NP-MRD: Showing NP-Card for methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate (NP0235742)

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Record Information

Version

2.0

Created at

2022-09-06 18:27:59 UTC

Updated at

2022-09-06 18:27:59 UTC

NP-MRD ID

NP0235742

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate

Description

Methyl (2R,2'S,5'R)-5'-(benzoyloxy)-2',6',6'-trimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate is found in Heliotropium filifolium. Based on a literature review very few articles have been published on methyl (2R,2'S,5'R)-5'-(benzoyloxy)-2',6',6'-trimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062220282D          

 30 33  0  0  1  0            999 V2000
    7.7859    3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0714    3.2577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    4.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425    3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9280    2.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9280    3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289    3.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440    2.8452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4289    2.1777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5315    2.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9440    1.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    3.5596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2940    4.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690    4.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    3.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    4.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    4.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1810    5.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    6.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    6.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690    5.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5315    3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603    4.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311    3.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 18 28  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
   -8.1912    2.4423   -0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0515    1.7845   -0.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0057    1.3532   -0.9349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0740    1.5568   -2.1678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8848    0.6864   -0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8469    0.4810    1.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7951   -0.1482    1.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6918   -0.6188    0.9687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7346   -0.4110   -0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7908    0.2196   -1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4741   -0.9885   -0.9072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5900   -1.1322    0.3057 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5306   -1.2712    1.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2221   -2.3904    0.1999 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8820   -2.5873   -1.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2882   -2.4962    1.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -1.3070    2.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4488   -0.0612    1.3031 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6292   -0.1302    0.5246 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6950    0.7507    0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5576    1.6295    1.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8966    0.6521   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9273    1.5444    0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0922    1.4872   -0.6964 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2406    0.5253   -1.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2163   -0.3789   -1.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0511   -0.3069   -1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2201    0.1099    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6379    1.1553    1.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6823    0.7113   -0.8610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8763    1.7912   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6897    3.0119    0.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8043    3.2282   -1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7135    0.8511    1.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866   -0.2993    2.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267    0.3843   -2.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0652   -0.2913   -1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6349   -1.9530   -1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763   -3.2405    0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9119   -2.1712   -1.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0388   -3.7024   -1.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752   -2.2969   -2.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2721   -2.6932    0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956   -3.3817    1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3605   -1.3735    2.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086   -1.2616    2.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5862    0.7909    2.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8694    2.3321    0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8929    2.1895   -0.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1297    0.4410   -2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3416   -1.1296   -2.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2568   -0.9990   -1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    1.9941    1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977    1.4903    0.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9714    0.7104    2.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167    1.3170   -0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0415    1.4240   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427   -0.0244   -1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8 13  1  0
 12 13  1  1
 12 11  1  0
 11  9  1  0
  9 10  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 18 28  1  0
 28 29  1  0
 28 30  1  0
 10  5  1  0
 27 22  1  0
  9  8  1  0
 28 12  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  7 35  1  0
 11 37  1  0
 11 38  1  0
 10 36  1  0
 14 39  1  1
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  1
 23 48  1  0
 24 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 30 58  1  0
M  END


  Mrv1652309062220282D          

 30 33  0  0  1  0            999 V2000
    7.7859    3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0714    3.2577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    4.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425    3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9280    2.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9280    3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289    3.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440    2.8452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4289    2.1777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5315    2.1307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9440    1.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    3.5596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2940    4.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690    4.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    3.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    4.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    4.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1810    5.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    6.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    6.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690    5.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5315    3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603    4.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311    3.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 18 28  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0235742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC=C2O[C@]3(CC2=C1)[C@@H](C)CC[C@@H](OC(=O)C1=CC=CC=C1)C3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O5/c1-16-10-13-21(29-23(27)17-8-6-5-7-9-17)24(2,3)25(16)15-19-14-18(22(26)28-4)11-12-20(19)30-25/h5-9,11-12,14,16,21H,10,13,15H2,1-4H3/t16-,21+,25+/m0/s1

> <INCHI_KEY>
ZCNGYPFWHGRPSJ-XUMWYHAOSA-N

> <FORMULA>
C25H28O5

> <MOLECULAR_WEIGHT>
408.494

> <EXACT_MASS>
408.193674002

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.41684254863431

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R,3'R,6'S)-3'-(benzoyloxy)-2',2',6'-trimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate

> <JCHEM_LOGP>
5.954414550333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.892317141895416

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
113.43870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R,3'R,6'S)-3'-(benzoyloxy)-2',2',6'-trimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      14.534   6.851   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.200   6.081   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.866   6.851   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.866   8.391   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.533   6.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.533   4.541   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.199   3.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.865   4.541   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.865   6.081   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.199   6.851   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.401   6.557   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.495   5.311   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.401   4.065   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.725   3.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.495   2.644   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.185   3.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.415   5.311   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.185   6.645   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.415   7.978   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.875   7.978   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.105   6.645   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.105   9.312   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.435   9.312   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.205  10.646   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.435  11.979   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.105  11.979   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.875  10.646   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.725   6.645   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.779   8.184   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.031   7.461   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   14   28                                             
CONECT   13   12    8                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   18   12   29   30                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2R,2's,5'r)-5'-(benzoyloxy)-2',6',6'-trimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylic acid	Generator

Chemical Formula

C₂₅H₂₈O₅

Average Mass

408.4940 Da

Monoisotopic Mass

408.19367 Da

IUPAC Name

methyl (2R,3'R,6'S)-3'-(benzoyloxy)-2',2',6'-trimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate

Traditional Name

methyl (2R,3'R,6'S)-3'-(benzoyloxy)-2',2',6'-trimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC=C2O[C@]3(CC2=C1)[C@@H](C)CC[C@@H](OC(=O)C1=CC=CC=C1)C3(C)C

InChI Identifier

InChI=1S/C25H28O5/c1-16-10-13-21(29-23(27)17-8-6-5-7-9-17)24(2,3)25(16)15-19-14-18(22(26)28-4)11-12-20(19)30-25/h5-9,11-12,14,16,21H,10,13,15H2,1-4H3/t16-,21+,25+/m0/s1

InChI Key

ZCNGYPFWHGRPSJ-XUMWYHAOSA-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
Heliotropium filifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzofuran
Coumaran
Benzoyl
Alkyl aryl ether
Dicarboxylic acid or derivatives
Methyl ester
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	5.95	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.44 m³·mol⁻¹	ChemAxon
Polarizability	44.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

162927699

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate (NP0235742)

MOL for NP0235742 (methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate)

3D MOL for NP0235742 (methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate)

3D SDF for NP0235742 (methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate)

3D-SDF for NP0235742 (methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate)

PDB for NP0235742 (methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate)

3D PDB for NP0235742 (methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate)

SMILES for NP0235742 (methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate)

INCHI for NP0235742 (methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate)

Structure for NP0235742 (methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate)

3D Structure for NP0235742 (methyl (2r,3'r,6's)-3'-(benzoyloxy)-2',2',6'-trimethyl-3h-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate)