NP-MRD: Showing NP-Card for (4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one (NP0328271)

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Record Information

Version

1.0

Created at

2022-09-12 11:35:45 UTC

Updated at

2022-09-12 11:35:45 UTC

NP-MRD ID

NP0328271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one

Description

(4AR,6S,8aS)-6-[(1S)-1-hydroxyethyl]-2H,4aH,6H,8aH-pyrano[3,2-b]pyran-2-one belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. (4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one is found in Diplodia corticola and Diplodia mutila. Based on a literature review very few articles have been published on (4aR,6S,8aS)-6-[(1S)-1-hydroxyethyl]-2H,4aH,6H,8aH-pyrano[3,2-b]pyran-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122213352D          

 14 15  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  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
    0.7145   -1.2375    0.0000 C   0  0  2  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
    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 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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  6  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
  4 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@H]1O[C@@H]2C=CC(=O)O[C@H]2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-6(11)7-2-3-9-8(13-7)4-5-10(12)14-9/h2-9,11H,1H3/t6-,7-,8+,9-/m0/s1

> <INCHI_KEY>
YMKWNRDVGOVSHY-MAUMQABQSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.202

> <EXACT_MASS>
196.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.249188232340586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,6S,8aS)-6-[(1S)-1-hydroxyethyl]-2H,4aH,6H,8aH-pyrano[3,2-b]pyran-2-one

> <JCHEM_LOGP>
0.7511050330000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.113173057005614

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.450368257289217

> <JCHEM_PKA_STRONGEST_BASIC>
-3.039163744619697

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
50.36220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,6S,8aS)-6-[(1S)-1-hydroxyethyl]-4aH,6H,8aH-pyrano[3,2-b]pyran-2-one

> <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       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13    4                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₂O₄

Average Mass

196.2020 Da

Monoisotopic Mass

196.07356 Da

IUPAC Name

(4aR,6S,8aS)-6-[(1S)-1-hydroxyethyl]-2H,4aH,6H,8aH-pyrano[3,2-b]pyran-2-one

Traditional Name

(4aR,6S,8aS)-6-[(1S)-1-hydroxyethyl]-4aH,6H,8aH-pyrano[3,2-b]pyran-2-one

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@H]1O[C@@H]2C=CC(=O)O[C@H]2C=C1

InChI Identifier

InChI=1S/C10H12O4/c1-6(11)7-2-3-9-8(13-7)4-5-10(12)14-9/h2-9,11H,1H3/t6-,7-,8+,9-/m0/s1

InChI Key

YMKWNRDVGOVSHY-MAUMQABQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Diplodia corticola	LOTUS Database	35616633
Diplodia mutila	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.75	ChemAxon
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	50.36 m³·mol⁻¹	ChemAxon
Polarizability	19.25 Å³	ChemAxon
Number of Rings	2	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

552832

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

637192

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one (NP0328271)

MOL for NP0328271 ((4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one)

3D MOL for NP0328271 ((4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one)

3D SDF for NP0328271 ((4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one)

3D-SDF for NP0328271 ((4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one)

PDB for NP0328271 ((4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one)

3D PDB for NP0328271 ((4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one)

SMILES for NP0328271 ((4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one)

INCHI for NP0328271 ((4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one)

Structure for NP0328271 ((4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one)

3D Structure for NP0328271 ((4ar,6s,8as)-6-[(1s)-1-hydroxyethyl]-4ah,6h,8ah-pyrano[3,2-b]pyran-2-one)