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Dihydrolanneaflavonol

Family: Plantae - Anacardiaceae
Kingdom: Plantae
Class: Flavonoid

Canonical Smiles	COc1c(O)cc(cc1O)[C@H]1Oc2cc3OC(C)(C)C=Cc3c(c2C(=O)[C@@H]1O)O
InChI	InChI=1S/C21H20O8/c1-21(2)5-4-10-13(29-21)8-14-15(16(10)24)17(25)18(26)19(28-14)9-6-11(22)20(27-3)12(23)7-9/h4-8,18-19,22-24,26H,1-3H3/t18-,19+/m0/s1
InChIKey	UJMAXNZYJVBCFP-RBUKOAKNSA-N
Formula	C₂₁H₂₀O₈
HBA	8
HBD	4
MW	400.38
Rotatable Bonds	2
TPSA	125.68
LogP	2.67
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	400.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Lannea alata	Anacardiaceae	Plantae	289715

Showing of synonyms

Okoth DA, Chenia HY, et al. (2013). Antibacterial and antioxidant activities of flavonoids from Lannea alata (Engl.) Engl. (Anacardiaceae). Phytochemistry Letters,2013,6(3),476-481. [View]

Pubchem: 102442213

Zinc: ZINC000238785898

No compound-protein relationship available.

SMILES: O1CC=Cc(c2)c1cc(c23)OC(CC3=O)c4ccccc4

Level: 1

Mol. Weight: 400.38 g/mol

SMILES: O=C1CCOc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 400.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 400.38 g/mol

Antibacterial

Radical scavenging

Absorption

Caco-2 (logPapp): -6.14
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.050
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.75

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.050
Plasma Protein Binding: 83.77
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 13.490
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.390
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.040
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.880
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: -11.610
Rat (Acute): 2.480
Rat (Chronic Oral): 3.310
Fathead Minnow: 4.200
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 487.660
Hydration Free Energy: -9.350
Log(D) at pH=7.4: 3.030
Log(P): 2.44
Log S: -5.58
Log(Vapor Pressure): -8.49
Melting Point: 229.79
pKa Acid: 6.13
pKa Basic: 4.39

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9324
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9324
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8870
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8870
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8427
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8427
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8269
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8269
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8135
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8135
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8048
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8048
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8020
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8020
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8006
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8006
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	5	0.7916
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	5	0.7916
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7836
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7836
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	4	0.7822
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	4	0.7822
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	5	0.7620
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	5	0.7620
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	6	0.7589
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	6	0.7589
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7576
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7576
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7547
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7547
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7515
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7515
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7498
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7498
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7489
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7489
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7477
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7477
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7405
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7405
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7397
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7397
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7369
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7369
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7308
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7308
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7299
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7299
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7274
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7274
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7260
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7260
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7245
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7245
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7241
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7241
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7218
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7218
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7199
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7199
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7195
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7195
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7150
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7150
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7113
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7113
Purine nucleoside phosphorylase	P9WP00	PUNA_MYCTO	Mycobacterium tuberculosis	4	0.7061
Purine nucleoside phosphorylase	P9WP00	PUNA_MYCTO	Mycobacterium tuberculosis	4	0.7061
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7023
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7023
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7019
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7019
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7018
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7018

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