NPASS Natural Product

Natural Product: NPC102256

Natural Product ID:	NPC102256
Common Name:	Schizandrin
IUPAC Name:
Synonyms:	Schisandrin
Molecular Formula:	C24H32O7
Standard InCHIKey:	YEFOAORQXAOVJQ-RZFZLAGVSA-N
Standard InCHI:	InChI=1S/C24H32O7/c1-13-9-14-10-16(26-3)20(28-5)22(30-7)18(14)19-15(12-24(13,2)25)11-17(27-4)21(29-6)23(19)31-8/h10-11,13,25H,9,12H2,1-8H3/t13-,24-/m0/s1
Canonical SMILES:	COc1c(OC)cc2c(c1OC)c1c(cc(c(c1OC)OC)OC)C[C@@H]([C@@](C2)(C)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	Isolation Part	Reference
NPO14100	Persea kusanoi	Species	Lauraceae	Eukaryota		UNPD*
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota		PMID[21232955]
NPO2263	Croton megistocarpus	Species	Euphorbiaceae	Eukaryota		UNPD*
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota		TCMID*
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	fruits	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota		HerDing*
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota		UNPD*
NPO33401	schisandra sphenathera	Species	Schisandraceae	Eukaryota	Stems	PMID[23237974]
NPO433	Geranium sibiricum	Species	Geraniaceae	Eukaryota		UNPD*
NPO4582	Baphicacanthus cusia	Species	Acanthaceae	Eukaryota		UNPD*

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Biological Activity

Activity Type	# Activity
EC50	1
IC50	18
Others	5
Potency	5

Activity Type	# Activity
Cell Line	11
Individual Protein	7
Organism	4
Others	7

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1086	Cell Line	SK-HEP1	Homo sapiens	IC50	=	71300	nM	18063366
NPT111	Cell Line	K562	Homo sapiens	IC50	=	25000	nM	18063366
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	50200	nM	18063366
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.0005	ug/ml	17129588
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	1.401	ug/ml	17129588
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.0035	ug/ml	17129588
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	3.135	ug/ml	17129588
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.054	ug/ml	17129588
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.094	ug/ml	17129588
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000	nM	23237974

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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 NPC102256 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	294
0.1-0.2	1234
0.2-0.3	2553
0.3-0.4	7207
0.4-0.5	6251
0.5-0.6	2575
0.6-0.7	6140
0.7-0.8	3660
0.8-0.85	667
0.85-0.9	262
0.9-0.95	31
0.95-1	15

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Similarity Score	Similarity Level	Natural Product ID
0.8643	High Similarity	NPC326144
0.8657	High Similarity	NPC204215
0.8657	High Similarity	NPC175067
0.8657	High Similarity	NPC127624
0.8662	High Similarity	NPC325720

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 NPC102256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	967
0.2-0.3	1552
0.3-0.4	2810
0.4-0.5	1787
0.5-0.6	1014
0.6-0.7	612
0.7-0.8	129
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6842	Remote Similarity	NPD7266	Discontinued
0.6852	Remote Similarity	NPD6788	Approved
0.6855	Remote Similarity	NPD4380	Phase 2
0.6859	Remote Similarity	NPD2533	Approved
0.6859	Remote Similarity	NPD4584	Approved

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Structure

CID102256 OpenBabel06191715442D 31 33 0 0 1 0 0 0 0 0999 V2000 1.5477 -4.0581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5040 -3.7610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1631 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7322 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4964 1.3988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4881 1.8215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3415 2.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0894 2.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8536 -2.5203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7643 -1.3334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3334 -1.3334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4227 -2.5203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1869 -3.1870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8536 -1.5774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4227 -1.5774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0083 -0.4227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5774 -0.4227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1869 -0.9107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2440 -0.9107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3416 0.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9107 0.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4309 0.0000 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 0.2440 -3.1870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3671 -4.1218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9191 -0.1786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4882 -0.1786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5857 1.1548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1548 1.1548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0975 1.3334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3334 1.3334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 31 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 24 1 6 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 16 26 1 0 0 0 0 17 21 2 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 23 2 0 0 0 0 20 22 1 0 0 0 0 20 28 1 0 0 0 0 21 23 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 2 1 6 0 0 0 24 25 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	3001664
ChEMBL	CHEMBL253688
ZINC

Physicochemical Properties

Molecular Weight:	432.21
ALogP:	0.1593
MLogP:	3.33
XLogP:	2.38
# Rotatable Bonds:	15
Polar Surface Area:	75.61
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	31

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