Flavone 3-methoxycarpachromene - Compound Card

Flavone 3-methoxycarpachromene

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Flavone 3-methoxycarpachromene

Structure
Zoomed Structure
  • Family: Plantae - Anacardiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone-Chromene
Canonical Smiles COc1c(oc2c(c1=O)c(O)c1c(c2)OC(C=C1)(C)C)c1ccc(cc1)O
InChI InChI=1S/C21H18O6/c1-21(2)9-8-13-14(27-21)10-15-16(17(13)23)18(24)20(25-3)19(26-15)11-4-6-12(22)7-5-11/h4-10,22-23H,1-3H3
InChIKey LZNQBDHNIGPIFL-UHFFFAOYSA-N
Formula C21H18O6
HBA 6
HBD 2
MW 366.37
Rotatable Bonds 2
TPSA 89.13
LogP 4.06
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 366.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pistacia atlantica Anacardiaceae Plantae 434234

Showing of synonyms

  • Adams M, Plitzko I, et al. (2009). HPLC-profiling for antiplasmodial compounds - 3-methoxycarpachromene from Pistacia atlantica. Phytochemistry Letters,2009,2(4),159-162. [View]
Pubchem: 163089376
Nmrshiftdb2: 70114898

No compound-protein relationship available.

Structure

SMILES: O1CC=Cc(c2)c1cc(c23)oc(cc3=O)-c4ccccc4

Level: 1

Mol. Weight: 366.37 g/mol

Structure

SMILES: O=c1ccoc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 366.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 366.37 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.790
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.250
Plasma Protein Binding
78.82
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
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
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.310
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.620
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.320
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.900
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.820
Rat (Acute)
2.660
Rat (Chronic Oral)
1.870
Fathead Minnow
5.050
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
491.650
Hydration Free Energy
-8.730
Log(D) at pH=7.4
3.730
Log(P)
4.73
Log S
-5.79
Log(Vapor Pressure)
-8.9
Melting Point
235.25
pKa Acid
8.0
pKa Basic
4.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9811
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9811
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9528
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9528
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9296
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9296
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9062
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9062
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8932
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8932
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8815
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8815
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8710
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8710
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8632
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8632
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8608
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8608
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8364
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8364
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8322
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8322
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8316
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8316
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8252
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8252
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8232
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8232
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8210
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8210
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8177
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8177
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8115
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8115
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7926
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7926
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7925
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7925
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7916
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7916
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7880
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7880
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7875
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7875
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7759
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7759
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7671
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7671
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7609
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7609
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7596
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7596
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7584
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7584
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7569
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7569
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7562
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7562
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7553
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7553
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7527
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7527
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7494
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7494
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7486
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7486
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7480
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7480
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7466
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7466
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7447
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7447
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7442
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7442
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7437
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7437
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7409
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7409
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7409
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7409
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7400
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7400
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7400
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7400
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7399
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7399
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7232
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7232
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7208
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7208
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7197
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7197
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7195
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7195
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7191
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7191
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7170
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7170
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7159
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7159
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7123
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7123
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7123
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7123
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7084
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7084
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7078
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7078
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7075
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7075
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7060
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7060
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7054
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7054
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7043
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7043
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7029
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7029
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7010
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7010
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7006
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7006
Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI Escherichia coli 3 0.7002
Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI Escherichia coli 3 0.7002

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