(2S,4aR,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-4-oxo-3,5,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-1H-picene-2-carboxylic acid

Details

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Internal ID ac75c6f9-be05-4ef7-84ce-52dfd851ec39
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (2S,4aR,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-4-oxo-3,5,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-1H-picene-2-carboxylic acid
SMILES (Canonical) CC12CCC(C(C1CCC3(C2CC=C4C3(CCC5(C4CC(CC5=O)(C)C(=O)O)C)C)C)(C)CO)O
SMILES (Isomeric) C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4C[C@](CC5=O)(C)C(=O)O)C)C)C)(C)CO)O
InChI InChI=1S/C30H46O5/c1-25(24(34)35)15-19-18-7-8-21-27(3)11-10-22(32)28(4,17-31)20(27)9-12-30(21,6)29(18,5)14-13-26(19,2)23(33)16-25/h7,19-22,31-32H,8-17H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,25-,26+,27-,28-,29+,30+/m0/s1
InChI Key MVTZJCYINFKILV-BQDBDJMVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C30H46O5
Molecular Weight 486.70 g/mol
Exact Mass 486.33452456 g/mol
Topological Polar Surface Area (TPSA) 94.80 Ų
XlogP 5.20
Atomic LogP (AlogP) 5.39
H-Bond Acceptor 4
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,4aR,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-4-oxo-3,5,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-1H-picene-2-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9773 97.73%
Caco-2 - 0.6155 61.55%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.8501 85.01%
OATP2B1 inhibitior - 0.5659 56.59%
OATP1B1 inhibitior + 0.8856 88.56%
OATP1B3 inhibitior - 0.3567 35.67%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior + 0.5470 54.70%
BSEP inhibitior + 0.8838 88.38%
P-glycoprotein inhibitior - 0.7046 70.46%
P-glycoprotein substrate - 0.7090 70.90%
CYP3A4 substrate + 0.6714 67.14%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8615 86.15%
CYP3A4 inhibition - 0.7229 72.29%
CYP2C9 inhibition - 0.9124 91.24%
CYP2C19 inhibition - 0.9395 93.95%
CYP2D6 inhibition - 0.9472 94.72%
CYP1A2 inhibition - 0.9081 90.81%
CYP2C8 inhibition - 0.5708 57.08%
CYP inhibitory promiscuity - 0.9342 93.42%
UGT catelyzed - 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7215 72.15%
Eye corrosion - 0.9931 99.31%
Eye irritation - 0.9432 94.32%
Skin irritation + 0.5814 58.14%
Skin corrosion - 0.9609 96.09%
Ames mutagenesis - 0.7754 77.54%
Human Ether-a-go-go-Related Gene inhibition - 0.4883 48.83%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.8250 82.50%
skin sensitisation - 0.9038 90.38%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity + 0.6884 68.84%
Acute Oral Toxicity (c) III 0.8019 80.19%
Estrogen receptor binding + 0.6770 67.70%
Androgen receptor binding + 0.6957 69.57%
Thyroid receptor binding + 0.5753 57.53%
Glucocorticoid receptor binding + 0.8428 84.28%
Aromatase binding + 0.6972 69.72%
PPAR gamma + 0.6157 61.57%
Honey bee toxicity - 0.8812 88.12%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.7400 74.00%
Fish aquatic toxicity + 0.9895 98.95%

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
CHEMBL221 P23219 Cyclooxygenase-1 93.89% 90.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.14% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.85% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.53% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.74% 96.09%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 86.48% 93.04%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.18% 82.69%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 84.95% 93.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.50% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.70% 100.00%
CHEMBL2581 P07339 Cathepsin D 81.18% 98.95%
CHEMBL2916 O14746 Telomerase reverse transcriptase 80.49% 90.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.20% 99.23%

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.
Melilotus officinalis

Cross-Links

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PubChem 14059504
LOTUS LTS0184966
wikiData Q105173304