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Retrojusticidin B

Family: Plantae - Arecaceae
Kingdom: Plantae
Class: Arylnaphthalene

Canonical Smiles	COc1cc2c(cc1OC)cc1c(c2c2ccc3c(c2)OCO3)COC1=O
InChI	InChI=1S/C21H16O6/c1-23-17-7-12-5-14-15(9-25-21(14)22)20(13(12)8-18(17)24-2)11-3-4-16-19(6-11)27-10-26-16/h3-8H,9-10H2,1-2H3
InChIKey	TXDMVCNSUVLKHW-UHFFFAOYSA-N
Formula	C₂₁H₁₆O₆
HBA	6
HBD	0
MW	364.35
Rotatable Bonds	3
TPSA	63.22
LogP	3.92
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	364.09
Number of Lipinski Rule Violations	0

#	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: 460888

Cas: 82001-16-9

Nmrshiftdb2: 60070873

Chembl: CHEMBL292540

Comptox: DTXSID80231512

Bindingdb: 50240576

CPRiL: 381985

SMILES: c1cccc(c2)c1c(c(c23)COC3=O)-c(c4)ccc(c45)OCO5

Level: 1

Mol. Weight: 364.35 g/mol

SMILES: O=C1OCc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 364.35 g/mol

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 364.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.02
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.780
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.05

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.350
Plasma Protein Binding: 74.8
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 10.950
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.760
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.140
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.100
Micronucleos: Toxic
NR-AhR: Toxic
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: -13.820
Rat (Acute): 2.580
Rat (Chronic Oral): 1.440
Fathead Minnow: 5.620
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 495.820
Hydration Free Energy: -5.890
Log(D) at pH=7.4: 2.910
Log(P): 3.34
Log S: -5.07
Log(Vapor Pressure): -8.71
Melting Point: 201.16
pKa Acid: 9.41
pKa Basic: 1.76

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9787
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9710
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.9325
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9186
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8753
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8661
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8632
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8626
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8606
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8604
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8499
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8488
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.8324
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.8252
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8210
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8168
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.8076
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.8052
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8030
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7984
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7914
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7852
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7851
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7815
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7803
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7767
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7725
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7722
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7707
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7706
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7678
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7655
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7644
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7627
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7604
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7603
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7568
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7534
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7520
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7495
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7467
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7466
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7465
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7463
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7454
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7433
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7432
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7419
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7410
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7386
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7338
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7314
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7308
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7306
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7304
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7294
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7276
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7248
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7241
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7236
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7228
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7216
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7204
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7177
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7168
Mitogen-activated protein kinase 1	P63086	MK01_RAT	Rattus norvegicus	3	0.7158
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7146
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7136
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7125
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7110
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7105
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7048
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7021
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7011

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