NP-MRD: Showing NP-Card for Stemar-13-ene (NP0045579)

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Record Information

Version

2.0

Created at

2022-03-17 19:32:11 UTC

Updated at

2022-03-17 19:32:11 UTC

NP-MRD ID

NP0045579

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Stemar-13-ene

Description

Stemar-13-ene belongs to the class of organic compounds known as stemarane diterpenoids. These are diterpenoids with a structure characterized by a stemarane skeleton. Some characteristics include the bicyclic system C/D that is constituted by a bicyclo[3.2.1]Octane fused to the bicyclic A/B system in a different fashion with respect to other tetracyclic diterpenes possessing the bicyclo[3.2.1]Octane system. Moreover, the two contiguous quaternary carbon atoms, C(9) and C(10), are present, the former being a spirocyclic atom. Oxygenation can happen at positions C(2), C(7), C(13), C(17), C(18), and C(19). Thus, stemar-13-ene is considered to be an isoprenoid lipid molecule. Stemar-13-ene is found in Pleospora bjoerlingii. Stemar-13-ene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221522D          

 20 23  0  0  1  0            999 V2000
   -0.6914    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1326    0.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254    1.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066    1.0544    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8498    1.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6894    1.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502    1.1080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6725    0.4357    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8495    0.2936    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9873   -0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356   -1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5957   -0.4579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2105   -0.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -0.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8371   -0.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3149    0.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9715    1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7091    1.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0777    1.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2877   -0.2941    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
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
  9 13  1  6  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  1  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  8 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0045579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@@H]2CC[C@H]3C(C)(C)CCC[C@]3(C)[C@@]22CC[C@@H]1C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-14-12-16-6-7-17-18(2,3)9-5-10-19(17,4)20(16)11-8-15(14)13-20/h12,15-17H,5-11,13H2,1-4H3/t15-,16+,17+,19+,20-/m1/s1

> <INCHI_KEY>
MCRAOCBPZAIHJQ-QBYKVAOYSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.4681

> <EXACT_MASS>
272.250401024

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
34.47191916731895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,7S,10S,13R)-2,6,6,12-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadec-11-ene

> <ALOGPS_LOGP>
6.02

> <JCHEM_LOGP>
5.558204495

> <ALOGPS_LOGS>
-6.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
86.7189

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.46e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stemar-13-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.291   0.440   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.248   0.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.981   1.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.626   1.968   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.453   3.331   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.020   3.369   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.880   2.068   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.989   0.813   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.452   0.548   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.710  -1.112   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.306  -1.946   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.112  -0.855   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.260  -0.101   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.630  -0.587   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.163  -0.732   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.054   0.523   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.414   1.923   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.790   2.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.612   3.450   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.270  -0.549   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9   14   20                                             
CONECT    9    8    4   10   13                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12    9                                                       
CONECT   14    8   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    7   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    8                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂

Average Mass

272.4681 Da

Monoisotopic Mass

272.25040 Da

IUPAC Name

(1R,2S,7S,10S,13R)-2,6,6,12-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadec-11-ene

Traditional Name

stemar-13-ene

CAS Registry Number

138883-56-4

SMILES

CC1=C[C@@H]2CC[C@H]3C(C)(C)CCC[C@]3(C)[C@@]22CC[C@@H]1C2

InChI Identifier

InChI=1S/C20H32/c1-14-12-16-6-7-17-18(2,3)9-5-10-19(17,4)20(16)11-8-15(14)13-20/h12,15-17H,5-11,13H2,1-4H3/t15-,16+,17+,19+,20-/m1/s1

InChI Key

MCRAOCBPZAIHJQ-QBYKVAOYSA-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
Oryza sativa	FooDB	KNAPSACK
Pleospora bjoerlingii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stemarane diterpenoids. These are diterpenoids with a structure characterized by a stemarane skeleton. Some characteristics include the bicyclic system C/D that is constituted by a bicyclo[3.2.1]Octane fused to the bicyclic A/B system in a different fashion with respect to other tetracyclic diterpenes possessing the bicyclo[3.2.1]Octane system. Moreover, the two contiguous quaternary carbon atoms, C(9) and C(10), are present, the former being a spirocyclic atom. Oxygenation can happen at positions C(2), C(7), C(13), C(17), C(18), and C(19).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Stemarane diterpenoids

Alternative Parents

Substituents

Stemarane diterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diterpene (CHEBI:50069 )
Labdane and halimane diterpenoids (LMPR0104030008 )

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	6.02	ALOGPS
logP	5.56	ChemAxon
logS	-6.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.72 m³·mol⁻¹	ChemAxon
Polarizability	34.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

FDB001469

KNApSAcK ID

C00000897

Chemspider ID

Not Available

KEGG Compound ID

C18223

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15161496

PDB ID

Not Available

ChEBI ID

50069

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Stemar-13-ene (NP0045579)

MOL for NP0045579 (Stemar-13-ene)

3D MOL for NP0045579 (Stemar-13-ene)

3D SDF for NP0045579 (Stemar-13-ene)

3D-SDF for NP0045579 (Stemar-13-ene)

PDB for NP0045579 (Stemar-13-ene)

3D PDB for NP0045579 (Stemar-13-ene)

SMILES for NP0045579 (Stemar-13-ene)

INCHI for NP0045579 (Stemar-13-ene)

Structure for NP0045579 (Stemar-13-ene)

3D Structure for NP0045579 (Stemar-13-ene)