secologanin profile

(-)-secologanin : An iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2S,3R,4S stereoisomer). [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	161276
CHEMBL ID	1235867
CHEBI ID	18002
SCHEMBL ID	431171
MeSH ID	M0075548

Synonym
CHEMBL1235867
CHEBI:18002 ,
methyl (2s,3r,4s)-3-ethenyl-2-(beta-d-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2h-pyran-5-carboxylate
methyl (2s,3r,4s)-4-(formylmethyl)-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2h-pyran-5-carboxylate
methyl (2s,3r,4s)-2-(beta-d-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2h-pyran-5-carboxylate
nsc-640525
secologanin
(-)-secologanin
C01852
19351-63-4
LMPR0102070002
F19BE380-C97E-46CC-89C6-F6BCAFC793EC
loniceroside
methyl (2s,3r,4s)-3-ethenyl-4-(2-oxoethyl)-2-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2h-pyran-5-carboxylate
3-ethenyl-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2h-pyran-5-carboxylic acid, methyl ester
unii-nk7b26k93t
nk7b26k93t ,
SCHEMBL431171
secologanin, analytical standard
HY-125598
CS-0092439
J-012529
ncgc00384550-01_c17h24o10_methyl (2s,3r,4s)-2-(beta-d-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2h-pyran-5-carboxylate
NCGC00384550-01
tert-butyl 3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4,5-dihydro-1,2-oxazole-3-carbonyl]amino]butanoate
DTXSID30941033
Q1531155
MS-26429
loniceroside (iridoid)
2h-pyran-5-carboxylic acid, 3-ethenyl-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-, methyl ester, (2s,3r,4s)-
AKOS040753996

Excerpt	Reference	Relevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51

Role	Description
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
pyrans
beta-D-glucoside	Any D-glucoside in which the anomeric centre has beta-configuration.
methyl ester	Any carboxylic ester resulting from the formal condensation of a carboxy group with methanol.
aldehyde	A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.
enoate ester	An alpha,beta-unsaturated carboxylic ester of general formula R(1)R(2)C=CR(3)-C(=O)OR(4) (R(4) =/= H) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.
secoiridoid glycoside	A glycoside of any secoiridoid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
Indole Alkaloid Biosynthesis	3	11
secologanin and strictosidine biosynthesis	3	32
emetine biosynthesis	5	15
vindoline, vindorosine and vinblastine biosynthesis	2	40
secologanin and strictosidine biosynthesis	13	36
vindoline and vinblastine biosynthesis	6	35
emetine biosynthesis	5	20
Secologanin and strictosidine biosynthesis	0	15

Assay ID	Title	Year	Journal	Article
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159	Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160	Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID730648	Binding affinity to recombinant Hsp90 alpha (unknown origin) by surface plasmon resonance	2013	Journal of medicinal chemistry, Feb-28, Volume: 56, Issue:4	A chemical-biological study reveals C9-type iridoids as novel heat shock protein 90 (Hsp90) inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (4.44)	18.7374
1990's	2 (4.44)	18.2507
2000's	16 (35.56)	29.6817
2010's	19 (42.22)	24.3611
2020's	6 (13.33)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (4.35%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	44 (95.65%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	2	1	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
histamine [no description available]	7.01	1	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
tryptamine [no description available]	9.83	10	aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines	human metabolite; mouse metabolite; plant metabolite
isopentenyl pyrophosphate isopentenyl pyrophosphate: substrate for isopentenyl pyrophosphate isomerase; RN given refers to unlabeled cpd; a nonpeptide mycobacterial antigen that stimulates gamma delta T cells. isopentenyl diphosphate : A prenol phosphate comprising 3-methylbut-3-en-1-ol having an O-diphosphate substituent.	1.99	1	prenol phosphate	antigen; antioxidant; epitope; Escherichia coli metabolite; mouse metabolite; phosphoantigen
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	1.98	1	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	2.15	1	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.07	1	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.53	2	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	3.32	6	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	2.13	1
yohimbine Yohimbine: A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.. yohimbine : An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.	1.98	1	methyl 17-hydroxy-20xi-yohimban-16-carboxylate	alpha-adrenergic antagonist; dopamine receptor D2 antagonist; serotonergic antagonist
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.17	1	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
kynuramine Kynuramine: An aromatic ketone containing the aniline structure (ANILINE COMPOUNDS).. kynuramine : A member of the class of kynurenamines that is aniline substituted at position 2 by a 3-aminopropanoyl group.	2.15	1	kynurenamines; primary amino compound	metabolite
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.75	3	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	3.12	1
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.17	1	benzenes; phenyl acetates
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	4.34	6	D-glucopyranose	epitope; mouse metabolite
loganin [no description available]	4.51	7	beta-D-glucoside; cyclopentapyran; enoate ester; iridoid monoterpenoid; methyl ester; monosaccharide derivative; secondary alcohol	anti-inflammatory agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; EC 3.4.23.46 (memapsin 2) inhibitor; neuroprotective agent; plant metabolite
loganic acid loganic acid: structure. loganic acid : A cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1, 6 and 7 by beta-D-glucosyloxy, hydroxy and methyl groups respectively	2.41	2	alpha,beta-unsaturated monocarboxylic acid; cyclopentapyran; glucoside	plant metabolite
catalposide [no description available]	2.08	1
sweroside [no description available]	2.51	2	glycoside
strictosidine [no description available]	9.62	8	alkaloid ester; beta-D-glucoside; indole alkaloid; methyl ester
secoxyloganin secoxyloganin: from Guettarda playpoda. secoxyloganin : A secoiridoid glycoside that is [(2R,3R,4S)-2-hydroxy-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]acetic acid in which the anometric hydroxy group has been converted to the corresponding beta-D-glucoside. It has been isolated from several plant species and exhibits antioxidant and anti-allergic properties.	7.52	2	beta-D-glucoside; dicarboxylic acid monoester; enoate ester; methyl ester; monosaccharide derivative; pyrans; secoiridoid glycoside	anti-allergic agent; antioxidant; plant metabolite
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	6.24	26
shikonin shikonin: a naphthazarin; has antineoplastic and angiogenesis inhibiting activities	3.12	1	hydroxy-1,4-naphthoquinone
glycosides [no description available]	2.01	1
sesquiterpenes [no description available]	2.15	1
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.13	1	cinnamate ester; tannin	food component; plant metabolite
nadp [no description available]	2	1
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	3.12	1
xylulose [no description available]	2.03	1	xylulose	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
catharanthine [no description available]	2.46	2	alkaloid ester; bridged compound; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound
monorden monorden: inhibits HSP90 Heat-Shock Proteins, DNA topoisomerase VI and human Topoisomerase II	2.08	1	cyclic ketone; enone; epoxide; macrolide antibiotic; monochlorobenzenes; phenols	antifungal agent; metabolite; tyrosine kinase inhibitor
raubasine raubasine: RN given refers to (19alpha)-isomer; structure	1.98	1	yohimban alkaloid
methyl chlorogenate methyl chlorogenate: from Eriobotrya japonica; structure in first source	2.13	1	quinic acid
tanespimycin CP 127374: analog of herbimycin A	2.08	1	1,4-benzoquinones; ansamycin; carbamate ester; organic heterobicyclic compound; secondary amino compound	antineoplastic agent; apoptosis inducer; Hsp90 inhibitor
6-o-coumaroylcatalpol [no description available]	2.08	1	cinnamate ester
vindoline [no description available]	2.04	1
6-O-feruloylcatalpol [no description available]	2.08	1	hydroxycinnamic acid	metabolite
methyl jasmonate [no description available]	2.17	1

Condition	Relationship Strength	Studies
Congenital Zika Syndrome [description not available]	2.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.25	1
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.25	1

secologanin

Description

Cross-References

Synonyms (31)

Research Excerpts

Bioavailability

Roles (1)

Drug Classes (6)

Pathways (5)

Bioassays (6)

Research

Studies (45)

Market Indicators

Research Demand Index: 35.02

Study Types