Compounds > alpha-cadinol
Page last updated: 2024-11-12

alpha-cadinol

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

Description

alpha-cadinol : A cadinane sesquiterpenoid that is cadin-4-ene carrying a hydroxy substituent at position 10. [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]

Cross-References

ID SourceID
PubMed CID10398656
CHEMBL ID486795
CHEBI ID132905
SCHEMBL ID4276031
MeSH IDM0412835

Synonyms (25)

Synonym
alpha-cadinol
(1r,4s,4ar,8ar)-4-isopropyl-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol
(-)-alpha-cadinol
481-34-5
CHEBI:132905
(1r,4s,4ar,8ar)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol
cadin-4-en-10-ol
CHEMBL486795
dc0yj4816p ,
unii-dc0yj4816p
alpha-cadinol, (-)-
l-alpha-cadinol
SCHEMBL4276031
(-)-.alpha.-cadinol
1-naphthalenol, 1,2,3,4,4a,7,8,8a-octahydro-1,6-dimethyl-4-(1-methylethyl)-, (1r,4s,4ar,8ar)-
l-.alpha.-cadinol
(1r-(1.alpha.,4.beta.,4a.beta.,8a.alpha.))-
cadinol, alpha-
.alpha.-cadinol, (-)-
1-naphthalenol, 1,2,3,4,4a,7,8,8a-octahydro-1,6-dimethyl-4-(1-methylethyl)-,
(1r,4s,4ar,8ar)-1,2,3,4,4a,7,8,8a-octahydro-1,6-dimethyl-4-(1-methylethyl)-1-naphthalenol
a-cadinol
Q4734900
(1r,4s,4ar,8ar)-1,6-dimethyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2h-naphthalen-1-ol
DTXSID701017679
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
fungicideA substance used to destroy fungal pests.
volatile oil componentAny plant metabolite that is found naturally as a component of a volatile oil.
[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 (4)

ClassDescription
cadinane sesquiterpenoidAny sesquiterpenoid with a cadinane skeleton.
carbobicyclic compoundA bicyclic compound in which all the ring atoms are carbon.
tertiary alcoholA 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.
octahydronaphthalenesAny carbobycyclic compound that is an octahydronaphthalene or a compound obtained from an octahydronaphthalene by formal substitution of one or more hydrogens.
[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 (21)

Assay IDTitleYearJournalArticle
AID297145Inhibition of SARS coronavirus-induced cytopathogenicity in Vero E6 cells at 20 uM2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus.
AID297147Inhibition of SARS virus-induced cytopathogenicity in Vero E6 cells at 3.3 uM2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus.
AID297149Antiviral activity against SARS coronavirus in Vero E6 cells assessed as inhibition of viral replication by ELISA2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus.
AID1464849Antiausteritic activity against human MIAPaCa2 cells in nutrient-deprived medium measured after 24 hrs by WST8 assay2017Bioorganic & medicinal chemistry letters, 11-01, Volume: 27, Issue:21
Discovery of potential antiausterity agents from the Japanese cypress Chamaecyparis obtusa.
AID401841Insecticidal activity against yellow fever mosquito larvae1997Journal of natural products, Jan, Volume: 60, Issue:1
Bioactive compounds from Taiwania cryptomerioides.
AID297151Selectivity index, Ratio of CC50 for Vero E6 cells to EC50 for SARS coronavirus2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus.
AID356416Chemoprevention index, ratio of IC50 for mouse Hepa-1c1c7 cells to drug level required to double NADPH:quinone reductase activity in mouse Hepa-1c1c7 cells2003Journal of natural products, Sep, Volume: 66, Issue:9
Constituents of the stem bark of Pongamia pinnata with the potential to induce quinone reductase.
AID401838Toxicity in Artemia salina1997Journal of natural products, Jan, Volume: 60, Issue:1
Bioactive compounds from Taiwania cryptomerioides.
AID356414Induction of NADPH:quinone reductase activity in mouse Hepa-1c1c7 cells assessed as drug level required to double specific enzyme activity2003Journal of natural products, Sep, Volume: 66, Issue:9
Constituents of the stem bark of Pongamia pinnata with the potential to induce quinone reductase.
AID297150Cytotoxicity against Vero E6 cells by MTT assay2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus.
AID1464852Antiausteritic activity against human KLM1 cells in nutrient-deprived medium measured after 24 hrs by WST8 assay2017Bioorganic & medicinal chemistry letters, 11-01, Volume: 27, Issue:21
Discovery of potential antiausterity agents from the Japanese cypress Chamaecyparis obtusa.
AID297148Inhibition of SARS virus-induced cytopathogenicity in Vero E6 cells at 1 uM2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus.
AID401840Cytotoxicity against human HT-29 cells after 7 days by MTT assay1997Journal of natural products, Jan, Volume: 60, Issue:1
Bioactive compounds from Taiwania cryptomerioides.
AID401837Cytotoxicity against human MCF7 cells after 7 days by MTT assay1997Journal of natural products, Jan, Volume: 60, Issue:1
Bioactive compounds from Taiwania cryptomerioides.
AID1464850Antiausteritic activity against human Capan1 cells in nutrient-deprived medium measured after 24 hrs by WST8 assay2017Bioorganic & medicinal chemistry letters, 11-01, Volume: 27, Issue:21
Discovery of potential antiausterity agents from the Japanese cypress Chamaecyparis obtusa.
AID297146Inhibition of SARS coronavirus-induced cytopathogenicity in Vero E6 cells at 10 uM2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus.
AID1464848Antiausteritic activity against human PANC1 cells in nutrient-deprived medium measured after 24 hrs by WST8 assay2017Bioorganic & medicinal chemistry letters, 11-01, Volume: 27, Issue:21
Discovery of potential antiausterity agents from the Japanese cypress Chamaecyparis obtusa.
AID1464851Antiausteritic activity against human PSN1 cells in nutrient-deprived medium measured after 24 hrs by WST8 assay2017Bioorganic & medicinal chemistry letters, 11-01, Volume: 27, Issue:21
Discovery of potential antiausterity agents from the Japanese cypress Chamaecyparis obtusa.
AID356415Inhibition of mouse Hepa-1c1c7 cells assessed as cell viability2003Journal of natural products, Sep, Volume: 66, Issue:9
Constituents of the stem bark of Pongamia pinnata with the potential to induce quinone reductase.
AID401839Cytotoxicity against human A549 cells after 7 days by MTT assay1997Journal of natural products, Jan, Volume: 60, Issue:1
Bioactive compounds from Taiwania cryptomerioides.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (20.00)18.2507
2000's2 (40.00)29.6817
2010's2 (40.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.66

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.

MetricThis Compound (vs All)
Research Demand Index28.66 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.66)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
niclosamide
Niclosamide: An antihelmintic that is active against most tapeworms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p48). niclosamide : A secondary carboxamide resulting from the formal condensation of the carboxy group of 5-chlorosalicylic acid with the amino group of 2-chloro-4-nitroaniline. It is an oral anthelmintic drug approved for use against tapeworm infections.		2.9510benzamides;
C-nitro compound;
monochlorobenzenes;
salicylanilides;
secondary carboxamide		anthelminthic drug;
anticoronaviral agent;
antiparasitic agent;
apoptosis inducer;
molluscicide;
piscicide;
STAT3 inhibitor
sulforaphane
sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.		2.0110isothiocyanate;
sulfoxide		antineoplastic agent;
antioxidant;
EC 3.5.1.98 (histone deacetylase) inhibitor;
plant metabolite
stearyl alcohol
octadecan-1-ol : A long-chain primary fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of 18 carbon atoms.. octadecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of eighteen carbon atoms.		2.0110long-chain primary fatty alcohol;
octadecanol		algal metabolite;
human metabolite;
plant metabolite
glycyrrhetinic acid
[no description available]		2.9510cyclic terpene ketone;
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		immunomodulator;
plant metabolite
glycyrrhizic acid
glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.		2.9510enone;
glucosiduronic acid;
pentacyclic triterpenoid;
tricarboxylic acid;
triterpenoid saponin		EC 3.4.21.5 (thrombin) inhibitor;
plant metabolite
colforsin
Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.		2.9510acetate ester;
cyclic ketone;
labdane diterpenoid;
organic heterotricyclic compound;
tertiary alpha-hydroxy ketone;
triol		adenylate cyclase agonist;
anti-HIV agent;
antihypertensive agent;
plant metabolite;
platelet aggregation inhibitor;
protein kinase A agonist
betulinic acid
[no description available]		3.3420hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite
arctigenin
arctigenin: precursor to catechols; in many plants		2.1510lignan
magnolol
[no description available]		2.9510biphenyls
honokiol
[no description available]		2.9510biphenyls
lupenone
lupenone: structure in first source		2.0110triterpenoidmetabolite
sugiol
sugiol: diterpene with anti-inflammatory activity from Calocedrus formosana bark; structure in first source. sugiol : An abietane diterpenoid that is ferruginol in which the methylene group para to the phenolic hydroxy group has been substituted by an oxo group.		2.9510abietane diterpenoid;
carbotricyclic compound;
cyclic terpene ketone;
meroterpenoid;
phenols		antineoplastic agent;
antioxidant;
antiviral agent;
plant metabolite;
radical scavenger
betulonic acid
betulonic acid: isolated from Rush javanica; strucure in first source		2.9510triterpenoidanticoronaviral agent
t-cadinol
T-cadinol: extract of scented myrrh; RN given refers to (1S-(1alpha,4alpha,4aalpha,8abeta)-isomer; RN for cpd without isomeric designation not avail 3/92; structure given in first source. tau-cadinol : A cadinane sesquiterpenoid that is cadin-4-ene carrying a hydroxy substituent at position 10.		2.1510cadinane sesquiterpenoid;
carbobicyclic compound;
octahydronaphthalenes;
tertiary alcohol		plant metabolite;
volatile oil component
helioxanthin
helioxanthin: structure in first source. helioxanthin : A furonaphthodioxole that is furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7(9H)-one substituted by a 1,3-benzodioxol-5-yl group at posiiton 10. It is a inhibitor of HBV, HCV and HSV-1 viruses.		1.9910benzodioxoles;
furonaphthodioxole;
lignan		anti-HBV agent;
antineoplastic agent;
plant metabolite
lupeol
[no description available]		2.0110pentacyclic triterpenoid;
secondary alcohol		anti-inflammatory drug;
plant metabolite
ferruginol
ferruginol: structure in first source. ferruginol : An abietane diterpenoid that is abieta-8,11,13-triene substituted by a hydroxy group at positions 12.		3.3320abietane diterpenoid;
carbotricyclic compound;
meroterpenoid;
phenols		antibacterial agent;
antineoplastic agent;
plant metabolite;
protective agent
hinokinin
hinokinin: suppresses expression of both HBsAg and HBeAg. hinokinin : A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 3,4-methylenedioxybenzyl group at positions 3 and 4 (the 3R,4R-diastereoisomer).		3.3920benzodioxoles;
gamma-lactone;
lignan		trypanocidal drug
oleic acid
Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.		2.0110octadec-9-enoic acidantioxidant;
Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
Escherichia coli metabolite;
mouse metabolite;
plant metabolite;
solvent
6,7-dehydroroyleanone
6,7-dehydroroyleanone: diterpene abietane quinone isolated from Salvia moorcraftiana or Lepechinia bullata (both Lamiaceae); Rn given from CA Index Guide; RN not in Chemline 12/84; structure given in first source		2.9510
valinomycin
Valinomycin: A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.. valinomycin : A twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.		2.9510cyclodepsipeptide;
macrocycle		antimicrobial agent;
antiviral agent;
bacterial metabolite;
potassium ionophore
savinin
savinin: a lignan from Pterocarpus santalinus inhibits tumor necrosis factor-alpha production and T cell proliferation; structure in first source. savinin : A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 1,3-benzodioxol-5-ylmethylidene group at position 3 and a 1,3-benzodioxol-5-ylmethyl group at position 4 (the 3E,4R-isomer). It exhibits antiviral activity against SARS-CoV-2.		2.9510benzodioxoles;
gamma-lactone;
lignan		anti-inflammatory agent;
anticoronaviral agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
plant metabolite;
T-cell proliferation inhibitor
stigmasterol 3-o-beta-d-glucopyranoside
stigmasterol 3-O-beta-D-glucopyranoside: an antioxidant from Monochoria vaginalis; structure in first source. stigmasterol 3-O-beta-D-glucoside : A steroid saponin that is (3beta,22E)-stigmasta-5,22-dien-3-ol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It is isolated from Symplocos lancifolia.		2.0110beta-D-glucoside;
monosaccharide derivative;
phytosterols;
steroid saponin		metabolite
5-methoxy-8,8-dimethyl-2-phenyl-4H,8H-pyrano[2,3-h]chromen-4-one
[no description available]		2.0110extended flavonoid
ConditionIndicatedRelationship StrengthStudiesTrials
Hepatocellular Carcinoma
[description not available]		02.0110
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.		02.0110
Benign Neoplasms
[description not available]		03.0310
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.		03.0310