NP-MRD: Showing NP-Card for Quillaic acid (NP0052096)

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Record Information

Version

2.0

Created at

2022-04-27 23:16:15 UTC

Updated at

2022-04-27 23:16:15 UTC

NP-MRD ID

NP0052096

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quillaic acid

Description

Quillaic acid, also known as quillaate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Quillaic acid is found in Gypsophila oldhamiana, Psammosilene tunicoides, Quillaja saponaria , Silene firma and Silene jenisseensis. Quillaic acid was first documented in 2020 (PMID: 33145015). Based on a literature review a significant number of articles have been published on quillaic acid (PMID: 32861772) (PMID: 35458600) (PMID: 34849072) (PMID: 34271297) (PMID: 34259519) (PMID: 34098155).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201162D          

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M  END

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M  END


  Mrv1652304282201162D          

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  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  6  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 15 12  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 17 19  1  1  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 16 26  1  6  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 11 29  1  1  0  0  0
  8 30  1  6  0  0  0
  5 31  1  6  0  0  0
  3 32  1  6  0  0  0
  3 33  1  1  0  0  0
 33 34  2  0  0  0  0
  2 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052096

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@]2([C@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(C=O)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O5/c1-25(2)13-14-30(24(34)35)19(15-25)18-7-8-21-26(3)11-10-22(32)27(4,17-31)20(26)9-12-28(21,5)29(18,6)16-23(30)33/h7,17,19-23,32-33H,8-16H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,23+,26-,27-,28+,29+,30+/m0/s1

> <INCHI_KEY>
MQUFAARYGOUYEV-UAWZMHPWSA-N

> <FORMULA>
C30H46O5

> <MOLECULAR_WEIGHT>
486.693

> <EXACT_MASS>
486.334524581

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.97896749274726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aR,5R,6aS,6bR,8aR,9S,10S,12aR,12bR,14bS)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
4.397098713000002

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.300946646411354

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.608656387061117

> <JCHEM_PKA_STRONGEST_BASIC>
-2.998806393319378

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
135.9318

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quillaic 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      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.173  -3.429   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.885  -2.095   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.264   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.650  -1.380   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.397  -2.103   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.757  -2.826   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   35                                                  
CONECT    3    2    4   32   33                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   31                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   30                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   18   29                                             
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   23                                                  
CONECT   16   15   17   20   26                                             
CONECT   17   16   18   19                                                  
CONECT   18   17   11                                                       
CONECT   19   17                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22   15                                                       
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   16   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   11                                                            
CONECT   30    8                                                            
CONECT   31    5                                                            
CONECT   32    3                                                            
CONECT   33    3   34                                                       
CONECT   34   33                                                            
CONECT   35    2                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Quillaate	Generator
(+)-Quillaic acid	MeSH
3 beta,16 alpha-Dihydroxy-23-oxoolean-12-en-28-Oic acid	MeSH
Quillaja sapogenin	MeSH

Chemical Formula

C₃₀H₄₆O₅

Average Mass

486.6930 Da

Monoisotopic Mass

486.33452 Da

IUPAC Name

(4aR,5R,6aS,6bR,8aR,9S,10S,12aR,12bR,14bS)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

quillaic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@]2([C@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(C=O)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=O

InChI Identifier

InChI=1S/C30H46O5/c1-25(2)13-14-30(24(34)35)19(15-25)18-7-8-21-26(3)11-10-22(32)27(4,17-31)20(26)9-12-28(21,5)29(18,6)16-23(30)33/h7,17,19-23,32-33H,8-16H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,23+,26-,27-,28+,29+,30+/m0/s1

InChI Key

MQUFAARYGOUYEV-UAWZMHPWSA-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
Gypsophila oldhamiana	LOTUS Database	35616633
Psammosilene tunicoides	-	KNApSAcK
Quillaja saponaria	Plant	KNApSAcK
Silene firma	LOTUS Database	35616633
Silene jenisseensis	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
Steroid
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

aldehyde (CHEBI:8710 )
hydroxy monocarboxylic acid (CHEBI:8710 )
pentacyclic triterpenoid (CHEBI:8710 )
Oleananes (C08972 )

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	4.84	ALOGPS
logP	4.4	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.61	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	135.93 m³·mol⁻¹	ChemAxon
Polarizability	55.98 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00003546

Chemspider ID

91986

KEGG Compound ID

C08972

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101810

PDB ID

Not Available

ChEBI ID

8710

Good Scents ID

Not Available

References

General References

Singh S, Florez H: Bioinformatic study to discover natural molecules with activity against COVID-19. F1000Res. 2020 Oct 6;9:1203. doi: 10.12688/f1000research.26731.1. eCollection 2020. [PubMed:33145015 ]
Clochard J, Jerz G, Schmieder P, Mitdank H, Troger M, Sama S, Weng A: A new acetylated triterpene saponin from Agrostemma githago L. modulates gene delivery efficiently and shows a high cellular tolerance. Int J Pharm. 2020 Nov 15;589:119822. doi: 10.1016/j.ijpharm.2020.119822. Epub 2020 Aug 27. [PubMed:32861772 ]
Wallace F, Fontana C, Ferreira F, Olivaro C: Structure Elucidation of Triterpenoid Saponins Found in an Immunoadjuvant Preparation of Quillaja brasiliensis Using Mass Spectrometry and (1)H and (13)C NMR Spectroscopy. Molecules. 2022 Apr 8;27(8). pii: molecules27082402. doi: 10.3390/molecules27082402. [PubMed:35458600 ]
Yazici Bektas N, Ersoy E, Boga M, Boran T, Cinar E, Ozhan G, Goren AC, Eroglu Ozkan E: Cytotoxic and apoptotic effects of Hypericum androsaemum on prostate adenocarcinoma (PC-3) and hepatocellular carcinoma (Hep G2) cell lines with identification of secondary metabolites by LC-HRMS. Turk J Chem. 2021 Oct 19;45(5):1621-1638. doi: 10.3906/kim-2104-17. eCollection 2021. [PubMed:34849072 ]
Li F, Wu ST, Qu MH, Wang YX, Ma CL, Yu BH, Wang GS: Bioactive oleanane-type saponins from Hylomecon Japonica. Phytochemistry. 2021 Oct;190:112870. doi: 10.1016/j.phytochem.2021.112870. Epub 2021 Jul 14. [PubMed:34271297 ]
Li W, Ma X, Li G, Zhang A, Wang D, Fan F, Ma X, Zhang X, Dai Z, Qian Z: De Novo Biosynthesis of the Oleanane-Type Triterpenoids of Tunicosaponins in Yeast. ACS Synth Biol. 2021 Aug 20;10(8):1874-1881. doi: 10.1021/acssynbio.1c00065. Epub 2021 Jul 14. [PubMed:34259519 ]
Qiu H, Su L, Wang H, Zhang Z: Chitosan elicitation of saponin accumulation in Psammosilene tunicoides hairy roots by modulating antioxidant activity, nitric oxide production and differential gene expression. Plant Physiol Biochem. 2021 Sep;166:115-127. doi: 10.1016/j.plaphy.2021.05.033. Epub 2021 May 27. [PubMed:34098155 ]
Hammami A, Farman M, Semmar N: Highlighting Aglycone-dependent Glycosylation Aspects in Caryophyllaceae Saponins by a Simplex Simulation Approach. Curr Top Med Chem. 2021;21(7):612-627. doi: 10.2174/1568026621666210114153216. [PubMed:33459236 ]
Li F, Wu ST, Qu MH, Wang YX, Ma CL, Yu BH, Wang GS: Triterpenoid saponins from the herb Hylomecon japonica. Phytochemistry. 2021 Jan;181:112542. doi: 10.1016/j.phytochem.2020.112542. Epub 2020 Oct 22. [PubMed:33130373 ]

Showing NP-Card for Quillaic acid (NP0052096)

MOL for NP0052096 (Quillaic acid)

3D MOL for NP0052096 (Quillaic acid)

3D SDF for NP0052096 (Quillaic acid)

3D-SDF for NP0052096 (Quillaic acid)

PDB for NP0052096 (Quillaic acid)

3D PDB for NP0052096 (Quillaic acid)

SMILES for NP0052096 (Quillaic acid)

INCHI for NP0052096 (Quillaic acid)

Structure for NP0052096 (Quillaic acid)

3D Structure for NP0052096 (Quillaic acid)