NP-MRD: Showing NP-Card for rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+ (NP0035132)

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Record Information

Version

2.0

Created at

2021-06-20 18:39:48 UTC

Updated at

2021-06-30 00:05:56 UTC

NP-MRD ID

NP0035132

Secondary Accession Numbers

None

Natural Product Identification

Common Name

rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+

Provided By

JEOL Database JEOL Logo

Description

rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+ is found in Conyza canadensis. rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+ was first documented in 2010 (Ding, Y., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120393D          

 72 75  0  0  0  0            999 V2000
    3.5451    1.3209   -4.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5360    0.3417   -3.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0893   -1.2626   -4.3522 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 72 75  0  0  0  0  0  0  0  0999 V2000
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 37 68  1  0
 32 65  1  0
 31 64  1  0
 23 59  1  0
 22 58  1  6
 24 60  1  1
  6 46  1  0
  6 47  1  0
  7 48  1  6
 26 61  1  1
  1 43  1  0
  1 44  1  0
  1 45  1  0
 27 62  1  0
 27 63  1  0
 15 52  1  0
 14 51  1  0
 21 57  1  0
 17 53  1  0
 12 50  1  0
 11 49  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 40 69  1  0
 40 70  1  0
 40 71  1  0
M  END


  Mrv1652306202120393D          

 72 75  0  0  0  0            999 V2000
    3.5451    1.3209   -4.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5360    0.3417   -3.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594   -0.9490   -3.9944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0893   -1.2626   -4.3522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -1.9457   -3.6861 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7485   -1.8759   -4.8050 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4451   -2.7935   -4.4906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3030   -2.0775   -3.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962   -2.4668   -3.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1103   -3.3313   -4.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3387   -1.7341   -2.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497   -0.9637   -1.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4578   -0.2461   -0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6816   -0.6892    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3073    0.0107    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6979    1.1435    1.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3257    1.8073    2.6352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4676    1.5981    1.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9864    2.7212    1.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6908    3.1619    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8511    0.8971    0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -4.1412   -3.8875 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0068   -4.8792   -3.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144   -3.9560   -2.9129 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2625   -3.3086   -3.6436 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9615   -2.9536   -1.7990 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9638   -3.0916   -0.6449 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7124   -2.0863    0.3592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6588   -2.3317    1.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0337   -3.3349    1.1825 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679   -1.1486    2.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328   -1.1264    2.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8488    0.0080    3.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068    0.9632    4.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439    2.0280    5.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458    2.1234    5.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8663    3.1780    6.3046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5111    1.1676    5.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7494    1.3819    5.7164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6540    0.2822    5.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1575    0.1143    4.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1736   -1.6671   -2.4274 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    2.3081   -3.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804    1.2718   -5.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3867    1.1866   -3.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -2.1974   -5.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3928   -0.8462   -4.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0078   -2.9714   -5.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4095   -1.8964   -2.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6688   -0.8321   -1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1628   -1.5881   -0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2580   -0.3284    1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7105    2.5274    2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9387    2.3829    1.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6898    3.5015    0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4256    4.0157    1.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983    1.2277   -0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3992   -4.7516   -4.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020   -4.8335   -3.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5481   -4.9274   -2.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0621   -2.9934   -1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9338   -4.0910   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865   -2.9153   -0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479   -0.3213    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -1.9877    3.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1371    0.8945    3.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4931    2.7721    5.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8094    3.0466    6.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190   -0.6056    6.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9720    0.0653    4.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5438    0.5618    6.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8954   -0.6242    4.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
 23 22  1  0  0  0  0
  5  3  1  6  0  0  0
 31 29  1  0  0  0  0
 24 26  1  0  0  0  0
 41 38  2  0  0  0  0
  5 42  1  0  0  0  0
 26 42  1  0  0  0  0
 29 30  2  0  0  0  0
  3  2  1  0  0  0  0
 38 36  1  0  0  0  0
  2  1  1  0  0  0  0
 29 28  1  0  0  0  0
  3  4  2  0  0  0  0
 36 35  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 38 39  1  0  0  0  0
 34 33  2  0  0  0  0
 16 15  1  0  0  0  0
 36 37  1  0  0  0  0
 15 14  2  0  0  0  0
 14 13  1  0  0  0  0
 33 32  1  0  0  0  0
 13 21  2  0  0  0  0
 33 41  1  0  0  0  0
 21 18  1  0  0  0  0
 18 16  2  0  0  0  0
 32 31  2  0  0  0  0
 18 19  1  0  0  0  0
 35 34  1  0  0  0  0
 16 17  1  0  0  0  0
 22  7  1  0  0  0  0
 13 12  1  0  0  0  0
  7  6  1  0  0  0  0
 12 11  2  0  0  0  0
  6  5  1  0  0  0  0
 11  9  1  0  0  0  0
  5 25  1  0  0  0  0
  9 10  2  0  0  0  0
  9  8  1  0  0  0  0
 25 24  1  0  0  0  0
 19 20  1  0  0  0  0
 24 22  1  0  0  0  0
 39 40  1  0  0  0  0
 35 67  1  0  0  0  0
 34 66  1  0  0  0  0
 41 72  1  0  0  0  0
 37 68  1  0  0  0  0
 32 65  1  0  0  0  0
 31 64  1  0  0  0  0
 23 59  1  0  0  0  0
 22 58  1  6  0  0  0
 24 60  1  1  0  0  0
  6 46  1  0  0  0  0
  6 47  1  0  0  0  0
  7 48  1  6  0  0  0
 26 61  1  1  0  0  0
  1 43  1  0  0  0  0
  1 44  1  0  0  0  0
  1 45  1  0  0  0  0
 27 62  1  0  0  0  0
 27 63  1  0  0  0  0
 15 52  1  0  0  0  0
 14 51  1  0  0  0  0
 21 57  1  0  0  0  0
 17 53  1  0  0  0  0
 12 50  1  0  0  0  0
 11 49  1  0  0  0  0
 20 54  1  0  0  0  0
 20 55  1  0  0  0  0
 20 56  1  0  0  0  0
 40 69  1  0  0  0  0
 40 70  1  0  0  0  0
 40 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035132

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)OC([H])([H])[C@@]2([H])O[C@]3(O[C@]2([H])[C@@]([H])(O[H])[C@@]([H])(OC(=O)C(\[H])=C(/[H])C2=C([H])C(OC([H])([H])[H])=C(O[H])C([H])=C2[H])C3([H])[H])C(=O)OC([H])([H])[H])C([H])=C1OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C29H30O13/c1-36-20-12-16(4-8-18(20)30)6-10-24(32)39-15-23-27-26(34)22(14-29(41-23,42-27)28(35)38-3)40-25(33)11-7-17-5-9-19(31)21(13-17)37-2/h4-13,22-23,26-27,30-31,34H,14-15H2,1-3H3/b10-6+,11-7+/t22-,23+,26-,27-,29+/m0/s1

> <INCHI_KEY>
PIOVWQJEQIKPND-LWVVXDACSA-N

> <FORMULA>
C29H30O13

> <MOLECULAR_WEIGHT>
586.546

> <EXACT_MASS>
586.168641026

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
56.97989279694455

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2S,3S,5R,7R)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-7-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
3.807338506333333

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.168408006813092

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.566608271896222

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6343679249518077

> <JCHEM_POLAR_SURFACE_AREA>
176.51

> <JCHEM_REFRACTIVITY>
144.0002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,3S,5R,7R)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-7-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 72 75  0  0  0  0  0  0  0  0999 V2000
    3.5451    1.3209   -4.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5360    0.3417   -3.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594   -0.9490   -3.9944 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0893   -1.2626   -4.3522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -1.9457   -3.6861 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7485   -1.8759   -4.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4451   -2.7935   -4.4906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3030   -2.0775   -3.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962   -2.4668   -3.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1103   -3.3313   -4.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3387   -1.7341   -2.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497   -0.9637   -1.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4578   -0.2461   -0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6816   -0.6892    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3073    0.0107    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6979    1.1435    1.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3257    1.8073    2.6352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4676    1.5981    1.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9864    2.7212    1.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6908    3.1619    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8511    0.8971    0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -4.1412   -3.8875 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0068   -4.8792   -3.2547 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144   -3.9560   -2.9129 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2625   -3.3086   -3.6436 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9615   -2.9536   -1.7990 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9638   -3.0916   -0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124   -2.0863    0.3592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6588   -2.3317    1.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0337   -3.3349    1.1825 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679   -1.1486    2.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328   -1.1264    2.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8488    0.0080    3.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068    0.9632    4.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439    2.0280    5.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458    2.1234    5.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8663    3.1780    6.3046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5111    1.1676    5.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7494    1.3819    5.7164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6540    0.2822    5.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1575    0.1143    4.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1736   -1.6671   -2.4274 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    2.3081   -3.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804    1.2718   -5.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3867    1.1866   -3.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -2.1974   -5.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3928   -0.8462   -4.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0078   -2.9714   -5.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4095   -1.8964   -2.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6688   -0.8321   -1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1628   -1.5881   -0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2580   -0.3284    1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7105    2.5274    2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9387    2.3829    1.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6898    3.5015    0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4256    4.0157    1.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983    1.2277   -0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3992   -4.7516   -4.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020   -4.8335   -3.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5481   -4.9274   -2.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0621   -2.9934   -1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9338   -4.0910   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865   -2.9153   -0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479   -0.3213    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -1.9877    3.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1371    0.8945    3.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4931    2.7721    5.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8094    3.0466    6.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190   -0.6056    6.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9720    0.0653    4.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5438    0.5618    6.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8954   -0.6242    4.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 23 22  1  0
  5  3  1  6
 31 29  1  0
 24 26  1  0
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 22  7  1  0
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 11  9  1  0
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 40 71  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.545   1.321  -4.074  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.536   0.342  -3.828  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.959  -0.949  -3.994  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.089  -1.263  -4.352  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.807  -1.946  -3.686  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.749  -1.876  -4.805  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.445  -2.793  -4.491  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.303  -2.078  -3.572  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.596  -2.467  -3.507  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.110  -3.331  -4.203  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.339  -1.734  -2.462  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.750  -0.964  -1.532  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.458  -0.246  -0.458  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.682  -0.689   0.066  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.307   0.011   1.098  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.698   1.143   1.617  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.326   1.807   2.635  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.468   1.598   1.134  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.986   2.721   1.755  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.691   3.162   1.367  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.851   0.897   0.096  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.034  -4.141  -3.888  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.007  -4.879  -3.255  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.214  -3.956  -2.913  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.263  -3.309  -3.644  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.962  -2.954  -1.799  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.964  -3.092  -0.645  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.712  -2.086   0.359  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.659  -2.332   1.175  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.034  -3.335   1.183  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.468  -1.149   2.037  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.533  -1.126   2.931  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.849   0.008   3.815  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.107   0.963   4.195  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.244   2.028   5.026  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.546   2.123   5.494  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.866   3.178   6.305  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.511   1.168   5.167  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.749   1.382   5.716  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.654   0.282   5.675  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.158   0.114   4.322  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.174  -1.667  -2.427  0.00  0.00           O+0
HETATM   43  H   UNK     0       3.109   2.308  -3.898  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.880   1.272  -5.115  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.387   1.187  -3.388  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.205  -2.197  -5.750  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.393  -0.846  -4.931  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.008  -2.971  -5.416  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.410  -1.896  -2.493  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.669  -0.832  -1.538  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.163  -1.588  -0.310  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.258  -0.328   1.498  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.710   2.527   2.881  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.939   2.383   1.527  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.690   3.502   0.326  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.426   4.016   1.998  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.898   1.228  -0.306  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.399  -4.752  -4.724  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.802  -4.833  -3.826  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.548  -4.927  -2.534  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.062  -2.993  -1.417  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.934  -4.091  -0.195  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.986  -2.915  -0.996  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.148  -0.321   1.884  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.196  -1.988   3.012  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.137   0.895   3.857  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.493   2.772   5.312  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.809   3.047   6.525  0.00  0.00           H+0
HETATM   69  H   UNK     0      -4.219  -0.606   6.146  0.00  0.00           H+0
HETATM   70  H   UNK     0      -4.972   0.065   4.652  0.00  0.00           H+0
HETATM   71  H   UNK     0      -5.544   0.562   6.247  0.00  0.00           H+0
HETATM   72  H   UNK     0      -2.895  -0.624   4.022  0.00  0.00           H+0
CONECT    1    2   43   44   45                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    3   42    6   25                                             
CONECT    6    7    5   46   47                                             
CONECT    7    8   22    6   48                                             
CONECT    8    7    9                                                       
CONECT    9   11   10    8                                                  
CONECT   10    9                                                            
CONECT   11   12    9   49                                                  
CONECT   12   13   11   50                                                  
CONECT   13   14   21   12                                                  
CONECT   14   15   13   51                                                  
CONECT   15   16   14   52                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16   53                                                       
CONECT   18   21   16   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   54   55   56                                             
CONECT   21   13   18   57                                                  
CONECT   22   23    7   24   58                                             
CONECT   23   22   59                                                       
CONECT   24   26   25   22   60                                             
CONECT   25    5   24                                                       
CONECT   26   24   42   27   61                                             
CONECT   27   26   28   62   63                                             
CONECT   28   29   27                                                       
CONECT   29   31   30   28                                                  
CONECT   30   29                                                            
CONECT   31   29   32   64                                                  
CONECT   32   33   31   65                                                  
CONECT   33   34   32   41                                                  
CONECT   34   33   35   66                                                  
CONECT   35   36   34   67                                                  
CONECT   36   38   35   37                                                  
CONECT   37   36   68                                                       
CONECT   38   41   36   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   69   70   71                                             
CONECT   41   38   33   72                                                  
CONECT   42    5   26                                                       
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    1                                                            
CONECT   46    6                                                            
CONECT   47    6                                                            
CONECT   48    7                                                            
CONECT   49   11                                                            
CONECT   50   12                                                            
CONECT   51   14                                                            
CONECT   52   15                                                            
CONECT   53   17                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   27                                                            
CONECT   64   31                                                            
CONECT   65   32                                                            
CONECT   66   34                                                            
CONECT   67   35                                                            
CONECT   68   37                                                            
CONECT   69   40                                                            
CONECT   70   40                                                            
CONECT   71   40                                                            
CONECT   72   41                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  150    0
END

RDKit          3D

72 75  0  0  0  0  0  0  0  0999 V2000
    3.5451    1.3209   -4.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5360    0.3417   -3.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0893   -1.2626   -4.3522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -1.9457   -3.6861 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7485   -1.8759   -4.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4451   -2.7935   -4.4906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3030   -2.0775   -3.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962   -2.4668   -3.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1103   -3.3313   -4.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3387   -1.7341   -2.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497   -0.9637   -1.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4578   -0.2461   -0.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6816   -0.6892    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3073    0.0107    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6979    1.1435    1.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4679   -1.1486    2.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328   -1.1264    2.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1068    0.9632    4.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439    2.0280    5.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7494    1.3819    5.7164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6540    0.2822    5.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1575    0.1143    4.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1736   -1.6671   -2.4274 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    2.3081   -3.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804    1.2718   -5.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2050   -2.1974   -5.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3928   -0.8462   -4.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3992   -4.7516   -4.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020   -4.8335   -3.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5481   -4.9274   -2.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0621   -2.9934   -1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9338   -4.0910   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865   -2.9153   -0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1479   -0.3213    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -1.9877    3.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1371    0.8945    3.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4931    2.7721    5.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8094    3.0466    6.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190   -0.6056    6.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9720    0.0653    4.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5438    0.5618    6.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8954   -0.6242    4.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 23 22  1  0
  5  3  1  6
 31 29  1  0
 24 26  1  0
 41 38  2  0
  5 42  1  0
 26 42  1  0
 29 30  2  0
  3  2  1  0
 38 36  1  0
  2  1  1  0
 29 28  1  0
  3  4  2  0
 36 35  2  0
 26 27  1  0
 27 28  1  0
 38 39  1  0
 34 33  2  0
 16 15  1  0
 36 37  1  0
 15 14  2  0
 14 13  1  0
 33 32  1  0
 13 21  2  0
 33 41  1  0
 21 18  1  0
 18 16  2  0
 32 31  2  0
 18 19  1  0
 35 34  1  0
 16 17  1  0
 22  7  1  0
 13 12  1  0
  7  6  1  0
 12 11  2  0
  6  5  1  0
 11  9  1  0
  5 25  1  0
  9 10  2  0
  9  8  1  0
 25 24  1  0
 19 20  1  0
 24 22  1  0
 39 40  1  0
 35 67  1  0
 34 66  1  0
 41 72  1  0
 37 68  1  0
 32 65  1  0
 31 64  1  0
 23 59  1  0
 22 58  1  6
 24 60  1  1
  6 46  1  0
  6 47  1  0
  7 48  1  6
 26 61  1  1
  1 43  1  0
  1 44  1  0
  1 45  1  0
 27 62  1  0
 27 63  1  0
 15 52  1  0
 14 51  1  0
 21 57  1  0
 17 53  1  0
 12 50  1  0
 11 49  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 40 69  1  0
 40 70  1  0
 40 71  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₀O₁₃

Average Mass

586.5460 Da

Monoisotopic Mass

586.16864 Da

IUPAC Name

methyl (1R,2S,3S,5R,7R)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-7-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate

Traditional Name

methyl (1R,2S,3S,5R,7R)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-7-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-6,8-dioxabicyclo[3.2.1]octane-5-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)OC([H])([H])[C@@]2([H])O[C@]3(O[C@]2([H])[C@@]([H])(O[H])[C@@]([H])(OC(=O)C(\[H])=C(/[H])C2=C([H])C(OC([H])([H])[H])=C(O[H])C([H])=C2[H])C3([H])[H])C(=O)OC([H])([H])[H])C([H])=C1OC([H])([H])[H]

InChI Identifier

InChI=1S/C29H30O13/c1-36-20-12-16(4-8-18(20)30)6-10-24(32)39-15-23-27-26(34)22(14-29(41-23,42-27)28(35)38-3)40-25(33)11-7-17-5-9-19(31)21(13-17)37-2/h4-13,22-23,26-27,30-31,34H,14-15H2,1-3H3/b10-6+,11-7+/t22-,23+,26-,27-,29+/m0/s1

InChI Key

PIOVWQJEQIKPND-LWVVXDACSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Erigeron canadensis	JEOL database	Ding, Y., et al, J. Nat. Prod. 73, 255 (2010)

Chemical Taxonomy

Classification

Not classified

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	2.65	ALOGPS
logP	3.81	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.57	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	176.51 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	144 m³·mol⁻¹	ChemAxon
Polarizability	56.98 Å³	ChemAxon
Number of Rings	4	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

Not Available

References

General References

Ding, Y., et al. (2010). Ding, Y., et al, J. Nat. Prod. 73, 255 (2010). J. Nat. Prod..

Showing NP-Card for rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+ (NP0035132)

MOL for NP0035132 (rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+)

3D MOL for NP0035132 (rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+)

3D SDF for NP0035132 (rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+)

3D-SDF for NP0035132 (rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+)

PDB for NP0035132 (rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+)

3D PDB for NP0035132 (rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+)

SMILES for NP0035132 (rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+)

INCHI for NP0035132 (rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+)

Structure for NP0035132 (rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+)

3D Structure for NP0035132 (rel-(1S,2R,3R,5S,7R)-methyl 7-feruloyloxymethyl-2-hydroxy-3-feruloyloxy-6+)