NP-MRD: Showing NP-Card for Hueafuranoid A (NP0011245)

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Record Information

Version

2.0

Created at

2021-01-05 21:00:20 UTC

Updated at

2021-07-15 17:08:22 UTC

NP-MRD ID

NP0011245

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hueafuranoid A

Provided By

NPAtlas

Description

6-Hydroxy-6-[(2S,5R)-5-[(1E)-4-hydroxy-4-methylhexa-1,5-dien-1-yl]-5-methyloxolan-2-yl]-2-methylhept-2-en-4-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Hueafuranoid A is found in Huea. Hueafuranoid A was first documented in 2012 (PMID: 23141910). Based on a literature review very few articles have been published on 6-hydroxy-6-[(2S,5R)-5-[(1E)-4-hydroxy-4-methylhexa-1,5-dien-1-yl]-5-methyloxolan-2-yl]-2-methylhept-2-en-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107453D          

 56 56  0  0  0  0            999 V2000
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   -4.1524    1.0705    0.0675 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242107453D          

 56 56  0  0  0  0            999 V2000
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   -2.6468   -3.1990   -0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5820   -2.5647    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -3.5345    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490   -1.1007   -2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7763   -2.7028   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792    0.1091   -1.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0261   -1.2765   -2.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1946   -2.6141   -0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505    0.7882    1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0804    1.0117    0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7144    1.1547   -0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -2.3801    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -0.7869   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347   -2.2386   -0.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4489    1.1985   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4974    0.7094    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4289   -0.2299    0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9019    1.4184    0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5265    2.4495   -2.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5862    2.9394   -0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7871    3.3553   -0.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  1  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  1  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  3  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24  9  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  2 27  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  5 31  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
  7 34  1  0  0  0  0
  8 35  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 10 38  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 13 43  1  6  0  0  0
 15 44  1  0  0  0  0
 15 45  1  0  0  0  0
 15 46  1  0  0  0  0
 16 47  1  0  0  0  0
 17 48  1  0  0  0  0
 17 49  1  0  0  0  0
 20 50  1  0  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
 22 53  1  0  0  0  0
 23 54  1  0  0  0  0
 23 55  1  0  0  0  0
 23 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011245

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@](C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])C(\[H])=C(/[H])[C@@]1(O[C@@]([H])(C([H])([H])C1([H])[H])[C@](O[H])(C([H])([H])[H])C([H])([H])C(=O)C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-7-18(4,22)10-8-11-19(5)12-9-17(24-19)20(6,23)14-16(21)13-15(2)3/h7-8,11,13,17,22-23H,1,9-10,12,14H2,2-6H3/b11-8+/t17-,18-,19-,20-/m0/s1

> <INCHI_KEY>
HYSXHSFJFJWWOB-DQQJITHMSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.54806851823799

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6S)-6-hydroxy-6-[(2S,5R)-5-[(1E,4R)-4-hydroxy-4-methylhexa-1,5-dien-1-yl]-5-methyloxolan-2-yl]-2-methylhept-2-en-4-one

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
3.208978704999999

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.434243771760197

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.853253459679213

> <JCHEM_PKA_STRONGEST_BASIC>
-1.35800851965007

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
98.90809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-6-hydroxy-6-[(2S,5R)-5-[(1E,4R)-4-hydroxy-4-methylhexa-1,5-dien-1-yl]-5-methyloxolan-2-yl]-2-methylhept-2-en-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 56  0  0  0  0  0  0  0  0999 V2000
   -6.8326    2.5763   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1822    2.0201    0.9598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4465    0.7424    0.7658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2173   -0.2179   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2089    0.1625    2.0119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1524    1.0705    0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3273   -0.1682   -0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1198   -0.3092    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2684   -1.5344    0.1013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9818   -2.7820    0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9436   -1.6474   -1.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4370   -0.9741   -1.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9732   -1.5486   -0.0798 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2218   -0.8696    0.3843 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0526    0.6084    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5816   -1.4337    1.6080 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3390   -1.1423   -0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5978   -0.4757   -0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568   -1.0293    0.7572 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0599    0.7688   -0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1707    1.3360   -0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0106    0.7563    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5826    2.6227   -1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870   -1.4157    0.7766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8213    2.0918   -1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3722    3.5072    0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1904    2.4961    1.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8711   -0.1825   -1.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3159   -0.0142   -0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0212   -1.2480    0.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9060    0.8628    2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5462    1.8270    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4264    1.4977   -0.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276   -0.9734   -0.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359    0.5130    0.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -3.1990   -0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5820   -2.5647    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -3.5345    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490   -1.1007   -2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7763   -2.7028   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792    0.1091   -1.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0261   -1.2765   -2.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1946   -2.6141   -0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505    0.7882    1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0804    1.0117    0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7144    1.1547   -0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -2.3801    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -0.7869   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347   -2.2386   -0.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4489    1.1985   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4974    0.7094    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4289   -0.2299    0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9019    1.4184    0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5265    2.4495   -2.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5862    2.9394   -0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7871    3.3553   -0.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  1
  3  6  1  0
  6  7  1  0
  7  8  2  0
  9  8  1  6
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  1
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
 13 24  1  0
 24  9  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  6
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -6.833   2.576  -0.050  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.182   2.020   0.960  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.447   0.742   0.766  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.217  -0.218  -0.122  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.209   0.163   2.012  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.152   1.071   0.068  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.327  -0.168  -0.176  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.120  -0.309   0.326  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.268  -1.534   0.101  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.982  -2.782   0.572  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.944  -1.647  -1.386  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.437  -0.974  -1.372  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.973  -1.549  -0.080  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.222  -0.870   0.384  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.053   0.608   0.608  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.582  -1.434   1.608  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.339  -1.142  -0.591  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.598  -0.476  -0.153  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.257  -1.029   0.757  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.060   0.769  -0.746  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.171   1.336  -0.345  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.011   0.756   0.720  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.583   2.623  -1.006  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.087  -1.416   0.777  0.00  0.00           O+0
HETATM   25  H   UNK     0      -6.821   2.092  -1.011  0.00  0.00           H+0
HETATM   26  H   UNK     0      -7.372   3.507   0.079  0.00  0.00           H+0
HETATM   27  H   UNK     0      -6.190   2.496   1.915  0.00  0.00           H+0
HETATM   28  H   UNK     0      -5.871  -0.183  -1.178  0.00  0.00           H+0
HETATM   29  H   UNK     0      -7.316  -0.014  -0.076  0.00  0.00           H+0
HETATM   30  H   UNK     0      -6.021  -1.248   0.242  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.906   0.863   2.645  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.546   1.827   0.584  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.426   1.498  -0.932  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.728  -0.973  -0.781  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.736   0.513   0.930  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.647  -3.199  -0.214  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.582  -2.565   1.487  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.208  -3.535   0.817  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.649  -1.101  -2.015  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.776  -2.703  -1.691  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.279   0.109  -1.291  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.026  -1.276  -2.259  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.195  -2.614  -0.254  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.450   0.788   1.510  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.080   1.012   0.834  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.714   1.155  -0.285  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.811  -2.380   1.527  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.013  -0.787  -1.591  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.535  -2.239  -0.565  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.449   1.198  -1.526  0.00  0.00           H+0
HETATM   51  H   UNK     0       6.497   0.709   1.705  0.00  0.00           H+0
HETATM   52  H   UNK     0       7.429  -0.230   0.446  0.00  0.00           H+0
HETATM   53  H   UNK     0       7.902   1.418   0.884  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.527   2.450  -2.094  0.00  0.00           H+0
HETATM   55  H   UNK     0       7.586   2.939  -0.665  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.787   3.355  -0.759  0.00  0.00           H+0
CONECT    1    2   25   26                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4    5    6                                             
CONECT    4    3   28   29   30                                             
CONECT    5    3   31                                                       
CONECT    6    3    7   32   33                                             
CONECT    7    6    8   34                                                  
CONECT    8    7    9   35                                                  
CONECT    9    8   10   11   24                                             
CONECT   10    9   36   37   38                                             
CONECT   11    9   12   39   40                                             
CONECT   12   11   13   41   42                                             
CONECT   13   12   14   24   43                                             
CONECT   14   13   15   16   17                                             
CONECT   15   14   44   45   46                                             
CONECT   16   14   47                                                       
CONECT   17   14   18   48   49                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   50                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   51   52   53                                             
CONECT   23   21   54   55   56                                             
CONECT   24   13    9                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    2                                                            
CONECT   28    4                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   20                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  112    0
END

RDKit          3D

56 56  0  0  0  0  0  0  0  0999 V2000
   -6.8326    2.5763   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1822    2.0201    0.9598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4465    0.7424    0.7658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2173   -0.2179   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2089    0.1625    2.0119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1524    1.0705    0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3273   -0.1682   -0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1198   -0.3092    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2684   -1.5344    0.1013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9818   -2.7820    0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9436   -1.6474   -1.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4370   -0.9741   -1.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9732   -1.5486   -0.0798 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2218   -0.8696    0.3843 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0526    0.6084    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5816   -1.4337    1.6080 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3390   -1.1423   -0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5978   -0.4757   -0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568   -1.0293    0.7572 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0599    0.7688   -0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1707    1.3360   -0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0106    0.7563    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5826    2.6227   -1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870   -1.4157    0.7766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8213    2.0918   -1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3722    3.5072    0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1904    2.4961    1.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8711   -0.1825   -1.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3159   -0.0142   -0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0212   -1.2480    0.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9060    0.8628    2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5462    1.8270    0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4264    1.4977   -0.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276   -0.9734   -0.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7359    0.5130    0.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -3.1990   -0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5820   -2.5647    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -3.5345    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490   -1.1007   -2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7763   -2.7028   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792    0.1091   -1.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0261   -1.2765   -2.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1946   -2.6141   -0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505    0.7882    1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0804    1.0117    0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7144    1.1547   -0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -2.3801    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -0.7869   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347   -2.2386   -0.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4489    1.1985   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4974    0.7094    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4289   -0.2299    0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9019    1.4184    0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5265    2.4495   -2.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5862    2.9394   -0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7871    3.3553   -0.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  1
  3  6  1  0
  6  7  1  0
  7  8  2  0
  9  8  1  6
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  1
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
 13 24  1  0
 24  9  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  6
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Hueafuranoid a	MeSH

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4720 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

(6S)-6-hydroxy-6-[(2S,5R)-5-[(1E,4R)-4-hydroxy-4-methylhexa-1,5-dien-1-yl]-5-methyloxolan-2-yl]-2-methylhept-2-en-4-one

Traditional Name

(6S)-6-hydroxy-6-[(2S,5R)-5-[(1E,4R)-4-hydroxy-4-methylhexa-1,5-dien-1-yl]-5-methyloxolan-2-yl]-2-methylhept-2-en-4-one

CAS Registry Number

Not Available

SMILES

CC(C)=CC(=O)CC(C)(O)[C@@H]1CC[C@@](C)(O1)\C=C\CC(C)(O)C=C

InChI Identifier

InChI=1S/C20H32O4/c1-7-18(4,22)10-8-11-19(5)12-9-17(24-19)20(6,23)14-16(21)13-15(2)3/h7-8,11,13,17,22-23H,1,9-10,12,14H2,2-6H3/b11-8+/t17-,18?,19-,20?/m0/s1

InChI Key

HYSXHSFJFJWWOB-DQQJITHMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Huea	NPAtlas	23141910

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
B'-hydroxy-alpha,beta-unsaturated-ketone
Beta-hydroxy ketone
Acryloyl-group
Enone
Oxolane
Alpha,beta-unsaturated ketone
Tertiary alcohol
Ketone
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.83	ALOGPS
logP	3.21	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	98.91 m³·mol⁻¹	ChemAxon
Polarizability	39.55 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA013801

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28650788

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71461461

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cui Y, Yim JH, Lee DS, Kim YC, Oh H: New diterpene furanoids from the Antarctic lichen Huea sp. Bioorg Med Chem Lett. 2012 Dec 15;22(24):7393-6. doi: 10.1016/j.bmcl.2012.10.063. Epub 2012 Oct 23. [PubMed:23141910 ]

Showing NP-Card for Hueafuranoid A (NP0011245)

MOL for NP0011245 (Hueafuranoid A)

3D MOL for NP0011245 (Hueafuranoid A)

3D SDF for NP0011245 (Hueafuranoid A)

3D-SDF for NP0011245 (Hueafuranoid A)

PDB for NP0011245 (Hueafuranoid A)

3D PDB for NP0011245 (Hueafuranoid A)

SMILES for NP0011245 (Hueafuranoid A)

INCHI for NP0011245 (Hueafuranoid A)

Structure for NP0011245 (Hueafuranoid A)

3D Structure for NP0011245 (Hueafuranoid A)