pachastrissamine

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

Description

pachastrissamine: a cytotoxic anhydrophytosphingosine from a marine sponge, Pachastrissa sp. ; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	9814817
CHEMBL ID	447577
SCHEMBL ID	766801
MeSH ID	M0442900

Synonyms (4)

Synonym
pachastrissamine
CHEMBL447577
SCHEMBL766801
(2s,3s,4s)-4-amino-2-tetradecyloxolan-3-ol

Research Excerpts

Treatment

Excerpt	Reference	Relevance
"Treatment of pachastrissamine with tetrahydro-2-furanol under acidic conditions led to smooth oxazolidine ring formation, furnishing jaspine A in a high yield."	( Enantioselective syntheses of pachastrissamine and jaspine A via hydroxylactonization of a chiral epoxy ester. Enomoto, M; Kuwahara, S; Urano, H, 2010)	1

Bioavailability

Excerpt	Reference	Relevance
" Jaspine B has been shown to inhibit sphingomyelin synthase, which synthesizes sphingomyelin from ceramide, a critical signal transducer; however, jaspine B's low bioavailability limits its application as a promising treatment option."	( Formulation, Characterization, and In Vitro/In Vivo Efficacy Studies of a Novel Liposomal Drug Delivery System of Amphiphilic Jaspine B for Treatment of Synovial Sarcoma. Aghazadeh-Habashi, A; Barrott, JJ; Khajeh Pour, S; Mateen, S; Pashikanti, S, 2022)	0.72

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

Bioassays (30)

Assay ID	Title	Year	Journal	Article
AID614533	Inhibition of N-terminal GST-fused PKClota (1-587) expressed in baculovirus expression system at 30 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID1370465	Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay	2018	Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3	Discovery of novel jaspine B analogues as autophagy inducer.
AID1370464	Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay	2018	Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3	Discovery of novel jaspine B analogues as autophagy inducer.
AID411726	Cytotoxicity against human A549 cells after 24 hrs by MTT assay in presence of 3-methyladenine	2009	Bioorganic & medicinal chemistry, Jan-01, Volume: 17, Issue:1	Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines.
AID614531	Inhibition of N-terminal GST-fused PKCdelta (1-676) expressed in baculovirus expression system at 30 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID411728	Induction of 3-methyladenine-induced autophagy in human A549 cells assessed as increase in ceramide levels	2009	Bioorganic & medicinal chemistry, Jan-01, Volume: 17, Issue:1	Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines.
AID614532	Inhibition of N-terminal GST-fused PKCepsilon (1-737) expressed in baculovirus expression system at 30 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID614543	Inhibition of N-terminal GST-fused PKCbeta2 (1-673) expressed in baculovirus expression system at 30 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID614534	Inhibition of N-terminal GST-fused PKCeta (1-683) expressed in baculovirus expression system at 30 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID614530	Inhibition of N-terminal GST-fused PKCgamma (1-697) expressed in baculovirus expression system at 30 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID411729	Induction of 3-methyladenine-induced autophagy in human A549 cells assessed as increase in dihydroceramide levels	2009	Bioorganic & medicinal chemistry, Jan-01, Volume: 17, Issue:1	Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines.
AID614542	Inhibition of N-terminal GST-fused PKCbeta1 (1-671) expressed in baculovirus expression system at 30 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID614539	Inhibition of N-terminal GST-fused sphingosine kinase 1 (1-384) expressed in baculovirus expression system assessed as inhibition of sphingosine phosphorylation after 1 hr by off-chip mobility shift assay	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID1143433	Antiproliferative activity against human MGC803 cells after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Jun-10, Volume: 80	Synthesis and preliminary biological evaluation of 1,2,3-triazole-Jaspine B hybrids as potential cytotoxic agents.
AID411724	Cytotoxicity against human A549 cells after 24 hrs by MTT assay	2009	Bioorganic & medicinal chemistry, Jan-01, Volume: 17, Issue:1	Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines.
AID1370463	Antiproliferative activity against mouse B16/F10 cells after 72 hrs by MTT assay	2018	Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3	Discovery of novel jaspine B analogues as autophagy inducer.
AID614538	Inhibition of N-terminal GST-fused PKClota (1-587) expressed in baculovirus expression system at 3 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID614541	Inhibition of N-terminal GST-fused PKCalpha (1-672) expressed in baculovirus expression system at 30 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID336470	Cytotoxicity against human A549 cells after 3 days	2002	Journal of natural products, Oct, Volume: 65, Issue:10	Pachastrissamine, a cytotoxic anhydrophytosphingosine from a marine sponge, Pachastrissa sp.
AID614536	Inhibition of N-terminal GST-fused PKCzeta (1-592) expressed in baculovirus expression system at 30 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID336472	Cytotoxicity against human SK-MEL-28 cells after 3 days	2002	Journal of natural products, Oct, Volume: 65, Issue:10	Pachastrissamine, a cytotoxic anhydrophytosphingosine from a marine sponge, Pachastrissa sp.
AID1143434	Antiproliferative activity against human MCF7 cells after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Jun-10, Volume: 80	Synthesis and preliminary biological evaluation of 1,2,3-triazole-Jaspine B hybrids as potential cytotoxic agents.
AID614540	Inhibition of N-terminal GST-fused sphingosine kinase 2 (1-618) expressed in baculovirus expression system assessed as inhibition of sphingosine phosphorylation after 1 hr by off-chip mobility shift assay	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID1370462	Antiproliferative activity against human A549 cells after 72 hrs by MTT assay	2018	Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3	Discovery of novel jaspine B analogues as autophagy inducer.
AID336469	Cytotoxicity against mouse P388 cells after 3 days	2002	Journal of natural products, Oct, Volume: 65, Issue:10	Pachastrissamine, a cytotoxic anhydrophytosphingosine from a marine sponge, Pachastrissa sp.
AID336471	Cytotoxicity against human HT-29 cells after 3 days	2002	Journal of natural products, Oct, Volume: 65, Issue:10	Pachastrissamine, a cytotoxic anhydrophytosphingosine from a marine sponge, Pachastrissa sp.
AID411725	Cytotoxicity against human A549 cells assessed as PI positive cells after 24 hrs by flow cytometry	2009	Bioorganic & medicinal chemistry, Jan-01, Volume: 17, Issue:1	Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines.
AID614535	Inhibition of N-terminal GST-fused PKCtheta (1-706) expressed in baculovirus expression system at 30 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
AID1143432	Antiproliferative activity against human EC9706 cells after 48 hrs by MTT assay	2014	European journal of medicinal chemistry, Jun-10, Volume: 80	Synthesis and preliminary biological evaluation of 1,2,3-triazole-Jaspine B hybrids as potential cytotoxic agents.
AID614537	Inhibition of N-terminal GST-fused PKCzeta (1-592) expressed in baculovirus expression system at 3 uM after 1 hr by off-chip mobility shift assay relative to control	2011	Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18	Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (47)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	12 (25.53)	29.6817
2010's	29 (61.70)	24.3611
2020's	6 (12.77)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.81

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 weak demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	10.81 (24.57)
Research Supply Index	3.87 (2.92)
Research Growth Index	4.68 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (10.81)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	2 (4.26%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	45 (95.74%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.05	1	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.53	2	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.02	1	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
acetylene [no description available]	2.05	1	alkyne; gas molecular entity; terminal acetylenic compound
ethylene oxide Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.	2.08	1	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
allyl alcohol allyl alcohol: structure. allylic alcohol : An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.).. allyl alcohol : A propenol in which the C=C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.	2.11	1	primary allylic alcohol; propenol	antibacterial agent; fungicide; herbicide; insecticide; plant metabolite
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	7.03	1	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	7.05	1	carbon oxoanion
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.	2.75	3	metal allergen; nickel group element atom; platinum group metal atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	7.03	1	cobalt group element atom
iodine [no description available]	2.11	1	halide anion; monoatomic iodine	human metabolite
pyrrolidine [no description available]	2.31	1	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
lissamine rhodamine b lissamine rhodamine B: RN given refers to parent cpd; Lissamine Rhodamine B refers to Na salt	2.11	1
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.1	1	1,2,3-triazole
oxazolidin-2-one Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.	2.11	1	carbamate ester; oxazolidinone	metabolite
phytosphingosine phytosphingosine: differ with an additional hydroxyl at C-4 & no double bond between C-4 & C-5	2.96	4	amino alcohol; sphingoid; triol	mouse metabolite; Saccharomyces cerevisiae metabolite
xylose xylopyranose: structure in first source	7.73	3	D-xylose
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	7.04	1	alkali metal atom
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	6.87	47	sphing-4-enine	human metabolite; mouse metabolite
n,n-dimethylsphingenine N,N-dimethylsphingosine: a sphingosine kinase inhibitor. N,N-dimethylsphingosine : A sphingoid that is sphingosine in which the two amino hydrogens are replaced by methyl groups.	2.06	1	aminodiol; sphingoid; tertiary amino compound	EC 2.7.1.91 (sphingosine kinase) inhibitor; metabolite
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.49	2	chalcogen; nonmetal atom	macronutrient
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	7.06	1	chalcogen; nonmetal atom	micronutrient
ribose ribopyranose : The pyranose form of ribose.	2.03	1	D-ribose; ribopyranose
sphingosine kinase [no description available]	8.4	6
glycolipids [no description available]	2.41	1
piperidines Piperidines: A family of hexahydropyridines.	2.04	1

Condition	Relationship Strength	Studies
Cancer of Stomach [description not available]	2.63	2
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.63	2
Benign Neoplasms [description not available]	2.41	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.	2.41	1
Synovioma [description not available]	2.41	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)	2.41	1
Rheumatoid Arthritis [description not available]	2.31	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.	2.31	1
Malignant Melanoma [description not available]	2.46	2
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	7.46	2
B16 Melanoma [description not available]	2.05	1

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