NP-MRD: Showing NP-Card for (3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate (NP0224471)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 02:50:00 UTC

Updated at

2022-09-06 02:50:00 UTC

NP-MRD ID

NP0224471

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate

Description

8Alpha-Isobutyryloxyartemin belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. (3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate is found in Artemisia pontica. 8Alpha-Isobutyryloxyartemin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006312D          

 27 29  0  0  0  0            999 V2000
10000.363710000.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.075310001.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.506710000.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.648710002.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3637 9998.7635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0788 9998.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7932 9998.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5077 9998.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7932 9999.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0788 9997.5249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6466 9999.1749    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.646610001.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.361910001.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3619 9999.5874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0764 9999.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.076410000.8249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.077510002.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.363010002.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.792010001.2378    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.792010002.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.862810001.0798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.377910000.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8628 9999.7449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6474 9999.9998    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.647410000.8247    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.552910000.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6078 9998.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 19 20  1  0  0  0  0
 18 13  1  0  0  0  0
 16 19  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 23 27  1  6  0  0  0
 22 26  2  0  0  0  0
 13 25  1  0  0  0  0
 24 14  1  0  0  0  0
 13  1  1  6  0  0  0
 25 12  1  1  0  0  0
 24 11  1  6  0  0  0
 14  5  1  6  0  0  0
 16  2  1  1  0  0  0
 19  3  1  1  0  0  0
 18  4  2  0  0  0  0
M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
   -3.7428   -0.6378    1.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3820    0.1250    0.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2317    1.2484    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5353    2.0288   -1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1032    2.3113   -0.7298 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0315    3.4785    0.0431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3301    1.1714   -0.1119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9906    1.5965    1.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0043    1.0206   -0.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7622   -0.1404   -0.1833 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0894   -0.1931   -0.5860 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1007    0.0031    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7581    0.2252    1.5395 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5405   -0.0419   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8608    1.0270   -1.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3713    0.2612    1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0439   -1.3528   -0.4612 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5174   -2.6395    0.0739 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1422   -3.4690   -1.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7598   -3.3647    0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7720   -4.5777    0.8278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8422   -2.5063    0.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3101   -1.2254    0.4029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1088   -0.1162   -0.1397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3879   -0.3873   -1.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6899   -0.4669    2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1132   -1.4563    1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1396    0.7952   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5663    1.9014    0.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0739    2.9985   -1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6869    1.5302   -2.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6257    2.5874   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9097    3.6198    0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486    0.8210    2.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0608    1.9531    1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6150    2.4772    1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2419    0.6552   -1.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5639    1.9456   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852    0.0697    0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458   -1.0166   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9729    1.1011   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4740    2.0149   -0.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5439    0.7103   -2.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6759   -0.6447    1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7499    0.8597    1.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2552    0.9064    0.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2903   -1.4143   -1.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -2.5297    0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835   -3.2063   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -3.3698   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -4.5319   -0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -1.1181    1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1163   -1.0370   -1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 23 17  1  0
  7 24  1  0
 10 17  1  0
 17 47  1  6
 18 48  1  1
 19 49  1  0
 19 50  1  0
 19 51  1  0
 23 52  1  1
 25 53  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  6
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  1
 14 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
M  END


  Mrv1652309272006312D          

 27 29  0  0  0  0            999 V2000
10000.363710000.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.075310001.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.506710000.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.648710002.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3637 9998.7635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0788 9998.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7932 9998.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5077 9998.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7932 9999.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0788 9997.5249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6466 9999.1749    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.646610001.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.361910001.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3619 9999.5874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0764 9999.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.076410000.8249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.077510002.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.363010002.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.792010001.2378    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.792010002.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.862810001.0798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.377910000.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8628 9999.7449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6474 9999.9998    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.647410000.8247    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.552910000.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6078 9998.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 19 20  1  0  0  0  0
 18 13  1  0  0  0  0
 16 19  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 23 27  1  6  0  0  0
 22 26  2  0  0  0  0
 13 25  1  0  0  0  0
 24 14  1  0  0  0  0
 13  1  1  6  0  0  0
 25 12  1  1  0  0  0
 24 11  1  6  0  0  0
 14  5  1  6  0  0  0
 16  2  1  1  0  0  0
 19  3  1  1  0  0  0
 18  4  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0224471

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@H](C)C(=O)O[C@]1([H])[C@@]1(O)C(=C)CC[C@@H](O)[C@]1(C)C[C@@H]2OC(=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O6/c1-9(2)16(21)24-12-8-18(5)13(20)7-6-10(3)19(18,23)15-14(12)11(4)17(22)25-15/h9,11-15,20,23H,3,6-8H2,1-2,4-5H3/t11-,12-,13+,14+,15-,18-,19-/m0/s1

> <INCHI_KEY>
OMGBWNREQPGSKP-PGGXUPQSSA-N

> <FORMULA>
C19H28O6

> <MOLECULAR_WEIGHT>
352.427

> <EXACT_MASS>
352.188588622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.390208589019345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aR,4S,5aS,6R,9aR,9bS)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate

> <ALOGPS_LOGP>
1.09

> <JCHEM_LOGP>
1.6334179013333328

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.697009983232316

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.861369141821573

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9765357805212984

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
88.89920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,4S,5aS,6R,9aR,9bS)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8667.3468667.437   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8668.6748669.747   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8671.3468668.207   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8666.0118671.287   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8667.3468664.359   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8668.6808663.586   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.0148664.359   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8671.3488663.586   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8670.0148665.899   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8668.6808662.046   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0    8666.0078665.126   0.000  0.00  0.00           H+0
HETATM   12  H   UNK     0    8666.0078669.747   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0    8667.3428668.976   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.3428665.896   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.6768666.666   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.6768668.206   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8668.6788671.287   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.3448670.517   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.0128668.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8670.0128670.517   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8664.5448668.682   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0    8663.6398667.436   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8664.5448666.190   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8666.0088666.666   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8666.0088668.206   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0    8662.0998667.436   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0    8664.0688664.726   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   16                                                            
CONECT    3   19                                                            
CONECT    4   18                                                            
CONECT    5    6   14                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6                                                            
CONECT   11   24                                                            
CONECT   12   25                                                            
CONECT   13   16   18   25    1                                             
CONECT   14   15   24    5                                                  
CONECT   15   14   16                                                       
CONECT   16   13   15   19    2                                             
CONECT   17   18   20                                                       
CONECT   18   17   13    4                                                  
CONECT   19   20   16    3                                                  
CONECT   20   17   19                                                       
CONECT   21   22   25                                                       
CONECT   22   23   21   26                                                  
CONECT   23   22   24   27                                                  
CONECT   24   23   25   14   11                                             
CONECT   25   24   21   13   12                                             
CONECT   26   22                                                            
CONECT   27   23                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
8a-Isobutyryloxyartemin	Generator
8Α-isobutyryloxyartemin	Generator
8alpha-Isobutyryloxyartemin	PhytoBank

Chemical Formula

C₁₉H₂₈O₆

Average Mass

352.4270 Da

Monoisotopic Mass

352.18859 Da

IUPAC Name

(3S,3aR,4S,5aS,6R,9aR,9bS)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate

Traditional Name

(3S,3aR,4S,5aS,6R,9aR,9bS)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@H](C)C(=O)O[C@]1([H])[C@@]1(O)C(=C)CC[C@@H](O)[C@]1(C)C[C@@H]2OC(=O)C(C)C

InChI Identifier

InChI=1S/C19H28O6/c1-9(2)16(21)24-12-8-18(5)13(20)7-6-10(3)19(18,23)15-14(12)11(4)17(22)25-15/h9,11-15,20,23H,3,6-8H2,1-2,4-5H3/t11-,12-,13+,14+,15-,18-,19-/m0/s1

InChI Key

OMGBWNREQPGSKP-PGGXUPQSSA-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
Artemisia pontica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.09	ALOGPS
logP	1.63	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.9 m³·mol⁻¹	ChemAxon
Polarizability	37.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15275721

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate (NP0224471)

MOL for NP0224471 ((3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate)

3D MOL for NP0224471 ((3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate)

3D SDF for NP0224471 ((3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate)

3D-SDF for NP0224471 ((3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate)

PDB for NP0224471 ((3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate)

3D PDB for NP0224471 ((3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate)

SMILES for NP0224471 ((3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate)

INCHI for NP0224471 ((3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate)

Structure for NP0224471 ((3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate)

3D Structure for NP0224471 ((3s,3ar,4s,5as,6r,9ar,9bs)-6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-2-oxo-octahydronaphtho[1,2-b]furan-4-yl 2-methylpropanoate)