Khellin - Compound Card

Khellin

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Khellin

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Chromone
    • Subclass: Furanochromone
Canonical Smiles COc1c2c(=O)cc(oc2c(c2c1cco2)OC)C
InChI InChI=1S/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3
InChIKey HSMPDPBYAYSOBC-UHFFFAOYSA-N
Formula C14H12O5
HBA 5
HBD 0
MW 260.24
Rotatable Bonds 2
TPSA 61.81
LogP 2.86
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 260.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ammi visnaga Apiaceae Plantae 1053409

Showing of synonyms

  • Badr J.M, Hadad G.M, et al. (2015). Validated HPLC method for simultaneous estimation of khellol glucoside, khellin and visnagin in Ammi visnaga L. fruits and pharmaceutical preparations. Nat Prod Res, 2015, 29(7), 593-601.. [View] [PubMed]
Pubchem: 3828
Kegg Ligand: C09010
Chebi: 6133
Nmrshiftdb2: 20191737
Bindingdb: 50480260
CPRiL: 15791
Structure

SMILES: c1coc(c12)cc3c(c2)c(=O)cco3

Level: 0

Mol. Weight: 260.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.48
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.210
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
82.68
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.590
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.740
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.240
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.700
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
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
3.620
Rat (Acute)
2.780
Rat (Chronic Oral)
2.220
Fathead Minnow
4.770
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
402.570
Hydration Free Energy
-10.030
Log(D) at pH=7.4
2.310
Log(P)
1.85
Log S
-3.78
Log(Vapor Pressure)
-6.18
Melting Point
148.76
pKa Acid
8.36
pKa Basic
4.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9736
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9541
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9277
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9001
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8888
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8867
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8762
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8724
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8701
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8690
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8617
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8603
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8593
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.8484
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8481
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8480
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8458
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8447
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8318
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 2 0.8266
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8158
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8131
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8129
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8127
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8092
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.8074
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.8047
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.8043
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8022
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.8009
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7971
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7945
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7940
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7938
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7909
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7895
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7888
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7887
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7874
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7870
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7858
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7854
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7846
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7803
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7799
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7798
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7794
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7792
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7792
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7790
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7787
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7781
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7758
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7755
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7733
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7732
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7729
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7720
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7709
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.7685
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7684
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7664
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7661
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7661
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7658
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7655
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7642
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7623
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7620
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7609
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7589
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 2 0.7581
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7572
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7560
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7507
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7501
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7495
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7494
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7491
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7488
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7485
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.7484
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.7444
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7444
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 4 0.7442
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7434
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7431
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7425
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7422
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7419
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7418
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7391
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7391
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7388
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7377
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7372
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7371
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7357
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7329
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7329
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7324
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7323
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7315
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7310
Actin nucleation-promoting factor WAS P42768 WASP_HUMAN Homo sapiens 3 0.7286
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7252
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7251
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7241
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7240
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7238
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7231
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7228
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7213
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7213
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7211
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7202
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7194
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7165
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7160
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7154
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7142
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7133
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7112
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7109
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7101
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7099
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7092
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7090
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 2 0.7090
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7084
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 2 0.7076
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7073
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7062
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7058
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7044
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7031
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7013

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