NP-MRD: Showing NP-Card for (1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate (NP0198909)

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Record Information

Version

2.0

Created at

2022-09-04 17:26:50 UTC

Updated at

2022-09-04 17:26:50 UTC

NP-MRD ID

NP0198909

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate

Description

3-Methyl-2-butenoic acid [(3aalpha,7abeta)-1beta-[(R)-1-(acetyloxy)ethyl]octahydro-4-methylene-7beta-(1-methylethyl)-2-oxo-1H-inden]-5alpha-yl ester belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate is found in Tussilago farfara. Based on a literature review very few articles have been published on 3-Methyl-2-butenoic acid [(3aalpha,7abeta)-1beta-[(R)-1-(acetyloxy)ethyl]octahydro-4-methylene-7beta-(1-methylethyl)-2-oxo-1H-inden]-5alpha-yl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219262D          

 27 28  0  0  1  0            999 V2000
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7179   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769   -1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -3.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150   -2.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  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  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  1  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 27 26  1  1  0  0  0
  2 27  1  0  0  0  0
 16 27  1  0  0  0  0
M  END

     RDKit          3D

 59 60  0  0  0  0  0  0  0  0999 V2000
    1.7900   -0.2305    2.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2234   -0.1392    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003   -0.9101    0.1103 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9218   -0.2566   -0.2787 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1289   -0.9019   -0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1033   -2.1366    0.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3829   -0.2761   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4597    0.9880   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2419    1.8376   -1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7461    1.6328   -1.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558   -0.7414   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6907   -0.8233   -0.6815 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2042   -2.2487   -0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -3.1334    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0722   -2.8855   -2.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0657   -0.1640    0.5944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1459    0.8556    0.4902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5436    0.3123    0.4079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9169   -0.5676    1.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4065    1.4242    0.2428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1450    1.6523   -0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0463    2.8428   -1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0079    0.8033   -1.8286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208    1.6704    1.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6555    2.4522    2.2856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5263    1.3960    2.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0857    0.7263    1.0407 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4185    0.3439    3.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6523   -0.8831    2.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9260   -1.9558    0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2899   -0.8591   -0.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7643    1.9067   -0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4770    2.8872   -1.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4722    1.4449   -1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5485    1.1404   -0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8309    1.5256   -2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7220    2.6985   -1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700   -1.5316   -1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9462    0.2298   -1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708   -0.3144   -1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2857   -2.2567   -0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125   -3.9580    0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429   -3.6698   -0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2013   -2.6637    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953   -3.4071   -2.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1311   -2.1087   -2.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -3.6449   -2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2770   -0.9007    1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722    1.4627   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6117   -0.2644   -0.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2426   -0.5006    2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9790   -0.3401    1.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9203   -1.6229    1.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5423    3.6752   -0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0564    3.1107   -2.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0463    2.6563   -0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491    0.7773    3.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488    2.3886    2.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    1.4546    0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 13 12  1  0
 12 11  1  0
 11  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  3  2  1  0
  2  1  2  3
  2 27  1  0
 27 26  1  0
 26 24  1  0
 24 25  2  0
 24 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 17 16  1  0
 16 12  1  0
 16 27  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 13 41  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 12 40  1  6
 11 38  1  0
 11 39  1  0
  3 30  1  1
  7 31  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
  1 28  1  0
  1 29  1  0
 27 59  1  6
 26 57  1  0
 26 58  1  0
 17 49  1  6
 18 50  1  6
 19 51  1  0
 19 52  1  0
 19 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 16 48  1  1
M  END


  Mrv1652309042219262D          

 27 28  0  0  1  0            999 V2000
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7179   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769   -1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -3.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150   -2.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  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  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  1  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 27 26  1  1  0  0  0
  2 27  1  0  0  0  0
 16 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198909

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O5/c1-11(2)8-20(25)27-19-10-16(12(3)4)22-17(13(19)5)9-18(24)21(22)14(6)26-15(7)23/h8,12,14,16-17,19,21-22H,5,9-10H2,1-4,6-7H3/t14-,16+,17+,19-,21+,22+/m1/s1

> <INCHI_KEY>
VUQPPZBQPRNJCH-VJTSRSJPSA-N

> <FORMULA>
C22H32O5

> <MOLECULAR_WEIGHT>
376.493

> <EXACT_MASS>
376.22497413

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.01139610912271

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3aR,5R,7S,7aS)-1-[(1R)-1-(acetyloxy)ethyl]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl 3-methylbut-2-enoate

> <JCHEM_LOGP>
3.9509078693333346

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.16527458479869

> <JCHEM_PKA_STRONGEST_BASIC>
-6.545611278071427

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
103.35739999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3aR,5R,7S,7aS)-1-[(1R)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1H-inden-5-yl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.788   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.789   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.340  -2.261   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.877  -3.085   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.401  -4.550   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.432  -5.694   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.895  -4.870   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12   17   27                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26    2   16                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
3-Methyl-2-butenoate [(3aalpha,7abeta)-1b-[(R)-1-(acetyloxy)ethyl]octahydro-4-methylene-7b-(1-methylethyl)-2-oxo-1H-inden]-5a-yl ester	Generator
3-Methyl-2-butenoate [(3aalpha,7abeta)-1beta-[(R)-1-(acetyloxy)ethyl]octahydro-4-methylene-7beta-(1-methylethyl)-2-oxo-1H-inden]-5alpha-yl ester	Generator
3-Methyl-2-butenoate [(3aalpha,7abeta)-1β-[(R)-1-(acetyloxy)ethyl]octahydro-4-methylene-7β-(1-methylethyl)-2-oxo-1H-inden]-5α-yl ester	Generator
3-Methyl-2-butenoic acid [(3aalpha,7abeta)-1b-[(R)-1-(acetyloxy)ethyl]octahydro-4-methylene-7b-(1-methylethyl)-2-oxo-1H-inden]-5a-yl ester	Generator
3-Methyl-2-butenoic acid [(3aalpha,7abeta)-1β-[(R)-1-(acetyloxy)ethyl]octahydro-4-methylene-7β-(1-methylethyl)-2-oxo-1H-inden]-5α-yl ester	Generator

Chemical Formula

C₂₂H₃₂O₅

Average Mass

376.4930 Da

Monoisotopic Mass

376.22497 Da

IUPAC Name

(1S,3aR,5R,7S,7aS)-1-[(1R)-1-(acetyloxy)ethyl]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl 3-methylbut-2-enoate

Traditional Name

(1S,3aR,5R,7S,7aS)-1-[(1R)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1H-inden-5-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H32O5/c1-11(2)8-20(25)27-19-10-16(12(3)4)22-17(13(19)5)9-18(24)21(22)14(6)26-15(7)23/h8,12,14,16-17,19,21-22H,5,9-10H2,1-4,6-7H3/t14-,16+,17+,19-,21+,22+/m1/s1

InChI Key

VUQPPZBQPRNJCH-VJTSRSJPSA-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
Tussilago farfara	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oplopane sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.95	ChemAxon
pKa (Strongest Acidic)	19.17	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.36 m³·mol⁻¹	ChemAxon
Polarizability	42.01 Å³	ChemAxon
Number of Rings	2	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

103884148

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101641866

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate (NP0198909)

MOL for NP0198909 ((1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate)

3D MOL for NP0198909 ((1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate)

3D SDF for NP0198909 ((1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate)

3D-SDF for NP0198909 ((1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate)

PDB for NP0198909 ((1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate)

3D PDB for NP0198909 ((1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate)

SMILES for NP0198909 ((1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate)

INCHI for NP0198909 ((1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate)

Structure for NP0198909 ((1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate)

3D Structure for NP0198909 ((1s,3ar,5r,7s,7as)-1-[(1r)-1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1h-inden-5-yl 3-methylbut-2-enoate)