NPASS Natural Product

Natural Product: NPC2634

Natural Product ID:	NPC2634
Common Name:	Guggulsterone
IUPAC Name:	(8R,9S,10R,13S,14S,17Z)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione
Synonyms:	(Z)-Gugglesterone; Guggulsterone
Molecular Formula:	C21H28O2
Standard InCHIKey:	WDXRGPWQVHZTQJ-OSJVMJFVSA-N
Standard InCHI:	InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4+/t15-,17+,18+,20+,21-/m1/s1
Canonical SMILES:	C/C=C/1C(=O)C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO13402	Eupatorium inulifolium	Species	Asteraceae	Eukaryota	UNPD*
NPO13567	Streptomyces sahachiroi	Species	Streptomycetaceae	Bacteria	UNPD*
NPO16197	Eucalyptus microcorys	Species	Myrtaceae	Eukaryota	UNPD*
NPO16488	Achromobacter piechaudii	Species	Alcaligenaceae	Bacteria	UNPD*
NPO16527	Baptisia minor	Species	Fabaceae	Eukaryota	UNPD*
NPO23598	Hedera rhombea	Species	Araliaceae	Eukaryota	UNPD*
NPO24302	Angylocalyx oligophyllus	Species	Fabaceae	Eukaryota	UNPD*
NPO24424	Tricalysia okelensis	Species	Rubiaceae	Eukaryota	UNPD*
NPO24749	Abutilon indicum	Species	Malvaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
IC50	19
Ki	6
Others	19
Potency	64

Activity Type	# Activity
Cell Line	22
Individual Protein	46
Organism	16
Others	22
Protein Family	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT103	Individual Protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency		33491.5	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency		31622.8	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency		39810.7	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency		10747.6	nM	PubChem BioAssay data set
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Potency		50118.7	nM	PubChem BioAssay data set
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Potency		39810.7	nM	PubChem BioAssay data set
NPT111	Cell Line	K562	Homo sapiens	Activity	=	84	%	22687747
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency		2984.9	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency		949.5	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency		13333.2	nM	PubChem BioAssay data set

Showing 1 to 10 of 89 entries

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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 NPC2634 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	100
0.1-0.2	1214
0.2-0.3	5876
0.3-0.4	11324
0.4-0.5	5450
0.5-0.6	4293
0.6-0.7	1980
0.7-0.8	504
0.8-0.85	89
0.85-0.9	30
0.9-0.95	21
0.95-1	8

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Similarity Score	Similarity Level	Natural Product ID
0.7805	Intermediate Similarity	NPC136948
0.7805	Intermediate Similarity	NPC58063
0.7805	Intermediate Similarity	NPC475740
0.7808	Intermediate Similarity	NPC246722
0.7808	Intermediate Similarity	NPC151045

Showing 1 to 5 of 200 entries

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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 NPC2634 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	121
0.1-0.2	1655
0.2-0.3	4294
0.3-0.4	2266
0.4-0.5	404
0.5-0.6	198
0.6-0.7	138
0.7-0.8	68
0.8-0.85	9
0.85-0.9	1
0.9-0.95	3
0.95-1	4

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6125	Remote Similarity	NPD6923	Approved
0.6125	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD6922	Approved
0.6125	Remote Similarity	NPD3698	Phase 2

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Structure

CID2634 OpenBabel06191715322D 23 26 0 0 1 0 0 0 0 0999 V2000 -1.7220 1.8436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5148 -0.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8386 1.4506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6773 -2.9025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8389 -2.4188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1904 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6765 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3526 -0.9663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3531 -2.9020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 -0.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5154 -2.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1907 -2.4179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8386 -1.4510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8384 0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6767 -0.9668 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9673 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6753 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5151 -1.4505 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0568 -2.9176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5414 0.4993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 4 16 2 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 22 2 0 0 0 0 15 6 1 1 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 6 0 0 0 18 21 1 6 0 0 0 19 23 2 0 0 0 0 20 2 1 6 0 0 0 21 3 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	6450278
ChEMBL	CHEMBL410683
ZINC

Physicochemical Properties

Molecular Weight:	312.21
ALogP:	1.2873
MLogP:	3.55
XLogP:	4.086
# Rotatable Bonds:	3
Polar Surface Area:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	23

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