PCIDB

KNApSAcK Metabolite C00003558

Metabolite

KNApSAcK Entry

id C00003558
Name Ursolic acid
CAS RN 77-52-1
Standard 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
Standard InChI (Main Layer) 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)

Cluster

Phytochemical cluster No. 51
KCF-S cluster No. 13

Link

ChEMBL

By standard InChI CHEMBL169
By standard InChI Main Layer CHEMBL297810 CHEMBL56048 CHEMBL300594 CHEMBL169 CHEMBL176234 CHEMBL491715 CHEMBL1316667 CHEMBL1555307 CHEMBL1593360 CHEMBL1979720

KEGG

By LinkDB C08988

CTD

By CAS RN C005466

Species

Summary

Plant class

class name count
asterids 26
rosids 14
Euphyllophyta 1

Family (Top 10)

family name count
Lamiaceae 10
Rosaceae 6
Rubiaceae 6
Moraceae 2
Myrtaceae 2
Ericaceae 2
Asteraceae 2
Nothofagaceae 1
Stilbaceae 1
Apocynaceae 1

List (41)

* NCBI
KNApSAcK organism *ID *family *plant class *kingdom
Arctostaphylos uva-ursi 84009 Ericaceae asterids Viridiplantae
Celtis philippinensis 213552 Cannabaceae rosids Viridiplantae
Chaenomeles japonica 320146 Rosaceae rosids Viridiplantae
Chiococca alba 28527 Rubiaceae asterids Viridiplantae
Conandron ramondioides Sieb.et Zucc. 121478 Gesneriaceae asterids Viridiplantae
Cotoneaster simonsii 36607 Rosaceae rosids Viridiplantae
Cyphanthera spinescens 195730 Solanaceae asterids Viridiplantae
Dracocephalum kotschyi 180015 Lamiaceae asterids Viridiplantae
Dryopteris crassirhizoma 97234 Dryopteridaceae Euphyllophyta Viridiplantae
Ehretia buxifolia 48522 Boraginaceae asterids Viridiplantae
Eucalyptus camaldulensis var.obtusa 3932 Myrtaceae rosids Viridiplantae
Eucalyptus cladocalyx 452569 Myrtaceae rosids Viridiplantae
Ficus microcarpa 66385 Moraceae rosids Viridiplantae
Inula cappa 313931 Asteraceae asterids Viridiplantae
Malus doumeri varl formosana 3749 Rosaceae rosids Viridiplantae
Malus spp. 3749 Rosaceae rosids Viridiplantae
Marsypianthes chamaedrys 986255 Lamiaceae asterids Viridiplantae
Morinda citrifolia L. 43522 Rubiaceae asterids Viridiplantae
Morus insignis 1031565 Moraceae rosids Viridiplantae
Myrica rubra 262757 Myricaceae rosids Viridiplantae
Nerium oleander 63479 Apocynaceae asterids Viridiplantae
Nothofagus pumilio 28950 Nothofagaceae rosids Viridiplantae
Nuxia sphaerocephala 69069 Stilbaceae asterids Viridiplantae
Oldenlandia diffusa 254027 Rubiaceae asterids Viridiplantae
Olea europaea 4146 Oleaceae asterids Viridiplantae
Ophiorrhiza liukiuensis 489897 Rubiaceae asterids Viridiplantae
Orthosiphon stamineus 260636 Lamiaceae asterids Viridiplantae
Palicourea coriacea 59595 Rubiaceae asterids Viridiplantae
Perilla frutescens (L.) Britton var.japonica Hara 4136 Lamiaceae asterids Viridiplantae
Petasites tricholobus 186966 Asteraceae asterids Viridiplantae
Prunella vulgaris 39358 Lamiaceae asterids Viridiplantae
Prunus avium 42229 Rosaceae rosids Viridiplantae
Punica granatum LINN. 22662 Lythraceae rosids Viridiplantae
Pyrus spp. 3766 Rosaceae rosids Viridiplantae
Rabdosia amethystoides 204130 Lamiaceae asterids Viridiplantae
Rubia wallichiana DECNE 25473 Rubiaceae asterids Viridiplantae
Salvia amplexicaulis Lam. 268888 Lamiaceae asterids Viridiplantae
Salvia syriaca L. 21880 Lamiaceae asterids Viridiplantae
Scutellaria strigillosa 4139 Lamiaceae asterids Viridiplantae
Thymus vulgaris 49992 Lamiaceae asterids Viridiplantae
Vaccinium macrocarpon 13750 Ericaceae asterids Viridiplantae

Human Protein / Gene in interaction

47 ChEMBL Protein in interactions

accession description class description compound assay ID (# of activities) # of diseases
(OMIM / KEGG)
P10635 Cytochrome P450 2D6 Cytochrome P450 2D6 CHEMBL1316667 CHEMBL1741321 (1)
1 / 0
P18031 Tyrosine-protein phosphatase non-receptor type 1 Tyr CHEMBL169 CHEMBL904966 (1) CHEMBL995832 (1)
CHEMBL972808 (1) CHEMBL1036591 (1)
CHEMBL963010 (1) CHEMBL1036431 (1)
CHEMBL1041807 (1) CHEMBL1041808 (2)
CHEMBL1041717 (1) CHEMBL1101504 (1)
CHEMBL1115822 (1) CHEMBL1781409 (1)
CHEMBL1816250 (1) CHEMBL1828245 (1)
CHEMBL2089751 (1) CHEMBL2149371 (1)
CHEMBL2149372 (2) CHEMBL2149377 (1)
CHEMBL2162374 (1) CHEMBL2210497 (1)
CHEMBL2344762 (1) CHEMBL2344763 (1)
0 / 0
O60218 Aldo-keto reductase family 1 member B10 Enzyme CHEMBL169 CHEMBL2168780 (1) CHEMBL2168783 (1)
CHEMBL2169016 (1)
0 / 0
P35354 Prostaglandin G/H synthase 2 Oxidoreductase CHEMBL169 CHEMBL1014032 (1) CHEMBL1003453 (1)
CHEMBL1003458 (1) CHEMBL1003459 (1)
0 / 3
P06746 DNA polymerase beta Enzyme CHEMBL169 CHEMBL1002742 (1)
0 / 0
Q13547 Histone deacetylase 1 Hydrolase CHEMBL169 CHEMBL1785663 (1)
0 / 0
P24666 Low molecular weight phosphotyrosine protein phosphatase Tyr CHEMBL169 CHEMBL2149373 (1) CHEMBL2149374 (1)
0 / 0
Q8TDU6 G-protein coupled bile acid receptor 1 Steroid-like ligand receptor CHEMBL169 CHEMBL1041788 (1) CHEMBL1041789 (1)
0 / 0
O75604 Ubiquitin carboxyl-terminal hydrolase 2 Enzyme CHEMBL1593360 CHEMBL1614331 (1)
0 / 0
P02545 Prelamin-A/C Unclassified protein CHEMBL1593360 CHEMBL1614544 (1)
11 / 10
P08047 Transcription factor Sp1 Unclassified protein CHEMBL169 CHEMBL1058704 (1)
0 / 0
P10828 Thyroid hormone receptor beta NR1A2 CHEMBL1316667 CHEMBL1613776 (1)
3 / 1
P10586 Receptor-type tyrosine-protein phosphatase F Receptor tyrosine-protein phosphatase CHEMBL169 CHEMBL963013 (1) CHEMBL1828251 (1)
CHEMBL2149376 (1)
0 / 0
P11712 Cytochrome P450 2C9 Cytochrome P450 2C9 CHEMBL1316667 CHEMBL1741325 (1)
0 / 1
P23219 Prostaglandin G/H synthase 1 Oxidoreductase CHEMBL169 CHEMBL1003454 (1) CHEMBL1003456 (1)
CHEMBL1003457 (1)
0 / 0
P28845 Corticosteroid 11-beta-dehydrogenase isozyme 1 Enzyme CHEMBL169 CHEMBL1072762 (1) CHEMBL1065225 (1)
1 / 1
Q9UQL6 Histone deacetylase 5 Hydrolase CHEMBL169 CHEMBL1785672 (1)
0 / 0
Q92830 Histone acetyltransferase KAT2A Enzyme CHEMBL169 CHEMBL1738606 (1)
0 / 0
P15121 Aldose reductase Enzyme CHEMBL169 CHEMBL2168781 (1)
0 / 0
P49841 Glycogen synthase kinase-3 beta Gsk CHEMBL169 CHEMBL1053705 (1)
0 / 0
Q04206 Transcription factor p65 Transcription Factor CHEMBL169 CHEMBL1109182 (1)
0 / 0
P83916 Chromobox protein homolog 1 Unclassified protein CHEMBL169 CHEMBL1794401 (1)
0 / 0
O94782 Ubiquitin carboxyl-terminal hydrolase 1 Enzyme CHEMBL1593360 CHEMBL1794467 (1)
0 / 0
P11511 Cytochrome P450 19A1 Cytochrome P450 19A1 CHEMBL169 CHEMBL978973 (1) CHEMBL978974 (1)
CHEMBL978975 (1)
2 / 2
Q96RI1 Bile acid receptor NR1H4 CHEMBL169 CHEMBL1041790 (1)
0 / 0
O15379 Histone deacetylase 3 Hydrolase CHEMBL169 CHEMBL1785662 (1)
0 / 0
P18433 Receptor-type tyrosine-protein phosphatase alpha Receptor tyrosine-protein phosphatase CHEMBL169 CHEMBL963014 (1) CHEMBL1828250 (1)
0 / 0
P05177 Cytochrome P450 1A2 Cytochrome P450 1A2 CHEMBL1316667 CHEMBL1741322 (1)
0 / 0
P56524 Histone deacetylase 4 Hydrolase CHEMBL169 CHEMBL1785671 (1)
1 / 1
P19838 Nuclear factor NF-kappa-B p105 subunit Transcription Factor CHEMBL169 CHEMBL1109181 (1)
0 / 0
P30305 M-phase inducer phosphatase 2 Ser_Thr_Tyr CHEMBL169 CHEMBL1828247 (1)
0 / 0
P33261 Cytochrome P450 2C19 Cytochrome P450 2C19 CHEMBL1316667 CHEMBL1741323 (1)
1 / 1
P08684 Cytochrome P450 3A4 Cytochrome P450 3A4 CHEMBL1316667 CHEMBL1741324 (1)
0 / 1
P27695 DNA-(apurinic or apyrimidinic site) lyase Enzyme CHEMBL169 CHEMBL1614211 (1)
0 / 0
Q07869 Peroxisome proliferator-activated receptor alpha NR1C1 CHEMBL169 CHEMBL1837228 (1) CHEMBL1837229 (2)
CHEMBL1837230 (1) CHEMBL1837231 (1)
CHEMBL1837232 (1) CHEMBL1837233 (1)
CHEMBL1839605 (1) CHEMBL1839606 (1)
CHEMBL1839607 (1) CHEMBL1839608 (1)
CHEMBL1839609 (1) CHEMBL1839610 (1)
CHEMBL1839611 (1) CHEMBL1839612 (1)
CHEMBL1839613 (1) CHEMBL1839614 (1)
CHEMBL1839615 (1)
0 / 0
P17706 Tyrosine-protein phosphatase non-receptor type 2 Tyr CHEMBL169 CHEMBL963011 (1) CHEMBL1828246 (1)
CHEMBL2344761 (1)
0 / 1
Q9UBN7 Histone deacetylase 6 Hydrolase CHEMBL169 CHEMBL1785670 (1)
0 / 0
P29350 Tyrosine-protein phosphatase non-receptor type 6 Tyr CHEMBL169 CHEMBL963012 (1) CHEMBL1828248 (1)
0 / 0
P80365 Corticosteroid 11-beta-dehydrogenase isozyme 2 Enzyme CHEMBL169 CHEMBL1072765 (1)
1 / 1
P23469 Receptor-type tyrosine-protein phosphatase epsilon Receptor tyrosine-protein phosphatase CHEMBL169 CHEMBL963015 (1)
0 / 0
P46063 ATP-dependent DNA helicase Q1 Enzyme CHEMBL169 CHEMBL1613829 (1)
0 / 0
O75874 Isocitrate dehydrogenase [NADP] cytoplasmic Enzyme CHEMBL169 CHEMBL2354311 (1)
1 / 0
O00255 Menin Unclassified protein CHEMBL169 CHEMBL1316667 CHEMBL1614257 (2) CHEMBL1614531 (1)
2 / 5
Q03164 Histone-lysine N-methyltransferase 2A Enzyme CHEMBL169 CHEMBL1316667 CHEMBL1614257 (2) CHEMBL1614531 (1)
1 / 3
Q13951 Core-binding factor subunit beta Unclassified protein CHEMBL1316667 CHEMBL1613933 (1)
0 / 1
Q01196 Runt-related transcription factor 1 Unclassified protein CHEMBL1316667 CHEMBL1613933 (1)
1 / 6
O94925 Glutaminase kidney isoform, mitochondrial Enzyme CHEMBL169 CHEMBL2114738 (1)
0 / 0

CTD interaction (20)

compound gene gene name gene description interaction interaction type form reference
pmid
C005466 9131 AIFM1
AIF
CMTX4
COWCK
COXPD6
PDCD8
apoptosis-inducing factor, mitochondrion-associated, 1 AIFM1 mutant form results in decreased susceptibility to ursolic acid decreases response to substance
mutant form 20630652
C005466 9131 AIFM1
AIF
CMTX4
COWCK
COXPD6
PDCD8
apoptosis-inducing factor, mitochondrion-associated, 1 ursolic acid results in increased localization of AIFM1 protein increases localization
protein 20630652
C005466 578 BAK1
BAK
BAK-LIKE
BCL2L7
CDN1
BCL2-antagonist/killer 1 ursolic acid results in increased activity of BAK1 protein increases activity
protein 20630652
C005466 581 BAX
BCL2L4
BCL2-associated X protein ursolic acid results in increased expression of BAX protein increases expression
protein 16012738
C005466 596 BCL2
Bcl-2
PPP1R50
B-cell CLL/lymphoma 2 ursolic acid results in decreased expression of BCL2 protein decreases expression
protein 16012738
C005466 836 CASP3
CPP32
CPP32B
SCA-1
caspase 3, apoptosis-related cysteine peptidase (EC:3.4.22.56) acetyl-aspartyl-glutamyl-valyl-aspartal inhibits the reaction [ursolic acid results in increased cleavage of and results in increased activity of CASP3 protein] decreases reaction
/ increases activity
/ increases cleavage
protein 16012738
C005466 836 CASP3
CPP32
CPP32B
SCA-1
caspase 3, apoptosis-related cysteine peptidase (EC:3.4.22.56) ursolic acid results in increased activity of CASP3 protein increases activity
protein 20005942
C005466 836 CASP3
CPP32
CPP32B
SCA-1
caspase 3, apoptosis-related cysteine peptidase (EC:3.4.22.56) ursolic acid results in increased cleavage of and results in increased activity of CASP3 protein increases activity
/ increases cleavage
protein 16012738
C005466 841 CASP8
ALPS2B
CAP4
Casp-8
FLICE
MACH
MCH5
caspase 8, apoptosis-related cysteine peptidase (EC:3.4.22.61) ursolic acid results in increased activity of CASP8 protein increases activity
protein 20005942
C005466 54205 CYCS
CYC
HCS
THC4
cytochrome c, somatic ursolic acid affects the localization of CYCS protein affects localization
protein 16012738
C005466 1557 CYP2C19
CPCJ
CYP2C
P450C2C
P450IIC19
cytochrome P450, family 2, subfamily C, polypeptide 19 (EC:1.14.13.48 1.14.13.49 1.14.13.80) ursolic acid inhibits the reaction [CYP2C19 protein results in increased metabolism of Mephenytoin] decreases reaction
/ increases metabolic processing
protein 15043991
C005466 1557 CYP2C19
CPCJ
CYP2C
P450C2C
P450IIC19
cytochrome P450, family 2, subfamily C, polypeptide 19 (EC:1.14.13.48 1.14.13.49 1.14.13.80) ursolic acid results in decreased activity of CYP2C19 protein decreases activity
protein 15043991
C005466 3383 ICAM1
BB2
CD54
P3.58
intercellular adhesion molecule 1 ursolic acid results in decreased expression of ICAM1 mRNA decreases expression
mRNA 21539908
C005466 3383 ICAM1
BB2
CD54
P3.58
intercellular adhesion molecule 1 ursolic acid results in decreased expression of ICAM1 protein decreases expression
protein 20005942
C005466 4313 MMP2
CLG4
CLG4A
MMP-II
MONA
TBE-1
matrix metallopeptidase 2 (gelatinase A, 72kDa gelatinase, 72kDa type IV collagenase) (EC:3.4.24.24) ursolic acid results in decreased expression of MMP2 mRNA decreases expression
mRNA 21539908
C005466 4318 MMP9
CLG4B
GELB
MANDP2
MMP-9
matrix metallopeptidase 9 (gelatinase B, 92kDa gelatinase, 92kDa type IV collagenase) (EC:3.4.24.35) ursolic acid results in decreased expression of MMP9 mRNA decreases expression
mRNA 21539908
C005466 142 PARP1
ADPRT
ADPRT_1
ADPRT1
ARTD1
PARP
PARP-1
PPOL
pADPRT-1
poly (ADP-ribose) polymerase 1 (EC:2.4.2.30) ursolic acid results in increased cleavage of PARP1 protein increases cleavage
protein 16012738
C005466 7040 TGFB1
CED
DPD1
LAP
TGFB
TGFbeta
transforming growth factor, beta 1 ursolic acid results in decreased expression of TGFB1 protein decreases expression
protein 21539908
C005466 7150 TOP1
TOPI
topoisomerase (DNA) I (EC:5.99.1.2) ursolic acid results in decreased activity of TOP1 protein decreases activity
protein 10860928
C005466 7153 TOP2A
TOP2
TP2A
topoisomerase (DNA) II alpha 170kDa (EC:5.99.1.3) ursolic acid results in decreased activity of TOP2A protein decreases activity
protein 10860928

Related Disease

Diseases related to proteins in ChEMBL interactions

OMIM (26)

OMIM preferred title UniProt
#218030 Apparent mineralocorticoid excess; ame P80365
#613546 Aromatase deficiency P11511
#139300 Aromatase excess syndrome; aexs P11511
#600430 Brachydactyly-mental retardation syndrome; bdmr P56524
#115200 Cardiomyopathy, dilated, 1a; cmd1a P02545
#212112 Cardiomyopathy, dilated, with hypergonadotropic hypogonadism P02545
#605588 Charcot-marie-tooth disease, axonal, type 2b1; cmt2b1 P02545
#604931 Cortisone reductase deficiency 1; cortrd1 P28845
#609535 Drug metabolism, poor, cyp2c19-related P33261
#608902 Drug metabolism, poor, cyp2d6-related P10635
#181350 Emery-dreifuss muscular dystrophy 2, autosomal dominant; edmd2 P02545
#137800 Glioma susceptibility 1; glm1 O75874
#605130 Hairy elbows, short stature, facial dysmorphism, and developmental delay Q03164
#610140 Heart-hand syndrome, slovenian type P02545
#176670 Hutchinson-gilford progeria syndrome; hgps P02545
#145000 Hyperparathyroidism 1; hrpt1 O00255
#151660 Lipodystrophy, familial partial, type 2; fpld2 P02545
#248370 Mandibuloacral dysplasia with type a lipodystrophy; mada P02545
#131100 Multiple endocrine neoplasia, type i; men1 O00255
#613205 Muscular dystrophy, congenital, lmna-related P02545
#159001 Muscular dystrophy, limb-girdle, type 1b; lgmd1b P02545
#601399 Platelet disorder, familial, with associated myeloid malignancy Q01196
#275210 Restrictive dermopathy, lethal P02545
#188570 Thyroid hormone resistance, generalized, autosomal dominant; grth P10828
#274300 Thyroid hormone resistance, generalized, autosomal recessive; grth P10828
#145650 Thyroid hormone resistance, selective pituitary; prth P10828

KEGG DISEASE (33)

KEGG disease name UniProt
H00033 Adrenal carcinoma O00255 (related)
H00034 Carcinoid O00255 (related)
H00045 Malignant islet cell carcinoma O00255 (related)
H00246 Primary hyperparathyroidism O00255 (related)
H01102 Pituitary adenomas O00255 (related)
H00264 Charcot-Marie-Tooth disease (CMT) P02545 (related)
H00294 Dilated cardiomyopathy (DCM) P02545 (related)
H00420 Familial partial lipodystrophy (FPL) P02545 (related)
H00563 Emery-Dreifuss muscular dystrophy P02545 (related)
H00590 Congenital muscular dystrophies (CMD/MDC) P02545 (related)
H00593 Limb-girdle muscular dystrophy (LGMD) P02545 (related)
H00601 Hutchinson-Gilford progeria syndrome P02545 (related)
H00663 Restrictive dermopathy P02545 (related)
H00665 Mandibuloacral dysplasia P02545 (related)
H01216 Left ventricular noncompaction (LVNC) P02545 (related)
H00036 Osteosarcoma P08684 (marker)
H00249 Thyroid hormone resistance syndrome P10828 (related)
H00599 46,XX disorders of sex development (Disorders related to androgen excess) P11511 (related)
H00794 Aromatase excess syndrome P11511 (related)
H01205 Coumarin resistance P11712 (related)
H00408 Type I diabetes mellitus P17706 (related)
H01111 Cortisone reductase deficiency (CRD) P28845 (related)
H01171 Poor drug metabolism (PM) P33261 (related)
H00017 Esophageal cancer P35354 (related)
H00025 Penile cancer P35354 (related)
H00046 Cholangiocarcinoma P35354 (related)
H00561 Brachydacytly-mental retardation syndrome and Smith-Magenis syndrome P56524 (related)
H00259 Apparent mineralocorticoid excess syndrome P80365 (related)
H00001 Acute lymphoblastic leukemia (ALL) (precursor B lymphoblastic leukemia) Q01196 (related)
Q01196 (marker)
Q03164 (related)
Q03164 (marker)
H00003 Acute myeloid leukemia (AML) Q01196 (related)
Q01196 (marker)
Q13951 (marker)
H00004 Chronic myeloid leukemia (CML) Q01196 (related)
H00978 Thrombocytopenia (THC) Q01196 (related)
H00002 Acute lymphoblastic leukemia (ALL) (precursor T lymphoblastic leukemia) Q03164 (related)

Diseases related to CTD interactions

12 disease from interactions of metabolites

MeSH disease OMIM compound disease name evidence type reference
pmid
D001284 C005466 Atrophy therapeutic
20869956
D006528 C005466 Carcinoma, Hepatocellular therapeutic
20630652
D002471 C005466 Cell Transformation, Neoplastic therapeutic
19329757
D003921 C005466 Diabetes Mellitus, Experimental therapeutic
20869956
D006943 C005466 Hyperglycemia therapeutic
20869956
D006949 C005466 Hyperlipidemias therapeutic
8847885
D006965 C005466 Hyperplasia therapeutic
19329757
D007249 C005466 Inflammation therapeutic
8847885
D008103 C005466 Liver Cirrhosis therapeutic
21172400
D017202 C005466 Myocardial Ischemia therapeutic
17052790
20020988
D009369 C005466 Neoplasms therapeutic
8847885
D012878 C005466 Skin Neoplasms therapeutic
19329757