NPASS Compound

Structure

CID161775 OpenBabel06191715532D 25 28 0 0 1 0 0 0 0 0999 V2000 -4.5612 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2764 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6287 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9432 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2303 3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6342 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6342 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2872 2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2085 3.9360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 -0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9213 2.7770 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 3 23 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 19 1 0 0 0 0 7 24 1 0 0 0 0 8 20 2 0 0 0 0 8 24 1 0 0 0 0 9 4 1 6 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 7 1 1 0 0 0 11 13 1 0 0 0 0 12 17 1 6 0 0 0 13 17 1 6 0 0 0 14 18 1 0 0 0 0 15 21 2 0 0 0 0 15 25 1 0 0 0 0 16 17 1 1 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 2 1 6 0 0 0 18 23 1 6 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.15
Volume:	339.281
LogP:	1.506
LogD:	1.871
LogS:	-2.945
# Rotatable Bonds:	5
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.706
Synthetic Accessibility Score:	5.196
Fsp3:	0.778
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.17
MDCK Permeability:	7.693561929045245e-05
Pgp-inhibitor:	0.309
Pgp-substrate:	0.61
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.411
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.724
Plasma Protein Binding (PPB):	26.248992919921875%
Volume Distribution (VD):	0.456
Pgp-substrate:	73.30015563964844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.238
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.682
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	4.034
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.505
AMES Toxicity:	0.249
Rat Oral Acute Toxicity:	0.878
Maximum Recommended Daily Dose:	0.322
Skin Sensitization:	0.459
Carcinogencity:	0.158
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC161775

Natural Product ID:	NPC161775
*Common Name:**	Chlorajapolide E
IUPAC Name:	n.a.
Synonyms:	Chlorajapolide E
Standard InCHIKey:	OUJYYGQZMSBQBK-JJPRHFNDSA-N
Standard InCHI:	InChI=1S/C18H24O7/c1-8(20)24-7-11-9-4-12(9)17(2)13(11)5-14-10(6-19)15(21)25-18(14,23-3)16(17)22/h9,11-13,16,19,22H,4-7H2,1-3H3/t9-,11-,12-,13+,16+,17+,18-/m1/s1
SMILES:	CC(=O)OC[C@@H]1[C@H]2C[C@H]2[C@@]2(C)[C@H]1CC1=C(CO)C(=O)O[C@]1([C@H]2O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669182
PubChem CID:	50993901
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1016/j.phytol.2016.01.005]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18451544]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	Whole plant	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	whole plants	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21650224]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21650224]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	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
IC50	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	<	10000.0	nM	PMID[449793]
NPT1997	Cell Line	OS-RC-2	Homo sapiens	IC50	<	10000.0	nM	PMID[449793]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	10000.0	nM	PMID[449793]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[449793]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PMID[449793]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[449793]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	<	10000.0	nM	PMID[449793]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	<	10000.0	nM	PMID[449793]

☑ 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 NPC161775 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	232
0.1-0.2	1665
0.2-0.3	5003
0.3-0.4	10089
0.4-0.5	12073
0.5-0.6	7540
0.6-0.7	5026
0.7-0.8	1055
0.8-0.85	8
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8846	High Similarity	NPC257853
0.8586	High Similarity	NPC329435
0.8558	High Similarity	NPC85670
0.82	Intermediate Similarity	NPC472640
0.82	Intermediate Similarity	NPC472641
0.819	Intermediate Similarity	NPC474822
0.819	Intermediate Similarity	NPC159533
0.8174	Intermediate Similarity	NPC84865
0.8137	Intermediate Similarity	NPC319861
0.8113	Intermediate Similarity	NPC471937
0.8103	Intermediate Similarity	NPC226049
0.8095	Intermediate Similarity	NPC471914
0.8056	Intermediate Similarity	NPC181994
0.8039	Intermediate Similarity	NPC111273
0.8039	Intermediate Similarity	NPC471915
0.8036	Intermediate Similarity	NPC470075
0.802	Intermediate Similarity	NPC110022
0.8019	Intermediate Similarity	NPC471938
0.8	Intermediate Similarity	NPC472642
0.7982	Intermediate Similarity	NPC206618
0.7963	Intermediate Similarity	NPC472820
0.7961	Intermediate Similarity	NPC165632
0.7946	Intermediate Similarity	NPC106446
0.7931	Intermediate Similarity	NPC27335
0.7925	Intermediate Similarity	NPC121423
0.7925	Intermediate Similarity	NPC295791
0.7925	Intermediate Similarity	NPC470972
0.7925	Intermediate Similarity	NPC472815
0.7921	Intermediate Similarity	NPC78594
0.7917	Intermediate Similarity	NPC254823
0.789	Intermediate Similarity	NPC38948
0.7885	Intermediate Similarity	NPC199099
0.7885	Intermediate Similarity	NPC205143
0.7876	Intermediate Similarity	NPC106228
0.7876	Intermediate Similarity	NPC138372
0.787	Intermediate Similarity	NPC470980
0.787	Intermediate Similarity	NPC472818
0.787	Intermediate Similarity	NPC477090
0.7857	Intermediate Similarity	NPC264153
0.785	Intermediate Similarity	NPC281378
0.7845	Intermediate Similarity	NPC129434
0.7838	Intermediate Similarity	NPC470076
0.7835	Intermediate Similarity	NPC321385
0.7833	Intermediate Similarity	NPC134902
0.783	Intermediate Similarity	NPC198992
0.783	Intermediate Similarity	NPC475617
0.7826	Intermediate Similarity	NPC230513
0.7826	Intermediate Similarity	NPC42673
0.781	Intermediate Similarity	NPC124512
0.781	Intermediate Similarity	NPC278386
0.781	Intermediate Similarity	NPC159763
0.7807	Intermediate Similarity	NPC290693
0.7807	Intermediate Similarity	NPC203862
0.7807	Intermediate Similarity	NPC152615
0.7798	Intermediate Similarity	NPC122816
0.7788	Intermediate Similarity	NPC31354
0.7788	Intermediate Similarity	NPC320231
0.7788	Intermediate Similarity	NPC98165
0.7788	Intermediate Similarity	NPC84949
0.7788	Intermediate Similarity	NPC471633
0.7788	Intermediate Similarity	NPC69576
0.7778	Intermediate Similarity	NPC472819
0.7768	Intermediate Similarity	NPC42658
0.7759	Intermediate Similarity	NPC154491
0.7759	Intermediate Similarity	NPC268530
0.7757	Intermediate Similarity	NPC472552
0.7748	Intermediate Similarity	NPC177047
0.7736	Intermediate Similarity	NPC16601
0.7736	Intermediate Similarity	NPC38855
0.7724	Intermediate Similarity	NPC192334
0.7724	Intermediate Similarity	NPC60150
0.7719	Intermediate Similarity	NPC5311
0.7719	Intermediate Similarity	NPC193382
0.7719	Intermediate Similarity	NPC310341
0.7719	Intermediate Similarity	NPC199428
0.7719	Intermediate Similarity	NPC99620
0.7714	Intermediate Similarity	NPC254121
0.7712	Intermediate Similarity	NPC471392
0.7706	Intermediate Similarity	NPC186668
0.7706	Intermediate Similarity	NPC239961
0.7705	Intermediate Similarity	NPC476824
0.77	Intermediate Similarity	NPC473891
0.7692	Intermediate Similarity	NPC159456
0.7692	Intermediate Similarity	NPC4021
0.7686	Intermediate Similarity	NPC473593
0.7685	Intermediate Similarity	NPC474124
0.7685	Intermediate Similarity	NPC472821
0.7685	Intermediate Similarity	NPC23584
0.7685	Intermediate Similarity	NPC165608
0.7677	Intermediate Similarity	NPC253604
0.7672	Intermediate Similarity	NPC29639
0.7672	Intermediate Similarity	NPC9674
0.7672	Intermediate Similarity	NPC232258
0.7672	Intermediate Similarity	NPC5883
0.7672	Intermediate Similarity	NPC44899
0.7672	Intermediate Similarity	NPC19028
0.7672	Intermediate Similarity	NPC304260
0.7672	Intermediate Similarity	NPC329905
0.7672	Intermediate Similarity	NPC153085
0.7672	Intermediate Similarity	NPC268326
0.767	Intermediate Similarity	NPC53555
0.767	Intermediate Similarity	NPC471483
0.767	Intermediate Similarity	NPC472812
0.7664	Intermediate Similarity	NPC472554
0.7658	Intermediate Similarity	NPC475030
0.7658	Intermediate Similarity	NPC31522
0.7652	Intermediate Similarity	NPC84987
0.7652	Intermediate Similarity	NPC196429
0.7652	Intermediate Similarity	NPC471355
0.7652	Intermediate Similarity	NPC243196
0.7652	Intermediate Similarity	NPC471353
0.7652	Intermediate Similarity	NPC157376
0.7652	Intermediate Similarity	NPC99728
0.7652	Intermediate Similarity	NPC87250
0.7652	Intermediate Similarity	NPC50305
0.7652	Intermediate Similarity	NPC27507
0.7652	Intermediate Similarity	NPC471354
0.7652	Intermediate Similarity	NPC473852
0.7652	Intermediate Similarity	NPC158344
0.7652	Intermediate Similarity	NPC474418
0.7652	Intermediate Similarity	NPC142066
0.7652	Intermediate Similarity	NPC309034
0.7652	Intermediate Similarity	NPC93883
0.7652	Intermediate Similarity	NPC471351
0.7652	Intermediate Similarity	NPC34390
0.7652	Intermediate Similarity	NPC77319
0.7652	Intermediate Similarity	NPC244402
0.7642	Intermediate Similarity	NPC470427
0.7642	Intermediate Similarity	NPC24599
0.7642	Intermediate Similarity	NPC476097
0.7642	Intermediate Similarity	NPC327664
0.7636	Intermediate Similarity	NPC471205
0.7632	Intermediate Similarity	NPC178289
0.7632	Intermediate Similarity	NPC284915
0.7627	Intermediate Similarity	NPC115349
0.7619	Intermediate Similarity	NPC240673
0.7619	Intermediate Similarity	NPC473153
0.7619	Intermediate Similarity	NPC17578
0.7615	Intermediate Similarity	NPC152966
0.7615	Intermediate Similarity	NPC473543
0.7615	Intermediate Similarity	NPC474550
0.7615	Intermediate Similarity	NPC473577
0.7615	Intermediate Similarity	NPC475585
0.7611	Intermediate Similarity	NPC317460
0.7611	Intermediate Similarity	NPC328074
0.7611	Intermediate Similarity	NPC470063
0.7611	Intermediate Similarity	NPC321272
0.7611	Intermediate Similarity	NPC470025
0.7607	Intermediate Similarity	NPC472004
0.7607	Intermediate Similarity	NPC17938
0.7607	Intermediate Similarity	NPC251226
0.7607	Intermediate Similarity	NPC470312
0.7607	Intermediate Similarity	NPC475136
0.7607	Intermediate Similarity	NPC474466
0.7603	Intermediate Similarity	NPC311534
0.7593	Intermediate Similarity	NPC165578
0.7593	Intermediate Similarity	NPC11956
0.7593	Intermediate Similarity	NPC58329
0.7593	Intermediate Similarity	NPC476471
0.7593	Intermediate Similarity	NPC475344
0.7589	Intermediate Similarity	NPC235014
0.7586	Intermediate Similarity	NPC83287
0.7586	Intermediate Similarity	NPC218093
0.7576	Intermediate Similarity	NPC32223
0.7573	Intermediate Similarity	NPC472811
0.757	Intermediate Similarity	NPC130792
0.757	Intermediate Similarity	NPC472826
0.7568	Intermediate Similarity	NPC300614
0.7568	Intermediate Similarity	NPC88701
0.7568	Intermediate Similarity	NPC217921
0.7568	Intermediate Similarity	NPC128795
0.7568	Intermediate Similarity	NPC90946
0.7568	Intermediate Similarity	NPC135015
0.7568	Intermediate Similarity	NPC48548
0.7565	Intermediate Similarity	NPC207637
0.7547	Intermediate Similarity	NPC73911
0.7547	Intermediate Similarity	NPC218064
0.7545	Intermediate Similarity	NPC475290
0.7545	Intermediate Similarity	NPC51719
0.7545	Intermediate Similarity	NPC82251
0.7545	Intermediate Similarity	NPC220217
0.7545	Intermediate Similarity	NPC119855
0.7544	Intermediate Similarity	NPC470027
0.7542	Intermediate Similarity	NPC67569
0.7542	Intermediate Similarity	NPC231518
0.7542	Intermediate Similarity	NPC40749
0.7542	Intermediate Similarity	NPC475219
0.7542	Intermediate Similarity	NPC233500
0.7524	Intermediate Similarity	NPC292178
0.7524	Intermediate Similarity	NPC86893
0.7523	Intermediate Similarity	NPC218513
0.7523	Intermediate Similarity	NPC473694
0.7523	Intermediate Similarity	NPC473523
0.7523	Intermediate Similarity	NPC475334
0.7523	Intermediate Similarity	NPC475623
0.7523	Intermediate Similarity	NPC196471
0.7523	Intermediate Similarity	NPC189588
0.7523	Intermediate Similarity	NPC55954
0.7523	Intermediate Similarity	NPC187302
0.7523	Intermediate Similarity	NPC10232

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 NPC161775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	2142
0.2-0.3	3823
0.3-0.4	2020
0.4-0.5	570
0.5-0.6	310
0.6-0.7	63
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.781	Intermediate Similarity	NPD4225	Approved
0.7672	Intermediate Similarity	NPD7516	Approved
0.7586	Intermediate Similarity	NPD7328	Approved
0.7586	Intermediate Similarity	NPD7327	Approved
0.7542	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8377	Approved
0.7458	Intermediate Similarity	NPD8294	Approved
0.7407	Intermediate Similarity	NPD7640	Approved
0.7407	Intermediate Similarity	NPD7639	Approved
0.7398	Intermediate Similarity	NPD7319	Approved
0.7395	Intermediate Similarity	NPD8380	Approved
0.7395	Intermediate Similarity	NPD8296	Approved
0.7395	Intermediate Similarity	NPD8379	Approved
0.7395	Intermediate Similarity	NPD8335	Approved
0.7395	Intermediate Similarity	NPD8378	Approved
0.735	Intermediate Similarity	NPD7115	Discovery
0.7339	Intermediate Similarity	NPD5344	Discontinued
0.7315	Intermediate Similarity	NPD7638	Approved
0.7295	Intermediate Similarity	NPD7507	Approved
0.7273	Intermediate Similarity	NPD7632	Discontinued
0.7257	Intermediate Similarity	NPD6686	Approved
0.713	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6371	Approved
0.6967	Remote Similarity	NPD7503	Approved
0.6937	Remote Similarity	NPD6648	Approved
0.6916	Remote Similarity	NPD7637	Suspended
0.687	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7492	Approved
0.6748	Remote Similarity	NPD6059	Approved
0.6748	Remote Similarity	NPD6054	Approved
0.6746	Remote Similarity	NPD6616	Approved
0.6698	Remote Similarity	NPD7524	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6694	Remote Similarity	NPD6016	Approved
0.6693	Remote Similarity	NPD7078	Approved
0.6693	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6641	Remote Similarity	NPD7736	Approved
0.664	Remote Similarity	NPD6370	Approved
0.664	Remote Similarity	NPD5988	Approved
0.6613	Remote Similarity	NPD6319	Approved
0.661	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6412	Phase 2
0.6571	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD8133	Approved
0.6504	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6009	Approved
0.6441	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4159	Approved
0.6404	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4632	Approved
0.6387	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5785	Approved
0.6356	Remote Similarity	NPD6008	Approved
0.6328	Remote Similarity	NPD8328	Phase 3
0.6321	Remote Similarity	NPD6695	Phase 3
0.6311	Remote Similarity	NPD6882	Approved
0.6311	Remote Similarity	NPD6053	Discontinued
0.6299	Remote Similarity	NPD8515	Approved
0.6299	Remote Similarity	NPD8513	Phase 3
0.6299	Remote Similarity	NPD8517	Approved
0.6299	Remote Similarity	NPD8516	Approved
0.6262	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6226	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7128	Approved
0.6218	Remote Similarity	NPD5739	Approved
0.6218	Remote Similarity	NPD6402	Approved
0.6218	Remote Similarity	NPD6675	Approved
0.6202	Remote Similarity	NPD7604	Phase 2
0.6197	Remote Similarity	NPD7625	Phase 1
0.6179	Remote Similarity	NPD8297	Approved
0.6167	Remote Similarity	NPD5697	Approved
0.6167	Remote Similarity	NPD5701	Approved
0.6161	Remote Similarity	NPD7983	Approved
0.6148	Remote Similarity	NPD4634	Approved
0.6147	Remote Similarity	NPD4249	Approved
0.614	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6902	Approved
0.6116	Remote Similarity	NPD6881	Approved
0.6116	Remote Similarity	NPD6899	Approved
0.6106	Remote Similarity	NPD6399	Phase 3
0.6098	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6929	Approved
0.6091	Remote Similarity	NPD4250	Approved
0.6091	Remote Similarity	NPD4251	Approved
0.6091	Remote Similarity	NPD7750	Discontinued
0.6077	Remote Similarity	NPD6067	Discontinued
0.6071	Remote Similarity	NPD3168	Discontinued
0.6066	Remote Similarity	NPD6372	Approved
0.6066	Remote Similarity	NPD6373	Approved
0.6066	Remote Similarity	NPD6014	Approved
0.6066	Remote Similarity	NPD6012	Approved
0.6066	Remote Similarity	NPD6013	Approved
0.6061	Remote Similarity	NPD8074	Phase 3
0.6055	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD5983	Phase 2
0.6038	Remote Similarity	NPD6931	Approved
0.6038	Remote Similarity	NPD6930	Phase 2
0.6034	Remote Similarity	NPD6084	Phase 2
0.6034	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD5362	Discontinued
0.6017	Remote Similarity	NPD1700	Approved
0.6016	Remote Similarity	NPD7102	Approved
0.6016	Remote Similarity	NPD7290	Approved
0.6016	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6011	Approved
0.5982	Remote Similarity	NPD6051	Approved
0.5982	Remote Similarity	NPD5328	Approved
0.5968	Remote Similarity	NPD6617	Approved
0.5968	Remote Similarity	NPD6869	Approved
0.5968	Remote Similarity	NPD6650	Approved
0.5968	Remote Similarity	NPD6847	Approved
0.5968	Remote Similarity	NPD6649	Approved
0.5968	Remote Similarity	NPD8130	Phase 1
0.5966	Remote Similarity	NPD5211	Phase 2
0.5948	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5956	Approved
0.5926	Remote Similarity	NPD5209	Approved
0.5913	Remote Similarity	NPD5282	Discontinued
0.5913	Remote Similarity	NPD7748	Approved
0.5909	Remote Similarity	NPD1694	Approved
0.5909	Remote Similarity	NPD5363	Approved
0.5909	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5776	Phase 2
0.5905	Remote Similarity	NPD6925	Approved
0.5897	Remote Similarity	NPD4755	Approved
0.5888	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7514	Phase 3
0.5888	Remote Similarity	NPD7525	Registered
0.5877	Remote Similarity	NPD7087	Discontinued
0.5877	Remote Similarity	NPD8034	Phase 2
0.5877	Remote Similarity	NPD6411	Approved
0.5877	Remote Similarity	NPD6079	Approved
0.5877	Remote Similarity	NPD8035	Phase 2
0.5877	Remote Similarity	NPD7515	Phase 2
0.5872	Remote Similarity	NPD5331	Approved
0.5872	Remote Similarity	NPD5332	Approved
0.5868	Remote Similarity	NPD5141	Approved
0.5865	Remote Similarity	NPD6336	Discontinued
0.5849	Remote Similarity	NPD6115	Approved
0.5849	Remote Similarity	NPD6118	Approved
0.5849	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6114	Approved
0.5849	Remote Similarity	NPD6697	Approved
0.5849	Remote Similarity	NPD7145	Approved
0.5847	Remote Similarity	NPD5696	Approved
0.5841	Remote Similarity	NPD1695	Approved
0.584	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4790	Discontinued
0.5826	Remote Similarity	NPD8171	Discontinued
0.5826	Remote Similarity	NPD4202	Approved
0.582	Remote Similarity	NPD6640	Phase 3
0.5818	Remote Similarity	NPD4786	Approved
0.5812	Remote Similarity	NPD4697	Phase 3
0.5812	Remote Similarity	NPD7839	Suspended
0.5812	Remote Similarity	NPD5221	Approved
0.5812	Remote Similarity	NPD5222	Approved
0.5812	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6933	Approved
0.5802	Remote Similarity	NPD6921	Approved
0.5798	Remote Similarity	NPD4700	Approved
0.5798	Remote Similarity	NPD5286	Approved
0.5798	Remote Similarity	NPD4696	Approved
0.5798	Remote Similarity	NPD5285	Approved
0.5781	Remote Similarity	NPD6274	Approved
0.578	Remote Similarity	NPD4270	Approved
0.578	Remote Similarity	NPD3667	Approved
0.578	Remote Similarity	NPD4269	Approved
0.5776	Remote Similarity	NPD6001	Approved
0.5766	Remote Similarity	NPD6893	Approved
0.5766	Remote Similarity	NPD1696	Phase 3
0.5763	Remote Similarity	NPD5173	Approved
0.5763	Remote Similarity	NPD7902	Approved
0.5752	Remote Similarity	NPD6903	Approved
0.5752	Remote Similarity	NPD5737	Approved
0.5752	Remote Similarity	NPD6672	Approved
0.5741	Remote Similarity	NPD4821	Approved
0.5741	Remote Similarity	NPD4822	Approved
0.5741	Remote Similarity	NPD6928	Phase 2
0.5741	Remote Similarity	NPD4820	Approved
0.5741	Remote Similarity	NPD4748	Discontinued
0.5741	Remote Similarity	NPD7332	Phase 2
0.5741	Remote Similarity	NPD4819	Approved
0.5739	Remote Similarity	NPD5693	Phase 1
0.5738	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7154	Phase 3
0.5725	Remote Similarity	NPD6845	Suspended
0.5714	Remote Similarity	NPD7146	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