NP-MRD: Showing NP-Card for (S)-1'-methylbutyl caffeate (NP0035599)

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Record Information

Version

2.0

Created at

2021-06-20 19:00:01 UTC

Updated at

2021-06-30 00:06:41 UTC

NP-MRD ID

NP0035599

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-1'-methylbutyl caffeate

Provided By

JEOL Database JEOL Logo

Description

(S)-1'-methylbutyl caffeate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (S)-1'-methylbutyl caffeate is found in Piper obliquum and Piper sanguineispicum. (S)-1'-methylbutyl caffeate was first documented in 2010 (Cabanillas, B. J., et al.). Based on a literature review very few articles have been published on (S)-1'-methylbutyl caffeate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121003D          

 36 36  0  0  0  0            999 V2000
    3.1726   -4.2082    1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8315   -2.7882    1.0882 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8748   -1.8236    2.2772 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5691   -0.3788    1.8583 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6879    0.5603    3.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179   -0.3355    1.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417    0.6553    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7114    1.5094    0.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.5255    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    1.3826   -0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014    1.3494   -1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0251    2.5609   -1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480    2.5875   -2.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0446    1.3932   -2.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3379    1.3497   -2.6194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4302    0.1881   -1.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1199   -0.9843   -1.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175    0.1536   -1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371   -4.8803    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4615   -4.5759    2.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1785   -4.2588    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352   -2.7833    0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5424   -2.4624    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400   -2.1542    3.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649   -1.8687    2.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781   -0.0791    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    0.5284    3.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4714    1.5932    2.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632    0.2959    3.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -0.2691    0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3868    2.1778   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4831    3.5008   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040    3.5388   -2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6239    2.2601   -2.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9997   -0.7151   -2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6680   -0.8088   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 18 11  2  0  0  0  0
  7  6  1  0  0  0  0
 14 16  2  0  0  0  0
  6  4  1  0  0  0  0
 11 12  1  0  0  0  0
  4  3  1  0  0  0  0
 12 13  2  0  0  0  0
  3  2  1  0  0  0  0
 13 14  1  0  0  0  0
  2  1  1  0  0  0  0
 11 10  1  0  0  0  0
 14 15  1  0  0  0  0
 16 18  1  0  0  0  0
 16 17  1  0  0  0  0
 10  9  2  0  0  0  0
  7  8  2  0  0  0  0
  4  5  1  0  0  0  0
 13 33  1  0  0  0  0
 18 36  1  0  0  0  0
 12 32  1  0  0  0  0
 10 31  1  0  0  0  0
  9 30  1  0  0  0  0
  4 26  1  6  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  2 22  1  0  0  0  0
  2 23  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
 15 34  1  0  0  0  0
 17 35  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
M  END

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    3.1726   -4.2082    1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8315   -2.7882    1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748   -1.8236    2.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5691   -0.3788    1.8583 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6879    0.5603    3.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179   -0.3355    1.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417    0.6553    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7114    1.5094    0.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.5255    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    1.3826   -0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014    1.3494   -1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0251    2.5609   -1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480    2.5875   -2.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0446    1.3932   -2.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3379    1.3497   -2.6194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4302    0.1881   -1.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1199   -0.9843   -1.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175    0.1536   -1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371   -4.8803    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4615   -4.5759    2.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1785   -4.2588    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352   -2.7833    0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5424   -2.4624    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400   -2.1542    3.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649   -1.8687    2.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781   -0.0791    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    0.5284    3.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4714    1.5932    2.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632    0.2959    3.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -0.2691    0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3868    2.1778   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4831    3.5008   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040    3.5388   -2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6239    2.2601   -2.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9997   -0.7151   -2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6680   -0.8088   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0
 18 11  2  0
  7  6  1  0
 14 16  2  0
  6  4  1  0
 11 12  1  0
  4  3  1  0
 12 13  2  0
  3  2  1  0
 13 14  1  0
  2  1  1  0
 11 10  1  0
 14 15  1  0
 16 18  1  0
 16 17  1  0
 10  9  2  0
  7  8  2  0
  4  5  1  0
 13 33  1  0
 18 36  1  0
 12 32  1  0
 10 31  1  0
  9 30  1  0
  4 26  1  6
  3 24  1  0
  3 25  1  0
  2 22  1  0
  2 23  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 15 34  1  0
 17 35  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
M  END


  Mrv1652306202121003D          

 36 36  0  0  0  0            999 V2000
    3.1726   -4.2082    1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8315   -2.7882    1.0882 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8748   -1.8236    2.2772 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5691   -0.3788    1.8583 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6879    0.5603    3.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179   -0.3355    1.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417    0.6553    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7114    1.5094    0.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.5255    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    1.3826   -0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014    1.3494   -1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0251    2.5609   -1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480    2.5875   -2.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0446    1.3932   -2.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3379    1.3497   -2.6194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4302    0.1881   -1.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1199   -0.9843   -1.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175    0.1536   -1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371   -4.8803    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4615   -4.5759    2.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1785   -4.2588    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352   -2.7833    0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5424   -2.4624    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400   -2.1542    3.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649   -1.8687    2.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781   -0.0791    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    0.5284    3.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4714    1.5932    2.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632    0.2959    3.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -0.2691    0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3868    2.1778   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4831    3.5008   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040    3.5388   -2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6239    2.2601   -2.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9997   -0.7151   -2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6680   -0.8088   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 18 11  2  0  0  0  0
  7  6  1  0  0  0  0
 14 16  2  0  0  0  0
  6  4  1  0  0  0  0
 11 12  1  0  0  0  0
  4  3  1  0  0  0  0
 12 13  2  0  0  0  0
  3  2  1  0  0  0  0
 13 14  1  0  0  0  0
  2  1  1  0  0  0  0
 11 10  1  0  0  0  0
 14 15  1  0  0  0  0
 16 18  1  0  0  0  0
 16 17  1  0  0  0  0
 10  9  2  0  0  0  0
  7  8  2  0  0  0  0
  4  5  1  0  0  0  0
 13 33  1  0  0  0  0
 18 36  1  0  0  0  0
 12 32  1  0  0  0  0
 10 31  1  0  0  0  0
  9 30  1  0  0  0  0
  4 26  1  6  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  2 22  1  0  0  0  0
  2 23  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
 15 34  1  0  0  0  0
 17 35  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035599

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(O[H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O4/c1-3-4-10(2)18-14(17)8-6-11-5-7-12(15)13(16)9-11/h5-10,15-16H,3-4H2,1-2H3/b8-6+/t10-/m0/s1

> <INCHI_KEY>
AGXDVPULWUXVDT-PCGIRMHASA-N

> <FORMULA>
C14H18O4

> <MOLECULAR_WEIGHT>
250.294

> <EXACT_MASS>
250.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.77027570414692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-pentan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.86

> <JCHEM_LOGP>
3.6486570453333322

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.612467920264038

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.208622589848167

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283760755332687

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
70.08320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-pentan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    3.1726   -4.2082    1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8315   -2.7882    1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748   -1.8236    2.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5691   -0.3788    1.8583 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6879    0.5603    3.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179   -0.3355    1.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417    0.6553    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7114    1.5094    0.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.5255    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    1.3826   -0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014    1.3494   -1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0251    2.5609   -1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480    2.5875   -2.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0446    1.3932   -2.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3379    1.3497   -2.6194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4302    0.1881   -1.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1199   -0.9843   -1.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175    0.1536   -1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371   -4.8803    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4615   -4.5759    2.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1785   -4.2588    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352   -2.7833    0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5424   -2.4624    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400   -2.1542    3.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649   -1.8687    2.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781   -0.0791    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    0.5284    3.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4714    1.5932    2.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632    0.2959    3.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -0.2691    0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3868    2.1778   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4831    3.5008   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040    3.5388   -2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6239    2.2601   -2.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9997   -0.7151   -2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6680   -0.8088   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0
 18 11  2  0
  7  6  1  0
 14 16  2  0
  6  4  1  0
 11 12  1  0
  4  3  1  0
 12 13  2  0
  3  2  1  0
 13 14  1  0
  2  1  1  0
 11 10  1  0
 14 15  1  0
 16 18  1  0
 16 17  1  0
 10  9  2  0
  7  8  2  0
  4  5  1  0
 13 33  1  0
 18 36  1  0
 12 32  1  0
 10 31  1  0
  9 30  1  0
  4 26  1  6
  3 24  1  0
  3 25  1  0
  2 22  1  0
  2 23  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 15 34  1  0
 17 35  1  0
  5 27  1  0
  5 28  1  0
  5 29  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       3.173  -4.208   1.512  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.832  -2.788   1.088  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.875  -1.824   2.277  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.569  -0.379   1.858  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.688   0.560   3.055  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.218  -0.336   1.361  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.942   0.655   0.478  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.711   1.509   0.072  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.475   0.526   0.083  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.002   1.383  -0.805  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.401   1.349  -1.255  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.025   2.561  -1.602  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.348   2.587  -2.059  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.045   1.393  -2.179  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.338   1.350  -2.619  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.430   0.188  -1.852  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.120  -0.984  -1.981  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.118   0.154  -1.398  0.00  0.00           C+0
HETATM   19  H   UNK     0       3.137  -4.880   0.649  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.462  -4.576   2.259  0.00  0.00           H+0
HETATM   21  H   UNK     0       4.178  -4.259   1.941  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.835  -2.783   0.632  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.542  -2.462   0.320  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.140  -2.154   3.022  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.865  -1.869   2.747  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.278  -0.079   1.076  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.693   0.528   3.486  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.471   1.593   2.764  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.963   0.296   3.833  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.045  -0.269   0.548  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.387   2.178  -1.224  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.483   3.501  -1.511  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.804   3.539  -2.313  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.624   2.260  -2.808  0.00  0.00           H+0
HETATM   35  H   UNK     0      -6.000  -0.715  -2.313  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.668  -0.809  -1.174  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    3    1   22   23                                             
CONECT    3    4    2   24   25                                             
CONECT    4    6    3    5   26                                             
CONECT    5    4   27   28   29                                             
CONECT    6    7    4                                                       
CONECT    7    9    6    8                                                  
CONECT    8    7                                                            
CONECT    9    7   10   30                                                  
CONECT   10   11    9   31                                                  
CONECT   11   18   12   10                                                  
CONECT   12   11   13   32                                                  
CONECT   13   12   14   33                                                  
CONECT   14   16   13   15                                                  
CONECT   15   14   34                                                       
CONECT   16   14   18   17                                                  
CONECT   17   16   35                                                       
CONECT   18   11   16   36                                                  
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    2                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    5                                                            
CONECT   28    5                                                            
CONECT   29    5                                                            
CONECT   30    9                                                            
CONECT   31   10                                                            
CONECT   32   12                                                            
CONECT   33   13                                                            
CONECT   34   15                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

RDKit          3D

36 36  0  0  0  0  0  0  0  0999 V2000
    3.1726   -4.2082    1.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8315   -2.7882    1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748   -1.8236    2.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5691   -0.3788    1.8583 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6879    0.5603    3.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179   -0.3355    1.3612 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417    0.6553    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7114    1.5094    0.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.5255    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    1.3826   -0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014    1.3494   -1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0251    2.5609   -1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480    2.5875   -2.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0446    1.3932   -2.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3379    1.3497   -2.6194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4302    0.1881   -1.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1199   -0.9843   -1.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1175    0.1536   -1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371   -4.8803    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4615   -4.5759    2.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1785   -4.2588    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352   -2.7833    0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5424   -2.4624    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1400   -2.1542    3.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649   -1.8687    2.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781   -0.0791    1.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    0.5284    3.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4714    1.5932    2.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632    0.2959    3.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -0.2691    0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3868    2.1778   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4831    3.5008   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040    3.5388   -2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6239    2.2601   -2.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9997   -0.7151   -2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6680   -0.8088   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0
 18 11  2  0
  7  6  1  0
 14 16  2  0
  6  4  1  0
 11 12  1  0
  4  3  1  0
 12 13  2  0
  3  2  1  0
 13 14  1  0
  2  1  1  0
 11 10  1  0
 14 15  1  0
 16 18  1  0
 16 17  1  0
 10  9  2  0
  7  8  2  0
  4  5  1  0
 13 33  1  0
 18 36  1  0
 12 32  1  0
 10 31  1  0
  9 30  1  0
  4 26  1  6
  3 24  1  0
  3 25  1  0
  2 22  1  0
  2 23  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 15 34  1  0
 17 35  1  0
  5 27  1  0
  5 28  1  0
  5 29  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(S)-1'-Methylbutyl caffeic acid	Generator

Chemical Formula

C₁₄H₁₈O₄

Average Mass

250.2940 Da

Monoisotopic Mass

250.12051 Da

IUPAC Name

(2S)-pentan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(2S)-pentan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C(O[H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C14H18O4/c1-3-4-10(2)18-14(17)8-6-11-5-7-12(15)13(16)9-11/h5-10,15-16H,3-4H2,1-2H3/b8-6+/t10-/m0/s1

InChI Key

AGXDVPULWUXVDT-PCGIRMHASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Piper obliquum	LOTUS Database	35616633
Piper sanguineispicum	JEOL database	Cabanillas, B. J., et al, J. Nat. Prod. 73, 1884 (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	3.86	ALOGPS
logP	3.65	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.08 m³·mol⁻¹	ChemAxon
Polarizability	27.77 Å³	ChemAxon
Number of Rings	1	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

26381072

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

70482

Good Scents ID

Not Available

References

General References

Cabanillas, B. J., et al. (2010). Cabanillas, B. J., et al, J. Nat. Prod. 73, 1884 (2010). J. Nat. Prod..

Showing NP-Card for (S)-1'-methylbutyl caffeate (NP0035599)

MOL for NP0035599 ((S)-1'-methylbutyl caffeate)

3D MOL for NP0035599 ((S)-1'-methylbutyl caffeate)

3D SDF for NP0035599 ((S)-1'-methylbutyl caffeate)

3D-SDF for NP0035599 ((S)-1'-methylbutyl caffeate)

PDB for NP0035599 ((S)-1'-methylbutyl caffeate)

3D PDB for NP0035599 ((S)-1'-methylbutyl caffeate)

SMILES for NP0035599 ((S)-1'-methylbutyl caffeate)

INCHI for NP0035599 ((S)-1'-methylbutyl caffeate)

Structure for NP0035599 ((S)-1'-methylbutyl caffeate)

3D Structure for NP0035599 ((S)-1'-methylbutyl caffeate)