6-[9-[1-formyl-(Z)-ethylidene]-1,6-dihydroxy-10-(3-hydroxypropyl)-6-methyl-(5S,6S)-spiro[4.5]dec-2-yl]-2-(4-methyl-3-pentenyl)-(2Z,4E)-2,4,6-heptatrienyl acetate

Details

• Internal ID: d1233aee-53e6-42d9-87c5-05d1c96731df
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: [(2Z,4E)-6-[(3S,4R,5S,6R,7Z,10S)-4,10-dihydroxy-6-(3-hydroxypropyl)-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-3-yl]-2-(4-methylpent-3-enyl)hepta-2,4,6-trienyl] acetate
• SMILES (Canonical): CC(=CCCC(=CC=CC(=C)C1CCC2(C1O)C(C(=C(C)C=O)CCC2(C)O)CCCO)COC(=O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/C=C/C(=C)[C@@H]1CC[C@@]2([C@@H]1O)[C@@H](/C(=C(/C)\C=O)/CC[C@]2(C)O)CCCO)/COC(=O)C)C
• InChI: InChI=1S/C32H48O6/c1-22(2)10-7-12-26(21-38-25(5)35)13-8-11-23(3)28-16-18-32(30(28)36)29(14-9-19-33)27(24(4)20-34)15-17-31(32,6)37/h8,10-11,13,20,28-30,33,36-37H,3,7,9,12,14-19,21H2,1-2,4-6H3/b11-8+,26-13-,27-24-/t28-,29+,30+,31-,32-/m0/s1
• InChI Key: KPFIRSWIEJGVNZ-DDKMFYJYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₆
• Molecular Weight: 528.70 g/mol
• Exact Mass: 528.34508925 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 5.54
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 12

Synonyms

• 6-[9-[1-formyl-(Z)-ethylidene]-1,6-dihydroxy-10-(3-hydroxypropyl)-6-methyl-(5S,6S)-spiro[4.5]dec-2-yl]-2-(4-methyl-3-pentenyl)-(2Z,4E)-2,4,6-heptatrienyl acetate
• NSC631941
• 16,15-dihydro-spiroiridal
• KPFIRSWIEJGVNZ-DDKMFYJYSA-
• BDBM50106244
• NSC-631941
• (+)-(6R,11S,14S,26R)-29-Acetoxy-26-hydroxy-15,28
• [(2Z,4E)-6-[(3S,4R,5S,6R,7Z,10S)-4,10-Dihydroxy-6-(3-hydroxypropyl)-10-methyl-7-(1-oxopropan-2-ylidene)spiro[4.5]decan-3-yl]-2-(4-methylpent-3-enyl)hepta-2,4,6-trienyl] acetate
• InChI=1/C32H48O6/c1-22(2)10-7-12-26(21-38-25(5)35)13-8-11-23(3)28-16-18-32(30(28)36)29(14-9-19-33)27(24(4)20-34)15-17-31(32,6)37/h8,10-11,13,20,28-30,33,36-37H,3,7,9,12,14-19,21H2,1-2,4-6H3/b11-8+,26-13-,27-24-/t28-,29+,30+,31-,32-/m0/s1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9291	92.91%
Caco-2	-	0.7467	74.67%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7995	79.95%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.8549	85.49%
OATP1B3 inhibitior	+	0.8342	83.42%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5869	58.69%
BSEP inhibitior	+	0.9831	98.31%
P-glycoprotein inhibitior	+	0.7481	74.81%
P-glycoprotein substrate	+	0.5765	57.65%
CYP3A4 substrate	+	0.7126	71.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9005	90.05%
CYP3A4 inhibition	-	0.8676	86.76%
CYP2C9 inhibition	-	0.7019	70.19%
CYP2C19 inhibition	-	0.8860	88.60%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.8998	89.98%
CYP2C8 inhibition	+	0.7016	70.16%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6813	68.13%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9374	93.74%
Skin irritation	-	0.5810	58.10%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8721	87.21%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5857	58.57%
skin sensitisation	-	0.8337	83.37%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5374	53.74%
Acute Oral Toxicity (c)	III	0.4623	46.23%
Estrogen receptor binding	+	0.7861	78.61%
Androgen receptor binding	+	0.7626	76.26%
Thyroid receptor binding	+	0.5290	52.90%
Glucocorticoid receptor binding	+	0.7385	73.85%
Aromatase binding	+	0.6449	64.49%
PPAR gamma	+	0.6043	60.43%
Honey bee toxicity	-	0.7659	76.59%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9910	99.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3638	Q8IV61	RAS guanyl releasing protein 3	41.7 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.49%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.47%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	92.88%	91.24%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.33%	95.50%
CHEMBL2581	P07339	Cathepsin D	89.98%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.56%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.42%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	87.24%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.36%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.34%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.64%	100.00%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	83.58%	95.52%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.18%	96.90%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.15%	86.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.65%	94.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.08%	97.25%
CHEMBL2664	P23526	Adenosylhomocysteinase	81.60%	86.67%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.15%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.91%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.41%	95.56%

Plants that contains it

• Iris cristata

Cross-Links

• PubChem: 9893161
• LOTUS: LTS0021346
• wikiData: Q104390233