UCSF

ZINC12661824

Draw Identity 99% 90% 80% 70%

Substance Information

In ZINC since Heavy atoms Benign functionality
May 20th, 2008 22 Yes

Popular Name: 9-CIS-RETINOIC ACID 9-CIS-RETINOIC ACID

Find On: PubMed — Wikipedia — Google

CAS Numbers: 5300-03-8 , [5300-03-8]

Download: MOL2 SDF SMILES Flexibase

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 5.80 11.58 -54.7 0 2 -1 40 299.434 5 ↓
Lo Low (pH 4.5-6) 5.80 11.01 -5.25 1 2 0 37 300.442 5 ↓

Vendor Notes

Note Type Comments Provided By
ALOGPS_SOLUBILITY 4.77e-03 g/l DrugBank-approved
UniProt Database Links AL8A1_BOVIN; AL8A1_DANRE; AL8A1_HUMAN; AL8A1_MOUSE; APOM_HUMAN; APOM_MOUSE; APOM_PIG; APOM_PONAB; APOM_RAT; COT2_BOVIN; COT2_CHICK; COT2_HUMAN; COT2_MOUSE; COT2_RAT; RXR_BIOGL; RXR_LYMST ChEBI
Reactome Database Links REACT_13793 ChEBI
Patent Database Links US2005085539; US2005137213; US2005176787; US2005266457; US2007185069; US2007190102; US2007253957; US2008096848; US2008194534; US2008214545; US2008216184; US2008261978; US2008293711; WO2005060663; WO2005097128; WO2005110994; WO2006041900; WO2007098089; WO2 ChEBI

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
RARA-1-E Retinoic Acid Receptor Alpha (cluster #1 Of 1), Eukaryotic Eukaryotes 7 0.52 Binding ≤ 10μM
RARB-2-E Retinoic Acid Receptor Beta (cluster #2 Of 2), Eukaryotic Eukaryotes 7 0.52 Binding ≤ 10μM
RARG-2-E Retinoic Acid Receptor Gamma (cluster #2 Of 2), Eukaryotic Eukaryotes 17 0.49 Binding ≤ 10μM
RXRA-1-E Retinoid X Receptor Alpha (cluster #1 Of 1), Eukaryotic Eukaryotes 32 0.48 Binding ≤ 10μM
RXRB-2-E Retinoid X Receptor Beta (cluster #2 Of 2), Eukaryotic Eukaryotes 15 0.50 Binding ≤ 10μM
RXRG-1-E Retinoid X Receptor Gamma (cluster #1 Of 1), Eukaryotic Eukaryotes 4 0.53 Binding ≤ 10μM
RARA-1-E Retinoic Acid Receptor Alpha (cluster #1 Of 1), Eukaryotic Eukaryotes 304 0.41 Functional ≤ 10μM
RARB-1-E Retinoic Acid Receptor Beta (cluster #1 Of 1), Eukaryotic Eukaryotes 52 0.46 Functional ≤ 10μM
RARG-1-E Retinoic Acid Receptor Gamma (cluster #1 Of 1), Eukaryotic Eukaryotes 74 0.45 Functional ≤ 10μM
RXRA-1-E Retinoid X Receptor Alpha (cluster #1 Of 1), Eukaryotic Eukaryotes 13 0.50 Functional ≤ 10μM
RXRB-1-E Retinoid X Receptor Beta (cluster #1 Of 1), Eukaryotic Eukaryotes 4 0.53 Functional ≤ 10μM
RXRG-2-E Retinoid X Receptor Gamma (cluster #2 Of 2), Eukaryotic Eukaryotes 5 0.53 Functional ≤ 10μM
Z50594-7-O Mus Musculus (cluster #7 Of 9), Other Other 58 0.46 Functional ≤ 10μM
Z80156-5-O HL-60 (Promyeloblast Leukemia Cells) (cluster #5 Of 12), Other Other 2 0.55 Functional ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
RARA_MOUSE P11416 Retinoic Acid Receptor Alpha, Mouse 7 0.52 Binding ≤ 1μM
RARA_HUMAN P10276 Retinoic Acid Receptor Alpha, Human 102 0.44 Binding ≤ 1μM
RARB_MOUSE P22605 Retinoic Acid Receptor Beta, Mouse 7 0.52 Binding ≤ 1μM
RARB_HUMAN P10826 Retinoic Acid Receptor Beta, Human 0.5 0.59 Binding ≤ 1μM
RARG_MOUSE P18911 Retinoic Acid Receptor Gamma, Mouse 17 0.49 Binding ≤ 1μM
RARG_HUMAN P13631 Retinoic Acid Receptor Gamma, Human 0.8 0.58 Binding ≤ 1μM
RXRA_HUMAN P19793 Retinoid X Receptor Alpha, Human 1.5 0.56 Binding ≤ 1μM
RXRA_MOUSE P28700 Retinoid X Receptor Alpha, Mouse 200 0.43 Binding ≤ 1μM
RXRB_MOUSE P28704 Retinoid X Receptor Beta, Mouse 12 0.50 Binding ≤ 1μM
RXRB_HUMAN P28702 Retinoid X Receptor Beta, Human 11 0.51 Binding ≤ 1μM
RXRG_HUMAN P48443 Retinoid X Receptor Gamma, Human 13 0.50 Binding ≤ 1μM
RXRG_MOUSE P28705 Retinoid X Receptor Gamma, Mouse 124 0.44 Binding ≤ 1μM
RARA_MOUSE P11416 Retinoic Acid Receptor Alpha, Mouse 7 0.52 Binding ≤ 10μM
RARA_HUMAN P10276 Retinoic Acid Receptor Alpha, Human 102 0.44 Binding ≤ 10μM
RARB_MOUSE P22605 Retinoic Acid Receptor Beta, Mouse 7 0.52 Binding ≤ 10μM
RARB_HUMAN P10826 Retinoic Acid Receptor Beta, Human 0.5 0.59 Binding ≤ 10μM
RARG_MOUSE P18911 Retinoic Acid Receptor Gamma, Mouse 17 0.49 Binding ≤ 10μM
RARG_HUMAN P13631 Retinoic Acid Receptor Gamma, Human 0.8 0.58 Binding ≤ 10μM
RXRA_MOUSE P28700 Retinoid X Receptor Alpha, Mouse 200 0.43 Binding ≤ 10μM
RXRA_HUMAN P19793 Retinoid X Receptor Alpha, Human 1.5 0.56 Binding ≤ 10μM
RXRB_HUMAN P28702 Retinoid X Receptor Beta, Human 11 0.51 Binding ≤ 10μM
RXRB_MOUSE P28704 Retinoid X Receptor Beta, Mouse 12 0.50 Binding ≤ 10μM
RXRG_HUMAN P48443 Retinoid X Receptor Gamma, Human 13 0.50 Binding ≤ 10μM
RXRG_MOUSE P28705 Retinoid X Receptor Gamma, Mouse 124 0.44 Binding ≤ 10μM
Z80156 Z80156 HL-60 (Promyeloblast Leukemia Cells) 2 0.55 Functional ≤ 10μM
Z50594 Z50594 Mus Musculus 58 0.46 Functional ≤ 10μM
RARA_HUMAN P10276 Retinoic Acid Receptor Alpha, Human 102 0.44 Functional ≤ 10μM
RARB_HUMAN P10826 Retinoic Acid Receptor Beta, Human 3 0.54 Functional ≤ 10μM
RARG_HUMAN P13631 Retinoic Acid Receptor Gamma, Human 1 0.57 Functional ≤ 10μM
RXRA_HUMAN P19793 Retinoid X Receptor Alpha, Human 1.5 0.56 Functional ≤ 10μM
RXRA_RAT Q05343 Retinoid X Receptor Alpha, Rat 13 0.50 Functional ≤ 10μM
RXRB_HUMAN P28702 Retinoid X Receptor Beta, Human 200 0.43 Functional ≤ 10μM
RXRG_HUMAN P48443 Retinoid X Receptor Gamma, Human 11 0.51 Functional ≤ 10μM

Direct Reactome Annotations (via ChEBI)

Description Species
Vitamins

Reactome Annotations from Targets (via Uniprot)

Description Species
Activation of gene expression by SREBF (SREBP)
BMAL1:CLOCK,NPAS2 activates circadian gene expression
Circadian Clock
Endogenous sterols
Import of palmitoyl-CoA into the mitochondrial matrix
Nuclear Receptor transcription pathway
PPARA activates gene expression
Recycling of bile acids and salts
Regulation of lipid metabolism by Peroxisome proliferator-activated receptor alp
Regulation of pyruvate dehydrogenase (PDH) complex
REV-ERBA represses gene expression
RORA activates circadian gene expression
Synthesis of bile acids and bile salts
Synthesis of bile acids and bile salts via 27-hydroxycholesterol
Synthesis of bile acids and bile salts via 7alpha-hydroxycholesterol
Transcriptional activation of mitochondrial biogenesis
Transcriptional Regulation of Adipocyte Differentiation in 3T3-L1 Pre-adipocytes
Transcriptional regulation of white adipocyte differentiation
YAP1- and WWTR1 (TAZ)-stimulated gene expression

Analogs ( Draw Identity 99% 90% 80% 70% )