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1,5,15-O-trimethylmorindol

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

Canonical Smiles	COCc1ccc2c(c1OC)C(=O)c1c(C2=O)c(OC)c(cc1)O
InChI	InChI=1S/C18H16O6/c1-22-8-9-4-5-10-13(17(9)23-2)15(20)11-6-7-12(19)18(24-3)14(11)16(10)21/h4-7,19H,8H2,1-3H3
InChIKey	HEVJQUHAJKODII-UHFFFAOYSA-N
Formula	C₁₈H₁₆O₆
HBA	6
HBD	1
MW	328.32
Rotatable Bonds	4
TPSA	82.06
LogP	2.33
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.22
Exact Mass	328.09
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: 16203753

Cas: 942609-65-6

Zinc: ZINC000014811208

Nmrshiftdb2: 60072017

Chembl: CHEMBL227461

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 328.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.57
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.620
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.38

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.760
Plasma Protein Binding: 52.14
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: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.800
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.840
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.160
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.360
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: Safe
T. Pyriformis: 2.770
Rat (Acute): 2.420
Rat (Chronic Oral): 2.790
Fathead Minnow: 4.770
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 441.010
Hydration Free Energy: -9.110
Log(D) at pH=7.4: 1.990
Log(P): 2.46
Log S: -5.31
Log(Vapor Pressure): -7.22
Melting Point: 175.09
pKa Acid: 6.53
pKa Basic: 4.07

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	0.9228
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9136
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9117
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.9038
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9027
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8909
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8874
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8747
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.8739
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8718
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8715
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8700
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8682
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8678
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8602
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8499
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.8480
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8461
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.8435
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8396
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.8347
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.8239
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.8136
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8122
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8045
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.8031
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7970
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7933
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7894
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7883
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7875
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7875
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7847
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7837
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7809
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7733
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7729
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7697
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7659
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7642
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7634
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7633
Aklavinone 12-hydroxylase RdmE	Q54530	DNRF_STREF	Streptomyces purpurascens	4	0.7623
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7623
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7618
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7613
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7599
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7598
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7594
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7588
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7581
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7581
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7573
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7515
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7510
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7510
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.7488
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7475
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7474
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7468
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7455
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7439
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7434
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7427
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7420
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7417
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7414
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7411
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7410
3',5'-cyclic-AMP phosphodiesterase 4B	Q07343	PDE4B_HUMAN	Homo sapiens	3	0.7409
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7396
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7389
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7374
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7367
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7365
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7360
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7350
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	3	0.7350
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7349
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7334
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7333
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7330
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7320
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7306
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7295
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7292
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7270
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7268
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7257
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7253
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7249
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7249
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7245
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7237
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7227
Metallo-beta-lactamase type 2	P26918	BLAB_AERHY	Aeromonas hydrophila	2	0.7213
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	2	0.7199
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7190
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7162
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7159
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7154
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7146
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7137
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7133
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7128
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7127
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7121
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7103
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7102
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7101
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7089
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7087
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7085
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7079
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7070
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7067
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7065
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7056
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7053
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7052
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7052
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7045
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7045
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7042
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7039
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7037
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7036
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7008
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7006

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