NP-MRD: Showing NP-Card for 6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one (NP0291651)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-09 22:49:20 UTC

Updated at

2022-09-09 22:49:20 UTC

NP-MRD ID

NP0291651

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one

Description

6-(2-Hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxy-7H-furo[3,2-g]chromen-7-one belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group. 6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one is found in Dorstenia foetida and Dorstenia turbinata. 6-(2-Hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxy-7H-furo[3,2-g]chromen-7-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201502232D          

 34 37  0  0  0  0            999 V2000
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2266   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0516   -1.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0681   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7825   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4970   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2115   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9259   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4970   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2115   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7825   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7825   -3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0681   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 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
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 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
  4 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
  3 34  2  0  0  0  0
 30 34  1  0  0  0  0
M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
   -6.1632   -0.6953    2.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4911   -1.2136    1.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3075   -0.4123    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2945   -0.4392   -0.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4992   -1.0882   -1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0284   -0.6825   -2.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2033    0.1585   -2.8558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1498    0.3457   -2.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0133    1.1181   -2.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    1.1381   -1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9571    1.8546   -1.3054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9968    1.8851   -0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9914    2.6087   -0.5251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1032    1.1256    0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953    1.0342    1.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0227    0.0471    1.6852 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5797   -1.2536    1.5850 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1037    0.2475    0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7247   -0.0691   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7508    1.5881    0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1258   -0.6850    1.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2278   -0.6269    0.3409 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3298   -0.0302    1.0412 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2324    0.3517    0.0615 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4188    1.0649    0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3293    1.4539   -0.2836 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7590   -0.7594   -0.7820 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4436   -0.2048   -1.8542 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6267   -1.6299   -1.3478 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8665   -0.8088   -2.1441 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7725   -1.9574   -0.1119 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8465   -2.9363   -0.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2544    0.3227    0.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1802    0.3600   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4901    0.3454    2.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0667   -1.3464    2.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4940   -0.7070    3.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9171   -1.7801   -0.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9648   -0.9870   -2.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8878    1.7270   -3.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124    2.0737    2.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    0.8098    2.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838   -0.0444    2.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2162   -1.3142    0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3208   -0.9014   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401    0.8261   -1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3289   -0.3965   -0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0935    2.4079    1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7131    1.5690    1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0620    1.8919   -0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1001    0.0937   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7351    1.0999   -0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9546    0.4329    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0437    1.9599    1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2592    2.3890   -0.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4444   -1.4069   -0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4325   -0.3547   -1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0282   -2.5197   -1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9082   -1.0006   -3.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5388   -2.2928    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0149   -3.4916   -1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4138   -0.2946    1.7620 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 34  2  0
 34 33  1  0
 33 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 34  3  1  0
 31 22  1  0
  8  4  1  0
 11 10  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  0
  6 39  1  0
  9 40  1  0
 33 62  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  1
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  6
 24 52  1  6
 25 53  1  0
 25 54  1  0
 26 55  1  0
 27 56  1  1
 28 57  1  0
 29 58  1  6
 30 59  1  0
 31 60  1  1
 32 61  1  0
M  END


  Mrv1533004201502232D          

 34 37  0  0  0  0            999 V2000
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2266   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0516   -1.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0681   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7825   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4970   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2115   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9259   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4970   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2115   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7825   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7825   -3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0681   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 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
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 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
  4 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
  3 34  2  0  0  0  0
 30 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291651

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=COC2=CC2=C1C=C(CC(O)C(C)(C)OC1OC(CO)C(O)C(O)C1O)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O11/c1-23(2,34-22-19(28)18(27)17(26)15(9-24)33-22)16(25)7-10-6-12-14(32-21(10)29)8-13-11(4-5-31-13)20(12)30-3/h4-6,8,15-19,22,24-28H,7,9H2,1-3H3

> <INCHI_KEY>
WDDNGOYKRPGWQA-UHFFFAOYSA-N

> <FORMULA>
C23H28O11

> <MOLECULAR_WEIGHT>
480.466

> <EXACT_MASS>
480.163161722

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.9438197952386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.39

> <JCHEM_LOGP>
-0.5157666066666663

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.131400576834505

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.201512766735704

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8113178532340846

> <JCHEM_POLAR_SURFACE_AREA>
168.27999999999997

> <JCHEM_REFRACTIVITY>
115.17250000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.592  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.926  -2.843   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.926  -4.383   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.260  -2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.490  -0.739   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.030  -3.407   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      15.593  -1.303   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      16.927  -2.073   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      18.261  -1.303   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      19.594  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.928  -1.303   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      22.262  -2.073   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      19.594  -3.613   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      20.928  -4.383   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      18.261  -4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      18.261  -5.923   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      16.927  -3.613   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      15.593  -4.383   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.592  -5.153   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.925  -5.153   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.459  -4.859   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25    6   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27    4   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    3   30                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈O₁₁

Average Mass

480.4660 Da

Monoisotopic Mass

480.16316 Da

IUPAC Name

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

Traditional Name

6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

COC1=C2C=COC2=CC2=C1C=C(CC(O)C(C)(C)OC1OC(CO)C(O)C(O)C1O)C(=O)O2

InChI Identifier

InChI=1S/C23H28O11/c1-23(2,34-22-19(28)18(27)17(26)15(9-24)33-22)16(25)7-10-6-12-14(32-21(10)29)8-13-11(4-5-31-13)20(12)30-3/h4-6,8,15-19,22,24-28H,7,9H2,1-3H3

InChI Key

WDDNGOYKRPGWQA-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
Dorstenia foetida	LOTUS Database	35616633
Dorstenia turbinata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

5-methoxypsoralens

Alternative Parents

Substituents

5-methoxypsoralen
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Benzofuran
Anisole
Pyranone
Alkyl aryl ether
Pyran
Benzenoid
Oxane
Fatty acyl
Monosaccharide
Heteroaromatic compound
Furan
Secondary alcohol
Lactone
Oxacycle
Polyol
Acetal
Ether
Organoheterocyclic compound
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
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	0.39	ALOGPS
logP	-0.52	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.8	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	115.17 m³·mol⁻¹	ChemAxon
Polarizability	47.94 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

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

73242141

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one (NP0291651)

MOL for NP0291651 (6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one)

3D MOL for NP0291651 (6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one)

3D SDF for NP0291651 (6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one)

3D-SDF for NP0291651 (6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one)

PDB for NP0291651 (6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one)

3D PDB for NP0291651 (6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one)

SMILES for NP0291651 (6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one)

INCHI for NP0291651 (6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one)

Structure for NP0291651 (6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one)

3D Structure for NP0291651 (6-(2-hydroxy-3-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-4-methoxyfuro[3,2-g]chromen-7-one)