Details of the Drug

General Information of Drug (ID: DMMCI4H)

Drug Name
HELENALIN
Synonyms
HELENALIN; 6754-13-8; PF 56; Helenalin A; HSDB 3490; NSC85236; UNII-4GUY9L896T; NSC 85236; BRN 0028081; MLS000728512; CHEBI:5635; 4GUY9L896T; 6alpha,8beta-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone; SMR000445626; Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone; (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione; Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 262.3
Logarithm of the Partition Coefficient (xlogp) 1.4
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C15H18O4
IUPAC Name
(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
Canonical SMILES
C[C@@H]1C[C@@H]2[C@H]([C@@H]([C@]3([C@H]1C=CC3=O)C)O)C(=C)C(=O)O2
InChI
InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1
InChIKey
ZVLOPMNVFLSSAA-XEPQRQSNSA-N
Cross-matching ID
PubChem CID
23205
ChEBI ID
CHEBI:5635
CAS Number
6754-13-8
TTD ID
D0Q6YP

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Angiotensin II receptor type-1 (AGTR1) TT8DBY3 AGTR1_HUMAN Inhibitor [1]
Nuclear factor NF-kappa-B (NFKB) TTSXVID NFKB1_HUMAN ; NFKB2_HUMAN ; TF65_HUMAN ; RELB_HUMAN ; REL_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cyclic AMP-dependent transcription factor ATF-4 (ATF4) OTRFV19J ATF4_HUMAN Gene/Protein Processing [3]
Cytochrome P450 2A13 (CYP2A13) OTVUDLT3 CP2AD_HUMAN Biotransformations [4]
Cytochrome P450 2B6 (CYP2B6) OTOYO4S7 CP2B6_HUMAN Biotransformations [4]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Biotransformations [4]
Cytochrome P450 3A5 (CYP3A5) OTSXFBXB CP3A5_HUMAN Biotransformations [4]
Cytochrome P450 3A7 (CYP3A7) OTTCDHHM CP3A7_HUMAN Biotransformations [4]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [3]
DNA damage-inducible transcript 4 protein (DDIT4) OTHY8SY4 DDIT4_HUMAN Gene/Protein Processing [3]
Transcription factor p65 (RELA) OTUJP9CN TF65_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Angiotensin II receptor type-1 (AGTR1) DTT AGTR1 8.95E-01 1.34E-02 0.07
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
2 Quantitative structure-activity relationship of sesquiterpene lactones as inhibitors of the transcription factor NF-kappaB. J Med Chem. 2004 Nov 18;47(24):6042-54.
3 Helenalin-induced apoptosis is dependent on production of reactive oxygen species and independent of induction of endoplasmic reticulum stress in renal cell carcinoma. Toxicol In Vitro. 2013 Mar;27(2):588-96. doi: 10.1016/j.tiv.2012.10.014. Epub 2012 Oct 30.
4 In vitro metabolism of helenalin and its inhibitory effect on human cytochrome P450 activity. Arch Toxicol. 2022 Mar;96(3):793-808. doi: 10.1007/s00204-021-03218-6. Epub 2022 Jan 6.
5 Apoptosis induction by a novel retinoid-related molecule requires nuclear factor-kappaB activation. Cancer Res. 2005 Jun 1;65(11):4909-17. doi: 10.1158/0008-5472.CAN-04-4124.