NP-MRD: Showing NP-Card for 5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol (NP0222956)

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Record Information

Version

2.0

Created at

2022-09-06 00:55:22 UTC

Updated at

2022-09-06 00:55:22 UTC

NP-MRD ID

NP0222956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol

Description

5-[2-(Furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-decahydronaphthalene-2,6-diol belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. 5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol is found in Dodonaea viscosa. 5-[2-(Furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-decahydronaphthalene-2,6-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161507012D          

 23 25  0  0  0  0            999 V2000
   -0.0980   -1.0942    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
    0.4323   -2.0127    0.0000 O   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  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
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    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
    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  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -4.1974    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  1  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
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 19 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222956

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(O)CCC2C(C)(C)C(O)CCC2(C)C1CCC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-18(2)15-7-11-20(4,22)16(6-5-14-9-12-23-13-14)19(15,3)10-8-17(18)21/h9,12-13,15-17,21-22H,5-8,10-11H2,1-4H3

> <INCHI_KEY>
RQAGOQPWWLBECE-UHFFFAOYSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.113048662386255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-decahydronaphthalene-2,6-diol

> <ALOGPS_LOGP>
4.04

> <JCHEM_LOGP>
3.7451816699999996

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.489432219695786

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.772174148147506

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8302643915680047

> <JCHEM_POLAR_SURFACE_AREA>
53.6

> <JCHEM_REFRACTIVITY>
91.70700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2H-naphthalene-2,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -0.183  -2.043   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  O   UNK     0       0.807  -3.757   0.000  0.00  0.00           O+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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.247  -7.835   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.771  -9.300   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.231  -9.300   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.755  -7.835   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   16                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6   15   16                                             
CONECT   15   14                                                            
CONECT   16   14    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₃

Average Mass

320.4730 Da

Monoisotopic Mass

320.23514 Da

IUPAC Name

5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-decahydronaphthalene-2,6-diol

Traditional Name

5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2H-naphthalene-2,6-diol

CAS Registry Number

Not Available

SMILES

CC1(O)CCC2C(C)(C)C(O)CCC2(C)C1CCC1=COC=C1

InChI Identifier

InChI=1S/C20H32O3/c1-18(2)15-7-11-20(4,22)16(6-5-14-9-12-23-13-14)19(15,3)10-8-17(18)21/h9,12-13,15-17,21-22H,5-8,10-11H2,1-4H3

InChI Key

RQAGOQPWWLBECE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dodonaea viscosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Heteroaromatic compound
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.04	ALOGPS
logP	3.75	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.71 m³·mol⁻¹	ChemAxon
Polarizability	37.11 Å³	ChemAxon
Number of Rings	3	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol (NP0222956)

MOL for NP0222956 (5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol)

3D MOL for NP0222956 (5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol)

3D SDF for NP0222956 (5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol)

3D-SDF for NP0222956 (5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol)

PDB for NP0222956 (5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol)

3D PDB for NP0222956 (5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol)

SMILES for NP0222956 (5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol)

INCHI for NP0222956 (5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol)

Structure for NP0222956 (5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol)

3D Structure for NP0222956 (5-[2-(furan-3-yl)ethyl]-1,1,4a,6-tetramethyl-hexahydro-2h-naphthalene-2,6-diol)