NP-MRD: Showing NP-Card for 5,10-epi-2,3-dihydroaromatin (NP0037228)

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Record Information

Version

2.0

Created at

2021-06-20 20:11:59 UTC

Updated at

2021-06-30 00:09:18 UTC

NP-MRD ID

NP0037228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,10-epi-2,3-dihydroaromatin

Provided By

JEOL Database JEOL Logo

Description

(3AR)-alpha-Methylene-3-oxo-3abeta,8alpha-dimethyl-6alpha-hydroxy-1,2,3,3a,4,5,6,7,8,8abeta-decahydroazulene-5alpha-acetic acid 5,6-lactone belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). 5,10-epi-2,3-dihydroaromatin is found in Ambrosia confertiflora, Ambrosia dumosa, Ambrosia tenuifolia , Dittrichia graveolens (L.) GREUTER , Francoeuria crispa, Inula graveolens, Parthenium schottii, Pulicaria crispa (Forssk.) Oliv., Telekia speciosa and Vicoa pentanema. 5,10-epi-2,3-dihydroaromatin was first documented in 2008 (Stavri, M., et al.). Based on a literature review very few articles have been published on (3aR)-alpha-Methylene-3-oxo-3abeta,8alpha-dimethyl-6alpha-hydroxy-1,2,3,3a,4,5,6,7,8,8abeta-decahydroazulene-5alpha-acetic acid 5,6-lactone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122123D          

 38 40  0  0  0  0            999 V2000
   -0.9725   -0.3672   -2.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8502   -1.1854   -1.4196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -2.3542   -1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7491   -2.6157   -1.8198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1963   -3.0818   -0.1960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -2.5798    0.1443 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3383   -2.8640    1.6263 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5778   -2.1830    2.2214 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1390   -3.0600    3.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3456   -0.7443    2.7385 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3263   -0.6039    3.8813 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1445    0.8990    4.0420 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3355    1.3939    2.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0715    2.5380    2.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9037    0.3203    1.7021 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1170    0.9009    0.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -0.0888    0.7391 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1556   -1.1304   -0.3182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7499   -0.5240   -3.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    0.4803   -2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -3.1710   -0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653   -2.6350    2.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -3.9553    1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3569   -2.1422    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932   -3.2399    4.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156   -2.5933    3.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543   -4.0343    2.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102   -0.4114    3.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362   -1.0613    3.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784   -1.0547    4.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8490    1.1503    4.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228    1.3299    4.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8071    1.6284    0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049    0.1220    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7874    1.4278    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694    0.8227    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109   -0.4264    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1439   -0.9083   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0  0  0  0
  8  7  1  0  0  0  0
 15 10  1  0  0  0  0
 17 18  1  0  0  0  0
 10  8  1  0  0  0  0
 18  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  0  0  0  0
 15 17  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  1  0  0  0  0
  2  1  2  3  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8  9  1  0  0  0  0
 10 28  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
  8 24  1  6  0  0  0
  7 22  1  0  0  0  0
  7 23  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
  6 21  1  6  0  0  0
 18 38  1  6  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
M  END

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.9725   -0.3672   -2.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8502   -1.1854   -1.4196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -2.3542   -1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7491   -2.6157   -1.8198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1963   -3.0818   -0.1960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -2.5798    0.1443 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3383   -2.8640    1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5778   -2.1830    2.2214 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1390   -3.0600    3.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3456   -0.7443    2.7385 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3263   -0.6039    3.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1445    0.8990    4.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    1.3939    2.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0715    2.5380    2.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9037    0.3203    1.7021 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1170    0.9009    0.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -0.0888    0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556   -1.1304   -0.3182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7499   -0.5240   -3.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    0.4803   -2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -3.1710   -0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653   -2.6350    2.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -3.9553    1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3569   -2.1422    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932   -3.2399    4.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156   -2.5933    3.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543   -4.0343    2.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102   -0.4114    3.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362   -1.0613    3.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784   -1.0547    4.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8490    1.1503    4.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228    1.3299    4.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8071    1.6284    0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049    0.1220    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7874    1.4278    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694    0.8227    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109   -0.4264    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1439   -0.9083   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0
  8  7  1  0
 15 10  1  0
 17 18  1  0
 10  8  1  0
 18  2  1  0
  2  3  1  0
  3  5  1  0
  6  5  1  0
 15 17  1  0
  3  4  2  0
  6  7  1  0
  2  1  2  3
 10 11  1  0
 11 12  1  0
  8  9  1  0
 10 28  1  1
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  6
 17 36  1  0
 17 37  1  0
  8 24  1  6
  7 22  1  0
  7 23  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
  6 21  1  6
 18 38  1  6
  1 19  1  0
  1 20  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
M  END


  Mrv1652306202122123D          

 38 40  0  0  0  0            999 V2000
   -0.9725   -0.3672   -2.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8502   -1.1854   -1.4196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -2.3542   -1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7491   -2.6157   -1.8198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1963   -3.0818   -0.1960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -2.5798    0.1443 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3383   -2.8640    1.6263 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5778   -2.1830    2.2214 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1390   -3.0600    3.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3456   -0.7443    2.7385 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3263   -0.6039    3.8813 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1445    0.8990    4.0420 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3355    1.3939    2.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0715    2.5380    2.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9037    0.3203    1.7021 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1170    0.9009    0.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -0.0888    0.7391 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1556   -1.1304   -0.3182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7499   -0.5240   -3.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    0.4803   -2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -3.1710   -0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653   -2.6350    2.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -3.9553    1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3569   -2.1422    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932   -3.2399    4.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156   -2.5933    3.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543   -4.0343    2.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102   -0.4114    3.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362   -1.0613    3.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784   -1.0547    4.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8490    1.1503    4.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228    1.3299    4.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8071    1.6284    0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049    0.1220    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7874    1.4278    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694    0.8227    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109   -0.4264    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1439   -0.9083   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0  0  0  0
  8  7  1  0  0  0  0
 15 10  1  0  0  0  0
 17 18  1  0  0  0  0
 10  8  1  0  0  0  0
 18  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  0  0  0  0
 15 17  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  1  0  0  0  0
  2  1  2  3  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8  9  1  0  0  0  0
 10 28  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
  8 24  1  6  0  0  0
  7 22  1  0  0  0  0
  7 23  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
  6 21  1  6  0  0  0
 18 38  1  6  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037228

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1C(=O)O[C@]2([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])C(=O)[C@]3(C([H])([H])[H])C([H])([H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-6-12-10(9(2)14(17)18-12)7-15(3)11(8)4-5-13(15)16/h8,10-12H,2,4-7H2,1,3H3/t8-,10+,11-,12+,15+/m0/s1

> <INCHI_KEY>
DCKYPAZZUYXYTC-ZGWNKZGNSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.051910821807013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4aR,7aS,8S,9aR)-4a,8-dimethyl-3-methylidene-dodecahydroazuleno[6,5-b]furan-2,5-dione

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
3.038337771666667

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.95908879335692

> <JCHEM_PKA_STRONGEST_BASIC>
-6.769647156963739

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
67.1131

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4aR,7aS,8S,9aR)-4a,8-dimethyl-3-methylidene-octahydroazuleno[6,5-b]furan-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.9725   -0.3672   -2.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8502   -1.1854   -1.4196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -2.3542   -1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7491   -2.6157   -1.8198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1963   -3.0818   -0.1960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -2.5798    0.1443 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3383   -2.8640    1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5778   -2.1830    2.2214 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1390   -3.0600    3.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3456   -0.7443    2.7385 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3263   -0.6039    3.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1445    0.8990    4.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    1.3939    2.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0715    2.5380    2.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9037    0.3203    1.7021 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1170    0.9009    0.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -0.0888    0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556   -1.1304   -0.3182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7499   -0.5240   -3.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    0.4803   -2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -3.1710   -0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653   -2.6350    2.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -3.9553    1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3569   -2.1422    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932   -3.2399    4.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156   -2.5933    3.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543   -4.0343    2.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102   -0.4114    3.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362   -1.0613    3.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784   -1.0547    4.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8490    1.1503    4.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228    1.3299    4.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8071    1.6284    0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049    0.1220    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7874    1.4278    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694    0.8227    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109   -0.4264    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1439   -0.9083   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0
  8  7  1  0
 15 10  1  0
 17 18  1  0
 10  8  1  0
 18  2  1  0
  2  3  1  0
  3  5  1  0
  6  5  1  0
 15 17  1  0
  3  4  2  0
  6  7  1  0
  2  1  2  3
 10 11  1  0
 11 12  1  0
  8  9  1  0
 10 28  1  1
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  6
 17 36  1  0
 17 37  1  0
  8 24  1  6
  7 22  1  0
  7 23  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
  6 21  1  6
 18 38  1  6
  1 19  1  0
  1 20  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 16 33  1  0
 16 34  1  0
 16 35  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      -0.973  -0.367  -2.472  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.850  -1.185  -1.420  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.729  -2.354  -1.212  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.749  -2.616  -1.820  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.196  -3.082  -0.196  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.108  -2.580   0.144  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.338  -2.864   1.626  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.578  -2.183   2.221  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.139  -3.060   3.353  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.346  -0.744   2.739  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.326  -0.604   3.881  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.145   0.899   4.042  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.336   1.394   2.633  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.072   2.538   2.282  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.904   0.320   1.702  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.117   0.901   0.964  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.232  -0.089   0.739  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.156  -1.130  -0.318  0.00  0.00           C+0
HETATM   19  H   UNK     0      -1.750  -0.524  -3.216  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.310   0.480  -2.611  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.832  -3.171  -0.435  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.565  -2.635   2.201  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.434  -3.955   1.720  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.357  -2.142   1.449  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.393  -3.240   4.134  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.016  -2.593   3.814  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.454  -4.034   2.963  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.310  -0.411   3.156  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.636  -1.061   3.633  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.678  -1.055   4.814  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.849   1.150   4.420  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.923   1.330   4.678  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.807   1.628   0.205  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.705   0.122   0.469  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.787   1.428   1.653  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.569   0.823   0.224  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.111  -0.426   1.305  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.144  -0.908  -0.733  0.00  0.00           H+0
CONECT    1    2   19   20                                                  
CONECT    2   18    3    1                                                  
CONECT    3    2    5    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6   18    5    7   21                                             
CONECT    7    8    6   22   23                                             
CONECT    8    7   10    9   24                                             
CONECT    9    8   25   26   27                                             
CONECT   10   15    8   11   28                                             
CONECT   11   10   12   29   30                                             
CONECT   12   11   13   31   32                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   10   17   13   16                                             
CONECT   16   15   33   34   35                                             
CONECT   17   18   15   36   37                                             
CONECT   18    6   17    2   38                                             
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    6                                                            
CONECT   22    7                                                            
CONECT   23    7                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
CONECT   26    9                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   16                                                            
CONECT   34   16                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   17                                                            
CONECT   38   18                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

RDKit          3D

38 40  0  0  0  0  0  0  0  0999 V2000
   -0.9725   -0.3672   -2.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8502   -1.1854   -1.4196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293   -2.3542   -1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7491   -2.6157   -1.8198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1963   -3.0818   -0.1960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -2.5798    0.1443 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3383   -2.8640    1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5778   -2.1830    2.2214 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1390   -3.0600    3.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3456   -0.7443    2.7385 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3263   -0.6039    3.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1445    0.8990    4.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    1.3939    2.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0715    2.5380    2.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9037    0.3203    1.7021 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1170    0.9009    0.9637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -0.0888    0.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556   -1.1304   -0.3182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7499   -0.5240   -3.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    0.4803   -2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -3.1710   -0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653   -2.6350    2.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -3.9553    1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3569   -2.1422    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932   -3.2399    4.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0156   -2.5933    3.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543   -4.0343    2.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102   -0.4114    3.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362   -1.0613    3.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784   -1.0547    4.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8490    1.1503    4.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228    1.3299    4.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8071    1.6284    0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049    0.1220    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7874    1.4278    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694    0.8227    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109   -0.4264    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1439   -0.9083   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0
  8  7  1  0
 15 10  1  0
 17 18  1  0
 10  8  1  0
 18  2  1  0
  2  3  1  0
  3  5  1  0
  6  5  1  0
 15 17  1  0
  3  4  2  0
  6  7  1  0
  2  1  2  3
 10 11  1  0
 11 12  1  0
  8  9  1  0
 10 28  1  1
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  6
 17 36  1  0
 17 37  1  0
  8 24  1  6
  7 22  1  0
  7 23  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
  6 21  1  6
 18 38  1  6
  1 19  1  0
  1 20  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
(3AR)-a-methylene-3-oxo-3abeta,8a-dimethyl-6a-hydroxy-1,2,3,3a,4,5,6,7,8,8abeta-decahydroazulene-5a-acetate 5,6-lactone	Generator
(3AR)-a-methylene-3-oxo-3abeta,8a-dimethyl-6a-hydroxy-1,2,3,3a,4,5,6,7,8,8abeta-decahydroazulene-5a-acetic acid 5,6-lactone	Generator
(3AR)-alpha-methylene-3-oxo-3abeta,8alpha-dimethyl-6alpha-hydroxy-1,2,3,3a,4,5,6,7,8,8abeta-decahydroazulene-5alpha-acetate 5,6-lactone	Generator
(3AR)-α-methylene-3-oxo-3abeta,8α-dimethyl-6α-hydroxy-1,2,3,3a,4,5,6,7,8,8abeta-decahydroazulene-5α-acetate 5,6-lactone	Generator
(3AR)-α-methylene-3-oxo-3abeta,8α-dimethyl-6α-hydroxy-1,2,3,3a,4,5,6,7,8,8abeta-decahydroazulene-5α-acetic acid 5,6-lactone	Generator

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(3aR,4aR,7aS,8S,9aR)-4a,8-dimethyl-3-methylidene-dodecahydroazuleno[6,5-b]furan-2,5-dione

Traditional Name

(3aR,4aR,7aS,8S,9aR)-4a,8-dimethyl-3-methylidene-octahydroazuleno[6,5-b]furan-2,5-dione

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1C(=O)O[C@]2([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])C(=O)[C@]3(C([H])([H])[H])C([H])([H])[C@]12[H]

InChI Identifier

InChI=1S/C15H20O3/c1-8-6-12-10(9(2)14(17)18-12)7-15(3)11(8)4-5-13(15)16/h8,10-12H,2,4-7H2,1,3H3/t8-,10+,11-,12+,15+/m0/s1

InChI Key

DCKYPAZZUYXYTC-ZGWNKZGNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₆D₆, 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
Ambrosia confertiflora	Plant	KNApSAcK
Ambrosia dumosa	Plant	KNApSAcK
Ambrosia tenuifolia	Plant	KNApSAcK
Dittrichia graveolens	Plant	KNApSAcK
Francoeuria crispa	-	KNApSAcK
Inula graveolens	Plant	KNApSAcK
Parthenium schottii	Plant	KNApSAcK
Pulicaria crispa (Forssk.) Oliv.	JEOL database	Stavri, M., et al, Phytochem. 69, 1915 (2008)
Telekia speciosa	Plant	KNApSAcK
Vicoa pentanema	-	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	1.48	ALOGPS
logP	3.04	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	19.96	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.11 m³·mol⁻¹	ChemAxon
Polarizability	27.05 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24893981

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stavri, M., et al. (2008). Stavri, M., et al, Phytochem. 69, 1915 (2008). Phytochem..

Showing NP-Card for 5,10-epi-2,3-dihydroaromatin (NP0037228)

MOL for NP0037228 (5,10-epi-2,3-dihydroaromatin)

3D MOL for NP0037228 (5,10-epi-2,3-dihydroaromatin)

3D SDF for NP0037228 (5,10-epi-2,3-dihydroaromatin)

3D-SDF for NP0037228 (5,10-epi-2,3-dihydroaromatin)

PDB for NP0037228 (5,10-epi-2,3-dihydroaromatin)

3D PDB for NP0037228 (5,10-epi-2,3-dihydroaromatin)

SMILES for NP0037228 (5,10-epi-2,3-dihydroaromatin)

INCHI for NP0037228 (5,10-epi-2,3-dihydroaromatin)

Structure for NP0037228 (5,10-epi-2,3-dihydroaromatin)

3D Structure for NP0037228 (5,10-epi-2,3-dihydroaromatin)