NPASS Compound

Structure

NPC196864 OpenBabel07101718292D 34 38 0 0 1 0 0 0 0 0999 V2000 2.2971 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3763 3.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6209 3.1323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1670 0.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3292 0.2720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4127 4.9632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9466 -0.4310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3010 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6157 0.3121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4631 2.5349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 1.1031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1375 0.9702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0330 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 0.9757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6369 1.9716 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6945 1.8718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 0.7687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3884 3.5321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3010 -2.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1670 -0.5243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0576 2.3060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3010 -0.0243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6945 1.2029 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5651 -0.5243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5955 2.3057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2146 4.0954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3010 -3.0243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4874 3.9660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1157 1.1781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1670 -1.5243 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 15 2 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 6 31 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 25 1 0 0 0 0 10 32 1 0 0 0 0 11 18 1 0 0 0 0 11 21 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 32 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 23 1 0 0 0 0 17 26 1 6 0 0 0 18 24 1 0 0 0 0 18 26 1 6 0 0 0 19 24 1 0 0 0 0 19 28 2 0 0 0 0 20 26 1 1 0 0 0 20 34 1 0 0 0 0 21 29 2 0 0 0 0 21 31 1 0 0 0 0 22 30 2 0 0 0 0 22 33 1 0 0 0 0 23 25 1 1 0 0 0 23 33 1 0 0 0 0 25 27 1 1 0 0 0 26 5 1 6 0 0 0 27 13 1 6 0 0 0 27 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.23
Volume:	478.479
LogP:	3.573
LogD:	3.081
LogS:	-5.152
# Rotatable Bonds:	4
TPSA:	92.04
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	6.155
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.275
MDCK Permeability:	3.1446405046153814e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.329
30% Bioavailability (F30%):	0.91

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.882
Plasma Protein Binding (PPB):	67.59274291992188%
Volume Distribution (VD):	0.918
Pgp-substrate:	28.203588485717773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.464
CYP2C19-inhibitor:	0.578
CYP2C19-substrate:	0.658
CYP2C9-inhibitor:	0.443
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.86
CYP3A4-substrate:	0.732

ADMET: Excretion

Clearance (CL):	11.549
Half-life (T1/2):	0.597

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.414
Drug-inuced Liver Injury (DILI):	0.332
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.129
Carcinogencity:	0.409
Eye Corrosion:	0.024
Eye Irritation:	0.066
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC196864

Natural Product ID:	NPC196864
*Common Name:**	Methylangolensate
IUPAC Name:	n.a.
Synonyms:	Methyl Angolensate; Methylangolensate
Standard InCHIKey:	YNMYHRYTRCKSMI-SQHTYAHXSA-N
Standard InCHI:	InChI=1S/C27H34O7/c1-15-17-7-9-25(4)23(16-8-10-32-14-16)33-22(30)13-27(15,25)34-20-12-19(28)24(2,3)18(26(17,20)5)11-21(29)31-6/h8,10,14,17-18,20,23H,1,7,9,11-13H2,2-6H3/t17-,18-,20-,23-,25-,26+,27-/m0/s1
SMILES:	C=C1[C@@H]2CC[C@@]3(C)[C@H](c4ccoc4)OC(=O)C[C@]13O[C@H]1CC(=O)C(C)(C)[C@H](CC(=O)OC)[C@@]21C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483006
PubChem CID:	21596327
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	rind	n.a.	DOI[10.1002/hlca.200800177]
NPO3136	Swietenia macrophylla	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579863]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17323995]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[17450509]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seed kernels	n.a.	n.a.	PMID[19908853]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20411928]
NPO3136	Swietenia macrophylla	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[25330401]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31895570]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3136	Swietenia macrophylla	Species	Meliaceae	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
EC50	1
Others	6

Activity Type	# Activity
Individual Protein	2
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	66.4	n.a.	PMID[498530]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	AFI	=	65.3	%	PMID[498535]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	20.27	%	PMID[498536]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	33.7	%	PMID[498536]
NPT194	Organism	Dengue virus 2	Dengue virus 2	EC50	=	4300.0	nM	PMID[498537]
NPT27	Others	Unspecified		CC50	=	116000.0	nM	PMID[498537]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	27.0	n.a.	PMID[498537]

☑ 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 NPC196864 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	420
0.1-0.2	1518
0.2-0.3	3203
0.3-0.4	6062
0.4-0.5	10557
0.5-0.6	10198
0.6-0.7	8639
0.7-0.8	1647
0.8-0.85	286
0.85-0.9	121
0.9-0.95	41
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477404
0.9722	High Similarity	NPC159927
0.9722	High Similarity	NPC469335
0.9592	High Similarity	NPC469850
0.9586	High Similarity	NPC476122
0.9524	High Similarity	NPC178932
0.9459	High Similarity	NPC469336
0.9456	High Similarity	NPC476201
0.9392	High Similarity	NPC282445
0.9379	High Similarity	NPC470941
0.9342	High Similarity	NPC477405
0.9333	High Similarity	NPC472772
0.9333	High Similarity	NPC249021
0.9333	High Similarity	NPC472283
0.9333	High Similarity	NPC167142
0.9329	High Similarity	NPC476262
0.9306	High Similarity	NPC142113
0.9276	High Similarity	NPC470939
0.9267	High Similarity	NPC107646
0.9267	High Similarity	NPC209364
0.9267	High Similarity	NPC60973
0.9216	High Similarity	NPC292389
0.9216	High Similarity	NPC469338
0.9216	High Similarity	NPC476197
0.9216	High Similarity	NPC419
0.9211	High Similarity	NPC305016
0.9205	High Similarity	NPC286722
0.92	High Similarity	NPC264943
0.9195	High Similarity	NPC469503
0.9178	High Similarity	NPC262198
0.9156	High Similarity	NPC469849
0.9156	High Similarity	NPC276551
0.9156	High Similarity	NPC470940
0.9155	High Similarity	NPC476943
0.915	High Similarity	NPC69028
0.915	High Similarity	NPC472771
0.915	High Similarity	NPC82851
0.9145	High Similarity	NPC473473
0.9145	High Similarity	NPC237155
0.9145	High Similarity	NPC475295
0.9139	High Similarity	NPC263265
0.9133	High Similarity	NPC30222
0.9116	High Similarity	NPC221809
0.9097	High Similarity	NPC470875
0.9091	High Similarity	NPC472773
0.9085	High Similarity	NPC475381
0.9085	High Similarity	NPC25255
0.9073	High Similarity	NPC35000
0.9067	High Similarity	NPC75906
0.906	High Similarity	NPC156189
0.9038	High Similarity	NPC472282
0.9038	High Similarity	NPC473766
0.9038	High Similarity	NPC473753
0.9038	High Similarity	NPC173516
0.9032	High Similarity	NPC476857
0.9032	High Similarity	NPC476858
0.9032	High Similarity	NPC476856
0.9026	High Similarity	NPC200782
0.9026	High Similarity	NPC193798
0.9026	High Similarity	NPC263432
0.9026	High Similarity	NPC329938
0.9026	High Similarity	NPC5079
0.902	High Similarity	NPC477403
0.9013	High Similarity	NPC204663
0.9013	High Similarity	NPC126723
0.9	High Similarity	NPC18135
0.8981	High Similarity	NPC471397
0.8981	High Similarity	NPC160651
0.8968	High Similarity	NPC224394
0.8968	High Similarity	NPC234660
0.8968	High Similarity	NPC663
0.8968	High Similarity	NPC51568
0.8961	High Similarity	NPC335761
0.8961	High Similarity	NPC191828
0.8961	High Similarity	NPC477402
0.8954	High Similarity	NPC195131
0.8951	High Similarity	NPC310830
0.8933	High Similarity	NPC46551
0.8917	High Similarity	NPC476861
0.8917	High Similarity	NPC472774
0.8917	High Similarity	NPC476853
0.8917	High Similarity	NPC476850
0.8917	High Similarity	NPC472775
0.8912	High Similarity	NPC476944
0.891	High Similarity	NPC476860
0.891	High Similarity	NPC470182
0.891	High Similarity	NPC123088
0.8904	High Similarity	NPC121158
0.8903	High Similarity	NPC197596
0.8903	High Similarity	NPC207978
0.8896	High Similarity	NPC474611
0.8896	High Similarity	NPC307383
0.8889	High Similarity	NPC220094
0.8882	High Similarity	NPC57998
0.8867	High Similarity	NPC472654
0.8867	High Similarity	NPC195325
0.8867	High Similarity	NPC470791
0.8867	High Similarity	NPC470790
0.8854	High Similarity	NPC23387
0.8851	High Similarity	NPC41182
0.8846	High Similarity	NPC302369
0.8846	High Similarity	NPC469846
0.8846	High Similarity	NPC134254
0.8846	High Similarity	NPC39986
0.8844	High Similarity	NPC223415
0.8839	High Similarity	NPC472653
0.8836	High Similarity	NPC20500
0.8831	High Similarity	NPC299038
0.8831	High Similarity	NPC45101
0.8824	High Similarity	NPC44675
0.8824	High Similarity	NPC214541
0.8819	High Similarity	NPC310043
0.88	High Similarity	NPC19747
0.8792	High Similarity	NPC346
0.8792	High Similarity	NPC471292
0.8792	High Similarity	NPC62799
0.879	High Similarity	NPC472664
0.8784	High Similarity	NPC238843
0.8784	High Similarity	NPC199044
0.8784	High Similarity	NPC251865
0.8782	High Similarity	NPC6326
0.8782	High Similarity	NPC18347
0.8782	High Similarity	NPC149896
0.8782	High Similarity	NPC472767
0.8782	High Similarity	NPC211777
0.8782	High Similarity	NPC117986
0.8774	High Similarity	NPC473368
0.8774	High Similarity	NPC475967
0.8766	High Similarity	NPC469485
0.8766	High Similarity	NPC41880
0.875	High Similarity	NPC214572
0.8742	High Similarity	NPC211625
0.8734	High Similarity	NPC93172
0.8734	High Similarity	NPC97574
0.8733	High Similarity	NPC255414
0.8733	High Similarity	NPC250228
0.8726	High Similarity	NPC198047
0.8726	High Similarity	NPC165218
0.8718	High Similarity	NPC287559
0.8716	High Similarity	NPC267632
0.8716	High Similarity	NPC470741
0.871	High Similarity	NPC173544
0.871	High Similarity	NPC261597
0.871	High Similarity	NPC81405
0.8701	High Similarity	NPC281258
0.8701	High Similarity	NPC92979
0.8693	High Similarity	NPC44577
0.869	High Similarity	NPC42400
0.8688	High Similarity	NPC82602
0.8688	High Similarity	NPC302392
0.8684	High Similarity	NPC212257
0.8671	High Similarity	NPC271657
0.8662	High Similarity	NPC188649
0.8662	High Similarity	NPC18986
0.8662	High Similarity	NPC471167
0.8662	High Similarity	NPC290400
0.8662	High Similarity	NPC96443
0.8662	High Similarity	NPC471166
0.8654	High Similarity	NPC140952
0.8654	High Similarity	NPC262872
0.8654	High Similarity	NPC474932
0.8645	High Similarity	NPC104736
0.8639	High Similarity	NPC67003
0.8639	High Similarity	NPC56197
0.8627	High Similarity	NPC116717
0.8627	High Similarity	NPC272590
0.8625	High Similarity	NPC271235
0.8625	High Similarity	NPC296558
0.8621	High Similarity	NPC46896
0.8618	High Similarity	NPC329180
0.8618	High Similarity	NPC69647
0.8618	High Similarity	NPC471001
0.8618	High Similarity	NPC125182
0.8616	High Similarity	NPC475779
0.8616	High Similarity	NPC121995
0.8616	High Similarity	NPC149945
0.8616	High Similarity	NPC478178
0.8609	High Similarity	NPC471174
0.8609	High Similarity	NPC71821
0.8609	High Similarity	NPC216755
0.8608	High Similarity	NPC471168
0.8608	High Similarity	NPC88841
0.8608	High Similarity	NPC288602
0.8591	High Similarity	NPC243577
0.859	High Similarity	NPC304692
0.859	High Similarity	NPC469847
0.859	High Similarity	NPC187149
0.859	High Similarity	NPC36655
0.8581	High Similarity	NPC75310
0.8562	High Similarity	NPC270312
0.8562	High Similarity	NPC472651
0.8562	High Similarity	NPC472764
0.8562	High Similarity	NPC100333
0.8562	High Similarity	NPC476224
0.8562	High Similarity	NPC470742
0.8562	High Similarity	NPC476936
0.8553	High Similarity	NPC56358
0.8544	High Similarity	NPC68848
0.8544	High Similarity	NPC472668
0.8543	High Similarity	NPC233763

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 NPC196864 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	1018
0.2-0.3	2081
0.3-0.4	2691
0.4-0.5	1918
0.5-0.6	811
0.6-0.7	247
0.7-0.8	30
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8581	High Similarity	NPD5761	Phase 2
0.8581	High Similarity	NPD5760	Phase 2
0.8137	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD8434	Phase 2
0.7651	Intermediate Similarity	NPD5494	Approved
0.7625	Intermediate Similarity	NPD920	Approved
0.7561	Intermediate Similarity	NPD7819	Suspended
0.7514	Intermediate Similarity	NPD6765	Approved
0.7514	Intermediate Similarity	NPD6764	Approved
0.75	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7411	Suspended
0.7425	Intermediate Similarity	NPD3749	Approved
0.741	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6785	Approved
0.7345	Intermediate Similarity	NPD6784	Approved
0.7325	Intermediate Similarity	NPD2796	Approved
0.7317	Intermediate Similarity	NPD3226	Approved
0.7296	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6599	Discontinued
0.725	Intermediate Similarity	NPD4628	Phase 3
0.7219	Intermediate Similarity	NPD7075	Discontinued
0.7216	Intermediate Similarity	NPD6559	Discontinued
0.7193	Intermediate Similarity	NPD1247	Approved
0.7188	Intermediate Similarity	NPD1243	Approved
0.7176	Intermediate Similarity	NPD919	Approved
0.717	Intermediate Similarity	NPD2346	Discontinued
0.7168	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3748	Approved
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6273	Approved
0.7093	Intermediate Similarity	NPD6959	Discontinued
0.7078	Intermediate Similarity	NPD6832	Phase 2
0.7073	Intermediate Similarity	NPD2534	Approved
0.7073	Intermediate Similarity	NPD2533	Approved
0.7073	Intermediate Similarity	NPD2532	Approved
0.7052	Intermediate Similarity	NPD6808	Phase 2
0.7045	Intermediate Similarity	NPD5844	Phase 1
0.7044	Intermediate Similarity	NPD2799	Discontinued
0.7041	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7019	Intermediate Similarity	NPD1549	Phase 2
0.7012	Intermediate Similarity	NPD6799	Approved
0.7006	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD6100	Approved
0.6993	Remote Similarity	NPD3267	Approved
0.6993	Remote Similarity	NPD3266	Approved
0.6982	Remote Similarity	NPD6801	Discontinued
0.697	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4380	Phase 2
0.6961	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7768	Phase 2
0.6957	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7236	Approved
0.6943	Remote Similarity	NPD8032	Phase 2
0.6933	Remote Similarity	NPD3750	Approved
0.6932	Remote Similarity	NPD7473	Discontinued
0.6919	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD8285	Discontinued
0.6905	Remote Similarity	NPD7458	Discontinued
0.6901	Remote Similarity	NPD5402	Approved
0.6901	Remote Similarity	NPD3817	Phase 2
0.6897	Remote Similarity	NPD8127	Discontinued
0.6894	Remote Similarity	NPD1551	Phase 2
0.6882	Remote Similarity	NPD1934	Approved
0.6879	Remote Similarity	NPD2313	Discontinued
0.6879	Remote Similarity	NPD3268	Approved
0.6871	Remote Similarity	NPD2800	Approved
0.6869	Remote Similarity	NPD8404	Phase 2
0.6867	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2344	Approved
0.6842	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7033	Discontinued
0.6824	Remote Similarity	NPD5890	Approved
0.6824	Remote Similarity	NPD5889	Approved
0.6821	Remote Similarity	NPD17	Approved
0.6818	Remote Similarity	NPD3926	Phase 2
0.6816	Remote Similarity	NPD7074	Phase 3
0.681	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3818	Discontinued
0.6797	Remote Similarity	NPD3972	Approved
0.6792	Remote Similarity	NPD4307	Phase 2
0.679	Remote Similarity	NPD2935	Discontinued
0.6786	Remote Similarity	NPD5403	Approved
0.6786	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6166	Phase 2
0.678	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5401	Approved
0.6765	Remote Similarity	NPD6585	Discontinued
0.6763	Remote Similarity	NPD3882	Suspended
0.6761	Remote Similarity	NPD7229	Phase 3
0.6761	Remote Similarity	NPD6232	Discontinued
0.676	Remote Similarity	NPD7054	Approved
0.6746	Remote Similarity	NPD7239	Suspended
0.6739	Remote Similarity	NPD8150	Discontinued
0.6728	Remote Similarity	NPD1510	Phase 2
0.6727	Remote Similarity	NPD7003	Approved
0.6722	Remote Similarity	NPD7472	Approved
0.6705	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7799	Discontinued
0.6702	Remote Similarity	NPD4107	Approved
0.6688	Remote Similarity	NPD1608	Approved
0.6687	Remote Similarity	NPD2309	Approved
0.6685	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD5711	Approved
0.6667	Remote Similarity	NPD5710	Approved
0.6648	Remote Similarity	NPD7251	Discontinued
0.6647	Remote Similarity	NPD1465	Phase 2
0.6647	Remote Similarity	NPD2801	Approved
0.6646	Remote Similarity	NPD1933	Approved
0.6626	Remote Similarity	NPD4308	Phase 3
0.6624	Remote Similarity	NPD2798	Approved
0.6624	Remote Similarity	NPD1019	Discontinued
0.6612	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7808	Phase 3
0.6611	Remote Similarity	NPD3751	Discontinued
0.6611	Remote Similarity	NPD7228	Approved
0.6605	Remote Similarity	NPD1607	Approved
0.6601	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7435	Discontinued
0.6593	Remote Similarity	NPD6797	Phase 2
0.6592	Remote Similarity	NPD2403	Approved
0.659	Remote Similarity	NPD6279	Approved
0.659	Remote Similarity	NPD37	Approved
0.659	Remote Similarity	NPD6280	Approved
0.6587	Remote Similarity	NPD3887	Approved
0.6584	Remote Similarity	NPD1240	Approved
0.6584	Remote Similarity	NPD2979	Phase 3
0.658	Remote Similarity	NPD4482	Phase 3
0.6578	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD4287	Approved
0.6575	Remote Similarity	NPD7286	Phase 2
0.6573	Remote Similarity	NPD3787	Discontinued
0.6571	Remote Similarity	NPD4967	Phase 2
0.6571	Remote Similarity	NPD4966	Approved
0.6571	Remote Similarity	NPD4965	Approved
0.6564	Remote Similarity	NPD7097	Phase 1
0.6562	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2797	Approved
0.6557	Remote Similarity	NPD7685	Pre-registration
0.6552	Remote Similarity	NPD8455	Phase 2
0.6545	Remote Similarity	NPD6005	Phase 3
0.6545	Remote Similarity	NPD6004	Phase 3
0.6545	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6002	Phase 3
0.6543	Remote Similarity	NPD6355	Discontinued
0.6536	Remote Similarity	NPD5585	Approved
0.6532	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7177	Discontinued
0.6514	Remote Similarity	NPD5353	Approved
0.6513	Remote Similarity	NPD7697	Approved
0.6513	Remote Similarity	NPD7696	Phase 3
0.6513	Remote Similarity	NPD7497	Discontinued
0.6513	Remote Similarity	NPD7698	Approved
0.6509	Remote Similarity	NPD1511	Approved
0.6503	Remote Similarity	NPD5953	Discontinued
0.6497	Remote Similarity	NPD1876	Approved
0.6497	Remote Similarity	NPD6234	Discontinued
0.6494	Remote Similarity	NPD6844	Discontinued
0.6485	Remote Similarity	NPD2438	Suspended
0.6481	Remote Similarity	NPD4140	Approved
0.6474	Remote Similarity	NPD9717	Approved
0.6467	Remote Similarity	NPD7240	Approved
0.6456	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1203	Approved
0.6452	Remote Similarity	NPD8407	Phase 2
0.645	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7783	Phase 2
0.6443	Remote Similarity	NPD6779	Approved
0.6443	Remote Similarity	NPD6781	Approved
0.6443	Remote Similarity	NPD6782	Approved
0.6443	Remote Similarity	NPD6780	Approved
0.6443	Remote Similarity	NPD6776	Approved
0.6443	Remote Similarity	NPD6777	Approved
0.6443	Remote Similarity	NPD6778	Approved
0.6442	Remote Similarity	NPD5124	Phase 1
0.6442	Remote Similarity	NPD4622	Approved
0.6442	Remote Similarity	NPD447	Suspended
0.6442	Remote Similarity	NPD4618	Approved
0.6442	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6386	Approved
0.6437	Remote Similarity	NPD6385	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