NPASS Natural Product

Natural Product: NPC317177

Natural Product ID:	NPC317177
Common Name:	Tretinoin
IUPAC Name:	(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
Synonyms:	Acticin; Atralin; Avita; Renova; Retin-A; Retin-A Micro; Tretin-X; Tretinoin; Vesanoid
Molecular Formula:	C20H28O2
Standard InCHIKey:	SHGAZHPCJJPHSC-YCNIQYBTSA-N
Standard 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+
Canonical SMILES:	C/C(=CC=CC(=CC(=O)O)C)/C=C/C1=C(C)CCCC1(C)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	blood			Geigy Scientific Tables, 8th Rev edition. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.

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Biological Activity

Activity Type	# Activity
AC50	5
EC50	92
ED50	26
GI50	84
IC50	648
Kd	62
Ki	28
Others	204
Potency	198

Activity Type	# Activity
Cell Line	737
Individual Protein	361
Organism	50
Others	195
Protein-Protein Interaction	1
Tissue	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		25929	nM	PubChem BioAssay data set
NPT1017	Organism	Cricetinae gen. sp.	Cricetinae gen. sp.	Activity	=	76.9	%	2578190
NPT1017	Organism	Cricetinae gen. sp.	Cricetinae gen. sp.	Activity	=	41.7	%	2578190
NPT1017	Organism	Cricetinae gen. sp.	Cricetinae gen. sp.	Activity	=	23.1	%	2578190
NPT1017	Organism	Cricetinae gen. sp.	Cricetinae gen. sp.	ED50	=	2.00E-11	nM	2578190
NPT1017	Organism	Cricetinae gen. sp.	Cricetinae gen. sp.	Activity	=	100	%	2578190
NPT1017	Organism	Cricetinae gen. sp.	Cricetinae gen. sp.	Activity	=	53.8	%	2578190
NPT1017	Organism	Cricetinae gen. sp.	Cricetinae gen. sp.	ED50	=	9.00E-12	nM	2578190
NPT1017	Organism	Cricetinae gen. sp.	Cricetinae gen. sp.	Activity	=	83.3	%	2578190

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Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC317177 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	57
0.1-0.2	732
0.2-0.3	5638
0.3-0.4	12833
0.4-0.5	6790
0.5-0.6	3995
0.6-0.7	769
0.7-0.8	64
0.8-0.85	7
0.85-0.9	0
0.9-0.95	1
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.6579	Remote Similarity	NPC69383
0.6579	Remote Similarity	NPC279666
0.6579	Remote Similarity	NPC313179
0.6585	Remote Similarity	NPC8571
0.6585	Remote Similarity	NPC473659

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Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC317177 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	64
0.1-0.2	1146
0.2-0.3	4536
0.3-0.4	2565
0.4-0.5	575
0.5-0.6	234
0.6-0.7	33
0.7-0.8	2
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	4

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.56	Remote Similarity	NPD7341	Phase 2
0.5604	Remote Similarity	NPD7515	Phase 2
0.5604	Remote Similarity	NPD6050	Approved
0.561	Remote Similarity	NPD6932	Approved
0.5625	Remote Similarity	NPD6926	Approved

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Structure

CID317177 OpenBabel06191716142D 22 22 0 0 0 0 0 0 0 0999 V2000 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 8.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 8.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 8 1 0 0 0 0 6 9 2 0 0 0 0 7 10 1 0 0 0 0 7 13 1 0 0 0 0 8 15 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 17 18 2 0 0 0 0 18 20 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	444795
ChEMBL	CHEMBL38
ZINC

Physicochemical Properties

Molecular Weight:	300.21
ALogP:	3.8871
MLogP:	3.44
XLogP:	6.254
# Rotatable Bonds:	11
Polar Surface Area:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	22

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