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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-MIJDYPGTSA-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]

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

Antibacterial

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: 55.22
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: 8.97
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
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: 4.06
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: -4.98
Rat (Acute): 3.19
Rat (Chronic Oral): 2.02
Fathead Minnow: 4.3
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 458.68
Hydration Free Energy: -6.98
Log(D) at pH=7.4: 1.62
Log(P): 1.68
Log S: -3.92
Log(Vapor Pressure): -9.32
Melting Point: 257.03
pKa Acid: 9.26
pKa Basic: 6.67

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.9010
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8942
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8623
Nitric oxide synthase, inducible	P35228	NOS2_HUMAN	Homo sapiens	3	0.8510
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8502
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8460
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.8395
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.8319
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8163
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8159
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.8061
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7990
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7871
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7837
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7835
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7816
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7800
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7754
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7754
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7737
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7722
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7708
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7668
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7659
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7635
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7604
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7602
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7575
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7571
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7559
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7544
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7543
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7539
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7539
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7536
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7531
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7519
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7518
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7496
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7481
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7474
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7471
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	2	0.7431
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7429
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7423
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7407
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7391
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7388
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7384
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7373
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7351
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7342
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7292
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7245
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7236
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7235
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7217
Genome polyprotein	Q99AU2	Q99AU2_9HEPC	Hepatitis C virus subtype 1b	4	0.7216
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7216
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7185
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7168
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	2	0.7148
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7139
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7131
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7127
Lactoylglutathione lyase	Q04760	LGUL_HUMAN	Homo sapiens	2	0.7108
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7104
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7071
Purine nucleoside phosphorylase, putative	A2E7Y6	A2E7Y6_TRIVA	Trichomonas vaginalis	2	0.7051
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7048
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	2	0.7041
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7037
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	2	0.7036
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7035
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7024
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7021
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7010

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