NP-MRD: Showing NP-Card for Guajadial C (NP0084072)

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Record Information

Version

2.0

Created at

2022-04-29 04:55:17 UTC

Updated at

2022-04-29 04:55:17 UTC

NP-MRD ID

NP0084072

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Guajadial C

Description

Guajadial C is found in Psidium guajava . Guajadial C was first documented in 2017 (PMID: 28578580). Based on a literature review very few articles have been published on Guajadial C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206552D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292206552D          

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 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 33 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084072

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@]3(C[C@]([H])(C4=CC=CC=C4)C4=C(O3)C(C=O)=C(O)C(C=O)=C4O)C=C1[C@@H](CC[C@H]2C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O5/c1-17(2)20-10-9-18(3)21-11-12-30(14-23(20)21)13-22(19-7-5-4-6-8-19)26-28(34)24(15-31)27(33)25(16-32)29(26)35-30/h4-8,14-18,20-22,33-34H,9-13H2,1-3H3/t18-,20+,21-,22-,30+/m1/s1

> <INCHI_KEY>
FKDKMNYVVXIPCC-VRANUHBXSA-N

> <FORMULA>
C30H34O5

> <MOLECULAR_WEIGHT>
474.597

> <EXACT_MASS>
474.240624195

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.16966670688178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R,4'aR,5'R,8'S)-5,7-dihydroxy-5'-methyl-4-phenyl-8'-(propan-2-yl)-3,4,4',4'a,5',6',7',8'-octahydro-3'H-spiro[1-benzopyran-2,2'-naphthalene]-6,8-dicarbaldehyde

> <ALOGPS_LOGP>
5.63

> <JCHEM_LOGP>
8.267171634666667

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.250549550849637

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.728810629218875

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9703008322963855

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
138.5488

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R,4'aR,5'R,8'S)-5,7-dihydroxy-8'-isopropyl-5'-methyl-4-phenyl-3,4,4',4'a,5',6',7',8'-octahydro-3'H-spiro[1-benzopyran-2,2'-naphthalene]-6,8-dicarbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       4.152  -4.414   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.922  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.462  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.232  -1.746   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.462  -0.413   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.772  -1.746   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.542  -0.413   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.772   0.921   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.232   0.921   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.462   2.255   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.232   3.588   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.772   3.588   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.542   2.255   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       8.002  -0.413   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      11.082  -0.413   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.852  -1.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.622  -0.413   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.162  -0.413   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.932  -1.746   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.472  -1.746   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.242  -0.413   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.242  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.472  -4.414   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.932  -4.414   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.162  -5.747   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.622  -5.747   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.932  -7.081   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      15.702  -3.080   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0      14.162  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.622  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.082  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.542  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.772  -4.414   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.542  -5.747   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.772  -7.081   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.232  -4.414   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.462  -5.747   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   32                                                  
CONECT    7    6    8   14   15                                             
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    7                                                            
CONECT   15    7   16                                                       
CONECT   16   15   17   30   31                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   28   29                                             
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   19                                                            
CONECT   29   19   24   30                                                  
CONECT   30   29   16                                                       
CONECT   31   16   32                                                       
CONECT   32    6   31   33                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₄O₅

Average Mass

474.5970 Da

Monoisotopic Mass

474.24062 Da

IUPAC Name

(2S,4R,4'aR,5'R,8'S)-5,7-dihydroxy-5'-methyl-4-phenyl-8'-(propan-2-yl)-3,4,4',4'a,5',6',7',8'-octahydro-3'H-spiro[1-benzopyran-2,2'-naphthalene]-6,8-dicarbaldehyde

Traditional Name

(2S,4R,4'aR,5'R,8'S)-5,7-dihydroxy-8'-isopropyl-5'-methyl-4-phenyl-3,4,4',4'a,5',6',7',8'-octahydro-3'H-spiro[1-benzopyran-2,2'-naphthalene]-6,8-dicarbaldehyde

CAS Registry Number

Not Available

SMILES

[H][C@]12CC[C@]3(C[C@]([H])(C4=CC=CC=C4)C4=C(O3)C(C=O)=C(O)C(C=O)=C4O)C=C1[C@@H](CC[C@H]2C)C(C)C

InChI Identifier

InChI=1S/C30H34O5/c1-17(2)20-10-9-18(3)21-11-12-30(14-23(20)21)13-22(19-7-5-4-6-8-19)26-28(34)24(15-31)27(33)25(16-32)29(26)35-30/h4-8,14-18,20-22,33-34H,9-13H2,1-3H3/t18-,20+,21-,22-,30+/m1/s1

InChI Key

FKDKMNYVVXIPCC-VRANUHBXSA-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

Classification

Not classified

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	5.63	ALOGPS
logP	8.27	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	6.73	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	138.55 m³·mol⁻¹	ChemAxon
Polarizability	53.17 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

C00053277

Chemspider ID

95502693

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134714902

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Qin XJ, Yu Q, Yan H, Khan A, Feng MY, Li PP, Hao XJ, An LK, Liu HY: Meroterpenoids with Antitumor Activities from Guava (Psidium guajava). J Agric Food Chem. 2017 Jun 21;65(24):4993-4999. doi: 10.1021/acs.jafc.7b01762. Epub 2017 Jun 9. [PubMed:28578580 ]

Showing NP-Card for Guajadial C (NP0084072)

MOL for NP0084072 (Guajadial C)

3D MOL for NP0084072 (Guajadial C)

3D SDF for NP0084072 (Guajadial C)

3D-SDF for NP0084072 (Guajadial C)

PDB for NP0084072 (Guajadial C)

3D PDB for NP0084072 (Guajadial C)

SMILES for NP0084072 (Guajadial C)

INCHI for NP0084072 (Guajadial C)

Structure for NP0084072 (Guajadial C)

3D Structure for NP0084072 (Guajadial C)