Thermospine

Details

• Internal ID: 9e16c9b2-ee40-46b1-b80f-cc806e15e248
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Anagyrine-type alkaloids
• IUPAC Name: (1R,9R,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2,4-dien-6-one
• SMILES (Canonical): C1CCN2CC3CC(C2C1)CN4C3=CC=CC4=O
• SMILES (Isomeric): C1CCN2C[C@H]3C[C@@H]([C@@H]2C1)CN4C3=CC=CC4=O
• InChI: InChI=1S/C15H20N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h3,5-6,11-13H,1-2,4,7-10H2/t11-,12-,13+/m1/s1
• InChI Key: FQEQMASDZFXSJI-UPJWGTAASA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀N₂O
• Molecular Weight: 244.33 g/mol
• Exact Mass: 244.157563266 g/mol
• Topological Polar Surface Area (TPSA): 23.60 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 486-90-8
• (-)-Thermopsine
• Thermospine
• l-Thermopsine
• THERMOPSINE,1-
• MLS000737996
• ANAGYRINE
• NSC 21725
• SMR000393674
• Rhombinine
• (7R,14R,14aS)-1,3,4,6,7,13,14,14a-octahydro-2H,11H-7,14-methanodipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one
• 486-89-5
• C15H20N2O
• NSC21725
• Opera_ID_848
• SCHEMBL564928
• 1,2-Benzenediol, 4-ethynyl-
• CHEMBL1324708
• SCHEMBL14476112
• (1R,9R,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2,4-dien-6-one
• DTXSID501317037
• GLXC-14390
• HMS2753N08
• 7,14-Methano-4H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocin-4-one, 7,7a,8,9,10,11,13,14-octahydro-, (7R-(7alpha,7aalpha,14alpha))-
• HY-N5009
• NSC-21725
• AC-34298
• MS-23461
• CS-0032069
• Q63392858
• (1R,9R,10S)-7,15-diazatetracyclo[7.7.1.0?,?.0??,??]heptadeca-2,4-dien-6-one
• (7R,7aS,14R)-7,7a,8,9,10,11,13,14-Octahydro-7,14-methanodipyrido[1,2-a:1',2'-e][1,5]diazocin-4(6H)-one
• 7,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one, 7,7a,8,9,10,11,13,14-octahydro-, [7R-(7.alpha.,7a.alpha.,14.alpha.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9940	99.40%
Caco-2	+	0.8666	86.66%
Blood Brain Barrier	+	0.9106	91.06%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7963	79.63%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.9564	95.64%
OATP1B3 inhibitior	+	0.9531	95.31%
MATE1 inhibitior	+	0.5800	58.00%
OCT2 inhibitior	+	0.8500	85.00%
BSEP inhibitior	-	0.7773	77.73%
P-glycoprotein inhibitior	-	0.9499	94.99%
P-glycoprotein substrate	-	0.6199	61.99%
CYP3A4 substrate	+	0.5350	53.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6675	66.75%
CYP3A4 inhibition	-	0.7448	74.48%
CYP2C9 inhibition	-	0.9072	90.72%
CYP2C19 inhibition	+	0.5878	58.78%
CYP2D6 inhibition	-	0.8923	89.23%
CYP1A2 inhibition	+	0.8778	87.78%
CYP2C8 inhibition	-	0.9490	94.90%
CYP inhibitory promiscuity	+	0.7900	79.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7120	71.20%
Eye corrosion	-	0.9709	97.09%
Eye irritation	-	0.9686	96.86%
Skin irritation	-	0.7008	70.08%
Skin corrosion	-	0.9361	93.61%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3795	37.95%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.7565	75.65%
skin sensitisation	-	0.8583	85.83%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.7320	73.20%
Acute Oral Toxicity (c)	III	0.4858	48.58%
Estrogen receptor binding	-	0.6327	63.27%
Androgen receptor binding	-	0.4900	49.00%
Thyroid receptor binding	-	0.5477	54.77%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6254	62.54%
PPAR gamma	-	0.5131	51.31%
Honey bee toxicity	-	0.9289	92.89%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.7400	74.00%
Fish aquatic toxicity	-	0.7183	71.83%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.93%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.60%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.44%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	91.26%	93.03%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.31%	93.99%
CHEMBL5805	Q9NR97	Toll-like receptor 8	87.77%	96.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.22%	82.69%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.62%	93.04%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.34%	93.40%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.96%	97.25%
CHEMBL4235	P28845	11-beta-hydroxysteroid dehydrogenase 1	85.81%	97.98%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.08%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.56%	99.23%
CHEMBL238	Q01959	Dopamine transporter	83.71%	95.88%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.65%	99.18%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.29%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.80%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.84%	96.09%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.83%	94.23%
CHEMBL3012	Q13946	Phosphodiesterase 7A	80.82%	99.29%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	80.12%	98.33%

Plants that contains it

• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clathrotropis glaucophylla
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euphorbia jolkinii
• Faramea multiflora
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Linnaea chinensis
• Lythrum salicaria
• Melolobium aethiopicum
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Pericopsis angolensis
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora flavescens
• Sophora koreensis
• Stenocereus laevigatus
• Syzygium polycephaloides
• Thermopsis rhombifolia
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 638234
• NPASS: NPC78058
• ChEMBL: CHEMBL1324708
• LOTUS: LTS0136977
• wikiData: Q63392858