NP-MRD: Showing NP-Card for epinoracalyphin (NP0038031)

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Record Information

Version

2.0

Created at

2021-06-20 20:49:23 UTC

Updated at

2021-06-30 00:10:35 UTC

NP-MRD ID

NP0038031

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epinoracalyphin

Provided By

JEOL Database JEOL Logo

Description

Epinoracalyphin belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. epinoracalyphin is found in Acalypha indica (Euphorbiaceae). epinoracalyphin was first documented in 2009 (Hungeling, M., et al.). Based on a literature review very few articles have been published on Epinoracalyphin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122493D          

 42 43  0  0  0  0            999 V2000
   -6.2454   -0.6548    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0420   -0.9169    1.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1195    0.1085    1.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2712    1.3562    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2073    2.3856    0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    3.4186    0.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    2.1203    1.6583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    1.0128    2.5656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9609    0.9024    3.1408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271   -0.2978    1.9185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1396   -1.2474    3.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555   -2.0000    3.8779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0523   -0.9476    0.8848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819   -1.1986    1.1696 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0624   -0.0186    0.8993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4698   -0.1828    1.1534 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1301    1.1869    0.9750 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5172    2.1162    1.8797 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543   -1.2347    0.2072 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4382   -1.4591    0.4762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2826   -2.5475    0.3748 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7516   -3.4916   -0.6007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213   -2.3206    0.2163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9020   -3.5560    0.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8324    0.1245    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8397   -1.5733    0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0314   -0.3844   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1380    1.6814    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    2.8380    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    1.3303    3.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3267    1.1593    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -1.5202    2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -0.4839    2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015    1.1458    1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9746    1.5686   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0164    2.9488    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754   -0.8993   -0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705   -2.2665   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5037   -2.9974    1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259   -4.2432   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479   -2.0576   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8578   -3.3562    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
  4  5  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 19  1  0  0  0  0
 19 21  1  0  0  0  0
 21 23  1  0  0  0  0
 23 14  1  0  0  0  0
  4  3  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
 10  3  1  0  0  0  0
  8  9  1  0  0  0  0
 19 20  1  0  0  0  0
 10 11  1  1  0  0  0
  5  6  2  0  0  0  0
 16 17  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
 11 12  3  0  0  0  0
 10 13  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 14 13  1  0  0  0  0
 14 32  1  1  0  0  0
 19 37  1  6  0  0  0
 20 38  1  0  0  0  0
 24 42  1  0  0  0  0
 23 41  1  6  0  0  0
 16 33  1  1  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 22 40  1  0  0  0  0
 21 39  1  1  0  0  0
 18 36  1  0  0  0  0
  4 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  1  0  0  0
  9 31  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -6.2454   -0.6548    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0420   -0.9169    1.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1195    0.1085    1.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2712    1.3562    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2073    2.3856    0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    3.4186    0.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    2.1203    1.6583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    1.0128    2.5656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9609    0.9024    3.1408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271   -0.2978    1.9185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1396   -1.2474    3.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555   -2.0000    3.8779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0523   -0.9476    0.8848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819   -1.1986    1.1696 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0624   -0.0186    0.8993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4698   -0.1828    1.1534 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1301    1.1869    0.9750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5172    2.1162    1.8797 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543   -1.2347    0.2072 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4382   -1.4591    0.4762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2826   -2.5475    0.3748 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7516   -3.4916   -0.6007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213   -2.3206    0.2163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9020   -3.5560    0.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8324    0.1245    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8397   -1.5733    0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0314   -0.3844   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1380    1.6814    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    2.8380    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    1.3303    3.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3267    1.1593    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -1.5202    2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -0.4839    2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015    1.1458    1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9746    1.5686   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0164    2.9488    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754   -0.8993   -0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705   -2.2665   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5037   -2.9974    1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259   -4.2432   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479   -2.0576   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8578   -3.3562    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
  4  5  1  0
 14 15  1  0
 15 16  1  0
 16 19  1  0
 19 21  1  0
 21 23  1  0
 23 14  1  0
  4  3  2  0
  5  7  1  0
  7  8  1  0
  8 10  1  0
 10  3  1  0
  8  9  1  0
 19 20  1  0
 10 11  1  1
  5  6  2  0
 16 17  1  0
  3  2  1  0
  2  1  1  0
 11 12  3  0
 10 13  1  0
 21 22  1  0
 23 24  1  0
 14 13  1  0
 14 32  1  1
 19 37  1  6
 20 38  1  0
 24 42  1  0
 23 41  1  6
 16 33  1  1
 17 34  1  0
 17 35  1  0
 22 40  1  0
 21 39  1  1
 18 36  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  1
  9 31  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END


  Mrv1652306202122493D          

 42 43  0  0  0  0            999 V2000
   -6.2454   -0.6548    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0420   -0.9169    1.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1195    0.1085    1.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2712    1.3562    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2073    2.3856    0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    3.4186    0.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    2.1203    1.6583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    1.0128    2.5656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9609    0.9024    3.1408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271   -0.2978    1.9185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1396   -1.2474    3.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555   -2.0000    3.8779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0523   -0.9476    0.8848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819   -1.1986    1.1696 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0624   -0.0186    0.8993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4698   -0.1828    1.1534 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1301    1.1869    0.9750 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5172    2.1162    1.8797 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543   -1.2347    0.2072 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4382   -1.4591    0.4762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2826   -2.5475    0.3748 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7516   -3.4916   -0.6007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213   -2.3206    0.2163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9020   -3.5560    0.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8324    0.1245    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8397   -1.5733    0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0314   -0.3844   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1380    1.6814    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    2.8380    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    1.3303    3.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3267    1.1593    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -1.5202    2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -0.4839    2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015    1.1458    1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9746    1.5686   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0164    2.9488    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754   -0.8993   -0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705   -2.2665   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5037   -2.9974    1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259   -4.2432   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479   -2.0576   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8578   -3.3562    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
  4  5  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 19  1  0  0  0  0
 19 21  1  0  0  0  0
 21 23  1  0  0  0  0
 23 14  1  0  0  0  0
  4  3  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
 10  3  1  0  0  0  0
  8  9  1  0  0  0  0
 19 20  1  0  0  0  0
 10 11  1  1  0  0  0
  5  6  2  0  0  0  0
 16 17  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
 11 12  3  0  0  0  0
 10 13  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 14 13  1  0  0  0  0
 14 32  1  1  0  0  0
 19 37  1  6  0  0  0
 20 38  1  0  0  0  0
 24 42  1  0  0  0  0
 23 41  1  6  0  0  0
 16 33  1  1  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 22 40  1  0  0  0  0
 21 39  1  1  0  0  0
 18 36  1  0  0  0  0
  4 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  1  0  0  0
  9 31  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038031

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2(C#N)C(OC([H])([H])[H])=C([H])C(=O)N([H])[C@]2([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O9/c1-22-6-2-7(17)15-12(21)13(6,4-14)24-11-10(20)9(19)8(18)5(3-16)23-11/h2,5,8-12,16,18-21H,3H2,1H3,(H,15,17)/t5-,8-,9+,10-,11+,12-,13-/m1/s1

> <INCHI_KEY>
WUVMCCRKWLRPJP-DTKWUBCZSA-N

> <FORMULA>
C13H18N2O9

> <MOLECULAR_WEIGHT>
346.292

> <EXACT_MASS>
346.101230168

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.59392091347536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2-hydroxy-4-methoxy-6-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,2,3,6-tetrahydropyridine-3-carbonitrile

> <ALOGPS_LOGP>
-1.61

> <JCHEM_LOGP>
-3.9852130636666665

> <ALOGPS_LOGS>
-0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.101405447558186

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.780901390378608

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4865029073392555

> <JCHEM_POLAR_SURFACE_AREA>
181.73

> <JCHEM_REFRACTIVITY>
74.35010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-hydroxy-4-methoxy-6-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,2-dihydropyridine-3-carbonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -6.2454   -0.6548    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0420   -0.9169    1.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1195    0.1085    1.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2712    1.3562    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2073    2.3856    0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    3.4186    0.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    2.1203    1.6583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    1.0128    2.5656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9609    0.9024    3.1408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271   -0.2978    1.9185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1396   -1.2474    3.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555   -2.0000    3.8779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0523   -0.9476    0.8848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819   -1.1986    1.1696 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0624   -0.0186    0.8993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4698   -0.1828    1.1534 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1301    1.1869    0.9750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5172    2.1162    1.8797 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543   -1.2347    0.2072 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4382   -1.4591    0.4762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2826   -2.5475    0.3748 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7516   -3.4916   -0.6007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213   -2.3206    0.2163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9020   -3.5560    0.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8324    0.1245    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8397   -1.5733    0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0314   -0.3844   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1380    1.6814    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    2.8380    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    1.3303    3.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3267    1.1593    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -1.5202    2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -0.4839    2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015    1.1458    1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9746    1.5686   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0164    2.9488    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754   -0.8993   -0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705   -2.2665   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5037   -2.9974    1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259   -4.2432   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479   -2.0576   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8578   -3.3562    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
  4  5  1  0
 14 15  1  0
 15 16  1  0
 16 19  1  0
 19 21  1  0
 21 23  1  0
 23 14  1  0
  4  3  2  0
  5  7  1  0
  7  8  1  0
  8 10  1  0
 10  3  1  0
  8  9  1  0
 19 20  1  0
 10 11  1  1
  5  6  2  0
 16 17  1  0
  3  2  1  0
  2  1  1  0
 11 12  3  0
 10 13  1  0
 21 22  1  0
 23 24  1  0
 14 13  1  0
 14 32  1  1
 19 37  1  6
 20 38  1  0
 24 42  1  0
 23 41  1  6
 16 33  1  1
 17 34  1  0
 17 35  1  0
 22 40  1  0
 21 39  1  1
 18 36  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  1
  9 31  1  0
  1 25  1  0
  1 26  1  0
  1 27  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      -6.245  -0.655   0.325  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.042  -0.917   1.039  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.120   0.109   1.181  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.271   1.356   0.689  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.207   2.386   0.795  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.266   3.419   0.142  0.00  0.00           O+0
HETATM    7  N   UNK     0      -2.191   2.120   1.658  0.00  0.00           N+0
HETATM    8  C   UNK     0      -2.246   1.013   2.566  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.961   0.902   3.141  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.827  -0.298   1.919  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.140  -1.247   3.018  0.00  0.00           C+0
HETATM   12  N   UNK     0      -3.356  -2.000   3.878  0.00  0.00           N+0
HETATM   13  O   UNK     0      -2.052  -0.948   0.885  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.682  -1.199   1.170  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.062  -0.019   0.899  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.470  -0.183   1.153  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.130   1.187   0.975  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.517   2.116   1.880  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.054  -1.235   0.207  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.438  -1.459   0.476  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.283  -2.547   0.375  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.752  -3.492  -0.601  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.221  -2.321   0.216  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.902  -3.556   0.480  0.00  0.00           O+0
HETATM   25  H   UNK     0      -6.832   0.125   0.821  0.00  0.00           H+0
HETATM   26  H   UNK     0      -6.840  -1.573   0.319  0.00  0.00           H+0
HETATM   27  H   UNK     0      -6.031  -0.384  -0.714  0.00  0.00           H+0
HETATM   28  H   UNK     0      -5.138   1.681   0.128  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.486   2.838   1.766  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.914   1.330   3.378  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.327   1.159   2.437  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.561  -1.520   2.212  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.600  -0.484   2.202  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.201   1.146   1.192  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.975   1.569  -0.039  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.016   2.949   1.795  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.975  -0.899  -0.835  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.671  -2.267  -0.028  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.504  -2.997   1.351  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.126  -4.243  -0.549  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.448  -2.058  -0.825  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.858  -3.356   0.432  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3    4   10    2                                                  
CONECT    4    5    3   28                                                  
CONECT    5    4    7    6                                                  
CONECT    6    5                                                            
CONECT    7    5    8   29                                                  
CONECT    8    7   10    9   30                                             
CONECT    9    8   31                                                       
CONECT   10    8    3   11   13                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   15   23   13   32                                             
CONECT   15   14   16                                                       
CONECT   16   15   19   17   33                                             
CONECT   17   18   16   34   35                                             
CONECT   18   17   36                                                       
CONECT   19   16   21   20   37                                             
CONECT   20   19   38                                                       
CONECT   21   19   23   22   39                                             
CONECT   22   21   40                                                       
CONECT   23   21   14   24   41                                             
CONECT   24   23   42                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    4                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   14                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   19                                                            
CONECT   38   20                                                            
CONECT   39   21                                                            
CONECT   40   22                                                            
CONECT   41   23                                                            
CONECT   42   24                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

RDKit          3D

42 43  0  0  0  0  0  0  0  0999 V2000
   -6.2454   -0.6548    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0420   -0.9169    1.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1195    0.1085    1.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2712    1.3562    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2073    2.3856    0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656    3.4186    0.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905    2.1203    1.6583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    1.0128    2.5656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9609    0.9024    3.1408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271   -0.2978    1.9185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1396   -1.2474    3.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555   -2.0000    3.8779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0523   -0.9476    0.8848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819   -1.1986    1.1696 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0624   -0.0186    0.8993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4698   -0.1828    1.1534 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1301    1.1869    0.9750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5172    2.1162    1.8797 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543   -1.2347    0.2072 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4382   -1.4591    0.4762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2826   -2.5475    0.3748 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7516   -3.4916   -0.6007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213   -2.3206    0.2163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9020   -3.5560    0.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8324    0.1245    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8397   -1.5733    0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0314   -0.3844   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1380    1.6814    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    2.8380    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    1.3303    3.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3267    1.1593    2.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -1.5202    2.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6002   -0.4839    2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015    1.1458    1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9746    1.5686   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0164    2.9488    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754   -0.8993   -0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705   -2.2665   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5037   -2.9974    1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259   -4.2432   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479   -2.0576   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8578   -3.3562    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
  4  5  1  0
 14 15  1  0
 15 16  1  0
 16 19  1  0
 19 21  1  0
 21 23  1  0
 23 14  1  0
  4  3  2  0
  5  7  1  0
  7  8  1  0
  8 10  1  0
 10  3  1  0
  8  9  1  0
 19 20  1  0
 10 11  1  1
  5  6  2  0
 16 17  1  0
  3  2  1  0
  2  1  1  0
 11 12  3  0
 10 13  1  0
 21 22  1  0
 23 24  1  0
 14 13  1  0
 14 32  1  1
 19 37  1  6
 20 38  1  0
 24 42  1  0
 23 41  1  6
 16 33  1  1
 17 34  1  0
 17 35  1  0
 22 40  1  0
 21 39  1  1
 18 36  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  1
  9 31  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈N₂O₉

Average Mass

346.2920 Da

Monoisotopic Mass

346.10123 Da

IUPAC Name

(2R,3R)-2-hydroxy-4-methoxy-6-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,2,3,6-tetrahydropyridine-3-carbonitrile

Traditional Name

(2R,3R)-2-hydroxy-4-methoxy-6-oxo-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,2-dihydropyridine-3-carbonitrile

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2(C#N)C(OC([H])([H])[H])=C([H])C(=O)N([H])[C@]2([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C13H18N2O9/c1-22-6-2-7(17)15-12(21)13(6,4-14)24-11-10(20)9(19)8(18)5(3-16)23-11/h2,5,8-12,16,18-21H,3H2,1H3,(H,15,17)/t5-,8-,9+,10-,11+,12-,13-/m1/s1

InChI Key

WUVMCCRKWLRPJP-DTKWUBCZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Acalypha indica	JEOL database	Hungeling, M., et al, Phytochemistry 70, 270 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Cyanogenic glycosides

Alternative Parents

Substituents

Cyanogenic glycoside
Hexose monosaccharide
O-glycosyl compound
Hydropyridine
Monosaccharide
Oxane
Vinylogous ester
Carboxamide group
Lactam
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Alkanolamine
Carboxylic acid derivative
Oxacycle
Carbonitrile
Nitrile
Azacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organopnictogen compound
Cyanide
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-1.6	ALOGPS
logP	-4	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	181.73 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.35 m³·mol⁻¹	ChemAxon
Polarizability	31.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102286668

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hungeling, M., et al. (2009). Hungeling, M., et al, Phytochemistry 70, 270 (2009). Phytochem..

Showing NP-Card for epinoracalyphin (NP0038031)

MOL for NP0038031 (epinoracalyphin)

3D MOL for NP0038031 (epinoracalyphin)

3D SDF for NP0038031 (epinoracalyphin)

3D-SDF for NP0038031 (epinoracalyphin)

PDB for NP0038031 (epinoracalyphin)

3D PDB for NP0038031 (epinoracalyphin)

SMILES for NP0038031 (epinoracalyphin)

INCHI for NP0038031 (epinoracalyphin)

Structure for NP0038031 (epinoracalyphin)

3D Structure for NP0038031 (epinoracalyphin)