NPASS Compound

Structure

NPC5741 OpenBabel07101718192D 37 41 0 0 1 0 0 0 0 0999 V2000 -1.1284 -0.3904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2165 -5.4095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3781 -2.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8781 -3.1883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7766 -3.3137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6101 -2.4794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2441 -5.8222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5121 -0.8222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9248 -1.0918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6460 -1.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6319 -1.7989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9863 -0.1041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5121 -3.8222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1902 -2.5335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4213 -1.0975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4753 -4.4436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0338 -1.5458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1428 -1.0918 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5121 -2.8222 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3781 -1.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9986 0.0523 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3781 -4.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6801 -2.0634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0270 -2.7705 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9929 -2.5117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3781 -2.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6460 -2.3222 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2517 -1.5458 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5446 -0.8387 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4412 -4.1847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2441 -0.8222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2441 -3.8222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7000 -3.2188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3781 -5.3222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1779 -2.6899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2318 -3.7364 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 16 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 7 34 1 0 0 0 0 8 10 2 0 0 0 0 8 20 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 27 1 0 0 0 0 11 35 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 35 1 0 0 0 0 16 30 2 0 0 0 0 16 36 1 0 0 0 0 17 18 1 0 0 0 0 18 28 1 1 0 0 0 19 26 1 0 0 0 0 19 27 1 1 0 0 0 20 26 1 0 0 0 0 20 31 2 0 0 0 0 21 29 1 1 0 0 0 21 37 1 0 0 0 0 22 32 2 0 0 0 0 22 34 1 0 0 0 0 23 15 1 6 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 36 1 6 0 0 0 25 28 1 1 0 0 0 25 33 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 15 1 1 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.24
Volume:	519.224
LogP:	3.242
LogD:	2.33
LogS:	-4.748
# Rotatable Bonds:	7
TPSA:	115.57
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.36
Synthetic Accessibility Score:	5.815
Fsp3:	0.621
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.353
MDCK Permeability:	2.0928579033352435e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.227
20% Bioavailability (F20%):	0.872
30% Bioavailability (F30%):	0.902

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	75.92522430419922%
Volume Distribution (VD):	2.065
Pgp-substrate:	19.32288932800293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.405
CYP2C9-inhibitor:	0.558
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.883
CYP3A4-substrate:	0.691

ADMET: Excretion

Clearance (CL):	7.767
Half-life (T1/2):	0.598

ADMET: Toxicity

hERG Blockers:	0.767
Human Hepatotoxicity (H-HT):	0.853
Drug-inuced Liver Injury (DILI):	0.266
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.132
Carcinogencity:	0.063
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC5741

Natural Product ID:	NPC5741
*Common Name:**	Turrapubin E
IUPAC Name:	methyl 2-[(1R,2S)-2-[(1aR,3S,3aR,4R,5R,6R,7aS)-5-acetyloxy-3-(furan-3-yl)-4-hydroxy-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate
Synonyms:
Standard InCHIKey:	SSWQNQTXPXQVMO-DFLDTDNRSA-N
Standard InCHI:	InChI=1S/C29H36O8/c1-15-23(27(5)10-8-20(31)26(3,4)19(27)13-22(32)34-7)24(36-16(2)30)25(33)28(6)18(17-9-11-35-14-17)12-21-29(15,28)37-21/h8-11,14,18-19,21,23-25,33H,1,12-13H2,2-7H3/t18-,19-,21+,23+,24+,25-,27-,28+,29+/m0/s1
SMILES:	C=C1[C@H]([C@H]([C@@H]([C@@]2(C)[C@@H](C[C@@H]3[C@]12O3)c1ccoc1)O)OC(=O)C)[C@@]1(C)C=CC(=O)C(C)(C)[C@@H]1CC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386293
PubChem CID:	71725866
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
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	twig	Dongfang, Hainan Province, China	2010-Mar	PMID[23734701]
NPO10033	Turraea pubescens	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
IC50	2
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[497531]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[497531]
NPT176	Organism	Artemia salina	Artemia salina	mortality	<	50.0	%	PMID[497531]

☑ 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 NPC5741 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	344
0.1-0.2	1345
0.2-0.3	3183
0.3-0.4	5639
0.4-0.5	10777
0.5-0.6	10472
0.6-0.7	9412
0.7-0.8	1187
0.8-0.85	259
0.85-0.9	65
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC471175
0.9605	High Similarity	NPC471169
0.9605	High Similarity	NPC175964
0.9241	High Similarity	NPC259943
0.9156	High Similarity	NPC84063
0.9114	High Similarity	NPC471167
0.9114	High Similarity	NPC471166
0.9057	High Similarity	NPC471168
0.9012	High Similarity	NPC472650
0.8951	High Similarity	NPC472765
0.8951	High Similarity	NPC472766
0.8929	High Similarity	NPC242068
0.8929	High Similarity	NPC247563
0.8924	High Similarity	NPC197137
0.8889	High Similarity	NPC472764
0.8875	High Similarity	NPC472668
0.8848	High Similarity	NPC471632
0.8839	High Similarity	NPC125182
0.8839	High Similarity	NPC69647
0.882	High Similarity	NPC472669
0.8817	High Similarity	NPC105395
0.8797	High Similarity	NPC92979
0.879	High Similarity	NPC268905
0.8758	High Similarity	NPC472767
0.8743	High Similarity	NPC478177
0.8727	High Similarity	NPC285227
0.872	High Similarity	NPC242334
0.872	High Similarity	NPC471397
0.871	High Similarity	NPC255414
0.8688	High Similarity	NPC470118
0.8667	High Similarity	NPC472659
0.8659	High Similarity	NPC173516
0.8642	High Similarity	NPC96443
0.8642	High Similarity	NPC290400
0.8634	High Similarity	NPC472671
0.8634	High Similarity	NPC474932
0.8623	High Similarity	NPC236004
0.8623	High Similarity	NPC471437
0.8623	High Similarity	NPC94763
0.8616	High Similarity	NPC302054
0.8616	High Similarity	NPC253201
0.8608	High Similarity	NPC116717
0.8606	High Similarity	NPC472673
0.8589	High Similarity	NPC472773
0.8589	High Similarity	NPC165218
0.8581	High Similarity	NPC5676
0.8571	High Similarity	NPC475066
0.8571	High Similarity	NPC214495
0.8571	High Similarity	NPC470119
0.8563	High Similarity	NPC469848
0.8562	High Similarity	NPC296807
0.8562	High Similarity	NPC141538
0.8562	High Similarity	NPC155939
0.8562	High Similarity	NPC264943
0.8554	High Similarity	NPC470995
0.8553	High Similarity	NPC33938
0.8553	High Similarity	NPC470996
0.8553	High Similarity	NPC472672
0.8545	High Similarity	NPC472774
0.8545	High Similarity	NPC476861
0.8545	High Similarity	NPC472775
0.8545	High Similarity	NPC476850
0.8544	High Similarity	NPC470997
0.8537	High Similarity	NPC476857
0.8537	High Similarity	NPC476856
0.8537	High Similarity	NPC276551
0.8537	High Similarity	NPC476858
0.8528	High Similarity	NPC472771
0.8528	High Similarity	NPC470792
0.8528	High Similarity	NPC197596
0.8519	High Similarity	NPC475226
0.8512	High Similarity	NPC469576
0.8509	High Similarity	NPC204663
0.8503	High Similarity	NPC159232
0.85	High Similarity	NPC237259
0.85	High Similarity	NPC34421
0.85	High Similarity	NPC98206
0.8494	Intermediate Similarity	NPC160651
0.8485	Intermediate Similarity	NPC478178
0.8485	Intermediate Similarity	NPC470875
0.8485	Intermediate Similarity	NPC149945
0.8481	Intermediate Similarity	NPC234494
0.8476	Intermediate Similarity	NPC472139
0.8476	Intermediate Similarity	NPC469338
0.8476	Intermediate Similarity	NPC292389
0.8471	Intermediate Similarity	NPC471174
0.8466	Intermediate Similarity	NPC477402
0.8466	Intermediate Similarity	NPC470789
0.8462	Intermediate Similarity	NPC469633
0.8462	Intermediate Similarity	NPC34056
0.8457	Intermediate Similarity	NPC195131
0.8457	Intermediate Similarity	NPC472776
0.8457	Intermediate Similarity	NPC299038
0.8457	Intermediate Similarity	NPC194499
0.8457	Intermediate Similarity	NPC472778
0.8457	Intermediate Similarity	NPC472777
0.8457	Intermediate Similarity	NPC88007
0.8457	Intermediate Similarity	NPC195954
0.8438	Intermediate Similarity	NPC75906
0.8434	Intermediate Similarity	NPC478179
0.8434	Intermediate Similarity	NPC476224
0.8434	Intermediate Similarity	NPC476853
0.8434	Intermediate Similarity	NPC472282
0.8424	Intermediate Similarity	NPC469849
0.8424	Intermediate Similarity	NPC123088
0.8424	Intermediate Similarity	NPC470940
0.8424	Intermediate Similarity	NPC271657
0.8421	Intermediate Similarity	NPC470938
0.8415	Intermediate Similarity	NPC117986
0.8415	Intermediate Similarity	NPC200782
0.8415	Intermediate Similarity	NPC149896
0.8415	Intermediate Similarity	NPC68848
0.8415	Intermediate Similarity	NPC69028
0.8387	Intermediate Similarity	NPC121158
0.8385	Intermediate Similarity	NPC57998
0.8383	Intermediate Similarity	NPC271235
0.8375	Intermediate Similarity	NPC291150
0.8375	Intermediate Similarity	NPC18135
0.8373	Intermediate Similarity	NPC472670
0.8373	Intermediate Similarity	NPC121995
0.8373	Intermediate Similarity	NPC307781
0.8373	Intermediate Similarity	NPC23387
0.8365	Intermediate Similarity	NPC470998
0.8365	Intermediate Similarity	NPC472654
0.8364	Intermediate Similarity	NPC477405
0.8364	Intermediate Similarity	NPC663
0.8364	Intermediate Similarity	NPC285567
0.8364	Intermediate Similarity	NPC224394
0.8364	Intermediate Similarity	NPC234660
0.8364	Intermediate Similarity	NPC51568
0.8364	Intermediate Similarity	NPC283209
0.8354	Intermediate Similarity	NPC216755
0.8354	Intermediate Similarity	NPC25255
0.8354	Intermediate Similarity	NPC302987
0.8344	Intermediate Similarity	NPC472772
0.8344	Intermediate Similarity	NPC469847
0.8344	Intermediate Similarity	NPC187149
0.8333	Intermediate Similarity	NPC469336
0.8323	Intermediate Similarity	NPC472651
0.8323	Intermediate Similarity	NPC308205
0.8323	Intermediate Similarity	NPC322546
0.8323	Intermediate Similarity	NPC182427
0.8323	Intermediate Similarity	NPC29695
0.8313	Intermediate Similarity	NPC476860
0.8313	Intermediate Similarity	NPC196846
0.8313	Intermediate Similarity	NPC5180
0.8303	Intermediate Similarity	NPC193798
0.8303	Intermediate Similarity	NPC5079
0.8303	Intermediate Similarity	NPC18347
0.8303	Intermediate Similarity	NPC18986
0.8303	Intermediate Similarity	NPC6326
0.8303	Intermediate Similarity	NPC329938
0.8293	Intermediate Similarity	NPC84349
0.8293	Intermediate Similarity	NPC475967
0.8293	Intermediate Similarity	NPC477403
0.8282	Intermediate Similarity	NPC469485
0.828	Intermediate Similarity	NPC251865
0.8274	Intermediate Similarity	NPC327922
0.8274	Intermediate Similarity	NPC472652
0.8272	Intermediate Similarity	NPC178932
0.8263	Intermediate Similarity	NPC214600
0.8263	Intermediate Similarity	NPC472141
0.8261	Intermediate Similarity	NPC272590
0.8258	Intermediate Similarity	NPC67003
0.8253	Intermediate Similarity	NPC476197
0.8253	Intermediate Similarity	NPC134254
0.8253	Intermediate Similarity	NPC39986
0.8253	Intermediate Similarity	NPC302369
0.825	Intermediate Similarity	NPC471001
0.8242	Intermediate Similarity	NPC472653
0.8232	Intermediate Similarity	NPC167142
0.8232	Intermediate Similarity	NPC36655
0.8232	Intermediate Similarity	NPC261597
0.8232	Intermediate Similarity	NPC173544
0.8221	Intermediate Similarity	NPC469850
0.8221	Intermediate Similarity	NPC214541
0.8221	Intermediate Similarity	NPC44675
0.8214	Intermediate Similarity	NPC270312
0.821	Intermediate Similarity	NPC469503
0.821	Intermediate Similarity	NPC294511
0.821	Intermediate Similarity	NPC121615
0.8204	Intermediate Similarity	NPC470182
0.8199	Intermediate Similarity	NPC156189
0.8193	Intermediate Similarity	NPC188649
0.8193	Intermediate Similarity	NPC79571
0.8193	Intermediate Similarity	NPC470939
0.8193	Intermediate Similarity	NPC82851
0.8193	Intermediate Similarity	NPC263432
0.8187	Intermediate Similarity	NPC477824
0.8187	Intermediate Similarity	NPC471007
0.8182	Intermediate Similarity	NPC307383
0.8182	Intermediate Similarity	NPC472779
0.8182	Intermediate Similarity	NPC475295
0.8182	Intermediate Similarity	NPC473473
0.8171	Intermediate Similarity	NPC41880
0.8155	Intermediate Similarity	NPC93172
0.8155	Intermediate Similarity	NPC97574
0.8144	Intermediate Similarity	NPC288602
0.8144	Intermediate Similarity	NPC88841
0.814	Intermediate Similarity	NPC262386

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 NPC5741 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	1020
0.2-0.3	2259
0.3-0.4	2700
0.4-0.5	1809
0.5-0.6	829
0.6-0.7	225
0.7-0.8	8
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
0.8221	Intermediate Similarity	NPD5760	Phase 2
0.8221	Intermediate Similarity	NPD5761	Phase 2
0.8011	Intermediate Similarity	NPD8434	Phase 2
0.7931	Intermediate Similarity	NPD6764	Approved
0.7931	Intermediate Similarity	NPD6765	Approved
0.7753	Intermediate Similarity	NPD6785	Approved
0.7753	Intermediate Similarity	NPD6784	Approved
0.75	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4628	Phase 3
0.7216	Intermediate Similarity	NPD8127	Discontinued
0.7186	Intermediate Similarity	NPD7236	Approved
0.7174	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7076	Intermediate Similarity	NPD7239	Suspended
0.7062	Intermediate Similarity	NPD7497	Discontinued
0.7017	Intermediate Similarity	NPD7799	Discontinued
0.6994	Remote Similarity	NPD6599	Discontinued
0.6988	Remote Similarity	NPD5762	Approved
0.6988	Remote Similarity	NPD5763	Approved
0.6978	Remote Similarity	NPD5844	Phase 1
0.6971	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7819	Suspended
0.6949	Remote Similarity	NPD7075	Discontinued
0.6927	Remote Similarity	NPD7199	Phase 2
0.6905	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8404	Phase 2
0.6886	Remote Similarity	NPD6005	Phase 3
0.6886	Remote Similarity	NPD6002	Phase 3
0.6886	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6004	Phase 3
0.6886	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6559	Discontinued
0.6864	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6801	Discontinued
0.6802	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7411	Suspended
0.6758	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6653	Approved
0.6744	Remote Similarity	NPD6799	Approved
0.6743	Remote Similarity	NPD3226	Approved
0.6742	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3817	Phase 2
0.6719	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7028	Phase 2
0.6705	Remote Similarity	NPD4380	Phase 2
0.6704	Remote Similarity	NPD7058	Phase 2
0.6704	Remote Similarity	NPD7057	Phase 3
0.6687	Remote Similarity	NPD6355	Discontinued
0.6686	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5494	Approved
0.6685	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3751	Discontinued
0.6649	Remote Similarity	NPD3818	Discontinued
0.6648	Remote Similarity	NPD5402	Approved
0.6648	Remote Similarity	NPD7458	Discontinued
0.6648	Remote Similarity	NPD1247	Approved
0.663	Remote Similarity	NPD919	Approved
0.6629	Remote Similarity	NPD1934	Approved
0.6629	Remote Similarity	NPD920	Approved
0.6627	Remote Similarity	NPD4140	Approved
0.6614	Remote Similarity	NPD8312	Approved
0.6614	Remote Similarity	NPD8313	Approved
0.6611	Remote Similarity	NPD4966	Approved
0.6611	Remote Similarity	NPD4965	Approved
0.6611	Remote Similarity	NPD4967	Phase 2
0.6597	Remote Similarity	NPD8150	Discontinued
0.6596	Remote Similarity	NPD8368	Discontinued
0.6587	Remote Similarity	NPD5735	Approved
0.6579	Remote Similarity	NPD8407	Phase 2
0.6578	Remote Similarity	NPD7074	Phase 3
0.657	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3750	Approved
0.657	Remote Similarity	NPD4110	Phase 3
0.6564	Remote Similarity	NPD5647	Approved
0.6564	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6166	Phase 2
0.6541	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6234	Discontinued
0.6536	Remote Similarity	NPD37	Approved
0.6534	Remote Similarity	NPD5403	Approved
0.6529	Remote Similarity	NPD6099	Approved
0.6529	Remote Similarity	NPD6100	Approved
0.6528	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7054	Approved
0.6524	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3787	Discontinued
0.6522	Remote Similarity	NPD6232	Discontinued
0.6522	Remote Similarity	NPD7507	Approved
0.6519	Remote Similarity	NPD3882	Suspended
0.6514	Remote Similarity	NPD2533	Approved
0.6514	Remote Similarity	NPD2534	Approved
0.6514	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5401	Approved
0.6514	Remote Similarity	NPD2532	Approved
0.6506	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7319	Approved
0.65	Remote Similarity	NPD2801	Approved
0.6494	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7472	Approved
0.6474	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7033	Discontinued
0.6471	Remote Similarity	NPD2799	Discontinued
0.6471	Remote Similarity	NPD3748	Approved
0.6471	Remote Similarity	NPD7228	Approved
0.6467	Remote Similarity	NPD8032	Phase 2
0.6461	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6190	Approved
0.6436	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD1551	Phase 2
0.6433	Remote Similarity	NPD2796	Approved
0.6429	Remote Similarity	NPD4111	Phase 1
0.6421	Remote Similarity	NPD7251	Discontinued
0.642	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1608	Approved
0.6418	Remote Similarity	NPD3057	Approved
0.6416	Remote Similarity	NPD2800	Approved
0.6409	Remote Similarity	NPD8455	Phase 2
0.6409	Remote Similarity	NPD1465	Phase 2
0.6407	Remote Similarity	NPD3268	Approved
0.6402	Remote Similarity	NPD6362	Approved
0.64	Remote Similarity	NPD4107	Approved
0.6395	Remote Similarity	NPD2346	Discontinued
0.6395	Remote Similarity	NPD1471	Phase 3
0.6393	Remote Similarity	NPD3749	Approved
0.6387	Remote Similarity	NPD7808	Phase 3
0.6386	Remote Similarity	NPD7435	Discontinued
0.6383	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8166	Discontinued
0.6378	Remote Similarity	NPD6959	Discontinued
0.6369	Remote Similarity	NPD6663	Approved
0.6368	Remote Similarity	NPD6797	Phase 2
0.6368	Remote Similarity	NPD7907	Approved
0.6359	Remote Similarity	NPD8435	Approved
0.6359	Remote Similarity	NPD8361	Approved
0.6359	Remote Similarity	NPD8360	Approved
0.6358	Remote Similarity	NPD1549	Phase 2
0.6353	Remote Similarity	NPD6353	Approved
0.6351	Remote Similarity	NPD4665	Approved
0.6344	Remote Similarity	NPD7315	Approved
0.634	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7768	Phase 2
0.6337	Remote Similarity	NPD3533	Approved
0.6337	Remote Similarity	NPD2935	Discontinued
0.6337	Remote Similarity	NPD2972	Approved
0.6335	Remote Similarity	NPD7240	Approved
0.6328	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7999	Approved
0.6322	Remote Similarity	NPD1243	Approved
0.6308	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD230	Phase 1
0.6287	Remote Similarity	NPD4482	Phase 3
0.6287	Remote Similarity	NPD6832	Phase 2
0.6286	Remote Similarity	NPD7003	Approved
0.6286	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD6233	Phase 2
0.6271	Remote Similarity	NPD1511	Approved
0.6269	Remote Similarity	NPD8285	Discontinued
0.6264	Remote Similarity	NPD2424	Discontinued
0.6257	Remote Similarity	NPD6651	Approved
0.6257	Remote Similarity	NPD7229	Phase 3
0.6256	Remote Similarity	NPD2491	Approved
0.625	Remote Similarity	NPD7095	Approved
0.625	Remote Similarity	NPD2354	Approved
0.625	Remote Similarity	NPD3887	Approved
0.6243	Remote Similarity	NPD2438	Suspended
0.6242	Remote Similarity	NPD8651	Approved
0.6242	Remote Similarity	NPD1876	Approved
0.6238	Remote Similarity	NPD7930	Approved
0.6238	Remote Similarity	NPD6778	Approved
0.6238	Remote Similarity	NPD6780	Approved
0.6238	Remote Similarity	NPD6781	Approved
0.6238	Remote Similarity	NPD6776	Approved
0.6238	Remote Similarity	NPD6782	Approved
0.6238	Remote Similarity	NPD6779	Approved
0.6238	Remote Similarity	NPD6777	Approved
0.6235	Remote Similarity	NPD17	Approved
0.6235	Remote Similarity	NPD1778	Approved
0.6228	Remote Similarity	NPD5736	Approved
0.6226	Remote Similarity	NPD7115	Discovery
0.6223	Remote Similarity	NPD3926	Phase 2
0.6221	Remote Similarity	NPD7097	Phase 1
0.622	Remote Similarity	NPD3972	Approved
0.6213	Remote Similarity	NPD2313	Discontinued
0.6213	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD6798	Discontinued
0.6213	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD2163	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