NP-MRD: Showing NP-Card for (2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid (NP0330024)

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Record Information

Version

2.0

Created at

2022-09-12 14:59:41 UTC

Updated at

2022-09-12 14:59:41 UTC

NP-MRD ID

NP0330024

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid

Description

(2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid is found in Pocillopora grandis.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122216592D          

 21 21  0  0  1  0            999 V2000
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  6  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  1  0  0  0
 10 19  2  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330024

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C[C@@](O)(CO)C\C1=N/C)N[C@@H]([C@H](C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H22N2O6/c1-7(17)10(12(18)19)15-9-5-13(20,6-16)4-8(14-2)11(9)21-3/h7,10,15-17,20H,4-6H2,1-3H3,(H,18,19)/b14-8+/t7-,10-,13+/m0/s1

> <INCHI_KEY>
BKSSMZDJVQTETM-YSQVGDKBSA-N

> <FORMULA>
C13H22N2O6

> <MOLECULAR_WEIGHT>
302.327

> <EXACT_MASS>
302.147786436

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.497528074972216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-3-hydroxy-2-{[(3E,5S)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid

> <JCHEM_LOGP>
-5.0108214697432105

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.638417177818035

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9335286930225797

> <JCHEM_PKA_STRONGEST_BASIC>
8.457198237871744

> <JCHEM_POLAR_SURFACE_AREA>
131.61

> <JCHEM_REFRACTIVITY>
75.68629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-3-hydroxy-2-{[(3E,5S)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.840   3.222   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7    9                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   10    3   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₂N₂O₆

Average Mass

302.3270 Da

Monoisotopic Mass

302.14779 Da

IUPAC Name

(2S,3S)-3-hydroxy-2-{[(3E,5S)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid

Traditional Name

(2S,3S)-3-hydroxy-2-{[(3E,5S)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C[C@@](O)(CO)C\C1=N/C)N[C@@H]([C@H](C)O)C(O)=O

InChI Identifier

InChI=1S/C13H22N2O6/c1-7(17)10(12(18)19)15-9-5-13(20,6-16)4-8(14-2)11(9)21-3/h7,10,15-17,20H,4-6H2,1-3H3,(H,18,19)/b14-8+/t7-,10-,13+/m0/s1

InChI Key

BKSSMZDJVQTETM-YSQVGDKBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pocillopora grandis	LOTUS Database	35616633

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	-5	ChemAxon
pKa (Strongest Acidic)	3.93	ChemAxon
pKa (Strongest Basic)	8.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	131.61 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	75.69 m³·mol⁻¹	ChemAxon
Polarizability	30.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid (NP0330024)

MOL for NP0330024 ((2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid)

3D MOL for NP0330024 ((2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid)

3D SDF for NP0330024 ((2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid)

3D-SDF for NP0330024 ((2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid)

PDB for NP0330024 ((2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid)

3D PDB for NP0330024 ((2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid)

SMILES for NP0330024 ((2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid)

INCHI for NP0330024 ((2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid)

Structure for NP0330024 ((2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid)

3D Structure for NP0330024 ((2s,3s)-3-hydroxy-2-{[(3e,5s)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-(methylimino)cyclohex-1-en-1-yl]amino}butanoic acid)