NP-MRD: Showing NP-Card for (-)-xylariamide A (NP0005877)

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Record Information

Version

2.0

Created at

2020-12-09 03:00:33 UTC

Updated at

2021-07-15 16:53:13 UTC

NP-MRD ID

NP0005877

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-xylariamide A

Provided By

NPAtlas

Description

(2R)-3-(3-chloro-4-hydroxyphenyl)-2-{[(2E)-1-hydroxy-4-methoxy-4-oxobut-2-en-1-ylidene]amino}propanoic acid belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (-)-xylariamide A is found in Xylaria sp. (-)-xylariamide A was first documented in 2005 (PMID: 15921427). Based on a literature review very few articles have been published on (2R)-3-(3-chloro-4-hydroxyphenyl)-2-{[(2E)-1-hydroxy-4-methoxy-4-oxobut-2-en-1-ylidene]amino}propanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118233D          

 36 36  0  0  0  0            999 V2000
    6.9308    1.5626   -1.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484    0.6586   -0.6795 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6851    0.8980   -0.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330    1.9187   -1.1858 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7640   -0.0282    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4846    0.2110    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158   -0.6670    0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456   -1.6990    1.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1359   -0.3923    0.7749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730   -1.2746    1.4324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7905   -1.8855    0.4986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6343   -0.8969   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -0.3606   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0451    0.5725   -2.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2428    1.0026   -1.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243    1.9396   -2.1501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5837    0.4458   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0973    0.9747    0.4480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8112   -0.4876    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177   -0.5906    2.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237    0.5930    2.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3431   -1.2259    3.3891 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6676    1.9590   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3254    2.4033   -1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4269    0.9958   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531   -0.9131    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034    1.0914   -0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182    0.4628    0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2011   -2.1216    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821   -2.6171    1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -2.4653   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277   -0.6521   -1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628    1.0027   -3.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8884    2.2058   -1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -0.8766    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -1.7439    4.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 10 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 12  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  5 26  1  0  0  0  0
  6 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  1  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 13 32  1  0  0  0  0
 14 33  1  0  0  0  0
 16 34  1  0  0  0  0
 19 35  1  0  0  0  0
 22 36  1  0  0  0  0
M  END

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    6.9308    1.5626   -1.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484    0.6586   -0.6795 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6851    0.8980   -0.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330    1.9187   -1.1858 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7640   -0.0282    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4846    0.2110    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158   -0.6670    0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456   -1.6990    1.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1359   -0.3923    0.7749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730   -1.2746    1.4324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7905   -1.8855    0.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343   -0.8969   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -0.3606   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0451    0.5725   -2.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2428    1.0026   -1.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243    1.9396   -2.1501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5837    0.4458   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0973    0.9747    0.4480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8112   -0.4876    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177   -0.5906    2.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237    0.5930    2.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3431   -1.2259    3.3891 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6676    1.9590   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3254    2.4033   -1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4269    0.9958   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531   -0.9131    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034    1.0914   -0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182    0.4628    0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2011   -2.1216    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821   -2.6171    1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -2.4653   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277   -0.6521   -1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628    1.0027   -3.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8884    2.2058   -1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -0.8766    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -1.7439    4.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 10 20  1  0
 20 21  2  0
 20 22  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 19 35  1  0
 22 36  1  0
M  END


  Mrv1652306242118233D          

 36 36  0  0  0  0            999 V2000
    6.9308    1.5626   -1.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484    0.6586   -0.6795 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6851    0.8980   -0.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330    1.9187   -1.1858 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7640   -0.0282    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4846    0.2110    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158   -0.6670    0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456   -1.6990    1.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1359   -0.3923    0.7749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730   -1.2746    1.4324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7905   -1.8855    0.4986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6343   -0.8969   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -0.3606   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0451    0.5725   -2.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2428    1.0026   -1.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243    1.9396   -2.1501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5837    0.4458   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0973    0.9747    0.4480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8112   -0.4876    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177   -0.5906    2.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237    0.5930    2.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3431   -1.2259    3.3891 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6676    1.9590   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3254    2.4033   -1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4269    0.9958   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531   -0.9131    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034    1.0914   -0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182    0.4628    0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2011   -2.1216    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821   -2.6171    1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -2.4653   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277   -0.6521   -1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628    1.0027   -3.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8884    2.2058   -1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -0.8766    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -1.7439    4.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 10 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 12  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  5 26  1  0  0  0  0
  6 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  1  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 13 32  1  0  0  0  0
 14 33  1  0  0  0  0
 16 34  1  0  0  0  0
 19 35  1  0  0  0  0
 22 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005877

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H14ClNO6/c1-22-13(19)5-4-12(18)16-10(14(20)21)7-8-2-3-11(17)9(15)6-8/h2-6,10,17H,7H2,1H3,(H,16,18)(H,20,21)/b5-4+/t10-/m1/s1

> <INCHI_KEY>
KCOKHEIACSQLBQ-ORAHPGNNSA-N

> <FORMULA>
C14H14ClNO6

> <MOLECULAR_WEIGHT>
327.72

> <EXACT_MASS>
327.0509649

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.152332864714197

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-3-(3-chloro-4-hydroxyphenyl)-2-[(2E)-3-(methyl carboxy)prop-2-enamido]propanoic acid

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
1.758599783

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.939740581073774

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4310175018141167

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9435697556607127

> <JCHEM_POLAR_SURFACE_AREA>
112.93000000000002

> <JCHEM_REFRACTIVITY>
78.0782

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(3-chloro-4-hydroxyphenyl)-2-[(2E)-3-(methyl carboxy)prop-2-enamido]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    6.9308    1.5626   -1.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484    0.6586   -0.6795 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6851    0.8980   -0.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330    1.9187   -1.1858 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7640   -0.0282    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4846    0.2110    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158   -0.6670    0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456   -1.6990    1.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1359   -0.3923    0.7749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730   -1.2746    1.4324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7905   -1.8855    0.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343   -0.8969   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -0.3606   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0451    0.5725   -2.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2428    1.0026   -1.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243    1.9396   -2.1501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5837    0.4458   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0973    0.9747    0.4480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8112   -0.4876    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177   -0.5906    2.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237    0.5930    2.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3431   -1.2259    3.3891 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6676    1.9590   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3254    2.4033   -1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4269    0.9958   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531   -0.9131    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034    1.0914   -0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182    0.4628    0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2011   -2.1216    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821   -2.6171    1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -2.4653   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277   -0.6521   -1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628    1.0027   -3.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8884    2.2058   -1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -0.8766    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -1.7439    4.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 10 20  1  0
 20 21  2  0
 20 22  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 19 35  1  0
 22 36  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  C   UNK     0       6.931   1.563  -1.346  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.048   0.659  -0.680  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.685   0.898  -0.634  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.233   1.919  -1.186  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.764  -0.028   0.052  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.485   0.211   0.085  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.516  -0.667   0.749  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.946  -1.699   1.310  0.00  0.00           O+0
HETATM    9  N   UNK     0       0.136  -0.392   0.775  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.773  -1.275   1.432  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.791  -1.886   0.499  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.634  -0.897  -0.178  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.263  -0.361  -1.392  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.045   0.573  -2.045  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.243   1.003  -1.490  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.024   1.940  -2.150  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.584   0.446  -0.275  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      -6.097   0.975   0.448  0.00  0.00          Cl+0
HETATM   19  C   UNK     0      -3.811  -0.488   0.388  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.418  -0.591   2.582  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.124   0.593   2.838  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.343  -1.226   3.389  0.00  0.00           O+0
HETATM   23  H   UNK     0       7.668   1.959  -0.609  0.00  0.00           H+0
HETATM   24  H   UNK     0       6.325   2.403  -1.742  0.00  0.00           H+0
HETATM   25  H   UNK     0       7.427   0.996  -2.161  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.153  -0.913   0.530  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.103   1.091  -0.392  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.218   0.463   0.309  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.201  -2.122   1.863  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.382  -2.617   1.089  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.223  -2.465  -0.262  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.328  -0.652  -1.894  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.763   1.003  -3.003  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.888   2.206  -1.681  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.166  -0.877   1.356  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.100  -1.744   4.213  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   28                                                  
CONECT   10    9   11   20   29                                             
CONECT   11   10   12   30   31                                             
CONECT   12   11   13   19                                                  
CONECT   13   12   14   32                                                  
CONECT   14   13   15   33                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   34                                                       
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   35                                                  
CONECT   20   10   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   36                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    5                                                            
CONECT   27    6                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   11                                                            
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   16                                                            
CONECT   35   19                                                            
CONECT   36   22                                                            
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
    6.9308    1.5626   -1.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484    0.6586   -0.6795 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6851    0.8980   -0.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330    1.9187   -1.1858 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7640   -0.0282    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4846    0.2110    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158   -0.6670    0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456   -1.6990    1.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1359   -0.3923    0.7749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730   -1.2746    1.4324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7905   -1.8855    0.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343   -0.8969   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -0.3606   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0451    0.5725   -2.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2428    1.0026   -1.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243    1.9396   -2.1501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5837    0.4458   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0973    0.9747    0.4480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8112   -0.4876    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177   -0.5906    2.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1237    0.5930    2.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3431   -1.2259    3.3891 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6676    1.9590   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3254    2.4033   -1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4269    0.9958   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531   -0.9131    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034    1.0914   -0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182    0.4628    0.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2011   -2.1216    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821   -2.6171    1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -2.4653   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277   -0.6521   -1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628    1.0027   -3.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8884    2.2058   -1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -0.8766    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -1.7439    4.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 10 20  1  0
 20 21  2  0
 20 22  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 19 35  1  0
 22 36  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R)-3-(3-Chloro-4-hydroxyphenyl)-2-{[(2E)-1-hydroxy-4-methoxy-4-oxobut-2-en-1-ylidene]amino}propanoate	Generator
SHA 14-1	MeSH
CXL-017	MeSH
Ethyl 2-amino-6-(3,5-dimethoxyphenyl)-4-(2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate	MeSH
CXL 017	MeSH

Chemical Formula

C₁₄H₁₄ClNO₆

Average Mass

327.7200 Da

Monoisotopic Mass

327.05096 Da

IUPAC Name

(2R)-3-(3-chloro-4-hydroxyphenyl)-2-[(2E)-3-(methyl carboxy)prop-2-enamido]propanoic acid

Traditional Name

(2R)-3-(3-chloro-4-hydroxyphenyl)-2-[(2E)-3-(methyl carboxy)prop-2-enamido]propanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C\C(=O)N[C@H](CC1=CC(Cl)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C14H14ClNO6/c1-22-13(19)5-4-12(18)16-10(14(20)21)7-8-2-3-11(17)9(15)6-8/h2-6,10,17H,7H2,1H3,(H,16,18)(H,20,21)/b5-4+/t10-/m1/s1

InChI Key

KCOKHEIACSQLBQ-ORAHPGNNSA-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
Xylaria sp.	NPAtlas	15921427

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine and derivatives

Alternative Parents

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
3-phenylpropanoic-acid
Amphetamine or derivatives
2-chlorophenol
2-halophenol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Halobenzene
Fatty acid ester
Chlorobenzene
Fatty acyl
Aryl chloride
Aryl halide
N-acyl-amine
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Secondary carboxylic acid amide
Carboxylic acid ester
Carboxamide group
Carboxylic acid
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.68	ALOGPS
logP	1.76	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-0.94	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.93 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	78.08 m³·mol⁻¹	ChemAxon
Polarizability	31.15 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

NPAtlas ID

NPA003210

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9465348

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11290362

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Davis RA: Isolation and structure elucidation of the new fungal metabolite (-)-xylariamide A. J Nat Prod. 2005 May;68(5):769-72. doi: 10.1021/np050025h. [PubMed:15921427 ]

Showing NP-Card for (-)-xylariamide A (NP0005877)

MOL for NP0005877 ((-)-xylariamide A)

3D MOL for NP0005877 ((-)-xylariamide A)

3D SDF for NP0005877 ((-)-xylariamide A)

3D-SDF for NP0005877 ((-)-xylariamide A)

PDB for NP0005877 ((-)-xylariamide A)

3D PDB for NP0005877 ((-)-xylariamide A)

SMILES for NP0005877 ((-)-xylariamide A)

INCHI for NP0005877 ((-)-xylariamide A)

Structure for NP0005877 ((-)-xylariamide A)

3D Structure for NP0005877 ((-)-xylariamide A)