NPASS Natural Product

Natural Product: NPC113733

Natural Product ID:	NPC113733
Common Name:	Stigmasterol
IUPAC Name:	(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:	stigmasterol
Molecular Formula:	C29H48O
Standard InCHIKey:	HCXVJBMSMIARIN-PHZDYDNGSA-N
Standard InCHI:	InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
Canonical SMILES:	CC[C@@H](C(C)C)/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10000	Rehmanniae radix praeparata	NA	NA	NA	TCMSP*
NPO10001	Gnidia subcordata	Species	Thymelaeaceae	Eukaryota	UNPD*
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	UNPD*
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	UNPD*
NPO10101	Rothmannia macrophylla	Species	Rubiaceae	Eukaryota	UNPD*
NPO10206	Anthemis fuscata	Species	Asteraceae	Eukaryota	UNPD*
NPO10230	Heynea trijuga	Species	Meliaceae	Eukaryota	UNPD*
NPO10250	Alectoria rigida	Species	Parmeliaceae	Eukaryota	UNPD*
NPO10308	Clerodendrum brachyanthum	Species	Lamiaceae	Eukaryota	UNPD*
NPO10341	Pseudogymnoascus pannorum	Species	Pseudeurotiaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
ED50	1
IC50	26
MIC	3
Others	27
Potency	1

Activity Type	# Activity
Cell Line	36
Individual Protein	10
Organism	10
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000	nM	11374975
NPT111	Cell Line	K562	Homo sapiens	IC50	=	11140	nM	22687747
NPT111	Cell Line	K562	Homo sapiens	Activity	=	43	%	22687747
NPT1306	Cell Line	WISH	Homo sapiens	IC50	>	100000	nM	11374975
NPT1307	Cell Line	Calu-1	Homo sapiens	IC50	>	100000	nM	11374975
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000	nM	11374975
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000	nM	19388709
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Inhibition	=	0	%	16643021
NPT1886	Cell Line	J774	Mus musculus	IC50	>	242300	nM	17637068
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	100000	nM	11374975

Showing 1 to 10 of 56 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 NPC113733 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	96
0.1-0.2	819
0.2-0.3	3690
0.3-0.4	11460
0.4-0.5	6073
0.5-0.6	4168
0.6-0.7	3133
0.7-0.8	1055
0.8-0.85	203
0.85-0.9	111
0.9-0.95	55
0.95-1	26

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Similarity Score	Similarity Level	Natural Product ID
0.8442	Intermediate Similarity	NPC99168
0.8442	Intermediate Similarity	NPC470396
0.8442	Intermediate Similarity	NPC475337
0.8472	Intermediate Similarity	NPC32055
0.8481	Intermediate Similarity	NPC20853

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 NPC113733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	1212
0.2-0.3	4103
0.3-0.4	2509
0.4-0.5	727
0.5-0.6	183
0.6-0.7	192
0.7-0.8	71
0.8-0.85	13
0.85-0.9	14
0.9-0.95	1
0.95-1	2

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6463	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4244	Approved
0.6463	Remote Similarity	NPD4691	Approved
0.6465	Remote Similarity	NPD4159	Approved
0.6471	Remote Similarity	NPD6412	Phase 2

Showing 1 to 5 of 200 entries

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Structure

CID113733 OpenBabel06191715472D 30 33 0 0 1 0 0 0 0 0999 V2000 -2.6329 5.3937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9993 6.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5418 5.6986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8089 3.7142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5364 2.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2057 4.6047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3514 3.0269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7482 3.9175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -1.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6902 -0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2254 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2251 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8456 1.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6910 1.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 -1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5721 5.5969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3817 2.9253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1753 4.7064 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6895 -0.9755 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6905 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3815 1.9503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5358 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 0.4877 0.0000 C 0 0 1 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 -2.5361 1.4626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5557 -1.4752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 8 9 2 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 2 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 20 4 1 1 0 0 0 20 25 1 0 0 0 0 21 7 1 6 0 0 0 22 28 1 0 0 0 0 23 30 1 6 0 0 0 24 11 1 1 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 25 29 1 6 0 0 0 26 29 1 6 0 0 0 27 28 1 6 0 0 0 28 5 1 6 0 0 0 29 6 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	5280794
ChEMBL	CHEMBL400247
ZINC

Physicochemical Properties

Molecular Weight:	412.37
ALogP:	1.2566
MLogP:	4.54
XLogP:	11.071
# Rotatable Bonds:	12
Polar Surface Area:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	30

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