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Friedelin
- Family: Plantae - Sterculiaceae
- Kingdom: Plantae
- Class: Fatty Acid
| Canonical Smiles | CC1C(=O)CCC2C1(CCC3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C)C)C)C)C)C |
|---|---|
| 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 |
| InChIKey | OFMXGFHWLZPCFL-UHFFFAOYSA-N |
| Formula | C30H50O |
| HBA | 1 |
| HBD | 0 |
| MW | 426.73 |
| Rotatable Bonds | 0 |
| TPSA | 17.07 |
| LogP | 8.46 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.97 |
| Exact Mass | 426.39 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cola lateritia | Sterculiaceae | Plantae | 577684 |
Showing of synonyms
Friedelin
559-74-0
Friedeline
Friedelanone
(-)-Friedelin
D:A-Friedooleanan-3-one
EINECS 209-205-1
UNII-AK21264UAD
AK21264UAD
CHEBI:5171
3-OXOFRIEDELANE
FRIEDELIN [MI]
NSC 55141
DTXSID101015732
NSC-55141
(4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethylicosahydropicen-3(2H)-one
24,25,26-TRINOROLEANAN-3-ONE, 5,9,13-TRIMETHYL-, (4.BETA.,5.BETA.,8.ALPHA.,9.BETA.,10.ALPHA.,13.ALPHA.,14.BETA.)-
3(2H)-PICENONE, EICOSAHYDRO-4,4A,6B,8A,11,11,12B,14A-OCTAMETHYL-, (4R-(4.ALPHA.,4A.ALPHA.,6A.BETA.,6B.ALPHA.,8A.ALPHA.,12A.ALPHA.,12B.BETA.,14A.ALPHA.,14B.BETA.))-
DTXCID901473918
24,25,26-trinoroleanan-3-one, 5,9,13-trimethyl-, (4beta,5beta,8alpha,9beta,10alpha,13alpha,14beta)-
D:A-Friedooleanan-3-one (VAN) (8CI)
D:A-Friedooleanan-3-one (VAN) (8CI)(9CI)
3(2H)-PICENONE, EICOSAHYDRO-4,4A,6B,8A,11,11,12B,14A-OCTAMETHYL-, (4R-(4ALPHA,4AALPHA,6ABETA,6BALPHA,8AALPHA,12AALPHA,12BBETA,14AALPHA,14BBETA))-
Ofmxgfhwlzpcfl-uhfffaoysa-n
Friedelan-3-one
CHEMBL485998
(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
24,25,26-Trinoroleanan-3-one, 5,9,13-trimethyl-,(4b,5b,8a,9b,10a,13a,14b)-
SR-05000002227
Fridelin
MFCD00017296
Friedelin (Standard)
Friedelin, technical grade
Friedelin, analytical standard
SCHEMBL193053
HY-N4110R
D:A-Friedooleanan-3-one (VAN)
OFMXGFHWLZPCFL-SVRPQWSVSA-N
HY-N4110
BDBM50241943
AKOS015897124
CCG-208470
FF66091
MS-27536
CS-0032118
NS00043099
C08626
SR-05000002227-2
SR-05000002227-3
Q15410972
3(2H)-Picenone, eicosahydro-4,4a,6b,8a,11,11,12b,14a-octamethyl-, (4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-
- Kamdem M, Ojo O, et al. (2022). Pentacyclic Triterpenoids, Phytosteroids and Fatty Acid Isolated from the Stem-bark of Cola lateritia K. Schum. (Sterculiaceae) of Cameroon origin; Evaluation of Their Antibacterial Activity. Arabian Journal of Chemistry, 2022, 15(1), 103506. [View]
Pubchem:
91472
Cas:
559-74-0
Gnps:
CCMSLIB00006401113
Zinc:
ZINC000004097720
Kegg Ligand:
C08626
Chebi:
5171
Nmrshiftdb2:
60019491
Metabolights:
MTBLC5171
Chembl:
CHEMBL485998
Bindingdb:
50241943
CPRiL:
64342
SMILES: C1CC(=O)CC(CC2)C1C3CCC(C4C23)C5C(CC4)CCCC5
Level: 0
Mol. Weight: 426.73 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.73
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.5
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.42
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.09
- Plasma Protein Binding
- 35.36
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.22
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.57
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.65
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.21
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -27.42
- Rat (Acute)
- 2.09
- Rat (Chronic Oral)
- 1.43
- Fathead Minnow
- 4.77
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 408.24
- Hydration Free Energy
- -3.7
- Log(D) at pH=7.4
- 7.39
- Log(P)
- 7.9
- Log S
- -7.04
- Log(Vapor Pressure)
- -7.33
- Melting Point
- 258.42
- pKa Acid
- 12.37
- pKa Basic
- 7.62
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8626 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7949 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7703 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7422 |