Decyloxycleomiscosin D - Compound Card

Decyloxycleomiscosin D

Select a section from the left sidebar

Decyloxycleomiscosin D

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles CCCCCCCCCOC[C@H]1Oc2c(O[C@@H]1c1cc(OC)c(c(c1)OC)O)c(OC)cc1c2oc(=O)cc1
InChI InChI=1S/C30H38O9/c1-5-6-7-8-9-10-11-14-36-18-24-27(20-16-21(33-2)26(32)22(17-20)34-3)39-29-23(35-4)15-19-12-13-25(31)38-28(19)30(29)37-24/h12-13,15-17,24,27,32H,5-11,14,18H2,1-4H3/t24-,27-/m1/s1
InChIKey YQSCMRURGKQZHU-SHQCIBLASA-N
Formula C30H38O9
HBA 9
HBD 1
MW 542.63
Rotatable Bonds 14
TPSA 105.82
LogP 6.17
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 542.25
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Citrus x paradisi Rutaceae Plantae 37656

Showing of synonyms

  • Noulala CGT, Ouete JLN, et al. (2023). Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant Citrus × paradisi Macfad (Rutaceae). Molecules. 2023, 28(3), 1078. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O=c(o1)ccc2ccc(c3c12)OC(CO3)c4ccccc4

Level: 1

Mol. Weight: 542.63 g/mol

Structure

SMILES: O1CCOc(c1c23)ccc2ccc(=O)o3

Level: 0

Mol. Weight: 542.63 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 542.63 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.72
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.42
Plasma Protein Binding
90.92
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
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.6
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.97
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.84
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.66
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
Safe
T. Pyriformis
-3137.61
Rat (Acute)
2.47
Rat (Chronic Oral)
2.01
Fathead Minnow
15.18
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
482.01
Hydration Free Energy
-2.84
Log(D) at pH=7.4
4.31
Log(P)
5.5
Log S
-5.35
Log(Vapor Pressure)
-8.35
Melting Point
118.04
pKa Acid
7.45
pKa Basic
2.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9661
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9515
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9484
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9458
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9385
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9285
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.9253
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9185
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9092
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8929
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8864
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.8773
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8756
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8732
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8719
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.8692
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8684
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8658
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8642
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8609
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8575
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8572
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8525
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8521
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8491
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8466
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8435
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8389
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8374
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8371
Ephrin type-A receptor 3 P29320 EPHA3_HUMAN Homo sapiens 4 0.8315
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8298
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8240
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8229
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8226
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8192
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8178
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.8140
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8112
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8105
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8099
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8075
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8048
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8041
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7935
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7919
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7902
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7847
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 4 0.7805
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7791
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7783
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7759
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7723
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7720
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7710
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7686
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7680
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7675
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7666
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 4 0.7665
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7646
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7640
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7627
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7622
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7616
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7600
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7600
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 4 0.7597
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7588
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7585
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7564
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7557
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7554
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7549
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7545
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7538
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7537
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7517
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.7514
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7499
Enterochelin uptake periplasmic binding protein Q0P8Q4 Q0P8Q4_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7498
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7493
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7492
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7481
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7470
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7465
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7462
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7462
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7455
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7450
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7439
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7434
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7418
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7414
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7411
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7409
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7407
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7401
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 4 0.7382
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 2 0.7382
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7374
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7362
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7353
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7346
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7345
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7341
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7336
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7335
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7327
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7325
Uracil-DNA glycosylase P9WFQ9 UNG_MYCTU Mycobacterium tuberculosis 4 0.7317
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7315
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7305
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7301
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7295
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7294
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7293
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7291
Pol protein Q000H7 Q000H7_9HIV1 Human immunodeficiency virus 1 3 0.7275
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7274
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7263
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7260
Orotidine 5'-phosphate decarboxylase Q5L0U0 PYRF_GEOKA Geobacillus kaustophilus 3 0.7245
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7245
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7239
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7237
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7220
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7192
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7190
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7181
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7180
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7178
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7170
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7169
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7169
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7168
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7165
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7165
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7164
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7158
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7150
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7146
Major histocompatibility complex class I-related gene protein Q95460 HMR1_HUMAN Homo sapiens 5 0.7125
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7121
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7116
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7114
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7111
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7092
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7089
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7087
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7086
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7081
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.7059
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7058
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7056
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7056
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7051
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7050
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7048
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7042
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7041
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7041
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7040
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7039
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7034
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7031
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7028
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7028
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7022
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7002
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7002

Download SDF