NP-MRD: Showing NP-Card for (2R)-taxiphyllin (NP0031271)

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Record Information

Version

2.0

Created at

2021-06-19 22:24:07 UTC

Updated at

2021-06-29 23:59:44 UTC

NP-MRD ID

NP0031271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2R)-taxiphyllin

Provided By

JEOL Database JEOL Logo

Description

(R)-4-hydroxymandelonitrile beta-D-glucoside is also known as taxiphyllin. (2R)-taxiphyllin is found in Girgensohnia oppositiflora, Guazuma ulmifolia, Henriettea fascicularis, Sorghum halepense and Triglochin maritima. It was first documented in 1975 (PMID: 1194256). Based on a literature review a significant number of articles have been published on (R)-4-hydroxymandelonitrile beta-D-glucoside (PMID: 10380623) (PMID: 12711800) (PMID: 16989538) (PMID: 17340339).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100243D          

 39 40  0  0  0  0            999 V2000
   -0.2069    0.8381    3.3113 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146    0.3607    2.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3207   -0.2100    0.9407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6632    0.1632   -0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3713    1.4241   -0.6541 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4076    2.4600    0.3176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159    3.7548   -0.2418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1024    4.7661    0.9092 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8508    4.3588    1.8937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    4.1299   -1.3057 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8276    5.3697   -1.9325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250    3.0330   -2.3719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2928    3.3333   -3.2838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    1.6642   -1.7312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3925    0.6598   -2.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559   -1.7298    0.9765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8267   -2.4801    1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877   -3.8759    1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359   -4.5280    1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224   -5.8876    1.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -3.8090    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -2.4138    0.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3065    0.1468    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6218    1.3630   -1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    3.7214   -0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0789    4.8237    1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1759    5.7648    0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5177    3.5153    2.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454    4.2488   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429    5.4486   -2.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104    3.0335   -2.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3884    2.5341   -3.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4487    1.6130   -1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690   -0.1978   -2.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892   -1.9762    1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -4.4304    1.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -6.2534    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -4.3350    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181   -1.8718    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  2  0  0  0  0
  3  4  1  0  0  0  0
 21 22  1  0  0  0  0
 22 16  2  0  0  0  0
 16  3  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  1  0  0  0  0
  3 23  1  6  0  0  0
 18 19  1  0  0  0  0
  3  2  1  0  0  0  0
 16 17  1  0  0  0  0
  5 14  1  0  0  0  0
 14 12  1  0  0  0  0
 12 10  1  0  0  0  0
 10  7  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
  2  1  3  0  0  0  0
  8  9  1  0  0  0  0
  7  8  1  0  0  0  0
  5  4  1  0  0  0  0
 22 39  1  0  0  0  0
 17 35  1  0  0  0  0
 18 36  1  0  0  0  0
 21 38  1  0  0  0  0
 20 37  1  0  0  0  0
  5 24  1  6  0  0  0
 10 29  1  1  0  0  0
 11 30  1  0  0  0  0
 12 31  1  6  0  0  0
 13 32  1  0  0  0  0
 14 33  1  1  0  0  0
 15 34  1  0  0  0  0
  8 26  1  0  0  0  0
  8 27  1  0  0  0  0
  7 25  1  6  0  0  0
  9 28  1  0  0  0  0
M  END

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.2069    0.8381    3.3113 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146    0.3607    2.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3207   -0.2100    0.9407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6632    0.1632   -0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3713    1.4241   -0.6541 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4076    2.4600    0.3176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159    3.7548   -0.2418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1024    4.7661    0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8508    4.3588    1.8937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    4.1299   -1.3057 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8276    5.3697   -1.9325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250    3.0330   -2.3719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2928    3.3333   -3.2838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    1.6642   -1.7312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3925    0.6598   -2.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559   -1.7298    0.9765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8267   -2.4801    1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877   -3.8759    1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359   -4.5280    1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224   -5.8876    1.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -3.8090    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -2.4138    0.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3065    0.1468    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6218    1.3630   -1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    3.7214   -0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0789    4.8237    1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1759    5.7648    0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5177    3.5153    2.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454    4.2488   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429    5.4486   -2.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104    3.0335   -2.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3884    2.5341   -3.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4487    1.6130   -1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690   -0.1978   -2.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892   -1.9762    1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -4.4304    1.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -6.2534    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -4.3350    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181   -1.8718    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  2  0
  3  4  1  0
 21 22  1  0
 22 16  2  0
 16  3  1  0
 17 18  2  0
 19 20  1  0
  3 23  1  6
 18 19  1  0
  3  2  1  0
 16 17  1  0
  5 14  1  0
 14 12  1  0
 12 10  1  0
 10  7  1  0
  7  6  1  0
  6  5  1  0
 10 11  1  0
 12 13  1  0
 14 15  1  0
  2  1  3  0
  8  9  1  0
  7  8  1  0
  5  4  1  0
 22 39  1  0
 17 35  1  0
 18 36  1  0
 21 38  1  0
 20 37  1  0
  5 24  1  6
 10 29  1  1
 11 30  1  0
 12 31  1  6
 13 32  1  0
 14 33  1  1
 15 34  1  0
  8 26  1  0
  8 27  1  0
  7 25  1  6
  9 28  1  0
M  END


  Mrv1652306202100243D          

 39 40  0  0  0  0            999 V2000
   -0.2069    0.8381    3.3113 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146    0.3607    2.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3207   -0.2100    0.9407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6632    0.1632   -0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3713    1.4241   -0.6541 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4076    2.4600    0.3176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159    3.7548   -0.2418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1024    4.7661    0.9092 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8508    4.3588    1.8937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    4.1299   -1.3057 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8276    5.3697   -1.9325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250    3.0330   -2.3719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2928    3.3333   -3.2838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    1.6642   -1.7312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3925    0.6598   -2.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559   -1.7298    0.9765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8267   -2.4801    1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877   -3.8759    1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359   -4.5280    1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224   -5.8876    1.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -3.8090    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -2.4138    0.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3065    0.1468    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6218    1.3630   -1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    3.7214   -0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0789    4.8237    1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1759    5.7648    0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5177    3.5153    2.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454    4.2488   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429    5.4486   -2.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104    3.0335   -2.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3884    2.5341   -3.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4487    1.6130   -1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690   -0.1978   -2.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892   -1.9762    1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -4.4304    1.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -6.2534    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -4.3350    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181   -1.8718    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  2  0  0  0  0
  3  4  1  0  0  0  0
 21 22  1  0  0  0  0
 22 16  2  0  0  0  0
 16  3  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  1  0  0  0  0
  3 23  1  6  0  0  0
 18 19  1  0  0  0  0
  3  2  1  0  0  0  0
 16 17  1  0  0  0  0
  5 14  1  0  0  0  0
 14 12  1  0  0  0  0
 12 10  1  0  0  0  0
 10  7  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
  2  1  3  0  0  0  0
  8  9  1  0  0  0  0
  7  8  1  0  0  0  0
  5  4  1  0  0  0  0
 22 39  1  0  0  0  0
 17 35  1  0  0  0  0
 18 36  1  0  0  0  0
 21 38  1  0  0  0  0
 20 37  1  0  0  0  0
  5 24  1  6  0  0  0
 10 29  1  1  0  0  0
 11 30  1  0  0  0  0
 12 31  1  6  0  0  0
 13 32  1  0  0  0  0
 14 33  1  1  0  0  0
 15 34  1  0  0  0  0
  8 26  1  0  0  0  0
  8 27  1  0  0  0  0
  7 25  1  6  0  0  0
  9 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031271

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10+,11+,12-,13+,14+/m0/s1

> <INCHI_KEY>
NVLTYOJHPBMILU-GMDXDWKASA-N

> <FORMULA>
C14H17NO7

> <MOLECULAR_WEIGHT>
311.2873

> <EXACT_MASS>
311.100501903

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.27918679299089

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-(4-hydroxyphenyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile

> <ALOGPS_LOGP>
-0.77

> <JCHEM_LOGP>
-1.1206164559999992

> <ALOGPS_LOGS>
-1.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.208896083272556

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.456334194181542

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084265018608

> <JCHEM_POLAR_SURFACE_AREA>
143.4

> <JCHEM_REFRACTIVITY>
72.07730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
taxiphyllin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.2069    0.8381    3.3113 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146    0.3607    2.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3207   -0.2100    0.9407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6632    0.1632   -0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3713    1.4241   -0.6541 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4076    2.4600    0.3176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159    3.7548   -0.2418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1024    4.7661    0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8508    4.3588    1.8937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    4.1299   -1.3057 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8276    5.3697   -1.9325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250    3.0330   -2.3719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2928    3.3333   -3.2838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    1.6642   -1.7312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3925    0.6598   -2.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559   -1.7298    0.9765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8267   -2.4801    1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877   -3.8759    1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359   -4.5280    1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224   -5.8876    1.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -3.8090    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -2.4138    0.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3065    0.1468    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6218    1.3630   -1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    3.7214   -0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0789    4.8237    1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1759    5.7648    0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5177    3.5153    2.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454    4.2488   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429    5.4486   -2.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104    3.0335   -2.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3884    2.5341   -3.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4487    1.6130   -1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690   -0.1978   -2.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892   -1.9762    1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -4.4304    1.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -6.2534    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -4.3350    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181   -1.8718    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  2  0
  3  4  1  0
 21 22  1  0
 22 16  2  0
 16  3  1  0
 17 18  2  0
 19 20  1  0
  3 23  1  6
 18 19  1  0
  3  2  1  0
 16 17  1  0
  5 14  1  0
 14 12  1  0
 12 10  1  0
 10  7  1  0
  7  6  1  0
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 12 13  1  0
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  2  1  3  0
  8  9  1  0
  7  8  1  0
  5  4  1  0
 22 39  1  0
 17 35  1  0
 18 36  1  0
 21 38  1  0
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  5 24  1  6
 10 29  1  1
 11 30  1  0
 12 31  1  6
 13 32  1  0
 14 33  1  1
 15 34  1  0
  8 26  1  0
  8 27  1  0
  7 25  1  6
  9 28  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  N   UNK     0      -0.207   0.838   3.311  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.015   0.361   2.274  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.321  -0.210   0.941  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.663   0.163  -0.045  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.371   1.424  -0.654  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.408   2.460   0.318  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.116   3.755  -0.242  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.102   4.766   0.909  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.851   4.359   1.894  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.156   4.130  -1.306  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.828   5.370  -1.933  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.225   3.033  -2.372  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.293   3.333  -3.284  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.444   1.664  -1.731  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.393   0.660  -2.756  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.356  -1.730   0.977  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.827  -2.480   1.117  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.788  -3.876   1.159  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.436  -4.528   1.062  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.522  -5.888   1.099  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.617  -3.809   0.926  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.580  -2.414   0.886  0.00  0.00           C+0
HETATM   23  H   UNK     0       1.307   0.147   0.614  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.622   1.363  -1.119  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.893   3.721  -0.674  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.079   4.824   1.402  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.176   5.765   0.560  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.518   3.515   2.258  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.145   4.249  -0.846  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.443   5.449  -2.690  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.310   3.034  -2.978  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.388   2.534  -3.841  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.449   1.613  -1.294  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.469  -0.198  -2.292  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.789  -1.976   1.195  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.715  -4.430   1.268  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.368  -6.253   1.228  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.565  -4.335   0.856  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.518  -1.872   0.785  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3    1                                                       
CONECT    3    4   16   23    2                                             
CONECT    4    3    5                                                       
CONECT    5   14    6    4   24                                             
CONECT    6    7    5                                                       
CONECT    7   10    6    8   25                                             
CONECT    8    9    7   26   27                                             
CONECT    9    8   28                                                       
CONECT   10   12    7   11   29                                             
CONECT   11   10   30                                                       
CONECT   12   14   10   13   31                                             
CONECT   13   12   32                                                       
CONECT   14    5   12   15   33                                             
CONECT   15   14   34                                                       
CONECT   16   22    3   17                                                  
CONECT   17   18   16   35                                                  
CONECT   18   17   19   36                                                  
CONECT   19   21   20   18                                                  
CONECT   20   19   37                                                       
CONECT   21   19   22   38                                                  
CONECT   22   21   16   39                                                  
CONECT   23    3                                                            
CONECT   24    5                                                            
CONECT   25    7                                                            
CONECT   26    8                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   15                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   20                                                            
CONECT   38   21                                                            
CONECT   39   22                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

RDKit          3D

39 40  0  0  0  0  0  0  0  0999 V2000
   -0.2069    0.8381    3.3113 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146    0.3607    2.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3207   -0.2100    0.9407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6632    0.1632   -0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3713    1.4241   -0.6541 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4076    2.4600    0.3176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159    3.7548   -0.2418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1024    4.7661    0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8508    4.3588    1.8937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    4.1299   -1.3057 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8276    5.3697   -1.9325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250    3.0330   -2.3719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2928    3.3333   -3.2838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    1.6642   -1.7312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3925    0.6598   -2.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559   -1.7298    0.9765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8267   -2.4801    1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877   -3.8759    1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359   -4.5280    1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224   -5.8876    1.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -3.8090    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800   -2.4138    0.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3065    0.1468    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6218    1.3630   -1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    3.7214   -0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0789    4.8237    1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1759    5.7648    0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5177    3.5153    2.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454    4.2488   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429    5.4486   -2.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3104    3.0335   -2.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3884    2.5341   -3.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4487    1.6130   -1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690   -0.1978   -2.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892   -1.9762    1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -4.4304    1.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -6.2534    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -4.3350    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181   -1.8718    0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  2  0
  3  4  1  0
 21 22  1  0
 22 16  2  0
 16  3  1  0
 17 18  2  0
 19 20  1  0
  3 23  1  6
 18 19  1  0
  3  2  1  0
 16 17  1  0
  5 14  1  0
 14 12  1  0
 12 10  1  0
 10  7  1  0
  7  6  1  0
  6  5  1  0
 10 11  1  0
 12 13  1  0
 14 15  1  0
  2  1  3  0
  8  9  1  0
  7  8  1  0
  5  4  1  0
 22 39  1  0
 17 35  1  0
 18 36  1  0
 21 38  1  0
 20 37  1  0
  5 24  1  6
 10 29  1  1
 11 30  1  0
 12 31  1  6
 13 32  1  0
 14 33  1  1
 15 34  1  0
  8 26  1  0
  8 27  1  0
  7 25  1  6
  9 28  1  0
M  END

View in JSmol

Synonyms

Value	Source
(R)-alpha-(beta-D-Glucopyranosyloxy)-4-hydroxybenzeneacetonitrile	ChEBI
(R)-p-Hydroxymandelonitrile-D-glucopyranoside	ChEBI
Taxiphyllin	ChEBI
(R)-a-(b-D-Glucopyranosyloxy)-4-hydroxybenzeneacetonitrile	Generator
(R)-Α-(β-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile	Generator
(R)-4-Hydroxymandelonitrile b-D-glucoside	Generator
(R)-4-Hydroxymandelonitrile β-D-glucoside	Generator

Chemical Formula

C₁₄H₁₇NO₇

Average Mass

311.2873 Da

Monoisotopic Mass

311.10050 Da

IUPAC Name

(2R)-2-(4-hydroxyphenyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile

Traditional Name

taxiphyllin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10+,11+,12-,13+,14+/m0/s1

InChI Key

NVLTYOJHPBMILU-GMDXDWKASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Chimonanthus fragrans	KNApSAcK Database	22123792
Girgensohnia oppositiflora	LOTUS Database	35616633
Guazuma ulmifolia	JEOL database	Seigler, D. S., et al, Phytochemistry 66, 1567 (2005)
Henriettea fascicularis	LOTUS Database	35616633
Macadamia ternifolia	KNApSAcK Database	22123792
Salsola tetrandra	KNApSAcK Database	22123792
Sorghum halepense	LOTUS Database	35616633
Triglochin maritima	LOTUS Database	35616633
Triglochin maritimum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound 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
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Secondary alcohol
Polyol
Oxacycle
Nitrile
Carbonitrile
Acetal
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Organopnictogen compound
Organic nitrogen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:16267 )
nitrile (CHEBI:16267 )
Cyanogenic glucosides derived from thyrosine (C01855 )

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	-0.77	ALOGPS
logP	-1.1	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	143.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.08 m³·mol⁻¹	ChemAxon
Polarizability	30.28 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00041914

Chemspider ID

96890

KEGG Compound ID

C01855

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

16267

Good Scents ID

Not Available

References

General References

Petruccioli M, Brimer L, Cicalini AR, Pulci V, Federici F: Production and properties of the linamarase and amygdalase activities of Penicillium aurantiogriseum P35. Biosci Biotechnol Biochem. 1999 May;63(5):805-12. doi: 10.1271/bbb.63.805. [PubMed:10380623 ]
Rosen MA, Farnden KJ, Conn EE: Stereochemical aspects of the biosynthesis of the epimeric cyanogenic glucosides dhurrin and taxiphyllin. J Biol Chem. 1975 Nov 10;250(21):8302-8. [PubMed:1194256 ]
Calderon AI, Terreaux C, Gupta MP, Hostettmann K, Schenk KJ: Taxiphyllin from Henriettella fascicularis. Acta Crystallogr C. 2003 Mar;59(Pt 3):o174-6. doi: 10.1107/s0108270103001355. Epub 2003 Feb 28. [PubMed:12711800 ]
Oueslati MH, Ben Jannet H, Mighri Z, Chriaa J, Abreu PM: Phytochemical constituents from Salsola tetrandra. J Nat Prod. 2006 Sep;69(9):1366-9. doi: 10.1021/np060222w. [PubMed:16989538 ]
Nahrstedt A, Kant JD, Hosel W: Aspects on the Biosynthesis of the Cyanogenic Glucoside Triglochinin in Triglochin maritima1. Planta Med. 1984 Oct;50(5):394-7. doi: 10.1055/s-2007-969747. [PubMed:17340339 ]
Seigler, D. S., et al. (2005). Seigler, D. S., et al, Phytochemistry 66, 1567 (2005) . Phytochem..

Showing NP-Card for (2R)-taxiphyllin (NP0031271)

MOL for NP0031271 ((2R)-taxiphyllin)

3D MOL for NP0031271 ((2R)-taxiphyllin)

3D SDF for NP0031271 ((2R)-taxiphyllin)

3D-SDF for NP0031271 ((2R)-taxiphyllin)

PDB for NP0031271 ((2R)-taxiphyllin)

3D PDB for NP0031271 ((2R)-taxiphyllin)

SMILES for NP0031271 ((2R)-taxiphyllin)

INCHI for NP0031271 ((2R)-taxiphyllin)

Structure for NP0031271 ((2R)-taxiphyllin)

3D Structure for NP0031271 ((2R)-taxiphyllin)