NPASS Compound

Structure

NPC170432 OpenBabel07101718312D 28 30 0 0 1 0 0 0 0 0999 V2000 -2.1369 3.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 2.4781 0.0000 C 0 0 2 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 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 2 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8005 2.5827 0.0000 C 0 0 2 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 -4.2072 1.6691 0.0000 C 0 0 1 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 -4.3301 -0.5000 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 -0.0000 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 -4.3005 3.4487 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 -5.1854 1.4612 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 -5.1962 -0.0000 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 -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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 18 1 0 0 0 0 4 6 2 0 0 0 0 4 26 1 0 0 0 0 5 1 1 6 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 3 1 1 0 0 0 7 11 1 0 0 0 0 7 27 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 24 2 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 16 28 1 0 0 0 0 17 27 1 0 0 0 0 17 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.15
Volume:	368.338
LogP:	-0.55
LogD:	0.32
LogS:	-0.93
# Rotatable Bonds:	5
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.26
Synthetic Accessibility Score:	4.818
Fsp3:	0.824
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.12
MDCK Permeability:	0.0001830918772611767
Pgp-inhibitor:	0.001
Pgp-substrate:	0.737
Human Intestinal Absorption (HIA):	0.913
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206
Plasma Protein Binding (PPB):	24.802833557128906%
Volume Distribution (VD):	0.314
Pgp-substrate:	43.26189041137695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.253
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.559
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.03

ADMET: Excretion

Clearance (CL):	1.331
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.328
Drug-inuced Liver Injury (DILI):	0.638
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.059
Carcinogencity:	0.244
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.647

Download Data

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

Natural Product: NPC170432

Natural Product ID:	NPC170432
*Common Name:**	6Beta-Hydroxyloganin
IUPAC Name:	methyl (1S,4aS,5S,6R,7R,7aR)-5,6-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:	6Beta-Hydroxyloganin
Standard InCHIKey:	QDEYKGKBMCIYCT-AZPIFPLPSA-N
Standard InCHI:	InChI=1S/C17H26O11/c1-5-8-9(12(21)10(5)19)6(15(24)25-2)4-26-16(8)28-17-14(23)13(22)11(20)7(3-18)27-17/h4-5,7-14,16-23H,3H2,1-2H3/t5-,7-,8-,9-,10-,11-,12+,13+,14-,16+,17+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@@H](C)[C@H]([C@H]3O)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492202
PubChem CID:	158641
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO33172	nyctanthes arbortristis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791475]
NPO33172	nyctanthes arbortristis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22608855]

☑ 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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	42.22	%	PMID[547516]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	65.77	%	PMID[547516]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	30.81	%	PMID[547516]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Survival	<	28.0	day	PMID[547516]

☑ 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 NPC170432 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	230
0.1-0.2	1522
0.2-0.3	5342
0.3-0.4	9760
0.4-0.5	12293
0.5-0.6	7551
0.6-0.7	5326
0.7-0.8	613
0.8-0.85	29
0.85-0.9	12
0.9-0.95	9
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9794	High Similarity	NPC475928
0.9697	High Similarity	NPC197813
0.9697	High Similarity	NPC80338
0.9697	High Similarity	NPC148270
0.9691	High Similarity	NPC474730
0.9691	High Similarity	NPC35185
0.9691	High Similarity	NPC4899
0.9691	High Similarity	NPC177013
0.9604	High Similarity	NPC193741
0.9592	High Similarity	NPC37240
0.9417	High Similarity	NPC475851
0.9417	High Similarity	NPC475924
0.9406	High Similarity	NPC110701
0.94	High Similarity	NPC127235
0.9388	High Similarity	NPC3488
0.9388	High Similarity	NPC287539
0.9293	High Similarity	NPC106668
0.92	High Similarity	NPC27687
0.898	High Similarity	NPC161293
0.8725	High Similarity	NPC80144
0.8687	High Similarity	NPC93869
0.8687	High Similarity	NPC6765
0.8627	High Similarity	NPC67296
0.8614	High Similarity	NPC37866
0.8614	High Similarity	NPC49833
0.8614	High Similarity	NPC249171
0.8586	High Similarity	NPC274588
0.8586	High Similarity	NPC63897
0.8544	High Similarity	NPC304163
0.8515	High Similarity	NPC304445
0.8515	High Similarity	NPC236580
0.8462	Intermediate Similarity	NPC473148
0.8416	Intermediate Similarity	NPC170527
0.8333	Intermediate Similarity	NPC261372
0.8333	Intermediate Similarity	NPC263674
0.8333	Intermediate Similarity	NPC58267
0.8302	Intermediate Similarity	NPC41681
0.8283	Intermediate Similarity	NPC231710
0.8283	Intermediate Similarity	NPC270908
0.8283	Intermediate Similarity	NPC120021
0.8283	Intermediate Similarity	NPC65665
0.8283	Intermediate Similarity	NPC470573
0.8283	Intermediate Similarity	NPC216826
0.8269	Intermediate Similarity	NPC28304
0.8269	Intermediate Similarity	NPC298255
0.8269	Intermediate Similarity	NPC216911
0.8235	Intermediate Similarity	NPC474297
0.8235	Intermediate Similarity	NPC284063
0.82	Intermediate Similarity	NPC235051
0.819	Intermediate Similarity	NPC261117
0.819	Intermediate Similarity	NPC310804
0.8173	Intermediate Similarity	NPC476320
0.8173	Intermediate Similarity	NPC476211
0.8173	Intermediate Similarity	NPC22149
0.8173	Intermediate Similarity	NPC255677
0.8173	Intermediate Similarity	NPC306344
0.8155	Intermediate Similarity	NPC472290
0.8155	Intermediate Similarity	NPC471150
0.8155	Intermediate Similarity	NPC86843
0.8137	Intermediate Similarity	NPC167893
0.8113	Intermediate Similarity	NPC329834
0.81	Intermediate Similarity	NPC246173
0.81	Intermediate Similarity	NPC117596
0.8095	Intermediate Similarity	NPC27474
0.8095	Intermediate Similarity	NPC476230
0.802	Intermediate Similarity	NPC472125
0.802	Intermediate Similarity	NPC472124
0.802	Intermediate Similarity	NPC66504
0.802	Intermediate Similarity	NPC472126
0.8019	Intermediate Similarity	NPC250545
0.8019	Intermediate Similarity	NPC195510
0.8019	Intermediate Similarity	NPC13171
0.8019	Intermediate Similarity	NPC222062
0.8	Intermediate Similarity	NPC473146
0.8	Intermediate Similarity	NPC471381
0.8	Intermediate Similarity	NPC186861
0.798	Intermediate Similarity	NPC31349
0.7961	Intermediate Similarity	NPC472873
0.7944	Intermediate Similarity	NPC234304
0.7944	Intermediate Similarity	NPC284929
0.7944	Intermediate Similarity	NPC197541
0.7944	Intermediate Similarity	NPC118761
0.7944	Intermediate Similarity	NPC329704
0.7944	Intermediate Similarity	NPC267869
0.7941	Intermediate Similarity	NPC61201
0.7931	Intermediate Similarity	NPC473228
0.7931	Intermediate Similarity	NPC470829
0.7925	Intermediate Similarity	NPC476228
0.7921	Intermediate Similarity	NPC307699
0.7905	Intermediate Similarity	NPC472015
0.7885	Intermediate Similarity	NPC241911
0.7879	Intermediate Similarity	NPC470657
0.787	Intermediate Similarity	NPC86095
0.7864	Intermediate Similarity	NPC71589
0.7851	Intermediate Similarity	NPC213634
0.7843	Intermediate Similarity	NPC294643
0.7843	Intermediate Similarity	NPC274274
0.7843	Intermediate Similarity	NPC473150
0.7826	Intermediate Similarity	NPC13710
0.7822	Intermediate Similarity	NPC50464
0.7807	Intermediate Similarity	NPC277583
0.7798	Intermediate Similarity	NPC54737
0.7748	Intermediate Similarity	NPC59489
0.7748	Intermediate Similarity	NPC139838
0.7714	Intermediate Similarity	NPC306041
0.7685	Intermediate Similarity	NPC471599
0.7679	Intermediate Similarity	NPC50223
0.767	Intermediate Similarity	NPC470379
0.767	Intermediate Similarity	NPC470373
0.7664	Intermediate Similarity	NPC244878
0.7652	Intermediate Similarity	NPC88945
0.7647	Intermediate Similarity	NPC92974
0.7647	Intermediate Similarity	NPC215556
0.7647	Intermediate Similarity	NPC93190
0.7642	Intermediate Similarity	NPC155529
0.7632	Intermediate Similarity	NPC132668
0.7624	Intermediate Similarity	NPC186148
0.7619	Intermediate Similarity	NPC101051
0.7619	Intermediate Similarity	NPC163228
0.7611	Intermediate Similarity	NPC471251
0.76	Intermediate Similarity	NPC158350
0.7593	Intermediate Similarity	NPC20673
0.7593	Intermediate Similarity	NPC219038
0.7589	Intermediate Similarity	NPC208307
0.7589	Intermediate Similarity	NPC118225
0.7586	Intermediate Similarity	NPC473304
0.7573	Intermediate Similarity	NPC216284
0.7573	Intermediate Similarity	NPC206614
0.7573	Intermediate Similarity	NPC474323
0.7573	Intermediate Similarity	NPC54065
0.7573	Intermediate Similarity	NPC303451
0.7573	Intermediate Similarity	NPC6414
0.7573	Intermediate Similarity	NPC297474
0.757	Intermediate Similarity	NPC151093
0.757	Intermediate Similarity	NPC45125
0.7568	Intermediate Similarity	NPC254538
0.7568	Intermediate Similarity	NPC474285
0.7549	Intermediate Similarity	NPC177629
0.7549	Intermediate Similarity	NPC207114
0.7549	Intermediate Similarity	NPC58219
0.7549	Intermediate Similarity	NPC217983
0.7549	Intermediate Similarity	NPC79549
0.7547	Intermediate Similarity	NPC54731
0.7547	Intermediate Similarity	NPC476009
0.7547	Intermediate Similarity	NPC91771
0.7547	Intermediate Similarity	NPC142529
0.7542	Intermediate Similarity	NPC281840
0.7524	Intermediate Similarity	NPC190294
0.7523	Intermediate Similarity	NPC94919
0.7522	Intermediate Similarity	NPC124053
0.7522	Intermediate Similarity	NPC41551
0.7522	Intermediate Similarity	NPC114961
0.7522	Intermediate Similarity	NPC27551
0.7521	Intermediate Similarity	NPC471249
0.75	Intermediate Similarity	NPC219900
0.75	Intermediate Similarity	NPC29821
0.75	Intermediate Similarity	NPC392
0.75	Intermediate Similarity	NPC471855
0.75	Intermediate Similarity	NPC133888
0.75	Intermediate Similarity	NPC177524
0.75	Intermediate Similarity	NPC63193
0.75	Intermediate Similarity	NPC229752
0.75	Intermediate Similarity	NPC27363
0.75	Intermediate Similarity	NPC475960
0.75	Intermediate Similarity	NPC57304
0.75	Intermediate Similarity	NPC184463
0.75	Intermediate Similarity	NPC171360
0.75	Intermediate Similarity	NPC293001
0.75	Intermediate Similarity	NPC35959
0.7479	Intermediate Similarity	NPC42675
0.7477	Intermediate Similarity	NPC474313
0.7477	Intermediate Similarity	NPC311904
0.7477	Intermediate Similarity	NPC181151
0.7477	Intermediate Similarity	NPC44004
0.7476	Intermediate Similarity	NPC155935
0.7476	Intermediate Similarity	NPC22918
0.7459	Intermediate Similarity	NPC152091
0.7456	Intermediate Similarity	NPC213320
0.7456	Intermediate Similarity	NPC122339
0.7456	Intermediate Similarity	NPC474750
0.7456	Intermediate Similarity	NPC63244
0.7453	Intermediate Similarity	NPC36954
0.7453	Intermediate Similarity	NPC476053
0.7451	Intermediate Similarity	NPC74139
0.7438	Intermediate Similarity	NPC318135
0.7436	Intermediate Similarity	NPC78836
0.7434	Intermediate Similarity	NPC471250
0.7431	Intermediate Similarity	NPC98859
0.7431	Intermediate Similarity	NPC4637
0.7431	Intermediate Similarity	NPC471401
0.7431	Intermediate Similarity	NPC150923
0.7429	Intermediate Similarity	NPC475912
0.7429	Intermediate Similarity	NPC476300
0.7429	Intermediate Similarity	NPC212486
0.7422	Intermediate Similarity	NPC75616
0.7419	Intermediate Similarity	NPC173347
0.7404	Intermediate Similarity	NPC19087
0.7404	Intermediate Similarity	NPC35809
0.7402	Intermediate Similarity	NPC289700
0.7402	Intermediate Similarity	NPC127656

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 NPC170432 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	2086
0.2-0.3	3831
0.3-0.4	1988
0.4-0.5	584
0.5-0.6	300
0.6-0.7	129
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.75	Intermediate Similarity	NPD6686	Approved
0.7377	Intermediate Similarity	NPD7507	Approved
0.7328	Intermediate Similarity	NPD8133	Approved
0.7241	Intermediate Similarity	NPD6053	Discontinued
0.72	Intermediate Similarity	NPD7319	Approved
0.719	Intermediate Similarity	NPD7503	Approved
0.7105	Intermediate Similarity	NPD6412	Phase 2
0.7075	Intermediate Similarity	NPD46	Approved
0.7075	Intermediate Similarity	NPD6698	Approved
0.7049	Intermediate Similarity	NPD8513	Phase 3
0.7009	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8515	Approved
0.6911	Remote Similarity	NPD8517	Approved
0.6911	Remote Similarity	NPD8516	Approved
0.6803	Remote Similarity	NPD7327	Approved
0.6803	Remote Similarity	NPD7328	Approved
0.6786	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6371	Approved
0.6774	Remote Similarity	NPD8033	Approved
0.6748	Remote Similarity	NPD7516	Approved
0.672	Remote Similarity	NPD6370	Approved
0.6719	Remote Similarity	NPD7736	Approved
0.6694	Remote Similarity	NPD8377	Approved
0.6694	Remote Similarity	NPD8294	Approved
0.6694	Remote Similarity	NPD6319	Approved
0.6641	Remote Similarity	NPD8293	Discontinued
0.664	Remote Similarity	NPD8378	Approved
0.664	Remote Similarity	NPD8335	Approved
0.664	Remote Similarity	NPD8379	Approved
0.664	Remote Similarity	NPD8296	Approved
0.664	Remote Similarity	NPD8380	Approved
0.6638	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7492	Approved
0.6585	Remote Similarity	NPD6009	Approved
0.6585	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6616	Approved
0.656	Remote Similarity	NPD6054	Approved
0.6545	Remote Similarity	NPD7983	Approved
0.6542	Remote Similarity	NPD4249	Approved
0.6535	Remote Similarity	NPD7829	Approved
0.6535	Remote Similarity	NPD7830	Approved
0.6532	Remote Similarity	NPD7641	Discontinued
0.6529	Remote Similarity	NPD6882	Approved
0.6514	Remote Similarity	NPD1695	Approved
0.6512	Remote Similarity	NPD7078	Approved
0.6508	Remote Similarity	NPD6015	Approved
0.6508	Remote Similarity	NPD6016	Approved
0.6496	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4250	Approved
0.6481	Remote Similarity	NPD4251	Approved
0.6476	Remote Similarity	NPD6435	Approved
0.6475	Remote Similarity	NPD4632	Approved
0.6457	Remote Similarity	NPD5988	Approved
0.6457	Remote Similarity	NPD8080	Discontinued
0.6455	Remote Similarity	NPD7838	Discovery
0.6452	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8451	Approved
0.6429	Remote Similarity	NPD6059	Approved
0.6417	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7642	Approved
0.6406	Remote Similarity	NPD8328	Phase 3
0.6393	Remote Similarity	NPD8297	Approved
0.6385	Remote Similarity	NPD8448	Approved
0.6385	Remote Similarity	NPD8074	Phase 3
0.6378	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7115	Discovery
0.6311	Remote Similarity	NPD6650	Approved
0.6311	Remote Similarity	NPD6649	Approved
0.6306	Remote Similarity	NPD5785	Approved
0.6296	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5368	Approved
0.6281	Remote Similarity	NPD6372	Approved
0.6281	Remote Similarity	NPD6373	Approved
0.6262	Remote Similarity	NPD7154	Phase 3
0.6262	Remote Similarity	NPD5362	Discontinued
0.625	Remote Similarity	NPD8267	Approved
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD8269	Approved
0.625	Remote Similarity	NPD8268	Approved
0.625	Remote Similarity	NPD8266	Approved
0.625	Remote Similarity	NPD8444	Approved
0.6241	Remote Similarity	NPD8391	Approved
0.6241	Remote Similarity	NPD8392	Approved
0.6241	Remote Similarity	NPD8390	Approved
0.6239	Remote Similarity	NPD5786	Approved
0.6231	Remote Similarity	NPD8340	Approved
0.6231	Remote Similarity	NPD8341	Approved
0.6231	Remote Similarity	NPD8299	Approved
0.6231	Remote Similarity	NPD8342	Approved
0.6207	Remote Similarity	NPD7638	Approved
0.6207	Remote Similarity	NPD4225	Approved
0.6204	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6881	Approved
0.6198	Remote Similarity	NPD6899	Approved
0.6195	Remote Similarity	NPD5778	Approved
0.6195	Remote Similarity	NPD5779	Approved
0.6194	Remote Similarity	NPD7260	Phase 2
0.6174	Remote Similarity	NPD7839	Suspended
0.6167	Remote Similarity	NPD7128	Approved
0.6167	Remote Similarity	NPD6008	Approved
0.6167	Remote Similarity	NPD6675	Approved
0.6167	Remote Similarity	NPD5739	Approved
0.6167	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD7640	Approved
0.6154	Remote Similarity	NPD7639	Approved
0.6148	Remote Similarity	NPD6012	Approved
0.6148	Remote Similarity	NPD6013	Approved
0.6148	Remote Similarity	NPD6014	Approved
0.6147	Remote Similarity	NPD5363	Approved
0.614	Remote Similarity	NPD5282	Discontinued
0.6132	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD5983	Phase 2
0.6116	Remote Similarity	NPD5701	Approved
0.6098	Remote Similarity	NPD4634	Approved
0.6098	Remote Similarity	NPD7102	Approved
0.6098	Remote Similarity	NPD7290	Approved
0.6098	Remote Similarity	NPD6883	Approved
0.6095	Remote Similarity	NPD4238	Approved
0.6095	Remote Similarity	NPD4802	Phase 2
0.609	Remote Similarity	NPD8336	Approved
0.609	Remote Similarity	NPD8337	Approved
0.6075	Remote Similarity	NPD5369	Approved
0.6071	Remote Similarity	NPD6101	Approved
0.6071	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7320	Approved
0.6066	Remote Similarity	NPD6011	Approved
0.6053	Remote Similarity	NPD6399	Phase 3
0.605	Remote Similarity	NPD8083	Approved
0.605	Remote Similarity	NPD8138	Approved
0.605	Remote Similarity	NPD8084	Approved
0.605	Remote Similarity	NPD8086	Approved
0.605	Remote Similarity	NPD8085	Approved
0.605	Remote Similarity	NPD8082	Approved
0.605	Remote Similarity	NPD8139	Approved
0.6048	Remote Similarity	NPD6869	Approved
0.6048	Remote Similarity	NPD6847	Approved
0.6048	Remote Similarity	NPD6617	Approved
0.6048	Remote Similarity	NPD8130	Phase 1
0.6031	Remote Similarity	NPD6067	Discontinued
0.6031	Remote Similarity	NPD7604	Phase 2
0.6029	Remote Similarity	NPD6845	Suspended
0.6019	Remote Similarity	NPD4270	Approved
0.6019	Remote Similarity	NPD4269	Approved
0.6016	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8275	Approved
0.6	Remote Similarity	NPD8276	Approved
0.5983	Remote Similarity	NPD6084	Phase 2
0.5983	Remote Similarity	NPD6083	Phase 2
0.5981	Remote Similarity	NPD4821	Approved
0.5981	Remote Similarity	NPD4820	Approved
0.5981	Remote Similarity	NPD4819	Approved
0.5981	Remote Similarity	NPD4822	Approved
0.597	Remote Similarity	NPD6033	Approved
0.5968	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD5344	Discontinued
0.5965	Remote Similarity	NPD6411	Approved
0.5965	Remote Similarity	NPD8034	Phase 2
0.5965	Remote Similarity	NPD8035	Phase 2
0.5963	Remote Similarity	NPD4788	Approved
0.595	Remote Similarity	NPD8081	Approved
0.5948	Remote Similarity	NPD5695	Phase 3
0.5943	Remote Similarity	NPD4268	Approved
0.5943	Remote Similarity	NPD4271	Approved
0.594	Remote Similarity	NPD6336	Discontinued
0.5932	Remote Similarity	NPD5696	Approved
0.5917	Remote Similarity	NPD5211	Phase 2
0.5912	Remote Similarity	NPD8338	Approved
0.5909	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD8393	Approved
0.5882	Remote Similarity	NPD5956	Approved
0.5882	Remote Similarity	NPD5285	Approved
0.5882	Remote Similarity	NPD4696	Approved
0.5882	Remote Similarity	NPD5286	Approved
0.5878	Remote Similarity	NPD6921	Approved
0.5859	Remote Similarity	NPD6274	Approved
0.5847	Remote Similarity	NPD4755	Approved
0.5833	Remote Similarity	NPD4252	Approved
0.5828	Remote Similarity	NPD7685	Pre-registration
0.5826	Remote Similarity	NPD7637	Suspended
0.582	Remote Similarity	NPD5141	Approved
0.5818	Remote Similarity	NPD5332	Approved
0.5818	Remote Similarity	NPD3669	Approved
0.5818	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5331	Approved
0.5794	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD5224	Approved
0.5785	Remote Similarity	NPD4633	Approved
0.5785	Remote Similarity	NPD5225	Approved
0.5785	Remote Similarity	NPD5226	Approved
0.5785	Remote Similarity	NPD7632	Discontinued
0.578	Remote Similarity	NPD1780	Approved
0.578	Remote Similarity	NPD1779	Approved
0.578	Remote Similarity	NPD4790	Discontinued
0.5776	Remote Similarity	NPD8171	Discontinued
0.5752	Remote Similarity	NPD7524	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