NP-MRD: Showing NP-Card for Repraesentin E (NP0006445)

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Record Information

Version

2.0

Created at

2020-12-09 03:27:30 UTC

Updated at

2021-07-15 16:54:49 UTC

NP-MRD ID

NP0006445

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Repraesentin E

Provided By

NPAtlas

Description

Repraesentin E belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Repraesentin E is found in Lactarius repraesentaneus. Repraesentin E was first documented in 2006 (PMID: 16794335). Based on a literature review very few articles have been published on Repraesentin E.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118273D          

 40 42  0  0  0  0            999 V2000
   -0.2340    2.4230   -1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5162    1.0870   -0.9498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9978    0.9802   -0.8580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4837   -0.2891   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597   -0.7784    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2944   -1.8377    1.1833 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5373   -2.3190   -0.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3264   -1.2736   -1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7483   -1.1761   -2.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1899   -0.3708    1.8039 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1151   -0.1011    1.1857 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6681   -1.1872    0.3184 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9791   -0.5203   -0.1290 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905   -0.9722   -1.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422   -0.8670    0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985   -1.5913    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169   -0.3936    0.6858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7217    0.9788   -0.0501 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4486    1.5841    0.9490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281    1.0984    0.3208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0957    2.7055   -2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    3.1864   -0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6504    2.3803   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587    0.3104   -1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    1.8713   -0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071    1.0836   -1.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -2.5676    1.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1710   -1.3363    1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024    0.5185    2.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634   -1.1879    2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8621    0.0358    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0488   -1.3986   -0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -2.1253    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.1742   -2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889   -1.8570   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -1.3608   -2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7819    0.2795    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264    1.3899   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9280    1.7779    1.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    1.9945    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 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
 13 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20  2  1  0  0  0  0
  8  4  1  0  0  0  0
 20 11  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2 24  1  6  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  6 27  1  0  0  0  0
  6 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  1  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
 17 37  1  0  0  0  0
 18 38  1  6  0  0  0
 19 39  1  0  0  0  0
 20 40  1  1  0  0  0
M  END

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -0.2340    2.4230   -1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5162    1.0870   -0.9498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9978    0.9802   -0.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4837   -0.2891   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597   -0.7784    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2944   -1.8377    1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373   -2.3190   -0.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3264   -1.2736   -1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7483   -1.1761   -2.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1899   -0.3708    1.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151   -0.1011    1.1857 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6681   -1.1872    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9791   -0.5203   -0.1290 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905   -0.9722   -1.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422   -0.8670    0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985   -1.5913    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169   -0.3936    0.6858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7217    0.9788   -0.0501 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4486    1.5841    0.9490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281    1.0984    0.3208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0957    2.7055   -2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    3.1864   -0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6504    2.3803   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587    0.3104   -1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    1.8713   -0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071    1.0836   -1.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -2.5676    1.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1710   -1.3363    1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024    0.5185    2.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634   -1.1879    2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8621    0.0358    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0488   -1.3986   -0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -2.1253    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.1742   -2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889   -1.8570   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -1.3608   -2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7819    0.2795    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264    1.3899   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9280    1.7779    1.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    1.9945    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 15 16  2  0
 15 17  1  0
 13 18  1  0
 18 19  1  0
 18 20  1  0
 20  2  1  0
  8  4  1  0
 20 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  6
 19 39  1  0
 20 40  1  1
M  END


  Mrv1652306242118273D          

 40 42  0  0  0  0            999 V2000
   -0.2340    2.4230   -1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5162    1.0870   -0.9498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9978    0.9802   -0.8580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4837   -0.2891   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597   -0.7784    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2944   -1.8377    1.1833 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5373   -2.3190   -0.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3264   -1.2736   -1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7483   -1.1761   -2.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1899   -0.3708    1.8039 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1151   -0.1011    1.1857 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6681   -1.1872    0.3184 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9791   -0.5203   -0.1290 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905   -0.9722   -1.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422   -0.8670    0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985   -1.5913    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169   -0.3936    0.6858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7217    0.9788   -0.0501 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4486    1.5841    0.9490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281    1.0984    0.3208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0957    2.7055   -2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    3.1864   -0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6504    2.3803   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587    0.3104   -1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    1.8713   -0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071    1.0836   -1.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -2.5676    1.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1710   -1.3363    1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024    0.5185    2.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634   -1.1879    2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8621    0.0358    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0488   -1.3986   -0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -2.1253    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.1742   -2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889   -1.8570   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -1.3608   -2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7819    0.2795    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264    1.3899   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9280    1.7779    1.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    1.9945    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 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
 13 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20  2  1  0  0  0  0
  8  4  1  0  0  0  0
 20 11  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2 24  1  6  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  6 27  1  0  0  0  0
  6 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  1  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
 17 37  1  0  0  0  0
 18 38  1  6  0  0  0
 19 39  1  0  0  0  0
 20 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0006445

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1(C([H])([H])[H])C([H])([H])[C@]2([H])C([H])([H])C3=C(C(=O)OC3([H])[H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]2([H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O5/c1-7-3-10-9(6-20-13(10)17)4-8-5-15(2,14(18)19)12(16)11(7)8/h7-8,11-12,16H,3-6H2,1-2H3,(H,18,19)/t7-,8+,11+,12-,15+/m1/s1

> <INCHI_KEY>
VGLFPPRJHYACEV-UHFFFAOYSA-N

> <FORMULA>
C15H20O5

> <MOLECULAR_WEIGHT>
280.32

> <EXACT_MASS>
280.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.40393514062597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,6S,7R,7aS,8R)-7-hydroxy-6,8-dimethyl-1-oxo-1H,3H,4H,4aH,5H,6H,7H,7aH,8H,9H-azuleno[5,6-c]furan-6-carboxylic acid

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
1.5133089716666666

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.323207135221498

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.20589365946165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1368439259070238

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
70.5113

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6S,7R,7aS,8R)-7-hydroxy-6,8-dimethyl-1-oxo-3H,4H,4aH,5H,7H,7aH,8H,9H-azuleno[5,6-c]furan-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -0.2340    2.4230   -1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5162    1.0870   -0.9498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9978    0.9802   -0.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4837   -0.2891   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597   -0.7784    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2944   -1.8377    1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373   -2.3190   -0.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3264   -1.2736   -1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7483   -1.1761   -2.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1899   -0.3708    1.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151   -0.1011    1.1857 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6681   -1.1872    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9791   -0.5203   -0.1290 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905   -0.9722   -1.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422   -0.8670    0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985   -1.5913    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7217    0.9788   -0.0501 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4486    1.5841    0.9490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281    1.0984    0.3208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0957    2.7055   -2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    3.1864   -0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6504    2.3803   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587    0.3104   -1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    1.8713   -0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071    1.0836   -1.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -2.5676    1.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1710   -1.3363    1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024    0.5185    2.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634   -1.1879    2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8621    0.0358    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0488   -1.3986   -0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -2.1253    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.1742   -2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889   -1.8570   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -1.3608   -2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7819    0.2795    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264    1.3899   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9280    1.7779    1.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    1.9945    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
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  5 10  1  0
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 11 12  1  0
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 13 14  1  0
 13 15  1  1
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 18 20  1  0
 20  2  1  0
  8  4  1  0
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  1 21  1  0
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  2 24  1  6
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  6 27  1  0
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 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  6
 19 39  1  0
 20 40  1  1
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      -0.234   2.423  -1.658  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.516   1.087  -0.950  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.998   0.980  -0.858  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.484  -0.289  -0.318  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.260  -0.778   0.890  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.294  -1.838   1.183  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.537  -2.319  -0.125  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.326  -1.274  -1.031  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.748  -1.176  -2.189  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.190  -0.371   1.804  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.115  -0.101   1.186  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.668  -1.187   0.318  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.979  -0.520  -0.129  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.390  -0.972  -1.486  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.042  -0.867   0.855  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.799  -1.591   1.849  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.317  -0.394   0.686  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.722   0.979  -0.050  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.449   1.584   0.949  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.228   1.098   0.321  0.00  0.00           C+0
HETATM   21  H   UNK     0      -1.096   2.705  -2.313  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.162   3.186  -0.862  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.650   2.380  -2.285  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.159   0.310  -1.657  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.405   1.871  -0.306  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.407   1.084  -1.893  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.802  -2.568   1.826  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.171  -1.336   1.629  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.502   0.519   2.385  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.063  -1.188   2.554  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.862   0.036   2.025  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.049  -1.399  -0.563  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.882  -2.125   0.871  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.922  -0.174  -2.058  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.089  -1.857  -1.425  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.514  -1.361  -2.069  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.782   0.280   1.276  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.926   1.390  -1.038  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.928   1.778   1.745  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.041   1.994   0.910  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    1    3   20   24                                             
CONECT    3    2    4   25   26                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7   27   28                                             
CONECT    7    6    8                                                       
CONECT    8    7    9    4                                                  
CONECT    9    8                                                            
CONECT   10    5   11   29   30                                             
CONECT   11   10   12   20   31                                             
CONECT   12   11   13   32   33                                             
CONECT   13   12   14   15   18                                             
CONECT   14   13   34   35   36                                             
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   37                                                       
CONECT   18   13   19   20   38                                             
CONECT   19   18   39                                                       
CONECT   20   18    2   11   40                                             
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    2                                                            
CONECT   25    3                                                            
CONECT   26    3                                                            
CONECT   27    6                                                            
CONECT   28    6                                                            
CONECT   29   10                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   14                                                            
CONECT   37   17                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

RDKit          3D

40 42  0  0  0  0  0  0  0  0999 V2000
   -0.2340    2.4230   -1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5162    1.0870   -0.9498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9978    0.9802   -0.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4837   -0.2891   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597   -0.7784    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2944   -1.8377    1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373   -2.3190   -0.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3264   -1.2736   -1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7483   -1.1761   -2.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1899   -0.3708    1.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151   -0.1011    1.1857 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6681   -1.1872    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9791   -0.5203   -0.1290 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905   -0.9722   -1.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422   -0.8670    0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985   -1.5913    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169   -0.3936    0.6858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7217    0.9788   -0.0501 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4486    1.5841    0.9490 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281    1.0984    0.3208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0957    2.7055   -2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    3.1864   -0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6504    2.3803   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587    0.3104   -1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    1.8713   -0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071    1.0836   -1.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -2.5676    1.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1710   -1.3363    1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024    0.5185    2.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0634   -1.1879    2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8621    0.0358    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0488   -1.3986   -0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -2.1253    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.1742   -2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889   -1.8570   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -1.3608   -2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7819    0.2795    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264    1.3899   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9280    1.7779    1.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    1.9945    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 15 16  2  0
 15 17  1  0
 13 18  1  0
 18 19  1  0
 18 20  1  0
 20  2  1  0
  8  4  1  0
 20 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  6
 19 39  1  0
 20 40  1  1
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
7-Hydroxy-6,8-dimethyl-1-oxo-1H,3H,4H,4ah,5H,6H,7H,7ah,8H,9H-azuleno[5,6-c]furan-6-carboxylate	Generator

Chemical Formula

C₁₅H₂₀O₅

Average Mass

280.3200 Da

Monoisotopic Mass

280.13107 Da

IUPAC Name

(4aS,6S,7R,7aS,8R)-7-hydroxy-6,8-dimethyl-1-oxo-1H,3H,4H,4aH,5H,6H,7H,7aH,8H,9H-azuleno[5,6-c]furan-6-carboxylic acid

Traditional Name

(4aS,6S,7R,7aS,8R)-7-hydroxy-6,8-dimethyl-1-oxo-3H,4H,4aH,5H,7H,7aH,8H,9H-azuleno[5,6-c]furan-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1CC2=C(COC2=O)CC2CC(C)(C(O)C12)C(O)=O

InChI Identifier

InChI=1S/C15H20O5/c1-7-3-10-9(6-20-13(10)17)4-8-5-15(2,14(18)19)12(16)11(7)8/h7-8,11-12,16H,3-6H2,1-2H3,(H,18,19)

InChI Key

VGLFPPRJHYACEV-UHFFFAOYSA-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
Lactarius repraesentaneus	NPAtlas	16794335

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Lactarane sesquiterpenoid
Sesquiterpenoid
Beta-hydroxy acid
2-furanone
Dicarboxylic acid or derivatives
Hydroxy acid
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.06	ALOGPS
logP	1.51	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.51 m³·mol⁻¹	ChemAxon
Polarizability	28.4 Å³	ChemAxon
Number of Rings	3	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

NPA015491

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78444315

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102384489

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kashiwabara M, Kamo T, Makabe H, Shibata H, Hirota M: Repraesentins D, E and F, new plant growth promoters from Lactarius repraesentaneus. Biosci Biotechnol Biochem. 2006 Jun;70(6):1502-5. doi: 10.1271/bbb.50639. [PubMed:16794335 ]

Showing NP-Card for Repraesentin E (NP0006445)

MOL for NP0006445 (Repraesentin E)

3D MOL for NP0006445 (Repraesentin E)

3D SDF for NP0006445 (Repraesentin E)

3D-SDF for NP0006445 (Repraesentin E)

PDB for NP0006445 (Repraesentin E)

3D PDB for NP0006445 (Repraesentin E)

SMILES for NP0006445 (Repraesentin E)

INCHI for NP0006445 (Repraesentin E)

Structure for NP0006445 (Repraesentin E)

3D Structure for NP0006445 (Repraesentin E)