NP-MRD: Showing NP-Card for (-)-Drimenol (NP0139217)

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Record Information

Version

1.0

Created at

2022-06-29 19:44:27 UTC

Updated at

2022-06-29 19:44:28 UTC

NP-MRD ID

NP0139217

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Drimenol

Description

Drimenol, also known as drim-7-en-11-ol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Thus, drimenol is considered to be an isoprenoid. (-)-Drimenol is found in Bazzania trilobata, Diplophyllum serrulatum, Drimys winteri, Lactarius uvidus, Persicaria hydropiper, Targionia hypophylla and Trichocolea tomentella. It was first documented in 2019 (PMID: 31807198). Based on a literature review a significant number of articles have been published on drimenol (PMID: 30935903) (PMID: 33036992) (PMID: 31676401) (PMID: 35446557) (PMID: 34829191) (PMID: 34468074).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    3.6032   -1.1553    0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385   -1.0175    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3419   -1.8631    0.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403   -1.8643    0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6858   -0.6348   -0.1709 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0600   -0.2812    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0561   -0.6745   -0.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4879   -1.0841    1.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2933    1.1521    0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5449    2.1532   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3061    1.6597   -0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2967    0.5199   -0.1131 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7028    0.8646    1.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415    0.0403   -0.8443 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4980    1.1511   -1.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5876    0.5506   -1.8275 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1097   -0.1756    0.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9999   -1.7630   -0.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8405   -1.7152    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764   -2.6331    1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5340   -2.0144    1.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056   -2.7978   -0.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6959   -0.9209   -1.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597   -1.2843   -1.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9018   -1.2469   -0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4597    0.2207   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9242   -0.7891    2.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5484   -0.7378    1.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5536   -2.1497    1.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0915    1.3294    1.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3813    1.3581    0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999    2.5721   -1.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2937    3.0354    0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3954    2.5300   -0.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321    1.2884   -1.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4423    0.0816    2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2562    1.8564    1.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8070    1.0127    1.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2066   -0.3794   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0080    1.7716   -1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8124    1.7401   -0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2909    0.2939   -2.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14  2  1  0
 12  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  6
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  6
 15 40  1  0
 15 41  1  0
 16 42  1  0
M  END


  Mrv1652306292221442D          

 16 17  0  0  1  0            999 V2000
   -1.4289    0.0000    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
   -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  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  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
    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0139217

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1CO

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

> <INCHI_KEY>
HMWSKUKBAWWOJL-KCQAQPDRSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
27.519600573642155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
3.3637087709999998

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.55114538109709

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2455290103081325

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
69.4007

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
drimenol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   10   16                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    6                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(-)-Drim-7-en-11-ol	ChEBI
(-)-Drimenol	ChEBI
(1S,2S,6S)-1,3,7,7-Tetramethylbicyclo[4.4.0]dec-3-ene-2-methanol	ChEBI
(1S-(1alpha,4Abeta,8aalpha))-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenemethanol	ChEBI
(5S,9S,10S)-(-)-Drim-7-en-11-ol	ChEBI
(5S,9S,10S)-Drim-7-en-11-ol	ChEBI
Drim-7-en-11-ol	ChEBI
(1S-(1a,4Abeta,8aalpha))-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenemethanol	Generator
(1S-(1Α,4abeta,8aalpha))-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenemethanol	Generator

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=CC[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1CO

InChI Identifier

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

InChI Key

HMWSKUKBAWWOJL-KCQAQPDRSA-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
Bazzania trilobata	LOTUS Database	35616633
Diplophyllum serrulatum	LOTUS Database	35616633
Drimys winteri	LOTUS Database	35616633
Lactarius uvidus	LOTUS Database	35616633
Persicaria hydropiper	LOTUS Database	35616633
Targionia hypophylla	LOTUS Database	35616633
Trichocolea tomentella	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Primary alcohols

Alternative Parents

Hydrocarbon derivatives

Substituents

Hydrocarbon derivative
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

primary alcohol (CHEBI:61148 )
naphthalenes (CHEBI:61148 )
sesquiterpenoid (CHEBI:61148 )
Drimane sesquiterpenoids (LMPR0103370001 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00020282

Chemspider ID

2338310

KEGG Compound ID

C19743

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3080551

PDB ID

Not Available

ChEBI ID

61148

Good Scents ID

rw1453791

References

General References

Lacey HJ, Gilchrist CLM, Crombie A, Kalaitzis JA, Vuong D, Rutledge PJ, Turner P, Pitt JI, Lacey E, Chooi YH, Piggott AM: Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis. Beilstein J Org Chem. 2019 Nov 5;15:2631-2643. doi: 10.3762/bjoc.15.256. eCollection 2019. [PubMed:31807198 ]
Russo A, Cardile V, Graziano ACE, Avola R, Montenegro I, Cuellar M, Villena J, Madrid A: Antigrowth activity and induction of apoptosis in human melanoma cells by Drymis winteri forst extract and its active components. Chem Biol Interact. 2019 May 25;305:79-85. doi: 10.1016/j.cbi.2019.03.029. Epub 2019 Mar 29. [PubMed:30935903 ]
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 ]
Kipanga PN, Liu M, Panda SK, Mai AH, Veryser C, Van Puyvelde L, De Borggraeve WM, Van Dijck P, Matasyoh J, Luyten W: Biofilm inhibiting properties of compounds from the leaves of Warburgia ugandensis Sprague subsp ugandensis against Candida and staphylococcal biofilms. J Ethnopharmacol. 2020 Feb 10;248:112352. doi: 10.1016/j.jep.2019.112352. Epub 2019 Oct 30. [PubMed:31676401 ]
Vo NNQ, Nomura Y, Kinugasa K, Takagi H, Takahashi S: Identification and Characterization of Bifunctional Drimenol Synthases of Marine Bacterial Origin. ACS Chem Biol. 2022 May 20;17(5):1226-1238. doi: 10.1021/acschembio.2c00163. Epub 2022 Apr 21. [PubMed:35446557 ]
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Showing NP-Card for (-)-Drimenol (NP0139217)

MOL for NP0139217 ((-)-Drimenol)

3D MOL for NP0139217 ((-)-Drimenol)

3D SDF for NP0139217 ((-)-Drimenol)

3D-SDF for NP0139217 ((-)-Drimenol)

PDB for NP0139217 ((-)-Drimenol)

3D PDB for NP0139217 ((-)-Drimenol)

SMILES for NP0139217 ((-)-Drimenol)

INCHI for NP0139217 ((-)-Drimenol)

Structure for NP0139217 ((-)-Drimenol)

3D Structure for NP0139217 ((-)-Drimenol)