NP-MRD: Showing NP-Card for methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate (NP0147376)

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Record Information

Version

2.0

Created at

2022-09-02 02:58:14 UTC

Updated at

2022-09-02 02:58:14 UTC

NP-MRD ID

NP0147376

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate

Description

Artoindonesianin C belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate is found in Artocarpus kemando, Artocarpus rigidus and Artocarpus teysmannii. Artoindonesianin C is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201500332D          

 34 38  0  0  0  0            999 V2000
   -4.1028   -2.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4011   -3.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -2.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6496   -2.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9728   -3.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4776   -4.0777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6146   -2.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269   -2.1967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500   -3.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517   -4.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7783   -3.6477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4800   -4.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2066   -3.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2314   -2.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9580   -2.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6597   -2.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651   -2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -3.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6349   -3.7338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083   -4.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8834   -4.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568   -5.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320   -6.1647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4551   -4.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7286   -5.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037   -6.1216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0268   -4.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -5.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4015   -4.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280   -5.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8297   -4.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1529   -6.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -3.9954    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 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
 23 25  2  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 30 34  2  0  0  0  0
  5 34  1  0  0  0  0
 10 34  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -4.2505   -3.4218   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1803   -2.1167   -0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3964   -1.4321   -0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9085   -1.4339   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -2.2136   -0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5376   -1.6667   -0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611   -2.4552   -0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -3.6337   -1.0921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043   -1.8928   -0.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120   -2.6388   -0.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7873   -3.9322   -1.2880 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -2.0841   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2889   -0.7792   -0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1806   -0.0252    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9207   -0.6080    0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805    0.1316    0.3219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3366   -0.3931    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4577    0.3434    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7568   -0.1530    0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7172    0.8902    0.7649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8342    0.4312    1.4067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9990    1.8935   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0325    2.3615   -0.9401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2733    2.3139   -0.6152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5891    3.2492   -1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696    1.7097    1.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5893    1.7067    1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196    2.6655    0.9169 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375    1.3317    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5589    1.8465    0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7721    1.0820    0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5879    1.8192   -0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6430    0.9373    1.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5277   -0.2045    0.0324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3854   -4.0029    0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -3.9506   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2676   -0.4297   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8877   -2.1032   -1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1948   -1.4367    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9077   -3.2367   -0.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5626   -4.5020   -1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0450   -2.6661   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6522    0.9470    1.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0948    3.0932   -2.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7088    3.2079   -1.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3783    4.3048   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3087    2.6951    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7148    1.1209    2.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4501    1.8925    0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6719    2.8406    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6573    1.5182   -0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5194    2.8929   -0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270    1.6196   -1.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5411    1.7856    2.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3223    0.0250    2.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6936    0.7561    1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 22 20  1  0
 20 21  1  1
 20 26  1  0
 26 27  1  0
 27 28  2  0
 27 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 14 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
 34 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  1  0
 10  9  2  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  4 19  2  0
 19 20  1  0
 19 18  1  0
  6 17  1  0
  9 15  1  0
 13 14  1  0
 25 44  1  0
 25 45  1  0
 25 46  1  0
 21 43  1  0
 26 47  1  0
 26 48  1  0
 29 49  1  0
 30 50  1  0
 32 51  1  0
 32 52  1  0
 32 53  1  0
 33 54  1  0
 33 55  1  0
 33 56  1  0
 12 42  1  0
 11 41  1  0
  5 40  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  1 35  1  0
  1 36  1  0
M  END


  Mrv1533004201500332D          

 34 38  0  0  0  0            999 V2000
   -4.1028   -2.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4011   -3.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -2.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6496   -2.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9728   -3.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4776   -4.0777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6146   -2.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269   -2.1967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500   -3.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517   -4.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7783   -3.6477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4800   -4.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2066   -3.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2314   -2.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9580   -2.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6597   -2.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651   -2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -3.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6349   -3.7338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083   -4.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8834   -4.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568   -5.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320   -6.1647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4551   -4.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7286   -5.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037   -6.1216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0268   -4.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -5.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4015   -4.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280   -5.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8297   -4.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1529   -6.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -3.9954    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 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
 23 25  2  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 30 34  2  0  0  0  0
  5 34  1  0  0  0  0
 10 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147376

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(O)CC(=O)C2=C3OC4=C5C=CC(C)(C)OC5=CC(O)=C4C(=O)C3=CC(C(C)=C)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C26H22O8/c1-11(2)13-8-14-21(29)19-15(27)9-17-12(6-7-25(3,4)34-17)22(19)33-23(14)18-16(28)10-26(31,20(13)18)24(30)32-5/h6-9,27,31H,1,10H2,2-5H3

> <INCHI_KEY>
ZYXATNOZMULVQS-UHFFFAOYSA-N

> <FORMULA>
C26H22O8

> <MOLECULAR_WEIGHT>
462.454

> <EXACT_MASS>
462.131467668

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
48.02163491087982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
3.883226067333333

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.699338112890082

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.146939013996658

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7778324785728077

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
123.08159999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -7.659  -5.503   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.349  -6.313   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.992  -5.584   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.946  -4.044   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.682  -6.394   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.625  -7.612   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.014  -5.006   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.488  -5.213   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.423  -4.100   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.213  -6.729   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.097  -7.539   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.453  -6.809   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.763  -7.619   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.119  -6.889   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.165  -5.350   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.522  -4.621   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.832  -5.431   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.402  -4.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.339  -5.744   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.785  -6.970   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.429  -7.699   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.382  -9.239   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.026  -9.968   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.980 -11.507   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.716  -9.158   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.360  -9.888   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.314 -11.427   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.050  -9.078   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.306  -9.807   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.616  -8.997   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.972  -9.727   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.282  -8.917   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.019 -11.266   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.570  -7.458   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   34                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   34                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   14   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   13   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   11   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   30    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₂O₈

Average Mass

462.4540 Da

Monoisotopic Mass

462.13147 Da

IUPAC Name

methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate

Traditional Name

methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(O)CC(=O)C2=C3OC4=C5C=CC(C)(C)OC5=CC(O)=C4C(=O)C3=CC(C(C)=C)=C12

InChI Identifier

InChI=1S/C26H22O8/c1-11(2)13-8-14-21(29)19-15(27)9-17-12(6-7-25(3,4)34-17)22(19)33-23(14)18-16(28)10-26(31,20(13)18)24(30)32-5/h6-9,27,31H,1,10H2,2-5H3

InChI Key

ZYXATNOZMULVQS-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
Artocarpus kemando	LOTUS Database	35616633
Artocarpus rigidus	LOTUS Database	35616633
Artocarpus teysmannii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Indanone
Indane
Styrene
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Oxacycle
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
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	3.05	ALOGPS
logP	3.88	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.15	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	123.08 m³·mol⁻¹	ChemAxon
Polarizability	48.02 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

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

10552003

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate (NP0147376)

MOL for NP0147376 (methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate)

3D MOL for NP0147376 (methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate)

3D SDF for NP0147376 (methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate)

3D-SDF for NP0147376 (methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate)

PDB for NP0147376 (methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate)

3D PDB for NP0147376 (methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate)

SMILES for NP0147376 (methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate)

INCHI for NP0147376 (methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate)

Structure for NP0147376 (methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate)

3D Structure for NP0147376 (methyl 7,14-dihydroxy-18,18-dimethyl-5,12-dioxo-9-(prop-1-en-2-yl)-2,17-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁶,²¹]henicosa-1(21),3,8,10,13,15,19-heptaene-7-carboxylate)