NP-MRD: Showing NP-Card for methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate (NP0235128)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 17:35:03 UTC

Updated at

2022-09-06 17:35:03 UTC

NP-MRD ID

NP0235128

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate

Description

(2S,3aR,4S,4'S,5'R,6S,7aR)-4'-(Benzoyloxy)-3a,4-dihydroxy-3',3a,4,4',5,5',6,6',7,7a-decahydro-5'-methyl-3-oxospiro[benzofuran-2(3H),2'-[2H]pyran]-6-carboxylic acid methyl ester belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate is found in Phyllanthus emblica. Based on a literature review very few articles have been published on (2S,3aR,4S,4'S,5'R,6S,7aR)-4'-(Benzoyloxy)-3a,4-dihydroxy-3',3a,4,4',5,5',6,6',7,7a-decahydro-5'-methyl-3-oxospiro[benzofuran-2(3H),2'-[2H]pyran]-6-carboxylic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062219352D          

 31 34  0  0  1  0            999 V2000
   -2.1434   -0.4125    0.0000 C   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
   -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
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5152    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1110    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3485    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5860    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1735    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 O   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
    0.7145   -0.4125    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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 13 29  1  6  0  0  0
 30 29  1  6  0  0  0
  9 30  1  0  0  0  0
 30 31  1  0  0  0  0
  5 31  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.8801    3.3822   -2.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7364    2.8209   -1.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7288    1.7224   -0.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8154    1.1715   -0.3725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4101    1.2646   -0.1604 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5888    0.2399    0.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8444   -1.1410    0.3673 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9536   -2.0438    1.4062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7064   -1.5177   -0.5034 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8981   -2.7739   -1.0703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4013   -1.5778    0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -1.7553    1.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3961   -1.3624   -0.8470 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6912   -0.4082   -0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.0752    0.4581 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8769   -0.2407    0.5175 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3333    0.3159    1.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6968    0.0542    2.7469 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5139    1.1683    1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1763    1.4228    0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2970    2.2239    0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7982    2.8076    1.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1541    2.5717    2.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    1.7549    2.8225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1633   -2.4087   -0.1126 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8471   -2.1559   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8923   -3.2193   -0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1191   -2.5936   -1.2468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0769   -0.8397   -1.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693   -0.5498   -1.5827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5090    0.8810   -1.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9898    2.9787   -3.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7255    4.4985   -2.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7730    3.1395   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    2.1729    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4743    0.5257    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259    0.2158    1.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7591   -1.1098   -0.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9313   -2.9786    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5446   -3.4359   -0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1210    0.0664   -1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    0.3955    0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2654   -1.2341    1.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7842    0.9644   -0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7837    2.3946   -0.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6851    3.4516    1.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5561    3.0345    3.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5355    1.5853    3.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270   -2.8935    0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874   -3.0315   -1.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4999   -1.2690   -1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1184   -2.0091   -2.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3577   -3.3211    0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910   -4.2012   -0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0076   -0.8280   -2.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8929    1.4026   -2.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875    1.3472   -1.1339 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 31  1  0
 31 30  1  0
 30 29  1  0
 13 29  1  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 15 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 13 11  1  0
 11 12  2  0
 11  9  1  0
  9 10  1  6
  9  7  1  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  9 30  1  0
 28 13  1  0
 24 19  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  1
 31 56  1  0
 31 57  1  0
 30 55  1  6
 14 41  1  0
 14 42  1  0
 15 43  1  1
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  1
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 10 40  1  0
  7 38  1  6
  8 39  1  0
  6 36  1  0
  6 37  1  0
M  END


  Mrv1652309062219352D          

 31 34  0  0  1  0            999 V2000
   -2.1434   -0.4125    0.0000 C   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
   -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
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5152    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1110    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3485    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5860    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3485    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1735    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 O   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
    0.7145   -0.4125    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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 13 29  1  6  0  0  0
 30 29  1  6  0  0  0
  9 30  1  0  0  0  0
 30 31  1  0  0  0  0
  5 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0235128

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1C[C@H]2O[C@@]3(C[C@H](OC(=O)C4=CC=CC=C4)[C@H](C)CO3)C(=O)[C@@]2(O)[C@@H](O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O9/c1-12-11-29-21(10-15(12)30-19(25)13-6-4-3-5-7-13)20(26)22(27)16(23)8-14(18(24)28-2)9-17(22)31-21/h3-7,12,14-17,23,27H,8-11H2,1-2H3/t12-,14+,15+,16+,17-,21+,22-/m1/s1

> <INCHI_KEY>
WOAOYJSNCNMIET-OPYGUJPJSA-N

> <FORMULA>
C22H26O9

> <MOLECULAR_WEIGHT>
434.441

> <EXACT_MASS>
434.157682417

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.92848682020463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S,3aR,4S,4'S,5'R,6S,7aR)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-hexahydro-3H-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate

> <JCHEM_LOGP>
2.200350674666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.498377456287955

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.10118943718548

> <JCHEM_PKA_STRONGEST_BASIC>
-3.363819724362373

> <JCHEM_POLAR_SURFACE_AREA>
128.59000000000003

> <JCHEM_REFRACTIVITY>
104.46310000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,3aR,4S,4'S,5'R,6S,7aR)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4H-spiro[1-benzofuran-2,2'-oxane]-6-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      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+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  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.828   3.072   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.132   2.016   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.608   3.481   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.807   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.347   2.104   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.117   3.437   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.347   4.771   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.807   4.771   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.117   6.105   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.347   7.438   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.117   8.772   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.657   8.772   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.427   7.438   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.657   6.105   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.117   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.657   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.347  -0.564   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.807  -0.564   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.132  -0.476   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -0.770   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   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   30                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   28   29                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   15   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   13                                                       
CONECT   29   13   30                                                       
CONECT   30   29    9   31                                                  
CONECT   31   30    5                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
(2S,3AR,4S,4's,5'r,6S,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-3',3a,4,4',5,5',6,6',7,7a-decahydro-5'-methyl-3-oxospiro[benzofuran-2(3H),2'-[2H]pyran]-6-carboxylate methyl ester	Generator

Chemical Formula

C₂₂H₂₆O₉

Average Mass

434.4410 Da

Monoisotopic Mass

434.15768 Da

IUPAC Name

methyl (2S,3aR,4S,4'S,5'R,6S,7aR)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-hexahydro-3H-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate

Traditional Name

methyl (2S,3aR,4S,4'S,5'R,6S,7aR)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4H-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1C[C@H]2O[C@@]3(C[C@H](OC(=O)C4=CC=CC=C4)[C@H](C)CO3)C(=O)[C@@]2(O)[C@@H](O)C1

InChI Identifier

InChI=1S/C22H26O9/c1-12-11-29-21(10-15(12)30-19(25)13-6-4-3-5-7-13)20(26)22(27)16(23)8-14(18(24)28-2)9-17(22)31-21/h3-7,12,14-17,23,27H,8-11H2,1-2H3/t12-,14+,15+,16+,17-,21+,22-/m1/s1

InChI Key

WOAOYJSNCNMIET-OPYGUJPJSA-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
Phyllanthus emblica	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
Benzoyl
Ketal
Dicarboxylic acid or derivatives
3-furanone
Monosaccharide
Oxane
Cyclic alcohol
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Ketone
1,2-diol
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
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	2.2	ChemAxon
pKa (Strongest Acidic)	11.1	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.46 m³·mol⁻¹	ChemAxon
Polarizability	42.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10248993

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21609770

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate (NP0235128)

MOL for NP0235128 (methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

3D MOL for NP0235128 (methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

3D SDF for NP0235128 (methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

3D-SDF for NP0235128 (methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

PDB for NP0235128 (methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

3D PDB for NP0235128 (methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

SMILES for NP0235128 (methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

INCHI for NP0235128 (methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

Structure for NP0235128 (methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)

3D Structure for NP0235128 (methyl (2s,3ar,4s,4's,5'r,6s,7ar)-4'-(benzoyloxy)-3a,4-dihydroxy-5'-methyl-3-oxo-tetrahydro-4h-spiro[1-benzofuran-2,2'-oxane]-6-carboxylate)