NPASS Natural Product

Natural Product: NPC199533

Natural Product ID:	NPC199533
Common Name:	Paepalantine-9-O-Beta-D-Glucopyranoside
IUPAC Name:	10-hydroxy-5,7-dimethoxy-3-methyl-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzo[g]isochromen-1-one
Synonyms:
Molecular Formula:	C22H24O11
Standard InCHIKey:	MLIAPYGFYBSVBC-FSFQXNNFSA-N
Standard InCHI:	InChI=1S/C22H24O11/c1-8-4-10-15(21(28)31-8)17(25)14-11(20(10)30-3)5-9(29-2)6-12(14)32-22-19(27)18(26)16(24)13(7-23)33-22/h4-6,13,16,18-19,22-27H,7H2,1-3H3/t13-,16-,18+,19-,22-/m1/s1
Canonical SMILES:	OC[C@H]1O[C@@H](Oc2cc(OC)cc3c2c(O)c2c(c3OC)cc(oc2=O)C)[C@@H]([C@H]([C@@H]1O)O)O
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
NPO26869	Cephalanthus pilulifera	Species	Rubiaceae	Eukaryota				UNPD*
NPO5130	Platycapnos saxicola	Species	Papaveraceae	Eukaryota				UNPD*

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Biological Activity

Activity Type	# Activity
EC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	TC50	=	160	ug/ml	11374977
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	38	ug/ml	11374977

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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 NPC199533 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	322
0.1-0.2	1219
0.2-0.3	2415
0.3-0.4	5158
0.4-0.5	6685
0.5-0.6	4132
0.6-0.7	3484
0.7-0.8	4387
0.8-0.85	2129
0.85-0.9	893
0.9-0.95	53
0.95-1	12

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Similarity Score	Similarity Level	Natural Product ID
0.8837	High Similarity	NPC237435
0.8837	High Similarity	NPC43211
0.8837	High Similarity	NPC135277
0.8837	High Similarity	NPC115760
0.8837	High Similarity	NPC470667

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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 NPC199533 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	887
0.2-0.3	1740
0.3-0.4	2597
0.4-0.5	1938
0.5-0.6	1071
0.6-0.7	401
0.7-0.8	134
0.8-0.85	52
0.85-0.9	13
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6988	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4287	Approved
0.7012	Intermediate Similarity	NPD1283	Approved
0.7018	Intermediate Similarity	NPD4308	Phase 3
0.7024	Intermediate Similarity	NPD6233	Phase 2

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Structure

CID199533 OpenBabel06191715592D 33 36 0 0 1 0 0 0 0 0999 V2000 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 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 0.5000 0.0000 C 0 0 2 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 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 0.0000 2.0000 0.0000 C 0 0 1 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 29 1 0 0 0 0 3 30 1 0 0 0 0 4 8 2 0 0 0 0 4 10 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 12 2 0 0 0 0 7 23 1 0 0 0 0 8 31 1 0 0 0 0 9 29 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 20 2 0 0 0 0 12 14 1 0 0 0 0 12 32 1 0 0 0 0 13 7 1 6 0 0 0 13 16 1 0 0 0 0 13 33 1 0 0 0 0 14 17 2 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 24 1 1 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 22 1 0 0 0 0 19 27 1 1 0 0 0 20 30 1 0 0 0 0 21 28 2 0 0 0 0 21 31 1 0 0 0 0 22 32 1 6 0 0 0 22 33 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10027431
ChEMBL	CHEMBL513919
ZINC

Physicochemical Properties

Molecular Weight:	464.13
ALogP:	-2.4017
MLogP:	2.67
XLogP:	0.337
# Rotatable Bonds:	13
Polar Surface Area:	164.37
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	33

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