NP-MRD: Showing NP-Card for (1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol (NP0177204)

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Record Information

Version

2.0

Created at

2022-09-03 15:00:44 UTC

Updated at

2022-09-03 15:00:44 UTC

NP-MRD ID

NP0177204

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol

Description

Penicieudesmol F belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Based on a literature review very few articles have been published on Penicieudesmol F.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032217002D          

 20 21  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   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
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   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
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0177204

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@H](O)[C@@H](O)[C@]2(C)CC[C@H](C[C@@]12O)C(C)(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C15H28O5/c1-9-6-11(17)12(18)13(2)5-4-10(7-15(9,13)20)14(3,19)8-16/h9-12,16-20H,4-8H2,1-3H3/t9-,10+,11-,12+,13-,14?,15+/m0/s1

> <INCHI_KEY>
JEQGOLIJMUAHSU-ARGBDDAASA-N

> <FORMULA>
C15H28O5

> <MOLECULAR_WEIGHT>
288.384

> <EXACT_MASS>
288.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
31.437919555980905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4S,4aR,6R,8aS)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-decahydronaphthalene-1,2,4a-triol

> <JCHEM_LOGP>
-0.5545969466666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.852807560019684

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.31196281126098

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0715917825437966

> <JCHEM_POLAR_SURFACE_AREA>
101.15

> <JCHEM_REFRACTIVITY>
74.4558

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,4aR,6R,8aS)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.232  -4.414   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.772  -1.746   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   19                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16                                                            
CONECT   18   12   19                                                       
CONECT   19   18    2    8   20                                             
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₈O₅

Average Mass

288.3840 Da

Monoisotopic Mass

288.19367 Da

IUPAC Name

(1S,2S,4S,4aR,6R,8aS)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-decahydronaphthalene-1,2,4a-triol

Traditional Name

(1S,2S,4S,4aR,6R,8aS)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@H](O)[C@@H](O)[C@]2(C)CC[C@H](C[C@@]12O)C(C)(O)CO

InChI Identifier

InChI=1S/C15H28O5/c1-9-6-11(17)12(18)13(2)5-4-10(7-15(9,13)20)14(3,19)8-16/h9-12,16-20H,4-8H2,1-3H3/t9-,10+,11-,12+,13-,14?,15+/m0/s1

InChI Key

JEQGOLIJMUAHSU-ARGBDDAASA-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 eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	-0.55	ChemAxon
pKa (Strongest Acidic)	13.31	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.46 m³·mol⁻¹	ChemAxon
Polarizability	31.44 Å³	ChemAxon
Number of Rings	2	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78315815

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146682531

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol (NP0177204)

MOL for NP0177204 ((1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol)

3D MOL for NP0177204 ((1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol)

3D SDF for NP0177204 ((1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol)

3D-SDF for NP0177204 ((1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol)

PDB for NP0177204 ((1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol)

3D PDB for NP0177204 ((1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol)

SMILES for NP0177204 ((1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol)

INCHI for NP0177204 ((1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol)

Structure for NP0177204 ((1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol)

3D Structure for NP0177204 ((1s,2s,4s,4ar,6r,8as)-6-(1,2-dihydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalene-1,2,4a-triol)