NP-MRD: Showing NP-Card for Methyl 15beta-hydroxy-19-trachylobanoate (NP0049897)

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Record Information

Version

2.0

Created at

2022-03-17 21:19:52 UTC

Updated at

2022-03-17 21:19:52 UTC

NP-MRD ID

NP0049897

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl 15beta-hydroxy-19-trachylobanoate

Description

(Ent-15beta)-15-Hydroxy-19-trachylobanoic 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 (ent-15beta)-15-Hydroxy-19-trachylobanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (ent-15beta)-15-hydroxy-19-trachylobanoic acid has been detected, but not quantified in, fats and oils. Methyl 15beta-hydroxy-19-trachylobanoate is found in Helianthus annuus and Xylopia aethiopica. This could make (ent-15beta)-15-hydroxy-19-trachylobanoic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309222D          

 23 27  0  0  0  0            999 V2000
    3.3487    0.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0775   -1.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1606   -0.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9865    0.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9247   -1.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1661    0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4712   -0.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0846   -1.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4796    0.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871   -1.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6188    0.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999   -0.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3150   -0.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9779   -0.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494   -1.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9357   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8303   -0.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1354   -0.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9744   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4714   -1.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513   -1.9538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5090   -0.4391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1628   -1.8253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 14  9  1  0  0  0  0
 17  1  1  0  0  0  0
 17  6  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18  7  1  0  0  0  0
 18 13  1  0  0  0  0
 18 16  1  0  0  0  0
 19  3  1  0  0  0  0
 19 11  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  1  0  0  0  0
 20  8  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049897

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12C3CC4(CCC5C(C)(CCCC5(C)C(O)=O)C4CC13)C2O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-17-6-4-7-18(2,16(22)23)13(17)5-8-20-10-12-11(9-14(17)20)19(12,3)15(20)21/h11-15,21H,4-10H2,1-3H3,(H,22,23)

> <INCHI_KEY>
MHVNHDYWKUKRRJ-UHFFFAOYSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.16372781646304

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
3.3147759520000006

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.635611169512259

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4000336115319366

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
86.96709999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.251   0.782   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.478  -3.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.300  -0.467   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.308   1.099   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.326  -3.074   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.777   0.938   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.213  -0.147   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.758  -3.132   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.629   0.677   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.523  -2.489   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.022   0.584   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.987  -0.789   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.055  -1.714   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.559  -0.621   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.519  -2.298   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.080  -1.927   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.150  -0.468   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.586  -1.554   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.819  -0.719   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.613  -1.989   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.776  -3.647   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.150  -0.820   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.504  -3.407   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4    6    7                                                       
CONECT    5    8   13                                                       
CONECT    6    4   17                                                       
CONECT    7    4   18                                                       
CONECT    8    5   20                                                       
CONECT    9   11   14                                                       
CONECT   10   12   20                                                       
CONECT   11    9   12   19                                                  
CONECT   12   10   11   19                                                  
CONECT   13    5   17   18                                                  
CONECT   14    9   17   20                                                  
CONECT   15   19   20   21                                                  
CONECT   16   18   22   23                                                  
CONECT   17    1    6   13   14                                             
CONECT   18    2    7   13   16                                             
CONECT   19    3   11   12   15                                             
CONECT   20    8   10   14   15                                             
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   16                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Value	Source
(ent-15b)-15-Hydroxy-19-trachylobanoate	Generator
(ent-15b)-15-Hydroxy-19-trachylobanoic acid	Generator
(ent-15beta)-15-Hydroxy-19-trachylobanoate	Generator
(ent-15Β)-15-hydroxy-19-trachylobanoate	Generator
(ent-15Β)-15-hydroxy-19-trachylobanoic acid	Generator
16-Hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylate	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4504 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

16-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

Traditional Name

16-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

CAS Registry Number

83508-81-0

SMILES

CC12C3CC4(CCC5C(C)(CCCC5(C)C(O)=O)C4CC13)C2O

InChI Identifier

InChI=1S/C20H30O3/c1-17-6-4-7-18(2,16(22)23)13(17)5-8-20-10-12-11(9-14(17)20)19(12,3)15(20)21/h11-15,21H,4-10H2,1-3H3,(H,22,23)

InChI Key

MHVNHDYWKUKRRJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helianthus annuus	LOTUS Database	35616633
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Xylopia aethiopica	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

Atisane diterpenoid
Kaurane diterpenoid
Villanovane, atisane, trachylobane or helvifulvane diterpenoid
Alkaloid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	2.33	ALOGPS
logP	3.31	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-0.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.97 m³·mol⁻¹	ChemAxon
Polarizability	36.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036839

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015790

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

131752061

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Methyl 15beta-hydroxy-19-trachylobanoate (NP0049897)

MOL for NP0049897 (Methyl 15beta-hydroxy-19-trachylobanoate)

3D MOL for NP0049897 (Methyl 15beta-hydroxy-19-trachylobanoate)

3D SDF for NP0049897 (Methyl 15beta-hydroxy-19-trachylobanoate)

3D-SDF for NP0049897 (Methyl 15beta-hydroxy-19-trachylobanoate)

PDB for NP0049897 (Methyl 15beta-hydroxy-19-trachylobanoate)

3D PDB for NP0049897 (Methyl 15beta-hydroxy-19-trachylobanoate)

SMILES for NP0049897 (Methyl 15beta-hydroxy-19-trachylobanoate)

INCHI for NP0049897 (Methyl 15beta-hydroxy-19-trachylobanoate)

Structure for NP0049897 (Methyl 15beta-hydroxy-19-trachylobanoate)

3D Structure for NP0049897 (Methyl 15beta-hydroxy-19-trachylobanoate)