NP-MRD: Showing NP-Card for (1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione (NP0193605)

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Record Information

Version

2.0

Created at

2022-09-04 11:05:50 UTC

Updated at

2022-09-04 11:05:51 UTC

NP-MRD ID

NP0193605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione

Description

(Z)-6,6',7,3'Alpha-Diligustilide belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. (1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione is found in Ligusticum porteri. (1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione was first documented in 2011 (PMID: 20879744). Based on a literature review very few articles have been published on (Z)-6,6',7,3'Alpha-Diligustilide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042213052D          

 28 32  0  0  1  0            999 V2000
    0.7310   -2.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1389   -2.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7217   -1.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -0.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7124    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1336    0.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407    0.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1070    1.1871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3926    1.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936    2.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201    2.7403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9463    2.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542    1.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1391    0.8152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9797    1.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7054    0.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081    1.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3852    2.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596    2.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9568    2.1218    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0363    0.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8382    0.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0713    1.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8732    1.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1062    2.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218    0.0393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8992    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  9  1  6  0  0  0
  5 14  1  0  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  1  0  0  0  0
 20 19  1  6  0  0  0
 15 20  1  0  0  0  0
 11 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  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 26  1  0  0  0  0
 26 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -3.4432   -2.7226   -2.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4433   -1.5798   -1.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4394   -1.1284   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0912   -0.6702   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9104    0.5714    0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0323    1.4297    0.4023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5845    2.7423    0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2871    3.8103    0.3894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1346    2.6778    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1119    3.4650    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0079    3.2110    1.1548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7978    2.9541    2.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5889    1.6293    2.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7478    1.2832    0.8296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4512    0.9074    0.3502 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2295   -0.3277    0.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4933   -0.4412    0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2105    0.5968   -0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4930    1.9345   -0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.9381    0.7422 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0134   -1.6913    0.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2041   -2.2145    0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2649   -1.6613   -0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6675   -2.6202   -1.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7881   -1.8971   -1.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0087   -2.3079    1.6828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0803   -1.4739    1.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1835   -1.6976    2.2482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4150   -2.3688   -1.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -3.2839   -2.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -3.4285   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1883   -0.7347   -2.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4274   -2.0140   -2.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2156   -0.3708   -0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7217   -1.9670    0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -1.3710   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9859    4.1848   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6671    4.0561    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584    3.7533    2.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1305    2.9613    3.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999    0.9226    2.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    1.7405    2.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4864    0.7894   -0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4742    0.3361   -1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0990    0.9299    0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477    1.9122   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    2.7692   -0.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2133    1.5664    1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844   -3.2011    1.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2098   -1.7937    0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3353   -0.6540   -0.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0962   -3.5517   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8176   -2.7802   -1.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4036   -2.6004   -2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3374   -1.1066   -2.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4837   -1.4125   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  2  0
 21 26  1  0
 26 27  1  0
 27 28  2  0
 27 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14  5  1  1
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
 17 21  1  0
 15 20  1  0
 15 16  1  0
 10 11  1  0
  9 14  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 24 52  1  0
 24 53  1  0
 23 50  1  0
 23 51  1  0
 22 49  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  1
 11 38  1  1
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  6
 10 37  1  0
  4 36  1  0
  3 34  1  0
  3 35  1  0
  2 32  1  0
  2 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END


  Mrv1652309042213052D          

 28 32  0  0  1  0            999 V2000
    0.7310   -2.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1389   -2.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7217   -1.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -0.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7124    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1336    0.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407    0.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1070    1.1871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3926    1.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936    2.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201    2.7403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9463    2.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542    1.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1391    0.8152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9797    1.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7054    0.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081    1.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3852    2.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596    2.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9568    2.1218    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0363    0.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8382    0.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0713    1.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8732    1.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1062    2.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218    0.0393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8992    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  9  1  6  0  0  0
  5 14  1  0  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  1  0  0  0  0
 20 19  1  6  0  0  0
 15 20  1  0  0  0  0
 11 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  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 26  1  0  0  0  0
 26 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0193605

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C1\OC(=O)C2=C1CC[C@H]1[C@@H]3CC[C@@]4(C21)\C(OC(=O)C4=C3)=C\CCC

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O4/c1-3-5-7-18-16-10-9-15-14-11-12-24(21(15)20(16)23(26)27-18)17(13-14)22(25)28-19(24)8-6-4-2/h7-8,13-15,21H,3-6,9-12H2,1-2H3/b18-7+,19-8-/t14-,15+,21?,24+/m1/s1

> <INCHI_KEY>
UBBRXVRQZJSDAK-FGUXGJARSA-N

> <FORMULA>
C24H28O4

> <MOLECULAR_WEIGHT>
380.484

> <EXACT_MASS>
380.198759382

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.43006464155067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,6E,10S,11S,16Z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0^{1,13}.0^{2,10}.0^{3,7}]octadeca-3(7),12-diene-4,14-dione

> <JCHEM_LOGP>
4.692869615666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.7186754254466745

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
110.22809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6E,10S,11S,16Z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0^{1,13}.0^{2,10}.0^{3,7}]octadeca-3(7),12-diene-4,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.365  -5.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.126  -3.849   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.347  -2.521   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.109  -1.182   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.330   0.147   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.249   0.124   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.636   1.645   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.066   2.216   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.733   2.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.735   4.251   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.277   5.115   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.766   3.814   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.715   2.791   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126   1.522   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.695   2.421   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.050   1.689   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.362   2.495   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.319   4.035   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.965   4.767   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.653   3.961   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.534   1.497   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.031   1.859   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.466   3.336   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.963   3.698   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.398   5.175   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.947   0.073   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.412   0.192   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.414  -0.981   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9    5   15                                             
CONECT   15   14   16   20                                                  
CONECT   16   15   17   27                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   11                                                  
CONECT   21   17   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   21   27                                                       
CONECT   27   26   16   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Value	Source
(Z)-6,6',7,3'a-Diligustilide	Generator
(Z)-6,6',7,3'Α-diligustilide	Generator

Chemical Formula

C₂₄H₂₈O₄

Average Mass

380.4840 Da

Monoisotopic Mass

380.19876 Da

IUPAC Name

(1S,6E,10S,11S,16Z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0^{1,13}.0^{2,10}.0^{3,7}]octadeca-3(7),12-diene-4,14-dione

Traditional Name

(1S,6E,10S,11S,16Z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0^{1,13}.0^{2,10}.0^{3,7}]octadeca-3(7),12-diene-4,14-dione

CAS Registry Number

Not Available

SMILES

CCC\C=C1\OC(=O)C2=C1CC[C@H]1[C@@H]3CC[C@@]4(C21)\C(OC(=O)C4=C3)=C\CCC

InChI Identifier

InChI=1S/C24H28O4/c1-3-5-7-18-16-10-9-15-14-11-12-24(21(15)20(16)23(26)27-18)17(13-14)22(25)28-19(24)8-6-4-2/h7-8,13-15,21H,3-6,9-12H2,1-2H3/b18-7+,19-8-/t14-,15+,21?,24+/m1/s1

InChI Key

UBBRXVRQZJSDAK-FGUXGJARSA-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
Ligusticum porteri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Dicarboxylic acid or derivatives
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	4.69	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.23 m³·mol⁻¹	ChemAxon
Polarizability	43.43 Å³	ChemAxon
Number of Rings	5	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

26345825

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54582271

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Brindis F, Rodriguez R, Bye R, Gonzalez-Andrade M, Mata R: (Z)-3-butylidenephthalide from Ligusticum porteri , an alpha-glucosidase inhibitor. J Nat Prod. 2011 Mar 25;74(3):314-20. doi: 10.1021/np100447a. Epub 2010 Sep 29. [PubMed:20879744 ]
LOTUS database [Link]

Showing NP-Card for (1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione (NP0193605)

MOL for NP0193605 ((1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione)

3D MOL for NP0193605 ((1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione)

3D SDF for NP0193605 ((1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione)

3D-SDF for NP0193605 ((1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione)

PDB for NP0193605 ((1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione)

3D PDB for NP0193605 ((1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione)

SMILES for NP0193605 ((1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione)

INCHI for NP0193605 ((1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione)

Structure for NP0193605 ((1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione)

3D Structure for NP0193605 ((1s,6e,10s,11s,16z)-6,16-dibutylidene-5,15-dioxapentacyclo[9.5.2.0¹,¹³.0²,¹⁰.0³,⁷]octadeca-3(7),12-diene-4,14-dione)