NP-MRD: Showing NP-Card for 3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate (NP0154661)

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Record Information

Version

2.0

Created at

2022-09-02 11:36:31 UTC

Updated at

2022-09-02 11:36:31 UTC

NP-MRD ID

NP0154661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate

Description

-(Hepta-1,3,5-trien-1-yl)-4-methyl-3,5-dioxo-3H,4H,5H,5bH-oxireno[2,3-዆]isochromen-4-yl 3,5-dihydroxyhexanoate belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center. 3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate is found in Penicillium griseofulvum. -(Hepta-1,3,5-trien-1-yl)-4-methyl-3,5-dioxo-3H,4H,5H,5bH-oxireno[2,3-዆]isochromen-4-yl 3,5-dihydroxyhexanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241510162D          

 31 33  0  0  0  0            999 V2000
   -0.1161   10.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9286   10.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2107    9.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0232    9.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054    8.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178    8.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000    7.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8697    6.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572    7.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    6.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842    5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283    6.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663    5.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    4.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663    4.2947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    4.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915    4.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205    4.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2788    4.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610    4.2012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    5.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913    4.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6216    5.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    6.0972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
  -11.0041   -1.7118   -1.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5247   -1.6799   -1.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8349   -1.1041   -0.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3853   -1.0351   -0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7406   -0.4514    0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2773   -0.3992    0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6351    0.1801    1.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788    0.2448    1.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4844    0.8256    2.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0335    0.8436    2.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3648    1.8363    2.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0935    1.9372    2.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    2.5811    3.3541 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7221    1.2036    1.3756 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3748    2.0115    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167    1.0906    1.5625 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218    0.4581    0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3515   -0.0077   -0.3795 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3616    0.3785    0.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1625   -0.3049   -0.1641 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5005   -0.3008    0.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1322    0.4780   -1.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9474   -0.2204   -2.5375 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3962   -0.3770   -2.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3611   -1.4405   -2.8359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0788   -0.1329    1.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7906   -1.1142    1.4255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3851   -0.2511    1.2682 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8881   -1.5469    1.4191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1267   -0.7306    0.2079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4632   -0.2942    0.1358 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2438   -1.8474   -0.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3806   -0.7206   -1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4476   -2.5521   -2.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0526   -2.1300   -2.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3518   -0.6748    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8493   -1.4604   -1.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2872   -0.0280    1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7280   -0.8203   -0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1416    0.6235    2.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798    1.2744    3.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892    2.6232    3.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5109    1.3869   -0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0323    2.9003    0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337    2.3772    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8264    1.3557    1.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4849   -0.2226    1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8613   -1.3508   -0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6457    0.3691    0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0932    0.4859   -1.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4626    1.5137   -1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9127    0.4005   -3.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7743    0.4698   -1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0337   -0.4520   -3.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5404   -1.3261   -1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8716   -1.9060   -3.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8022   -1.2556   -0.7155 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
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  1
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 14 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  1
 29 30  1  0
 30 31  1  0
 31  8  1  0
 28 10  1  0
 30 28  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  9 41  1  0
 11 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  6
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  6
 24 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 30 57  1  6
M  END


  Mrv1533004241510162D          

 31 33  0  0  0  0            999 V2000
   -0.1161   10.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9286   10.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2107    9.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0232    9.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054    8.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178    8.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000    7.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8697    6.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572    7.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    6.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842    5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283    6.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663    5.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    4.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663    4.2947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    4.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915    4.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205    4.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2788    4.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610    4.2012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    5.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913    4.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6216    5.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    6.0972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=CC=CC=CC1=CC2=CC(=O)C(C)(OC(=O)CC(O)CC(C)O)C(=O)C22OC2O1

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O8/c1-4-5-6-7-8-9-17-11-15-12-18(26)22(3,20(28)23(15)21(29-17)31-23)30-19(27)13-16(25)10-14(2)24/h4-9,11-12,14,16,21,24-25H,10,13H2,1-3H3

> <INCHI_KEY>
GWWPRBVUUXKASM-UHFFFAOYSA-N

> <FORMULA>
C23H26O8

> <MOLECULAR_WEIGHT>
430.453

> <EXACT_MASS>
430.162767797

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.488081048037124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-6H,7H,8H,8bH-oxireno[2,3-዆]isochromen-7-yl 3,5-dihydroxyhexanoate

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
2.0243903539999994

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.765736924886031

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.831220856766425

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5453013041240418

> <JCHEM_POLAR_SURFACE_AREA>
122.66000000000001

> <JCHEM_REFRACTIVITY>
115.9388

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-8bH-oxireno[2,3-዆]isochromen-7-yl 3,5-dihydroxyhexanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.217  19.152   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.733  18.884   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.260  17.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.777  17.170   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.303  15.723   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.820  15.455   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.347  14.008   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.357  12.829   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.840  13.096   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.850  11.916   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  12.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.344  11.004   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.173  11.271   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.870   9.557   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.646   9.289   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.870   8.017   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.463   7.247   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.463   5.707   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.797   8.017   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.131   7.247   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.131   5.707   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.464   8.017   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.798   7.247   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.132   8.017   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.798   5.707   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.387   9.289   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.914   7.842   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.377  10.469   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.904   9.022   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.894  10.202   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.883  11.381   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                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   26                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   14   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   10   29   30                                             
CONECT   29   28   30                                                       
CONECT   30   29   28   31                                                  
CONECT   31   30    8                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
-(Hepta-1,3,5-trien-1-yl)-4-methyl-3,5-dioxo-3H,4H,5H,5BH-oxireno[2,3-]isochromen-4-yl 3,5-dihydroxyhexanoic acid	Generator
-(Hepta-1,3,5-trien-1-yl)-4-methyl-3,5-dioxo-3H,4H,5H,5BH-oxireno[2,3-዆]isochromen-4-yl 3,5-dihydroxyhexanoic acid	Generator

Chemical Formula

C₂₃H₂₆O₈

Average Mass

430.4530 Da

Monoisotopic Mass

430.16277 Da

IUPAC Name

3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-6H,7H,8H,8bH-oxireno[2,3-዆]isochromen-7-yl 3,5-dihydroxyhexanoate

Traditional Name

3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-8bH-oxireno[2,3-዆]isochromen-7-yl 3,5-dihydroxyhexanoate

CAS Registry Number

Not Available

SMILES

CC=CC=CC=CC1=CC2=CC(=O)C(C)(OC(=O)CC(O)CC(C)O)C(=O)C22OC2O1

InChI Identifier

InChI=1S/C23H26O8/c1-4-5-6-7-8-9-17-11-15-12-18(26)22(3,20(28)23(15)21(29-17)31-23)30-19(27)13-16(25)10-14(2)24/h4-9,11-12,14,16,21,24-25H,10,13H2,1-3H3

InChI Key

GWWPRBVUUXKASM-UHFFFAOYSA-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
Penicillium griseofulvum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaphilones

Sub Class

Not Available

Direct Parent

Azaphilones

Alternative Parents

Substituents

Azaphilone
Beta-hydroxy acid
Fatty acid ester
Cyclohexenone
Alpha-acyloxy ketone
Hydroxy acid
Fatty acyl
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Oxirane
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen compound
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	2.18	ALOGPS
logP	2.02	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	14.83	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	122.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	115.94 m³·mol⁻¹	ChemAxon
Polarizability	45.49 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate (NP0154661)

MOL for NP0154661 (3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate)

3D MOL for NP0154661 (3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate)

3D SDF for NP0154661 (3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate)

3D-SDF for NP0154661 (3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate)

PDB for NP0154661 (3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate)

3D PDB for NP0154661 (3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate)

SMILES for NP0154661 (3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate)

INCHI for NP0154661 (3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate)

Structure for NP0154661 (3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate)

3D Structure for NP0154661 (3-(hepta-1,3,5-trien-1-yl)-7-methyl-6,8-dioxo-1ah-oxireno[2,3-j]isochromen-7-yl 3,5-dihydroxyhexanoate)