(3S)-5-[(1R,2S,3R,4aR,8aR)-5-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3-hydroxy-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpentanoic acid

Details

Top
Internal ID c36702e3-834a-43f9-a2ee-4069b9ceb13c
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
IUPAC Name (3S)-5-[(1R,2S,3R,4aR,8aR)-5-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3-hydroxy-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpentanoic acid
SMILES (Canonical) CC1C(CC2(C(C1(C)CCC(C)CC(=O)O)CCC=C2COC(=O)C=CC3=CC(=C(C=C3)O)O)C)O
SMILES (Isomeric) C[C@@H]1[C@@H](C[C@@]2([C@@H]([C@@]1(C)CC[C@H](C)CC(=O)O)CCC=C2COC(=O)/C=C/C3=CC(=C(C=C3)O)O)C)O
InChI InChI=1S/C29H40O7/c1-18(14-26(33)34)12-13-28(3)19(2)24(32)16-29(4)21(6-5-7-25(28)29)17-36-27(35)11-9-20-8-10-22(30)23(31)15-20/h6,8-11,15,18-19,24-25,30-32H,5,7,12-14,16-17H2,1-4H3,(H,33,34)/b11-9+/t18-,19+,24+,25+,28-,29-/m0/s1
InChI Key WBXJTEOASUIUIA-QZEJUCPHSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C29H40O7
Molecular Weight 500.60 g/mol
Exact Mass 500.27740361 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 5.50
Atomic LogP (AlogP) 5.29
H-Bond Acceptor 6
H-Bond Donor 4
Rotatable Bonds 9

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (3S)-5-[(1R,2S,3R,4aR,8aR)-5-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3-hydroxy-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpentanoic acid

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9809 98.09%
Caco-2 - 0.8063 80.63%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.8978 89.78%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9065 90.65%
OATP1B3 inhibitior + 0.8965 89.65%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8292 82.92%
BSEP inhibitior + 0.9474 94.74%
P-glycoprotein inhibitior + 0.6723 67.23%
P-glycoprotein substrate + 0.5074 50.74%
CYP3A4 substrate + 0.6727 67.27%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8751 87.51%
CYP3A4 inhibition - 0.7129 71.29%
CYP2C9 inhibition - 0.8229 82.29%
CYP2C19 inhibition - 0.7349 73.49%
CYP2D6 inhibition - 0.8789 87.89%
CYP1A2 inhibition + 0.5806 58.06%
CYP2C8 inhibition + 0.6456 64.56%
CYP inhibitory promiscuity - 0.8618 86.18%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9000 90.00%
Carcinogenicity (trinary) Non-required 0.6821 68.21%
Eye corrosion - 0.9951 99.51%
Eye irritation - 0.9503 95.03%
Skin irritation - 0.5703 57.03%
Skin corrosion - 0.9658 96.58%
Ames mutagenesis - 0.7478 74.78%
Human Ether-a-go-go-Related Gene inhibition + 0.8320 83.20%
Micronuclear - 0.7700 77.00%
Hepatotoxicity - 0.6250 62.50%
skin sensitisation - 0.8379 83.79%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity - 0.8146 81.46%
Acute Oral Toxicity (c) III 0.5791 57.91%
Estrogen receptor binding + 0.8454 84.54%
Androgen receptor binding + 0.7973 79.73%
Thyroid receptor binding + 0.6254 62.54%
Glucocorticoid receptor binding + 0.8250 82.50%
Aromatase binding + 0.7680 76.80%
PPAR gamma + 0.5984 59.84%
Honey bee toxicity - 0.7364 73.64%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 1.0000 100.00%

Targets

Top

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.78% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.78% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.20% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.07% 94.45%
CHEMBL2581 P07339 Cathepsin D 93.97% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.87% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 93.71% 90.17%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 92.39% 99.15%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.84% 89.00%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 90.94% 94.62%
CHEMBL4208 P20618 Proteasome component C5 90.12% 90.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.56% 96.00%
CHEMBL1951 P21397 Monoamine oxidase A 89.55% 91.49%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 88.69% 90.71%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.59% 95.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.52% 99.17%
CHEMBL340 P08684 Cytochrome P450 3A4 86.45% 91.19%
CHEMBL3359 P21462 Formyl peptide receptor 1 85.23% 93.56%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 83.55% 89.62%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.46% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.25% 95.89%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.77% 91.07%

Plants that contains it

Top
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.
Nuxia sphaerocephala

Cross-Links

Top
PubChem 11598539
LOTUS LTS0009958
wikiData Q105301140