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Name |
Andrographolide
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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
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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
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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
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InChIKey |
BOJKULTULYSRAS-OTESTREVSA-N
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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
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CAS | 5508-58-7 | |
PubChem CID | 5318517 | |
ChEMBL ID | CHEMBL186141 |
Chemical Classification: |
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Endophyte ID | Endophyte Name | Family | Genus | Taxonomy ID | GenBank ID | Closest GenBank ID | Reference | |
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Endophyte ID | Endophyte Name | Family | Genus | Taxonomy ID | GenBank ID | Closest GenBank ID | Reference |
Bioactivity Name | Target ID | Target Name | Target Type | Target Organism | Target Organism ID | Potency of Bioactivity | Activity Type | Value | Unit | Endophyte ID | Endophyte Name | |
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Bioactivity Name | Target ID | Target Name | Target Type | Target Organism | Target Organism ID | Potency of Bioactivity | Activity Type | Value | Unit | Endophyte ID | Endophyte Name |
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 |
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 |
Blood-Brain-Barrier Penetration (BBB): | 0.826 | Plasma Protein Binding (PPB): | 36.14% |
Volume Distribution (VD): | 0.557 | Fu: | 57.76% |
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 |
Clearance (CL): | 5.338 | Half-life (T1/2): | 0.668 |
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 |
Similar NPs | Similar Drugs | ||||||
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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 |