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Moracin O

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Stilbenoid

Canonical Smiles	Oc1cc(O)cc(c1)c1oc2c(c1)cc1c(c2)O[C@H](C1)C(O)(C)C
InChI	InChI=1S/C19H18O5/c1-19(2,22)18-7-11-3-10-6-15(23-16(10)9-17(11)24-18)12-4-13(20)8-14(21)5-12/h3-6,8-9,18,20-22H,7H2,1-2H3/t18-/m1/s1
InChIKey	HMTMYIWMPJSCAZ-GOSISDBHSA-N
Formula	C₁₉H₁₈O₅
HBA	5
HBD	3
MW	326.35
Rotatable Bonds	2
TPSA	83.06
LogP	3.59
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.26
Exact Mass	326.12
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: 42604718

Cas: 123702-97-6

Zinc: ZINC000014610079

Chembl: CHEMBL1795432

Bindingdb: 50346796

CPRiL: 123648

SMILES: O1CCc(c2)c1cc(c23)oc(c3)-c4ccccc4

Level: 1

Mol. Weight: 326.35 g/mol

SMILES: c1coc(c12)cc3c(c2)CCO3

Level: 0

Mol. Weight: 326.35 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 326.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.84
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.79
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.91

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.9
Plasma Protein Binding: 82.19
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: 6.12
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 2.12
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.84
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.68
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 0.6
Rat (Acute): 1.89
Rat (Chronic Oral): 2.32
Fathead Minnow: 4.67
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 435.96
Hydration Free Energy: -11.67
Log(D) at pH=7.4: 3.26
Log(P): 3.19
Log S: -4.16
Log(Vapor Pressure): -9.94
Melting Point: 276.12
pKa Acid: 8.64
pKa Basic: 6.73

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9352
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9343
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.9318
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9284
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.9225
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.9083
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9062
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9043
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	4	0.8983
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8971
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.8856
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8818
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8781
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8705
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.8676
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8665
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8617
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8552
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8548
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8533
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8508
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8393
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8373
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8313
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.8266
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8119
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8040
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8009
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7952
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7919
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7912
Cholinesterase	P06276	CHLE_HUMAN	Homo sapiens	3	0.7902
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7900
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7882
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7804
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7786
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7734
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7728
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7708
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7705
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7699
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7674
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7633
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7607
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.7602
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7592
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7585
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7584
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7537
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7537
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7498
Glycoside Hydrolase Family 13	Q65MI2	Q65MI2_BACLD	Bacillus licheniformis	3	0.7491
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7448
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7439
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7437
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7402
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7392
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7392
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7364
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7364
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7362
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.7354
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7332
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.7330
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7325
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7301
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7293
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7292
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7281
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7243
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7241
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7233
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7227
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7226
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7211
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7202
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7176
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	4	0.7175
Rac-like GTP-binding protein ARAC7	O82480	RAC7_ARATH	Arabidopsis thaliana	3	0.7159
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7135
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7117
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7113
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7107
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7103
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7096
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7089
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7089
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7071
Putative FAD-dependent oxygenase EncM	Q9KHK2	Q9KHK2_9ACTN	Streptomyces maritimus	3	0.7063
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7051
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7041
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7000

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