benzoylaconine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

benzoylaconine: alkaloid isolated from Aconitum carmichaeli [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

benzoylaconine : A diterpene alkaloid with formula C32H45NO10 that is isolated from several Aconitum species. [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]

Flora	Rank	Flora Definition	Family	Family Definition
Aconitum	genus	A plant genus of the family RANUNCULACEAE. Members contain a number of diterpenoid alkaloids including: aconitans, hypaconitine, ACONITINE, jesaconitine, ignavine, napelline, and mesaconitine. The common name of Wolfbane is similar to the common name for ARNICA.[MeSH]	Ranunculaceae	The buttercup plant family of the order RANUNCULALES, class MAGNOLIOPSIDA. The leaves are usually alternate and stalkless. The flowers usually have two to five free sepals and may be radially symmetrical or irregular.[MeSH]

Cross-References

ID Source	ID
PubMed CID	20055771
CHEMBL ID	2062825
CHEBI ID	132633
SCHEMBL ID	2977326
MeSH ID	M0136695

Synonyms (15)

Synonym
picraconitine
benzoylaconine
isaconitine
aconine benzoate
CHEBI:132633
14-o-benzoylaconine
(1alpha,3alpha,6alpha,14alpha,15alpha,16beta)-20-ethyl-3,8,13,15-tetrahydroxy-1,6,16-trimethoxy-4-(methoxymethyl)aconitan-14-yl benzoate
aconine 14-benzoate
14-benzoylaconine
466-24-0
20-ethyl-3alpha,8,13,15alpha-tetrahydroxy-1alpha,6alpha,16beta-trimethoxy-4-(methoxymethyl)aconitan-14alpha-yl benzoate
CHEMBL2062825
benzoylaconitine
SCHEMBL2977326
[(1s,2r,3r,4r,5r,6s,7s,8r,9r,13r,14r,16s,17s,18r)-11-ethyl-5,7,8,14-tetrahydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate

Research Excerpts

Pharmacokinetics

Excerpt	Reference	Relevance
" The validated method was employed to simultaneous quantitation and successfully used for the first time for the pharmacokinetic evaluation of the six Aconitum alkaloids after intravenous drop administration of "SHEN-FU" injectable powder in phase I clinical trial."	( Simultaneous quantitation of aconitine, mesaconitine, hypaconitine, benzoylaconine, benzoylmesaconine and benzoylhypaconine in human plasma by liquid chromatography-tandem mass spectrometry and pharmacokinetics evaluation of "SHEN-FU" injectable powder. Chen, LJ; Duan, JG; Li, R; Tang, MH; Wang, XH; Wei, YQ; Zhang, F; Zhao, X, 2008)	0.58
"05), while T1/2, AUC0-t and Cmax of BAC, BHA increased (P<0."	( The effects of Rhizoma Zingiberis on pharmacokinetics of six Aconitum alkaloids in herb couple of Radix Aconiti Lateralis-Rhizoma Zingiberis. Cai, BC; Cui, XB; Li, JS; Li, W; Peng, WW; Wen, HM; Yang, GM; Zhang, YX, 2013)	0.39
" Compared with single-herb extracts, alkaloids in plasma (except methylephedrine, benzoylmesaconine and benzoylhypaconine) showed slower elimination (the mean residence time or half-life was longer), although the maximum plasma concentration and area under the plasma concentration curve values decreased."	( Simultaneous quantification and pharmacokinetics of alkaloids in Herba Ephedrae-Radix Aconiti Lateralis extracts. Huo, H; Li, H; Luo, J; Song, S; Tang, Q; Xing, X, )	0.13

Compound-Compound Interactions

Excerpt	Reference	Relevance
" The potential risk of drug-drug interactions (DDIs) arising from co-administration of Aconitum alkaloids and other drugs against specific targets such as P-glycoprotein (P-gp) must be evaluated."	( Induction of P-glycoprotein expression and activity by Aconitum alkaloids: Implication for clinical drug-drug interactions. Feng, L; He, S; Li, F; Li, N; Lin, N; Liu, L; Liu, S; Liu, Z; Lu, L; Ou, R; Wu, J; Zhang, G; Zhu, Y, 2016)	0.43

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

Role	Description
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
phytotoxin	Any toxin produced by a plant.
[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]

Drug Classes (9)

Class	Description
benzoate ester	Esters of benzoic acid or substituted benzoic acids.
bridged compound	A polycyclic compound in which two rings have two or more atoms in common.
diterpene alkaloid
organic heteropolycyclic compound
polyether	Any ether that contains more than one ether linkage.
secondary alcohol	A secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
tertiary alcohol	A tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
tetrol	A polyol that contains 4 hydroxy groups.
tertiary amino compound	A compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups.
[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]

Bioassays (10)

Assay ID	Title	Year	Journal	Article
AID676146	Antiinflammatory activity in mouse peritoneal macrophages assessed as inhibition of nitric oxide production at 10 uM	2012	Journal of natural products, Jun-22, Volume: 75, Issue:6	Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii.
AID676148	Cytotoxicity against human A549 cells at 10 uM after 96 hrs by MTT assay	2012	Journal of natural products, Jun-22, Volume: 75, Issue:6	Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii.
AID676145	Hepatoprotective activity against DL-galactosamine-induced cell death in rat WB-F344 cells at 10 uM incubated for 1 hr prior to DL-galactosamine-challenge measured after 24 hrs by MTT assay	2012	Journal of natural products, Jun-22, Volume: 75, Issue:6	Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii.
AID676144	Antioxidant activity in rat liver microsome assessed as inhibition of FeSO4-induced lipid peroxidation at 10 uM incubated for 15 mins prior to FeSO4-challenge measured after 15 mins by modified thiobarbituric acid method	2012	Journal of natural products, Jun-22, Volume: 75, Issue:6	Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii.
AID676152	Cytotoxicity against human HCT8 cells at 10 uM after 96 hrs by MTT assay	2012	Journal of natural products, Jun-22, Volume: 75, Issue:6	Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii.
AID676150	Cytotoxicity against human Ketr3 cells at 10 uM after 96 hrs by MTT assay	2012	Journal of natural products, Jun-22, Volume: 75, Issue:6	Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii.
AID676147	Cytotoxicity against human BGC823 cells at 10 uM after 96 hrs by MTT assay	2012	Journal of natural products, Jun-22, Volume: 75, Issue:6	Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii.
AID676151	Cytotoxicity against human Bel7402 cells at 10 uM after 96 hrs by MTT assay	2012	Journal of natural products, Jun-22, Volume: 75, Issue:6	Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii.
AID676149	Cytotoxicity against human MCF7 cells at 10 uM after 96 hrs by MTT assay	2012	Journal of natural products, Jun-22, Volume: 75, Issue:6	Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii.
AID676143	Neuroprotective activity against serum starvation-induced cell death in rat PC12 cells assessed as cell viability at 10 uM incubated for 24 hrs prior to serum starvation measured after 24 hrs by MTT assay (Rvb = 55.1+/-4.2%)	2012	Journal of natural products, Jun-22, Volume: 75, Issue:6	Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (3.70)	18.7374
1990's	1 (3.70)	18.2507
2000's	6 (22.22)	29.6817
2010's	14 (51.85)	24.3611
2020's	5 (18.52)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.60

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	23.60 (24.57)
Research Supply Index	3.40 (2.92)
Research Growth Index	5.36 (4.65)
Search Engine Demand Index	23.28 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (23.60)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (3.45%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	28 (96.55%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
jervine jervine: teratogen from Veratrum grandiflorum; RN given refers to parent cpd(3beta,23beta)-isomer; structure	3.18	1	piperidines
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	2.08	1	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2.21	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
imiquimod Imiquimod: A topically-applied aminoquinoline immune modulator that induces interferon production. It is used in the treatment of external genital and perianal warts, superficial CARCINOMA, BASAL CELL; and ACTINIC KERATOSIS.. imiquimod : An imidazoquinoline fused [4,5-c] carrying isobutyl and amino substituents at N-1 and C-4 respectively. A prescription medication, it acts as an immune response modifier and is used to treat genital warts, superficial basal cell carcinoma, and actinic keratosis.	2.6	1	imidazoquinoline	antineoplastic agent; interferon inducer
liquiritigenin liquiritigenin: structure given in first source; isolated from Pterocarpus marsupium. 4',7-dihydroxyflavanone : A dihydroxyflavanone in which the two hydroxy substituents are located at positions 4' and 7.. liquiritigenin : A dihydroxyflavanone compound having the two hydroxy substituents at the 4'- and 7-positions. Isolated from the root of Glycyrrhizae uralensis, it is a selective agonist for oestrogen receptor beta.	2.08	1	4',7-dihydroxyflavanone	hormone agonist; plant metabolite
atractylenolide iii atractylenolide III: from Atractylodes macrocephala Koidz; structure in first source	2.08	1	naphthofuran	metabolite
aconine aconine: alkaloid isolated from Aconitum carmichaeli; structure in Merck. aconine : A diterpene alkaloid with formula C25H41NO9 that is isolated from several Aconitum species.	3.66	9
cyclopamine [no description available]	3.18	1	piperidines	glioma-associated oncogene inhibitor
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.08	1	cinnamic acid	plant metabolite
sesquiterpenes [no description available]	2.08	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.	2.08	1	cinnamate ester; tannin	food component; plant metabolite
napelline napelline: RN given for (1alpha,12alpha,15beta)-isomer; structure in first source	2.17	1	kaurane diterpenoid
atractylenolide i atractylenolide I: from Atractylodes macrocephala Koidz; structure in first source	2.08	1
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2.01	1	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
songorine songorine: RN given refers to parent cpd; diterpene alkaloid from Aconitum karakolicum Rap.	2.69	2
hypaconitine hypaconitine: RN given refers to the (1alpha,6alpha,14alpha,15alpha,16beta)-isomer	7.98	4
benzoylhypaconine benzoylhypaconine: Aconitum alkaloid in serum. benzoylhypaconine : A diterpene alkaloid with formula C31H43NO9 that is isolated from several Aconitum species.	8.15	5
deoxyaconitine deoxyaconitine: diterpene alkaloid from Aconitum karakolicum Rap.. deoxyaconitine : A diterpene alkaloid with formula C34H47NO10 that is isolated from several Aconitum species.	2.07	1	acetate ester; benzoate ester; bridged compound; diol; diterpene alkaloid; organic heteropolycyclic compound; polyether; secondary alcohol; tertiary amino compound	plant metabolite
benzoylmesaconine benzoylmesaconine: structure in first source. benzoylmesaconine : A diterpene alkaloid with formula C31H43NO10 that is isolated from several Aconitum species.	8.59	8	benzoate ester; bridged compound; diterpene alkaloid; organic heteropolycyclic compound; polyether; secondary alcohol; tertiary alcohol; tertiary amino compound; tetrol	analgesic; antiinfective agent; plant metabolite
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.25	1
denudatine [no description available]	2.17	1
neoline neoline: Aconitum jaluense; structure in first source. neoline : A diterpene alkaloid with formula C24H39NO6 that is isolated from several Aconitum species.	2.94	3
tridihexethyl mesaconitine: RN given refers to parent cpd(1alpha,3alpha,6alpha,14alpha,15alpha,16beta)-isomer	3.02	4
talatisamine talatisamine: diterpenoid alkaloids found in folk medicine caowu; RN given refers to ((1alpha,14alpha,16beta)-isomer); RN for cpd without isomeric designation not avail 8/91	2.17	1
aconitine Aconitine: A C19 norditerpenoid alkaloid (DITERPENES) from the root of ACONITUM; DELPHINIUM and larkspurs. It activates VOLTAGE-GATED SODIUM CHANNELS. It has been used to induce ARRHYTHMIAS in experimental animals and it has anti-inflammatory and anti-neuralgic properties.. aconitine : A diterpenoid that is 20-ethyl-3alpha,13,15alpha-trihydroxy-1alpha,6alpha,16beta-trimethoxy-4-(methoxymethyl)aconitane-8,14alpha-diol having acetate and benzoate groups at the 8- and 14-positions respectively.	5.73	25
isotalatizidine isotalatizidine: structure in first source. isotalatizidine : A diterpene alkaloid that is aconitane bearing hydroxy groups at the 1alpha, 8, and 14alpha positions and substituted at on the nitrogen and at positions 4 and 16beta by ethyl, methoxymethyl, and methoxy groups, respectively.	2.6	1

Condition	Relationship Strength	Studies
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.6	1
Palmoplantaris Pustulosis [description not available]	2.6	1
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	2.6	1
Rheumatoid Arthritis [description not available]	2.25	1
Synovioma [description not available]	2.25	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.25	1
Sarcoma, Synovial A malignant neoplasm arising from tenosynovial tissue of the joints and in synovial cells of tendons and bursae. The legs are the most common site, but the tumor can occur in the abdominal wall and other trunk muscles. There are two recognized types: the monophasic (characterized by sheaths of monotonous spindle cells) and the biphasic (characterized by slit-like spaces or clefts within the tumor, lined by cuboidal or tall columnar epithelial cells). These sarcomas occur most commonly in the second and fourth decades of life. (From Dorland, 27th ed; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1363)	2.25	1
Anasarca [description not available]	2.25	1
Innate Inflammatory Response [description not available]	2.25	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.25	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.25	1
Peripheral Nerve Injury [description not available]	2.21	1
Allodynia [description not available]	2.21	1
Nerve Pain [description not available]	2.21	1
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.21	1
Peripheral Nerve Injuries Injuries to the PERIPHERAL NERVES.	2.21	1
Plant Poisoning Poisoning by the ingestion of plants or its leaves, berries, roots or stalks. The manifestations in both humans and animals vary in severity from mild to life threatening. In animals, especially domestic animals, it is usually the result of ingesting moldy or fermented forage.	3	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.04	1
Arrhythmia [description not available]	2.02	1
Gagging Contraction of the muscle of the PHARYNX caused by stimulation of sensory receptors on the SOFT PALATE, by psychic stimuli, or systemically by drugs.	2.02	1
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	2.02	1

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