NPASS Compound

Structure

NPC82602 OpenBabel07101718252D 38 43 0 0 1 0 0 0 0 0999 V2000 2.6831 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5543 0.9605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7888 1.2348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3857 1.1855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3639 1.3934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6105 -1.5736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1947 -0.2158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5657 -0.5746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0971 0.8073 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4084 -0.0363 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3635 0.9627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4759 1.4234 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6332 0.8850 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 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 -3.4981 -2.0342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2960 -0.4969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2063 1.5011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4311 2.4224 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8289 0.5594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8639 0.5274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6781 -0.1140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7456 1.3457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 4 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 34 1 0 0 0 0 7 12 1 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 24 1 0 0 0 0 9 27 1 0 0 0 0 10 11 2 0 0 0 0 10 34 1 0 0 0 0 12 21 1 0 0 0 0 12 24 1 6 0 0 0 13 11 1 1 0 0 0 13 35 1 0 0 0 0 14 9 1 6 0 0 0 14 18 1 0 0 0 0 14 36 1 0 0 0 0 15 24 1 1 0 0 0 15 25 1 0 0 0 0 16 26 1 1 0 0 0 16 37 1 0 0 0 0 17 25 1 6 0 0 0 17 38 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 1 0 0 0 19 20 1 0 0 0 0 19 29 1 6 0 0 0 20 22 1 0 0 0 0 20 30 1 1 0 0 0 21 31 2 0 0 0 0 21 35 1 0 0 0 0 22 36 1 0 0 0 0 22 37 1 6 0 0 0 23 26 1 0 0 0 0 23 32 2 0 0 0 0 23 38 1 0 0 0 0 24 1 1 1 0 0 0 25 26 1 1 0 0 0 26 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.21
Volume:	501.85
LogP:	0.967
LogD:	0.692
LogS:	-3.549
# Rotatable Bonds:	4
TPSA:	185.35
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.246
Synthetic Accessibility Score:	5.446
Fsp3:	0.769
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:	-5.8
MDCK Permeability:	0.00015100855671335012
Pgp-inhibitor:	0.467
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.176
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	66.4302749633789%
Volume Distribution (VD):	0.641
Pgp-substrate:	27.488439559936523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.141
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.222
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.204
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	2.735
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.176
AMES Toxicity:	0.111
Rat Oral Acute Toxicity:	0.914
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.107
Carcinogencity:	0.954
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC82602

Natural Product ID:	NPC82602
*Common Name:**	Borapetoside A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GCXIISSOWSXMCD-MZYRCUENSA-N
Standard InCHI:	InChI=1S/C26H34O12/c1-24-8-13(11-5-6-34-10-11)35-21(31)12(24)7-17-25(2)15(24)3-4-16(26(25,33)23(32)38-17)37-22-20(30)19(29)18(28)14(9-27)36-22/h5-6,10,12-20,22,27-30,33H,3-4,7-9H2,1-2H3/t12-,13-,14+,15-,16-,17-,18+,19-,20+,22-,24+,25-,26-/m0/s1
SMILES:	C[C@@]12C[C@@H](c3ccoc3)OC(=O)[C@@H]1C[C@H]1[C@]3(C)[C@H]2CC[C@@H]([C@@]3(C(=O)O1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097583
PubChem CID:	21636215
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20356064]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22283497]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	leaf	Putz City, Chiayi County, Taiwan	2009-Nov	PMID[25999202]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28742368]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29397715]
NPO26700	Tinospora crispa	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	2
Others	2

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[534142]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	>	10000.0	nM	PMID[534142]
NPT32	Organism	Mus musculus	Mus musculus	FC	=	2.0	n.a.	PMID[534143]

☑ 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 NPC82602 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	374
0.1-0.2	1444
0.2-0.3	3300
0.3-0.4	5508
0.4-0.5	9854
0.5-0.6	9977
0.6-0.7	9203
0.7-0.8	2571
0.8-0.85	314
0.85-0.9	115
0.9-0.95	28
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC169299
0.9688	High Similarity	NPC160818
0.956	High Similarity	NPC97574
0.956	High Similarity	NPC93172
0.95	High Similarity	NPC100333
0.9494	High Similarity	NPC207978
0.9494	High Similarity	NPC211777
0.9434	High Similarity	NPC198047
0.9367	High Similarity	NPC475967
0.9321	High Similarity	NPC271235
0.9313	High Similarity	NPC477405
0.9273	High Similarity	NPC262386
0.9259	High Similarity	NPC472651
0.9255	High Similarity	NPC276551
0.9255	High Similarity	NPC470182
0.925	High Similarity	NPC200782
0.925	High Similarity	NPC82851
0.9245	High Similarity	NPC262872
0.9202	High Similarity	NPC472652
0.9198	High Similarity	NPC470875
0.9193	High Similarity	NPC292389
0.9193	High Similarity	NPC469338
0.9182	High Similarity	NPC45101
0.9177	High Similarity	NPC214541
0.9177	High Similarity	NPC44675
0.9136	High Similarity	NPC271657
0.9136	High Similarity	NPC146991
0.9136	High Similarity	NPC469849
0.9136	High Similarity	NPC470940
0.913	High Similarity	NPC69028
0.9125	High Similarity	NPC307383
0.9107	High Similarity	NPC470938
0.9085	High Similarity	NPC471397
0.908	High Similarity	NPC472141
0.9074	High Similarity	NPC302369
0.9074	High Similarity	NPC134254
0.9074	High Similarity	NPC39986
0.9074	High Similarity	NPC472139
0.9068	High Similarity	NPC335761
0.9068	High Similarity	NPC472653
0.9062	High Similarity	NPC249021
0.9062	High Similarity	NPC299038
0.9062	High Similarity	NPC261597
0.9062	High Similarity	NPC36655
0.9051	High Similarity	NPC147168
0.9051	High Similarity	NPC476939
0.9051	High Similarity	NPC476940
0.9051	High Similarity	NPC476201
0.9024	High Similarity	NPC472774
0.9024	High Similarity	NPC173516
0.9024	High Similarity	NPC472282
0.9024	High Similarity	NPC476850
0.9024	High Similarity	NPC476861
0.9024	High Similarity	NPC472775
0.9018	High Similarity	NPC123088
0.9012	High Similarity	NPC263432
0.9012	High Similarity	NPC117986
0.9012	High Similarity	NPC5079
0.9012	High Similarity	NPC18347
0.9012	High Similarity	NPC149896
0.8994	High Similarity	NPC282445
0.897	High Similarity	NPC160651
0.8957	High Similarity	NPC469846
0.8957	High Similarity	NPC419
0.8957	High Similarity	NPC234660
0.8957	High Similarity	NPC472773
0.8957	High Similarity	NPC51568
0.8951	High Similarity	NPC477402
0.8944	High Similarity	NPC472778
0.8944	High Similarity	NPC472777
0.8944	High Similarity	NPC472776
0.8944	High Similarity	NPC187149
0.8938	High Similarity	NPC476262
0.8931	High Similarity	NPC469503
0.8902	High Similarity	NPC476858
0.8902	High Similarity	NPC476856
0.8902	High Similarity	NPC476857
0.8896	High Similarity	NPC329938
0.8896	High Similarity	NPC472771
0.8868	High Similarity	NPC18135
0.8848	High Similarity	NPC307781
0.8848	High Similarity	NPC472670
0.8834	High Similarity	NPC25255
0.8834	High Similarity	NPC470789
0.8834	High Similarity	NPC305016
0.8827	High Similarity	NPC286722
0.882	High Similarity	NPC35000
0.882	High Similarity	NPC469336
0.882	High Similarity	NPC264943
0.8812	High Similarity	NPC44577
0.8805	High Similarity	NPC476122
0.8797	High Similarity	NPC7388
0.8797	High Similarity	NPC476942
0.8797	High Similarity	NPC476941
0.8795	High Similarity	NPC476853
0.878	High Similarity	NPC193798
0.878	High Similarity	NPC96443
0.878	High Similarity	NPC290400
0.8773	High Similarity	NPC475295
0.8773	High Similarity	NPC473473
0.8773	High Similarity	NPC475226
0.8773	High Similarity	NPC477403
0.8765	High Similarity	NPC126723
0.8765	High Similarity	NPC107646
0.8765	High Similarity	NPC472665
0.8765	High Similarity	NPC209364
0.8758	High Similarity	NPC30222
0.8758	High Similarity	NPC57998
0.8758	High Similarity	NPC178932
0.875	High Similarity	NPC159232
0.8743	High Similarity	NPC472673
0.8742	High Similarity	NPC125182
0.8742	High Similarity	NPC69647
0.8742	High Similarity	NPC195325
0.8735	High Similarity	NPC23387
0.8735	High Similarity	NPC214600
0.8734	High Similarity	NPC476937
0.8734	High Similarity	NPC476938
0.8728	High Similarity	NPC105395
0.8728	High Similarity	NPC242068
0.8728	High Similarity	NPC247563
0.872	High Similarity	NPC475381
0.8712	High Similarity	NPC472772
0.8712	High Similarity	NPC472283
0.8704	High Similarity	NPC281258
0.8696	High Similarity	NPC268905
0.869	High Similarity	NPC470995
0.8688	High Similarity	NPC196864
0.8688	High Similarity	NPC477404
0.8675	High Similarity	NPC476860
0.8667	High Similarity	NPC188649
0.8667	High Similarity	NPC470939
0.8667	High Similarity	NPC470792
0.865	High Similarity	NPC469485
0.8647	High Similarity	NPC94763
0.8647	High Similarity	NPC236004
0.8639	High Similarity	NPC285227
0.8625	High Similarity	NPC472654
0.8623	High Similarity	NPC475779
0.8616	High Similarity	NPC470941
0.8616	High Similarity	NPC255414
0.8616	High Similarity	NPC250228
0.8616	High Similarity	NPC221809
0.8614	High Similarity	NPC88841
0.8614	High Similarity	NPC288602
0.8606	High Similarity	NPC191828
0.8598	High Similarity	NPC167142
0.8598	High Similarity	NPC173544
0.8589	High Similarity	NPC296807
0.8589	High Similarity	NPC155939
0.8589	High Similarity	NPC141538
0.858	High Similarity	NPC75906
0.8571	High Similarity	NPC159927
0.8571	High Similarity	NPC476936
0.8571	High Similarity	NPC469335
0.8553	High Similarity	NPC346
0.8547	High Similarity	NPC478177
0.8547	High Similarity	NPC470181
0.8545	High Similarity	NPC237155
0.8545	High Similarity	NPC472671
0.8544	High Similarity	NPC251865
0.8544	High Similarity	NPC476944
0.8538	High Similarity	NPC471437
0.8537	High Similarity	NPC60973
0.8528	High Similarity	NPC98206
0.8528	High Similarity	NPC253201
0.8528	High Similarity	NPC34421
0.8528	High Similarity	NPC237259
0.8528	High Similarity	NPC302054
0.8521	High Similarity	NPC296558
0.8521	High Similarity	NPC242334
0.8521	High Similarity	NPC472765
0.8521	High Similarity	NPC472766
0.8512	High Similarity	NPC478178
0.8512	High Similarity	NPC121995
0.8503	High Similarity	NPC283209
0.8503	High Similarity	NPC476197
0.8503	High Similarity	NPC663
0.8503	High Similarity	NPC285567
0.8503	High Similarity	NPC224394
0.8497	Intermediate Similarity	NPC11062
0.8491	Intermediate Similarity	NPC5676
0.8491	Intermediate Similarity	NPC41182
0.8485	Intermediate Similarity	NPC88007
0.8485	Intermediate Similarity	NPC470119
0.8485	Intermediate Similarity	NPC470118
0.8485	Intermediate Similarity	NPC197137
0.8485	Intermediate Similarity	NPC214495
0.8485	Intermediate Similarity	NPC194499
0.8485	Intermediate Similarity	NPC475066
0.8481	Intermediate Similarity	NPC476946
0.8476	Intermediate Similarity	NPC92979
0.8476	Intermediate Similarity	NPC469850
0.8466	Intermediate Similarity	NPC33938
0.8466	Intermediate Similarity	NPC472672
0.8462	Intermediate Similarity	NPC473753
0.8462	Intermediate Similarity	NPC473766
0.8462	Intermediate Similarity	NPC472764
0.8457	Intermediate Similarity	NPC470997
0.8452	Intermediate Similarity	NPC472664

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 NPC82602 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	999
0.2-0.3	2250
0.3-0.4	2730
0.4-0.5	1774
0.5-0.6	792
0.6-0.7	252
0.7-0.8	34
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
0.8364	Intermediate Similarity	NPD5760	Phase 2
0.8364	Intermediate Similarity	NPD5761	Phase 2
0.8249	Intermediate Similarity	NPD8434	Phase 2
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7746	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8312	Approved
0.7582	Intermediate Similarity	NPD8313	Approved
0.7569	Intermediate Similarity	NPD6764	Approved
0.7569	Intermediate Similarity	NPD6765	Approved
0.7542	Intermediate Similarity	NPD7228	Approved
0.7486	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7251	Discontinued
0.7459	Intermediate Similarity	NPD7074	Phase 3
0.7444	Intermediate Similarity	NPD3818	Discontinued
0.7444	Intermediate Similarity	NPD7799	Discontinued
0.7432	Intermediate Similarity	NPD7808	Phase 3
0.7432	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6797	Phase 2
0.7414	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6784	Approved
0.7405	Intermediate Similarity	NPD6785	Approved
0.7403	Intermediate Similarity	NPD7054	Approved
0.7386	Intermediate Similarity	NPD7075	Discontinued
0.7377	Intermediate Similarity	NPD7240	Approved
0.7363	Intermediate Similarity	NPD7472	Approved
0.7363	Intermediate Similarity	NPD8404	Phase 2
0.733	Intermediate Similarity	NPD4967	Phase 2
0.733	Intermediate Similarity	NPD4966	Approved
0.733	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD4628	Phase 3
0.7283	Intermediate Similarity	NPD7685	Pre-registration
0.7282	Intermediate Similarity	NPD7435	Discontinued
0.7247	Intermediate Similarity	NPD6234	Discontinued
0.7241	Intermediate Similarity	NPD6599	Discontinued
0.7216	Intermediate Similarity	NPD8455	Phase 2
0.7216	Intermediate Similarity	NPD7819	Suspended
0.7207	Intermediate Similarity	NPD5494	Approved
0.7182	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7199	Phase 2
0.7159	Intermediate Similarity	NPD37	Approved
0.7159	Intermediate Similarity	NPD6801	Discontinued
0.7158	Intermediate Similarity	NPD3751	Discontinued
0.715	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6778	Approved
0.7128	Intermediate Similarity	NPD6780	Approved
0.7128	Intermediate Similarity	NPD6776	Approved
0.7128	Intermediate Similarity	NPD6782	Approved
0.7128	Intermediate Similarity	NPD6781	Approved
0.7128	Intermediate Similarity	NPD6777	Approved
0.7128	Intermediate Similarity	NPD6779	Approved
0.7127	Intermediate Similarity	NPD3787	Discontinued
0.712	Intermediate Similarity	NPD5844	Phase 1
0.7107	Intermediate Similarity	NPD7696	Phase 3
0.7107	Intermediate Similarity	NPD7697	Approved
0.7107	Intermediate Similarity	NPD7698	Approved
0.709	Intermediate Similarity	NPD8150	Discontinued
0.7086	Intermediate Similarity	NPD7458	Discontinued
0.7079	Intermediate Similarity	NPD5402	Approved
0.7079	Intermediate Similarity	NPD3817	Phase 2
0.7074	Intermediate Similarity	NPD8407	Phase 2
0.7072	Intermediate Similarity	NPD8127	Discontinued
0.7071	Intermediate Similarity	NPD8320	Phase 1
0.7071	Intermediate Similarity	NPD8319	Approved
0.7065	Intermediate Similarity	NPD7874	Approved
0.7065	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7701	Phase 2
0.7045	Intermediate Similarity	NPD4380	Phase 2
0.7043	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7783	Phase 2
0.703	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8368	Discontinued
0.7	Intermediate Similarity	NPD3749	Approved
0.6994	Remote Similarity	NPD6799	Approved
0.6985	Remote Similarity	NPD7870	Phase 2
0.6985	Remote Similarity	NPD7871	Phase 2
0.6971	Remote Similarity	NPD5403	Approved
0.6961	Remote Similarity	NPD919	Approved
0.6954	Remote Similarity	NPD5401	Approved
0.6946	Remote Similarity	NPD7801	Approved
0.6944	Remote Similarity	NPD3882	Suspended
0.6939	Remote Similarity	NPD7700	Phase 2
0.6939	Remote Similarity	NPD7699	Phase 2
0.6931	Remote Similarity	NPD8151	Discontinued
0.6927	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7473	Discontinued
0.6914	Remote Similarity	NPD6273	Approved
0.691	Remote Similarity	NPD7411	Suspended
0.6897	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD920	Approved
0.6872	Remote Similarity	NPD6535	Approved
0.6872	Remote Similarity	NPD1934	Approved
0.6872	Remote Similarity	NPD6534	Approved
0.685	Remote Similarity	NPD7680	Approved
0.6848	Remote Similarity	NPD6232	Discontinued
0.6842	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7236	Approved
0.6833	Remote Similarity	NPD1465	Phase 2
0.6821	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6823	Phase 2
0.6798	Remote Similarity	NPD3226	Approved
0.6798	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD1247	Approved
0.6793	Remote Similarity	NPD6959	Discontinued
0.6765	Remote Similarity	NPD7097	Phase 1
0.6763	Remote Similarity	NPD7930	Approved
0.6761	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2533	Approved
0.6761	Remote Similarity	NPD2532	Approved
0.6761	Remote Similarity	NPD2534	Approved
0.6753	Remote Similarity	NPD8361	Approved
0.6753	Remote Similarity	NPD8360	Approved
0.6753	Remote Similarity	NPD8435	Approved
0.6746	Remote Similarity	NPD6355	Discontinued
0.6744	Remote Similarity	NPD7266	Discontinued
0.6744	Remote Similarity	NPD2346	Discontinued
0.6744	Remote Similarity	NPD1471	Phase 3
0.6742	Remote Similarity	NPD7239	Suspended
0.673	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3926	Phase 2
0.67	Remote Similarity	NPD7999	Approved
0.6684	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD6674	Discontinued
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7768	Phase 2
0.6651	Remote Similarity	NPD7907	Approved
0.6649	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2801	Approved
0.6647	Remote Similarity	NPD5763	Approved
0.6647	Remote Similarity	NPD5762	Approved
0.6647	Remote Similarity	NPD1933	Approved
0.6635	Remote Similarity	NPD4665	Approved
0.6635	Remote Similarity	NPD4111	Phase 1
0.6628	Remote Similarity	NPD2799	Discontinued
0.6628	Remote Similarity	NPD7033	Discontinued
0.6609	Remote Similarity	NPD1549	Phase 2
0.6591	Remote Similarity	NPD6190	Approved
0.659	Remote Similarity	NPD6099	Approved
0.659	Remote Similarity	NPD2796	Approved
0.659	Remote Similarity	NPD6100	Approved
0.659	Remote Similarity	NPD1551	Phase 2
0.6585	Remote Similarity	NPD7507	Approved
0.6585	Remote Similarity	NPD7584	Approved
0.6585	Remote Similarity	NPD7583	Approved
0.6573	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1653	Approved
0.6553	Remote Similarity	NPD7585	Approved
0.6552	Remote Similarity	NPD3057	Approved
0.6552	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6832	Phase 2
0.6536	Remote Similarity	NPD1512	Approved
0.6535	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4107	Approved
0.6534	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD3750	Approved
0.6526	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7095	Approved
0.6509	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2935	Discontinued
0.6489	Remote Similarity	NPD7229	Phase 3
0.6482	Remote Similarity	NPD6212	Phase 3
0.6482	Remote Similarity	NPD6213	Phase 3
0.6482	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD1243	Approved
0.6477	Remote Similarity	NPD2800	Approved
0.6471	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2972	Approved
0.6471	Remote Similarity	NPD3533	Approved
0.6471	Remote Similarity	NPD2313	Discontinued
0.6471	Remote Similarity	NPD6798	Discontinued
0.6468	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD2344	Approved
0.6457	Remote Similarity	NPD6004	Phase 3
0.6457	Remote Similarity	NPD6005	Phase 3
0.6457	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6002	Phase 3
0.6453	Remote Similarity	NPD447	Suspended

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