NPASS Natural Product

Natural Product: NPC115343

Natural Product ID:	NPC115343
Common Name:	Pancratistatin
IUPAC Name:	(1R,2S,3S,4S,4aR,11bR)-1,2,3,4,7-pentahydroxy-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
Synonyms:	(+)-Pancratistatin; Pancratistatin
Molecular Formula:	C14H15NO8
Standard InCHIKey:	VREZDOWOLGNDPW-ALTGWBOUSA-N
Standard InCHI:	InChI=1S/C14H15NO8/c16-8-5-3-1-4-13(23-2-22-4)9(17)6(3)14(21)15-7(5)10(18)12(20)11(8)19/h1,5,7-8,10-12,16-20H,2H2,(H,15,21)/t5-,7-,8-,10+,11+,12+/m1/s1
Canonical SMILES:	O[C@@H]1[C@@H](O)[C@H](O)[C@H]2[C@H]([C@@H]1O)N=C(c1c2cc2OCOc2c1O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10448.1	Prunus cerasoides var. campanulata	Varieties	Rosaceae	Eukaryota	UNPD*
NPO11192	Hedera helix	Species	Araliaceae	Eukaryota	TCM_Taiwan*
NPO2063	Pausinystalia pachyceras	Species	Rubiaceae	Eukaryota	UNPD*
NPO29135	Oenanthe crocata	Species	Apiaceae	Eukaryota	TCM_Taiwan*
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	TCM_Taiwan*
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	TCMSP*
NPO30275	Zephyranthes grandiflora	Species	Amaryllidaceae	Eukaryota	TCM_Taiwan*
NPO32582	narcissus cv. ice follies	Species	Amaryllidaceae	Eukaryota	PMID[22413911]
NPO32739	pancratium littorale	Species	Amaryllidaceae	Eukaryota	PMID[1336040]
NPO33009	Hymenocallis	Genus	Amaryllidaceae	Eukaryota	PMID[8277308]

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Biological Activity

Activity Type	# Activity
ED50	17
GI50	94
IC50	5
Others	32

Activity Type	# Activity
Cell Line	120
Organism	26
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1081	Cell Line	BXPC-3	Homo sapiens	Inhibition	=	0.028	ug/ml	15125958
NPT1081	Cell Line	BXPC-3	Homo sapiens	ED50	=	0.02	ug/ml	17346078
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.02	ug/ml	15043403
NPT1081	Cell Line	BXPC-3	Homo sapiens	ED50	=	0.043	ug/ml	16124772
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI	=	0.028	ug/ml	16441059
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.02	ug/ml	22413911
NPT111	Cell Line	K562	Homo sapiens	GI50		37.33	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		30.9	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		36.39	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		43.85	nM	PubChem BioAssay data set

Showing 1 to 10 of 147 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 NPC115343 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	253
0.1-0.2	1211
0.2-0.3	3847
0.3-0.4	8420
0.4-0.5	4432
0.5-0.6	6491
0.6-0.7	5342
0.7-0.8	874
0.8-0.85	5
0.85-0.9	3
0.9-0.95	7
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.7368	Intermediate Similarity	NPC318805
0.7368	Intermediate Similarity	NPC475096
0.7368	Intermediate Similarity	NPC477702
0.7368	Intermediate Similarity	NPC277867
0.7368	Intermediate Similarity	NPC161700

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 NPC115343 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	679
0.2-0.3	1280
0.3-0.4	2841
0.4-0.5	2252
0.5-0.6	1384
0.6-0.7	488
0.7-0.8	52
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6432	Remote Similarity	NPD7930	Approved
0.6432	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6779	Approved
0.6439	Remote Similarity	NPD6782	Approved
0.6439	Remote Similarity	NPD6780	Approved

Showing 1 to 5 of 200 entries

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Structure

CID115343 OpenBabel06191715472D 23 26 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 2 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 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -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 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 22 1 0 0 0 0 2 23 1 0 0 0 0 3 6 1 0 0 0 0 4 13 2 0 0 0 0 4 22 1 0 0 0 0 5 3 1 1 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 6 0 0 0 8 11 1 0 0 0 0 8 16 1 1 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 1 0 0 0 11 12 1 0 0 0 0 11 19 1 6 0 0 0 12 20 1 1 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	441597
ChEMBL	CHEMBL419335
ZINC

Physicochemical Properties

Molecular Weight:	325.08
ALogP:	-3.356
MLogP:	2.01
XLogP:	-1.48
# Rotatable Bonds:	6
Polar Surface Area:	152.2
# H-Bond Aceptor:	6
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	23

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