Friedelin

  • GreenMolBD CID : 630
  • Molecular Formula : C30H50O
  • Molecular Weight : 426.729
  • Exact Molecular Mass : 426.386
  • IUPAC Name : (4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bS)-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
  • InChI : InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22+,23-,24+,26+,27+,28-,29+,30-/m0/s1
  • InChI Key : OFMXGFHWLZPCFL-SVRPQWSVSA-N
  • Canonical SMILES : CC1C(=O)CCC2C1(CCC3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C)C)C)C)C)C
  • Isomeric SMILES : CC1C(=O)CCC2C1(CCC3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C)C)C)C)C)C
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

1.2. Taxonomy Tree

1.3. Alternative Parent

Cyclic ketones; Organic oxides; Hydrocarbon derivatives;

1.4. Molecular Framework

Aliphatic homopolycyclic compounds

1.5. Substituents

Triterpenoid; Cyclic ketone; Ketone; Organic oxygen compound; Organic oxide; Hydrocarbon derivative; Organooxygen compound; Carbonyl group; Aliphatic homopolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
8.457 17.07 0 1 31 0 0 0 12.9744 678.47 480.991 0.628958

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-240.567044 2.71 -4.665 -10.28531 0.95517 5.62

4. Compound Reactivity

DLP nRFG nLMR
4 1 2

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Carcinogen Non-Mutagen Toxic 1.2581 4973.61 0.00931582 Moderate Weak Mild Degradable 3.31E-5 0.144054

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes No Yes Yes Yes Yes

7. Synonyms

Name
Friedelin
Friedeline
559-74-0
D:A-Friedooleanan-3-one
Friedelan-3-one
(-)-Friedelin
CHEBI:5171
CHEMBL485998
(4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethylicosahydropicen-3(2H)-one
3-friedelanone
(4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bS)-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
UNII-AK21264UAD
EINECS 209-205-1
NSC 55141
DA-friedooleanan-3-one
Friedelin, technical grade
Ambotz559-74-0
AC1Q6P5F
Friedelin, analytical standard
SCHEMBL193053
AC1L3M57
AK21264UAD
MolPort-003-873-398
ZINC4097720
BDBM50241943
MFCD00017296
AKOS015897124
API0008506
CCG-208470
AN-45933
CC-28852
DR002631
PL059596
W2470
C08626
D:A-Friedooleanan-3-one (VAN) (8CI)(9CI)
559F740
C-22187
I07-0276
(4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-docosahydropicen-3-one
SR-05000002227
SR-05000002227-2
SR-05000002227-3

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Friedelin
Ageratum conyzoides L 9
Coix lachryma Linn. Seed 8
Crataeva nurvala Fruit 8
Ficus elastica Bark of Aerial Root 3
Garcinia cowa Roxb Stem 7
Ichnocarpus frutescens Stem 3 , 9
Lumnitzera racemosa Stem 1
Microcos paniculata Leaf 3
Scoparia dulcia L Whole Plant 4 , 6

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
459 G-protein coupled bile acid receptor 1 Homo sapiens >10000 10.1021/jm900872z 19911773
154 nitric oxide synthase 2, inducible Nos2 Mus musculus 50 344829
155 Nitric Oxide Synthase, inducible Mus musculus >50000 10.1016/j.bmc.2008.09.021 18926710

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
347233023LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01291375Source Record URL
152036543AKos Consulting & SolutionsSource URLSource DetailAKOS015897124Source Record URL
104225333ISpharmSource URLSource DetailI07-0276Source Record URL
162245530Chembase.cnSource URLSource Detail151376Source Record URL
251917171AvaChem ScientificSource URLSource Detail2365Source Record URL
251915823AvaChem ScientificSource URLSource Detail559-74-0Source Record URL
254779811Boc SciencesSource URLSource Detail559-74-0Source Record URL
252350077AHH Chemical co.,ltdSource URLSource DetailMT-52012Source Record URL
252215443Race ChemicalSource URLSource DetailRV022504073Source Record URL
318504910CambridgeChemSource URLSource DetailCB20884Source Record URL
310116661Aurora Fine Chemicals LLCSource URLSource DetailA17.888.944Source Record URL
24888367Sigma-AldrichSource URLSource Detail855022_ALDRICHSource Record URL
329769873Sigma-AldrichSource URLSource Detail92187_SIALSource Record URL
103130154AAA ChemistrySource URLSource DetailAR-1F3290Source Record URL
274951569ChemFacesSource URLSource DetailCFN98936Source Record URL
350089862DC ChemicalsSource URLSource DetailDCM-048Source Record URL
91639099MolPortSource URLSource DetailMolPort-003-873-398Source Record URL
104404872ABI ChemSource URLSource DetailAC1L3M57Source Record URL
117623319ABI ChemSource URLSource DetailAC1Q6P5FSource Record URL
252551542AK Scientific, Inc. (AKSCI)Source URLSource DetailW2470Source Record URL
329978111Acorn PharmaTech Product ListSource URLSource DetailACN-035539Source Record URL
318265724Chem-Space.com DatabaseSource URLSource DetailCSC000048937Source Record URL
257140009ZINCSource URLSource DetailZINC4097720Source Record URL
57334876NovoSeekSource URLSource Detail91472Source Record URL
29204152R&D ChemicalsSource URLSource Detail0034Source Record URL
349124680Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0642826Source Record URL
341842618OChemSource URLSource Detail12490Source Record URL
355169499MuseChemSource URLSource DetailR024681Source Record URL
223674024AN PharmaTechSource URLSource DetailAN-45933Source Record URL
3615558961717 CheMall CorporationSource URLSource DetailBG04712243Source Record URL
316426983abcr GmbHSource URLSource DetailAB166208Source Record URL
354302355iChemical Technology USA IncSource URLSource DetailEBD2198828Source Record URL
126689178ChemMolSource URLSource Detail49427828Source Record URL