(Z,6R)-6-[(3R,3aR,6S,7S,9bR)-6-(3-methoxy-3-oxopropyl)-3a,9b-dimethyl-7-prop-1-en-2-yl-2,3,4,5,6,7,8,9-octahydro-1H-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

Details

Top
Internal ID 334a8e39-ba71-4451-a434-42ce1f756f90
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (Z,6R)-6-[(3R,3aR,6S,7S,9bR)-6-(3-methoxy-3-oxopropyl)-3a,9b-dimethyl-7-prop-1-en-2-yl-2,3,4,5,6,7,8,9-octahydro-1H-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid
SMILES (Canonical) CC(CCC=C(C)C(=O)O)C1CCC2(C1(CCC3=C2CCC(C3CCC(=O)OC)C(=C)C)C)C
SMILES (Isomeric) C[C@H](CC/C=C(/C)\C(=O)O)[C@H]1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]([C@@H]3CCC(=O)OC)C(=C)C)C)C
InChI InChI=1S/C30H46O4/c1-19(2)22-11-13-26-24(23(22)12-14-27(31)34-7)15-17-29(5)25(16-18-30(26,29)6)20(3)9-8-10-21(4)28(32)33/h10,20,22-23,25H,1,8-9,11-18H2,2-7H3,(H,32,33)/b21-10-/t20-,22-,23+,25-,29-,30+/m1/s1
InChI Key UPSFXEHDOPIMAJ-ISZOBLOUSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C30H46O4
Molecular Weight 470.70 g/mol
Exact Mass 470.33960994 g/mol
Topological Polar Surface Area (TPSA) 63.60 Ų
XlogP 7.50
Atomic LogP (AlogP) 7.50
H-Bond Acceptor 3
H-Bond Donor 1
Rotatable Bonds 9

Synonyms

Top
(Z,6R)-6-[(3R,3aR,6S,7S,9bR)-6-(3-methoxy-3-oxopropyl)-3a,9b-dimethyl-7-prop-1-en-2-yl-2,3,4,5,6,7,8,9-octahydro-1H-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid
UPSFXEHDOPIMAJ-ISZOBLOUSA-N

2D Structure

Top
2D Structure of (Z,6R)-6-[(3R,3aR,6S,7S,9bR)-6-(3-methoxy-3-oxopropyl)-3a,9b-dimethyl-7-prop-1-en-2-yl-2,3,4,5,6,7,8,9-octahydro-1H-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9806 98.06%
Caco-2 - 0.5943 59.43%
Blood Brain Barrier + 0.9250 92.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.6788 67.88%
OATP2B1 inhibitior - 0.7161 71.61%
OATP1B1 inhibitior + 0.7682 76.82%
OATP1B3 inhibitior - 0.3407 34.07%
MATE1 inhibitior - 0.6400 64.00%
OCT2 inhibitior - 0.7271 72.71%
BSEP inhibitior + 0.8886 88.86%
P-glycoprotein inhibitior + 0.6830 68.30%
P-glycoprotein substrate + 0.5196 51.96%
CYP3A4 substrate + 0.6762 67.62%
CYP2C9 substrate - 0.8074 80.74%
CYP2D6 substrate - 0.9167 91.67%
CYP3A4 inhibition - 0.7563 75.63%
CYP2C9 inhibition - 0.8033 80.33%
CYP2C19 inhibition - 0.8680 86.80%
CYP2D6 inhibition - 0.9425 94.25%
CYP1A2 inhibition - 0.6596 65.96%
CYP2C8 inhibition + 0.5348 53.48%
CYP inhibitory promiscuity - 0.8000 80.00%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9020 90.20%
Carcinogenicity (trinary) Non-required 0.6886 68.86%
Eye corrosion - 0.9878 98.78%
Eye irritation - 0.9181 91.81%
Skin irritation - 0.5694 56.94%
Skin corrosion - 0.9720 97.20%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4177 41.77%
Micronuclear - 0.7100 71.00%
Hepatotoxicity + 0.5553 55.53%
skin sensitisation - 0.6828 68.28%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.7581 75.81%
Acute Oral Toxicity (c) III 0.7635 76.35%
Estrogen receptor binding + 0.6825 68.25%
Androgen receptor binding + 0.8118 81.18%
Thyroid receptor binding + 0.6153 61.53%
Glucocorticoid receptor binding + 0.8186 81.86%
Aromatase binding + 0.6991 69.91%
PPAR gamma + 0.6192 61.92%
Honey bee toxicity - 0.7649 76.49%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.6200 62.00%
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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.26% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.00% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.42% 98.95%
CHEMBL240 Q12809 HERG 94.42% 89.76%
CHEMBL340 P08684 Cytochrome P450 3A4 92.92% 91.19%
CHEMBL4227 P25090 Lipoxin A4 receptor 92.81% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.69% 94.45%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 91.60% 96.38%
CHEMBL221 P23219 Cyclooxygenase-1 89.64% 90.17%
CHEMBL233 P35372 Mu opioid receptor 89.52% 97.93%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 88.67% 95.50%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 88.61% 93.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 88.17% 93.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 85.15% 99.17%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.96% 92.62%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 84.56% 95.17%
CHEMBL2964 P36507 Dual specificity mitogen-activated protein kinase kinase 2 84.22% 80.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.82% 95.56%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.02% 94.33%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.58% 90.71%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 81.58% 96.47%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 81.50% 96.90%
CHEMBL1871 P10275 Androgen Receptor 81.11% 96.43%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.01% 100.00%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 80.77% 97.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.28% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.18% 99.23%
CHEMBL1937 Q92769 Histone deacetylase 2 80.17% 94.75%

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.
Kadsura heteroclita
Schisandra sphenanthera
Ulmus parvifolia

Cross-Links

Top
PubChem 6443936
NPASS NPC261317