NPASS Compound

Structure

NPC97574 OpenBabel07101718182D 38 42 0 0 1 0 0 0 0 0999 V2000 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8769 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3769 -0.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 11 1 0 0 0 0 3 4 1 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 34 1 0 0 0 0 7 15 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 10 12 2 0 0 0 0 10 34 1 0 0 0 0 11 28 2 0 0 0 0 11 35 1 0 0 0 0 13 3 1 6 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 24 1 0 0 0 0 14 26 1 6 0 0 0 15 23 1 0 0 0 0 15 29 1 6 0 0 0 16 37 1 6 0 0 0 17 12 1 1 0 0 0 17 36 1 0 0 0 0 18 9 1 6 0 0 0 18 20 1 0 0 0 0 18 38 1 0 0 0 0 19 23 1 0 0 0 0 19 26 1 1 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 22 1 0 0 0 0 21 31 1 6 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 35 1 6 0 0 0 24 33 2 0 0 0 0 24 36 1 0 0 0 0 25 37 1 6 0 0 0 25 38 1 0 0 0 0 26 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.22
Volume:	510.407
LogP:	0.622
LogD:	1.261
LogS:	-2.497
# Rotatable Bonds:	6
TPSA:	185.35
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.31
Synthetic Accessibility Score:	5.255
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:	-6.338
MDCK Permeability:	0.00015457894187420607
Pgp-inhibitor:	0.01
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.882
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102
Plasma Protein Binding (PPB):	58.98722457885742%
Volume Distribution (VD):	0.667
Pgp-substrate:	27.063730239868164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.147
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	2.78
Half-life (T1/2):	0.769

ADMET: Toxicity

hERG Blockers:	0.172
Human Hepatotoxicity (H-HT):	0.452
Drug-inuced Liver Injury (DILI):	0.564
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.199
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.051
Carcinogencity:	0.226
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC97574

Natural Product ID:	NPC97574
*Common Name:**	Tinosposinenside C
IUPAC Name:	[(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4a,5,6,6a,7,8,9,10,10a-decahydro-1H-benzo[f]isochromen-10-yl] acetate
Synonyms:	Tinosposinenside C
Standard InCHIKey:	WAJJNHUEVQGAOS-DPAXXLBTSA-N
Standard InCHI:	InChI=1S/C26H36O12/c1-11(28)35-23-15(29)7-16(37-25-22(32)21(31)20(30)18(9-27)38-25)13-3-4-14-24(33)36-17(12-5-6-34-10-12)8-26(14,2)19(13)23/h5-6,10,13-23,25,27,29-32H,3-4,7-9H2,1-2H3/t13-,14+,15+,16-,17+,18-,19+,20-,21+,22-,23+,25-,26-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2C[C@H](O)[C@@H]([C@@H]3[C@@H]2CC[C@@H]2[C@@]3(C)C[C@H](OC2=O)c2cocc2)OC(=O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251087
PubChem CID:	24763077
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
NPO15960	Tinospora sinensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18020421]
NPO15960	Tinospora sinensis	Species	Menispermaceae	Eukaryota	Stems	n.a.	n.a.	PMID[28358196]
NPO15960	Tinospora sinensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15960	Tinospora sinensis	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	3300000.0	nM	PMID[492582]

☑ 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 NPC97574 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	361
0.1-0.2	1460
0.2-0.3	3302
0.3-0.4	5691
0.4-0.5	9641
0.5-0.6	9327
0.6-0.7	9428
0.7-0.8	3083
0.8-0.85	261
0.85-0.9	107
0.9-0.95	27
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC93172
0.9677	High Similarity	NPC211777
0.9677	High Similarity	NPC207978
0.9615	High Similarity	NPC198047
0.956	High Similarity	NPC82602
0.9551	High Similarity	NPC200782
0.9434	High Similarity	NPC100333
0.943	High Similarity	NPC470182
0.9423	High Similarity	NPC262872
0.9379	High Similarity	NPC169299
0.9379	High Similarity	NPC160818
0.9325	High Similarity	NPC262386
0.9299	High Similarity	NPC307383
0.9231	High Similarity	NPC476262
0.9226	High Similarity	NPC476201
0.9226	High Similarity	NPC469503
0.9187	High Similarity	NPC271657
0.9182	High Similarity	NPC82851
0.9167	High Similarity	NPC282445
0.913	High Similarity	NPC472141
0.9125	High Similarity	NPC477405
0.9125	High Similarity	NPC472139
0.9125	High Similarity	NPC472773
0.9097	High Similarity	NPC476122
0.9074	High Similarity	NPC472775
0.9074	High Similarity	NPC472774
0.9068	High Similarity	NPC276551
0.9062	High Similarity	NPC18347
0.9062	High Similarity	NPC149896
0.9062	High Similarity	NPC472771
0.9062	High Similarity	NPC69028
0.9057	High Similarity	NPC475967
0.9032	High Similarity	NPC125182
0.9032	High Similarity	NPC69647
0.9018	High Similarity	NPC471397
0.9018	High Similarity	NPC271235
0.9012	High Similarity	NPC470875
0.9006	High Similarity	NPC302369
0.9006	High Similarity	NPC292389
0.9006	High Similarity	NPC134254
0.9006	High Similarity	NPC39986
0.9006	High Similarity	NPC469338
0.8994	High Similarity	NPC299038
0.8994	High Similarity	NPC472778
0.8994	High Similarity	NPC472776
0.8994	High Similarity	NPC249021
0.8994	High Similarity	NPC472777
0.8994	High Similarity	NPC45101
0.8987	High Similarity	NPC35000
0.8987	High Similarity	NPC469336
0.8981	High Similarity	NPC476940
0.8981	High Similarity	NPC476939
0.8981	High Similarity	NPC147168
0.8957	High Similarity	NPC173516
0.8951	High Similarity	NPC146991
0.8951	High Similarity	NPC470940
0.8951	High Similarity	NPC469849
0.8929	High Similarity	NPC470938
0.8924	High Similarity	NPC178932
0.8924	High Similarity	NPC30222
0.8903	High Similarity	NPC255414
0.8902	High Similarity	NPC160651
0.8896	High Similarity	NPC472670
0.8896	High Similarity	NPC307781
0.8889	High Similarity	NPC234660
0.8889	High Similarity	NPC419
0.8889	High Similarity	NPC51568
0.8882	High Similarity	NPC335761
0.8882	High Similarity	NPC472653
0.8875	High Similarity	NPC472772
0.8868	High Similarity	NPC264943
0.8841	High Similarity	NPC472282
0.8841	High Similarity	NPC472651
0.8834	High Similarity	NPC476856
0.8834	High Similarity	NPC476857
0.8834	High Similarity	NPC476858
0.8827	High Similarity	NPC5079
0.8827	High Similarity	NPC263432
0.8827	High Similarity	NPC188649
0.882	High Similarity	NPC475226
0.8788	High Similarity	NPC472673
0.8788	High Similarity	NPC472652
0.8774	High Similarity	NPC5676
0.8773	High Similarity	NPC288602
0.8773	High Similarity	NPC88841
0.8765	High Similarity	NPC477402
0.8758	High Similarity	NPC167142
0.8758	High Similarity	NPC36655
0.8758	High Similarity	NPC261597
0.875	High Similarity	NPC44675
0.875	High Similarity	NPC214541
0.8742	High Similarity	NPC268905
0.8734	High Similarity	NPC477404
0.8734	High Similarity	NPC159927
0.8734	High Similarity	NPC469335
0.8734	High Similarity	NPC196864
0.8727	High Similarity	NPC476861
0.8727	High Similarity	NPC476850
0.8727	High Similarity	NPC476853
0.8726	High Similarity	NPC7388
0.8726	High Similarity	NPC476942
0.8726	High Similarity	NPC476941
0.8712	High Similarity	NPC470792
0.8712	High Similarity	NPC329938
0.8712	High Similarity	NPC290400
0.8712	High Similarity	NPC117986
0.8712	High Similarity	NPC96443
0.871	High Similarity	NPC476944
0.8704	High Similarity	NPC474611
0.8704	High Similarity	NPC475295
0.8704	High Similarity	NPC473473
0.8688	High Similarity	NPC253201
0.8688	High Similarity	NPC57998
0.8688	High Similarity	NPC302054
0.8679	High Similarity	NPC18135
0.8675	High Similarity	NPC296558
0.8671	High Similarity	NPC195325
0.8671	High Similarity	NPC472654
0.8667	High Similarity	NPC121995
0.8667	High Similarity	NPC23387
0.8662	High Similarity	NPC470941
0.8662	High Similarity	NPC476938
0.8662	High Similarity	NPC476937
0.8659	High Similarity	NPC476197
0.8659	High Similarity	NPC469846
0.8654	High Similarity	NPC41182
0.865	High Similarity	NPC25255
0.8642	High Similarity	NPC286722
0.8642	High Similarity	NPC195954
0.8642	High Similarity	NPC472283
0.8642	High Similarity	NPC88007
0.8642	High Similarity	NPC187149
0.8642	High Similarity	NPC194499
0.8634	High Similarity	NPC281258
0.8625	High Similarity	NPC44577
0.8625	High Similarity	NPC472672
0.8606	High Similarity	NPC476860
0.8606	High Similarity	NPC123088
0.8598	High Similarity	NPC470939
0.8598	High Similarity	NPC68848
0.8598	High Similarity	NPC18986
0.8598	High Similarity	NPC193798
0.8589	High Similarity	NPC477403
0.8589	High Similarity	NPC472671
0.8581	High Similarity	NPC121158
0.858	High Similarity	NPC477824
0.858	High Similarity	NPC126723
0.858	High Similarity	NPC107646
0.858	High Similarity	NPC209364
0.8571	High Similarity	NPC34421
0.8571	High Similarity	NPC237259
0.8571	High Similarity	NPC98206
0.8563	High Similarity	NPC472765
0.8563	High Similarity	NPC472766
0.8555	High Similarity	NPC247563
0.8555	High Similarity	NPC105395
0.8555	High Similarity	NPC242068
0.8554	High Similarity	NPC475779
0.8544	High Similarity	NPC250228
0.8538	High Similarity	NPC11062
0.8537	High Similarity	NPC470789
0.8537	High Similarity	NPC475381
0.8528	High Similarity	NPC470119
0.8528	High Similarity	NPC475066
0.8528	High Similarity	NPC214495
0.8526	High Similarity	NPC476946
0.8519	High Similarity	NPC141538
0.8519	High Similarity	NPC469850
0.8519	High Similarity	NPC296807
0.8519	High Similarity	NPC92979
0.8519	High Similarity	NPC155939
0.8512	High Similarity	NPC470995
0.8509	High Similarity	NPC294511
0.8509	High Similarity	NPC33938
0.8509	High Similarity	NPC121615
0.8503	High Similarity	NPC270312
0.8503	High Similarity	NPC472764
0.85	High Similarity	NPC476936
0.85	High Similarity	NPC470997
0.8485	Intermediate Similarity	NPC79571
0.848	Intermediate Similarity	NPC470181
0.848	Intermediate Similarity	NPC472665
0.8471	Intermediate Similarity	NPC236004
0.8471	Intermediate Similarity	NPC94763
0.8471	Intermediate Similarity	NPC251865
0.8466	Intermediate Similarity	NPC469485
0.8462	Intermediate Similarity	NPC294512
0.8462	Intermediate Similarity	NPC475237
0.8462	Intermediate Similarity	NPC475641
0.8452	Intermediate Similarity	NPC67003
0.8443	Intermediate Similarity	NPC120012
0.8438	Intermediate Similarity	NPC234494
0.8434	Intermediate Similarity	NPC283209
0.8434	Intermediate Similarity	NPC165218
0.8434	Intermediate Similarity	NPC285567
0.8428	Intermediate Similarity	NPC221809
0.8424	Intermediate Similarity	NPC8389
0.8424	Intermediate Similarity	NPC305016
0.8424	Intermediate Similarity	NPC287559
0.8421	Intermediate Similarity	NPC56953

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 NPC97574 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	1035
0.2-0.3	2210
0.3-0.4	2671
0.4-0.5	1873
0.5-0.6	744
0.6-0.7	258
0.7-0.8	50
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
0.8293	Intermediate Similarity	NPD5760	Phase 2
0.8293	Intermediate Similarity	NPD5761	Phase 2
0.8286	Intermediate Similarity	NPD8434	Phase 2
0.8	Intermediate Similarity	NPD6559	Discontinued
0.7719	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD8313	Approved
0.7709	Intermediate Similarity	NPD8312	Approved
0.7705	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7074	Phase 3
0.767	Intermediate Similarity	NPD3818	Discontinued
0.7627	Intermediate Similarity	NPD7054	Approved
0.7627	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7472	Approved
0.7572	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7228	Approved
0.7556	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5494	Approved
0.7527	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7251	Discontinued
0.7459	Intermediate Similarity	NPD7808	Phase 3
0.7455	Intermediate Similarity	NPD4628	Phase 3
0.7444	Intermediate Similarity	NPD6797	Phase 2
0.7442	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7819	Suspended
0.743	Intermediate Similarity	NPD5844	Phase 1
0.7414	Intermediate Similarity	NPD7075	Discontinued
0.7403	Intermediate Similarity	NPD7240	Approved
0.7387	Intermediate Similarity	NPD8404	Phase 2
0.7384	Intermediate Similarity	NPD37	Approved
0.7356	Intermediate Similarity	NPD4965	Approved
0.7356	Intermediate Similarity	NPD4966	Approved
0.7356	Intermediate Similarity	NPD4967	Phase 2
0.7356	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD8455	Phase 2
0.7308	Intermediate Similarity	NPD6764	Approved
0.7308	Intermediate Similarity	NPD6765	Approved
0.7308	Intermediate Similarity	NPD7685	Pre-registration
0.7306	Intermediate Similarity	NPD7435	Discontinued
0.7288	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD6234	Discontinued
0.7267	Intermediate Similarity	NPD6599	Discontinued
0.7267	Intermediate Similarity	NPD4380	Phase 2
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.72	Intermediate Similarity	NPD5402	Approved
0.7191	Intermediate Similarity	NPD8127	Discontinued
0.7184	Intermediate Similarity	NPD6801	Discontinued
0.7182	Intermediate Similarity	NPD7799	Discontinued
0.7182	Intermediate Similarity	NPD3751	Discontinued
0.7176	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6166	Phase 2
0.7151	Intermediate Similarity	NPD6784	Approved
0.7151	Intermediate Similarity	NPD6785	Approved
0.7151	Intermediate Similarity	NPD3787	Discontinued
0.715	Intermediate Similarity	NPD6778	Approved
0.715	Intermediate Similarity	NPD6782	Approved
0.715	Intermediate Similarity	NPD6777	Approved
0.715	Intermediate Similarity	NPD6779	Approved
0.715	Intermediate Similarity	NPD6781	Approved
0.715	Intermediate Similarity	NPD6776	Approved
0.715	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7783	Phase 2
0.7128	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7696	Phase 3
0.7128	Intermediate Similarity	NPD7697	Approved
0.7128	Intermediate Similarity	NPD7698	Approved
0.7127	Intermediate Similarity	NPD7473	Discontinued
0.7126	Intermediate Similarity	NPD7411	Suspended
0.7121	Intermediate Similarity	NPD8151	Discontinued
0.7119	Intermediate Similarity	NPD3749	Approved
0.7111	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3817	Phase 2
0.7097	Intermediate Similarity	NPD8407	Phase 2
0.7093	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD920	Approved
0.7087	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1934	Approved
0.7085	Intermediate Similarity	NPD7874	Approved
0.7085	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7701	Phase 2
0.7065	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6232	Discontinued
0.7049	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1465	Phase 2
0.7035	Intermediate Similarity	NPD6273	Approved
0.7027	Intermediate Similarity	NPD8368	Discontinued
0.7021	Intermediate Similarity	NPD8150	Discontinued
0.7018	Intermediate Similarity	NPD6799	Approved
0.7005	Intermediate Similarity	NPD8319	Approved
0.7005	Intermediate Similarity	NPD7871	Phase 2
0.7005	Intermediate Similarity	NPD8320	Phase 1
0.7005	Intermediate Similarity	NPD7870	Phase 2
0.7	Intermediate Similarity	NPD6959	Discontinued
0.6994	Remote Similarity	NPD5403	Approved
0.699	Remote Similarity	NPD6823	Phase 2
0.6983	Remote Similarity	NPD919	Approved
0.6977	Remote Similarity	NPD2532	Approved
0.6977	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2534	Approved
0.6977	Remote Similarity	NPD2533	Approved
0.6977	Remote Similarity	NPD5401	Approved
0.6966	Remote Similarity	NPD3882	Suspended
0.6965	Remote Similarity	NPD7801	Approved
0.6964	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7699	Phase 2
0.6959	Remote Similarity	NPD7700	Phase 2
0.6949	Remote Similarity	NPD2801	Approved
0.6941	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3226	Approved
0.6906	Remote Similarity	NPD1247	Approved
0.6891	Remote Similarity	NPD6534	Approved
0.6891	Remote Similarity	NPD6535	Approved
0.6885	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7768	Phase 2
0.6869	Remote Similarity	NPD7680	Approved
0.6864	Remote Similarity	NPD7266	Discontinued
0.6864	Remote Similarity	NPD2346	Discontinued
0.686	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1653	Approved
0.6837	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1549	Phase 2
0.6805	Remote Similarity	NPD2796	Approved
0.6805	Remote Similarity	NPD1551	Phase 2
0.6786	Remote Similarity	NPD7097	Phase 1
0.6784	Remote Similarity	NPD6674	Discontinued
0.6784	Remote Similarity	NPD7497	Discontinued
0.6784	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD8435	Approved
0.6771	Remote Similarity	NPD8361	Approved
0.6771	Remote Similarity	NPD8360	Approved
0.6766	Remote Similarity	NPD1933	Approved
0.6765	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2799	Discontinued
0.6746	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3750	Approved
0.6744	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3926	Phase 2
0.6725	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6100	Approved
0.6706	Remote Similarity	NPD6099	Approved
0.6706	Remote Similarity	NPD2935	Discontinued
0.6699	Remote Similarity	NPD7930	Approved
0.6687	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7319	Approved
0.6686	Remote Similarity	NPD2800	Approved
0.6686	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1243	Approved
0.6685	Remote Similarity	NPD7229	Phase 3
0.6683	Remote Similarity	NPD7583	Approved
0.6683	Remote Similarity	NPD7584	Approved
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD6213	Phase 3
0.6667	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD7907	Approved
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4665	Approved
0.6651	Remote Similarity	NPD4111	Phase 1
0.665	Remote Similarity	NPD7585	Approved
0.6647	Remote Similarity	NPD7033	Discontinued
0.6647	Remote Similarity	NPD3748	Approved
0.6634	Remote Similarity	NPD7999	Approved
0.6631	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1511	Approved
0.6627	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6190	Approved
0.6595	Remote Similarity	NPD5710	Approved
0.6595	Remote Similarity	NPD5711	Approved
0.6592	Remote Similarity	NPD7028	Phase 2
0.6587	Remote Similarity	NPD2313	Discontinued
0.6585	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7239	Suspended
0.657	Remote Similarity	NPD5763	Approved
0.657	Remote Similarity	NPD2344	Approved
0.657	Remote Similarity	NPD5762	Approved
0.6568	Remote Similarity	NPD447	Suspended
0.6554	Remote Similarity	NPD1512	Approved
0.6552	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4110	Phase 3
0.6552	Remote Similarity	NPD7003	Approved
0.655	Remote Similarity	NPD1510	Phase 2
0.655	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8059	Phase 3
0.6512	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1608	Approved
0.6503	Remote Similarity	NPD7507	Approved
0.6495	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD3057	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