(1R,3aR,3bS,4R,5aS,7aS,8aR,11aR,13aS,16aS,16bS,17aS)-1,4-Dihydroxy-1,4,5a,13,13-pentamethyl-3a,3b,4,5a,6,7,11,11a,13a,14,16b,17a-dodecahydro-2H,10H-7a,16a-epoxy-3,9,12,17-tetraoxacyclopenta[3',3a']azuleno[6',5':5,6]cycloocta[1,2,3-cd]-as-indacene-2,5,10,16(1H,8H,13H)-tetrone

Details

• Internal ID: 9eaf4e12-3034-4fc6-add2-b1b2d25dd43c
• Taxonomy: Organoheterocyclic compounds > Furopyrans
• IUPAC Name: (1S,3R,7R,10S,15S,17S,18R,21R,22S,23R,25S,29S)-18,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.115,22.01,13.03,7.03,10.017,21.025,29]nonacos-12-ene-5,14,19,24-tetrone
• SMILES (Canonical): CC1(C2CC=C3C(=O)C45C6C(C7C(O4)C(C(=O)O7)(C)O)C(C(=O)C6(CCC3(O5)CC28C(O1)CC(=O)O8)C)(C)O)C
• SMILES (Isomeric): C[C@]12CC[C@]34C[C@@]56[C@@H](CC=C3C(=O)[C@]7([C@H]1[C@@H]([C@@H]8[C@H](O7)[C@@](C(=O)O8)(C)O)[C@@](C2=O)(C)O)O4)C(O[C@@H]5CC(=O)O6)(C)C
• InChI: InChI=1S/C29H34O11/c1-23(2)13-7-6-12-19(31)29-18-16(17-20(39-29)26(5,35)22(33)36-17)25(4,34)21(32)24(18,3)8-9-27(12,40-29)11-28(13)14(37-23)10-15(30)38-28/h6,13-14,16-18,20,34-35H,7-11H2,1-5H3/t13-,14+,16+,17+,18-,20-,24-,25+,26+,27-,28+,29-/m0/s1
• InChI Key: ZZPMADXAHXHKCG-YDNGANRXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₁
• Molecular Weight: 558.60 g/mol
• Exact Mass: 558.21011190 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.66
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• (1R,3aR,3bS,4R,5aS,7aS,8aR,11aR,13aS,16aS,16bS,17aS)-1,4-Dihydroxy-1,4,5a,13,13-pentamethyl-3a,3b,4,5a,6,7,11,11a,13a,14,16b,17a-dodecahydro-2H,10H-7a,16a-epoxy-3,9,12,17-tetraoxacyclopenta[3',3a']azuleno[6',5':5,6]cycloocta[1,2,3-cd]-as-indacene-2,5,10,16(1H,8H,13H)-tetrone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9584	95.84%
Caco-2	-	0.7675	76.75%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8227	82.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8574	85.74%
OATP1B3 inhibitior	+	0.9702	97.02%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9234	92.34%
P-glycoprotein inhibitior	+	0.6689	66.89%
P-glycoprotein substrate	+	0.5474	54.74%
CYP3A4 substrate	+	0.6866	68.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8992	89.92%
CYP3A4 inhibition	-	0.8413	84.13%
CYP2C9 inhibition	-	0.8356	83.56%
CYP2C19 inhibition	-	0.8992	89.92%
CYP2D6 inhibition	-	0.9455	94.55%
CYP1A2 inhibition	-	0.5277	52.77%
CYP2C8 inhibition	+	0.6803	68.03%
CYP inhibitory promiscuity	-	0.9505	95.05%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4142	41.42%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.8980	89.80%
Skin irritation	+	0.5738	57.38%
Skin corrosion	-	0.8641	86.41%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6454	64.54%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5332	53.32%
skin sensitisation	-	0.7941	79.41%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6628	66.28%
Acute Oral Toxicity (c)	III	0.3977	39.77%
Estrogen receptor binding	+	0.7780	77.80%
Androgen receptor binding	+	0.7546	75.46%
Thyroid receptor binding	+	0.6346	63.46%
Glucocorticoid receptor binding	+	0.7278	72.78%
Aromatase binding	+	0.7321	73.21%
PPAR gamma	+	0.6961	69.61%
Honey bee toxicity	-	0.7401	74.01%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5868	58.68%
Fish aquatic toxicity	+	0.9825	98.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.26%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.49%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.49%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.33%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.98%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.54%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.22%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.16%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.36%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.61%	86.33%
CHEMBL2581	P07339	Cathepsin D	81.75%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.07%	94.45%

Plants that contains it

• Schisandra neglecta

Cross-Links

• PubChem: 46182906
• NPASS: NPC102635