NPASS Compound

Structure

NPC62725 OpenBabel07101718302D 71 78 0 0 1 0 0 0 0 0999 V2000 -1.7101 1.9747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0589 4.3108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0715 4.3108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0589 -2.3361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0715 -2.3361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7101 0.9873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8551 -1.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8551 -0.4937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5652 1.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4203 1.9747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8551 1.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8551 -1.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4203 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5652 0.4937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4203 2.9620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7101 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4203 1.9747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5652 0.4937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2753 1.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7101 2.9620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4057 1.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5652 -2.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8551 1.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7101 1.9747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4057 0.4937 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4203 -2.9620 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7101 -0.9873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8551 0.4937 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4203 -0.9873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2608 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4203 -3.9494 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2608 -0.9873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2753 -4.4430 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4057 -1.4810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1304 -3.9494 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8405 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8405 -0.9873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9854 0.4937 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9854 -1.4810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9854 1.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5506 -0.9873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1304 -2.9620 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1304 -0.9873 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4203 0.9873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5652 3.4557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5652 -1.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7101 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8551 0.4937 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5652 1.4810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2608 1.9747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7101 -2.9620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1158 0.4937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5652 -4.4430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1158 -1.4810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2753 -5.4304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4057 -2.4684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9854 -4.4430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6956 0.4937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8405 1.9747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4203 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2753 1.4810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1304 1.9747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5506 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2753 -2.4684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2753 -1.4810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6956 -1.4810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1304 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9854 -2.4684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 47 1 0 0 0 0 3 47 1 0 0 0 0 4 48 1 0 0 0 0 5 48 1 0 0 0 0 7 50 1 0 0 0 0 9 10 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 25 2 0 0 0 0 12 30 1 0 0 0 0 13 16 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 31 1 0 0 0 0 15 49 1 0 0 0 0 16 51 1 0 0 0 0 17 19 1 0 0 0 0 17 47 1 0 0 0 0 18 20 1 0 0 0 0 18 50 1 0 0 0 0 19 52 1 0 0 0 0 20 52 1 0 0 0 0 21 65 1 0 0 0 0 22 26 1 0 0 0 0 22 47 1 0 0 0 0 23 53 1 0 0 0 0 24 54 1 0 0 0 0 25 26 1 0 0 0 0 25 50 1 0 0 0 0 26 52 1 6 0 0 0 27 23 1 1 0 0 0 27 32 1 0 0 0 0 27 66 1 0 0 0 0 28 24 1 6 0 0 0 28 33 1 0 0 0 0 28 67 1 0 0 0 0 29 48 1 0 0 0 0 29 49 1 1 0 0 0 30 49 1 1 0 0 0 30 51 1 0 0 0 0 31 48 1 0 0 0 0 31 68 1 1 0 0 0 32 34 1 0 0 0 0 32 55 1 1 0 0 0 33 35 1 0 0 0 0 33 56 1 1 0 0 0 34 36 1 0 0 0 0 34 57 1 1 0 0 0 35 37 1 0 0 0 0 35 58 1 6 0 0 0 36 43 1 0 0 0 0 36 59 1 6 0 0 0 37 44 1 0 0 0 0 37 60 1 1 0 0 0 38 39 1 0 0 0 0 38 40 1 0 0 0 0 38 61 1 6 0 0 0 39 41 1 0 0 0 0 39 69 1 1 0 0 0 40 42 1 1 0 0 0 40 70 1 0 0 0 0 41 45 1 0 0 0 0 41 71 1 6 0 0 0 42 62 2 0 0 0 0 42 65 1 0 0 0 0 43 66 1 0 0 0 0 43 69 1 1 0 0 0 44 67 1 0 0 0 0 44 71 1 6 0 0 0 45 68 1 1 0 0 0 45 70 1 0 0 0 0 46 63 2 0 0 0 0 46 64 1 0 0 0 0 49 6 1 1 0 0 0 50 51 1 1 0 0 0 51 8 1 1 0 0 0 52 46 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1012.56
Volume:	998.601
LogP:	3.778
LogD:	3.395
LogS:	-3.458
# Rotatable Bonds:	14
TPSA:	301.05
# H-Bond Aceptor:	19
# H-Bond Donor:	10
# Rings:	8
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.055
Synthetic Accessibility Score:	6.402
Fsp3:	0.923
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.993
MDCK Permeability:	5.855594281456433e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.94
20% Bioavailability (F20%):	0.141
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	85.0993881225586%
Volume Distribution (VD):	0.267
Pgp-substrate:	8.472020149230957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.225
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.015

ADMET: Excretion

Clearance (CL):	0.722
Half-life (T1/2):	0.556

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.181
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.633
Skin Sensitization:	0.024
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.796

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC62725

Natural Product ID:	NPC62725
*Common Name:**	{Oleanolic Acid 3-O-Beta-D-Glucopyranosyl(1->2)-[Beta-D-Galactopyranosyl(1->3)]-Beta-D-Glucuronopyranoside-6-O-N-Butyl Ester}
IUPAC Name:	(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6S)-6-butoxycarbonyl-5-hydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	ZVBYEOQPQROTOB-NPGFZERMSA-N
Standard InCHI:	InChI=1S/C52H84O19/c1-9-10-21-65-42(62)40-38(61)39(69-43-36(59)34(57)32(55)27(23-53)66-43)41(71-44-37(60)35(58)33(56)28(24-54)67-44)45(70-40)68-31-14-15-49(6)29(48(31,4)5)13-16-51(8)30(49)12-11-25-26-22-47(2,3)17-19-52(26,46(63)64)20-18-50(25,51)7/h11,26-41,43-45,53-61H,9-10,12-24H2,1-8H3,(H,63,64)/t26-,27+,28+,29-,30+,31-,32-,33+,34-,35-,36+,37+,38-,39-,40-,41+,43-,44-,45+,49-,50+,51+,52-/m0/s1
SMILES:	CCCCOC(=O)[C@@H]1[C@H]([C@@H]([C@H]([C@H](O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3CC=C3[C@@H]5CC(C)(C)CC[C@@]5(CC[C@@]43C)C(=O)O)C2(C)C)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510256
PubChem CID:	16099399
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	48
IC50	1
Others	9

Activity Type	# Activity
Cell Line	49
NON-MOLECULAR	3
Organism	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[569788]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[569788]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	22300.0	nM	PMID[569788]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	23200.0	nM	PMID[569788]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	=	7770.0	nM	PMID[569788]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	34100.0	nM	PMID[569788]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	=	24400.0	nM	PMID[569788]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	=	19400.0	nM	PMID[569788]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	=	33200.0	nM	PMID[569788]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	=	29200.0	nM	PMID[569788]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	=	22800.0	nM	PMID[569788]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	=	19000.0	nM	PMID[569788]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	33300.0	nM	PMID[569788]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	43900.0	nM	PMID[569788]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	=	20100.0	nM	PMID[569788]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	=	21800.0	nM	PMID[569788]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	34200.0	nM	PMID[569788]
NPT386	Cell Line	KM12	Homo sapiens	GI50	=	30800.0	nM	PMID[569788]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	=	36600.0	nM	PMID[569788]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	27700.0	nM	PMID[569788]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	=	26000.0	nM	PMID[569788]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	=	22500.0	nM	PMID[569788]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	=	18000.0	nM	PMID[569788]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	=	17800.0	nM	PMID[569788]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	=	40900.0	nM	PMID[569788]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	=	33100.0	nM	PMID[569788]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	=	26200.0	nM	PMID[569788]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	=	20900.0	nM	PMID[569788]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	>	100000.0	nM	PMID[569788]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	>	100000.0	nM	PMID[569788]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	=	28800.0	nM	PMID[569788]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	=	66800.0	nM	PMID[569788]
NPT401	Cell Line	786-0	Homo sapiens	GI50	=	26200.0	nM	PMID[569788]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	=	20600.0	nM	PMID[569788]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	=	33400.0	nM	PMID[569788]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	=	58500.0	nM	PMID[569788]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	=	21800.0	nM	PMID[569788]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	=	33300.0	nM	PMID[569788]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	=	49200.0	nM	PMID[569788]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	34700.0	nM	PMID[569788]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	38400.0	nM	PMID[569788]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	=	74000.0	nM	PMID[569788]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	14500.0	nM	PMID[569788]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	=	30600.0	nM	PMID[569788]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	=	21500.0	nM	PMID[569788]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	48000.0	nM	PMID[569788]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	=	20900.0	nM	PMID[569788]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.06	mg	PMID[569788]
NPT2	Others	Unspecified		Activity	=	11.0	%	PMID[569788]
NPT2	Others	Unspecified		Activity	=	49.3	%	PMID[569788]
NPT2	Others	Unspecified		Activity	=	71.0	%	PMID[569788]
NPT2	Others	Unspecified		IC50	=	473.0	molar ratio	PMID[569788]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[569788]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	20600.0	nM	PMID[569788]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	26700.0	nM	PMID[569788]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	38000.0	nM	PMID[569788]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC62725 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	286
0.1-0.2	1994
0.2-0.3	5428
0.3-0.4	10455
0.4-0.5	11085
0.5-0.6	6855
0.6-0.7	3698
0.7-0.8	1941
0.8-0.85	359
0.85-0.9	122
0.9-0.95	347
0.95-1	127

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC64715
1.0	High Similarity	NPC86222
1.0	High Similarity	NPC31838
1.0	High Similarity	NPC114484
1.0	High Similarity	NPC297263
1.0	High Similarity	NPC159309
1.0	High Similarity	NPC222580
1.0	High Similarity	NPC104372
1.0	High Similarity	NPC301449
1.0	High Similarity	NPC22956
1.0	High Similarity	NPC171544
1.0	High Similarity	NPC223301
1.0	High Similarity	NPC11242
0.9911	High Similarity	NPC236870
0.9911	High Similarity	NPC80986
0.9911	High Similarity	NPC21691
0.9911	High Similarity	NPC10607
0.9911	High Similarity	NPC187290
0.9911	High Similarity	NPC4749
0.9911	High Similarity	NPC162574
0.9911	High Similarity	NPC475591
0.9911	High Similarity	NPC213952
0.991	High Similarity	NPC236657
0.991	High Similarity	NPC118440
0.9823	High Similarity	NPC283417
0.9823	High Similarity	NPC281148
0.9823	High Similarity	NPC257211
0.9823	High Similarity	NPC302543
0.9823	High Similarity	NPC44716
0.9823	High Similarity	NPC235405
0.9823	High Similarity	NPC200049
0.9823	High Similarity	NPC2370
0.9823	High Similarity	NPC30735
0.9823	High Similarity	NPC258617
0.9821	High Similarity	NPC187618
0.9821	High Similarity	NPC302887
0.982	High Similarity	NPC309780
0.982	High Similarity	NPC208381
0.982	High Similarity	NPC192791
0.982	High Similarity	NPC180550
0.982	High Similarity	NPC473884
0.982	High Similarity	NPC39211
0.982	High Similarity	NPC157868
0.982	High Similarity	NPC6377
0.982	High Similarity	NPC114441
0.982	High Similarity	NPC469945
0.982	High Similarity	NPC472949
0.982	High Similarity	NPC214484
0.982	High Similarity	NPC475171
0.982	High Similarity	NPC11551
0.982	High Similarity	NPC35405
0.9737	High Similarity	NPC33068
0.9737	High Similarity	NPC247315
0.9737	High Similarity	NPC470477
0.9737	High Similarity	NPC471963
0.9737	High Similarity	NPC160452
0.9737	High Similarity	NPC471962
0.9735	High Similarity	NPC235438
0.9735	High Similarity	NPC107966
0.9735	High Similarity	NPC249848
0.9735	High Similarity	NPC313110
0.9735	High Similarity	NPC131469
0.9735	High Similarity	NPC40775
0.973	High Similarity	NPC286347
0.9652	High Similarity	NPC475368
0.9652	High Similarity	NPC181066
0.9652	High Similarity	NPC470218
0.9652	High Similarity	NPC469947
0.9652	High Similarity	NPC284449
0.9649	High Similarity	NPC202666
0.9649	High Similarity	NPC262199
0.9649	High Similarity	NPC14617
0.9649	High Similarity	NPC471961
0.9649	High Similarity	NPC471964
0.9646	High Similarity	NPC242840
0.9646	High Similarity	NPC31193
0.9646	High Similarity	NPC75417
0.964	High Similarity	NPC224121
0.9565	High Similarity	NPC23275
0.9561	High Similarity	NPC471965
0.9558	High Similarity	NPC294112
0.9554	High Similarity	NPC109588
0.955	High Similarity	NPC37134
0.955	High Similarity	NPC291903
0.9487	High Similarity	NPC470475
0.9483	High Similarity	NPC285091
0.9478	High Similarity	NPC478066
0.9464	High Similarity	NPC300419
0.9464	High Similarity	NPC473824
0.9464	High Similarity	NPC475119
0.9459	High Similarity	NPC164389
0.9459	High Similarity	NPC475486
0.9391	High Similarity	NPC275343
0.9381	High Similarity	NPC232237
0.9381	High Similarity	NPC105800
0.9375	High Similarity	NPC476992
0.9375	High Similarity	NPC26626
0.9375	High Similarity	NPC288205
0.9375	High Similarity	NPC51465
0.9375	High Similarity	NPC75287
0.9375	High Similarity	NPC305267
0.9322	High Similarity	NPC470476
0.9298	High Similarity	NPC135849
0.9298	High Similarity	NPC25663
0.9298	High Similarity	NPC51564
0.9298	High Similarity	NPC207738
0.9292	High Similarity	NPC123522
0.9292	High Similarity	NPC85154
0.9292	High Similarity	NPC470876
0.9292	High Similarity	NPC323359
0.9292	High Similarity	NPC33012
0.9292	High Similarity	NPC473452
0.9292	High Similarity	NPC8524
0.9292	High Similarity	NPC475209
0.9292	High Similarity	NPC286457
0.9292	High Similarity	NPC475514
0.9292	High Similarity	NPC191827
0.9292	High Similarity	NPC309223
0.9292	High Similarity	NPC69811
0.9292	High Similarity	NPC102505
0.9292	High Similarity	NPC220160
0.9292	High Similarity	NPC104137
0.9279	High Similarity	NPC1046
0.9279	High Similarity	NPC102439
0.9279	High Similarity	NPC104400
0.9279	High Similarity	NPC109079
0.9279	High Similarity	NPC10320
0.9279	High Similarity	NPC471383
0.9279	High Similarity	NPC79718
0.9279	High Similarity	NPC473373
0.9279	High Similarity	NPC101744
0.9279	High Similarity	NPC324875
0.9279	High Similarity	NPC475516
0.9279	High Similarity	NPC257468
0.9279	High Similarity	NPC104071
0.9279	High Similarity	NPC292677
0.9279	High Similarity	NPC276093
0.9279	High Similarity	NPC80843
0.9279	High Similarity	NPC469946
0.9279	High Similarity	NPC475504
0.9279	High Similarity	NPC139044
0.925	High Similarity	NPC476776
0.9244	High Similarity	NPC269484
0.9244	High Similarity	NPC252657
0.9244	High Similarity	NPC107536
0.9244	High Similarity	NPC470912
0.9244	High Similarity	NPC305793
0.9244	High Similarity	NPC11577
0.9244	High Similarity	NPC9470
0.9244	High Similarity	NPC141600
0.9244	High Similarity	NPC115656
0.9244	High Similarity	NPC244296
0.9244	High Similarity	NPC472267
0.9244	High Similarity	NPC273878
0.9244	High Similarity	NPC280029
0.9244	High Similarity	NPC470518
0.9244	High Similarity	NPC97918
0.9244	High Similarity	NPC477196
0.9244	High Similarity	NPC265841
0.9244	High Similarity	NPC252289
0.9244	High Similarity	NPC88311
0.9244	High Similarity	NPC82380
0.9244	High Similarity	NPC47995
0.9244	High Similarity	NPC1314
0.9231	High Similarity	NPC130229
0.9217	High Similarity	NPC473645
0.9217	High Similarity	NPC476991
0.9211	High Similarity	NPC473459
0.9211	High Similarity	NPC237191
0.9204	High Similarity	NPC160415
0.9204	High Similarity	NPC161674
0.9204	High Similarity	NPC58448
0.9204	High Similarity	NPC471384
0.9196	High Similarity	NPC475287
0.9196	High Similarity	NPC163183
0.9196	High Similarity	NPC475208
0.9196	High Similarity	NPC150400
0.9196	High Similarity	NPC473826
0.9196	High Similarity	NPC166422
0.9196	High Similarity	NPC295823
0.9196	High Similarity	NPC73318
0.9196	High Similarity	NPC323341
0.9196	High Similarity	NPC241909
0.9196	High Similarity	NPC475467
0.9196	High Similarity	NPC309714
0.9196	High Similarity	NPC238935
0.9196	High Similarity	NPC258885
0.9196	High Similarity	NPC473343
0.9196	High Similarity	NPC114287
0.9196	High Similarity	NPC133818
0.9196	High Similarity	NPC46665
0.9196	High Similarity	NPC251263
0.9196	High Similarity	NPC134835
0.9196	High Similarity	NPC192600
0.9196	High Similarity	NPC219180
0.9196	High Similarity	NPC114304
0.9196	High Similarity	NPC96641
0.9196	High Similarity	NPC174720
0.9196	High Similarity	NPC151543
0.9196	High Similarity	NPC124296

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC62725 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	2289
0.2-0.3	3839
0.3-0.4	1762
0.4-0.5	569
0.5-0.6	254
0.6-0.7	126
0.7-0.8	38
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9649	High Similarity	NPD8328	Phase 3
0.9464	High Similarity	NPD8295	Clinical (unspecified phase)
0.8348	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7736	Approved
0.8067	Intermediate Similarity	NPD8133	Approved
0.7903	Intermediate Similarity	NPD8517	Approved
0.7903	Intermediate Similarity	NPD8516	Approved
0.7903	Intermediate Similarity	NPD8515	Approved
0.7903	Intermediate Similarity	NPD8513	Phase 3
0.7874	Intermediate Similarity	NPD8293	Discontinued
0.7752	Intermediate Similarity	NPD7319	Approved
0.7698	Intermediate Similarity	NPD6370	Approved
0.7656	Intermediate Similarity	NPD7507	Approved
0.7578	Intermediate Similarity	NPD7492	Approved
0.7563	Intermediate Similarity	NPD6412	Phase 2
0.754	Intermediate Similarity	NPD8377	Approved
0.754	Intermediate Similarity	NPD6319	Approved
0.754	Intermediate Similarity	NPD6059	Approved
0.754	Intermediate Similarity	NPD8294	Approved
0.754	Intermediate Similarity	NPD6054	Approved
0.7519	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6686	Approved
0.748	Intermediate Similarity	NPD8335	Approved
0.748	Intermediate Similarity	NPD8378	Approved
0.748	Intermediate Similarity	NPD8379	Approved
0.748	Intermediate Similarity	NPD8296	Approved
0.748	Intermediate Similarity	NPD8380	Approved
0.7478	Intermediate Similarity	NPD7902	Approved
0.7462	Intermediate Similarity	NPD7078	Approved
0.7398	Intermediate Similarity	NPD6882	Approved
0.7398	Intermediate Similarity	NPD8297	Approved
0.7368	Intermediate Similarity	NPD7748	Approved
0.7344	Intermediate Similarity	NPD8033	Approved
0.7344	Intermediate Similarity	NPD6015	Approved
0.7344	Intermediate Similarity	NPD6016	Approved
0.7302	Intermediate Similarity	NPD6009	Approved
0.7295	Intermediate Similarity	NPD6372	Approved
0.7295	Intermediate Similarity	NPD6373	Approved
0.7287	Intermediate Similarity	NPD5988	Approved
0.725	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7900	Approved
0.7193	Intermediate Similarity	NPD7515	Phase 2
0.719	Intermediate Similarity	NPD7128	Approved
0.719	Intermediate Similarity	NPD6402	Approved
0.719	Intermediate Similarity	NPD6675	Approved
0.719	Intermediate Similarity	NPD5739	Approved
0.7177	Intermediate Similarity	NPD6650	Approved
0.7177	Intermediate Similarity	NPD6649	Approved
0.7177	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7328	Approved
0.7109	Intermediate Similarity	NPD7327	Approved
0.7073	Intermediate Similarity	NPD6899	Approved
0.7073	Intermediate Similarity	NPD7320	Approved
0.7073	Intermediate Similarity	NPD6881	Approved
0.7063	Intermediate Similarity	NPD4632	Approved
0.7054	Intermediate Similarity	NPD7516	Approved
0.704	Intermediate Similarity	NPD8130	Phase 1
0.7015	Intermediate Similarity	NPD6033	Approved
0.6992	Remote Similarity	NPD5697	Approved
0.6992	Remote Similarity	NPD5701	Approved
0.696	Remote Similarity	NPD7290	Approved
0.696	Remote Similarity	NPD6883	Approved
0.696	Remote Similarity	NPD7102	Approved
0.6947	Remote Similarity	NPD7503	Approved
0.6947	Remote Similarity	NPD6921	Approved
0.694	Remote Similarity	NPD8074	Phase 3
0.6905	Remote Similarity	NPD6847	Approved
0.6905	Remote Similarity	NPD6617	Approved
0.6905	Remote Similarity	NPD6869	Approved
0.6897	Remote Similarity	NPD8034	Phase 2
0.6897	Remote Similarity	NPD6411	Approved
0.6897	Remote Similarity	NPD8035	Phase 2
0.688	Remote Similarity	NPD6014	Approved
0.688	Remote Similarity	NPD6012	Approved
0.688	Remote Similarity	NPD6013	Approved
0.6842	Remote Similarity	NPD7604	Phase 2
0.6825	Remote Similarity	NPD4634	Approved
0.6818	Remote Similarity	NPD5983	Phase 2
0.68	Remote Similarity	NPD6011	Approved
0.6772	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7115	Discovery
0.6741	Remote Similarity	NPD6336	Discontinued
0.6724	Remote Similarity	NPD6101	Approved
0.6724	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6399	Phase 3
0.6694	Remote Similarity	NPD7638	Approved
0.6639	Remote Similarity	NPD7640	Approved
0.6639	Remote Similarity	NPD7639	Approved
0.6614	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6083	Phase 2
0.6612	Remote Similarity	NPD6084	Phase 2
0.6612	Remote Similarity	NPD4755	Approved
0.661	Remote Similarity	NPD7983	Approved
0.6593	Remote Similarity	NPD6067	Discontinued
0.6577	Remote Similarity	NPD7645	Phase 2
0.6567	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD6274	Approved
0.6562	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4225	Approved
0.6555	Remote Similarity	NPD5778	Approved
0.6555	Remote Similarity	NPD5779	Approved
0.6555	Remote Similarity	NPD8171	Discontinued
0.6541	Remote Similarity	NPD7100	Approved
0.6541	Remote Similarity	NPD7101	Approved
0.6529	Remote Similarity	NPD4697	Phase 3
0.6522	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD8080	Discontinued
0.6508	Remote Similarity	NPD6008	Approved
0.6504	Remote Similarity	NPD5285	Approved
0.6504	Remote Similarity	NPD5286	Approved
0.6504	Remote Similarity	NPD4700	Approved
0.6504	Remote Similarity	NPD4696	Approved
0.6466	Remote Similarity	NPD6335	Approved
0.6449	Remote Similarity	NPD8448	Approved
0.6444	Remote Similarity	NPD6909	Approved
0.6444	Remote Similarity	NPD6908	Approved
0.6441	Remote Similarity	NPD5328	Approved
0.6439	Remote Similarity	NPD6868	Approved
0.6434	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8392	Approved
0.6429	Remote Similarity	NPD8391	Approved
0.6429	Remote Similarity	NPD8390	Approved
0.6429	Remote Similarity	NPD7329	Approved
0.6423	Remote Similarity	NPD8341	Approved
0.6423	Remote Similarity	NPD8342	Approved
0.6423	Remote Similarity	NPD8340	Approved
0.6423	Remote Similarity	NPD8299	Approved
0.6423	Remote Similarity	NPD5696	Approved
0.641	Remote Similarity	NPD3573	Approved
0.64	Remote Similarity	NPD5225	Approved
0.64	Remote Similarity	NPD5226	Approved
0.64	Remote Similarity	NPD5224	Approved
0.64	Remote Similarity	NPD5211	Phase 2
0.64	Remote Similarity	NPD4633	Approved
0.6393	Remote Similarity	NPD5222	Approved
0.6393	Remote Similarity	NPD5221	Approved
0.6393	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6317	Approved
0.6391	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4767	Approved
0.6378	Remote Similarity	NPD4768	Approved
0.6377	Remote Similarity	NPD8451	Approved
0.6364	Remote Similarity	NPD8415	Approved
0.6356	Remote Similarity	NPD6672	Approved
0.6356	Remote Similarity	NPD5737	Approved
0.6349	Remote Similarity	NPD5174	Approved
0.6349	Remote Similarity	NPD5175	Approved
0.6343	Remote Similarity	NPD6314	Approved
0.6343	Remote Similarity	NPD6313	Approved
0.6341	Remote Similarity	NPD5173	Approved
0.6333	Remote Similarity	NPD6079	Approved
0.6328	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD3618	Phase 1
0.632	Remote Similarity	NPD5223	Approved
0.6312	Remote Similarity	NPD5956	Approved
0.6311	Remote Similarity	NPD5695	Phase 3
0.6303	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5141	Approved
0.6294	Remote Similarity	NPD8450	Suspended
0.6286	Remote Similarity	NPD8336	Approved
0.6286	Remote Similarity	NPD8337	Approved
0.6279	Remote Similarity	NPD4729	Approved
0.6279	Remote Similarity	NPD4730	Approved
0.6276	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD6698	Approved
0.625	Remote Similarity	NPD46	Approved
0.6242	Remote Similarity	NPD7799	Discontinued
0.6232	Remote Similarity	NPD7829	Approved
0.6232	Remote Similarity	NPD7830	Approved
0.6224	Remote Similarity	NPD8449	Approved
0.622	Remote Similarity	NPD4754	Approved
0.6218	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3669	Approved
0.6207	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD8444	Approved
0.6202	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5248	Approved
0.6183	Remote Similarity	NPD5247	Approved
0.6183	Remote Similarity	NPD5251	Approved
0.6183	Remote Similarity	NPD5249	Phase 3
0.6183	Remote Similarity	NPD5250	Approved
0.6174	Remote Similarity	NPD1779	Approved
0.6174	Remote Similarity	NPD1780	Approved
0.616	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5128	Approved
0.6154	Remote Similarity	NPD7260	Phase 2
0.6154	Remote Similarity	NPD4786	Approved
0.6142	Remote Similarity	NPD7632	Discontinued
0.6122	Remote Similarity	NPD6333	Approved
0.6122	Remote Similarity	NPD6334	Approved
0.6121	Remote Similarity	NPD3667	Approved
0.6111	Remote Similarity	NPD8338	Approved
0.6103	Remote Similarity	NPD7641	Discontinued
0.6098	Remote Similarity	NPD5282	Discontinued
0.6074	Remote Similarity	NPD6940	Discontinued
0.605	Remote Similarity	NPD6098	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data