NP-MRD: Showing NP-Card for psoralenoside (NP0029546)

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Record Information

Version

2.0

Created at

2021-06-19 21:08:33 UTC

Updated at

2021-06-29 23:56:58 UTC

NP-MRD ID

NP0029546

Secondary Accession Numbers

None

Natural Product Identification

Common Name

psoralenoside

Provided By

JEOL Database JEOL Logo

Description

psoralenoside is found in Psoralea corylifolia and Ficus carica . psoralenoside was first documented in 2006 (Qlao, C.-F., et al.). Based on a literature review very few articles have been published on (2Z)-3-(6-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-5-yl)prop-2-enoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123083D          

 44 46  0  0  0  0            999 V2000
    1.1908   -0.6853    0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404   -1.7697    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -2.4320   -0.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425   -2.5343    1.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -2.0562    2.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335   -0.7060    3.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3554   -0.5259    3.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6749    0.7462    4.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7647    1.3119    5.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4455    2.6333    5.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2295    2.9239    4.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628    1.7783    4.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549    1.6468    3.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7396    0.3824    2.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9409    0.1644    2.2976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099    0.9650    1.1109 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6291    0.2627   -0.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7837    1.0153   -1.2536 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1474    0.2024   -2.3918 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2476   -0.0405   -2.1562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    1.2873   -1.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4392    2.1056   -2.6822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8935    1.9910   -0.3171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3076    2.1218   -0.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232    1.2144    0.9700 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1470    1.9678    2.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7004   -1.7836   -1.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -3.5483    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -2.6989    3.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459   -1.3540    3.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6699    0.8161    5.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    3.4558    5.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    2.4864    3.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    1.9269    1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4500    0.2709   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8015    0.3461   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3842    2.3628   -2.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5123    3.0169   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6698    2.4314    0.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1716    0.2641    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9194    1.4576    2.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 25  1  0  0  0  0
 25 23  1  0  0  0  0
 23 21  1  0  0  0  0
  8  7  2  0  0  0  0
 12 13  2  0  0  0  0
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  4  2  1  0  0  0  0
 14 15  1  0  0  0  0
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  2  3  1  0  0  0  0
  2  1  2  0  0  0  0
 18 19  1  0  0  0  0
 16 15  1  0  0  0  0
 16 34  1  1  0  0  0
 21 39  1  6  0  0  0
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 25 43  1  6  0  0  0
 26 44  1  0  0  0  0
 19 36  1  0  0  0  0
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 18 35  1  1  0  0  0
 20 38  1  0  0  0  0
 13 33  1  0  0  0  0
  7 30  1  0  0  0  0
  9 31  1  0  0  0  0
 10 32  1  0  0  0  0
  5 29  1  0  0  0  0
  4 28  1  0  0  0  0
  3 27  1  0  0  0  0
M  END

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    1.1908   -0.6853    0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404   -1.7697    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -2.4320   -0.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425   -2.5343    1.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -2.0562    2.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335   -0.7060    3.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3554   -0.5259    3.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6749    0.7462    4.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7647    1.3119    5.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4455    2.6333    5.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2295    2.9239    4.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628    1.7783    4.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549    1.6468    3.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7396    0.3824    2.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9409    0.1644    2.2976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099    0.9650    1.1109 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6291    0.2627   -0.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7837    1.0153   -1.2536 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1474    0.2024   -2.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2476   -0.0405   -2.1562 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4392    2.1056   -2.6822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8935    1.9910   -0.3171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3076    2.1218   -0.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232    1.2144    0.9700 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1470    1.9678    2.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7004   -1.7836   -1.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -3.5483    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -2.6989    3.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459   -1.3540    3.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6699    0.8161    5.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    3.4558    5.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    2.4864    3.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    1.9269    1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233    1.9546   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -0.7786   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352    0.7204   -3.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8015    0.3461   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9194    1.4576    2.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
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 25 23  1  0
 23 21  1  0
  8  7  2  0
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M  END


  Mrv1652306192123083D          

 44 46  0  0  0  0            999 V2000
    1.1908   -0.6853    0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404   -1.7697    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -2.4320   -0.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425   -2.5343    1.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -2.0562    2.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335   -0.7060    3.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3554   -0.5259    3.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6749    0.7462    4.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7647    1.3119    5.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4455    2.6333    5.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2295    2.9239    4.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628    1.7783    4.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549    1.6468    3.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7396    0.3824    2.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9409    0.1644    2.2976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099    0.9650    1.1109 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.7837    1.0153   -1.2536 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1474    0.2024   -2.3918 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2476   -0.0405   -2.1562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    1.2873   -1.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4392    2.1056   -2.6822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8935    1.9910   -0.3171 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.1470    1.9678    2.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7004   -1.7836   -1.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0459   -1.3540    3.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6699    0.8161    5.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    3.4558    5.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5878    1.9269    1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4500    0.2709   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8015    0.3461   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5123    3.0169   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6698    2.4314    0.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
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 25 23  1  0  0  0  0
 23 21  1  0  0  0  0
  8  7  2  0  0  0  0
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  2  1  2  0  0  0  0
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 18 35  1  1  0  0  0
 20 38  1  0  0  0  0
 13 33  1  0  0  0  0
  7 30  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0029546

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(\[H])C1=C(O[C@@]2([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C([H])=C2OC([H])=C([H])C2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O9/c18-7-12-14(21)15(22)16(23)17(26-12)25-11-6-10-9(3-4-24-10)5-8(11)1-2-13(19)20/h1-6,12,14-18,21-23H,7H2,(H,19,20)/b2-1-/t12-,14-,15+,16-,17-/m0/s1

> <INCHI_KEY>
XRLPSAYLYDMYGX-VJFVWWCPSA-N

> <FORMULA>
C17H18O9

> <MOLECULAR_WEIGHT>
366.322

> <EXACT_MASS>
366.09508216

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
34.8570660040615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-(6-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-5-yl)prop-2-enoic acid

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-0.2764237543333333

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.20011151500884

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.998151171681292

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8498408534376236

> <JCHEM_POLAR_SURFACE_AREA>
149.82

> <JCHEM_REFRACTIVITY>
86.02630000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-(6-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-5-yl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    1.1908   -0.6853    0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404   -1.7697    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -2.4320   -0.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425   -2.5343    1.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -2.0562    2.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335   -0.7060    3.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3554   -0.5259    3.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6749    0.7462    4.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7647    1.3119    5.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4455    2.6333    5.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2295    2.9239    4.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628    1.7783    4.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549    1.6468    3.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7396    0.3824    2.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9409    0.1644    2.2976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099    0.9650    1.1109 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6291    0.2627   -0.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7837    1.0153   -1.2536 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1474    0.2024   -2.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2476   -0.0405   -2.1562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    1.2873   -1.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4392    2.1056   -2.6822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8935    1.9910   -0.3171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3076    2.1218   -0.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232    1.2144    0.9700 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1470    1.9678    2.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7004   -1.7836   -1.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -3.5483    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -2.6989    3.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459   -1.3540    3.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6699    0.8161    5.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    3.4558    5.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    2.4864    3.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    1.9269    1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233    1.9546   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -0.7786   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352    0.7204   -3.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4500    0.2709   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8015    0.3461   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3842    2.3628   -2.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5123    3.0169   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6698    2.4314    0.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1716    0.2641    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9194    1.4576    2.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 25  1  0
 25 23  1  0
 23 21  1  0
  8  7  2  0
 12 13  2  0
 13 14  1  0
 14  6  2  0
  6  7  1  0
 12  8  1  0
 21 18  1  0
 18 17  1  0
 17 16  1  0
 21 22  1  0
 23 24  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 25 26  1  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
 14 15  1  0
 19 20  1  0
  2  3  1  0
  2  1  2  0
 18 19  1  0
 16 15  1  0
 16 34  1  1
 21 39  1  6
 22 40  1  0
 23 41  1  1
 24 42  1  0
 25 43  1  6
 26 44  1  0
 19 36  1  0
 19 37  1  0
 18 35  1  1
 20 38  1  0
 13 33  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
  5 29  1  0
  4 28  1  0
  3 27  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0       1.191  -0.685   0.345  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.640  -1.770   0.303  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.444  -2.432  -0.852  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.043  -2.534   1.409  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.186  -2.056   2.641  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.134  -0.706   3.122  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.355  -0.526   3.799  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.675   0.746   4.306  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.765   1.312   5.018  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.446   2.633   5.232  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.230   2.924   4.700  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.763   1.778   4.130  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.455   1.647   3.468  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.740   0.382   2.932  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.941   0.164   2.298  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.110   0.965   1.111  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.629   0.263  -0.039  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.784   1.015  -1.254  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.147   0.202  -2.392  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.248  -0.041  -2.156  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.268   1.287  -1.525  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.439   2.106  -2.682  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.894   1.991  -0.317  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.308   2.122  -0.533  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.623   1.214   0.970  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.147   1.968   2.076  0.00  0.00           O+0
HETATM   27  H   UNK     0       0.700  -1.784  -1.553  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.255  -3.548   1.164  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.656  -2.699   3.381  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.046  -1.354   3.931  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.670   0.816   5.338  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.949   3.456   5.721  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.133   2.486   3.392  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.588   1.927   1.196  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.223   1.955  -1.155  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.626  -0.779  -2.477  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.235   0.720  -3.351  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.450   0.271  -1.245  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.801   0.346  -1.709  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.384   2.363  -2.680  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.512   3.017  -0.236  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.670   2.431   0.322  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.172   0.264   0.953  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.919   1.458   2.879  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    3    1                                                  
CONECT    3    2   27                                                       
CONECT    4    5    2   28                                                  
CONECT    5    6    4   29                                                  
CONECT    6   14    7    5                                                  
CONECT    7    8    6   30                                                  
CONECT    8    7   12    9                                                  
CONECT    9    8   10   31                                                  
CONECT   10    9   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   13    8   11                                                  
CONECT   13   12   14   33                                                  
CONECT   14   13    6   15                                                  
CONECT   15   14   16                                                       
CONECT   16   25   17   15   34                                             
CONECT   17   18   16                                                       
CONECT   18   21   17   19   35                                             
CONECT   19   20   18   36   37                                             
CONECT   20   19   38                                                       
CONECT   21   23   18   22   39                                             
CONECT   22   21   40                                                       
CONECT   23   25   21   24   41                                             
CONECT   24   23   42                                                       
CONECT   25   16   23   26   43                                             
CONECT   26   25   44                                                       
CONECT   27    3                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    7                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   13                                                            
CONECT   34   16                                                            
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   19                                                            
CONECT   38   20                                                            
CONECT   39   21                                                            
CONECT   40   22                                                            
CONECT   41   23                                                            
CONECT   42   24                                                            
CONECT   43   25                                                            
CONECT   44   26                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

RDKit          3D

44 46  0  0  0  0  0  0  0  0999 V2000
    1.1908   -0.6853    0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404   -1.7697    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -2.4320   -0.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425   -2.5343    1.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -2.0562    2.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335   -0.7060    3.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3554   -0.5259    3.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6749    0.7462    4.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7647    1.3119    5.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4455    2.6333    5.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2295    2.9239    4.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628    1.7783    4.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549    1.6468    3.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7396    0.3824    2.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9409    0.1644    2.2976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099    0.9650    1.1109 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6291    0.2627   -0.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7837    1.0153   -1.2536 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1474    0.2024   -2.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2476   -0.0405   -2.1562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    1.2873   -1.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4392    2.1056   -2.6822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8935    1.9910   -0.3171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3076    2.1218   -0.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232    1.2144    0.9700 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1470    1.9678    2.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7004   -1.7836   -1.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -3.5483    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -2.6989    3.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459   -1.3540    3.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6699    0.8161    5.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    3.4558    5.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    2.4864    3.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    1.9269    1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233    1.9546   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -0.7786   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352    0.7204   -3.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4500    0.2709   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8015    0.3461   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3842    2.3628   -2.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5123    3.0169   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6698    2.4314    0.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1716    0.2641    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9194    1.4576    2.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 25  1  0
 25 23  1  0
 23 21  1  0
  8  7  2  0
 12 13  2  0
 13 14  1  0
 14  6  2  0
  6  7  1  0
 12  8  1  0
 21 18  1  0
 18 17  1  0
 17 16  1  0
 21 22  1  0
 23 24  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 25 26  1  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
 14 15  1  0
 19 20  1  0
  2  3  1  0
  2  1  2  0
 18 19  1  0
 16 15  1  0
 16 34  1  1
 21 39  1  6
 22 40  1  0
 23 41  1  1
 24 42  1  0
 25 43  1  6
 26 44  1  0
 19 36  1  0
 19 37  1  0
 18 35  1  1
 20 38  1  0
 13 33  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
  5 29  1  0
  4 28  1  0
  3 27  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2Z)-3-(6-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-5-yl)prop-2-enoate	Generator

Chemical Formula

C₁₇H₁₈O₉

Average Mass

366.3220 Da

Monoisotopic Mass

366.09508 Da

IUPAC Name

(2Z)-3-(6-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-5-yl)prop-2-enoic acid

Traditional Name

(2Z)-3-(6-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-5-yl)prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(\[H])=C(\[H])C1=C(O[C@@]2([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C([H])=C2OC([H])=C([H])C2=C1[H]

InChI Identifier

InChI=1S/C17H18O9/c18-7-12-14(21)15(22)16(23)17(26-12)25-11-6-10-9(3-4-24-10)5-8(11)1-2-13(19)20/h1-6,12,14-18,21-23H,7H2,(H,19,20)/b2-1-/t12-,14-,15+,16-,17-/m0/s1

InChI Key

XRLPSAYLYDMYGX-VJFVWWCPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cullen corylifolium	JEOL database	Qlao, C.-F., et al, Chem. Pharm. Bull. 54, 714 (2006)
Ficus carica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Coumaric acid
Coumaric acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Benzofuran
Styrene
Monosaccharide
Oxane
Benzenoid
Furan
Heteroaromatic compound
Secondary alcohol
Polyol
Organoheterocyclic compound
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Primary alcohol
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	-0.14	ALOGPS
logP	-0.28	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.03 m³·mol⁻¹	ChemAxon
Polarizability	34.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

82965079

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154831577

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Qlao, C.-F., et al. (2006). Qlao, C.-F., et al, Chem. Pharm. Bull. 54, 714 (2006). Chem. Pharm. Bull..

Showing NP-Card for psoralenoside (NP0029546)

MOL for NP0029546 (psoralenoside)

3D MOL for NP0029546 (psoralenoside)

3D SDF for NP0029546 (psoralenoside)

3D-SDF for NP0029546 (psoralenoside)

PDB for NP0029546 (psoralenoside)

3D PDB for NP0029546 (psoralenoside)

SMILES for NP0029546 (psoralenoside)

INCHI for NP0029546 (psoralenoside)

Structure for NP0029546 (psoralenoside)

3D Structure for NP0029546 (psoralenoside)