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Pobeguinine

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

Canonical Smiles	C/C=C\1/COC(=O)[C@@H]2[C@H]1C[C@@H]1N(C2=O)CCc2c1[nH]c1c2cccc1
InChI	InChI=1S/C20H20N2O3/c1-2-11-10-25-20(24)17-14(11)9-16-18-13(7-8-22(16)19(17)23)12-5-3-4-6-15(12)21-18/h2-6,14,16-17,21H,7-10H2,1H3/b11-2-/t14-,16-,17+/m0/s1
InChIKey	BKIFWXBEJYBPMT-BXWXAXRQSA-N
Formula	C₂₀H₂₀N₂O₃
HBA	3
HBD	1
MW	336.39
Rotatable Bonds	0
TPSA	62.4
LogP	2.73
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	336.15
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]

Pubchem: 155563291

Chembl: CHEMBL4571926

No compound-protein relationship available.

SMILES: O=C1OCC(=C)C(C2)C1C(=O)N(CC3)C2c(c3c45)[nH]c4cccc5

Level: 0

Mol. Weight: 336.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.95
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.11

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.93
Plasma Protein Binding: 55.42
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.96
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.07
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.42
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.08
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: -3.9
Rat (Acute): 3.18
Rat (Chronic Oral): 2.02
Fathead Minnow: 4.55
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 460.36
Hydration Free Energy: -6.97
Log(D) at pH=7.4: 1.61
Log(P): 1.67
Log S: -3.95
Log(Vapor Pressure): -9.33
Melting Point: 271.45
pKa Acid: 9.27
pKa Basic: 6.67

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Hexokinase-4	P35557	HXK4_HUMAN	Homo sapiens	3	0.8958
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8788
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8367
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8310
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8270
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8233
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8024
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7988
Nitric oxide synthase, inducible	P35228	NOS2_HUMAN	Homo sapiens	3	0.7893
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7883
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.7853
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7849
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7846
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7831
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7800
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7786
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7739
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7739
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7738
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7732
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7710
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7688
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7631
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7590
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7589
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7559
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7509
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7507
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7448
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7434
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7432
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7429
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7427
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7418
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7400
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7389
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7336
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7335
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7251
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7237
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7232
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7221
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7191
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7186
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7175
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7156
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7150
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7143
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7131
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7129
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7117
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7104
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	2	0.7100
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7089
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7056
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7050
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7044
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7027
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7026
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7018
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7009

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