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Dihydromorine

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	Oc1ccc(c(c1)O)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1O)O
InChI	InChI=1S/C15H12O7/c16-6-1-2-8(9(18)3-6)15-14(21)13(20)12-10(19)4-7(17)5-11(12)22-15/h1-5,14-19,21H/t14-,15+/m0/s1
InChIKey	QIWOFDHUQPJCJF-LSDHHAIUSA-N
Formula	C₁₅H₁₂O₇
HBA	7
HBD	5
MW	304.25
Rotatable Bonds	1
TPSA	127.45
LogP	1.19
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.13
Exact Mass	304.06
Number of Lipinski Rule Violations	0

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

Showing of synonyms

Kapche GD, Amadou D, et al. (2011). Hepatoprotective and antioxidant arylbenzofurans and flavonoids from the twigs of Morus mesozygia.. Planta medica,2011, 77(10), 1044-1047. [View] [PubMed]

Pubchem: 5458714

Cas: 18422-83-8

Zinc: ZINC000001573788

Nmrshiftdb2: 60030603

Chembl: CHEMBL463453

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 304.25 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 304.25 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 304.25 g/mol

Antioxidant

Hepatoprotective

Absorption

Caco-2 (logPapp): -6.19
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.250
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.34

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.740
Plasma Protein Binding: 80.56
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 11.500
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.350
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.150
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.670
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: 1.650
Rat (Acute): 2.340
Rat (Chronic Oral): 3.320
Fathead Minnow: 3.880
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 478.560
Hydration Free Energy: -10.780
Log(D) at pH=7.4: 1.580
Log(P): 1.0
Log S: -3.17
Log(Vapor Pressure): -7.71
Melting Point: 244.45
pKa Acid: 4.99
pKa Basic: 5.86

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9302
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9263
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9189
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9119
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9029
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.9011
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8975
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8959
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8934
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8857
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8831
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8796
Dihydrofolate reductase	O30463	O30463_MYCAV	Mycobacterium avium	4	0.8786
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8722
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8688
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.8685
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8672
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8656
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8654
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8636
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8613
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8586
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8572
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8541
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8534
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8521
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.8512
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8505
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8490
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	5	0.8476
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8475
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8421
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8411
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8368
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8358
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8315
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8268
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	5	0.8174
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8151
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.8146
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8144
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8100
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8086
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.8062
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	5	0.8046
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8042
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8039
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8038
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8032
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.8024
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8022
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8017
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8013
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8006
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8001
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7973
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7969
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7963
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	4	0.7947
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.7936
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7925
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7889
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7871
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	4	0.7866
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7822
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7787
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7768
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7740
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7727
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7723
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7704
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7680
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7664
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7653
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7633
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7592
Cyclin-dependent kinase 6	Q00534	CDK6_HUMAN	Homo sapiens	5	0.7575
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7563
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7560
Dihydrofolate reductase	P00381	DYR_LACCA	Lacticaseibacillus casei	4	0.7554
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7548
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7515
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.7513
Quercetin 2,3-dioxygenase	Q7SIC2	QDOI_ASPJA	Aspergillus japonicus	4	0.7513
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7508
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7499
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7479
Glycosyltransferase	A4F1R4	A4F1R4_CLITE	Clitoria ternatea	5	0.7473
Dihydrofolate reductase	Q83AB2	Q83AB2_COXBU	Coxiella burnetii	4	0.7445
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7404
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7403
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7399
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7389
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7383
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7378
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7368
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7345
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7342
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7327
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7316
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7305
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7296
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7293
GTPase KRas	P01116	RASK_HUMAN	Homo sapiens	3	0.7286
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7284
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7280
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7276
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7274
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7272
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7269
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7244
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7240
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	6	0.7232
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7226
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7223
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7194
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7187
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7174
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.7145
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7140
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7130
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7129
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7125
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7097
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7084
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	4	0.7082
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7080
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7054
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7049
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7047
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7045
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7040
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7038
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7036
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7034
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7027
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7027
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7002

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