NP-MRD: Showing NP-Card for (2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate (NP0146918)

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Record Information

Version

2.0

Created at

2022-09-02 02:24:59 UTC

Updated at

2022-09-02 02:24:59 UTC

NP-MRD ID

NP0146918

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate

Description

72948-20-0 Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate is found in Teucrium bicolor, Teucrium creticum, Teucrium flavum, Teucrium japonicum, Teucrium polium, Teucrium sandrasicum and Teucrium scorodonia. Based on a literature review very few articles have been published on 72948-20-0.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204252D          

 29 33  0  0  1  0            999 V2000
    0.5549    1.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    1.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8259    2.2001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7559    0.7729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5799    0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569   -0.0013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9110    0.8224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1746    1.1945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014    1.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377    0.9020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0281    1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3837    0.0783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1175    0.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7028   -0.1260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5172    0.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8893    0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7045    0.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8364   -0.1986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1026   -0.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3308   -0.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5155   -0.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434   -1.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933   -0.3733    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7393   -1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489   -1.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -1.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2666   -0.4530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4429   -0.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149    0.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  2  0  0  0  0
 12 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 29  1  1  0  0  0
M  END

     RDKit          3D

 57 61  0  0  0  0  0  0  0  0999 V2000
    4.2496    0.0512    2.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332   -0.5179    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3614   -1.5695    1.2566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8670    0.1366    0.9132 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4586   -0.3965   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4130    0.3867   -1.0434 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1189   -0.3186   -2.3580 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2715   -0.4572   -3.1163 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -1.6631   -2.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7552   -1.4871   -1.3339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1532   -2.8725   -0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8032   -0.5044   -0.2038 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2095    0.0827   -0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296   -0.2678    1.1201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2801   -0.4862    1.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2590    0.3476    1.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4866   -0.2265    1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2410   -1.3513    0.7033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9523   -1.5492    0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0799   -1.3903    1.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683   -1.2266    1.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009   -1.6647    1.7517 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1461    0.6403   -0.3272 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4673    1.2873    0.9918 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3578    2.4574    0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3484    2.5421   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0191    1.7389   -1.3799 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5923    2.4755   -2.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457    1.8994   -2.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4436    0.6816    3.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1249    0.7293    2.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5378   -0.7010    3.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2098   -1.4537   -0.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678   -0.4230   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3032    0.2031   -2.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5605   -1.3898   -3.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2465   -2.3773   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2909   -2.1686   -3.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5244   -1.2430   -2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4109   -3.2416   -0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517   -3.5095   -1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1754   -2.7665   -0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8468   -0.3246   -0.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2103    1.1805   -0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947    0.5171    1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0853    1.2925    2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4752    0.1800    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4849   -2.4139    0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762    1.4705   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084    0.5679    1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5591    1.6125    1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7189    3.3908    0.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9321    2.5133    1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148    3.6117   -0.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860    2.2790    0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071    3.5938   -2.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679    2.0928   -3.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  0
  7  6  1  0
  6  5  1  1
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 23 12  1  0
 12 13  1  0
 13 14  1  0
 14 20  1  0
 20 21  1  0
 21 22  2  0
 14 15  1  0
 15 19  2  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 12 10  1  0
 12 21  1  1
 16 15  1  0
 27  6  1  0
 27 29  1  6
 11 40  1  0
 11 41  1  0
 11 42  1  0
 10 39  1  6
  9 37  1  0
  9 38  1  0
  7 35  1  6
  8 36  1  0
  5 33  1  0
  5 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 23 49  1  6
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 28 56  1  0
 28 57  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  1
 19 48  1  0
 17 47  1  0
 16 46  1  0
M  END


  Mrv1652309022204252D          

 29 33  0  0  1  0            999 V2000
    0.5549    1.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    1.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8259    2.2001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7559    0.7729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5799    0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569   -0.0013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9110    0.8224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1746    1.1945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014    1.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377    0.9020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0281    1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3837    0.0783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1175    0.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7028   -0.1260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5172    0.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8893    0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7045    0.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8364   -0.1986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1026   -0.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3308   -0.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5155   -0.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1434   -1.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933   -0.3733    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7393   -1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489   -1.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -1.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2666   -0.4530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4429   -0.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149    0.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  2  0  0  0  0
 12 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0146918

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](O)[C@]2(COC(C)=O)[C@H](CCC[C@]22CO2)[C@@]11C[C@H](OC1=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O7/c1-13-8-18(24)22(12-27-14(2)23)17(4-3-6-20(22)11-28-20)21(13)9-16(29-19(21)25)15-5-7-26-10-15/h5,7,10,13,16-18,24H,3-4,6,8-9,11-12H2,1-2H3/t13-,16+,17-,18+,20+,21-,22+/m1/s1

> <INCHI_KEY>
LOZYVHYKXUKJDA-UYUQIPAXSA-N

> <FORMULA>
C22H28O7

> <MOLECULAR_WEIGHT>
404.459

> <EXACT_MASS>
404.183503242

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.91258501924271

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,4'aS,5'R,5''S,6'R,8'S,8'aR)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
1.7236359159999997

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.519174144393332

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8682501670256255

> <JCHEM_POLAR_SURFACE_AREA>
98.5

> <JCHEM_REFRACTIVITY>
100.33029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4'aS,5'R,5''S,6'R,8'S,8'aR)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'H-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.036   2.888   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.574   2.813   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.408   4.107   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.278   1.443   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.816   1.367   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.520  -0.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.434   1.535   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.059   2.230   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.723   2.378   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.097   1.684   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.386   2.527   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.183   0.146   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.553   0.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.645  -0.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.165   0.011   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.860   1.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.382   1.150   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.628  -0.371   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.258  -1.074   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.951  -1.610   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.429  -1.374   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.734  -2.749   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.894  -0.697   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.980  -2.235   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.691  -3.078   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.317  -2.383   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.231  -0.846   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.693  -0.931   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.388   0.443   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23   27                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   21   23                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   14   21                                                       
CONECT   21   20   12   22                                                  
CONECT   22   21                                                            
CONECT   23   12    6   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    6   28   29                                             
CONECT   28   27   29                                                       
CONECT   29   28   27                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₇

Average Mass

404.4590 Da

Monoisotopic Mass

404.18350 Da

IUPAC Name

[(2R,4'aS,5'R,5''S,6'R,8'S,8'aR)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate

Traditional Name

(2R,4'aS,5'R,5''S,6'R,8'S,8'aR)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'H-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](O)[C@]2(COC(C)=O)[C@H](CCC[C@]22CO2)[C@@]11C[C@H](OC1=O)C1=COC=C1

InChI Identifier

InChI=1S/C22H28O7/c1-13-8-18(24)22(12-27-14(2)23)17(4-3-6-20(22)11-28-20)21(13)9-16(29-19(21)25)15-5-7-26-10-15/h5,7,10,13,16-18,24H,3-4,6,8-9,11-12H2,1-2H3/t13-,16+,17-,18+,20+,21-,22+/m1/s1

InChI Key

LOZYVHYKXUKJDA-UYUQIPAXSA-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
Teucrium bicolor	LOTUS Database	35616633
Teucrium creticum	LOTUS Database	35616633
Teucrium flavum	LOTUS Database	35616633
Teucrium japonicum	LOTUS Database	35616633
Teucrium polium	LOTUS Database	35616633
Teucrium sandrasicum	LOTUS Database	35616633
Teucrium scorodonia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Furan
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Ether
Oxirane
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	2.14	ALOGPS
logP	1.72	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	14.52	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	98.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.33 m³·mol⁻¹	ChemAxon
Polarizability	41.91 Å³	ChemAxon
Number of Rings	5	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

C00023533

Chemspider ID

137425

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156030

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate (NP0146918)

MOL for NP0146918 ((2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D MOL for NP0146918 ((2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D SDF for NP0146918 ((2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D-SDF for NP0146918 ((2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

PDB for NP0146918 ((2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D PDB for NP0146918 ((2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

SMILES for NP0146918 ((2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

INCHI for NP0146918 ((2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

Structure for NP0146918 ((2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)

3D Structure for NP0146918 ((2r,4'as,5'r,5''s,6'r,8's,8'ar)-5''-(furan-3-yl)-8'-hydroxy-6'-methyl-2''-oxo-hexahydro-2'h-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolan]-8'a-ylmethyl acetate)