NP-MRD: Showing NP-Card for (1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile (NP0164046)

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Record Information

Version

2.0

Created at

2022-09-02 22:51:19 UTC

Updated at

2022-09-02 22:51:19 UTC

NP-MRD ID

NP0164046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

Description

(1R,4S)-4-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. (1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile is found in Passiflora biflora. Based on a literature review very few articles have been published on (1R,4S)-4-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032200512D          

 30 32  0  0  1  0            999 V2000
   -3.8542    8.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1091    7.5775    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5571    6.9644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8120    6.1798    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2600    5.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5149    4.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9629    4.1690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1559    4.3405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039    3.7274    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7969    3.8989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449    3.2858    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3071    3.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8592    4.5120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123    2.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6574    2.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1676    2.0163    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6525    1.3488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4226    2.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588    2.9428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3068    2.3297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6658    2.7712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9207    1.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2178    3.3843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0248    3.2128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6190    6.0082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8739    5.2236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1710    6.6213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9780    6.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9161    7.4060    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4681    8.0190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  6  0  0  0
 11 12  1  1  0  0  0
 12 13  3  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  6  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
    4.5173   -2.7268    1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2289   -1.6830    0.2243 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3780   -0.6701    0.7237 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9018   -0.0027   -0.4190 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7688    0.7195   -0.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6456    0.2613   -0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465    1.1370   -0.5464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6840    0.7144   -1.1940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8561    1.1488   -0.5969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2871    0.1968    0.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5030   -0.3760   -0.0244 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5760    0.6002   -0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4349    1.3609   -0.0803 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4854   -1.2061   -1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9953   -2.4086   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4382   -2.5661    0.3900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9254   -3.7449    0.9311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8013   -1.4017    1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7045    2.5174    0.0321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4367    3.4615   -0.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6563    2.5324    1.1126 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2219    2.5162    2.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7460    1.3344    0.9285 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4696    1.6438    1.5157 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9979    0.7685   -1.1134 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5368    1.7674   -0.3284 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0825   -0.2153   -1.5201 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1645    0.4037   -2.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4756   -0.9883   -0.2546 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5086   -1.8817   -0.5273 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4461   -2.4705    1.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6711   -2.9311    1.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625   -3.6686    0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7308   -2.1094   -0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6252   -0.8369   -1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8549    0.4325   -1.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4577   -0.8035   -0.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2939    2.1542   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6020    1.2781   -1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1029   -0.8869   -2.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0978   -3.2122   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5425   -2.5081    0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083   -4.0453    0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4501   -0.9200    1.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8670   -1.6935    1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6705    2.7778    0.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6871    4.3557   -0.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322    3.4439    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2042    3.4435    2.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1435    0.4328    1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8154    2.5317    1.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5679    1.2242   -2.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8999    2.2543    0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5931   -0.9625   -2.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8387    1.1630   -2.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.3195    0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3353   -1.3368   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 18  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
 11 12  1  6
 12 13  3  0
  9 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
  4 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29  2  1  0
 23  7  1  0
 14 11  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  6
  4 35  1  6
  6 36  1  0
  6 37  1  0
  7 38  1  6
  9 39  1  6
 18 44  1  0
 18 45  1  0
 16 42  1  6
 17 43  1  0
 15 41  1  0
 14 40  1  0
 19 46  1  1
 20 47  1  0
 21 48  1  1
 22 49  1  0
 23 50  1  1
 24 51  1  0
 25 52  1  6
 26 53  1  0
 27 54  1  6
 28 55  1  0
 29 56  1  1
 30 57  1  0
M  END


  Mrv1652309032200512D          

 30 32  0  0  1  0            999 V2000
   -3.8542    8.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1091    7.5775    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5571    6.9644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8120    6.1798    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2600    5.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5149    4.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9629    4.1690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1559    4.3405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039    3.7274    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7969    3.8989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449    3.2858    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3071    3.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8592    4.5120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123    2.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6574    2.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1676    2.0163    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6525    1.3488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4226    2.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588    2.9428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3068    2.3297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6658    2.7712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9207    1.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2178    3.3843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0248    3.2128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6190    6.0082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8739    5.2236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1710    6.6213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9780    6.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9161    7.4060    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4681    8.0190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  6  0  0  0
 11 12  1  1  0  0  0
 12 13  3  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  6  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0164046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@]3(C[C@H](O)C=C3)C#N)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H27NO11/c1-7-10(21)12(23)14(25)16(28-7)27-5-9-11(22)13(24)15(26)17(29-9)30-18(6-19)3-2-8(20)4-18/h2-3,7-17,20-26H,4-5H2,1H3/t7-,8-,9-,10-,11-,12+,13+,14+,15-,16-,17+,18+/m1/s1

> <INCHI_KEY>
VKYWQQIUMKKPIN-NYFRUAASSA-N

> <FORMULA>
C18H27NO11

> <MOLECULAR_WEIGHT>
433.41

> <EXACT_MASS>
433.158410693

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.85555100794364

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S)-4-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

> <ALOGPS_LOGP>
-1.82

> <JCHEM_LOGP>
-3.404176472333334

> <ALOGPS_LOGS>
-0.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.44160072496329

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.915443538097565

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9133000556887625

> <JCHEM_POLAR_SURFACE_AREA>
202.31999999999996

> <JCHEM_REFRACTIVITY>
95.49560000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.71e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S)-4-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.194  15.609   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.670  14.145   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.640  13.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -7.116  11.536   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -6.085  10.391   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -6.561   8.926   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.531   7.782   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.024   8.102   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.994   6.958   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.488   7.278   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.457   6.134   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.573   7.278   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.604   8.422   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.703   5.228   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.227   3.764   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.313   3.764   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.218   2.518   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.789   5.228   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.470   5.493   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.439   4.349   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.976   5.173   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.452   3.708   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -6.007   6.317   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -7.513   5.997   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -8.622  11.215   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -9.098   9.751   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -9.653  12.360   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -11.159  12.040   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -9.177  13.824   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -10.207  14.969   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14   18                                             
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11                                                       
CONECT   19    9   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    7   24                                                  
CONECT   24   23                                                            
CONECT   25    4   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    2   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₇NO₁₁

Average Mass

433.4100 Da

Monoisotopic Mass

433.15841 Da

IUPAC Name

(1R,4S)-4-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

Traditional Name

(1R,4S)-4-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@]3(C[C@H](O)C=C3)C#N)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C18H27NO11/c1-7-10(21)12(23)14(25)16(28-7)27-5-9-11(22)13(24)15(26)17(29-9)30-18(6-19)3-2-8(20)4-18/h2-3,7-17,20-26H,4-5H2,1H3/t7-,8-,9-,10-,11-,12+,13+,14+,15-,16-,17+,18+/m1/s1

InChI Key

VKYWQQIUMKKPIN-NYFRUAASSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Passiflora biflora	LOTUS Database	35616633

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
O-glycosyl compound
Disaccharide
Oxane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Nitrile
Carbonitrile
Acetal
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
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	-1.8	ALOGPS
logP	-3.4	ChemAxon
logS	-0.75	ALOGPS
pKa (Strongest Acidic)	11.92	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	202.32 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.5 m³·mol⁻¹	ChemAxon
Polarizability	40.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

162997244

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile (NP0164046)

MOL for NP0164046 ((1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile)

3D MOL for NP0164046 ((1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile)

3D SDF for NP0164046 ((1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile)

3D-SDF for NP0164046 ((1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile)

PDB for NP0164046 ((1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile)

3D PDB for NP0164046 ((1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile)

SMILES for NP0164046 ((1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile)

INCHI for NP0164046 ((1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile)

Structure for NP0164046 ((1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile)

3D Structure for NP0164046 ((1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile)