NPASS Compound

Structure

NPC222524 OpenBabel07101719132D 27 30 0 0 1 0 0 0 0 0999 V2000 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 -1.7321 2.0000 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 -3.4641 -1.0000 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 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 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 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 0.8660 -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 1 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 2.5981 -2.5000 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 -1.7321 -0.0000 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 -0.8660 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 -4.0000 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 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 13 19 2 0 0 0 0 14 15 1 0 0 0 0 15 9 1 6 0 0 0 15 22 1 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 18 2 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.16
Volume:	374.039
LogP:	2.402
LogD:	2.774
LogS:	-3.875
# Rotatable Bonds:	4
TPSA:	57.23
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.829
Synthetic Accessibility Score:	2.823
Fsp3:	0.381
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:	-4.815
MDCK Permeability:	2.83828721876489e-05
Pgp-inhibitor:	0.62
Pgp-substrate:	0.834
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.237

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.701
Plasma Protein Binding (PPB):	80.21894073486328%
Volume Distribution (VD):	0.979
Pgp-substrate:	14.460362434387207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.552
CYP2C19-substrate:	0.926
CYP2C9-inhibitor:	0.257
CYP2C9-substrate:	0.824
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.589
CYP3A4-substrate:	0.872

ADMET: Excretion

Clearance (CL):	5.271
Half-life (T1/2):	0.374

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.34
Drug-inuced Liver Injury (DILI):	0.586
AMES Toxicity:	0.169
Rat Oral Acute Toxicity:	0.428
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.094
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC222524

Natural Product ID:	NPC222524
*Common Name:**	(-)-8-Oxotetrahydroplamatine
IUPAC Name:	(13aS)-2,3,9,10-tetramethoxy-5,6,13,13a-tetrahydroisoquinolino[2,1-b]isoquinolin-8-one
Synonyms:
Standard InCHIKey:	DMFHLLHXYQJPJS-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C21H23NO5/c1-24-16-6-5-13-9-15-14-11-18(26-3)17(25-2)10-12(14)7-8-22(15)21(23)19(13)20(16)27-4/h5-6,10-11,15H,7-9H2,1-4H3/t15-/m0/s1
SMILES:	COc1cc2CCN3[C@H](c2cc1OC)Cc1c(C3=O)c(OC)c(cc1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468804
PubChem CID:	157076
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
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087586]
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]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19860383]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25747495]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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
EC50	1
IC50	2
Others	5

Activity Type	# Activity
Cell Line	1
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	307000.0	nM	PMID[547869]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	22.4	n.a.	PMID[547869]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	140000.0	nM	PMID[547869]
NPT27	Others	Unspecified		CC50	=	3000000.0	nM	PMID[547869]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	7470000.0	nM	PMID[547869]
NPT2	Others	Unspecified		Ratio CC50/IC50	<	1.0	n.a.	PMID[547869]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	14100.0	nM	PMID[547869]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	18.8	n.a.	PMID[547869]

☑ 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 NPC222524 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	335
0.1-0.2	1731
0.2-0.3	7236
0.3-0.4	10362
0.4-0.5	4796
0.5-0.6	12147
0.6-0.7	5367
0.7-0.8	640
0.8-0.85	62
0.85-0.9	12
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9581	High Similarity	NPC169387
0.9581	High Similarity	NPC477259
0.9524	High Similarity	NPC208890
0.9249	High Similarity	NPC477258
0.9195	High Similarity	NPC24228
0.8941	High Similarity	NPC27887
0.8895	High Similarity	NPC116007
0.8678	High Similarity	NPC83511
0.8625	High Similarity	NPC210437
0.8625	High Similarity	NPC476144
0.8625	High Similarity	NPC106295
0.8625	High Similarity	NPC51957
0.8625	High Similarity	NPC16107
0.8571	High Similarity	NPC7467
0.8563	High Similarity	NPC153631
0.8539	High Similarity	NPC226708
0.8528	High Similarity	NPC119669
0.8375	Intermediate Similarity	NPC136860
0.8375	Intermediate Similarity	NPC476567
0.8375	Intermediate Similarity	NPC128019
0.8343	Intermediate Similarity	NPC469816
0.8343	Intermediate Similarity	NPC469815
0.8306	Intermediate Similarity	NPC46744
0.8306	Intermediate Similarity	NPC73020
0.8306	Intermediate Similarity	NPC215098
0.8306	Intermediate Similarity	NPC14622
0.8306	Intermediate Similarity	NPC70290
0.8306	Intermediate Similarity	NPC124302
0.8294	Intermediate Similarity	NPC476569
0.8263	Intermediate Similarity	NPC469817
0.8263	Intermediate Similarity	NPC276588
0.8263	Intermediate Similarity	NPC110416
0.8263	Intermediate Similarity	NPC295691
0.8263	Intermediate Similarity	NPC138487
0.8263	Intermediate Similarity	NPC5238
0.8263	Intermediate Similarity	NPC127674
0.8263	Intermediate Similarity	NPC278799
0.8263	Intermediate Similarity	NPC39701
0.8263	Intermediate Similarity	NPC172765
0.8263	Intermediate Similarity	NPC54379
0.8263	Intermediate Similarity	NPC41178
0.8263	Intermediate Similarity	NPC189266
0.8263	Intermediate Similarity	NPC193949
0.8263	Intermediate Similarity	NPC2413
0.8263	Intermediate Similarity	NPC204828
0.8263	Intermediate Similarity	NPC207757
0.8263	Intermediate Similarity	NPC249797
0.8263	Intermediate Similarity	NPC184026
0.8263	Intermediate Similarity	NPC216459
0.825	Intermediate Similarity	NPC474915
0.825	Intermediate Similarity	NPC213206
0.825	Intermediate Similarity	NPC328750
0.825	Intermediate Similarity	NPC188163
0.8226	Intermediate Similarity	NPC2173
0.8226	Intermediate Similarity	NPC328700
0.8226	Intermediate Similarity	NPC202771
0.8226	Intermediate Similarity	NPC119818
0.8218	Intermediate Similarity	NPC303581
0.8218	Intermediate Similarity	NPC67978
0.8216	Intermediate Similarity	NPC72788
0.8216	Intermediate Similarity	NPC120671
0.8216	Intermediate Similarity	NPC226652
0.8216	Intermediate Similarity	NPC314100
0.8214	Intermediate Similarity	NPC146288
0.8197	Intermediate Similarity	NPC125924
0.8193	Intermediate Similarity	NPC476579
0.8187	Intermediate Similarity	NPC314682
0.8176	Intermediate Similarity	NPC135006
0.8162	Intermediate Similarity	NPC207239
0.8125	Intermediate Similarity	NPC308267
0.8107	Intermediate Similarity	NPC234392
0.8107	Intermediate Similarity	NPC31311
0.8061	Intermediate Similarity	NPC476151
0.8024	Intermediate Similarity	NPC220858
0.8024	Intermediate Similarity	NPC97221
0.8024	Intermediate Similarity	NPC88249
0.8024	Intermediate Similarity	NPC151895
0.8024	Intermediate Similarity	NPC192768
0.8011	Intermediate Similarity	NPC71124
0.8	Intermediate Similarity	NPC241055
0.8	Intermediate Similarity	NPC38964
0.7978	Intermediate Similarity	NPC241704
0.7976	Intermediate Similarity	NPC326316
0.7976	Intermediate Similarity	NPC81733
0.7968	Intermediate Similarity	NPC5374
0.7964	Intermediate Similarity	NPC477565
0.7964	Intermediate Similarity	NPC103379
0.7947	Intermediate Similarity	NPC268077
0.7939	Intermediate Similarity	NPC185838
0.7933	Intermediate Similarity	NPC121400
0.7931	Intermediate Similarity	NPC238530
0.7931	Intermediate Similarity	NPC276944
0.7931	Intermediate Similarity	NPC231198
0.7931	Intermediate Similarity	NPC232514
0.7929	Intermediate Similarity	NPC233029
0.7929	Intermediate Similarity	NPC210148
0.7919	Intermediate Similarity	NPC82056
0.791	Intermediate Similarity	NPC227683
0.7904	Intermediate Similarity	NPC428
0.7904	Intermediate Similarity	NPC246587
0.7904	Intermediate Similarity	NPC476571
0.7904	Intermediate Similarity	NPC475959
0.7904	Intermediate Similarity	NPC135538
0.7904	Intermediate Similarity	NPC24233
0.7904	Intermediate Similarity	NPC147390
0.7898	Intermediate Similarity	NPC86469
0.7895	Intermediate Similarity	NPC476443
0.7895	Intermediate Similarity	NPC207971
0.7895	Intermediate Similarity	NPC247639
0.7895	Intermediate Similarity	NPC133817
0.7895	Intermediate Similarity	NPC25084
0.7892	Intermediate Similarity	NPC254957
0.7889	Intermediate Similarity	NPC32154
0.7886	Intermediate Similarity	NPC13916
0.7886	Intermediate Similarity	NPC264850
0.7865	Intermediate Similarity	NPC308943
0.7857	Intermediate Similarity	NPC92541
0.7849	Intermediate Similarity	NPC476572
0.7844	Intermediate Similarity	NPC321505
0.7844	Intermediate Similarity	NPC179825
0.7844	Intermediate Similarity	NPC191376
0.7836	Intermediate Similarity	NPC80129
0.7836	Intermediate Similarity	NPC99659
0.7836	Intermediate Similarity	NPC325871
0.7836	Intermediate Similarity	NPC187022
0.7829	Intermediate Similarity	NPC24465
0.7826	Intermediate Similarity	NPC166979
0.7803	Intermediate Similarity	NPC118804
0.7803	Intermediate Similarity	NPC106786
0.7802	Intermediate Similarity	NPC102760
0.779	Intermediate Similarity	NPC220961
0.7778	Intermediate Similarity	NPC267414
0.7778	Intermediate Similarity	NPC35680
0.7771	Intermediate Similarity	NPC59567
0.7765	Intermediate Similarity	NPC476568
0.7742	Intermediate Similarity	NPC473716
0.7742	Intermediate Similarity	NPC475597
0.7738	Intermediate Similarity	NPC144863
0.7733	Intermediate Similarity	NPC93593
0.7727	Intermediate Similarity	NPC168409
0.7725	Intermediate Similarity	NPC130926
0.7709	Intermediate Similarity	NPC10908
0.7709	Intermediate Similarity	NPC317439
0.7709	Intermediate Similarity	NPC76682
0.7709	Intermediate Similarity	NPC63646
0.7709	Intermediate Similarity	NPC198498
0.7709	Intermediate Similarity	NPC227060
0.7709	Intermediate Similarity	NPC317145
0.7709	Intermediate Similarity	NPC115284
0.7709	Intermediate Similarity	NPC276890
0.7702	Intermediate Similarity	NPC266425
0.7701	Intermediate Similarity	NPC111485
0.7701	Intermediate Similarity	NPC216816
0.7688	Intermediate Similarity	NPC126519
0.7688	Intermediate Similarity	NPC57512
0.7688	Intermediate Similarity	NPC170503
0.7688	Intermediate Similarity	NPC203784
0.7674	Intermediate Similarity	NPC477564
0.7674	Intermediate Similarity	NPC2295
0.767	Intermediate Similarity	NPC475393
0.7667	Intermediate Similarity	NPC129518
0.7667	Intermediate Similarity	NPC2314
0.7667	Intermediate Similarity	NPC41376
0.7667	Intermediate Similarity	NPC251580
0.7667	Intermediate Similarity	NPC12424
0.7661	Intermediate Similarity	NPC85747
0.7661	Intermediate Similarity	NPC8337
0.7657	Intermediate Similarity	NPC266753
0.7657	Intermediate Similarity	NPC27410
0.7657	Intermediate Similarity	NPC232924
0.7657	Intermediate Similarity	NPC306902
0.7657	Intermediate Similarity	NPC166014
0.7657	Intermediate Similarity	NPC160298
0.7657	Intermediate Similarity	NPC477559
0.765	Intermediate Similarity	NPC298339
0.7647	Intermediate Similarity	NPC219162
0.7647	Intermediate Similarity	NPC60538
0.7647	Intermediate Similarity	NPC207824
0.7647	Intermediate Similarity	NPC63152
0.764	Intermediate Similarity	NPC284842
0.7637	Intermediate Similarity	NPC327005
0.763	Intermediate Similarity	NPC244112
0.7625	Intermediate Similarity	NPC160193
0.7616	Intermediate Similarity	NPC476580
0.7602	Intermediate Similarity	NPC46990
0.76	Intermediate Similarity	NPC477080
0.7596	Intermediate Similarity	NPC99723
0.7588	Intermediate Similarity	NPC55470
0.7588	Intermediate Similarity	NPC130941
0.7584	Intermediate Similarity	NPC317272
0.7584	Intermediate Similarity	NPC250846
0.7584	Intermediate Similarity	NPC42549
0.7584	Intermediate Similarity	NPC476432
0.7584	Intermediate Similarity	NPC256012
0.7584	Intermediate Similarity	NPC268503
0.7584	Intermediate Similarity	NPC240841
0.7584	Intermediate Similarity	NPC24264
0.7582	Intermediate Similarity	NPC293093
0.7572	Intermediate Similarity	NPC470708
0.7571	Intermediate Similarity	NPC324144

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 NPC222524 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	735
0.2-0.3	1013
0.3-0.4	1854
0.4-0.5	2556
0.5-0.6	1991
0.6-0.7	672
0.7-0.8	95
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8625	High Similarity	NPD4584	Approved
0.8596	High Similarity	NPD5313	Approved
0.8596	High Similarity	NPD5312	Approved
0.8409	Intermediate Similarity	NPD6618	Phase 2
0.8405	Intermediate Similarity	NPD3639	Approved
0.8405	Intermediate Similarity	NPD3641	Approved
0.8405	Intermediate Similarity	NPD3640	Phase 3
0.8306	Intermediate Similarity	NPD4420	Approved
0.825	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8226	Intermediate Similarity	NPD5006	Approved
0.8226	Intermediate Similarity	NPD5005	Approved
0.8167	Intermediate Similarity	NPD7291	Discontinued
0.8166	Intermediate Similarity	NPD5978	Approved
0.8166	Intermediate Similarity	NPD5977	Approved
0.8144	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7110	Phase 1
0.7988	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD6297	Approved
0.7903	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD4166	Phase 2
0.788	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7298	Approved
0.7831	Intermediate Similarity	NPD5457	Discontinued
0.7819	Intermediate Similarity	NPD5071	Phase 2
0.7802	Intermediate Similarity	NPD6853	Approved
0.7802	Intermediate Similarity	NPD6851	Approved
0.7766	Intermediate Similarity	NPD5564	Approved
0.7765	Intermediate Similarity	NPD824	Approved
0.7737	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6107	Approved
0.7719	Intermediate Similarity	NPD6876	Approved
0.7719	Intermediate Similarity	NPD6875	Approved
0.7709	Intermediate Similarity	NPD8252	Approved
0.7709	Intermediate Similarity	NPD8099	Discontinued
0.7709	Intermediate Similarity	NPD8251	Approved
0.7667	Intermediate Similarity	NPD8156	Discontinued
0.7667	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4017	Approved
0.765	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4772	Phase 2
0.7572	Intermediate Similarity	NPD6385	Approved
0.7572	Intermediate Similarity	NPD6386	Approved
0.7572	Intermediate Similarity	NPD4773	Phase 2
0.7554	Intermediate Similarity	NPD7280	Phase 3
0.7554	Intermediate Similarity	NPD7281	Phase 3
0.7554	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2898	Approved
0.7461	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD2968	Approved
0.7459	Intermediate Similarity	NPD2971	Approved
0.7459	Intermediate Similarity	NPD4078	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6031	Approved
0.7442	Intermediate Similarity	NPD6030	Approved
0.7433	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8053	Approved
0.7419	Intermediate Similarity	NPD8054	Approved
0.7412	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD6788	Approved
0.7374	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6873	Phase 2
0.7354	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5242	Approved
0.7345	Intermediate Similarity	NPD5967	Approved
0.7344	Intermediate Similarity	NPD6834	Approved
0.734	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6844	Discontinued
0.7317	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6894	Phase 1
0.7302	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4107	Approved
0.7267	Intermediate Similarity	NPD3124	Discontinued
0.7263	Intermediate Similarity	NPD1309	Phase 2
0.7263	Intermediate Similarity	NPD1307	Phase 2
0.7256	Intermediate Similarity	NPD5718	Phase 2
0.7246	Intermediate Similarity	NPD6997	Phase 2
0.7241	Intermediate Similarity	NPD1670	Discontinued
0.724	Intermediate Similarity	NPD6181	Discontinued
0.7225	Intermediate Similarity	NPD2490	Approved
0.7225	Intermediate Similarity	NPD2488	Approved
0.7219	Intermediate Similarity	NPD7190	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2974	Approved
0.7216	Intermediate Similarity	NPD2975	Approved
0.7216	Intermediate Similarity	NPD2973	Approved
0.7213	Intermediate Similarity	NPD4481	Phase 3
0.7209	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD8149	Discontinued
0.7198	Intermediate Similarity	NPD5186	Approved
0.7198	Intermediate Similarity	NPD5183	Approved
0.7198	Intermediate Similarity	NPD4010	Discontinued
0.7195	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD2904	Discontinued
0.7173	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4482	Phase 3
0.7151	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5241	Discontinued
0.7143	Intermediate Similarity	NPD743	Approved
0.7143	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7225	Discontinued
0.7143	Intermediate Similarity	NPD7802	Discontinued
0.7135	Intermediate Similarity	NPD7248	Discontinued
0.7129	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3057	Approved
0.7113	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4580	Approved
0.7097	Intermediate Similarity	NPD6020	Phase 2
0.7095	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7048	Phase 3
0.7083	Intermediate Similarity	NPD2492	Phase 1
0.7083	Intermediate Similarity	NPD5910	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3446	Phase 1
0.7072	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3452	Approved
0.7071	Intermediate Similarity	NPD3450	Approved
0.7071	Intermediate Similarity	NPD2493	Approved
0.7071	Intermediate Similarity	NPD2494	Approved
0.7052	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7177	Discontinued
0.7041	Intermediate Similarity	NPD6896	Approved
0.7041	Intermediate Similarity	NPD6895	Approved
0.7039	Intermediate Similarity	NPD7047	Phase 3
0.7035	Intermediate Similarity	NPD2972	Approved
0.7035	Intermediate Similarity	NPD3533	Approved
0.7035	Intermediate Similarity	NPD3448	Approved
0.7035	Intermediate Similarity	NPD2491	Approved
0.7031	Intermediate Similarity	NPD6040	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3051	Approved
0.701	Intermediate Similarity	NPD5676	Approved
0.7006	Intermediate Similarity	NPD4474	Approved
0.7006	Intermediate Similarity	NPD4475	Approved
0.7	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7833	Phase 2
0.6978	Remote Similarity	NPD7831	Phase 2
0.6973	Remote Similarity	NPD2970	Approved
0.6973	Remote Similarity	NPD2969	Approved
0.6971	Remote Similarity	NPD2421	Approved
0.6971	Remote Similarity	NPD2420	Approved
0.6971	Remote Similarity	NPD7598	Phase 2
0.697	Remote Similarity	NPD7810	Phase 3
0.697	Remote Similarity	NPD8095	Phase 1
0.697	Remote Similarity	NPD7811	Phase 3
0.6965	Remote Similarity	NPD4582	Approved
0.6965	Remote Similarity	NPD4583	Approved
0.6959	Remote Similarity	NPD7668	Phase 2
0.6957	Remote Similarity	NPD5025	Approved
0.6952	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7907	Approved
0.6949	Remote Similarity	NPD7427	Discontinued
0.6947	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4859	Phase 1
0.6944	Remote Similarity	NPD7317	Phase 3
0.6943	Remote Similarity	NPD7693	Approved
0.6938	Remote Similarity	NPD2899	Discontinued
0.6935	Remote Similarity	NPD27	Approved
0.6935	Remote Similarity	NPD2489	Approved
0.6932	Remote Similarity	NPD1424	Approved
0.6923	Remote Similarity	NPD5968	Phase 3
0.6919	Remote Similarity	NPD6071	Discontinued
0.6919	Remote Similarity	NPD6747	Phase 1
0.6915	Remote Similarity	NPD4004	Approved
0.6915	Remote Similarity	NPD4002	Approved
0.6914	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6748	Discontinued
0.6897	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5890	Approved
0.6889	Remote Similarity	NPD5889	Approved
0.6879	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2649	Approved
0.6872	Remote Similarity	NPD2651	Approved
0.6868	Remote Similarity	NPD2560	Approved
0.6868	Remote Similarity	NPD7318	Phase 3
0.6868	Remote Similarity	NPD2563	Approved
0.6866	Remote Similarity	NPD6625	Approved
0.6864	Remote Similarity	NPD3140	Approved
0.6864	Remote Similarity	NPD3109	Approved
0.6864	Remote Similarity	NPD3110	Approved
0.6864	Remote Similarity	NPD3142	Approved
0.6862	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4111	Phase 1
0.6857	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4665	Approved
0.6856	Remote Similarity	NPD5620	Clinical (unspecified phase)

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