NP-MRD: Showing NP-Card for (3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate (NP0156908)

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Record Information

Version

2.0

Created at

2022-09-02 14:11:15 UTC

Updated at

2022-09-02 14:11:15 UTC

NP-MRD ID

NP0156908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate

Description

Badkhysin belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. (3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate is found in Daucus littoralis. (3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate was first documented in 2012 (PMID: 22145745). Based on a literature review very few articles have been published on Badkhysin (PMID: 24320993).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022216112D          

 25 27  0  0  1  0            999 V2000
    2.2340    4.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660    3.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751    2.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  1  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  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    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
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  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
    2.8409   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  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  2  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 16  1  1  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 25 23  1  6  0  0  0
  8 25  1  0  0  0  0
 19 25  1  0  0  0  0
M  END

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
    4.9451    0.2466   -2.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1307    0.4362   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1457    0.3806    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4581    0.5889    1.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906    0.1267   -0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438   -0.0461   -1.3488 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7165    0.0603    0.7357 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3672   -0.1859    0.2711 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842   -1.6301    0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1247   -2.2045    0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2067   -3.6320    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2960   -1.7412    0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5935   -2.3836    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7896   -3.5479    0.7451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5470   -1.3654   -0.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9190   -0.2418   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6561    0.9786   -0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4689   -0.3374   -0.2317 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9831    0.5595    0.8381 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6155    1.8118    0.6928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    2.5504   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1343    3.3968   -1.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972    2.1602    0.2498 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5222    2.3734   -0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082    0.8164    0.8318 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2611    0.9987   -2.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5206   -0.7569   -2.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9142    0.3826   -2.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1741    0.6310   -0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3762    1.6821    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5251    0.3304    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8340   -0.0169    2.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3685   -0.1779   -0.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6400   -1.8327    1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8502   -2.2450   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058   -4.2783    0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076   -3.9761    1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8476   -3.6023    2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6115   -1.5617   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8332    1.6892   -0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465    1.4244   -1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6270    0.7155   -1.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9150   -0.2289   -1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3243    0.1483    1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0883    2.9423    1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1350    3.3341   -1.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4566    1.6479   -1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5146    2.6512   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2403    0.9285    1.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 18 16  1  0
 16 17  1  0
 16 15  2  0
 15 13  1  0
 13 14  2  0
 25  8  1  0
 13 12  1  0
 25 19  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  8 33  1  6
  9 34  1  0
  9 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 18 43  1  6
 19 44  1  1
 23 45  1  1
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  1
 17 40  1  0
 17 41  1  0
 17 42  1  0
 15 39  1  0
M  END


  Mrv1652309022216112D          

 25 27  0  0  1  0            999 V2000
    2.2340    4.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660    3.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751    2.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  1  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  0  0  0  0  0  0  0  0  0  0
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    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
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  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
    2.8409   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  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  2  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 16  1  1  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 25 23  1  6  0  0  0
  8 25  1  0  0  0  0
 19 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@H]1CC(C)=C2[C@H]([C@@H]3OC(=O)[C@H](C)[C@H]13)C(C)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O5/c1-6-9(2)19(22)24-14-8-11(4)15-13(21)7-10(3)16(15)18-17(14)12(5)20(23)25-18/h6-7,12,14,16-18H,8H2,1-5H3/b9-6-/t12-,14+,16-,17-,18+/m1/s1

> <INCHI_KEY>
KRHKMQZMQZFVBI-ZCGJXKNNSA-N

> <FORMULA>
C20H24O5

> <MOLECULAR_WEIGHT>
344.407

> <EXACT_MASS>
344.162373873

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.19989951762089

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
3.334312567333333

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.018204863827485

> <JCHEM_PKA_STRONGEST_BASIC>
-5.348221050742794

> <JCHEM_POLAR_SURFACE_AREA>
69.67000000000002

> <JCHEM_REFRACTIVITY>
94.11680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.170   7.909   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.737   7.347   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.507   5.824   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.073   5.261   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.145   5.426   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.665   3.341   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.530   1.186   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    8   19                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₅

Average Mass

344.4070 Da

Monoisotopic Mass

344.16237 Da

IUPAC Name

(3R,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(3R,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@H]1CC(C)=C2[C@H]([C@@H]3OC(=O)[C@H](C)[C@H]13)C(C)=CC2=O

InChI Identifier

InChI=1S/C20H24O5/c1-6-9(2)19(22)24-14-8-11(4)15-13(21)7-10(3)16(15)18-17(14)12(5)20(23)25-18/h6-7,12,14,16-18H,8H2,1-5H3/b9-6-/t12-,14+,16-,17-,18+/m1/s1

InChI Key

KRHKMQZMQZFVBI-ZCGJXKNNSA-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
Daucus littoralis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Organooxygen compound
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	3.12	ALOGPS
logP	3.33	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	15.02	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.12 m³·mol⁻¹	ChemAxon
Polarizability	36.2 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

C00013025

Chemspider ID

10046668

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11872340

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dracinsky M, Budesinsky M, Warzajtis B, Rychlewska U: Solution and solid-state effects on NMR chemical shifts in sesquiterpene lactones: NMR, X-ray, and theoretical methods. J Phys Chem A. 2012 Jan 12;116(1):680-8. doi: 10.1021/jp209408b. Epub 2011 Dec 29. [PubMed:22145745 ]
Kasaian J, Iranshahy M, Masullo M, Piacente S, Ebrahimi F, Iranshahi M: Sesquiterpene lactones from Ferula oopoda and their cytotoxic properties. J Asian Nat Prod Res. 2014;16(3):248-53. doi: 10.1080/10286020.2013.866099. Epub 2013 Dec 10. [PubMed:24320993 ]
LOTUS database [Link]

Showing NP-Card for (3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate (NP0156908)

MOL for NP0156908 ((3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0156908 ((3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0156908 ((3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0156908 ((3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

PDB for NP0156908 ((3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0156908 ((3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0156908 ((3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0156908 ((3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

Structure for NP0156908 ((3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0156908 ((3r,3ar,4s,9ar,9bs)-3,6,9-trimethyl-2,7-dioxo-3h,3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)