NP-MRD: Showing NP-Card for (3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid (NP0035313)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-20 18:47:35 UTC

Updated at

2021-06-30 00:06:13 UTC

NP-MRD ID

NP0035313

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid

Provided By

JEOL Database JEOL Logo

Description

(2S)-2-[(4aS)-3-Oxo-7beta-hydroxy-8beta,8abeta-dimethyl-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-2-yl]propionic acid belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. (3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid is found in Chloranthus anhuiensis. (3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid was first documented in 2010 (Wu, B., et al.). Based on a literature review very few articles have been published on (2S)-2-[(4aS)-3-Oxo-7beta-hydroxy-8beta,8abeta-dimethyl-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-2-yl]propionic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120473D          

 41 42  0  0  0  0            999 V2000
    2.1647   -1.8315    3.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599   -0.3823    3.3923 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0759    0.4135    4.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208    0.1463    5.1193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8224    1.4817    4.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3572    0.3533    2.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -0.0081    1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713    0.7425   -0.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0340    0.0526   -1.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    2.2379    0.0277 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6215    3.0522    0.9260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8429    2.8816    0.5539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2282    1.4083    0.4995 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6016    1.2886    0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3511    0.6253   -0.5017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6602    1.0356   -1.9567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    2.3610    0.5762 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1966    1.5720    1.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0419    1.8916    2.6937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5815   -2.4264    2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -1.8979    3.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4736   -2.2981    4.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -0.4433    3.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776    1.6660    4.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8797   -0.9201    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.9481   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0520    0.6318   -2.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763   -0.0742   -0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719    2.7142   -0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8818    4.1164    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428    2.7715    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    3.3710   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    3.4022    1.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244    0.9661    1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1241    1.7375    0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536   -0.4304   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860    0.3514   -2.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    2.0481   -2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345    0.9937   -2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487    2.0056   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    3.4127    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0  0  0  0
 18 17  1  0  0  0  0
 10  8  1  0  0  0  0
 18 19  2  0  0  0  0
  6  2  1  0  0  0  0
 12 13  1  0  0  0  0
  2  3  1  0  0  0  0
 12 11  1  0  0  0  0
  3  4  2  0  0  0  0
 13 15  1  0  0  0  0
  3  5  1  0  0  0  0
 15  8  1  0  0  0  0
 13 14  1  0  0  0  0
 10 11  1  0  0  0  0
 15 16  1  0  0  0  0
 10 17  1  0  0  0  0
  8  9  1  6  0  0  0
  8  7  1  0  0  0  0
 10 29  1  6  0  0  0
  7  6  2  0  0  0  0
  2  1  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 13 34  1  1  0  0  0
 15 36  1  6  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
  7 25  1  0  0  0  0
 17 40  1  0  0  0  0
 17 41  1  0  0  0  0
  2 23  1  1  0  0  0
  5 24  1  0  0  0  0
 14 35  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
M  END

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    2.1647   -1.8315    3.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599   -0.3823    3.3923 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0759    0.4135    4.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208    0.1463    5.1193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8224    1.4817    4.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3572    0.3533    2.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -0.0081    1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713    0.7425   -0.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0340    0.0526   -1.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    2.2379    0.0277 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6215    3.0522    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8429    2.8816    0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2282    1.4083    0.4995 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6016    1.2886    0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3511    0.6253   -0.5017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6602    1.0356   -1.9567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    2.3610    0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    1.5720    1.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0419    1.8916    2.6937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5815   -2.4264    2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -1.8979    3.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4736   -2.2981    4.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -0.4433    3.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776    1.6660    4.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8797   -0.9201    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.9481   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0520    0.6318   -2.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763   -0.0742   -0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719    2.7142   -0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8818    4.1164    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428    2.7715    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    3.3710   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    3.4022    1.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244    0.9661    1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1241    1.7375    0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536   -0.4304   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860    0.3514   -2.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    2.0481   -2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345    0.9937   -2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487    2.0056   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    3.4127    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0
 18 17  1  0
 10  8  1  0
 18 19  2  0
  6  2  1  0
 12 13  1  0
  2  3  1  0
 12 11  1  0
  3  4  2  0
 13 15  1  0
  3  5  1  0
 15  8  1  0
 13 14  1  0
 10 11  1  0
 15 16  1  0
 10 17  1  0
  8  9  1  6
  8  7  1  0
 10 29  1  6
  7  6  2  0
  2  1  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  1
 15 36  1  6
 11 30  1  0
 11 31  1  0
  7 25  1  0
 17 40  1  0
 17 41  1  0
  2 23  1  1
  5 24  1  0
 14 35  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
M  END


  Mrv1652306202120473D          

 41 42  0  0  0  0            999 V2000
    2.1647   -1.8315    3.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599   -0.3823    3.3923 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0759    0.4135    4.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208    0.1463    5.1193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8224    1.4817    4.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3572    0.3533    2.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -0.0081    1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713    0.7425   -0.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0340    0.0526   -1.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    2.2379    0.0277 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6215    3.0522    0.9260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8429    2.8816    0.5539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2282    1.4083    0.4995 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6016    1.2886    0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3511    0.6253   -0.5017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6602    1.0356   -1.9567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    2.3610    0.5762 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1966    1.5720    1.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0419    1.8916    2.6937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5815   -2.4264    2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -1.8979    3.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4736   -2.2981    4.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -0.4433    3.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776    1.6660    4.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8797   -0.9201    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.9481   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0520    0.6318   -2.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763   -0.0742   -0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719    2.7142   -0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8818    4.1164    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428    2.7715    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    3.3710   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    3.4022    1.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244    0.9661    1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1241    1.7375    0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536   -0.4304   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860    0.3514   -2.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    2.0481   -2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345    0.9937   -2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487    2.0056   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    3.4127    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0  0  0  0
 18 17  1  0  0  0  0
 10  8  1  0  0  0  0
 18 19  2  0  0  0  0
  6  2  1  0  0  0  0
 12 13  1  0  0  0  0
  2  3  1  0  0  0  0
 12 11  1  0  0  0  0
  3  4  2  0  0  0  0
 13 15  1  0  0  0  0
  3  5  1  0  0  0  0
 15  8  1  0  0  0  0
 13 14  1  0  0  0  0
 10 11  1  0  0  0  0
 15 16  1  0  0  0  0
 10 17  1  0  0  0  0
  8  9  1  6  0  0  0
  8  7  1  0  0  0  0
 10 29  1  6  0  0  0
  7  6  2  0  0  0  0
  2  1  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 13 34  1  1  0  0  0
 15 36  1  6  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
  7 25  1  0  0  0  0
 17 40  1  0  0  0  0
 17 41  1  0  0  0  0
  2 23  1  1  0  0  0
  5 24  1  0  0  0  0
 14 35  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035313

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(C1=C([H])[C@]2(C([H])([H])[H])[C@]([H])(C([H])([H])C1=O)C([H])([H])C([H])([H])[C@@]([H])(O[H])[C@@]2([H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-8(14(18)19)11-7-15(3)9(2)12(16)5-4-10(15)6-13(11)17/h7-10,12,16H,4-6H2,1-3H3,(H,18,19)/t8-,9+,10-,12+,15-/m0/s1

> <INCHI_KEY>
OZBUHIIPYQKAED-JEFOQBOOSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.258086780562216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(4aS,7R,8S,8aS)-7-hydroxy-8,8a-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]propanoic acid

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.8266324613333342

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.30113974729551

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4697398183909565

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9174780789740774

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
71.65189999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(4aS,7R,8S,8aS)-7-hydroxy-8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    2.1647   -1.8315    3.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599   -0.3823    3.3923 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0759    0.4135    4.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208    0.1463    5.1193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8224    1.4817    4.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3572    0.3533    2.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -0.0081    1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713    0.7425   -0.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0340    0.0526   -1.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    2.2379    0.0277 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6215    3.0522    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8429    2.8816    0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2282    1.4083    0.4995 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6016    1.2886    0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3511    0.6253   -0.5017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6602    1.0356   -1.9567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    2.3610    0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    1.5720    1.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0419    1.8916    2.6937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5815   -2.4264    2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -1.8979    3.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4736   -2.2981    4.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -0.4433    3.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776    1.6660    4.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8797   -0.9201    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.9481   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0520    0.6318   -2.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763   -0.0742   -0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719    2.7142   -0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8818    4.1164    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428    2.7715    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    3.3710   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    3.4022    1.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244    0.9661    1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1241    1.7375    0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536   -0.4304   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860    0.3514   -2.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    2.0481   -2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345    0.9937   -2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487    2.0056   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    3.4127    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0
 18 17  1  0
 10  8  1  0
 18 19  2  0
  6  2  1  0
 12 13  1  0
  2  3  1  0
 12 11  1  0
  3  4  2  0
 13 15  1  0
  3  5  1  0
 15  8  1  0
 13 14  1  0
 10 11  1  0
 15 16  1  0
 10 17  1  0
  8  9  1  6
  8  7  1  0
 10 29  1  6
  7  6  2  0
  2  1  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  1
 15 36  1  6
 11 30  1  0
 11 31  1  0
  7 25  1  0
 17 40  1  0
 17 41  1  0
  2 23  1  1
  5 24  1  0
 14 35  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
  1 20  1  0
  1 21  1  0
  1 22  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       2.165  -1.831   3.456  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.660  -0.382   3.392  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.076   0.414   4.560  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.021   0.146   5.119  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.822   1.482   4.929  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.357   0.353   2.099  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.458  -0.008   1.163  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.171   0.743  -0.134  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.034   0.053  -1.218  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.584   2.238   0.028  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.622   3.052   0.926  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.843   2.882   0.554  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.228   1.408   0.500  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.602   1.289   0.142  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.351   0.625  -0.502  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.660   1.036  -1.957  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.011   2.361   0.576  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.197   1.572   1.854  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.042   1.892   2.694  0.00  0.00           O+0
HETATM   20  H   UNK     0       2.582  -2.426   2.637  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.072  -1.898   3.411  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.474  -2.298   4.399  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.747  -0.443   3.538  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.578   1.666   4.317  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.880  -0.920   1.308  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.650  -0.948  -1.450  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.052   0.632  -2.148  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.076  -0.074  -0.903  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.572   2.714  -0.962  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.882   4.116   0.866  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.743   2.772   1.979  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.052   3.371  -0.405  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.473   3.402   1.286  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.124   0.966   1.498  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.124   1.738   0.829  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.654  -0.430  -0.434  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.186   0.351  -2.667  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.315   2.048  -2.184  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.734   0.994  -2.164  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.749   2.006  -0.151  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.239   3.413   0.786  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    6    3    1   23                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3   24                                                       
CONECT    6   18    2    7                                                  
CONECT    7    8    6   25                                                  
CONECT    8   10   15    9    7                                             
CONECT    9    8   26   27   28                                             
CONECT   10    8   11   17   29                                             
CONECT   11   12   10   30   31                                             
CONECT   12   13   11   32   33                                             
CONECT   13   12   15   14   34                                             
CONECT   14   13   35                                                       
CONECT   15   13    8   16   36                                             
CONECT   16   15   37   38   39                                             
CONECT   17   18   10   40   41                                             
CONECT   18    6   17   19                                                  
CONECT   19   18                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    2                                                            
CONECT   24    5                                                            
CONECT   25    7                                                            
CONECT   26    9                                                            
CONECT   27    9                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   16                                                            
CONECT   38   16                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   17                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   84    0
END

RDKit          3D

41 42  0  0  0  0  0  0  0  0999 V2000
    2.1647   -1.8315    3.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599   -0.3823    3.3923 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0759    0.4135    4.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208    0.1463    5.1193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8224    1.4817    4.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3572    0.3533    2.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -0.0081    1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713    0.7425   -0.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0340    0.0526   -1.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    2.2379    0.0277 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6215    3.0522    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8429    2.8816    0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2282    1.4083    0.4995 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6016    1.2886    0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3511    0.6253   -0.5017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6602    1.0356   -1.9567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    2.3610    0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    1.5720    1.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0419    1.8916    2.6937 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5815   -2.4264    2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -1.8979    3.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4736   -2.2981    4.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7467   -0.4433    3.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776    1.6660    4.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8797   -0.9201    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -0.9481   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0520    0.6318   -2.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763   -0.0742   -0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719    2.7142   -0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8818    4.1164    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428    2.7715    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    3.3710   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    3.4022    1.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244    0.9661    1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1241    1.7375    0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536   -0.4304   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860    0.3514   -2.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    2.0481   -2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345    0.9937   -2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487    2.0056   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    3.4127    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 18  1  0
 18 17  1  0
 10  8  1  0
 18 19  2  0
  6  2  1  0
 12 13  1  0
  2  3  1  0
 12 11  1  0
  3  4  2  0
 13 15  1  0
  3  5  1  0
 15  8  1  0
 13 14  1  0
 10 11  1  0
 15 16  1  0
 10 17  1  0
  8  9  1  6
  8  7  1  0
 10 29  1  6
  7  6  2  0
  2  1  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  1
 15 36  1  6
 11 30  1  0
 11 31  1  0
  7 25  1  0
 17 40  1  0
 17 41  1  0
  2 23  1  1
  5 24  1  0
 14 35  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2S)-2-[(4AS)-3-oxo-7b-hydroxy-8b,8abeta-dimethyl-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-2-yl]propionate	Generator
(2S)-2-[(4AS)-3-oxo-7b-hydroxy-8b,8abeta-dimethyl-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-2-yl]propionic acid	Generator
(2S)-2-[(4AS)-3-oxo-7beta-hydroxy-8beta,8abeta-dimethyl-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-2-yl]propionate	Generator
(2S)-2-[(4AS)-3-oxo-7β-hydroxy-8β,8abeta-dimethyl-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-2-yl]propionate	Generator
(2S)-2-[(4AS)-3-oxo-7β-hydroxy-8β,8abeta-dimethyl-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-2-yl]propionic acid	Generator

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

(2S)-2-[(4aS,7R,8S,8aS)-7-hydroxy-8,8a-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]propanoic acid

Traditional Name

(2S)-2-[(4aS,7R,8S,8aS)-7-hydroxy-8,8a-dimethyl-3-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]([H])(C1=C([H])[C@]2(C([H])([H])[H])[C@]([H])(C([H])([H])C1=O)C([H])([H])C([H])([H])[C@@]([H])(O[H])[C@@]2([H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H22O4/c1-8(14(18)19)11-7-15(3)9(2)12(16)5-4-10(15)6-13(11)17/h7-10,12,16H,4-6H2,1-3H3,(H,18,19)/t8-,9+,10-,12+,15-/m0/s1

InChI Key

OZBUHIIPYQKAED-JEFOQBOOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Chloranthus anhuiensis	JEOL database	Wu, B., et al, J. Nat. Prod. 73, 1069 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.85	ALOGPS
logP	1.83	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	4.47	ChemAxon
pKa (Strongest Basic)	-0.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.65 m³·mol⁻¹	ChemAxon
Polarizability	28.26 Å³	ChemAxon
Number of Rings	2	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

28287727

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46849837

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu, B., et al. (2010). Wu, B., et al, J. Nat. Prod. 73, 1069 (2010). J. Nat. Prod..

Showing NP-Card for (3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid (NP0035313)

MOL for NP0035313 ((3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid)

3D MOL for NP0035313 ((3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid)

3D SDF for NP0035313 ((3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid)

3D-SDF for NP0035313 ((3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid)

PDB for NP0035313 ((3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid)

3D PDB for NP0035313 ((3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid)

SMILES for NP0035313 ((3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid)

INCHI for NP0035313 ((3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid)

Structure for NP0035313 ((3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid)

3D Structure for NP0035313 ((3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid)