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(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6S)-5-Hydroxy-6-(hydroxymethyl)-2-[(4S,5'R,7S,8R,9S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]-2,3-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

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 1eb6d818-bff0-4e27-9bc2-864069baa940
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
IUPAC Name (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6S)-5-hydroxy-6-(hydroxymethyl)-2-[(4S,5'R,7S,8R,9S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]-2,3-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C51H84O23/c1-20-7-12-50(66-19-20)21(2)32-27(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)51(74-47-42(65)39(62)35(58)30(17-54)69-47)44(71-46-41(64)38(61)34(57)29(16-53)68-46)43(36(59)31(18-55)73-51)70-45-40(63)37(60)33(56)28(15-52)67-45/h20-47,52-65H,5-19H2,1-4H3/t20-,21+,22?,23?,24?,25?,26?,27+,28-,29-,30-,31+,32+,33-,34-,35-,36+,37+,38+,39+,40-,41-,42-,43+,44-,45+,46+,47+,48+,49+,50?,51+/m1/s1
InChI Key JWWCJQFYNBGCAX-UOUUDHCBSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C51H84O23
Molecular Weight 1065.20 g/mol
Exact Mass 1064.54033892 g/mol
Topological Polar Surface Area (TPSA) 366.00 Ų
XlogP -0.20
Atomic LogP (AlogP) -3.32
H-Bond Acceptor 23
H-Bond Donor 14
Rotatable Bonds 11

Synonyms

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Macrostemonoside A
(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6S)-5-Hydroxy-6-(hydroxymethyl)-2-[(4S,5'R,7S,8R,9S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]-2,3-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6S)-5-Hydroxy-6-(hydroxymethyl)-2-[(4S,5'R,7S,8R,9S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]-2,3-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]o
beta-D-Galactopyranoside, (3-beta,5alpha,25R)-spirostan-3-yl O-beta-D-glucopyranosyl-(1-2)-O-(beta-D-glucopyranosyl-(1-3))-O-beta-D-glucopyranosyl-(1-4)-
Tigogenin-3-O-beta-D-glucopyranosyl(1-2)(beta-D-glucopyranosyl(1-3))-beta-D-glucopyranosyl(1-4)-beta-D-galactopyranoside

2D Structure

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2D Structure of (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6S)-5-Hydroxy-6-(hydroxymethyl)-2-[(4S,5'R,7S,8R,9S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]-2,3-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5000 50.00%
Caco-2 - 0.8840 88.40%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.7438 74.38%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9012 90.12%
OATP1B3 inhibitior + 0.9496 94.96%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior - 0.6325 63.25%
P-glycoprotein inhibitior + 0.7365 73.65%
P-glycoprotein substrate - 0.5961 59.61%
CYP3A4 substrate + 0.7488 74.88%
CYP2C9 substrate - 0.8054 80.54%
CYP2D6 substrate - 0.8164 81.64%
CYP3A4 inhibition - 0.9467 94.67%
CYP2C9 inhibition - 0.8999 89.99%
CYP2C19 inhibition - 0.8879 88.79%
CYP2D6 inhibition - 0.9555 95.55%
CYP1A2 inhibition - 0.9151 91.51%
CYP2C8 inhibition + 0.6693 66.93%
CYP inhibitory promiscuity - 0.8947 89.47%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6323 63.23%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.9056 90.56%
Skin irritation - 0.7290 72.90%
Skin corrosion - 0.9529 95.29%
Ames mutagenesis - 0.6233 62.33%
Human Ether-a-go-go-Related Gene inhibition + 0.7512 75.12%
Micronuclear - 0.8900 89.00%
Hepatotoxicity - 0.9375 93.75%
skin sensitisation - 0.9466 94.66%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.6333 63.33%
Mitochondrial toxicity - 0.5125 51.25%
Nephrotoxicity - 0.8372 83.72%
Acute Oral Toxicity (c) I 0.7624 76.24%
Estrogen receptor binding + 0.7908 79.08%
Androgen receptor binding + 0.7316 73.16%
Thyroid receptor binding - 0.5857 58.57%
Glucocorticoid receptor binding + 0.5430 54.30%
Aromatase binding + 0.6544 65.44%
PPAR gamma + 0.7282 72.82%
Honey bee toxicity - 0.5363 53.63%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.8557 85.57%

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 98.86% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.58% 91.11%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 95.33% 95.58%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.23% 97.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 95.18% 96.61%
CHEMBL237 P41145 Kappa opioid receptor 94.96% 98.10%
CHEMBL4618 P09960 Leukotriene A4 hydrolase 93.05% 97.86%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 89.96% 95.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.66% 100.00%
CHEMBL233 P35372 Mu opioid receptor 89.64% 97.93%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 88.73% 89.05%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.30% 95.89%
CHEMBL259 P32245 Melanocortin receptor 4 87.84% 95.38%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 87.42% 91.24%
CHEMBL226 P30542 Adenosine A1 receptor 87.37% 95.93%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 86.75% 96.38%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 86.26% 95.83%
CHEMBL206 P03372 Estrogen receptor alpha 86.11% 97.64%
CHEMBL5255 O00206 Toll-like receptor 4 86.09% 92.50%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 85.94% 92.86%
CHEMBL2996 Q05655 Protein kinase C delta 85.64% 97.79%
CHEMBL2842 P42345 Serine/threonine-protein kinase mTOR 85.56% 92.78%
CHEMBL204 P00734 Thrombin 85.53% 96.01%
CHEMBL325 Q13547 Histone deacetylase 1 85.46% 95.92%
CHEMBL2815 P04629 Nerve growth factor receptor Trk-A 83.59% 87.16%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.67% 97.25%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 82.05% 100.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.70% 92.94%
CHEMBL2534 O15530 3-phosphoinositide dependent protein kinase-1 81.67% 95.36%
CHEMBL5028 O14672 ADAM10 81.09% 97.50%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.93% 94.45%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 80.81% 97.50%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 80.79% 100.00%
CHEMBL4302 P08183 P-glycoprotein 1 80.57% 92.98%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 80.25% 96.77%

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.
Allium macrostemon

Cross-Links

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PubChem 197480
NPASS NPC183925