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Malafilin

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(=O)O3)C(=CC2=O)C)C
InChI	InChI=1S/C26H28O9/c1-12-9-16(28)20-13(2)10-19(33-24(29)15-7-8-17(31-5)18(11-15)32-6)22-23(21(12)20)34-25(30)26(22,4)35-14(3)27/h7-9,11,19,21-23H,10H2,1-6H3/t19-,21+,22+,23-,26-/m0/s1
InChIKey	UAEWOIGDYDJTTM-JOLDKRDUSA-N
Formula	C₂₆H₂₈O₉
HBA	9
HBD	0
MW	484.5
Rotatable Bonds	5
TPSA	114.43
LogP	2.96
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.46
Exact Mass	484.17
Number of Lipinski Rule Violations	0

#	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: 25149678

Zinc: ZINC000145169019

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 484.5 g/mol

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

Level: 0

Mol. Weight: 484.5 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 484.5 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: Non-Substrate
Skin Permeability: -2.9

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.570
Plasma Protein Binding: 83.03
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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.170
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.480
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.880
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.010
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: Safe
T. Pyriformis: -272.120
Rat (Acute): 3.030
Rat (Chronic Oral): 2.570
Fathead Minnow: 4.880
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 466.570
Hydration Free Energy: -2.570
Log(D) at pH=7.4: 2.880
Log(P): 2.75
Log S: -4.87
Log(Vapor Pressure): -7.97
Melting Point: 183.35
pKa Acid: 7.36
pKa Basic: 2.76

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	0.8895
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8895
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8676
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8676
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8577
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8577
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7899
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7899
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7768
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7768
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
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7537
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7537
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7434
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7434
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7363
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7363
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7354
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7354
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7285
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7285
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7271
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7271
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7261
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7261
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7225
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7225
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7180
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7180
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7152
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7152
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7131
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7131
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7099
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7099
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7094
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7094
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7093
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7093
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7083
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7083
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7074
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7074
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7072
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7072
Cytochrome P450 3A4	P08684	CP3A4_HUMAN	Homo sapiens	3	0.7064
Cytochrome P450 3A4	P08684	CP3A4_HUMAN	Homo sapiens	3	0.7064
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7061
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7061
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7056
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7056
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	2	0.7043
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	2	0.7043
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7015
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7015
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7015
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7015
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7014
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7014
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7006
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7006

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