NPASS Natural Product

Natural Product: NPC258501

Natural Product ID:	NPC258501
Common Name:	Catalpol
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(1aS,1bS,2S,5aR,6S,6aS)-6-hydroxy-1a-(hydroxymethyl)-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Catalpol
Molecular Formula:	C15H22O10
Standard InCHIKey:	LHDWRKICQLTVDL-PZYDOOQISA-N
Standard InCHI:	InChI=1S/C15H22O10/c16-3-6-9(19)10(20)11(21)14(23-6)24-13-7-5(1-2-22-13)8(18)12-15(7,4-17)25-12/h1-2,5-14,16-21H,3-4H2/t5-,6-,7-,8+,9-,10+,11-,12+,13+,14+,15-/m1/s1
Canonical SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@]2(CO)O[C@H]2[C@H]3O)[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	Reference
NPO10000	Rehmanniae radix praeparata	NA	NA	NA	TCMSP*
NPO10003	Veronica cymbalaria	Species	Plantaginaceae	Eukaryota	UNPD*
NPO10011	Myrsine capitellata	Species	Primulaceae	Eukaryota	UNPD*
NPO10035	Ficus pantoniana	Species	Moraceae	Eukaryota	UNPD*
NPO10092	Hesperocyparis bakeri	Species	Cupressaceae	Eukaryota	UNPD*
NPO10102	Pithecellobium albicans	Species	Fabaceae	Eukaryota	UNPD*
NPO10553	Heterophyllaea pustulata	Species	Rubiaceae	Eukaryota	UNPD*
NPO11255	Veronica thomsonii	Species	Plantaginaceae	Eukaryota	UNPD*
NPO11342	Sideritis trojana	Species	Lamiaceae	Eukaryota	UNPD*
NPO11397	Cladophora rupestris	Species	Cladophoraceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
GI50	10
IC50	7
Others	19
Potency	1

Activity Type	# Activity
Cell Line	14
Individual Protein	12
Organism	7
Others	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	54.03	%	22137340
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	75.78	%	22137340
NPT1183	Cell Line	WiDr	Homo sapiens	GI50	>	100000	nM	17178223
NPT1183	Cell Line	WiDr	Homo sapiens	GI50	>	100000	nM	20231098
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000	nM	26859776
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	8.2	day	15043410
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	73.3	%	15043410
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	-0.01	mg/kg/day	15043410
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	0.017	mg/kg/day	15043410
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	-66.1	%	15043410

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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 NPC258501 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	127
0.1-0.2	1569
0.2-0.3	5231
0.3-0.4	11779
0.4-0.5	7443
0.5-0.6	3711
0.6-0.7	962
0.7-0.8	53
0.8-0.85	3
0.85-0.9	4
0.9-0.95	4
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.6667	Remote Similarity	NPC235824
0.6667	Remote Similarity	NPC474297
0.6667	Remote Similarity	NPC476541
0.6667	Remote Similarity	NPC476539
0.6667	Remote Similarity	NPC476538

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 NPC258501 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	2613
0.2-0.3	4125
0.3-0.4	1645
0.4-0.5	446
0.5-0.6	174
0.6-0.7	18
0.7-0.8	0
0.8-0.85	0
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
0.561	Remote Similarity	NPD6015	Approved
0.561	Remote Similarity	NPD8513	Phase 3
0.561	Remote Similarity	NPD6016	Approved
0.5612	Remote Similarity	NPD4268	Approved
0.5612	Remote Similarity	NPD4271	Approved

Showing 1 to 5 of 56 entries

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Structure

CID258501 OpenBabel06191716062D 25 28 0 0 1 0 0 0 0 0999 V2000 -0.2514 3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6146 3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8108 1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4062 0.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2514 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9448 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6146 1.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9448 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0787 3.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2127 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4807 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2127 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6768 2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9349 0.0982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9727 1.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8108 3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0787 4.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3467 3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0787 1.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3467 1.8917 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 2 2 0 0 0 0 2 22 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 1 1 6 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 3 1 1 0 0 0 6 9 1 0 0 0 0 6 23 1 0 0 0 0 7 13 1 0 0 0 0 7 15 1 6 0 0 0 8 12 1 0 0 0 0 8 18 1 1 0 0 0 9 10 1 0 0 0 0 9 19 1 6 0 0 0 10 11 1 0 0 0 0 10 20 1 1 0 0 0 11 14 1 0 0 0 0 11 21 1 6 0 0 0 12 15 1 6 0 0 0 12 25 1 0 0 0 0 13 22 1 0 0 0 0 13 24 1 1 0 0 0 14 23 1 0 0 0 0 14 24 1 1 0 0 0 15 4 1 6 0 0 0 15 25 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	91520
ChEMBL	CHEMBL513223
ZINC

Physicochemical Properties

Molecular Weight:	362.12
ALogP:	-4.3433
MLogP:	2.01
XLogP:	-2.707
# Rotatable Bonds:	10
Polar Surface Area:	161.6
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	25

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