NPs Basic Information

Name
Andrographolide
Molecular Formula C20H30O5
IUPAC Name*
(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
SMILES
C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C/C=C/3\[C@@H](COC3=O)O)(C)CO)O
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
InChIKey
BOJKULTULYSRAS-OTESTREVSA-N
Synonyms
Andrographolide; 5508-58-7; CHEBI:65408; (S,E)-4-Hydroxy-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2(3H)-one; HMPL004; Andro; 410105JHGR; NSC-383468; 3alpha,14,15,18-tetrahydroxy-5b,9bH,10a-labda-8(20),12-dien-16-oic acid gamma-Lactone; (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one; 3-(2-(Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl)ethylidene)dihydro-4-hydroxyfuran-2(3H)-one; (1R-(1-alpha(E(S)),4abeta,5alpha,6alpha,8aalpha))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3H)-furanone; (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; (3E,4S)-4-hydroxy-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethylidene}dihydrofuran-2(3H)-one; 2(3H)-Furanone, 3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, (3E,4S)-; UNII-410105JHGR; HMPL-004; NSC383468; NCGC00095597-01; 2(3H)-FURANONE, 3-(2-((1R,4AS,5R,6R,8AS)-DECAHYDRO-6-HYDROXY-5-(HYDROXYMETHYL)-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL)ETHYLIDENE)DIHYDRO-4-HYDROXY-, (3E,4S)-; EINECS 226-852-5; NSC 383468; Andrographolide, 98%; ANDROGRAPHOLIDE [MI]; DSSTox_CID_25980; DSSTox_RID_81270; DSSTox_GSID_45980; ANDROGRAPHOLIDE [INCI]; BIDD:ER0530; CHEMBL186141; GTPL9675; MEGxp0_000978; ANDROGRAPHOLIDE [USP-RS]; ANDROGRAPHOLIDE [WHO-DD]; DTXSID3045980; SCHEMBL12056309; ACon1_002113; (3E,4S)-3-(2-((1R,4AS,5R,6R,8AS)-DECAHYDRO-6-HYDROXY-5-(HYDROXYMETHYL)-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL)ETHYLIDENE)DIHYDRO-4-HYDROXY-2(3H)-FURANONE; 869807-57-8; ACT03252; Andrographolide, analytical standard; HY-N0191; ZINC3881797; Tox21_111508; BDBM50084419; MFCD07778082; AKOS015920075; CCG-208428; CS-3334; DB05767; NCGC00179817-01; NCGC00179817-02; AS-13637; CAS-5508-58-7; C20214; 508A587; A830479; Q-100624; Q4759444; BRD-K89282837-001-01-0; ANDROGRAPHOLIDE (CONSTITUENT OF ANDROGRAPHIS) [DSC]; Andrographolide, United States Pharmacopeia (USP) Reference Standard; (3E)-3-[2-[(1R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decalin-1-yl]ethylidene]-4-hydroxy-tetrahydrofuran-2-one;Andrographolide; (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decalin-1-yl]ethylidene]-4-hydroxy-tetrahydrofuran-2-one; (5beta,9R,10alpha,14S)-3alpha,14,15,18-Tetrahydroxylabdane-8(20),12-diene-16-oic acid gamma-lactone; (S,E)-4-Hydroxy-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2; 2(3H)-Furanone, 3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-, (1R-(1-alpha(E(S*)),4a-beta,5-alpha,6-alpha,8a-alpha))-; 2(3H)-Furanone,3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-,(3E,4S)-; 3.ALPHA.,14,15,18-TETRAHYDROXY-5.BETA.,9.BETA.H,10.ALPHA.-LABDA-8(20),12-DIEN-16-OIC ACID .GAMMA.-LACTONE
CAS 5508-58-7
PubChem CID 5318517
ChEMBL ID CHEMBL186141
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Organoheterocyclic compou
      • Class: Lactones
        • Subclass: Gamma butyrolactones
          • Direct Parent: Gamma butyrolactones

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 350.4 ALogp: 2.2
HBD: 3 HBA: 5
Rotatable Bonds: 3 Lipinski's rule of five: Accepted
Polar Surface Area: 87.0 Aromatic Rings: 3
Heavy Atoms: 25 QED Weighted: 0.414

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.818 MDCK Permeability: 0.00002850
Pgp-inhibitor: 0 Pgp-substrate: 0.536
Human Intestinal Absorption (HIA): 0.019 20% Bioavailability (F20%): 0.108
30% Bioavailability (F30%): 0.177

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.826 Plasma Protein Binding (PPB): 36.14%
Volume Distribution (VD): 0.557 Fu: 57.76%

ADMET: Metabolism

CYP1A2-inhibitor: 0.029 CYP1A2-substrate: 0.113
CYP2C19-inhibitor: 0.009 CYP2C19-substrate: 0.449
CYP2C9-inhibitor: 0.003 CYP2C9-substrate: 0.066
CYP2D6-inhibitor: 0.002 CYP2D6-substrate: 0.201
CYP3A4-inhibitor: 0.56 CYP3A4-substrate: 0.188

ADMET: Excretion

Clearance (CL): 5.338 Half-life (T1/2): 0.668

ADMET: Toxicity

hERG Blockers: 0.02 Human Hepatotoxicity (H-HT): 0.023
Drug-inuced Liver Injury (DILI): 0.058 AMES Toxicity: 0.719
Rat Oral Acute Toxicity: 0.586 Maximum Recommended Daily Dose: 0.966
Skin Sensitization: 0.127 Carcinogencity: 0.032
Eye Corrosion: 0.005 Eye Irritation: 0.111
Respiratory Toxicity: 0.592
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC002172 0.614 D04VIS 1.000
ENC002493 0.429 D0S0NK 0.373
ENC000956 0.370 D06XMU 0.283
ENC002494 0.369 D0T2PL 0.271
ENC002407 0.360 D08SVH 0.271
ENC003214 0.353 D05BTM 0.271
ENC003143 0.344 D04DJN 0.270
ENC001844 0.333 D0KR5B 0.264
ENC003014 0.333 D0D1SG 0.264
ENC002490 0.333 D0R7JT 0.259
*Note: the compound similarity was calculated by RDKIT.