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Microfolione

Family: Ptaeroxylaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Prenylated Flavanone

Canonical Smiles	COc1c2O[C@H](CC(=O)c2c(c(c1O)CC=C(C)C)O)c1ccccc1
InChI	InChI=1S/C21H22O5/c1-12(2)9-10-14-18(23)17-15(22)11-16(13-7-5-4-6-8-13)26-20(17)21(25-3)19(14)24/h4-9,16,23-24H,10-11H2,1-3H3/t16-/m1/s1
InChIKey	IMGRRXXTMXIKTA-MRXNPFEDSA-N
Formula	C₂₁H₂₂O₅
HBA	5
HBD	2
MW	354.4
Rotatable Bonds	4
TPSA	75.99
LogP	4.32
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	354.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cedrelopsis microfoliolata	Ptaeroxylaceae	Plantae	1304322

Showing of synonyms

Koorbanally NA, Randrianarivelojosia M, et al. (2002). Bioactive Constituents of Cedrelopsis microfoliata. Journal of natural products, 2002, 65(9), 1349–1352. [View]

Pubchem: 637437

Cas: 462112-95-4

Zinc: ZINC000014819381

Nmrshiftdb2: 10006980

Chembl: CHEMBL498989

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 224.26 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 148.16 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.57
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.640
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.99

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.130
Plasma Protein Binding: 85.8
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 9.860
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.790
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.400
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.590
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -0.300
Rat (Acute): 2.110
Rat (Chronic Oral): 2.760
Fathead Minnow: 4.920
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 407.450
Hydration Free Energy: -8.950
Log(D) at pH=7.4: 3.130
Log(P): 5.03
Log S: -5.64
Log(Vapor Pressure): -7.82
Melting Point: 129.73
pKa Acid: 7.11
pKa Basic: 5.26

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9278
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9205
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.9058
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.9053
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8997
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8919
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8914
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8752
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8694
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8676
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8663
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.8658
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8643
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8568
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8549
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8495
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8477
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8388
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8378
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8276
BMP-2-inducible protein kinase	Q9NSY1	BMP2K_HUMAN	Homo sapiens	3	0.8275
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8252
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8241
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	4	0.8232
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8108
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8056
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7905
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7904
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7862
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7839
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7779
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7768
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7766
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7762
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7724
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7709
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7705
Dipeptidyl peptidase 4	P22411	DPP4_PIG	Sus scrofa	3	0.7697
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7688
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7661
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7651
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7649
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7641
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7629
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7622
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.7598
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7588
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7545
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7539
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7534
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7534
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7525
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7514
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7507
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7500
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7455
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7444
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7435
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	4	0.7433
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7430
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7416
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7415
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7409
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7405
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7403
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7398
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7398
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7384
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7382
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7380
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7369
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7361
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7355
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7343
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7329
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7326
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7325
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7316
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7289
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7277
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7267
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7240
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	4	0.7240
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7239
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7237
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7231
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7228
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7200
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.7195
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7190
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7175
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7171
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7171
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7171
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7153
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7146
Thymidylate synthase	P04818	TYSY_HUMAN	Homo sapiens	4	0.7116
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	3	0.7108
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7105
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7104
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7098
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7097
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7085
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7085
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7084
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	2	0.7082
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7055
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7054
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7047
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7026
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	4	0.7024
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7014
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7012
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7011
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7003

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