NP-MRD: Showing NP-Card for methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate (NP0260001)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 02:02:31 UTC

Updated at

2022-09-08 02:02:31 UTC

NP-MRD ID

NP0260001

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

Description

Methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylate belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate is found in Helichrysum chionosphaerum. Methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241518262D          

 23 26  0  0  0  0            999 V2000
    7.2722   -1.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4799   -1.5526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2830   -0.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8783   -0.1803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4907   -0.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4017   -1.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8548    0.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3958    0.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5726    0.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2085    0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7909    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6675   -0.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2508   -1.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4229   -1.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8600   -0.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3317   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236    0.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036    1.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276    1.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3567    0.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6307    0.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8107    0.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9137   -0.4925    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  5 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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 10 20  1  0  0  0  0
 15 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260001

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(C)CCCC2(C)C1CCC13CCC(CC21)C(=C)C3

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O2/c1-14-13-21-10-6-15(14)12-17(21)19(2)8-5-9-20(3,18(22)23-4)16(19)7-11-21/h15-17H,1,5-13H2,2-4H3

> <INCHI_KEY>
BJAYKFMSRRFYLE-UHFFFAOYSA-N

> <FORMULA>
C21H32O2

> <MOLECULAR_WEIGHT>
316.485

> <EXACT_MASS>
316.24023027

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.19635856763914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
4.953724820333335

> <ALOGPS_LOGS>
-6.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.10197694302196

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
92.13269999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

> <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      13.575  -3.328   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.096  -2.898   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.728  -1.403   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.840  -0.337   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.249  -0.973   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.083  -2.504   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.929   0.409   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.072   1.688   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.536   1.586   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.856   0.204   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.076   1.532   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.713  -1.075   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.935  -2.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.389  -2.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.339  -1.172   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.353  -0.156   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.711   1.148   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.927   2.217   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.651   1.901   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.266   0.287   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.044   0.720   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.513   0.891   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.572  -0.919   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   12                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   20                                             
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20   23                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   10   15                                                  
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   15                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
Methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0,.0,]hexadecane-5-carboxylic acid	Generator

Chemical Formula

C₂₁H₃₂O₂

Average Mass

316.4850 Da

Monoisotopic Mass

316.24023 Da

IUPAC Name

methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

Traditional Name

methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C)CCCC2(C)C1CCC13CCC(CC21)C(=C)C3

InChI Identifier

InChI=1S/C21H32O2/c1-14-13-21-10-6-15(14)12-17(21)19(2)8-5-9-20(3,18(22)23-4)16(19)7-11-21/h15-17H,1,5-13H2,2-4H3

InChI Key

BJAYKFMSRRFYLE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helichrysum chionosphaerum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Alkaloid or derivatives
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.35	ALOGPS
logP	4.95	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.13 m³·mol⁻¹	ChemAxon
Polarizability	37.2 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

58859397

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate (NP0260001)

MOL for NP0260001 (methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D MOL for NP0260001 (methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D SDF for NP0260001 (methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D-SDF for NP0260001 (methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

PDB for NP0260001 (methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D PDB for NP0260001 (methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

SMILES for NP0260001 (methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

INCHI for NP0260001 (methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

Structure for NP0260001 (methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)

3D Structure for NP0260001 (methyl 5,9-dimethyl-13-methylidenetetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate)