NP-MRD: Showing NP-Card for 4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one (NP0245334)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 06:22:44 UTC

Updated at

2022-09-07 06:22:44 UTC

NP-MRD ID

NP0245334

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one

Description

4-Hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one is found in Rhabdastrella globostellata. 4-Hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241514192D          

 16 16  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9266   -0.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0760   -1.9851    0.0000 C   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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 10  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(O)C(OC1=O)C(O)C=CC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C11H18O5/c1-6(2)4-5-7(12)9-8(13)10(15-3)11(14)16-9/h4-10,12-13H,1-3H3

> <INCHI_KEY>
BHBCJEWOTYVESN-UHFFFAOYSA-N

> <FORMULA>
C11H18O5

> <MOLECULAR_WEIGHT>
230.26

> <EXACT_MASS>
230.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.040122689889802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
0.43742790899999984

> <ALOGPS_LOGS>
-0.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.873474952366326

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.784130525220224

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3585703505611315

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
57.2235

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.109  -2.943   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.267  -1.375   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.172  -2.621   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.703  -2.460   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.330  -1.053   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.609  -3.706   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₈O₅

Average Mass

230.2600 Da

Monoisotopic Mass

230.11542 Da

IUPAC Name

4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one

Traditional Name

4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one

CAS Registry Number

Not Available

SMILES

COC1C(O)C(OC1=O)C(O)C=CC(C)C

InChI Identifier

InChI=1S/C11H18O5/c1-6(2)4-5-7(12)9-8(13)10(15-3)11(14)16-9/h4-10,12-13H,1-3H3

InChI Key

BHBCJEWOTYVESN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rhabdastrella globostellata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	0.42	ALOGPS
logP	0.44	ChemAxon
logS	-0.86	ALOGPS
pKa (Strongest Acidic)	12.78	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.22 m³·mol⁻¹	ChemAxon
Polarizability	24.04 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one (NP0245334)

MOL for NP0245334 (4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one)

3D MOL for NP0245334 (4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one)

3D SDF for NP0245334 (4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one)

3D-SDF for NP0245334 (4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one)

PDB for NP0245334 (4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one)

3D PDB for NP0245334 (4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one)

SMILES for NP0245334 (4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one)

INCHI for NP0245334 (4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one)

Structure for NP0245334 (4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one)

3D Structure for NP0245334 (4-hydroxy-5-(1-hydroxy-4-methylpent-2-en-1-yl)-3-methoxyoxolan-2-one)