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6-[(3S,5R,7S,10S,13R,14R,17R)-3,7-dihydroxy-4,4,10,13,14-pentamethyl-11,15-dioxo-2,3,5,6,7,12,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic 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 323dc976-84b4-463a-8231-2bc299caf0b8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name 6-[(3S,5R,7S,10S,13R,14R,17R)-3,7-dihydroxy-4,4,10,13,14-pentamethyl-11,15-dioxo-2,3,5,6,7,12,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acid
SMILES (Canonical) CC(CC(=O)CC(C)C(=O)O)C1CC(=O)C2(C1(CC(=O)C3=C2C(CC4C3(CCC(C4(C)C)O)C)O)C)C
SMILES (Isomeric) CC(CC(=O)CC(C)C(=O)O)[C@H]1CC(=O)[C@@]2([C@@]1(CC(=O)C3=C2[C@H](C[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)O)C)C
InChI InChI=1S/C30H44O7/c1-15(10-17(31)11-16(2)26(36)37)18-12-23(35)30(7)25-19(32)13-21-27(3,4)22(34)8-9-28(21,5)24(25)20(33)14-29(18,30)6/h15-16,18-19,21-22,32,34H,8-14H2,1-7H3,(H,36,37)/t15?,16?,18-,19+,21+,22+,28+,29-,30+/m1/s1
InChI Key LWPLEHFGBRFRKI-DUEUHSNMSA-N
Popularity 12 references in papers

Physical and Chemical Properties

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Molecular Formula C30H44O7
Molecular Weight 516.70 g/mol
Exact Mass 516.30870374 g/mol
Topological Polar Surface Area (TPSA) 129.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 4.13
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 6

Synonyms

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6-[(3S,5R,7S,10S,13R,14R,17R)-3,7-dihydroxy-4,4,10,13,14-pentamethyl-11,15-dioxo-2,3,5,6,7,12,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acid

2D Structure

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2D Structure of 6-[(3S,5R,7S,10S,13R,14R,17R)-3,7-dihydroxy-4,4,10,13,14-pentamethyl-11,15-dioxo-2,3,5,6,7,12,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9936 99.36%
Caco-2 - 0.6794 67.94%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.8772 87.72%
OATP2B1 inhibitior - 0.5663 56.63%
OATP1B1 inhibitior + 0.8808 88.08%
OATP1B3 inhibitior - 0.3579 35.79%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6032 60.32%
BSEP inhibitior + 0.7344 73.44%
P-glycoprotein inhibitior - 0.4626 46.26%
P-glycoprotein substrate - 0.5722 57.22%
CYP3A4 substrate + 0.6507 65.07%
CYP2C9 substrate - 0.7735 77.35%
CYP2D6 substrate - 0.9031 90.31%
CYP3A4 inhibition - 0.8336 83.36%
CYP2C9 inhibition - 0.9379 93.79%
CYP2C19 inhibition - 0.9621 96.21%
CYP2D6 inhibition - 0.9619 96.19%
CYP1A2 inhibition - 0.9570 95.70%
CYP2C8 inhibition - 0.5935 59.35%
CYP inhibitory promiscuity - 0.8844 88.44%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7059 70.59%
Eye corrosion - 0.9957 99.57%
Eye irritation - 0.9328 93.28%
Skin irritation + 0.7169 71.69%
Skin corrosion - 0.9548 95.48%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4307 43.07%
Micronuclear - 0.7700 77.00%
Hepatotoxicity - 0.6468 64.68%
skin sensitisation - 0.6491 64.91%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 1.0000 100.00%
Mitochondrial toxicity + 0.9875 98.75%
Nephrotoxicity - 0.8178 81.78%
Acute Oral Toxicity (c) III 0.6954 69.54%
Estrogen receptor binding + 0.6155 61.55%
Androgen receptor binding + 0.6982 69.82%
Thyroid receptor binding + 0.5846 58.46%
Glucocorticoid receptor binding + 0.7904 79.04%
Aromatase binding + 0.7358 73.58%
PPAR gamma + 0.5938 59.38%
Honey bee toxicity - 0.7560 75.60%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 1.0000 100.00%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1825 P01375 TNF-alpha 8.81 nM
 Kd
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL221 P23219 Cyclooxygenase-1 99.19% 90.17%
CHEMBL2581 P07339 Cathepsin D 96.15% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.49% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.98% 91.11%
CHEMBL2850 P49840 Glycogen synthase kinase-3 alpha 93.74% 88.84%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.84% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.05% 97.09%
CHEMBL1937 Q92769 Histone deacetylase 2 87.07% 94.75%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.97% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.13% 95.56%
CHEMBL2996 Q05655 Protein kinase C delta 83.90% 97.79%
CHEMBL2959 Q08881 Tyrosine-protein kinase ITK/TSK 83.60% 95.00%
CHEMBL340 P08684 Cytochrome P450 3A4 83.12% 91.19%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.63% 100.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.72% 90.71%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 81.41% 85.11%
CHEMBL5028 O14672 ADAM10 81.00% 97.50%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 5317488
LOTUS LTS0256763
wikiData Q77420772