KNApSAcK Metabolite C00003741
Metabolite
KNApSAcK Entry
| id | C00003741 |
|---|---|
| Name | Betulinic acid |
| CAS RN | 472-15-1 |
| Standard InChI | InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1 |
| Standard InChI (Main Layer) | InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33) |
Cluster
| Phytochemical cluster | No. 51 |
|---|---|
| KCF-S cluster | No. 23 |
Link
ChEMBL
| By standard InChI | CHEMBL269277 |
|---|---|
| By standard InChI Main Layer | CHEMBL269277 CHEMBL71690 CHEMBL519059 CHEMBL1318530 CHEMBL2005635 |
KEGG
| By LinkDB | C08619 |
|---|
CTD
| By CAS RN | C002070 |
|---|
Species
Summary
Plant class
| class name | count |
|---|---|
| asterids | 99 |
| rosids | 38 |
| eudicotyledons | 9 |
| Magnoliophyta | 3 |
| Liliopsida | 1 |
Family (Top 10)
| family name | count |
|---|---|
| Ebenaceae | 75 |
| Fabaceae | 7 |
| Myrtaceae | 6 |
| Ericaceae | 5 |
| Rhamnaceae | 4 |
| Lamiaceae | 4 |
| Clusiaceae | 3 |
| Pentaphylacaceae | 3 |
| Oleaceae | 2 |
| Malvaceae | 2 |
List (156)
* NCBI
Human Protein / Gene in interaction
34 ChEMBL Protein in interactions
| accession | description | class description | compound | assay ID (# of activities) |
# of diseases
(OMIM / KEGG) |
|---|---|---|---|---|---|
| P10635 | Cytochrome P450 2D6 | Cytochrome P450 2D6 | CHEMBL1318530 |
CHEMBL1741321
(1)
|
1 / 0 |
| P49798 | Regulator of G-protein signaling 4 | Unclassified protein | CHEMBL269277 |
CHEMBL1794499
(1)
|
2 / 0 |
| O60218 | Aldo-keto reductase family 1 member B10 | Enzyme | CHEMBL269277 |
CHEMBL2168780
(1)
|
0 / 0 |
| P06746 | DNA polymerase beta | Enzyme | CHEMBL269277 |
CHEMBL921744
(1)
CHEMBL921745
(1)
CHEMBL993810 (1) CHEMBL1614079 (1) |
0 / 0 |
| Q8TDU6 | G-protein coupled bile acid receptor 1 | Steroid-like ligand receptor | CHEMBL269277 |
CHEMBL1041788
(1)
CHEMBL1041789
(1)
|
0 / 0 |
| O75604 | Ubiquitin carboxyl-terminal hydrolase 2 | Enzyme | CHEMBL1318530 |
CHEMBL1614331
(1)
|
0 / 0 |
| P02545 | Prelamin-A/C | Unclassified protein | CHEMBL1318530 |
CHEMBL1614544
(1)
|
11 / 10 |
| Q02156 | Protein kinase C epsilon type | Eta | CHEMBL269277 |
CHEMBL997494
(1)
|
0 / 0 |
| P11712 | Cytochrome P450 2C9 | Cytochrome P450 2C9 | CHEMBL1318530 |
CHEMBL1741325
(1)
|
0 / 1 |
| P15559 | NAD(P)H dehydrogenase [quinone] 1 | Enzyme | CHEMBL269277 |
CHEMBL1004305
(1)
|
0 / 0 |
| P11387 | DNA topoisomerase 1 | Isomerase | CHEMBL269277 |
CHEMBL1108448
(1)
|
0 / 0 |
| P11388 | DNA topoisomerase 2-alpha | Isomerase | CHEMBL269277 |
CHEMBL1108449
(1)
|
0 / 0 |
| Q16665 | Hypoxia-inducible factor 1-alpha | Transcription Factor | CHEMBL1318530 |
CHEMBL1614456
(1)
CHEMBL1613803
(1)
|
0 / 0 |
| P08151 | Zinc finger protein GLI1 | Unclassified protein | CHEMBL269277 |
CHEMBL972431
(1)
CHEMBL987100
(2)
CHEMBL987104 (1) CHEMBL987105 (1) CHEMBL987107 (1) CHEMBL987108 (1) |
0 / 0 |
| O75496 | Geminin | Unclassified protein | CHEMBL269277 CHEMBL71690 |
CHEMBL2114843
(2)
CHEMBL2114780
(1)
|
0 / 0 |
| P15121 | Aldose reductase | Enzyme | CHEMBL269277 |
CHEMBL2168781
(1)
|
0 / 0 |
| P49841 | Glycogen synthase kinase-3 beta | Gsk | CHEMBL269277 |
CHEMBL1053705
(1)
|
0 / 0 |
| P43220 | Glucagon-like peptide 1 receptor | Glucagon-like peptide receptor | CHEMBL71690 |
CHEMBL2114931
(1)
|
0 / 0 |
| Q04206 | Transcription factor p65 | Transcription Factor | CHEMBL269277 |
CHEMBL1109182
(1)
|
0 / 0 |
| Q9Y253 | DNA polymerase eta | Enzyme | CHEMBL71690 |
CHEMBL1794569
(1)
|
1 / 1 |
| Q9HC16 | DNA dC->dU-editing enzyme APOBEC-3G | Enzyme | CHEMBL71690 |
CHEMBL1963863
(1)
|
0 / 0 |
| Q96RI1 | Bile acid receptor | NR1H4 | CHEMBL269277 |
CHEMBL1041790
(1)
|
0 / 0 |
| Q13133 | Oxysterols receptor LXR-alpha | NR1H3 | CHEMBL269277 |
CHEMBL1007705
(1)
CHEMBL1007709
(1)
CHEMBL1008515 (1) |
0 / 0 |
| P05177 | Cytochrome P450 1A2 | Cytochrome P450 1A2 | CHEMBL1318530 |
CHEMBL1741322
(1)
|
0 / 0 |
| P55055 | Oxysterols receptor LXR-beta | NR1H3 | CHEMBL269277 |
CHEMBL1007707
(1)
CHEMBL1007710
(1)
CHEMBL1008519 (1) |
0 / 0 |
| P19838 | Nuclear factor NF-kappa-B p105 subunit | Transcription Factor | CHEMBL269277 |
CHEMBL1109181
(1)
|
0 / 0 |
| P05771 | Protein kinase C beta type | Alpha | CHEMBL269277 |
CHEMBL997493
(1)
|
0 / 0 |
| P33261 | Cytochrome P450 2C19 | Cytochrome P450 2C19 | CHEMBL1318530 |
CHEMBL1741323
(1)
|
1 / 1 |
| P08684 | Cytochrome P450 3A4 | Cytochrome P450 3A4 | CHEMBL1318530 |
CHEMBL1741324
(1)
|
0 / 1 |
| Q9UBT6 | DNA polymerase kappa | Enzyme | CHEMBL269277 CHEMBL1318530 |
CHEMBL1794536
(2)
|
0 / 0 |
| O75874 | Isocitrate dehydrogenase [NADP] cytoplasmic | Enzyme | CHEMBL71690 |
CHEMBL2354311
(1)
|
1 / 0 |
| Q8IUX4 | DNA dC->dU-editing enzyme APOBEC-3F | Enzyme | CHEMBL269277 |
CHEMBL1963966
(1)
|
0 / 0 |
| Q9UBT2 | SUMO-activating enzyme subunit 2 | Enzyme | CHEMBL269277 |
CHEMBL1614105
(1)
CHEMBL1614290
(1)
|
0 / 0 |
| Q9UBE0 | SUMO-activating enzyme subunit 1 | Unclassified protein | CHEMBL269277 |
CHEMBL1614105
(1)
CHEMBL1614290
(1)
|
0 / 0 |
CTD interaction (20)
| compound | gene | gene name | gene description | interaction | interaction type | form |
reference
pmid |
|---|---|---|---|---|---|---|---|
| C002070 | 207 |
AKT1
AKT CWS6 PKB PKB-ALPHA PRKBA RAC RAC-ALPHA |
v-akt murine thymoma viral oncogene homolog 1 (EC:2.7.11.1) | 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline inhibits the reaction [betulinic acid results in increased phosphorylation of AKT1 protein] |
decreases reaction
/ increases phosphorylation |
protein |
16077934
|
| C002070 | 207 |
AKT1
AKT CWS6 PKB PKB-ALPHA PRKBA RAC RAC-ALPHA |
v-akt murine thymoma viral oncogene homolog 1 (EC:2.7.11.1) | betulinic acid results in increased phosphorylation of AKT1 protein |
increases phosphorylation
|
protein |
16077934
|
| C002070 | 581 |
BAX
BCL2L4 |
BCL2-associated X protein | [2-(1H-indazol-4-yl)-6-(4-methanesulfonylpiperazin-1-ylmethyl)-4-morpholin-4-ylthieno(3,2-d)pyrimidine co-treated with betulinic acid analog] results in increased activity of BAX protein |
affects cotreatment
/ increases activity |
protein |
23000516
|
| C002070 | 581 |
BAX
BCL2L4 |
BCL2-associated X protein | CA 074 methyl ester inhibits the reaction [[2-(1H-indazol-4-yl)-6-(4-methanesulfonylpiperazin-1-ylmethyl)-4-morpholin-4-ylthieno(3,2-d)pyrimidine co-treated with betulinic acid analog] results in increased activity of BAX protein] |
affects cotreatment
/ decreases reaction / increases activity |
protein |
23000516
|
| C002070 | 332 |
BIRC5
API4 EPR-1 |
baculoviral IAP repeat containing 5 | 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline inhibits the reaction [betulinic acid results in increased expression of BIRC5] |
decreases reaction
/ increases expression |
16077934
|
|
| C002070 | 332 |
BIRC5
API4 EPR-1 |
baculoviral IAP repeat containing 5 | betulinic acid results in increased expression of BIRC5 |
increases expression
|
16077934
|
|
| C002070 | 332 |
BIRC5
API4 EPR-1 |
baculoviral IAP repeat containing 5 | BIRC5 protein results in decreased susceptibility to betulinic acid |
decreases response to substance
|
protein |
16077934
|
| C002070 | 836 |
CASP3
CPP32 CPP32B SCA-1 |
caspase 3, apoptosis-related cysteine peptidase (EC:3.4.22.56) | 2-(1H-indazol-4-yl)-6-(4-methanesulfonylpiperazin-1-ylmethyl)-4-morpholin-4-ylthieno(3,2-d)pyrimidine promotes the reaction [betulinic acid analog results in increased cleavage of CASP3 protein] |
increases cleavage
/ increases reaction |
protein |
23000516
|
| C002070 | 836 |
CASP3
CPP32 CPP32B SCA-1 |
caspase 3, apoptosis-related cysteine peptidase (EC:3.4.22.56) | betulinic acid analog results in increased cleavage of CASP3 protein |
increases cleavage
|
protein |
23000516
|
| C002070 | 836 |
CASP3
CPP32 CPP32B SCA-1 |
caspase 3, apoptosis-related cysteine peptidase (EC:3.4.22.56) | betulinic acid results in increased activity of CASP3 protein |
increases activity
|
protein |
22260869
|
| C002070 | 836 |
CASP3
CPP32 CPP32B SCA-1 |
caspase 3, apoptosis-related cysteine peptidase (EC:3.4.22.56) | CA 074 methyl ester inhibits the reaction [2-(1H-indazol-4-yl)-6-(4-methanesulfonylpiperazin-1-ylmethyl)-4-morpholin-4-ylthieno(3,2-d)pyrimidine promotes the reaction [betulinic acid analog results in increased cleavage of CASP3 protein]] |
decreases reaction
/ increases cleavage / increases reaction |
protein |
23000516
|
| C002070 | 840 |
CASP7
CASP-7 CMH-1 ICE-LAP3 LICE2 MCH3 |
caspase 7, apoptosis-related cysteine peptidase (EC:3.4.22.60) | betulinic acid results in increased activity of CASP7 protein |
increases activity
|
protein |
22260869
|
| C002070 | 1956 |
EGFR
ERBB ERBB1 HER1 PIG61 mENA |
epidermal growth factor receptor (EC:2.7.10.1) | 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline inhibits the reaction [betulinic acid results in increased phosphorylation of EGFR protein] |
decreases reaction
/ increases phosphorylation |
protein |
16077934
|
| C002070 | 1956 |
EGFR
ERBB ERBB1 HER1 PIG61 mENA |
epidermal growth factor receptor (EC:2.7.10.1) | betulinic acid results in increased phosphorylation of EGFR protein |
increases phosphorylation
|
protein |
16077934
|
| C002070 | 5594 |
MAPK1
ERK ERK2 ERT1 MAPK2 P42MAPK PRKM1 PRKM2 p38 p40 p41 p41mapk |
mitogen-activated protein kinase 1 (EC:2.7.11.24) | 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline inhibits the reaction [betulinic acid results in increased phosphorylation of MAPK1 protein] |
decreases reaction
/ increases phosphorylation |
protein |
16077934
|
| C002070 | 5594 |
MAPK1
ERK ERK2 ERT1 MAPK2 P42MAPK PRKM1 PRKM2 p38 p40 p41 p41mapk |
mitogen-activated protein kinase 1 (EC:2.7.11.24) | betulinic acid results in increased phosphorylation of MAPK1 protein |
increases phosphorylation
|
protein |
16077934
|
| C002070 | 5595 |
MAPK3
ERK-1 ERK1 ERT2 HS44KDAP HUMKER1A P44ERK1 P44MAPK PRKM3 p44-ERK1 p44-MAPK |
mitogen-activated protein kinase 3 (EC:2.7.11.24) | 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline inhibits the reaction [betulinic acid results in increased phosphorylation of MAPK3 protein] |
decreases reaction
/ increases phosphorylation |
protein |
16077934
|
| C002070 | 5595 |
MAPK3
ERK-1 ERK1 ERT2 HS44KDAP HUMKER1A P44ERK1 P44MAPK PRKM3 p44-ERK1 p44-MAPK |
mitogen-activated protein kinase 3 (EC:2.7.11.24) | betulinic acid results in increased phosphorylation of MAPK3 protein |
increases phosphorylation
|
protein |
16077934
|
| C002070 | 7150 |
TOP1
TOPI |
topoisomerase (DNA) I (EC:5.99.1.2) | betulinic acid results in decreased activity of TOP1 protein |
decreases activity
|
protein |
10860928
|
| C002070 | 7153 |
TOP2A
TOP2 TP2A |
topoisomerase (DNA) II alpha 170kDa (EC:5.99.1.3) | betulinic acid results in decreased activity of TOP2A protein |
decreases activity
|
protein |
10860928
|
Related Disease
Diseases related to proteins in ChEMBL interactions
OMIM (17)
| OMIM | preferred title | UniProt |
|---|---|---|
| #115200 | Cardiomyopathy, dilated, 1a; cmd1a |
P02545
|
| #212112 | Cardiomyopathy, dilated, with hypergonadotropic hypogonadism |
P02545
|
| #605588 | Charcot-marie-tooth disease, axonal, type 2b1; cmt2b1 |
P02545
|
| #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
|
| #610140 | Heart-hand syndrome, slovenian type |
P02545
|
| #176670 | Hutchinson-gilford progeria syndrome; hgps |
P02545
|
| #151660 | Lipodystrophy, familial partial, type 2; fpld2 |
P02545
|
| #248370 | Mandibuloacral dysplasia with type a lipodystrophy; mada |
P02545
|
| #613205 | Muscular dystrophy, congenital, lmna-related |
P02545
|
| #159001 | Muscular dystrophy, limb-girdle, type 1b; lgmd1b |
P02545
|
| #275210 | Restrictive dermopathy, lethal |
P02545
|
| #604906 | Schizophrenia 9; sczd9 |
P49798
|
| #181500 | Schizophrenia; sczd |
P49798
|
| #278750 | Xeroderma pigmentosum, variant type; xpv |
Q9Y253
|
KEGG DISEASE (14)
| KEGG | disease name | UniProt |
|---|---|---|
| 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)
|
| H01205 | Coumarin resistance |
P11712
(related)
|
| H01171 | Poor drug metabolism (PM) |
P33261
(related)
|
| H00403 | Disorders of nucleotide excision repair |
Q9Y253
(related)
|