Details of the Drug

General Information of Drug (ID: DM4SOAW)

Drug Name
URSOLIC ACID
Synonyms
Ursolic acid; Prunol; Malol; Urson; 77-52-1; 3beta-Hydroxyurs-12-en-28-oic acid; (3beta)-3-Hydroxyurs-12-en-28-oic acid; 3beta-Hydroxy-12-ursen-28-ic acid; UNII-P3M2575F3F; CHEBI:9908; CCRIS 7123; EINECS 201-034-0; CHEMBL169; Merotaine; AI3-03109; NSC4060; P3M2575F3F; NSC-4060; Urs-12-en-28-oic acid, 3-hydroxy-, (3beta)-; HNMR; .beta.-Ursolic acid; NSC 4060; NSC 167406
Indication
Disease Entry ICD 11 Status REF
Metabolic syndrome x 5C50-5D2Z Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 456.7
Logarithm of the Partition Coefficient (xlogp) 7.3
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C30H48O3
IUPAC Name
(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Canonical SMILES
C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)C(=O)O
InChI
InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
InChIKey
WCGUUGGRBIKTOS-GPOJBZKASA-N
Cross-matching ID
PubChem CID
64945
ChEBI ID
CHEBI:9908
CAS Number
77-52-1
UNII
P3M2575F3F
DrugBank ID
DB15588
TTD ID
D07LUJ
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1) TTN7BL9 DHI1_HUMAN Inhibitor [2]
Glycogen phosphorylase muscle form (GP) TTZHY6R PYGM_HUMAN Inhibitor [3]
Herpes simplex virus DNA polymerase UL30 (HSV UL30) TTIU7X1 DPOL_HHV11 Inhibitor [4]
Phospholipase A2 (PLA2G1B) TT9V5JH PA21B_HUMAN Inhibitor [5]
PTPN1 messenger RNA (PTPN1 mRNA) TTELIN2 PTN1_HUMAN Inhibitor [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [7]
Acetyl-CoA carboxylase 1 (ACACA) OT5CQPZY ACACA_HUMAN Post-Translational Modifications [8]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [9]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [10]
Apoptosis-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_HUMAN Drug Response [11]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [12]
Bcl-2 homologous antagonist/killer (BAK1) OTDP6ILW BAK_HUMAN Gene/Protein Processing [11]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [13]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Gene/Protein Processing [13]
Cyclin-dependent kinase 4 (CDK4) OT7EP05T CDK4_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Metabolic syndrome x
ICD Disease Classification 5C50-5D2Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Glycogen phosphorylase muscle form (GP) DTT PYGM 2.69E-01 -0.23 -0.14
Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1) DTT HSD11B1 2.03E-01 -0.01 -0.08
PTPN1 messenger RNA (PTPN1 mRNA) DTT PTPN1 9.44E-01 7.21E-03 0.08
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Experimental Cancer Drug Sensitivity Information

Cancer Drug Sensitivity Data Curated from 1 Cell Line(s) in Breast Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
MCF-7 CTRP1 4.7358 5.8612 4.7336 44.7525
Cancer Drug Sensitivity Data Curated from 2 Cell Line(s) in Central Nervous System Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
LN-229 CTRP1 3.3701 3.9741 3.3701 64.2509
GaMG CTRP1 5.965 7.8974 3.2184 1.1066
Cancer Drug Sensitivity Data Curated from 6 Cell Line(s) in Endometrium Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
JHUEM-2 CTRP1 3.4633 4.1951 3.4633 62.9169
HEC-151 CTRP1 4.069 4.7259 4.069 54.266
KLE CTRP1 4.5056 7.3245 2.6377 8.6589
HEC-59 CTRP1 4.8519 6.4929 3.2561 2.5306
HEC-108 CTRP1 5.9885 10.9215 1.9126 9.9864
Ishikawa (Heraklio) 02 ER- CTRP1 5.0852 6.0333 3.5559 0.3562
⏷ Show the Full List of 6 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 19 Cell Line(s) in Haematopoietic And Lymphoid Tissue Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
PL21 CTRP1 2.4049 4.2752 2.4021 76.2093
WSU-DLCL2 CTRP1 2.5742 3.1063 2.5742 75.6176
THP-1 CTRP1 2.761 3.9673 2.7609 72.7071
OCI-AML-3 CTRP1 2.8692 3.6333 2.8692 71.3905
GDM-1 CTRP1 3.1974 4.6548 3.1962 66.4481
NOMO-1 CTRP1 3.212 3.8249 3.212 66.508
NU-DUL-1 CTRP1 3.386 5.1653 3.3797 63.5641
SU-DHL-5 CTRP1 3.4883 4.0174 3.4883 62.5616
BL-70 CTRP1 3.6859 4.2345 3.5172 4.0004
KMS-11 CTRP1 4.1567 5.0299 4.1566 53.0126
EJM CTRP1 4.3534 5.0118 4.3534 50.2032
RPMI-8226 CTRP1 4.4466 6.7528 4.3689 48.9504
LP-1 CTRP1 4.6417 5.658 4.6408 46.0895
SKM-1 CTRP1 4.6822 6.33 4.661 45.5928
AMO1 CTRP1 4.8459 5.6238 4.8457 43.1692
MOLM-16 CTRP1 8.7244 10.1351 7.3432 2.1437
U-937 CTRP1 8.9863 23.1409 1.1421 33.1704
SU-DHL-4 CTRP1 9.5965 11.1646 7.342 0.8665
OCI-Ly10 CTRP1 10.7082 18.6638 4.6138 16.1382
⏷ Show the Full List of 19 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 1 Cell Line(s) in Kidney Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
RCC10RGB CTRP1 4.365 5.184 4.365 50.0374
Cancer Drug Sensitivity Data Curated from 27 Cell Line(s) in Large Intestine Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
SW480 CTRP1 2.8275 4.441 2.826 71.3094
SNU-81 CTRP1 3.091 4.6509 3.0893 67.8162
SNU-C5 CTRP1 3.3398 4.133 3.3398 64.6777
CW-2 CTRP1 3.4487 4.2252 3.4487 63.1248
LS180 CTRP1 3.4903 4.1044 3.4903 62.5329
SNU-175 CTRP1 3.6749 5.0144 3.6737 59.8187
SNU-61 CTRP1 4.0082 5.2414 4.007 55.1136
SNU-C4 CTRP1 4.0359 4.9366 4.0358 54.7378
HT115 CTRP1 4.5532 5.6061 4.5522 47.3531
KM12 CTRP1 4.5893 5.5347 4.5888 46.8362
COLO 678 CTRP1 4.6852 7.8657 4.395 46.211
SW948 CTRP1 4.9842 7.556 4.8002 42.0691
COLO 320 CTRP1 5.291 9.2729 4.5774 40.2435
CL-40 CTRP1 5.3697 6.8288 5.3395 35.8922
CL-34 CTRP1 5.4908 6.3021 5.4896 33.9641
MDST8 CTRP1 8.0797 12.2168 5.8672 16.5947
SW620 CTRP1 8.7034 12.2586 6.3237 10.6336
LS123 CTRP1 8.7493 11.3757 6.7828 6.6516
NCI-H508 CTRP1 8.7994 11.0316 6.9784 4.8739
RCM-1 [Human ESC] CTRP1 9.0144 11.7981 6.7562 6.1179
HCT 8 CTRP1 9.1372 10.2332 7.5027 0.5384
HT-29 CTRP1 9.2116 10.3537 7.4881 0.5395
HCT 116 CTRP1 9.3364 10.7502 7.3896 0.893
SNU-1040 CTRP1 9.4244 10.8777 7.3785 0.8577
LoVo CTRP1 9.6922 11.854 7.1115 2.0423
HT-55 CTRP1 9.7112 11.3224 7.3303 0.8151
RKO CTRP1 10.1322 11.563 7.4063 0.283
⏷ Show the Full List of 27 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 4 Cell Line(s) in Liver Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
SNU-398 CTRP1 4.224 5.3341 4.2232 52.0485
SNU-449 CTRP1 5.3451 8.2803 2.7372 5.4207
JHH-6 CTRP1 5.574 6.4552 3.5868 0.0808
Hep-G2 CTRP1 6.0964 7.7332 5.9696 26.2389
Cancer Drug Sensitivity Data Curated from 44 Cell Line(s) in Lung Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
NCI-H1105 CTRP1 2.5238 3.2229 2.5238 76.3164
NCI-H2342 CTRP1 2.5862 3.5221 2.5862 75.3427
NCI-H3255 CTRP1 2.8386 4.056 2.8385 71.6221
NCI-H2081 CTRP1 3.0391 4.2895 3.0388 68.8046
NCI-H2122 CTRP1 3.1437 3.7689 3.1437 67.4844
NCI-H1836 CTRP1 3.1864 3.8971 3.1864 66.8718
T3M-10 CTRP1 3.3009 4.5754 3.3004 65.119
NCI-H1963 CTRP1 3.307 5.5639 3.2831 64.0186
HCC1195 CTRP1 3.331 4.5803 3.3306 64.7068
HCC2935 CTRP1 3.4576 4.1307 3.4576 62.9998
LXF 289 CTRP1 3.6924 4.849 3.2242 6.5671
NCI-H596 CTRP1 3.7161 4.6023 3.7161 59.3034
NCI-H841 CTRP1 3.8252 4.7092 3.8252 57.7453
NCI-H1694 CTRP1 3.9146 5.1348 3.9137 56.4457
COR-L51 CTRP1 3.9169 5.0484 3.9164 56.4229
HCC1833 CTRP1 3.9383 5.4659 3.9335 56.0486
COLO 699 CTRP1 4.0658 4.8867 4.0658 54.3116
NCI-H2030 CTRP1 4.0719 5.2475 4.071 54.2125
NCI-H2073 CTRP1 4.1767 5.0275 4.1767 52.7271
HCC4006 CTRP1 4.2135 4.845 4.2135 52.2025
NCI-H1435 CTRP1 4.3016 6.7481 2.7711 8.2046
NCI-H460 CTRP1 4.3242 5.133 4.3241 50.6211
CAL-12T CTRP1 4.3729 5.8604 4.3652 49.9261
NCI-H1876 CTRP1 4.3998 5.3777 4.3994 49.5418
SCLC-21H CTRP1 4.481 5.1762 4.481 48.3801
NCI-H2141 CTRP1 4.5097 6.9674 4.4037 48.1417
SK-LU-1 CTRP1 4.6088 5.7297 4.6071 46.5622
NCI-H2023 CTRP1 4.622 6.2955 4.6008 46.4407
NCI-H1930 CTRP1 4.7581 6.448 3.2223 3.0009
RERF-LC-KJ CTRP1 4.836 7.5399 2.7622 6.5684
NCI-H441 CTRP1 4.9537 7.4838 4.7835 42.422
HCC1359 CTRP1 4.9725 6.1493 4.9678 41.3895
COLO 668 CTRP1 5.2463 8.5751 2.5397 7.2349
HCC2108 CTRP1 5.3953 7.2854 5.3033 35.9308
NCI-H1781 CTRP1 5.4415 6.7018 5.4251 34.7745
NCI-H1915 CTRP1 5.5297 7.4701 3.1907 1.7873
NCI-H2172 CTRP1 5.8045 8.063 5.5598 31.2052
NCI-H2286 CTRP1 5.8138 7.3961 3.3447 0.6674
HCC827 CTRP1 6.056 7.6452 5.9466 26.6838
COR-L23 CTRP1 7.7433 8.4474 7.4686 4.1466
Sq-1 CTRP1 8.0269 9.2065 7.3258 4.2631
NCI-H2110 CTRP1 8.2222 17.5895 3.299 29.7498
NCI-H1755 CTRP1 8.5837 10.6553 7.0159 5.1661
HCC15 CTRP1 9.171 11.3182 7.0693 3.2624
⏷ Show the Full List of 44 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 23 Cell Line(s) in Ovary Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
COV434 CTRP1 3.0899 3.9636 3.0899 68.2327
RMG-I CTRP1 3.1777 4.3828 3.1775 66.8858
RMUG-S CTRP1 3.1847 4.9823 3.1794 66.2688
JHOC-5 CTRP1 3.5975 5.062 3.5953 60.8605
OVK18 CTRP1 3.7701 4.6211 3.77 58.5341
OVCAR-4 CTRP1 3.9496 4.8859 3.9495 55.9687
OVCAR-8 CTRP1 4.1302 4.7914 4.1302 53.392
OVKATE CTRP1 4.1829 4.9374 4.1829 52.6394
Caov-3 CTRP1 4.2807 5.2024 4.2805 51.2416
JHOS-4 CTRP1 4.5204 7.3735 2.6244 8.7232
JHOM-1 CTRP1 4.6297 5.8951 4.6255 46.2744
OAW42 CTRP1 4.7802 5.618 4.7799 44.1084
A2780 CTRP1 4.8321 5.9592 4.8293 43.3817
COV318 CTRP1 4.8992 6.6626 3.2074 2.7986
OVMANA CTRP1 5.0322 6.5247 3.3382 1.6065
IGROV-1 CTRP1 5.2188 6.1077 5.2176 37.8488
COV362 CTRP1 5.3944 6.3762 5.3909 35.3574
OV-90 CTRP1 6.5047 10.6094 5.2436 28.6961
SNU-840 CTRP1 7.0164 13.2433 4.4412 30.2187
EFO-27 CTRP1 7.1005 9.6557 6.2748 17.8045
TYK-nu CTRP1 8.9103 12.2029 6.4954 8.5612
OV7 CTRP1 9.5239 13.7784 6.1523 9.4848
COV644 CTRP1 9.8452 11.3515 7.3736 0.5325
⏷ Show the Full List of 23 Cancer Drug Sensitivity Data of This Drug
Cancer Drug Sensitivity Data Curated from 1 Cell Line(s) in Pancreas Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
PaTu 8902 CTRP1 5.3957 6.8253 3.3863 0.8476
Cancer Drug Sensitivity Data Curated from 1 Cell Line(s) in Prostate Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
PaCa-3 CTRP1 5.8721 12.0648 1.2952 14.4669
Cancer Drug Sensitivity Data Curated from 5 Cell Line(s) in Skin Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
SK-MEL-5 CTRP1 3.9686 5.7039 3.9573 55.5612
A-375 CTRP1 5.3219 5.8839 5.3219 36.3683
Hs 852.T CTRP1 6.1479 7.9723 3.2658 0.7375
SK-MEL-28 CTRP1 8.6645 10.0328 7.3549 2.1834
SK-MEL-1 CTRP1 9.4367 11.7142 7.041 2.9416
Cancer Drug Sensitivity Data Curated from 2 Cell Line(s) in Soft Tissue Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
RKN CTRP1 5.4516 6.5191 5.4449 34.5621
HT-1080 CTRP1 8.1709 9.4099 7.3323 3.7051
Cancer Drug Sensitivity Data Curated from 3 Cell Line(s) in Stomach Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
AGS CTRP1 4.3227 5.0689 4.3226 50.6427
MKN74 CTRP1 4.7817 7.6773 2.6602 7.5836
SNG-M CTRP1 5.6866 10.3495 1.9882 10.2521
Cancer Drug Sensitivity Data Curated from 1 Cell Line(s) in Upper Aerodigestive Tract Tissue
Cell Line Original Dataset IC50 IC90 EC50 AUC
SCC-9 CTRP1 4.6369 5.5079 4.6367 46.1542

References

1 ClinicalTrials.gov (NCT02337933) Effect of Ursolic Acid Administration on Insulin Sensitivity and Metabolic Syndrome. U.S. National Institutes of Health.
2 11beta-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational a... Bioorg Med Chem. 2010 Feb 15;18(4):1507-15.
3 Synthesis of 3-deoxypentacyclic triterpene derivatives as inhibitors of glycogen phosphorylase. J Nat Prod. 2009 Aug;72(8):1414-8.
4 DNA polymerase beta inhibitors from Baeckea gunniana. J Nat Prod. 1999 Dec;62(12):1624-6.
5 Synthesis of benzoyl phenyl benzoates as effective inhibitors for phospholipase A2 and hyaluronidase enzymes. Bioorg Med Chem Lett. 2005 Sep 15;15(18):4100-4.
6 Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica. Bioorg Med Chem Lett. 2009 Dec 1;19(23):6745-9.
7 Inhibition of cell proliferation, invasion and migration by ursolic acid in human lung cancer cell lines. Toxicol In Vitro. 2011 Oct;25(7):1274-80. doi: 10.1016/j.tiv.2011.04.014. Epub 2011 Apr 20.
8 Ursolic acid induces autophagy in U87MG cells via ROS-dependent endoplasmic reticulum stress. Chem Biol Interact. 2014 Jul 25;218:28-41. doi: 10.1016/j.cbi.2014.04.017. Epub 2014 May 5.
9 Molecular mechanism of ursolic acid induced apoptosis in poorly differentiated endometrial cancer HEC108 cells. Oncol Rep. 2005 Aug;14(2):507-12.
10 Selective in vitro anti-melanoma activity of ursolic and oleanolic acids. Toxicol Mech Methods. 2018 Feb;28(2):148-156. doi: 10.1080/15376516.2017.1373881. Epub 2017 Sep 29.
11 Ursolic acid induces doxorubicin-resistant HepG2 cell death via the release of apoptosis-inducing factor. Cancer Lett. 2010 Dec 1;298(1):128-38. doi: 10.1016/j.canlet.2010.06.010. Epub 2010 Jul 13.
12 Ursolic acid reduces Adriamycin resistance of human ovarian cancer cells through promoting the HuR translocation from cytoplasm to nucleus. Environ Toxicol. 2021 Feb;36(2):267-275. doi: 10.1002/tox.23032. Epub 2020 Oct 3.
13 Oleanolic acid and ursolic acid induce apoptosis in four human liver cancer cell lines. Toxicol In Vitro. 2010 Apr;24(3):842-8. doi: 10.1016/j.tiv.2009.12.008. Epub 2009 Dec 22.