Andrographolide

Identification

Generic Name
Andrographolide
DrugBank Accession Number
DB05767
Background

Andrographolide (HMPL-004) is a botanical product extracted from a herb that occurs naturally in China. The herb has an extensive history of use in TCM for the treatment of upper respiratory tract infections and other inflammatory and infectious diseases.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 350.455
Monoisotopic: 350.209324066
Chemical Formula
C20H30O5
Synonyms
  • 3α,14,15,18-tetrahydroxy-5b,9bH,10a-labda-8(20),12-dien-16-oic acid γ-Lactone
External IDs
  • HMPL-004
  • HMPL004

Pharmacology

Indication

Investigated for use/treatment in ulcerative colitis.

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Pharmacodynamics

Not Available

Mechanism of action

HMPL-004 acts on multiple cellular targets in the inflammatory signal transduction pathways resulting in suppressed inflammation cytokine expression including TNF-α, IL-1β and IL-6. HMPL-004 was demonstrated to inhibit TNF-α and IL-1β production in cell-based assays. HMPL-004 is also able to inhibit NF-kB activation. NF-kB is a family of transcriptional factors that regulate a wide spectrum of genes critically involved in host defence and inflammation. The mechanism of action of HMPL-004 was further supported in laboratory IBD animal models. Treatment of IBD rats with HMPL-004 caused a significant drop in plasma cytokine concentrations, including TNF-α and IL-1β.

TargetActionsOrganism
UTumor necrosis factorNot AvailableHumans
UInterleukin-1 betaNot AvailableHumans
UInterleukin-6Not AvailableHumans
UNuclear factor NF-kappa-B p100 subunitNot AvailableHumans
UNuclear factor NF-kappa-B p105 subunitNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbciximabThe risk or severity of bleeding can be increased when Andrographolide is combined with Abciximab.
AbrocitinibThe risk or severity of bleeding and thrombocytopenia can be increased when Andrographolide is combined with Abrocitinib.
AceclofenacThe risk or severity of bleeding can be increased when Aceclofenac is combined with Andrographolide.
AcemetacinThe risk or severity of bleeding can be increased when Acemetacin is combined with Andrographolide.
AcenocoumarolThe risk or severity of bleeding can be increased when Andrographolide is combined with Acenocoumarol.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactones
Sub Class
Gamma butyrolactones
Direct Parent
Gamma butyrolactones
Alternative Parents
Tetrahydrofurans / Enoate esters / Secondary alcohols / Cyclic alcohols and derivatives / Oxacyclic compounds / Monocarboxylic acids and derivatives / Primary alcohols / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Alcohol / Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Enoate ester / Gamma butyrolactone / Hydrocarbon derivative
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
secondary alcohol, primary alcohol, gamma-lactone, carbobicyclic compound, labdane diterpenoid (CHEBI:65408)
Affected organisms
Not Available

Chemical Identifiers

UNII
410105JHGR
CAS number
5508-58-7
InChI Key
BOJKULTULYSRAS-OTESTREVSA-N
InChI
InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1
IUPAC Name
(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
SMILES
[H][C@]12CCC(=C)[C@@H](C\C=C3/[C@H](O)COC3=O)[C@]1(C)CC[C@@H](O)[C@@]2(C)CO

References

General References
Not Available
PubChem Compound
5318517
PubChem Substance
347827741
ChemSpider
4477067
BindingDB
50084419
ChEBI
65408
ChEMBL
CHEMBL186141
ZINC
ZINC000003881797
Wikipedia
Andrographolide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusTreatmentAcute Exacerbation of Chronic Bronchitis (AECB)1
4Unknown StatusTreatmentAcute Tonsillitis1
4Unknown StatusTreatmentAcute Tracheobronchitis1
3TerminatedTreatmentUlcerative Colitis2
2CompletedTreatmentCrohn's Disease (CD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.284 mg/mLALOGPS
logP1.57ALOGPS
logP1.66Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)13.48Chemaxon
pKa (Strongest Basic)-2.8Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area86.99 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity94.93 m3·mol-1Chemaxon
Polarizability38.27 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0159-0029000000-ba800d55dfc663f742a2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4j-0019000000-25a210618c0718588eac
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pbm-0049000000-8434c56f20900b80f9a6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1394000000-f69c00e86ac49f699d0f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-003v-2098000000-652cb509a614bd920e29
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9681000000-6f3aaf6c20f2eb37f3af
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-195.6312579
predicted
DarkChem Lite v0.1.0
[M-H]-190.2163579
predicted
DarkChem Lite v0.1.0
[M-H]-181.89417
predicted
DeepCCS 1.0 (2019)
[M+H]+195.7212579
predicted
DarkChem Lite v0.1.0
[M+H]+190.0616579
predicted
DarkChem Lite v0.1.0
[M+H]+183.79454
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.8002579
predicted
DarkChem Lite v0.1.0
[M+Na]+189.6206579
predicted
DarkChem Lite v0.1.0
[M+Na]+189.70705
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tumor necrosis factor receptor binding
Specific Function
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...
Gene Name
TNF
Uniprot ID
P01375
Uniprot Name
Tumor necrosis factor
Molecular Weight
25644.15 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein domain specific binding
Specific Function
Potent proinflammatory cytokine. Initially discovered as the major endogenous pyrogen, induces prostaglandin synthesis, neutrophil influx and activation, T-cell activation and cytokine production, ...
Gene Name
IL1B
Uniprot ID
P01584
Uniprot Name
Interleukin-1 beta
Molecular Weight
30747.7 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Interleukin-6 receptor binding
Specific Function
Cytokine with a wide variety of biological functions. It is a potent inducer of the acute phase response. Plays an essential role in the final differentiation of B-cells into Ig-secreting cells Inv...
Gene Name
IL6
Uniprot ID
P05231
Uniprot Name
Interleukin-6
Molecular Weight
23717.965 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
Gene Name
NFKB2
Uniprot ID
Q00653
Uniprot Name
Nuclear factor NF-kappa-B p100 subunit
Molecular Weight
96748.355 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcriptional repressor activity, rna polymerase ii transcription regulatory region sequence-specific binding
Specific Function
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
Gene Name
NFKB1
Uniprot ID
P19838
Uniprot Name
Nuclear factor NF-kappa-B p105 subunit
Molecular Weight
105355.175 Da

Drug created at November 18, 2007 18:27 / Updated at June 12, 2020 16:52