NPASS Compound

Structure

NPC16601 OpenBabel07101718242D 26 29 0 0 1 0 0 0 0 0999 V2000 3.5491 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -4.8090 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 3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 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 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -4.3090 0.0000 C 0 0 0 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 3.5491 -1.8090 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 4.4152 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2812 -2.8090 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 2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 1 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 6.1472 -3.3090 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 1.3578 0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.6910 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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 18 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 14 1 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 6 0 0 0 13 20 1 0 0 0 0 14 24 1 6 0 0 0 15 19 1 1 0 0 0 15 25 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 19 1 6 0 0 0 19 9 1 1 0 0 0 19 25 1 0 0 0 0 20 23 1 1 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	362.446
LogP:	3.541
LogD:	3.21
LogS:	-4.555
# Rotatable Bonds:	3
TPSA:	85.36
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	5.535
Fsp3:	0.7
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:	-5.067
MDCK Permeability:	3.185258901794441e-05
Pgp-inhibitor:	0.188
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.783
Plasma Protein Binding (PPB):	74.63358306884766%
Volume Distribution (VD):	1.741
Pgp-substrate:	21.332612991333008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.643
CYP2C19-inhibitor:	0.81
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.79
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.901
CYP3A4-substrate:	0.756

ADMET: Excretion

Clearance (CL):	9.358
Half-life (T1/2):	0.523

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.395
Drug-inuced Liver Injury (DILI):	0.25
AMES Toxicity:	0.187
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.823
Skin Sensitization:	0.819
Carcinogencity:	0.391
Eye Corrosion:	0.095
Eye Irritation:	0.229
Respiratory Toxicity:	0.543

Download Data

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

Natural Product: NPC16601

Natural Product ID:	NPC16601
*Common Name:**	WPFQQVQRNHAKQJ-AUZPMGFGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WPFQQVQRNHAKQJ-AUZPMGFGSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-10(2)6-16(21)24-14-7-15-19(25-15)9-20(23)13(11(3)17(22)26-20)8-18(19,5)12(14)4/h6,12,14-15,23H,7-9H2,1-5H3/t12-,14-,15+,18+,19+,20+/m0/s1
SMILES:	CC(=CC(=O)O[C@H]1C[C@H]2O[C@]32[C@]([C@H]1C)(C)CC1=C(C)C(=O)O[C@@]1(C3)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512446
PubChem CID:	636792
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO8462	Ligulariopsis shichuana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027747]
NPO8462	Ligulariopsis shichuana	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	13.0	mm	PMID[512639]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	16.0	mm	PMID[512639]

☑ 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 NPC16601 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	202
0.1-0.2	1406
0.2-0.3	4416
0.3-0.4	7770
0.4-0.5	14272
0.5-0.6	7217
0.6-0.7	5762
0.7-0.8	1511
0.8-0.85	96
0.85-0.9	37
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9479	High Similarity	NPC471938
0.9381	High Similarity	NPC471937
0.9375	High Similarity	NPC471914
0.9355	High Similarity	NPC471915
0.9293	High Similarity	NPC181994
0.9175	High Similarity	NPC109195
0.9175	High Similarity	NPC475038
0.914	High Similarity	NPC472641
0.914	High Similarity	NPC472640
0.9053	High Similarity	NPC165632
0.9032	High Similarity	NPC78594
0.8969	High Similarity	NPC324841
0.8947	High Similarity	NPC111273
0.8936	High Similarity	NPC7349
0.8925	High Similarity	NPC472642
0.8854	High Similarity	NPC209297
0.8854	High Similarity	NPC475380
0.8842	High Similarity	NPC105490
0.8842	High Similarity	NPC140277
0.8842	High Similarity	NPC161998
0.8812	High Similarity	NPC471205
0.8763	High Similarity	NPC475446
0.8763	High Similarity	NPC100912
0.8763	High Similarity	NPC311241
0.875	High Similarity	NPC472441
0.875	High Similarity	NPC276110
0.8713	High Similarity	NPC51719
0.871	High Similarity	NPC242448
0.87	High Similarity	NPC120009
0.8673	High Similarity	NPC72647
0.8673	High Similarity	NPC107806
0.866	High Similarity	NPC194132
0.8627	High Similarity	NPC122816
0.8587	High Similarity	NPC253604
0.8586	High Similarity	NPC38855
0.8544	High Similarity	NPC38948
0.8542	High Similarity	NPC110022
0.8542	High Similarity	NPC472812
0.8515	High Similarity	NPC45897
0.8515	High Similarity	NPC474822
0.8511	High Similarity	NPC93411
0.85	High Similarity	NPC11974
0.8495	Intermediate Similarity	NPC131813
0.8485	Intermediate Similarity	NPC278673
0.8485	Intermediate Similarity	NPC325229
0.8485	Intermediate Similarity	NPC275086
0.8478	Intermediate Similarity	NPC32223
0.8469	Intermediate Similarity	NPC234993
0.8469	Intermediate Similarity	NPC134072
0.8462	Intermediate Similarity	NPC206618
0.8447	Intermediate Similarity	NPC475074
0.8438	Intermediate Similarity	NPC472811
0.8438	Intermediate Similarity	NPC329842
0.8416	Intermediate Similarity	NPC476081
0.8416	Intermediate Similarity	NPC472815
0.8416	Intermediate Similarity	NPC162973
0.8416	Intermediate Similarity	NPC472552
0.8384	Intermediate Similarity	NPC205143
0.8384	Intermediate Similarity	NPC51499
0.835	Intermediate Similarity	NPC471206
0.835	Intermediate Similarity	NPC81630
0.8333	Intermediate Similarity	NPC78973
0.8333	Intermediate Similarity	NPC165608
0.8317	Intermediate Similarity	NPC472554
0.8316	Intermediate Similarity	NPC472809
0.8316	Intermediate Similarity	NPC472810
0.8286	Intermediate Similarity	NPC322912
0.8269	Intermediate Similarity	NPC216636
0.8269	Intermediate Similarity	NPC187435
0.8269	Intermediate Similarity	NPC319438
0.8269	Intermediate Similarity	NPC67321
0.8265	Intermediate Similarity	NPC57117
0.8235	Intermediate Similarity	NPC121423
0.8235	Intermediate Similarity	NPC58329
0.8218	Intermediate Similarity	NPC471413
0.8218	Intermediate Similarity	NPC476767
0.8208	Intermediate Similarity	NPC177047
0.82	Intermediate Similarity	NPC287668
0.8173	Intermediate Similarity	NPC477090
0.8173	Intermediate Similarity	NPC218158
0.8173	Intermediate Similarity	NPC34768
0.8172	Intermediate Similarity	NPC311070
0.8165	Intermediate Similarity	NPC471816
0.8163	Intermediate Similarity	NPC139692
0.8163	Intermediate Similarity	NPC152778
0.8163	Intermediate Similarity	NPC53555
0.8163	Intermediate Similarity	NPC162615
0.8163	Intermediate Similarity	NPC205034
0.8155	Intermediate Similarity	NPC160583
0.8155	Intermediate Similarity	NPC281378
0.8155	Intermediate Similarity	NPC187302
0.8155	Intermediate Similarity	NPC196471
0.8155	Intermediate Similarity	NPC23584
0.8155	Intermediate Similarity	NPC189588
0.8155	Intermediate Similarity	NPC120321
0.8155	Intermediate Similarity	NPC97487
0.8155	Intermediate Similarity	NPC10232
0.8137	Intermediate Similarity	NPC198992
0.8137	Intermediate Similarity	NPC471412
0.8119	Intermediate Similarity	NPC474440
0.8113	Intermediate Similarity	NPC475030
0.8113	Intermediate Similarity	NPC299590
0.8105	Intermediate Similarity	NPC471219
0.81	Intermediate Similarity	NPC202833
0.81	Intermediate Similarity	NPC260796
0.81	Intermediate Similarity	NPC242848
0.8095	Intermediate Similarity	NPC302788
0.8085	Intermediate Similarity	NPC102048
0.8085	Intermediate Similarity	NPC306951
0.8081	Intermediate Similarity	NPC470255
0.8061	Intermediate Similarity	NPC72845
0.8061	Intermediate Similarity	NPC473675
0.8058	Intermediate Similarity	NPC11956
0.8056	Intermediate Similarity	NPC42658
0.8043	Intermediate Similarity	NPC10636
0.8041	Intermediate Similarity	NPC470734
0.8041	Intermediate Similarity	NPC170633
0.8039	Intermediate Similarity	NPC47024
0.8039	Intermediate Similarity	NPC477721
0.8039	Intermediate Similarity	NPC251680
0.8039	Intermediate Similarity	NPC477716
0.8037	Intermediate Similarity	NPC472666
0.8021	Intermediate Similarity	NPC166857
0.802	Intermediate Similarity	NPC477719
0.802	Intermediate Similarity	NPC199099
0.802	Intermediate Similarity	NPC477718
0.8019	Intermediate Similarity	NPC306265
0.8019	Intermediate Similarity	NPC50124
0.8	Intermediate Similarity	NPC220217
0.8	Intermediate Similarity	NPC472818
0.8	Intermediate Similarity	NPC472645
0.8	Intermediate Similarity	NPC119855
0.8	Intermediate Similarity	NPC239961
0.7981	Intermediate Similarity	NPC472821
0.798	Intermediate Similarity	NPC472303
0.7979	Intermediate Similarity	NPC476927
0.7963	Intermediate Similarity	NPC469655
0.7963	Intermediate Similarity	NPC474846
0.7963	Intermediate Similarity	NPC469656
0.7961	Intermediate Similarity	NPC268829
0.7961	Intermediate Similarity	NPC25177
0.7961	Intermediate Similarity	NPC247701
0.7961	Intermediate Similarity	NPC477717
0.7961	Intermediate Similarity	NPC295110
0.7961	Intermediate Similarity	NPC222875
0.7959	Intermediate Similarity	NPC310479
0.7959	Intermediate Similarity	NPC209816
0.7959	Intermediate Similarity	NPC182136
0.7959	Intermediate Similarity	NPC221111
0.7959	Intermediate Similarity	NPC280149
0.7957	Intermediate Similarity	NPC170303
0.7944	Intermediate Similarity	NPC475586
0.7941	Intermediate Similarity	NPC218107
0.7941	Intermediate Similarity	NPC473154
0.7938	Intermediate Similarity	NPC291665
0.7938	Intermediate Similarity	NPC106332
0.7928	Intermediate Similarity	NPC13713
0.7928	Intermediate Similarity	NPC290693
0.7925	Intermediate Similarity	NPC472820
0.7925	Intermediate Similarity	NPC179380
0.7921	Intermediate Similarity	NPC16967
0.7921	Intermediate Similarity	NPC473153
0.7921	Intermediate Similarity	NPC162346
0.7921	Intermediate Similarity	NPC473964
0.7921	Intermediate Similarity	NPC29952
0.7905	Intermediate Similarity	NPC472819
0.79	Intermediate Similarity	NPC191521
0.79	Intermediate Similarity	NPC469697
0.7885	Intermediate Similarity	NPC238397
0.7885	Intermediate Similarity	NPC476769
0.7885	Intermediate Similarity	NPC471363
0.7879	Intermediate Similarity	NPC289479
0.7879	Intermediate Similarity	NPC249034
0.7879	Intermediate Similarity	NPC124374
0.787	Intermediate Similarity	NPC472214
0.787	Intermediate Similarity	NPC472215
0.7864	Intermediate Similarity	NPC219285
0.7864	Intermediate Similarity	NPC477968
0.7864	Intermediate Similarity	NPC470761
0.7864	Intermediate Similarity	NPC477971
0.7864	Intermediate Similarity	NPC473219
0.7864	Intermediate Similarity	NPC228251
0.7864	Intermediate Similarity	NPC20113
0.7864	Intermediate Similarity	NPC161527
0.7864	Intermediate Similarity	NPC477972
0.7857	Intermediate Similarity	NPC314727
0.7857	Intermediate Similarity	NPC474396
0.7857	Intermediate Similarity	NPC83287
0.7857	Intermediate Similarity	NPC50488
0.785	Intermediate Similarity	NPC102843
0.785	Intermediate Similarity	NPC470024
0.785	Intermediate Similarity	NPC325054
0.785	Intermediate Similarity	NPC476765
0.7849	Intermediate Similarity	NPC469802
0.7843	Intermediate Similarity	NPC475709
0.7843	Intermediate Similarity	NPC473244
0.7843	Intermediate Similarity	NPC120446
0.7843	Intermediate Similarity	NPC136781
0.7843	Intermediate Similarity	NPC473963
0.7835	Intermediate Similarity	NPC471796

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 NPC16601 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1613
0.2-0.3	3877
0.3-0.4	2303
0.4-0.5	772
0.5-0.6	237
0.6-0.7	152
0.7-0.8	22
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8113	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD7639	Approved
0.8039	Intermediate Similarity	NPD7640	Approved
0.8037	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD5344	Discontinued
0.7941	Intermediate Similarity	NPD7638	Approved
0.7864	Intermediate Similarity	NPD6648	Approved
0.7857	Intermediate Similarity	NPD7328	Approved
0.7857	Intermediate Similarity	NPD7327	Approved
0.7788	Intermediate Similarity	NPD7516	Approved
0.7767	Intermediate Similarity	NPD4225	Approved
0.7757	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD6686	Approved
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.7414	Intermediate Similarity	NPD8294	Approved
0.7414	Intermediate Similarity	NPD8377	Approved
0.7383	Intermediate Similarity	NPD7632	Discontinued
0.735	Intermediate Similarity	NPD8033	Approved
0.732	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7507	Approved
0.7213	Intermediate Similarity	NPD7319	Approved
0.7172	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7115	Discovery
0.7059	Intermediate Similarity	NPD7503	Approved
0.7027	Intermediate Similarity	NPD6008	Approved
0.7019	Intermediate Similarity	NPD7637	Suspended
0.7	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7838	Discovery
0.6923	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD3168	Discontinued
0.6923	Remote Similarity	NPD46	Approved
0.69	Remote Similarity	NPD6695	Phase 3
0.6887	Remote Similarity	NPD7748	Approved
0.6875	Remote Similarity	NPD7128	Approved
0.6875	Remote Similarity	NPD6402	Approved
0.6875	Remote Similarity	NPD6675	Approved
0.6875	Remote Similarity	NPD5739	Approved
0.6852	Remote Similarity	NPD7902	Approved
0.6814	Remote Similarity	NPD5701	Approved
0.6814	Remote Similarity	NPD5697	Approved
0.681	Remote Similarity	NPD6882	Approved
0.6789	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7320	Approved
0.6754	Remote Similarity	NPD6881	Approved
0.6754	Remote Similarity	NPD6899	Approved
0.6754	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6009	Approved
0.6698	Remote Similarity	NPD7515	Phase 2
0.6696	Remote Similarity	NPD6373	Approved
0.6696	Remote Similarity	NPD6372	Approved
0.6696	Remote Similarity	NPD6013	Approved
0.6696	Remote Similarity	NPD6014	Approved
0.6696	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6051	Approved
0.6638	Remote Similarity	NPD7102	Approved
0.6638	Remote Similarity	NPD6371	Approved
0.6638	Remote Similarity	NPD7290	Approved
0.6638	Remote Similarity	NPD6883	Approved
0.6636	Remote Similarity	NPD6399	Phase 3
0.6635	Remote Similarity	NPD7524	Approved
0.6635	Remote Similarity	NPD7750	Discontinued
0.6613	Remote Similarity	NPD7492	Approved
0.661	Remote Similarity	NPD8133	Approved
0.661	Remote Similarity	NPD4632	Approved
0.6609	Remote Similarity	NPD6011	Approved
0.6607	Remote Similarity	NPD5211	Phase 2
0.6602	Remote Similarity	NPD1694	Approved
0.66	Remote Similarity	NPD7525	Registered
0.66	Remote Similarity	NPD6930	Phase 2
0.66	Remote Similarity	NPD6931	Approved
0.6581	Remote Similarity	NPD8130	Phase 1
0.6581	Remote Similarity	NPD6617	Approved
0.6581	Remote Similarity	NPD6649	Approved
0.6581	Remote Similarity	NPD6847	Approved
0.6581	Remote Similarity	NPD6869	Approved
0.6581	Remote Similarity	NPD6650	Approved
0.6574	Remote Similarity	NPD7900	Approved
0.6574	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6616	Approved
0.6557	Remote Similarity	NPD6054	Approved
0.6557	Remote Similarity	NPD6319	Approved
0.6557	Remote Similarity	NPD6059	Approved
0.6545	Remote Similarity	NPD6084	Phase 2
0.6545	Remote Similarity	NPD4755	Approved
0.6545	Remote Similarity	NPD6083	Phase 2
0.6538	Remote Similarity	NPD3618	Phase 1
0.6525	Remote Similarity	NPD6053	Discontinued
0.6525	Remote Similarity	NPD8297	Approved
0.6522	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5695	Phase 3
0.6508	Remote Similarity	NPD8293	Discontinued
0.6508	Remote Similarity	NPD7078	Approved
0.6504	Remote Similarity	NPD6015	Approved
0.6504	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD6929	Approved
0.6491	Remote Similarity	NPD5141	Approved
0.6486	Remote Similarity	NPD5696	Approved
0.6481	Remote Similarity	NPD5778	Approved
0.6481	Remote Similarity	NPD5779	Approved
0.6481	Remote Similarity	NPD4202	Approved
0.6457	Remote Similarity	NPD7736	Approved
0.6452	Remote Similarity	NPD5988	Approved
0.6452	Remote Similarity	NPD6370	Approved
0.6441	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7332	Phase 2
0.6436	Remote Similarity	NPD7514	Phase 3
0.6429	Remote Similarity	NPD5286	Approved
0.6429	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD4700	Approved
0.6429	Remote Similarity	NPD4696	Approved
0.641	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7604	Phase 2
0.64	Remote Similarity	NPD8328	Phase 3
0.6389	Remote Similarity	NPD5693	Phase 1
0.6389	Remote Similarity	NPD8034	Phase 2
0.6389	Remote Similarity	NPD8035	Phase 2
0.6389	Remote Similarity	NPD7087	Discontinued
0.6381	Remote Similarity	NPD6684	Approved
0.6381	Remote Similarity	NPD7146	Approved
0.6381	Remote Similarity	NPD7334	Approved
0.6381	Remote Similarity	NPD7521	Approved
0.6381	Remote Similarity	NPD6409	Approved
0.6381	Remote Similarity	NPD5330	Approved
0.6373	Remote Similarity	NPD6902	Approved
0.6371	Remote Similarity	NPD5983	Phase 2
0.6364	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD1695	Approved
0.6355	Remote Similarity	NPD5328	Approved
0.6337	Remote Similarity	NPD7645	Phase 2
0.6321	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD3573	Approved
0.6316	Remote Similarity	NPD5226	Approved
0.6316	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5224	Approved
0.6316	Remote Similarity	NPD4633	Approved
0.6303	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5776	Phase 2
0.63	Remote Similarity	NPD6925	Approved
0.6293	Remote Similarity	NPD5357	Phase 1
0.6286	Remote Similarity	NPD6893	Approved
0.6273	Remote Similarity	NPD5282	Discontinued
0.6262	Remote Similarity	NPD6672	Approved
0.6262	Remote Similarity	NPD6903	Approved
0.6262	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5737	Approved
0.6261	Remote Similarity	NPD5174	Approved
0.6261	Remote Similarity	NPD5175	Approved
0.624	Remote Similarity	NPD8516	Approved
0.624	Remote Similarity	NPD8513	Phase 3
0.624	Remote Similarity	NPD8515	Approved
0.624	Remote Similarity	NPD8517	Approved
0.6239	Remote Similarity	NPD6079	Approved
0.6239	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7145	Approved
0.6228	Remote Similarity	NPD5223	Approved
0.6228	Remote Similarity	NPD4159	Approved
0.6226	Remote Similarity	NPD4519	Discontinued
0.6226	Remote Similarity	NPD4623	Approved
0.6226	Remote Similarity	NPD4249	Approved
0.6218	Remote Similarity	NPD4634	Approved
0.6216	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6898	Phase 1
0.621	Remote Similarity	NPD7100	Approved
0.621	Remote Similarity	NPD7101	Approved
0.6204	Remote Similarity	NPD4753	Phase 2
0.619	Remote Similarity	NPD3666	Approved
0.619	Remote Similarity	NPD3665	Phase 1
0.619	Remote Similarity	NPD3133	Approved
0.6179	Remote Similarity	NPD6317	Approved
0.6172	Remote Similarity	NPD6336	Discontinued
0.6168	Remote Similarity	NPD4251	Approved
0.6168	Remote Similarity	NPD4250	Approved
0.6161	Remote Similarity	NPD5221	Approved
0.6161	Remote Similarity	NPD4697	Phase 3
0.6161	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5222	Approved
0.6154	Remote Similarity	NPD3667	Approved
0.6154	Remote Similarity	NPD5209	Approved
0.6154	Remote Similarity	NPD4767	Approved
0.6154	Remote Similarity	NPD4768	Approved
0.6147	Remote Similarity	NPD5785	Approved
0.6142	Remote Similarity	NPD6067	Discontinued
0.6139	Remote Similarity	NPD6932	Approved
0.6132	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6314	Approved
0.6129	Remote Similarity	NPD6313	Approved
0.6129	Remote Similarity	NPD6335	Approved
0.6126	Remote Similarity	NPD6001	Approved
0.6121	Remote Similarity	NPD4754	Approved
0.6117	Remote Similarity	NPD4820	Approved
0.6117	Remote Similarity	NPD5790	Clinical (unspecified phase)

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