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Showing NP-Card for Atractyligenin (NP0338708)

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Record Information
Version2.0
Created at2024-09-11 17:11:15 UTC
Updated at2024-09-11 17:11:15 UTC
NP-MRD IDNP0338708
Secondary Accession NumbersNone
Natural Product Identification
Common NameAtractyligenin
Description Atractyligenin was first documented in 2022 (PMID: 36154826). Based on a literature review a small amount of articles have been published on Atractyligenin (PMID: 38612735) (PMID: 38032344) (PMID: 36442242) (PMID: 36094050).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0338708 (Atractyligenin)


  Mrv2104 05262319432D          

 23 26  0  0  0  0            999 V2000
    1.9428    0.5259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6190   -0.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1046   -0.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9144   -0.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856    2.0642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4570    1.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283    2.0642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8902   -1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283   -0.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4570   -0.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -0.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856    0.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4570    0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283    0.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    0.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6474    0.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093   -0.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0806   -0.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2425   -1.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712   -2.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999   -1.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0521   -1.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144   -0.7687    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
  2 17  1  0  0  0  0
  3  4  2  0  0  0  0
  3 21  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 13  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
  9 18  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 23  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
Download

3D MOL for NP0338708 (Atractyligenin)

Download
3D SDF for NP0338708 (Atractyligenin)

  Mrv2104 05262319432D          

 23 26  0  0  0  0            999 V2000
    1.9428    0.5259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6190   -0.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1046   -0.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9144   -0.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856    2.0642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4570    1.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283    2.0642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8902   -1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283   -0.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4570   -0.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -0.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856    0.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4570    0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283    0.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    0.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6474    0.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093   -0.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0806   -0.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2425   -1.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712   -2.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999   -1.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0521   -1.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144   -0.7687    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
  2 17  1  0  0  0  0
  3  4  2  0  0  0  0
  3 21  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 13  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
  9 18  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 23  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338708

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(O)CC(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C19H28O4/c1-10-11-3-4-15-18(2)9-12(20)7-13(17(22)23)14(18)5-6-19(15,8-11)16(10)21/h11-16,20-21H,1,3-9H2,2H3,(H,22,23)

> <INCHI_KEY>
YRHWUYVCCPXYMB-UHFFFAOYNA-N

> <FORMULA>
C19H28O4

> <MOLECULAR_WEIGHT>
320.429

> <EXACT_MASS>
320.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.19300137960901

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,15-dihydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

> <JCHEM_LOGP>
1.7901943283333328

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.241716521649332

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.586914603255659

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7380403608206755

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
85.89359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7,15-dihydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0338708 (Atractyligenin)
Download
PDB for NP0338708 (Atractyligenin)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  O   UNK     0       3.626   0.982   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.022  -0.377   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.929  -1.737   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.440  -1.737   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.080   3.853   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.720   3.098   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.360   3.853   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.662  -2.342   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.360  -0.831   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.720  -1.284   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.080  -0.679   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.080   0.831   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.720   1.586   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.360   0.679   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.001   1.435   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.208   0.679   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.511  -0.831   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.150  -1.435   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.453  -3.098   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.813  -3.853   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.173  -2.946   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.964  -2.191   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.440  -1.435   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    5    7   13                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10   14   18                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13    6   12   14                                                  
CONECT   14    9   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17    2   16   18   22                                             
CONECT   18    9   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21    3   20   22                                                  
CONECT   22   17   21                                                       
CONECT   23   11                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

Download
3D PDB for NP0338708 (Atractyligenin)
Download
SMILES for NP0338708 (Atractyligenin)
CC12CC(O)CC(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O
Download
INCHI for NP0338708 (Atractyligenin)
InChI=1/C19H28O4/c1-10-11-3-4-15-18(2)9-12(20)7-13(17(22)23)14(18)5-6-19(15,8-11)16(10)21/h11-16,20-21H,1,3-9H2,2H3,(H,22,23)
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View in JSmol
SynonymsNot Available
Chemical FormulaC19H28O4
Average Mass320.4290 Da
Monoisotopic Mass320.19876 Da
IUPAC Name7,15-dihydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid
Traditional Name7,15-dihydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC12CC(O)CC(C1CCC13CC(CCC21)C(=C)C3O)C(O)=O
InChI Identifier
InChI=1/C19H28O4/c1-10-11-3-4-15-18(2)9-12(20)7-13(17(22)23)14(18)5-6-19(15,8-11)16(10)21/h11-16,20-21H,1,3-9H2,2H3,(H,22,23)
InChI KeyYRHWUYVCCPXYMB-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.79ChemAxon
pKa (Strongest Acidic)4.59ChemAxon
pKa (Strongest Basic)-0.74ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity85.89 m³·mol⁻¹ChemAxon
Polarizability35.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Badalamenti N, Maggio A, Fontana G, Bruno M, Lauricella M, D'Anneo A: Synthetic Derivatives of Natural ent-Kaurane Atractyligenin Disclose Anticancer Properties in Colon Cancer Cells, Triggering Apoptotic Cell Demise. Int J Mol Sci. 2024 Mar 31;25(7):3925. doi: 10.3390/ijms25073925. [PubMed:38612735  ] 
  2. Lang R, Czech C, Haas M, Skurk T: Consumption of Roasted Coffee Leads to Conjugated Metabolites of Atractyligenin in Human Plasma. J Agric Food Chem. 2023 Dec 13;71(49):19516-19522. doi: 10.1021/acs.jafc.3c05252.  Epub 2023 Nov 30. [PubMed:38032344  ] 
  3. Lang R, Beusch A, Dirndorfer S: Metabolites of dietary atractyligenin glucoside in coffee drinkers' urine. Food Chem. 2023 Mar 30;405(Pt B):135026. doi: 10.1016/j.foodchem.2022.135026.  Epub 2022 Nov 23. [PubMed:36442242  ] 
  4. Badalamenti N, Vaglica A, Maggio A, Bruno M, Quassinti L, Bramucci M, Maggi F: Cytotoxic activity of several ent-kaurane derivatives of atractyligenin. Synthesis of unreported diterpenic skeleton by chemical rearrangement. Phytochemistry. 2022 Dec;204:113435. doi: 10.1016/j.phytochem.2022.113435. Epub  2022 Sep 22. [PubMed:36154826  ] 
  5. Hoang MH, Nguyen TAT, Nguyen VNH, Vo TN: Cafestol analogues from Coffea canephora: in vitro inhibition and molecular docking to alpha-glucosidase. Nat Prod Res. 2024 Jan-Feb;38(3):379-385. doi: 10.1080/14786419.2022.2123479.  Epub 2022 Sep 12. [PubMed:36094050  ]