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Yangambin

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Lignan
- Subclass: Diepoxylignan

Canonical Smiles	COc1cc(cc(c1OC)OC)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1cc(OC)c(c(c1)OC)OC
InChI	InChI=1S/C24H30O8/c1-25-17-7-13(8-18(26-2)23(17)29-5)21-15-11-32-22(16(15)12-31-21)14-9-19(27-3)24(30-6)20(10-14)28-4/h7-10,15-16,21-22H,11-12H2,1-6H3/t15-,16-,21+,22+/m0/s1
InChIKey	HRLFUIXSXUASEX-RZTYQLBFSA-N
Formula	C₂₄H₃₀O₈
HBA	8
HBD	0
MW	446.5
Rotatable Bonds	8
TPSA	73.84
LogP	3.81
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	446.19
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Artemisia arborescens	Asteraceae	Plantae	72386

Showing of synonyms

Marco JA, Sanz-Cervera JF, et al. (1997). Sesquiterpene lactones and lignans from Artemisia arborescens.. Phytochemistry,1997,44(6),1133-1137. [View]

Pubchem: 443028

Cas: 13060-14-5

Gnps: CCMSLIB00006497784

Zinc: ZINC000004098936

Kegg Ligand: C10894

Chebi: 10088

Nmrshiftdb2: 60030013

Chembl: CHEMBL454592

Bindingdb: 50443539

CPRiL: 71267

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 446.5 g/mol

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 446.5 g/mol

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 446.5 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 446.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.790
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.3

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.980
Plasma Protein Binding: 72.46
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.550
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.130
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.320
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 7.240
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: Safe
T. Pyriformis: -146.540
Rat (Acute): 2.860
Rat (Chronic Oral): 2.070
Fathead Minnow: 4.970
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: 467.550
Hydration Free Energy: -3.010
Log(D) at pH=7.4: 2.960
Log(P): 2.89
Log S: -3.51
Log(Vapor Pressure): -7.66
Melting Point: 123.49
pKa Acid: 9.67
pKa Basic: 1.98

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9734
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9734
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9525
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9525
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9093
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9093
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.9049
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.9049
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	4	0.9022
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	4	0.9022
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8833
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8833
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8782
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8782
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8737
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8737
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8734
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8734
cAMP-dependent protein kinase catalytic subunit alpha	P05132	KAPCA_MOUSE	Mus musculus	5	0.8571
cAMP-dependent protein kinase catalytic subunit alpha	P05132	KAPCA_MOUSE	Mus musculus	5	0.8571
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8542
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8542
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.8404
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.8404
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8370
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8370
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8317
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8317
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7935
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7935
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7731
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7731
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7731
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7731
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7725
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7725
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7710
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7710
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7661
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7661
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7591
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7591
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7574
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7574
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7544
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7544
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7503
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7503
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7496
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7496
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7459
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7459
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7453
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7453
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7440
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7440
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7395
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7395
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7391
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7391
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7370
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7370
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7360
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7360
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7359
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7359
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7355
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7355
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7329
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7329
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7324
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7324
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7305
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7305
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7298
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7298
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7285
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7285
Tryptase alpha/beta-1	Q15661	TRYB1_HUMAN	Homo sapiens	3	0.7284
Tryptase alpha/beta-1	Q15661	TRYB1_HUMAN	Homo sapiens	3	0.7284
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7277
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7277
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7270
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7270
Beta-lactamase	Q79MP6	Q79MP6_PSEAI	Pseudomonas aeruginosa	2	0.7268
Beta-lactamase	Q79MP6	Q79MP6_PSEAI	Pseudomonas aeruginosa	2	0.7268
Aminopeptidase N	P04825	AMPN_ECOLI	Escherichia coli	3	0.7256
Aminopeptidase N	P04825	AMPN_ECOLI	Escherichia coli	3	0.7256
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7252
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7252
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7240
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7240
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7238
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7238
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7232
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7232
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7225
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7225
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7217
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7217
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7214
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7214
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	3	0.7195
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	3	0.7195
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7193
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7193
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7193
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7193
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7184
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7184
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7183
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7183
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	2	0.7179
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	2	0.7179
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7166
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7166
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7161
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7161
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7146
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7146
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7139
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7139
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7133
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7133
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7120
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7120
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7113
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7113
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7103
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7103
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7102
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7102
Cell division protein FtsZ	P0A029	FTSZ_STAAM	Staphylococcus aureus	3	0.7088
Cell division protein FtsZ	P0A029	FTSZ_STAAM	Staphylococcus aureus	3	0.7088
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7075
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7075
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7074
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7074
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7065
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7065
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7056
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7056
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7053
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7053
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7038
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7038
RIO-type serine/threonine-protein kinase Rio1	O28471	RIO1_ARCFU	Archaeoglobus fulgidus	2	0.7034
RIO-type serine/threonine-protein kinase Rio1	O28471	RIO1_ARCFU	Archaeoglobus fulgidus	2	0.7034
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7016
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7016
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7015
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7015
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7000
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7000

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