hemiasterlin

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

Description

hemiasterlin: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	5352092
CHEMBL ID	185151
SCHEMBL ID	57313
MeSH ID	M0440841

Synonyms (17)

Synonym
nsc-695242
NSC695242 ,
hemiasterlin
CHEMBL185151
(e,4s)-4-[[(2s)-3,3-dimethyl-2-[[(2s)-3-methyl-2-(methylamino)-3-(1-methylindol-3-yl)butanoyl]amino]butanoyl]-methylamino]-2,5-dimethylhex-2-enoic acid
milnamide b
l-valinamide, n,beta,beta,1-tetramethyl-l-tryptophyl-n-((1s,2e)-3-carboxy-1-(1-methylethyl)-2-buten-1-yl)-n,3-dimethyl-
6s0t7u2i3f ,
157207-90-4
(-)-hemiasterlin
unii-6s0t7u2i3f
SCHEMBL57313
l-valinamide, n,.beta.,.beta.,1-tetramethyl-l-tryptophyl-n-((1s,2e)-3-carboxy-1-(1-methylethyl)-2-buten-1-yl)-n,3-dimethyl-
Q27265411
(s,e)-2,5-dimethyl-4-((s)-n,3,3-trimethyl-2-((s)-3-methyl-3-(1-methyl-1h-indol-3-yl)-2-(methylamino)butanamido)butanamido)hex-2-enoic acid
HY-117371
AKOS040752003

Research Excerpts

Overview

Hemiasterlin is a natural product derived from marine sponges. It binds to the Vinca-peptide site in tubulin, disrupts normal microtubule dynamics, and, at stoichiometric amounts, depolymerizes microtubules.

Excerpt	Reference	Relevance
"Hemiasterlin is an antimitotic marine natural product with reported sub-nanomolar potency against several cancer cell lines. "	( Expeditious Total Synthesis of Hemiasterlin through a Convergent Multicomponent Strategy and Its Use in Targeted Cancer Therapeutics. Carroll, JS; Charoenpattarapreeda, J; Spring, DR; Walsh, SJ, 2020)	2.29
"Hemiasterlin is a natural product derived from marine sponges that, like other structurally diverse peptide-like molecules, binds to the Vinca-peptide site in tubulin, disrupts normal microtubule dynamics, and, at stoichiometric amounts, depolymerizes microtubules. "	( HTI-286, a synthetic analogue of the tripeptide hemiasterlin, is a potent antimicrotubule agent that circumvents P-glycoprotein-mediated resistance in vitro and in vivo. Andersen, RJ; Annable, T; Ayral-Kaloustian, S; Baxter, M; Beyer, C; Discafani, CM; Fojo, T; Greenberger, LM; Hardy, C; Hari, M; Hernandez, R; Khafizova, G; Loganzo, F; Musto, S; Nieman, JA; Poruchynsky, MS; Singanallore, T; Tan, X; Zask, A, 2003)	2.02
"Hemiasterlin is a potent antimitotic peptide that interferes with microtubule dynamics at picomolar concentrations in cell culture. "	( A missense mutation in Caenorhabditis elegans prohibitin 2 confers an atypical multidrug resistance. Doundoulakis, T; Harran, PG; Roth, MG; Zubovych, I, 2006)	1.78

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

Bioassays (7)

Assay ID	Title	Year	Journal	Article
AID354406	Cytotoxicity activity against human MCF7 cells expressing p53 mutant by MTT assay	2003	Journal of natural products, Feb, Volume: 66, Issue:2	Synthesis and antimitotic/cytotoxic activity of hemiasterlin analogues.
AID248904	Concentration required to kill human epidermoid KB-3-1 cell lines containing very low levels of P-glycoprotein after 3 days of continuous exposure	2004	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 14, Issue:21	Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment.
AID248874	Concentration required to kill human epidermoid KB85 cell lines containing moderate levels of P-glycoprotein after 3 days of continuous exposure	2004	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 14, Issue:21	Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment.
AID248889	Concentration required to kill human epidermoid KBV1 cell lines containing very high levels of P-glycoprotein after 3 days of continuous exposure	2004	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 14, Issue:21	Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment.
AID252057	Percent inhibition of bovine microtubule-assisted protein (MAP) rich tubulin polymerisation at concentration of 0.3 uM; Not applicable	2004	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 14, Issue:21	Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment.
AID1304574	Antiproliferative activity against human MCF7 cells after 20 hrs by microculture tetrazolium assay	2016	Journal of natural products, Mar-25, Volume: 79, Issue:3	The Halicylindramides, Farnesoid X Receptor Antagonizing Depsipeptides from a Petrosia sp. Marine Sponge Collected in Korea.
AID354405	Antimitotic activity against human MCF7 cells expressing p53 mutant by MTT assay	2003	Journal of natural products, Feb, Volume: 66, Issue:2	Synthesis and antimitotic/cytotoxic activity of hemiasterlin analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (30)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	16 (53.33)	29.6817
2010's	13 (43.33)	24.3611
2020's	1 (3.33)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.28

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	29.28 (24.57)
Research Supply Index	3.50 (2.92)
Research Growth Index	4.42 (4.65)
Search Engine Demand Index	36.71 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (29.28)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	2 (6.67%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	28 (93.33%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
indole [no description available]	2.15	1	0	indole; polycyclic heteroarene	Escherichia coli metabolite
nocodazole [no description available]	2.03	1	0	aromatic ketone; benzimidazoles; carbamate ester; thiophenes	antimitotic; antineoplastic agent; microtubule-destabilising agent; tubulin modulator
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	3.43	1	1	mitomycin	alkylating agent; antineoplastic agent
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.02	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	2.04	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	7.01	1	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
thiazoles [no description available]	2.05	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	2.05	1	0	organic cation	geroprotector; herbicide
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.15	1	0	metal allergen; nickel group element atom; platinum group metal atom
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).	2.42	2	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
docetaxel anhydrous Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.	3.43	1	1	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
cryptophycin cryptophycin: a potent antitumor cyclic depsipeptide active against drug-resistant cells; from cyanobacteria (blue-green algae) of the genus Nostoc; structure given in first source;	2.42	2	0
phalloidine Phalloidine: Very toxic polypeptide isolated mainly from AMANITA phalloides (Agaricaceae) or death cup; causes fatal liver, kidney and CNS damage in mushroom poisoning; used in the study of liver damage.. phalloidin : A homodetic bicyclic heptapeptide having a sulfide bridge.	2.03	1	0	homodetic cyclic peptide
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.77	3	0	stilbene
fosbretabulin fosbretabulin: a microtubule destabilizing agent isolated from Combretum caffrum; structure in first source	2.04	1	0
hemiasterlin a hemiasterlin A: potent cytotoxic peptide from marine sponge, Hemiasterella minor; structure given in first source	7.01	1	0
myxothiazol myxothiazol: strobilurin analogue; methoxyacrylamide derivative; antifungal antibiotic from Myxococcus fulvus; structure given in first source. myxothiazol : A 2,4'-bi-1,3-thiazole substituted at the 4-position with a (1E,3S,4R,5E)-7-amino-3,5-dimethoxy-4-methyl-7-oxohepta-1,5-dien-1-yl] group and at the 2'-position with a (2S,3E,5E)-7-methylocta-3,5-dien-2-yl group. It is an inhibitor of coenzyme Q - cytochrome c reductase.	2.05	1	0
phomopsin phomopsin: RN for cpd not in Chemline 7/18/83	2.02	1	0	oligopeptide
pregna-4,17-diene-3,16-dione pregna-4,17-diene-3,16-dione: steroid from guggulu extract; RN & N1 from C1 Form index; RN given refers to cpd without isomeric designation; structure in first source; antagonist of farnesoid X receptor	2.13	1	0	3-hydroxy steroid	androgen
hti-286 HTI-286: a synthetic analog of the tripeptide hemiasterlin; structure in first source	5.68	10	2
dolastatin 10 dolastatin 10: from mollusk Dolabella auricularia; contains four amino acids, dolavaline, dolaisoleucine, dolaproine, valine and the primary amine dolaphenine; deo-dolastatin 10 is a new dolastatin 10 chiral derivative with MW of 784. dolastatin 10 : A tetrapeptide that is isolated from the sea hare Dolabella auricularia. It is a potent anticancer agent which inhibits tubulin polymerization.	2.71	3	0	1,3-thiazoles; tetrapeptide	animal metabolite; antineoplastic agent; apoptosis inducer; marine metabolite; microtubule-destabilising agent
dolastatin 15 dolastatin 15: from Dolabella auricularia; seven subunit depsipeptide	2.02	1	0
arenastatin a [no description available]	2.13	1	0
halipeptin a halipeptin A: 17-membered cyclic depsipeptide	2.13	1	0
cis-3,4',5-trimethoxy-3'-aminostilbene cis-3,4',5-trimethoxy-3'-aminostilbene: structure in first source	2.5	2	0
mk 2206 MK 2206: a protein kinase inhibitor and antineoplastic agent	2.13	1	0	organic heterotricyclic compound	EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor
piperidines Piperidines: A family of hexahydropyridines.	2.05	1	0
ly 355703 cryptophycin 52: an antimitotic antitumor agent; structure in first source	2.02	1	0
chondroitin sulfates Chondroitin Sulfates: Derivatives of chondroitin which have a sulfate moiety esterified to the galactosamine moiety of chondroitin. Chondroitin sulfate A, or chondroitin 4-sulfate, and chondroitin sulfate C, or chondroitin 6-sulfate, have the sulfate esterified in the 4- and 6-positions, respectively. Chondroitin sulfate B (beta heparin; DERMATAN SULFATE) is a misnomer and this compound is not a true chondroitin sulfate.	2.53	2	0
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.02	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor

Condition	Relationship Strength	Studies	Trials
B16 Melanoma [description not available]	2.46	2	0
Bladder Cancer [description not available]	8.87	2	1
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	3.87	2	1
Cancer of Skin [description not available]	2.11	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.11	1	0
Skin Neoplasms Tumors or cancer of the SKIN.	2.11	1	0
Cancer of Ovary [description not available]	2.74	3	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	2.74	3	0
Hepatocellular Carcinoma [description not available]	2.03	1	0
Cancer of Liver [description not available]	2.03	1	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.03	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.03	1	0
Cancer of Prostate [description not available]	3.43	1	1
Hormone-Dependent Neoplasms [description not available]	3.43	1	1
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	3.43	1	1
Cancer of Lung [description not available]	2.04	1	0
Lung Neoplasms Tumors or cancer of the LUNG.	2.04	1	0

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