NPASS Compound

Structure

NPC146991 OpenBabel07101718242D 37 42 0 0 1 0 0 0 0 0999 V2000 2.5177 0.4845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6785 -1.9382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8392 1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1368 0.9638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8392 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0847 1.1652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3570 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8763 1.6785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9208 -0.3942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0355 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5177 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6785 0.9691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1962 -0.4845 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9072 1.6785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4227 2.5177 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4536 2.5177 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9691 1.6785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6785 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3570 -1.9382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4536 0.8392 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8392 -0.4845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5177 -0.4845 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8392 -0.4845 0.0000 C 0 0 1 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 -4.3608 2.5177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9072 3.3570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9691 3.3570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3570 -2.9072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8392 -2.4227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5692 0.3260 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1962 -1.4536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4227 0.8392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6785 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9691 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 6 1 0 0 0 0 3 13 2 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 25 1 0 0 0 0 7 26 1 0 0 0 0 8 33 1 0 0 0 0 9 15 1 0 0 0 0 9 24 1 0 0 0 0 10 27 1 0 0 0 0 11 12 2 0 0 0 0 11 33 1 0 0 0 0 13 21 1 0 0 0 0 13 24 1 0 0 0 0 14 20 1 0 0 0 0 14 36 1 1 0 0 0 15 12 1 6 0 0 0 15 34 1 0 0 0 0 16 10 1 6 0 0 0 16 17 1 0 0 0 0 16 35 1 0 0 0 0 17 18 1 0 0 0 0 17 28 1 1 0 0 0 18 19 1 0 0 0 0 18 29 1 6 0 0 0 19 22 1 0 0 0 0 19 30 1 1 0 0 0 20 24 1 1 0 0 0 20 25 1 0 0 0 0 21 31 2 0 0 0 0 21 34 1 0 0 0 0 22 35 1 0 0 0 0 22 37 1 6 0 0 0 23 32 2 0 0 0 0 23 36 1 0 0 0 0 24 1 1 1 0 0 0 25 26 1 1 0 0 0 26 23 1 1 0 0 0 26 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	518.18
Volume:	487.787
LogP:	1.071
LogD:	0.601
LogS:	-3.096
# Rotatable Bonds:	4
TPSA:	165.12
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	6.256
Fsp3:	0.615
Lipinski Rule-of-5:	Rejected
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:	-5.824
MDCK Permeability:	4.8771555157145485e-05
Pgp-inhibitor:	0.299
Pgp-substrate:	0.955
Human Intestinal Absorption (HIA):	0.904
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	82.24466705322266%
Volume Distribution (VD):	1.233
Pgp-substrate:	14.782389640808105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.745
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.581
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.354

ADMET: Excretion

Clearance (CL):	1.561
Half-life (T1/2):	0.703

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.263
Rat Oral Acute Toxicity:	0.657
Maximum Recommended Daily Dose:	0.845
Skin Sensitization:	0.088
Carcinogencity:	0.837
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.859

Download Data

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

Natural Product: NPC146991

Natural Product ID:	NPC146991
*Common Name:**	Fibleucinoside
IUPAC Name:	n.a.
Synonyms:	Fibleucinoside
Standard InCHIKey:	CLMFOKCFOQCBFM-MDETZSQFSA-N
Standard InCHI:	InChI=1S/C26H30O11/c1-24-9-15(12-5-8-33-11-12)34-21(31)13(24)3-6-25(2)20(24)14-4-7-26(25,23(32)36-14)37-22-19(30)18(29)17(28)16(10-27)35-22/h3-5,7-8,11,14-20,22,27-30H,6,9-10H2,1-2H3/t14-,15-,16-,17-,18+,19-,20+,22+,24-,25-,26+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@]23C=C[C@@H](OC2=O)[C@@H]2[C@@]3(C)CC=C3[C@@]2(C)C[C@@H](OC3=O)c2cocc2)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399973
PubChem CID:	44445725
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994701]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18829331]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	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	1
Others	12

Activity Type	# Activity
Individual Protein	1
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	>	100000.0	nM	PMID[465842]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	15.64	%	PMID[465843]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	18.8	%	PMID[465843]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	24.26	%	PMID[465843]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	22.82	%	PMID[465843]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	24.01	%	PMID[465843]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	23.88	%	PMID[465843]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	14.91	%	PMID[465843]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	19.05	%	PMID[465843]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	19.82	%	PMID[465843]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	21.31	%	PMID[465843]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	22.01	%	PMID[465843]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.11	%	PMID[465843]

☑ 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 NPC146991 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	1384
0.2-0.3	3170
0.3-0.4	6046
0.4-0.5	10736
0.5-0.6	10045
0.6-0.7	8408
0.7-0.8	2337
0.8-0.85	149
0.85-0.9	61
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9383	High Similarity	NPC262386
0.9359	High Similarity	NPC262872
0.9317	High Similarity	NPC169299
0.9317	High Similarity	NPC160818
0.9286	High Similarity	NPC44577
0.9241	High Similarity	NPC211777
0.9182	High Similarity	NPC198047
0.9136	High Similarity	NPC82602
0.9119	High Similarity	NPC207978
0.9012	High Similarity	NPC100333
0.8951	High Similarity	NPC93172
0.8951	High Similarity	NPC97574
0.8931	High Similarity	NPC45101
0.8917	High Similarity	NPC147168
0.8889	High Similarity	NPC271657
0.8889	High Similarity	NPC470182
0.8827	High Similarity	NPC477405
0.882	High Similarity	NPC477402
0.8805	High Similarity	NPC44675
0.8805	High Similarity	NPC214541
0.8782	High Similarity	NPC476942
0.8782	High Similarity	NPC476941
0.8782	High Similarity	NPC7388
0.8773	High Similarity	NPC276551
0.8765	High Similarity	NPC5079
0.8765	High Similarity	NPC18347
0.8765	High Similarity	NPC149896
0.8765	High Similarity	NPC69028
0.8758	High Similarity	NPC477403
0.8758	High Similarity	NPC307383
0.872	High Similarity	NPC470875
0.8718	High Similarity	NPC476937
0.8718	High Similarity	NPC476938
0.8712	High Similarity	NPC234660
0.8712	High Similarity	NPC39986
0.8712	High Similarity	NPC292389
0.8712	High Similarity	NPC51568
0.8712	High Similarity	NPC302369
0.8712	High Similarity	NPC134254
0.8712	High Similarity	NPC469338
0.8704	High Similarity	NPC335761
0.8696	High Similarity	NPC36655
0.8696	High Similarity	NPC261597
0.8688	High Similarity	NPC281258
0.8679	High Similarity	NPC476939
0.8679	High Similarity	NPC476940
0.8659	High Similarity	NPC470940
0.8659	High Similarity	NPC469849
0.865	High Similarity	NPC117986
0.865	High Similarity	NPC82851
0.865	High Similarity	NPC200782
0.865	High Similarity	NPC263432
0.8645	High Similarity	NPC137295
0.8642	High Similarity	NPC475967
0.8634	High Similarity	NPC469485
0.8614	High Similarity	NPC471397
0.8614	High Similarity	NPC271235
0.8599	High Similarity	NPC250228
0.8589	High Similarity	NPC25255
0.8589	High Similarity	NPC472653
0.858	High Similarity	NPC187149
0.858	High Similarity	NPC173544
0.858	High Similarity	NPC286722
0.858	High Similarity	NPC249021
0.8571	High Similarity	NPC264943
0.8562	High Similarity	NPC469503
0.8554	High Similarity	NPC472282
0.8554	High Similarity	NPC173516
0.8554	High Similarity	NPC472651
0.8545	High Similarity	NPC123088
0.8545	High Similarity	NPC476858
0.8545	High Similarity	NPC476857
0.8545	High Similarity	NPC476856
0.8537	High Similarity	NPC290400
0.8537	High Similarity	NPC96443
0.8537	High Similarity	NPC193798
0.8528	High Similarity	NPC473473
0.8528	High Similarity	NPC475295
0.8526	High Similarity	NPC86935
0.8519	High Similarity	NPC60973
0.8519	High Similarity	NPC209364
0.8509	High Similarity	NPC282445
0.8503	High Similarity	NPC472652
0.8494	Intermediate Similarity	NPC23387
0.8476	Intermediate Similarity	NPC305016
0.8466	Intermediate Similarity	NPC472283
0.8457	Intermediate Similarity	NPC35000
0.8457	Intermediate Similarity	NPC469336
0.8447	Intermediate Similarity	NPC476201
0.8443	Intermediate Similarity	NPC476850
0.8443	Intermediate Similarity	NPC472774
0.8443	Intermediate Similarity	NPC476861
0.8443	Intermediate Similarity	NPC472775
0.8443	Intermediate Similarity	NPC476853
0.8438	Intermediate Similarity	NPC46551
0.8434	Intermediate Similarity	NPC476860
0.8424	Intermediate Similarity	NPC329938
0.8405	Intermediate Similarity	NPC107646
0.8405	Intermediate Similarity	NPC126723
0.8402	Intermediate Similarity	NPC159232
0.8395	Intermediate Similarity	NPC178932
0.8395	Intermediate Similarity	NPC30222
0.8395	Intermediate Similarity	NPC57998
0.8393	Intermediate Similarity	NPC160651
0.8383	Intermediate Similarity	NPC475779
0.8377	Intermediate Similarity	NPC220094
0.8373	Intermediate Similarity	NPC472773
0.8373	Intermediate Similarity	NPC419
0.8365	Intermediate Similarity	NPC470941
0.8364	Intermediate Similarity	NPC475381
0.8354	Intermediate Similarity	NPC299038
0.8354	Intermediate Similarity	NPC472778
0.8354	Intermediate Similarity	NPC472777
0.8354	Intermediate Similarity	NPC472776
0.8344	Intermediate Similarity	NPC476262
0.8324	Intermediate Similarity	NPC470938
0.8323	Intermediate Similarity	NPC476122
0.8313	Intermediate Similarity	NPC472771
0.8313	Intermediate Similarity	NPC470939
0.8312	Intermediate Similarity	NPC310830
0.8304	Intermediate Similarity	NPC236004
0.8303	Intermediate Similarity	NPC237155
0.8303	Intermediate Similarity	NPC472779
0.8302	Intermediate Similarity	NPC346
0.8293	Intermediate Similarity	NPC263265
0.8291	Intermediate Similarity	NPC476944
0.8274	Intermediate Similarity	NPC478178
0.8274	Intermediate Similarity	NPC472141
0.8274	Intermediate Similarity	NPC214600
0.8263	Intermediate Similarity	NPC472139
0.8263	Intermediate Similarity	NPC469846
0.8253	Intermediate Similarity	NPC470789
0.825	Intermediate Similarity	NPC10088
0.8242	Intermediate Similarity	NPC472772
0.8228	Intermediate Similarity	NPC470741
0.8225	Intermediate Similarity	NPC473766
0.8225	Intermediate Similarity	NPC473753
0.821	Intermediate Similarity	NPC476936
0.821	Intermediate Similarity	NPC477404
0.821	Intermediate Similarity	NPC196864
0.821	Intermediate Similarity	NPC159927
0.821	Intermediate Similarity	NPC469335
0.8208	Intermediate Similarity	NPC478177
0.8198	Intermediate Similarity	NPC469576
0.8198	Intermediate Similarity	NPC94763
0.8187	Intermediate Similarity	NPC262198
0.8187	Intermediate Similarity	NPC276676
0.8182	Intermediate Similarity	NPC242068
0.8182	Intermediate Similarity	NPC247563
0.8153	Intermediate Similarity	NPC90296
0.815	Intermediate Similarity	NPC124828
0.815	Intermediate Similarity	NPC469633
0.8148	Intermediate Similarity	NPC69647
0.8148	Intermediate Similarity	NPC125182
0.8148	Intermediate Similarity	NPC195325
0.8141	Intermediate Similarity	NPC476943
0.8129	Intermediate Similarity	NPC470995
0.8129	Intermediate Similarity	NPC302392
0.8121	Intermediate Similarity	NPC469850
0.8118	Intermediate Similarity	NPC478179
0.811	Intermediate Similarity	NPC75906
0.8107	Intermediate Similarity	NPC261184
0.8103	Intermediate Similarity	NPC472665
0.8095	Intermediate Similarity	NPC188649
0.8092	Intermediate Similarity	NPC471437
0.8089	Intermediate Similarity	NPC90953
0.8084	Intermediate Similarity	NPC473368
0.8079	Intermediate Similarity	NPC105395
0.807	Intermediate Similarity	NPC242334
0.807	Intermediate Similarity	NPC327922
0.8065	Intermediate Similarity	NPC92941
0.8063	Intermediate Similarity	NPC142113
0.8059	Intermediate Similarity	NPC472670
0.8059	Intermediate Similarity	NPC121995
0.8059	Intermediate Similarity	NPC307781
0.8049	Intermediate Similarity	NPC18135
0.8047	Intermediate Similarity	NPC165218
0.8047	Intermediate Similarity	NPC224394
0.8047	Intermediate Similarity	NPC663
0.8047	Intermediate Similarity	NPC288602
0.8047	Intermediate Similarity	NPC88841
0.8046	Intermediate Similarity	NPC195972
0.8037	Intermediate Similarity	NPC472654
0.8036	Intermediate Similarity	NPC191828
0.8025	Intermediate Similarity	NPC255414
0.8025	Intermediate Similarity	NPC221809
0.8024	Intermediate Similarity	NPC167142
0.8012	Intermediate Similarity	NPC41182
0.8	Intermediate Similarity	NPC243577
0.8	Intermediate Similarity	NPC268905
0.8	Intermediate Similarity	NPC223415
0.8	Intermediate Similarity	NPC470181
0.7988	Intermediate Similarity	NPC18986
0.7976	Intermediate Similarity	NPC474611
0.7976	Intermediate Similarity	NPC475226
0.7965	Intermediate Similarity	NPC472766
0.7965	Intermediate Similarity	NPC296558
0.7965	Intermediate Similarity	NPC472765
0.7965	Intermediate Similarity	NPC472673
0.7962	Intermediate Similarity	NPC186626

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 NPC146991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	999
0.2-0.3	2193
0.3-0.4	2712
0.4-0.5	1909
0.5-0.6	786
0.6-0.7	225
0.7-0.8	34
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7824	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8434	Phase 2
0.7798	Intermediate Similarity	NPD5761	Phase 2
0.7798	Intermediate Similarity	NPD5760	Phase 2
0.7472	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6559	Discontinued
0.7363	Intermediate Similarity	NPD8312	Approved
0.7363	Intermediate Similarity	NPD8313	Approved
0.7348	Intermediate Similarity	NPD6764	Approved
0.7348	Intermediate Similarity	NPD6765	Approved
0.7291	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6797	Phase 2
0.7189	Intermediate Similarity	NPD6784	Approved
0.7189	Intermediate Similarity	NPD6785	Approved
0.7186	Intermediate Similarity	NPD4628	Phase 3
0.7184	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7075	Discontinued
0.7158	Intermediate Similarity	NPD7251	Discontinued
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7127	Intermediate Similarity	NPD7799	Discontinued
0.712	Intermediate Similarity	NPD7808	Phase 3
0.712	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6599	Discontinued
0.7077	Intermediate Similarity	NPD7435	Discontinued
0.7044	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3751	Discontinued
0.7033	Intermediate Similarity	NPD3818	Discontinued
0.7029	Intermediate Similarity	NPD6801	Discontinued
0.7005	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8404	Phase 2
0.6995	Remote Similarity	NPD7054	Approved
0.6989	Remote Similarity	NPD8455	Phase 2
0.6968	Remote Similarity	NPD8150	Discontinued
0.6957	Remote Similarity	NPD7472	Approved
0.6954	Remote Similarity	NPD8320	Phase 1
0.6954	Remote Similarity	NPD8319	Approved
0.6951	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5402	Approved
0.694	Remote Similarity	NPD7228	Approved
0.6936	Remote Similarity	NPD5403	Approved
0.6923	Remote Similarity	NPD6777	Approved
0.6923	Remote Similarity	NPD6779	Approved
0.6923	Remote Similarity	NPD6776	Approved
0.6923	Remote Similarity	NPD6781	Approved
0.6923	Remote Similarity	NPD6778	Approved
0.6923	Remote Similarity	NPD6782	Approved
0.6923	Remote Similarity	NPD6780	Approved
0.6919	Remote Similarity	NPD5401	Approved
0.6906	Remote Similarity	NPD3787	Discontinued
0.6882	Remote Similarity	NPD7685	Pre-registration
0.6866	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7874	Approved
0.686	Remote Similarity	NPD6799	Approved
0.6857	Remote Similarity	NPD7458	Discontinued
0.6832	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7783	Phase 2
0.6831	Remote Similarity	NPD6166	Phase 2
0.6831	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7696	Phase 3
0.6818	Remote Similarity	NPD7697	Approved
0.6818	Remote Similarity	NPD4380	Phase 2
0.6818	Remote Similarity	NPD7698	Approved
0.6798	Remote Similarity	NPD7819	Suspended
0.6796	Remote Similarity	NPD5494	Approved
0.6791	Remote Similarity	NPD7240	Approved
0.6778	Remote Similarity	NPD3749	Approved
0.6776	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8407	Phase 2
0.6766	Remote Similarity	NPD7701	Phase 2
0.676	Remote Similarity	NPD3817	Phase 2
0.6743	Remote Similarity	NPD920	Approved
0.6742	Remote Similarity	NPD37	Approved
0.674	Remote Similarity	NPD919	Approved
0.6738	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4966	Approved
0.6722	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4965	Approved
0.6722	Remote Similarity	NPD4967	Phase 2
0.672	Remote Similarity	NPD5844	Phase 1
0.6719	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD8368	Discontinued
0.67	Remote Similarity	NPD7870	Phase 2
0.67	Remote Similarity	NPD7871	Phase 2
0.6686	Remote Similarity	NPD6273	Approved
0.6686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD6535	Approved
0.6667	Remote Similarity	NPD7801	Approved
0.6667	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD7199	Phase 2
0.665	Remote Similarity	NPD7699	Phase 2
0.665	Remote Similarity	NPD7700	Phase 2
0.6648	Remote Similarity	NPD6234	Discontinued
0.6631	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3882	Suspended
0.6629	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7236	Approved
0.6576	Remote Similarity	NPD8127	Discontinued
0.6576	Remote Similarity	NPD6959	Discontinued
0.6576	Remote Similarity	NPD1247	Approved
0.6575	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3226	Approved
0.6569	Remote Similarity	NPD8151	Discontinued
0.6559	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.654	Remote Similarity	NPD7907	Approved
0.654	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD2532	Approved
0.6534	Remote Similarity	NPD2533	Approved
0.6534	Remote Similarity	NPD2534	Approved
0.6529	Remote Similarity	NPD7097	Phase 1
0.6524	Remote Similarity	NPD4665	Approved
0.6524	Remote Similarity	NPD4111	Phase 1
0.6519	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7239	Suspended
0.6517	Remote Similarity	NPD3057	Approved
0.6517	Remote Similarity	NPD6823	Phase 2
0.6517	Remote Similarity	NPD3533	Approved
0.6517	Remote Similarity	NPD2972	Approved
0.6514	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD2346	Discontinued
0.6512	Remote Similarity	NPD1471	Phase 3
0.6509	Remote Similarity	NPD6355	Discontinued
0.6505	Remote Similarity	NPD5676	Approved
0.65	Remote Similarity	NPD4107	Approved
0.6494	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7033	Discontinued
0.6477	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD4482	Phase 3
0.6467	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD1934	Approved
0.6462	Remote Similarity	NPD8435	Approved
0.6453	Remote Similarity	NPD1551	Phase 2
0.6452	Remote Similarity	NPD6232	Discontinued
0.6444	Remote Similarity	NPD7028	Phase 2
0.6437	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD2800	Approved
0.6436	Remote Similarity	NPD7473	Discontinued
0.6429	Remote Similarity	NPD1465	Phase 2
0.6416	Remote Similarity	NPD5763	Approved
0.6416	Remote Similarity	NPD5762	Approved
0.6412	Remote Similarity	NPD1933	Approved
0.64	Remote Similarity	NPD3750	Approved
0.6398	Remote Similarity	NPD8513	Phase 3
0.6398	Remote Similarity	NPD8516	Approved
0.6398	Remote Similarity	NPD8517	Approved
0.6398	Remote Similarity	NPD8515	Approved
0.6395	Remote Similarity	NPD2799	Discontinued
0.6391	Remote Similarity	NPD6233	Phase 2
0.6379	Remote Similarity	NPD1549	Phase 2
0.6378	Remote Similarity	NPD8361	Approved
0.6378	Remote Similarity	NPD8360	Approved
0.6364	Remote Similarity	NPD6213	Phase 3
0.6364	Remote Similarity	NPD6212	Phase 3
0.6364	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6190	Approved
0.6359	Remote Similarity	NPD7768	Phase 2
0.6359	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2796	Approved
0.6355	Remote Similarity	NPD2491	Approved
0.6348	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD1243	Approved
0.6341	Remote Similarity	NPD7999	Approved
0.6337	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7930	Approved
0.6331	Remote Similarity	NPD6798	Discontinued
0.6331	Remote Similarity	NPD2313	Discontinued
0.633	Remote Similarity	NPD3926	Phase 2
0.6324	Remote Similarity	NPD7680	Approved
0.6322	Remote Similarity	NPD6005	Phase 3
0.6322	Remote Similarity	NPD7266	Discontinued
0.6322	Remote Similarity	NPD6002	Phase 3
0.6322	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6004	Phase 3
0.6322	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7583	Approved
0.6311	Remote Similarity	NPD7584	Approved
0.631	Remote Similarity	NPD6832	Phase 2
0.6307	Remote Similarity	NPD7003	Approved
0.6301	Remote Similarity	NPD3748	Approved
0.6287	Remote Similarity	NPD5647	Approved
0.6287	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD970	Clinical (unspecified phase)
0.628	Remote Similarity	NPD1091	Approved
0.628	Remote Similarity	NPD7585	Approved
0.6275	Remote Similarity	NPD3448	Approved
0.6272	Remote Similarity	NPD7095	Approved
0.6271	Remote Similarity	NPD2354	Approved
0.6271	Remote Similarity	NPD3887	Approved
0.627	Remote Similarity	NPD7057	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data