ANPDB

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Naucleidinal

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

Canonical Smiles	O=C[C@@H]1[C@@H](C)OC=C2[C@H]1C[C@@H]1N(C2=O)CCc2c1[nH]c1c2cccc1
InChI	InChI=1S/C20H20N2O3/c1-11-15(9-23)14-8-18-19-13(12-4-2-3-5-17(12)21-19)6-7-22(18)20(24)16(14)10-25-11/h2-5,9-11,14-15,18,21H,6-8H2,1H3/t11-,14+,15-,18+/m1/s1
InChIKey	KCMWOWTUEWHAMM-OPNLHGRLSA-N
Formula	C₂₀H₂₀N₂O₃
HBA	3
HBD	1
MW	336.39
Rotatable Bonds	1
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: 10969739

Gnps: CCMSLIB00004680014

Zinc: ZINC000014612614

Chebi: 141926

Nmrshiftdb2: 60081341

Chembl: CHEMBL4450885

No compound-protein relationship available.

SMILES: c1cccc2[nH]c(c3c12)C4N(CC3)C(=O)C=5C(C4)CCOC5

Level: 0

Mol. Weight: 336.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.88
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.770
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.06

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.450
Plasma Protein Binding: 51.77
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: 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: 11.120
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.120
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.930
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.610
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: -5.870
Rat (Acute): 3.310
Rat (Chronic Oral): 1.610
Fathead Minnow: 4.060
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: 441.480
Hydration Free Energy: -7.210
Log(D) at pH=7.4: 1.970
Log(P): 2.19
Log S: -4.0
Log(Vapor Pressure): -9.43
Melting Point: 234.02
pKa Acid: 9.22
pKa Basic: 6.42

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.9173
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9065
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.9026
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8946
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8906
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8536
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8529
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8486
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8416
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.8326
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8241
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8118
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7991
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7940
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7932
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7899
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7888
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7878
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7871
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7822
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7768
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7748
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7745
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7741
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7730
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7725
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7722
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7671
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7661
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7656
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7650
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7647
Nitric oxide synthase, inducible	P35228	NOS2_HUMAN	Homo sapiens	3	0.7559
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7555
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7515
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7511
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7505
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7479
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7438
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7417
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7415
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7414
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7402
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7395
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7394
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7350
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7348
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7322
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7318
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7295
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7289
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7253
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7249
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7225
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7192
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7187
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7175
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7169
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	2	0.7149
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7148
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7143
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7130
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7117
Lactoylglutathione lyase	Q04760	LGUL_HUMAN	Homo sapiens	2	0.7102
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7093
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7092
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	2	0.7061
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7054
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7045
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7041
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	3	0.7035
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7033
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7028
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7028
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7027
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7022
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7020
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7002
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7001

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