NP-MRD: Showing NP-Card for (6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one (NP0268249)

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Record Information

Version

2.0

Created at

2022-09-08 13:18:40 UTC

Updated at

2022-09-08 13:18:40 UTC

NP-MRD ID

NP0268249

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one

Description

Iguesterin belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. (6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one is found in Catha edulis, Gymnosporia cassinoides, Lydenburgia cassinoides, Salacia reticulata and Tripterygium regelii. (6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one was first documented in 2010 (PMID: 20167482). Based on a literature review a small amount of articles have been published on Iguesterin (PMID: 33037698) (PMID: 35985974) (PMID: 32985017).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082215182D          

 30 34  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082215182D          

 30 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0268249

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@]2(C)CC[C@]3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5[C@]4(C)CC[C@@]3(C)[C@@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O2/c1-17-9-10-25(3)11-13-27(5)22-8-7-19-18(2)24(30)21(29)16-20(19)26(22,4)12-14-28(27,6)23(25)15-17/h7-9,16,23,30H,10-15H2,1-6H3/t23-,25-,26+,27-,28+/m1/s1

> <INCHI_KEY>
FLMDVQMCMIGPEK-IPTPSVHJSA-N

> <FORMULA>
C28H36O2

> <MOLECULAR_WEIGHT>
404.594

> <EXACT_MASS>
404.271530399

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.0897482353731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6bS,8aS,12aR,12bS,14aR)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,6b,7,8,8a,9,12,12a,12b,13,14,14a-dodecahydropicen-2-one

> <JCHEM_LOGP>
5.433154622

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.752585316164986

> <JCHEM_PKA_STRONGEST_BASIC>
-3.462479182709436

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
127.40379999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6bS,8aS,12aR,12bS,14aR)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7H-picen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.208  -1.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.438  -2.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.208  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.438  -5.184   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.898  -5.184   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -6.517   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.128  -6.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.588  -6.517   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.818  -5.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.048  -6.517   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.278  -5.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.508  -6.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.032  -6.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.802  -5.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.032  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.802  -2.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.342  -2.516   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.112  -1.183   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.112  -3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.652  -3.850   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.342  -5.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.112  -6.517   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.508  -3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.262  -2.516   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.278  -2.516   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.818  -2.516   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.588  -3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.358  -2.516   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.128  -3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.898  -2.516   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   29                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   27                                             
CONECT   10    9                                                            
CONECT   11    9   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14   22                                                  
CONECT   22   21                                                            
CONECT   23   15   11   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    9   28   29                                             
CONECT   28   27                                                            
CONECT   29   27    5   30                                                  
CONECT   30   29    2                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
(9 beta,13 alpha,14 beta)-3-Hydroxy-9,13-dimethyl-24,25,26,30-tetranoroleana-1(10),3,5,7,20(29)-pentaen-2-one	MeSH
(9 beta,13 alpha,14 beta)-3-Hydroxy-9,13-dimethyl-24,25,26,30-tetranoroleana-1(10),3,5,7,20-pentaen-2-one	MeSH
Isoiguesterin	MeSH

Chemical Formula

C₂₈H₃₆O₂

Average Mass

404.5940 Da

Monoisotopic Mass

404.27153 Da

IUPAC Name

(6bS,8aS,12aR,12bS,14aR)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,6b,7,8,8a,9,12,12a,12b,13,14,14a-dodecahydropicen-2-one

Traditional Name

(6bS,8aS,12aR,12bS,14aR)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7H-picen-2-one

CAS Registry Number

Not Available

SMILES

CC1=CC[C@]2(C)CC[C@]3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5[C@]4(C)CC[C@@]3(C)[C@@H]2C1

InChI Identifier

InChI=1S/C28H36O2/c1-17-9-10-25(3)11-13-27(5)22-8-7-19-18(2)24(30)21(29)16-20(19)26(22,4)12-14-28(27,6)23(25)15-17/h7-9,16,23,30H,10-15H2,1-6H3/t23-,25-,26+,27-,28+/m1/s1

InChI Key

FLMDVQMCMIGPEK-IPTPSVHJSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Catha edulis	LOTUS Database	35616633
Gymnosporia cassinoides	LOTUS Database	35616633
Lydenburgia cassinoides	LOTUS Database	35616633
Salacia reticulata	LOTUS Database	35616633
Tripterygium regelii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Enol
Organic oxide
Hydrocarbon derivative
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	5.43	ChemAxon
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	127.4 m³·mol⁻¹	ChemAxon
Polarizability	48.09 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00042072

Chemspider ID

24677584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46881919

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Adhikari B, Marasini BP, Rayamajhee B, Bhattarai BR, Lamichhane G, Khadayat K, Adhikari A, Khanal S, Parajuli N: Potential roles of medicinal plants for the treatment of viral diseases focusing on COVID-19: A review. Phytother Res. 2021 Mar;35(3):1298-1312. doi: 10.1002/ptr.6893. Epub 2020 Oct 9. [PubMed:33037698 ]
Yang F, Jiang XL, Tariq A, Sadia S, Ahmed Z, Sardans J, Aleem M, Ullah R, Bussmann RW: Potential medicinal plants involved in inhibiting 3CL(pro) activity: A practical alternate approach to combating COVID-19. J Integr Med. 2022 Nov;20(6):488-496. doi: 10.1016/j.joim.2022.08.001. Epub 2022 Aug 9. [PubMed:35985974 ]
Boozari M, Hosseinzadeh H: Natural products for COVID-19 prevention and treatment regarding to previous coronavirus infections and novel studies. Phytother Res. 2021 Feb;35(2):864-876. doi: 10.1002/ptr.6873. Epub 2020 Sep 27. [PubMed:32985017 ]
Ryu YB, Park SJ, Kim YM, Lee JY, Seo WD, Chang JS, Park KH, Rho MC, Lee WS: SARS-CoV 3CLpro inhibitory effects of quinone-methide triterpenes from Tripterygium regelii. Bioorg Med Chem Lett. 2010 Mar 15;20(6):1873-6. doi: 10.1016/j.bmcl.2010.01.152. Epub 2010 Feb 4. [PubMed:20167482 ]
LOTUS database [Link]

Showing NP-Card for (6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one (NP0268249)

MOL for NP0268249 ((6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one)

3D MOL for NP0268249 ((6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one)

3D SDF for NP0268249 ((6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one)

3D-SDF for NP0268249 ((6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one)

PDB for NP0268249 ((6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one)

3D PDB for NP0268249 ((6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one)

SMILES for NP0268249 ((6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one)

INCHI for NP0268249 ((6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one)

Structure for NP0268249 ((6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one)

3D Structure for NP0268249 ((6bs,8as,12ar,12bs,14ar)-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-8,9,12,12a,13,14-hexahydro-7h-picen-2-one)