NP-MRD: Showing NP-Card for (1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate (NP0240367)

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Record Information

Version

1.0

Created at

2022-09-07 00:10:46 UTC

Updated at

2022-09-07 00:10:46 UTC

NP-MRD ID

NP0240367

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate

Description

(1S,2S,4aR,7R,8aR)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-decahydronaphthalen-2-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. (1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate is found in Pluchea arguta. Based on a literature review very few articles have been published on (1S,2S,4aR,7R,8aR)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-decahydronaphthalen-2-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072202102D          

 28 30  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2461   -0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4336    0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2461    0.6320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0213    0.9142    0.0000 C   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
    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 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  6  0  0  0
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  6  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    4.4855    1.5306   -1.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3960    0.8715   -0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6148    0.6369    0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6256    0.0147    1.6379 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8593    1.1015    0.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0345    0.8617    0.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1188    0.3624    0.2925 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9229    0.7450   -0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6946    0.2441    0.2393 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5361    1.0076   -0.1765 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8011    0.9727   -1.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2451    2.3610    0.1358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6891    0.5674    0.6676 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7156   -0.0512   -0.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0055    0.4554   -0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    1.4765    0.6523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301   -0.1233   -0.8077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7295   -1.3573   -1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0828    0.7315   -1.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4950   -0.1659   -0.2666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8659    0.5042    1.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448   -0.3798    1.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5487   -1.5863    1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5627   -1.2295    0.2465 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1637   -1.8273   -1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -1.8754    0.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0659   -1.1148    0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1238   -1.7163    0.3864 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6063    1.7199   -1.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4278    1.8997   -1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8401    1.5354    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8303    1.0993    1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3825   -0.1788    0.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450    0.7951    1.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    0.2888   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202    1.8492   -0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8926    0.5665    1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3409    1.9307   -1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4427    0.1667   -1.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1735    1.0536   -2.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375    2.8632   -0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332    1.4355    1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3173   -2.0861   -0.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6323   -1.8342   -2.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -1.0943   -2.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1823   -0.9813   -0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5206    1.5566    1.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2797   -0.0057    1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9438    0.5011    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6918    0.1902    2.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1869   -0.7305    2.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0946   -2.1204    2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823   -2.2925    0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5911   -2.8724   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9478   -2.0029   -1.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475   -1.3046   -1.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704   -2.8969    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7692   -2.0689    1.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 24  1  0
 24 25  1  6
 24 23  1  0
 23 22  1  0
 22 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 17 15  1  1
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 13 10  1  0
 10 11  1  0
 10 12  1  1
 24 26  1  0
 26 27  1  0
 27 28  2  0
 27  7  1  0
 10  9  1  0
 20 17  1  0
  6 31  1  0
  6 32  1  0
  6 33  1  0
  1 29  1  0
  1 30  1  0
  7 34  1  1
  8 35  1  0
  8 36  1  0
  9 37  1  1
 25 54  1  0
 25 55  1  0
 25 56  1  0
 23 52  1  0
 23 53  1  0
 22 50  1  0
 22 51  1  0
 13 42  1  1
 18 43  1  0
 18 44  1  0
 18 45  1  0
 20 46  1  6
 21 47  1  0
 21 48  1  0
 21 49  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 26 57  1  0
 26 58  1  0
M  END


  Mrv1652309072202102D          

 28 30  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2461   -0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4336    0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2461    0.6320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0213    0.9142    0.0000 C   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
    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 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  6  0  0  0
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  6  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  6  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0240367

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=C)[C@H]1C[C@@H]2[C@](C)(CC[C@H](OC(=O)[C@]3(C)O[C@@H]3C)[C@@]2(C)O)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O7/c1-11(17(23)26-6)13-9-15-19(3,10-14(13)22)8-7-16(20(15,4)25)27-18(24)21(5)12(2)28-21/h12-13,15-16,25H,1,7-10H2,2-6H3/t12-,13-,15-,16+,19-,20+,21-/m1/s1

> <INCHI_KEY>
QTONZIOQMXPFGE-AKFLGSBASA-N

> <FORMULA>
C21H30O7

> <MOLECULAR_WEIGHT>
394.464

> <EXACT_MASS>
394.199153306

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.834782026724845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4aR,7R,8aR)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-decahydronaphthalen-2-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

> <JCHEM_LOGP>
2.3392236090000007

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.86598503374972

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.492772390837523

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3273738030865196

> <JCHEM_POLAR_SURFACE_AREA>
102.43

> <JCHEM_REFRACTIVITY>
99.31289999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4aR,7R,8aR)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2H-naphthalen-2-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.325   1.180   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.659  -1.180   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.143   1.447   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.659   1.180   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.106   1.706   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    2    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   24                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   17   21                                                  
CONECT   21   20                                                            
CONECT   22   13   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    9   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26    7   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,4AR,7R,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-decahydronaphthalen-2-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylic acid	Generator

Chemical Formula

C₂₁H₃₀O₇

Average Mass

394.4640 Da

Monoisotopic Mass

394.19915 Da

IUPAC Name

(1S,2S,4aR,7R,8aR)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-decahydronaphthalen-2-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

Traditional Name

(1S,2S,4aR,7R,8aR)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2H-naphthalen-2-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C)[C@H]1C[C@@H]2[C@](C)(CC[C@H](OC(=O)[C@]3(C)O[C@@H]3C)[C@@]2(C)O)CC1=O

InChI Identifier

InChI=1S/C21H30O7/c1-11(17(23)26-6)13-9-15-19(3,10-14(13)22)8-7-16(20(15,4)25)27-18(24)21(5)12(2)28-21/h12-13,15-16,25H,1,7-10H2,2-6H3/t12-,13-,15-,16+,19-,20+,21-/m1/s1

InChI Key

QTONZIOQMXPFGE-AKFLGSBASA-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
Pluchea arguta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Dicarboxylic acid or derivatives
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.34	ChemAxon
pKa (Strongest Acidic)	12.49	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	102.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.31 m³·mol⁻¹	ChemAxon
Polarizability	41.83 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	Yes	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

163046390

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,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate (NP0240367)

MOL for NP0240367 ((1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

3D MOL for NP0240367 ((1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

3D SDF for NP0240367 ((1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

3D-SDF for NP0240367 ((1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

PDB for NP0240367 ((1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

3D PDB for NP0240367 ((1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

SMILES for NP0240367 ((1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

INCHI for NP0240367 ((1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

Structure for NP0240367 ((1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

3D Structure for NP0240367 ((1s,2s,4ar,7r,8ar)-1-hydroxy-7-(3-methoxy-3-oxoprop-1-en-2-yl)-1,4a-dimethyl-6-oxo-hexahydro-2h-naphthalen-2-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)