Loganic Acid

Details

• Internal ID: 085051c1-fc59-4eb6-9227-6b0f3cba52b1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• InChI: InChI=1S/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6+,8-,9+,10+,11+,12-,13+,15-,16-/m0/s1
• InChI Key: JNNGEAWILNVFFD-CDJYTOATSA-N
• Popularity: 326 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₁₀
• Molecular Weight: 376.36 g/mol
• Exact Mass: 376.13694696 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.24
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 22255-40-9
• UX3J3KK2UG
• CHEBI:30632
• (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• DTXSID80944913
• (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta(c)pyran-4-carboxylic acid
• (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-1,4a,5,6,7,7a-hexahydrocyclopenta(c)pyran-4-carboxylic acid
• RefChem:153948
• DTXCID801373242
• 244-875-9
• MFCD00017417
• C16H24O10
• (1S,4aS,6S,7R,7aS)-6-Hydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• Loganic-acid
• Loganin acid
• EINECS 244-875-9
• Spectrum_001509
• SpecPlus_000543
• Loganic acid (Standard)
• Spectrum2_001971
• Spectrum3_001930
• Spectrum4_001690
• Spectrum5_000340
• UNII-UX3J3KK2UG
• BSPBio_003530
• KBioGR_001960
• KBioSS_001989
• DivK1c_006639
• SCHEMBL308008
• SPECTRUM1504071
• SPBio_002121
• orb1300215
• CHEMBL1081585
• HY-N0513R
• KBio1_001583
• KBio2_001989
• KBio2_004557
• KBio2_007125
• KBio3_002760
• JNNGEAWILNVFFD-CDJYTOATSA-N
• HY-N0513
• CCG-39437
• AKOS032962058
• FL65690
• SDCCGMLS-0066805.P001
• Loganic acid, >=95% (LC/MS-ELSD)
• NCGC00178007-01
• NCGC00178007-02
• MS-26101
• CS-0009052
• S9191
• C01512
• 255L409
• Q19597767
• (1S,4AS,6S,7R,7AS)-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID
• (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxyl
• (1S-(1alpha,4aalpha,6alpha,7alpha,7aalpha))-1-(beta-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta(c)pyran-4-carboxylic acid
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, (1S-(1.ALPHA.,4A.ALPHA.,6.ALPHA.,7.ALPHA.,7A.ALPHA.))-
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A.ALPHA.,5,6,7,7A.ALPHA.-HEXAHYDRO-6.ALPHA.-HYDROXY-7.ALPHA.-METHYL-
• EQV

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7275	72.75%
Caco-2	-	0.8903	89.03%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6384	63.84%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	-	0.7737	77.37%
OATP1B3 inhibitior	+	0.9524	95.24%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9340	93.40%
P-glycoprotein inhibitior	-	0.9070	90.70%
P-glycoprotein substrate	-	0.8694	86.94%
CYP3A4 substrate	+	0.5444	54.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.9398	93.98%
CYP2C9 inhibition	-	0.9222	92.22%
CYP2C19 inhibition	-	0.9125	91.25%
CYP2D6 inhibition	-	0.9058	90.58%
CYP1A2 inhibition	-	0.8383	83.83%
CYP2C8 inhibition	-	0.7895	78.95%
CYP inhibitory promiscuity	-	0.8323	83.23%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7232	72.32%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9601	96.01%
Skin irritation	-	0.7151	71.51%
Skin corrosion	-	0.9453	94.53%
Ames mutagenesis	-	0.5747	57.47%
Human Ether-a-go-go-Related Gene inhibition	-	0.5798	57.98%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7714	77.14%
skin sensitisation	-	0.8822	88.22%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7727	77.27%
Acute Oral Toxicity (c)	III	0.4815	48.15%
Estrogen receptor binding	+	0.5361	53.61%
Androgen receptor binding	-	0.5663	56.63%
Thyroid receptor binding	+	0.5505	55.05%
Glucocorticoid receptor binding	-	0.5314	53.14%
Aromatase binding	+	0.5568	55.68%
PPAR gamma	-	0.4837	48.37%
Honey bee toxicity	-	0.8879	88.79%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.6666	66.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.90%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.68%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.70%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	87.70%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.59%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.44%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.49%	99.17%
CHEMBL4208	P20618	Proteasome component C5	85.22%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.90%	97.25%
CHEMBL2581	P07339	Cathepsin D	83.57%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.62%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.57%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.48%	95.56%
CHEMBL1811	P34995	Prostanoid EP1 receptor	80.16%	95.71%

Plants that contains it

• Acacia aulacocarpa
• Alangium platanifolium
• Alangium premnifolium
• Anemonastrum flaccidum
• Ardisia neriifolia
• Aspidosperma subincanum
• Blumenbachia insignis
• Catharanthus roseus
• Cephalaria procera
• Cornus officinalis
• Cryptocarya aschersoniana
• Desfontainia spinosa
• Dipsacus asperoides
• Dipsacus inermis
• Eupatorium argentinum
• Fagraea auriculata
• Fontanesia fortunei
• Garcinia madruno
• Gentiana crassa subsp. rigescens
• Gentiana crassicaulis
• Gentiana dahurica
• Gentiana lutea
• Gentiana macrophylla
• Gentiana manshurica
• Gentiana olivieri
• Gentiana pedicellata
• Gentiana scabra
• Gentiana septemfida
• Gentiana straminea
• Gentiana thunbergii
• Gentiana tibetica
• Gentiana triflora
• Guatteria ucayalina
• Guettarda platypoda
• Guettarda speciosa
• Ixanthus viscosus
• Juniperus brevifolia
• Lippia origanoides
• Lomelosia variifolia
• Lonicera caerulea
• Lonicera japonica
• Lonicera periclymenum
• Ophiorrhiza kuroiwai
• Patrinia scabra
• Pedicularis longiflora
• Pedicularis torta
• Penstemon barbatus
• Peritassa compta
• Picconia excelsa
• Psiadia dentata
• Rauvolfia grandiflora
• Scaevola racemigera
• Scutellaria lateriflora
• Simira williamsii
• Strychnos axillaris
• Strychnos cocculoides
• Strychnos lucida
• Strychnos nux-vomica
• Tripterospermum trinervium
• Vinca major

Cross-Links

• PubChem: 89640
• NPASS: NPC287539
• LOTUS: LTS0231203
• wikiData: Q19597767