5-O-methylhoslundin - Compound Card

5-O-methylhoslundin

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5-O-methylhoslundin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles COc1cc2oc(cc(=O)c2c(c1c1coc(c(c1=O)OC)C)OC)c1ccccc1
InChI InChI=1S/C24H20O7/c1-13-23(28-3)22(26)15(12-30-13)20-18(27-2)11-19-21(24(20)29-4)16(25)10-17(31-19)14-8-6-5-7-9-14/h5-12H,1-4H3
InChIKey YZMKUGIAIUCXMP-UHFFFAOYSA-N
Formula C24H20O7
HBA 7
HBD 0
MW 420.42
Rotatable Bonds 5
TPSA 88.11
LogP 4.41
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 420.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bidens pilosa Asteraceae Plantae 42337

Showing of synonyms

  • Sarker SD, Bartholomew B, et al. (2000). 5-O-methylhoslundin: An unusual flavonoid from Bidens pilosa (Asteraceae). Biochemical Systematics and Ecology,2000,28(6),591-593. [View] [PubMed]
Pubchem: 15726099
Chebi: 185658
Nmrshiftdb2: 60060100

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)-c4c(=O)ccoc4

Level: 2

Mol. Weight: 420.42 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)-c3c(=O)ccoc3

Level: 1

Mol. Weight: 420.42 g/mol

Structure

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

Level: 1

Mol. Weight: 420.42 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 420.42 g/mol

Structure

SMILES: O=c1ccocc1

Level: 0

Mol. Weight: 420.42 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 420.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.590
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.670
Plasma Protein Binding
95.58
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.210
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.910
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.040
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.080
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
-59.120
Rat (Acute)
2.510
Rat (Chronic Oral)
1.580
Fathead Minnow
6.050
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
536.040
Hydration Free Energy
-3.780
Log(D) at pH=7.4
2.820
Log(P)
3.81
Log S
-5.19
Log(Vapor Pressure)
-9.03
Melting Point
183.14
pKa Acid
8.54
pKa Basic
2.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9553
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9553
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9453
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9453
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9219
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9219
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9190
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9190
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9073
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9073
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.9039
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.9039
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8926
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8926
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8846
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8846
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8619
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8619
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8568
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8568
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8415
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8415
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8412
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8412
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8409
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8409
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8369
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8369
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8305
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8305
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8265
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8265
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8166
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8166
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8087
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8087
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 4 0.7906
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 4 0.7906
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7861
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7861
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7834
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7834
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7821
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7821
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7766
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7766
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 3 0.7760
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 3 0.7760
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7745
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7745
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7718
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7718
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7698
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7698
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 4 0.7695
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 4 0.7695
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7692
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7692
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7670
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7670
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7653
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7653
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7648
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7648
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7609
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7609
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7606
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7606
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7603
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7603
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7595
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7595
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7580
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7580
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7570
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7570
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7518
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7518
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 5 0.7507
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 5 0.7507
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7494
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7494
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7488
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7488
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7476
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7476
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7456
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7456
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7447
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7447
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7436
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7436
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7434
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7434
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7426
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7426
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7423
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7423
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7400
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7400
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7390
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7390
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7386
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7386
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7369
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7369
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7365
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7365
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7338
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7338
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7338
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7338
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7306
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7306
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7296
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7296
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7289
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7289
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7288
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7288
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 2 0.7231
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 2 0.7231
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7195
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7195
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7178
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7178
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7178
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7178
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7168
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7168
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7168
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7168
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7162
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7162
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7147
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7147
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7142
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7142
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7100
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7100
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7092
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7092
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 2 0.7082
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 2 0.7082
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7077
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7077
Genome polyprotein Q9WMX2 POLG_HCVCO Hepatitis C virus genotype 1b 4 0.7072
Genome polyprotein Q9WMX2 POLG_HCVCO Hepatitis C virus genotype 1b 4 0.7072
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7058
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7058
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7053
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7053
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7030
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7030
Neutrophil collagenase P22894 MMP8_HUMAN Homo sapiens 3 0.7021
Neutrophil collagenase P22894 MMP8_HUMAN Homo sapiens 3 0.7021
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7019
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7019
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7013
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7013
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7013
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7013
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7012
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7012
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7010
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7010

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