NP-MRD: Showing NP-Card for variediene (NP0342004)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-12-01 18:59:04 UTC

Updated at

2025-02-11 21:35:13 UTC

NP-MRD ID

NP0342004

Natural Product DOI

https://doi.org/10.57994/3497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

variediene

Description

Variediene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. variediene was first documented in 2016 (PMID: 26546087). Based on a literature review a small amount of articles have been published on variediene (PMID: 36101897) (PMID: 35084065) (PMID: 31476106).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02282319092D          

 22 24  0  0  1  0            999 V2000
    0.7041   -0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123   -0.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2333    0.4331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0144    1.2285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8098    1.2662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4544    1.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8750    2.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9779    2.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433    1.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244    0.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5193    2.0383    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1002    0.4940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3907   -0.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556   -0.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8367    1.1622    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    1.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1033    2.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5811    1.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1124    0.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3794    1.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3130    0.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7336    0.0419    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
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 11  1  6  0  0  0
  5 12  1  0  0  0  0
 12 10  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  3 14  1  0  0  0  0
  4 15  1  1  0  0  0
  4 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
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0342004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC\C(C)=C\CC\C(C)=C1\C[C@@]1(C)CCC(C)(C)[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-14-7-6-8-15(2)17-13-20(5)12-11-19(3,4)18(20)16(17)10-9-14/h7,16,18H,6,8-13H2,1-5H3/b14-7+,17-15-/t16-,18-,20-/m1/s1

> <INCHI_KEY>
IYERWQNZLUNKRO-VODJRPGGSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.476

> <EXACT_MASS>
272.25040103

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
34.1119395881351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1Z,5E,9S,10R,14R)-2,6,11,11,14-pentamethyltricyclo[7.6.0.0^{10,14}]pentadeca-1,5-diene

> <JCHEM_LOGP>
5.717214636666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
89.23039999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1Z,5E,9S,10R,14R)-2,6,11,11,14-pentamethyltricyclo[7.6.0.0^{10,14}]pentadeca-1,5-diene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-FEB-23         0                                  
HETATM    1  C   UNK     0       1.314  -1.556   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.703  -0.066   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.435   0.808   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.027   2.293   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.512   2.363   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.715   3.325   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.633   4.421   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.692   4.515   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   2.477   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.592   0.992   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0      -0.969   3.805   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0      -2.054   0.922   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.596  -0.519   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.850  -0.039   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       1.562   2.169   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       0.668   3.693   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.059   4.354   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.951   3.098   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.077   1.831   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.441   2.710   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.318   1.175   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.236   0.078   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   15   16                                             
CONECT    5    4    6   11   12                                             
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   12                                                       
CONECT   11    5                                                            
CONECT   12    5   10   13   14                                             
CONECT   13   12                                                            
CONECT   14   12    3                                                       
CONECT   15    4                                                            
CONECT   16    4   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂

Average Mass

272.4760 Da

Monoisotopic Mass

272.25040 Da

IUPAC Name

(1Z,5E,9S,10R,14R)-2,6,11,11,14-pentamethyltricyclo[7.6.0.0^{10,14}]pentadeca-1,5-diene

Traditional Name

(1Z,5E,9S,10R,14R)-2,6,11,11,14-pentamethyltricyclo[7.6.0.0^{10,14}]pentadeca-1,5-diene

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC\C(C)=C\CC\C(C)=C1\C[C@@]1(C)CCC(C)(C)[C@@]21[H]

InChI Identifier

InChI=1S/C20H32/c1-14-7-6-8-15(2)17-13-20(5)12-11-19(3,4)18(20)16(17)10-9-14/h7,16,18H,6,8-13H2,1-5H3/b14-7+,17-15-/t16-,18-,20-/m1/s1

InChI Key

IYERWQNZLUNKRO-VODJRPGGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C6D6, experimental)	[email protected]	Not Available	Not Available	2024-12-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C6D6, experimental)	[email protected]	Not Available	Not Available	2024-12-01	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-12-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C6D6, experimental)	[email protected]	Not Available	Not Available	2024-12-01	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-12-01	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-12-01	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Prauserella Prauserella		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.72	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.23 m³·mol⁻¹	ChemAxon
Polarizability	34.11 Å³	ChemAxon
Number of Rings	3	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-26717

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171904526

PDB ID

Not Available

ChEBI ID

177888

Good Scents ID

Not Available

References

General References

Jiang L, Lv K, Zhu G, Lin Z, Zhang X, Xing C, Yang H, Zhang W, Wang Z, Liu C, Qu X, Hsiang T, Zhang L, Liu X: Norditerpenoids biosynthesized by variediene synthase-associated P450 machinery along with modifications by the host cell Aspergillus oryzae. Synth Syst Biotechnol. 2022 Aug 23;7(4):1142-1147. doi: 10.1016/j.synbio.2022.08.002. eCollection 2022 Dec. [PubMed:36101897 ]
Liang LF, Dickschat JS: Enzymatic Synthesis of Variediene Analogs. Chemistry. 2022 Mar 10;28(15):e202200095. doi: 10.1002/chem.202200095. Epub 2022 Feb 9. [PubMed:35084065 ]
Rinkel J, Steiner ST, Bian G, Chen R, Liu T, Dickschat JS: A Family of Related Fungal and Bacterial Di- and Sesterterpenes: Studies on Fusaterpenol and Variediene. Chembiochem. 2020 Feb 17;21(4):486-491. doi: 10.1002/cbic.201900462. Epub 2019 Nov 7. [PubMed:31476106 ]
Qin B, Matsuda Y, Mori T, Okada M, Quan Z, Mitsuhashi T, Wakimoto T, Abe I: An Unusual Chimeric Diterpene Synthase from Emericella variecolor and Its Functional Conversion into a Sesterterpene Synthase by Domain Swapping. Angew Chem Int Ed Engl. 2016 Jan 26;55(5):1658-61. doi: 10.1002/anie.201509263. Epub 2015 Nov 6. [PubMed:26546087 ]

Showing NP-Card for variediene (NP0342004)

MOL for NP0342004 (variediene)

3D MOL for NP0342004 (variediene)

3D SDF for NP0342004 (variediene)

3D-SDF for NP0342004 (variediene)

PDB for NP0342004 (variediene)

3D PDB for NP0342004 (variediene)

SMILES for NP0342004 (variediene)

INCHI for NP0342004 (variediene)

Structure for NP0342004 (variediene)

3D Structure for NP0342004 (variediene)