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(+)-eudesmin

Family: Plantae - Rutaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	COc1cc(ccc1OC)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc(c(c1)OC)OC
InChI	InChI=1S/C22H26O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-28-22(16(15)12-27-21)14-6-8-18(24-2)20(10-14)26-4/h5-10,15-16,21-22H,11-12H2,1-4H3/t15-,16-,21+,22+/m0/s1
InChIKey	PEUUVVGQIVMSAW-RZTYQLBFSA-N
Formula	C₂₂H₂₆O₆
HBA	6
HBD	0
MW	386.44
Rotatable Bonds	6
TPSA	55.38
LogP	3.8
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.45
Exact Mass	386.17
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fagara heitzii	Rutaceae	Plantae	—

Showing of synonyms

Mbaze LM, Lado JA, et al. (2009). Oxidative burst inhibitory and cytotoxic amides and lignans from the stem bark of Fagara heitzii (Rutaceae).. Phytochemistry,2009, 70(11-12), 1442-1447. [View] [PubMed]

Pubchem: 73117

Cas: 29106-36-3

Gnps: CCMSLIB00006442798

Zinc: ZINC000001668160

Kegg Ligand: C10561

Chebi: 23

Nmrshiftdb2: 60030980

Chembl: CHEMBL519099

CPRiL: 60474

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 386.44 g/mol

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 386.44 g/mol

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 386.44 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 386.44 g/mol

Suppressive on phagocytosis response upon activation with serum

Absorption

Caco-2 (logPapp): -4.75
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.580
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.58

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.130
Plasma Protein Binding: 76.97
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-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: 10.710
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.280
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.390
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 6.550
Micronucleos: Safe
NR-AhR: Safe
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: Toxic
T. Pyriformis: -22.250
Rat (Acute): 2.640
Rat (Chronic Oral): 1.810
Fathead Minnow: 4.480
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: 445.990
Hydration Free Energy: -5.110
Log(D) at pH=7.4: 2.670
Log(P): 3.08
Log S: -3.96
Log(Vapor Pressure): -7.09
Melting Point: 131.72
pKa Acid: 10.29
pKa Basic: 3.66

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.9393
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9233
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.8989
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8968
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8940
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8874
cAMP-dependent protein kinase catalytic subunit alpha	P05132	KAPCA_MOUSE	Mus musculus	5	0.8783
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8598
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8516
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8469
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8383
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8317
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8216
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8199
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.8096
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7962
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7819
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7804
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7798
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7749
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7746
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7738
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7728
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7728
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7712
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7706
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7608
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7564
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	2	0.7558
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7547
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7542
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7539
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7538
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7534
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7532
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	3	0.7518
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7513
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7487
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7477
clade A/E 93TH057 HIV-1 gp120 core	A0A0M3KKW9	A0A0M3KKW9_9HIV1	Human immunodeficiency virus 1	2	0.7477
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	3	0.7474
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7464
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7461
Decaprenylphosphoryl-beta-D-ribose oxidase	I6X8C4	I6X8C4_MYCTU	Mycobacterium tuberculosis	3	0.7443
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7440
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7428
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7415
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7404
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7395
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7393
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7391
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7384
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7368
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7359
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7348
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7346
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7337
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7333
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7330
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7324
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7309
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7303
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7301
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7299
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7289
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7289
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7285
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7280
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7277
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	4	0.7274
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	4	0.7264
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7250
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	2	0.7249
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7249
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7225
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7225
Cell division protein FtsZ	P0A029	FTSZ_STAAM	Staphylococcus aureus	3	0.7220
Beta-lactamase	Q79MP6	Q79MP6_PSEAI	Pseudomonas aeruginosa	2	0.7210
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7201
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7195
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7191
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7187
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7185
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7184
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7179
Aminopeptidase N	P04825	AMPN_ECOLI	Escherichia coli	3	0.7177
Tryptase alpha/beta-1	Q15661	TRYB1_HUMAN	Homo sapiens	3	0.7171
Interleukin-1 receptor-associated kinase 4	Q9NWZ3	IRAK4_HUMAN	Homo sapiens	3	0.7167
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7154
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7148
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7143
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7138
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7130
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7128
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7127
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7120
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7117
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7099
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7090
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7083
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7083
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7073
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7073
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7071
DNA topoisomerase 1	P06612	TOP1_ECOLI	Escherichia coli	3	0.7070
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7070
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7061
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7054
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7046
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7044
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7038
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7036
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7035
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7030
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7023
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7023
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7015
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7007
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7003
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7002
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7001

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