(4R)-2-(1,2-dihydroxy-2-methylpropyl)-4-ethenyl-2-hydroxy-4,10-dimethyl-2H,3H,4H,5H-pyrano[3,2-c]chromen-5-one - Compound Card

(4R)-2-(1,2-dihydroxy-2-methylpropyl)-4-ethenyl-2-hydroxy-4,10-dimethyl-2H,3H,4H,5H-pyrano[3,2-c]chromen-5-one

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(4R)-2-(1,2-dihydroxy-2-methylpropyl)-4-ethenyl-2-hydroxy-4,10-dimethyl-2H,3H,4H,5H-pyrano[3,2-c]chromen-5-one

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles C=C[C@@]1(C)CC(O)(Oc2c1c(=O)oc1c2c(C)ccc1)C(C(O)(C)C)O
InChI InChI=1S/C20H24O6/c1-6-19(5)10-20(24,17(22)18(3,4)23)26-15-13-11(2)8-7-9-12(13)25-16(21)14(15)19/h6-9,17,22-24H,1,10H2,2-5H3/t17?,19-,20?/m0/s1
InChIKey KXBAKXZOYFTMPG-SYYJFZTOSA-N
Formula C20H24O6
HBA 6
HBD 3
MW 360.41
Rotatable Bonds 3
TPSA 100.13
LogP 2.15
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 360.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ethulia conyzoides Asteraceae Plantae 434659

Showing of synonyms

  • Bohlmann F, Balbaa S, et al. (1981). A terpene-coumarin derivative from Ethulia Conyzoides. Phytochemistry,1981,20,177-177. [View]
Pubchem: 162938130

No compound-protein relationship available.

Structure

SMILES: O1CCCc(c1c23)c(=O)oc2cccc3

Level: 0

Mol. Weight: 360.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.44
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.95
Plasma Protein Binding
70.19
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.8
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.49
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.52
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.72
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.63
Rat (Acute)
2.89
Rat (Chronic Oral)
2.14
Fathead Minnow
4.31
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
397.92
Hydration Free Energy
-10.57
Log(D) at pH=7.4
2.03
Log(P)
2.14
Log S
-3.19
Log(Vapor Pressure)
-8.76
Melting Point
154.93
pKa Acid
6.16
pKa Basic
6.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8651
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8651
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8106
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8106
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8103
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8103
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8097
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8097
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7838
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7838
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7834
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7834
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7823
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7823
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7802
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7802
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7802
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7802
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7704
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7704
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7691
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7691
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7667
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7667
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7608
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7608
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7442
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7442
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7424
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7424
Prothrombin P00734 THRB_HUMAN Homo sapiens 4 0.7385
Prothrombin P00734 THRB_HUMAN Homo sapiens 4 0.7385
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7362
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7362
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7338
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7338
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7332
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7332
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7324
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7324
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7316
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7316
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7303
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7303
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7290
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7290
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7251
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7251
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7243
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7243
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7159
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7159
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.7135
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.7135
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7126
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7126
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7113
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7113
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7081
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7081
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7030
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7030
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7022
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7022
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7005
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7005
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7004
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7004

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