NP-MRD: Showing NP-Card for (2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol (NP0227869)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 07:20:32 UTC

Updated at

2022-09-06 07:20:32 UTC

NP-MRD ID

NP0227869

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol

Description

(3S,5R,6R,7E,9S)-Megastigman-7-ene-3,5,6,9-tetrol 9-O-beta-D-glucopyranoside belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. (2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol is found in Equisetum ramosissimum, Glochidion zeylanicum, Sinocrassula indica and Staphylea bumalda. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol (3S,5R,6R,7E,9S)-Megastigman-7-ene-3,5,6,9-tetrol 9-O-beta-D-glucopyranoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006262D          

 28 29  0  0  0  0            999 V2000
 9997.7060 9998.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4208 9998.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1352 9998.5683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.8513 9998.1566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.279210000.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.995310001.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2792 9997.3312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.7094 9998.1566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.7094 9999.8069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1352 9999.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8062 9997.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2594 9996.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8048 9999.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7336 9999.1940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8466 9996.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2756 9998.5685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.5612 9998.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5612 9997.3310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.2756 9996.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9900 9997.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9900 9998.1560    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.2799 9999.8063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.5655 9999.3939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5655 9998.5689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.2799 9998.1565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.9943 9998.5689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.9943 9999.3939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.9904 9998.9809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  6  0  0  0
  5  6  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 27  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  1 21  1  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  0  0  0  0
 18 15  1  6  0  0  0
 16 13  1  6  0  0  0
 16 14  1  1  0  0  0
 24  4  1  6  0  0  0
 22  5  1  6  0  0  0
 27  9  1  1  0  0  0
 26  8  1  6  0  0  0
 25  7  1  1  0  0  0
 21 28  1  6  0  0  0
M  END

     RDKit          3D

 62 63  0  0  0  0  0  0  0  0999 V2000
   -1.5730    3.3310    0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022    2.0028   -0.2655 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1593    1.6179    0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9874    0.8656   -0.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515    0.4800   -0.0581 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7443    1.4794    0.8536 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178   -0.8055    0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5090   -0.5724    1.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069   -1.9481   -0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398   -1.0674    1.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5424   -1.4432   -0.0143 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9007   -1.2377    0.3153 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1700   -0.7740   -1.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460    0.4506   -1.1778 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2098    1.7012   -1.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    0.5355   -2.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1285    1.0348    0.1140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7780    0.5110   -0.9957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1344    0.7165   -1.0036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8484    0.0477   -0.0433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8224    0.7527    1.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5821   -0.0160    2.2051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4961   -1.3948    0.1244 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1557   -2.2024   -0.8023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0158   -1.6696    0.0544 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3385   -1.1836    1.1559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4613   -0.9550   -1.1658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1421   -1.4077   -2.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5596    3.1207    1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5487    3.6963    0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7457    4.0486    0.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2091    2.1202   -1.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4895    1.9759    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6395    0.5219   -1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4672    2.3794    0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9097    0.2500    2.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089   -1.4982    2.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4370   -0.4653    1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8747   -2.4306    0.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312   -2.7198   -0.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -1.5490   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8200   -1.8635    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1197   -0.0942    1.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4551   -2.5643   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0248   -1.0483    1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1298   -0.4990   -1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7026   -1.5253   -1.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6942    2.5721   -1.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5008    1.9847   -0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1391    1.5305   -1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891    0.2761   -3.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745    1.0178   -1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9286    0.0774   -0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2576    1.7520    1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8031    0.8012    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4827    0.3343    3.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8448   -1.7172    1.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0818   -1.8867   -0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8826   -2.7646   -0.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921   -1.9200    1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3778   -1.1309   -1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811   -1.6315   -3.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  6
 27 18  1  0
 14  5  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
 18 52  1  6
 20 53  1  6
 21 54  1  0
 21 55  1  0
 22 56  1  0
 23 57  1  1
 24 58  1  0
 25 59  1  6
 26 60  1  0
 27 61  1  6
 28 62  1  0
  3 33  1  0
  4 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  0
 13 46  1  0
 13 47  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
M  END


  Mrv1652309272006262D          

 28 29  0  0  0  0            999 V2000
 9997.7060 9998.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4208 9998.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1352 9998.5683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.8513 9998.1566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.279210000.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.995310001.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2792 9997.3312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.7094 9998.1566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.7094 9999.8069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1352 9999.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8062 9997.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2594 9996.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8048 9999.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7336 9999.1940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8466 9996.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2756 9998.5685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.5612 9998.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5612 9997.3310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.2756 9996.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9900 9997.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9900 9998.1560    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.2799 9999.8063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.5655 9999.3939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5655 9998.5689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.2799 9998.1565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.9943 9998.5689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.9943 9999.3939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.9904 9998.9809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  6  0  0  0
  5  6  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 27  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  1 21  1  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  0  0  0  0
 18 15  1  6  0  0  0
 16 13  1  6  0  0  0
 16 14  1  1  0  0  0
 24  4  1  6  0  0  0
 22  5  1  6  0  0  0
 27  9  1  1  0  0  0
 26  8  1  6  0  0  0
 25  7  1  1  0  0  0
 21 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0227869

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)\C=C\[C@@]1(O)C(C)(C)C[C@H](O)C[C@@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C19H34O9/c1-10(27-16-15(24)14(23)13(22)12(9-20)28-16)5-6-19(26)17(2,3)7-11(21)8-18(19,4)25/h5-6,10-16,20-26H,7-9H2,1-4H3/b6-5+/t10-,11-,12+,13+,14-,15+,16+,18+,19+/m0/s1

> <INCHI_KEY>
XZRJEYQBLXDNNU-DRKFIVKCSA-N

> <FORMULA>
C19H34O9

> <MOLECULAR_WEIGHT>
406.472

> <EXACT_MASS>
406.220282675

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
42.66022889743777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2S,3E)-4-[(1R,2R,4S)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.87

> <JCHEM_LOGP>
-1.8235505783333337

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.808087319040109

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.131255940746776

> <JCHEM_PKA_STRONGEST_BASIC>
-2.737440428746381

> <JCHEM_POLAR_SURFACE_AREA>
160.07

> <JCHEM_REFRACTIVITY>
99.10339999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2S,3E)-4-[(1R,2R,4S)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8662.3848663.994   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.7198663.226   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.0528663.994   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8666.3898663.226   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8669.0558667.847   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8670.3918668.617   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8669.0558661.685   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8671.7248663.226   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8671.7248666.306   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8665.0528665.536   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.5728661.926   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.5518660.228   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.7028665.178   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8658.7038665.162   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8657.0478660.913   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8659.7158663.994   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8658.3818663.225   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8658.3818661.685   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8659.7158660.915   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.0488661.685   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8661.0488663.225   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8669.0568666.305   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8667.7228665.535   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0    8667.7228663.995   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.0568663.225   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8670.3898663.995   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8670.3898665.535   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0    8661.0498664.764   0.000  0.00  0.00           O+0
CONECT    1    2   21                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3   24                                                       
CONECT    5    6   22                                                       
CONECT    6    5                                                            
CONECT    7   25                                                            
CONECT    8   26                                                            
CONECT    9   27                                                            
CONECT   10    3                                                            
CONECT   11   20                                                            
CONECT   12   20                                                            
CONECT   13   16                                                            
CONECT   14   16                                                            
CONECT   15   18                                                            
CONECT   16   17   21   13   14                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   15                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   11   12                                             
CONECT   21   16   20    1   28                                             
CONECT   22   27   23    5                                                  
CONECT   23   22   24                                                       
CONECT   24   25   23    4                                                  
CONECT   25   24   26    7                                                  
CONECT   26   25   27    8                                                  
CONECT   27   22   26    9                                                  
CONECT   28   21                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Value	Source
(3S,5R,6R,7E,9S)-Megastigman-7-ene-3,5,6,9-tetrol 9-O-b-D-glucopyranoside	Generator
(3S,5R,6R,7E,9S)-Megastigman-7-ene-3,5,6,9-tetrol 9-O-β-D-glucopyranoside	Generator
Megastigman-7-ene-3,5,6,9-tetrol 9-O-beta-D-glucopyranoside	PhytoBank
Megastigman-7-ene-3,5,6,9-tetrol 9-O-β-D-glucopyranoside	PhytoBank
Megastigman-7-ene-3,5,6,9-tetrol 9-(beta-D-glucopyranoside)	PhytoBank
Megastigman-7-ene-3,5,6,9-tetrol 9-(β-D-glucopyranoside)	PhytoBank
(3S,5R,6R,7E,9S)-Megastigman-7-ene-3,5,6,9-tetrol 9-O-beta-D-glucopyranoside	PhytoBank
(3S,5R,6R,7E,9S)-Megastigman-7-ene-3,5,6,9-tetrol 9-(beta-D-glucopyranoside)	PhytoBank
(3S,5R,6R,7E,9S)-Megastigman-7-ene-3,5,6,9-tetrol 9-(β-D-glucopyranoside)	PhytoBank
(3S,5R,6R,7E,9S)-Megastigm-7-ene-3,5,6,9-tetrol 9-O-beta-D-glucopyranoside	PhytoBank
(3S,5R,6R,7E,9S)-Megastigm-7-ene-3,5,6,9-tetrol 9-O-β-D-glucopyranoside	PhytoBank
(3S,5R,6R,7E,9S)-Megastigm-7-ene-3,5,6,9-tetrol 9-(beta-D-glucopyranoside)	PhytoBank
(3S,5R,6R,7E,9S)-Megastigm-7-ene-3,5,6,9-tetrol 9-(β-D-glucopyranoside)	PhytoBank
trans-(3S,5R,6R,9S)-Megastigman-7-ene-3,5,6,9-tetraol 9-O-beta-D-glucopyranoside	PhytoBank
trans-(3S,5R,6R,9S)-Megastigman-7-ene-3,5,6,9-tetraol 9-O-β-D-glucopyranoside	PhytoBank
trans-(3S,5R,6R,9S)-Megastigman-7-ene-3,5,6,9-tetraol 9-O-glucose	PhytoBank

Chemical Formula

C₁₉H₃₄O₉

Average Mass

406.4720 Da

Monoisotopic Mass

406.22028 Da

IUPAC Name

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2S,3E)-4-[(1R,2R,4S)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol

Traditional Name

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2S,3E)-4-[(1R,2R,4S)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

C[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)\C=C\[C@@]1(O)C(C)(C)C[C@H](O)C[C@@]1(C)O

InChI Identifier

InChI=1S/C19H34O9/c1-10(27-16-15(24)14(23)13(22)12(9-20)28-16)5-6-19(26)17(2,3)7-11(21)8-18(19,4)25/h5-6,10-16,20-26H,7-9H2,1-4H3/b6-5+/t10-,11-,12+,13+,14-,15+,16+,18+,19+/m0/s1

InChI Key

XZRJEYQBLXDNNU-DRKFIVKCSA-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
Equisetum ramosissimum	LOTUS Database	35616633
Glochidion zeylanicum	LOTUS Database	35616633
Sinocrassula indica	LOTUS Database	35616633
Staphylea bumalda	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Sesquiterpenoid
Fatty acyl glycoside of mono- or disaccharide
Ionone derivative
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Cyclohexanol
Oxane
Monosaccharide
Cyclitol or derivatives
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen 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	-0.87	ALOGPS
logP	-1.8	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.13	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	160.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.1 m³·mol⁻¹	ChemAxon
Polarizability	42.66 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

6325609

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol (NP0227869)

MOL for NP0227869 ((2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol)

3D MOL for NP0227869 ((2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol)

3D SDF for NP0227869 ((2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol)

3D-SDF for NP0227869 ((2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol)

PDB for NP0227869 ((2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol)

3D PDB for NP0227869 ((2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol)

SMILES for NP0227869 ((2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol)

INCHI for NP0227869 ((2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol)

Structure for NP0227869 ((2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol)

3D Structure for NP0227869 ((2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(2s,3e)-4-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-yl]oxy}oxane-3,4,5-triol)