Gravelliferone - Compound Card

Gravelliferone

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Gravelliferone

Structure
Zoomed Structure
  • Family: Rutaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles OC(=O)COc1c(oc2c(c1=O)c(C)cc(c2)C)c1ccccc1Cl
InChI InChI=1S/C19H15ClO5/c1-10-7-11(2)16-14(8-10)25-18(12-5-3-4-6-13(12)20)19(17(16)23)24-9-15(21)22/h3-8H,9H2,1-2H3,(H,21,22)
InChIKey JPSHLARIFIFAFL-UHFFFAOYSA-N
Formula C19H15ClO5
HBA 4
HBD 1
MW 358.78
Rotatable Bonds 4
TPSA 76.74
LogP 4.19
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.16
Exact Mass 358.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Clausena anisata Rutaceae Plantae 159034

Showing of synonyms

  • Tatsimo SJN, Tamokou JDD, et al. (2015). LC-MS guided isolation of antibacterial and cytotoxic constituents from Clausena anisata. Med Chem Res, 2015, 24, 1468–1479. [View]
Pubchem: 1413358

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 222.24 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Cancer cell growth inhibitory

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.890
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.76

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
2.230
Plasma Protein Binding
96.33
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.330
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.180
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.520
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.390
Micronucleos
Toxic
NR-AhR
Safe
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
5.090
Rat (Acute)
2.270
Rat (Chronic Oral)
2.200
Fathead Minnow
4.610
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
433.200
Hydration Free Energy
-8.430
Log(D) at pH=7.4
0.160
Log(P)
3.77
Log S
-4.65
Log(Vapor Pressure)
-8.63
Melting Point
189.07
pKa Acid
4.56
pKa Basic
3.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9357
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8972
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8812
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8795
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8794
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 4 0.8792
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8727
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 3 0.8668
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 3 0.8623
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8616
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8448
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8424
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 3 0.8389
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 4 0.8379
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8271
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8266
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8229
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 3 0.8170
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8137
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8126
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8077
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.8050
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8013
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8000
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7999
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7984
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7968
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7942
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7924
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7923
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7819
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7808
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7806
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7772
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7764
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7759
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7737
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7716
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7705
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7692
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 3 0.7650
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7608
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7597
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7585
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7574
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7569
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7568
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7553
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7542
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7521
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7497
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7497
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7491
Carbonic anhydrase 13 Q8N1Q1 CAH13_HUMAN Homo sapiens 3 0.7480
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7480
Beta-1,4-galactosyltransferase 1 P08037 B4GT1_BOVIN Bos taurus 3 0.7452
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7437
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7434
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7421
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 4 0.7406
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 3 0.7396
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7391
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7372
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7371
Cytosol aminopeptidase P00727 AMPL_BOVIN Bos taurus 2 0.7364
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7355
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7342
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7338
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7338
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7337
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7333
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7300
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7286
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7260
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7255
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7248
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7243
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7242
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7238
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7232
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7210
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 3 0.7206
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 2 0.7204
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7200
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7194
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7193
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7180
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7160
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7154
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7132
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7116
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7102
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7089
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7088
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7087
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7086
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7084
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7084
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7081
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7071
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7066
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7063
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7050
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7040
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7031
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7030
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7029
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7023
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7021
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7016
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7008
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7007
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7006
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7001
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7000

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