NP-MRD: Showing NP-Card for 5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol (NP0222530)

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Record Information

Version

2.0

Created at

2022-09-06 00:23:38 UTC

Updated at

2022-09-06 00:23:38 UTC

NP-MRD ID

NP0222530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol

Description

5-[2-(Furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-decahydronaphthalene-2,3-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-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol is found in Austroeupatorium inulifolium. 5-[2-(Furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-decahydronaphthalene-2,3-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251507292D          

 23 25  0  0  0  0            999 V2000
    0.7145   -2.0625    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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 O   0  0  0  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 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
    2.1434   -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
    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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>
NP0222530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(O)C(O)C(CO)C1CCC(=C)C2CCC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O4/c1-12-3-5-16-14(10-20)18(22)17(21)9-19(16,2)15(12)6-4-13-7-8-23-11-13/h7-8,11,14-18,20-22H,1,3-6,9-10H2,2H3

> <INCHI_KEY>
OIVWMUPVCLMKJG-UHFFFAOYSA-N

> <FORMULA>
C19H28O4

> <MOLECULAR_WEIGHT>
320.429

> <EXACT_MASS>
320.198759382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.66639114940999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
1.864716737333333

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.007001842648805

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.69547018505098

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6344410113624948

> <JCHEM_POLAR_SURFACE_AREA>
73.83

> <JCHEM_REFRACTIVITY>
88.59570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -3.850   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  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   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       5.335  -3.080   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   11   16                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   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

C₁₉H₂₈O₄

Average Mass

320.4290 Da

Monoisotopic Mass

320.19876 Da

IUPAC Name

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

Traditional Name

5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol

CAS Registry Number

Not Available

SMILES

CC12CC(O)C(O)C(CO)C1CCC(=C)C2CCC1=COC=C1

InChI Identifier

InChI=1S/C19H28O4/c1-12-3-5-16-14(10-20)18(22)17(21)9-19(16,2)15(12)6-4-13-7-8-23-11-13/h7-8,11,14-18,20-22H,1,3-6,9-10H2,2H3

InChI Key

OIVWMUPVCLMKJG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Austroeupatorium inulaefolium	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
Furan
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
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	1.86	ALOGPS
logP	1.86	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.7	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.6 m³·mol⁻¹	ChemAxon
Polarizability	35.67 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

73189501

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-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol (NP0222530)

MOL for NP0222530 (5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol)

3D MOL for NP0222530 (5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol)

3D SDF for NP0222530 (5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol)

3D-SDF for NP0222530 (5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol)

PDB for NP0222530 (5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol)

3D PDB for NP0222530 (5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol)

SMILES for NP0222530 (5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol)

INCHI for NP0222530 (5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol)

Structure for NP0222530 (5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol)

3D Structure for NP0222530 (5-[2-(furan-3-yl)ethyl]-1-(hydroxymethyl)-4a-methyl-6-methylidene-octahydronaphthalene-2,3-diol)