Shikonin
PubChem CID: 479503
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| Compound Synonyms | shikonin, 517-89-5, Isoarnebin 4, (R)-5,8-Dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione, Tokyo Violet, (R)-(+)-Shikonin, Shikonin S, (+)-Shikonin, UNII-3IK6592UBW, Shikonine, NSC 252844, CCRIS 6492, HSDB 8100, BRN 2058010, Anchusin, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione, 3IK6592UBW, CHEBI:81068, DTXSID30199653, 1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-, C.I. 75535, (+)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone, C17412, 1,4-NAPHTHOQUINONE, 5,8-DIHYDROXY-2-(1-HYDROXY-4-METHYL-3-PENTENYL)-, (+)-, (-)-Shikonin, 1,4-naphthalenedione, 5,8-dihydroxy-2-((1r)-1-hydroxy-4-methyl-3-pentenyl)-, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dihydronaphthalene-1,4-dione, SR-05000001466, C.I. 75535, Isoarnebin 4, Shikonin?, NSC-252844, 1,4-Naphthalenedione, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-pentenyl]-, 5,8-DIHYDROXY-2-((1R)-1-HYDROXY-4-METHYLPENT-3-ENYL)NAPHTHALENE-1,4-DIONE, Shikonin,(S), MFCD00075680, Shikonin (Standard), SCHEMBL33969, BSPBio_001270, MLS006010149, HY-N0822R, DTXCID90122144, HMS1792P11, HMS1990P11, HMS2089L09, HMS3403P11, HY-N0822, s8279, AKOS015900416, CCG-208272, CS-5906, FS65933, NCGC00163489-01, NCGC00163489-02, NCGC00163489-04, NCGC00163489-05, AC-26871, AS-13554, BP-30212, SMR002530673, C15906, SR-05000001466-1, SR-05000001466-3, Q27155024 |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 94.8 |
| Hydrogen Bond Donor Count | 3.0 |
| Pfizer 3 75 Rule | True |
| Scaffold Graph Level | CC1CCC(C)C2CCCCC12 |
| Np Classifier Class | Naphthoquinones |
| Deep Smiles | CC=CC[C@H]C=CC=O)ccC6=O))cO)ccc6O))))))))))O))))C |
| Heavy Atom Count | 21.0 |
| Classyfire Class | Naphthalenes |
| Scaffold Graph Node Level | OC1CCC(O)C2CCCCC12 |
| Classyfire Subclass | Naphthoquinones |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 501.0 |
| Database Name | cmaup_ingredients;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 1.0 |
| Uniprot Id | P11387, P18031, P25044, P35610, O75908, n.a., P46063, Q16637, P10636, P10828, P00352, Q9F4F7, P97697, P02791, Q92830, Q13951, Q96KQ7, P11473, Q9UBT6, Q9IGQ6, O42275, P81908, P27695, P30613, P14618, Q9S446, P30304, P30305, Q02880, P00533, Q8WTS6 |
| Iupac Name | 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione |
| Prediction Hob | 1.0 |
| Veber Rule | True |
| Classyfire Superclass | Benzenoids |
| Target Id | NPT143, NPT178, NPT1214, NPT2584, NPT47, NPT93, NPT51, NPT46, NPT94, NPT6230, NPT52, NPT3060, NPT911, NPT285, NPT1385 |
| Xlogp | 3.0 |
| Gsk 4 400 Rule | True |
| Molecular Formula | C16H16O5 |
| Scaffold Graph Node Bond Level | O=C1C=CC(=O)c2ccccc21 |
| Prediction Swissadme | 0.0 |
| Inchi Key | NEZONWMXZKDMKF-SNVBAGLBSA-N |
| Silicos It Class | Soluble |
| Fcsp3 | 0.25 |
| Logs | -3.46 |
| Rotatable Bond Count | 3.0 |
| Logd | 2.936 |
| Synonyms | arnebin-4, shikonin |
| Esol Class | Soluble |
| Functional Groups | CC1=CC(=O)ccC1=O, CC=C(C)C, CO, cO |
| Compound Name | Shikonin |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 288.1 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 288.1 |
| Hydrogen Bond Acceptor Count | 5.0 |
| Molecular Weight | 288.29 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 1.0 |
| Total Bond Stereocenter Count | 0.0 |
| Lipinski Rule Of 5 | True |
| Esol | -3.505682371428571 |
| Inchi | InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1 |
| Smiles | CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C |
| Nring | 2.0 |
| Np Classifier Biosynthetic Pathway | Polyketides |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Np Classifier Superclass | Naphthalenes |
- 1. Outgoing r'ship
FOUND_INto/from Alkanna Tinctoria (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/12210768 - 2. Outgoing r'ship
FOUND_INto/from Arnebia Euchroma (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 3. Outgoing r'ship
FOUND_INto/from Arnebia Guttata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Arnebia Nobilis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Eucalyptus Coccifera (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 6. Outgoing r'ship
FOUND_INto/from Isodon Japonica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 7. Outgoing r'ship
FOUND_INto/from Lithospermum Erythrorhizon (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 8. Outgoing r'ship
FOUND_INto/from Lithospermum Officinale (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 9. Outgoing r'ship
FOUND_INto/from Onosma Hispida (Plant) Rel Props:Reference:ISBN:9770972795006 - 10. Outgoing r'ship
FOUND_INto/from Onosma Paniculata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 11. Outgoing r'ship
FOUND_INto/from Rhizomnium Magnifolium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 12. Outgoing r'ship
FOUND_INto/from Strychnos Usambarensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all