NPASS Compound

Structure

NPC472474 OpenBabel07101718292D 36 42 0 0 1 0 0 0 0 0999 V2000 -3.6808 -3.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8903 -2.0932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0714 -0.3706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6646 0.5430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9013 -1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4898 0.8854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2852 1.7689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9067 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1807 2.7635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8717 0.8854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7634 2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -2.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4836 -1.1796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6808 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2634 1.5610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -2.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4890 -1.0751 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6808 -0.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6701 0.6475 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8147 -1.2024 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 2.0823 -0.1615 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1808 1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0942 3.1702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 3 0 0 0 0 0 0 0 0 0 3 5 1 0 0 0 0 3 21 1 0 0 0 0 4 6 1 0 0 0 0 4 22 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 11 1 0 0 0 0 7 25 1 0 0 0 0 8 12 1 0 0 0 0 8 26 1 0 0 0 0 9 13 2 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 10 24 1 0 0 0 0 12 30 1 0 0 0 0 13 34 1 0 0 0 0 14 35 1 0 0 0 0 15 23 2 0 0 0 0 15 34 1 0 0 0 0 16 24 2 0 0 0 0 16 35 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 18 31 1 0 0 0 0 19 30 1 0 0 0 0 19 32 1 0 0 0 0 20 29 1 0 0 0 0 20 36 1 0 0 0 0 21 1 1 6 0 0 0 21 25 1 0 0 0 0 22 2 1 1 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 31 1 1 0 0 0 26 32 1 6 0 0 0 27 31 1 1 0 0 0 28 32 1 6 0 0 0 29 11 1 1 0 0 0 30 36 1 6 0 0 0 33 36 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.29
Volume:	523.868
LogP:	4.018
LogD:	4.048
LogS:	-3.905
# Rotatable Bonds:	2
TPSA:	55.82
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	6.405
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.842
MDCK Permeability:	1.6279920600936748e-05
Pgp-inhibitor:	0.894
Pgp-substrate:	0.53
Human Intestinal Absorption (HIA):	0.38
20% Bioavailability (F20%):	0.846
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	97.45929718017578%
Volume Distribution (VD):	1.566
Pgp-substrate:	3.2150719165802%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.665
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.991
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	11.617
Half-life (T1/2):	0.19

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.995
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.994
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.021
Carcinogencity:	0.918
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.761

Download Data

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

Natural Product: NPC472474

Natural Product ID:	NPC472474
*Common Name:**	RCEGLXVYHHYXSF-LGJFMGMLSA-N
IUPAC Name:	n.a.
Synonyms:	Neothiobinupharidine Beta-Sulfoxide
Standard InCHIKey:	RCEGLXVYHHYXSF-LGJFMGMLSA-N
Standard InCHI:	InChI=1S/C30H42N2O3S/c1-21-3-5-27(23-9-13-34-15-23)31-18-29(11-7-25(21)31)17-30(36(33)20-29)12-8-26-22(2)4-6-28(32(26)19-30)24-10-14-35-16-24/h9-10,13-16,21-22,25-28H,3-8,11-12,17-20H2,1-2H3/t21-,22-,25+,26+,27+,28+,29-,30-,36?/m1/s1
SMILES:	CC1CCC(N2C1CCC3(C2)CC4(CCC5C(CCC(N5C4)C6=COC=C6)C)S(=O)C3)C7=COC=C7
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL342635
PubChem CID:	44358921
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000222] Quinolizines

*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
NPO33085	nuphar pumilum	Species	Nymphaeaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[14643343]
NPO33085	nuphar pumilum	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16413779]

☑ 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	12

Activity Type	# Activity
Cell Line	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	10.6	%	PMID[510118]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	18.5	%	PMID[510118]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	12.8	%	PMID[510118]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	15.7	%	PMID[510118]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	5.8	%	PMID[510119]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	10.0	%	PMID[510119]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	-3.7	%	PMID[510119]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	7.7	%	PMID[510119]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	9.1	%	PMID[510119]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	-0.4	%	PMID[510119]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	-1.8	%	PMID[510119]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	6.8	%	PMID[510119]

☑ 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 NPC472474 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	340
0.1-0.2	1581
0.2-0.3	5398
0.3-0.4	14936
0.4-0.5	17047
0.5-0.6	3248
0.6-0.7	132
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476236
1.0	High Similarity	NPC469964
0.9811	High Similarity	NPC70840
0.9811	High Similarity	NPC473245
0.9811	High Similarity	NPC176304
0.9398	High Similarity	NPC76433
0.9398	High Similarity	NPC186957
0.9398	High Similarity	NPC289167
0.9286	High Similarity	NPC297647
0.8113	Intermediate Similarity	NPC208170
0.8113	Intermediate Similarity	NPC216149
0.7784	Intermediate Similarity	NPC223873
0.7744	Intermediate Similarity	NPC473444
0.7744	Intermediate Similarity	NPC26589
0.6995	Remote Similarity	NPC471651
0.6833	Remote Similarity	NPC471649
0.6573	Remote Similarity	NPC471646
0.6573	Remote Similarity	NPC471647
0.6522	Remote Similarity	NPC28054
0.6446	Remote Similarity	NPC317217
0.6412	Remote Similarity	NPC327527
0.6412	Remote Similarity	NPC476917
0.6402	Remote Similarity	NPC243704
0.6398	Remote Similarity	NPC133817
0.6398	Remote Similarity	NPC476443
0.6391	Remote Similarity	NPC74612
0.639	Remote Similarity	NPC268170
0.6389	Remote Similarity	NPC189908
0.6369	Remote Similarity	NPC477038
0.6369	Remote Similarity	NPC477965
0.6347	Remote Similarity	NPC477967
0.6337	Remote Similarity	NPC476925
0.6322	Remote Similarity	NPC471006
0.6319	Remote Similarity	NPC150895
0.6316	Remote Similarity	NPC477039
0.6316	Remote Similarity	NPC477040
0.6316	Remote Similarity	NPC477123
0.6316	Remote Similarity	NPC477966
0.631	Remote Similarity	NPC16922
0.6302	Remote Similarity	NPC471648
0.63	Remote Similarity	NPC471650
0.6242	Remote Similarity	NPC208906
0.6242	Remote Similarity	NPC144745
0.6235	Remote Similarity	NPC179354
0.6229	Remote Similarity	NPC266425
0.6215	Remote Similarity	NPC307682
0.6207	Remote Similarity	NPC298190
0.6199	Remote Similarity	NPC23086
0.6199	Remote Similarity	NPC46536
0.6199	Remote Similarity	NPC138139
0.6172	Remote Similarity	NPC473005
0.6168	Remote Similarity	NPC473969
0.6165	Remote Similarity	NPC163867
0.6163	Remote Similarity	NPC83178
0.6143	Remote Similarity	NPC93574
0.6143	Remote Similarity	NPC255861
0.6127	Remote Similarity	NPC207294
0.6127	Remote Similarity	NPC472358
0.6127	Remote Similarity	NPC112706
0.6119	Remote Similarity	NPC149571
0.6114	Remote Similarity	NPC89133
0.6108	Remote Similarity	NPC45389
0.6082	Remote Similarity	NPC65735
0.6082	Remote Similarity	NPC243269
0.6082	Remote Similarity	NPC188377
0.6082	Remote Similarity	NPC83115
0.6074	Remote Similarity	NPC105249
0.6069	Remote Similarity	NPC319140
0.6069	Remote Similarity	NPC95567
0.6067	Remote Similarity	NPC92941
0.6066	Remote Similarity	NPC41216
0.6059	Remote Similarity	NPC36255
0.605	Remote Similarity	NPC27887
0.6048	Remote Similarity	NPC131801
0.6048	Remote Similarity	NPC212918
0.6047	Remote Similarity	NPC75557
0.6047	Remote Similarity	NPC71274
0.6047	Remote Similarity	NPC303010
0.6039	Remote Similarity	NPC477258
0.6039	Remote Similarity	NPC174783
0.6034	Remote Similarity	NPC146872
0.603	Remote Similarity	NPC222524
0.6023	Remote Similarity	NPC61788
0.6022	Remote Similarity	NPC214239
0.6012	Remote Similarity	NPC329922
0.6012	Remote Similarity	NPC329694
0.6012	Remote Similarity	NPC474260
0.6012	Remote Similarity	NPC81912
0.6	Remote Similarity	NPC42400
0.6	Remote Similarity	NPC470742
0.6	Remote Similarity	NPC310830
0.599	Remote Similarity	NPC128683
0.599	Remote Similarity	NPC473007
0.5989	Remote Similarity	NPC473982
0.5989	Remote Similarity	NPC56197
0.5989	Remote Similarity	NPC471817
0.5988	Remote Similarity	NPC45536
0.598	Remote Similarity	NPC477259
0.598	Remote Similarity	NPC169387
0.5978	Remote Similarity	NPC476947
0.5978	Remote Similarity	NPC470741
0.5977	Remote Similarity	NPC137570
0.5977	Remote Similarity	NPC476016
0.5976	Remote Similarity	NPC4898
0.5971	Remote Similarity	NPC473004
0.5968	Remote Similarity	NPC470999
0.5967	Remote Similarity	NPC220094
0.5967	Remote Similarity	NPC236532
0.5967	Remote Similarity	NPC476943
0.5965	Remote Similarity	NPC471549
0.5965	Remote Similarity	NPC473379
0.5963	Remote Similarity	NPC473006
0.5956	Remote Similarity	NPC20500
0.5956	Remote Similarity	NPC476436
0.5955	Remote Similarity	NPC470740
0.5955	Remote Similarity	NPC218838
0.5954	Remote Similarity	NPC473885
0.5954	Remote Similarity	NPC230979
0.5954	Remote Similarity	NPC471074
0.5952	Remote Similarity	NPC217180
0.5952	Remote Similarity	NPC312525
0.5946	Remote Similarity	NPC142113
0.5943	Remote Similarity	NPC474279
0.5943	Remote Similarity	NPC474438
0.5934	Remote Similarity	NPC90953
0.5931	Remote Similarity	NPC329731
0.5931	Remote Similarity	NPC472533
0.5931	Remote Similarity	NPC4910
0.593	Remote Similarity	NPC272899
0.593	Remote Similarity	NPC476351
0.5928	Remote Similarity	NPC205523
0.5922	Remote Similarity	NPC477526
0.592	Remote Similarity	NPC327005
0.5912	Remote Similarity	NPC471316
0.5912	Remote Similarity	NPC215109
0.5912	Remote Similarity	NPC307401
0.5912	Remote Similarity	NPC170604
0.5911	Remote Similarity	NPC102760
0.5909	Remote Similarity	NPC38964
0.5909	Remote Similarity	NPC59502
0.5905	Remote Similarity	NPC112937
0.5905	Remote Similarity	NPC477527
0.5905	Remote Similarity	NPC100863
0.5904	Remote Similarity	NPC471007
0.5897	Remote Similarity	NPC471652
0.5896	Remote Similarity	NPC311781
0.5896	Remote Similarity	NPC130275
0.5896	Remote Similarity	NPC118853
0.5892	Remote Similarity	NPC223415
0.589	Remote Similarity	NPC471521
0.589	Remote Similarity	NPC473356
0.5889	Remote Similarity	NPC158525
0.5888	Remote Similarity	NPC284842
0.5886	Remote Similarity	NPC474830
0.5882	Remote Similarity	NPC346
0.5882	Remote Similarity	NPC137710
0.5882	Remote Similarity	NPC276676
0.5876	Remote Similarity	NPC21460
0.5874	Remote Similarity	NPC473008
0.5873	Remote Similarity	NPC471001
0.5872	Remote Similarity	NPC26285
0.5872	Remote Similarity	NPC283284
0.5872	Remote Similarity	NPC289911
0.587	Remote Similarity	NPC205765
0.5869	Remote Similarity	NPC43069
0.5869	Remote Similarity	NPC97086
0.5869	Remote Similarity	NPC140577
0.5869	Remote Similarity	NPC232533
0.5869	Remote Similarity	NPC243483
0.5869	Remote Similarity	NPC67346
0.5862	Remote Similarity	NPC474829
0.5862	Remote Similarity	NPC471559
0.586	Remote Similarity	NPC199044
0.586	Remote Similarity	NPC238843
0.5856	Remote Similarity	NPC46896
0.5856	Remote Similarity	NPC281104
0.5854	Remote Similarity	NPC177331
0.5854	Remote Similarity	NPC21425
0.5851	Remote Similarity	NPC250228
0.5851	Remote Similarity	NPC476938
0.5851	Remote Similarity	NPC10088
0.5851	Remote Similarity	NPC476937
0.5851	Remote Similarity	NPC470941
0.5849	Remote Similarity	NPC226652
0.5849	Remote Similarity	NPC138830
0.5849	Remote Similarity	NPC120671
0.5849	Remote Similarity	NPC72788
0.5849	Remote Similarity	NPC314100
0.5847	Remote Similarity	NPC202260
0.5843	Remote Similarity	NPC17681
0.5843	Remote Similarity	NPC477645
0.5842	Remote Similarity	NPC196846
0.5842	Remote Similarity	NPC476122
0.5842	Remote Similarity	NPC477404
0.5842	Remote Similarity	NPC196864
0.5842	Remote Similarity	NPC476936
0.5838	Remote Similarity	NPC473152
0.5838	Remote Similarity	NPC475818
0.5833	Remote Similarity	NPC471863
0.5833	Remote Similarity	NPC478075

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 NPC472474 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	664
0.2-0.3	992
0.3-0.4	2822
0.4-0.5	3422
0.5-0.6	983
0.6-0.7	48
0.7-0.8	1
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
0.7374	Intermediate Similarity	NPD5262	Discontinued
0.7043	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD3862	Approved
0.6578	Remote Similarity	NPD3861	Approved
0.6567	Remote Similarity	NPD5564	Approved
0.6436	Remote Similarity	NPD6862	Phase 2
0.6416	Remote Similarity	NPD3142	Approved
0.6416	Remote Similarity	NPD3140	Approved
0.6364	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7577	Discontinued
0.634	Remote Similarity	NPD4503	Phase 2
0.633	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5228	Phase 3
0.63	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD3124	Discontinued
0.6257	Remote Similarity	NPD5355	Approved
0.6257	Remote Similarity	NPD5356	Approved
0.625	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD4483	Discontinued
0.6224	Remote Similarity	NPD6597	Approved
0.6224	Remote Similarity	NPD6598	Approved
0.6212	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6834	Approved
0.6193	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6813	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5980	Discovery
0.6172	Remote Similarity	NPD7627	Approved
0.6172	Remote Similarity	NPD7626	Approved
0.6161	Remote Similarity	NPD8161	Suspended
0.6141	Remote Similarity	NPD6322	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7291	Discontinued
0.6129	Remote Similarity	NPD5025	Approved
0.6119	Remote Similarity	NPD6990	Approved
0.6119	Remote Similarity	NPD6989	Approved
0.6108	Remote Similarity	NPD6890	Discontinued
0.6105	Remote Similarity	NPD5977	Approved
0.6105	Remote Similarity	NPD5978	Approved
0.6085	Remote Similarity	NPD7317	Phase 3
0.6085	Remote Similarity	NPD6844	Discontinued
0.608	Remote Similarity	NPD7713	Phase 3
0.6078	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD3640	Phase 3
0.6075	Remote Similarity	NPD3639	Approved
0.6075	Remote Similarity	NPD3641	Approved
0.6071	Remote Similarity	NPD3446	Phase 1
0.607	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD6039	Approved
0.6053	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6321	Discontinued
0.6041	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD3659	Discontinued
0.6038	Remote Similarity	NPD6250	Discontinued
0.6034	Remote Similarity	NPD7162	Approved
0.603	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD7318	Phase 3
0.6009	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.599	Remote Similarity	NPD6618	Phase 2
0.599	Remote Similarity	NPD6734	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD1670	Discontinued
0.5989	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7811	Phase 3
0.5952	Remote Similarity	NPD7810	Phase 3
0.5947	Remote Similarity	NPD5890	Approved
0.5947	Remote Similarity	NPD5889	Approved
0.5946	Remote Similarity	NPD160	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD5688	Approved
0.5944	Remote Similarity	NPD743	Approved
0.5944	Remote Similarity	NPD5689	Approved
0.5942	Remote Similarity	NPD4466	Phase 1
0.5936	Remote Similarity	NPD6390	Discontinued
0.5931	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.593	Remote Similarity	NPD5313	Approved
0.593	Remote Similarity	NPD5312	Approved
0.5924	Remote Similarity	NPD4107	Approved
0.5924	Remote Similarity	NPD6748	Discontinued
0.5918	Remote Similarity	NPD5186	Approved
0.5918	Remote Similarity	NPD5183	Approved
0.5915	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD3802	Phase 3
0.5907	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD3873	Phase 3
0.5904	Remote Similarity	NPD3869	Phase 3
0.59	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD4482	Phase 3
0.5879	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD1309	Phase 2
0.5876	Remote Similarity	NPD1307	Phase 2
0.5872	Remote Similarity	NPD7272	Discontinued
0.5872	Remote Similarity	NPD5676	Approved
0.587	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.5869	Remote Similarity	NPD3533	Approved
0.5869	Remote Similarity	NPD3448	Approved
0.5869	Remote Similarity	NPD3057	Approved
0.5869	Remote Similarity	NPD2972	Approved
0.5869	Remote Similarity	NPD2491	Approved
0.5864	Remote Similarity	NPD4424	Discontinued
0.5864	Remote Similarity	NPD6386	Approved
0.5864	Remote Similarity	NPD6385	Approved
0.5864	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD6873	Phase 2
0.5862	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.586	Remote Similarity	NPD6066	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6894	Phase 1
0.5856	Remote Similarity	NPD2567	Approved
0.5856	Remote Similarity	NPD2569	Approved
0.5847	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.5845	Remote Similarity	NPD5480	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD2512	Phase 3
0.584	Remote Similarity	NPD4369	Phase 2
0.5837	Remote Similarity	NPD7047	Phase 3
0.5837	Remote Similarity	NPD6871	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4618	Approved
0.5833	Remote Similarity	NPD4622	Approved
0.5829	Remote Similarity	NPD4098	Discontinued
0.5829	Remote Similarity	NPD7598	Phase 2
0.5825	Remote Similarity	NPD7693	Approved
0.5821	Remote Similarity	NPD5485	Approved
0.5821	Remote Similarity	NPD5484	Approved
0.582	Remote Similarity	NPD7427	Discontinued
0.5812	Remote Similarity	NPD6585	Discontinued
0.5812	Remote Similarity	NPD2592	Discontinued
0.5811	Remote Similarity	NPD4989	Phase 2
0.5811	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6874	Approved
0.5799	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD4679	Discontinued
0.5792	Remote Similarity	NPD5293	Phase 2
0.5787	Remote Similarity	NPD6107	Approved
0.5784	Remote Similarity	NPD8064	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD44	Approved
0.5784	Remote Similarity	NPD7280	Phase 3
0.5784	Remote Similarity	NPD6364	Approved
0.5784	Remote Similarity	NPD7281	Phase 3
0.5782	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD4773	Phase 2
0.5781	Remote Similarity	NPD4772	Phase 2
0.5779	Remote Similarity	NPD246	Approved
0.5779	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.5777	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD8164	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD2200	Suspended
0.5765	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD4420	Approved
0.5753	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6997	Phase 2
0.5751	Remote Similarity	NPD6279	Approved
0.5751	Remote Similarity	NPD7298	Approved
0.5751	Remote Similarity	NPD7248	Discontinued
0.5751	Remote Similarity	NPD6280	Approved
0.5738	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD2904	Discontinued
0.5736	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.573	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7820	Phase 3
0.5722	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD4474	Approved
0.5722	Remote Similarity	NPD4475	Approved
0.5721	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD7316	Discontinued
0.5721	Remote Similarity	NPD5005	Approved
0.5721	Remote Similarity	NPD5006	Approved
0.5714	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4584	Approved
0.5714	Remote Similarity	NPD4661	Approved
0.5714	Remote Similarity	NPD5159	Phase 2
0.5714	Remote Similarity	NPD4662	Approved
0.5714	Remote Similarity	NPD5157	Phase 1
0.5708	Remote Similarity	NPD7556	Discontinued
0.5707	Remote Similarity	NPD2247	Approved
0.5707	Remote Similarity	NPD2249	Approved
0.5707	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4505	Phase 1
0.5701	Remote Similarity	NPD6826	Discontinued
0.5701	Remote Similarity	NPD5457	Discontinued
0.57	Remote Similarity	NPD1194	Discontinued
0.57	Remote Similarity	NPD6891	Phase 2
0.5699	Remote Similarity	NPD4127	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD6677	Suspended
0.5698	Remote Similarity	NPD2595	Approved
0.5698	Remote Similarity	NPD6382	Discontinued
0.5698	Remote Similarity	NPD2594	Approved
0.5695	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD5967	Approved
0.5691	Remote Similarity	NPD7440	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