Showing Compound Aucubin (FDB015466)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:51 UTC

Update date

2019-11-26 03:11:37 UTC

Primary ID

FDB015466

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Aucubin

Description

Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety.; Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally.; Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis.; The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1.

CAS Number

479-98-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Aucuboside	HMDB
Rhimantin	HMDB
Rhinanthin	HMDB
Aucubin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	50 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.2	ChemAxon
logS	-0.84	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	149.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.18 m³·mol⁻¹	ChemAxon
Polarizability	33.65 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H22O9

IUPAC name

2-{[5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

InChI Identifier

InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2

InChI Key

RJWJHRPNHPHBRN-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O

Average Molecular Weight

346.3298

Monoisotopic Molecular Weight

346.126382302

Classification

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 52.02%; H 6.40%; O 41.58%	DFC
Melting Point	Mp 181°	DFC
Boiling Point	Not Available
Experimental Water Solubility	356 mg/mL at 20 oC	BEILSTEIN
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]21D -171.4 (H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Aucubin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00or-4719000000-a03c5ea19b82d7991f35	Spectrum
Predicted GC-MS	Aucubin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01b9-2252049000-fb4fdbe14aa2fef93db3	Spectrum
Predicted GC-MS	Aucubin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02vr-0904000000-0dc8cc1fee5ec1d7b66a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0901000000-23ae99445d0f902ebb10	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1900000000-0197bf91c00175908c8f	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00nb-0917000000-5b5a2c303dee5ed5b778	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0159-1901000000-dcbc777e43693cc64c6f	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-5900000000-66eed55623a37e730cdc	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0209000000-6d1f85d0258419cba6e0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-005a-5925000000-7b6e750efe6aab6eda8d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uxr-6910000000-9a98e60322aa35e884b0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00mk-0709000000-9b62837c71245c712dd9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-0901000000-8bd04921ef01bfdb1bb4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-07bs-4900000000-1f7344e04d4a474d0b71	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

308989

ChEMBL ID

Not Available

KEGG Compound ID

C09771

Pubchem Compound ID

348157

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36562

CRC / DFC (Dictionary of Food Compounds) ID

KCL41-H:KCL37-K

EAFUS ID

Not Available

Dr. Duke ID

AUCUBIN

BIGG ID

Not Available

KNApSAcK ID

C00003073

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Aucubin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Antidote	50247	An agent that counteracts a poison or toxin, neutralizing its harmful effects. It plays a biological role in reversing toxicity, and has therapeutic applications in treating poisoning, overdose, and envenomation. Key medical uses include emergency treatment for snake bites, drug overdose, and chemical exposure.	DUKE
Anti-edemic		An agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti leukemic	35610	An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti prolactin		An agent that inhibits prolactin production, a hormone regulating lactation and reproductive processes. Therapeutically, it's used to treat hyperprolactinemia, prolactinomas, and associated disorders, such as galactorrhea, infertility, and menstrual irregularities.	DUKE
Anti-staphylococcic	33282	An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.	DUKE
Candidicide		An agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.	DUKE
Cathartic	75325	An agent that induces bowel movements, relieving constipation by stimulating intestinal motility. Its biological role is to increase water and electrolyte secretion in the gut. Therapeutically, cathartics are used to treat constipation, prepare the bowel for surgery or exams, and manage opioid-induced constipation. Key medical uses include laxative therapy and colonoscopy preparation.	DUKE
Collagenic		An agent that stimulates collagen production, the primary protein in connective tissue, promoting tissue repair and regeneration. It has therapeutic applications in wound healing, orthopedics, and dermatology, with key medical uses including skin rejuvenation, joint health, and bone fracture repair.	DUKE
Diuretic	35498	An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.	DUKE
Hepatoprotective	62868	An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.	DUKE
Lactagogue		An agent that stimulates milk production, aiding breastfeeding. It promotes lactation, commonly used to treat low milk supply, and supports maternal health in postpartum care.	DUKE
Laxative	50503	An agent that stimulates bowel movements, relieving constipation by softening stool or increasing intestinal motility. Therapeutically, laxatives are used to treat constipation, prepare the bowel for medical procedures, and manage certain medical conditions, such as irritable bowel syndrome.	DUKE
Paralytic		An agent that induces temporary paralysis or muscle relaxation, used therapeutically to facilitate surgical procedures, manage muscle spasms, and treat conditions like tetanus and seizures, by blocking nerve transmission to muscles.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
RNA inhibitor	35222	An agent that blocks RNA function, reducing gene expression. It has therapeutic applications in treating viral infections, cancer, and genetic disorders, with key medical uses including antiviral therapy and oncology treatments.	DUKE
Uricosuric		A substance that increases uric acid excretion in the urine, reducing blood plasma concentration. It plays a biological role in preventing uric acid buildup. Therapeutically, it's used to treat gout and hyperuricemia, managing symptoms and preventing complications. Key medical uses include reducing uric acid levels and alleviating gout attacks.	DUKE