NP-MRD: Showing NP-Card for (-)-Licamichauxiioic acid B (NP0076780)

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Record Information

Version

2.0

Created at

2022-04-28 21:58:18 UTC

Updated at

2022-04-28 21:58:18 UTC

NP-MRD ID

NP0076780

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Licamichauxiioic acid B

Description

(1S,4S,5R,9S,10S)-5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadec-13(16)-ene-5-carboxylic acid belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. (-)-Licamichauxiioic acid B is found in Licania michauxii. Based on a literature review very few articles have been published on (1S,4S,5R,9S,10S)-5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadec-13(16)-ene-5-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282223582D          

 23 26  0  0  1  0            999 V2000
    3.3179    1.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667    0.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099    0.0351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2043    0.2129    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9555    0.9995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5123    1.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344    1.2014    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5353    0.5473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8407   -0.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0598    1.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5166    1.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0434    2.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8890    2.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8975    0.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105    0.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745    0.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101   -0.6494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161    1.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5988   -0.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603   -0.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4881   -1.3115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -1.0523    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  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
  4 10  1  1  0  0  0
  8 11  1  6  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  1  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  2  0  0  0  0
  5 19  1  1  0  0  0
  3 20  1  6  0  0  0
  3 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076780

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CCC[C@](C)([C@H]1CC[C@]13C=C(CC[C@@H]21)C(=C)C3=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O3/c1-12-13-5-6-15-18(2)8-4-9-19(3,17(22)23)14(18)7-10-20(15,11-13)16(12)21/h11,14-15H,1,4-10H2,2-3H3,(H,22,23)/t14-,15-,18+,19+,20-/m0/s1

> <INCHI_KEY>
QGDCXKQHEOTKNK-OFDAHSHWSA-N

> <FORMULA>
C20H26O3

> <MOLECULAR_WEIGHT>
314.425

> <EXACT_MASS>
314.188194697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.60332951172647

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5R,9S,10S)-5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-13(16)-ene-5-carboxylic acid

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
4.246902285666667

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.584229630835114

> <JCHEM_PKA_STRONGEST_BASIC>
-5.240214059044333

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
88.95859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,9S,10S)-5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-13(16)-ene-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.193   2.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.658   1.202   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.618   0.065   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.115   0.397   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.650   1.866   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.690   3.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.118   2.243   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.999   1.022   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.569  -0.447   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -0.758   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.112   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.964   2.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.081   4.116   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.659   3.819   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.675   1.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.193   1.177   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.512   0.307   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.766  -1.212   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.203   3.340   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.718  -1.013   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.339  -1.449   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.511  -2.448   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.888  -1.964   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20   21                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   19                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   17                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8   18                                                  
CONECT   18   17                                                            
CONECT   19    5                                                            
CONECT   20    3                                                            
CONECT   21    3   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
(1S,4S,5R,9S,10S)-5,9-Dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0,.0,]hexadec-13(16)-ene-5-carboxylate	Generator

Chemical Formula

C₂₀H₂₆O₃

Average Mass

314.4250 Da

Monoisotopic Mass

314.18819 Da

IUPAC Name

(1S,4S,5R,9S,10S)-5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-13(16)-ene-5-carboxylic acid

Traditional Name

(1S,4S,5R,9S,10S)-5,9-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-13(16)-ene-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@]12CCC[C@](C)([C@H]1CC[C@]13C=C(CC[C@@H]21)C(=C)C3=O)C(O)=O

InChI Identifier

InChI=1S/C20H26O3/c1-12-13-5-6-15-18(2)8-4-9-19(3,17(22)23)14(18)7-10-20(15,11-13)16(12)21/h11,14-15H,1,4-10H2,2-3H3,(H,22,23)/t14-,15-,18+,19+,20-/m0/s1

InChI Key

QGDCXKQHEOTKNK-OFDAHSHWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Licania michauxii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
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	3.68	ALOGPS
logP	4.25	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.96 m³·mol⁻¹	ChemAxon
Polarizability	34.6 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

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

163105644

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Licamichauxiioic acid B (NP0076780)

MOL for NP0076780 ((-)-Licamichauxiioic acid B)

3D MOL for NP0076780 ((-)-Licamichauxiioic acid B)

3D SDF for NP0076780 ((-)-Licamichauxiioic acid B)

3D-SDF for NP0076780 ((-)-Licamichauxiioic acid B)

PDB for NP0076780 ((-)-Licamichauxiioic acid B)

3D PDB for NP0076780 ((-)-Licamichauxiioic acid B)

SMILES for NP0076780 ((-)-Licamichauxiioic acid B)

INCHI for NP0076780 ((-)-Licamichauxiioic acid B)

Structure for NP0076780 ((-)-Licamichauxiioic acid B)

3D Structure for NP0076780 ((-)-Licamichauxiioic acid B)