NP-MRD: Showing NP-Card for 5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde (NP0318254)

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Record Information

Version

2.0

Created at

2022-09-11 18:38:35 UTC

Updated at

2022-09-11 18:38:35 UTC

NP-MRD ID

NP0318254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde

Description

5,5,9-Trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-14-carbaldehyde belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. 5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde is found in Baccharis minutiflora. 5,5,9-Trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-14-carbaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241514362D          

 21 24  0  0  0  0            999 V2000
    3.8136   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -0.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -1.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294    0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    0.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257    0.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -1.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9506   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6469   -0.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586    1.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5987   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -1.1523    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2  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
 12 13  1  0  0  0  0
 13 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  0  0  0  0
 12 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0318254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCCC2(C)C3CCC4CC3(CC4C=O)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O/c1-18(2)8-4-9-19(3)16(18)7-10-20-11-14(5-6-17(19)20)15(12-20)13-21/h13-17H,4-12H2,1-3H3

> <INCHI_KEY>
YNZWSYDADVNWOJ-UHFFFAOYSA-N

> <FORMULA>
C20H32O

> <MOLECULAR_WEIGHT>
288.475

> <EXACT_MASS>
288.24531565

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.25139756330113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
4.740893141000001

> <ALOGPS_LOGS>
-6.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.652112203637667

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0272203912800535

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
86.63479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.01e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       7.119  -2.655   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.821  -1.826   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.230  -3.248   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.863  -0.692   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.402   0.777   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.899   1.113   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.857  -0.022   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.408   1.452   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.318  -1.491   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.285  -2.656   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.774  -2.341   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.208  -0.872   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.322   0.124   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.752   0.996   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.296   2.224   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.874   1.924   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.328   0.347   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.466  -0.449   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.306  -1.583   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.984  -0.707   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.519  -2.151   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   17                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    7   12                                                  
CONECT   18   14   19   20                                                  
CONECT   19   18   12                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O

Average Mass

288.4750 Da

Monoisotopic Mass

288.24532 Da

IUPAC Name

5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde

Traditional Name

5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC1(C)CCCC2(C)C3CCC4CC3(CC4C=O)CCC12

InChI Identifier

InChI=1S/C20H32O/c1-18(2)8-4-9-19(3)16(18)7-10-20-11-14(5-6-17(19)20)15(12-20)13-21/h13-17H,4-12H2,1-3H3

InChI Key

YNZWSYDADVNWOJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Baccharis minutiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	4.86	ALOGPS
logP	4.74	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	18.65	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.63 m³·mol⁻¹	ChemAxon
Polarizability	35.25 Å³	ChemAxon
Number of Rings	4	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde (NP0318254)

MOL for NP0318254 (5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde)

3D MOL for NP0318254 (5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde)

3D SDF for NP0318254 (5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde)

3D-SDF for NP0318254 (5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde)

PDB for NP0318254 (5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde)

3D PDB for NP0318254 (5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde)

SMILES for NP0318254 (5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde)

INCHI for NP0318254 (5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde)

Structure for NP0318254 (5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde)

3D Structure for NP0318254 (5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde)