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(3S,3'R,4S,5R,5'S,10S,13S,14S,16R,17S)-3,16-dihydroxy-4-(hydroxymethyl)-3',4,10,13,14-pentamethyl-5'-propanoylspiro[2,3,5,6,7,11,12,16-octahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-15-one

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 ed6646c3-181c-4d22-8a68-8549ca06f80f
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (3S,3'R,4S,5R,5'S,10S,13S,14S,16R,17S)-3,16-dihydroxy-4-(hydroxymethyl)-3',4,10,13,14-pentamethyl-5'-propanoylspiro[2,3,5,6,7,11,12,16-octahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-15-one
SMILES (Canonical) CCC(=O)C1CC(C2(O1)C(C(=O)C3(C2(CCC4=C3CCC5C4(CCC(C5(C)CO)O)C)C)C)O)C
SMILES (Isomeric) CCC(=O)[C@@H]1C[C@H]([C@@]2(O1)[C@H](C(=O)[C@@]3([C@@]2(CCC4=C3CC[C@@H]5[C@@]4(CC[C@@H]([C@]5(C)CO)O)C)C)C)O)C
InChI InChI=1S/C29H44O6/c1-7-19(31)20-14-16(2)29(35-20)24(34)23(33)28(6)18-8-9-21-25(3,17(18)10-13-27(28,29)5)12-11-22(32)26(21,4)15-30/h16,20-22,24,30,32,34H,7-15H2,1-6H3/t16-,20+,21-,22+,24+,25-,26-,27+,28-,29-/m1/s1
InChI Key KWZWSZIGIKJZCY-XPRZMMGKSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C29H44O6
Molecular Weight 488.70 g/mol
Exact Mass 488.31378912 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 3.20
Atomic LogP (AlogP) 3.75
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3S,3'R,4S,5R,5'S,10S,13S,14S,16R,17S)-3,16-dihydroxy-4-(hydroxymethyl)-3',4,10,13,14-pentamethyl-5'-propanoylspiro[2,3,5,6,7,11,12,16-octahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-15-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9884 98.84%
Caco-2 - 0.5863 58.63%
Blood Brain Barrier + 0.8356 83.56%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7620 76.20%
OATP2B1 inhibitior - 0.7087 70.87%
OATP1B1 inhibitior + 0.8328 83.28%
OATP1B3 inhibitior + 0.9710 97.10%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior + 0.6293 62.93%
BSEP inhibitior + 0.6883 68.83%
P-glycoprotein inhibitior - 0.5093 50.93%
P-glycoprotein substrate - 0.5765 57.65%
CYP3A4 substrate + 0.6863 68.63%
CYP2C9 substrate - 0.8236 82.36%
CYP2D6 substrate - 0.7885 78.85%
CYP3A4 inhibition + 0.6110 61.10%
CYP2C9 inhibition - 0.8531 85.31%
CYP2C19 inhibition - 0.8813 88.13%
CYP2D6 inhibition - 0.9311 93.11%
CYP1A2 inhibition - 0.9143 91.43%
CYP2C8 inhibition + 0.5211 52.11%
CYP inhibitory promiscuity - 0.8034 80.34%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4824 48.24%
Eye corrosion - 0.9910 99.10%
Eye irritation - 0.9101 91.01%
Skin irritation + 0.7038 70.38%
Skin corrosion - 0.9384 93.84%
Ames mutagenesis - 0.5970 59.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6479 64.79%
Micronuclear - 0.8300 83.00%
Hepatotoxicity - 0.6925 69.25%
skin sensitisation - 0.9322 93.22%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.9778 97.78%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity - 0.5618 56.18%
Acute Oral Toxicity (c) III 0.6482 64.82%
Estrogen receptor binding + 0.7367 73.67%
Androgen receptor binding + 0.7598 75.98%
Thyroid receptor binding + 0.5996 59.96%
Glucocorticoid receptor binding + 0.8342 83.42%
Aromatase binding + 0.7734 77.34%
PPAR gamma - 0.5000 50.00%
Honey bee toxicity - 0.8092 80.92%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9763 97.63%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.07% 97.25%
CHEMBL2581 P07339 Cathepsin D 94.26% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.30% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.01% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 91.22% 90.17%
CHEMBL4040 P28482 MAP kinase ERK2 88.63% 83.82%
CHEMBL218 P21554 Cannabinoid CB1 receptor 85.42% 96.61%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.26% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.80% 89.00%
CHEMBL1902 P62942 FK506-binding protein 1A 83.40% 97.05%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 82.03% 95.50%
CHEMBL340 P08684 Cytochrome P450 3A4 81.90% 91.19%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 81.73% 94.80%
CHEMBL1871 P10275 Androgen Receptor 81.70% 96.43%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.35% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.72% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 80.50% 96.09%
CHEMBL259 P32245 Melanocortin receptor 4 80.45% 95.38%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 80.07% 85.11%

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.
Eucomis comosa

Cross-Links

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PubChem 163015919
LOTUS LTS0144923
wikiData Q105147240