23,24-dihydrocucurbitacin b profile

23,24-dihydrocucurbitacin B: from the leaves of Morierina montana Vieill; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

23,24-dihydrocucurbitacin B : A 23,24-dihydrocucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at position 5; a hydroxy function at C-25 is acetylated. [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]

Related Flora

Flora	Rank	Flora Definition	Family	Family Definition
Morierina	genus	[no description available]	Rubiaceae	The Madder plant family of the order Gentianales (formerly Rubiales), subclass Asteridae, class Magnoliopsida includes important medicinal plants that provide QUININE; IPECAC; and COFFEE. They have opposite leaves and interpetiolar stipules.[MeSH]
Morierina montana	species	[no description available]	Rubiaceae	The Madder plant family of the order Gentianales (formerly Rubiales), subclass Asteridae, class Magnoliopsida includes important medicinal plants that provide QUININE; IPECAC; and COFFEE. They have opposite leaves and interpetiolar stipules.[MeSH]

ID Source	ID
PubMed CID	267250
CHEMBL ID	553851
CHEBI ID	62217
MeSH ID	M0455087

Synonym
dihydrocucurbitacin b
13201-14-4
cucurbitacin b, dihydro-
nsc106401
nsc-106401
23,24-dihydrocucurbitacin b
CHEMBL553851
chebi:62217 ,
[(6r)-6-[(2s,8s,9r,10r,13r,14s,16r,17r)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1h-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxoheptan-2-yl] acetate
25-acetoxy-2beta,16alpha,20-trihydroxy-10alpha-cucurbit-5-ene-3,11,22-trione
2beta,16alpha,20,25-tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9beta,10alpha-lanost-5-en-25-yl acetate
2beta,16alpha,20,25-tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanost-5-ene-3,11,22-trione, 25-acetate
(2s,4r)-2,16beta,20-trihydroxy-9beta,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholest-5-en-25-yl acetate
C20787
(2.beta.,9.beta.,10.alpha.,16.alpha.)-25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-19-norlanost-5-ene-3,11,22-trione
19-norlanost-5-ene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (2.beta.,9.beta.,10.alpha.,16.alpha.)-
AKOS037514506
Q27131690
CS-0032304
HY-N4171
(10alpha)-25-(acetyloxy)-2beta,16alpha,20-trihydroxy-9beta-methyl-19-norlanost-5-ene-3,11,22-trione
MS-30184
DTXSID701314710

Class	Description
23,24-dihydrocucurbitacin	Any cucurbitacin whose C(23)-C(24) double bond has been reduced.
secondary alpha-hydroxy ketone	An alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing one hydrogen and one organyl group. Secondary alpha-hydroxy ketones are also known as acyloins, and are formally derived from reductive coupling of two carboxylic acid groups.
tertiary alpha-hydroxy ketone	An alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing two 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 (19)

Assay ID	Title	Year	Journal	Article
AID1225622	Inhibition of HSP90 in human MCF7 cells assessed as Her2 degradation at 0.5 times to 5 times IC50 after 24 hrs by Western blot analysis	2015	Journal of natural products, Apr-24, Volume: 78, Issue:4	Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID319042	Antiviral activity against HIV1 in C8166 cells after 72 hrs	2008	Journal of natural products, Jan, Volume: 71, Issue:1	Octanorcucurbitane and cucurbitane triterpenoids from the tubers of Hemsleya endecaphylla with HIV-1 inhibitory activity.
AID422394	Inhibition of STAT3 upto 10 uM by Western blotting	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Cucurbitane-type triterpenoids from the stems of Cucumis melo.
AID657121	Cytotoxicity against human A549 cells after 72 hrs by MTT assay	2012	Bioorganic & medicinal chemistry, May-01, Volume: 20, Issue:9	Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives.
AID657120	Cytotoxicity against human A549 cells after 48 hrs by MTT assay	2012	Bioorganic & medicinal chemistry, May-01, Volume: 20, Issue:9	Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives.
AID422391	Cytotoxicity against human A549 cells upto 10 uM after 72 hrs by SRB assay	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Cucurbitane-type triterpenoids from the stems of Cucumis melo.
AID422392	Cytotoxicity against human Bel7402 cells upto 10 uM after 72 hrs by SRB assay	2009	Journal of natural products, May-22, Volume: 72, Issue:5	Cucurbitane-type triterpenoids from the stems of Cucumis melo.
AID1225624	Inhibition of HSP90 in human MCF7 cells assessed as Raf degradation at 0.5 times to 5 times IC50 after 24 hrs by Western blot analysis	2015	Journal of natural products, Apr-24, Volume: 78, Issue:4	Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID1225626	Inhibition of HSP90 in human MCF7 cells assessed as induction of heat shock response-mediated HSP70 production at 0.5 times to 5 times IC50 after 24 hrs by Western blot analysis	2015	Journal of natural products, Apr-24, Volume: 78, Issue:4	Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID1225621	Inhibition of HSP90 in human MCF7 cells assessed as pAkt degradation at 0.5 times to 5 times IC50 after 24 hrs by Western blot analysis	2015	Journal of natural products, Apr-24, Volume: 78, Issue:4	Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID1225605	Cytotoxicity against human MCF7 cells assessed as growth inhibition after 72 hrs by MTS/PMS assay	2015	Journal of natural products, Apr-24, Volume: 78, Issue:4	Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID1386642	Inhibition of AChE (unknown origin) at 10 uM using acetylthiocholine iodide as substrate preincubated for 10 mins followed by substrate addition measured after 10 mins by Ellman's method	2018	Journal of natural products, 09-28, Volume: 81, Issue:9	Colocynthenins A-D, Ring-A seco-Cucurbitane Triterpenoids from the Fruits of Citrullus colocynthis.
AID1225623	Inhibition of HSP90 in human MCF7 cells assessed as Cdk6 degradation at 0.5 times to 5 times IC50 after 24 hrs by Western blot analysis	2015	Journal of natural products, Apr-24, Volume: 78, Issue:4	Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID1683897	Induction of LDR uptake in human HepG2 cells at 5 uM by DIL probe based fluorescence assay	2020	Journal of natural products, 12-24, Volume: 83, Issue:12	Lipid-Lowering Activities of Cucurbitacins Isolated from
AID1225625	Inhibition of HSP90 in human MCF7 cells assessed as induction of heat shock response-mediated HSP90 production at 0.5 times to 5 times IC50 after 24 hrs by Western blot analysis	2015	Journal of natural products, Apr-24, Volume: 78, Issue:4	Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID1225627	Inhibition of HSP90 in human MCF7 cells assessed as induction of heat shock response-mediated HSP27 production at 0.5 times to 5 times IC50 after 24 hrs by Western blot analysis	2015	Journal of natural products, Apr-24, Volume: 78, Issue:4	Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.
AID319043	Cytotoxicity against human C8166 cells by MTT method	2008	Journal of natural products, Jan, Volume: 71, Issue:1	Octanorcucurbitane and cucurbitane triterpenoids from the tubers of Hemsleya endecaphylla with HIV-1 inhibitory activity.
AID657122	Ratio of IC50 for human A549 cells after 48 hrs to IC50 for human A549 cells after 72 hrs	2012	Bioorganic & medicinal chemistry, May-01, Volume: 20, Issue:9	Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives.
AID319044	Selectivity index, ratio of CC50 for human C8166 cells to EC50 for HIV1	2008	Journal of natural products, Jan, Volume: 71, Issue:1	Octanorcucurbitane and cucurbitane triterpenoids from the tubers of Hemsleya endecaphylla with HIV-1 inhibitory activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	11 (68.75)	29.6817
2010's	3 (18.75)	24.3611
2020's	2 (12.50)	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	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	16 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.03	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.03	1	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.02	1	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	2.04	1	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
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).	2.07	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
cucurbitacins [no description available]	2.02	1	11-oxo steroid
celastrol [no description available]	2.11	1	monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory drug; antineoplastic agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Hsp90 inhibitor; metabolite
cucurbitacin r cucurbitacin R: from Cayaponia tayuya roots; structure in first source. 23,24-dihydrocucurbitacin D : A 23,24-dihydrocucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at position 5.	2.77	3	23,24-dihydrocucurbitacin; secondary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone
huperzine a [no description available]	2.17	1	organic heterotricyclic compound; primary amino compound; pyridone; sesquiterpene alkaloid	EC 3.1.1.7 (acetylcholinesterase) inhibitor; neuroprotective agent; nootropic agent; plant metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.44	2	prostaglandins E	human metabolite; mouse metabolite; oxytocic
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	2.43	2	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
cucurbitacin b [no description available]	3	4	cucurbitacin; secondary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone
cucurbitacin d cucurbitacin D: toxic constituent in edible gourd; see also records for cucurbitacins & specific cucurbitacins. cucurbitacin D : A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 5 and 23.	2.11	1	cucurbitacin; secondary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone
nsc 106399 cucurbitacin E: RN refers to (9beta,10alpha,16alpha,23E)-isomer; structure given in first source. cucurbitacin E : A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 1, 5 and 23.	2.77	3	cucurbitacin; tertiary alpha-hydroxy ketone
cucurbitacin i cucurbitacin I: toxic constituent in edible gourd; see also records for cucurbitacins & specific cucurbitacins. cucurbitacin I : A cucurbitacin that is 9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene substituted by hydroxy groups at positions 2, 16, 20 and 25 and oxo groups at positions 1, 11 and 22.	3	4	cucurbitacin; tertiary alpha-hydroxy ketone	antineoplastic agent; plant metabolite
geldanamycin [no description available]	2.11	1	1,4-benzoquinones; ansamycin; carbamate ester; organic heterobicyclic compound	antimicrobial agent; antineoplastic agent; antiviral agent; cysteine protease inhibitor; Hsp90 inhibitor
gedunin [no description available]	2.11	1	acetate ester; enone; epoxide; furans; lactone; limonoid; organic heteropentacyclic compound; pentacyclic triterpenoid	antimalarial; antineoplastic agent; Hsp90 inhibitor; plant metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.03	1
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	2.03	1

Condition	Relationship Strength	Studies
Benign Neoplasms [description not available]	2.11	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.11	1
Elevated Cholesterol [description not available]	2.25	1
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	2.25	1
B16 Melanoma [description not available]	2.05	1
Metastase [description not available]	2.05	1
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.05	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.03	1
Delayed Hypersensitivity [description not available]	2.03	1
Innate Inflammatory Response [description not available]	2.03	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.	2.03	1
Cancer of Colon [description not available]	2.04	1
Colonic Neoplasms Tumors or cancer of the COLON.	2.04	1
Anasarca [description not available]	2.43	2
Ache [description not available]	2.43	2
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.43	2
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.43	2
Adjuvant Arthritis [description not available]	2.03	1
Pleurisy INFLAMMATION of PLEURA, the lining of the LUNG. When PARIETAL PLEURA is involved, there is pleuritic CHEST PAIN.	2.03	1
Breast Cancer [description not available]	7.03	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.03	1
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.03	1

23,24-dihydrocucurbitacin b

Description

Cross-References

Synonyms (23)

Drug Classes (3)

Bioassays (19)

Research

Studies (16)

Market Indicators

Research Demand Index: 11.53

Study Types

23,24-dihydrocucurbitacin b

Description

Related Flora

Cross-References

Synonyms (23)

Drug Classes (3)

Bioassays (19)

Research

Studies (16)

Market Indicators

Research Demand Index: 11.53

Study Types

Related Drugs (19)

Related Conditions (22)