NP-MRD: Showing NP-Card for cipadonoid B (NP0038542)

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Record Information

Version

1.0

Created at

2021-06-20 21:12:25 UTC

Updated at

2021-06-30 00:11:23 UTC

NP-MRD ID

NP0038542

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cipadonoid B

Provided By

JEOL Database JEOL Logo

Description

2,2,6Alpha-Trimethyl-5-oxo-6-[1alpha-(3-furanyl)-3-oxo-5-methylene-8aalpha-methyl-3,5,6,7,8,8a-hexahydro-1H-2-benzopyran-6beta-yl]-3-cyclohexene-1alpha-acetic acid methyl ester belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. cipadonoid B is found in Cipadessa cinerascens. It was first documented in 2009 (Fang, X., et al.). Based on a literature review very few articles have been published on 2,2,6alpha-Trimethyl-5-oxo-6-[1alpha-(3-furanyl)-3-oxo-5-methylene-8aalpha-methyl-3,5,6,7,8,8a-hexahydro-1H-2-benzopyran-6beta-yl]-3-cyclohexene-1alpha-acetic acid methyl ester.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123123D          

 65 68  0  0  0  0            999 V2000
    1.3318    3.2605   -0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4244    1.9178   -0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9160    1.2063   -1.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2788    1.5034   -2.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7475    0.9321   -3.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7947    1.3151   -4.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0696    0.0382   -4.1469 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087   -0.7567   -3.2867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6574   -1.7677   -4.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1720   -1.6130   -5.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7618   -2.8080   -5.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390   -3.6970   -4.7538 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9600   -3.0694   -3.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095    0.1519   -2.3835 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8817    0.8910   -3.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4746   -0.7234   -1.2980 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1180    0.0666   -0.1627 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2293    1.1556    0.4957 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4780    0.7170    1.8514 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9310    1.9840    2.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6113    0.2221    2.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5956    0.9165    3.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5630   -1.1264    3.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4305   -1.8301    3.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1063   -1.3468    2.8696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6634   -0.7399    4.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6815   -2.5966    2.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532   -0.3758    1.6410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9745    0.2091    1.0797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6359   -0.6514    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006   -1.5721   -0.5771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9039   -0.2062   -0.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6033   -0.9104   -1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7689    3.8193    0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9449    2.2477   -1.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2219   -1.3342   -2.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117   -0.7345   -6.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2772   -3.1696   -6.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7707   -3.6672   -2.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339    1.4296   -4.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257    0.1964   -3.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    1.6285   -2.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442   -1.4239   -0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -1.3516   -1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0110    0.5632   -0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -0.6409    0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9810    1.8851    0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0989    2.4525    2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5953    1.7727    3.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7127    2.7475    2.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812   -1.4868    3.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515   -2.7931    3.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1928   -3.0906    1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059   -2.3438    2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8125    1.1714    0.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5900   -0.4531   -1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716   -0.8279   -2.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358   -1.9598   -0.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
 23 21  1  0  0  0  0
 28 29  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 18 17  1  0  0  0  0
 25 27  1  0  0  0  0
  2  3  1  0  0  0  0
 21 22  2  0  0  0  0
 14 16  1  0  0  0  0
 29 30  1  0  0  0  0
 16 17  1  0  0  0  0
 30 31  2  0  0  0  0
 19 18  1  0  0  0  0
 30 32  1  0  0  0  0
 14  3  1  0  0  0  0
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 25 28  1  0  0  0  0
  2  1  2  3  0  0  0
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 19 21  1  0  0  0  0
  8  9  1  0  0  0  0
  9 13  2  0  0  0  0
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 19 20  1  1  0  0  0
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 29 61  1  0  0  0  0
 29 62  1  0  0  0  0
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 27 59  1  0  0  0  0
 33 63  1  0  0  0  0
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 33 65  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
 13 40  1  0  0  0  0
 11 39  1  0  0  0  0
 10 38  1  0  0  0  0
 15 41  1  0  0  0  0
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 15 43  1  0  0  0  0
 20 49  1  0  0  0  0
 20 50  1  0  0  0  0
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M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
    1.3318    3.2605   -0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4244    1.9178   -0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202123123D          

 65 68  0  0  0  0            999 V2000
    1.3318    3.2605   -0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4244    1.9178   -0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9160    1.2063   -1.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2788    1.5034   -2.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7475    0.9321   -3.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1720   -1.6130   -5.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4339    1.4296   -4.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257    0.1964   -3.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    1.6285   -2.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2534   -1.3516   -1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0110    0.5632   -0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -0.6409    0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0989    2.4525    2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5953    1.7727    3.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4515   -2.7931    3.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6643   -0.3976    3.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1310    0.0935    4.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7619   -3.3406    3.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1928   -3.0906    1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059   -2.3438    2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -1.0364    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973    0.3897    1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5900   -0.4531   -1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716   -0.8279   -2.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358   -1.9598   -0.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
 23 21  1  0  0  0  0
 28 29  1  0  0  0  0
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 18 17  1  0  0  0  0
 25 27  1  0  0  0  0
  2  3  1  0  0  0  0
 21 22  2  0  0  0  0
 14 16  1  0  0  0  0
 29 30  1  0  0  0  0
 16 17  1  0  0  0  0
 30 31  2  0  0  0  0
 19 18  1  0  0  0  0
 30 32  1  0  0  0  0
 14  3  1  0  0  0  0
 32 33  1  0  0  0  0
 25 28  1  0  0  0  0
  2  1  2  3  0  0  0
 28 19  1  0  0  0  0
  5  6  2  0  0  0  0
 19 21  1  0  0  0  0
  8  9  1  0  0  0  0
  9 13  2  0  0  0  0
 18  2  1  0  0  0  0
 23 24  2  0  0  0  0
 14  8  1  0  0  0  0
 13 12  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  2  0  0  0  0
 10  9  1  0  0  0  0
  3  4  2  0  0  0  0
 14 15  1  6  0  0  0
  4  5  1  0  0  0  0
 19 20  1  1  0  0  0
 23 52  1  0  0  0  0
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 28 60  1  6  0  0  0
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 17 47  1  0  0  0  0
  4 36  1  0  0  0  0
  8 37  1  1  0  0  0
 29 61  1  0  0  0  0
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 33 63  1  0  0  0  0
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  1 34  1  0  0  0  0
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 20 49  1  0  0  0  0
 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038542

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1C2=C([H])C(=O)O[C@@]([H])(C3=C([H])OC([H])=C3[H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])[C@@]1(C(=O)C([H])=C([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]1([H])C([H])([H])C(=O)OC([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O6/c1-16-18(27(5)20(14-22(29)31-6)25(2,3)10-8-21(27)28)7-11-26(4)19(16)13-23(30)33-24(26)17-9-12-32-15-17/h8-10,12-13,15,18,20,24H,1,7,11,14H2,2-6H3/t18-,20+,24-,26+,27-/m0/s1

> <INCHI_KEY>
FXAFBVCVQVUWAF-DTZNGXDKSA-N

> <FORMULA>
C27H32O6

> <MOLECULAR_WEIGHT>
452.547

> <EXACT_MASS>
452.21988875

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.842294692008295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(1R,6R)-6-[(1R,6S,8aR)-1-(furan-3-yl)-8a-methyl-5-methylidene-3-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-6-yl]-2,2,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
4.764362628999999

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.885695484063754

> <JCHEM_POLAR_SURFACE_AREA>
82.81

> <JCHEM_REFRACTIVITY>
124.24459999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,6R)-6-[(1R,6S,8aR)-1-(furan-3-yl)-8a-methyl-5-methylidene-3-oxo-1,6,7,8-tetrahydroisochromen-6-yl]-2,2,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
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    1.7707   -3.6672   -2.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
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 14  3  1  0
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 18  2  1  0
 23 24  2  0
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 13 12  1  0
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 14 15  1  6
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 20 49  1  0
 20 50  1  0
 20 51  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       1.332   3.260  -0.491  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.424   1.918  -0.558  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.916   1.206  -1.736  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.279   1.503  -2.279  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.748   0.932  -3.551  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.795   1.315  -4.055  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.070   0.038  -4.147  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.909  -0.757  -3.287  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.657  -1.768  -4.114  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.172  -1.613  -5.435  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.762  -2.808  -5.771  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.639  -3.697  -4.754  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.960  -3.069  -3.761  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.810   0.152  -2.384  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.882   0.891  -3.218  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.475  -0.723  -1.298  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.118   0.067  -0.163  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.229   1.156   0.496  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.478   0.717   1.851  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.931   1.984   2.562  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.611   0.222   2.779  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.596   0.917   3.041  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.563  -1.126   3.372  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.431  -1.830   3.414  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.106  -1.347   2.870  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.663  -0.740   4.060  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.682  -2.597   2.409  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.353  -0.376   1.641  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.975   0.209   1.080  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.636  -0.651   0.023  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.101  -1.572  -0.577  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.904  -0.206  -0.197  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.603  -0.910  -1.225  0.00  0.00           C+0
HETATM   34  H   UNK     0       1.769   3.819   0.332  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.848   3.857  -1.259  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.945   2.248  -1.856  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.222  -1.334  -2.654  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.112  -0.735  -6.063  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.277  -3.170  -6.650  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.771  -3.667  -2.880  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.434   1.430  -4.061  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.626   0.196  -3.622  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.432   1.629  -2.623  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.744  -1.424  -0.882  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.253  -1.352  -1.749  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.011   0.563  -0.568  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.504  -0.641   0.577  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.981   1.885   0.844  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.099   2.453   2.032  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.595   1.773   3.579  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.713   2.748   2.662  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.481  -1.487   3.823  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.452  -2.793   3.923  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.804  -1.487   4.853  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.664  -0.398   3.784  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.131   0.094   4.523  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.762  -3.341   3.212  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.193  -3.091   1.561  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.706  -2.344   2.118  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.764  -1.036   0.874  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.697   0.390   1.878  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.813   1.171   0.594  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.590  -0.453  -1.338  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.072  -0.828  -2.178  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.736  -1.960  -0.945  0.00  0.00           H+0
CONECT    1    2   34   35                                                  
CONECT    2    3    1   18                                                  
CONECT    3    2   14    4                                                  
CONECT    4    3    5   36                                                  
CONECT    5    7    6    4                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   14   37                                             
CONECT    9    8   13   10                                                  
CONECT   10   11    9   38                                                  
CONECT   11   12   10   39                                                  
CONECT   12   13   11                                                       
CONECT   13    9   12   40                                                  
CONECT   14   16    3    8   15                                             
CONECT   15   14   41   42   43                                             
CONECT   16   14   17   44   45                                             
CONECT   17   18   16   46   47                                             
CONECT   18   17   19    2   48                                             
CONECT   19   18   28   21   20                                             
CONECT   20   19   49   50   51                                             
CONECT   21   23   22   19                                                  
CONECT   22   21                                                            
CONECT   23   21   24   52                                                  
CONECT   24   25   23   53                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25   54   55   56                                             
CONECT   27   25   57   58   59                                             
CONECT   28   29   25   19   60                                             
CONECT   29   28   30   61   62                                             
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   63   64   65                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    4                                                            
CONECT   37    8                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   13                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
CONECT   60   28                                                            
CONECT   61   29                                                            
CONECT   62   29                                                            
CONECT   63   33                                                            
CONECT   64   33                                                            
CONECT   65   33                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  136    0
END

RDKit          3D

65 68  0  0  0  0  0  0  0  0999 V2000
    1.3318    3.2605   -0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4244    1.9178   -0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9160    1.2063   -1.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2788    1.5034   -2.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9087   -0.7567   -3.2867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6574   -1.7677   -4.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1720   -1.6130   -5.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7618   -2.8080   -5.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390   -3.6970   -4.7538 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9600   -3.0694   -3.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095    0.1519   -2.3835 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8817    0.8910   -3.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4746   -0.7234   -1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1180    0.0666   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2293    1.1556    0.4957 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4780    0.7170    1.8514 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9310    1.9840    2.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6113    0.2221    2.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5956    0.9165    3.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5630   -1.1264    3.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4305   -1.8301    3.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1063   -1.3468    2.8696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6634   -0.7399    4.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6815   -2.5966    2.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532   -0.3758    1.6410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9745    0.2091    1.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6359   -0.6514    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006   -1.5721   -0.5771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9039   -0.2062   -0.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6033   -0.9104   -1.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7689    3.8193    0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2219   -1.3342   -2.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117   -0.7345   -6.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2772   -3.1696   -6.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7707   -3.6672   -2.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339    1.4296   -4.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257    0.1964   -3.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    1.6285   -2.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442   -1.4239   -0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -1.3516   -1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0110    0.5632   -0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -0.6409    0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9810    1.8851    0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0989    2.4525    2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5953    1.7727    3.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7127    2.7475    2.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812   -1.4868    3.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8042   -1.4866    4.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1928   -3.0906    1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059   -2.3438    2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644   -1.0364    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5900   -0.4531   -1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716   -0.8279   -2.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358   -1.9598   -0.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0
  7  8  1  0
 23 21  1  0
 28 29  1  0
 24 25  1  0
 25 26  1  1
 18 17  1  0
 25 27  1  0
  2  3  1  0
 21 22  2  0
 14 16  1  0
 29 30  1  0
 16 17  1  0
 30 31  2  0
 19 18  1  0
 30 32  1  0
 14  3  1  0
 32 33  1  0
 25 28  1  0
  2  1  2  3
 28 19  1  0
  5  6  2  0
 19 21  1  0
  8  9  1  0
  9 13  2  0
 18  2  1  0
 23 24  2  0
 14  8  1  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  3  4  2  0
 14 15  1  6
  4  5  1  0
 19 20  1  1
 23 52  1  0
 24 53  1  0
 28 60  1  6
 18 48  1  1
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
  4 36  1  0
  8 37  1  1
 29 61  1  0
 29 62  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
 27 57  1  0
 27 58  1  0
 27 59  1  0
 33 63  1  0
 33 64  1  0
 33 65  1  0
  1 34  1  0
  1 35  1  0
 13 40  1  0
 11 39  1  0
 10 38  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 20 49  1  0
 20 50  1  0
 20 51  1  0
M  END

View in JSmol

Synonyms

Value	Source
2,2,6a-Trimethyl-5-oxo-6-[1a-(3-furanyl)-3-oxo-5-methylene-8aalpha-methyl-3,5,6,7,8,8a-hexahydro-1H-2-benzopyran-6b-yl]-3-cyclohexene-1a-acetate methyl ester	Generator
2,2,6a-Trimethyl-5-oxo-6-[1a-(3-furanyl)-3-oxo-5-methylene-8aalpha-methyl-3,5,6,7,8,8a-hexahydro-1H-2-benzopyran-6b-yl]-3-cyclohexene-1a-acetic acid methyl ester	Generator
2,2,6alpha-Trimethyl-5-oxo-6-[1alpha-(3-furanyl)-3-oxo-5-methylene-8aalpha-methyl-3,5,6,7,8,8a-hexahydro-1H-2-benzopyran-6beta-yl]-3-cyclohexene-1alpha-acetate methyl ester	Generator
2,2,6Α-trimethyl-5-oxo-6-[1α-(3-furanyl)-3-oxo-5-methylene-8aalpha-methyl-3,5,6,7,8,8a-hexahydro-1H-2-benzopyran-6β-yl]-3-cyclohexene-1α-acetate methyl ester	Generator
2,2,6Α-trimethyl-5-oxo-6-[1α-(3-furanyl)-3-oxo-5-methylene-8aalpha-methyl-3,5,6,7,8,8a-hexahydro-1H-2-benzopyran-6β-yl]-3-cyclohexene-1α-acetic acid methyl ester	Generator

Chemical Formula

C₂₇H₃₂O₆

Average Mass

452.5470 Da

Monoisotopic Mass

452.21989 Da

IUPAC Name

methyl 2-[(1R,6R)-6-[(1R,6S,8aR)-1-(furan-3-yl)-8a-methyl-5-methylidene-3-oxo-3,5,6,7,8,8a-hexahydro-1H-isochromen-6-yl]-2,2,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

Traditional Name

methyl [(1R,6R)-6-[(1R,6S,8aR)-1-(furan-3-yl)-8a-methyl-5-methylidene-3-oxo-1,6,7,8-tetrahydroisochromen-6-yl]-2,2,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1C2=C([H])C(=O)O[C@@]([H])(C3=C([H])OC([H])=C3[H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])[C@@]1(C(=O)C([H])=C([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]1([H])C([H])([H])C(=O)OC([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C27H32O6/c1-16-18(27(5)20(14-22(29)31-6)25(2,3)10-8-21(27)28)7-11-26(4)19(16)13-23(30)33-24(26)17-9-12-32-15-17/h8-10,12-13,15,18,20,24H,1,7,11,14H2,2-6H3/t18-,20+,24-,26+,27-/m0/s1

InChI Key

FXAFBVCVQVUWAF-DTZNGXDKSA-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
Cipadessa cinerascens	JEOL database	Fang, X., et al, Tetrahedron 65, 7408 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Cyclohexenone
Dicarboxylic acid or derivatives
Furan
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.84	ALOGPS
logP	4.76	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	82.81 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.24 m³·mol⁻¹	ChemAxon
Polarizability	47.84 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

74156829

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53348317

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fang, X., et al. (2009). Fang, X., et al, Tetrahedron 65, 7408 (2009). Tetrahedron.

Showing NP-Card for cipadonoid B (NP0038542)

MOL for NP0038542 (cipadonoid B)

3D MOL for NP0038542 (cipadonoid B)

3D SDF for NP0038542 (cipadonoid B)

3D-SDF for NP0038542 (cipadonoid B)

PDB for NP0038542 (cipadonoid B)

3D PDB for NP0038542 (cipadonoid B)

SMILES for NP0038542 (cipadonoid B)

INCHI for NP0038542 (cipadonoid B)

Structure for NP0038542 (cipadonoid B)

3D Structure for NP0038542 (cipadonoid B)