NPASS Natural Product

Natural Product: NPC229548

Natural Product ID:	NPC229548
Common Name:	6-O-E-Feruloyl Catalpol
IUPAC Name:	[(1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:
Molecular Formula:	C25H30O13
Standard InCHIKey:	RMSKZOXJAHOIER-GGKKSNITSA-N
Standard InCHI:	InChI=1S/C25H30O13/c1-33-14-8-11(2-4-13(14)28)3-5-16(29)36-21-12-6-7-34-23(17(12)25(10-27)22(21)38-25)37-24-20(32)19(31)18(30)15(9-26)35-24/h2-8,12,15,17-24,26-28,30-32H,9-10H2,1H3/b5-3+/t12-,15-,17-,18-,19+,20-,21+,22+,23+,24+,25-/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]3OC(=O)/C=C/c2ccc(c(c2)OC)O)[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
NPO10092	Hesperocyparis bakeri	Species	Cupressaceae	Eukaryota	UNPD*
NPO14720	Neopicrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	TM-MC*
NPO14818	Neofusicoccum mangiferae	Species	Botryosphaeriaceae	Eukaryota	UNPD*
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	TCMID*
NPO30110	Veronica lavaudiana	Species	Plantaginaceae	Eukaryota	PMID[21568305]
NPO3093	Phyllanthus tenellus	Species	Phyllanthaceae	Eukaryota	UNPD*
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	TM-MC*
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	TCMID*

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Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	3
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000	nM	26859776
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000	nM	26859776
NPT2	Others	Unspecified		IC50	>	10000	nM	26859776
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000	nM	26859776

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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 NPC229548 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	254
0.1-0.2	1115
0.2-0.3	2427
0.3-0.4	5515
0.4-0.5	6941
0.5-0.6	4749
0.6-0.7	6528
0.7-0.8	2986
0.8-0.85	287
0.85-0.9	63
0.9-0.95	14
0.95-1	10

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Similarity Score	Similarity Level	Natural Product ID
0.8267	Intermediate Similarity	NPC471664
0.8267	Intermediate Similarity	NPC471665
0.8267	Intermediate Similarity	NPC471988
0.8267	Intermediate Similarity	NPC199459
0.8267	Intermediate Similarity	NPC52277

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 NPC229548 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	825
0.2-0.3	1802
0.3-0.4	2782
0.4-0.5	1962
0.5-0.6	1075
0.6-0.7	422
0.7-0.8	41
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.64	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD5588	Approved
0.6407	Remote Similarity	NPD5960	Phase 3
0.6412	Remote Similarity	NPD3750	Approved

Showing 1 to 5 of 200 entries

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Structure

CID229548 OpenBabel06191716022D 38 42 0 0 1 0 0 0 0 0999 V2000 7.8416 -3.1779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9364 -0.1169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2891 -0.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9145 -0.3248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6199 -1.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 5.5762 -1.8111 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 5.2672 -0.8600 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 7.2235 -1.2758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5544 -2.0190 0.0000 C 0 0 0 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 2.6418 -1.1873 0.0000 C 0 0 0 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 -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 0.9945 -1.7226 0.0000 C 0 0 1 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 8.2017 -1.4837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3328 -0.2363 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 6.8634 -2.9700 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 1.9727 -1.9305 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 33 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 13 1 0 0 0 0 5 16 1 0 0 0 0 6 7 2 0 0 0 0 7 34 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 12 6 1 6 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 28 1 0 0 0 0 14 33 1 0 0 0 0 15 9 1 1 0 0 0 15 18 1 0 0 0 0 15 35 1 0 0 0 0 16 29 2 0 0 0 0 16 36 1 0 0 0 0 17 23 1 0 0 0 0 17 25 1 6 0 0 0 18 19 1 0 0 0 0 18 30 1 6 0 0 0 19 20 1 0 0 0 0 19 31 1 1 0 0 0 20 24 1 0 0 0 0 20 32 1 6 0 0 0 21 22 1 0 0 0 0 21 36 1 1 0 0 0 22 25 1 6 0 0 0 22 38 1 0 0 0 0 23 34 1 0 0 0 0 23 37 1 1 0 0 0 24 35 1 0 0 0 0 24 37 1 1 0 0 0 25 10 1 6 0 0 0 25 38 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	24121289
ChEMBL	CHEMBL2332349
ZINC

Physicochemical Properties

Molecular Weight:	538.17
ALogP:	-4.1251
MLogP:	2.78
XLogP:	-0.656
# Rotatable Bonds:	16
Polar Surface Area:	197.13
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	38

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