NP-MRD: Showing NP-Card for 9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one (NP0296646)

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Record Information

Version

2.0

Created at

2022-09-10 06:21:12 UTC

Updated at

2022-09-10 06:21:13 UTC

NP-MRD ID

NP0296646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one

Description

9-Hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-2H,8H,9H-furo[2,3-h]chromen-2-one belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. 9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one is found in Peucedanum praeruptorum. 9-Hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-2H,8H,9H-furo[2,3-h]chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191518462D          

 31 34  0  0  0  0            999 V2000
    1.8480   -2.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -1.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9788   -0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7122   -2.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0148   -1.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7161   -2.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903   -2.9331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3915   -3.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658   -4.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0670   -4.6270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186   -2.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8198   -3.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -2.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713   -1.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4431   -1.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4688   -0.8940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -0.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3664    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6256   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4502   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4949   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9295   -2.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703   -1.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2357   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4111   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784   -1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0751   -2.3078    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
  2  4  1  0  0  0  0
  4  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  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  2  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    1.4206   -1.8532   -1.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0378   -0.4249   -1.4595 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1213   -0.2158   -2.8287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029   -0.2679   -1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1577   -1.1784   -1.7263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4803   -1.2382   -1.4495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9555   -2.3824   -0.8380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1332   -2.0990   -0.1894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7638   -1.7616    1.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308   -1.4566    1.9842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0364   -1.0952   -0.7552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3434   -1.6103   -0.9451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6538   -0.4377   -2.0418 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3903    0.9375   -1.8632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833   -1.0089   -2.6359 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7313   -2.2261   -3.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9439    0.5688   -0.7976 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2950    0.3920   -1.1909 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740    1.0462   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3577    1.5602   -0.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9165    2.1735    0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1592    2.2483    2.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689    2.8513    3.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8719    2.9027    4.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108    2.3723    4.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9127    2.4374    5.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277    1.7967    3.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8949    1.7470    2.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.1399    0.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0373    0.4805    0.6844 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1546   -0.8374    1.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7600   -2.3134   -0.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2524   -2.4381   -2.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.9605   -0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9122    0.7282   -3.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4816   -0.3709    0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7059    0.7694   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909   -0.4094   -0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6956   -3.0784   -0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262   -0.9331    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3072   -2.6389    1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0596   -0.4798    2.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1915   -0.2707    0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7638   -1.8219   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4369   -0.4969   -2.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8357    1.4937   -2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9013   -0.3407   -3.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6919   -2.2722   -3.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6825    1.6179   -1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9362    1.5000   -1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9169    2.5789    0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6678    3.2610    3.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2215    3.3626    5.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286    1.0178    1.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102   -1.0656    1.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 15  6  1  0
 30 17  1  0
 29 19  1  0
 28 22  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  6 38  1  1
  8 39  1  1
  9 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  0
 13 45  1  6
 14 46  1  0
 15 47  1  6
 16 48  1  0
 17 49  1  1
 20 50  1  0
 21 51  1  0
 23 52  1  0
 24 53  1  0
 30 54  1  1
 31 55  1  0
M  END


  Mrv1533004191518462D          

 31 34  0  0  0  0            999 V2000
    1.8480   -2.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -1.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9788   -0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7122   -2.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0148   -1.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7161   -2.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903   -2.9331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3915   -3.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658   -4.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0670   -4.6270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186   -2.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8198   -3.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -2.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713   -1.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4431   -1.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4688   -0.8940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -0.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3664    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6256   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4502   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4949   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9295   -2.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703   -1.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2357   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4111   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8784   -1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0751   -2.3078    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
  2  4  1  0  0  0  0
  4  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  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  2  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)(COC1OC(CO)C(O)C(O)C1O)C1OC2=CC=C3C=CC(=O)OC3=C2C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O11/c1-20(27,7-28-19-16(26)15(25)13(23)10(6-21)30-19)18-14(24)12-9(29-18)4-2-8-3-5-11(22)31-17(8)12/h2-5,10,13-16,18-19,21,23-27H,6-7H2,1H3

> <INCHI_KEY>
ZSGPHDPEQZJRBT-UHFFFAOYSA-N

> <FORMULA>
C20H24O11

> <MOLECULAR_WEIGHT>
440.401

> <EXACT_MASS>
440.131861593

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.0751643867885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-2H,8H,9H-furo[2,3-h]chromen-2-one

> <ALOGPS_LOGP>
-1.07

> <JCHEM_LOGP>
-2.0043481523333333

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.665785369028942

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.080339148304725

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834236673704

> <JCHEM_POLAR_SURFACE_AREA>
175.36999999999998

> <JCHEM_REFRACTIVITY>
101.50539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8H,9H-furo[2,3-h]chromen-2-one

> <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       3.450  -4.350   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.638  -3.041   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.827  -1.732   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.329  -3.853   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.028  -3.125   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.337  -3.936   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.289  -5.475   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.598  -6.286   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.549  -7.826   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.858  -8.637   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.955  -5.558   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.264  -6.370   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.003  -4.019   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.360  -3.291   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.694  -3.208   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.742  -1.669   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.947  -2.230   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.060  -0.694   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.556  -0.327   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.284   1.030   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.823   1.078   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.635  -0.231   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.174  -0.183   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.985  -1.492   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.257  -2.849   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.068  -4.158   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.718  -2.897   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.907  -1.588   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.367  -1.636   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.373  -2.812   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.740  -4.308   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   17                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    2   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   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   29                                                  
CONECT   29   28   19   30                                                  
CONECT   30   29   17   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₁₁

Average Mass

440.4010 Da

Monoisotopic Mass

440.13186 Da

IUPAC Name

9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-2H,8H,9H-furo[2,3-h]chromen-2-one

Traditional Name

9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8H,9H-furo[2,3-h]chromen-2-one

CAS Registry Number

Not Available

SMILES

CC(O)(COC1OC(CO)C(O)C(O)C1O)C1OC2=CC=C3C=CC(=O)OC3=C2C1O

InChI Identifier

InChI=1S/C20H24O11/c1-20(27,7-28-19-16(26)15(25)13(23)10(6-21)30-19)18-14(24)12-9(29-18)4-2-8-3-5-11(22)31-17(8)12/h2-5,10,13-16,18-19,21,23-27H,6-7H2,1H3

InChI Key

ZSGPHDPEQZJRBT-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
Peucedanum praeruptorum	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Angular furanocoumarins

Alternative Parents

Substituents

Angular furanocoumarin
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Coumaran
Alkyl aryl ether
Pyranone
Monosaccharide
Oxane
Benzenoid
Pyran
Heteroaromatic compound
Tertiary alcohol
Lactone
Secondary alcohol
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Ether
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.1	ALOGPS
logP	-2	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.51 m³·mol⁻¹	ChemAxon
Polarizability	43.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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 9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one (NP0296646)

MOL for NP0296646 (9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

3D MOL for NP0296646 (9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

3D SDF for NP0296646 (9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

3D-SDF for NP0296646 (9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

PDB for NP0296646 (9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

3D PDB for NP0296646 (9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

SMILES for NP0296646 (9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

INCHI for NP0296646 (9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

Structure for NP0296646 (9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)

3D Structure for NP0296646 (9-hydroxy-8-(2-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8h,9h-furo[2,3-h]chromen-2-one)