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Scirpusin B

Family: Plantae - Arecaceae
Kingdom: Plantae
Class: Stilbenoid
- Subclass: Hydroxystilbene

Canonical Smiles	Oc1cc(/C=C/c2ccc(c(c2)O)O)c2c(c1)OC(C2c1cc(O)cc(c1)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C28H22O8/c29-18-9-17(10-19(30)12-18)27-26-15(3-1-14-2-5-21(32)23(34)7-14)8-20(31)13-25(26)36-28(27)16-4-6-22(33)24(35)11-16/h1-13,27-35H/b3-1+
InChIKey	MTYSFTYBAMMIGE-HNQUOIGGSA-N
Formula	C₂₈H₂₂O₈
HBA	8
HBD	7
MW	486.48
Rotatable Bonds	4
TPSA	150.84
LogP	5.06
Number Rings	5
Number Aromatic Rings	4
Heavy Atom Count	36
Formal Charge	0
Fraction CSP3	0.07
Exact Mass	486.13
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Syagrus romanzoffiana	Arecaceae	Plantae	290277

Showing of synonyms

El-Hawary S.S, Fathy F.I, et al. (2021). Anticholinesterase activity and metabolite profiling of Syagrus romanzoffiana (Cham.) Glassman leaves and fruits via UPLC–QTOF–PDA–MS. Natural product research, 2021, 35(10), 1671-1675. [View] [PubMed]

Pubchem: 5458999

Cas: 69297-49-0

Nmrshiftdb2: 70127905

Chembl: CHEMBL514088

CPRiL: 152417

SMILES: c1ccccc1C=Cc2cccc(c23)OC(c4ccccc4)C3c5ccccc5

Level: 3

Mol. Weight: 486.48 g/mol

SMILES: c1ccccc1C=Cc2cccc(c23)OCC3c4ccccc4

Level: 2

Mol. Weight: 486.48 g/mol

SMILES: c1ccccc1C=Cc2cccc(c23)OC(C3)c4ccccc4

Level: 2

Mol. Weight: 486.48 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C2c4ccccc4

Level: 2

Mol. Weight: 486.48 g/mol

SMILES: c1ccccc1C=Cc2cccc(c23)OCC3

Level: 1

Mol. Weight: 486.48 g/mol

SMILES: c1cccc(c12)OCC2c3ccccc3

Level: 1

Mol. Weight: 486.48 g/mol

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 486.48 g/mol

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 486.48 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 486.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.26
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.220
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.36

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.210
Plasma Protein Binding: 79.5
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 8.330
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.460
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.370
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.860
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -750.710
Rat (Acute): 2.130
Rat (Chronic Oral): 3.580
Fathead Minnow: 7.340
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 642.030
Hydration Free Energy: -3.270
Log(D) at pH=7.4: 2.440
Log(P): 4.03
Log S: -4.09
Log(Vapor Pressure): -11.58
Melting Point: 324.6
pKa Acid: 7.64
pKa Basic: 10.4

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9046
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8982
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8879
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8788
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8557
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.8405
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8360
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8359
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8313
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.8294
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8273
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8150
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8028
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8003
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7919
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7889
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7876
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7769
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7710
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7704
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7696
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7694
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7630
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	4	0.7592
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7562
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7518
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7467
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7462
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	4	0.7421
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7421
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7413
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7407
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.7403
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7401
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7387
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7326
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7301
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7289
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7274
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7235
Aminopeptidase N	P04825	AMPN_ECOLI	Escherichia coli	3	0.7213
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7211
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7199
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7189
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7160
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7155
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7095
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7084
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7084
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7083
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7068
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7064

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