NP-MRD: Showing NP-Card for Drimenin (NP0051869)

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Record Information

Version

2.0

Created at

2022-04-27 23:04:29 UTC

Updated at

2022-04-27 23:04:29 UTC

NP-MRD ID

NP0051869

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Drimenin

Description

Drimenin 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. Drimenin is found in Cinnamodendron corticosum, Drimys winteri , Persicaria minor, Polygonum minus, Porella canariensis, Porella cordaeana and Porella spp.. Drimenin was first documented in 2005 (PMID: 17193193). Based on a literature review a significant number of articles have been published on Drimenin (PMID: 29634269) (PMID: 33036992) (PMID: 34707350) (PMID: 20361301) (PMID: 19251287).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -2.6489    0.2223   -1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7798    0.3543    0.0636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2976    1.6657    0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1642   -0.7282    1.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1592   -1.0894    2.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141   -0.5265    1.8040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -0.5073    0.3380 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5436   -1.8867   -0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463    0.4797   -0.2792 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1129    0.6274   -1.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3434    0.9792   -1.9073 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2647    0.7337   -1.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7045    0.9768   -0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1696   -0.1849   -0.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0897   -0.9127    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826   -2.1174    0.5811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.0512    0.2392 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6647    1.1734   -1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861    0.0728   -0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3761   -0.6463   -1.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3966    2.4302   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3055    1.4741    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    1.9719    1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1098   -0.4291    1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5307   -1.6007    0.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753   -2.2051    2.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4725   -0.7858    3.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9624   -1.0281    2.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2180    0.5518    2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6421   -2.6055    0.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4527   -2.1775   -0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3675   -2.1400   -0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0074    1.4806    0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561   -0.3066   -2.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    1.5067   -2.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663    1.4998   -2.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9073    1.8387   -0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2047    1.0546   -1.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512    0.7332    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  2  1  0
  9  7  1  0
 12 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 17 39  1  1
 13 37  1  0
 13 38  1  0
 11 36  1  0
 10 34  1  0
 10 35  1  0
  9 33  1  1
M  END


  Mrv1652304282201042D          

 17 19  0  0  1  0            999 V2000
    2.8571    0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8124    2.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9878    2.2242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5978    1.4972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0325    0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7732    1.4714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3386    2.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7286    2.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    2.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626    1.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232    1.1532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406    0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373    0.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079    0.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981    2.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8155    3.0749    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
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
  5 15  1  1  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051869

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]2(C)[C@H]3C(=O)OCC3=CC[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-14(2)7-4-8-15(3)11(14)6-5-10-9-17-13(16)12(10)15/h5,11-12H,4,6-9H2,1-3H3/t11-,12+,15-/m0/s1

> <INCHI_KEY>
BQNSBENKJCLJGN-ZOWXZIJZSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.57158491239716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5aS,9aS,9bR)-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-1-one

> <ALOGPS_LOGP>
4.34

> <JCHEM_LOGP>
3.041859042666666

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.139984536832808

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
67.5228

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
drimenin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.333   1.534   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.061   2.891   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.250   4.200   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.711   4.152   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.983   2.795   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.794   1.486   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.443   2.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.632   4.056   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.360   5.413   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.899   5.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.863   3.689   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.977   2.153   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.449   1.571   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.816   0.075   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.255   1.438   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.530   5.056   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.256   5.740   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   16   17                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   15                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   13                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13                                                            
CONECT   15    5                                                            
CONECT   16    3                                                            
CONECT   17    3                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3390 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

(5aS,9aS,9bR)-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-1-one

Traditional Name

drimenin

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@H]3C(=O)OCC3=CC[C@@H]12

InChI Identifier

InChI=1S/C15H22O2/c1-14(2)7-4-8-15(3)11(14)6-5-10-9-17-13(16)12(10)15/h5,11-12H,4,6-9H2,1-3H3/t11-,12+,15-/m0/s1

InChI Key

BQNSBENKJCLJGN-ZOWXZIJZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cinnamodendron corticosum	LOTUS Database	35616633
Drimys winteri	Plant	KNApSAcK
Persicaria minor	LOTUS Database	35616633
Polygonum minus	Plant	KNApSAcK
Porella canariensis	LOTUS Database	35616633
Porella cordaeana	LOTUS Database	35616633
Porella spp.	Plant	KNApSAcK

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
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

naphthofuran (CHEBI:4715 )
Drimane sesquiterpenoids (C09399 )
Sesquiterpenoids (C15) (C09399 )

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	4.34	ALOGPS
logP	3.04	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.52 m³·mol⁻¹	ChemAxon
Polarizability	26.57 Å³	ChemAxon
Number of Rings	3	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

C00003252

Chemspider ID

390708

KEGG Compound ID

C09399

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442202

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Arias HR, Feuerbach D, Schmidt B, Heydenreich M, Paz C, Ortells MO: Drimane Sesquiterpenoids Noncompetitively Inhibit Human alpha4beta2 Nicotinic Acetylcholine Receptors with Higher Potency Compared to Human alpha3beta4 and alpha7 Subtypes. J Nat Prod. 2018 Apr 27;81(4):811-817. doi: 10.1021/acs.jnatprod.7b00893. Epub 2018 Apr 10. [PubMed:29634269 ]
Socolsky C, Muruaga N, Bardon A: Drimanes and other terpenoids from the fern Thelypteris hispidula (Decne.) Reed. Chem Biodivers. 2005 Aug;2(8):1105-8. doi: 10.1002/cbdv.200590079. [PubMed:17193193 ]
Paz C, Viscardi S, Iturra A, Marin V, Miranda F, Barra PJ, Mendez I, Duran P: Antifungal Effects of Drimane Sesquiterpenoids Isolated from Drimys winteri against Gaeumannomyces graminis var. tritici. Appl Environ Microbiol. 2020 Nov 24;86(24). pii: AEM.01834-20. doi: 10.1128/AEM.01834-20. Print 2020 Nov 24. [PubMed:33036992 ]
Omoboyowa DA, Balogun TA, Omomule OM, Saibu OA: Identification of Terpenoids From Abrus precatorius Against Parkinson's Disease Proteins Using In Silico Approach. Bioinform Biol Insights. 2021 Oct 20;15:11779322211050757. doi: 10.1177/11779322211050757. eCollection 2021. [PubMed:34707350 ]
Rukachaisirikul V, Khamthong N, Sukpondma Y, Phongpaichit S, Hutadilok-Towatana N, Graidist P, Sakayaroj J, Kirtikara K: Cyclohexene, diketopiperazine, lactone and phenol derivatives from the sea fan-derived fungi Nigrospora sp. PSU-F11 and PSU-F12. Arch Pharm Res. 2010 Mar;33(3):375-80. doi: 10.1007/s12272-010-0305-3. Epub 2010 Mar 30. [PubMed:20361301 ]
Allouche N, Apel C, Martin MT, Dumontet V, Gueritte F, Litaudon M: Cytotoxic sesquiterpenoids from Winteraceae of Caledonian rainforest. Phytochemistry. 2009 Mar;70(4):546-53. doi: 10.1016/j.phytochem.2009.01.012. Epub 2009 Feb 27. [PubMed:19251287 ]

Showing NP-Card for Drimenin (NP0051869)

MOL for NP0051869 (Drimenin)

3D MOL for NP0051869 (Drimenin)

3D SDF for NP0051869 (Drimenin)

3D-SDF for NP0051869 (Drimenin)

PDB for NP0051869 (Drimenin)

3D PDB for NP0051869 (Drimenin)

SMILES for NP0051869 (Drimenin)

INCHI for NP0051869 (Drimenin)

Structure for NP0051869 (Drimenin)

3D Structure for NP0051869 (Drimenin)