NP-MRD: Showing NP-Card for ent-17-Hydroxy-15-kauren-19-oic acid (NP0048581)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:58:44 UTC

Updated at

2022-03-17 20:58:44 UTC

NP-MRD ID

NP0048581

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-17-Hydroxy-15-kauren-19-oic acid

Description

Ent-17-Hydroxy-15-kauren-19-oic acid, also known as 17-hydroxy-(4alpha)-kaur-15-en-18-Oic 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-17-Hydroxy-15-kauren-19-oic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, ent-17-hydroxy-15-kauren-19-Oic acid has been detected, but not quantified in, corns and green vegetables. ent-17-Hydroxy-15-kauren-19-oic acid is found in Annona glabra, Aristolochia rodriguesii , Espeletiopsis guacharaca, Helianthus annuus, Helianthus grosseserratus, Helianthus petiolaris, Mikania hirsutissima, Othonna sedifolia and Tithonia longiradiata. This could make ent-17-hydroxy-15-kauren-19-Oic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309182D          

 23 26  0  0  0  0            999 V2000
    2.7366    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7827    2.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314    2.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    2.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    1.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7382    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778    1.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862    2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032    1.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    2.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    0.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5084    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  3  1  0  0  0  0
  9  6  1  0  0  0  0
 13  4  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  6  1  0  0  0  0
 16  5  1  0  0  0  0
 18  1  1  0  0  0  0
 18  7  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  2  1  0  0  0  0
 19  8  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20  9  1  0  0  0  0
 20 10  1  0  0  0  0
 20 11  1  0  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 22 17  2  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048581

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCCC(C)(C1CCC13CC(CCC21)C(CO)=C3)C(O)=O

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

> <INCHI_KEY>
XEQHVCXFKPCQNM-UHFFFAOYSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.48564963904714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
3.4691259373333336

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.097540831177977

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.653083461079406

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8813357949416099

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
90.21079999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-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       5.108   0.826   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.061   5.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.129   1.420   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.170   0.028   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.722   0.398   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.099   4.917   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.618   1.124   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.628   2.877   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.569   4.626   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.053   2.140   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.378   3.797   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.265   2.796   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.045   1.193   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.263   2.606   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.105   3.741   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.076   1.981   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.934   4.833   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.606   2.284   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.616   4.037   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.933   3.166   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.194   1.568   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.904   6.373   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.282   4.089   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3    7    8                                                       
CONECT    4    5   13                                                       
CONECT    5    4   16                                                       
CONECT    6    9   15                                                       
CONECT    7    3   18                                                       
CONECT    8    3   19                                                       
CONECT    9    6   20                                                       
CONECT   10   13   20                                                       
CONECT   11   14   20                                                       
CONECT   12   14   21                                                       
CONECT   13    4   10   14                                                  
CONECT   14   11   12   13                                                  
CONECT   15    6   18   19                                                  
CONECT   16    5   18   20                                                  
CONECT   17   19   22   23                                                  
CONECT   18    1    7   15   16                                             
CONECT   19    2    8   15   17                                             
CONECT   20    9   10   11   16                                             
CONECT   21   12                                                            
CONECT   22   17                                                            
CONECT   23   17                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
ent-17-Hydroxy-15-kauren-19-Oate	Generator
17-Hydroxy-(4alpha)-kaur-15-en-18-Oic acid	HMDB
17-Hydroxy-ent-kaur-15-en-19-Oic acid	HMDB
14-(Hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylate	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4504 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid

Traditional Name

14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-ene-5-carboxylic acid

CAS Registry Number

35030-38-7

SMILES

CC12CCCC(C)(C1CCC13CC(CCC21)C(CO)=C3)C(O)=O

InChI Identifier

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

InChI Key

XEQHVCXFKPCQNM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annona glabra	LOTUS Database	35616633
Aristolochia rodriguesii	Plant	KNApSAcK
Espeletiopsis guacharaca	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Helianthus grosseserratus	LOTUS Database	35616633
Helianthus petiolaris	LOTUS Database	35616633
Mikania hirsutissima	LOTUS Database	35616633
Othonna sedifolia	LOTUS Database	35616633
Tithonia longiradiata	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	3.37	ALOGPS
logP	3.47	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.9	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	2	ChemAxon
Refractivity	90.21 m³·mol⁻¹	ChemAxon
Polarizability	36.49 Å³	ChemAxon
Number of Rings	4	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

HMDB0036724

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015661

KNApSAcK ID

Not Available

Chemspider ID

26503684

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13890715

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for ent-17-Hydroxy-15-kauren-19-oic acid (NP0048581)

MOL for NP0048581 (ent-17-Hydroxy-15-kauren-19-oic acid)

3D MOL for NP0048581 (ent-17-Hydroxy-15-kauren-19-oic acid)

3D SDF for NP0048581 (ent-17-Hydroxy-15-kauren-19-oic acid)

3D-SDF for NP0048581 (ent-17-Hydroxy-15-kauren-19-oic acid)

PDB for NP0048581 (ent-17-Hydroxy-15-kauren-19-oic acid)

3D PDB for NP0048581 (ent-17-Hydroxy-15-kauren-19-oic acid)

SMILES for NP0048581 (ent-17-Hydroxy-15-kauren-19-oic acid)

INCHI for NP0048581 (ent-17-Hydroxy-15-kauren-19-oic acid)

Structure for NP0048581 (ent-17-Hydroxy-15-kauren-19-oic acid)

3D Structure for NP0048581 (ent-17-Hydroxy-15-kauren-19-oic acid)