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Moracin R

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Benzofuran
- Subclass: Prenylated Benzofuran

Canonical Smiles	Oc1cc(O)cc(c1)c1cc2c(o1)cc(c(c2)CC(C(O)(C)C)O)O
InChI	InChI=1S/C19H20O6/c1-19(2,24)18(23)7-10-3-11-6-16(25-17(11)9-15(10)22)12-4-13(20)8-14(21)5-12/h3-6,8-9,18,20-24H,7H2,1-2H3
InChIKey	TYECGXQALROZJT-UHFFFAOYSA-N
Formula	C₁₉H₂₀O₆
HBA	6
HBD	5
MW	344.36
Rotatable Bonds	4
TPSA	114.29
LogP	2.89
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.26
Exact Mass	344.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Morus mesozygia	Moraceae	Plantae	3054370

Showing of synonyms

Fozing CDA (2009). Prenylated arylbenzofuran derivatives from Morus mesozygia with antioxidant activity.. Phytochemistry,2009, 70(2), 216-221. [View] [PubMed]

Pubchem: 42605183

Nmrshiftdb2: 80005334

Chembl: CHEMBL3397399

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(c2)-c3ccccc3

Level: 1

Mol. Weight: 344.36 g/mol

SMILES: c1coc(c12)cccc2

Level: 0

Mol. Weight: 344.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 344.36 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -5.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.12
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.75
Plasma Protein Binding: 59.54
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: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.07
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.61
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.8
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.52
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 1.09
Rat (Acute): 2.26
Rat (Chronic Oral): 3.34
Fathead Minnow: 4.34
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 461.17
Hydration Free Energy: -12.42
Log(D) at pH=7.4: 2.77
Log(P): 2.06
Log S: -3.19
Log(Vapor Pressure): -8.69
Melting Point: 246.75
pKa Acid: 7.8
pKa Basic: 6.9

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9480
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9353
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.9311
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9276
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.9230
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.8920
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8905
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8851
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8842
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8840
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8787
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8777
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8759
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8715
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8703
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8672
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8576
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8524
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.8494
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8452
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8365
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8320
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8300
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8291
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8287
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8273
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.8260
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8219
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.8217
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8193
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8189
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8188
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8171
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8135
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8102
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8100
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8011
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8005
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7989
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.7977
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7968
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7917
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7901
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7895
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7829
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7812
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7807
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7799
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	3	0.7791
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7784
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7776
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	4	0.7751
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7748
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7731
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7722
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7719
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7710
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7709
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7696
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7693
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7656
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7646
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.7594
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7589
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7573
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.7547
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7546
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7538
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7538
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7537
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7534
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7532
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7528
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7513
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.7501
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7478
Vitamin D 25-hydroxylase	Q6VVX0	CP2R1_HUMAN	Homo sapiens	5	0.7450
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7448
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7440
Bifunctional adenosylcobalamin biosynthesis protein CobU	Q05599	COBU_SALTY	Salmonella typhimurium	4	0.7417
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.7411
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7406
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7380
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7370
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7367
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7331
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7312
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7298
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	Q6NVY1	HIBCH_HUMAN	Homo sapiens	3	0.7291
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7283
Vitamin D3 receptor	P11473	VDR_HUMAN	Homo sapiens	5	0.7270
Cellular retinol-binding protein type II	Q8UVG6	Q8UVG6_DANRE	Danio rerio	3	0.7268
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7265
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7263
Oxysterols receptor LXR-beta	P55055	NR1H2_HUMAN	Homo sapiens	3	0.7261
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7261
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7216
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7208
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7201
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7182
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7164
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7162
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7143
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7137
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	5	0.7127
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7123
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	4	0.7120
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7114
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.7101
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7100
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7089
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7071
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7067
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7054
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7041
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7041
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7037
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7029
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7025
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7019
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7015
Metallophosphoesterase	A3DJ38	A3DJ38_HUNT2	Clostridium thermocellum	2	0.7011

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