(R)-(+) oxypeucedanin hydrate - Compound Card

(R)-(+) oxypeucedanin hydrate

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(R)-(+) oxypeucedanin hydrate

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles O=c1ccc2c(o1)cc1c(c2OC[C@H](C(O)(C)C)O)cco1
InChI InChI=1S/C16H16O6/c1-16(2,19)13(17)8-21-15-9-3-4-14(18)22-12(9)7-11-10(15)5-6-20-11/h3-7,13,17,19H,8H2,1-2H3/t13-/m1/s1
InChIKey PEWFWDOPJISUOK-CYBMUJFWSA-N
Formula C16H16O6
HBA 6
HBD 2
MW 304.3
Rotatable Bonds 4
TPSA 93.04
LogP 2.05
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.31
Exact Mass 304.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ficus exasperata Moraceae Plantae 459060

Showing of synonyms

  • Dongfack MD, Lallemand MC, et al. (2012). A new sphingolipid and furanocoumarins with antimicrobial activity from Ficus exasperata.. Chemical & pharmaceutical bulletin,2012, 60(8), 1072-1075. [View] [PubMed]
Pubchem: 53319618

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)cc3c(c2)ccc(=O)o3

Level: 0

Mol. Weight: 304.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.260
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.120
Plasma Protein Binding
69.37
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
10.000
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.270
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.530
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.900
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
1.050
Rat (Acute)
2.570
Rat (Chronic Oral)
2.370
Fathead Minnow
4.510
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
416.700
Hydration Free Energy
-13.330
Log(D) at pH=7.4
1.690
Log(P)
1.33
Log S
-2.91
Log(Vapor Pressure)
-8.54
Melting Point
181.8
pKa Acid
6.75
pKa Basic
6.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9791
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.9458
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9321
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9240
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.9168
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.9061
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8944
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8941
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8818
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8768
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8683
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8654
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8546
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8541
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8398
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8366
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8310
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8247
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8194
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8103
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.8096
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8023
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8013
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8010
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 2 0.7966
Calmodulin-2 P0DP24 CALM2_HUMAN Homo sapiens 3 0.7939
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7916
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7909
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7895
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7895
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7895
Mucosa-associated lymphoid tissue lymphoma translocation protein 1 Q9UDY8 MALT1_HUMAN Homo sapiens 3 0.7895
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7873
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7846
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7822
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7809
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7789
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7785
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7779
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7765
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7762
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7756
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7756
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7736
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7727
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7716
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7708
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7687
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7677
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7671
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7669
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7663
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7659
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7631
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7616
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 3 0.7610
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7601
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7584
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7579
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7578
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 2 0.7570
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7567
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7563
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7549
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7544
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7535
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 2 0.7531
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7517
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7515
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7515
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7512
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7508
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7507
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7492
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7492
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7481
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7476
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7472
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7465
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7464
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7464
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7454
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7442
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 2 0.7438
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7437
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7421
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7407
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7405
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7401
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7400
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7387
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7379
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7361
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7351
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7349
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 2 0.7342
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7339
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7332
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7327
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 3 0.7321
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7320
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7319
Phospholipase A2, membrane associated P14555 PA2GA_HUMAN Homo sapiens 2 0.7313
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7312
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7312
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7300
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7298
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7296
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7293
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7285
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7261
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7254
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7252
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7250
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7247
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7245
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7236
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7231
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7227
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7221
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7219
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 2 0.7216
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7206
Interleukin-2 P60568 IL2_HUMAN Homo sapiens 2 0.7202
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7198
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7197
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7188
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7174
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7171
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7170
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7167
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7159
Cytochrome P450 2C9 P11712 CP2C9_HUMAN Homo sapiens 2 0.7151
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7146
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7144
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7129
F420H(2)-dependent reductase Rv1155 O06553 F420R_MYCTU Mycobacterium tuberculosis 3 0.7114
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7113
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 3 0.7112
Pentalenic acid synthase Q825I8 CYP28_STRAW Streptomyces avermitilis 2 0.7092
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7084
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7081
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7071
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7063
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7057
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7055
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 2 0.7050
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7046
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7034
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7032
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7029
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7026
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7021
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7018
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7018
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7016
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7015

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