NPASS Compound

Structure

NPC169387 OpenBabel07101719242D 26 30 0 0 1 0 0 0 0 0999 V2000 -2.5981 4.5000 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 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 0.0000 -1.0000 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 -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 5.0029 -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 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 0.8660 0.5000 0.0000 C 0 0 1 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 3.4641 -1.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 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 -2.5981 3.5000 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 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 21 1 0 0 0 0 7 12 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 25 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 12 18 2 0 0 0 0 13 14 1 0 0 0 0 14 7 1 1 0 0 0 14 21 1 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.13
Volume:	348.187
LogP:	2.609
LogD:	2.844
LogS:	-4.618
# Rotatable Bonds:	2
TPSA:	57.23
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.831
Synthetic Accessibility Score:	2.979
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.909
MDCK Permeability:	3.408387055969797e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.738
Plasma Protein Binding (PPB):	94.44005584716797%
Volume Distribution (VD):	1.06
Pgp-substrate:	4.860580921173096%

ADMET: Metabolism

CYP1A2-inhibitor:	0.586
CYP1A2-substrate:	0.883
CYP2C19-inhibitor:	0.931
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.599
CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.648
CYP2D6-substrate:	0.853
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.73

ADMET: Excretion

Clearance (CL):	6.708
Half-life (T1/2):	0.217

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.707
Drug-inuced Liver Injury (DILI):	0.637
AMES Toxicity:	0.119
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.085
Carcinogencity:	0.923
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC169387

Natural Product ID:	NPC169387
*Common Name:**	DESORMZUMYIKSG-AWEZNQCLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DESORMZUMYIKSG-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C20H19NO5/c1-23-15-4-3-12-7-14-13-9-17-16(25-10-26-17)8-11(13)5-6-21(14)20(22)18(12)19(15)24-2/h3-4,8-9,14H,5-7,10H2,1-2H3/t14-/m0/s1
SMILES:	COc1ccc2C[C@H]3c4cc5c(cc4CCN3C(=O)c2c1OC)OCO5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468974
PubChem CID:	133161
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*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
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18396905]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18396905]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1525	Pericampylus glaucus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1525	Pericampylus glaucus	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	1

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	3400000.0	nM	PMID[450825]
NPT27	Others	Unspecified		CC50	>	3400000.0	nM	PMID[450825]

☑ 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 NPC169387 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	326
0.1-0.2	1666
0.2-0.3	6200
0.3-0.4	11381
0.4-0.5	4773
0.5-0.6	12407
0.6-0.7	5229
0.7-0.8	624
0.8-0.85	49
0.85-0.9	34
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477259
0.9653	High Similarity	NPC477258
0.9598	High Similarity	NPC24228
0.9581	High Similarity	NPC222524
0.9353	High Similarity	NPC27887
0.9302	High Similarity	NPC116007
0.9143	High Similarity	NPC208890
0.908	High Similarity	NPC83511
0.8933	High Similarity	NPC226708
0.8729	High Similarity	NPC469815
0.8729	High Similarity	NPC469816
0.8689	High Similarity	NPC14622
0.8689	High Similarity	NPC70290
0.8689	High Similarity	NPC124302
0.8689	High Similarity	NPC215098
0.8689	High Similarity	NPC73020
0.8689	High Similarity	NPC46744
0.8683	High Similarity	NPC41178
0.8683	High Similarity	NPC216459
0.8683	High Similarity	NPC138487
0.8631	High Similarity	NPC146288
0.8621	High Similarity	NPC303581
0.8621	High Similarity	NPC67978
0.8602	High Similarity	NPC202771
0.8602	High Similarity	NPC2173
0.8602	High Similarity	NPC119818
0.8602	High Similarity	NPC328700
0.8595	High Similarity	NPC226652
0.8595	High Similarity	NPC72788
0.8595	High Similarity	NPC314100
0.8595	High Similarity	NPC120671
0.8579	High Similarity	NPC125924
0.8541	High Similarity	NPC207239
0.8523	High Similarity	NPC308267
0.8521	High Similarity	NPC234392
0.8521	High Similarity	NPC31311
0.84	Intermediate Similarity	NPC241055
0.8387	Intermediate Similarity	NPC71124
0.8343	Intermediate Similarity	NPC233029
0.8343	Intermediate Similarity	NPC210148
0.8342	Intermediate Similarity	NPC5374
0.8333	Intermediate Similarity	NPC231198
0.8333	Intermediate Similarity	NPC232514
0.8333	Intermediate Similarity	NPC276944
0.8333	Intermediate Similarity	NPC238530
0.8324	Intermediate Similarity	NPC121400
0.8323	Intermediate Similarity	NPC475959
0.8316	Intermediate Similarity	NPC268077
0.8295	Intermediate Similarity	NPC86469
0.827	Intermediate Similarity	NPC254957
0.8263	Intermediate Similarity	NPC51957
0.8263	Intermediate Similarity	NPC476144
0.8263	Intermediate Similarity	NPC207971
0.8263	Intermediate Similarity	NPC106295
0.8263	Intermediate Similarity	NPC16107
0.8263	Intermediate Similarity	NPC210437
0.8218	Intermediate Similarity	NPC153631
0.8214	Intermediate Similarity	NPC7467
0.8208	Intermediate Similarity	NPC106786
0.8207	Intermediate Similarity	NPC166979
0.8187	Intermediate Similarity	NPC102760
0.8176	Intermediate Similarity	NPC119669
0.8171	Intermediate Similarity	NPC59567
0.814	Intermediate Similarity	NPC93593
0.8125	Intermediate Similarity	NPC168409
0.8118	Intermediate Similarity	NPC473716
0.8118	Intermediate Similarity	NPC475597
0.8103	Intermediate Similarity	NPC111485
0.8057	Intermediate Similarity	NPC477559
0.8057	Intermediate Similarity	NPC306902
0.8057	Intermediate Similarity	NPC232924
0.8057	Intermediate Similarity	NPC266753
0.8057	Intermediate Similarity	NPC160298
0.8056	Intermediate Similarity	NPC2314
0.8024	Intermediate Similarity	NPC128019
0.8024	Intermediate Similarity	NPC136860
0.8024	Intermediate Similarity	NPC476567
0.8021	Intermediate Similarity	NPC63152
0.8	Intermediate Similarity	NPC477080
0.7978	Intermediate Similarity	NPC476432
0.7978	Intermediate Similarity	NPC24264
0.7977	Intermediate Similarity	NPC470708
0.7966	Intermediate Similarity	NPC476569
0.7959	Intermediate Similarity	NPC46990
0.7958	Intermediate Similarity	NPC267414
0.794	Intermediate Similarity	NPC55470
0.7933	Intermediate Similarity	NPC247389
0.7931	Intermediate Similarity	NPC184026
0.7931	Intermediate Similarity	NPC2413
0.7931	Intermediate Similarity	NPC193949
0.7931	Intermediate Similarity	NPC127674
0.7931	Intermediate Similarity	NPC204828
0.7931	Intermediate Similarity	NPC189266
0.7931	Intermediate Similarity	NPC276588
0.7931	Intermediate Similarity	NPC207757
0.7931	Intermediate Similarity	NPC54379
0.7931	Intermediate Similarity	NPC5238
0.7931	Intermediate Similarity	NPC469817
0.7931	Intermediate Similarity	NPC249797
0.7931	Intermediate Similarity	NPC39701
0.7931	Intermediate Similarity	NPC172765
0.7931	Intermediate Similarity	NPC278799
0.7931	Intermediate Similarity	NPC295691
0.7931	Intermediate Similarity	NPC110416
0.7921	Intermediate Similarity	NPC225774
0.7921	Intermediate Similarity	NPC16805
0.7921	Intermediate Similarity	NPC167546
0.7921	Intermediate Similarity	NPC302527
0.7914	Intermediate Similarity	NPC237579
0.7907	Intermediate Similarity	NPC223125
0.7904	Intermediate Similarity	NPC213206
0.7904	Intermediate Similarity	NPC328750
0.7904	Intermediate Similarity	NPC188163
0.7904	Intermediate Similarity	NPC474915
0.7877	Intermediate Similarity	NPC219341
0.7861	Intermediate Similarity	NPC471650
0.7861	Intermediate Similarity	NPC476579
0.7853	Intermediate Similarity	NPC135006
0.7844	Intermediate Similarity	NPC314682
0.7833	Intermediate Similarity	NPC210918
0.7833	Intermediate Similarity	NPC298979
0.7829	Intermediate Similarity	NPC78733
0.7824	Intermediate Similarity	NPC475654
0.7819	Intermediate Similarity	NPC141440
0.7816	Intermediate Similarity	NPC148898
0.7816	Intermediate Similarity	NPC223124
0.7812	Intermediate Similarity	NPC193906
0.7812	Intermediate Similarity	NPC23080
0.7806	Intermediate Similarity	NPC80472
0.7796	Intermediate Similarity	NPC73492
0.7796	Intermediate Similarity	NPC299990
0.7796	Intermediate Similarity	NPC116284
0.7784	Intermediate Similarity	NPC476443
0.7784	Intermediate Similarity	NPC133817
0.7778	Intermediate Similarity	NPC86144
0.7778	Intermediate Similarity	NPC304659
0.7772	Intermediate Similarity	NPC35680
0.7772	Intermediate Similarity	NPC241704
0.7747	Intermediate Similarity	NPC474708
0.7746	Intermediate Similarity	NPC470088
0.7733	Intermediate Similarity	NPC476151
0.773	Intermediate Similarity	NPC148693
0.773	Intermediate Similarity	NPC294790
0.773	Intermediate Similarity	NPC118633
0.7725	Intermediate Similarity	NPC225745
0.7723	Intermediate Similarity	NPC38964
0.7722	Intermediate Similarity	NPC306669
0.7717	Intermediate Similarity	NPC207721
0.7713	Intermediate Similarity	NPC18306
0.7708	Intermediate Similarity	NPC33256
0.7708	Intermediate Similarity	NPC470646
0.7705	Intermediate Similarity	NPC149090
0.7705	Intermediate Similarity	NPC227683
0.7705	Intermediate Similarity	NPC19520
0.7701	Intermediate Similarity	NPC151895
0.7701	Intermediate Similarity	NPC88249
0.7701	Intermediate Similarity	NPC192768
0.7701	Intermediate Similarity	NPC97221
0.7701	Intermediate Similarity	NPC220858
0.7692	Intermediate Similarity	NPC475845
0.7688	Intermediate Similarity	NPC32154
0.7667	Intermediate Similarity	NPC189470
0.7665	Intermediate Similarity	NPC7018
0.7657	Intermediate Similarity	NPC81733
0.7657	Intermediate Similarity	NPC326316
0.765	Intermediate Similarity	NPC6152
0.765	Intermediate Similarity	NPC75958
0.7647	Intermediate Similarity	NPC82056
0.7644	Intermediate Similarity	NPC103379
0.7644	Intermediate Similarity	NPC477565
0.7637	Intermediate Similarity	NPC474324
0.7637	Intermediate Similarity	NPC57812
0.7634	Intermediate Similarity	NPC114364
0.7634	Intermediate Similarity	NPC320223
0.7627	Intermediate Similarity	NPC76079
0.7622	Intermediate Similarity	NPC229166
0.7622	Intermediate Similarity	NPC128560
0.7622	Intermediate Similarity	NPC199465
0.7619	Intermediate Similarity	NPC252107
0.7616	Intermediate Similarity	NPC469978
0.7616	Intermediate Similarity	NPC185838
0.7605	Intermediate Similarity	NPC180647
0.7598	Intermediate Similarity	NPC118804
0.7594	Intermediate Similarity	NPC220961
0.7592	Intermediate Similarity	NPC82763
0.7592	Intermediate Similarity	NPC281581
0.7588	Intermediate Similarity	NPC308943
0.7586	Intermediate Similarity	NPC147390
0.7586	Intermediate Similarity	NPC24233
0.7586	Intermediate Similarity	NPC476571
0.7586	Intermediate Similarity	NPC428
0.7586	Intermediate Similarity	NPC246587
0.7586	Intermediate Similarity	NPC135538
0.7584	Intermediate Similarity	NPC247639
0.7584	Intermediate Similarity	NPC25084
0.7582	Intermediate Similarity	NPC13916
0.7582	Intermediate Similarity	NPC264850
0.7579	Intermediate Similarity	NPC230098
0.7568	Intermediate Similarity	NPC4669
0.7566	Intermediate Similarity	NPC475981

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 NPC169387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	723
0.2-0.3	1034
0.3-0.4	1927
0.4-0.5	2631
0.5-0.6	1907
0.6-0.7	622
0.7-0.8	91
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8689	High Similarity	NPD4420	Approved
0.8602	High Similarity	NPD5005	Approved
0.8602	High Similarity	NPD5006	Approved
0.8362	Intermediate Similarity	NPD5313	Approved
0.8362	Intermediate Similarity	NPD5312	Approved
0.8263	Intermediate Similarity	NPD4584	Approved
0.8201	Intermediate Similarity	NPD5457	Discontinued
0.8087	Intermediate Similarity	NPD6618	Phase 2
0.8059	Intermediate Similarity	NPD3641	Approved
0.8059	Intermediate Similarity	NPD3639	Approved
0.8059	Intermediate Similarity	NPD3640	Phase 3
0.7943	Intermediate Similarity	NPD5977	Approved
0.7943	Intermediate Similarity	NPD5978	Approved
0.7935	Intermediate Similarity	NPD7280	Phase 3
0.7935	Intermediate Similarity	NPD7281	Phase 3
0.7904	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7291	Discontinued
0.7816	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4166	Phase 2
0.7778	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD6297	Approved
0.7708	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7110	Phase 1
0.767	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD5564	Approved
0.7606	Intermediate Similarity	NPD6851	Approved
0.7606	Intermediate Similarity	NPD6853	Approved
0.7568	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD5071	Phase 2
0.7528	Intermediate Similarity	NPD7298	Approved
0.7527	Intermediate Similarity	NPD6107	Approved
0.75	Intermediate Similarity	NPD2492	Phase 1
0.7462	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD824	Approved
0.7457	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8252	Approved
0.7419	Intermediate Similarity	NPD8099	Discontinued
0.7419	Intermediate Similarity	NPD8251	Approved
0.7416	Intermediate Similarity	NPD6875	Approved
0.7416	Intermediate Similarity	NPD6876	Approved
0.7409	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD8156	Discontinued
0.7374	Intermediate Similarity	NPD6385	Approved
0.7374	Intermediate Similarity	NPD6386	Approved
0.7368	Intermediate Similarity	NPD2971	Approved
0.7368	Intermediate Similarity	NPD4078	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2968	Approved
0.736	Intermediate Similarity	NPD4017	Approved
0.7314	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2898	Approved
0.7291	Intermediate Similarity	NPD4859	Phase 1
0.7286	Intermediate Similarity	NPD4107	Approved
0.7278	Intermediate Similarity	NPD4773	Phase 2
0.7278	Intermediate Similarity	NPD4772	Phase 2
0.7249	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD1670	Discontinued
0.7225	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4481	Phase 3
0.7209	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6625	Approved
0.7182	Intermediate Similarity	NPD6873	Phase 2
0.717	Intermediate Similarity	NPD6997	Phase 2
0.7166	Intermediate Similarity	NPD5242	Approved
0.7165	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4482	Phase 3
0.7158	Intermediate Similarity	NPD5967	Approved
0.7151	Intermediate Similarity	NPD6030	Approved
0.7151	Intermediate Similarity	NPD6031	Approved
0.715	Intermediate Similarity	NPD8053	Approved
0.715	Intermediate Similarity	NPD8054	Approved
0.7143	Intermediate Similarity	NPD2490	Approved
0.7143	Intermediate Similarity	NPD2488	Approved
0.7136	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2975	Approved
0.7136	Intermediate Similarity	NPD2974	Approved
0.7136	Intermediate Similarity	NPD2973	Approved
0.7135	Intermediate Similarity	NPD7190	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6788	Approved
0.7119	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6834	Approved
0.7077	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3885	Approved
0.7065	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD743	Approved
0.7049	Intermediate Similarity	NPD6844	Discontinued
0.7049	Intermediate Similarity	NPD7248	Discontinued
0.7044	Intermediate Similarity	NPD3057	Approved
0.7044	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3349	Phase 2
0.7041	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6894	Phase 1
0.703	Intermediate Similarity	NPD4580	Approved
0.702	Intermediate Similarity	NPD7296	Approved
0.7016	Intermediate Similarity	NPD6020	Phase 2
0.7014	Intermediate Similarity	NPD7048	Phase 3
0.7005	Intermediate Similarity	NPD5910	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3452	Approved
0.6995	Remote Similarity	NPD2494	Approved
0.6995	Remote Similarity	NPD3450	Approved
0.6995	Remote Similarity	NPD2493	Approved
0.6989	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1307	Phase 2
0.6989	Remote Similarity	NPD1309	Phase 2
0.6986	Remote Similarity	NPD4885	Approved
0.6985	Remote Similarity	NPD6181	Discontinued
0.6983	Remote Similarity	NPD3124	Discontinued
0.6967	Remote Similarity	NPD7047	Phase 3
0.6967	Remote Similarity	NPD8149	Discontinued
0.6961	Remote Similarity	NPD3448	Approved
0.6961	Remote Similarity	NPD2972	Approved
0.6961	Remote Similarity	NPD2491	Approved
0.6961	Remote Similarity	NPD3533	Approved
0.6959	Remote Similarity	NPD5718	Phase 2
0.6957	Remote Similarity	NPD7317	Phase 3
0.6954	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD5676	Approved
0.6937	Remote Similarity	NPD4846	Phase 2
0.6931	Remote Similarity	NPD4010	Discontinued
0.6931	Remote Similarity	NPD5186	Approved
0.6931	Remote Similarity	NPD5183	Approved
0.6931	Remote Similarity	NPD3051	Approved
0.6927	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2904	Discontinued
0.6913	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7225	Discontinued
0.6895	Remote Similarity	NPD2970	Approved
0.6895	Remote Similarity	NPD2969	Approved
0.6893	Remote Similarity	NPD4582	Approved
0.6893	Remote Similarity	NPD4583	Approved
0.689	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5025	Approved
0.6884	Remote Similarity	NPD7907	Approved
0.6882	Remote Similarity	NPD7318	Phase 3
0.6878	Remote Similarity	NPD7802	Discontinued
0.6875	Remote Similarity	NPD7177	Discontinued
0.6875	Remote Similarity	NPD7701	Phase 2
0.6872	Remote Similarity	NPD5241	Discontinued
0.6872	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD27	Approved
0.6859	Remote Similarity	NPD2489	Approved
0.6845	Remote Similarity	NPD4002	Approved
0.6845	Remote Similarity	NPD4004	Approved
0.6842	Remote Similarity	NPD6071	Discontinued
0.6832	Remote Similarity	NPD5582	Discontinued
0.6828	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7584	Approved
0.6825	Remote Similarity	NPD3816	Phase 1
0.6825	Remote Similarity	NPD3815	Phase 1
0.6823	Remote Similarity	NPD3446	Phase 1
0.6821	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5754	Discontinued
0.6814	Remote Similarity	NPD7810	Phase 3
0.6814	Remote Similarity	NPD7811	Phase 3
0.6809	Remote Similarity	NPD7831	Phase 2
0.6809	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7833	Phase 2
0.68	Remote Similarity	NPD7668	Phase 2
0.6794	Remote Similarity	NPD5950	Discontinued
0.6791	Remote Similarity	NPD4665	Approved
0.6791	Remote Similarity	NPD4111	Phase 1
0.6791	Remote Similarity	NPD2560	Approved
0.6791	Remote Similarity	NPD2563	Approved
0.6788	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7693	Approved
0.6782	Remote Similarity	NPD6493	Phase 3
0.6776	Remote Similarity	NPD7427	Discontinued
0.6776	Remote Similarity	NPD5980	Discovery
0.6772	Remote Similarity	NPD7400	Phase 3
0.6761	Remote Similarity	NPD6895	Approved
0.6761	Remote Similarity	NPD6896	Approved
0.6758	Remote Similarity	NPD7224	Discontinued
0.6758	Remote Similarity	NPD7223	Discontinued
0.6758	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6747	Phase 1
0.6751	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD1933	Approved
0.6739	Remote Similarity	NPD4210	Discontinued

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