(S)-(-) oxypeucedanin hydrate - Compound Card

(S)-(-) oxypeucedanin hydrate

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(S)-(-) 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-/m0/s1
InChIKey PEWFWDOPJISUOK-ZDUSSCGKSA-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: 899657
Nmrshiftdb2: 60032257

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
69.51
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
9.970
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.240
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
0.980
Rat (Acute)
2.570
Rat (Chronic Oral)
2.370
Fathead Minnow
4.490
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
417.550
Hydration Free Energy
-13.340
Log(D) at pH=7.4
1.650
Log(P)
1.34
Log S
-2.95
Log(Vapor Pressure)
-8.53
Melting Point
180.04
pKa Acid
6.76
pKa Basic
6.41
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 0.9781
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.9403
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9325
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9245
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9206
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.8914
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8813
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8699
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8658
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8641
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8454
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8434
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8429
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8428
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8398
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8255
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8253
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8189
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.8152
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8100
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.8095
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8031
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8022
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7954
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7909
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7902
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7875
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7866
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7849
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7841
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7840
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7818
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7803
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7796
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7786
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7785
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7784
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7779
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7772
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7755
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7750
Calmodulin-2 P0DP24 CALM2_HUMAN Homo sapiens 3 0.7745
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7730
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7719
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7706
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7690
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7674
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7659
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7651
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7639
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7638
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7634
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7627
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7617
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7602
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7598
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7561
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7558
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7557
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 2 0.7553
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7545
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7544
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7538
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7523
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7523
Transcriptional regulator Q8NMG3 Q8NMG3_CORGL Corynebacterium glutamicum 3 0.7504
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7504
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7487
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7485
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7480
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7476
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7468
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7460
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7457
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7439
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7437
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 2 0.7431
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7430
Mucosa-associated lymphoid tissue lymphoma translocation protein 1 Q9UDY8 MALT1_HUMAN Homo sapiens 3 0.7418
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7418
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7410
Prothrombin P00734 THRB_HUMAN Homo sapiens 4 0.7407
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7404
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7403
Phospholipase A2, membrane associated P14555 PA2GA_HUMAN Homo sapiens 2 0.7389
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 2 0.7384
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7383
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7376
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7366
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7365
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7359
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7355
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7346
Pol polyprotein P32542 POL_EIAVC Equine infectious anemia virus 4 0.7336
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7324
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7290
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7281
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7276
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 2 0.7274
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7271
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7269
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7268
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7261
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7255
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7253
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7247
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 2 0.7244
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7237
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7237
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7233
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7230
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7230
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 2 0.7225
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 2 0.7225
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 2 0.7211
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7207
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7200
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7200
F420H(2)-dependent reductase Rv1155 O06553 F420R_MYCTU Mycobacterium tuberculosis 3 0.7182
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7161
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7160
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7157
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7154
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7141
Interleukin-2 P60568 IL2_HUMAN Homo sapiens 2 0.7141
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7138
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7133
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7128
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7124
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7114
Pentalenic acid synthase Q825I8 CYP28_STRAW Streptomyces avermitilis 2 0.7092
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7077
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.7072
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7070
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7070
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7069
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7063
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7058
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7053
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7053
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7052
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7051
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7039
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7025
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7023
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7021
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7019
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7019
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 3 0.7004
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7001

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