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Spinosine

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 05d36bef-2144-442d-92c7-001de97b330d
Taxonomy Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name (13aS)-2,3-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-10,11-diol
SMILES (Canonical) COC1=C(C=C2C3CC4=CC(=C(C=C4CN3CCC2=C1)O)O)OC
SMILES (Isomeric) COC1=C(C=C2[C@@H]3CC4=CC(=C(C=C4CN3CCC2=C1)O)O)OC
InChI InChI=1S/C19H21NO4/c1-23-18-8-11-3-4-20-10-13-7-17(22)16(21)6-12(13)5-15(20)14(11)9-19(18)24-2/h6-9,15,21-22H,3-5,10H2,1-2H3/t15-/m0/s1
InChI Key VAKIESMDOCVMDV-HNNXBMFYSA-N
Popularity 3 references in papers

Physical and Chemical Properties

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Molecular Formula C19H21NO4
Molecular Weight 327.40 g/mol
Exact Mass 327.14705815 g/mol
Topological Polar Surface Area (TPSA) 62.20 Ų
XlogP 2.60
Atomic LogP (AlogP) 2.77
H-Bond Acceptor 5
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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S-(-)-Spinosine
175274-51-8
(S)-2,3-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-10,11-diol
(?)-Spinosine
SCHEMBL123459
DTXSID20938639
CHEBI:191167
(13aS)-2,3-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-10,11-diol
6H-Dibenzo(a,g)quinolizine-10,11-diol, 5,8,13,13a-tetrahydro-2,3-dimethoxy-, (13aS)-
6H-Dibenzo(a,g)quinolizine-10,11-diol, 5,8,13,13a-tetrahydro-2,3-dimethoxy-, (S)-

2D Structure

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2D Structure of Spinosine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7194 71.94%
Caco-2 + 0.7344 73.44%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.7392 73.92%
OATP2B1 inhibitior - 0.8542 85.42%
OATP1B1 inhibitior + 0.9421 94.21%
OATP1B3 inhibitior + 0.9601 96.01%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.5000 50.00%
BSEP inhibitior - 0.4504 45.04%
P-glycoprotein inhibitior - 0.6247 62.47%
P-glycoprotein substrate + 0.5463 54.63%
CYP3A4 substrate + 0.5512 55.12%
CYP2C9 substrate + 0.7865 78.65%
CYP2D6 substrate + 0.7790 77.90%
CYP3A4 inhibition - 0.9290 92.90%
CYP2C9 inhibition - 0.9150 91.50%
CYP2C19 inhibition - 0.5720 57.20%
CYP2D6 inhibition + 0.6856 68.56%
CYP1A2 inhibition + 0.8094 80.94%
CYP2C8 inhibition - 0.7565 75.65%
CYP inhibitory promiscuity - 0.8867 88.67%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6763 67.63%
Eye corrosion - 0.9892 98.92%
Eye irritation - 0.7990 79.90%
Skin irritation - 0.7199 71.99%
Skin corrosion - 0.9356 93.56%
Ames mutagenesis - 0.7854 78.54%
Human Ether-a-go-go-Related Gene inhibition - 0.5274 52.74%
Micronuclear + 0.6300 63.00%
Hepatotoxicity - 0.6500 65.00%
skin sensitisation - 0.8828 88.28%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity + 0.4939 49.39%
Acute Oral Toxicity (c) III 0.4964 49.64%
Estrogen receptor binding + 0.6843 68.43%
Androgen receptor binding - 0.6093 60.93%
Thyroid receptor binding + 0.7288 72.88%
Glucocorticoid receptor binding + 0.7615 76.15%
Aromatase binding - 0.5742 57.42%
PPAR gamma + 0.5301 53.01%
Honey bee toxicity - 0.8382 83.82%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.6351 63.51%
Fish aquatic toxicity - 0.3737 37.37%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.36% 96.09%
CHEMBL241 Q14432 Phosphodiesterase 3A 94.58% 92.94%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.29% 91.11%
CHEMBL217 P14416 Dopamine D2 receptor 94.16% 95.62%
CHEMBL2041 P07949 Tyrosine-protein kinase receptor RET 92.81% 91.79%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.04% 85.14%
CHEMBL2581 P07339 Cathepsin D 90.77% 98.95%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 89.89% 93.40%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 88.89% 91.03%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 87.68% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.61% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.29% 95.89%
CHEMBL2056 P21728 Dopamine D1 receptor 86.53% 91.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 86.31% 93.99%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.81% 94.45%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 84.88% 89.62%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.46% 95.56%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 83.17% 82.38%
CHEMBL4208 P20618 Proteasome component C5 82.64% 90.00%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 82.39% 90.24%
CHEMBL4247 Q9UM73 ALK tyrosine kinase receptor 82.22% 96.86%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 82.04% 90.71%
CHEMBL1744525 P43490 Nicotinamide phosphoribosyltransferase 81.00% 96.25%
CHEMBL4040 P28482 MAP kinase ERK2 80.35% 83.82%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.03% 99.17%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Annona spinescens
Annona squamosa

Cross-Links

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PubChem 177294
NPASS NPC88372
LOTUS LTS0077522
wikiData Q82915014