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Malafil

Family: Plantae - Apiaceae
Kingdom: Plantae
Class: Coumarin
- Subclass: Monoterpene Coumarin

Canonical Smiles	COc1cc(ccc1OC)C(=O)O[C@H]1CC(=C2[C@H]([C@H]3[C@@H]1[C@](C)(OC(=O)C=C(C)C)C(=O)O3)C(=CC2=O)C)C
InChI	InChI=1S/C29H32O9/c1-14(2)10-22(31)38-29(5)25-21(36-27(32)17-8-9-19(34-6)20(13-17)35-7)12-16(4)23-18(30)11-15(3)24(23)26(25)37-28(29)33/h8-11,13,21,24-26H,12H2,1-7H3/t21-,24+,25+,26-,29-/m0/s1
InChIKey	REYNGRMDLJMCID-BBFXAVQYSA-N
Formula	C₂₉H₃₂O₉
HBA	9
HBD	0
MW	524.57
Rotatable Bonds	6
TPSA	114.43
LogP	3.9
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	38
Formal Charge	0
Fraction CSP3	0.45
Exact Mass	524.2
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ferula ferulago	Apiaceae	Plantae	49865

Showing of synonyms

El-Razek MHA, Ohta S, et al. (2001). Monoterpene coumarins from Ferula ferulago. Phytochemistry,2001,57(8),1201-1203. [View] [PubMed]

Pubchem: 25149784

Zinc: ZINC000145181955

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC(CC2)C(CC(=O)O3)C3C(C=24)C=CC4=O

Level: 1

Mol. Weight: 524.57 g/mol

SMILES: O=C1C=CC(C1=2)C3C(CC(=O)O3)CCC2

Level: 0

Mol. Weight: 524.57 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 524.57 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.77
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.640
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.63

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.600
Plasma Protein Binding: 91.77
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.610
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.530
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.750
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.420
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -1034.400
Rat (Acute): 3.080
Rat (Chronic Oral): 2.690
Fathead Minnow: 7.300
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 472.120
Hydration Free Energy: -2.850
Log(D) at pH=7.4: 3.650
Log(P): 3.82
Log S: -5.44
Log(Vapor Pressure): -7.84
Melting Point: 176.0
pKa Acid: 7.76
pKa Basic: 2.35

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8980
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8980
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8596
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8596
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8579
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8579
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7630
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7630
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7605
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7605
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7438
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7438
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7410
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7410
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7398
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7398
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7395
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7395
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7376
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7376
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7359
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7359
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7269
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7269
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7259
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7259
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7229
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7229
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7208
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7208
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7185
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7185
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7155
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7155
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7120
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7120
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7095
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7095
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7065
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7065
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7050
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7050
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7040
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7040
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7025
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7025
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7019
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7019
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7015
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7015
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7005
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7005

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