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Strictosamide

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

Canonical Smiles	OC[C@H]1O[C@@H](O[C@@H]2OC=C3[C@H]([C@H]2C=C)C[C@@H]2N(C3=O)CCc3c2[nH]c2c3cccc2)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C26H30N2O8/c1-2-12-15-9-18-20-14(13-5-3-4-6-17(13)27-20)7-8-28(18)24(33)16(15)11-34-25(12)36-26-23(32)22(31)21(30)19(10-29)35-26/h2-6,11-12,15,18-19,21-23,25-27,29-32H,1,7-10H2/t12-,15+,18+,19-,21-,22+,23-,25+,26+/m1/s1
InChIKey	LBRPLJCNRZUXLS-IUNANRIWSA-N
Formula	C₂₆H₃₀N₂O₈
HBA	8
HBD	5
MW	498.53
Rotatable Bonds	4
TPSA	144.71
LogP	0.47
Number Rings	6
Number Aromatic Rings	2
Heavy Atom Count	36
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	498.2
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Mitragyna inermis	Rubiaceae	Plantae	170023
2	Nauclea pobeguinii	Rubiaceae	Plantae	43525

Showing of synonyms

Kuete V, Sandjo LP, et al. (2015). Cytotoxicity of selected Cameroonian medicinal plants and Nauclea pobeguinii towards multi-factorial drug-resistant cancer cells.. BMC complementary and alternative medicine,2015, 15, 309. [View] [PubMed]
Donfack E, Lenta B, et al. (2012). Naucleactonin D, an Indole Alkaloid and other Chemical Constituents from Roots and Fruits of Mitragyna inermis. Zeitschrift für Naturforschung B. 2012, 67(11), 1159-1165. [View]

Pubchem: 10345799

Cas: 23141-25-5

Gnps: CCMSLIB00004680054

Zinc: ZINC000028541549

Kegg Ligand: C16724

Chebi: 80684

Nmrshiftdb2: 60023918

Chembl: CHEMBL4438424

Comptox: DTXSID60438421

Bindingdb: 50531272

CPRiL: 164020

SMILES: c1cccc2[nH]c(c3c12)C4N(CC3)C(=O)C=5C(C4)CC(OC5)OC6CCCCO6

Level: 1

Mol. Weight: 498.53 g/mol

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

Level: 0

Mol. Weight: 498.53 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 498.53 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -6.16
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.140
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.64

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.030
Plasma Protein Binding: 66.99
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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.540
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.550
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.290
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.920
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: -1366.840
Rat (Acute): 3.880
Rat (Chronic Oral): 3.100
Fathead Minnow: 4.170
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 524.350
Hydration Free Energy: -2.930
Log(D) at pH=7.4: 1.800
Log(P): 0.3
Log S: -2.91
Log(Vapor Pressure): -13.09
Melting Point: 201.53
pKa Acid: 4.99
pKa Basic: 6.84

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	0.9393
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.9251
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.9223
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.9192
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.9146
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.9086
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.9074
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.9011
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8953
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8855
Nitric oxide synthase, inducible	P35228	NOS2_HUMAN	Homo sapiens	3	0.8852
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8799
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8778
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8763
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8585
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.8581
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8414
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.8371
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8357
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8232
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8188
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8172
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.8067
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.8013
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8010
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.8003
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7980
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7967
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7935
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7910
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7897
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7875
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7855
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7849
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7817
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7791
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7783
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7781
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7777
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7775
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7775
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7764
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	3	0.7764
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7752
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7745
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7714
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7701
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7670
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7669
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.7661
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7605
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7604
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7602
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7597
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7590
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7588
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7580
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7577
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7568
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7559
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7558
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7532
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7502
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7490
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7467
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7464
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7452
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7445
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7444
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7414
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7399
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7382
Lactoylglutathione lyase	Q04760	LGUL_HUMAN	Homo sapiens	2	0.7366
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7358
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	2	0.7354
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7350
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7344
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7340
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	2	0.7331
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7323
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7314
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7306
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7302
Casein kinase I isoform gamma-2	P78368	KC1G2_HUMAN	Homo sapiens	3	0.7295
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	2	0.7294
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7289
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7282
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7265
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7250
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7244
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7233
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7213
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7208
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7202
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7190
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7185
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7177
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.7168
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7155
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7152
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7138
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7131
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7124
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7105
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	2	0.7104
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	2	0.7094
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7073
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7073
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7073
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7071
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7069
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7069
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase	P12995	BIOA_ECOLI	Escherichia coli	2	0.7059
Genome polyprotein	P27395	POLG_JAEV1	Japanese encephalitis virus	2	0.7044
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7037
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7024
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7019
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7016
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7006
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7003
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7002
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7002
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7001
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7001
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7000

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