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Lariciresinol 4’-monomethyletherdiacetate

Family: Plantae - Meliaceae
Kingdom: Plantae
Class: Lignan
- Subclass: Enterolignan

Canonical Smiles	COc1cc(ccc1OC(=O)C)C[C@H]1CO[C@@H]([C@H]1COC(=O)C)c1ccc(c(c1)OC)OC
InChI	InChI=1S/C25H30O8/c1-15(26)31-14-20-19(10-17-6-8-22(33-16(2)27)23(11-17)29-4)13-32-25(20)18-7-9-21(28-3)24(12-18)30-5/h6-9,11-12,19-20,25H,10,13-14H2,1-5H3/t19-,20-,25+/m0/s1
InChIKey	STHQLLZVDDDCQI-ZYLNGJIFSA-N
Formula	C₂₅H₃₀O₈
HBA	8
HBD	0
MW	458.51
Rotatable Bonds	9
TPSA	89.52
LogP	3.75
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	458.19
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Turrea nilotica	Meliaceae	Plantae	992803

Showing of synonyms

Ayoub S.M, Kingston D.G. (1984). Lariciresinol Derivatives from Turrea nilotica and Monechma ciliatum. Journal of natural products, 1984, 47(5), 875-6. [View] [PubMed]

Pubchem: 21722909

Nmrshiftdb2: 60075186

No compound-protein relationship available.

SMILES: c1ccccc1CC2CC(OC2)c3ccccc3

Level: 2

Mol. Weight: 458.51 g/mol

SMILES: C1OCCC1Cc2ccccc2

Level: 1

Mol. Weight: 458.51 g/mol

SMILES: O1CCCC1c2ccccc2

Level: 1

Mol. Weight: 458.51 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 458.51 g/mol

SMILES: C1CCOC1

Level: 0

Mol. Weight: 458.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.7
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.680
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.68

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.870
Plasma Protein Binding: 84.42
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: 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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.540
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.580
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.750
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.540
Micronucleos: Safe
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: -129.270
Rat (Acute): 2.720
Rat (Chronic Oral): 2.160
Fathead Minnow: 4.960
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 466.190
Hydration Free Energy: -2.740
Log(D) at pH=7.4: 3.080
Log(P): 2.93
Log S: -4.62
Log(Vapor Pressure): -7.72
Melting Point: 84.3
pKa Acid: 9.94
pKa Basic: 3.76

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9338
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9225
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9053
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9039
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9024
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8975
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8971
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8968
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8965
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8908
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8865
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8795
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8788
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8713
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8644
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8612
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.8493
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8393
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8339
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	4	0.8331
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.8315
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8299
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8296
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8284
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.8284
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8251
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8143
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8142
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8126
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.8113
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8064
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8060
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8012
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.8004
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7867
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7787
Ferrichrome outer membrane transporter/phage receptor	P06971	FHUA_ECOLI	Escherichia coli	3	0.7726
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7719
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7713
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7708
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7708
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7693
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7682
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7680
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7641
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7612
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7611
Cytochrome b-c1 complex subunit 1, mitochondrial	P31800	QCR1_BOVIN	Bos taurus	3	0.7603
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7603
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7598
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7576
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7567
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7563
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7551
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7537
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7522
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7515
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7514
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7513
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	3	0.7478
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7475
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7466
Aspartokinase 1, chloroplastic	Q9LYU8	AK1_ARATH	Arabidopsis thaliana	3	0.7460
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7414
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7396
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7394
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	4	0.7390
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7390
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7385
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7379
Thymidylate synthase	Q4JQW2	TYSY_VZVO	Varicella-zoster virus	3	0.7376
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7370
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7365
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7363
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7356
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7352
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7349
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7342
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7337
Pol protein	Q000H7	Q000H7_9HIV1	Human immunodeficiency virus 1	3	0.7331
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7329
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7326
Decaprenylphosphoryl-beta-D-ribose oxidase	I6X8C4	I6X8C4_MYCTU	Mycobacterium tuberculosis	3	0.7321
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7320
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7319
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7317
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7301
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7295
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7294
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7288
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7277
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7276
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7275
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7274
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7271
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7266
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7266
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7263
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7260
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7258
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7240
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7239
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7238
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7237
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7234
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7232
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7230
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7228
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7204
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7198
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7190
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7184
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7177
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7176
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7175
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7171
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	2	0.7170
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7164
Phosphoenolpyruvate carboxykinase [GTP]	A5TYT6	PCKG_MYCTA	Mycobacterium tuberculosis	3	0.7164
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7160
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7157
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7156
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7152
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7151
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7148
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7138
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7130
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	3	0.7128
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7120
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7115
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	2	0.7114
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7110
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7109
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7103
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7102
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7101
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7099
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7096
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7083
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7079
Ferric enterobactin-binding periplasmic protein FepB	P0AEL6	FEPB_ECOLI	Escherichia coli	3	0.7070
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7054
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7051
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7047
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7044
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7043
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7030
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7028
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7026
Mitogen-activated protein kinase 14	P47811	MK14_MOUSE	Mus musculus	3	0.7025
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7021
Inosine-5'-monophosphate dehydrogenase	P50097	IMDH_TRIFO	Tritrichomonas foetus	2	0.7020
Amino-acid acetyltransferase	Q5FAK7	Q5FAK7_NEIG1	Neisseria gonorrhoeae	2	0.7018
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7016
Tryptase alpha/beta-1	Q15661	TRYB1_HUMAN	Homo sapiens	3	0.7015
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7014
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	4	0.7011
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7011
Nucleoside diphosphate kinase	A5J299	A5J299_PENVA	Penaeus vannamei	2	0.7009
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7005
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7002
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7001

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