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Robustin

Family: Plantae - Rutaceae
Kingdom: Plantae
Class: Coumarin
- Subclass: Arylpyranocoumarin

Canonical Smiles	COc1c2C=CC(Oc2cc2c1c(O)c(c(=O)o2)c1ccc2c(c1)OCO2)(C)C
InChI	InChI=1S/C22H18O7/c1-22(2)7-6-12-14(29-22)9-16-18(20(12)25-3)19(23)17(21(24)28-16)11-4-5-13-15(8-11)27-10-26-13/h4-9,23H,10H2,1-3H3
InChIKey	LCSCNPZJBMHOJH-UHFFFAOYSA-N
Formula	C₂₂H₁₈O₇
HBA	7
HBD	1
MW	394.38
Rotatable Bonds	2
TPSA	87.36
LogP	4.09
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.23
Exact Mass	394.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Zanthoxylum tessmannii	Rutaceae	Plantae	1291627

Showing of synonyms

Kenmoe Djeukeu C, Kouam Kenmogne A, et al. (2019). A New Aromatic Amide from the Roots of Zanthoxylum tessmannii (Rutaceae).. Chemistry & biodiversity,2019, 16(4), e1800590. [View] [PubMed]

Pubchem: 54708253

Cas: 22044-61-7

Zinc: ZINC000014687503

Nmrshiftdb2: 80005655

No compound-protein relationship available.

SMILES: O1COc(c12)ccc(c2)-c(c3)c(=O)oc(c34)cc5c(c4)C=CCO5

Level: 1

Mol. Weight: 394.38 g/mol

SMILES: c1cc(=O)oc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 394.38 g/mol

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 394.38 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -4.45
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.59
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.06

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.77
Plasma Protein Binding: 85.24
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.38
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.06
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.16
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.69
Micronucleos: Toxic
NR-AhR: Toxic
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: -25.57
Rat (Acute): 3.05
Rat (Chronic Oral): 1.9
Fathead Minnow: 5.25
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 487.34
Hydration Free Energy: -5.75
Log(D) at pH=7.4: 3.11
Log(P): 4.05
Log S: -5.87
Log(Vapor Pressure): -8.81
Melting Point: 194.86
pKa Acid: 7.78
pKa Basic: 2.02

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9463
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9394
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9046
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.8982
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8566
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8535
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8521
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8491
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8441
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8357
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8312
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8310
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8229
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8063
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8052
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8025
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7882
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7881
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7858
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7719
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	3	0.7645
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7644
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7620
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7590
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7567
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7566
Beta-elicitin cinnamomin	P15569	ELIB_PHYCI	Phytophthora cinnamomi	3	0.7496
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7487
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7440
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7426
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7386
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7341
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7298
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7295
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7295
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7231
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7216
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7191
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7190
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	3	0.7186
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7186
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7186
Nuclear receptor coactivator 2	Q15596	NCOA2_HUMAN	Homo sapiens	3	0.7152
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7141
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7140
Reductase homolog	Q9ZGC1	Q9ZGC1_STRCY	Streptomyces cyanogenus	3	0.7095
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7090
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7057
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7031
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7016
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7014
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7003

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