NP-MRD: Showing NP-Card for 2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol (NP0327112)

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Record Information

Version

1.0

Created at

2022-09-12 09:22:12 UTC

Updated at

2022-09-12 09:22:12 UTC

NP-MRD ID

NP0327112

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol

Description

7-Epi-alpha-eudesmol 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. 2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol is found in Callicarpa americana and Laggera alata. It was first documented in 2000 (PMID: 10898657). Based on a literature review a small amount of articles have been published on 7-epi-alpha-eudesmol (PMID: 27829890).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122211222D          

 16 17  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  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
    0.7145   -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
    2.1434    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  2  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
    5.0013   -2.0625    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
    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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 10 15  1  0  0  0  0
 16 15  1  1  0  0  0
  2 16  1  0  0  0  0
  6 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327112

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC[C@]2(C)CC[C@@H](C[C@@H]12)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h6,12-13,16H,5,7-10H2,1-4H3/t12-,13-,15+/m0/s1

> <INCHI_KEY>
FCSRUSQUAVXUKK-KCQAQPDRSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
27.316396393585762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2S,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]propan-2-ol

> <JCHEM_LOGP>
3.4737942476666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.317402208596036

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9103682739600937

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
69.434

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2S,4aR,8aR)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]propan-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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       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  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   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  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.232  -4.414   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.772  -1.746   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   16                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   10   16                                                       
CONECT   16   15    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
[2S-(2alpha,4Abeta,8aalpha)]-1,2,3,4,4a,5,6,8a-octahydro-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol	ChEBI
[2S-(2a,4Abeta,8aalpha)]-1,2,3,4,4a,5,6,8a-octahydro-a,a,4a,8-tetramethyl-2-naphthalenemethanol	Generator
[2S-(2Α,4abeta,8aalpha)]-1,2,3,4,4a,5,6,8a-octahydro-α,α,4a,8-tetramethyl-2-naphthalenemethanol	Generator
7-Epi-a-eudesmol	Generator
7-Epi-α-eudesmol	Generator

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

2-[(2S,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]propan-2-ol

Traditional Name

2-[(2S,4aR,8aR)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]propan-2-ol

CAS Registry Number

Not Available

SMILES

CC1=CCC[C@]2(C)CC[C@@H](C[C@@H]12)C(C)(C)O

InChI Identifier

InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h6,12-13,16H,5,7-10H2,1-4H3/t12-,13-,15+/m0/s1

InChI Key

FCSRUSQUAVXUKK-KCQAQPDRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Callicarpa americana	LOTUS Database	35616633
Laggera alata	LOTUS Database	35616633

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
Organic oxygen compound
Hydrocarbon derivative
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	3.47	ChemAxon
pKa (Strongest Acidic)	19.32	ChemAxon
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.43 m³·mol⁻¹	ChemAxon
Polarizability	27.32 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00012803

Chemspider ID

10380314

KEGG Compound ID

Not Available

BioCyc ID

CPD-20134

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12304196

PDB ID

Not Available

ChEBI ID

138040

Good Scents ID

rw1552481

References

General References

Rabe P, Schmitz T, Dickschat JS: Mechanistic investigations on six bacterial terpene cyclases. Beilstein J Org Chem. 2016 Aug 15;12:1839-1850. doi: 10.3762/bjoc.12.173. eCollection 2016. [PubMed:27829890 ]
Tellez MR, Dayan FE, Schrader KK, Wedge DE, Duke SO: Composition and some biological activities of the essential oil of Callicarpa americana (L.). J Agric Food Chem. 2000 Jul;48(7):3008-12. doi: 10.1021/jf991026g. [PubMed:10898657 ]
LOTUS database [Link]

Showing NP-Card for 2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol (NP0327112)

MOL for NP0327112 (2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol)

3D MOL for NP0327112 (2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol)

3D SDF for NP0327112 (2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol)

3D-SDF for NP0327112 (2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol)

PDB for NP0327112 (2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol)

3D PDB for NP0327112 (2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol)

SMILES for NP0327112 (2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol)

INCHI for NP0327112 (2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol)

Structure for NP0327112 (2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol)

3D Structure for NP0327112 (2-[(2s,4ar,8ar)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-2-yl]propan-2-ol)