NP-MRD: Showing NP-Card for [(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid (NP0286810)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 15:34:13 UTC

Updated at

2022-09-09 15:34:13 UTC

NP-MRD ID

NP0286810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid

Description

[(1R,4E)-1-hydroxy-1-methyl-7-(propan-2-yl)-1,2,3,3a,4,5,6,8a-octahydroazulen-4-ylidene]methanesulfonic acid belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. [(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid is found in Alisma plantago-aquatica. Based on a literature review very few articles have been published on [(1R,4E)-1-hydroxy-1-methyl-7-(propan-2-yl)-1,2,3,3a,4,5,6,8a-octahydroazulen-4-ylidene]methanesulfonic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092217342D          

 20 21  0  0  1  0            999 V2000
    2.1986   -0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3158    0.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    0.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    0.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    1.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    1.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    2.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333    1.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    0.8586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8556    0.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853    0.0499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    2.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977    3.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6025    3.8184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2072    4.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1636    3.2136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0413    4.4232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    2.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    1.5261    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  6  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2C(CC[C@@]2(C)O)\C(CC1)=C\S(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O4S/c1-10(2)11-4-5-12(9-20(17,18)19)13-6-7-15(3,16)14(13)8-11/h8-10,13-14,16H,4-7H2,1-3H3,(H,17,18,19)/b12-9+/t13?,14?,15-/m1/s1

> <INCHI_KEY>
DGQQFMFGQBQZSD-CNOPSNAFSA-N

> <FORMULA>
C15H24O4S

> <MOLECULAR_WEIGHT>
300.41

> <EXACT_MASS>
300.139530427

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.5992762821155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,4E)-1-hydroxy-1-methyl-7-(propan-2-yl)-1,2,3,3a,4,5,6,8a-octahydroazulen-4-ylidene]methanesulfonic acid

> <JCHEM_LOGP>
1.26927318666544

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.62243321694182

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.2217289208565436

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9305623358202156

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
79.92069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,4E)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       4.104  -1.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.667   0.257   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.189   0.487   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.706   1.461   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.205   1.119   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.001   2.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.001   3.619   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.464   4.095   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.369   2.849   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.464   1.603   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.597   0.560   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.159   0.093   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.205   4.579   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.862   6.080   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0       2.991   7.128   0.000  0.00  0.00           S+0
HETATM   16  O   UNK     0       4.120   8.175   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.039   5.999   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.944   8.257   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.706   4.236   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.375   2.849   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11   12                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   13   20                                                       
CONECT   20   19    4                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
[(1R,4E)-1-Hydroxy-1-methyl-7-(propan-2-yl)-1,2,3,3a,4,5,6,8a-octahydroazulen-4-ylidene]methanesulfonate	Generator
[(1R,4E)-1-Hydroxy-1-methyl-7-(propan-2-yl)-1,2,3,3a,4,5,6,8a-octahydroazulen-4-ylidene]methanesulphonate	Generator
[(1R,4E)-1-Hydroxy-1-methyl-7-(propan-2-yl)-1,2,3,3a,4,5,6,8a-octahydroazulen-4-ylidene]methanesulphonic acid	Generator

Chemical Formula

C₁₅H₂₄O₄S

Average Mass

300.4100 Da

Monoisotopic Mass

300.13953 Da

IUPAC Name

[(1R,4E)-1-hydroxy-1-methyl-7-(propan-2-yl)-1,2,3,3a,4,5,6,8a-octahydroazulen-4-ylidene]methanesulfonic acid

Traditional Name

[(1R,4E)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2C(CC[C@@]2(C)O)\C(CC1)=C\S(O)(=O)=O

InChI Identifier

InChI=1S/C15H24O4S/c1-10(2)11-4-5-12(9-20(17,18)19)13-6-7-15(3,16)14(13)8-11/h8-10,13-14,16H,4-7H2,1-3H3,(H,17,18,19)/b12-9+/t13?,14?,15-/m1/s1

InChI Key

DGQQFMFGQBQZSD-CNOPSNAFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alisma plantago-aquatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Tertiary alcohol
Sulfonyl
Organosulfonic acid
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Cyclic alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
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	1.27	ChemAxon
pKa (Strongest Acidic)	-0.22	ChemAxon
pKa (Strongest Basic)	-0.93	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.92 m³·mol⁻¹	ChemAxon
Polarizability	32.6 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

4479258

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321552

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid (NP0286810)

MOL for NP0286810 ([(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid)

3D MOL for NP0286810 ([(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid)

3D SDF for NP0286810 ([(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid)

3D-SDF for NP0286810 ([(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid)

PDB for NP0286810 ([(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid)

3D PDB for NP0286810 ([(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid)

SMILES for NP0286810 ([(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid)

INCHI for NP0286810 ([(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid)

Structure for NP0286810 ([(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid)

3D Structure for NP0286810 ([(1r,4e)-1-hydroxy-7-isopropyl-1-methyl-2,3,3a,5,6,8a-hexahydroazulen-4-ylidene]methanesulfonic acid)