Compound Information

General Information of the Compound

Compound ID

CP0042977

Compound Name

9-cis retinoic acid

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Synonyms

Alitretinoin

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Structure

Formula

C20H28O2

Molecular Weight

300.442

Canonical SMILES

C\C(\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C(\C)=C\C(O)=O

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InChI

InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+

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InChIKey

SHGAZHPCJJPHSC-ZVCIMWCZSA-N

CAS

5300-03-8

Physicochemical Property

logP	5.6026
Rotatable Bonds	5
Heavy Atom Count	22
Polar Areas	37.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Complexity	22

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID

CID: 449171

SID: 14898408

ChEMBL ID

CHEMBL705

DrugBank ID

DB00523

Map of Molecular Bioactivity Related to the Compound

Map of Molecular Bioactivity Related to the Compound Compound Cell Line Protein Bioactivity Value: <= 0.1 μM > 0.1 μM and <= 10 μM > 10 μM Imprecise Activity

Table of Molecular Bioactivities Related to the Compound

Protein ID: PT01475, Retinoic acid receptor alpha

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000044	CV-1 Cell Line Info	Chlorocebus aethiops (Green monkey)	3
1	AC50 = 19 nM Bioactivity Info	TI LI LO TS
2	EC50 = 191 nM Bioactivity Info	TI LI LO TS
3	EC50 = 220 nM Bioactivity Info	TI LI LO TS
CL000026	CHO-K1 Cell Line Info	Cricetulus griseus (Chinese hamster)	1
1	EC50 = 1 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 23 nM
2	EC50 = 45 nM
3	EC50 = 102 nM
4	EC50 = 191 nM
5	IC50 = 7 nM
6	Kd = 11 nM
7	Kd = 90 nM
8	Kd = 93 nM
9	Ki = 22.3 nM

Protein ID: PT01452, Retinoic acid receptor beta

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000044	CV-1 Cell Line Info	Chlorocebus aethiops (Green monkey)	3
1	AC50 = 2 nM Bioactivity Info	TI LI LO TS
2	EC50 = 29 nM Bioactivity Info	TI LI LO TS
3	EC50 = 50 nM Bioactivity Info	TI LI LO TS
CL000026	CHO-K1 Cell Line Info	Cricetulus griseus (Chinese hamster)	1
1	EC50 = 0.8 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 3.3 nM
2	EC50 = 22 nM
3	EC50 = 50 nM
4	IC50 = 7 nM
5	Kd = 7 nM
6	Kd = 97 nM
7	Kd = 100 nM
8	Ki = 0.5 nM
9	Ki = 0.7 nM
10	Ki = 10.9 nM

Protein ID: PT01806, Retinoic acid receptor gamma

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000044	CV-1 Cell Line Info	Chlorocebus aethiops (Green monkey)	3
1	AC50 = 3 nM Bioactivity Info	TI LI LO TS
2	EC50 = 45 nM Bioactivity Info	TI LI LO TS
3	EC50 = 50 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 6 nM
2	EC50 = 12 nM
3	EC50 = 45 nM
4	IC50 = 17 nM
5	Kd = 0.8 nM
6	Kd = 22 nM
7	Kd = 148 nM
8	Kd = 150 nM
9	Ki = 20 nM

Protein ID: PT01930, Retinoic acid receptor RXR-alpha

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000044	CV-1 Cell Line Info	Chlorocebus aethiops (Green monkey)	4
1	AC50 = 7 nM Bioactivity Info	TI LI LO TS
2	EC50 = 100 nM Bioactivity Info	TI LI LO TS
3	EC50 = 195 nM Bioactivity Info	TI LI LO TS
4	EC50 = 250 nM Bioactivity Info	TI LI LO TS
CL000043	U2OS Cell Line Info	Homo sapiens (Human)	1
1	EC50 = 6 nM Bioactivity Info	TI LI LO TS
CL000006	HEK293 Cell Line Info	Homo sapiens (Human)	3
1	EC50 = 10 nM Bioactivity Info	TI LI LO TS
2	EC50 = 120 nM Bioactivity Info	TI LI LO TS
3	EC50 = 170 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 4 nM
2	EC50 = 6 nM
3	EC50 = 13 nM
4	EC50 = 26 nM
5	EC50 = 100 nM
6	IC50 = 32 nM
7	Kd = 1.5 nM
8	Kd = 3 nM
9	Kd = 8 nM
10	Kd = 9 nM
11	Kd = 13 nM
12	Kd = 14 nM
13	Kd = 16 nM
14	Kd = 50 nM
15	Kd = 240 nM
16	Kd = 1560 nM
17	Kd = 1810 nM
18	Ki = 8 nM
19	Ki = 8.4 nM
20	Ki = 478 nM
21	Ki = 583 nM

Protein ID: PT04149, Retinoic acid receptor RXR-alpha

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000184	RK3E Cell Line Info	Rattus norvegicus (Rat)	1
1	EC50 = 120 nM Bioactivity Info	TI LI LO TS

Protein ID: PT03152, Retinoic acid receptor RXR-alpha

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000044	CV-1 Cell Line Info	Chlorocebus aethiops (Green monkey)	1
1	EC50 = 200 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	IC50 = 82 nM
2	Kd = 32 nM

Protein ID: PT01474, Retinoic acid receptor RXR-beta

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000043	U2OS Cell Line Info	Homo sapiens (Human)	1
1	EC50 = 6 nM Bioactivity Info	TI LI LO TS
CL000044	CV-1 Cell Line Info	Chlorocebus aethiops (Green monkey)	1
1	EC50 = 200 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 2.6 nM
2	EC50 = 200 nM
3	IC50 = 12 nM
4	Kd = 11 nM
5	Kd = 15 nM
6	Kd = 35 nM
7	Ki = 7.4 nM
8	Ki = 9 nM

Protein ID: PT02538, Retinoic acid receptor RXR-beta

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000044	CV-1 Cell Line Info	Chlorocebus aethiops (Green monkey)	1
1	EC50 = 128 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	Kd = 12 nM
2	Kd = 15 nM

Protein ID: PT02226, Retinoic acid receptor RXR-gamma

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000044	CV-1 Cell Line Info	Chlorocebus aethiops (Green monkey)	1
1	EC50 = 124 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	Kd = 4 nM

Protein ID: PT02769, Retinoic acid receptor RXR-gamma

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000044	CV-1 Cell Line Info	Chlorocebus aethiops (Green monkey)	1
1	EC50 = 140 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 4.3 nM
2	EC50 = 140 nM
3	IC50 = 4 nM
4	Kd = 14 nM
5	Kd = 16 nM
6	Kd = 30 nM
7	Ki = 13 nM
8	Ki = 14 nM
9	Ki = 27 nM

Clinical Information about the Compound

Drug 1 ( Alitretinoin )

Drug Name	Alitretinoin
Company	Ligand Pharmaceuticals
Indication	Kaposi sarcoma Approved
Target(s)	Retinoic acid receptor RXR-beta (RXRB) Target Info Agonist Retinoic acid receptor RXR-alpha (RXRA) Target Info Agonist Retinoic acid receptor beta (RARB) Target Info Agonist Retinoic acid receptor RXR-gamma (RXRG) Target Info Agonist Retinoic acid receptor gamma (RARG) Target Info Modulator

Cite

About MolBiC

Correspondence

Prof. Feng ZHU

Prof. Leo, Lianyi Han