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(E,3S,6R)-3-methyl-6-[(3S,5R,6R,8R,9S,10R,13R,14S,15S,17R)-3,5,6,15-tetrahydroxy-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]hept-4-enoic acid

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 46981139-16f4-4e12-a369-fc8274437d1b
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids > 3-hydroxysteroids > 3-beta-hydroxysteroids
IUPAC Name (E,3S,6R)-3-methyl-6-[(3S,5R,6R,8R,9S,10R,13R,14S,15S,17R)-3,5,6,15-tetrahydroxy-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]hept-4-enoic acid
SMILES (Canonical) CC(CC(=O)O)C=CC(C)C1CC(C2C1(CCC3C2CC(C4(C3(CCC(C4)O)C)O)O)C)O
SMILES (Isomeric) C[C@@H](CC(=O)O)/C=C/[C@@H](C)[C@H]1C[C@@H]([C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@H]([C@@]4([C@@]3(CC[C@@H](C4)O)C)O)O)C)O
InChI InChI=1S/C27H44O6/c1-15(11-23(31)32)5-6-16(2)20-13-21(29)24-18-12-22(30)27(33)14-17(28)7-10-26(27,4)19(18)8-9-25(20,24)3/h5-6,15-22,24,28-30,33H,7-14H2,1-4H3,(H,31,32)/b6-5+/t15-,16-,17+,18-,19+,20-,21+,22-,24-,25-,26-,27+/m1/s1
InChI Key BCOCYZFBZDJHOV-YUKSPCHPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H44O6
Molecular Weight 464.60 g/mol
Exact Mass 464.31378912 g/mol
Topological Polar Surface Area (TPSA) 118.00 Ų
XlogP 3.30
Atomic LogP (AlogP) 3.37
H-Bond Acceptor 5
H-Bond Donor 5
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (E,3S,6R)-3-methyl-6-[(3S,5R,6R,8R,9S,10R,13R,14S,15S,17R)-3,5,6,15-tetrahydroxy-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]hept-4-enoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9490 94.90%
Caco-2 - 0.7503 75.03%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.6814 68.14%
OATP2B1 inhibitior - 0.5703 57.03%
OATP1B1 inhibitior + 0.8193 81.93%
OATP1B3 inhibitior + 0.8803 88.03%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.5627 56.27%
P-glycoprotein inhibitior - 0.6408 64.08%
P-glycoprotein substrate - 0.5273 52.73%
CYP3A4 substrate + 0.7263 72.63%
CYP2C9 substrate - 0.8080 80.80%
CYP2D6 substrate - 0.8685 86.85%
CYP3A4 inhibition - 0.8507 85.07%
CYP2C9 inhibition - 0.9174 91.74%
CYP2C19 inhibition - 0.8196 81.96%
CYP2D6 inhibition - 0.9694 96.94%
CYP1A2 inhibition - 0.8515 85.15%
CYP2C8 inhibition + 0.4603 46.03%
CYP inhibitory promiscuity - 0.9664 96.64%
UGT catelyzed + 1.0000 100.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6980 69.80%
Eye corrosion - 0.9949 99.49%
Eye irritation - 0.9564 95.64%
Skin irritation + 0.7165 71.65%
Skin corrosion - 0.9291 92.91%
Ames mutagenesis - 0.6670 66.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4378 43.78%
Micronuclear - 0.9000 90.00%
Hepatotoxicity - 0.5469 54.69%
skin sensitisation - 0.8323 83.23%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.9750 97.50%
Nephrotoxicity - 0.9037 90.37%
Acute Oral Toxicity (c) I 0.4488 44.88%
Estrogen receptor binding + 0.7510 75.10%
Androgen receptor binding + 0.7755 77.55%
Thyroid receptor binding + 0.5813 58.13%
Glucocorticoid receptor binding + 0.7077 70.77%
Aromatase binding + 0.6621 66.21%
PPAR gamma - 0.5000 50.00%
Honey bee toxicity - 0.6673 66.73%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9885 98.85%

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 99.04% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.93% 97.25%
CHEMBL221 P23219 Cyclooxygenase-1 95.19% 90.17%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.96% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.55% 94.45%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 92.96% 82.69%
CHEMBL2581 P07339 Cathepsin D 91.17% 98.95%
CHEMBL236 P41143 Delta opioid receptor 88.55% 99.35%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.30% 97.09%
CHEMBL4227 P25090 Lipoxin A4 receptor 87.96% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.54% 100.00%
CHEMBL218 P21554 Cannabinoid CB1 receptor 86.13% 96.61%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 85.12% 89.05%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 84.32% 93.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.96% 95.89%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 82.98% 91.11%
CHEMBL2179 P04062 Beta-glucocerebrosidase 82.79% 85.31%
CHEMBL4302 P08183 P-glycoprotein 1 82.32% 92.98%
CHEMBL3776 Q14790 Caspase-8 82.01% 97.06%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.95% 91.07%
CHEMBL340 P08684 Cytochrome P450 3A4 81.75% 91.19%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 81.25% 97.50%
CHEMBL299 P17252 Protein kinase C alpha 81.20% 98.03%
CHEMBL2413 P32246 C-C chemokine receptor type 1 80.84% 89.50%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 80.54% 95.71%
CHEMBL1163125 O60885 Bromodomain-containing protein 4 80.49% 97.31%
CHEMBL226 P30542 Adenosine A1 receptor 80.36% 95.93%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.36% 94.33%
CHEMBL2001 Q9H244 Purinergic receptor P2Y12 80.03% 96.00%

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.
Lippia origanoides

Cross-Links

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PubChem 21634650
NPASS NPC181297
LOTUS LTS0060125
wikiData Q104923537