NP-MRD: Showing NP-Card for 3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid (NP0220981)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 22:26:15 UTC

Updated at

2022-09-05 22:26:15 UTC

NP-MRD ID

NP0220981

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid

Description

3-{[(1S,2R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. 3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid is found in Baccharis neaei. Based on a literature review very few articles have been published on 3-{[(1S,2R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062200262D          

 29 31  0  0  1  0            999 V2000
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9139   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7643    2.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3770    3.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7387    4.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1452    4.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832    4.3213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399    3.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
  5 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  2  0  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
   -1.0957   -2.0049    2.9601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5319   -2.1227    1.5682 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9223   -2.2537    1.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6071   -2.3799    0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1643   -1.1856   -0.5766 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9709   -0.0750   -0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8212    1.1787   -0.5693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4946    2.2795   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032    2.1632    0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2583    3.5820   -0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0990    4.6418   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9896    5.8057   -0.6889 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9414    4.3728    0.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7083   -1.3848   -1.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083   -2.2127   -2.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8033   -3.5322   -1.9096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1353   -0.7948   -2.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0391    0.0792   -2.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9340   -0.4298   -1.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772   -1.1683   -0.6084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0229   -0.9167    0.6918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7829    0.3236    1.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862   -1.1874    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699   -0.3419   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6963    1.0162    0.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1755    2.2105    0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6866    3.2266    0.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4770    2.6619    1.7269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5291    1.3670    1.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0326   -2.6211    3.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3824   -0.9760    3.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3828   -2.3731    3.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901   -3.0167    1.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522   -1.5112    2.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259   -3.2393    2.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6979   -2.3451    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3521   -3.3445   -0.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0374   -0.0596    1.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445   -0.3622   -0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5443    3.5416   -1.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828    3.8254   -0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4948    5.1266    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638   -1.7010   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1640   -2.1321   -3.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6439   -3.8106   -1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5175   -0.9208   -3.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6257    0.0719   -3.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2033    1.1599   -2.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5280    0.4083   -1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7001   -1.0374   -2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6319   -2.2081   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7230    0.6128    1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    0.2800    2.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5439    1.2240    0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5463   -2.2774    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8559   -1.3878    1.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5899   -0.2911   -1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4956   -0.8619    0.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4751    2.3858   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4121    4.2642    0.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0996    0.6584    2.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
  5 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 14  2  0
 14 15  1  0
 15 16  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 29  2  0
 29 28  1  0
 28 27  1  0
 27 26  2  0
 21  2  1  0
 26 25  1  0
 14  5  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
 10 40  1  0
 10 41  1  0
 13 42  1  0
 20 51  1  6
 19 49  1  0
 19 50  1  0
 18 47  1  0
 18 48  1  0
 17 46  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 29 61  1  0
 27 60  1  0
 26 59  1  0
M  END


  Mrv1652309062200262D          

 29 31  0  0  1  0            999 V2000
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9139   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7643    2.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3770    3.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7387    4.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1452    4.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832    4.3213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399    3.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
  5 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0220981

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@]2(COC(=O)CC(O)=O)[C@H](CCC=C2CO)[C@@]1(C)CCC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O6/c1-16-6-10-23(15-29-21(27)12-20(25)26)18(13-24)4-3-5-19(23)22(16,2)9-7-17-8-11-28-14-17/h4,8,11,14,16,19,24H,3,5-7,9-10,12-13,15H2,1-2H3,(H,25,26)/t16-,19-,22+,23-/m1/s1

> <INCHI_KEY>
IVLSJOYTYVWEHN-XHBDVGQISA-N

> <FORMULA>
C23H32O6

> <MOLECULAR_WEIGHT>
404.503

> <EXACT_MASS>
404.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.90055921055034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(1S,2R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid

> <JCHEM_LOGP>
3.6574320236666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.141684404370821

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.206670277951569

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7368272428393174

> <JCHEM_POLAR_SURFACE_AREA>
96.97000000000001

> <JCHEM_REFRACTIVITY>
108.4044

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1S,2R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.573  -0.294   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.427   4.976   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.704   6.335   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.379   7.720   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.271   8.789   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.089   8.066   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.821   6.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14   20                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    5   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    5   21                                                  
CONECT   21   20    2   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
3-{[(1S,2R,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methoxy}-3-oxopropanoate	Generator

Chemical Formula

C₂₃H₃₂O₆

Average Mass

404.5030 Da

Monoisotopic Mass

404.21989 Da

IUPAC Name

3-{[(1S,2R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid

Traditional Name

3-{[(1S,2R,4aS,8aR)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@]2(COC(=O)CC(O)=O)[C@H](CCC=C2CO)[C@@]1(C)CCC1=COC=C1

InChI Identifier

InChI=1S/C23H32O6/c1-16-6-10-23(15-29-21(27)12-20(25)26)18(13-24)4-3-5-19(23)22(16,2)9-7-17-8-11-28-14-17/h4,8,11,14,16,19,24H,3,5-7,9-10,12-13,15H2,1-2H3,(H,25,26)/t16-,19-,22+,23-/m1/s1

InChI Key

IVLSJOYTYVWEHN-XHBDVGQISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Baccharis neaei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Dicarboxylic acid or derivatives
1,3-dicarbonyl compound
Furan
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.66	ChemAxon
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.97 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	108.4 m³·mol⁻¹	ChemAxon
Polarizability	43.9 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	Yes	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

163009995

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid (NP0220981)

MOL for NP0220981 (3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid)

3D MOL for NP0220981 (3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid)

3D SDF for NP0220981 (3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid)

3D-SDF for NP0220981 (3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid)

PDB for NP0220981 (3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid)

3D PDB for NP0220981 (3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid)

SMILES for NP0220981 (3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid)

INCHI for NP0220981 (3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid)

Structure for NP0220981 (3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid)

3D Structure for NP0220981 (3-{[(1s,2r,4as,8ar)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methoxy}-3-oxopropanoic acid)