NP-MRD: Showing NP-Card for (1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol (NP0220774)

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Record Information

Version

2.0

Created at

2022-09-05 22:10:57 UTC

Updated at

2022-09-05 22:10:57 UTC

NP-MRD ID

NP0220774

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol

Description

J3.574.713C belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review very few articles have been published on J3.574.713C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200102D          

 13 13  0  0  1  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  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
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
  4  2  1  1  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  1  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0220774

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O3/c1-6(2)7-4-5-10(3,13)9(12)8(7)11/h4-9,11-13H,1-3H3/t7-,8-,9-,10+/m1/s1

> <INCHI_KEY>
XGHAQANKWRPDSO-KYXWUPHJSA-N

> <FORMULA>
C10H18O3

> <MOLECULAR_WEIGHT>
186.251

> <EXACT_MASS>
186.12559444

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
20.433882928754265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,3S,6S)-3-methyl-6-(propan-2-yl)cyclohex-4-ene-1,2,3-triol

> <JCHEM_LOGP>
0.3020093083333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.17682987078674

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.856857663909423

> <JCHEM_PKA_STRONGEST_BASIC>
-3.324998457083491

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
51.2205

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,6S)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   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  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₈O₃

Average Mass

186.2510 Da

Monoisotopic Mass

186.12559 Da

IUPAC Name

(1R,2R,3S,6S)-3-methyl-6-(propan-2-yl)cyclohex-4-ene-1,2,3-triol

Traditional Name

(1R,2R,3S,6S)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H18O3/c1-6(2)7-4-5-10(3,13)9(12)8(7)11/h4-9,11-13H,1-3H3/t7-,8-,9-,10+/m1/s1

InChI Key

XGHAQANKWRPDSO-KYXWUPHJSA-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 menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclitol or derivatives
Tertiary alcohol
Secondary alcohol
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	0.3	ChemAxon
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	51.22 m³·mol⁻¹	ChemAxon
Polarizability	20.43 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

132583192

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol (NP0220774)

MOL for NP0220774 ((1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol)

3D MOL for NP0220774 ((1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol)

3D SDF for NP0220774 ((1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol)

3D-SDF for NP0220774 ((1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol)

PDB for NP0220774 ((1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol)

3D PDB for NP0220774 ((1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol)

SMILES for NP0220774 ((1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol)

INCHI for NP0220774 ((1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol)

Structure for NP0220774 ((1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol)

3D Structure for NP0220774 ((1r,2r,3s,6s)-6-isopropyl-3-methylcyclohex-4-ene-1,2,3-triol)