NP-MRD: Showing NP-Card for Fern 9(11)-ene (NP0052219)

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Record Information

Version

2.0

Created at

2022-04-27 23:21:32 UTC

Updated at

2022-04-27 23:21:32 UTC

NP-MRD ID

NP0052219

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fern 9(11)-ene

Description

Fernene, also known as fern-9(11)-ene, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Fern 9(11)-ene is found in Adiantum capillus-veneris, Adiantum caudatum, Adiantum raddianum, Adiantum edgeworthii, Adiantum lunulatum , Adiantum pedatum, Albizia odoratissima , Alsophila podophylla, Alsophila spinulosa, Cyathea lepifera, Cyathea podophylla, Davallia mariesii, Diplopterygium glaucum, Dryopteris crassirhizoma, Goniophlebium mengtzeense, Lophosoria quadripinnata, Neocheiropteris fortunei, Oleandra wallichii, Phlebodium aureum, Plagiogyria glauca, Polypodium subpetiolatum and Polypodium virginianum. Fern 9(11)-ene was first documented in 2009 (PMID: 19848435). Based on a literature review a small amount of articles have been published on Fernene (PMID: 30051576) (PMID: 22370784).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201212D          

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     RDKit          3D

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 10 27  1  1  0  0  0
  5 28  1  6  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052219

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@]1(C)[C@H]3CC[C@H]4C(C)(C)CCC[C@]4(C)C3=CC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50/c1-20(2)21-10-13-25-28(21,6)18-19-29(7)23-11-12-24-26(3,4)15-9-16-27(24,5)22(23)14-17-30(25,29)8/h14,20-21,23-25H,9-13,15-19H2,1-8H3/t21-,23+,24+,25-,27-,28-,29-,30+/m1/s1

> <INCHI_KEY>
ZHDRLFGZQZCZKX-BQOUFORSSA-N

> <FORMULA>
C30H50

> <MOLECULAR_WEIGHT>
410.73

> <EXACT_MASS>
410.39125161

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
53.63896419163752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5R,6R,9R,10S,14S,19S)-2,5,10,14,18,18-hexamethyl-6-(propan-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-12-ene

> <ALOGPS_LOGP>
7.99

> <JCHEM_LOGP>
8.620923877666668

> <ALOGPS_LOGS>
-7.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
130.46529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,6R,9R,10S,14S,19S)-6-isopropyl-2,5,10,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-12-ene

> <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      13.521   2.092   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.271   0.747   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.481  -0.575   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.941  -0.552   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.191   0.793   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.981   2.115   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.651   0.817   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.902   2.162   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.362   2.185   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.572   0.864   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.321  -0.482   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.861  -0.505   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.611  -1.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.151  -1.874   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.531  -1.803   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.991  -1.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.242  -0.435   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.032   0.887   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.019   2.047   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.603   1.442   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.740  -0.092   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.580  -1.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.878  -2.616   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.123  -0.606   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.318  -1.667   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.071  -1.827   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.822   2.209   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.442   2.139   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.774  -1.411   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.511  -2.115   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   29   30                                             
CONECT    4    3    5   14                                                  
CONECT    5    4    6    7   28                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18   27                                             
CONECT   11   10   12   15   26                                             
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    4                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21   25                                             
CONECT   18   17   10   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   17                                                            
CONECT   26   11                                                            
CONECT   27   10                                                            
CONECT   28    5                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
Fern-9(11)-ene	MeSH

Chemical Formula

C₃₀H₅₀

Average Mass

410.7300 Da

Monoisotopic Mass

410.39125 Da

IUPAC Name

(1R,2R,5R,6R,9R,10S,14S,19S)-2,5,10,14,18,18-hexamethyl-6-(propan-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-12-ene

Traditional Name

(1R,2R,5R,6R,9R,10S,14S,19S)-6-isopropyl-2,5,10,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-12-ene

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@]1(C)[C@H]3CC[C@H]4C(C)(C)CCC[C@]4(C)C3=CC[C@@]21C

InChI Identifier

InChI=1S/C30H50/c1-20(2)21-10-13-25-28(21,6)18-19-29(7)23-11-12-24-26(3,4)15-9-16-27(24,5)22(23)14-17-30(25,29)8/h14,20-21,23-25H,9-13,15-19H2,1-8H3/t21-,23+,24+,25-,27-,28-,29-,30+/m1/s1

InChI Key

ZHDRLFGZQZCZKX-BQOUFORSSA-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
Adiantum capillus-veneris	LOTUS Database	35616633
Adiantum caudatum	LOTUS Database	35616633
Adiantum cuneatum	LOTUS Database	35616633
Adiantum edgeworthii	LOTUS Database	35616633
Adiantum lunulatum	Plant	KNApSAcK
Adiantum pedatum	LOTUS Database	35616633
Albizia odoratissima	Plant	KNApSAcK
Alsophila podophylla	LOTUS Database	35616633
Alsophila spinulosa	LOTUS Database	35616633
Cyathea lepifera	LOTUS Database	35616633
Cyathea podophylla	Plant	KNApSAcK
Davallia mariesii	LOTUS Database	35616633
Diplopterygium glaucum	LOTUS Database	35616633
Dryopteris crassirhizoma	Plant	KNApSAcK
Goniophlebium mengtzeense	LOTUS Database	35616633
Lophosoria quadripinnata	LOTUS Database	35616633
Neocheiropteris fortunei	LOTUS Database	35616633
Oleandra wallichii	LOTUS Database	35616633
Phlebodium aureum	LOTUS Database	35616633
Plagiogyria glauca	LOTUS Database	35616633
Polypodium subpetiolatum	LOTUS Database	35616633
Polypodium virginianum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroid
Delta-5-steroid
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

triterpenoid (CHEBI:5016 )
Hopanes (C08625 )

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	7.99	ALOGPS
logP	8.62	ChemAxon
logS	-7.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	130.47 m³·mol⁻¹	ChemAxon
Polarizability	53.64 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00003746

Chemspider ID

390293

KEGG Compound ID

C08625

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441679

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Maier MS, Rosso ML, Fazio AT, Adler MT, Bertoni MD: Fernene triterpenoids from the lichen Pyxine berteriana. J Nat Prod. 2009 Oct;72(10):1902-4. doi: 10.1021/np900442y. [PubMed:19848435 ]
Kuhnert E, Li Y, Lan N, Yue Q, Chen L, Cox RJ, An Z, Yokoyama K, Bills GF: Enfumafungin synthase represents a novel lineage of fungal triterpene cyclases. Environ Microbiol. 2018 Sep;20(9):3325-3342. doi: 10.1111/1462-2920.14333. Epub 2018 Sep 13. [PubMed:30051576 ]
Yuan XH, Xu GB, Wu WL, Yang T, Li GY: Peniciside, a new triterpenoid glycoside, from the fungus Penicillium sp. 169. Arch Pharm Res. 2012 Feb;35(2):311-4. doi: 10.1007/s12272-012-0210-z. Epub 2012 Feb 28. [PubMed:22370784 ]

Showing NP-Card for Fern 9(11)-ene (NP0052219)

MOL for NP0052219 (Fern 9(11)-ene)

3D MOL for NP0052219 (Fern 9(11)-ene)

3D SDF for NP0052219 (Fern 9(11)-ene)

3D-SDF for NP0052219 (Fern 9(11)-ene)

PDB for NP0052219 (Fern 9(11)-ene)

3D PDB for NP0052219 (Fern 9(11)-ene)

SMILES for NP0052219 (Fern 9(11)-ene)

INCHI for NP0052219 (Fern 9(11)-ene)

Structure for NP0052219 (Fern 9(11)-ene)

3D Structure for NP0052219 (Fern 9(11)-ene)