Grosheimin

Details

• Internal ID: 7a6196bc-1f28-49c7-90d3-8d5630b8a36c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,9,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione
• SMILES (Canonical): CC1C2C(CC1=O)C(=C)CC(C3C2OC(=O)C3=C)O
• SMILES (Isomeric): C[C@H]1[C@H]2[C@@H](CC1=O)C(=C)C[C@@H]([C@@H]3[C@@H]2OC(=O)C3=C)O
• InChI: InChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7,9,11-14,17H,1,3-5H2,2H3/t7-,9+,11+,12+,13-,14-/m1/s1
• InChI Key: YGMIBVIKXJJQQJ-MSOSQAFRSA-N
• Popularity: 38 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.25
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• Grosshemin
• Grossheimin
• 22489-66-3
• UNII-ML3SLU81RH
• ML3SLU81RH
• NSC 295425
• CHEBI:5547
• NSC-295425
• 4-beta-H-Guaia-10(14),11(13)-dien-12-oic acid, 6-alpha,8-alpha-dihydroxy-3-oxo-, 12,6-lactone
• AZULENO(4,5-B)FURAN-2,8(3H,4H)-DIONE, OCTAHYDRO-4-HYDROXY-9-METHYL-3,6-BIS(METHYLENE)-, (3AR,4S,6AR,9S,9AR,9BR)-
• Azuleno(4,5-b)furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta))-
• Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)-
• Groshemin
• MLS001164143
• CHEMBL271958
• SCHEMBL1711489
• GTPL12468
• DTXSID60945165
• HMS2864F18
• HY-N10412
• (3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,9,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione
• SMR000539503
• CS-0527771
• C09472
• BRD-K20815397-001-03-7
• Q27106805
• 4.BETA.H-GUAIA-10(14),11(13)-DIEN-12-OIC ACID, 6.ALPHA.,8.ALPHA.-DIHYDROXY-3-OXO-, 12,6-LACTONE
• 4betaH-GUAIA-10(14),11(13)-DIEN-12-OIC ACID, 6alpha,8alpha-DIHYDROXY-3-OXO-, 12,6-LACTONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9898	98.98%
Caco-2	-	0.5309	53.09%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5179	51.79%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8797	87.97%
OATP1B3 inhibitior	+	0.9517	95.17%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9623	96.23%
P-glycoprotein inhibitior	-	0.8927	89.27%
P-glycoprotein substrate	-	0.8700	87.00%
CYP3A4 substrate	+	0.5375	53.75%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8681	86.81%
CYP3A4 inhibition	-	0.8435	84.35%
CYP2C9 inhibition	-	0.9205	92.05%
CYP2C19 inhibition	-	0.8731	87.31%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	-	0.7031	70.31%
CYP2C8 inhibition	-	0.9405	94.05%
CYP inhibitory promiscuity	-	0.9672	96.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9325	93.25%
Carcinogenicity (trinary)	Non-required	0.5236	52.36%
Eye corrosion	-	0.9246	92.46%
Eye irritation	+	0.7509	75.09%
Skin irritation	+	0.5214	52.14%
Skin corrosion	-	0.8153	81.53%
Ames mutagenesis	-	0.5554	55.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5990	59.90%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.7620	76.20%
skin sensitisation	-	0.7430	74.30%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6768	67.68%
Acute Oral Toxicity (c)	III	0.3998	39.98%
Estrogen receptor binding	-	0.5092	50.92%
Androgen receptor binding	-	0.5303	53.03%
Thyroid receptor binding	-	0.5508	55.08%
Glucocorticoid receptor binding	+	0.5747	57.47%
Aromatase binding	-	0.8061	80.61%
PPAR gamma	-	0.8145	81.45%
Honey bee toxicity	-	0.7356	73.56%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5050	50.50%
Fish aquatic toxicity	+	0.9647	96.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.67%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.58%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.88%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.22%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.73%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.42%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.25%	95.89%

Plants that contains it

• Centaurea behen
• Centaurea scabiosa
• Colchicum soboliferum
• Cynara cardunculus
• Pleiotaxis rugosa
• Psorothamnus spinosus
• Trachelospermum asiaticum
• Youngia japonica

Cross-Links

• PubChem: 442256
• NPASS: NPC309757
• ChEMBL: CHEMBL271958
• LOTUS: LTS0260185
• wikiData: Q27106805