NP-MRD: Showing NP-Card for pelargonidin 3,5-diglucoside (NP0233553)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 15:12:06 UTC

Updated at

2022-09-06 15:12:06 UTC

NP-MRD ID

NP0233553

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pelargonidin 3,5-diglucoside

Description

Pelargonin belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. It is the 3,5-O-diglucoside of pelargonidin. Pelargonin is an extremely weak basic (essentially neutral) compound (based on its pKa). Pelargonin is an anthocyanin. pelargonidin 3,5-diglucoside is found in Lathyrus odoratus, Pelargonium dolomiticum and Saraca indica. pelargonidin 3,5-diglucoside was first documented in 2000 (PMID: 10637045). Pelargonin is a pigment, found in barberries, the petals of the scarlet pelargonium flower pomegranates, and red wine (PMID: 16395794) (PMID: 21936496) (PMID: 23132311) (PMID: 23216001).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307072019552D          

 42 46  0  0  0  0            999 V2000
 9998.9219 9999.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.496810000.4078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.496810002.0640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4968 9997.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0676 9999.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.772010000.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7833 9996.6999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0676 9997.9349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3445 9999.5869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1995 9997.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3424 9997.9390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.912310003.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.9102 9998.3520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7720 9997.1150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4954 9999.5846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7809 9999.1721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7809 9998.3470    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.4954 9997.9346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2099 9998.3470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2099 9999.1721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.7716 9999.5880    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0571 9999.1755    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0571 9998.3504    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7716 9997.9380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.4861 9998.3504    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.4861 9999.1755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.921910002.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.207410001.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.207310000.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.921810000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.200610002.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.486210003.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.771610002.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.771610002.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.486110001.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.200610002.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.061910001.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.347510002.0619    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
 9999.632910001.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.632910000.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.347310000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.061910000.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0  0  0  0
 10 13  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 26  1  0  0  0  0
 25 26  1  0  0  0  0
 21  6  1  6  0  0  0
 22  9  1  1  0  0  0
 25 10  1  6  0  0  0
 23 11  1  6  0  0  0
 24 14  1  1  0  0  0
 20  1  1  6  0  0  0
 15  2  1  1  0  0  0
 18  4  1  6  0  0  0
 16  5  1  6  0  0  0
 17  8  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 31  1  0  0  0  0
 31 12  1  0  0  0  0
  1 30  1  0  0  0  0
 28  3  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 42  6  1  0  0  0  0
 37 34  1  0  0  0  0
 39 27  2  0  0  0  0
 30 40  2  0  0  0  0
M  CHG  1  38   1
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
   -6.1676   -3.0459    2.0288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9642   -2.3149    2.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4809   -2.0904    0.6105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2935   -1.3627    0.6861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9233   -0.9392   -0.6325 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0885    0.0505   -0.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000    1.0712   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727    0.7680   -0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9886    1.7718   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3290    1.5067    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6398    0.1893    0.3792 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8946   -0.2907    0.6615 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3295   -1.2853   -0.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7011   -1.3598   -0.2025 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1970   -2.7245   -0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7709   -2.9484   -2.0045 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3255   -1.0276    1.1202 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9312    0.2504    1.0739 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4473   -1.1666    2.3072 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6874   -2.3326    3.0522 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9718   -0.9796    2.0380 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3613   -0.1504    2.9476 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093    2.5542    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8051    3.8724   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7038    4.9204    0.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    4.1194   -0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907    3.0727   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6435    3.3338   -0.6191 O   0  0  0  0  0  3  0  0  0  0  0  0
   -1.6019    2.3814   -0.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414    2.8331   -1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0501    4.0521   -1.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2540    4.6446   -2.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4391    4.0564   -1.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6809    4.5967   -1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3666    2.8674   -0.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1293    2.2672   -0.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621   -2.1701   -1.4166 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2378   -2.2564   -2.5670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7156   -3.3925   -0.5816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7890   -3.4203    0.4617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1096   -3.4142   -0.0360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0582   -3.7606   -0.9759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6465   -2.8563    1.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0306   -1.3884    2.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2011   -2.9581    2.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2357   -1.5442    0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9403   -0.6503   -1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3545   -0.2498   -0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6436    0.4931    0.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0804   -0.6293   -0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3159   -2.7048   -0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8970   -3.5298    0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9939   -3.5771   -1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1941   -1.7269    1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1110    0.4128    0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7242   -0.3298    3.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8657   -2.8868    3.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284   -1.9686    1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9408    0.1154    3.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334    2.3896    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9260    5.4541    0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1046    5.1155   -0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    4.5363   -2.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265    5.5879   -2.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1614    5.2375   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2755    2.3566   -0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1127    1.3801   -0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002   -2.0907   -1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9427   -1.5553   -2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117   -4.3001   -1.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9417   -3.7007    0.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1452   -4.2052    0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5695   -2.9736   -1.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  2  0
  5 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 41  3  1  0
 29  7  1  0
 36 30  1  0
 27  9  1  0
 21 12  1  0
  1 43  1  0
  2 44  1  0
  2 45  1  0
  3 46  1  6
  5 47  1  6
  8 48  1  0
 12 49  1  1
 14 50  1  6
 15 51  1  0
 15 52  1  0
 16 53  1  0
 17 54  1  1
 18 55  1  0
 19 56  1  1
 20 57  1  0
 21 58  1  6
 22 59  1  0
 23 60  1  0
 25 61  1  0
 26 62  1  0
 31 63  1  0
 32 64  1  0
 34 65  1  0
 35 66  1  0
 36 67  1  0
 37 68  1  6
 38 69  1  0
 39 70  1  6
 40 71  1  0
 41 72  1  1
 42 73  1  0
M  CHG  1  28   1
M  END


  Mrv1652307072019552D          

 42 46  0  0  0  0            999 V2000
 9998.9219 9999.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.496810000.4078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.496810002.0640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4968 9997.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0676 9999.5828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.772010000.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7833 9996.6999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0676 9997.9349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3445 9999.5869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1995 9997.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3424 9997.9390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.912310003.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.9102 9998.3520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7720 9997.1150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4954 9999.5846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7809 9999.1721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7809 9998.3470    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.4954 9997.9346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2099 9998.3470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2099 9999.1721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.7716 9999.5880    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0571 9999.1755    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0571 9998.3504    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7716 9997.9380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.4861 9998.3504    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.4861 9999.1755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.921910002.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.207410001.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.207310000.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.921810000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.200610002.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.486210003.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.771610002.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.771610002.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.486110001.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.200610002.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.061910001.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.347510002.0619    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
 9999.632910001.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.632910000.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.347310000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.061910000.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0  0  0  0
 10 13  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 26  1  0  0  0  0
 25 26  1  0  0  0  0
 21  6  1  6  0  0  0
 22  9  1  1  0  0  0
 25 10  1  6  0  0  0
 23 11  1  6  0  0  0
 24 14  1  1  0  0  0
 20  1  1  6  0  0  0
 15  2  1  1  0  0  0
 18  4  1  6  0  0  0
 16  5  1  6  0  0  0
 17  8  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 31  1  0  0  0  0
 31 12  1  0  0  0  0
  1 30  1  0  0  0  0
 28  3  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 42  6  1  0  0  0  0
 37 34  1  0  0  0  0
 39 27  2  0  0  0  0
 30 40  2  0  0  0  0
M  CHG  1  38   1
M  END
> <DATABASE_ID>
NP0233553

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O15/c28-8-17-19(32)21(34)23(36)26(41-17)39-15-6-12(31)5-14-13(15)7-16(25(38-14)10-1-3-11(30)4-2-10)40-27-24(37)22(35)20(33)18(9-29)42-27/h1-7,17-24,26-29,32-37H,8-9H2,(H-,30,31)/p+1/t17-,18-,19-,20-,21+,22+,23-,24-,26-,27-/m1/s1

> <INCHI_KEY>
SLCKJKWFULXZBD-ZOTFFYTFSA-O

> <FORMULA>
C27H31O15

> <MOLECULAR_WEIGHT>
595.529

> <EXACT_MASS>
595.165746718

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
57.27706591405306

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-hydroxy-2-(4-hydroxyphenyl)-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
-1.9919000000000002

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.369900666728402

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.660003787521519

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483953504161706

> <JCHEM_POLAR_SURFACE_AREA>
252.35999999999996

> <JCHEM_REFRACTIVITY>
146.421

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-2-(4-hydroxyphenyl)-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUL-20         0                                  
HETATM    1  O   UNK     0    8664.6548665.888   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8661.9948667.428   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8661.9948670.519   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8661.9948661.274   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8659.3268665.888   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8669.9748667.436   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8660.6628660.506   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8659.3268662.812   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8667.3108665.896   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8672.6398662.819   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8667.3068662.819   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8673.9708672.827   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8673.9668663.590   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8669.9748661.281   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8661.9918665.891   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.6588665.121   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8660.6588663.581   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8661.9918662.811   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8663.3258663.581   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8663.3258665.121   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.9748665.898   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.6408665.128   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.6408663.587   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8669.9748662.818   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8671.3078663.587   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0    8671.3078665.128   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0    8664.6548670.516   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8663.3208669.746   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8663.3208668.206   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8664.6548667.436   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8672.6418672.059   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8671.3088672.829   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8669.9748672.058   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8669.9748670.519   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8671.3078669.749   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8672.6418670.519   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8668.6498669.746   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0    8667.3158670.516   0.000  0.00  0.00           O+1
HETATM   39  C   UNK     0    8665.9818669.746   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0    8665.9818668.206   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0    8667.3158667.436   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0    8668.6498668.206   0.000  0.00  0.00           C+0
CONECT    1   20   30                                                       
CONECT    2   15                                                            
CONECT    3   28                                                            
CONECT    4    7   18                                                       
CONECT    5   16                                                            
CONECT    6   21   42                                                       
CONECT    7    4                                                            
CONECT    8   17                                                            
CONECT    9   22                                                            
CONECT   10   13   25                                                       
CONECT   11   23                                                            
CONECT   12   31                                                            
CONECT   13   10                                                            
CONECT   14   24                                                            
CONECT   15   16   20    2                                                  
CONECT   16   15   17    5                                                  
CONECT   17   16   18    8                                                  
CONECT   18   17   19    4                                                  
CONECT   19   18   20                                                       
CONECT   20   15   19    1                                                  
CONECT   21   22   26    6                                                  
CONECT   22   21   23    9                                                  
CONECT   23   22   24   11                                                  
CONECT   24   23   25   14                                                  
CONECT   25   24   26   10                                                  
CONECT   26   21   25                                                       
CONECT   27   28   39                                                       
CONECT   28   27   29    3                                                  
CONECT   29   28   30                                                       
CONECT   30   29    1   40                                                  
CONECT   31   32   36   12                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   42   38   34                                                  
CONECT   38   37   39                                                       
CONECT   39   40   38   27                                                  
CONECT   40   39   41   30                                                  
CONECT   41   40   42                                                       
CONECT   42   41   37    6                                                  
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
Pelargonidin 3,5-di-beta-D-glucopyranoside	ChEBI
Pelargonidin 3,5-di-beta-D-glucoside	ChEBI
Pelargonidin 3,5-di-O-beta-D-glucoside	ChEBI
Pelargonidin 3,5-di-O-beta-glucoside	ChEBI
Pelargonidin 3,5-diglucoside	ChEBI
Pelargonidin 3,5-O-diglucoside	ChEBI
Pelargonidin 3,5-di-b-D-glucopyranoside	Generator
Pelargonidin 3,5-di-β-D-glucopyranoside	Generator
Pelargonidin 3,5-di-b-D-glucoside	Generator
Pelargonidin 3,5-di-β-D-glucoside	Generator
Pelargonidin 3,5-di-O-b-D-glucoside	Generator
Pelargonidin 3,5-di-O-β-D-glucoside	Generator
Pelargonidin 3,5-di-O-b-glucoside	Generator
Pelargonidin 3,5-di-O-β-glucoside	Generator
3,5-Bis(beta-D-glucopyranosyloxy)-7-hydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium	HMDB
3,5-Bis(β-D-glucopyranosyloxy)-7-hydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium	HMDB
Pelargonidin 3,5-di-O-glucoside	HMDB
Pelargonidin 3-O-glucoside-5-O-glucoside	HMDB
Pelargonidin-3,5-di-O-diglucoside	HMDB
Pelargonin	HMDB
Pelargonin (glycoside)	HMDB
Pelargonin chloride	HMDB

Chemical Formula

C₂₇H₃₁O₁₅

Average Mass

595.5290 Da

Monoisotopic Mass

595.16575 Da

IUPAC Name

7-hydroxy-2-(4-hydroxyphenyl)-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1lambda4-chromen-1-ylium

Traditional Name

7-hydroxy-2-(4-hydroxyphenyl)-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1lambda4-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H30O15/c28-8-17-19(32)21(34)23(36)26(41-17)39-15-6-12(31)5-14-13(15)7-16(25(38-14)10-1-3-11(30)4-2-10)40-27-24(37)22(35)20(33)18(9-29)42-27/h1-7,17-24,26-29,32-37H,8-9H2,(H-,30,31)/p+1/t17-,18-,19-,20-,21+,22+,23-,24-,26-,27-/m1/s1

InChI Key

SLCKJKWFULXZBD-ZOTFFYTFSA-O

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
Lathyrus odoratus	LOTUS Database	35616633
Pelargonium dolomiticum	LOTUS Database	35616633
Saraca indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-5-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Anthocyanidin-5-o-glycoside
Flavonoid-3-o-glycoside
4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin glycoside (CHEBI:7951 )
Anthocyanidins (C08725 )
Anthocyanidins and anthocyanins (C08725 )

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	-0.03	ALOGPS
logP	-2	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.66	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	252.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.42 m³·mol⁻¹	ChemAxon
Polarizability	57.28 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0033681

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Pelargonin

METLIN ID

Not Available

PubChem Compound

441772

PDB ID

Not Available

ChEBI ID

133365

Good Scents ID

Not Available

References

General References

Gonnet JF, Fenet B: "Cyclamen Red" colors based on a macrocyclic anthocyanin in carnation flowers. J Agric Food Chem. 2000 Jan;48(1):22-6. doi: 10.1021/jf9907642. [PubMed:10637045 ]
Tian Q, Giusti MM, Stoner GD, Schwartz SJ: Screening for anthocyanins using high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry with precursor-ion analysis, product-ion analysis, common-neutral-loss analysis, and selected reaction monitoring. J Chromatogr A. 2005 Oct 14;1091(1-2):72-82. doi: 10.1016/j.chroma.2005.07.036. [PubMed:16395794 ]
Karasawa K, Uzuhashi Y, Hirota M, Otani H: A matured fruit extract of date palm tree (Phoenix dactylifera L.) stimulates the cellular immune system in mice. J Agric Food Chem. 2011 Oct 26;59(20):11287-93. doi: 10.1021/jf2029225. Epub 2011 Oct 3. [PubMed:21936496 ]
Karasawa K, Otani H: Anti-allergic properties of a matured fruit extract of the date palm tree (Phoenix dactylifera L.) in mite-sensitized mice. J Nutr Sci Vitaminol (Tokyo). 2012;58(4):272-7. doi: 10.3177/jnsv.58.272. [PubMed:23132311 ]
Deng GF, Xu XR, Zhang Y, Li D, Gan RY, Li HB: Phenolic compounds and bioactivities of pigmented rice. Crit Rev Food Sci Nutr. 2013;53(3):296-306. doi: 10.1080/10408398.2010.529624. [PubMed:23216001 ]
LOTUS database [Link]

Showing NP-Card for pelargonidin 3,5-diglucoside (NP0233553)

MOL for NP0233553 (pelargonidin 3,5-diglucoside)

3D MOL for NP0233553 (pelargonidin 3,5-diglucoside)

3D SDF for NP0233553 (pelargonidin 3,5-diglucoside)

3D-SDF for NP0233553 (pelargonidin 3,5-diglucoside)

PDB for NP0233553 (pelargonidin 3,5-diglucoside)

3D PDB for NP0233553 (pelargonidin 3,5-diglucoside)

SMILES for NP0233553 (pelargonidin 3,5-diglucoside)

INCHI for NP0233553 (pelargonidin 3,5-diglucoside)

Structure for NP0233553 (pelargonidin 3,5-diglucoside)

3D Structure for NP0233553 (pelargonidin 3,5-diglucoside)