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5(S)-5-carboxystrictisidine

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

Canonical Smiles	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H]([C@H]2C=C)C[C@@H]2N[C@@H](Cc3c2[nH]c2c3cccc2)C(=O)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C28H34N2O11/c1-3-12-14(8-18-21-15(9-19(29-18)25(35)36)13-6-4-5-7-17(13)30-21)16(26(37)38-2)11-39-27(12)41-28-24(34)23(33)22(32)20(10-31)40-28/h3-7,11-12,14,18-20,22-24,27-34H,1,8-10H2,2H3,(H,35,36)/t12-,14+,18+,19+,20-,22-,23+,24-,27+,28+/m1/s1
InChIKey	LHKZIVMTXZLOTP-RMKGEEGASA-N
Formula	C₂₈H₃₄N₂O₁₁
HBA	11
HBD	7
MW	574.58
Rotatable Bonds	8
TPSA	200.03
LogP	-0.15
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	574.22
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Mussaenda luteola	Rubiaceae	Plantae	43523

Showing of synonyms

Mohamed S.M, Backheet E.Y, et al. (2016). Newcycloartane saponin and monoterpenoid glucoindole alkaloids from Mussaenda luteola. Fitoterapia, 2016, 110, 129-34. [View] [PubMed]

Pubchem: 10483216

Cas: 34371-47-6

Gnps: CCMSLIB00004685119

Zinc: ZINC000058553460

Nmrshiftdb2: 60023909

Chembl: CHEMBL4442305

No compound-protein relationship available.

SMILES: c1cccc2[nH]c(c3c12)C(NCC3)CC4C=COC(C4)OC5CCCCO5

Level: 2

Mol. Weight: 574.58 g/mol

SMILES: C1COC=CC1CC(NCC2)c(c2c34)[nH]c3cccc4

Level: 1

Mol. Weight: 574.58 g/mol

SMILES: O1C=CCCC1OC2CCCCO2

Level: 1

Mol. Weight: 574.58 g/mol

SMILES: C1CNCc(c1c23)[nH]c2cccc3

Level: 0

Mol. Weight: 574.58 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 574.58 g/mol

SMILES: C1=COCCC1

Level: 0

Mol. Weight: 574.58 g/mol

Antitrypanosomal

Absorption

Caco-2 (logPapp): -6.55
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.060
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 3.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.920
Plasma Protein Binding: 63.54
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: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-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: 2.930
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.850
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.270
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 8.130
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: Safe
T. Pyriformis: -9322.310
Rat (Acute): 2.460
Rat (Chronic Oral): 3.550
Fathead Minnow: 20.250
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: 430.050
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -0.710
Log(P): -1.06
Log S: -2.64
Log(Vapor Pressure): -12.36
Melting Point: 166.06
pKa Acid: 1.68
pKa Basic: 7.41

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	3	0.8732
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	3	0.8274
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8226
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8141
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7882
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	3	0.7858
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7856
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7837
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	B1MKD5	B1MKD5_MYCA9	Mycobacteroides abscessus	3	0.7775
Acidic mammalian chitinase	Q9BZP6	CHIA_HUMAN	Homo sapiens	3	0.7522
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7442
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase	Q9WY79	MURE_THEMA	Thermotoga maritima	3	0.7434
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7426
Mitochondrial dynamics protein MIEF1	Q9NQG6	MID51_HUMAN	Homo sapiens	2	0.7425
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7400
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7340
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7335
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7308
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	3	0.7289
Malate dehydrogenase	P10584	MDH_THETH	Thermus thermophilus	3	0.7232
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7217
Type 4 fimbrial biogenesis protein PilM	G3XD28	G3XD28_PSEAE	Pseudomonas aeruginosa	3	0.7201
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7199
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7100
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7070
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7064
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7063
Interleukin enhancer-binding factor 2	Q9CXY6	ILF2_MOUSE	Mus musculus	2	0.7044
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7035
Histidinol dehydrogenase	P06988	HISX_ECOLI	Escherichia coli	2	0.7031

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