NP-MRD: Showing NP-Card for dysoline (NP0042659)

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Record Information

Version

2.0

Created at

2021-06-21 00:16:08 UTC

Updated at

2021-06-30 00:17:52 UTC

NP-MRD ID

NP0042659

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dysoline

Provided By

JEOL Database JEOL Logo

Description

Dysoline belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group. dysoline is found in Dysoxylum binectariferum. dysoline was first documented in 2019 (PMID: 30653329). Based on a literature review very few articles have been published on Dysoline.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102163D          

 41 43  0  0  0  0            999 V2000
   -3.3368   -3.5067    4.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5505   -3.3561    3.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308   -4.2374    2.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8262   -4.0185    1.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -4.7990    0.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719   -2.8232    1.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1688   -2.5142    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494   -3.3341   -0.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401   -1.3590    0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -1.0097   -1.0702 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0574    0.3522   -1.6746 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8099    0.5805   -2.9909 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2705    0.4570   -2.8861 N   0  0  1  0  0  0  0  0  0  0  0  0
    3.8715    1.6324   -2.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6671   -0.8092   -2.2442 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9695   -1.1263   -0.8999 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4523   -0.2396    0.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6294   -0.5594    1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136    0.5512    1.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -0.8558    2.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9805   -1.9900    2.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -2.2295    3.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6612   -3.5771    5.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9899   -2.6400    4.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9647   -4.4037    4.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2624   -5.1159    2.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678   -4.0845   -0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1819   -1.7418   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217    0.3794   -1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638    1.1773   -0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -0.1522   -3.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.5597   -3.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9612    1.5289   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003    1.8316   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747    2.5226   -2.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4437   -1.6213   -2.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7559   -0.8217   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305   -2.1438   -0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233   -0.3355    0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2243    0.4066    0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653   -0.2036    3.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0  0  0  0
 21 22  1  0  0  0  0
  7  8  1  0  0  0  0
  6 21  2  0  0  0  0
 18 19  1  0  0  0  0
  6  4  1  0  0  0  0
  2  1  1  0  0  0  0
 21 20  1  0  0  0  0
 10  9  1  0  0  0  0
 10 16  1  0  0  0  0
  4  3  1  0  0  0  0
 20 18  2  0  0  0  0
  3  2  2  0  0  0  0
 18  9  1  0  0  0  0
  2 22  1  0  0  0  0
 10 11  1  0  0  0  0
 16 15  1  0  0  0  0
 15 13  1  0  0  0  0
 13 12  1  0  0  0  0
 12 11  1  0  0  0  0
  9  7  2  0  0  0  0
 16 17  1  0  0  0  0
  7  6  1  0  0  0  0
 13 14  1  0  0  0  0
  3 26  1  0  0  0  0
 20 41  1  0  0  0  0
  8 27  1  0  0  0  0
 19 40  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
 10 28  1  6  0  0  0
 16 38  1  1  0  0  0
 15 36  1  0  0  0  0
 15 37  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 17 39  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -3.3368   -3.5067    4.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5505   -3.3561    3.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308   -4.2374    2.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8262   -4.0185    1.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -4.7990    0.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719   -2.8232    1.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1688   -2.5142    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494   -3.3341   -0.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401   -1.3590    0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -1.0097   -1.0702 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0574    0.3522   -1.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099    0.5805   -2.9909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2705    0.4570   -2.8861 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8715    1.6324   -2.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6671   -0.8092   -2.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9695   -1.1263   -0.8999 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4523   -0.2396    0.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6294   -0.5594    1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136    0.5512    1.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -0.8558    2.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9805   -1.9900    2.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -2.2295    3.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6612   -3.5771    5.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9899   -2.6400    4.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9647   -4.4037    4.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2624   -5.1159    2.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678   -4.0845   -0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1819   -1.7418   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217    0.3794   -1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638    1.1773   -0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -0.1522   -3.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.5597   -3.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9612    1.5289   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003    1.8316   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747    2.5226   -2.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4437   -1.6213   -2.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7559   -0.8217   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305   -2.1438   -0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233   -0.3355    0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2243    0.4066    0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653   -0.2036    3.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
 21 22  1  0
  7  8  1  0
  6 21  2  0
 18 19  1  0
  6  4  1  0
  2  1  1  0
 21 20  1  0
 10  9  1  0
 10 16  1  0
  4  3  1  0
 20 18  2  0
  3  2  2  0
 18  9  1  0
  2 22  1  0
 10 11  1  0
 16 15  1  0
 15 13  1  0
 13 12  1  0
 12 11  1  0
  9  7  2  0
 16 17  1  0
  7  6  1  0
 13 14  1  0
  3 26  1  0
 20 41  1  0
  8 27  1  0
 19 40  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 10 28  1  6
 16 38  1  1
 15 36  1  0
 15 37  1  0
 12 31  1  0
 12 32  1  0
 11 29  1  0
 11 30  1  0
 17 39  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
M  END


  Mrv1652306212102163D          

 41 43  0  0  0  0            999 V2000
   -3.3368   -3.5067    4.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5505   -3.3561    3.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308   -4.2374    2.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8262   -4.0185    1.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -4.7990    0.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719   -2.8232    1.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1688   -2.5142    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494   -3.3341   -0.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401   -1.3590    0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -1.0097   -1.0702 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0574    0.3522   -1.6746 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8099    0.5805   -2.9909 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2705    0.4570   -2.8861 N   0  0  1  0  0  0  0  0  0  0  0  0
    3.8715    1.6324   -2.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6671   -0.8092   -2.2442 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9695   -1.1263   -0.8999 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4523   -0.2396    0.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6294   -0.5594    1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136    0.5512    1.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -0.8558    2.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9805   -1.9900    2.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -2.2295    3.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6612   -3.5771    5.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9899   -2.6400    4.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9647   -4.4037    4.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2624   -5.1159    2.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678   -4.0845   -0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1819   -1.7418   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217    0.3794   -1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638    1.1773   -0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -0.1522   -3.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.5597   -3.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9612    1.5289   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003    1.8316   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747    2.5226   -2.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4437   -1.6213   -2.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7559   -0.8217   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305   -2.1438   -0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233   -0.3355    0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2243    0.4066    0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653   -0.2036    3.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0  0  0  0
 21 22  1  0  0  0  0
  7  8  1  0  0  0  0
  6 21  2  0  0  0  0
 18 19  1  0  0  0  0
  6  4  1  0  0  0  0
  2  1  1  0  0  0  0
 21 20  1  0  0  0  0
 10  9  1  0  0  0  0
 10 16  1  0  0  0  0
  4  3  1  0  0  0  0
 20 18  2  0  0  0  0
  3  2  2  0  0  0  0
 18  9  1  0  0  0  0
  2 22  1  0  0  0  0
 10 11  1  0  0  0  0
 16 15  1  0  0  0  0
 15 13  1  0  0  0  0
 13 12  1  0  0  0  0
 12 11  1  0  0  0  0
  9  7  2  0  0  0  0
 16 17  1  0  0  0  0
  7  6  1  0  0  0  0
 13 14  1  0  0  0  0
  3 26  1  0  0  0  0
 20 41  1  0  0  0  0
  8 27  1  0  0  0  0
 19 40  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
 10 28  1  6  0  0  0
 16 38  1  1  0  0  0
 15 36  1  0  0  0  0
 15 37  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 17 39  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042659

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(=O)C([H])=C(O2)C([H])([H])[H])C(O[H])=C1[C@@]1([H])C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO5/c1-8-5-10(18)15-13(22-8)6-11(19)14(16(15)21)9-3-4-17(2)7-12(9)20/h5-6,9,12,19-21H,3-4,7H2,1-2H3/t9-,12+/m0/s1

> <INCHI_KEY>
PXUUTWRMWAPTOI-JOYOIKCWSA-N

> <FORMULA>
C16H19NO5

> <MOLECULAR_WEIGHT>
305.33

> <EXACT_MASS>
305.126322716

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.959635492266102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-6-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-2-methyl-4H-chromen-4-one

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
0.7442504260541992

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.476033890076033

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.681926489791491

> <JCHEM_PKA_STRONGEST_BASIC>
7.3234001014904155

> <JCHEM_POLAR_SURFACE_AREA>
90.23

> <JCHEM_REFRACTIVITY>
83.06920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-6-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-2-methylchromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -3.3368   -3.5067    4.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5505   -3.3561    3.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308   -4.2374    2.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8262   -4.0185    1.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -4.7990    0.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719   -2.8232    1.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1688   -2.5142    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494   -3.3341   -0.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401   -1.3590    0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -1.0097   -1.0702 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0574    0.3522   -1.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099    0.5805   -2.9909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2705    0.4570   -2.8861 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8715    1.6324   -2.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6671   -0.8092   -2.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9695   -1.1263   -0.8999 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4523   -0.2396    0.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6294   -0.5594    1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136    0.5512    1.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -0.8558    2.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9805   -1.9900    2.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -2.2295    3.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6612   -3.5771    5.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9899   -2.6400    4.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9647   -4.4037    4.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2624   -5.1159    2.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678   -4.0845   -0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1819   -1.7418   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217    0.3794   -1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638    1.1773   -0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -0.1522   -3.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.5597   -3.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9612    1.5289   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003    1.8316   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747    2.5226   -2.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4437   -1.6213   -2.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7559   -0.8217   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305   -2.1438   -0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233   -0.3355    0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2243    0.4066    0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653   -0.2036    3.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
 21 22  1  0
  7  8  1  0
  6 21  2  0
 18 19  1  0
  6  4  1  0
  2  1  1  0
 21 20  1  0
 10  9  1  0
 10 16  1  0
  4  3  1  0
 20 18  2  0
  3  2  2  0
 18  9  1  0
  2 22  1  0
 10 11  1  0
 16 15  1  0
 15 13  1  0
 13 12  1  0
 12 11  1  0
  9  7  2  0
 16 17  1  0
  7  6  1  0
 13 14  1  0
  3 26  1  0
 20 41  1  0
  8 27  1  0
 19 40  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 10 28  1  6
 16 38  1  1
 15 36  1  0
 15 37  1  0
 12 31  1  0
 12 32  1  0
 11 29  1  0
 11 30  1  0
 17 39  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.337  -3.507   4.825  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.551  -3.356   3.560  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.631  -4.237   2.554  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.826  -4.019   1.343  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.865  -4.799   0.398  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.972  -2.823   1.312  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.169  -2.514   0.200  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.149  -3.334  -0.904  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.640  -1.359   0.183  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.441  -1.010  -1.070  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.057   0.352  -1.675  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.810   0.581  -2.991  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.271   0.457  -2.886  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.872   1.632  -2.261  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.667  -0.809  -2.244  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.970  -1.126  -0.900  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.452  -0.240   0.123  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.629  -0.559   1.340  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.414   0.551   1.479  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.178  -0.856   2.439  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.981  -1.990   2.424  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.744  -2.229   3.539  0.00  0.00           O+0
HETATM   23  H   UNK     0      -2.661  -3.577   5.683  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.990  -2.640   4.969  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.965  -4.404   4.816  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.262  -5.116   2.576  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.768  -4.085  -0.749  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.182  -1.742  -1.847  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.022   0.379  -1.872  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.264   1.177  -0.985  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.459  -0.152  -3.730  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.540   1.560  -3.405  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.961   1.529  -2.212  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.500   1.832  -1.252  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.675   2.523  -2.869  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.444  -1.621  -2.948  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.756  -0.822  -2.110  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.231  -2.144  -0.585  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.423  -0.336   0.136  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.224   0.407   0.941  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.165  -0.204   3.309  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3   22                                                  
CONECT    3    4    2   26                                                  
CONECT    4    5    6    3                                                  
CONECT    5    4                                                            
CONECT    6   21    4    7                                                  
CONECT    7    8    9    6                                                  
CONECT    8    7   27                                                       
CONECT    9   10   18    7                                                  
CONECT   10    9   16   11   28                                             
CONECT   11   10   12   29   30                                             
CONECT   12   13   11   31   32                                             
CONECT   13   15   12   14                                                  
CONECT   14   13   33   34   35                                             
CONECT   15   16   13   36   37                                             
CONECT   16   10   15   17   38                                             
CONECT   17   16   39                                                       
CONECT   18   19   20    9                                                  
CONECT   19   18   40                                                       
CONECT   20   21   18   41                                                  
CONECT   21   22    6   20                                                  
CONECT   22   21    2                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    8                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   14                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
   -3.3368   -3.5067    4.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5505   -3.3561    3.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308   -4.2374    2.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8262   -4.0185    1.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -4.7990    0.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719   -2.8232    1.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1688   -2.5142    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494   -3.3341   -0.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401   -1.3590    0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4411   -1.0097   -1.0702 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0574    0.3522   -1.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099    0.5805   -2.9909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2705    0.4570   -2.8861 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8715    1.6324   -2.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6671   -0.8092   -2.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9695   -1.1263   -0.8999 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4523   -0.2396    0.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6294   -0.5594    1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136    0.5512    1.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -0.8558    2.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9805   -1.9900    2.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -2.2295    3.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6612   -3.5771    5.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9899   -2.6400    4.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9647   -4.4037    4.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2624   -5.1159    2.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678   -4.0845   -0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1819   -1.7418   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217    0.3794   -1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638    1.1773   -0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -0.1522   -3.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.5597   -3.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9612    1.5289   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003    1.8316   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747    2.5226   -2.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4437   -1.6213   -2.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7559   -0.8217   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305   -2.1438   -0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233   -0.3355    0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2243    0.4066    0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653   -0.2036    3.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
 21 22  1  0
  7  8  1  0
  6 21  2  0
 18 19  1  0
  6  4  1  0
  2  1  1  0
 21 20  1  0
 10  9  1  0
 10 16  1  0
  4  3  1  0
 20 18  2  0
  3  2  2  0
 18  9  1  0
  2 22  1  0
 10 11  1  0
 16 15  1  0
 15 13  1  0
 13 12  1  0
 12 11  1  0
  9  7  2  0
 16 17  1  0
  7  6  1  0
 13 14  1  0
  3 26  1  0
 20 41  1  0
  8 27  1  0
 19 40  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 10 28  1  6
 16 38  1  1
 15 36  1  0
 15 37  1  0
 12 31  1  0
 12 32  1  0
 11 29  1  0
 11 30  1  0
 17 39  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₉NO₅

Average Mass

305.3300 Da

Monoisotopic Mass

305.12632 Da

IUPAC Name

5,7-dihydroxy-6-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-2-methyl-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-6-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-2-methylchromen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C(=O)C([H])=C(O2)C([H])([H])[H])C(O[H])=C1[C@@]1([H])C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C16H19NO5/c1-8-5-10(18)15-13(22-8)6-11(19)14(16(15)21)9-3-4-17(2)7-12(9)20/h5-6,9,12,19-21H,3-4,7H2,1-2H3/t9-,12+/m0/s1

InChI Key

PXUUTWRMWAPTOI-JOYOIKCWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Dysoxylum binectariferum	JEOL database	Jain, S. K., et al, Tetrahedron Lett. 54, 7140 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Substituents

Phenylpiperidine
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Aralkylamine
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
1,2-aminoalcohol
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Amine
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	0.97	ALOGPS
logP	0.74	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	6.68	ChemAxon
pKa (Strongest Basic)	7.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.07 m³·mol⁻¹	ChemAxon
Polarizability	31.96 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

30900774

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73291698

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Coffin A, Ready JM: Selective Synthesis of (+)-Dysoline. Org Lett. 2019 Feb 1;21(3):648-651. doi: 10.1021/acs.orglett.8b03777. Epub 2019 Jan 17. [PubMed:30653329 ]
Jain, S. K., et al. (2013). Jain, S. K., et al, Tetrahedron Lett. 54, 7140 (2013). Tetrahedron Lett.

Showing NP-Card for dysoline (NP0042659)

MOL for NP0042659 (dysoline)

3D MOL for NP0042659 (dysoline)

3D SDF for NP0042659 (dysoline)

3D-SDF for NP0042659 (dysoline)

PDB for NP0042659 (dysoline)

3D PDB for NP0042659 (dysoline)

SMILES for NP0042659 (dysoline)

INCHI for NP0042659 (dysoline)

Structure for NP0042659 (dysoline)

3D Structure for NP0042659 (dysoline)