NP-MRD: Showing NP-Card for butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate (NP0289657)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 19:57:01 UTC

Updated at

2022-09-09 19:57:01 UTC

NP-MRD ID

NP0289657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate

Description

Hycandinic acid ester 1 belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1. butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate is found in Hydrastis canadensis. butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate was first documented in 2013 (PMID: 23888695). Based on a literature review very few articles have been published on Hycandinic acid ester 1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092221572D          

 29 30  0  0  1  0            999 V2000
   -1.7410   -7.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266   -7.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121   -7.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -7.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168   -7.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313   -7.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313   -6.7465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5458   -7.9840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0155   -8.6159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8280   -7.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6404   -7.0654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9226   -6.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1707   -7.6974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9832   -7.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -8.4727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4189   -9.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367   -9.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2313   -8.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5135   -8.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3260   -8.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6081   -7.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4206   -7.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9509   -7.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7634   -7.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6687   -8.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1990   -9.1636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9169   -9.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8563   -8.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0761   -8.6159    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  2  0  0  0  0
 20 28  1  0  0  0  0
 15 29  1  0  0  0  0
  8 29  1  0  0  0  0
M  END

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
    8.0409    1.0659    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8226   -0.1663    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3801   -0.6325    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4643    0.4254   -0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1297   -0.0047   -0.3293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4822   -0.3363    0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0486   -0.2691    1.9673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0681   -0.7891    0.8109 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6351   -1.0615    2.0830 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9611   -1.9477   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6833   -1.8921   -0.9556 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4437   -3.1577   -1.4952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -1.4533   -0.0528 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4422   -2.2901    1.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027   -0.0288    0.3478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0336    0.9353   -0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728    1.8140   -1.0759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5131    0.8803   -0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644    1.7396   -0.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7176    1.7479   -0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4272    2.7018   -1.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8053    2.7448   -1.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5300    1.8143   -0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9304    1.8474   -0.9251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8665    0.8548   -0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6059   -0.0695    0.5319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8820   -1.0385    1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4907    0.8545   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442    0.3481    0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0848    1.0658    1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9007    2.0018    0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3714    1.0510    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1642    0.0056   -0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4430   -0.9877    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3457   -1.5136   -0.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0877   -1.0298    1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7201    0.6213   -1.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5101    1.3572    0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161   -1.9313    2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232   -1.9169   -0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0446   -2.9174    0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8350   -1.1331   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883   -3.3750   -2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -1.5878   -0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8328   -3.1707    0.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190    0.0197    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0042    0.1258    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7620    2.4898   -1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946    3.4388   -2.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3639    3.4868   -2.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4385    1.1621   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5435   -1.7014    1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1747   -1.6040    0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2410   -0.5089    2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0114    0.0861    0.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5396    0.5445   -0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3807    1.2845    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 29  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  2  0
 29  8  1  0
 28 20  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  6
 12 43  1  0
 13 44  1  6
 14 45  1  0
 15 46  1  1
 29 56  1  0
 29 57  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
M  END


  Mrv1652309092221572D          

 29 30  0  0  1  0            999 V2000
   -1.7410   -7.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266   -7.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121   -7.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -7.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168   -7.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313   -7.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313   -6.7465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5458   -7.9840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0155   -8.6159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8280   -7.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6404   -7.0654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9226   -6.2902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1707   -7.6974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9832   -7.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -8.4727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4189   -9.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367   -9.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2313   -8.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5135   -8.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3260   -8.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6081   -7.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4206   -7.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9509   -7.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7634   -7.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6687   -8.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1990   -9.1636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9169   -9.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8563   -8.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0761   -8.6159    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  2  0  0  0  0
 20 28  1  0  0  0  0
 15 29  1  0  0  0  0
  8 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCOC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@@H](C1)C(=O)\C=C\C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O8/c1-3-4-9-29-20(26)21(27)11-14(19(25)17(24)12-21)15(22)7-5-13-6-8-16(23)18(10-13)28-2/h5-8,10,14,17,19,23-25,27H,3-4,9,11-12H2,1-2H3/b7-5+/t14-,17+,19-,21+/m0/s1

> <INCHI_KEY>
XNOOTNIUGJXYKK-RSCBJFFSSA-N

> <FORMULA>
C21H28O8

> <MOLECULAR_WEIGHT>
408.447

> <EXACT_MASS>
408.178417862

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.49561299230896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
butyl (1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate

> <JCHEM_LOGP>
1.5286737339999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.800225789562157

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.507830222475892

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2062388279486616

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
105.52729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
butyl (1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.250 -14.903   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.916 -14.133   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.583 -14.903   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.751 -14.133   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.085 -14.903   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.418 -14.133   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.418 -12.593   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.752 -14.903   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.762 -16.083   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.279 -13.456   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.795 -13.189   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.322 -11.742   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.785 -14.369   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.302 -14.101   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.259 -15.816   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.249 -16.995   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.722 -18.443   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.765 -16.728   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.292 -15.281   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.808 -15.013   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.335 -13.566   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.852 -13.299   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.842 -14.479   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.358 -14.211   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.315 -15.926   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.305 -17.105   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.778 -18.553   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.798 -16.193   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.742 -16.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   29                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   29                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   20                                                       
CONECT   29   15    8                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Value	Source
Hycandinate ester 1	Generator

Chemical Formula

C₂₁H₂₈O₈

Average Mass

408.4470 Da

Monoisotopic Mass

408.17842 Da

IUPAC Name

butyl (1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate

Traditional Name

butyl (1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCOC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@@H](C1)C(=O)\C=C\C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C21H28O8/c1-3-4-9-29-20(26)21(27)11-14(19(25)17(24)12-21)15(22)7-5-13-6-8-16(23)18(10-13)28-2/h5-8,10,14,17,19,23-25,27H,3-4,9,11-12H2,1-2H3/b7-5+/t14-,17+,19-,21+/m0/s1

InChI Key

XNOOTNIUGJXYKK-RSCBJFFSSA-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
Hydrastis canadensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
B'-hydroxy-alpha,beta-unsaturated-ketone
Phenol
Cyclohexanol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Acryloyl-group
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.53	ChemAxon
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	105.53 m³·mol⁻¹	ChemAxon
Polarizability	42.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

100916732

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang Y, Zhang Y, Ren FX, Yu NJ, Xu R, Zhao YM: [Chemical constituents from the roots of Angelica polymorpha Maxim]. Yao Xue Xue Bao. 2013 May;48(5):718-22. [PubMed:23888695 ]
LOTUS database [Link]

Showing NP-Card for butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate (NP0289657)

MOL for NP0289657 (butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate)

3D MOL for NP0289657 (butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate)

3D SDF for NP0289657 (butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate)

3D-SDF for NP0289657 (butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate)

PDB for NP0289657 (butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate)

3D PDB for NP0289657 (butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate)

SMILES for NP0289657 (butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate)

INCHI for NP0289657 (butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate)

Structure for NP0289657 (butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate)

3D Structure for NP0289657 (butyl (1r,3r,4s,5r)-1,3,4-trihydroxy-5-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylate)