NPASS Compound

Structure

NPC475641 OpenBabel07101718202D 46 51 0 0 1 0 0 0 0 0999 V2000 -0.2788 3.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0491 -1.0570 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 1.3578 2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7810 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 6.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -3.2989 2.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8867 3.2058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3479 3.7058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0491 -1.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 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 -2.3479 2.7058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 2.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 2 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 3.3090 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 1.8171 -0.1910 0.0000 C 0 0 2 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 2 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 3.5491 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -1.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2989 4.0148 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 6 42 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 21 2 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 22 1 0 0 0 0 13 43 1 0 0 0 0 14 23 1 0 0 0 0 15 25 1 0 0 0 0 15 28 1 0 0 0 0 16 26 1 0 0 0 0 16 27 1 0 0 0 0 17 22 2 0 0 0 0 17 43 1 0 0 0 0 18 34 1 0 0 0 0 18 37 2 0 0 0 0 19 23 1 0 0 0 0 19 29 2 0 0 0 0 20 38 2 0 0 0 0 20 44 1 0 0 0 0 21 33 1 0 0 0 0 23 22 1 1 0 0 0 24 14 1 6 0 0 0 24 29 1 0 0 0 0 24 45 1 0 0 0 0 25 35 1 1 0 0 0 25 36 1 0 0 0 0 26 34 1 1 0 0 0 26 39 1 0 0 0 0 27 35 1 1 0 0 0 27 46 1 0 0 0 0 28 40 2 0 0 0 0 28 42 1 0 0 0 0 29 36 1 0 0 0 0 30 31 1 0 0 0 0 30 32 1 0 0 0 0 30 44 1 1 0 0 0 31 34 1 6 0 0 0 31 35 1 0 0 0 0 32 36 1 1 0 0 0 32 45 1 0 0 0 0 33 41 2 0 0 0 0 33 46 1 0 0 0 0 34 3 1 6 0 0 0 35 4 1 6 0 0 0 36 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	634.28
Volume:	641.411
LogP:	3.249
LogD:	2.252
LogS:	-4.751
# Rotatable Bonds:	10
TPSA:	138.57
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.196
Synthetic Accessibility Score:	5.393
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.258
MDCK Permeability:	5.962197610642761e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.121
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.872
Plasma Protein Binding (PPB):	76.31279754638672%
Volume Distribution (VD):	2.373
Pgp-substrate:	13.852192878723145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.691
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.371
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.936
CYP3A4-substrate:	0.582

ADMET: Excretion

Clearance (CL):	8.274
Half-life (T1/2):	0.605

ADMET: Toxicity

hERG Blockers:	0.688
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.838
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.856
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.254
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC475641

Natural Product ID:	NPC475641
*Common Name:**	PONWNFBYSMNLAS-GBCPFXQBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PONWNFBYSMNLAS-GBCPFXQBSA-N
Standard InCHI:	InChI=1S/C36H42O10/c1-19-23(22-12-13-43-17-22)14-24-29(19)36(5)25(15-28(40)42-6)35(4)27(46-33(41)21-10-8-7-9-11-21)16-26(39)34(3,18-37)31(35)30(32(36)45-24)44-20(2)38/h7-13,17-18,23-27,30-32,39H,14-16H2,1-6H3/t23-,24-,25+,26-,27+,30-,31+,32-,34-,35+,36-/m1/s1
SMILES:	COC(=O)C[C@H]1[C@@]2(C)[C@@H](OC(=O)c3ccccc3)C[C@H]([C@@]([C@@H]2[C@H]([C@@H]2[C@@]1(C)C1=C(C)[C@@H](C[C@H]1O2)c1ccoc1)OC(=O)C)(C)C=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510032
PubChem CID:	44584369
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
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932	Melia azedarach	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	Activity	=	100.0	%	PMID[556223]

☑ 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 NPC475641 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	350
0.1-0.2	1331
0.2-0.3	2707
0.3-0.4	5090
0.4-0.5	10544
0.5-0.6	8551
0.6-0.7	7244
0.7-0.8	6247
0.8-0.85	469
0.85-0.9	133
0.9-0.95	29
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475237
0.9688	High Similarity	NPC118086
0.9437	High Similarity	NPC62692
0.9437	High Similarity	NPC61967
0.9437	High Similarity	NPC27541
0.9437	High Similarity	NPC126984
0.943	High Similarity	NPC475226
0.9337	High Similarity	NPC11062
0.9321	High Similarity	NPC310572
0.9193	High Similarity	NPC470792
0.9152	High Similarity	NPC294512
0.9125	High Similarity	NPC214495
0.9125	High Similarity	NPC470119
0.9125	High Similarity	NPC475066
0.9074	High Similarity	NPC471003
0.9074	High Similarity	NPC188649
0.9068	High Similarity	NPC472671
0.903	High Similarity	NPC296558
0.9024	High Similarity	NPC121995
0.9018	High Similarity	NPC283209
0.9018	High Similarity	NPC288602
0.9018	High Similarity	NPC88841
0.9018	High Similarity	NPC285567
0.9006	High Similarity	NPC88007
0.9006	High Similarity	NPC194499
0.9006	High Similarity	NPC195954
0.8994	High Similarity	NPC472672
0.8988	High Similarity	NPC176413
0.8988	High Similarity	NPC56953
0.8963	High Similarity	NPC276735
0.8957	High Similarity	NPC79571
0.8957	High Similarity	NPC68848
0.8957	High Similarity	NPC18986
0.8951	High Similarity	NPC474611
0.8938	High Similarity	NPC253201
0.8938	High Similarity	NPC34421
0.8938	High Similarity	NPC237259
0.8938	High Similarity	NPC98206
0.8938	High Similarity	NPC302054
0.8909	High Similarity	NPC86800
0.8896	High Similarity	NPC8389
0.8889	High Similarity	NPC472776
0.8889	High Similarity	NPC472778
0.8889	High Similarity	NPC472777
0.8889	High Similarity	NPC304692
0.8875	High Similarity	NPC182427
0.8875	High Similarity	NPC121615
0.8875	High Similarity	NPC29695
0.8875	High Similarity	NPC322546
0.8875	High Similarity	NPC308205
0.8875	High Similarity	NPC294511
0.8855	High Similarity	NPC270312
0.8827	High Similarity	NPC41880
0.8827	High Similarity	NPC104736
0.8805	High Similarity	NPC472654
0.8795	High Similarity	NPC472670
0.8795	High Similarity	NPC277618
0.8795	High Similarity	NPC472141
0.8795	High Similarity	NPC307781
0.8788	High Similarity	NPC14499
0.8788	High Similarity	NPC475039
0.8788	High Similarity	NPC476035
0.878	High Similarity	NPC287559
0.8773	High Similarity	NPC197137
0.8773	High Similarity	NPC7059
0.8773	High Similarity	NPC470118
0.8773	High Similarity	NPC469847
0.8765	High Similarity	NPC141538
0.8765	High Similarity	NPC296807
0.8765	High Similarity	NPC155939
0.875	High Similarity	NPC212257
0.875	High Similarity	NPC88593
0.8735	High Similarity	NPC56358
0.872	High Similarity	NPC84349
0.872	High Similarity	NPC475967
0.8698	High Similarity	NPC285227
0.869	High Similarity	NPC271235
0.8688	High Similarity	NPC195325
0.8679	High Similarity	NPC71821
0.8675	High Similarity	NPC472139
0.8667	High Similarity	NPC470789
0.8659	High Similarity	NPC299038
0.8642	High Similarity	NPC469503
0.8639	High Similarity	NPC470995
0.8634	High Similarity	NPC228842
0.8629	High Similarity	NPC472663
0.8629	High Similarity	NPC472662
0.8625	High Similarity	NPC471007
0.8614	High Similarity	NPC472771
0.8614	High Similarity	NPC200782
0.8606	High Similarity	NPC140952
0.858	High Similarity	NPC291742
0.858	High Similarity	NPC116717
0.858	High Similarity	NPC472673
0.858	High Similarity	NPC472652
0.858	High Similarity	NPC18135
0.8571	High Similarity	NPC105395
0.8571	High Similarity	NPC125182
0.8571	High Similarity	NPC471001
0.8571	High Similarity	NPC211625
0.8571	High Similarity	NPC475779
0.8571	High Similarity	NPC69647
0.8563	High Similarity	NPC302369
0.8563	High Similarity	NPC134254
0.8563	High Similarity	NPC39986
0.8563	High Similarity	NPC472773
0.8563	High Similarity	NPC469846
0.8562	High Similarity	NPC216755
0.8562	High Similarity	NPC255414
0.8554	High Similarity	NPC472653
0.8545	High Similarity	NPC81405
0.8538	High Similarity	NPC469848
0.8537	High Similarity	NPC476262
0.8537	High Similarity	NPC92979
0.8529	High Similarity	NPC302392
0.8528	High Similarity	NPC246164
0.8528	High Similarity	NPC268905
0.8528	High Similarity	NPC476201
0.8528	High Similarity	NPC33938
0.8521	High Similarity	NPC472651
0.8519	High Similarity	NPC196846
0.8519	High Similarity	NPC470997
0.8512	High Similarity	NPC261184
0.8506	High Similarity	NPC470938
0.8503	High Similarity	NPC82851
0.8488	Intermediate Similarity	NPC94763
0.8476	Intermediate Similarity	NPC282445
0.8476	Intermediate Similarity	NPC114880
0.8471	Intermediate Similarity	NPC255787
0.8471	Intermediate Similarity	NPC160651
0.8466	Intermediate Similarity	NPC242068
0.8466	Intermediate Similarity	NPC247563
0.8466	Intermediate Similarity	NPC186746
0.8462	Intermediate Similarity	NPC308156
0.8462	Intermediate Similarity	NPC93172
0.8462	Intermediate Similarity	NPC470875
0.8462	Intermediate Similarity	NPC97574
0.8457	Intermediate Similarity	NPC254588
0.8457	Intermediate Similarity	NPC470791
0.8457	Intermediate Similarity	NPC470790
0.8457	Intermediate Similarity	NPC234494
0.8452	Intermediate Similarity	NPC471168
0.8452	Intermediate Similarity	NPC165218
0.8452	Intermediate Similarity	NPC472669
0.8447	Intermediate Similarity	NPC471174
0.8443	Intermediate Similarity	NPC472299
0.8443	Intermediate Similarity	NPC335761
0.8439	Intermediate Similarity	NPC167340
0.8439	Intermediate Similarity	NPC469633
0.8434	Intermediate Similarity	NPC167142
0.8434	Intermediate Similarity	NPC472772
0.8434	Intermediate Similarity	NPC261597
0.8434	Intermediate Similarity	NPC36655
0.8424	Intermediate Similarity	NPC214541
0.8424	Intermediate Similarity	NPC469336
0.8424	Intermediate Similarity	NPC44675
0.8424	Intermediate Similarity	NPC75310
0.8424	Intermediate Similarity	NPC25351
0.8421	Intermediate Similarity	NPC82602
0.8421	Intermediate Similarity	NPC472660
0.8412	Intermediate Similarity	NPC472764
0.8412	Intermediate Similarity	NPC478179
0.8412	Intermediate Similarity	NPC472282
0.8412	Intermediate Similarity	NPC476850
0.8412	Intermediate Similarity	NPC476861
0.8412	Intermediate Similarity	NPC472775
0.8412	Intermediate Similarity	NPC100333
0.8412	Intermediate Similarity	NPC472774
0.8412	Intermediate Similarity	NPC472784
0.8405	Intermediate Similarity	NPC156189
0.8402	Intermediate Similarity	NPC469849
0.8402	Intermediate Similarity	NPC276551
0.8402	Intermediate Similarity	NPC123088
0.8402	Intermediate Similarity	NPC470182
0.8402	Intermediate Similarity	NPC472664
0.8393	Intermediate Similarity	NPC472668
0.8393	Intermediate Similarity	NPC471167
0.8393	Intermediate Similarity	NPC329938
0.8393	Intermediate Similarity	NPC69028
0.8393	Intermediate Similarity	NPC471166
0.8391	Intermediate Similarity	NPC472665
0.8385	Intermediate Similarity	NPC62799
0.8385	Intermediate Similarity	NPC470999
0.8383	Intermediate Similarity	NPC307383
0.8382	Intermediate Similarity	NPC236004
0.8382	Intermediate Similarity	NPC471437
0.8382	Intermediate Similarity	NPC469576
0.8375	Intermediate Similarity	NPC251865
0.8375	Intermediate Similarity	NPC84479
0.8364	Intermediate Similarity	NPC57998
0.8364	Intermediate Similarity	NPC178932
0.8363	Intermediate Similarity	NPC471397
0.8363	Intermediate Similarity	NPC327922
0.8363	Intermediate Similarity	NPC472765
0.8363	Intermediate Similarity	NPC472766
0.8354	Intermediate Similarity	NPC291150
0.8343	Intermediate Similarity	NPC469338
0.8343	Intermediate Similarity	NPC292389
0.8343	Intermediate Similarity	NPC476197
0.8343	Intermediate Similarity	NPC477405

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 NPC475641 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	777
0.2-0.3	1602
0.3-0.4	2572
0.4-0.5	2261
0.5-0.6	1139
0.6-0.7	386
0.7-0.8	106
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8728	High Similarity	NPD8434	Phase 2
0.8424	Intermediate Similarity	NPD5761	Phase 2
0.8424	Intermediate Similarity	NPD5760	Phase 2
0.7921	Intermediate Similarity	NPD6765	Approved
0.7921	Intermediate Similarity	NPD6764	Approved
0.7914	Intermediate Similarity	NPD4628	Phase 3
0.7907	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7819	Suspended
0.7816	Intermediate Similarity	NPD8127	Discontinued
0.7784	Intermediate Similarity	NPD6273	Approved
0.7747	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD6784	Approved
0.7747	Intermediate Similarity	NPD6785	Approved
0.7722	Intermediate Similarity	NPD6559	Discontinued
0.7688	Intermediate Similarity	NPD4965	Approved
0.7688	Intermediate Similarity	NPD4967	Phase 2
0.7688	Intermediate Similarity	NPD4966	Approved
0.7674	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5844	Phase 1
0.7644	Intermediate Similarity	NPD7075	Discontinued
0.764	Intermediate Similarity	NPD7473	Discontinued
0.7602	Intermediate Similarity	NPD6599	Discontinued
0.7588	Intermediate Similarity	NPD8404	Phase 2
0.7586	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6232	Discontinued
0.7557	Intermediate Similarity	NPD5494	Approved
0.7544	Intermediate Similarity	NPD3226	Approved
0.7541	Intermediate Similarity	NPD8313	Approved
0.7541	Intermediate Similarity	NPD8312	Approved
0.7529	Intermediate Similarity	NPD920	Approved
0.7529	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD37	Approved
0.7514	Intermediate Similarity	NPD6801	Discontinued
0.7514	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD7799	Discontinued
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD3818	Discontinued
0.7457	Intermediate Similarity	NPD7411	Suspended
0.7447	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD3749	Approved
0.7429	Intermediate Similarity	NPD3817	Phase 2
0.7425	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7228	Approved
0.7401	Intermediate Similarity	NPD919	Approved
0.7399	Intermediate Similarity	NPD4380	Phase 2
0.7386	Intermediate Similarity	NPD7768	Phase 2
0.7371	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6799	Approved
0.7345	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7458	Discontinued
0.7337	Intermediate Similarity	NPD7685	Pre-registration
0.7333	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5402	Approved
0.7314	Intermediate Similarity	NPD1934	Approved
0.731	Intermediate Similarity	NPD2533	Approved
0.731	Intermediate Similarity	NPD2534	Approved
0.731	Intermediate Similarity	NPD2532	Approved
0.7305	Intermediate Similarity	NPD2346	Discontinued
0.7294	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7236	Approved
0.7293	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6166	Phase 2
0.7289	Intermediate Similarity	NPD2799	Discontinued
0.7288	Intermediate Similarity	NPD3882	Suspended
0.7283	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2796	Approved
0.7246	Intermediate Similarity	NPD1551	Phase 2
0.7243	Intermediate Similarity	NPD7240	Approved
0.7241	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8150	Discontinued
0.7228	Intermediate Similarity	NPD7074	Phase 3
0.7225	Intermediate Similarity	NPD5403	Approved
0.7225	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6959	Discontinued
0.7222	Intermediate Similarity	NPD1247	Approved
0.7213	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5401	Approved
0.7209	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6005	Phase 3
0.7202	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6004	Phase 3
0.7202	Intermediate Similarity	NPD6002	Phase 3
0.7202	Intermediate Similarity	NPD1471	Phase 3
0.7186	Intermediate Similarity	NPD7033	Discontinued
0.7184	Intermediate Similarity	NPD7239	Suspended
0.7182	Intermediate Similarity	NPD7229	Phase 3
0.7176	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2801	Approved
0.7175	Intermediate Similarity	NPD8455	Phase 2
0.7174	Intermediate Similarity	NPD7054	Approved
0.716	Intermediate Similarity	NPD1549	Phase 2
0.7157	Intermediate Similarity	NPD7497	Discontinued
0.7152	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7135	Intermediate Similarity	NPD7472	Approved
0.7134	Intermediate Similarity	NPD2313	Discontinued
0.7134	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8407	Phase 2
0.7118	Intermediate Similarity	NPD1243	Approved
0.7117	Intermediate Similarity	NPD6832	Phase 2
0.7112	Intermediate Similarity	NPD7808	Phase 3
0.7112	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD5763	Approved
0.7101	Intermediate Similarity	NPD5762	Approved
0.7101	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2344	Approved
0.7091	Intermediate Similarity	NPD8032	Phase 2
0.7079	Intermediate Similarity	NPD1465	Phase 2
0.7076	Intermediate Similarity	NPD7003	Approved
0.7076	Intermediate Similarity	NPD3750	Approved
0.7063	Intermediate Similarity	NPD1608	Approved
0.7059	Intermediate Similarity	NPD8368	Discontinued
0.7059	Intermediate Similarity	NPD7251	Discontinued
0.7059	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2935	Discontinued
0.7035	Intermediate Similarity	NPD6190	Approved
0.703	Intermediate Similarity	NPD3764	Approved
0.7027	Intermediate Similarity	NPD3751	Discontinued
0.7018	Intermediate Similarity	NPD2800	Approved
0.7006	Intermediate Similarity	NPD5735	Approved
0.7005	Intermediate Similarity	NPD6797	Phase 2
0.6995	Remote Similarity	NPD3787	Discontinued
0.6994	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7435	Discontinued
0.6982	Remote Similarity	NPD3748	Approved
0.6982	Remote Similarity	NPD1510	Phase 2
0.6979	Remote Similarity	NPD8360	Approved
0.6979	Remote Similarity	NPD8435	Approved
0.6979	Remote Similarity	NPD8361	Approved
0.6977	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4110	Phase 3
0.697	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1511	Approved
0.6941	Remote Similarity	NPD6099	Approved
0.6941	Remote Similarity	NPD6100	Approved
0.6936	Remote Similarity	NPD2309	Approved
0.6928	Remote Similarity	NPD6798	Discontinued
0.6923	Remote Similarity	NPD7097	Phase 1
0.6905	Remote Similarity	NPD447	Suspended
0.6902	Remote Similarity	NPD7315	Approved
0.69	Remote Similarity	NPD7696	Phase 3
0.69	Remote Similarity	NPD7680	Approved
0.69	Remote Similarity	NPD7698	Approved
0.69	Remote Similarity	NPD7697	Approved
0.6897	Remote Similarity	NPD8151	Discontinued
0.689	Remote Similarity	NPD5647	Approved
0.6886	Remote Similarity	NPD6663	Approved
0.6886	Remote Similarity	NPD6233	Phase 2
0.6879	Remote Similarity	NPD8166	Discontinued
0.6875	Remote Similarity	NPD1512	Approved
0.6875	Remote Similarity	NPD17	Approved
0.6867	Remote Similarity	NPD7095	Approved
0.6866	Remote Similarity	NPD7871	Phase 2
0.6866	Remote Similarity	NPD7870	Phase 2
0.6864	Remote Similarity	NPD1607	Approved
0.6864	Remote Similarity	NPD6653	Approved
0.6863	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7874	Approved
0.6853	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1240	Approved
0.6845	Remote Similarity	NPD7177	Discontinued
0.6842	Remote Similarity	NPD2438	Suspended
0.6834	Remote Similarity	NPD6779	Approved
0.6834	Remote Similarity	NPD6777	Approved
0.6834	Remote Similarity	NPD6781	Approved
0.6834	Remote Similarity	NPD6778	Approved
0.6834	Remote Similarity	NPD6776	Approved
0.6834	Remote Similarity	NPD6782	Approved
0.6834	Remote Similarity	NPD6780	Approved
0.6829	Remote Similarity	NPD7783	Phase 2
0.6829	Remote Similarity	NPD2797	Approved
0.6829	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3268	Approved
0.6825	Remote Similarity	NPD5953	Discontinued
0.6816	Remote Similarity	NPD7028	Phase 2
0.6813	Remote Similarity	NPD7058	Phase 2
0.6813	Remote Similarity	NPD7057	Phase 3
0.6812	Remote Similarity	NPD7930	Approved
0.6811	Remote Similarity	NPD5711	Approved
0.6811	Remote Similarity	NPD5710	Approved
0.6811	Remote Similarity	NPD6808	Phase 2
0.6809	Remote Similarity	NPD7286	Phase 2
0.6805	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1933	Approved
0.6788	Remote Similarity	NPD2798	Approved
0.6788	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4308	Phase 3

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