NPASS Compound

Structure

NPC265380 OpenBabel07101718312D 49 55 0 0 1 0 0 0 0 0999 V2000 8.6603 1.0000 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 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 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 9.5263 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 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 1.7321 -0.0000 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 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 6.0622 -0.5000 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 7 2 0 0 0 0 1 12 1 0 0 0 0 2 7 1 0 0 0 0 2 15 2 0 0 0 0 3 8 1 0 0 0 0 3 10 2 0 0 0 0 4 9 2 0 0 0 0 4 13 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 33 1 0 0 0 0 7 34 1 0 0 0 0 8 14 2 0 0 0 0 8 22 1 0 0 0 0 9 17 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 35 1 0 0 0 0 11 36 1 0 0 0 0 12 18 2 0 0 0 0 12 37 1 0 0 0 0 13 30 2 0 0 0 0 13 38 1 0 0 0 0 14 47 1 0 0 0 0 15 18 1 0 0 0 0 15 48 1 0 0 0 0 16 6 1 6 0 0 0 16 24 1 0 0 0 0 16 49 1 0 0 0 0 17 25 2 0 0 0 0 17 31 1 0 0 0 0 18 26 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 19 30 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 20 31 2 0 0 0 0 21 25 1 0 0 0 0 21 27 2 0 0 0 0 22 39 2 0 0 0 0 23 40 1 0 0 0 0 24 28 1 0 0 0 0 24 41 1 1 0 0 0 25 42 1 0 0 0 0 26 43 2 0 0 0 0 27 44 1 0 0 0 0 28 29 1 0 0 0 0 28 45 1 6 0 0 0 29 32 1 0 0 0 0 29 46 1 1 0 0 0 30 48 1 0 0 0 0 31 47 1 0 0 0 0 32 21 1 6 0 0 0 32 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	680.1
Volume:	614.656
LogP:	1.775
LogD:	0.987
LogS:	-5.254
# Rotatable Bonds:	3
TPSA:	312.41
# H-Bond Aceptor:	17
# H-Bond Donor:	12
# Rings:	7
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.071
Synthetic Accessibility Score:	4.828
Fsp3:	0.188
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.499
MDCK Permeability:	3.7486752262338996e-06
Pgp-inhibitor:	0.023
Pgp-substrate:	0.346
Human Intestinal Absorption (HIA):	0.994
20% Bioavailability (F20%):	0.182
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	82.71784973144531%
Volume Distribution (VD):	0.609
Pgp-substrate:	39.67662811279297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.247
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.312
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	2.536
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.996
AMES Toxicity:	0.287
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.216
Skin Sensitization:	0.873
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.829
Respiratory Toxicity:	0.006

Download Data

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

Natural Product: NPC265380

Natural Product ID:	NPC265380
*Common Name:**	3-O-Demethylswertipunicoside
IUPAC Name:	1,3,6,7-tetrahydroxy-4-(1,4,6,8-tetrahydroxy-9-oxoxanthen-2-yl)-2-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]xanthen-9-one
Synonyms:	3-O-Demethylswertipunicoside
Standard InCHIKey:	SSBJLFDANWAXNG-KPTZWRFBSA-N
Standard InCHI:	InChI=1S/C32H24O17/c33-6-16-24(41)28(45)29(46)32(49-16)21-25(42)17(31-20(27(21)44)22(39)8-3-10(35)11(36)5-14(8)47-31)9-4-13(38)30-19(23(9)40)26(43)18-12(37)1-7(34)2-15(18)48-30/h1-5,16,24,28-29,32-38,40-42,44-46H,6H2/t16-,24-,28+,29-,32+/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)c(c2cc(O)c3c(c2O)c(=O)c2c(o3)cc(cc2O)O)c2c(c1O)c(=O)c1c(o2)cc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1214707
PubChem CID:	10372399
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1021/jo00025a032]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50072a022]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20677781]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14238	Swertia punicea	Species	Gentianaceae	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	157.8	%	PMID[571061]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	95.5	%	PMID[571061]

☑ 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 NPC265380 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	512
0.1-0.2	2016
0.2-0.3	4416
0.3-0.4	10488
0.4-0.5	7753
0.5-0.6	4189
0.6-0.7	5429
0.7-0.8	4781
0.8-0.85	1661
0.85-0.9	1330
0.9-0.95	117
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC185275
0.9759	High Similarity	NPC471789
0.9701	High Similarity	NPC324742
0.9532	High Similarity	NPC179947
0.9477	High Similarity	NPC473618
0.9394	High Similarity	NPC272560
0.9337	High Similarity	NPC14662
0.9302	High Similarity	NPC49690
0.9286	High Similarity	NPC289396
0.9286	High Similarity	NPC186847
0.9286	High Similarity	NPC472454
0.9286	High Similarity	NPC212038
0.9286	High Similarity	NPC257667
0.9286	High Similarity	NPC81332
0.9286	High Similarity	NPC262580
0.9286	High Similarity	NPC271848
0.9281	High Similarity	NPC475212
0.9277	High Similarity	NPC224851
0.9268	High Similarity	NPC228383
0.9261	High Similarity	NPC477082
0.9253	High Similarity	NPC477083
0.9253	High Similarity	NPC477081
0.9244	High Similarity	NPC150977
0.9226	High Similarity	NPC103307
0.9222	High Similarity	NPC243877
0.9217	High Similarity	NPC477840
0.9212	High Similarity	NPC477841
0.9212	High Similarity	NPC220912
0.9186	High Similarity	NPC117668
0.9172	High Similarity	NPC65333
0.9167	High Similarity	NPC326877
0.9162	High Similarity	NPC320741
0.9162	High Similarity	NPC171985
0.9138	High Similarity	NPC469650
0.9138	High Similarity	NPC261623
0.9138	High Similarity	NPC111490
0.9133	High Similarity	NPC132111
0.9112	High Similarity	NPC74559
0.9107	High Similarity	NPC477154
0.9107	High Similarity	NPC6588
0.9107	High Similarity	NPC260266
0.9107	High Similarity	NPC117854
0.9102	High Similarity	NPC259757
0.9096	High Similarity	NPC476247
0.9096	High Similarity	NPC219927
0.9091	High Similarity	NPC160543
0.9091	High Similarity	NPC472724
0.9091	High Similarity	NPC472720
0.9091	High Similarity	NPC472721
0.9091	High Similarity	NPC93065
0.9091	High Similarity	NPC187632
0.9091	High Similarity	NPC31208
0.9091	High Similarity	NPC469652
0.908	High Similarity	NPC318119
0.9075	High Similarity	NPC125352
0.9059	High Similarity	NPC100251
0.9059	High Similarity	NPC174700
0.9053	High Similarity	NPC107627
0.904	High Similarity	NPC264302
0.9036	High Similarity	NPC142252
0.9036	High Similarity	NPC134783
0.9034	High Similarity	NPC240200
0.9034	High Similarity	NPC290289
0.9034	High Similarity	NPC223534
0.9034	High Similarity	NPC158214
0.9029	High Similarity	NPC112380
0.9029	High Similarity	NPC304322
0.9023	High Similarity	NPC321916
0.9023	High Similarity	NPC129533
0.9023	High Similarity	NPC123259
0.9012	High Similarity	NPC216307
0.9006	High Similarity	NPC98583
0.9	High Similarity	NPC476365
0.8994	High Similarity	NPC295082
0.8988	High Similarity	NPC7688
0.8988	High Similarity	NPC36
0.8988	High Similarity	NPC36916
0.8988	High Similarity	NPC7154
0.8988	High Similarity	NPC125039
0.8988	High Similarity	NPC58223
0.8988	High Similarity	NPC72787
0.8982	High Similarity	NPC474034
0.8982	High Similarity	NPC474033
0.8977	High Similarity	NPC139683
0.8977	High Similarity	NPC269625
0.8977	High Similarity	NPC73929
0.8977	High Similarity	NPC469649
0.8977	High Similarity	NPC47905
0.8977	High Similarity	NPC260521
0.8976	High Similarity	NPC101731
0.8976	High Similarity	NPC188967
0.8976	High Similarity	NPC174953
0.8971	High Similarity	NPC231254
0.897	High Similarity	NPC185526
0.897	High Similarity	NPC36852
0.897	High Similarity	NPC223787
0.897	High Similarity	NPC262286
0.896	High Similarity	NPC476622
0.896	High Similarity	NPC476621
0.896	High Similarity	NPC476620
0.896	High Similarity	NPC476618
0.896	High Similarity	NPC476623
0.896	High Similarity	NPC476619
0.8953	High Similarity	NPC99591
0.8947	High Similarity	NPC121333
0.8947	High Similarity	NPC28589
0.8947	High Similarity	NPC4200
0.8947	High Similarity	NPC248593
0.8941	High Similarity	NPC177480
0.8935	High Similarity	NPC120593
0.8935	High Similarity	NPC128293
0.8933	High Similarity	NPC97924
0.8933	High Similarity	NPC40078
0.8933	High Similarity	NPC471091
0.8929	High Similarity	NPC63438
0.8929	High Similarity	NPC152659
0.8929	High Similarity	NPC41301
0.8929	High Similarity	NPC7483
0.8929	High Similarity	NPC248638
0.8929	High Similarity	NPC272064
0.8929	High Similarity	NPC236521
0.8929	High Similarity	NPC273959
0.8929	High Similarity	NPC146134
0.8927	High Similarity	NPC269046
0.8922	High Similarity	NPC34089
0.8922	High Similarity	NPC305987
0.8922	High Similarity	NPC158188
0.8922	High Similarity	NPC266314
0.8922	High Similarity	NPC26326
0.8922	High Similarity	NPC471211
0.8922	High Similarity	NPC472632
0.8922	High Similarity	NPC113163
0.8922	High Similarity	NPC471212
0.8922	High Similarity	NPC84324
0.8922	High Similarity	NPC196179
0.8922	High Similarity	NPC66618
0.8922	High Similarity	NPC288131
0.8922	High Similarity	NPC165970
0.8916	High Similarity	NPC95936
0.8916	High Similarity	NPC473990
0.8916	High Similarity	NPC154304
0.8916	High Similarity	NPC53545
0.8916	High Similarity	NPC117418
0.8916	High Similarity	NPC190487
0.8916	High Similarity	NPC250214
0.8914	High Similarity	NPC476203
0.8909	High Similarity	NPC138243
0.8902	High Similarity	NPC255799
0.8895	High Similarity	NPC236191
0.8895	High Similarity	NPC149846
0.8895	High Similarity	NPC310794
0.8895	High Similarity	NPC239549
0.8895	High Similarity	NPC51774
0.8889	High Similarity	NPC471416
0.8889	High Similarity	NPC34287
0.8889	High Similarity	NPC279209
0.8889	High Similarity	NPC102277
0.8882	High Similarity	NPC247973
0.8882	High Similarity	NPC474024
0.8882	High Similarity	NPC8965
0.8876	High Similarity	NPC224280
0.8876	High Similarity	NPC50960
0.8876	High Similarity	NPC326520
0.8876	High Similarity	NPC37183
0.8876	High Similarity	NPC234052
0.8876	High Similarity	NPC471788
0.8876	High Similarity	NPC470457
0.8876	High Similarity	NPC62261
0.887	High Similarity	NPC237202
0.887	High Similarity	NPC65489
0.8869	High Similarity	NPC472448
0.8869	High Similarity	NPC25152
0.8869	High Similarity	NPC81679
0.8869	High Similarity	NPC83922
0.8869	High Similarity	NPC52204
0.8862	High Similarity	NPC472630
0.8862	High Similarity	NPC470326
0.8862	High Similarity	NPC14353
0.8862	High Similarity	NPC56085
0.8862	High Similarity	NPC471976
0.8862	High Similarity	NPC472631
0.8862	High Similarity	NPC228785
0.8855	High Similarity	NPC210084
0.8855	High Similarity	NPC78225
0.8855	High Similarity	NPC78103
0.8855	High Similarity	NPC472598
0.8855	High Similarity	NPC99597
0.8855	High Similarity	NPC469584
0.8855	High Similarity	NPC475267
0.8855	High Similarity	NPC474208
0.8855	High Similarity	NPC48208
0.8855	High Similarity	NPC474836
0.8855	High Similarity	NPC162869
0.8855	High Similarity	NPC474055
0.8855	High Similarity	NPC291508
0.8855	High Similarity	NPC156057
0.8851	High Similarity	NPC472387
0.8851	High Similarity	NPC475783
0.8848	High Similarity	NPC113906
0.8848	High Similarity	NPC200761

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 NPC265380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	454
0.1-0.2	1000
0.2-0.3	2058
0.3-0.4	2679
0.4-0.5	1720
0.5-0.6	830
0.6-0.7	266
0.7-0.8	105
0.8-0.85	18
0.85-0.9	20
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8988	High Similarity	NPD6166	Phase 2
0.8988	High Similarity	NPD6168	Clinical (unspecified phase)
0.8988	High Similarity	NPD6167	Clinical (unspecified phase)
0.8947	High Similarity	NPD7993	Clinical (unspecified phase)
0.8698	High Similarity	NPD6959	Discontinued
0.8683	High Similarity	NPD4868	Clinical (unspecified phase)
0.8675	High Similarity	NPD2393	Clinical (unspecified phase)
0.8671	High Similarity	NPD7074	Phase 3
0.8639	High Similarity	NPD5494	Approved
0.8614	High Similarity	NPD1934	Approved
0.8563	High Similarity	NPD7472	Approved
0.8563	High Similarity	NPD2801	Approved
0.8506	High Similarity	NPD7054	Approved
0.8506	High Similarity	NPD5844	Phase 1
0.8494	Intermediate Similarity	NPD4380	Phase 2
0.8448	Intermediate Similarity	NPD3818	Discontinued
0.8418	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD7808	Phase 3
0.8409	Intermediate Similarity	NPD6797	Phase 2
0.8362	Intermediate Similarity	NPD7251	Discontinued
0.8343	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD3882	Suspended
0.8235	Intermediate Similarity	NPD1465	Phase 2
0.8218	Intermediate Similarity	NPD6232	Discontinued
0.8198	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8192	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7473	Discontinued
0.8167	Intermediate Similarity	NPD8313	Approved
0.8167	Intermediate Similarity	NPD8312	Approved
0.8133	Intermediate Similarity	NPD1511	Approved
0.8092	Intermediate Similarity	NPD7075	Discontinued
0.8036	Intermediate Similarity	NPD1512	Approved
0.8035	Intermediate Similarity	NPD7768	Phase 2
0.8023	Intermediate Similarity	NPD7819	Suspended
0.8012	Intermediate Similarity	NPD7411	Suspended
0.7977	Intermediate Similarity	NPD5402	Approved
0.7977	Intermediate Similarity	NPD3817	Phase 2
0.7976	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD6559	Discontinued
0.7939	Intermediate Similarity	NPD1549	Phase 2
0.7919	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD8151	Discontinued
0.7879	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6801	Discontinued
0.7816	Intermediate Similarity	NPD8455	Phase 2
0.7784	Intermediate Similarity	NPD3749	Approved
0.7753	Intermediate Similarity	NPD1247	Approved
0.7735	Intermediate Similarity	NPD3751	Discontinued
0.7709	Intermediate Similarity	NPD3787	Discontinued
0.7706	Intermediate Similarity	NPD7390	Discontinued
0.7667	Intermediate Similarity	NPD3926	Phase 2
0.7651	Intermediate Similarity	NPD1510	Phase 2
0.7638	Intermediate Similarity	NPD7783	Phase 2
0.7638	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD7228	Approved
0.7605	Intermediate Similarity	NPD2796	Approved
0.7594	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD6778	Approved
0.7577	Intermediate Similarity	NPD6781	Approved
0.7577	Intermediate Similarity	NPD6779	Approved
0.7577	Intermediate Similarity	NPD6782	Approved
0.7577	Intermediate Similarity	NPD6777	Approved
0.7577	Intermediate Similarity	NPD6780	Approved
0.7577	Intermediate Similarity	NPD6776	Approved
0.7572	Intermediate Similarity	NPD5403	Approved
0.7558	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7698	Approved
0.7551	Intermediate Similarity	NPD7696	Phase 3
0.7551	Intermediate Similarity	NPD7697	Approved
0.7515	Intermediate Similarity	NPD1613	Approved
0.7515	Intermediate Similarity	NPD943	Approved
0.7515	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD6799	Approved
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7462	Intermediate Similarity	NPD7435	Discontinued
0.746	Intermediate Similarity	NPD8150	Discontinued
0.7457	Intermediate Similarity	NPD5401	Approved
0.7444	Intermediate Similarity	NPD919	Approved
0.7444	Intermediate Similarity	NPD6234	Discontinued
0.7443	Intermediate Similarity	NPD6599	Discontinued
0.7429	Intermediate Similarity	NPD1653	Approved
0.741	Intermediate Similarity	NPD1240	Approved
0.7398	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD2935	Discontinued
0.7385	Intermediate Similarity	NPD7699	Phase 2
0.7385	Intermediate Similarity	NPD7700	Phase 2
0.7384	Intermediate Similarity	NPD6190	Approved
0.7371	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2800	Approved
0.7363	Intermediate Similarity	NPD7199	Phase 2
0.736	Intermediate Similarity	NPD37	Approved
0.7356	Intermediate Similarity	NPD2533	Approved
0.7356	Intermediate Similarity	NPD2534	Approved
0.7356	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4966	Approved
0.7327	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7874	Approved
0.7326	Intermediate Similarity	NPD3750	Approved
0.7323	Intermediate Similarity	NPD6823	Phase 2
0.7321	Intermediate Similarity	NPD1607	Approved
0.732	Intermediate Similarity	NPD6534	Approved
0.732	Intermediate Similarity	NPD6535	Approved
0.7317	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD7801	Approved
0.7288	Intermediate Similarity	NPD3226	Approved
0.7288	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7240	Approved
0.7287	Intermediate Similarity	NPD7685	Pre-registration
0.7277	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD230	Phase 1
0.7257	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3027	Phase 3
0.7225	Intermediate Similarity	NPD4628	Phase 3
0.7209	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD920	Approved
0.7164	Intermediate Similarity	NPD8320	Phase 1
0.7164	Intermediate Similarity	NPD8319	Approved
0.7159	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD5953	Discontinued
0.7135	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5406	Approved
0.7093	Intermediate Similarity	NPD5405	Approved
0.7093	Intermediate Similarity	NPD5404	Approved
0.7093	Intermediate Similarity	NPD1551	Phase 2
0.7093	Intermediate Similarity	NPD5408	Approved
0.7092	Intermediate Similarity	NPD6213	Phase 3
0.7092	Intermediate Similarity	NPD6212	Phase 3
0.7092	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8127	Discontinued
0.7069	Intermediate Similarity	NPD1243	Approved
0.7068	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4908	Phase 1
0.7062	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD447	Suspended
0.7056	Intermediate Similarity	NPD4360	Phase 2
0.7056	Intermediate Similarity	NPD4363	Phase 3
0.7052	Intermediate Similarity	NPD2346	Discontinued
0.7045	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7286	Phase 2
0.7035	Intermediate Similarity	NPD3748	Approved
0.7035	Intermediate Similarity	NPD2799	Discontinued
0.7018	Intermediate Similarity	NPD6651	Approved
0.701	Intermediate Similarity	NPD7584	Approved
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7458	Discontinued
0.6994	Remote Similarity	NPD6100	Approved
0.6994	Remote Similarity	NPD6099	Approved
0.6989	Remote Similarity	NPD2309	Approved
0.6982	Remote Similarity	NPD2313	Discontinued
0.6979	Remote Similarity	NPD7549	Discontinued
0.6978	Remote Similarity	NPD6844	Discontinued
0.6952	Remote Similarity	NPD7229	Phase 3
0.6952	Remote Similarity	NPD5710	Approved
0.6952	Remote Similarity	NPD5711	Approved
0.6946	Remote Similarity	NPD7680	Approved
0.6939	Remote Similarity	NPD4287	Approved
0.6932	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD9494	Approved
0.6901	Remote Similarity	NPD7907	Approved
0.6895	Remote Similarity	NPD7177	Discontinued
0.6887	Remote Similarity	NPD4111	Phase 1
0.6887	Remote Similarity	NPD4665	Approved
0.6882	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1933	Approved
0.6857	Remote Similarity	NPD7266	Discontinued
0.6848	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD8166	Discontinued
0.6836	Remote Similarity	NPD7003	Approved
0.6825	Remote Similarity	NPD5242	Approved
0.682	Remote Similarity	NPD8059	Phase 3
0.682	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD5353	Approved
0.6805	Remote Similarity	NPD2861	Phase 2
0.6796	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6674	Discontinued
0.6766	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD8285	Discontinued
0.6747	Remote Similarity	NPD1610	Phase 2
0.6744	Remote Similarity	NPD6233	Phase 2
0.674	Remote Similarity	NPD6273	Approved
0.6739	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD8053	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