NP-MRD: Showing NP-Card for 3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one (NP0196590)

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Record Information

Version

2.0

Created at

2022-09-04 14:42:34 UTC

Updated at

2022-09-04 14:42:34 UTC

NP-MRD ID

NP0196590

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one

Description

Subglutinol B belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one is found in Fusarium subglutinans. Based on a literature review very few articles have been published on Subglutinol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042216422D          

 31 34  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042216422D          

 31 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0196590

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C[C@H]1C[C@]2(C)[C@H](CC[C@]3(C)[C@H](CC4=C(O)C(C)=C(C)OC4=O)C(=C)CC[C@@H]23)O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O4/c1-15(2)12-19-14-27(7)22-9-8-16(3)21(26(22,6)11-10-23(27)31-19)13-20-24(28)17(4)18(5)30-25(20)29/h12,19,21-23,28H,3,8-11,13-14H2,1-2,4-7H3/t19-,21+,22+,23-,26+,27-/m0/s1

> <INCHI_KEY>
SXNPXUJAUIINIU-ZZJUZBICSA-N

> <FORMULA>
C27H38O4

> <MOLECULAR_WEIGHT>
426.597

> <EXACT_MASS>
426.277009704

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.8697179933561

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(2R,3aS,5aR,6R,9aR,9bS)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-dodecahydronaphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethyl-2H-pyran-2-one

> <JCHEM_LOGP>
5.4198618843333355

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.657564932613568

> <JCHEM_PKA_STRONGEST_BASIC>
-4.197269855591476

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
125.84279999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R,3aS,5aR,6R,9aR,9bS)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1H-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.411  -1.636   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.128  -1.588   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.856  -0.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.395  -0.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207  -1.492   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.746  -1.444   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.076  -0.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.740  -0.268   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.166  -0.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.475  -0.039   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.832  -0.767   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.141   0.045   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.880  -2.306   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.053  -2.386   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.557  -2.753   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.829  -4.110   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.290  -4.158   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.479  -2.849   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.751  -4.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.939  -2.897   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.211  -4.254   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.328  -4.302   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.056  -5.659   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.245  -6.968   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.595  -5.707   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.323  -7.064   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.406  -4.398   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.946  -4.447   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.678  -3.041   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.139  -2.993   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.348  -1.467   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    5   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    2   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   22   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₄

Average Mass

426.5970 Da

Monoisotopic Mass

426.27701 Da

IUPAC Name

3-{[(2R,3aS,5aR,6R,9aR,9bS)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-dodecahydronaphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethyl-2H-pyran-2-one

Traditional Name

3-{[(2R,3aS,5aR,6R,9aR,9bS)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1H-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one

CAS Registry Number

Not Available

SMILES

CC(C)=C[C@H]1C[C@]2(C)[C@H](CC[C@]3(C)[C@H](CC4=C(O)C(C)=C(C)OC4=O)C(=C)CC[C@@H]23)O1

InChI Identifier

InChI=1S/C27H38O4/c1-15(2)12-19-14-27(7)22-9-8-16(3)21(26(22,6)11-10-23(27)31-19)13-20-24(28)17(4)18(5)30-25(20)29/h12,19,21-23,28H,3,8-11,13-14H2,1-2,4-7H3/t19-,21+,22+,23-,26+,27-/m0/s1

InChI Key

SXNPXUJAUIINIU-ZZJUZBICSA-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
Fusarium subglutinans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Pyranone
Pyran
Heteroaromatic compound
Vinylogous acid
Oxolane
Lactone
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	5.42	ChemAxon
pKa (Strongest Acidic)	7.66	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	125.84 m³·mol⁻¹	ChemAxon
Polarizability	49.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

24699332

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54691259

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one (NP0196590)

MOL for NP0196590 (3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one)

3D MOL for NP0196590 (3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one)

3D SDF for NP0196590 (3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one)

3D-SDF for NP0196590 (3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one)

PDB for NP0196590 (3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one)

3D PDB for NP0196590 (3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one)

SMILES for NP0196590 (3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one)

INCHI for NP0196590 (3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one)

Structure for NP0196590 (3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one)

3D Structure for NP0196590 (3-{[(2r,3as,5ar,6r,9ar,9bs)-5a,9b-dimethyl-7-methylidene-2-(2-methylprop-1-en-1-yl)-octahydro-1h-naphtho[2,1-b]furan-6-yl]methyl}-4-hydroxy-5,6-dimethylpyran-2-one)