NP-MRD: Showing NP-Card for (1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione (NP0292308)

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Record Information

Version

2.0

Created at

2022-09-09 23:46:36 UTC

Updated at

2022-09-09 23:46:36 UTC

NP-MRD ID

NP0292308

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione

Description

13,14-Dimethoxy-13bbeta,13cbeta-dihydrodifuro[3,2-g:3',2'-G']cyclobuta[1,2-c:4,3-C']bis[1]benzopyran-6,7(6abetaH,6bbetaH)-dione belongs to the class of organic compounds known as linear furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring linearly fused to a coumarin. (1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione is found in Citrus medica. Based on a literature review very few articles have been published on 13,14-Dimethoxy-13bbeta,13cbeta-dihydrodifuro[3,2-g:3',2'-G']cyclobuta[1,2-c:4,3-C']bis[1]benzopyran-6,7(6abetaH,6bbetaH)-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102201462D          

 32 38  0  0  1  0            999 V2000
    4.2506    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6796   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3941   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3941    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0071    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8511    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6796    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6796   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2506   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4256   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7112    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6691    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0047    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8252    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256   -1.2375    0.0000 C   0  0  1  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  3 11  2  0  0  0  0
  7 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  6  0  0  0
 15 16  1  0  0  0  0
 16  4  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 32 30  1  6  0  0  0
 15 32  1  0  0  0  0
 17 32  1  0  0  0  0
M  END

     RDKit          3D

 48 54  0  0  0  0  0  0  0  0999 V2000
    2.4526    0.5582    2.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360    0.5430    1.2626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3302    0.8575    0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6780   -0.0842   -0.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    0.3338   -1.8056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649    1.6572   -2.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8122    2.5755   -1.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0166    3.8942   -1.6160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954    4.3822   -0.6237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9641    3.3278    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3980    2.1984   -0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4733   -0.5321   -2.6769 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262   -1.8746   -2.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -2.6210   -3.0099 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2378   -2.3868   -1.2926 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4332   -1.3958   -0.1308 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1283   -1.9232    0.3471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1587   -1.4028    0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1165   -2.1271   -0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3705   -1.6045   -0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7162   -0.3345   -0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8234    0.3940   -0.7742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6701    1.5767   -0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4103    1.6256    0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8041    0.4085    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5632   -0.1347    0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7019    0.7138    1.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9204    0.6849    2.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8275   -3.4101   -1.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259   -3.9928   -0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5247   -5.2764   -0.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5139   -3.2337   -0.2763 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3316    0.5350    3.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9544    1.5308    2.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7424   -0.2442    2.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7088    1.9780   -3.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955    5.4161   -0.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5075    3.3701    1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1911   -2.8992   -1.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2762   -1.7769    0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255   -2.0618    1.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0761   -2.2145   -1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3669    2.4024   -0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9607    2.4440    0.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304    1.4369    3.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6139   -0.3193    2.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0300    0.8312    2.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2349   -3.8255    0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 26  1  0
 26 25  2  0
 25 24  1  0
 24 23  2  0
 23 22  1  0
 22 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 32  1  0
 32 15  1  0
 15 16  1  0
 16  4  1  0
  4  5  2  0
  5 12  1  0
 12 13  1  0
 13 14  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  3  2  0
  3  2  1  0
  2  1  1  0
 32 30  1  0
 30 31  2  0
 30 29  1  0
 18 26  1  0
 16 17  1  0
  3  4  1  0
 21 25  1  0
 29 19  1  0
 13 15  1  0
 11  7  1  0
 28 45  1  0
 28 46  1  0
 28 47  1  0
 24 44  1  0
 23 43  1  0
 20 42  1  0
 17 41  1  1
 32 48  1  1
 15 39  1  6
 16 40  1  1
  6 36  1  0
  9 37  1  0
 10 38  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END


  Mrv1652309102201462D          

 32 38  0  0  1  0            999 V2000
    4.2506    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6796   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3941   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3941    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0071    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8511    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6796    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6796   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2506   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4256   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7112    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6691    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0047    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8252    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256   -1.2375    0.0000 C   0  0  1  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  3 11  2  0  0  0  0
  7 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  6  0  0  0
 15 16  1  0  0  0  0
 16  4  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 32 30  1  6  0  0  0
 15 32  1  0  0  0  0
 17 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292308

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=COC2=CC2=C1[C@H]1[C@H]([C@@H]3[C@H]1C1=C(OC3=O)C=C3OC=CC3=C1OC)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C24H16O8/c1-27-21-9-3-5-29-11(9)7-13-15(21)17-18-16-14(8-12-10(4-6-30-12)22(16)28-2)32-24(26)20(18)19(17)23(25)31-13/h3-8,17-20H,1-2H3/t17-,18+,19-,20+

> <INCHI_KEY>
CCLGJTQMQHAJLX-FGYAAKKASA-N

> <FORMULA>
C24H16O8

> <MOLECULAR_WEIGHT>
432.384

> <EXACT_MASS>
432.084517475

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
40.85244211714264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,14S,15R)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0^{2,14}.0^{3,11}.0^{5,9}.0^{18,26}.0^{20,24}]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione

> <JCHEM_LOGP>
2.7295274719999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5344069491755064

> <JCHEM_POLAR_SURFACE_AREA>
97.34

> <JCHEM_REFRACTIVITY>
107.757

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,14S,15R)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0^{2,14}.0^{3,11}.0^{5,9}.0^{18,26}.0^{20,24}]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione

> <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       7.935   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.935   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.268   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.268   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.602  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.936  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.936   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.080   2.570   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.454   3.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.922   3.816   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.602   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.602  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.268  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.268  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.935  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.935  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.395  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.061   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.727  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.393   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.393   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.249   2.570   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.875   3.977   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.407   3.816   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.727   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.061   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.395   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.395   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.727  -2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.061  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.061  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.395  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    3    7                                                  
CONECT   12    5   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   32                                                  
CONECT   16   15    4   17                                                  
CONECT   17   16   18   32                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   18   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   19   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   15   17                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₁₆O₈

Average Mass

432.3840 Da

Monoisotopic Mass

432.08452 Da

IUPAC Name

(1R,2S,14S,15R)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0^{2,14}.0^{3,11}.0^{5,9}.0^{18,26}.0^{20,24}]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione

Traditional Name

(1R,2S,14S,15R)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0^{2,14}.0^{3,11}.0^{5,9}.0^{18,26}.0^{20,24}]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione

CAS Registry Number

Not Available

SMILES

COC1=C2C=COC2=CC2=C1[C@H]1[C@H]([C@@H]3[C@H]1C1=C(OC3=O)C=C3OC=CC3=C1OC)C(=O)O2

InChI Identifier

InChI=1S/C24H16O8/c1-27-21-9-3-5-29-11(9)7-13-15(21)17-18-16-14(8-12-10(4-6-30-12)22(16)28-2)32-24(26)20(18)19(17)23(25)31-13/h3-8,17-20H,1-2H3/t17-,18+,19-,20+

InChI Key

CCLGJTQMQHAJLX-FGYAAKKASA-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
Citrus medica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring linearly fused to a coumarin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Linear furanocoumarins

Alternative Parents

Substituents

Linear furanocoumarin
3,4-dihydrocoumarin
Chromane
Benzopyran
1-benzopyran
Benzofuran
Anisole
Alkyl aryl ether
Benzenoid
Dicarboxylic acid or derivatives
Heteroaromatic compound
Furan
Carboxylic acid ester
Lactone
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	2.73	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	97.34 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	107.76 m³·mol⁻¹	ChemAxon
Polarizability	40.85 Å³	ChemAxon
Number of Rings	7	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

9319641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11144530

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione (NP0292308)

MOL for NP0292308 ((1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione)

3D MOL for NP0292308 ((1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione)

3D SDF for NP0292308 ((1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione)

3D-SDF for NP0292308 ((1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione)

PDB for NP0292308 ((1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione)

3D PDB for NP0292308 ((1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione)

SMILES for NP0292308 ((1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione)

INCHI for NP0292308 ((1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione)

Structure for NP0292308 ((1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione)

3D Structure for NP0292308 ((1r,2s,14s,15r)-4,25-dimethoxy-8,12,17,21-tetraoxaheptacyclo[13.11.0.0²,¹⁴.0³,¹¹.0⁵,⁹.0¹⁸,²⁶.0²⁰,²⁴]hexacosa-3(11),4,6,9,18(26),19,22,24-octaene-13,16-dione)