NP-MRD: Showing NP-Card for (2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid (NP0291332)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-09 22:22:53 UTC

Updated at

2022-09-09 22:22:53 UTC

NP-MRD ID

NP0291332

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid

Description

(2S)-2-({[(3R,3aR,4S,6aR,8S,9aR,9bS)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. (2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid is found in Saussurea pulchella. Based on a literature review very few articles have been published on (2S)-2-({[(3R,3aR,4S,6aR,8S,9aR,9bS)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200222D          

 31 34  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3791    0.2666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0676    0.7211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8055    0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4940    0.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4446    1.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1332    2.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8710    1.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9204    0.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2318    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0183    1.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2804    1.9136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7068    1.9991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 31 30  1  1  0  0  0
  2 31  1  0  0  0  0
 25 31  1  0  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
   -3.6214    1.6441   -2.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2985    0.4430   -1.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0339   -0.1496   -2.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9479    0.2363   -1.5413 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3019   -0.0356   -2.0994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786   -0.3422   -0.1716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1931   -0.0864    0.6407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1736    1.3091    0.7798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505    1.5806    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3792    2.5585    1.7918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0438    0.4843    0.6143 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7159   -0.2651    1.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5490   -1.2872    1.1963 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7303   -0.8990    0.4863 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7120   -0.1386    1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9252    0.2485    0.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0936   -0.4859    0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1928   -0.0861   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1920    1.0710   -0.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0318    1.8219   -0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9293    1.4268   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3400   -2.0937   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8164   -3.2323    0.0619 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4601   -2.0922   -0.9434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4625   -0.7016    0.2755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4595   -0.4528    1.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3321   -0.3269    2.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7864   -0.3576    0.6445 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7495    0.2328    1.4297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3709    0.5433   -0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1386   -0.2625   -0.9648 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4958    2.1860   -2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9678    2.1321   -3.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146   -1.2511   -2.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912    0.2591   -3.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814    1.3569   -1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5693    0.6699   -2.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7063   -1.4165   -0.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9473   -0.4781    1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070    0.9427   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719   -0.7657    2.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2642    0.3727    2.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0941   -2.1427    0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085   -0.2527   -0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3238    0.7859    1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0660   -0.7771    2.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1483   -1.4038    1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1090   -0.6871   -0.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0488    1.3977   -1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0524    2.7336   -1.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0559    2.0636   -0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1303   -2.8479   -0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3122   -1.8178    0.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1853   -0.1472    3.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638   -0.4037    3.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0833   -1.3231    0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5036   -0.4202    1.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1427    0.5674   -1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1048    1.5213   -0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633   -1.1590   -1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 30  1  0
 30 31  1  0
 31 25  1  0
 25  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14 22  1  0
 22 24  1  0
 22 23  2  0
 11  6  1  0
  6  4  1  0
  4  5  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 25 26  1  0
 26 27  2  3
 26 28  1  0
  2 31  1  0
  6  7  1  0
 21 16  1  0
 29 57  1  0
 28 56  1  6
 30 58  1  0
 30 59  1  0
 31 60  1  6
 25 53  1  6
  7 39  1  1
 11 40  1  6
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  6
 15 45  1  0
 15 46  1  0
 17 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 24 52  1  0
  6 38  1  6
  4 36  1  1
  5 37  1  0
  3 34  1  0
  3 35  1  0
  1 32  1  0
  1 33  1  0
 27 54  1  0
 27 55  1  0
M  END


  Mrv1652309102200222D          

 31 34  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3791    0.2666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0676    0.7211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8055    0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4940    0.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4446    1.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1332    2.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8710    1.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9204    0.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2318    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0183    1.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2804    1.9136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7068    1.9991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 31 30  1  1  0  0  0
  2 31  1  0  0  0  0
 25 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291332

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1C[C@@H]2[C@@H]([C@@H]3OC(=O)[C@@H](CN[C@@H](CC4=CC=CC=C4)C(O)=O)[C@@H]3[C@@H](O)CC2=C)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C24H29NO6/c1-12-8-19(27)21-16(11-25-17(23(28)29)9-14-6-4-3-5-7-14)24(30)31-22(21)20-13(2)18(26)10-15(12)20/h3-7,15-22,25-27H,1-2,8-11H2,(H,28,29)/t15-,16-,17-,18-,19-,20-,21+,22-/m0/s1

> <INCHI_KEY>
UPFWZEIMZFQXJN-ZFBPGJDDSA-N

> <FORMULA>
C24H29NO6

> <MOLECULAR_WEIGHT>
427.497

> <EXACT_MASS>
427.199487658

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.83603113881393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-({[(3R,3aR,4S,6aR,8S,9aR,9bS)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid

> <JCHEM_LOGP>
-1.365765407779007

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.37441046021662

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5672200917825565

> <JCHEM_PKA_STRONGEST_BASIC>
9.820071219188947

> <JCHEM_POLAR_SURFACE_AREA>
116.09

> <JCHEM_REFRACTIVITY>
112.6585

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-({[(3R,3aR,4S,6aR,8S,9aR,9bS)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3H-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       3.482   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.665   3.341   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.530   1.186   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      11.908   0.498   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      13.193   1.346   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.570   0.657   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.855   1.506   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.763   3.043   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.049   3.891   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.426   3.202   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.518   1.665   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.233   0.817   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.101   2.883   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.723   3.572   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      14.386   3.732   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.996  -3.052   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   14   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    7   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30    2   25                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-({[(3R,3ar,4S,6ar,8S,9ar,9BS)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoate	Generator

Chemical Formula

C₂₄H₂₉NO₆

Average Mass

427.4970 Da

Monoisotopic Mass

427.19949 Da

IUPAC Name

(2S)-2-({[(3R,3aR,4S,6aR,8S,9aR,9bS)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid

Traditional Name

(2S)-2-({[(3R,3aR,4S,6aR,8S,9aR,9bS)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3H-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

O[C@H]1C[C@@H]2[C@@H]([C@@H]3OC(=O)[C@@H](CN[C@@H](CC4=CC=CC=C4)C(O)=O)[C@@H]3[C@@H](O)CC2=C)C1=C

InChI Identifier

InChI=1S/C24H29NO6/c1-12-8-19(27)21-16(11-25-17(23(28)29)9-14-6-4-3-5-7-14)24(30)31-22(21)20-13(2)18(26)10-15(12)20/h3-7,15-22,25-27H,1-2,8-11H2,(H,28,29)/t15-,16-,17-,18-,19-,20-,21+,22-/m0/s1

InChI Key

UPFWZEIMZFQXJN-ZFBPGJDDSA-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
Saussurea pulchella	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
Guaianolide-skeleton
Sesquiterpenoid
Guaiane sesquiterpenoid
3-phenylpropanoic-acid
L-alpha-amino acid
Amphetamine or derivatives
Alpha-amino acid or derivatives
Alpha-amino acid
Aralkylamine
Benzenoid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tetrahydrofuran
Cyclic alcohol
Amino acid
Secondary alcohol
Lactone
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	-1.4	ChemAxon
pKa (Strongest Acidic)	1.57	ChemAxon
pKa (Strongest Basic)	9.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.66 m³·mol⁻¹	ChemAxon
Polarizability	43.84 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

162922207

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid (NP0291332)

MOL for NP0291332 ((2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid)

3D MOL for NP0291332 ((2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid)

3D SDF for NP0291332 ((2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid)

3D-SDF for NP0291332 ((2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid)

PDB for NP0291332 ((2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid)

3D PDB for NP0291332 ((2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid)

SMILES for NP0291332 ((2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid)

INCHI for NP0291332 ((2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid)

Structure for NP0291332 ((2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid)

3D Structure for NP0291332 ((2s)-2-({[(3r,3ar,4s,6ar,8s,9ar,9bs)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-3-yl]methyl}amino)-3-phenylpropanoic acid)