ANPDB

Select a section from the left sidebar

5,15-O-dimethylmorindol

Family: Plantae - Rubiaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Anthraquinone

Canonical Smiles	COCc1ccc2c(c1O)C(=O)c1c(C2=O)c(OC)c(cc1)O
InChI	InChI=1S/C17H14O6/c1-22-7-8-3-4-9-12(14(8)19)15(20)10-5-6-11(18)17(23-2)13(10)16(9)21/h3-6,18-19H,7H2,1-2H3
InChIKey	KKHLOCIPXRSWKM-UHFFFAOYSA-N
Formula	C₁₇H₁₄O₆
HBA	6
HBD	2
MW	314.29
Rotatable Bonds	3
TPSA	93.06
LogP	2.03
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.18
Exact Mass	314.08
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Morinda lucida	Rubiaceae	Plantae	339305

Showing of synonyms

Longue Ekon J, Zra T, et al. (2020). New anthraquinone derivatives from the stem barks of Morinda lucida Benth. Phytochemistry Letters, 2020, 39, 94-98. [View]

Pubchem: 11674044

Cas: 877238-55-6

Nmrshiftdb2: 60072016

Chembl: CHEMBL445667

Comptox: DTXSID80470429

No compound-protein relationship available.

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 314.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.48
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.720
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.21

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.850
Plasma Protein Binding: 52.72
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: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.540
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.600
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.270
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.200
Micronucleos: Toxic
NR-AhR: Toxic
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: 3.600
Rat (Acute): 2.500
Rat (Chronic Oral): 3.160
Fathead Minnow: 4.520
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 433.950
Hydration Free Energy: -8.770
Log(D) at pH=7.4: 1.940
Log(P): 2.72
Log S: -5.65
Log(Vapor Pressure): -7.58
Melting Point: 176.58
pKa Acid: 6.03
pKa Basic: 4.61

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	0.9179
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9154
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9105
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8998
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8971
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8810
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8714
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8713
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8681
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8674
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8503
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8459
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8414
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8411
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8348
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8334
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.8297
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8205
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8077
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7954
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7906
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7871
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7844
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.7828
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7825
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7769
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7728
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	4	0.7646
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7620
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7620
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7619
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7616
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7596
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7591
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7587
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7580
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7576
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7575
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7557
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7547
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7533
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7524
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.7510
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7496
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7484
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7441
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7420
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7395
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7394
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7373
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7356
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7348
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7338
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7320
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7313
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7306
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7297
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7293
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7283
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7280
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7279
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7276
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7269
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7263
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7257
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7253
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7239
Aklavinone 12-hydroxylase RdmE	Q54530	DNRF_STREF	Streptomyces purpurascens	4	0.7236
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7232
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	4	0.7224
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7209
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7168
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7164
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7163
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7157
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7152
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7148
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7139
3',5'-cyclic-AMP phosphodiesterase 4B	Q07343	PDE4B_HUMAN	Homo sapiens	3	0.7133
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7130
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7115
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7110
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7099
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7098
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7091
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7078
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7075
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7073
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7071
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7071
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7044
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7034
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7031
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7031
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7028
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7023
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7014

Download SDF