-2H-spiro[azuleno[4,5-b]furan-3,2'-oxetane]-4-yl 2-(hydroxymethyl)prop-2-enoate

> <ALOGPS_LOGP>
0.69

> <JCHEM_LOGP>
1.043972017666666

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.211935185126237

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.609405904980207

> <JCHEM_PKA_STRONGEST_BASIC>
-2.831627736645924

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
98.0727

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aS,4S,4'R,6aR,8S,9S,9aR,9bS)-8-hydroxy-4',9-dimethyl-6-methylidene-2-oxo-octahydro-3aH-spiro[azuleno[4,5-b]furan-3,2'-oxetane]-4-yl 2-(hydroxymethyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.957   6.012   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.271   4.634   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.765   4.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.573   5.286   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.594   6.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.810   7.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.307   7.408   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.283   8.600   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.215   7.513   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.120   9.050   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.403   9.900   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.741   9.736   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.542   8.885   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.646  11.273   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.733  11.959   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.277   4.455   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.668   2.965   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.692   1.774   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.205   2.876   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.867   3.836   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.248   5.247   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.659   5.865   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.186   5.807   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.370   3.555   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.735   4.267   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.480   5.786   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.114   3.581   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.143   2.032   0.000  0.00  0.00           C+0
CONECT    1    2    7   26                                                  
CONECT    2    1    3   24                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    4   17   20   22                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    3                                                       
CONECT   20   16   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   16                                                       
CONECT   23   21                                                            
CONECT   24    2   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25    1                                                       
CONECT   27   25                                                            
CONECT   28   24                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
(3S,3AS,4S,4'r,6ar,8S,9S,9ar,9BS)-8-hydroxy-4',9-dimethyl-6-methylidene-2-oxo-decahydro-2H-spiro[azuleno[4,5-b]furan-3,2'-oxetane]-4-yl 2-(hydroxymethyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₁H₂₈O₇

Average Mass

392.4480 Da

Monoisotopic Mass

392.18350 Da

IUPAC Name

(3S,3aS,4S,4'R,6aR,8S,9S,9aR,9bS)-8-hydroxy-4',9-dimethyl-6-methylidene-2-oxo-decahydro-2H-spiro[azuleno[4,5-b]furan-3,2'-oxetane]-4-yl 2-(hydroxymethyl)prop-2-enoate

Traditional Name

(3S,3aS,4S,4'R,6aR,8S,9S,9aR,9bS)-8-hydroxy-4',9-dimethyl-6-methylidene-2-oxo-octahydro-3aH-spiro[azuleno[4,5-b]furan-3,2'-oxetane]-4-yl 2-(hydroxymethyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@]2(O1)[C@@H]1[C@@H](OC2=O)[C@H]2[C@H](C)[C@@H](O)C[C@H]2C(=C)C[C@@H]1OC(=O)C(=C)CO

InChI Identifier

InChI=1S/C21H28O7/c1-9-5-15(26-19(24)10(2)8-22)17-18(16-12(4)14(23)6-13(9)16)27-20(25)21(17)7-11(3)28-21/h11-18,22-23H,1-2,5-8H2,3-4H3/t11-,12-,13+,14+,15+,16+,17+,18+,21+/m1/s1

InChI Key

ASHNISLKCRABOJ-JDNQVCSQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 clementei	Plant	KNApSAcK

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
Beta-hydroxy acid
Hydroxy acid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Oxetane
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	0.69	ALOGPS
logP	1.04	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.61	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.07 m³·mol⁻¹	ChemAxon
Polarizability	40.47 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

162892513

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Clementein C (NP0064069)

MOL for NP0064069 (Clementein C)

3D MOL for NP0064069 (Clementein C)

3D SDF for NP0064069 (Clementein C)

3D-SDF for NP0064069 (Clementein C)

PDB for NP0064069 (Clementein C)

3D PDB for NP0064069 (Clementein C)

SMILES for NP0064069 (Clementein C)

INCHI for NP0064069 (Clementein C)

Structure for NP0064069 (Clementein C)

3D Structure for NP0064069 (Clementein C)