NPASS Natural Product

Natural Product: NPC320665

Natural Product ID:	NPC320665
Common Name:	Gestrinone
IUPAC Name:	(8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
Synonyms:	A-46745; Dimetriose; Gestrinone; R-2323; RU-2323
Molecular Formula:	C21H24O2
Standard InCHIKey:	BJJXHLWLUDYTGC-ANULTFPQSA-N
Standard InCHI:	InChI=1S/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1
Canonical SMILES:	CC[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@@]2(O)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			PMID[11076067]

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Biological Activity

Activity Type	# Activity
AC50	3
Kd	1
Potency	37

Activity Type	# Activity
Individual Protein	10
Organism	2
Others	29

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Value	Unit	Reference
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	26601.1	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	37575.1	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	15089	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	5955.7	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	21313.8	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	29.8	nM	PubChem BioAssay data set
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	89125.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	40533.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	9441.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	13335.9	nM	PubChem BioAssay data set

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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 NPC320665 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	123
0.1-0.2	842
0.2-0.3	3553
0.3-0.4	11361
0.4-0.5	7217
0.5-0.6	5292
0.6-0.7	2136
0.7-0.8	358
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7188	Intermediate Similarity	NPC305039
0.7188	Intermediate Similarity	NPC474245
0.7188	Intermediate Similarity	NPC77168
0.7188	Intermediate Similarity	NPC118011
0.7188	Intermediate Similarity	NPC36668

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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 NPC320665 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	1246
0.2-0.3	3895
0.3-0.4	2773
0.4-0.5	649
0.5-0.6	198
0.6-0.7	176
0.7-0.8	66
0.8-0.85	14
0.85-0.9	8
0.9-0.95	0
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6364	Remote Similarity	NPD6614	Approved
0.6364	Remote Similarity	NPD6412	Phase 2
0.6373	Remote Similarity	NPD7515	Phase 2
0.6383	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6052	Approved

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Structure

CID320665 OpenBabel06191716152D 23 26 0 0 1 0 0 0 0 0999 V2000 1.7268 0.8799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7216 1.6182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5232 -3.3963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0438 -1.9395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6823 -2.9112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2035 -1.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5223 -0.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8391 -1.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6815 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 -0.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2040 -3.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3638 -2.9107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0440 -2.9102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3635 -1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5226 -1.4548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6820 -1.9404 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8411 -1.4553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8409 -0.4851 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9104 -3.4097 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8662 0.4997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 3 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 7 1 0 0 0 0 5 14 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 8 16 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 22 2 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 7 1 1 0 0 0 18 19 1 0 0 0 0 19 20 1 6 0 0 0 20 21 1 1 0 0 0 21 23 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	27812
ChEMBL	CHEMBL1868702
ZINC

Physicochemical Properties

Molecular Weight:	308.18
ALogP:	1.2607
MLogP:	3.55
XLogP:	2.615
# Rotatable Bonds:	3
Polar Surface Area:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	23

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