NP-MRD: Showing NP-Card for argutosine A (NP0039975)

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Record Information

Version

2.0

Created at

2021-06-20 22:15:25 UTC

Updated at

2021-06-30 00:13:36 UTC

NP-MRD ID

NP0039975

Secondary Accession Numbers

None

Natural Product Identification

Common Name

argutosine A

Provided By

JEOL Database JEOL Logo

Description

Argutosin A 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. argutosine A is found in Incarvillea arguta. argutosine A was first documented in 2010 (Fu, J.-J., et al.). Based on a literature review very few articles have been published on Argutosin A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100153D          

 39 40  0  0  0  0            999 V2000
    2.2494   -3.0760   -1.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9998   -1.7805   -1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247   -0.7509   -2.6198 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1738    0.1480   -2.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -1.2396   -0.1434 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9900   -2.1394    1.0354 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5575   -1.5412    2.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2818   -1.5604    3.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578   -1.0232    2.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5487   -1.3042    3.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9717   -0.8892    3.7309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4826    0.0923    2.6771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9556   -0.2470    1.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6127    0.6839    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3812   -0.2576    1.2247 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1905    1.1796    1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829   -0.9457   -0.0931 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1744   -3.8580   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365   -3.4044   -2.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1989   -0.1808   -2.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3526   -1.2048   -3.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -0.3952   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418   -0.2962   -0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -2.2707    1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290   -3.1319    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919   -1.8732    4.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840   -0.4401    4.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -1.7924    3.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5797    0.0781    2.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    1.1121    2.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062   -1.2640    1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3916    1.7362    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912    0.4539   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7023    0.5696    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0428    1.7435    0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076    1.7410    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807    1.1879    1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.8921   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -0.3148   -0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
 17  5  1  0  0  0  0
 15 13  1  0  0  0  0
  9 10  2  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
 15 16  1  6  0  0  0
 13 14  1  0  0  0  0
 15  9  1  0  0  0  0
  5  2  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  5  1  0  0  0  0
  2  3  1  0  0  0  0
  7  9  1  0  0  0  0
  2  1  2  3  0  0  0
 15 17  1  0  0  0  0
  3  4  1  0  0  0  0
  6 24  1  0  0  0  0
  6 25  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
  5 23  1  1  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 10 26  1  0  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
 13 31  1  6  0  0  0
 14 32  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  4 22  1  0  0  0  0
M  END

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    2.2494   -3.0760   -1.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9998   -1.7805   -1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247   -0.7509   -2.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738    0.1480   -2.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -1.2396   -0.1434 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9900   -2.1394    1.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575   -1.5412    2.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2818   -1.5604    3.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578   -1.0232    2.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5487   -1.3042    3.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9717   -0.8892    3.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4826    0.0923    2.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556   -0.2470    1.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6127    0.6839    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3812   -0.2576    1.2247 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1905    1.1796    1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829   -0.9457   -0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1744   -3.8580   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365   -3.4044   -2.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1989   -0.1808   -2.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3526   -1.2048   -3.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -0.3952   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418   -0.2962   -0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -2.2707    1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290   -3.1319    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919   -1.8732    4.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840   -0.4401    4.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -1.7924    3.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5797    0.0781    2.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    1.1121    2.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062   -1.2640    1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3916    1.7362    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912    0.4539   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7023    0.5696    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0428    1.7435    0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076    1.7410    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807    1.1879    1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.8921   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -0.3148   -0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
 17  5  1  0
 15 13  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 15 16  1  6
 13 14  1  0
 15  9  1  0
  5  2  1  0
  6  7  1  0
  7  8  2  0
  6  5  1  0
  2  3  1  0
  7  9  1  0
  2  1  2  3
 15 17  1  0
  3  4  1  0
  6 24  1  0
  6 25  1  0
 17 38  1  0
 17 39  1  0
  5 23  1  1
 16 35  1  0
 16 36  1  0
 16 37  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  6
 14 32  1  0
 14 33  1  0
 14 34  1  0
  3 20  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  4 22  1  0
M  END


  Mrv1652306212100153D          

 39 40  0  0  0  0            999 V2000
    2.2494   -3.0760   -1.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9998   -1.7805   -1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247   -0.7509   -2.6198 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1738    0.1480   -2.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -1.2396   -0.1434 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9900   -2.1394    1.0354 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5575   -1.5412    2.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2818   -1.5604    3.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578   -1.0232    2.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5487   -1.3042    3.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9717   -0.8892    3.7309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4826    0.0923    2.6771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9556   -0.2470    1.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6127    0.6839    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3812   -0.2576    1.2247 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1905    1.1796    1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829   -0.9457   -0.0931 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1744   -3.8580   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365   -3.4044   -2.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1989   -0.1808   -2.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3526   -1.2048   -3.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -0.3952   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418   -0.2962   -0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -2.2707    1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290   -3.1319    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919   -1.8732    4.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840   -0.4401    4.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -1.7924    3.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5797    0.0781    2.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    1.1121    2.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062   -1.2640    1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3916    1.7362    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912    0.4539   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7023    0.5696    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0428    1.7435    0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076    1.7410    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807    1.1879    1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.8921   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -0.3148   -0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
 17  5  1  0  0  0  0
 15 13  1  0  0  0  0
  9 10  2  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
 15 16  1  6  0  0  0
 13 14  1  0  0  0  0
 15  9  1  0  0  0  0
  5  2  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  5  1  0  0  0  0
  2  3  1  0  0  0  0
  7  9  1  0  0  0  0
  2  1  2  3  0  0  0
 15 17  1  0  0  0  0
  3  4  1  0  0  0  0
  6 24  1  0  0  0  0
  6 25  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
  5 23  1  1  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 10 26  1  0  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
 13 31  1  6  0  0  0
 14 32  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  4 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039975

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(=C([H])[H])[C@]1([H])C([H])([H])C(=O)C2=C([H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]2(C([H])([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-10(9-16)12-7-14(17)13-6-4-5-11(2)15(13,3)8-12/h6,11-12,16H,1,4-5,7-9H2,2-3H3/t11-,12-,15+/m1/s1

> <INCHI_KEY>
FPGPQYSZUYXEAO-JMSVASOKSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.131909895093855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4aS,5R)-3-(3-hydroxyprop-1-en-2-yl)-4a,5-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.5712548736666676

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.951123082313913

> <JCHEM_PKA_STRONGEST_BASIC>
-1.944977584846748

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
69.9203

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4aS,5R)-3-(3-hydroxyprop-1-en-2-yl)-4a,5-dimethyl-2,3,4,5,6,7-hexahydronaphthalen-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    2.2494   -3.0760   -1.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9998   -1.7805   -1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247   -0.7509   -2.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738    0.1480   -2.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -1.2396   -0.1434 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9900   -2.1394    1.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575   -1.5412    2.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2818   -1.5604    3.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578   -1.0232    2.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5487   -1.3042    3.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9717   -0.8892    3.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4826    0.0923    2.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556   -0.2470    1.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6127    0.6839    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3812   -0.2576    1.2247 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1905    1.1796    1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829   -0.9457   -0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1744   -3.8580   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365   -3.4044   -2.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1989   -0.1808   -2.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3526   -1.2048   -3.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -0.3952   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418   -0.2962   -0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -2.2707    1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290   -3.1319    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919   -1.8732    4.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840   -0.4401    4.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -1.7924    3.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5797    0.0781    2.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    1.1121    2.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062   -1.2640    1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3916    1.7362    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912    0.4539   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7023    0.5696    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0428    1.7435    0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076    1.7410    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807    1.1879    1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.8921   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -0.3148   -0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
 17  5  1  0
 15 13  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 15 16  1  6
 13 14  1  0
 15  9  1  0
  5  2  1  0
  6  7  1  0
  7  8  2  0
  6  5  1  0
  2  3  1  0
  7  9  1  0
  2  1  2  3
 15 17  1  0
  3  4  1  0
  6 24  1  0
  6 25  1  0
 17 38  1  0
 17 39  1  0
  5 23  1  1
 16 35  1  0
 16 36  1  0
 16 37  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  6
 14 32  1  0
 14 33  1  0
 14 34  1  0
  3 20  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  4 22  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       2.249  -3.076  -1.786  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.000  -1.781  -1.520  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.125  -0.751  -2.620  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.174   0.148  -2.299  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.598  -1.240  -0.143  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.990  -2.139   1.035  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.558  -1.541   2.351  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.282  -1.560   3.343  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.158  -1.023   2.419  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.549  -1.304   3.527  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.972  -0.889   3.731  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.483   0.092   2.677  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.956  -0.247   1.269  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.613   0.684   0.243  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.381  -0.258   1.225  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.191   1.180   1.288  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.083  -0.946  -0.093  0.00  0.00           C+0
HETATM   18  H   UNK     0       2.174  -3.858  -1.039  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.537  -3.404  -2.782  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.199  -0.181  -2.736  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.353  -1.205  -3.590  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.960  -0.395  -2.118  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.142  -0.296  -0.006  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.079  -2.271   1.058  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.529  -3.132   0.972  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.092  -1.873   4.336  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.084  -0.440   4.724  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.594  -1.792   3.718  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.580   0.078   2.685  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.191   1.112   2.956  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.306  -1.264   1.037  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.392   1.736   0.447  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.291   0.454  -0.777  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.702   0.570   0.270  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.043   1.744   0.378  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.208   1.741   2.139  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.281   1.188   1.397  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.461  -1.892  -0.225  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.195  -0.315  -0.945  0.00  0.00           H+0
CONECT    1    2   18   19                                                  
CONECT    2    5    3    1                                                  
CONECT    3    2    4   20   21                                             
CONECT    4    3   22                                                       
CONECT    5   17    2    6   23                                             
CONECT    6    7    5   24   25                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9   10   15    7                                                  
CONECT   10    9   11   26                                                  
CONECT   11   10   12   27   28                                             
CONECT   12   11   13   29   30                                             
CONECT   13   15   12   14   31                                             
CONECT   14   13   32   33   34                                             
CONECT   15   13   16    9   17                                             
CONECT   16   15   35   36   37                                             
CONECT   17    5   15   38   39                                             
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    5                                                            
CONECT   24    6                                                            
CONECT   25    6                                                            
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   12                                                            
CONECT   31   13                                                            
CONECT   32   14                                                            
CONECT   33   14                                                            
CONECT   34   14                                                            
CONECT   35   16                                                            
CONECT   36   16                                                            
CONECT   37   16                                                            
CONECT   38   17                                                            
CONECT   39   17                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

RDKit          3D

39 40  0  0  0  0  0  0  0  0999 V2000
    2.2494   -3.0760   -1.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9998   -1.7805   -1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247   -0.7509   -2.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738    0.1480   -2.2985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -1.2396   -0.1434 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9900   -2.1394    1.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575   -1.5412    2.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2818   -1.5604    3.3432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578   -1.0232    2.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5487   -1.3042    3.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9717   -0.8892    3.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4826    0.0923    2.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556   -0.2470    1.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6127    0.6839    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3812   -0.2576    1.2247 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1905    1.1796    1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829   -0.9457   -0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1744   -3.8580   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365   -3.4044   -2.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1989   -0.1808   -2.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3526   -1.2048   -3.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -0.3952   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418   -0.2962   -0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -2.2707    1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290   -3.1319    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919   -1.8732    4.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840   -0.4401    4.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -1.7924    3.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5797    0.0781    2.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    1.1121    2.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062   -1.2640    1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3916    1.7362    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912    0.4539   -0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7023    0.5696    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0428    1.7435    0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076    1.7410    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807    1.1879    1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.8921   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -0.3148   -0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
 17  5  1  0
 15 13  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 15 16  1  6
 13 14  1  0
 15  9  1  0
  5  2  1  0
  6  7  1  0
  7  8  2  0
  6  5  1  0
  2  3  1  0
  7  9  1  0
  2  1  2  3
 15 17  1  0
  3  4  1  0
  6 24  1  0
  6 25  1  0
 17 38  1  0
 17 39  1  0
  5 23  1  1
 16 35  1  0
 16 36  1  0
 16 37  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  6
 14 32  1  0
 14 33  1  0
 14 34  1  0
  3 20  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  4 22  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3390 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

(3S,4aS,5R)-3-(3-hydroxyprop-1-en-2-yl)-4a,5-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-one

Traditional Name

(3S,4aS,5R)-3-(3-hydroxyprop-1-en-2-yl)-4a,5-dimethyl-2,3,4,5,6,7-hexahydronaphthalen-1-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C(=C([H])[H])[C@]1([H])C([H])([H])C(=O)C2=C([H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]2(C([H])([H])[H])C1([H])[H]

InChI Identifier

InChI=1S/C15H22O2/c1-10(9-16)12-7-14(17)13-6-4-5-11(2)15(13,3)8-12/h6,11-12,16H,1,4-5,7-9H2,2-3H3/t11-,12-,15+/m1/s1

InChI Key

FPGPQYSZUYXEAO-JMSVASOKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Incarvillea arguta	JEOL database	Fu, J.-J., et al, Chem. Pharm. Bull. 58, 1263 (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
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	3.05	ALOGPS
logP	2.57	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	16.95	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.92 m³·mol⁻¹	ChemAxon
Polarizability	27.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

28287886

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46930872

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fu, J.-J., et al. (2010). Fu, J.-J., et al, Chem. Pharm. Bull. 58, 1263 (2010). Chem. Pharm. Bull..

Showing NP-Card for argutosine A (NP0039975)

MOL for NP0039975 (argutosine A)

3D MOL for NP0039975 (argutosine A)

3D SDF for NP0039975 (argutosine A)

3D-SDF for NP0039975 (argutosine A)

PDB for NP0039975 (argutosine A)

3D PDB for NP0039975 (argutosine A)

SMILES for NP0039975 (argutosine A)

INCHI for NP0039975 (argutosine A)

Structure for NP0039975 (argutosine A)

3D Structure for NP0039975 (argutosine A)