NP-MRD: Showing NP-Card for Ciliaric acid (NP0046744)

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Record Information

Version

2.0

Created at

2022-03-17 20:28:50 UTC

Updated at

2022-03-17 20:28:50 UTC

NP-MRD ID

NP0046744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ciliaric acid

Description

Ciliaric acid, also known as ciliarate, 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. Ciliaric acid is found in Helianthus occidentalis, Helianthus petiolaris, Helianthus salicifolius, Psiadia punctulata and Xylopia aethiopica. Ciliaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223402D          

 23 27  0  0  0  0            999 V2000
    0.6643   -0.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4235   -0.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1832   -0.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198    0.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607    1.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7272    0.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973    0.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729    0.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430    0.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7277   -0.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6643    0.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314    1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    1.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6010   -1.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -0.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -1.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7277   -1.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4240   -1.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875   -0.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8039    0.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9430   -0.1893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3101   -0.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265   -1.5186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 10 19  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  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
 19 22  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC34CC1C2CC3C1(C)CCCC(C)(C1CC4O)C(O)=O

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

> <INCHI_KEY>
REFPIPGRFRVTDA-UHFFFAOYSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.2313538021033

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
3.1588684920000007

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.635589846513509

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4031043639739539

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
87.12109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.30e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.240  -0.236   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.657  -1.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.075  -0.236   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.957   1.772   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.540   2.481   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.357   1.418   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.422   0.472   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.429   0.827   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.494   0.709   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.358  -0.472   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.240   1.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.059   1.890   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.177   3.426   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.122  -2.244   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.059  -1.181   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.059  -2.716   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.358  -3.426   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.658  -2.599   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.777  -1.063   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.367   0.354   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.494  -0.353   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.312  -1.418   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.903  -2.835   0.000  0.00  0.00           O+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7   12                                             
CONECT    7    6    8                                                       
CONECT    8    3    4    7    9                                             
CONECT    9    8                                                            
CONECT   10   11   15   19                                                  
CONECT   11   10   12                                                       
CONECT   12    6   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    1   10   14   16                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   10   18   20   22                                             
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22   19   21   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Value	Source
Ciliarate	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4504 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC12CC34CC1C2CC3C1(C)CCCC(C)(C1CC4O)C(O)=O

InChI Identifier

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

InChI Key

REFPIPGRFRVTDA-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 L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helianthus occidentalis	LOTUS Database	35616633
Helianthus petiolaris	LOTUS Database	35616633
Helianthus salicifolius	LOTUS Database	35616633
Psiadia punctulata	LOTUS Database	35616633
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	2.28	ALOGPS
logP	3.16	ChemAxon
logS	-3.8	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	87.12 m³·mol⁻¹	ChemAxon
Polarizability	36.23 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005712

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

73028428

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ciliaric acid (NP0046744)

MOL for NP0046744 (Ciliaric acid)

3D MOL for NP0046744 (Ciliaric acid)

3D SDF for NP0046744 (Ciliaric acid)

3D-SDF for NP0046744 (Ciliaric acid)

PDB for NP0046744 (Ciliaric acid)

3D PDB for NP0046744 (Ciliaric acid)

SMILES for NP0046744 (Ciliaric acid)

INCHI for NP0046744 (Ciliaric acid)

Structure for NP0046744 (Ciliaric acid)

3D Structure for NP0046744 (Ciliaric acid)