(2S,3R,4S,4aR)-2,3,7-trihydroxy-4-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,4a,5-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

Details

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Internal ID fb2e5bba-08cb-447c-ab82-bd16e2a6ef05
Taxonomy Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Phenanthridines and derivatives
IUPAC Name (2S,3R,4S,4aR)-2,3,7-trihydroxy-4-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,4a,5-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
SMILES (Canonical) C1OC2=C(O1)C(=C3C(=C2)C4=CC(C(C(C4NC3=O)OC5C(OC(C(C5O)O)O)CO)O)O)O
SMILES (Isomeric) C1OC2=C(O1)C(=C3C(=C2)C4=C[C@@H]([C@H]([C@H]([C@@H]4NC3=O)O[C@@H]5[C@H](O[C@H]([C@@H]([C@H]5O)O)O)CO)O)O)O
InChI InChI=1S/C20H23NO12/c22-3-9-17(14(26)15(27)20(29)32-9)33-18-11-6(1-7(23)12(18)24)5-2-8-16(31-4-30-8)13(25)10(5)19(28)21-11/h1-2,7,9,11-12,14-15,17-18,20,22-27,29H,3-4H2,(H,21,28)/t7-,9+,11+,12+,14+,15+,17+,18-,20+/m0/s1
InChI Key FSIQVSYWJNFNEG-NPTQTVEQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H23NO12
Molecular Weight 469.40 g/mol
Exact Mass 469.12202517 g/mol
Topological Polar Surface Area (TPSA) 208.00 Ų
XlogP -3.30
Atomic LogP (AlogP) -3.46
H-Bond Acceptor 12
H-Bond Donor 8
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,4S,4aR)-2,3,7-trihydroxy-4-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,4a,5-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8197 81.97%
Caco-2 - 0.9048 90.48%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.5374 53.74%
OATP2B1 inhibitior - 0.7077 70.77%
OATP1B1 inhibitior + 0.8207 82.07%
OATP1B3 inhibitior + 0.9458 94.58%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior - 0.6989 69.89%
P-glycoprotein inhibitior - 0.8453 84.53%
P-glycoprotein substrate - 0.6283 62.83%
CYP3A4 substrate + 0.6299 62.99%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8682 86.82%
CYP3A4 inhibition - 0.6649 66.49%
CYP2C9 inhibition - 0.7969 79.69%
CYP2C19 inhibition - 0.7277 72.77%
CYP2D6 inhibition - 0.7846 78.46%
CYP1A2 inhibition - 0.6320 63.20%
CYP2C8 inhibition - 0.5799 57.99%
CYP inhibitory promiscuity + 0.5438 54.38%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6059 60.59%
Eye corrosion - 0.9870 98.70%
Eye irritation - 0.9362 93.62%
Skin irritation - 0.7859 78.59%
Skin corrosion - 0.9362 93.62%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6827 68.27%
Micronuclear + 0.7900 79.00%
Hepatotoxicity + 0.5022 50.22%
skin sensitisation - 0.8126 81.26%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity - 0.7415 74.15%
Acute Oral Toxicity (c) III 0.5882 58.82%
Estrogen receptor binding + 0.6518 65.18%
Androgen receptor binding + 0.6426 64.26%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding - 0.5000 50.00%
Aromatase binding + 0.5699 56.99%
PPAR gamma + 0.6300 63.00%
Honey bee toxicity - 0.6910 69.10%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity - 0.4744 47.44%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.56% 91.11%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 97.88% 96.77%
CHEMBL2581 P07339 Cathepsin D 95.75% 98.95%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 93.18% 83.57%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.32% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.24% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.93% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.34% 96.09%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 91.11% 96.21%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.05% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.92% 94.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.49% 95.89%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.60% 92.62%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.00% 100.00%
CHEMBL3401 O75469 Pregnane X receptor 84.56% 94.73%
CHEMBL4296 Q15858 Sodium channel protein type IX alpha subunit 83.76% 96.11%
CHEMBL4208 P20618 Proteasome component C5 82.91% 90.00%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 82.32% 86.92%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 82.23% 89.34%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.51% 97.28%
CHEMBL218 P21554 Cannabinoid CB1 receptor 80.16% 96.61%

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.
Pancratium maritimum

Cross-Links

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PubChem 162927914
LOTUS LTS0126510
wikiData Q105000657