Compounds > nigranoic acid
Page last updated: 2024-11-12

nigranoic acid

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

Description

nigranoic acid: from stem of Schisandra sphaerandra; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

nigranoic acid : A tetracyclic triterpenoid that is 3,4-secocycloarta-4(28),24-(Z)-diene substituted by carboxy groups at positions 3 and 26. Isolated from Schisandra henryi and Schisandra propinqua, it exhibits cytotoxic and anti-HIV activities. [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]

FloraRankFlora DefinitionFamilyFamily Definition
Schisandra propinquaspecies[no description available]SchisandraceaeA plant family of the order AUSTROBAILEYALES, class MAGNOLIOPSIDA.[MeSH]
Schisandra henryispecies[no description available]SchisandraceaeA plant family of the order AUSTROBAILEYALES, class MAGNOLIOPSIDA.[MeSH]

Cross-References

ID SourceID
PubMed CID10814237
CHEMBL ID480082
CHEBI ID66626
MeSH IDM0264591

Synonyms (14)

Synonym
nigranoic acid
(z,6r)-6-(2-carboxyethyl-isopropenyl-dimethyl-[?]yl)-2-methyl-hept-2-enoic acid
3,4-secocycloarta-4(28),24-(z)-diene-3,26-dioic acid
chebi:66626 ,
CHEMBL480082
39111-07-4
(2z,6r)-6-[(1r,3as,3bs,6s,6ar,7as,9ar)-6a-(2-carboxyethyl)-3a,9a-dimethyl-6-(prop-1-en-2-yl)dodecahydro-1h-cyclopenta[a]cyclopropa[e]naphthalen-1-yl]-2-methylhept-2-enoic acid
bdbm50478414
Q27135245
CS-0090496
HY-122935
MS-28711
DTXSID301319075
AKOS040740859
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
HIV-1 reverse transcriptase inhibitorAn entity which inhibits the activity of HIV-1 reverse transcriptase.
[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 (2)

ClassDescription
tetracyclic triterpenoidAny triterpenoid consisting of a tetracyclic skeleton.
dicarboxylic acidAny carboxylic acid containing two carboxy 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]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1IC50 (µMol)159.40000.00011.076810.0000AID354556
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID1859372Inhibition of HIV-1 protease relative to control2022European journal of medicinal chemistry, Apr-05, Volume: 233Natural products and synthetic analogues against HIV: A perspective to develop new potential anti-HIV drugs.
AID354569Inhibition of DNA dependent DNA polymerase at 200 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354570Inhibition of DNA dependent DNA polymerase1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354560Inhibition of HIV1 reverse transcriptase mutant1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354564Inhibition of DNA polymerase alpha1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354567Inhibition of RNA polymerase at 200 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID569567Therapeutic index, ratio of CC50 for human C1866 cells to EC50 for HIV1-3B2011Bioorganic & medicinal chemistry letters, Feb-01, Volume: 21, Issue:3
Compounds from Kadsura angustifolia with anti-HIV activity.
AID354566Inhibition of DNA polymerase beta1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354571Inhibition of RNaseH at 200 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354565Inhibition of DNA polymerase beta at 200 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID380078Antiviral activity against HIV1 infected in human C8166 cells assessed as inhibition of viral-induced cytopathic effect2006Journal of natural products, Feb, Volume: 69, Issue:2
Triterpenoids from Schisandra lancifolia with anti-HIV-1 activity.
AID354563Inhibition of DNA polymerase alpha at 200 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354562Inhibition of AMV reverse transcriptase1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354557Inhibition of HIV2 reverse transcriptase at 200 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID569566Antiviral activity against HIV1-3B infected in human C1866 cells assessed as inhibition of virus-induced cytopathic effect2011Bioorganic & medicinal chemistry letters, Feb-01, Volume: 21, Issue:3
Compounds from Kadsura angustifolia with anti-HIV activity.
AID354558Inhibition of HIV2 reverse transcriptase1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354572Inhibition of RNaseH1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354561Inhibition of AMV reverse transcriptase at 200 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354559Inhibition of HIV1 reverse transcriptase mutant at 200 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID569565Cytotoxicity against human C1866 cells2011Bioorganic & medicinal chemistry letters, Feb-01, Volume: 21, Issue:3
Compounds from Kadsura angustifolia with anti-HIV activity.
AID354555Inhibition of HIV1 reverse transcriptase at 200 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354568Inhibition of RNA polymerase1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID354556Inhibition of HIV1 reverse transcriptase1996Journal of natural products, May, Volume: 59, Issue:5
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.
AID380077Cytotoxicity against human C8166 cells by MTT assay2006Journal of natural products, Feb, Volume: 69, Issue:2
Triterpenoids from Schisandra lancifolia with anti-HIV-1 activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (5.88)18.2507
2000's3 (17.65)29.6817
2010's11 (64.71)24.3611
2020's2 (11.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.29

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.

MetricThis Compound (vs All)
Research Demand Index12.29 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index5.18 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.29)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
1-butanol
1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.		2.110alkyl alcohol;
primary alcohol;
short-chain primary fatty alcohol		human metabolite;
mouse metabolite;
protic solvent
guaiacol
Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.		2.0510guaiacolsdisinfectant;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
expectorant;
plant metabolite
methanol
Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.		2.110alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
chloroform
Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.		2.110chloromethanes;
one-carbon compound		carcinogenic agent;
central nervous system drug;
inhalation anaesthetic;
non-polar solvent;
refrigerant
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.		2.4520azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
dihydroguaiaretic acid
dihydroguaiaretic acid: lignan extracted form Larrea divaricata; inhibitory to beef heart mitochondrial succinoxidase & NADH-oxidase; RN given refers to cpd without isomeric designation		2.0510
schisantherin d
schisantherin D: a lignan from the fruits of Schisandra sphenanthera		2.0610
naringenin
(S)-naringenin : The (S)-enantiomer of naringenin.		3.5110(2S)-flavan-4-one;
naringenin		expectorant;
plant metabolite
lignans
Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)		2.0510
sesquiterpenes
[no description available]		2.0810
schizandrin
[no description available]		2.0610
quercetin
[no description available]		3.51107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
vitexin
[no description available]		3.5110C-glycosyl compound;
trihydroxyflavone		antineoplastic agent;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
plant metabolite;
platelet aggregation inhibitor
3-methylquercetin
isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.		3.51107-hydroxyflavonol;
monomethoxyflavone;
tetrahydroxyflavone		anticoagulant;
EC 1.14.18.1 (tyrosinase) inhibitor;
metabolite
orientin
orientin: structure given in first source; RN given refers to the (D-glucopyranosyl)-isomer. orientin : A C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8.		3.51103'-hydroxyflavonoid;
C-glycosyl compound;
tetrahydroxyflavone		antioxidant;
metabolite
schisantherin b
schisantherin B: lignan isolated from fruit of Schisandra sphenanthera; RN given refers to schisanterin B and gomisin B		2.0610tannin
corosolic acid
[no description available]		2.110triterpenoidmetabolite
interiotherin b
interiotherin B: isolated from kadsura interior; structure given in first source. interiotherin B : A lignan with a dibenzocyclooctadiene skeleton attached to a fatty acid ester side chain. It is isolated from Kadsura interior and has been shown to exhibit anti-HIV activity.		2.0610aromatic ether;
fatty acid ester;
lignan;
organic heteropentacyclic compound;
oxacycle		anti-HIV agent;
metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		02.0610
HIV Coinfection
[description not available]		03.3310
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		03.3310
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)		02.0810
Cerebral Ischemia
[description not available]		07.1110
Injury, Ischemia-Reperfusion
[description not available]		02.1110
Brain Ischemia
Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.		02.1110
Reperfusion Injury
Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.		07.1110
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		0210