NP-MRD: Showing NP-Card for (3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid (NP0200786)

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Record Information

Version

2.0

Created at

2022-09-04 19:42:07 UTC

Updated at

2022-09-04 19:42:08 UTC

NP-MRD ID

NP0200786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid

Description

(3R,4R,5R)-3-amino-4,5-dihydroxy-5-{[(1S)-1-[(3R)-8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]-3-methylbutyl]-C-hydroxycarbonimidoyl}pentanoic acid belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. Based on a literature review very few articles have been published on (3R,4R,5R)-3-amino-4,5-dihydroxy-5-{[(1S)-1-[(3R)-8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]-3-methylbutyl]-C-hydroxycarbonimidoyl}pentanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042221422D          

 30 31  0  0  1  0            999 V2000
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19  5  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 19 30  1  0  0  0  0
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
   -1.3303    4.6835   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9382    3.4844    0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3671    3.6777    2.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6365    2.2243    0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902    1.0287    1.1000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2110    0.9312    0.9626 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9408   -0.0760    0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6211   -1.3995    1.1354 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4283    0.1950    0.7998 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6564    1.5585    0.6606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8377   -0.5702   -0.4381 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6151   -1.9364   -0.2964 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2309   -0.2510   -0.8822 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4662   -0.8756   -2.1534 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911   -0.6770    0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6187   -0.3116   -0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6764    0.2674   -1.5813 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8018   -0.5867    0.2060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8621   -0.2305    0.6546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3735   -0.1598    0.7812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9244   -1.4539    0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0967   -1.9405    0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6308   -3.1287    0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0138   -3.8569   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8103   -3.3737   -1.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1975   -4.1011   -2.0847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742   -2.1637   -0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0055   -1.6734   -1.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3683   -2.2487   -2.1065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5066   -0.4644   -0.7020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949    4.7689   -1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331    4.7123   -0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1220    5.5888    0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1503    3.3528    0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6532    3.1444    2.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3560    4.7817    2.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4042    3.2991    2.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3515    2.1000   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7179    2.3404    0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4952    1.2970    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4124   -2.0682    0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -0.1454    1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5437    1.7762   -0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1487   -0.2302   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3463   -2.4894   -0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973    0.8512   -1.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6531   -0.7546   -2.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7503   -1.8730   -2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2146   -0.1586    1.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2504   -1.7757    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7288   -1.0529    1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5595   -1.0517    1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5983    0.0452    1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835    0.6513    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6191   -1.3775    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5699   -3.5131    0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3998   -4.7990   -0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4119   -3.9919   -2.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
  5 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 19  1  0
 27 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  1
  8 41  1  0
  9 42  1  1
 10 43  1  0
 11 44  1  6
 12 45  1  0
 13 46  1  6
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 18 51  1  0
 19 52  1  1
 20 53  1  0
 20 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 26 58  1  0
M  END


  Mrv1652309042221422D          

 30 31  0  0  1  0            999 V2000
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19  5  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 19 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0200786

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@H](N=C(O)[C@H](O)[C@H](O)[C@H](N)CC(O)=O)[C@H]1CC2=CC=CC(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H28N2O8/c1-9(2)6-12(22-19(28)18(27)17(26)11(21)8-15(24)25)14-7-10-4-3-5-13(23)16(10)20(29)30-14/h3-5,9,11-12,14,17-18,23,26-27H,6-8,21H2,1-2H3,(H,22,28)(H,24,25)/t11-,12+,14-,17-,18-/m1/s1

> <INCHI_KEY>
LOXFXXGTOVWWQV-YPXRGCATSA-N

> <FORMULA>
C20H28N2O8

> <MOLECULAR_WEIGHT>
424.45

> <EXACT_MASS>
424.18456587

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.81645623077857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R,5R)-3-amino-4,5-dihydroxy-5-{[(1S)-1-[(3R)-8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]-3-methylbutyl]-C-hydroxycarbonimidoyl}pentanoic acid

> <JCHEM_LOGP>
-1.4472113878420705

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.863880497855612

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.273223375729505

> <JCHEM_PKA_STRONGEST_BASIC>
9.324263452661985

> <JCHEM_POLAR_SURFACE_AREA>
182.89999999999998

> <JCHEM_REFRACTIVITY>
104.86569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,5R)-3-amino-4,5-dihydroxy-5-{[(1S)-1-[(3R)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-C-hydroxycarbonimidoyl}pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.667  -7.700   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       8.002  -6.160   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.003  -8.470   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.669  -6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    5   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   19                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
(3R,4R,5R)-3-Amino-4,5-dihydroxy-5-{[(1S)-1-[(3R)-8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]-3-methylbutyl]-C-hydroxycarbonimidoyl}pentanoate	Generator

Chemical Formula

C₂₀H₂₈N₂O₈

Average Mass

424.4500 Da

Monoisotopic Mass

424.18457 Da

IUPAC Name

(3R,4R,5R)-3-amino-4,5-dihydroxy-5-{[(1S)-1-[(3R)-8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]-3-methylbutyl]-C-hydroxycarbonimidoyl}pentanoic acid

Traditional Name

(3R,4R,5R)-3-amino-4,5-dihydroxy-5-{[(1S)-1-[(3R)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-C-hydroxycarbonimidoyl}pentanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)C[C@H](N=C(O)[C@H](O)[C@H](O)[C@H](N)CC(O)=O)[C@H]1CC2=CC=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C20H28N2O8/c1-9(2)6-12(22-19(28)18(27)17(26)11(21)8-15(24)25)14-7-10-4-3-5-13(23)16(10)20(29)30-14/h3-5,9,11-12,14,17-18,23,26-27H,6-8,21H2,1-2H3,(H,22,28)(H,24,25)/t11-,12+,14-,17-,18-/m1/s1

InChI Key

LOXFXXGTOVWWQV-YPXRGCATSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Beta amino acids and derivatives

Alternative Parents

Substituents

Beta amino acid or derivatives
Benzopyran
Isochromane
2-benzopyran
Medium-chain hydroxy acid
Medium-chain fatty acid
Heterocyclic fatty acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Hydroxy fatty acid
Amino fatty acid
Branched fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Benzenoid
1,3-aminoalcohol
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Amino acid
Lactone
1,2-diol
1,2-aminoalcohol
Organoheterocyclic compound
Carboxylic acid
Oxacycle
Carboximidic acid
Carboximidic acid derivative
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic nitrogen compound
Primary aliphatic amine
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Amine
Alcohol
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-1.4	ChemAxon
pKa (Strongest Acidic)	3.27	ChemAxon
pKa (Strongest Basic)	9.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	182.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	104.87 m³·mol⁻¹	ChemAxon
Polarizability	41.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163029739

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid (NP0200786)

MOL for NP0200786 ((3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid)

3D MOL for NP0200786 ((3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid)

3D SDF for NP0200786 ((3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid)

3D-SDF for NP0200786 ((3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid)

PDB for NP0200786 ((3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid)

3D PDB for NP0200786 ((3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid)

SMILES for NP0200786 ((3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid)

INCHI for NP0200786 ((3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid)

Structure for NP0200786 ((3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid)

3D Structure for NP0200786 ((3r,4r,5r)-3-amino-4,5-dihydroxy-5-{[(1s)-1-[(3r)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]-c-hydroxycarbonimidoyl}pentanoic acid)