NP-MRD: Showing NP-Card for 4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate (NP0222250)

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Record Information

Version

2.0

Created at

2022-09-06 00:02:35 UTC

Updated at

2022-09-06 00:02:35 UTC

NP-MRD ID

NP0222250

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate

Description

4,5-Dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. 4,5-Dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191514172D          

 46 50  0  0  0  0            999 V2000
   -7.4409   -4.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1859   -3.8653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3790   -3.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1240   -2.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3171   -2.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7650   -3.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9580   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -3.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -1.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200   -4.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8269   -4.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  0  0  0  0
 24 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 18 40  1  0  0  0  0
 23 40  1  0  0  0  0
 16 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 12 43  1  0  0  0  0
 43 44  1  0  0  0  0
  6 45  1  0  0  0  0
 45 46  2  0  0  0  0
  3 46  1  0  0  0  0
M  END


  Mrv1533004191514172D          

 46 50  0  0  0  0            999 V2000
   -7.4409   -4.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1859   -3.8653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3790   -3.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1240   -2.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3171   -2.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7650   -3.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9580   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -3.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -1.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200   -4.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8269   -4.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  0  0  0  0
 24 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 18 40  1  0  0  0  0
 23 40  1  0  0  0  0
 16 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 12 43  1  0  0  0  0
 43 44  1  0  0  0  0
  6 45  1  0  0  0  0
 45 46  2  0  0  0  0
  3 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222250

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=CC(=O)OC2C(C)OC(OC3C=C(CO)C4C3C=COC4OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O15/c1-14-28(45-21(34)8-5-15-3-6-17(40-2)7-4-15)25(37)27(39)30(42-14)43-19-11-16(12-32)22-18(19)9-10-41-29(22)46-31-26(38)24(36)23(35)20(13-33)44-31/h3-11,14,18-20,22-33,35-39H,12-13H2,1-2H3

> <INCHI_KEY>
UAGRGXCEWYZPRL-UHFFFAOYSA-N

> <FORMULA>
C31H40O15

> <MOLECULAR_WEIGHT>
652.646

> <EXACT_MASS>
652.236720588

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
66.79678059165867

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-1.029576129000001

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.484245279604103

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.936885958490455

> <JCHEM_PKA_STRONGEST_BASIC>
-2.741513063081543

> <JCHEM_POLAR_SURFACE_AREA>
223.28999999999996

> <JCHEM_REFRACTIVITY>
156.0773

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0     -13.890  -8.680   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -13.414  -7.215   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -11.907  -6.895   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.432  -5.430   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.925  -5.110   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.895  -6.255   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.388  -5.934   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.358  -7.079   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.852  -6.759   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.821  -7.903   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.376  -5.294   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.869  -4.974   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.393  -3.509   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.424  -2.365   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.680   2.552   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.258   4.087   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.591   4.857   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.591   6.397   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.925   7.167   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.925   4.087   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.259   4.857   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.925   2.547   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.259   1.777   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.315  -7.583   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -9.371  -7.719   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -10.877  -8.039   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   46                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   45                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   43                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   41                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   40                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   40                                                  
CONECT   24   23   25   37                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   26   36                                                  
CONECT   36   35                                                            
CONECT   37   24   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   18   23                                                  
CONECT   41   16   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   12   44                                                  
CONECT   44   43                                                            
CONECT   45    6   46                                                       
CONECT   46   45    3                                                       
MASTER        0    0    0    0    0    0    0    0   46    0  100    0
END

View in JSmol

Synonyms

Value	Source
4,5-Dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₃₁H₄₀O₁₅

Average Mass

652.6460 Da

Monoisotopic Mass

652.23672 Da

IUPAC Name

4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate

Traditional Name

4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=CC(=O)OC2C(C)OC(OC3C=C(CO)C4C3C=COC4OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C=C1

InChI Identifier

InChI=1S/C31H40O15/c1-14-28(45-21(34)8-5-15-3-6-17(40-2)7-4-15)25(37)27(39)30(42-14)43-19-11-16(12-32)22-18(19)9-10-41-29(22)46-31-26(38)24(36)23(35)20(13-33)44-31/h3-11,14,18-20,22-33,35-39H,12-13H2,1-2H3

InChI Key

UAGRGXCEWYZPRL-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Cinnamic acid or derivatives
Cinnamic acid ester
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Monoterpenoid
Aromatic monoterpenoid
Bicyclic monoterpenoid
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
Fatty acid ester
Alkyl aryl ether
Monosaccharide
Monocyclic benzene moiety
Oxane
Fatty acyl
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Polyol
Ether
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Primary alcohol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.14	ALOGPS
logP	-1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	223.29 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	156.08 m³·mol⁻¹	ChemAxon
Polarizability	66.8 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

74169051

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate (NP0222250)

MOL for NP0222250 (4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D MOL for NP0222250 (4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D SDF for NP0222250 (4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0222250 (4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

PDB for NP0222250 (4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D PDB for NP0222250 (4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

SMILES for NP0222250 (4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

INCHI for NP0222250 (4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

Structure for NP0222250 (4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D Structure for NP0222250 (4,5-dihydroxy-6-{[7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-2-methyloxan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)