ANPDB

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Naucleidinal

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

Canonical Smiles	O=CC1[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-DEPLHBLFSA-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: 137628428

Gnps: CCMSLIB00004680014

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

Antibacterial

Absorption

Caco-2 (logPapp): -4.88
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.77
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.07

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.45
Plasma Protein Binding: 47.08
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: 11.09
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.18
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.93
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.62
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: -6.51
Rat (Acute): 3.31
Rat (Chronic Oral): 1.61
Fathead Minnow: 4.15
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: 439.38
Hydration Free Energy: -7.25
Log(D) at pH=7.4: 1.97
Log(P): 2.17
Log S: -3.97
Log(Vapor Pressure): -9.33
Melting Point: 224.22
pKa Acid: 9.19
pKa Basic: 6.44

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase, inducible	P35228	NOS2_HUMAN	Homo sapiens	3	0.9091
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8923
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8766
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8690
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8530
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8505
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8383
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8368
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.8285
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8231
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8218
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8198
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8142
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8123
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.8096
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8037
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.8037
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7966
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7936
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7888
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7888
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7865
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7852
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7852
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7833
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7822
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7820
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7793
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7782
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7769
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7752
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7745
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7721
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7697
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7682
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7668
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7664
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7661
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7602
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7573
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7534
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7486
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7480
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	3	0.7479
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7460
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7451
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7437
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7395
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7392
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7387
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7375
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.7312
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.7300
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7295
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7287
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7271
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7249
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.7241
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7198
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7194
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7179
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7175
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7167
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7156
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	2	0.7152
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7148
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7147
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7146
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7145
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7142
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7141
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7134
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7115
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7114
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7107
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7107
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7091
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7082
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7067
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7065
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7063
Casein kinase I isoform gamma-2	P78368	KC1G2_HUMAN	Homo sapiens	3	0.7057
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7036
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7030
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7007

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