NP-MRD: Showing NP-Card for 11-Keto-beta-boswellic acid (NP0078167)

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Record Information

Version

2.0

Created at

2022-04-28 23:17:39 UTC

Updated at

2022-04-28 23:17:39 UTC

NP-MRD ID

NP0078167

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Keto-beta-boswellic acid

Description

11-Keto-beta-boswellic acid, also known as 11-keto-b-boswellate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 11-Keto-beta-boswellic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 11-Keto-beta-boswellic acid has been detected, but not quantified in, herbs and spices. 11-Keto-beta-boswellic acid is found in Boswellia papyrifera, Boswellia sacra and Boswellia serrata . This could make 11-keto-beta-boswellic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02241216372D          

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M  END

     RDKit          3D

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M  END

  Mrv0541 02241216372D          

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    1.1784   -0.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9650    1.6206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6073    2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784    2.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6073    3.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784    2.0331    0.0000 H   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
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  7 10  1  0  0  0  0
 12  7  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  1  0  0  0  0
 15 18  1  0  0  0  0
 20 15  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 19 22  1  0  0  0  0
  3 23  1  6  0  0  0
  4 24  1  0  0  0  0
  4 25  1  6  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
  5 28  1  6  0  0  0
  6 29  1  1  0  0  0
  7 30  1  6  0  0  0
 10 31  1  1  0  0  0
 13 32  1  6  0  0  0
 12 33  2  0  0  0  0
 18 34  1  1  0  0  0
 20 35  1  1  0  0  0
 19 36  1  6  0  0  0
 15 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0078167

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@@H](O)[C@](C)(C(O)=O)[C@]3([H])CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-17-8-11-26(3)14-15-28(5)19(23(26)18(17)2)16-20(31)24-27(4)12-10-22(32)30(7,25(33)34)21(27)9-13-29(24,28)6/h16-18,21-24,32H,8-15H2,1-7H3,(H,33,34)/t17-,18+,21-,22-,23+,24-,26-,27+,28-,29-,30-/m1/s1

> <INCHI_KEY>
YIMHGPSYDOGBPI-YZCVQEKWSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.6838

> <EXACT_MASS>
470.33960996

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
54.728694037900254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid

> <ALOGPS_LOGP>
5.50

> <JCHEM_LOGP>
6.018300012666666

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.7170741270522

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.397946163151363

> <JCHEM_PKA_STRONGEST_BASIC>
-3.037561665711503

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
134.34199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-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      -3.135   0.715   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.469  -0.055   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.469  -1.595   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.135  -2.365   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.801  -1.595   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.801  -0.055   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.468   0.715   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.468  -2.365   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.866  -1.595   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.866  -0.055   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.866   3.025   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.468   2.255   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.200   0.715   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.200   2.255   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.533   3.025   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.533  -0.055   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.867   0.715   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.867   2.255   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.867   5.335   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.533   4.565   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.201   3.025   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.201   4.565   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.802  -2.365   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.224  -3.454   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.365  -3.699   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.825  -4.941   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.711  -3.055   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0      -1.801  -3.135   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0      -1.801   1.485   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      -0.468  -0.825   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0       0.866   1.485   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.200  -0.825   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.801   3.025   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.867   3.795   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.200   5.335   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.867   6.875   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0       2.200   3.795   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   24   25                                             
CONECT    5    4    6    8   28                                             
CONECT    6    1    7    5   29                                             
CONECT    7    6   10   12   30                                             
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   13    7   31                                             
CONECT   11   12   14                                                       
CONECT   12    7   11   33                                                  
CONECT   13   10   14   16   32                                             
CONECT   14   11   15   13                                                  
CONECT   15   14   18   20   37                                             
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   21   15   34                                             
CONECT   19   20   22   36                                                  
CONECT   20   15   19   35                                                  
CONECT   21   18   22                                                       
CONECT   22   21   19                                                       
CONECT   23    3                                                            
CONECT   24    4   26   27                                                  
CONECT   25    4                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28    5                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31   10                                                            
CONECT   32   13                                                            
CONECT   33   12                                                            
CONECT   34   18                                                            
CONECT   35   20                                                            
CONECT   36   19                                                            
CONECT   37   15                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
11-Keto-b-boswellate	Generator
11-Keto-b-boswellic acid	Generator
11-Keto-beta-boswellate	Generator
11-Keto-β-boswellate	Generator
11-Keto-β-boswellic acid	Generator
11-oxo-b-Boswellic acid	HMDB
3-Hydroxy-11-oxo-(3alpha,4beta)-urs-12-en-23-Oic acid	HMDB
3a-Hydroxy-11-oxo-12-ursen-24-Oic acid	HMDB
Urs-12-en-24-Oic acid, 3alpha-hydroxy-11-oxo- (8ci)	HMDB
11-Keto-boswellic acid	HMDB

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6838 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid

Traditional Name

(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@@H](O)[C@](C)(C(O)=O)[C@]3([H])CC[C@@]12C

InChI Identifier

InChI=1S/C30H46O4/c1-17-8-11-26(3)14-15-28(5)19(23(26)18(17)2)16-20(31)24-27(4)12-10-22(32)30(7,25(33)34)21(27)9-13-29(24,28)6/h16-18,21-24,32H,8-15H2,1-7H3,(H,33,34)/t17-,18+,21-,22-,23+,24-,26-,27+,28-,29-,30-/m1/s1

InChI Key

YIMHGPSYDOGBPI-YZCVQEKWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Boswellia papyrifera	Plant	KNApSAcK
Boswellia sacra	LOTUS Database	35616633
Boswellia serrata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
15-hydroxysteroid
Hydroxysteroid
Steroid
Beta-hydroxy acid
Cyclohexenone
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	5.5	ALOGPS
logP	6.02	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	134.34 m³·mol⁻¹	ChemAxon
Polarizability	54.73 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

HMDB0036671

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015601

KNApSAcK ID

Not Available

Chemspider ID

8023261

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9847548

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 11-Keto-beta-boswellic acid (NP0078167)

MOL for NP0078167 (11-Keto-beta-boswellic acid)

3D MOL for NP0078167 (11-Keto-beta-boswellic acid)

3D SDF for NP0078167 (11-Keto-beta-boswellic acid)

3D-SDF for NP0078167 (11-Keto-beta-boswellic acid)

PDB for NP0078167 (11-Keto-beta-boswellic acid)

3D PDB for NP0078167 (11-Keto-beta-boswellic acid)

SMILES for NP0078167 (11-Keto-beta-boswellic acid)

INCHI for NP0078167 (11-Keto-beta-boswellic acid)

Structure for NP0078167 (11-Keto-beta-boswellic acid)

3D Structure for NP0078167 (11-Keto-beta-boswellic acid)