Paraherquamide

Details

• Internal ID: b05bb5b5-6dcc-41f3-8f70-7a5779bdf32d
• Taxonomy: Organoheterocyclic compounds > Azaspirodecane derivatives
• IUPAC Name: (1'S,6'R,7'R,8R,9'S)-6'-hydroxy-4,4,6',10',10',13'-hexamethylspiro[10H-[1,4]dioxepino[2,3-g]indole-8,11'-3,13-diazatetracyclo[5.5.2.01,9.03,7]tetradecane]-9,14'-dione
• SMILES (Canonical): CC1(C=COC2=C(O1)C=CC3=C2NC(=O)C34CC56CN7CCC(C7(CC5C4(C)C)C(=O)N6C)(C)O)C
• SMILES (Isomeric): C[C@]1(CCN2[C@]13C[C@@H]4[C@](C2)(C[C@@]5(C4(C)C)C6=C(C7=C(C=C6)OC(C=CO7)(C)C)NC5=O)N(C3=O)C)O
• InChI: InChI=1S/C28H35N3O5/c1-23(2)10-12-35-20-17(36-23)8-7-16-19(20)29-21(32)27(16)14-26-15-31-11-9-25(5,34)28(31,22(33)30(26)6)13-18(26)24(27,3)4/h7-8,10,12,18,34H,9,11,13-15H2,1-6H3,(H,29,32)/t18-,25+,26+,27+,28-/m0/s1
• InChI Key: UVZZDDLIOJPDKX-ITKQZBBDSA-N
• Popularity: 41 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₅N₃O₅
• Molecular Weight: 493.60 g/mol
• Exact Mass: 493.25767123 g/mol
• Topological Polar Surface Area (TPSA): 91.30 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.80
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• Paraherquamide A
• 77392-58-6
• (-)-Paraherquamide
• (-)-Paraherquamide A
• UNII-R72VB4E4KC
• BRN 3599562
• R72VB4E4KC
• C28H35N3O5
• (1'S,6'R,7'R,8R,9'S)-6'-hydroxy-4,4,6',10',10',13'-hexamethylspiro[10H-[1,4]dioxepino[2,3-g]indole-8,11'-3,13-diazatetracyclo[5.5.2.01,9.03,7]tetradecane]-9,14'-dione
• PARAHERQUAMIDE [MI]
• SCHEMBL1547700
• DTXSID70998607
• NSC784317
• AT37274
• NSC-784317
• LS-101267
• Q27287870
• (1'R,5'AS,7'R,8'AS,9'AR)-2',3',8'A,9'-TETRAHYDRO-1'-HYDROXY-1',4,4,8',8',11'-HEXAMETHYLSPIRO(4H,8H-(1,4)DIOXEPINO(2,3-G)INDOLE-8,7'(8'H)-(5H,6H-5A,9A)(IMINOMETHANO)(1H)CYCLOPENT(F)INDOLIZINE)-9,10'(10H)-DIONE
• 1',9-Dihydroxy-1',4,4,8',8',11'-hexamethyl-2',3',8'a,9'-tetrahydro-1'H,4H,5'H,6'H,8'H-spiro[1,4-dioxepino[2,3-g]indole-8,7'-[5a,9a](epiminomethano)cyclopenta[f]indolizin]-10'-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9328	93.28%
Caco-2	-	0.6629	66.29%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4074	40.74%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.8692	86.92%
OATP1B3 inhibitior	+	0.9254	92.54%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9647	96.47%
P-glycoprotein inhibitior	+	0.6985	69.85%
P-glycoprotein substrate	+	0.6874	68.74%
CYP3A4 substrate	+	0.7089	70.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6707	67.07%
CYP3A4 inhibition	-	0.8962	89.62%
CYP2C9 inhibition	-	0.7982	79.82%
CYP2C19 inhibition	-	0.7884	78.84%
CYP2D6 inhibition	-	0.8732	87.32%
CYP1A2 inhibition	-	0.9410	94.10%
CYP2C8 inhibition	+	0.5363	53.63%
CYP inhibitory promiscuity	-	0.9730	97.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5774	57.74%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9426	94.26%
Skin irritation	-	0.7763	77.63%
Skin corrosion	-	0.9302	93.02%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8746	87.46%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.5402	54.02%
skin sensitisation	-	0.8602	86.02%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.6800	68.00%
Acute Oral Toxicity (c)	III	0.6116	61.16%
Estrogen receptor binding	+	0.7971	79.71%
Androgen receptor binding	+	0.7681	76.81%
Thyroid receptor binding	+	0.7061	70.61%
Glucocorticoid receptor binding	+	0.7023	70.23%
Aromatase binding	+	0.7667	76.67%
PPAR gamma	+	0.6736	67.36%
Honey bee toxicity	-	0.8198	81.98%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9291	92.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5697	Q9GZT9	Egl nine homolog 1	97.15%	93.40%
CHEMBL2581	P07339	Cathepsin D	96.61%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.55%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.59%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.32%	93.99%
CHEMBL3922	P50579	Methionine aminopeptidase 2	92.52%	97.28%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.46%	99.23%
CHEMBL4208	P20618	Proteasome component C5	89.68%	90.00%
CHEMBL1937	Q92769	Histone deacetylase 2	89.58%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.45%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.21%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.57%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.96%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.91%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.54%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.10%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.70%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.23%	82.69%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.09%	100.00%

Plants that contains it

• Fissistigma balansae

Cross-Links

• PubChem: 156934
• NPASS: NPC84130
• LOTUS: LTS0080559
• wikiData: Q27287870