General Information of the Compound
Compound ID
CP0040160
Compound Name
9-cis-retinoic acid (9cRA)
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Synonyms
15-Apo-beta-caroten-15-oic acid
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
302-79-4
9(Z)-Retinoic acid
9-cis-RA
9-trans-retinoic acid
A-Acido (Argentina)
A-Vitaminsyre
A-Vitaminsyre [Denmark]
AGN 192013
AGN100335
ALRT 1057
AT-RA
ATRA
Aberel
Aberela
Aberela (TN)
Aberela [Norway]
Accutane Roche
Acid A Vit (Belgium, Netherlands)
Acid, Retinoic
Acid, Vitamin A
Acid, all-trans-Retinoic
Acid, beta-all-trans-Retinoic
Acid, trans-Retinoic
Acide retinoique (French) (DSL)
Acnavit
Acnavit [Denmark]
Airol
Aknefug
Aknoten
All Trans Retinoic Acid
All trans-Retinoic acid
All-(E)-Retinoic acid
All-trans Retinoic Acid
All-trans-Retinoic acid
All-trans-Tretinoin
All-trans-Vitamin A acid
All-trans-Vitamin A1 acid
All-trans-b-Retinoic acid
All-trans-beta-Retinoic acid
Alltrans-retinoic acid
Atra-IV
Atragen
Atralin
Avita (TN)
Avita Gel
Avitoin
Avitoin [Norway]
B-Retinoic acid
BAL4079
BML2-E05
Beta all trans Retinoic Acid
Beta-Ra
Beta-Retinoic acid
Beta-all-trans-Retinoic acid
Betarretin
Cordes VAS [Germany]
Cordes vas
Dermairol
Effederm
Effederm [France]
Epi-aberel
Eudyna
LGD 100057
Lsotretinoin
Nexret
PDT-002-002
Panretin Gel
Panretyn
Potassium Salt, Tretinoin
R 2625
REA
RETINOIC ACID, ALL TRANS
Renova
Renova (TN)
Retacnyl
Retin A
Retin A (TN)
Retin-A
Retin-A (TN)
Retin-A Micro
Retinoate
Retinoic acid
Retinoic acid, all-trans-
Retinoic acid, all-trans-(8CI)
Retinova
Retionic acid
Retisol-A
Ro 1-5488
Salt, Tretinoin Potassium
Salt, Tretinoin Sodium
Salt, Tretinoin Zinc
Sodium Salt, Tretinoin
Solage
Stieva-A
Stieva-A (TN)
Stieva-a Forte
TRETINON
Trans Retinoic Acid
Trans-Retinoicacid
Tretin M
Tretinoin
Tretinoin (JAN/USP/INN)
Tretinoin (TN)
Tretinoin 01% cream or placebo
Tretinoin Potassium Salt
Tretinoin Sodium Salt
Tretinoin Zinc Salt
Tretinoin [USAN:INN:BAN]
Tretinoin liposome
Tretinoin/All-Trans Retinoic Acid
Tretinoina
Tretinoina [INN-Spanish]
Tretinoine
Tretinoine (French) (EINECS)
Tretinoine [INN-French]
Tretinoino
Tretinoino [INN-Spanish]
Tretinoinum
Tretinoinum [INN-Latin]
Tri-Luma
Vesanoid
Vesanoid (TN)
Vesanoid, Airol, Renova, Atralin, Retin-A, Avita, Tretinoin
Vesnaroid
Vitamin A acid
Vitamin A acid, all-trans-
Vitamin A1 acid, all-trans-
Vitinoin
Zinc Salt, Tretinoin
[3H]Retinoic acid
all-(E)-Retinoic acid
all-trans-Retinoic acid
all-trans-Tretinoin
all-trans-Vitamin A acid
all-trans-Vitamin A1 acid
beta-Ra
beta-Retinoic acid
trans-Retinoic acid
tretinoin
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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-YCNIQYBTSA-N
CAS
5300-03-8
302-79-4
56573-65-0
7005-78-9
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: 444795
SID: 12014646
ChEMBL ID
CHEMBL38
DrugBank ID
DB00755
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: PT06300, Indoleamine 2,3-dioxygenase 2
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000025 HEK-293T
 Cell Line Info 
Homo sapiens (Human)  1
1
IC50 = 28700 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Protein ID: PT01621, Retinoic acid receptor alpha
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000053 COS-7
 Cell Line Info 
Chlorocebus aethiops (Green monkey)  1
1
EC50 = 1.2 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000044 CV-1
 Cell Line Info 
Chlorocebus aethiops (Green monkey)  1
1
EC50 = 22 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 5 nM
2 IC50 = 6 nM
3 Kd = 15 nM
Protein ID: PT01475, Retinoic acid receptor alpha
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000035 NIH 3T3
 Cell Line Info 
Mus musculus (Mouse)  1
1
EC50 = 6.31 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000044 CV-1
 Cell Line Info 
Chlorocebus aethiops (Green monkey)  3
1
EC50 = 7 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
EC50 = 350 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
3
EC50 = 436 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000053 COS-7
 Cell Line Info 
Chlorocebus aethiops (Green monkey)  1
1
EC50 = 17 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000017 HeLa
 Cell Line Info 
Homo sapiens (Human)  1
1
Kd = 2.3 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 5 nM
2 EC50 = 16.1 nM
3 EC50 = 27 nM
4 EC50 = 50 nM
5 EC50 = 240 nM
6 EC50 = 350 nM
7 IC50 = 0.78 nM
8 IC50 = 0.89 nM
9 IC50 = 15 nM
10 IC50 = 9000 nM
11 Kd = 14 nM
12 Kd = 15 nM
13 Kd = 16 nM
14 Ki = 0.1 nM
15 Ki = 16 nM
16 Ki = 187 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
EC50 = 1 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
EC50 = 78 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
3
EC50 = 80 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000035 NIH 3T3
 Cell Line Info 
Mus musculus (Mouse)  2
1
EC50 = 6.31 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
EC50 = 25.12 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000053 COS-7
 Cell Line Info 
Chlorocebus aethiops (Green monkey)  1
1
EC50 = 12 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000017 HeLa
 Cell Line Info 
Homo sapiens (Human)  1
1
Kd = 0.4 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 1.5 nM
2 EC50 = 12 nM
3 EC50 = 17.6 nM
4 EC50 = 38 nM
5 EC50 = 80 nM
6 IC50 = 0.9 nM
7 IC50 = 0.94 nM
8 IC50 = 13 nM
9 IC50 = 3000 nM
10 Kd = 7 nM
11 Kd = 11 nM
12 Kd = 12 nM
13 Kd = 13 nM
14 Kd = 17 nM
15 Ki = 0.4 nM
16 Ki = 0.5 nM
17 Ki = 7 nM
18 Ki = 17.4 nM
Protein ID: PT02120, Retinoic acid receptor beta
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000053 COS-7
 Cell Line Info 
Chlorocebus aethiops (Green monkey)  1
1
EC50 = 1.2 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000044 CV-1
 Cell Line Info 
Chlorocebus aethiops (Green monkey)  1
1
EC50 = 2 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 5 nM
2 Kd = 13 nM
Protein ID: PT01806, Retinoic acid receptor gamma
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000053 COS-7
 Cell Line Info 
Chlorocebus aethiops (Green monkey)  1
1
EC50 = 0.2 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000044 CV-1
 Cell Line Info 
Chlorocebus aethiops (Green monkey)  3
1
EC50 = 0.7 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
EC50 = 10 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
3
EC50 = 19 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000035 NIH 3T3
 Cell Line Info 
Mus musculus (Mouse)  1
1
EC50 = 50.12 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 0.5 nM
2 EC50 = 6 nM
3 EC50 = 8 nM
4 EC50 = 10 nM
5 EC50 = 14.7 nM
6 IC50 = 0.5 nM
7 IC50 = 0.62 nM
8 IC50 = 18 nM
9 Kd = 0.2 nM
10 Kd = 0.3 nM
11 Kd = 3 nM
12 Kd = 16 nM
13 Kd = 17 nM
14 Kd = 18 nM
15 Kd = 19 nM
16 Ki = 0.5 nM
17 Ki = 0.6 nM
18 Ki = 0.7 nM
19 Ki = 3 nM
20 Ki = 18.5 nM
Protein ID: PT02121, Retinoic acid receptor gamma
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000053 COS-7
 Cell Line Info 
Chlorocebus aethiops (Green monkey)  1
1
EC50 = 0.6 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 4 nM
2 Kd = 18 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)  2
1
EC50 = 900 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
EC50 = 1015 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 430 nM
2 EC50 = 900 nM
3 EC50 > 10000 nM
4 IC50 > 1000 nM
5 Kd = 9 nM
6 Kd = 53 nM
7 Kd > 200 nM
8 Ki = 0.4 nM
9 Ki = 350 nM
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 > 2000 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 > 2000 nM
2 IC50 > 50000 nM
3 Kd = 1000 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 = 1211 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 > 50000 nM
2 Kd = 306 nM
3 Kd = 1000 nM
Protein ID: PT01474, 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 = 1400 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 4.5 nM
2 EC50 = 1400 nM
3 IC50 > 1000 nM
4 Ki = 0.5 nM
5 Ki = 881 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)  2
1
EC50 = 6 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
EC50 = 961 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 > 50000 nM
2 Kd = 350 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 = 1100 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 2 nM
2 EC50 = 1100 nM
3 IC50 = 350 nM
4 Kd = 306 nM
5 Kd = 350 nM
6 Ki = 1.4 nM
7 Ki = 288 nM
Clinical Information about the Compound
Drug 1 ( Tretinoin )
Drug Name Tretinoin
Company Roche Pharmaceuticals
Indication
Acne vulgaris
Approved
Acute promyelocytic leukaemia
Phase 2
Target(s)
Retinoic acid receptor gamma (RARG)
 Target Info 
Agonist