Andrographolide
PubChem CID: 5318517
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| Compound Synonyms | Andrographolide, 5508-58-7, CHEBI:65408, HMPL004, UNII-410105JHGR, DTXSID3045980, 410105JHGR, EINECS 226-852-5, (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, NSC 383468, NSC-383468, Andro, DTXCID1025980, 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, ANDROGRAPHOLIDE (USP-RS), ANDROGRAPHOLIDE [USP-RS], (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, (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)-, 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)-, HMPL-004, NSC383468, NCGC00095597-01, (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, (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, 869807-57-8, MFCD07778082, Andrographiside aglycon, Andrographolide, 98%, Andrographolide (Standard), ANDROGRAPHOLIDE [MI], BIDD:ER0530, CHEMBL186141, GTPL9675, MEGxp0_000978, ANDROGRAPHOLIDE [WHO-DD], SCHEMBL12056309, ACon1_002113, HY-N0191R, Andrographolide, analytical standard, HY-N0191, Tox21_111508, BDBM50084419, AKOS015920075, CCG-208428, CS-3334, DB05767, FA17902, NCGC00179817-01, NCGC00179817-02, AS-13637, CAS-5508-58-7, A2459, NS00018311, C20214, ANDROGRAPHOLIDE (CONSTITUENT OF ANDROGRAPHIS), Q4759444, BRD-K89282837-001-01-0, ANDROGRAPHOLIDE (CONSTITUENT OF ANDROGRAPHIS) [DSC], Andrographolide, United States Pharmacopeia (USP) Reference Standard, (1R-(1-alpha(E(S)),4a-beta,5alpha,6alpha,8a-alpha))-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-methylene-decalin-1-yl]ethylidene]-4-hydroxy-tetrahydrofuran-2-one, 226-852-5, 3.ALPHA.,14,15,18-TETRAHYDROXY-5.BETA.,9.BETA.H,10.ALPHA.-LABDA-8(20),12-DIEN-16-OIC ACID .GAMMA.-LACTONE, 3alpha,14,15,18-TETRAHYDROXY-5beta,9betaH,10alpha-LABDA-8(20),12-DIEN-16-OIC ACID gamma-LACTONE |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 87.0 |
| Hydrogen Bond Donor Count | 3.0 |
| Pfizer 3 75 Rule | True |
| Scaffold Graph Level | CC1CCCC1CCC1C(C)CCC2CCCCC21 |
| Np Classifier Class | Labdane diterpenoids |
| Deep Smiles | OC[C@]C)[C@H]O)CC[C@@][C@@H]6CCC=C)[C@H]6C/C=C[C@H]O)COC5=O)))))))))))))C |
| Heavy Atom Count | 25.0 |
| Classyfire Class | Lactones |
| Scaffold Graph Node Level | CC1CCC2CCCCC2C1CCC1CCOC1O |
| Classyfire Subclass | Gamma butyrolactones |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 597.0 |
| Database Name | cmaup_ingredients;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 6.0 |
| Uniprot Id | n.a., P31749, O42275, P81908, Q9NUW8, Q9NPD5, Q9Y6L6, P19838, P40763, P52789, Q96RI1, P10275 |
| 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 |
| Prediction Hob | 1.0 |
| Veber Rule | True |
| Classyfire Superclass | Organoheterocyclic compounds |
| Target Id | NPT163, NPT540 |
| Xlogp | 2.2 |
| Gsk 4 400 Rule | True |
| Molecular Formula | C20H30O5 |
| Scaffold Graph Node Bond Level | C=C1CCC2CCCCC2C1CC=C1CCOC1=O |
| Prediction Swissadme | 1.0 |
| Inchi Key | BOJKULTULYSRAS-OTESTREVSA-N |
| Silicos It Class | Soluble |
| Fcsp3 | 0.75 |
| Logs | -2.836 |
| Rotatable Bond Count | 3.0 |
| Logd | 1.245 |
| Synonyms | andrographolide |
| Esol Class | Soluble |
| Functional Groups | C/C=C1CCOC1=O, C=C(C)C, CO |
| Compound Name | Andrographolide |
| Prediction Hob Swissadme | 1.0 |
| Exact Mass | 350.209 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 350.209 |
| Hydrogen Bond Acceptor Count | 5.0 |
| Molecular Weight | 350.4 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 6.0 |
| Total Bond Stereocenter Count | 1.0 |
| Lipinski Rule Of 5 | True |
| Esol | -3.1756210000000005 |
| 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 |
| 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 |
| Nring | 3.0 |
| Np Classifier Biosynthetic Pathway | Terpenoids |
| Defined Bond Stereocenter Count | 1.0 |
| Egan Rule | True |
| Np Classifier Superclass | Diterpenoids |
- 1. Outgoing r'ship
FOUND_INto/from Ambrosia Artemisiifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Andrographis Echioides (Plant) Rel Props:Reference:ISBN:9788172361266 - 3. Outgoing r'ship
FOUND_INto/from Andrographis Paniculata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Basilicum Polystachyon (Plant) Rel Props:Source_db:npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Carum Carvi (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2011.10643949 - 6. Outgoing r'ship
FOUND_INto/from Holmskioldia Sanguinea (Plant) Rel Props:Reference:ISBN:9770972795006 - 7. Outgoing r'ship
FOUND_INto/from Inula Racemosa (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/21953688 - 8. Outgoing r'ship
FOUND_INto/from Mentha Arvensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 9. Outgoing r'ship
FOUND_INto/from Mentha Canadensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 10. Outgoing r'ship
FOUND_INto/from Nelumbo Nucifera (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 11. Outgoing r'ship
FOUND_INto/from Psidium Guajava (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2018.1431152