Showing Compound Acteoside (FDB013409)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:41 UTC

Update date

2019-11-26 03:08:23 UTC

Primary ID

FDB013409

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Acteoside

Description

Acteoside belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a significant number of articles have been published on Acteoside.

CAS Number

61276-17-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Kusaginin	HMDB
Verbascoside	HMDB
6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator
Acteoside	MeSH

Predicted Properties

Property	Value	Source
Water Solubility	0.97 g/L	ALOGPS
logP	1.09	ALOGPS
logP	0.82	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.01	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	245.29 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	148.4 m³·mol⁻¹	ChemAxon
Polarizability	61.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C29H36O15

IUPAC name

6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

InChI Identifier

InChI=1S/C29H36O15/c1-13-22(36)23(37)24(38)29(41-13)44-27-25(39)28(40-9-8-15-3-6-17(32)19(34)11-15)42-20(12-30)26(27)43-21(35)7-4-14-2-5-16(31)18(33)10-14/h2-7,10-11,13,20,22-34,36-39H,8-9,12H2,1H3/b7-4+

InChI Key

FBSKJMQYURKNSU-QPJJXVBHSA-N

Isomeric SMILES

CC1OC(OC2C(O)C(OCCC3=CC(O)=C(O)C=C3)OC(CO)C2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C(O)C(O)C1O

Average Molecular Weight

624.5871

Monoisotopic Molecular Weight

624.205420482

Classification

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
12-hydroxysteroid
Hydroxysteroid
Steroid
Fatty acid ester
Fatty acyl
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Cucurbitaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 55.77%; H 5.81%; O 38.42%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -84.9 (c, 1.15 in MeOH)	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	Acteoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0c01-8920533000-c097428fe1e65a0969d1	Spectrum
Predicted GC-MS	Acteoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00gv-9700035000-c5b8ef4573cf92ca120f	Spectrum
Predicted GC-MS	Acteoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Acteoside, TMS_2_15, 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	splash10-06vi-0610905000-d3e010321fe0d919d876	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08g0-0902400000-dd983ed069c1287efa62	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-07vs-0936300000-3704d6fa7e12bff5166c	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-024i-1711907000-8d66cf1f56e75f6558ad	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ta-1931400000-86ecba3eeab93093ef6c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-2912000000-635e9beb27d765412134	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0570-0901305000-40ef60910d55528838e9	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dr-0901400000-fe1d9b802f028f7ea31c	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-3900000000-bc1225604dad02608b43	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-0900326000-747bb65451dcebe8e624	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052k-2932361000-4483352c20c5b4367f6b	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1921010000-240b10f30c5ca197eb79	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4572852

ChEMBL ID

Not Available

KEGG Compound ID

C10501

Pubchem Compound ID

5459010

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

468

DrugBank ID

Not Available

HMDB ID

HMDB34843

CRC / DFC (Dictionary of Food Compounds) ID

DVR38-T:HWS46-Y

EAFUS ID

Not Available

Dr. Duke ID

VERBASCOSIDE

BIGG ID

Not Available

KNApSAcK ID

C00002783

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

Not Available

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
Aldose reductase inhibitor	48550	An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Analgesic	35480	An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.	DUKE
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
Anti feedant		A substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.	DUKE
Anti hepatotoxic	62868	An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.	DUKE
Anti hypertensive	52217	An agent that lowers blood pressure, reducing the risk of cardiovascular disease. It plays a biological role in relaxing blood vessels, decreasing cardiac workload, and improving blood flow. Therapeutically, it's used to manage hypertension, heart failure, and stroke, with key medical applications in preventing organ damage and improving overall cardiovascular health.	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 septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Anti-staph		An antimicrobial agent that targets Staphylococcus bacteria, reducing Staph infections. Therapeutically, it's used to treat skin, respiratory, and bloodstream infections, and to prevent MRSA (methicillin-resistant Staphylococcus aureus) infections.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Cytotoxic	52209	An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Hypertensive		An agent that increases blood pressure, used therapeutically to treat hypotension (low blood pressure) and shock, and medically to manage conditions such as orthostatic hypotension and postural hypotension.	DUKE
Immunosuppressant	35705	An agent that suppresses the immune system, reducing inflammation and preventing rejection in organ transplants, and treating autoimmune diseases such as rheumatoid arthritis and lupus.	DUKE
Lipoxygenase inhibitor	35856	An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.	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
Phytoalexin	26115	A plant-derived compound that plays a biological role in defense against pathogens. It has therapeutic applications as an antimicrobial, antioxidant, and anti-inflammatory agent, with key medical uses in managing infections, cancer, and neurodegenerative diseases.	DUKE
Protein kinase C inhibitor	37700	An agent that blocks protein kinase C activity, reducing cell signaling and inflammation. Therapeutically, it's used to treat cancer, cardiovascular diseases, and neurological disorders, with key medical applications in managing Alzheimer's disease, diabetes, and stroke.	DUKE