NPASS Compound

Structure

NPC45101 OpenBabel07101718282D 36 40 0 0 1 0 0 0 0 0999 V2000 -2.2971 0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9201 -3.1761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0355 -3.4708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1670 -0.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1317 -0.6396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1775 -1.4553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9466 0.4310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3010 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6157 -0.3121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6790 -0.9959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1375 -0.9702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0330 0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 -0.9757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0576 -0.7687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9606 -1.7134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3010 2.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6830 -2.3369 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7521 -1.9716 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1670 0.5243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4648 -1.7134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1870 -2.4959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3010 0.0243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6945 -1.2029 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5651 0.5243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9578 -1.7882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3010 3.0243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8320 -3.3258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3158 -0.7246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3957 -2.0788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1157 -1.1781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1670 1.5243 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 0.5752 -2.3810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 6 32 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 25 1 0 0 0 0 10 33 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 33 1 0 0 0 0 14 16 1 0 0 0 0 14 27 1 0 0 0 0 15 22 1 0 0 0 0 16 26 1 6 0 0 0 17 26 1 1 0 0 0 17 35 1 0 0 0 0 18 28 2 0 0 0 0 18 36 1 0 0 0 0 19 29 2 0 0 0 0 19 34 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 20 30 1 1 0 0 0 21 24 1 0 0 0 0 21 26 1 6 0 0 0 22 25 1 1 0 0 0 22 34 1 0 0 0 0 23 31 2 0 0 0 0 23 32 1 0 0 0 0 24 36 1 0 0 0 0 25 27 1 1 0 0 0 26 5 1 6 0 0 0 27 12 1 6 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.22
Volume:	496.059
LogP:	3.081
LogD:	1.141
LogS:	-3.575
# Rotatable Bonds:	4
TPSA:	121.5
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.376
Synthetic Accessibility Score:	6.515
Fsp3:	0.667
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:	-5.335
MDCK Permeability:	8.794525638222694e-05
Pgp-inhibitor:	0.783
Pgp-substrate:	0.413
Human Intestinal Absorption (HIA):	0.299
20% Bioavailability (F20%):	0.249
30% Bioavailability (F30%):	0.832

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.261
Plasma Protein Binding (PPB):	70.22168731689453%
Volume Distribution (VD):	1.395
Pgp-substrate:	30.190170288085938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.298
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.468
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.528
CYP3A4-substrate:	0.477

ADMET: Excretion

Clearance (CL):	8.238
Half-life (T1/2):	0.338

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.371
Drug-inuced Liver Injury (DILI):	0.883
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.167
Carcinogencity:	0.27
Eye Corrosion:	0.033
Eye Irritation:	0.026
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC45101

Natural Product ID:	NPC45101
*Common Name:**	WZMQOORLOIIGRA-KFHOXVFPSA-N
IUPAC Name:	n.a.
Synonyms:	Rel-Khayseneganin D
Standard InCHIKey:	WZMQOORLOIIGRA-KFHOXVFPSA-N
Standard InCHI:	InChI=1S/C27H34O9/c1-14-16-7-9-25(4)22(15-8-10-33-13-15)34-19(29)12-27(14,25)35-17-11-18(28)36-24(2,3)21(26(16,17)5)20(30)23(31)32-6/h8,10,13,16-17,20-22,30H,1,7,9,11-12H2,2-6H3/t16-,17-,20+,21-,22-,25-,26-,27-/m0/s1
SMILES:	C=C1[C@@H]2CC[C@@]3(C)[C@H](c4ccoc4)OC(=O)C[C@]13O[C@H]1CC(=O)OC(C)(C)[C@H]([C@H](C(=O)OC)O)[C@@]21C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332192
PubChem CID:	71658779
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
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193039]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23210623]
NPO6774	Khaya senegalensis	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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[515378]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[515378]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[515378]

☑ 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 NPC45101 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	349
0.1-0.2	1344
0.2-0.3	3071
0.3-0.4	5404
0.4-0.5	10178
0.5-0.6	10456
0.6-0.7	9440
0.7-0.8	2010
0.8-0.85	261
0.85-0.9	127
0.9-0.95	56
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC477405
0.9477	High Similarity	NPC477402
0.9423	High Similarity	NPC472775
0.9423	High Similarity	NPC472774
0.9423	High Similarity	NPC472651
0.9392	High Similarity	NPC470941
0.9363	High Similarity	NPC472652
0.9355	High Similarity	NPC472773
0.9342	High Similarity	NPC44675
0.9342	High Similarity	NPC214541
0.9299	High Similarity	NPC476853
0.9295	High Similarity	NPC276551
0.9295	High Similarity	NPC271657
0.929	High Similarity	NPC69028
0.929	High Similarity	NPC200782
0.929	High Similarity	NPC263432
0.929	High Similarity	NPC472771
0.929	High Similarity	NPC82851
0.9286	High Similarity	NPC477403
0.9286	High Similarity	NPC475967
0.9236	High Similarity	NPC470875
0.9231	High Similarity	NPC302369
0.9231	High Similarity	NPC39986
0.9231	High Similarity	NPC134254
0.9231	High Similarity	NPC469338
0.9231	High Similarity	NPC292389
0.9226	High Similarity	NPC472653
0.9226	High Similarity	NPC25255
0.9226	High Similarity	NPC470789
0.9226	High Similarity	NPC335761
0.9221	High Similarity	NPC472772
0.9221	High Similarity	NPC249021
0.9221	High Similarity	NPC261597
0.9221	High Similarity	NPC36655
0.9216	High Similarity	NPC264943
0.9211	High Similarity	NPC44577
0.9182	High Similarity	NPC82602
0.9177	High Similarity	NPC472282
0.9172	High Similarity	NPC476858
0.9172	High Similarity	NPC476856
0.9172	High Similarity	NPC469849
0.9172	High Similarity	NPC123088
0.9172	High Similarity	NPC470940
0.9172	High Similarity	NPC476857
0.9167	High Similarity	NPC193798
0.9167	High Similarity	NPC18347
0.9167	High Similarity	NPC149896
0.9167	High Similarity	NPC211777
0.9167	High Similarity	NPC5079
0.9167	High Similarity	NPC329938
0.9167	High Similarity	NPC207978
0.9161	High Similarity	NPC237155
0.9156	High Similarity	NPC126723
0.9156	High Similarity	NPC469485
0.915	High Similarity	NPC282445
0.9125	High Similarity	NPC169299
0.9125	High Similarity	NPC160818
0.9119	High Similarity	NPC471397
0.9119	High Similarity	NPC271235
0.9114	High Similarity	NPC23387
0.9108	High Similarity	NPC51568
0.9108	High Similarity	NPC198047
0.9108	High Similarity	NPC234660
0.9097	High Similarity	NPC187149
0.9097	High Similarity	NPC173544
0.9085	High Similarity	NPC469503
0.9085	High Similarity	NPC476201
0.9057	High Similarity	NPC173516
0.9057	High Similarity	NPC476850
0.9057	High Similarity	NPC476861
0.9051	High Similarity	NPC476860
0.9051	High Similarity	NPC470182
0.9045	High Similarity	NPC117986
0.9038	High Similarity	NPC262872
0.9	High Similarity	NPC160651
0.8994	High Similarity	NPC93172
0.8994	High Similarity	NPC97574
0.8974	High Similarity	NPC167142
0.8974	High Similarity	NPC299038
0.8974	High Similarity	NPC286722
0.8974	High Similarity	NPC472777
0.8974	High Similarity	NPC472776
0.8974	High Similarity	NPC472778
0.8968	High Similarity	NPC476262
0.8968	High Similarity	NPC281258
0.8968	High Similarity	NPC469336
0.8954	High Similarity	NPC476122
0.8938	High Similarity	NPC100333
0.8933	High Similarity	NPC137295
0.8931	High Similarity	NPC146991
0.8924	High Similarity	NPC96443
0.8924	High Similarity	NPC290400
0.8917	High Similarity	NPC307383
0.8917	High Similarity	NPC475295
0.8917	High Similarity	NPC473473
0.891	High Similarity	NPC263265
0.891	High Similarity	NPC107646
0.891	High Similarity	NPC209364
0.8903	High Similarity	NPC178932
0.8903	High Similarity	NPC57998
0.8889	High Similarity	NPC125182
0.8889	High Similarity	NPC69647
0.8882	High Similarity	NPC250228
0.8882	High Similarity	NPC472766
0.8882	High Similarity	NPC472765
0.8861	High Similarity	NPC305016
0.8861	High Similarity	NPC475381
0.8854	High Similarity	NPC472283
0.8841	High Similarity	NPC262386
0.8839	High Similarity	NPC147168
0.8831	High Similarity	NPC196864
0.8831	High Similarity	NPC477404
0.8827	High Similarity	NPC472659
0.882	High Similarity	NPC472764
0.8816	High Similarity	NPC346
0.8808	High Similarity	NPC476944
0.8805	High Similarity	NPC470939
0.8805	High Similarity	NPC472767
0.8805	High Similarity	NPC188649
0.8797	High Similarity	NPC472779
0.879	High Similarity	NPC60973
0.878	High Similarity	NPC471437
0.878	High Similarity	NPC236004
0.878	High Similarity	NPC94763
0.8774	High Similarity	NPC18135
0.8773	High Similarity	NPC159232
0.8766	High Similarity	NPC472654
0.8766	High Similarity	NPC195325
0.8758	High Similarity	NPC478178
0.8758	High Similarity	NPC255414
0.8758	High Similarity	NPC475779
0.8758	High Similarity	NPC149945
0.8758	High Similarity	NPC472141
0.8758	High Similarity	NPC214600
0.875	High Similarity	NPC472139
0.875	High Similarity	NPC469846
0.875	High Similarity	NPC288602
0.875	High Similarity	NPC88841
0.8726	High Similarity	NPC35000
0.8718	High Similarity	NPC75906
0.8712	High Similarity	NPC470995
0.871	High Similarity	NPC159927
0.871	High Similarity	NPC156189
0.871	High Similarity	NPC469335
0.8684	High Similarity	NPC86935
0.8683	High Similarity	NPC470938
0.8679	High Similarity	NPC475226
0.8675	High Similarity	NPC121158
0.8675	High Similarity	NPC478177
0.8667	High Similarity	NPC471632
0.8662	High Similarity	NPC30222
0.8645	High Similarity	NPC470790
0.8645	High Similarity	NPC470791
0.8642	High Similarity	NPC121995
0.8636	High Similarity	NPC221809
0.8634	High Similarity	NPC663
0.8634	High Similarity	NPC224394
0.8634	High Similarity	NPC165218
0.8634	High Similarity	NPC419
0.8627	High Similarity	NPC41182
0.8627	High Similarity	NPC5676
0.8625	High Similarity	NPC191828
0.8618	High Similarity	NPC476946
0.8618	High Similarity	NPC243577
0.8616	High Similarity	NPC88007
0.8616	High Similarity	NPC194499
0.8616	High Similarity	NPC475066
0.8608	High Similarity	NPC469850
0.8599	High Similarity	NPC268905
0.8599	High Similarity	NPC476940
0.8599	High Similarity	NPC476939
0.8591	High Similarity	NPC310830
0.859	High Similarity	NPC46551
0.8589	High Similarity	NPC473766
0.8589	High Similarity	NPC476224
0.8589	High Similarity	NPC478179
0.8589	High Similarity	NPC473753
0.858	High Similarity	NPC261184
0.8571	High Similarity	NPC470792
0.8571	High Similarity	NPC68848
0.8571	High Similarity	NPC262198
0.8571	High Similarity	NPC6326
0.8571	High Similarity	NPC18986
0.8562	High Similarity	NPC251865
0.8562	High Similarity	NPC472671
0.8562	High Similarity	NPC474611
0.8554	High Similarity	NPC469576
0.8553	High Similarity	NPC204663
0.8545	High Similarity	NPC285227
0.8544	High Similarity	NPC253201
0.8544	High Similarity	NPC302054
0.8543	High Similarity	NPC67003
0.8543	High Similarity	NPC90296
0.8537	High Similarity	NPC327922
0.8537	High Similarity	NPC296558
0.8533	High Similarity	NPC476943
0.8519	High Similarity	NPC476197
0.8509	High Similarity	NPC287559
0.8503	High Similarity	NPC469633
0.85	High Similarity	NPC195131

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 NPC45101 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	982
0.2-0.3	2118
0.3-0.4	2640
0.4-0.5	1884
0.5-0.6	918
0.6-0.7	282
0.7-0.8	28
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8491	Intermediate Similarity	NPD5761	Phase 2
0.8491	Intermediate Similarity	NPD5760	Phase 2
0.8363	Intermediate Similarity	NPD8434	Phase 2
0.7952	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6764	Approved
0.7657	Intermediate Similarity	NPD6765	Approved
0.7605	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7075	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7486	Intermediate Similarity	NPD6784	Approved
0.7486	Intermediate Similarity	NPD6785	Approved
0.7458	Intermediate Similarity	NPD6559	Discontinued
0.7425	Intermediate Similarity	NPD6599	Discontinued
0.7396	Intermediate Similarity	NPD7819	Suspended
0.7337	Intermediate Similarity	NPD6801	Discontinued
0.7293	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8313	Approved
0.7278	Intermediate Similarity	NPD8312	Approved
0.7259	Intermediate Similarity	NPD8404	Phase 2
0.7251	Intermediate Similarity	NPD5402	Approved
0.7229	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5494	Approved
0.7169	Intermediate Similarity	NPD6799	Approved
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7151	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD5403	Approved
0.7126	Intermediate Similarity	NPD919	Approved
0.7126	Intermediate Similarity	NPD5401	Approved
0.7119	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6166	Phase 2
0.7118	Intermediate Similarity	NPD4380	Phase 2
0.7117	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5844	Phase 1
0.7069	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3749	Approved
0.7059	Intermediate Similarity	NPD3226	Approved
0.7045	Intermediate Similarity	NPD8127	Discontinued
0.7039	Intermediate Similarity	NPD3818	Discontinued
0.7024	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2532	Approved
0.7024	Intermediate Similarity	NPD2533	Approved
0.7024	Intermediate Similarity	NPD2534	Approved
0.7012	Intermediate Similarity	NPD2346	Discontinued
0.7011	Intermediate Similarity	NPD3882	Suspended
0.6994	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2799	Discontinued
0.6983	Remote Similarity	NPD7473	Discontinued
0.6982	Remote Similarity	NPD6273	Approved
0.6978	Remote Similarity	NPD7251	Discontinued
0.6977	Remote Similarity	NPD7411	Suspended
0.6961	Remote Similarity	NPD7074	Phase 3
0.6959	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1247	Approved
0.6944	Remote Similarity	NPD7799	Discontinued
0.694	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7808	Phase 3
0.6936	Remote Similarity	NPD1934	Approved
0.6923	Remote Similarity	NPD6797	Phase 2
0.6923	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6355	Discontinued
0.691	Remote Similarity	NPD6232	Discontinued
0.6909	Remote Similarity	NPD1471	Phase 3
0.6909	Remote Similarity	NPD5762	Approved
0.6909	Remote Similarity	NPD5763	Approved
0.6907	Remote Similarity	NPD7435	Discontinued
0.6906	Remote Similarity	NPD7054	Approved
0.6905	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7236	Approved
0.689	Remote Similarity	NPD7033	Discontinued
0.6868	Remote Similarity	NPD7472	Approved
0.6865	Remote Similarity	NPD8407	Phase 2
0.6854	Remote Similarity	NPD6959	Discontinued
0.6851	Remote Similarity	NPD7228	Approved
0.6851	Remote Similarity	NPD3751	Discontinued
0.6848	Remote Similarity	NPD6099	Approved
0.6848	Remote Similarity	NPD6100	Approved
0.6848	Remote Similarity	NPD1551	Phase 2
0.6839	Remote Similarity	NPD37	Approved
0.6826	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4966	Approved
0.6818	Remote Similarity	NPD4967	Phase 2
0.6818	Remote Similarity	NPD4965	Approved
0.6816	Remote Similarity	NPD3787	Discontinued
0.6813	Remote Similarity	NPD6832	Phase 2
0.6802	Remote Similarity	NPD7239	Suspended
0.68	Remote Similarity	NPD8455	Phase 2
0.68	Remote Similarity	NPD1465	Phase 2
0.6796	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD8368	Discontinued
0.6793	Remote Similarity	NPD7685	Pre-registration
0.6778	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3926	Phase 2
0.6766	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1549	Phase 2
0.6763	Remote Similarity	NPD7458	Discontinued
0.676	Remote Similarity	NPD7199	Phase 2
0.6753	Remote Similarity	NPD6778	Approved
0.6753	Remote Similarity	NPD6776	Approved
0.6753	Remote Similarity	NPD6781	Approved
0.6753	Remote Similarity	NPD6780	Approved
0.6753	Remote Similarity	NPD6782	Approved
0.6753	Remote Similarity	NPD6777	Approved
0.6753	Remote Similarity	NPD6779	Approved
0.6747	Remote Similarity	NPD2796	Approved
0.6742	Remote Similarity	NPD6234	Discontinued
0.674	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7698	Approved
0.6735	Remote Similarity	NPD7697	Approved
0.6735	Remote Similarity	NPD7696	Phase 3
0.6728	Remote Similarity	NPD2313	Discontinued
0.6726	Remote Similarity	NPD2800	Approved
0.6726	Remote Similarity	NPD1243	Approved
0.6723	Remote Similarity	NPD7768	Phase 2
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD447	Suspended
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2801	Approved
0.6703	Remote Similarity	NPD7240	Approved
0.6701	Remote Similarity	NPD8320	Phase 1
0.6701	Remote Similarity	NPD8319	Approved
0.67	Remote Similarity	NPD7874	Approved
0.67	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7907	Approved
0.6686	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4111	Phase 1
0.6683	Remote Similarity	NPD4665	Approved
0.6683	Remote Similarity	NPD7701	Phase 2
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7095	Approved
0.6647	Remote Similarity	NPD6190	Approved
0.6647	Remote Similarity	NPD2935	Discontinued
0.6646	Remote Similarity	NPD1608	Approved
0.6632	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7229	Phase 3
0.663	Remote Similarity	NPD5710	Approved
0.663	Remote Similarity	NPD5711	Approved
0.6628	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7097	Phase 1
0.6626	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6798	Discontinued
0.6626	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD7871	Phase 2
0.6616	Remote Similarity	NPD7870	Phase 2
0.6607	Remote Similarity	NPD2344	Approved
0.6599	Remote Similarity	NPD3057	Approved
0.659	Remote Similarity	NPD1512	Approved
0.6588	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3750	Approved
0.6587	Remote Similarity	NPD4308	Phase 3
0.6585	Remote Similarity	NPD6233	Phase 2
0.6584	Remote Similarity	NPD5647	Approved
0.6584	Remote Similarity	NPD7801	Approved
0.6582	Remote Similarity	NPD4107	Approved
0.6568	Remote Similarity	NPD2424	Discontinued
0.6566	Remote Similarity	NPD6653	Approved
0.6566	Remote Similarity	NPD7497	Discontinued
0.6564	Remote Similarity	NPD7700	Phase 2
0.6564	Remote Similarity	NPD7699	Phase 2
0.6557	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8360	Approved
0.6545	Remote Similarity	NPD8435	Approved
0.6545	Remote Similarity	NPD8361	Approved
0.6541	Remote Similarity	NPD9717	Approved
0.6541	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8285	Discontinued
0.6524	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3268	Approved
0.6524	Remote Similarity	NPD3764	Approved
0.6522	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2797	Approved
0.6515	Remote Similarity	NPD3533	Approved
0.6515	Remote Similarity	NPD2972	Approved
0.6513	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD1933	Approved
0.6506	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6535	Approved
0.6495	Remote Similarity	NPD6534	Approved
0.6491	Remote Similarity	NPD4110	Phase 3
0.6491	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7003	Approved
0.6488	Remote Similarity	NPD1510	Phase 2
0.6488	Remote Similarity	NPD3748	Approved
0.6485	Remote Similarity	NPD8151	Discontinued

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