NP-MRD: Showing NP-Card for 6-hydroxy-galanthindole (NP0039237)

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Record Information

Version

2.0

Created at

2021-06-20 21:43:42 UTC

Updated at

2021-06-30 00:12:27 UTC

NP-MRD ID

NP0039237

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-galanthindole

Provided By

JEOL Database JEOL Logo

Description

7-[6-(Hydroxymethyl)-2H-1,3-benzodioxol-5-yl]-1-methyl-1H-indol-6-ol belongs to the class of organic compounds known as galanthindole-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids based on a 7-arylindole or 7-aryl-2,3-dihydroindole skeleton. 6-hydroxy-galanthindole is found in Narcissus. 6-hydroxy-galanthindole was first documented in 2010 (Rezanka, T. et al.). Based on a literature review very few articles have been published on 7-[6-(hydroxymethyl)-2H-1,3-benzodioxol-5-yl]-1-methyl-1H-indol-6-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123433D          

 37 40  0  0  0  0            999 V2000
   -2.4708    0.9937    1.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9491    0.0003    0.6741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9188   -0.9142    1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1122   -1.7373   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319   -1.3104   -1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -1.7848   -2.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0561   -1.1651   -3.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400   -0.0803   -2.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3955    0.4328   -3.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508    0.4643   -1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8604    1.6842   -0.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    2.9087   -1.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9206    4.0573   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750    4.0399   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    2.8747   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    1.6737   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130    0.4124   -0.5457 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7755    0.2215   -1.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190    5.2748    0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425    6.0766   -0.1336 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4604    5.3050   -0.6191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088   -0.2024   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822    0.9382    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8162    1.9760    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    0.7837    2.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905   -0.9092    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8118   -2.5612   -0.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5678   -2.6349   -2.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689   -1.5340   -4.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583    0.7384   -3.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    2.9528   -1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400    2.8980    0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1780    0.4950    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269   -0.4553   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2347   -0.6372   -1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0704    6.8183   -0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496    6.6028    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 10  8  1  0  0  0  0
 14 15  1  0  0  0  0
 22 10  2  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
 10 11  1  0  0  0  0
 14 13  2  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  2  0  0  0  0
 13 21  1  0  0  0  0
 21 20  1  0  0  0  0
 20 19  1  0  0  0  0
 19 14  1  0  0  0  0
  3  2  1  0  0  0  0
 16 17  1  0  0  0  0
  2 22  1  0  0  0  0
 17 18  1  0  0  0  0
  6  5  2  0  0  0  0
  8  9  1  0  0  0  0
 22  5  1  0  0  0  0
  2  1  1  0  0  0  0
  7 29  1  0  0  0  0
  6 28  1  0  0  0  0
  4 27  1  0  0  0  0
  3 26  1  0  0  0  0
 12 31  1  0  0  0  0
 15 32  1  0  0  0  0
 20 36  1  0  0  0  0
 20 37  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
 18 35  1  0  0  0  0
  9 30  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
M  END

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -2.4708    0.9937    1.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9491    0.0003    0.6741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9188   -0.9142    1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1122   -1.7373   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319   -1.3104   -1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -1.7848   -2.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0561   -1.1651   -3.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400   -0.0803   -2.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3955    0.4328   -3.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508    0.4643   -1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8604    1.6842   -0.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    2.9087   -1.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9206    4.0573   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750    4.0399   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    2.8747   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    1.6737   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130    0.4124   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7755    0.2215   -1.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190    5.2748    0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425    6.0766   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    5.3050   -0.6191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088   -0.2024   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822    0.9382    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8162    1.9760    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    0.7837    2.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905   -0.9092    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8118   -2.5612   -0.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5678   -2.6349   -2.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689   -1.5340   -4.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583    0.7384   -3.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    2.9528   -1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400    2.8980    0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1780    0.4950    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269   -0.4553   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2347   -0.6372   -1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0704    6.8183   -0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496    6.6028    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
 12 13  1  0
 10  8  1  0
 14 15  1  0
 22 10  2  0
 15 16  2  0
 16 11  1  0
 10 11  1  0
 14 13  2  0
  8  7  2  0
  7  6  1  0
  5  4  1  0
  4  3  2  0
 13 21  1  0
 21 20  1  0
 20 19  1  0
 19 14  1  0
  3  2  1  0
 16 17  1  0
  2 22  1  0
 17 18  1  0
  6  5  2  0
  8  9  1  0
 22  5  1  0
  2  1  1  0
  7 29  1  0
  6 28  1  0
  4 27  1  0
  3 26  1  0
 12 31  1  0
 15 32  1  0
 20 36  1  0
 20 37  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
  9 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END


  Mrv1652306202123433D          

 37 40  0  0  0  0            999 V2000
   -2.4708    0.9937    1.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9491    0.0003    0.6741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9188   -0.9142    1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1122   -1.7373   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319   -1.3104   -1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -1.7848   -2.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0561   -1.1651   -3.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400   -0.0803   -2.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3955    0.4328   -3.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508    0.4643   -1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8604    1.6842   -0.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    2.9087   -1.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9206    4.0573   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750    4.0399   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    2.8747   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    1.6737   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130    0.4124   -0.5457 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7755    0.2215   -1.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190    5.2748    0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425    6.0766   -0.1336 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4604    5.3050   -0.6191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088   -0.2024   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822    0.9382    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8162    1.9760    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    0.7837    2.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905   -0.9092    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8118   -2.5612   -0.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5678   -2.6349   -2.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689   -1.5340   -4.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583    0.7384   -3.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    2.9528   -1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400    2.8980    0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1780    0.4950    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269   -0.4553   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2347   -0.6372   -1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0704    6.8183   -0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496    6.6028    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 10  8  1  0  0  0  0
 14 15  1  0  0  0  0
 22 10  2  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
 10 11  1  0  0  0  0
 14 13  2  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  2  0  0  0  0
 13 21  1  0  0  0  0
 21 20  1  0  0  0  0
 20 19  1  0  0  0  0
 19 14  1  0  0  0  0
  3  2  1  0  0  0  0
 16 17  1  0  0  0  0
  2 22  1  0  0  0  0
 17 18  1  0  0  0  0
  6  5  2  0  0  0  0
  8  9  1  0  0  0  0
 22  5  1  0  0  0  0
  2  1  1  0  0  0  0
  7 29  1  0  0  0  0
  6 28  1  0  0  0  0
  4 27  1  0  0  0  0
  3 26  1  0  0  0  0
 12 31  1  0  0  0  0
 15 32  1  0  0  0  0
 20 36  1  0  0  0  0
 20 37  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
 18 35  1  0  0  0  0
  9 30  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039237

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C2C([H])=C([H])N(C2=C1C1=C([H])C2=C(OC([H])([H])O2)C([H])=C1C([H])([H])O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H15NO4/c1-18-5-4-10-2-3-13(20)16(17(10)18)12-7-15-14(21-9-22-15)6-11(12)8-19/h2-7,19-20H,8-9H2,1H3

> <INCHI_KEY>
HGCJOEXPTYHGLS-UHFFFAOYSA-N

> <FORMULA>
C17H15NO4

> <MOLECULAR_WEIGHT>
297.31

> <EXACT_MASS>
297.100107967

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.95382776039577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[6-(hydroxymethyl)-2H-1,3-benzodioxol-5-yl]-1-methyl-1H-indol-6-ol

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.4952276153333335

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.047598661990339

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.289178728231022

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7885461155134106

> <JCHEM_POLAR_SURFACE_AREA>
63.85000000000001

> <JCHEM_REFRACTIVITY>
81.74110000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-[6-(hydroxymethyl)-2H-1,3-benzodioxol-5-yl]-1-methylindol-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -2.4708    0.9937    1.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9491    0.0003    0.6741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9188   -0.9142    1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1122   -1.7373   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319   -1.3104   -1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -1.7848   -2.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0561   -1.1651   -3.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400   -0.0803   -2.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3955    0.4328   -3.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508    0.4643   -1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8604    1.6842   -0.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    2.9087   -1.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9206    4.0573   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750    4.0399   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    2.8747   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    1.6737   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130    0.4124   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7755    0.2215   -1.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190    5.2748    0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425    6.0766   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    5.3050   -0.6191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088   -0.2024   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822    0.9382    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8162    1.9760    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    0.7837    2.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905   -0.9092    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8118   -2.5612   -0.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5678   -2.6349   -2.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689   -1.5340   -4.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583    0.7384   -3.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    2.9528   -1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400    2.8980    0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1780    0.4950    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269   -0.4553   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2347   -0.6372   -1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0704    6.8183   -0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496    6.6028    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
 12 13  1  0
 10  8  1  0
 14 15  1  0
 22 10  2  0
 15 16  2  0
 16 11  1  0
 10 11  1  0
 14 13  2  0
  8  7  2  0
  7  6  1  0
  5  4  1  0
  4  3  2  0
 13 21  1  0
 21 20  1  0
 20 19  1  0
 19 14  1  0
  3  2  1  0
 16 17  1  0
  2 22  1  0
 17 18  1  0
  6  5  2  0
  8  9  1  0
 22  5  1  0
  2  1  1  0
  7 29  1  0
  6 28  1  0
  4 27  1  0
  3 26  1  0
 12 31  1  0
 15 32  1  0
 20 36  1  0
 20 37  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
  9 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.471   0.994   1.611  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.949   0.000   0.674  0.00  0.00           N+0
HETATM    3  C   UNK     0      -3.919  -0.914   1.003  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.112  -1.737  -0.076  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.232  -1.310  -1.105  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.007  -1.785  -2.412  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.056  -1.165  -3.217  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.340  -0.080  -2.733  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.396   0.433  -3.588  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.551   0.464  -1.444  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.860   1.684  -0.996  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.558   2.909  -1.052  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.921   4.057  -0.637  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.375   4.040  -0.188  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.107   2.875  -0.133  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.491   1.674  -0.538  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.313   0.412  -0.546  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.776   0.222  -1.878  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.819   5.275   0.167  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.343   6.077  -0.134  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.460   5.305  -0.619  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.509  -0.202  -0.628  0.00  0.00           C+0
HETATM   23  H   UNK     0      -1.382   0.938   1.666  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.816   1.976   1.285  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.880   0.784   2.604  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.391  -0.909   1.977  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.812  -2.561  -0.125  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.568  -2.635  -2.791  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.869  -1.534  -4.221  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.358   0.738  -3.039  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.581   2.953  -1.417  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.140   2.898   0.199  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.178   0.495   0.121  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.727  -0.455  -0.227  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.235  -0.637  -1.887  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.070   6.818  -0.894  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.650   6.603   0.777  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    3   22    1                                                  
CONECT    3    4    2   26                                                  
CONECT    4    5    3   27                                                  
CONECT    5    4    6   22                                                  
CONECT    6    7    5   28                                                  
CONECT    7    8    6   29                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8   30                                                       
CONECT   10    8   22   11                                                  
CONECT   11   12   16   10                                                  
CONECT   12   11   13   31                                                  
CONECT   13   12   14   21                                                  
CONECT   14   15   13   19                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   11   17                                                  
CONECT   17   16   18   33   34                                             
CONECT   18   17   35                                                       
CONECT   19   20   14                                                       
CONECT   20   21   19   36   37                                             
CONECT   21   13   20                                                       
CONECT   22   10    2    5                                                  
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    9                                                            
CONECT   31   12                                                            
CONECT   32   15                                                            
CONECT   33   17                                                            
CONECT   34   17                                                            
CONECT   35   18                                                            
CONECT   36   20                                                            
CONECT   37   20                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

RDKit          3D

37 40  0  0  0  0  0  0  0  0999 V2000
   -2.4708    0.9937    1.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9491    0.0003    0.6741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9188   -0.9142    1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1122   -1.7373   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319   -1.3104   -1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0075   -1.7848   -2.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0561   -1.1651   -3.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400   -0.0803   -2.7330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3955    0.4328   -3.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508    0.4643   -1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8604    1.6842   -0.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    2.9087   -1.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9206    4.0573   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750    4.0399   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    2.8747   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    1.6737   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130    0.4124   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7755    0.2215   -1.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190    5.2748    0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425    6.0766   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    5.3050   -0.6191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088   -0.2024   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822    0.9382    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8162    1.9760    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    0.7837    2.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3905   -0.9092    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8118   -2.5612   -0.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5678   -2.6349   -2.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689   -1.5340   -4.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3583    0.7384   -3.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    2.9528   -1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400    2.8980    0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1780    0.4950    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269   -0.4553   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2347   -0.6372   -1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0704    6.8183   -0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496    6.6028    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
 12 13  1  0
 10  8  1  0
 14 15  1  0
 22 10  2  0
 15 16  2  0
 16 11  1  0
 10 11  1  0
 14 13  2  0
  8  7  2  0
  7  6  1  0
  5  4  1  0
  4  3  2  0
 13 21  1  0
 21 20  1  0
 20 19  1  0
 19 14  1  0
  3  2  1  0
 16 17  1  0
  2 22  1  0
 17 18  1  0
  6  5  2  0
  8  9  1  0
 22  5  1  0
  2  1  1  0
  7 29  1  0
  6 28  1  0
  4 27  1  0
  3 26  1  0
 12 31  1  0
 15 32  1  0
 20 36  1  0
 20 37  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
  9 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₅NO₄

Average Mass

297.3100 Da

Monoisotopic Mass

297.10011 Da

IUPAC Name

7-[6-(hydroxymethyl)-2H-1,3-benzodioxol-5-yl]-1-methyl-1H-indol-6-ol

Traditional Name

7-[6-(hydroxymethyl)-2H-1,3-benzodioxol-5-yl]-1-methylindol-6-ol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C2C([H])=C([H])N(C2=C1C1=C([H])C2=C(OC([H])([H])O2)C([H])=C1C([H])([H])O[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C17H15NO4/c1-18-5-4-10-2-3-13(20)16(17(10)18)12-7-15-14(21-9-22-15)6-11(12)8-19/h2-7,19-20H,8-9H2,1H3

InChI Key

HGCJOEXPTYHGLS-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Narcissus	JEOL database	Rezanka, T. et al, Phytochemistry 71, 301 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galanthindole-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids based on a 7-arylindole or 7-aryl-2,3-dihydroindole skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Galanthindole-type amaryllidaceae alkaloids

Direct Parent

Galanthindole-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Galanthindole-type amaryllidaceae alkaloid
N-alkylindole
Hydroxyindole
Benzodioxole
Indole
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
N-methylpyrrole
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Organoheterocyclic compound
Acetal
Azacycle
Oxacycle
Hydrocarbon derivative
Aromatic alcohol
Alcohol
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	2.64	ALOGPS
logP	2.5	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.85 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.74 m³·mol⁻¹	ChemAxon
Polarizability	30.95 Å³	ChemAxon
Number of Rings	4	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

28287229

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101499250

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rezanka, T. et al. (2010). Rezanka, T. et al, Phytochemistry 71, 301 (2010). Phytochem..

Showing NP-Card for 6-hydroxy-galanthindole (NP0039237)

MOL for NP0039237 (6-hydroxy-galanthindole)

3D MOL for NP0039237 (6-hydroxy-galanthindole)

3D SDF for NP0039237 (6-hydroxy-galanthindole)

3D-SDF for NP0039237 (6-hydroxy-galanthindole)

PDB for NP0039237 (6-hydroxy-galanthindole)

3D PDB for NP0039237 (6-hydroxy-galanthindole)

SMILES for NP0039237 (6-hydroxy-galanthindole)

INCHI for NP0039237 (6-hydroxy-galanthindole)

Structure for NP0039237 (6-hydroxy-galanthindole)

3D Structure for NP0039237 (6-hydroxy-galanthindole)