NP-MRD: Showing NP-Card for Isoamericanoic acid A (NP0009308)

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Record Information

Version

2.0

Created at

2020-12-09 06:43:34 UTC

Updated at

2021-07-15 17:02:54 UTC

NP-MRD ID

NP0009308

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoamericanoic acid A

Provided By

NPAtlas

Description

Isoamericanoic acid A is also known as isoamericanoate a. Isoamericanoic acid A is found in Morinda citrifolia and Ophioceras dolichostomum. Isoamericanoic acid A was first documented in 2003 (PMID: 14646313). Based on a literature review a small amount of articles have been published on Isoamericanoic acid A (PMID: 20552522) (PMID: 17987501).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106343D          

 41 43  0  0  0  0            999 V2000
    5.7900    3.8418   -0.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8196    2.6224   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0238    1.9463   -0.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5869    1.8717   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6304    0.5777    0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.1982    0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -1.5747    0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -2.3684    0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492   -1.7844    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572   -0.4348    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876    0.3487    0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229    0.0990    0.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2813   -0.7109   -0.1592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5111    0.0876   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053   -0.3732    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7817    0.4763    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864    1.8146    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8052    2.6391    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944    2.2847   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3106    3.6005   -0.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213    1.4186   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -2.0509    0.4409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7640   -3.0597   -0.6184 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8290   -4.3369   -0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -2.4905    0.8524 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798    2.0602   -0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6655    2.4237   -0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063    0.0797    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4947   -2.0036    0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4571   -3.4250    0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    1.3938    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772   -0.7831   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469   -1.4154    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7344    0.1089    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7545    3.5976    0.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0153    4.3135   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    1.8295   -0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -2.1728    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -2.8036   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093   -3.0401   -1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6841   -4.4095    0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 11  6  1  0  0  0  0
 21 14  1  0  0  0  0
 25  9  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
 11 31  1  0  0  0  0
 13 32  1  6  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 18 35  1  0  0  0  0
 20 36  1  0  0  0  0
 21 37  1  0  0  0  0
 22 38  1  1  0  0  0
 23 39  1  0  0  0  0
 23 40  1  0  0  0  0
 24 41  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    5.7900    3.8418   -0.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8196    2.6224   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0238    1.9463   -0.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5869    1.8717   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6304    0.5777    0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.1982    0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -1.5747    0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -2.3684    0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492   -1.7844    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572   -0.4348    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876    0.3487    0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229    0.0990    0.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2813   -0.7109   -0.1592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5111    0.0876   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053   -0.3732    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7817    0.4763    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864    1.8146    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8052    2.6391    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944    2.2847   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3106    3.6005   -0.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213    1.4186   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -2.0509    0.4409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7640   -3.0597   -0.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290   -4.3369   -0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -2.4905    0.8524 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798    2.0602   -0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6655    2.4237   -0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063    0.0797    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4947   -2.0036    0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4571   -3.4250    0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    1.3938    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772   -0.7831   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469   -1.4154    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7344    0.1089    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7545    3.5976    0.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0153    4.3135   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    1.8295   -0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -2.1728    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -2.8036   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093   -3.0401   -1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6841   -4.4095    0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 13 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 11  6  1  0
 21 14  1  0
 25  9  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
 11 31  1  0
 13 32  1  6
 15 33  1  0
 16 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  1
 23 39  1  0
 23 40  1  0
 24 41  1  0
M  END


  Mrv1652306242106343D          

 41 43  0  0  0  0            999 V2000
    5.7900    3.8418   -0.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8196    2.6224   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0238    1.9463   -0.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5869    1.8717   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6304    0.5777    0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.1982    0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -1.5747    0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -2.3684    0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492   -1.7844    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572   -0.4348    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876    0.3487    0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229    0.0990    0.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2813   -0.7109   -0.1592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5111    0.0876   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053   -0.3732    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7817    0.4763    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864    1.8146    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8052    2.6391    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944    2.2847   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3106    3.6005   -0.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213    1.4186   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -2.0509    0.4409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7640   -3.0597   -0.6184 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8290   -4.3369   -0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -2.4905    0.8524 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798    2.0602   -0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6655    2.4237   -0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063    0.0797    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4947   -2.0036    0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4571   -3.4250    0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    1.3938    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772   -0.7831   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469   -1.4154    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7344    0.1089    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7545    3.5976    0.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0153    4.3135   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    1.8295   -0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -2.1728    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -2.8036   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093   -3.0401   -1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6841   -4.4095    0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 11  6  1  0  0  0  0
 21 14  1  0  0  0  0
 25  9  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
 11 31  1  0  0  0  0
 13 32  1  6  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 18 35  1  0  0  0  0
 20 36  1  0  0  0  0
 21 37  1  0  0  0  0
 22 38  1  1  0  0  0
 23 39  1  0  0  0  0
 23 40  1  0  0  0  0
 24 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009308

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C2O[C@]([H])(C([H])([H])O[H])[C@]([H])(OC2=C1[H])C1=C([H])C([H])=C(O[H])C(O[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O7/c19-9-16-18(11-3-4-12(20)13(21)8-11)25-15-7-10(2-6-17(22)23)1-5-14(15)24-16/h1-8,16,18-21H,9H2,(H,22,23)/b6-2+/t16-,18-/m1/s1

> <INCHI_KEY>
RVKSBQRLCFURSH-QFNLJVBBSA-N

> <FORMULA>
C18H16O7

> <MOLECULAR_WEIGHT>
344.319

> <EXACT_MASS>
344.089602855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
35.01052253416715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[(2R,3R)-3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
2.195993387333333

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.207265120868671

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5012303431120455

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904140632676404

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
88.22440000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(2R,3R)-3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    5.7900    3.8418   -0.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8196    2.6224   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0238    1.9463   -0.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5869    1.8717   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6304    0.5777    0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.1982    0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -1.5747    0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -2.3684    0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492   -1.7844    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572   -0.4348    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876    0.3487    0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229    0.0990    0.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2813   -0.7109   -0.1592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5111    0.0876   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053   -0.3732    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7817    0.4763    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864    1.8146    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8052    2.6391    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944    2.2847   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3106    3.6005   -0.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213    1.4186   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -2.0509    0.4409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7640   -3.0597   -0.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290   -4.3369   -0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -2.4905    0.8524 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798    2.0602   -0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6655    2.4237   -0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063    0.0797    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4947   -2.0036    0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4571   -3.4250    0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    1.3938    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772   -0.7831   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469   -1.4154    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7344    0.1089    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7545    3.5976    0.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0153    4.3135   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    1.8295   -0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -2.1728    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -2.8036   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093   -3.0401   -1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6841   -4.4095    0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 13 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 11  6  1  0
 21 14  1  0
 25  9  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
 11 31  1  0
 13 32  1  6
 15 33  1  0
 16 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  1
 23 39  1  0
 23 40  1  0
 24 41  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0       5.790   3.842  -0.484  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.820   2.622  -0.253  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.024   1.946  -0.153  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.587   1.872  -0.082  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.630   0.578   0.162  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.423  -0.198   0.337  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.496  -1.575   0.596  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.398  -2.368   0.772  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.149  -1.784   0.691  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.057  -0.435   0.437  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.188   0.349   0.262  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.223   0.099   0.365  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.281  -0.711  -0.159  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.511   0.088  -0.015  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.705  -0.373   0.447  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.782   0.476   0.535  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.686   1.815   0.160  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.805   2.639   0.267  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.494   2.285  -0.304  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.311   3.600  -0.698  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.421   1.419  -0.386  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.299  -2.051   0.441  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.764  -3.060  -0.618  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.829  -4.337  -0.070  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.021  -2.490   0.852  0.00  0.00           O+0
HETATM   26  H   UNK     0       7.680   2.060  -0.919  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.666   2.424  -0.166  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.606   0.080   0.234  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.495  -2.004   0.654  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.457  -3.425   0.971  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.012   1.394   0.070  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.077  -0.783  -1.254  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.747  -1.415   0.729  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.734   0.109   0.903  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.755   3.598   0.003  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.015   4.314  -0.681  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.483   1.829  -0.762  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.956  -2.173   1.326  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.784  -2.804  -0.974  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.109  -3.040  -1.504  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.684  -4.410   0.400  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   26                                                       
CONECT    4    2    5   27                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   29                                                  
CONECT    8    7    9   30                                                  
CONECT    9    8   10   25                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    6   31                                                  
CONECT   12   10   13                                                       
CONECT   13   12   14   22   32                                             
CONECT   14   13   15   21                                                  
CONECT   15   14   16   33                                                  
CONECT   16   15   17   34                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   35                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19   36                                                       
CONECT   21   19   14   37                                                  
CONECT   22   13   23   25   38                                             
CONECT   23   22   24   39   40                                             
CONECT   24   23   41                                                       
CONECT   25   22    9                                                       
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31   11                                                            
CONECT   32   13                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   18                                                            
CONECT   36   20                                                            
CONECT   37   21                                                            
CONECT   38   22                                                            
CONECT   39   23                                                            
CONECT   40   23                                                            
CONECT   41   24                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
    5.7900    3.8418   -0.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8196    2.6224   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0238    1.9463   -0.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5869    1.8717   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6304    0.5777    0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.1982    0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -1.5747    0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -2.3684    0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492   -1.7844    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572   -0.4348    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876    0.3487    0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229    0.0990    0.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2813   -0.7109   -0.1592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5111    0.0876   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053   -0.3732    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7817    0.4763    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864    1.8146    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8052    2.6391    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944    2.2847   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3106    3.6005   -0.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213    1.4186   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -2.0509    0.4409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7640   -3.0597   -0.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290   -4.3369   -0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -2.4905    0.8524 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798    2.0602   -0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6655    2.4237   -0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063    0.0797    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4947   -2.0036    0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4571   -3.4250    0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123    1.3938    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772   -0.7831   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469   -1.4154    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7344    0.1089    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7545    3.5976    0.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0153    4.3135   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    1.8295   -0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -2.1728    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -2.8036   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093   -3.0401   -1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6841   -4.4095    0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 13 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 11  6  1  0
 21 14  1  0
 25  9  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
 11 31  1  0
 13 32  1  6
 15 33  1  0
 16 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  1
 23 39  1  0
 23 40  1  0
 24 41  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Isoamericanoate a	Generator
(2E)-3-[(2R,3R)-3-(3,4-Dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enoate	Generator

Chemical Formula

C₁₈H₁₆O₇

Average Mass

344.3190 Da

Monoisotopic Mass

344.08960 Da

IUPAC Name

(2E)-3-[(2R,3R)-3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enoic acid

Traditional Name

(2E)-3-[(2R,3R)-3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

OC[C@H]1OC2=C(O[C@@H]1C1=CC(O)=C(O)C=C1)C=C(\C=C\C(O)=O)C=C2

InChI Identifier

InChI=1S/C18H16O7/c19-9-16-18(11-3-4-12(20)13(21)8-11)25-15-7-10(2-6-17(22)23)1-5-14(15)24-16/h1-8,16,18-21H,9H2,(H,22,23)/b6-2+/t16-,18-/m1/s1

InChI Key

RVKSBQRLCFURSH-QFNLJVBBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Morinda citrifolia	Plant	KNApSAcK
Ophioceras dolichostomum	NPAtlas	20552522

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	1.84	ALOGPS
logP	2.2	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.22 m³·mol⁻¹	ChemAxon
Polarizability	35.01 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA020511

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00056316

Chemspider ID

78441573

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102288397

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dong JY, Wang L, Song HC, Wang LM, Shen KZ, Sun R, Li GH, Li L, Zhang KQ: Ophiocerol, a novel macrocylic neolignan from the aquatic fungus Ophioceras dolichostomum YMF1.00988. Nat Prod Res. 2010 Jul;24(11):1004-12. doi: 10.1080/14786410902854126. [PubMed:20552522 ]
Lin CF, Ni CL, Huang YL, Sheu SJ, Chen CC: Lignans and anthraquinones from the fruits of Morinda citrifolia. Nat Prod Res. 2007 Nov;21(13):1199-204. doi: 10.1080/14786410601132451. [PubMed:17987501 ]
Takahasi H, Yanagi K, Ueda M, Nakade K, Fukuyama Y: Structures of 1,4-benzodioxane derivatives from the seeds of Phytolacca americana and their neuritogenic activity in primary cultured rat cortical neurons. Chem Pharm Bull (Tokyo). 2003 Dec;51(12):1377-81. doi: 10.1248/cpb.51.1377. [PubMed:14646313 ]

Showing NP-Card for Isoamericanoic acid A (NP0009308)

MOL for NP0009308 (Isoamericanoic acid A)

3D MOL for NP0009308 (Isoamericanoic acid A)

3D SDF for NP0009308 (Isoamericanoic acid A)

3D-SDF for NP0009308 (Isoamericanoic acid A)

PDB for NP0009308 (Isoamericanoic acid A)

3D PDB for NP0009308 (Isoamericanoic acid A)

SMILES for NP0009308 (Isoamericanoic acid A)

INCHI for NP0009308 (Isoamericanoic acid A)

Structure for NP0009308 (Isoamericanoic acid A)

3D Structure for NP0009308 (Isoamericanoic acid A)