Rehmannic acid

Details

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Internal ID 69263962-515c-4ba3-b715-4353767ace2e
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (4R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-4-[(Z)-2-methylbut-2-enoyl]oxy-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
SMILES (Canonical) CC=C(C)C(=O)OC1CC(CC2C1(CCC3(C2=CCC4C3(CCC5C4(CCC(=O)C5(C)C)C)C)C)C(=O)O)(C)C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@@H]1CC(C[C@@H]2[C@]1(CC[C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCC(=O)C5(C)C)C)C)C)C(=O)O)(C)C
InChI InChI=1S/C35H52O5/c1-10-21(2)28(37)40-27-20-30(3,4)19-23-22-11-12-25-32(7)15-14-26(36)31(5,6)24(32)13-16-34(25,9)33(22,8)17-18-35(23,27)29(38)39/h10-11,23-25,27H,12-20H2,1-9H3,(H,38,39)/b21-10-/t23-,24-,25+,27+,32-,33+,34+,35-/m0/s1
InChI Key KCLIRHUTOPOHKJ-LSZVMECJSA-N
Popularity 38 references in papers

Physical and Chemical Properties

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Molecular Formula C35H52O5
Molecular Weight 552.80 g/mol
Exact Mass 552.38147475 g/mol
Topological Polar Surface Area (TPSA) 80.70 Ų
XlogP 7.80
Atomic LogP (AlogP) 7.93
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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LANTADENE A
467-81-2
HSDB 3503
22-beta-Angeloyloxyoleanolic acid
UNII-9SK62WCU1W
9SK62WCU1W
Olean-12-en-28-oic acid, 22beta-hydroxy-3-oxo-, 2-methylcrotonate, (Z)-
22-((2-Methyl-1-oxo-2-butenyl)oxy)-3-oxo-olean-12-en-28-oic acid, 22-beta(Z)-
Olean-12-en-28-oic acid, 22-((2-methyl-1-oxo-2-butenyl)oxy)-3-oxo-, (22beta(Z))-
Olean-12-en-28-oic acid, 22-beta-hydroxy-3-oxo-, 2-methylcrotonate, (Z)-
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Rehmannic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9931 99.31%
Caco-2 - 0.6530 65.30%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.8962 89.62%
OATP2B1 inhibitior - 0.8569 85.69%
OATP1B1 inhibitior + 0.8076 80.76%
OATP1B3 inhibitior - 0.5942 59.42%
MATE1 inhibitior - 0.5200 52.00%
OCT2 inhibitior - 0.6321 63.21%
BSEP inhibitior + 0.9780 97.80%
P-glycoprotein inhibitior + 0.7386 73.86%
P-glycoprotein substrate - 0.7007 70.07%
CYP3A4 substrate + 0.6585 65.85%
CYP2C9 substrate - 0.8058 80.58%
CYP2D6 substrate - 0.9141 91.41%
CYP3A4 inhibition - 0.8230 82.30%
CYP2C9 inhibition - 0.7889 78.89%
CYP2C19 inhibition - 0.8501 85.01%
CYP2D6 inhibition - 0.9627 96.27%
CYP1A2 inhibition - 0.5884 58.84%
CYP2C8 inhibition + 0.6093 60.93%
CYP inhibitory promiscuity - 0.9388 93.88%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9743 97.43%
Carcinogenicity (trinary) Non-required 0.6146 61.46%
Eye corrosion - 0.9924 99.24%
Eye irritation - 0.9133 91.33%
Skin irritation + 0.5880 58.80%
Skin corrosion - 0.9569 95.69%
Ames mutagenesis - 0.7378 73.78%
Human Ether-a-go-go-Related Gene inhibition + 0.6744 67.44%
Micronuclear - 0.6700 67.00%
Hepatotoxicity - 0.8125 81.25%
skin sensitisation - 0.6365 63.65%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity + 0.4930 49.30%
Acute Oral Toxicity (c) III 0.4698 46.98%
Estrogen receptor binding + 0.7350 73.50%
Androgen receptor binding + 0.7175 71.75%
Thyroid receptor binding + 0.6834 68.34%
Glucocorticoid receptor binding + 0.8228 82.28%
Aromatase binding + 0.7834 78.34%
PPAR gamma + 0.7088 70.88%
Honey bee toxicity - 0.7780 77.80%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 1.0000 100.00%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 96.82% 91.11%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 93.94% 93.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.19% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.15% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.70% 99.23%
CHEMBL4302 P08183 P-glycoprotein 1 87.27% 92.98%
CHEMBL221 P23219 Cyclooxygenase-1 86.85% 90.17%
CHEMBL340 P08684 Cytochrome P450 3A4 86.56% 91.19%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.20% 94.45%
CHEMBL1937 Q92769 Histone deacetylase 2 84.64% 94.75%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.54% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.30% 100.00%
CHEMBL2581 P07339 Cathepsin D 84.15% 98.95%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 83.55% 93.03%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.45% 91.07%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.59% 82.69%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.26% 92.94%

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.
Lantana camara
Lippia turbinata
Lycium chinense
Varronia multispicata

Cross-Links

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PubChem 6436598
NPASS NPC40918
ChEMBL CHEMBL510691
LOTUS LTS0153696
wikiData Q27273075