NP-MRD: Showing NP-Card for 7beta-Hydroxyfruticolone (NP0026970)

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Record Information

Version

2.0

Created at

2021-06-19 18:43:15 UTC

Updated at

2021-06-29 23:52:49 UTC

NP-MRD ID

NP0026970

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7beta-Hydroxyfruticolone

Provided By

JEOL Database JEOL Logo

Description

7beta-Hydroxyfruticolone is found in Teucrium fruticans. 7beta-Hydroxyfruticolone was first documented in 2004 (Coll, J., et al.). Based on a literature review very few articles have been published on [(1R,4S,4aR,5S,6S,7R,8aS)-5-[2-(furan-3-yl)ethyl]-4,7-dihydroxy-5,6-dimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120433D          

 59 62  0  0  0  0            999 V2000
   -0.5788    0.6106   -7.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341   -0.1970   -5.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5214   -1.4188   -5.9052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5214    0.6269   -4.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4321   -0.0343   -3.5883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3158    1.0263   -2.4563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5678    1.9117   -2.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5885    3.0276   -3.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8953    1.3252   -2.1140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9122    2.3230   -2.2630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8012    0.9253   -0.6352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1900    0.5061   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6611   -0.1294   -0.3783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0598   -1.5046   -0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5163   -0.4069    1.1711 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.1070    0.3506    4.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463   -0.0765    5.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2812    0.9383   -2.3896 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.1565    2.6719   -3.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600   -0.0620   -8.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1773    0.4913   -2.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5442    1.8408   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5891   -0.3467   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3465   -1.4623   -2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
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 21 20  1  0  0  0  0
 22 13  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  9 11  1  0  0  0  0
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 20 19  1  0  0  0  0
  6  5  1  6  0  0  0
 19 18  2  0  0  0  0
  7  8  2  0  0  0  0
 18 17  1  0  0  0  0
 13 15  1  1  0  0  0
 25 23  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
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 13 14  1  0  0  0  0
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  5  4  1  0  0  0  0
 22 23  1  0  0  0  0
  4  2  1  0  0  0  0
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  2  3  2  0  0  0  0
 11 12  1  0  0  0  0
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 10 36  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192120433D          

 59 62  0  0  0  0            999 V2000
   -0.5788    0.6106   -7.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341   -0.1970   -5.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0452    1.7734   -2.6081 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1945    3.2746   -2.4139 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1565    2.6719   -3.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600   -0.0620   -8.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2947    1.2655   -7.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3310   -0.6392   -3.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -0.7039   -3.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1773    0.4913   -2.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5633    2.9736   -2.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442    1.8408   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5891   -0.3467   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1726    0.2501    0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9094    1.3262   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3465   -1.4623   -2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257   -1.9231   -0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2666   -2.2475   -0.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799   -1.2056    1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -0.8445    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1906    1.2165    1.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9004    1.5782    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1471    0.6039    4.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9347   -0.2593    6.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1093   -0.1591    3.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1331    1.3656   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980   -0.7287    0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6767   -2.1551   -1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1216   -0.3270   -0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3730    1.1474   -0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535    0.1482   -3.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893    1.5434   -2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    3.6769   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542    3.8839   -2.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0  0  0  0
 22 13  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  9 11  1  0  0  0  0
 11 13  1  0  0  0  0
 25 26  1  0  0  0  0
 23 24  1  0  0  0  0
 20 19  1  0  0  0  0
  6  5  1  6  0  0  0
 19 18  2  0  0  0  0
  7  8  2  0  0  0  0
 18 17  1  0  0  0  0
 13 15  1  1  0  0  0
 25 23  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 26 27  1  0  0  0  0
 13 14  1  0  0  0  0
 27  6  1  0  0  0  0
  5  4  1  0  0  0  0
 22 23  1  0  0  0  0
  4  2  1  0  0  0  0
 22  6  1  0  0  0  0
  2  1  1  0  0  0  0
 27 28  1  0  0  0  0
  2  3  2  0  0  0  0
 11 12  1  0  0  0  0
 28 29  1  0  0  0  0
 22 51  1  1  0  0  0
 17 21  2  0  0  0  0
  9 10  1  0  0  0  0
 27 29  1  6  0  0  0
 21 50  1  0  0  0  0
 19 49  1  0  0  0  0
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 28 58  1  0  0  0  0
 28 59  1  0  0  0  0
 25 54  1  0  0  0  0
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 26 56  1  0  0  0  0
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 23 52  1  1  0  0  0
  9 35  1  6  0  0  0
 11 37  1  1  0  0  0
 24 53  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
 15 44  1  0  0  0  0
 15 45  1  0  0  0  0
 16 46  1  0  0  0  0
 16 47  1  0  0  0  0
 14 41  1  0  0  0  0
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 14 43  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 10 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026970

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C(=O)[C@]2(C([H])([H])OC(=O)C([H])([H])[H])[C@]([H])([C@@]([H])(O[H])C([H])([H])C([H])([H])[C@@]22OC2([H])[H])[C@@](C([H])([H])[H])(C([H])([H])C([H])([H])C2=C([H])OC([H])=C2[H])[C@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O7/c1-13-17(25)19(26)22(12-28-14(2)23)18(16(24)5-8-21(22)11-29-21)20(13,3)7-4-15-6-9-27-10-15/h6,9-10,13,16-18,24-25H,4-5,7-8,11-12H2,1-3H3/t13-,16+,17-,18-,20+,21+,22+/m1/s1

> <INCHI_KEY>
RDODYPGIYNDBAE-MJVBHVPDSA-N

> <FORMULA>
C22H30O7

> <MOLECULAR_WEIGHT>
406.475

> <EXACT_MASS>
406.199153306

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.63222891671925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,4S,4aR,5S,6S,7R,8aS)-5-[2-(furan-3-yl)ethyl]-4,7-dihydroxy-5,6-dimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.559933977333333

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.892511767242578

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.12436680788096

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7681522197514226

> <JCHEM_POLAR_SURFACE_AREA>
109.50000000000001

> <JCHEM_REFRACTIVITY>
102.7752

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,4aR,5S,6S,7R,8aS)-5-[2-(furan-3-yl)ethyl]-4,7-dihydroxy-5,6-dimethyl-8-oxo-hexahydrospiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
   -0.5788    0.6106   -7.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341   -0.1970   -5.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5214   -1.4188   -5.9052 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3158    1.0263   -2.4563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5678    1.9117   -2.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5885    3.0276   -3.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8953    1.3252   -2.1140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9122    2.3230   -2.2630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8012    0.9253   -0.6352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1900    0.5061   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6611   -0.1294   -0.3783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0598   -1.5046   -0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5163   -0.4069    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1507    0.7852    2.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544    0.3871    3.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1070    0.3506    4.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463   -0.0765    5.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2190   -0.3053    5.4802 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0740   -0.0224    4.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998    0.4598   -0.9693 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9607   -0.4163   -0.7026 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9220   -1.5925   -1.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607    0.3425   -0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812    0.9383   -2.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0452    1.7734   -2.6081 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1945    3.2746   -2.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1565    2.6719   -3.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600   -0.0620   -8.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5013    1.1956   -7.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2947    1.2655   -7.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3310   -0.6392   -3.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -0.7039   -3.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1773    0.4913   -2.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5633    2.9736   -2.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442    1.8408   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5891   -0.3467   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1726    0.2501    0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9094    1.3262   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3465   -1.4623   -2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257   -1.9231   -0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2666   -2.2475   -0.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799   -1.2056    1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -0.8445    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1906    1.2165    1.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9004    1.5782    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1471    0.6039    4.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9347   -0.2593    6.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1093   -0.1591    3.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1331    1.3656   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980   -0.7287    0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6767   -2.1551   -1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1216   -0.3270   -0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3730    1.1474   -0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535    0.1482   -3.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893    1.5434   -2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    3.6769   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542    3.8839   -2.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 22 13  1  0
  6  7  1  0
  7  9  1  0
  9 11  1  0
 11 13  1  0
 25 26  1  0
 23 24  1  0
 20 19  1  0
  6  5  1  6
 19 18  2  0
  7  8  2  0
 18 17  1  0
 13 15  1  1
 25 23  1  0
 15 16  1  0
 16 17  1  0
 26 27  1  0
 13 14  1  0
 27  6  1  0
  5  4  1  0
 22 23  1  0
  4  2  1  0
 22  6  1  0
  2  1  1  0
 27 28  1  0
  2  3  2  0
 11 12  1  0
 28 29  1  0
 22 51  1  1
 17 21  2  0
  9 10  1  0
 27 29  1  6
 21 50  1  0
 19 49  1  0
 18 48  1  0
 28 58  1  0
 28 59  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 23 52  1  1
  9 35  1  6
 11 37  1  1
 24 53  1  0
  5 33  1  0
  5 34  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 10 36  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.579   0.611  -7.208  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.534  -0.197  -5.948  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.521  -1.419  -5.905  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.521   0.627  -4.867  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.432  -0.034  -3.588  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.316   1.026  -2.456  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.568   1.912  -2.593  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.589   3.028  -3.122  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.895   1.325  -2.114  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.912   2.323  -2.263  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.801   0.925  -0.635  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.190   0.506  -0.117  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.661  -0.129  -0.378  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.060  -1.505  -0.971  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.516  -0.407   1.171  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.151   0.785   2.068  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.054   0.387   3.504  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.107   0.351   4.462  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.546  -0.077   5.643  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.219  -0.305   5.480  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.074  -0.022   4.186  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.300   0.460  -0.969  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.961  -0.416  -0.703  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.922  -1.593  -1.493  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.261   0.343  -0.989  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.281   0.938  -2.390  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.045   1.773  -2.608  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.194   3.275  -2.414  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.157   2.672  -3.717  0.00  0.00           O+0
HETATM   30  H   UNK     0      -0.560  -0.062  -8.070  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.501   1.196  -7.240  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.295   1.266  -7.260  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.331  -0.639  -3.490  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.429  -0.704  -3.620  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.177   0.491  -2.761  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.563   2.974  -2.909  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.544   1.841  -0.085  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.589  -0.347  -0.675  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.173   0.250   0.945  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.909   1.326  -0.219  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.346  -1.462  -2.019  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.926  -1.923  -0.444  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.267  -2.248  -0.861  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.780  -1.206   1.329  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.449  -0.845   1.550  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.191   1.216   1.766  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.900   1.578   1.979  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.147   0.604   4.310  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.935  -0.259   6.635  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.109  -0.159   3.906  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.133   1.366  -0.365  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.998  -0.729   0.344  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.677  -2.155  -1.240  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.122  -0.327  -0.878  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.373   1.147  -0.252  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.353   0.148  -3.144  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.189   1.543  -2.504  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.146   3.677  -2.086  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.354   3.884  -2.110  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   33   34                                             
CONECT    6    7    5   27   22                                             
CONECT    7    6    9    8                                                  
CONECT    8    7                                                            
CONECT    9    7   11   10   35                                             
CONECT   10    9   36                                                       
CONECT   11    9   13   12   37                                             
CONECT   12   11   38   39   40                                             
CONECT   13   22   11   15   14                                             
CONECT   14   13   41   42   43                                             
CONECT   15   13   16   44   45                                             
CONECT   16   15   17   46   47                                             
CONECT   17   18   16   21                                                  
CONECT   18   19   17   48                                                  
CONECT   19   20   18   49                                                  
CONECT   20   21   19                                                       
CONECT   21   20   17   50                                                  
CONECT   22   13   23    6   51                                             
CONECT   23   24   25   22   52                                             
CONECT   24   23   53                                                       
CONECT   25   26   23   54   55                                             
CONECT   26   25   27   56   57                                             
CONECT   27   26    6   28   29                                             
CONECT   28   27   29   58   59                                             
CONECT   29   28   27                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  124    0
END

RDKit          3D

59 62  0  0  0  0  0  0  0  0999 V2000
   -0.5788    0.6106   -7.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341   -0.1970   -5.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5214   -1.4188   -5.9052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5214    0.6269   -4.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4321   -0.0343   -3.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158    1.0263   -2.4563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5678    1.9117   -2.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5885    3.0276   -3.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8953    1.3252   -2.1140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9122    2.3230   -2.2630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8012    0.9253   -0.6352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1900    0.5061   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6611   -0.1294   -0.3783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0598   -1.5046   -0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5163   -0.4069    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1507    0.7852    2.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544    0.3871    3.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1070    0.3506    4.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463   -0.0765    5.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2190   -0.3053    5.4802 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0740   -0.0224    4.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998    0.4598   -0.9693 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9607   -0.4163   -0.7026 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9220   -1.5925   -1.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607    0.3425   -0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812    0.9383   -2.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0452    1.7734   -2.6081 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1945    3.2746   -2.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1565    2.6719   -3.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600   -0.0620   -8.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5013    1.1956   -7.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2947    1.2655   -7.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3310   -0.6392   -3.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -0.7039   -3.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1773    0.4913   -2.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5633    2.9736   -2.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5442    1.8408   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5891   -0.3467   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1726    0.2501    0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9094    1.3262   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3465   -1.4623   -2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257   -1.9231   -0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2666   -2.2475   -0.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799   -1.2056    1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -0.8445    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1906    1.2165    1.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9004    1.5782    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1471    0.6039    4.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9347   -0.2593    6.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1093   -0.1591    3.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1331    1.3656   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980   -0.7287    0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6767   -2.1551   -1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1216   -0.3270   -0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3730    1.1474   -0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535    0.1482   -3.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893    1.5434   -2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    3.6769   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542    3.8839   -2.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 22 13  1  0
  6  7  1  0
  7  9  1  0
  9 11  1  0
 11 13  1  0
 25 26  1  0
 23 24  1  0
 20 19  1  0
  6  5  1  6
 19 18  2  0
  7  8  2  0
 18 17  1  0
 13 15  1  1
 25 23  1  0
 15 16  1  0
 16 17  1  0
 26 27  1  0
 13 14  1  0
 27  6  1  0
  5  4  1  0
 22 23  1  0
  4  2  1  0
 22  6  1  0
  2  1  1  0
 27 28  1  0
  2  3  2  0
 11 12  1  0
 28 29  1  0
 22 51  1  1
 17 21  2  0
  9 10  1  0
 27 29  1  6
 21 50  1  0
 19 49  1  0
 18 48  1  0
 28 58  1  0
 28 59  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 23 52  1  1
  9 35  1  6
 11 37  1  1
 24 53  1  0
  5 33  1  0
  5 34  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 10 36  1  0
M  END

View in JSmol

Synonyms

Value	Source
[(1R,4S,4AR,5S,6S,7R,8as)-5-[2-(furan-3-yl)ethyl]-4,7-dihydroxy-5,6-dimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₇

Average Mass

406.4750 Da

Monoisotopic Mass

406.19915 Da

IUPAC Name

[(1R,4S,4aR,5S,6S,7R,8aS)-5-[2-(furan-3-yl)ethyl]-4,7-dihydroxy-5,6-dimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

Traditional Name

(1R,4S,4aR,5S,6S,7R,8aS)-5-[2-(furan-3-yl)ethyl]-4,7-dihydroxy-5,6-dimethyl-8-oxo-hexahydrospiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C(=O)[C@]2(C([H])([H])OC(=O)C([H])([H])[H])[C@]([H])([C@@]([H])(O[H])C([H])([H])C([H])([H])[C@@]22OC2([H])[H])[C@@](C([H])([H])[H])(C([H])([H])C([H])([H])C2=C([H])OC([H])=C2[H])[C@]1([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H30O7/c1-13-17(25)19(26)22(12-28-14(2)23)18(16(24)5-8-21(22)11-29-21)20(13,3)7-4-15-6-9-27-10-15/h6,9-10,13,16-18,24-25H,4-5,7-8,11-12H2,1-3H3/t13-,16+,17-,18-,20+,21+,22+/m1/s1

InChI Key

RDODYPGIYNDBAE-MJVBHVPDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Teucrium fruticans	JEOL database	Coll, J., et al, Phytochemistry 65, 387 (2004)

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	1.58	ALOGPS
logP	1.56	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.12	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	102.78 m³·mol⁻¹	ChemAxon
Polarizability	42.63 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

Not Available

Chemspider ID

9638731

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11463891

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Coll, J., et al. (2004). Coll, J., et al, Phytochemistry 65, 387 (2004). Phytochem..

Showing NP-Card for 7beta-Hydroxyfruticolone (NP0026970)

MOL for NP0026970 (7beta-Hydroxyfruticolone)

3D MOL for NP0026970 (7beta-Hydroxyfruticolone)

3D SDF for NP0026970 (7beta-Hydroxyfruticolone)

3D-SDF for NP0026970 (7beta-Hydroxyfruticolone)

PDB for NP0026970 (7beta-Hydroxyfruticolone)

3D PDB for NP0026970 (7beta-Hydroxyfruticolone)

SMILES for NP0026970 (7beta-Hydroxyfruticolone)

INCHI for NP0026970 (7beta-Hydroxyfruticolone)

Structure for NP0026970 (7beta-Hydroxyfruticolone)

3D Structure for NP0026970 (7beta-Hydroxyfruticolone)