UCSF

ZINC12358651

Substance Information

In ZINC since Heavy atoms Benign functionality
May 9th, 2008 22 Yes

CAS Numbers: , 302-79-4 , 4759-48-2 , [302-79-4]

Other Names:

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid; (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; 2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen

(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate;(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid;3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate;3,7-Dimeth

(all-E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; 15-Apo-beta-caroten-15-oic acid; 2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohex

(all-E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid; 302-79

(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ECL); 302-79-4; AGN 100335; Acide retinoique (French) (DSL); C00777; Retinoate; Retino

retin-

13-CIS-RETINOIC ACID

3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2E,4E,6E,8E-tetraenoic acid

302-79-4; Avita (TN); D00094; Renova (TN); Retin A (TN); Tretinoin (JAN/USP/INN); Tretinoin (TN); Vesanoid (TN)

302-79-4; CPD000058245; Retinoic acid; SAM002264647

302-79-4; Prestwick_424; Retinoic acid

9-trans-retinoic acid

Airol

alitretinoin

All-trans Retinoic Acid (Tretinoin)

All-trans-retinoic acid

all-trans-Retinoic acid, 97%

ATRA

Atralin

Avita

BAN

C20H28O2.C7H8O2; LS-178647; MEQUINOL; TRETINOIN; SOLAGE

CHEBI:8815; CHEBI:45376

CPD000058245; Retinoic acid; SAM002264647; trans-Retinoic acid

DIMETHYLTRIMETHYLCYCLOHEXENYLNONATETRAENOICACI

DNC000117

FDA

INN

Isotretinoin

LS-143476; Retinoic acid, all-trans-, sodium salt; Retinoic acid, sodium salt; Sodium retinoate; Vitamin A acid sodium salt

MFCD00001551

NA

Nexret

NSC-122758

QA-7791

Renova

Renova; Retin-A; Retisol-A; Stieva-A; Vesanoid

Retacnyl

Retin-A

Retin-A Micro

Retinoic Acid

Retinoic acid, 98%

Retinova

trans-Retinoic acid

Tretinoin (BAN

Tretinoin (FDA

Tretinoin (Retinoic acid)

Tretinoin/All-Trans Retinoic Acid

tretinon

USAN

USP)

Vesanoid

Vesanoid, Airol, Renova, Atralin, Retin-A, Avita, Stieva-A, all-trans retinoic acid

Vitamin A acid

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

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 11.61 -54.04 0 2 -1 40 299.434 5
Lo Low (pH 4.5-6) 5.80 11.03 -5.3 1 2 0 37 300.442 5

Vendor Notes

Note Type Comments Provided By
Mp [°C] 179 - 184 Acros Organics
MP 180 TCI
Melting_Point 180-182? Alfa-Aesar
Melting_Point 180-182° Alfa-Aesar
UniProt Database Links 2A5B_HUMAN; 2A5D_HUMAN; AB1IP_HUMAN; ACL6B_MOUSE; ADA10_PIG; ADH7_HUMAN; ADH7_MOUSE; ADIG_MOUSE; AGO3_BOVIN; AGO3_HUMAN; AGO3_MOUSE; AHR_HUMAN; AHR_MOUSE; AHR_RAT; AL1A1_BOVIN; AL1A1_CHICK; AL1A1_HORSE; AL1A1_HUMAN; AL1A1_MACFA; AL1A1_MESAU; AL1A1_MOUSE ChEBI
Purity 95+% Matrix Scientific
Purity 98% Fluorochem
Patent Database Links EP0930075; EP1523982; EP1527770; GB2156676; US2004132796; US2005070571; US2005070575; US2005085539; US2006199840; US2007202065; US2007232572; US2008188559; US2008194534 ChEBI
H phrase H312: Harmful in contact with skin Acros Organics
H phrase H312: Harmful in contact with skin; H335: May cause respiratory irritation; H302: Harmful if swallowed; H319: Causes serious eye irritation; H315: Causes skin irritation; H361d: Suspected of damaging the unborn child Acros Organics
Warnings IRRITANT Matrix Scientific
Therapy keratolytic SMDC Iconix
therap keratolytic, antiacne, antineoplastic MicroSource Spectrum
PUBCHEM_SUBSTANCE_COMMENT NCC_SAMPLE_SUPPLIER : LightBiologicals; NCC_SUPPLIER_STRUCTURE_ID : R-8595 NIH Clinical Collection via PubChem
Target Others Selleck Chemicals
P phrase P280: Wear protective gloves/protective clothing/eye protection/face protection Acros Organics
P phrase P280: Wear protective gloves/protective clothing/eye protection/face protection; P281: Use personal protective equipment as required; P302 + P352: IF ON SKIN: Wash with plenty of soap and water; P261: Avoid breathing dust/fume/gas/mist/vapors/spray; P301+ Acros Organics
R phrase R21/22: Harmful in contact with skin and if swallowed. Acros Organics
R phrase R21/22: Harmful in contact with skin and if swallowed.; R36/37/38: Irritating to eyes, respiratory system and skin.; R63: Possible risk of harm to the unborn child. Acros Organics
Reactome Database Links REACT_13550; REACT_13572; REACT_13626 ChEBI
Target Retinoid Receptor Selleck Chemicals
S phrase S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Acros Organics
S phrase S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. Acros Organics
PUBCHEM_SUBSTANCE_COMMENT SAMPLE_SUPPLIER: LightBiologicals; SUPPLIER_STRUCTURE_ID: R-8595 NIH Clinical Collection via PubChem
Hazard XN: Harmful Acros Organics

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
RABP1-1-E Cellular Retinoic Acid-binding Protein I (cluster #1 Of 1), Eukaryotic Eukaryotes 0 0.00 Binding ≤ 10μM
RABP2-1-E Cellular Retinoic Acid-binding Protein II (cluster #1 Of 1), Eukaryotic Eukaryotes 2 0.55 Binding ≤ 10μM
RARA-1-E Retinoic Acid Receptor Alpha (cluster #1 Of 1), Eukaryotic Eukaryotes 6 0.52 Binding ≤ 10μM
RARB-2-E Retinoic Acid Receptor Beta (cluster #2 Of 2), Eukaryotic Eukaryotes 5 0.53 Binding ≤ 10μM
RARG-2-E Retinoic Acid Receptor Gamma (cluster #2 Of 2), Eukaryotic Eukaryotes 4 0.53 Binding ≤ 10μM
RXRA-1-E Retinoid X Receptor Alpha (cluster #1 Of 1), Eukaryotic Eukaryotes 82 0.45 Binding ≤ 10μM
RXRB-2-E Retinoid X Receptor Beta (cluster #2 Of 2), Eukaryotic Eukaryotes 306 0.41 Binding ≤ 10μM
RXRG-1-E Retinoid X Receptor Gamma (cluster #1 Of 1), Eukaryotic Eukaryotes 350 0.41 Binding ≤ 10μM
RARA-1-E Retinoic Acid Receptor Alpha (cluster #1 Of 1), Eukaryotic Eukaryotes 7 0.52 Functional ≤ 10μM
RARB-1-E Retinoic Acid Receptor Beta (cluster #1 Of 1), Eukaryotic Eukaryotes 80 0.45 Functional ≤ 10μM
RARG-1-E Retinoic Acid Receptor Gamma (cluster #1 Of 1), Eukaryotic Eukaryotes 6 0.52 Functional ≤ 10μM
RXRA-1-E Retinoid X Receptor Alpha (cluster #1 Of 1), Eukaryotic Eukaryotes 900 0.38 Functional ≤ 10μM
RXRB-1-E Retinoid X Receptor Beta (cluster #1 Of 1), Eukaryotic Eukaryotes 54 0.46 Functional ≤ 10μM
RXRG-2-E Retinoid X Receptor Gamma (cluster #2 Of 2), Eukaryotic Eukaryotes 1225 0.38 Functional ≤ 10μM
Z50518-2-O Human Herpesvirus 4 (cluster #2 Of 5), Other Other 15 0.50 Functional ≤ 10μM
Z50594-7-O Mus Musculus (cluster #7 Of 9), Other Other 31 0.48 Functional ≤ 10μM
Z80135-1-O F9 (cluster #1 Of 1), Other Other 200 0.43 Functional ≤ 10μM
Z80156-5-O HL-60 (Promyeloblast Leukemia Cells) (cluster #5 Of 12), Other Other 5 0.53 Functional ≤ 10μM
Z80166-10-O HT-29 (Colon Adenocarcinoma Cells) (cluster #10 Of 12), Other Other 4300 0.34 Functional ≤ 10μM
Z80224-2-O MCF7 (Breast Carcinoma Cells) (cluster #2 Of 14), Other Other 585 0.40 Functional ≤ 10μM
Z80377-2-O PaCa2 (cluster #2 Of 2), Other Other 9500 0.32 Functional ≤ 10μM
Z80390-8-O PC-3 (Prostate Carcinoma Cells) (cluster #8 Of 10), Other Other 2000 0.36 Functional ≤ 10μM
Z80475-1-O SK-BR-3 (Breast Adenocarcinoma) (cluster #1 Of 3), Other Other 2 0.55 Functional ≤ 10μM
Z80712-1-O T47D (Breast Carcinoma Cells) (cluster #1 Of 7), Other Other 6 0.52 Functional ≤ 10μM
Z81170-2-O LNCaP (Prostate Carcinoma) (cluster #2 Of 5), Other Other 500 0.40 Functional ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
RABP1_MOUSE P62965 Cellular Retinoic Acid-binding Protein I, Mouse 0.4 0.60 Binding ≤ 1μM
RABP1_CHICK P40220 Cellular Retinoic Acid-binding Protein I, Chick 370 0.41 Binding ≤ 1μM
RABP2_MOUSE P22935 Cellular Retinoic Acid-binding Protein II, Mouse 2 0.55 Binding ≤ 1μM
RARA_HUMAN P10276 Retinoic Acid Receptor Alpha, Human 0.1 0.64 Binding ≤ 1μM
RARA_MOUSE P11416 Retinoic Acid Receptor Alpha, Mouse 15 0.50 Binding ≤ 1μM
RARB_HUMAN P10826 Retinoic Acid Receptor Beta, Human 0.4 0.60 Binding ≤ 1μM
RARB_MOUSE P22605 Retinoic Acid Receptor Beta, Mouse 13 0.50 Binding ≤ 1μM
RARG_MOUSE P18911 Retinoic Acid Receptor Gamma, Mouse 18 0.49 Binding ≤ 1μM
RARG_HUMAN P13631 Retinoic Acid Receptor Gamma, Human 0.2 0.62 Binding ≤ 1μM
RXRA_MOUSE P28700 Retinoid X Receptor Alpha, Mouse 1000 0.38 Binding ≤ 1μM
RXRA_HUMAN P19793 Retinoid X Receptor Alpha, Human 0.4 0.60 Binding ≤ 1μM
RXRB_MOUSE P28704 Retinoid X Receptor Beta, Mouse 1000 0.38 Binding ≤ 1μM
RXRB_HUMAN P28702 Retinoid X Receptor Beta, Human 0.5 0.59 Binding ≤ 1μM
RXRG_MOUSE P28705 Retinoid X Receptor Gamma, Mouse 350 0.41 Binding ≤ 1μM
RXRG_HUMAN P48443 Retinoid X Receptor Gamma, Human 1.4 0.56 Binding ≤ 1μM
RABP1_MOUSE P62965 Cellular Retinoic Acid-binding Protein I, Mouse 0.4 0.60 Binding ≤ 10μM
RABP1_CHICK P40220 Cellular Retinoic Acid-binding Protein I, Chick 370 0.41 Binding ≤ 10μM
RABP2_MOUSE P22935 Cellular Retinoic Acid-binding Protein II, Mouse 2 0.55 Binding ≤ 10μM
RARA_MOUSE P11416 Retinoic Acid Receptor Alpha, Mouse 15 0.50 Binding ≤ 10μM
RARA_HUMAN P10276 Retinoic Acid Receptor Alpha, Human 0.1 0.64 Binding ≤ 10μM
RARB_HUMAN P10826 Retinoic Acid Receptor Beta, Human 0.4 0.60 Binding ≤ 10μM
RARB_MOUSE P22605 Retinoic Acid Receptor Beta, Mouse 13 0.50 Binding ≤ 10μM
RARG_MOUSE P18911 Retinoic Acid Receptor Gamma, Mouse 18 0.49 Binding ≤ 10μM
RARG_HUMAN P13631 Retinoic Acid Receptor Gamma, Human 0.2 0.62 Binding ≤ 10μM
RXRA_HUMAN P19793 Retinoid X Receptor Alpha, Human 0.4 0.60 Binding ≤ 10μM
RXRA_MOUSE P28700 Retinoid X Receptor Alpha, Mouse 1000 0.38 Binding ≤ 10μM
RXRB_MOUSE P28704 Retinoid X Receptor Beta, Mouse 1000 0.38 Binding ≤ 10μM
RXRB_HUMAN P28702 Retinoid X Receptor Beta, Human 0.5 0.59 Binding ≤ 10μM
RXRG_HUMAN P48443 Retinoid X Receptor Gamma, Human 1.4 0.56 Binding ≤ 10μM
RXRG_MOUSE P28705 Retinoid X Receptor Gamma, Mouse 350 0.41 Binding ≤ 10μM
Z80135 Z80135 F9 200 0.43 Functional ≤ 10μM
Z80156 Z80156 HL-60 (Promyeloblast Leukemia Cells) 5 0.53 Functional ≤ 10μM
Z80166 Z80166 HT-29 (Colon Adenocarcinoma Cells) 4300 0.34 Functional ≤ 10μM
Z50518 Z50518 Human Herpesvirus 4 15.4 0.50 Functional ≤ 10μM
Z81170 Z81170 LNCaP (Prostate Carcinoma) 10000 0.32 Functional ≤ 10μM
Z80224 Z80224 MCF7 (Breast Carcinoma Cells) 580 0.40 Functional ≤ 10μM
Z50594 Z50594 Mus Musculus 31 0.48 Functional ≤ 10μM
Z80377 Z80377 PaCa2 9500 0.32 Functional ≤ 10μM
Z80390 Z80390 PC-3 (Prostate Carcinoma Cells) 2000 0.36 Functional ≤ 10μM
RARA_HUMAN P10276 Retinoic Acid Receptor Alpha, Human 240 0.42 Functional ≤ 10μM
RARB_HUMAN P10826 Retinoic Acid Receptor Beta, Human 1 0.57 Functional ≤ 10μM
RARG_HUMAN P13631 Retinoic Acid Receptor Gamma, Human 0.1 0.64 Functional ≤ 10μM
RXRA_HUMAN P19793 Retinoid X Receptor Alpha, Human 1084 0.38 Functional ≤ 10μM
RXRB_HUMAN P28702 Retinoid X Receptor Beta, Human 1394 0.37 Functional ≤ 10μM
RXRG_HUMAN P48443 Retinoid X Receptor Gamma, Human 1100 0.38 Functional ≤ 10μM
Z80475 Z80475 SK-BR-3 (Breast Adenocarcinoma) 1.7 0.56 Functional ≤ 10μM
Z80712 Z80712 T47D (Breast Carcinoma Cells) 200 0.43 Functional ≤ 10μM

Direct Reactome Annotations (via ChEBI)

Description Species
Import of palmitoyl-CoA into the mitochondrial matrix
Miscellaneous substrates
Regulation of pyruvate dehydrogenase (PDH) complex
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% )