(7Z,9S,10S,11S,12Z,14S,16Z,20S,21S,22Z,24Z,26Z)-31-chloro-4,10,14,20-tetrahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.05,33]tetratriaconta-1(33),2,4,7,12,16,22,24,26,30-decaene-6,18,28,32,34-pentone

Details

• Internal ID: 1f277e18-ab9c-4663-875c-1c5ecb0174e2
• Taxonomy: Phenylpropanoids and polyketides > Macrolactams
• IUPAC Name: (7Z,9S,10S,11S,12Z,14S,16Z,20S,21S,22Z,24Z,26Z)-31-chloro-4,10,14,20-tetrahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.05,33]tetratriaconta-1(33),2,4,7,12,16,22,24,26,30-decaene-6,18,28,32,34-pentone
• SMILES (Canonical): CC1C=CC=CC=C(C(=O)NC2=C(C(=O)C3=C(C2=O)C=C(C(=C3C(=O)C(=CC(C(C(C=CC(CC=C(C(=O)CC1O)C)O)C)O)C)C)O)C)Cl)C
• SMILES (Isomeric): C[C@H]1/C=C\C=C/C=C(\C(=O)NC2=C(C(=O)C3=C(C2=O)C=C(C(=C3C(=O)/C(=C\[C@@H]([C@H]([C@H](/C=C\[C@H](C/C=C(\C(=O)C[C@@H]1O)/C)O)C)O)C)/C)O)C)Cl)/C
• InChI: InChI=1S/C40H46ClNO9/c1-20-11-9-8-10-12-23(4)40(51)42-34-33(41)39(50)31-28(38(34)49)18-26(7)37(48)32(31)36(47)25(6)17-24(5)35(46)22(3)14-16-27(43)15-13-21(2)30(45)19-29(20)44/h8-14,16-18,20,22,24,27,29,35,43-44,46,48H,15,19H2,1-7H3,(H,42,51)/b10-8-,11-9-,16-14-,21-13-,23-12-,25-17-/t20-,22-,24-,27-,29-,35-/m0/s1
• InChI Key: AXEGRHYJHHPVDH-GGBROUGNSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₆ClNO₉
• Molecular Weight: 720.20 g/mol
• Exact Mass: 719.2861097 g/mol
• Topological Polar Surface Area (TPSA): 178.00 Ų
• XlogP: 6.10
• Atomic LogP (AlogP): 5.69
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.8467	84.67%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6772	67.72%
OATP2B1 inhibitior	+	0.7236	72.36%
OATP1B1 inhibitior	+	0.8319	83.19%
OATP1B3 inhibitior	+	0.9354	93.54%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9770	97.70%
P-glycoprotein inhibitior	+	0.7418	74.18%
P-glycoprotein substrate	+	0.6917	69.17%
CYP3A4 substrate	+	0.7193	71.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8715	87.15%
CYP3A4 inhibition	-	0.5510	55.10%
CYP2C9 inhibition	-	0.6576	65.76%
CYP2C19 inhibition	-	0.5631	56.31%
CYP2D6 inhibition	-	0.8676	86.76%
CYP1A2 inhibition	-	0.5240	52.40%
CYP2C8 inhibition	+	0.7100	71.00%
CYP inhibitory promiscuity	-	0.5391	53.91%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7358	73.58%
Carcinogenicity (trinary)	Non-required	0.4459	44.59%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9196	91.96%
Skin irritation	-	0.7840	78.40%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7215	72.15%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.8482	84.82%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6406	64.06%
Acute Oral Toxicity (c)	III	0.5975	59.75%
Estrogen receptor binding	+	0.8122	81.22%
Androgen receptor binding	+	0.7777	77.77%
Thyroid receptor binding	+	0.6189	61.89%
Glucocorticoid receptor binding	+	0.7557	75.57%
Aromatase binding	+	0.5747	57.47%
PPAR gamma	+	0.7245	72.45%
Honey bee toxicity	-	0.7168	71.68%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9700	97.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	440 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.24%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.85%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	95.55%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.22%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.21%	95.56%
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	94.97%	95.52%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	94.55%	96.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	93.44%	90.71%
CHEMBL5145	P15056	Serine/threonine-protein kinase B-raf	90.37%	97.90%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	90.28%	85.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.24%	89.00%
CHEMBL217	P14416	Dopamine D2 receptor	89.02%	95.62%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.98%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.88%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.68%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.64%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.41%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.31%	96.09%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	84.29%	88.84%
CHEMBL3401	O75469	Pregnane X receptor	84.10%	94.73%
CHEMBL4530	P00488	Coagulation factor XIII	83.58%	96.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.43%	86.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.21%	96.90%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.11%	96.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.02%	96.67%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.89%	89.34%
CHEMBL4208	P20618	Proteasome component C5	80.70%	90.00%

Plants that contains it

• Hypericum geminiflorum

Cross-Links

• PubChem: 101636761
• LOTUS: LTS0016829
• wikiData: Q105197597