NP-MRD: Showing NP-Card for 5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid (NP0319149)

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Record Information

Version

2.0

Created at

2022-09-11 20:02:31 UTC

Updated at

2022-09-11 20:02:31 UTC

NP-MRD ID

NP0319149

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Description

5,9-Dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylic acid 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. 5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid is found in Mikania hirsutissima, Mikania luetzelburgii, Mikania vitifolia and Montanoa tomentosa. 5,9-Dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201502232D          

 33 37  0  0  0  0            999 V2000
    1.8257    0.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8136   -1.4224    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
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  1  2  1  0  0  0  0
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  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004201502232D          

 33 37  0  0  0  0            999 V2000
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 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319149

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3OC(=O)C=CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O4/c1-19-21-11-12-23-27(2)15-7-16-28(3,26(31)32)22(27)14-17-29(23,18-21)25(19)33-24(30)13-10-20-8-5-4-6-9-20/h4-6,8-10,13,21-23,25H,1,7,11-12,14-18H2,2-3H3,(H,31,32)

> <INCHI_KEY>
JYMRFFRJCMWZHS-UHFFFAOYSA-N

> <FORMULA>
C29H36O4

> <MOLECULAR_WEIGHT>
448.603

> <EXACT_MASS>
448.261359639

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.33100993047243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
5.54

> <JCHEM_LOGP>
6.766817875333335

> <ALOGPS_LOGS>
-6.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.47203155132474

> <JCHEM_PKA_STRONGEST_BASIC>
-6.827499720126689

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
128.29279999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.53e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       3.408   1.452   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.857  -0.022   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.899   1.113   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.402   0.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.863  -0.692   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.821  -1.826   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.119  -2.655   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.318  -1.491   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.285  -2.656   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.774  -2.341   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.208  -0.872   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.322   0.124   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.752   0.996   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.296   2.224   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.874   1.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.328   0.347   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.466  -0.449   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.984  -0.707   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  O   UNK     0      -0.562  -3.102   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.006  -3.639   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.192  -2.658   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.262  -5.158   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.075  -6.139   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.332  -7.657   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.145  -8.639   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.402 -10.157   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.845 -10.694   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.032  -9.713   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.775  -8.194   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.230  -3.248   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.166  -4.471   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.703  -3.447   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   16                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   31                                             
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16   19                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2   11                                                  
CONECT   17   13   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31    6   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
5,9-Dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0,.0,]hexadecane-5-carboxylate	Generator
5,9-Dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate	Generator

Chemical Formula

C₂₉H₃₆O₄

Average Mass

448.6030 Da

Monoisotopic Mass

448.26136 Da

IUPAC Name

5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Traditional Name

5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC12CCCC(C)(C1CCC13CC(CCC21)C(=C)C3OC(=O)C=CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C29H36O4/c1-19-21-11-12-23-27(2)15-7-16-28(3,26(31)32)22(27)14-17-29(23,18-21)25(19)33-24(30)13-10-20-8-5-4-6-9-20/h4-6,8-10,13,21-23,25H,1,7,11-12,14-18H2,2-3H3,(H,31,32)

InChI Key

JYMRFFRJCMWZHS-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Mikania hirsutissima	LOTUS Database	35616633
Mikania luetzelburgii	LOTUS Database	35616633
Mikania vitifolia	LOTUS Database	35616633
Montanoa tomentosa	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
Cinnamic acid or derivatives
Cinnamic acid ester
Styrene
Fatty acid ester
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	5.54	ALOGPS
logP	6.77	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	4.47	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.29 m³·mol⁻¹	ChemAxon
Polarizability	50.33 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

75049195

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid (NP0319149)

MOL for NP0319149 (5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D MOL for NP0319149 (5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D SDF for NP0319149 (5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D-SDF for NP0319149 (5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

PDB for NP0319149 (5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D PDB for NP0319149 (5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

SMILES for NP0319149 (5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

INCHI for NP0319149 (5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

Structure for NP0319149 (5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)

3D Structure for NP0319149 (5,9-dimethyl-14-methylidene-15-[(3-phenylprop-2-enoyl)oxy]tetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid)