2-[(3,5-dihydroxy)-(Z)-4-(3-methylbut-1-enyl)phenyl]benzofuran-6-ol - Compound Card

2-[(3,5-dihydroxy)-(Z)-4-(3-methylbut-1-enyl)phenyl]benzofuran-6-ol

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2-[(3,5-dihydroxy)-(Z)-4-(3-methylbut-1-enyl)phenyl]benzofuran-6-ol

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Benzofuran
Canonical Smiles CC(/C=C\c1c(O)cc(cc1O)c1cc2c(o1)cc(cc2)O)C
InChI InChI=1S/C19H18O4/c1-11(2)3-6-15-16(21)7-13(8-17(15)22)18-9-12-4-5-14(20)10-19(12)23-18/h3-11,20-22H,1-2H3/b6-3-
InChIKey YVWWLJFWZOKLLA-UTCJRWHESA-N
Formula C19H18O4
HBA 4
HBD 3
MW 310.35
Rotatable Bonds 3
TPSA 73.83
LogP 4.89
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.16
Exact Mass 310.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artocarpus communis Moraceae Plantae 194251

Showing of synonyms

  • Kuete V, Ango PY, et al. (2011). Antimicrobial activities of the methanol extract and compounds from Artocarpus communis (Moraceae).. BMC complementary and alternative medicine,2011, 11, 42. [View] [PubMed]
Pubchem: 90656874

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(c2)-c3ccccc3

Level: 1

Mol. Weight: 310.35 g/mol

Structure

SMILES: c1coc(c12)cccc2

Level: 0

Mol. Weight: 310.35 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 310.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.86
Plasma Protein Binding
78.39
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
1.78
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
2.23
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.1
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.41
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.91
Rat (Acute)
1.99
Rat (Chronic Oral)
3.1
Fathead Minnow
4.88
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
438.15
Hydration Free Energy
-11.8
Log(D) at pH=7.4
4.63
Log(P)
5.06
Log S
-5.32
Log(Vapor Pressure)
-8.4
Melting Point
199.33
pKa Acid
7.07
pKa Basic
7.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9693
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9462
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9335
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.9068
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8908
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8740
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8706
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8644
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8642
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8639
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8496
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8354
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8293
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8287
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8285
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8224
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8209
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.8173
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8137
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.8120
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8085
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8085
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8034
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7955
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7921
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7921
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7867
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7866
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7833
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7746
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7652
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7564
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7551
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7542
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7530
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7492
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7492
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7483
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7474
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7413
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7404
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7378
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7376
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7271
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7209
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7200
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7191
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7169
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7158
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7151
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7143
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7126
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7115
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7100
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7097
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7091
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7087
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7087
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7087
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7085
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7082
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7079
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7079
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7075
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7055
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7046
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7014
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7002
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7002

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