NPASS Compound

Structure

NPC196846 OpenBabel07101718292D 30 35 0 0 1 0 0 0 0 0999 V2000 3.2170 -1.4913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9962 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5633 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2386 -1.8054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6819 1.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8733 1.2019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7042 -1.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7557 -2.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3975 -0.5774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5185 -1.9948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4084 -0.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3921 -0.4728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7340 1.0053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9517 -0.2198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9908 0.3362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0127 0.5441 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7042 0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.8131 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8143 -2.3040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4285 0.3260 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3986 -0.6735 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6357 0.5070 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3399 -1.0108 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4084 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6357 -1.3201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0515 -2.9506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4132 1.4819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6000 0.5053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3884 0.6065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 17 2 0 0 0 0 7 11 1 0 0 0 0 7 18 1 0 0 0 0 8 10 2 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 29 1 0 0 0 0 13 15 2 0 0 0 0 13 29 1 0 0 0 0 14 23 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 16 24 1 6 0 0 0 17 24 1 0 0 0 0 17 25 1 0 0 0 0 18 25 1 1 0 0 0 18 26 1 0 0 0 0 19 26 1 0 0 0 0 19 27 2 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 30 1 6 0 0 0 21 23 1 1 0 0 0 21 26 1 0 0 0 0 22 25 1 6 0 0 0 22 28 1 0 0 0 0 23 1 1 1 0 0 0 24 2 1 6 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.23
Volume:	428.892
LogP:	3.296
LogD:	3.0
LogS:	-4.763
# Rotatable Bonds:	1
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	5.36
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.884
MDCK Permeability:	2.9032755264779553e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.717
30% Bioavailability (F30%):	0.416

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.964
Plasma Protein Binding (PPB):	96.45763397216797%
Volume Distribution (VD):	2.369
Pgp-substrate:	4.780052185058594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.287
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.606
CYP2C9-inhibitor:	0.236
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.133
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.914
CYP3A4-substrate:	0.518

ADMET: Excretion

Clearance (CL):	11.086
Half-life (T1/2):	0.323

ADMET: Toxicity

hERG Blockers:	0.778
Human Hepatotoxicity (H-HT):	0.486
Drug-inuced Liver Injury (DILI):	0.081
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.988
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.618
Carcinogencity:	0.867
Eye Corrosion:	0.008
Eye Irritation:	0.061
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC196846

Natural Product ID:	NPC196846
*Common Name:**	Ceramicines B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AEPJQKVEJDKGIZ-RTBHCFDSSA-N
Standard InCHI:	InChI=1S/C26H32O4/c1-23-10-8-19(27)26(4)18-7-11-24(2)16(15-9-12-29-13-15)5-6-17(24)25(18,3)22(28)20(21(23)26)30-14-23/h6,8-10,12-13,16,18,20-22,28H,5,7,11,14H2,1-4H3/t16-,18-,20+,21-,22+,23-,24-,25-,26-/m0/s1
SMILES:	O[C@@H]1[C@@H]2OC[C@]3([C@H]2[C@]([C@@H]2[C@]1(C)C1=CC[C@H]([C@]1(C)CC2)c1cocc1)(C)C(=O)C=C3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515208
PubChem CID:	42609928
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
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19081726]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21428417]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[21428417]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23395661]
NPO5587	Chisocheton ceramicus	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	3
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	15.0	ug.mL-1	PMID[473580]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.23	ug.mL-1	PMID[473580]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	8.8	n.a.	PMID[473581]
NPT27	Others	Unspecified		CC50	=	15900.0	nM	PMID[473581]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1800.0	nM	PMID[473581]

☑ 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 NPC196846 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	351
0.1-0.2	1256
0.2-0.3	2809
0.3-0.4	5454
0.4-0.5	10881
0.5-0.6	10710
0.6-0.7	9809
0.7-0.8	1105
0.8-0.85	207
0.85-0.9	93
0.9-0.95	17
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC296807
0.9726	High Similarity	NPC155939
0.9726	High Similarity	NPC141538
0.9724	High Similarity	NPC470996
0.958	High Similarity	NPC470999
0.9517	High Similarity	NPC234494
0.9514	High Similarity	NPC302987
0.9448	High Similarity	NPC471007
0.9384	High Similarity	NPC471001
0.9384	High Similarity	NPC470998
0.9329	High Similarity	NPC92979
0.9324	High Similarity	NPC33938
0.932	High Similarity	NPC470997
0.9257	High Similarity	NPC471000
0.9247	High Similarity	NPC471174
0.9241	High Similarity	NPC185456
0.9205	High Similarity	NPC197137
0.915	High Similarity	NPC470792
0.9133	High Similarity	NPC34421
0.9133	High Similarity	NPC237259
0.9133	High Similarity	NPC98206
0.9116	High Similarity	NPC216755
0.9067	High Similarity	NPC471002
0.902	High Similarity	NPC84349
0.8954	High Similarity	NPC470118
0.894	High Similarity	NPC246164
0.8897	High Similarity	NPC56197
0.8896	High Similarity	NPC472671
0.8896	High Similarity	NPC475226
0.8882	High Similarity	NPC253201
0.8882	High Similarity	NPC302054
0.8874	High Similarity	NPC272590
0.8874	High Similarity	NPC116717
0.8874	High Similarity	NPC291150
0.8867	High Similarity	NPC472654
0.8851	High Similarity	NPC5676
0.8831	High Similarity	NPC470119
0.8831	High Similarity	NPC214495
0.8831	High Similarity	NPC475066
0.8816	High Similarity	NPC472672
0.8816	High Similarity	NPC121615
0.8816	High Similarity	NPC294511
0.8811	High Similarity	NPC476947
0.8808	High Similarity	NPC5180
0.8803	High Similarity	NPC218838
0.8784	High Similarity	NPC199044
0.8784	High Similarity	NPC238843
0.8782	High Similarity	NPC471003
0.8767	High Similarity	NPC67003
0.8742	High Similarity	NPC125182
0.8742	High Similarity	NPC69647
0.8716	High Similarity	NPC243577
0.871	High Similarity	NPC469847
0.871	High Similarity	NPC472776
0.871	High Similarity	NPC472777
0.871	High Similarity	NPC472778
0.8693	High Similarity	NPC268905
0.8688	High Similarity	NPC470995
0.8671	High Similarity	NPC471006
0.8667	High Similarity	NPC471292
0.8658	High Similarity	NPC251865
0.8654	High Similarity	NPC475967
0.8649	High Similarity	NPC52412
0.8634	High Similarity	NPC285227
0.8618	High Similarity	NPC195325
0.8616	High Similarity	NPC307781
0.8616	High Similarity	NPC472670
0.8609	High Similarity	NPC255414
0.8608	High Similarity	NPC283209
0.86	High Similarity	NPC34056
0.8599	High Similarity	NPC470789
0.8591	High Similarity	NPC476946
0.859	High Similarity	NPC194499
0.859	High Similarity	NPC299038
0.8581	High Similarity	NPC214541
0.8581	High Similarity	NPC44675
0.8571	High Similarity	NPC29695
0.8571	High Similarity	NPC308205
0.8571	High Similarity	NPC182427
0.8571	High Similarity	NPC322546
0.8562	High Similarity	NPC228842
0.8562	High Similarity	NPC310572
0.8553	High Similarity	NPC276551
0.8544	High Similarity	NPC69028
0.8535	High Similarity	NPC307383
0.8531	High Similarity	NPC61788
0.8523	High Similarity	NPC121158
0.8519	High Similarity	NPC475641
0.8519	High Similarity	NPC475237
0.8516	High Similarity	NPC178932
0.8514	High Similarity	NPC90296
0.8509	High Similarity	NPC472673
0.85	High Similarity	NPC472141
0.85	High Similarity	NPC470875
0.8493	Intermediate Similarity	NPC46896
0.8491	Intermediate Similarity	NPC224394
0.8491	Intermediate Similarity	NPC469338
0.8491	Intermediate Similarity	NPC472773
0.8491	Intermediate Similarity	NPC663
0.8491	Intermediate Similarity	NPC292389
0.8491	Intermediate Similarity	NPC285567
0.8487	Intermediate Similarity	NPC71821
0.8471	Intermediate Similarity	NPC88007
0.8471	Intermediate Similarity	NPC261597
0.8471	Intermediate Similarity	NPC7059
0.8462	Intermediate Similarity	NPC264943
0.8462	Intermediate Similarity	NPC35000
0.8462	Intermediate Similarity	NPC469336
0.8457	Intermediate Similarity	NPC118086
0.8456	Intermediate Similarity	NPC205765
0.8452	Intermediate Similarity	NPC469503
0.8447	Intermediate Similarity	NPC472651
0.8446	Intermediate Similarity	NPC90953
0.8442	Intermediate Similarity	NPC156189
0.8438	Intermediate Similarity	NPC469849
0.8438	Intermediate Similarity	NPC470940
0.8435	Intermediate Similarity	NPC4764
0.8431	Intermediate Similarity	NPC93666
0.8428	Intermediate Similarity	NPC472771
0.8428	Intermediate Similarity	NPC68848
0.8428	Intermediate Similarity	NPC5079
0.8428	Intermediate Similarity	NPC18986
0.8428	Intermediate Similarity	NPC79571
0.8428	Intermediate Similarity	NPC200782
0.8425	Intermediate Similarity	NPC158525
0.8415	Intermediate Similarity	NPC236004
0.8415	Intermediate Similarity	NPC94763
0.84	Intermediate Similarity	NPC263337
0.8397	Intermediate Similarity	NPC57998
0.8397	Intermediate Similarity	NPC30222
0.8395	Intermediate Similarity	NPC271235
0.8395	Intermediate Similarity	NPC471397
0.8395	Intermediate Similarity	NPC472652
0.8393	Intermediate Similarity	NPC247563
0.8393	Intermediate Similarity	NPC242068
0.8387	Intermediate Similarity	NPC18135
0.8378	Intermediate Similarity	NPC471996
0.8375	Intermediate Similarity	NPC472139
0.8375	Intermediate Similarity	NPC234660
0.8375	Intermediate Similarity	NPC165218
0.8375	Intermediate Similarity	NPC477405
0.8375	Intermediate Similarity	NPC51568
0.8366	Intermediate Similarity	NPC250228
0.8365	Intermediate Similarity	NPC8389
0.8365	Intermediate Similarity	NPC287559
0.8365	Intermediate Similarity	NPC477402
0.8354	Intermediate Similarity	NPC187149
0.8354	Intermediate Similarity	NPC304692
0.8354	Intermediate Similarity	NPC36655
0.8354	Intermediate Similarity	NPC195954
0.8344	Intermediate Similarity	NPC82602
0.8333	Intermediate Similarity	NPC478179
0.8333	Intermediate Similarity	NPC472774
0.8333	Intermediate Similarity	NPC476850
0.8333	Intermediate Similarity	NPC476861
0.8333	Intermediate Similarity	NPC173516
0.8333	Intermediate Similarity	NPC472775
0.8333	Intermediate Similarity	NPC100333
0.8333	Intermediate Similarity	NPC75906
0.8323	Intermediate Similarity	NPC470938
0.8323	Intermediate Similarity	NPC212257
0.8323	Intermediate Similarity	NPC470182
0.8323	Intermediate Similarity	NPC123088
0.8313	Intermediate Similarity	NPC82851
0.8313	Intermediate Similarity	NPC207978
0.8313	Intermediate Similarity	NPC263432
0.8313	Intermediate Similarity	NPC478177
0.8313	Intermediate Similarity	NPC329938
0.8313	Intermediate Similarity	NPC5741
0.8313	Intermediate Similarity	NPC211777
0.8313	Intermediate Similarity	NPC188649
0.8303	Intermediate Similarity	NPC469576
0.8303	Intermediate Similarity	NPC471437
0.8302	Intermediate Similarity	NPC472823
0.8301	Intermediate Similarity	NPC346
0.8291	Intermediate Similarity	NPC104736
0.8289	Intermediate Similarity	NPC476944
0.8284	Intermediate Similarity	NPC105395
0.8282	Intermediate Similarity	NPC472766
0.8282	Intermediate Similarity	NPC472765
0.8272	Intermediate Similarity	NPC93172
0.8272	Intermediate Similarity	NPC97574
0.8272	Intermediate Similarity	NPC121995
0.8272	Intermediate Similarity	NPC475779
0.8272	Intermediate Similarity	NPC478178
0.8263	Intermediate Similarity	NPC11062
0.8261	Intermediate Similarity	NPC288602
0.8261	Intermediate Similarity	NPC471168
0.8261	Intermediate Similarity	NPC88841
0.8261	Intermediate Similarity	NPC198047
0.8258	Intermediate Similarity	NPC470790
0.8258	Intermediate Similarity	NPC470791
0.8253	Intermediate Similarity	NPC469633
0.825	Intermediate Similarity	NPC472653
0.825	Intermediate Similarity	NPC335761
0.8239	Intermediate Similarity	NPC472772
0.8239	Intermediate Similarity	NPC45101
0.8235	Intermediate Similarity	NPC56731
0.8228	Intermediate Similarity	NPC25351
0.8228	Intermediate Similarity	NPC281258

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 NPC196846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	866
0.2-0.3	1943
0.3-0.4	2709
0.4-0.5	2023
0.5-0.6	996
0.6-0.7	285
0.7-0.8	13
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
0.7907	Intermediate Similarity	NPD8434	Phase 2
0.7824	Intermediate Similarity	NPD6765	Approved
0.7824	Intermediate Similarity	NPD6764	Approved
0.7644	Intermediate Similarity	NPD6785	Approved
0.7644	Intermediate Similarity	NPD6784	Approved
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7381	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD8127	Discontinued
0.7239	Intermediate Similarity	NPD6273	Approved
0.717	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1471	Phase 3
0.7056	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5494	Approved
0.7022	Intermediate Similarity	NPD6559	Discontinued
0.7006	Intermediate Similarity	NPD7458	Discontinued
0.6975	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6599	Discontinued
0.6964	Remote Similarity	NPD7028	Phase 2
0.6962	Remote Similarity	NPD5735	Approved
0.6959	Remote Similarity	NPD3882	Suspended
0.6957	Remote Similarity	NPD5763	Approved
0.6957	Remote Similarity	NPD5762	Approved
0.6957	Remote Similarity	NPD2344	Approved
0.6951	Remote Similarity	NPD7236	Approved
0.6941	Remote Similarity	NPD7819	Suspended
0.6941	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7075	Discontinued
0.6897	Remote Similarity	NPD7199	Phase 2
0.6893	Remote Similarity	NPD3818	Discontinued
0.6882	Remote Similarity	NPD1934	Approved
0.6869	Remote Similarity	NPD8404	Phase 2
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4380	Phase 2
0.6855	Remote Similarity	NPD6355	Discontinued
0.6854	Remote Similarity	NPD5844	Phase 1
0.6832	Remote Similarity	NPD2799	Discontinued
0.6806	Remote Similarity	NPD3057	Approved
0.6802	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3972	Approved
0.679	Remote Similarity	NPD6099	Approved
0.679	Remote Similarity	NPD2796	Approved
0.679	Remote Similarity	NPD6100	Approved
0.6788	Remote Similarity	NPD2309	Approved
0.6784	Remote Similarity	NPD6801	Discontinued
0.678	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4966	Approved
0.6763	Remote Similarity	NPD4965	Approved
0.6763	Remote Similarity	NPD4967	Phase 2
0.6748	Remote Similarity	NPD2346	Discontinued
0.6746	Remote Similarity	NPD7239	Suspended
0.6744	Remote Similarity	NPD2801	Approved
0.673	Remote Similarity	NPD8032	Phase 2
0.6727	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4110	Phase 3
0.6727	Remote Similarity	NPD8166	Discontinued
0.6727	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD2972	Approved
0.6719	Remote Similarity	NPD3533	Approved
0.6719	Remote Similarity	NPD2491	Approved
0.6711	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1876	Approved
0.6707	Remote Similarity	NPD6799	Approved
0.6707	Remote Similarity	NPD1549	Phase 2
0.6707	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3226	Approved
0.6705	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1247	Approved
0.6704	Remote Similarity	NPD7799	Discontinued
0.6688	Remote Similarity	NPD9494	Approved
0.6687	Remote Similarity	NPD4140	Approved
0.6686	Remote Similarity	NPD6234	Discontinued
0.6686	Remote Similarity	NPD919	Approved
0.6686	Remote Similarity	NPD920	Approved
0.6685	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6166	Phase 2
0.6685	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8312	Approved
0.6667	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD2800	Approved
0.6648	Remote Similarity	NPD7685	Pre-registration
0.6648	Remote Similarity	NPD7473	Discontinued
0.6646	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3448	Approved
0.663	Remote Similarity	NPD7074	Phase 3
0.6629	Remote Similarity	NPD3926	Phase 2
0.6629	Remote Similarity	NPD3749	Approved
0.6627	Remote Similarity	NPD7003	Approved
0.6627	Remote Similarity	NPD3750	Approved
0.6611	Remote Similarity	NPD7228	Approved
0.6611	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3817	Phase 2
0.6608	Remote Similarity	NPD2649	Approved
0.6608	Remote Similarity	NPD2651	Approved
0.6606	Remote Similarity	NPD2424	Discontinued
0.6605	Remote Similarity	NPD6353	Approved
0.6603	Remote Similarity	NPD8651	Approved
0.6598	Remote Similarity	NPD7497	Discontinued
0.659	Remote Similarity	NPD37	Approved
0.6581	Remote Similarity	NPD1608	Approved
0.6578	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7054	Approved
0.6575	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6798	Discontinued
0.6562	Remote Similarity	NPD2313	Discontinued
0.6548	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6004	Phase 3
0.6545	Remote Similarity	NPD6005	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
0.6538	Remote Similarity	NPD5327	Phase 3
0.6538	Remote Similarity	NPD7472	Approved
0.6533	Remote Similarity	NPD5676	Approved
0.6532	Remote Similarity	NPD7411	Suspended
0.6528	Remote Similarity	NPD4107	Approved
0.6524	Remote Similarity	NPD1510	Phase 2
0.6524	Remote Similarity	NPD3748	Approved
0.6519	Remote Similarity	NPD5647	Approved
0.6519	Remote Similarity	NPD3751	Discontinued
0.6519	Remote Similarity	NPD2163	Approved
0.6519	Remote Similarity	NPD2798	Approved
0.6517	Remote Similarity	NPD6959	Discontinued
0.6516	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5402	Approved
0.6509	Remote Similarity	NPD1511	Approved
0.6508	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7095	Approved
0.65	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5403	Approved
0.6491	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7157	Approved
0.6481	Remote Similarity	NPD3620	Phase 2
0.6481	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6232	Discontinued
0.6471	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2532	Approved
0.6471	Remote Similarity	NPD2534	Approved
0.6471	Remote Similarity	NPD2533	Approved
0.6471	Remote Similarity	NPD5401	Approved
0.6471	Remote Similarity	NPD8150	Discontinued
0.6467	Remote Similarity	NPD1241	Discontinued
0.6467	Remote Similarity	NPD7251	Discontinued
0.6467	Remote Similarity	NPD7240	Approved
0.646	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.646	Remote Similarity	NPD3268	Approved
0.646	Remote Similarity	NPD3764	Approved
0.6452	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8407	Phase 2
0.6433	Remote Similarity	NPD1512	Approved
0.6432	Remote Similarity	NPD7808	Phase 3
0.6424	Remote Similarity	NPD7033	Discontinued
0.642	Remote Similarity	NPD5977	Approved
0.642	Remote Similarity	NPD5978	Approved
0.642	Remote Similarity	NPD6663	Approved
0.6413	Remote Similarity	NPD6797	Phase 2
0.641	Remote Similarity	NPD4482	Phase 3
0.6405	Remote Similarity	NPD9092	Discovery
0.6402	Remote Similarity	NPD1607	Approved
0.6402	Remote Similarity	NPD6653	Approved
0.64	Remote Similarity	NPD6279	Approved
0.64	Remote Similarity	NPD6844	Discontinued
0.64	Remote Similarity	NPD6280	Approved
0.6391	Remote Similarity	NPD2354	Approved
0.6391	Remote Similarity	NPD3887	Approved
0.639	Remote Similarity	NPD4111	Phase 1
0.639	Remote Similarity	NPD4665	Approved
0.6389	Remote Similarity	NPD7229	Phase 3
0.6389	Remote Similarity	NPD3787	Discontinued
0.6387	Remote Similarity	NPD2932	Approved
0.6387	Remote Similarity	NPD17	Approved
0.6386	Remote Similarity	NPD1551	Phase 2
0.6384	Remote Similarity	NPD7057	Phase 3
0.6384	Remote Similarity	NPD7058	Phase 2
0.6384	Remote Similarity	NPD7768	Phase 2
0.638	Remote Similarity	NPD1240	Approved
0.638	Remote Similarity	NPD4060	Phase 1
0.6378	Remote Similarity	NPD8368	Discontinued
0.6374	Remote Similarity	NPD4662	Approved
0.6374	Remote Similarity	NPD4661	Approved
0.6369	Remote Similarity	NPD1243	Approved
0.6368	Remote Similarity	NPD2488	Approved
0.6368	Remote Similarity	NPD2490	Approved
0.6364	Remote Similarity	NPD7097	Phase 1
0.6364	Remote Similarity	NPD8455	Phase 2
0.6364	Remote Similarity	NPD1465	Phase 2
0.6358	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD2797	Approved
0.6344	Remote Similarity	NPD4419	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data