NP-MRD: Showing NP-Card for O-methyl-alloptaeroxylin (NP0027752)

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Record Information

Version

2.0

Created at

2021-06-19 19:49:37 UTC

Updated at

2021-06-29 23:54:03 UTC

NP-MRD ID

NP0027752

Secondary Accession Numbers

None

Natural Product Identification

Common Name

O-methyl-alloptaeroxylin

Provided By

JEOL Database JEOL Logo

Description

5-Methoxy-2,8,8-trimethyl-4H,8H-pyrano[2,3-f]chromen-4-one is also known as perforatin a. O-methyl-alloptaeroxylin is found in Cedrelopsis gracilis. O-methyl-alloptaeroxylin was first documented in 2004 (Mulholland, D. A., et al.). Based on a literature review very few articles have been published on 5-methoxy-2,8,8-trimethyl-4H,8H-pyrano[2,3-f]chromen-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121493D          

 36 38  0  0  0  0            999 V2000
    0.6702    0.1187   -7.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4006    0.5033   -6.2863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126    0.4579   -4.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853    0.0503   -4.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234    0.0227   -2.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657    0.4024   -2.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    0.8139   -2.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585    1.1794   -1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    1.5919   -2.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3774    1.9582   -1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6278    1.6632   -3.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916    1.2887   -4.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615    1.3650   -5.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2859    0.8430   -4.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    0.3590   -0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -0.0440   -0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866   -0.4584   -1.0727 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9631   -1.9120   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861    0.4560   -0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434   -0.3947   -2.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351    0.7769   -7.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    0.2220   -8.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -0.9302   -6.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418   -0.2561   -4.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5817    1.0985   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988    2.7758   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3263    2.2815   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5792    1.9879   -4.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5575    0.6499   -0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802   -0.0799    0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318   -2.5885   -0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358   -2.0509    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8067   -2.2373   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513    1.4960   -1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958    0.4234    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440    0.1719   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  2  0  0  0  0
  9  8  1  0  0  0  0
 14  7  1  0  0  0  0
  7  8  1  0  0  0  0
 14 12  1  0  0  0  0
  5 20  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 20  1  0  0  0  0
 12 11  1  0  0  0  0
  9 10  1  0  0  0  0
 14  3  2  0  0  0  0
 12 13  2  0  0  0  0
  7  6  2  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
 17 18  1  0  0  0  0
  4  3  1  0  0  0  0
 17 19  1  0  0  0  0
  5  6  1  0  0  0  0
  2  1  1  0  0  0  0
 11 28  1  0  0  0  0
  4 24  1  0  0  0  0
 15 29  1  0  0  0  0
 16 30  1  0  0  0  0
 10 25  1  0  0  0  0
 10 26  1  0  0  0  0
 10 27  1  0  0  0  0
 18 31  1  0  0  0  0
 18 32  1  0  0  0  0
 18 33  1  0  0  0  0
 19 34  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    0.6702    0.1187   -7.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4006    0.5033   -6.2863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126    0.4579   -4.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853    0.0503   -4.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234    0.0227   -2.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657    0.4024   -2.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    0.8139   -2.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585    1.1794   -1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    1.5919   -2.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3774    1.9582   -1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6278    1.6632   -3.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916    1.2887   -4.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615    1.3650   -5.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2859    0.8430   -4.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    0.3590   -0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -0.0440   -0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866   -0.4584   -1.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631   -1.9120   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861    0.4560   -0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434   -0.3947   -2.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351    0.7769   -7.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    0.2220   -8.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -0.9302   -6.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418   -0.2561   -4.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5817    1.0985   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988    2.7758   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3263    2.2815   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5792    1.9879   -4.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5575    0.6499   -0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802   -0.0799    0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318   -2.5885   -0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358   -2.0509    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8067   -2.2373   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513    1.4960   -1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958    0.4234    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440    0.1719   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  2  0
  9  8  1  0
 14  7  1  0
  7  8  1  0
 14 12  1  0
  5 20  1  0
  6 15  1  0
 15 16  2  0
 16 17  1  0
 17 20  1  0
 12 11  1  0
  9 10  1  0
 14  3  2  0
 12 13  2  0
  7  6  2  0
  3  2  1  0
  5  4  2  0
 17 18  1  0
  4  3  1  0
 17 19  1  0
  5  6  1  0
  2  1  1  0
 11 28  1  0
  4 24  1  0
 15 29  1  0
 16 30  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END


  Mrv1652306192121493D          

 36 38  0  0  0  0            999 V2000
    0.6702    0.1187   -7.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4006    0.5033   -6.2863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126    0.4579   -4.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853    0.0503   -4.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234    0.0227   -2.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657    0.4024   -2.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    0.8139   -2.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585    1.1794   -1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    1.5919   -2.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3774    1.9582   -1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6278    1.6632   -3.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916    1.2887   -4.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615    1.3650   -5.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2859    0.8430   -4.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    0.3590   -0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -0.0440   -0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866   -0.4584   -1.0727 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9631   -1.9120   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861    0.4560   -0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434   -0.3947   -2.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351    0.7769   -7.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    0.2220   -8.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -0.9302   -6.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418   -0.2561   -4.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5817    1.0985   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988    2.7758   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3263    2.2815   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5792    1.9879   -4.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5575    0.6499   -0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802   -0.0799    0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318   -2.5885   -0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358   -2.0509    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8067   -2.2373   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513    1.4960   -1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958    0.4234    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440    0.1719   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  2  0  0  0  0
  9  8  1  0  0  0  0
 14  7  1  0  0  0  0
  7  8  1  0  0  0  0
 14 12  1  0  0  0  0
  5 20  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 20  1  0  0  0  0
 12 11  1  0  0  0  0
  9 10  1  0  0  0  0
 14  3  2  0  0  0  0
 12 13  2  0  0  0  0
  7  6  2  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
 17 18  1  0  0  0  0
  4  3  1  0  0  0  0
 17 19  1  0  0  0  0
  5  6  1  0  0  0  0
  2  1  1  0  0  0  0
 11 28  1  0  0  0  0
  4 24  1  0  0  0  0
 15 29  1  0  0  0  0
 16 30  1  0  0  0  0
 10 25  1  0  0  0  0
 10 26  1  0  0  0  0
 10 27  1  0  0  0  0
 18 31  1  0  0  0  0
 18 32  1  0  0  0  0
 18 33  1  0  0  0  0
 19 34  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027752

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C(OC2=C([H])C(OC([H])([H])[H])=C3C(=O)C([H])=C(OC3=C12)C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O4/c1-9-7-11(17)14-13(18-4)8-12-10(15(14)19-9)5-6-16(2,3)20-12/h5-8H,1-4H3

> <INCHI_KEY>
KADZFFQFRJPWDH-UHFFFAOYSA-N

> <FORMULA>
C16H16O4

> <MOLECULAR_WEIGHT>
272.3

> <EXACT_MASS>
272.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.476218364368115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-2,8,8-trimethyl-4H,8H-pyrano[2,3-f]chromen-4-one

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
2.6145054056666663

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.250296002463354

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5410029263872715

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
77.96380000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxy-2,8,8-trimethylpyrano[2,3-f]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    0.6702    0.1187   -7.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4006    0.5033   -6.2863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126    0.4579   -4.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853    0.0503   -4.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234    0.0227   -2.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657    0.4024   -2.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    0.8139   -2.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585    1.1794   -1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    1.5919   -2.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3774    1.9582   -1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6278    1.6632   -3.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916    1.2887   -4.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615    1.3650   -5.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2859    0.8430   -4.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    0.3590   -0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -0.0440   -0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866   -0.4584   -1.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631   -1.9120   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861    0.4560   -0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434   -0.3947   -2.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351    0.7769   -7.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    0.2220   -8.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -0.9302   -6.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418   -0.2561   -4.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5817    1.0985   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988    2.7758   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3263    2.2815   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5792    1.9879   -4.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5575    0.6499   -0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802   -0.0799    0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318   -2.5885   -0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358   -2.0509    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8067   -2.2373   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513    1.4960   -1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958    0.4234    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440    0.1719   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  2  0
  9  8  1  0
 14  7  1  0
  7  8  1  0
 14 12  1  0
  5 20  1  0
  6 15  1  0
 15 16  2  0
 16 17  1  0
 17 20  1  0
 12 11  1  0
  9 10  1  0
 14  3  2  0
 12 13  2  0
  7  6  2  0
  3  2  1  0
  5  4  2  0
 17 18  1  0
  4  3  1  0
 17 19  1  0
  5  6  1  0
  2  1  1  0
 11 28  1  0
  4 24  1  0
 15 29  1  0
 16 30  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.670   0.119  -7.136  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.401   0.503  -6.286  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.213   0.458  -4.932  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.985   0.050  -4.336  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.123   0.023  -2.946  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.066   0.402  -2.120  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.143   0.814  -2.710  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.159   1.179  -1.852  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.368   1.592  -2.372  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.377   1.958  -1.330  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.628   1.663  -3.681  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.592   1.289  -4.658  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.861   1.365  -5.849  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.286   0.843  -4.106  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.252   0.359  -0.673  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.431  -0.044  -0.194  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.587  -0.458  -1.073  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.963  -1.912  -0.763  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.786   0.456  -0.798  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.343  -0.395  -2.492  0.00  0.00           O+0
HETATM   21  H   UNK     0       1.535   0.777  -7.004  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.329   0.222  -8.171  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.942  -0.930  -6.979  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.842  -0.256  -4.928  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.582   1.099  -0.684  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.999   2.776  -0.708  0.00  0.00           H+0
HETATM   27  H   UNK     0      -5.326   2.281  -1.770  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.579   1.988  -4.083  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.558   0.650  -0.013  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.580  -0.080   0.882  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.132  -2.588  -0.995  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.236  -2.051   0.289  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.807  -2.237  -1.383  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.551   1.496  -1.055  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.096   0.423   0.252  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.644   0.172  -1.419  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    3    1                                                       
CONECT    3   14    2    4                                                  
CONECT    4    5    3   24                                                  
CONECT    5   20    4    6                                                  
CONECT    6   15    7    5                                                  
CONECT    7   14    8    6                                                  
CONECT    8    9    7                                                       
CONECT    9   11    8   10                                                  
CONECT   10    9   25   26   27                                             
CONECT   11    9   12   28                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12                                                            
CONECT   14    7   12    3                                                  
CONECT   15    6   16   29                                                  
CONECT   16   15   17   30                                                  
CONECT   17   16   20   18   19                                             
CONECT   18   17   31   32   33                                             
CONECT   19   17   34   35   36                                             
CONECT   20    5   17                                                       
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    4                                                            
CONECT   25   10                                                            
CONECT   26   10                                                            
CONECT   27   10                                                            
CONECT   28   11                                                            
CONECT   29   15                                                            
CONECT   30   16                                                            
CONECT   31   18                                                            
CONECT   32   18                                                            
CONECT   33   18                                                            
CONECT   34   19                                                            
CONECT   35   19                                                            
CONECT   36   19                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
    0.6702    0.1187   -7.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4006    0.5033   -6.2863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126    0.4579   -4.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853    0.0503   -4.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234    0.0227   -2.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657    0.4024   -2.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    0.8139   -2.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585    1.1794   -1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    1.5919   -2.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3774    1.9582   -1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6278    1.6632   -3.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916    1.2887   -4.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615    1.3650   -5.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2859    0.8430   -4.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    0.3590   -0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -0.0440   -0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5866   -0.4584   -1.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631   -1.9120   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861    0.4560   -0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434   -0.3947   -2.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351    0.7769   -7.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    0.2220   -8.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -0.9302   -6.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418   -0.2561   -4.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5817    1.0985   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988    2.7758   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3263    2.2815   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5792    1.9879   -4.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5575    0.6499   -0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802   -0.0799    0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318   -2.5885   -0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358   -2.0509    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8067   -2.2373   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513    1.4960   -1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958    0.4234    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440    0.1719   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  2  0
  9  8  1  0
 14  7  1  0
  7  8  1  0
 14 12  1  0
  5 20  1  0
  6 15  1  0
 15 16  2  0
 16 17  1  0
 17 20  1  0
 12 11  1  0
  9 10  1  0
 14  3  2  0
 12 13  2  0
  7  6  2  0
  3  2  1  0
  5  4  2  0
 17 18  1  0
  4  3  1  0
 17 19  1  0
  5  6  1  0
  2  1  1  0
 11 28  1  0
  4 24  1  0
 15 29  1  0
 16 30  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Perforatin a	Kegg

Chemical Formula

C₁₆H₁₆O₄

Average Mass

272.3000 Da

Monoisotopic Mass

272.10486 Da

IUPAC Name

5-methoxy-2,8,8-trimethyl-4H,8H-pyrano[2,3-f]chromen-4-one

Traditional Name

5-methoxy-2,8,8-trimethylpyrano[2,3-f]chromen-4-one

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C(OC2=C([H])C(OC([H])([H])[H])=C3C(=O)C([H])=C(OC3=C12)C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C16H16O4/c1-9-7-11(17)14-13(18-4)8-12-10(15(14)19-9)5-6-16(2,3)20-12/h5-8H,1-4H3

InChI Key

KADZFFQFRJPWDH-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Cedrelopsis gracilis	JEOL database	Mulholland, D. A., et al, Phytochemistry 65, 2929 (2004)
Cedrelopsis grevei	KNApSAcK Database	22123792
Harrisonia abyssinica	KNApSAcK Database	22123792
Harrisonia perforata	KNApSAcK Database	22123792
Neochamaelea pulverulenta	KNApSAcK Database	22123792
Ptaeroxylon obliquum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

chromenes (CHEBI:2108 )
chromones (C09014 )

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	3.16	ALOGPS
logP	2.61	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.25	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.96 m³·mol⁻¹	ChemAxon
Polarizability	29.48 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

C00002436

Chemspider ID

390536

KEGG Compound ID

C09014

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

Mulholland, D. A., et al. (2004). Mulholland, D. A., et al, Phytochemistry 65, 2929 (2004). Phytochem..

Showing NP-Card for O-methyl-alloptaeroxylin (NP0027752)

MOL for NP0027752 (O-methyl-alloptaeroxylin)

3D MOL for NP0027752 (O-methyl-alloptaeroxylin)

3D SDF for NP0027752 (O-methyl-alloptaeroxylin)

3D-SDF for NP0027752 (O-methyl-alloptaeroxylin)

PDB for NP0027752 (O-methyl-alloptaeroxylin)

3D PDB for NP0027752 (O-methyl-alloptaeroxylin)

SMILES for NP0027752 (O-methyl-alloptaeroxylin)

INCHI for NP0027752 (O-methyl-alloptaeroxylin)

Structure for NP0027752 (O-methyl-alloptaeroxylin)

3D Structure for NP0027752 (O-methyl-alloptaeroxylin)