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Kirkinone B
- Family: Plantae - Ochnaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Biisoflavone
| Canonical Smiles | COc1ccc2c(c1)O[C@H]([C@@H](C2=O)[C@@H]1[C@H](Oc2c(C1=O)ccc(c2)OC)c1ccc(cc1)O)c1ccc(cc1)O |
|---|---|
| InChI | InChI=1S/C32H26O8/c1-37-21-11-13-23-25(15-21)39-31(17-3-7-19(33)8-4-17)27(29(23)35)28-30(36)24-14-12-22(38-2)16-26(24)40-32(28)18-5-9-20(34)10-6-18/h3-16,27-28,31-34H,1-2H3/t27-,28+,31+,32- |
| InChIKey | OCEUAEPEYXQDRI-COWFKMKXSA-N |
| Formula | C32H26O8 |
| HBA | 8 |
| HBD | 2 |
| MW | 538.55 |
| Rotatable Bonds | 5 |
| TPSA | 111.52 |
| LogP | 5.68 |
| Number Rings | 6 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.19 |
| Exact Mass | 538.16 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ochna kirkii | Ochnaceae | Plantae | 2699567 |
Showing of synonyms
Kirkinone B
No compound-protein relationship available.
SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)C(c5ccccc5)Oc(c46)cccc6
Level: 3
Mol. Weight: 538.55 g/mol
SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)COc(c45)cccc5
Level: 2
Mol. Weight: 538.55 g/mol
SMILES: c1cccc(c12)OCC(C2=O)C(C3=O)COc(c34)cccc4
Level: 1
Mol. Weight: 538.55 g/mol
SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3
Level: 1
Mol. Weight: 538.55 g/mol
SMILES: c1cccc(c12)OCCC2=O
Level: 0
Mol. Weight: 538.55 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 538.55 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.21
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.660
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 3.39
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.640
- Plasma Protein Binding
- 95.13
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.730
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.330
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.490
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.830
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -8013.330
- Rat (Acute)
- 2.740
- Rat (Chronic Oral)
- 2.460
- Fathead Minnow
- 25.830
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 479.580
- Hydration Free Energy
- -2.780
- Log(D) at pH=7.4
- 4.490
- Log(P)
- 4.93
- Log S
- -6.92
- Log(Vapor Pressure)
- -12.94
- Melting Point
- 269.97
- pKa Acid
- 7.6
- pKa Basic
- 1.02
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9728 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.9499 |
| Geranylgeranyl transferase type-2 subunit alpha | Q08602 | PGTA_RAT | Rattus norvegicus | 3 | 0.9374 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.9199 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9184 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.9178 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.9072 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 3 | 0.9062 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8981 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.8947 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.8881 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8825 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.8823 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.8734 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8725 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.8723 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.8604 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 3 | 0.8560 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 4 | 0.8533 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.8518 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8507 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8499 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8491 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8463 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.8456 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.8440 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8424 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8420 |
| Genome polyprotein | Q99AU2 | Q99AU2_9HEPC | Hepatitis C virus subtype 1b | 3 | 0.8337 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8329 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8266 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.8265 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8244 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.8227 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.8198 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8128 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8111 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.8009 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7996 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7967 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7943 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7933 |
| Orf1a polyprotein | Q692E5 | Q692E5_CVHSA | SARS coronavirus TJF | 3 | 0.7933 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7914 |
| Annexin A5 | P08758 | ANXA5_HUMAN | Homo sapiens | 3 | 0.7912 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7909 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7908 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7879 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7864 |
| Cytochrome P450 2C5 | P00179 | CP2C5_RABIT | Oryctolagus cuniculus | 3 | 0.7840 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7829 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7808 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7798 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7774 |
| UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase | Q8DNV6 | Q8DNV6_STRR6 | Streptococcus pneumoniae | 3 | 0.7730 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7727 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7726 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7719 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7700 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7654 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.7648 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7644 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7636 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7617 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7608 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7605 |
| Uncharacterized protein | Q55S71 | Q55S71_CRYNB | Cryptococcus neoformans var. neoformans serotype D | 3 | 0.7603 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7593 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7589 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7545 |
| Polymerase basic protein 2 | Q2LG68 | Q2LG68_9INFA | Influenza A virus) | 4 | 0.7522 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7516 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7499 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 3 | 0.7497 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 4 | 0.7487 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 4 | 0.7478 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7469 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | P49354 | FNTA_HUMAN | Homo sapiens | 3 | 0.7464 |
| Glycogen phosphorylase, liver form | P06737 | PYGL_HUMAN | Homo sapiens | 3 | 0.7455 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7449 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7431 |
| Metallo-beta-lactamase type 2 | P52699 | BLAB_SERMA | Serratia marcescens | 3 | 0.7422 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7412 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.7399 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7388 |
| Orf1ab polyprotein | Q6T1E9 | Q6T1E9_CVHSA | SARS coronavirus CUHK-L2 | 3 | 0.7378 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7363 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7349 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7349 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7337 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7331 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.7323 |
| Geranylgeranyl transferase type-2 subunit alpha | Q08602 | PGTA_RAT | Rattus norvegicus | 3 | 0.7317 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7315 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7314 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7313 |
| Histone demethylase UTY | O14607 | UTY_HUMAN | Homo sapiens | 3 | 0.7311 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7308 |
| Isoleucine--tRNA ligase | P56690 | SYI_THET8 | Thermus thermophilus | 3 | 0.7301 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7293 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7285 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7284 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7273 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7273 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 4 | 0.7251 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 4 | 0.7247 |
| Pol protein | Q000H7 | Q000H7_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.7246 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7241 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.7239 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 5 | 0.7229 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7221 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7216 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 3 | 0.7210 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 4 | 0.7195 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 2 | 0.7173 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7164 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 3 | 0.7153 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 4 | 0.7147 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7134 |
| Secoisolariciresinol dehydrogenase | Q94KL8 | SILD_PODPE | Podophyllum peltatum | 3 | 0.7115 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7096 |
| Putative HMP/thiamine-binding protein YkoF | O34911 | YKOF_BACSU | Bacillus subtilis | 3 | 0.7094 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7072 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7058 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 4 | 0.7043 |
| Probable nicotinate-nucleotide adenylyltransferase | Q9HX21 | NADD_PSEAE | Pseudomonas aeruginosa | 3 | 0.7041 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7040 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7024 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 4 | 0.7013 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7011 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 2 | 0.7001 |