NPASS Compound

Structure

NPC475381 OpenBabel07101718322D 36 42 0 0 1 0 0 0 0 0999 V2000 -2.5377 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0260 -1.5960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5144 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2758 -0.5795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9294 -1.3053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4856 -1.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9535 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6918 -1.9535 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8459 -0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6918 -3.9070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5377 -3.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8459 -3.4186 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8459 0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6918 0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -0.9767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8459 -2.4419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8459 -0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6918 1.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 -3.9070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 1.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4410 -2.1512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 0.4884 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -4.3953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 0.4884 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 13 1 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 27 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 25 1 0 0 0 0 10 32 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 12 32 1 0 0 0 0 13 29 2 0 0 0 0 13 33 1 0 0 0 0 14 20 1 0 0 0 0 15 26 1 6 0 0 0 15 27 1 0 0 0 0 16 24 1 0 0 0 0 16 26 1 6 0 0 0 17 27 1 1 0 0 0 17 33 1 0 0 0 0 18 19 1 1 0 0 0 18 21 1 0 0 0 0 18 34 1 0 0 0 0 19 24 1 0 0 0 0 19 30 2 0 0 0 0 20 25 1 1 0 0 0 20 35 1 0 0 0 0 21 26 1 1 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 22 36 1 0 0 0 0 23 31 2 0 0 0 0 23 35 1 0 0 0 0 25 28 1 1 0 0 0 26 5 1 6 0 0 0 27 28 1 1 0 0 0 28 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.23
Volume:	490.088
LogP:	3.636
LogD:	2.919
LogS:	-5.127
# Rotatable Bonds:	3
TPSA:	107.87
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	5.847
Fsp3:	0.75
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:	-5.369
MDCK Permeability:	1.2053968021064065e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.233
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102
Plasma Protein Binding (PPB):	84.5265884399414%
Volume Distribution (VD):	2.407
Pgp-substrate:	17.6357364654541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.558
CYP2C9-inhibitor:	0.444
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.476
CYP3A4-substrate:	0.587

ADMET: Excretion

Clearance (CL):	6.968
Half-life (T1/2):	0.401

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.683
Drug-inuced Liver Injury (DILI):	0.769
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.74
Skin Sensitization:	0.124
Carcinogencity:	0.062
Eye Corrosion:	0.057
Eye Irritation:	0.16
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC475381

Natural Product ID:	NPC475381
*Common Name:**	AZGNIKZHFDJEPU-KZMMSGJGSA-N
IUPAC Name:	n.a.
Synonyms:	1,2-Epoxygedunin
Standard InCHIKey:	AZGNIKZHFDJEPU-KZMMSGJGSA-N
Standard InCHI:	InChI=1S/C28H34O8/c1-13(29)33-17-11-16-24(2,3)19(30)18-21(34-18)26(16,5)15-7-9-25(4)20(14-8-10-32-12-14)35-23(31)22-28(25,36-22)27(15,17)6/h8,10,12,15-18,20-22H,7,9,11H2,1-6H3/t15-,16+,17-,18+,20+,21+,22-,25+,26-,27+,28-/m1/s1
SMILES:	CC(=O)OC1CC2C(C(=O)C3C(C2(C4C1(C56C(O5)C(=O)OC(C6(CC4)C)C7=COC=C7)C)C)O3)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504580
PubChem CID:	44566660
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
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134742]
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	2
Others	3

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Activity	=	81.0	%	PMID[458464]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.58	ug.mL-1	PMID[458464]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.98	ug.mL-1	PMID[458464]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	0.93	%	PMID[458464]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	2.04	%	PMID[458464]

☑ 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 NPC475381 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	451
0.1-0.2	1679
0.2-0.3	3652
0.3-0.4	6844
0.4-0.5	10761
0.5-0.6	9981
0.6-0.7	8211
0.7-0.8	886
0.8-0.85	133
0.85-0.9	51
0.9-0.95	44
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC107646
0.9735	High Similarity	NPC286722
0.9673	High Similarity	NPC470939
0.9671	High Similarity	NPC475295
0.9671	High Similarity	NPC473473
0.9669	High Similarity	NPC209364
0.9539	High Similarity	NPC126723
0.9484	High Similarity	NPC39986
0.9484	High Similarity	NPC302369
0.9484	High Similarity	NPC469846
0.9484	High Similarity	NPC476197
0.9484	High Similarity	NPC134254
0.9481	High Similarity	NPC335761
0.9419	High Similarity	NPC5079
0.9416	High Similarity	NPC237155
0.9412	High Similarity	NPC60973
0.9359	High Similarity	NPC234660
0.9359	High Similarity	NPC51568
0.9355	High Similarity	NPC472653
0.9355	High Similarity	NPC305016
0.9355	High Similarity	NPC25255
0.9351	High Similarity	NPC472283
0.9304	High Similarity	NPC472282
0.9304	High Similarity	NPC473753
0.9304	High Similarity	NPC473766
0.9299	High Similarity	NPC476857
0.9299	High Similarity	NPC476858
0.9299	High Similarity	NPC476856
0.9295	High Similarity	NPC193798
0.9286	High Similarity	NPC263265
0.9245	High Similarity	NPC160651
0.9245	High Similarity	NPC271235
0.9221	High Similarity	NPC469850
0.9216	High Similarity	NPC476201
0.9187	High Similarity	NPC302392
0.9182	High Similarity	NPC476861
0.9182	High Similarity	NPC476853
0.9182	High Similarity	NPC173516
0.9182	High Similarity	NPC476850
0.9177	High Similarity	NPC123088
0.9177	High Similarity	NPC476860
0.9172	High Similarity	NPC290400
0.9172	High Similarity	NPC82851
0.9172	High Similarity	NPC117986
0.9172	High Similarity	NPC96443
0.915	High Similarity	NPC18135
0.9125	High Similarity	NPC471397
0.9119	High Similarity	NPC23387
0.9114	High Similarity	NPC477405
0.9114	High Similarity	NPC469338
0.9114	High Similarity	NPC292389
0.9103	High Similarity	NPC249021
0.9097	High Similarity	NPC476262
0.9085	High Similarity	NPC469335
0.9085	High Similarity	NPC159927
0.9085	High Similarity	NPC476122
0.9085	High Similarity	NPC196864
0.9085	High Similarity	NPC477404
0.9068	High Similarity	NPC470995
0.9062	High Similarity	NPC472651
0.9057	High Similarity	NPC469849
0.9057	High Similarity	NPC276551
0.9057	High Similarity	NPC470940
0.9051	High Similarity	NPC69028
0.9051	High Similarity	NPC263432
0.9045	High Similarity	NPC477403
0.9013	High Similarity	NPC221809
0.9006	High Similarity	NPC472652
0.9	High Similarity	NPC470875
0.8987	High Similarity	NPC191828
0.8981	High Similarity	NPC167142
0.8961	High Similarity	NPC46551
0.8947	High Similarity	NPC262198
0.894	High Similarity	NPC86935
0.8938	High Similarity	NPC271657
0.8931	High Similarity	NPC149896
0.8931	High Similarity	NPC18347
0.8931	High Similarity	NPC329938
0.8924	High Similarity	NPC473368
0.891	High Similarity	NPC282445
0.8889	High Similarity	NPC470941
0.8868	High Similarity	NPC477402
0.8861	High Similarity	NPC187149
0.8861	High Similarity	NPC45101
0.8861	High Similarity	NPC299038
0.8854	High Similarity	NPC214541
0.8854	High Similarity	NPC44675
0.8854	High Similarity	NPC469336
0.8846	High Similarity	NPC469503
0.8841	High Similarity	NPC469848
0.8827	High Similarity	NPC472774
0.8827	High Similarity	NPC472775
0.8812	High Similarity	NPC200782
0.8812	High Similarity	NPC197596
0.8812	High Similarity	NPC472771
0.8805	High Similarity	NPC307383
0.8805	High Similarity	NPC475967
0.879	High Similarity	NPC178932
0.8758	High Similarity	NPC472773
0.8742	High Similarity	NPC36655
0.8742	High Similarity	NPC261597
0.8742	High Similarity	NPC472772
0.8734	High Similarity	NPC264943
0.872	High Similarity	NPC82602
0.8718	High Similarity	NPC156189
0.8704	High Similarity	NPC470182
0.8696	High Similarity	NPC188649
0.8696	High Similarity	NPC207978
0.8696	High Similarity	NPC472668
0.8679	High Similarity	NPC469485
0.8671	High Similarity	NPC57998
0.8671	High Similarity	NPC30222
0.8667	High Similarity	NPC160818
0.8667	High Similarity	NPC476943
0.8667	High Similarity	NPC169299
0.8667	High Similarity	NPC159232
0.8659	High Similarity	NPC327922
0.865	High Similarity	NPC478178
0.865	High Similarity	NPC475779
0.8642	High Similarity	NPC472669
0.8642	High Similarity	NPC88841
0.8642	High Similarity	NPC288602
0.8625	High Similarity	NPC173544
0.8623	High Similarity	NPC262386
0.8616	High Similarity	NPC35000
0.8616	High Similarity	NPC281258
0.8608	High Similarity	NPC75906
0.8608	High Similarity	NPC44577
0.8598	High Similarity	NPC476224
0.859	High Similarity	NPC19747
0.858	High Similarity	NPC211777
0.858	High Similarity	NPC471166
0.858	High Similarity	NPC6326
0.858	High Similarity	NPC471167
0.8571	High Similarity	NPC474611
0.8571	High Similarity	NPC474932
0.8571	High Similarity	NPC142113
0.8563	High Similarity	NPC236004
0.8545	High Similarity	NPC296558
0.8537	High Similarity	NPC97574
0.8537	High Similarity	NPC93172
0.8535	High Similarity	NPC470791
0.8535	High Similarity	NPC470790
0.8528	High Similarity	NPC476035
0.8528	High Similarity	NPC14499
0.8528	High Similarity	NPC475039
0.8528	High Similarity	NPC419
0.8528	High Similarity	NPC663
0.8528	High Similarity	NPC224394
0.8528	High Similarity	NPC471168
0.8528	High Similarity	NPC198047
0.8526	High Similarity	NPC71821
0.8526	High Similarity	NPC255414
0.8519	High Similarity	NPC470789
0.8516	High Similarity	NPC41182
0.8512	High Similarity	NPC167340
0.8509	High Similarity	NPC88007
0.8509	High Similarity	NPC195954
0.8491	Intermediate Similarity	NPC268905
0.8485	Intermediate Similarity	NPC478179
0.8477	Intermediate Similarity	NPC310043
0.8477	Intermediate Similarity	NPC310830
0.8466	Intermediate Similarity	NPC68848
0.8462	Intermediate Similarity	NPC478177
0.8457	Intermediate Similarity	NPC262872
0.8452	Intermediate Similarity	NPC476944
0.8452	Intermediate Similarity	NPC94763
0.8447	Intermediate Similarity	NPC204663
0.8447	Intermediate Similarity	NPC41880
0.8442	Intermediate Similarity	NPC121158
0.8434	Intermediate Similarity	NPC242334
0.843	Intermediate Similarity	NPC105395
0.8424	Intermediate Similarity	NPC472141
0.8424	Intermediate Similarity	NPC121995
0.8421	Intermediate Similarity	NPC220094
0.8418	Intermediate Similarity	NPC69647
0.8418	Intermediate Similarity	NPC195325
0.8418	Intermediate Similarity	NPC125182
0.8418	Intermediate Similarity	NPC471001
0.8418	Intermediate Similarity	NPC472654
0.8415	Intermediate Similarity	NPC165218
0.8415	Intermediate Similarity	NPC472139
0.8411	Intermediate Similarity	NPC214572
0.8405	Intermediate Similarity	NPC287559
0.8395	Intermediate Similarity	NPC469847
0.8395	Intermediate Similarity	NPC472777
0.8395	Intermediate Similarity	NPC472778
0.8395	Intermediate Similarity	NPC195131
0.8395	Intermediate Similarity	NPC194499
0.8395	Intermediate Similarity	NPC472776
0.8387	Intermediate Similarity	NPC223415
0.8387	Intermediate Similarity	NPC243577
0.8373	Intermediate Similarity	NPC270312
0.8373	Intermediate Similarity	NPC100333
0.8365	Intermediate Similarity	NPC212257
0.8364	Intermediate Similarity	NPC276735
0.8364	Intermediate Similarity	NPC146991
0.8354	Intermediate Similarity	NPC18986
0.8353	Intermediate Similarity	NPC470181
0.8344	Intermediate Similarity	NPC346

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 NPC475381 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	1108
0.2-0.3	2346
0.3-0.4	2713
0.4-0.5	1719
0.5-0.6	666
0.6-0.7	212
0.7-0.8	12
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
0.8272	Intermediate Similarity	NPD5761	Phase 2
0.8272	Intermediate Similarity	NPD5760	Phase 2
0.8182	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD8434	Phase 2
0.7571	Intermediate Similarity	NPD6764	Approved
0.7571	Intermediate Similarity	NPD6765	Approved
0.7515	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.744	Intermediate Similarity	NPD6599	Discontinued
0.7403	Intermediate Similarity	NPD6784	Approved
0.7403	Intermediate Similarity	NPD6785	Approved
0.7399	Intermediate Similarity	NPD5494	Approved
0.7341	Intermediate Similarity	NPD919	Approved
0.731	Intermediate Similarity	NPD7819	Suspended
0.7297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD920	Approved
0.7251	Intermediate Similarity	NPD6801	Discontinued
0.7247	Intermediate Similarity	NPD3751	Discontinued
0.7239	Intermediate Similarity	NPD1471	Phase 3
0.7216	Intermediate Similarity	NPD3787	Discontinued
0.7213	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6799	Approved
0.7184	Intermediate Similarity	NPD3749	Approved
0.7182	Intermediate Similarity	NPD6559	Discontinued
0.7168	Intermediate Similarity	NPD3817	Phase 2
0.7168	Intermediate Similarity	NPD5402	Approved
0.7159	Intermediate Similarity	NPD1247	Approved
0.7158	Intermediate Similarity	NPD8285	Discontinued
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4628	Phase 3
0.7093	Intermediate Similarity	NPD7411	Suspended
0.7069	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5403	Approved
0.7056	Intermediate Similarity	NPD7799	Discontinued
0.7041	Intermediate Similarity	NPD5401	Approved
0.7041	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7236	Approved
0.7017	Intermediate Similarity	NPD5844	Phase 1
0.7017	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD8404	Phase 2
0.7011	Intermediate Similarity	NPD8313	Approved
0.7011	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD7473	Discontinued
0.6989	Remote Similarity	NPD8150	Discontinued
0.6983	Remote Similarity	NPD3926	Phase 2
0.6977	Remote Similarity	NPD3226	Approved
0.697	Remote Similarity	NPD2796	Approved
0.6966	Remote Similarity	NPD8127	Discontinued
0.6944	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6166	Phase 2
0.6936	Remote Similarity	NPD4380	Phase 2
0.6932	Remote Similarity	NPD3882	Suspended
0.6928	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7435	Discontinued
0.6919	Remote Similarity	NPD7239	Suspended
0.6901	Remote Similarity	NPD6273	Approved
0.6893	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7458	Discontinued
0.6872	Remote Similarity	NPD6959	Discontinued
0.6868	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD4107	Approved
0.6851	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1243	Approved
0.6845	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6232	Discontinued
0.6832	Remote Similarity	NPD6832	Phase 2
0.6826	Remote Similarity	NPD2346	Discontinued
0.6818	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7251	Discontinued
0.6807	Remote Similarity	NPD3748	Approved
0.6805	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3818	Discontinued
0.6774	Remote Similarity	NPD7808	Phase 3
0.6765	Remote Similarity	NPD3887	Approved
0.6761	Remote Similarity	NPD1934	Approved
0.6757	Remote Similarity	NPD6797	Phase 2
0.6744	Remote Similarity	NPD2532	Approved
0.6744	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2534	Approved
0.6744	Remote Similarity	NPD2533	Approved
0.6742	Remote Similarity	NPD7768	Phase 2
0.6735	Remote Similarity	NPD4482	Phase 3
0.6727	Remote Similarity	NPD6355	Discontinued
0.672	Remote Similarity	NPD7685	Pre-registration
0.6716	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7874	Approved
0.6707	Remote Similarity	NPD8032	Phase 2
0.6707	Remote Similarity	NPD2799	Discontinued
0.6703	Remote Similarity	NPD7074	Phase 3
0.6703	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD8407	Phase 2
0.6686	Remote Similarity	NPD1549	Phase 2
0.6684	Remote Similarity	NPD6781	Approved
0.6684	Remote Similarity	NPD6777	Approved
0.6684	Remote Similarity	NPD6780	Approved
0.6684	Remote Similarity	NPD6778	Approved
0.6684	Remote Similarity	NPD6782	Approved
0.6684	Remote Similarity	NPD6776	Approved
0.6684	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD37	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.6649	Remote Similarity	NPD7054	Approved
0.6649	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4965	Approved
0.6648	Remote Similarity	NPD4966	Approved
0.6648	Remote Similarity	NPD4967	Phase 2
0.6647	Remote Similarity	NPD7097	Phase 1
0.6646	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7907	Approved
0.6633	Remote Similarity	NPD8320	Phase 1
0.6633	Remote Similarity	NPD7870	Phase 2
0.6633	Remote Similarity	NPD8319	Approved
0.6633	Remote Similarity	NPD7871	Phase 2
0.6631	Remote Similarity	NPD8368	Discontinued
0.6627	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7472	Approved
0.6608	Remote Similarity	NPD3750	Approved
0.6595	Remote Similarity	NPD7228	Approved
0.6585	Remote Similarity	NPD7095	Approved
0.6576	Remote Similarity	NPD2403	Approved
0.6575	Remote Similarity	NPD6234	Discontinued
0.6571	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD1551	Phase 2
0.6562	Remote Similarity	NPD8435	Approved
0.6557	Remote Similarity	NPD6808	Phase 2
0.6557	Remote Similarity	NPD7229	Phase 3
0.6556	Remote Similarity	NPD7058	Phase 2
0.6556	Remote Similarity	NPD7057	Phase 3
0.655	Remote Similarity	NPD2800	Approved
0.6545	Remote Similarity	NPD6798	Discontinued
0.6545	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2313	Discontinued
0.6538	Remote Similarity	NPD4111	Phase 1
0.6536	Remote Similarity	NPD1465	Phase 2
0.6536	Remote Similarity	NPD8455	Phase 2
0.6536	Remote Similarity	NPD2801	Approved
0.6535	Remote Similarity	NPD7701	Phase 2
0.6531	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD2344	Approved
0.6529	Remote Similarity	NPD5762	Approved
0.6529	Remote Similarity	NPD2353	Approved
0.6529	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5763	Approved
0.6527	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1933	Approved
0.652	Remote Similarity	NPD7801	Approved
0.6515	Remote Similarity	NPD4580	Approved
0.6512	Remote Similarity	NPD7003	Approved
0.6509	Remote Similarity	NPD7033	Discontinued
0.6506	Remote Similarity	NPD6233	Phase 2
0.6503	Remote Similarity	NPD7199	Phase 2
0.65	Remote Similarity	NPD7497	Discontinued
0.65	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD17	Approved
0.6477	Remote Similarity	NPD8361	Approved
0.6477	Remote Similarity	NPD8360	Approved
0.6474	Remote Similarity	NPD6190	Approved
0.6474	Remote Similarity	NPD2968	Approved
0.6474	Remote Similarity	NPD2971	Approved
0.6471	Remote Similarity	NPD2935	Discontinued
0.6471	Remote Similarity	NPD2438	Suspended
0.6467	Remote Similarity	NPD4307	Phase 2
0.6467	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.646	Remote Similarity	NPD3972	Approved
0.6459	Remote Similarity	NPD4665	Approved
0.6455	Remote Similarity	NPD7240	Approved
0.645	Remote Similarity	NPD3057	Approved
0.6447	Remote Similarity	NPD2975	Approved
0.6447	Remote Similarity	NPD2974	Approved
0.6447	Remote Similarity	NPD2973	Approved
0.6446	Remote Similarity	NPD3764	Approved
0.6446	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3266	Approved
0.6442	Remote Similarity	NPD5980	Discovery
0.6442	Remote Similarity	NPD3267	Approved
0.6439	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD7783	Phase 2
0.6429	Remote Similarity	NPD6535	Approved
0.6429	Remote Similarity	NPD6534	Approved
0.642	Remote Similarity	NPD1512	Approved
0.6414	Remote Similarity	NPD7700	Phase 2
0.6414	Remote Similarity	NPD7699	Phase 2
0.6412	Remote Similarity	NPD1510	Phase 2

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