NP-MRD: Showing NP-Card for (1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate (NP0221863)

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Record Information

Version

2.0

Created at

2022-09-05 23:32:49 UTC

Updated at

2022-09-05 23:32:49 UTC

NP-MRD ID

NP0221863

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate

Description

Isofruticolone belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. (1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate is found in Teucrium fruticans. (1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate was first documented in 2004 (PMID: 14759529). Based on a literature review very few articles have been published on Isofruticolone (PMID: 16122769).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062201322D          

 28 31  0  0  1  0            999 V2000
    1.2753    1.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0308    1.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6955    2.0457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1217    0.7370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8773    0.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681   -0.4142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2186    0.3718    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6632    0.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0246    0.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -0.0621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3861    0.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3296   -0.8481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3631   -1.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1472   -0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4606   -1.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2782   -1.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6696   -2.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4813   -2.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5915   -1.5925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8479   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236   -1.0242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2731   -1.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8286   -2.4202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -1.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9116   -1.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622   -0.5903    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3761   -0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9861    0.2157    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  6  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  1  0  0  0
 12 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 12 21  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 28  1  1  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
   -4.7124    3.2485    1.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    2.8970    1.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4150    3.7027    1.4668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8682    1.6393    0.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4978    1.2483    0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4233   -0.1473    0.1467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9793   -0.2092   -1.2428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0978   -1.5237   -1.7058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473    0.4677   -2.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3495   -0.2469   -2.1086 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2818    0.2824   -3.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0103   -0.1989   -0.6768 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5307    1.1408   -0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033   -1.2131   -0.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0842   -1.4940    0.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0363   -0.4491    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493   -0.1541   -0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8445    0.8882    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0600    1.2300    1.5528 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9668    0.4466    1.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0530   -0.7609    0.1800 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2213   -1.0216    1.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -0.3569    2.3544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3755   -2.3085    2.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132   -2.3643    1.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2801   -1.0055    1.0966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7168   -0.8554    1.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535   -0.3884    2.2065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8485    4.3249    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1495    3.0546    0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224    2.6572    1.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1749    1.3446    1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9889    2.0158    0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9171    0.3625   -1.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7194   -1.5338   -2.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3399    0.3737   -3.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795    1.5505   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1554   -1.3243   -2.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1803    0.7836   -2.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    0.9451   -3.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6846   -0.5477   -3.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065    1.2290   -0.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0289    1.8847   -1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5054    1.5637    0.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6315   -1.0087   -1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5599   -2.1858   -1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5913   -1.9341    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435   -2.3614   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6215   -0.6684   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8104    1.3684    0.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2085    0.5963    2.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -1.7741   -0.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5167   -2.3071    3.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2794   -3.1204    1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -2.8663    2.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6411   -3.0138    0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3106   -1.7630    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3463   -0.1393    0.6405 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 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 21 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 20  2  0
 20 19  1  0
 19 18  1  0
 18 17  2  0
 12 10  1  0
 17 16  1  0
 26  6  1  0
 26 28  1  1
 11 39  1  0
 11 40  1  0
 11 41  1  0
 10 38  1  6
  9 36  1  0
  9 37  1  0
  7 34  1  1
  8 35  1  0
  5 32  1  0
  5 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 21 52  1  6
 24 53  1  0
 24 54  1  0
 25 55  1  0
 25 56  1  0
 27 57  1  0
 27 58  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 20 51  1  0
 18 50  1  0
 17 49  1  0
M  END


  Mrv1652309062201322D          

 28 31  0  0  1  0            999 V2000
    1.2753    1.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0308    1.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6955    2.0457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1217    0.7370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8773    0.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681   -0.4142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2186    0.3718    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6632    0.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0246    0.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5801   -0.0621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3861    0.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3296   -0.8481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3631   -1.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1472   -0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4606   -1.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2782   -1.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6696   -2.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4813   -2.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5915   -1.5925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8479   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236   -1.0242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2731   -1.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8286   -2.4202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -1.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9116   -1.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622   -0.5903    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3761   -0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9861    0.2157    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  6  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  1  0  0  0
 12 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 12 21  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0221863

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H](O)[C@]2(COC(C)=O)[C@H](C(=O)CC[C@]22CO2)[C@@]1(C)CCC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O6/c1-14-10-18(25)22(13-27-15(2)23)19(17(24)5-8-21(22)12-28-21)20(14,3)7-4-16-6-9-26-11-16/h6,9,11,14,18-19,25H,4-5,7-8,10,12-13H2,1-3H3/t14-,18-,19-,20+,21+,22-/m1/s1

> <INCHI_KEY>
XFXPUVAJQDQQQD-ZRXGRRBWSA-N

> <FORMULA>
C22H30O6

> <MOLECULAR_WEIGHT>
390.476

> <EXACT_MASS>
390.204238686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.62923254237241

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,4aR,5S,6R,8R,8aR)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

> <JCHEM_LOGP>
2.1750327159999996

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.172792903847867

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.500799667208721

> <JCHEM_PKA_STRONGEST_BASIC>
-2.768066075255072

> <JCHEM_POLAR_SURFACE_AREA>
89.27000000000001

> <JCHEM_REFRACTIVITY>
101.25709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aR,5S,6R,8R,8aR)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

> <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       2.381   3.525   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.791   2.906   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.032   3.819   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.961   1.376   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.371   0.757   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.541  -0.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.008   0.694   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.971   1.833   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.513   1.023   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.550  -0.116   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.054   0.213   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.082  -1.583   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.144  -3.122   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.608  -1.789   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.193  -3.213   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.719  -3.419   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.450  -4.775   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.965  -4.499   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.171  -2.973   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.783  -2.305   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.577  -1.912   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.110  -3.379   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.147  -4.518   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.605  -3.708   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.568  -2.569   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.036  -1.102   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.569  -0.634   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.707   0.403   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   21   26                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   21                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21   12    6   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    6   27   28                                             
CONECT   27   26   28                                                       
CONECT   28   27   26                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₆

Average Mass

390.4760 Da

Monoisotopic Mass

390.20424 Da

IUPAC Name

[(1R,4aR,5S,6R,8R,8aR)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

Traditional Name

(1R,4aR,5S,6R,8R,8aR)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](O)[C@]2(COC(C)=O)[C@H](C(=O)CC[C@]22CO2)[C@@]1(C)CCC1=COC=C1

InChI Identifier

InChI=1S/C22H30O6/c1-14-10-18(25)22(13-27-15(2)23)19(17(24)5-8-21(22)12-28-21)20(14,3)7-4-16-6-9-26-11-16/h6,9,11,14,18-19,25H,4-5,7-8,10,12-13H2,1-3H3/t14-,18-,19-,20+,21+,22-/m1/s1

InChI Key

XFXPUVAJQDQQQD-ZRXGRRBWSA-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 fruticans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Heteroaromatic compounds

Sub Class

Not Available

Direct Parent

Heteroaromatic compounds

Alternative Parents

Substituents

Cyclic alcohol
Furan
Heteroaromatic compound
Carboxylic acid ester
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
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	2.18	ChemAxon
pKa (Strongest Acidic)	14.5	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	101.26 m³·mol⁻¹	ChemAxon
Polarizability	41.63 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023539

Chemspider ID

10222437

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21596556

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Coll J, Tandron Y: Isolation and structure elucidation of three neo-clerodane diterpenes from Teucrium fruticans L. (LABIATAE). Phytochemistry. 2005 Oct;66(19):2298-303. doi: 10.1016/j.phytochem.2005.07.003. [PubMed:16122769 ]
Coll J, Tandron Y: Neo-clerodane diterpenes from Teucrium fruticans. Phytochemistry. 2004 Feb;65(4):387-92. doi: 10.1016/j.phytochem.2003.09.018. [PubMed:14759529 ]
LOTUS database [Link]

Showing NP-Card for (1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate (NP0221863)

MOL for NP0221863 ((1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

3D MOL for NP0221863 ((1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

3D SDF for NP0221863 ((1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

3D-SDF for NP0221863 ((1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

PDB for NP0221863 ((1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

3D PDB for NP0221863 ((1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

SMILES for NP0221863 ((1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

INCHI for NP0221863 ((1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

Structure for NP0221863 ((1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)

3D Structure for NP0221863 ((1r,4ar,5s,6r,8r,8ar)-5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6-dimethyl-4-oxo-hexahydrospiro[naphthalene-1,2'-oxiran]-8a-ylmethyl acetate)