NP-MRD: Showing NP-Card for (R)-(+)-umbelactone (NP0028035)

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Record Information

Version

2.0

Created at

2021-06-19 20:01:58 UTC

Updated at

2021-06-29 23:54:33 UTC

NP-MRD ID

NP0028035

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-(+)-umbelactone

Provided By

JEOL Database JEOL Logo

Description

(R)-(+)-umbelactone is found in Crypteronia paniculata. (R)-(+)-umbelactone was first documented in 2005 (Deng, J.-Z., et al.). Based on a literature review very few articles have been published on umbelactonyl caffeate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122013D          

 35 36  0  0  0  0            999 V2000
   -2.0550   -3.9440    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569   -4.5156   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1476   -5.7559   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438   -5.8696   -2.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8803   -6.8662   -3.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -4.6919   -2.8983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -3.7422   -1.8215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0484   -2.5186   -2.2793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0526   -1.4572   -1.3096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9145   -0.7232   -1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0954   -0.9058   -1.9107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982    0.3300   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026    1.1928    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1735    2.2668    1.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0126    2.6693    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098    3.7018    2.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856    4.3403    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572    5.3554    3.8149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    3.9590    2.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330    4.5981    2.5557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3665    2.9362    1.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944   -4.7064    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068   -3.1498    0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164   -3.5293    1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838   -6.5651   -0.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116   -3.4709   -1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -2.7981   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6795   -2.1470   -3.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0479    0.3540    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    1.1089   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    2.1734    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403    3.9854    3.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    5.5118    4.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2862    5.2693    3.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3016    2.6855    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  0  0  0  0
 10 11  2  0  0  0  0
 15 16  2  0  0  0  0
  9  8  1  0  0  0  0
 16 17  1  0  0  0  0
  7  6  1  0  0  0  0
 17 19  2  0  0  0  0
 14 13  1  0  0  0  0
 21 14  2  0  0  0  0
 13 12  2  0  0  0  0
  6  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  2  0  0  0  0
  2  7  1  0  0  0  0
  4  5  2  0  0  0  0
 12 10  1  0  0  0  0
  2  1  1  0  0  0  0
 14 15  1  0  0  0  0
 19 20  1  0  0  0  0
 10  9  1  0  0  0  0
 17 18  1  0  0  0  0
  7  8  1  0  0  0  0
 21 35  1  0  0  0  0
 15 31  1  0  0  0  0
 16 32  1  0  0  0  0
 13 30  1  0  0  0  0
 12 29  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  7 26  1  1  0  0  0
  3 25  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
 20 34  1  0  0  0  0
 18 33  1  0  0  0  0
M  END

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.0550   -3.9440    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569   -4.5156   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1476   -5.7559   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438   -5.8696   -2.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8803   -6.8662   -3.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -4.6919   -2.8983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -3.7422   -1.8215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0484   -2.5186   -2.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0526   -1.4572   -1.3096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9145   -0.7232   -1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0954   -0.9058   -1.9107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982    0.3300   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026    1.1928    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1735    2.2668    1.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0126    2.6693    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098    3.7018    2.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856    4.3403    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572    5.3554    3.8149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    3.9590    2.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330    4.5981    2.5557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3665    2.9362    1.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944   -4.7064    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068   -3.1498    0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164   -3.5293    1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838   -6.5651   -0.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116   -3.4709   -1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -2.7981   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6795   -2.1470   -3.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0479    0.3540    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    1.1089   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    2.1734    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403    3.9854    3.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    5.5118    4.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2862    5.2693    3.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3016    2.6855    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  0
 10 11  2  0
 15 16  2  0
  9  8  1  0
 16 17  1  0
  7  6  1  0
 17 19  2  0
 14 13  1  0
 21 14  2  0
 13 12  2  0
  6  4  1  0
  4  3  1  0
  3  2  2  0
  2  7  1  0
  4  5  2  0
 12 10  1  0
  2  1  1  0
 14 15  1  0
 19 20  1  0
 10  9  1  0
 17 18  1  0
  7  8  1  0
 21 35  1  0
 15 31  1  0
 16 32  1  0
 13 30  1  0
 12 29  1  0
  8 27  1  0
  8 28  1  0
  7 26  1  1
  3 25  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 20 34  1  0
 18 33  1  0
M  END


  Mrv1652306192122013D          

 35 36  0  0  0  0            999 V2000
   -2.0550   -3.9440    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569   -4.5156   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1476   -5.7559   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438   -5.8696   -2.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8803   -6.8662   -3.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -4.6919   -2.8983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -3.7422   -1.8215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0484   -2.5186   -2.2793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0526   -1.4572   -1.3096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9145   -0.7232   -1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0954   -0.9058   -1.9107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982    0.3300   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026    1.1928    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1735    2.2668    1.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0126    2.6693    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098    3.7018    2.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856    4.3403    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572    5.3554    3.8149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    3.9590    2.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330    4.5981    2.5557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3665    2.9362    1.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944   -4.7064    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068   -3.1498    0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164   -3.5293    1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838   -6.5651   -0.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116   -3.4709   -1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -2.7981   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6795   -2.1470   -3.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0479    0.3540    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    1.1089   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    2.1734    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403    3.9854    3.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    5.5118    4.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2862    5.2693    3.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3016    2.6855    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  0  0  0  0
 10 11  2  0  0  0  0
 15 16  2  0  0  0  0
  9  8  1  0  0  0  0
 16 17  1  0  0  0  0
  7  6  1  0  0  0  0
 17 19  2  0  0  0  0
 14 13  1  0  0  0  0
 21 14  2  0  0  0  0
 13 12  2  0  0  0  0
  6  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  2  0  0  0  0
  2  7  1  0  0  0  0
  4  5  2  0  0  0  0
 12 10  1  0  0  0  0
  2  1  1  0  0  0  0
 14 15  1  0  0  0  0
 19 20  1  0  0  0  0
 10  9  1  0  0  0  0
 17 18  1  0  0  0  0
  7  8  1  0  0  0  0
 21 35  1  0  0  0  0
 15 31  1  0  0  0  0
 16 32  1  0  0  0  0
 13 30  1  0  0  0  0
 12 29  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  7 26  1  1  0  0  0
  3 25  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
 20 34  1  0  0  0  0
 18 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028035

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(O[H])C([H])=C(\C([H])=C(/[H])C(=O)OC([H])([H])[C@]2([H])OC(=O)C([H])=C2C([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O6/c1-9-6-15(19)21-13(9)8-20-14(18)5-3-10-2-4-11(16)12(17)7-10/h2-7,13,16-17H,8H2,1H3/b5-3+/t13-/m0/s1

> <INCHI_KEY>
HBXZQGVBVFMZGQ-LQPUYASZSA-N

> <FORMULA>
C15H14O6

> <MOLECULAR_WEIGHT>
290.271

> <EXACT_MASS>
290.079038171

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.151243947749215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-3-methyl-5-oxo-2,5-dihydrofuran-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
2.576401993

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.208988023777206

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.880689464088683

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283760187513136

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
75.02140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R)-3-methyl-5-oxo-2H-furan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.0550   -3.9440    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569   -4.5156   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1476   -5.7559   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438   -5.8696   -2.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8803   -6.8662   -3.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -4.6919   -2.8983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -3.7422   -1.8215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0484   -2.5186   -2.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0526   -1.4572   -1.3096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9145   -0.7232   -1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0954   -0.9058   -1.9107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982    0.3300   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026    1.1928    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1735    2.2668    1.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0126    2.6693    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098    3.7018    2.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856    4.3403    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572    5.3554    3.8149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    3.9590    2.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330    4.5981    2.5557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3665    2.9362    1.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944   -4.7064    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068   -3.1498    0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164   -3.5293    1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838   -6.5651   -0.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116   -3.4709   -1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -2.7981   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6795   -2.1470   -3.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0479    0.3540    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    1.1089   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    2.1734    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403    3.9854    3.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    5.5118    4.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2862    5.2693    3.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3016    2.6855    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  0
 10 11  2  0
 15 16  2  0
  9  8  1  0
 16 17  1  0
  7  6  1  0
 17 19  2  0
 14 13  1  0
 21 14  2  0
 13 12  2  0
  6  4  1  0
  4  3  1  0
  3  2  2  0
  2  7  1  0
  4  5  2  0
 12 10  1  0
  2  1  1  0
 14 15  1  0
 19 20  1  0
 10  9  1  0
 17 18  1  0
  7  8  1  0
 21 35  1  0
 15 31  1  0
 16 32  1  0
 13 30  1  0
 12 29  1  0
  8 27  1  0
  8 28  1  0
  7 26  1  1
  3 25  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 20 34  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.055  -3.944   0.652  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.857  -4.516  -0.706  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.148  -5.756  -1.095  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.744  -5.870  -2.494  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.880  -6.866  -3.178  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.199  -4.692  -2.898  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.241  -3.742  -1.821  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.048  -2.519  -2.279  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.053  -1.457  -1.310  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.915  -0.723  -1.253  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.095  -0.906  -1.911  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.098   0.330  -0.236  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.103   1.193   0.018  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.174   2.267   1.019  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.013   2.669   1.659  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.010   3.702   2.604  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.186   4.340   2.902  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.257   5.355   3.815  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.361   3.959   2.264  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.533   4.598   2.556  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.367   2.936   1.323  0.00  0.00           C+0
HETATM   22  H   UNK     0      -2.394  -4.706   1.361  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.807  -3.150   0.634  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.116  -3.529   1.032  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.584  -6.565  -0.537  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.212  -3.471  -1.564  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.094  -2.798  -2.457  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.680  -2.147  -3.244  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.048   0.354   0.284  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.840   1.109  -0.522  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.954   2.173   1.428  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.940   3.985   3.085  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.637   5.512   4.165  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.286   5.269   3.223  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.302   2.686   0.832  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    3    7    1                                                  
CONECT    3    4    2   25                                                  
CONECT    4    6    3    5                                                  
CONECT    5    4                                                            
CONECT    6    7    4                                                       
CONECT    7    6    2    8   26                                             
CONECT    8    9    7   27   28                                             
CONECT    9    8   10                                                       
CONECT   10   11   12    9                                                  
CONECT   11   10                                                            
CONECT   12   13   10   29                                                  
CONECT   13   14   12   30                                                  
CONECT   14   13   21   15                                                  
CONECT   15   16   14   31                                                  
CONECT   16   15   17   32                                                  
CONECT   17   16   19   18                                                  
CONECT   18   17   33                                                       
CONECT   19   21   17   20                                                  
CONECT   20   19   34                                                       
CONECT   21   19   14   35                                                  
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28    8                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   15                                                            
CONECT   32   16                                                            
CONECT   33   18                                                            
CONECT   34   20                                                            
CONECT   35   21                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

RDKit          3D

35 36  0  0  0  0  0  0  0  0999 V2000
   -2.0550   -3.9440    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569   -4.5156   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1476   -5.7559   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438   -5.8696   -2.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8803   -6.8662   -3.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -4.6919   -2.8983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -3.7422   -1.8215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0484   -2.5186   -2.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0526   -1.4572   -1.3096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9145   -0.7232   -1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0954   -0.9058   -1.9107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982    0.3300   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026    1.1928    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1735    2.2668    1.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0126    2.6693    1.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098    3.7018    2.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856    4.3403    2.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572    5.3554    3.8149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    3.9590    2.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330    4.5981    2.5557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3665    2.9362    1.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944   -4.7064    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068   -3.1498    0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164   -3.5293    1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838   -6.5651   -0.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116   -3.4709   -1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0941   -2.7981   -2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6795   -2.1470   -3.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0479    0.3540    0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402    1.1089   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    2.1734    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403    3.9854    3.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    5.5118    4.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2862    5.2693    3.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3016    2.6855    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  0
 10 11  2  0
 15 16  2  0
  9  8  1  0
 16 17  1  0
  7  6  1  0
 17 19  2  0
 14 13  1  0
 21 14  2  0
 13 12  2  0
  6  4  1  0
  4  3  1  0
  3  2  2  0
  2  7  1  0
  4  5  2  0
 12 10  1  0
  2  1  1  0
 14 15  1  0
 19 20  1  0
 10  9  1  0
 17 18  1  0
  7  8  1  0
 21 35  1  0
 15 31  1  0
 16 32  1  0
 13 30  1  0
 12 29  1  0
  8 27  1  0
  8 28  1  0
  7 26  1  1
  3 25  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 20 34  1  0
 18 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
Umbelactonyl caffeic acid	Generator

Chemical Formula

C₁₅H₁₄O₆

Average Mass

290.2710 Da

Monoisotopic Mass

290.07904 Da

IUPAC Name

[(2R)-3-methyl-5-oxo-2,5-dihydrofuran-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

[(2R)-3-methyl-5-oxo-2H-furan-2-yl]methyl (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)OC([H])([H])[C@]2([H])OC(=O)C([H])=C2C([H])([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C15H14O6/c1-9-6-15(19)21-13(9)8-20-14(18)5-3-10-2-4-11(16)12(17)7-10/h2-7,13,16-17H,8H2,1H3/b5-3+/t13-/m0/s1

InChI Key

HBXZQGVBVFMZGQ-LQPUYASZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Crypteronia paniculata	JEOL database	Deng, J.-Z., et al, J. Nat. Prod. 68, 465 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Carboxylic acid ester
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.09	ALOGPS
logP	2.58	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	5.88	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	75.02 m³·mol⁻¹	ChemAxon
Polarizability	29.15 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

9912540

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11737833

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Deng, J.-Z., et al. (2005). Deng, J.-Z., et al, J. Nat. Prod. 68, 465 (2005). J. Nat. Prod..

Showing NP-Card for (R)-(+)-umbelactone (NP0028035)

MOL for NP0028035 ((R)-(+)-umbelactone)

3D MOL for NP0028035 ((R)-(+)-umbelactone)

3D SDF for NP0028035 ((R)-(+)-umbelactone)

3D-SDF for NP0028035 ((R)-(+)-umbelactone)

PDB for NP0028035 ((R)-(+)-umbelactone)

3D PDB for NP0028035 ((R)-(+)-umbelactone)

SMILES for NP0028035 ((R)-(+)-umbelactone)

INCHI for NP0028035 ((R)-(+)-umbelactone)

Structure for NP0028035 ((R)-(+)-umbelactone)

3D Structure for NP0028035 ((R)-(+)-umbelactone)