NP-MRD: Showing NP-Card for 1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one (NP0307205)

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Record Information

Version

2.0

Created at

2022-09-11 00:10:36 UTC

Updated at

2022-09-11 00:10:36 UTC

NP-MRD ID

NP0307205

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one

Description

Cladosporiumin H belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. Based on a literature review very few articles have been published on Cladosporiumin H.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112202102D          

 20 20  0  0  1  0            999 V2000
    3.1830   -2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3251   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -0.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001   -1.7696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806   -0.3495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8011   -0.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860    0.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367   -1.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681    0.3649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389    0.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8519    0.7455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -1.8646    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307205

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(CC(C)O)CC(=O)C1=C(O)[C@@H](N=C1O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H23NO5/c1-7(2)12-13(18)11(14(19)15-12)10(17)6-9(20-4)5-8(3)16/h7-9,12,16,18H,5-6H2,1-4H3,(H,15,19)/t8?,9?,12-/m0/s1

> <INCHI_KEY>
VFIOHWSOAKTWFU-KWPJZBAWSA-N

> <FORMULA>
C14H23NO5

> <MOLECULAR_WEIGHT>
285.34

> <EXACT_MASS>
285.157622845

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.833772025381144

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2S)-3,5-dihydroxy-2-(propan-2-yl)-2H-pyrrol-4-yl]-5-hydroxy-3-methoxyhexan-1-one

> <JCHEM_LOGP>
0.8529087519999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.754958257408067

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.2159083805290685

> <JCHEM_PKA_STRONGEST_BASIC>
1.5889902902066049

> <JCHEM_POLAR_SURFACE_AREA>
99.35000000000001

> <JCHEM_REFRACTIVITY>
75.05050000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(5S)-2,4-dihydroxy-5-isopropyl-5H-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       5.942  -4.251   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.608  -3.481   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.608  -1.941   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.274  -1.171   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.941  -1.941   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.941  -3.481   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.607  -1.171   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.800  -1.797   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.120  -3.303   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.830  -0.652   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.362  -0.813   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.267   0.432   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.988  -2.220   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.060   0.681   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.446   0.361   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.590   1.392   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.942  -1.171   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.275  -1.941   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.609  -1.171   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.275  -3.481   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   15                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15                                                       
CONECT   15   14    7   16                                                  
CONECT   16   15                                                            
CONECT   17    3   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₃NO₅

Average Mass

285.3400 Da

Monoisotopic Mass

285.15762 Da

IUPAC Name

1-[(2S)-3,5-dihydroxy-2-(propan-2-yl)-2H-pyrrol-4-yl]-5-hydroxy-3-methoxyhexan-1-one

Traditional Name

1-[(5S)-2,4-dihydroxy-5-isopropyl-5H-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one

CAS Registry Number

Not Available

SMILES

COC(CC(C)O)CC(=O)C1=C(O)[C@@H](N=C1O)C(C)C

InChI Identifier

InChI=1S/C14H23NO5/c1-7(2)12-13(18)11(14(19)15-12)10(17)6-9(20-4)5-8(3)16/h7-9,12,16,18H,5-6H2,1-4H3,(H,15,19)/t8?,9?,12-/m0/s1

InChI Key

VFIOHWSOAKTWFU-KWPJZBAWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Vinylogous acids

Sub Class

Not Available

Direct Parent

Vinylogous acids

Alternative Parents

Substituents

Vinylogous acid
Cyclic carboximidic acid
Secondary alcohol
Ketone
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Enol
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.85	ChemAxon
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	1.59	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.35 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	75.05 m³·mol⁻¹	ChemAxon
Polarizability	30.83 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78441717

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590264

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one (NP0307205)

MOL for NP0307205 (1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one)

3D MOL for NP0307205 (1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one)

3D SDF for NP0307205 (1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one)

3D-SDF for NP0307205 (1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one)

PDB for NP0307205 (1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one)

3D PDB for NP0307205 (1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one)

SMILES for NP0307205 (1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one)

INCHI for NP0307205 (1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one)

Structure for NP0307205 (1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one)

3D Structure for NP0307205 (1-[(5s)-2,4-dihydroxy-5-isopropyl-5h-pyrrol-3-yl]-5-hydroxy-3-methoxyhexan-1-one)