NP-MRD: Showing NP-Card for (1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate (NP0295636)

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Record Information

Version

2.0

Created at

2022-09-10 04:43:44 UTC

Updated at

2022-09-10 04:43:45 UTC

NP-MRD ID

NP0295636

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate

Description

(1S)-alpha-Methylene-2alpha-hydroxy-3beta-[1-(hydroxymethyl)ethenyl]-4alpha-ethenyl-4-methyl-6alpha-[[(Z)-2-(hydroxymethyl)-4-acetoxy-2-butenoyl]oxy]cyclohexane-1beta-acetic acid methyl ester belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. (1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate is found in Centaurea aspera. Based on a literature review very few articles have been published on (1S)-alpha-Methylene-2alpha-hydroxy-3beta-[1-(hydroxymethyl)ethenyl]-4alpha-ethenyl-4-methyl-6alpha-[[(Z)-2-(hydroxymethyl)-4-acetoxy-2-butenoyl]oxy]cyclohexane-1beta-acetic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102206432D          

 32 32  0  0  1  0            999 V2000
    0.4663    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
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 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  1  0  0  0
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 22 23  2  0  0  0  0
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 24 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 64 64  0  0  0  0  0  0  0  0999 V2000
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    1.7643    0.9445   -0.9265 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4428    1.9271   -1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9716    2.8476   -0.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4339    2.8211    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287    3.7508    2.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5145    2.0494    1.5470 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1711   -1.6638    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7254   -2.5883   -0.7997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329   -1.0715    0.9560 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1509    0.0436    1.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254   -0.2319    2.9363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3634    1.4482    1.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    1.8089    0.4791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1096    2.4565    2.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122    3.8135    2.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0961   -1.2791    0.9939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3701   -2.4165    1.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8619   -1.3588   -0.2576 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0796   -0.5336   -0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2146    0.5600    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2416   -0.9417   -1.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9938   -1.0149   -2.4951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910   -4.1239   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7740   -2.1378   -3.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9297    0.0795   -2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5486   -0.1605   -3.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112   -2.9405   -0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -1.8665   -2.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1847    0.0739   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7201    0.2986   -0.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235    2.2657   -1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0718    2.0185   -1.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6061    3.1897    2.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5475    4.5182    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874    4.1747    2.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2539   -1.7458    0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6499   -1.9059    1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6944   -2.1706   -1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1549   -2.0104    1.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7313   -1.2450    3.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8812    0.5645    3.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890    4.4300    2.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    3.8407    1.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642    4.2486    1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5051   -0.4508    1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880   -2.4971    2.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3337   -2.4379   -0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3493   -0.2367   -3.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
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 28  3  1  0
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 17 18  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  3  2  1  6
  2  1  2  3
  6 19  1  0
 25 54  1  0
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 25 56  1  0
 21 52  1  0
 21 53  1  0
 19 51  1  1
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 27 58  1  0
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 31 63  1  0
 32 64  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  6
 17 48  1  0
 17 49  1  0
 18 50  1  0
 11 42  1  0
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 15 45  1  0
 15 46  1  0
 15 47  1  0
  2 35  1  0
  1 33  1  0
  1 34  1  0
M  END


  Mrv1652309102206432D          

 32 32  0  0  1  0            999 V2000
    0.4663    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  8  9  2  0  0  0  0
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 19 26  1  0  0  0  0
 26 27  1  6  0  0  0
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 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0295636

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=C)[C@H]1[C@H](O)[C@@H](C(=C)CO)[C@@](C)(C[C@@H]1OC(=O)C(\CO)=C/COC(C)=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O9/c1-7-23(5)10-17(32-22(29)16(12-25)8-9-31-15(4)26)18(14(3)21(28)30-6)20(27)19(23)13(2)11-24/h7-8,17-20,24-25,27H,1-3,9-12H2,4-6H3/b16-8-/t17-,18+,19+,20-,23+/m0/s1

> <INCHI_KEY>
IWDKJDOUWOTZPS-UPUSNDMNSA-N

> <FORMULA>
C23H32O9

> <MOLECULAR_WEIGHT>
452.5

> <EXACT_MASS>
452.20463261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.916666671825794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3R,4R,5S)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2Z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate

> <JCHEM_LOGP>
0.5436772746666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.832835801024544

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.238301951734837

> <JCHEM_PKA_STRONGEST_BASIC>
-2.72833544057322

> <JCHEM_POLAR_SURFACE_AREA>
139.59

> <JCHEM_REFRACTIVITY>
116.10409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4R,5S)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2Z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.870   4.937   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   28                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   10   18                                                       
CONECT   18   17                                                            
CONECT   19    6   20   26                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   19   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    3   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

View in JSmol

Synonyms

Value	Source
(1S)-a-Methylene-2a-hydroxy-3b-[1-(hydroxymethyl)ethenyl]-4a-ethenyl-4-methyl-6a-[[(Z)-2-(hydroxymethyl)-4-acetoxy-2-butenoyl]oxy]cyclohexane-1b-acetate methyl ester	Generator
(1S)-a-Methylene-2a-hydroxy-3b-[1-(hydroxymethyl)ethenyl]-4a-ethenyl-4-methyl-6a-[[(Z)-2-(hydroxymethyl)-4-acetoxy-2-butenoyl]oxy]cyclohexane-1b-acetic acid methyl ester	Generator
(1S)-alpha-Methylene-2alpha-hydroxy-3beta-[1-(hydroxymethyl)ethenyl]-4alpha-ethenyl-4-methyl-6alpha-[[(Z)-2-(hydroxymethyl)-4-acetoxy-2-butenoyl]oxy]cyclohexane-1beta-acetate methyl ester	Generator
(1S)-Α-methylene-2α-hydroxy-3β-[1-(hydroxymethyl)ethenyl]-4α-ethenyl-4-methyl-6α-[[(Z)-2-(hydroxymethyl)-4-acetoxy-2-butenoyl]oxy]cyclohexane-1β-acetate methyl ester	Generator
(1S)-Α-methylene-2α-hydroxy-3β-[1-(hydroxymethyl)ethenyl]-4α-ethenyl-4-methyl-6α-[[(Z)-2-(hydroxymethyl)-4-acetoxy-2-butenoyl]oxy]cyclohexane-1β-acetic acid methyl ester	Generator

Chemical Formula

C₂₃H₃₂O₉

Average Mass

452.5000 Da

Monoisotopic Mass

452.20463 Da

IUPAC Name

(1S,2S,3R,4R,5S)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2Z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate

Traditional Name

(1S,2S,3R,4R,5S)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2Z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C)[C@H]1[C@H](O)[C@@H](C(=C)CO)[C@@](C)(C[C@@H]1OC(=O)C(\CO)=C/COC(C)=O)C=C

InChI Identifier

InChI=1S/C23H32O9/c1-7-23(5)10-17(32-22(29)16(12-25)8-9-31-15(4)26)18(14(3)21(28)30-6)20(27)19(23)13(2)11-24/h7-8,17-20,24-25,27H,1-3,9-12H2,4-6H3/b16-8-/t17-,18+,19+,20-,23+/m0/s1

InChI Key

IWDKJDOUWOTZPS-UPUSNDMNSA-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 aspera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Elemane sesquiterpenoids

Alternative Parents

Substituents

Elemane sesquiterpenoid
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Cyclohexanol
Fatty acid ester
Fatty acyl
Hydroxy acid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Primary alcohol
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	0.54	ChemAxon
pKa (Strongest Acidic)	14.24	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	116.1 m³·mol⁻¹	ChemAxon
Polarizability	46.92 Å³	ChemAxon
Number of Rings	1	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

97301589

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate (NP0295636)

MOL for NP0295636 ((1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate)

3D MOL for NP0295636 ((1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate)

3D SDF for NP0295636 ((1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate)

3D-SDF for NP0295636 ((1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate)

PDB for NP0295636 ((1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate)

3D PDB for NP0295636 ((1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate)

SMILES for NP0295636 ((1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate)

INCHI for NP0295636 ((1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate)

Structure for NP0295636 ((1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate)

3D Structure for NP0295636 ((1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (2z)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate)