NP-MRD: Showing NP-Card for (+)-Heraclenol 3'-O-beta-D-glucopyranoside (NP0075412)

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Record Information

Version

2.0

Created at

2022-04-28 20:41:55 UTC

Updated at

2022-04-28 20:41:55 UTC

NP-MRD ID

NP0075412

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Heraclenol 3'-O-beta-D-glucopyranoside

Description

Heraclenol 3'-O-beta-D-glucopyranoside belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. (+)-Heraclenol 3'-O-beta-D-glucopyranoside is found in Angelica archangelica and Prangos pabularia . (+)-Heraclenol 3'-O-beta-D-glucopyranoside was first documented in 2018 (PMID: 29224384). Based on a literature review very few articles have been published on Heraclenol 3'-O-beta-D-glucopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222422D          

 33 36  0  0  1  0            999 V2000
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -4.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7878   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023   -5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023   -6.4729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7878   -6.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878   -7.7104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5023   -8.1229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2168   -7.7104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2168   -6.8854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9312   -6.4729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9312   -8.1229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023   -8.9479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -8.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -8.9479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -5.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2003   -4.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  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
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  6  0  0  0
 15 20  1  1  0  0  0
 14 21  1  6  0  0  0
 21 22  1  0  0  0  0
 10 23  1  0  0  0  0
 10 24  1  0  0  0  0
  9 25  1  1  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
  4 28  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  2  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
  1 33  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    0.7842   -0.4103    2.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6722   -1.1602    1.6700 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2034   -2.5727    2.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827   -1.3713    0.9452 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5282   -0.3474    0.4931 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5287   -0.4046   -0.9028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9398    0.7898   -1.4396 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2597    0.6392   -2.9120 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2666   -0.2794   -3.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1107    1.4210   -0.7597 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7489    2.4914    0.0581 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8863    0.3821   -0.0021 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6471   -0.3511   -0.9072 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0146   -0.4990    0.8637 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2547   -0.1953    2.1765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3798   -0.5166    0.7973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5514   -0.2483    1.5508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7712   -1.3886   -0.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871   -0.8330   -1.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9509   -0.3853   -1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0720   -1.2094   -1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1594   -2.4673   -1.3995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3973   -2.8955   -1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1909   -1.8248   -1.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3530   -0.7518   -0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5619    0.5797   -0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4677    1.4264   -0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7027    2.7517   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320    3.6147   -0.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3715    3.0916   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3878    3.8928   -0.2153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167    1.8302   -0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1801    0.9491   -0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1276   -0.8076    3.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7753   -0.2970    3.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3839    0.6355    2.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7452   -2.5390    2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9785   -2.9021    2.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -3.2675    1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727    0.6676    0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619    1.4923   -1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5685    1.6100   -3.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3290    0.3475   -3.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7907    0.0121   -3.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8220    1.8524   -1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6309    3.3269   -0.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6323    0.9472    0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0204   -1.1367   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2715   -1.5594    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865   -1.0000    2.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638    0.4621    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050   -0.6195    2.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312   -1.6699   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1996   -2.3604   -0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7816   -3.8904   -1.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2733   -1.7708   -0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5804    0.9290   -0.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7181    3.1281    0.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7594    4.6619    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  6
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 33  2  0
 33 32  1  0
 32 30  1  0
 30 31  2  0
 30 29  1  0
 29 28  2  0
 28 27  1  0
 27 26  2  0
 26 25  1  0
 25 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 14  5  1  0
 21 20  1  0
 27 33  1  0
 24 25  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  5 40  1  6
  7 41  1  6
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  6
 11 46  1  0
 12 47  1  1
 13 48  1  0
 14 49  1  1
 15 50  1  0
 16 51  1  6
 17 52  1  0
 18 53  1  0
 18 54  1  0
 29 59  1  0
 28 58  1  0
 26 57  1  0
 23 55  1  0
 24 56  1  0
M  END


  Mrv1652304282222422D          

 33 36  0  0  1  0            999 V2000
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -4.8229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7878   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023   -5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023   -6.4729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7878   -6.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878   -7.7104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5023   -8.1229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2168   -7.7104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2168   -6.8854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9312   -6.4729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9312   -8.1229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023   -8.9479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -8.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734   -8.9479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -5.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2003   -4.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3429   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  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
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  6  0  0  0
 15 20  1  1  0  0  0
 14 21  1  6  0  0  0
 21 22  1  0  0  0  0
 10 23  1  0  0  0  0
 10 24  1  0  0  0  0
  9 25  1  1  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
  4 28  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  2  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
  1 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075412

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O11/c1-22(2,33-21-17(28)16(27)15(26)12(8-23)31-21)13(24)9-30-20-18-11(5-6-29-18)7-10-3-4-14(25)32-19(10)20/h3-7,12-13,15-17,21,23-24,26-28H,8-9H2,1-2H3/t12-,13-,15-,16+,17-,21+/m1/s1

> <INCHI_KEY>
CDKAMOZNCWECGP-DOKKCILGSA-N

> <FORMULA>
C22H26O11

> <MOLECULAR_WEIGHT>
466.439

> <EXACT_MASS>
466.147511657

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.35780511915891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-[(2R)-2-hydroxy-3-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butoxy]-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
0.15

> <JCHEM_LOGP>
-0.6093091563333333

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.949454731466059

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.169576270276833

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9005548370158083

> <JCHEM_POLAR_SURFACE_AREA>
168.28

> <JCHEM_REFRACTIVITY>
110.578

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-[(2R)-2-hydroxy-3-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butoxy]furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.137  -2.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.137  -4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.197  -6.693   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.137  -7.463   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.137  -9.003   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.471  -9.773   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.804 -10.543   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.804 -12.083   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.471 -12.853   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.471 -14.393   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.804 -15.163   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.138 -14.393   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.138 -12.853   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.472 -12.083   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.472 -15.163   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.804 -16.703   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.137 -15.163   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.137 -16.703   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.701 -11.107   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.241  -8.439   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.197  -9.773   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.602  -4.859   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.507  -3.613   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.602  -2.367   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.531  -5.153   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.864  -5.153   0.000  0.00  0.00           O+0
CONECT    1    2    6   33                                                  
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   28                                                  
CONECT    5    4    6   26                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11   23   24                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21   14   22                                                       
CONECT   22   21                                                            
CONECT   23   10                                                            
CONECT   24   10                                                            
CONECT   25    9                                                            
CONECT   26    5   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    4                                                       
CONECT   29    2   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    1                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
Heraclenol 3'-O-b-D-glucopyranoside	Generator
Heraclenol 3'-O-β-D-glucopyranoside	Generator

Chemical Formula

C₂₂H₂₆O₁₁

Average Mass

466.4390 Da

Monoisotopic Mass

466.14751 Da

IUPAC Name

9-[(2R)-2-hydroxy-3-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butoxy]-7H-furo[3,2-g]chromen-7-one

Traditional Name

9-[(2R)-2-hydroxy-3-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butoxy]furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC(C)(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C2

InChI Identifier

InChI=1S/C22H26O11/c1-22(2,33-21-17(28)16(27)15(26)12(8-23)31-21)13(24)9-30-20-18-11(5-6-29-18)7-10-3-4-14(25)32-19(10)20/h3-7,12-13,15-17,21,23-24,26-28H,8-9H2,1-2H3/t12-,13-,15-,16+,17-,21+/m1/s1

InChI Key

CDKAMOZNCWECGP-DOKKCILGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Angelica archangelica	LOTUS Database	35616633
Prangos pabularia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Benzofuran
Alkyl aryl ether
Pyranone
Monosaccharide
Oxane
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Secondary alcohol
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organic oxygen 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	0.15	ALOGPS
logP	-0.61	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	168.28 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	110.58 m³·mol⁻¹	ChemAxon
Polarizability	45.36 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037263

Chemspider ID

10180980

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21573687

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Numonov S, Bobakulov K, Numonova M, Sharopov F, Setzer WN, Khalilov Q, Begmatov N, Habasi M, Aisa HA: New coumarin from the roots of Prangos pabularia. Nat Prod Res. 2018 Oct;32(19):2325-2332. doi: 10.1080/14786419.2017.1413558. Epub 2017 Dec 11. [PubMed:29224384 ]

Showing NP-Card for (+)-Heraclenol 3'-O-beta-D-glucopyranoside (NP0075412)

MOL for NP0075412 ((+)-Heraclenol 3'-O-beta-D-glucopyranoside)

3D MOL for NP0075412 ((+)-Heraclenol 3'-O-beta-D-glucopyranoside)

3D SDF for NP0075412 ((+)-Heraclenol 3'-O-beta-D-glucopyranoside)

3D-SDF for NP0075412 ((+)-Heraclenol 3'-O-beta-D-glucopyranoside)

PDB for NP0075412 ((+)-Heraclenol 3'-O-beta-D-glucopyranoside)

3D PDB for NP0075412 ((+)-Heraclenol 3'-O-beta-D-glucopyranoside)

SMILES for NP0075412 ((+)-Heraclenol 3'-O-beta-D-glucopyranoside)

INCHI for NP0075412 ((+)-Heraclenol 3'-O-beta-D-glucopyranoside)

Structure for NP0075412 ((+)-Heraclenol 3'-O-beta-D-glucopyranoside)

3D Structure for NP0075412 ((+)-Heraclenol 3'-O-beta-D-glucopyranoside)