NP-MRD: Showing NP-Card for Guavanoic acid (NP0075388)

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Record Information

Version

2.0

Created at

2022-04-28 20:40:08 UTC

Updated at

2022-04-28 20:40:08 UTC

NP-MRD ID

NP0075388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Guavanoic acid

Description

Guavanoic acid, also known as guavanoate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Guavanoic acid is found in Psidium guajava . Guavanoic acid was first documented in 2002 (PMID: 12377233). Based on a literature review a small amount of articles have been published on Guavanoic acid (PMID: 32357815) (PMID: 33479677) (PMID: 25829790) (PMID: 19815393).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222402D          

 38 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282222402D          

 38 42  0  0  1  0            999 V2000
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   -0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907    1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7766   -0.7392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5050   -0.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5338    0.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2047   -0.7890    0.0000 C   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
  6  7  1  6  0  0  0
  5  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 13 16  1  1  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 11 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
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 27  1  6  0  0  0
 22 28  1  1  0  0  0
 20 29  1  6  0  0  0
 12 30  1  6  0  0  0
  4 31  1  6  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  1 34  1  1  0  0  0
  1 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@]2(CC[C@]1(C)OC(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H50O6/c1-18-24-20-9-10-23-28(5)17-21(34)25(35)27(3,4)22(28)11-12-30(23,7)29(20,6)13-15-32(24,26(36)37)16-14-31(18,8)38-19(2)33/h9,18,21-25,34-35H,10-17H2,1-8H3,(H,36,37)/t18-,21-,22+,23-,24+,25+,28+,29-,30-,31+,32-/m1/s1

> <INCHI_KEY>
MJTXEUZBYBMCSL-CYHUXCCFSA-N

> <FORMULA>
C32H50O6

> <MOLECULAR_WEIGHT>
530.746

> <EXACT_MASS>
530.36073933

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
61.05453161162376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4aR,6aS,6bR,8aR,10R,11R,12aR,12bR,14bS)-2-(acetyloxy)-10,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-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>
5.47

> <JCHEM_LOGP>
4.6328199880000005

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.627313693364574

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.549253165769176

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1598164618201263

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
145.89309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4aR,6aS,6bR,8aR,10R,11R,12aR,12bR,14bS)-2-(acetyloxy)-10,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-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      11.344  -0.564   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   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804   2.104   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  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.023   3.635   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.574   3.437   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.804   4.771   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.397  -2.103   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.650  -1.380   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      14.009  -0.657   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.063   0.882   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      15.315  -1.473   0.000  0.00  0.00           C+0
CONECT    1    2    6   34   35                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   15   31                                             
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   17   30                                             
CONECT   13   12    8   14   16                                             
CONECT   14   13   15                                                       
CONECT   15   14    4                                                       
CONECT   16   13                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   11   21   29                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24   27                                                  
CONECT   24   23   19   25   26                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23                                                            
CONECT   28   22                                                            
CONECT   29   20                                                            
CONECT   30   12                                                            
CONECT   31    4   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    1                                                            
CONECT   35    1   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
Guavanoate	Generator
20beta-Acetoxy-2alpha,3beta-dihydroxyurs-12-en-28-Oic acid	MeSH

Chemical Formula

C₃₂H₅₀O₆

Average Mass

530.7460 Da

Monoisotopic Mass

530.36074 Da

IUPAC Name

(1R,2S,4aR,6aS,6bR,8aR,10R,11R,12aR,12bR,14bS)-2-(acetyloxy)-10,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-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

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

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@]2(CC[C@]1(C)OC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C32H50O6/c1-18-24-20-9-10-23-28(5)17-21(34)25(35)27(3,4)22(28)11-12-30(23,7)29(20,6)13-15-32(24,26(36)37)16-14-31(18,8)38-19(2)33/h9,18,21-25,34-35H,10-17H2,1-8H3,(H,36,37)/t18-,21-,22+,23-,24+,25+,28+,29-,30-,31+,32-/m1/s1

InChI Key

MJTXEUZBYBMCSL-CYHUXCCFSA-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
Psidium guajava	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
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
1,2-diol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	5.47	ALOGPS
logP	4.63	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.55	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	145.89 m³·mol⁻¹	ChemAxon
Polarizability	61.05 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037224

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

101211343

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Adewole KE, Ishola AA: A Computational Approach to Investigate the HDAC6 and HDAC10 Binding Propensity of Psidium guajava-derived Compounds as Potential Anticancer Agents. Curr Drug Discov Technol. 2021;18(3):423-436. doi: 10.2174/1568009620666200502013657. [PubMed:32357815 ]
Begum S, Hassan SI, Siddiqui BS, Shaheen F, Ghayur MN, Gilani AH: Triterpenoids from the leaves of Psidium guajava. Phytochemistry. 2002 Oct;61(4):399-403. doi: 10.1016/s0031-9422(02)00190-5. [PubMed:12377233 ]
Govindaraju K, Suganya KSU: In vitro anti-diabetic assessment of guavanoic acid functionalized gold nanoparticles in regulating glucose transport using L6 rat skeletal muscle cells. RSC Med Chem. 2020 Jun 5;11(7):814-822. doi: 10.1039/d0md00125b. eCollection 2020 Jul 1. [PubMed:33479677 ]
Mathur R, Dutta S, Velpandian T, Mathur SR: Psidium guajava Linn. leaf extract affects hepatic glucose transporter-2 to attenuate early onset of insulin resistance consequent to high fructose intake: An experimental study. Pharmacognosy Res. 2015 Apr-Jun;7(2):166-75. doi: 10.4103/0974-8490.151459. [PubMed:25829790 ]
Khaleel Basha S, Govindaraju K, Manikandan R, Ahn JS, Bae EY, Singaravelu G: Phytochemical mediated gold nanoparticles and their PTP 1B inhibitory activity. Colloids Surf B Biointerfaces. 2010 Feb 1;75(2):405-9. doi: 10.1016/j.colsurfb.2009.09.008. Epub 2009 Sep 16. [PubMed:19815393 ]

Showing NP-Card for Guavanoic acid (NP0075388)

MOL for NP0075388 (Guavanoic acid)

3D MOL for NP0075388 (Guavanoic acid)

3D SDF for NP0075388 (Guavanoic acid)

3D-SDF for NP0075388 (Guavanoic acid)

PDB for NP0075388 (Guavanoic acid)

3D PDB for NP0075388 (Guavanoic acid)

SMILES for NP0075388 (Guavanoic acid)

INCHI for NP0075388 (Guavanoic acid)

Structure for NP0075388 (Guavanoic acid)

3D Structure for NP0075388 (Guavanoic acid)