NP-MRD: Showing NP-Card for 1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde (NP0007705)

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Record Information

Version

2.0

Created at

2020-12-09 04:30:53 UTC

Updated at

2021-07-15 16:58:18 UTC

NP-MRD ID

NP0007705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde

Provided By

NPAtlas

Description

1-(1-B-Glucopyranosyl)-1H-indole-3-carbaldehyde belongs to the class of organic compounds known as 1-pyranosylindoles. These are nucleoside and nucleotide analogs with a structure that consists of an indole base which is N-substituted at the 1-position with a pyranose moiety. Nucleotide analogues contain a phosphate group linked to the C5 carbon atom of the pyranose. 1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde is found in Cortinarius brunneus. Based on a literature review very few articles have been published on 1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119023D          

 39 41  0  0  0  0            999 V2000
   -5.0535   -0.9017   -2.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8265   -1.1273   -2.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292   -0.6575   -1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -0.8097   -1.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9003   -0.2231   -0.3494 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5212   -0.1497    0.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1853    0.3446   -1.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637    0.6966   -0.7272 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4153    2.1082   -0.1479 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7123    2.5192    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1779   -0.2550    0.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4834   -0.4609   -0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5327   -1.6063    0.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9575   -2.1594    1.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0298   -1.5541    0.2657 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5111   -2.4235   -0.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    0.3249    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9398    1.0672    1.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213    1.5291    2.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266    1.2758    1.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3107    0.5505    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245    0.0883   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096   -1.7002   -3.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -1.3566   -2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444    0.4120    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0359    0.8138   -1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    2.8441   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7998    2.0804    0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5495    3.3521    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754    0.2125    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5499   -1.2338   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8718   -2.2997   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3702   -1.4813    2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6093   -1.8775    1.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9864   -3.2925   -0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9693    1.2466    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    2.0933    2.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2234    1.6631    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2455    0.3476   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22  3  1  0  0  0  0
 15  6  1  0  0  0  0
 22 17  1  0  0  0  0
  2 23  1  0  0  0  0
  4 24  1  0  0  0  0
  6 25  1  1  0  0  0
  8 26  1  6  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  1  0  0  0
 12 31  1  0  0  0  0
 13 32  1  6  0  0  0
 14 33  1  0  0  0  0
 15 34  1  1  0  0  0
 16 35  1  0  0  0  0
 18 36  1  0  0  0  0
 19 37  1  0  0  0  0
 20 38  1  0  0  0  0
 21 39  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.0535   -0.9017   -2.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8265   -1.1273   -2.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292   -0.6575   -1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -0.8097   -1.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9003   -0.2231   -0.3494 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5212   -0.1497    0.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1853    0.3446   -1.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637    0.6966   -0.7272 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4153    2.1082   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7123    2.5192    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1779   -0.2550    0.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4834   -0.4609   -0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5327   -1.6063    0.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9575   -2.1594    1.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0298   -1.5541    0.2657 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5111   -2.4235   -0.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    0.3249    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9398    1.0672    1.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213    1.5291    2.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266    1.2758    1.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3107    0.5505    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245    0.0883   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096   -1.7002   -3.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -1.3566   -2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444    0.4120    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0359    0.8138   -1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    2.8441   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7998    2.0804    0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5495    3.3521    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754    0.2125    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5499   -1.2338   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8718   -2.2997   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3702   -1.4813    2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6093   -1.8775    1.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9864   -3.2925   -0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9693    1.2466    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    2.0933    2.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2234    1.6631    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2455    0.3476   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 15  6  1  0
 22 17  1  0
  2 23  1  0
  4 24  1  0
  6 25  1  1
  8 26  1  6
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 13 32  1  6
 14 33  1  0
 15 34  1  1
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
M  END


  Mrv1652306242119023D          

 39 41  0  0  0  0            999 V2000
   -5.0535   -0.9017   -2.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8265   -1.1273   -2.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292   -0.6575   -1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -0.8097   -1.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9003   -0.2231   -0.3494 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5212   -0.1497    0.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1853    0.3446   -1.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637    0.6966   -0.7272 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4153    2.1082   -0.1479 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7123    2.5192    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1779   -0.2550    0.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4834   -0.4609   -0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5327   -1.6063    0.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9575   -2.1594    1.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0298   -1.5541    0.2657 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5111   -2.4235   -0.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    0.3249    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9398    1.0672    1.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213    1.5291    2.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266    1.2758    1.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3107    0.5505    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245    0.0883   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096   -1.7002   -3.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -1.3566   -2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444    0.4120    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0359    0.8138   -1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    2.8441   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7998    2.0804    0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5495    3.3521    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754    0.2125    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5499   -1.2338   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8718   -2.2997   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3702   -1.4813    2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6093   -1.8775    1.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9864   -3.2925   -0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9693    1.2466    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    2.0933    2.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2234    1.6631    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2455    0.3476   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22  3  1  0  0  0  0
 15  6  1  0  0  0  0
 22 17  1  0  0  0  0
  2 23  1  0  0  0  0
  4 24  1  0  0  0  0
  6 25  1  1  0  0  0
  8 26  1  6  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  1  0  0  0
 12 31  1  0  0  0  0
 13 32  1  6  0  0  0
 14 33  1  0  0  0  0
 15 34  1  1  0  0  0
 16 35  1  0  0  0  0
 18 36  1  0  0  0  0
 19 37  1  0  0  0  0
 20 38  1  0  0  0  0
 21 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007705

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]1([H])O[C@@]([H])(N2C([H])=C(C([H])=O)C3=C([H])C([H])=C([H])C([H])=C23)[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H17NO6/c17-6-8-5-16(10-4-2-1-3-9(8)10)15-14(21)13(20)12(19)11(7-18)22-15/h1-6,11-15,18-21H,7H2/t11-,12-,13+,14-,15+/m0/s1

> <INCHI_KEY>
WJFHBZYDHHWPRW-UHFFFAOYSA-N

> <FORMULA>
C15H17NO6

> <MOLECULAR_WEIGHT>
307.302

> <EXACT_MASS>
307.105587271

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.566062087463227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indole-3-carbaldehyde

> <ALOGPS_LOGP>
0.00

> <JCHEM_LOGP>
-0.4057759299999995

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.273553678136174

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.360470994273278

> <JCHEM_PKA_STRONGEST_BASIC>
-2.980496995625175

> <JCHEM_POLAR_SURFACE_AREA>
112.15

> <JCHEM_REFRACTIVITY>
76.28729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indole-3-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.0535   -0.9017   -2.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8265   -1.1273   -2.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292   -0.6575   -1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -0.8097   -1.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9003   -0.2231   -0.3494 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5212   -0.1497    0.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1853    0.3446   -1.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637    0.6966   -0.7272 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4153    2.1082   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7123    2.5192    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1779   -0.2550    0.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4834   -0.4609   -0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5327   -1.6063    0.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9575   -2.1594    1.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0298   -1.5541    0.2657 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5111   -2.4235   -0.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    0.3249    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9398    1.0672    1.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213    1.5291    2.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266    1.2758    1.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3107    0.5505    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245    0.0883   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096   -1.7002   -3.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -1.3566   -2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444    0.4120    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0359    0.8138   -1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    2.8441   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7998    2.0804    0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5495    3.3521    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754    0.2125    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5499   -1.2338   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8718   -2.2997   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3702   -1.4813    2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6093   -1.8775    1.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9864   -3.2925   -0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9693    1.2466    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    2.0933    2.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2234    1.6631    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2455    0.3476   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 15  6  1  0
 22 17  1  0
  2 23  1  0
  4 24  1  0
  6 25  1  1
  8 26  1  6
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 13 32  1  6
 14 33  1  0
 15 34  1  1
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -5.053  -0.902  -2.171  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.826  -1.127  -2.318  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.829  -0.658  -1.387  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.463  -0.810  -1.391  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.900  -0.223  -0.349  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.521  -0.150   0.019  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.185   0.345  -1.079  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.464   0.697  -0.727  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.415   2.108  -0.148  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.712   2.519   0.232  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.178  -0.255   0.162  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.483  -0.461  -0.286  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.533  -1.606   0.283  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.958  -2.159   1.496  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.030  -1.554   0.266  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.511  -2.424  -0.694  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.904   0.325   0.355  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.940   1.067   1.542  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.121   1.529   2.077  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.327   1.276   1.457  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.311   0.551   0.294  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.124   0.088  -0.240  0.00  0.00           C+0
HETATM   23  H   UNK     0      -3.510  -1.700  -3.183  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.947  -1.357  -2.180  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.644   0.412   0.941  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.036   0.814  -1.696  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.093   2.844  -0.912  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.800   2.080   0.751  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.550   3.352   0.777  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.275   0.213   1.182  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.550  -1.234  -0.901  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.872  -2.300  -0.516  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.370  -1.481   2.090  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.609  -1.878   1.242  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.986  -3.293  -0.641  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.969   1.247   2.001  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.081   2.093   2.991  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.223   1.663   1.922  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.245   0.348  -0.196  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   24                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    7   15   25                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   11   26                                             
CONECT    9    8   10   27   28                                             
CONECT   10    9   29                                                       
CONECT   11    8   12   13   30                                             
CONECT   12   11   31                                                       
CONECT   13   11   14   15   32                                             
CONECT   14   13   33                                                       
CONECT   15   13   16    6   34                                             
CONECT   16   15   35                                                       
CONECT   17    5   18   22                                                  
CONECT   18   17   19   36                                                  
CONECT   19   18   20   37                                                  
CONECT   20   19   21   38                                                  
CONECT   21   20   22   39                                                  
CONECT   22   21    3   17                                                  
CONECT   23    2                                                            
CONECT   24    4                                                            
CONECT   25    6                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   18                                                            
CONECT   37   19                                                            
CONECT   38   20                                                            
CONECT   39   21                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
   -5.0535   -0.9017   -2.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8265   -1.1273   -2.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292   -0.6575   -1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -0.8097   -1.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9003   -0.2231   -0.3494 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5212   -0.1497    0.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1853    0.3446   -1.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637    0.6966   -0.7272 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4153    2.1082   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7123    2.5192    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1779   -0.2550    0.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4834   -0.4609   -0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5327   -1.6063    0.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9575   -2.1594    1.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0298   -1.5541    0.2657 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5111   -2.4235   -0.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    0.3249    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9398    1.0672    1.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213    1.5291    2.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266    1.2758    1.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3107    0.5505    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1245    0.0883   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096   -1.7002   -3.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -1.3566   -2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444    0.4120    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0359    0.8138   -1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    2.8441   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7998    2.0804    0.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5495    3.3521    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754    0.2125    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5499   -1.2338   -0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8718   -2.2997   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3702   -1.4813    2.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6093   -1.8775    1.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9864   -3.2925   -0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9693    1.2466    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    2.0933    2.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2234    1.6631    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2455    0.3476   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 15  6  1  0
 22 17  1  0
  2 23  1  0
  4 24  1  0
  6 25  1  1
  8 26  1  6
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 13 32  1  6
 14 33  1  0
 15 34  1  1
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₅H₁₇NO₆

Average Mass

307.3020 Da

Monoisotopic Mass

307.10559 Da

IUPAC Name

1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indole-3-carbaldehyde

Traditional Name

1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indole-3-carbaldehyde

CAS Registry Number

Not Available

SMILES

OCC1OC(C(O)C(O)C1O)N1C=C(C=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C15H17NO6/c17-6-8-5-16(10-4-2-1-3-9(8)10)15-14(21)13(20)12(19)11(7-18)22-15/h1-6,11-15,18-21H,7H2

InChI Key

WJFHBZYDHHWPRW-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cortinarius brunneus	NPAtlas	18421759

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-pyranosylindoles. These are nucleoside and nucleotide analogs with a structure that consists of an indole base which is N-substituted at the 1-position with a pyranose moiety. Nucleotide analogues contain a phosphate group linked to the C5 carbon atom of the pyranose.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Nucleoside and nucleotide analogues

Sub Class

1-pyranosylindoles

Direct Parent

1-pyranosylindoles

Alternative Parents

Substituents

1-pyranosylindole
Hexose monosaccharide
Glycosyl compound
N-glycosyl compound
N-alkylindole
Indole
Indole or derivatives
Aryl-aldehyde
Monosaccharide
Oxane
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Vinylogous amide
Secondary alcohol
Organoheterocyclic compound
Polyol
Azacycle
Oxacycle
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aldehyde
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	ALOGPS
logP	-0.41	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	76.29 m³·mol⁻¹	ChemAxon
Polarizability	30.57 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA002017

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78443909

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74040279

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde (NP0007705)

MOL for NP0007705 (1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde)

3D MOL for NP0007705 (1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde)

3D SDF for NP0007705 (1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde)

3D-SDF for NP0007705 (1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde)

PDB for NP0007705 (1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde)

3D PDB for NP0007705 (1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde)

SMILES for NP0007705 (1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde)

INCHI for NP0007705 (1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde)

Structure for NP0007705 (1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde)

3D Structure for NP0007705 (1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde)