(1S,2S,3S,4R,8R,9R,14S)-8-formyl-12,14-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadecane-2,4-dicarboxylic acid

Details

• Internal ID: 26f644ca-702d-486b-986f-0c18923111f6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > C20-gibberellins > C20-gibberellin 6-carboxylic acids
• IUPAC Name: (1S,2S,3S,4R,8R,9R,14S)-8-formyl-12,14-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadecane-2,4-dicarboxylic acid
• SMILES (Canonical): CC1(CCCC2(C1C(C34C2CCC(C3)(C(=C)C4O)O)C(=O)O)C=O)C(=O)O
• SMILES (Isomeric): C[C@]1(CCC[C@@]2([C@@H]1[C@@H]([C@@]34[C@H]2CCC(C3)(C(=C)[C@H]4O)O)C(=O)O)C=O)C(=O)O
• InChI: InChI=1S/C20H26O7/c1-10-14(22)20-8-19(10,27)7-4-11(20)18(9-21)6-3-5-17(2,16(25)26)13(18)12(20)15(23)24/h9,11-14,22,27H,1,3-8H2,2H3,(H,23,24)(H,25,26)/t11-,12+,13+,14+,17+,18+,19?,20-/m0/s1
• InChI Key: ODFFXPNOCMSXHG-ZCVYMCAASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₇
• Molecular Weight: 378.40 g/mol
• Exact Mass: 378.16785316 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 1.23
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9755	97.55%
Caco-2	-	0.6146	61.46%
Blood Brain Barrier	+	0.5027	50.27%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6937	69.37%
OATP2B1 inhibitior	-	0.8619	86.19%
OATP1B1 inhibitior	+	0.8695	86.95%
OATP1B3 inhibitior	+	0.8141	81.41%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5907	59.07%
BSEP inhibitior	-	0.9278	92.78%
P-glycoprotein inhibitior	-	0.8961	89.61%
P-glycoprotein substrate	-	0.6789	67.89%
CYP3A4 substrate	+	0.6314	63.14%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.8548	85.48%
CYP3A4 inhibition	-	0.8903	89.03%
CYP2C9 inhibition	-	0.8685	86.85%
CYP2C19 inhibition	-	0.9072	90.72%
CYP2D6 inhibition	-	0.9478	94.78%
CYP1A2 inhibition	-	0.8121	81.21%
CYP2C8 inhibition	-	0.6090	60.90%
CYP inhibitory promiscuity	-	0.9617	96.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5935	59.35%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9137	91.37%
Skin irritation	+	0.5887	58.87%
Skin corrosion	-	0.9101	91.01%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6560	65.60%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7667	76.67%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.8307	83.07%
Acute Oral Toxicity (c)	I	0.3610	36.10%
Estrogen receptor binding	+	0.7684	76.84%
Androgen receptor binding	+	0.6561	65.61%
Thyroid receptor binding	+	0.6282	62.82%
Glucocorticoid receptor binding	+	0.7294	72.94%
Aromatase binding	+	0.5389	53.89%
PPAR gamma	-	0.6372	63.72%
Honey bee toxicity	-	0.8840	88.40%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9972	99.72%

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	91.23%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.24%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	87.60%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.89%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.30%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.23%	91.19%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.76%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.53%	93.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.87%	100.00%

Plants that contains it

• Helianthus annuus

Cross-Links

• PubChem: 163189079
• LOTUS: LTS0091858
• wikiData: Q105189809