NPASS Compound

Structure

NPC204663 OpenBabel07101718312D 38 42 0 0 1 0 0 0 0 0999 V2000 2.2011 -0.7886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2820 1.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0810 -1.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5684 -1.1153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2432 -0.1993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1315 -0.3419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6606 -4.3664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1536 -1.1785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1284 -1.1785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0278 -2.4168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0278 -0.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2738 -1.2760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8560 0.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6410 0.3216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2263 -0.7886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4378 1.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8524 -0.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6533 -1.5773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0278 -1.4420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5936 -0.4620 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4620 -0.4620 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1836 -2.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1316 1.6058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9982 0.3510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5936 -1.1153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2738 -0.3012 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4620 -1.1153 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6533 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5936 1.4877 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6606 -2.4168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3343 2.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3730 -2.4779 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1836 -3.8790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4297 -0.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4378 0.0254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7955 1.3046 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 5 27 1 0 0 0 0 7 34 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 35 1 0 0 0 0 10 19 1 0 0 0 0 10 22 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 27 1 0 0 0 0 13 23 1 0 0 0 0 14 17 2 0 0 0 0 14 35 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 30 2 0 0 0 0 16 36 1 0 0 0 0 17 25 1 0 0 0 0 18 12 1 6 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 19 28 1 1 0 0 0 20 26 1 0 0 0 0 20 36 1 6 0 0 0 21 28 1 6 0 0 0 21 38 1 0 0 0 0 22 31 2 0 0 0 0 22 34 1 0 0 0 0 23 32 2 0 0 0 0 23 37 1 0 0 0 0 24 28 1 0 0 0 0 24 33 2 0 0 0 0 25 27 1 6 0 0 0 25 37 1 0 0 0 0 27 29 1 6 0 0 0 28 6 1 1 0 0 0 29 13 1 6 0 0 0 29 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.24
Volume:	528.015
LogP:	3.65
LogD:	2.58
LogS:	-5.007
# Rotatable Bonds:	6
TPSA:	118.34
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.417
Synthetic Accessibility Score:	6.281
Fsp3:	0.655
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:	-5.157
MDCK Permeability:	4.648727554013021e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.142
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.333
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.722
Plasma Protein Binding (PPB):	77.0372543334961%
Volume Distribution (VD):	0.789
Pgp-substrate:	20.381454467773438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.356
CYP2C19-substrate:	0.375
CYP2C9-inhibitor:	0.628
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.843
CYP3A4-substrate:	0.71

ADMET: Excretion

Clearance (CL):	9.184
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.445
Drug-inuced Liver Injury (DILI):	0.709
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.987
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.242
Carcinogencity:	0.667
Eye Corrosion:	0.004
Eye Irritation:	0.02
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC204663

Natural Product ID:	NPC204663
*Common Name:**	Cipatrijugin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CABATAPDJFTPNH-AVUMIFSASA-N
Standard InCHI:	InChI=1S/C29H36O9/c1-15-18-12-27(5)25(17-8-9-35-14-17)37-23(32)13-29(15,27)38-21-11-20(36-16(2)30)26(3,4)19(10-22(31)34-7)28(21,6)24(18)33/h8-9,14,18-21,25H,1,10-13H2,2-7H3/t18-,19-,20+,21-,25-,27-,28+,29-/m0/s1
SMILES:	C=C1[C@@H]2C[C@@]3(C)[C@H](c4ccoc4)OC(=O)C[C@]13O[C@H]1C[C@H](C(C)(C)[C@H](CC(=O)OC)[C@@]1(C)C2=O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400865
PubChem CID:	23626010
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17655260]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[19296669]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	Longlin County of Guangxi Province, China	2012-JUL	PMID[25970729]
NPO4584	Cipadessa cinerascens	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[528932]
NPT111	Cell Line	K562	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[528932]

☑ 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 NPC204663 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	424
0.1-0.2	1563
0.2-0.3	3322
0.3-0.4	6453
0.4-0.5	11622
0.5-0.6	9678
0.6-0.7	8366
0.7-0.8	919
0.8-0.85	275
0.85-0.9	58
0.9-0.95	11
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC195131
0.9735	High Similarity	NPC6326
0.9735	High Similarity	NPC472767
0.9545	High Similarity	NPC149945
0.9484	High Similarity	NPC476224
0.9484	High Similarity	NPC472764
0.9423	High Similarity	NPC472766
0.9423	High Similarity	NPC472765
0.9267	High Similarity	NPC156189
0.9167	High Similarity	NPC165218
0.9167	High Similarity	NPC472669
0.9156	High Similarity	NPC472772
0.9156	High Similarity	NPC167142
0.9103	High Similarity	NPC471166
0.9103	High Similarity	NPC471167
0.9103	High Similarity	NPC472668
0.9073	High Similarity	NPC470791
0.9073	High Similarity	NPC470790
0.9067	High Similarity	NPC470941
0.9045	High Similarity	NPC471168
0.9013	High Similarity	NPC196864
0.9013	High Similarity	NPC159927
0.9013	High Similarity	NPC469335
0.9013	High Similarity	NPC477404
0.8981	High Similarity	NPC472771
0.8981	High Similarity	NPC197596
0.8974	High Similarity	NPC474932
0.8947	High Similarity	NPC329180
0.8931	High Similarity	NPC478178
0.8924	High Similarity	NPC472773
0.8903	High Similarity	NPC469850
0.8889	High Similarity	NPC476122
0.8854	High Similarity	NPC237155
0.8841	High Similarity	NPC478177
0.8834	High Similarity	NPC471632
0.882	High Similarity	NPC327922
0.8816	High Similarity	NPC221809
0.8812	High Similarity	NPC214600
0.8805	High Similarity	NPC224394
0.8805	High Similarity	NPC663
0.8782	High Similarity	NPC264943
0.8782	High Similarity	NPC471175
0.8782	High Similarity	NPC469336
0.8774	High Similarity	NPC476201
0.8773	High Similarity	NPC469848
0.8758	High Similarity	NPC478179
0.8758	High Similarity	NPC472775
0.8758	High Similarity	NPC472774
0.8742	High Similarity	NPC470939
0.8726	High Similarity	NPC471169
0.8726	High Similarity	NPC175964
0.872	High Similarity	NPC94763
0.872	High Similarity	NPC471437
0.872	High Similarity	NPC236004
0.8718	High Similarity	NPC178932
0.8718	High Similarity	NPC282445
0.8712	High Similarity	NPC285227
0.871	High Similarity	NPC116717
0.871	High Similarity	NPC18135
0.8701	High Similarity	NPC472654
0.8688	High Similarity	NPC476197
0.8679	High Similarity	NPC191828
0.8675	High Similarity	NPC223415
0.8671	High Similarity	NPC249021
0.8671	High Similarity	NPC472283
0.8662	High Similarity	NPC476262
0.8654	High Similarity	NPC84063
0.8654	High Similarity	NPC469503
0.8654	High Similarity	NPC29695
0.8654	High Similarity	NPC182427
0.8654	High Similarity	NPC75906
0.865	High Similarity	NPC472659
0.8642	High Similarity	NPC476853
0.8627	High Similarity	NPC262198
0.8616	High Similarity	NPC477403
0.8608	High Similarity	NPC263265
0.8608	High Similarity	NPC126723
0.8598	High Similarity	NPC159232
0.8571	High Similarity	NPC292389
0.8571	High Similarity	NPC469338
0.8571	High Similarity	NPC477405
0.8571	High Similarity	NPC419
0.8562	High Similarity	NPC470789
0.8562	High Similarity	NPC305016
0.8562	High Similarity	NPC25255
0.8562	High Similarity	NPC477402
0.8553	High Similarity	NPC45101
0.8553	High Similarity	NPC469847
0.8553	High Similarity	NPC286722
0.8543	High Similarity	NPC20500
0.8528	High Similarity	NPC173516
0.8528	High Similarity	NPC476861
0.8528	High Similarity	NPC476850
0.8519	High Similarity	NPC476858
0.8519	High Similarity	NPC476857
0.8519	High Similarity	NPC469849
0.8519	High Similarity	NPC476856
0.8519	High Similarity	NPC276551
0.8519	High Similarity	NPC476860
0.8519	High Similarity	NPC470940
0.8519	High Similarity	NPC123088
0.8509	High Similarity	NPC5741
0.8509	High Similarity	NPC329938
0.8509	High Similarity	NPC193798
0.8509	High Similarity	NPC82851
0.8509	High Similarity	NPC69028
0.8506	High Similarity	NPC471292
0.85	High Similarity	NPC473473
0.85	High Similarity	NPC475226
0.85	High Similarity	NPC475295
0.8497	Intermediate Similarity	NPC238843
0.8497	Intermediate Similarity	NPC199044
0.8497	Intermediate Similarity	NPC142113
0.8494	Intermediate Similarity	NPC469576
0.8491	Intermediate Similarity	NPC209364
0.8491	Intermediate Similarity	NPC107646
0.8491	Intermediate Similarity	NPC60973
0.8481	Intermediate Similarity	NPC57998
0.8476	Intermediate Similarity	NPC471397
0.8476	Intermediate Similarity	NPC160651
0.8471	Intermediate Similarity	NPC291150
0.8467	Intermediate Similarity	NPC476943
0.8466	Intermediate Similarity	NPC23387
0.8466	Intermediate Similarity	NPC470875
0.8462	Intermediate Similarity	NPC195325
0.8457	Intermediate Similarity	NPC469846
0.8447	Intermediate Similarity	NPC475381
0.8443	Intermediate Similarity	NPC167340
0.8443	Intermediate Similarity	NPC469633
0.8442	Intermediate Similarity	NPC34056
0.8438	Intermediate Similarity	NPC472776
0.8438	Intermediate Similarity	NPC299038
0.8438	Intermediate Similarity	NPC472778
0.8438	Intermediate Similarity	NPC475066
0.8438	Intermediate Similarity	NPC472777
0.8438	Intermediate Similarity	NPC197137
0.8438	Intermediate Similarity	NPC261597
0.8438	Intermediate Similarity	NPC36655
0.8438	Intermediate Similarity	NPC470118
0.8431	Intermediate Similarity	NPC470741
0.8431	Intermediate Similarity	NPC80635
0.8428	Intermediate Similarity	NPC214541
0.8428	Intermediate Similarity	NPC44675
0.8428	Intermediate Similarity	NPC92979
0.8418	Intermediate Similarity	NPC322546
0.8418	Intermediate Similarity	NPC308205
0.8415	Intermediate Similarity	NPC472282
0.8415	Intermediate Similarity	NPC472651
0.8415	Intermediate Similarity	NPC473753
0.8415	Intermediate Similarity	NPC473766
0.8408	Intermediate Similarity	NPC5180
0.8402	Intermediate Similarity	NPC470938
0.84	Intermediate Similarity	NPC310830
0.8397	Intermediate Similarity	NPC19747
0.8395	Intermediate Similarity	NPC200782
0.8395	Intermediate Similarity	NPC263432
0.8387	Intermediate Similarity	NPC62799
0.8387	Intermediate Similarity	NPC346
0.8385	Intermediate Similarity	NPC475967
0.8385	Intermediate Similarity	NPC472779
0.8383	Intermediate Similarity	NPC477824
0.8377	Intermediate Similarity	NPC251865
0.8377	Intermediate Similarity	NPC84479
0.8375	Intermediate Similarity	NPC469485
0.8375	Intermediate Similarity	NPC41880
0.8366	Intermediate Similarity	NPC121158
0.8365	Intermediate Similarity	NPC30222
0.8364	Intermediate Similarity	NPC472673
0.8364	Intermediate Similarity	NPC472652
0.8363	Intermediate Similarity	NPC105395
0.8363	Intermediate Similarity	NPC247563
0.8363	Intermediate Similarity	NPC242068
0.8355	Intermediate Similarity	NPC56197
0.8354	Intermediate Similarity	NPC272590
0.8344	Intermediate Similarity	NPC211625
0.8344	Intermediate Similarity	NPC220094
0.8344	Intermediate Similarity	NPC471001
0.8344	Intermediate Similarity	NPC134254
0.8344	Intermediate Similarity	NPC302369
0.8344	Intermediate Similarity	NPC39986
0.8333	Intermediate Similarity	NPC250228
0.8333	Intermediate Similarity	NPC471174
0.8333	Intermediate Similarity	NPC472653
0.8333	Intermediate Similarity	NPC216755
0.8333	Intermediate Similarity	NPC224418
0.8333	Intermediate Similarity	NPC255414
0.8323	Intermediate Similarity	NPC173544
0.8323	Intermediate Similarity	NPC187149
0.8313	Intermediate Similarity	NPC35000
0.8312	Intermediate Similarity	NPC267632
0.8302	Intermediate Similarity	NPC476939
0.8302	Intermediate Similarity	NPC476940
0.8293	Intermediate Similarity	NPC470182
0.8291	Intermediate Similarity	NPC46551
0.8291	Intermediate Similarity	NPC476936
0.8284	Intermediate Similarity	NPC470181
0.8282	Intermediate Similarity	NPC5079
0.8282	Intermediate Similarity	NPC188649
0.8278	Intermediate Similarity	NPC470742
0.8272	Intermediate Similarity	NPC474611

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 NPC204663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	1026
0.2-0.3	2284
0.3-0.4	2736
0.4-0.5	1802
0.5-0.6	751
0.6-0.7	196
0.7-0.8	9
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
0.8662	High Similarity	NPD5760	Phase 2
0.8662	High Similarity	NPD5761	Phase 2
0.811	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD8434	Phase 2
0.76	Intermediate Similarity	NPD6764	Approved
0.76	Intermediate Similarity	NPD6765	Approved
0.75	Intermediate Similarity	NPD920	Approved
0.743	Intermediate Similarity	NPD6784	Approved
0.743	Intermediate Similarity	NPD6785	Approved
0.7378	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7819	Suspended
0.7256	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5494	Approved
0.7118	Intermediate Similarity	NPD7411	Suspended
0.7093	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1247	Approved
0.7073	Intermediate Similarity	NPD1243	Approved
0.7069	Intermediate Similarity	NPD919	Approved
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.7035	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3749	Approved
0.7011	Intermediate Similarity	NPD7075	Discontinued
0.6994	Remote Similarity	NPD2796	Approved
0.6983	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6599	Discontinued
0.6957	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD6273	Approved
0.6923	Remote Similarity	NPD6559	Discontinued
0.6901	Remote Similarity	NPD3226	Approved
0.6872	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2533	Approved
0.6864	Remote Similarity	NPD2534	Approved
0.6864	Remote Similarity	NPD2532	Approved
0.6855	Remote Similarity	NPD6832	Phase 2
0.6848	Remote Similarity	NPD6002	Phase 3
0.6848	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6005	Phase 3
0.6848	Remote Similarity	NPD6004	Phase 3
0.6848	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7236	Approved
0.6826	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4628	Phase 3
0.6805	Remote Similarity	NPD6799	Approved
0.6796	Remote Similarity	NPD7799	Discontinued
0.6782	Remote Similarity	NPD6801	Discontinued
0.6766	Remote Similarity	NPD2800	Approved
0.6765	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6808	Phase 2
0.6744	Remote Similarity	NPD7239	Suspended
0.6743	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD3748	Approved
0.6722	Remote Similarity	NPD3926	Phase 2
0.6707	Remote Similarity	NPD1549	Phase 2
0.6707	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3817	Phase 2
0.6704	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4380	Phase 2
0.6649	Remote Similarity	NPD7685	Pre-registration
0.6648	Remote Similarity	NPD7473	Discontinued
0.6647	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2346	Discontinued
0.6629	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD8032	Phase 2
0.6618	Remote Similarity	NPD8404	Phase 2
0.6612	Remote Similarity	NPD3818	Discontinued
0.6611	Remote Similarity	NPD7199	Phase 2
0.6611	Remote Similarity	NPD6959	Discontinued
0.661	Remote Similarity	NPD5402	Approved
0.6599	Remote Similarity	NPD7497	Discontinued
0.6597	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1934	Approved
0.659	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6099	Approved
0.6587	Remote Similarity	NPD6100	Approved
0.6587	Remote Similarity	NPD1551	Phase 2
0.6576	Remote Similarity	NPD5844	Phase 1
0.6573	Remote Similarity	NPD7768	Phase 2
0.6573	Remote Similarity	NPD3882	Suspended
0.657	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3266	Approved
0.6562	Remote Similarity	NPD3267	Approved
0.6548	Remote Similarity	NPD2344	Approved
0.6545	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3750	Approved
0.6529	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7033	Discontinued
0.6522	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2403	Approved
0.65	Remote Similarity	NPD1876	Approved
0.6497	Remote Similarity	NPD17	Approved
0.6494	Remote Similarity	NPD5403	Approved
0.6489	Remote Similarity	NPD8313	Approved
0.6489	Remote Similarity	NPD8312	Approved
0.6488	Remote Similarity	NPD2935	Discontinued
0.6486	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5710	Approved
0.6484	Remote Similarity	NPD5711	Approved
0.6484	Remote Similarity	NPD7229	Phase 3
0.6484	Remote Similarity	NPD6232	Discontinued
0.648	Remote Similarity	NPD8285	Discontinued
0.6474	Remote Similarity	NPD5401	Approved
0.6463	Remote Similarity	NPD2313	Discontinued
0.6463	Remote Similarity	NPD3268	Approved
0.6452	Remote Similarity	NPD7074	Phase 3
0.645	Remote Similarity	NPD5763	Approved
0.645	Remote Similarity	NPD5762	Approved
0.6429	Remote Similarity	NPD1510	Phase 2
0.6425	Remote Similarity	NPD5353	Approved
0.642	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1019	Discontinued
0.642	Remote Similarity	NPD5647	Approved
0.6417	Remote Similarity	NPD5953	Discontinued
0.6417	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6166	Phase 2
0.6407	Remote Similarity	NPD6651	Approved
0.6398	Remote Similarity	NPD7054	Approved
0.6398	Remote Similarity	NPD7286	Phase 2
0.6395	Remote Similarity	NPD2309	Approved
0.6389	Remote Similarity	NPD7057	Phase 3
0.6389	Remote Similarity	NPD4966	Approved
0.6389	Remote Similarity	NPD7058	Phase 2
0.6389	Remote Similarity	NPD4965	Approved
0.6389	Remote Similarity	NPD4967	Phase 2
0.6386	Remote Similarity	NPD1240	Approved
0.6386	Remote Similarity	NPD4140	Approved
0.6375	Remote Similarity	NPD3972	Approved
0.6375	Remote Similarity	NPD1608	Approved
0.6369	Remote Similarity	NPD2801	Approved
0.6364	Remote Similarity	NPD7472	Approved
0.6349	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5889	Approved
0.6348	Remote Similarity	NPD5890	Approved
0.6347	Remote Similarity	NPD6355	Discontinued
0.6343	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5327	Phase 3
0.6328	Remote Similarity	NPD7458	Discontinued
0.6319	Remote Similarity	NPD6234	Discontinued
0.6313	Remote Similarity	NPD37	Approved
0.6313	Remote Similarity	NPD6280	Approved
0.6313	Remote Similarity	NPD6279	Approved
0.631	Remote Similarity	NPD6653	Approved
0.631	Remote Similarity	NPD1607	Approved
0.6304	Remote Similarity	NPD7315	Approved
0.6302	Remote Similarity	NPD8150	Discontinued
0.6301	Remote Similarity	NPD3887	Approved
0.6296	Remote Similarity	NPD7251	Discontinued
0.6292	Remote Similarity	NPD7028	Phase 2
0.6292	Remote Similarity	NPD6585	Discontinued
0.6287	Remote Similarity	NPD4307	Phase 2
0.6281	Remote Similarity	NPD4107	Approved
0.6278	Remote Similarity	NPD1465	Phase 2
0.6273	Remote Similarity	NPD9717	Approved
0.6269	Remote Similarity	NPD7435	Discontinued
0.6265	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD3764	Approved
0.6263	Remote Similarity	NPD7808	Phase 3
0.6258	Remote Similarity	NPD6362	Approved
0.6258	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD3751	Discontinued
0.6257	Remote Similarity	NPD7228	Approved
0.625	Remote Similarity	NPD1933	Approved
0.625	Remote Similarity	NPD447	Suspended
0.625	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD6797	Phase 2
0.6243	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4287	Approved
0.6229	Remote Similarity	NPD1511	Approved
0.6228	Remote Similarity	NPD6663	Approved
0.6226	Remote Similarity	NPD5585	Approved
0.622	Remote Similarity	NPD2798	Approved
0.6216	Remote Similarity	NPD3787	Discontinued
0.6213	Remote Similarity	NPD6353	Approved
0.6199	Remote Similarity	NPD2438	Suspended
0.6198	Remote Similarity	NPD8407	Phase 2
0.619	Remote Similarity	NPD2979	Phase 3
0.619	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD2654	Approved
0.6183	Remote Similarity	NPD5242	Approved
0.6179	Remote Similarity	NPD7907	Approved
0.6178	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7097	Phase 1
0.6169	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD4482	Phase 3
0.6168	Remote Similarity	NPD1296	Phase 2
0.6167	Remote Similarity	NPD6385	Approved
0.6167	Remote Similarity	NPD6386	Approved
0.6159	Remote Similarity	NPD2797	Approved
0.6159	Remote Similarity	NPD1203	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