NP-MRD: Showing NP-Card for methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate (NP0248843)

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Record Information

Version

2.0

Created at

2022-09-07 11:14:44 UTC

Updated at

2022-09-07 11:14:44 UTC

NP-MRD ID

NP0248843

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

Description

Methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate is found in Theobroma grandiflorum. Methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191520032D          

 34 37  0  0  0  0            999 V2000
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 15 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -2.9528    0.4223   -4.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3343    0.2509   -3.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897    1.0992   -2.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3982    2.0387   -2.2556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9279    0.8975   -0.7306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0928   -0.1775   -0.7089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4132   -1.1757    0.2131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9483   -0.6851    1.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0070   -1.4007    2.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3831   -2.2807    3.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7503   -2.4861    3.4992 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5714   -2.9549    3.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9338   -2.7372    3.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -3.4242    4.3738 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2860   -1.8471    2.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916   -1.5794    2.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280   -2.1452    2.9121 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8486   -0.6585    1.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8614   -0.0069    0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1186    0.9564   -0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1007    1.6205   -1.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223    2.5295   -2.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6143    2.8187   -2.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8401    3.7346   -3.5545 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6412    2.1643   -1.8937 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3890    1.2418   -0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.3049    0.9730 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3257   -1.1588    1.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8908   -1.4647    0.2064 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3089   -1.8642   -1.0820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919   -0.2598    0.6445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8307   -0.1988   -0.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    1.0165    0.4000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7835    2.0544    0.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6447    1.2742   -4.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1482    0.5784   -5.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759   -0.4592   -4.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2599    1.8091   -0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -2.1179    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4761   -1.9942    3.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -3.6489    4.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8119   -3.4596    4.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8849   -0.4737    1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917    1.4130   -0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5180    3.0466   -2.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9712    4.7239   -3.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6487    2.3905   -2.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2636    0.7736   -0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1272   -2.3017    0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522   -2.0909   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9669   -0.3442    1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0599   -1.0409   -0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4216    1.2810    1.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6348    1.7327   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 28  2  0
 28 27  1  0
 27 19  1  0
 19 18  2  0
 18 16  1  0
 16 17  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
  7 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33  5  1  0
 28  9  1  0
 26 20  1  0
 16 15  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  1
  7 39  1  6
 11 40  1  0
 12 41  1  0
 14 42  1  0
 18 43  1  0
 21 44  1  0
 22 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  0
 29 49  1  1
 30 50  1  0
 31 51  1  1
 32 52  1  0
 33 53  1  1
 34 54  1  0
M  END


  Mrv1533004191520032D          

 34 37  0  0  0  0            999 V2000
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 15 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248843

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1OC(OC2=C(O)C=C(O)C3=C2OC(=CC3=O)C2=CC=C(O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O12/c1-31-21(30)20-16(28)15(27)17(29)22(34-20)33-18-12(26)6-10(24)14-11(25)7-13(32-19(14)18)8-2-4-9(23)5-3-8/h2-7,15-17,20,22-24,26-29H,1H3

> <INCHI_KEY>
OBCWIMFOZUOMAM-UHFFFAOYSA-N

> <FORMULA>
C22H20O12

> <MOLECULAR_WEIGHT>
476.39

> <EXACT_MASS>
476.095476084

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.709641689489345

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
0.6012243126666668

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.360843275309572

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.955999799908985

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868336342882495

> <JCHEM_POLAR_SURFACE_AREA>
192.44

> <JCHEM_REFRACTIVITY>
111.67570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20    9   15                                                  
CONECT   22   19   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29    7   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    5   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	Generator

Chemical Formula

C₂₂H₂₀O₁₂

Average Mass

476.3900 Da

Monoisotopic Mass

476.09548 Da

IUPAC Name

methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

Traditional Name

methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1OC(OC2=C(O)C=C(O)C3=C2OC(=CC3=O)C2=CC=C(O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C22H20O12/c1-31-21(30)20-16(28)15(27)17(29)22(34-20)33-18-12(26)6-10(24)14-11(25)7-13(32-19(14)18)8-2-4-9(23)5-3-8/h2-7,15-17,20,22-24,26-29H,1H3

InChI Key

OBCWIMFOZUOMAM-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
Theobroma grandiflorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidospermatan-type alkaloids

Sub Class

Not Available

Direct Parent

Aspidospermatan-type alkaloids

Alternative Parents

Substituents

Aspidosperma alkaloid
Plumeran-type alkaloid
Carbazole
Indolecarboxylic acid derivative
Quinolidine
Benzamide
Benzoic acid or derivatives
Indole or derivatives
Indolizidine
Anisole
Benzoyl
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Benzenoid
N-alkylpyrrolidine
Piperidine
Tertiary carboxylic acid amide
Pyrrolidine
Methyl ester
Tertiary amine
Amino acid or derivatives
Tertiary aliphatic amine
Carboxylic acid ester
Carboxamide group
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
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	1.43	ALOGPS
logP	0.6	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.96	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.68 m³·mol⁻¹	ChemAxon
Polarizability	44.71 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

75072217

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate (NP0248843)

MOL for NP0248843 (methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

3D MOL for NP0248843 (methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

3D SDF for NP0248843 (methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

3D-SDF for NP0248843 (methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

PDB for NP0248843 (methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

3D PDB for NP0248843 (methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

SMILES for NP0248843 (methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

INCHI for NP0248843 (methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

Structure for NP0248843 (methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

3D Structure for NP0248843 (methyl 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)