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Osajin
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Isoflavone
| Canonical Smiles | CC(=CCc1c2OC(C)(C)C=Cc2c2c(c1O)c(=O)c(co2)c1ccc(cc1)O)C |
|---|---|
| InChI | InChI=1S/C25H24O5/c1-14(2)5-10-17-21(27)20-22(28)19(15-6-8-16(26)9-7-15)13-29-24(20)18-11-12-25(3,4)30-23(17)18/h5-9,11-13,26-27H,10H2,1-4H3 |
| InChIKey | DCTLJGWMHPGCOS-UHFFFAOYSA-N |
| Formula | C25H24O5 |
| HBA | 5 |
| HBD | 2 |
| MW | 404.46 |
| Rotatable Bonds | 3 |
| TPSA | 79.9 |
| LogP | 5.56 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.24 |
| Exact Mass | 404.16 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ormocarpum kirkii | Leguminosae/Fabaceae | Plantae | 77284 |
Showing of synonyms
Osajin
482-53-1
3'-DEOXYPOMIFERIN
UNII-83R5N9X74B
5'-O-DEMETHYLSCANDINONE
5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one
83R5N9X74B
OSAJIN [MI]
NSC 21565
NSC-21565
4H,8H-Benzo(1,2-b:3,4-b')dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-
4H,8H-BENZO(1,2-B:3,4-B')DIPYRAN-4-ONE, 5-HYDROXY-3-(4-HYDROXYPHENYL)-8,8-DIMETHYL-6-(3-METHYL-2-BUTEN-1-YL)-
4H,8H-BENZO(1,2-B:3,4-B')DIPYRAN-4-ONE, 5-HYDROXY-3-(4-HYDROXYPHENYL)-8,8-DIMETHYL-6-(3-METHYL-2-BUTENYL)-
4H,8H-BENZO(1,2-B:3,4-B)DIPYRAN-4-ONE, 5-HYDROXY-3-(P-HYDROXYPHENYL)-8,8-DIMETHYL-6-(3-METHYL-2-BUTENYL)-
5-hydroxy-3-(3-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)-4H,8H-pyrano(2,3-h)chromen-4-one
5-hydroxy-3-(3-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)-4H,8H-pyrano[2,3-h]chromen-4-one
5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano(2,3-h)chromen-4-one
OSAJIN [INCI]
4H,8H-Benzo(1,2-b:3,4-b')dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-(8CI)
CHEBI:7797
NSC21565
4H,8H-Benzo(1,2-b:3,4-b')dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)- (8CI)
MFCD00076045
Spectrum_000234
SpecPlus_000197
Spectrum2_000175
Spectrum3_000225
Spectrum4_001527
Spectrum5_000034
Oprea1_003228
Oprea1_066678
BSPBio_001869
KBioGR_001934
KBioSS_000714
SPECTRUM201595
MLS001049118
DivK1c_006293
SCHEMBL571689
SPBio_000069
CHEMBL238188
MEGxp0_001415
ACon1_002463
KBio1_001237
KBio2_000714
KBio2_003282
KBio2_005850
KBio3_001369
DTXSID10964028
DCTLJGWMHPGCOS-UHFFFAOYSA-N
HMS2269P11
EX-A4870
HY-N3125
BDBM50442397
CCG-38383
LMPK12050201
STK396323
Osajin, >=95% (LC/MS-ELSD)
AKOS000546821
SDCCGMLS-0066875.P001
NCGC00095510-01
NCGC00095510-02
NCGC00095510-03
NCGC00169822-01
NCGC00169822-02
AC-36736
DA-66378
FO137893
MS-26916
SMR000386948
CS-0023313
NS00015839
G12205
SR-01000738732
SR-01000738732-2
BRD-K01836637-001-03-6
BRD-K01836637-001-12-7
Q27107586
B0005-142884
4H,2-b:3,4-b']dipyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-
4H,2-b:3,4-b']dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-
5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-4H,8H-pyrano[2,3-f]chromen-4-one
5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one
5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one
5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-h]chromen-4-one
5-Hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-3-butenyl)-4H,8H-benzo(1,2-b:3,4-b')dipyran-4-one
- Adem FA, Mbaveng AT, et al. (2019). Cytotoxicity of isoflavones and biflavonoids from Ormocarpum kirkii towards multi-factorial drug resistant cancer. Phytomedicine, 2019, 58, 152853. [View]
Pubchem:
95168
Cas:
482-53-1
Gnps:
CCMSLIB00004702207
Zinc:
ZINC000000538127
Kegg Ligand:
C10511
Chebi:
7797
Nmrshiftdb2:
60114895
Chembl:
CHEMBL238188
Bindingdb:
50442397
CPRiL:
82624
SMILES: C1=CCOc(cc2)c1c(c23)occ(c3=O)-c4ccccc4
Level: 1
Mol. Weight: 404.46 g/mol
SMILES: O=c1ccoc(c12)c3c(cc2)OCC=C3
Level: 0
Mol. Weight: 404.46 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 404.46 g/mol
Anticancer
Absorption
- Caco-2 (logPapp)
- -4.7
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.74
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.72
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.13
- Plasma Protein Binding
- 77.91
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.35
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.98
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.31
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.01
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -20.45
- Rat (Acute)
- 2.94
- Rat (Chronic Oral)
- 1.86
- Fathead Minnow
- 5.33
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 517.86
- Hydration Free Energy
- -5.77
- Log(D) at pH=7.4
- 4.62
- Log(P)
- 6.21
- Log S
- -6.5
- Log(Vapor Pressure)
- -10.19
- Melting Point
- 238.19
- pKa Acid
- 8.11
- pKa Basic
- 5.89
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.9672 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9501 |
| Tyrosine-protein kinase SYK | P43405 | KSYK_HUMAN | Homo sapiens | 3 | 0.9266 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 5 | 0.9128 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.9094 |
| TetR family transcriptional regulator | Q58L87 | Q58L87_MYCSM | Mycolicibacterium smegmatis | 3 | 0.8846 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8648 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8513 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8182 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.8171 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8073 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8009 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7993 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7915 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7907 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 3 | 0.7905 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7810 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7750 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 4 | 0.7715 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7689 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7624 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7613 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7574 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7571 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7567 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7562 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7519 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7514 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 3 | 0.7510 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7509 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7503 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7469 |
| Serine/threonine-protein kinase Nek2 | P51955 | NEK2_HUMAN | Homo sapiens | 3 | 0.7457 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7455 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7412 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7404 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7382 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7380 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7375 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7371 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7358 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7338 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7273 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7261 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7252 |
| Beta-2-microglobulin | P61769 | B2MG_HUMAN | Homo sapiens | 3 | 0.7234 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7224 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7220 |
| Ribonuclease TTHA0252 | Q5SLP1 | RNSE_THET8 | Thermus thermophilus | 3 | 0.7207 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7203 |
| Ketimine reductase mu-crystallin | O54983 | CRYM_MOUSE | Mus musculus | 2 | 0.7187 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7184 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7138 |
| Transthyretin | P02767 | TTHY_RAT | Rattus norvegicus | 2 | 0.7107 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7092 |
| NmrA-like family domain-containing protein 1 | Q9HBL8 | NMRL1_HUMAN | Homo sapiens | 2 | 0.7085 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7081 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7078 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7068 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7063 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7062 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7047 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7034 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7028 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7021 |