(1R,2S,3S,5S,6S,8S,9S,10S,11R,15S,16S)-3,9,10,15-tetrahydroxy-16-methoxy-6-(methoxymethyl)-12,12-dimethyl-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadecan-7-one

Details

• Internal ID: b5b22c09-8d4e-4889-81ab-840fba7694c8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
• IUPAC Name: (1R,2S,3S,5S,6S,8S,9S,10S,11R,15S,16S)-3,9,10,15-tetrahydroxy-16-methoxy-6-(methoxymethyl)-12,12-dimethyl-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadecan-7-one
• SMILES (Canonical): CC1(CCC(C23C1C(C(C45C2C(CC(C4)C(C5=O)COC)O)(OC3OC)O)O)O)C
• SMILES (Isomeric): CC1(CC[C@@H]([C@]23[C@@H]1[C@@H]([C@]([C@]45[C@H]2[C@H](C[C@H](C4)[C@H](C5=O)COC)O)(O[C@@H]3OC)O)O)O)C
• InChI: InChI=1S/C22H34O8/c1-19(2)6-5-13(24)21-14-12(23)7-10-8-20(14,16(25)11(10)9-28-3)22(27,17(26)15(19)21)30-18(21)29-4/h10-15,17-18,23-24,26-27H,5-9H2,1-4H3/t10-,11-,12+,13+,14-,15-,17+,18+,20+,21-,22-/m1/s1
• InChI Key: YRVQGTNACPWQGA-AEIVECIVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₈
• Molecular Weight: 426.50 g/mol
• Exact Mass: 426.22536804 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): 0.05
• H-Bond Acceptor: 8
• 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	+	0.9021	90.21%
Caco-2	-	0.6969	69.69%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7610	76.10%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.8645	86.45%
OATP1B3 inhibitior	+	0.8940	89.40%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9042	90.42%
BSEP inhibitior	-	0.8020	80.20%
P-glycoprotein inhibitior	-	0.7957	79.57%
P-glycoprotein substrate	-	0.5452	54.52%
CYP3A4 substrate	+	0.6979	69.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8339	83.39%
CYP3A4 inhibition	-	0.8968	89.68%
CYP2C9 inhibition	-	0.8053	80.53%
CYP2C19 inhibition	-	0.8383	83.83%
CYP2D6 inhibition	-	0.9522	95.22%
CYP1A2 inhibition	-	0.8075	80.75%
CYP2C8 inhibition	-	0.6486	64.86%
CYP inhibitory promiscuity	-	0.9818	98.18%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7195	71.95%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9477	94.77%
Skin irritation	-	0.7119	71.19%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6709	67.09%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5636	56.36%
skin sensitisation	-	0.8853	88.53%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5199	51.99%
Acute Oral Toxicity (c)	III	0.3746	37.46%
Estrogen receptor binding	+	0.7647	76.47%
Androgen receptor binding	+	0.7659	76.59%
Thyroid receptor binding	+	0.6112	61.12%
Glucocorticoid receptor binding	+	0.6498	64.98%
Aromatase binding	+	0.6701	67.01%
PPAR gamma	+	0.5500	55.00%
Honey bee toxicity	-	0.8038	80.38%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8637	86.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1871	P10275	Androgen Receptor	95.34%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.34%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.86%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.34%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.01%	96.09%
CHEMBL3922	P50579	Methionine aminopeptidase 2	91.22%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.48%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.36%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.90%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.52%	91.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.00%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.51%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.18%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.68%	85.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.62%	96.38%
CHEMBL1937	Q92769	Histone deacetylase 2	84.44%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.25%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.90%	97.25%
CHEMBL5957	P21589	5'-nucleotidase	82.52%	97.78%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.14%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.87%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.62%	95.56%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	80.91%	98.99%
CHEMBL259	P32245	Melanocortin receptor 4	80.34%	95.38%
CHEMBL340	P08684	Cytochrome P450 3A4	80.22%	91.19%

Plants that contains it

• Isodon parvifolius

Cross-Links

• PubChem: 162968013
• LOTUS: LTS0104165
• wikiData: Q105353135