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Latifoliaindole A

Family: Plantae - Rubiaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Monoterpenoid Indole Alkaloid

Canonical Smiles	C/C=C(/c1cc2c3[nH]c4c(c3CCn2c(=O)c1O)cccc4)\C=O
InChI	InChI=1S/C19H16N2O3/c1-2-11(10-22)14-9-16-17-13(7-8-21(16)19(24)18(14)23)12-5-3-4-6-15(12)20-17/h2-6,9-10,20,23H,7-8H2,1H3/b11-2+
InChIKey	SSXJDMGJJARZQV-BIIKFXOESA-N
Formula	C₁₉H₁₆N₂O₃
HBA	4
HBD	2
MW	320.35
Rotatable Bonds	2
TPSA	75.09
LogP	2.86
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.16
Exact Mass	320.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Nauclea latifolia	Rubiaceae	Plantae	43573

Showing of synonyms

Kezetas Bankeu JJ, Kenou Kagho DU, et al. (2019). Constituents from Nauclea latifolia with Anti-Haemophilus influenzae Type b Inhibitory Activities.. Journal of natural products,2019, 82(9), 2580-2585. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccc(=O)n(CC2)c1c(c2c34)[nH]c3cccc4

Level: 0

Mol. Weight: 320.35 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -4.95
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.51
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.43

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.84
Plasma Protein Binding: 52.32
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 3.86
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.24
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.11
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.97
Micronucleos: Toxic
NR-AhR: Safe
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: 0.29
Rat (Acute): 2.96
Rat (Chronic Oral): 1.85
Fathead Minnow: 4.58
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 469.92
Hydration Free Energy: -11.53
Log(D) at pH=7.4: 1.93
Log(P): 2.38
Log S: -4.23
Log(Vapor Pressure): -9.66
Melting Point: 255.35
pKa Acid: 9.28
pKa Basic: 6.74

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9136
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9065
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8953
Phosphodiesterase	Q53I60	Q53I60_TRYCR	Trypanosoma cruzi	4	0.8846
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.8806
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.8767
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8757
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8743
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8737
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8620
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8600
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8555
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8392
Nitric oxide synthase, inducible	P35228	NOS2_HUMAN	Homo sapiens	3	0.8351
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	4	0.8300
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8290
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8289
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8230
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8210
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8173
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8164
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8109
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7981
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7967
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7951
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7944
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	4	0.7884
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7871
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7861
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7852
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7839
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7805
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7765
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7740
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7719
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7705
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7700
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7700
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7692
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7684
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7682
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7674
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7622
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7598
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7597
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7595
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	4	0.7591
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7567
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7560
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7558
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7513
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7506
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7494
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7491
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7462
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7455
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7450
Matrix metalloproteinase-9	P14780	MMP9_HUMAN	Homo sapiens	3	0.7439
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7438
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7402
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7402
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7394
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7392
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7386
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7375
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7355
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7349
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7345
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7328
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7310
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7303
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7302
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7302
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7268
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7245
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7230
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7230
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7212
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7207
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7187
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7185
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7170
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7155
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7154
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7144
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	3	0.7143
Cellular retinoic acid-binding protein 1	P62964	RABP1_BOVIN	Bos taurus	4	0.7135
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7127
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7123
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7113
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7112
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7109
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7103
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7092
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7091
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7087
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7086
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7083
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7073
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7072
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7047
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7032
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7028
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7024
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7022
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	2	0.7021
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7020
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7019
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	2	0.7007
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7001

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