NPASS Compound

Structure

NPC236004 OpenBabel07101719252D 40 45 0 0 1 0 0 0 0 0999 V2000 2.6748 0.6669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9838 -0.4600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3333 -0.5268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1504 -2.2293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0755 4.8157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7073 2.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3903 -1.3800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8767 -0.9150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1870 -0.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7766 -1.1063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3903 1.3800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3690 3.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6210 0.3742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8750 -1.2043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0592 1.3506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7805 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5935 -0.9200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3903 0.4600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0439 -0.2813 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8100 3.8473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1870 1.8400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5935 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7968 0.4600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9838 0.4600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8750 0.2843 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1870 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4158 -0.4600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7968 -1.3800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3435 2.2255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1023 3.7285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1870 2.7600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7968 1.3800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3742 -1.7605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1632 4.6968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3742 0.8405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2366 -0.3095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1593 1.1593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9838 1.3800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 4 28 1 0 0 0 0 5 36 1 0 0 0 0 6 37 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 26 1 0 0 0 0 10 38 1 0 0 0 0 11 18 1 0 0 0 0 11 21 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 38 1 0 0 0 0 14 27 1 0 0 0 0 14 29 1 0 0 0 0 15 31 2 0 0 0 0 15 39 1 0 0 0 0 16 24 1 0 0 0 0 17 22 1 0 0 0 0 17 28 1 1 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 1 0 0 0 19 28 1 0 0 0 0 20 32 2 0 0 0 0 20 36 1 0 0 0 0 21 33 2 0 0 0 0 21 40 1 0 0 0 0 22 23 1 0 0 0 0 23 30 1 0 0 0 0 23 34 2 0 0 0 0 24 26 1 6 0 0 0 24 40 1 0 0 0 0 25 27 1 1 0 0 0 25 30 1 0 0 0 0 25 39 1 0 0 0 0 26 2 1 6 0 0 0 27 3 1 6 0 0 0 28 29 1 6 0 0 0 29 30 1 6 0 0 0 29 35 1 0 0 0 0 30 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	556.23
Volume:	545.544
LogP:	2.546
LogD:	1.534
LogS:	-4.668
# Rotatable Bonds:	7
TPSA:	138.57
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	6.199
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.304
MDCK Permeability:	2.9330243705771863e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.144
Human Intestinal Absorption (HIA):	0.352
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.529
Plasma Protein Binding (PPB):	77.97940826416016%
Volume Distribution (VD):	1.053
Pgp-substrate:	17.600221633911133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.288
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.233
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.924
CYP3A4-substrate:	0.607

ADMET: Excretion

Clearance (CL):	2.493
Half-life (T1/2):	0.642

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.474
Drug-inuced Liver Injury (DILI):	0.477
AMES Toxicity:	0.526
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.407
Skin Sensitization:	0.451
Carcinogencity:	0.906
Eye Corrosion:	0.005
Eye Irritation:	0.016
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC236004

Natural Product ID:	NPC236004
*Common Name:**	Moluccensin I
IUPAC Name:	n.a.
Synonyms:	Moluccensin I
Standard InCHIKey:	DXAWUJPEJQPCGT-IQXSIFHKSA-N
Standard InCHI:	InChI=1S/C30H36O10/c1-15(31)39-25-27(3)14-29(35)28(4,19(27)12-20(32)36-5)17-7-9-26(2)18(22(17)23(34)30(25,29)37-6)11-21(33)40-24(26)16-8-10-38-13-16/h8,10,13,17,19,24-25,35H,7,9,11-12,14H2,1-6H3/t17-,19-,24-,25-,26+,27-,28+,29+,30+/m0/s1
SMILES:	COC(=O)C[C@H]1[C@]2(C)C[C@]3([C@]1(C)[C@H]1CC[C@@]4(C(=C1C(=O)[C@]3([C@H]2OC(=O)C)OC)CC(=O)O[C@H]4c1ccoc1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076925
PubChem CID:	46184328
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112995]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20146503]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	Thai	n.a.	PMID[21733687]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22724531]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26114936]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	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	6
MIC	2
Others	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT845	Cell Line	BT-474	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[482295]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[482295]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[482295]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[482295]
NPT4025	Organism	Staphylococcus hominis	Staphylococcus hominis	MIC	=	256.0	ug.mL-1	PMID[482295]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	223.0	ug.mL-1	PMID[482295]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	10.7	%	PMID[482296]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	28.7	%	PMID[482296]
NPT2	Others	Unspecified		IC50	>	27000.0	nM	PMID[482297]

☑ 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 NPC236004 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	388
0.1-0.2	1494
0.2-0.3	3375
0.3-0.4	5724
0.4-0.5	10830
0.5-0.6	10122
0.6-0.7	9179
0.7-0.8	1163
0.8-0.85	295
0.85-0.9	97
0.9-0.95	24
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9876	High Similarity	NPC94763
0.9755	High Similarity	NPC478177
0.9632	High Similarity	NPC469576
0.9627	High Similarity	NPC327922
0.9573	High Similarity	NPC469633
0.9503	High Similarity	NPC478178
0.95	High Similarity	NPC165218
0.9286	High Similarity	NPC470938
0.9277	High Similarity	NPC471437
0.9273	High Similarity	NPC159232
0.9207	High Similarity	NPC478179
0.9152	High Similarity	NPC472766
0.9152	High Similarity	NPC472765
0.9091	High Similarity	NPC476224
0.9091	High Similarity	NPC472764
0.9042	High Similarity	NPC285227
0.903	High Similarity	NPC149945
0.9024	High Similarity	NPC469338
0.9024	High Similarity	NPC292389
0.9012	High Similarity	NPC36655
0.9012	High Similarity	NPC261597
0.9012	High Similarity	NPC247563
0.9012	High Similarity	NPC242068
0.9006	High Similarity	NPC214541
0.9006	High Similarity	NPC44675
0.8982	High Similarity	NPC472659
0.8976	High Similarity	NPC173516
0.897	High Similarity	NPC469849
0.897	High Similarity	NPC276551
0.897	High Similarity	NPC470940
0.8963	High Similarity	NPC82851
0.8963	High Similarity	NPC6326
0.8957	High Similarity	NPC477403
0.8957	High Similarity	NPC475967
0.8941	High Similarity	NPC470181
0.8922	High Similarity	NPC471397
0.8922	High Similarity	NPC271235
0.8916	High Similarity	NPC214600
0.8916	High Similarity	NPC470875
0.8902	High Similarity	NPC472653
0.8902	High Similarity	NPC105395
0.8902	High Similarity	NPC477402
0.8896	High Similarity	NPC187149
0.8889	High Similarity	NPC264943
0.8876	High Similarity	NPC469848
0.8869	High Similarity	NPC470995
0.8862	High Similarity	NPC472775
0.8862	High Similarity	NPC472774
0.8862	High Similarity	NPC472651
0.8848	High Similarity	NPC5079
0.8848	High Similarity	NPC149896
0.8848	High Similarity	NPC472767
0.8848	High Similarity	NPC69028
0.8824	High Similarity	NPC471632
0.8817	High Similarity	NPC169299
0.8817	High Similarity	NPC160818
0.881	High Similarity	NPC472652
0.881	High Similarity	NPC160651
0.8795	High Similarity	NPC39986
0.8795	High Similarity	NPC663
0.8795	High Similarity	NPC224394
0.8795	High Similarity	NPC134254
0.8795	High Similarity	NPC302369
0.8795	High Similarity	NPC472773
0.8795	High Similarity	NPC51568
0.8795	High Similarity	NPC477405
0.8795	High Similarity	NPC234660
0.8788	High Similarity	NPC25255
0.878	High Similarity	NPC195131
0.878	High Similarity	NPC45101
0.878	High Similarity	NPC249021
0.878	High Similarity	NPC286722
0.878	High Similarity	NPC299038
0.878	High Similarity	NPC472777
0.878	High Similarity	NPC472776
0.878	High Similarity	NPC472778
0.878	High Similarity	NPC470118
0.875	High Similarity	NPC476850
0.875	High Similarity	NPC476861
0.8743	High Similarity	NPC476857
0.8743	High Similarity	NPC470182
0.8743	High Similarity	NPC271657
0.8743	High Similarity	NPC476856
0.8743	High Similarity	NPC476858
0.8743	High Similarity	NPC123088
0.8735	High Similarity	NPC472668
0.8735	High Similarity	NPC329938
0.8735	High Similarity	NPC197596
0.8735	High Similarity	NPC18347
0.8735	High Similarity	NPC200782
0.8735	High Similarity	NPC193798
0.8735	High Similarity	NPC472771
0.8727	High Similarity	NPC475295
0.8727	High Similarity	NPC473473
0.8727	High Similarity	NPC475226
0.872	High Similarity	NPC469485
0.872	High Similarity	NPC204663
0.872	High Similarity	NPC209364
0.8713	High Similarity	NPC477824
0.869	High Similarity	NPC472141
0.8683	High Similarity	NPC472139
0.8683	High Similarity	NPC469846
0.8683	High Similarity	NPC472669
0.8683	High Similarity	NPC471168
0.8675	High Similarity	NPC335761
0.8675	High Similarity	NPC470789
0.8667	High Similarity	NPC472283
0.8667	High Similarity	NPC173544
0.8667	High Similarity	NPC197137
0.8659	High Similarity	NPC155939
0.8659	High Similarity	NPC296807
0.8659	High Similarity	NPC141538
0.865	High Similarity	NPC476201
0.865	High Similarity	NPC469503
0.8647	High Similarity	NPC82602
0.8647	High Similarity	NPC472650
0.8639	High Similarity	NPC476853
0.8639	High Similarity	NPC472282
0.8631	High Similarity	NPC476860
0.8623	High Similarity	NPC263432
0.8623	High Similarity	NPC188649
0.8623	High Similarity	NPC470939
0.8623	High Similarity	NPC471167
0.8623	High Similarity	NPC5741
0.8623	High Similarity	NPC470792
0.8623	High Similarity	NPC117986
0.8623	High Similarity	NPC96443
0.8623	High Similarity	NPC290400
0.8623	High Similarity	NPC471166
0.8614	High Similarity	NPC474932
0.8606	High Similarity	NPC107646
0.8606	High Similarity	NPC126723
0.8598	High Similarity	NPC282445
0.858	High Similarity	NPC23387
0.8571	High Similarity	NPC88841
0.8571	High Similarity	NPC288602
0.8563	High Similarity	NPC475381
0.8563	High Similarity	NPC191828
0.8555	High Similarity	NPC262386
0.8554	High Similarity	NPC167142
0.8554	High Similarity	NPC472772
0.8545	High Similarity	NPC469336
0.8545	High Similarity	NPC92979
0.8545	High Similarity	NPC476262
0.8537	High Similarity	NPC33938
0.8537	High Similarity	NPC44577
0.8528	High Similarity	NPC470997
0.8521	High Similarity	NPC259943
0.8512	High Similarity	NPC211777
0.8503	High Similarity	NPC472671
0.8503	High Similarity	NPC237155
0.8503	High Similarity	NPC307383
0.8503	High Similarity	NPC472779
0.8494	Intermediate Similarity	NPC60973
0.8485	Intermediate Similarity	NPC178932
0.8485	Intermediate Similarity	NPC34421
0.8485	Intermediate Similarity	NPC98206
0.8485	Intermediate Similarity	NPC253201
0.8485	Intermediate Similarity	NPC302054
0.8485	Intermediate Similarity	NPC57998
0.8485	Intermediate Similarity	NPC237259
0.848	Intermediate Similarity	NPC472673
0.848	Intermediate Similarity	NPC242334
0.8476	Intermediate Similarity	NPC18135
0.8476	Intermediate Similarity	NPC116717
0.8471	Intermediate Similarity	NPC97574
0.8471	Intermediate Similarity	NPC475779
0.8471	Intermediate Similarity	NPC93172
0.8466	Intermediate Similarity	NPC234494
0.8466	Intermediate Similarity	NPC472654
0.8466	Intermediate Similarity	NPC69647
0.8466	Intermediate Similarity	NPC471001
0.8466	Intermediate Similarity	NPC125182
0.8462	Intermediate Similarity	NPC198047
0.8457	Intermediate Similarity	NPC255414
0.8452	Intermediate Similarity	NPC305016
0.8443	Intermediate Similarity	NPC88007
0.8443	Intermediate Similarity	NPC214495
0.8443	Intermediate Similarity	NPC475066
0.8443	Intermediate Similarity	NPC470119
0.8434	Intermediate Similarity	NPC471175
0.8434	Intermediate Similarity	NPC281258
0.8424	Intermediate Similarity	NPC470996
0.8424	Intermediate Similarity	NPC268905
0.8424	Intermediate Similarity	NPC246164
0.8424	Intermediate Similarity	NPC472672
0.8421	Intermediate Similarity	NPC473766
0.8421	Intermediate Similarity	NPC473753
0.8421	Intermediate Similarity	NPC100333
0.8415	Intermediate Similarity	NPC159927
0.8415	Intermediate Similarity	NPC156189
0.8415	Intermediate Similarity	NPC196846
0.8415	Intermediate Similarity	NPC469335
0.8415	Intermediate Similarity	NPC476122
0.8412	Intermediate Similarity	NPC261184
0.8402	Intermediate Similarity	NPC68848
0.8402	Intermediate Similarity	NPC207978
0.8395	Intermediate Similarity	NPC346
0.8393	Intermediate Similarity	NPC262872
0.8383	Intermediate Similarity	NPC175964

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 NPC236004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	1035
0.2-0.3	2322
0.3-0.4	2755
0.4-0.5	1731
0.5-0.6	695
0.6-0.7	266
0.7-0.8	14
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8659	High Similarity	NPD5761	Phase 2
0.8659	High Similarity	NPD5760	Phase 2
0.8212	Intermediate Similarity	NPD8434	Phase 2
0.8129	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD6764	Approved
0.8034	Intermediate Similarity	NPD6765	Approved
0.7857	Intermediate Similarity	NPD6785	Approved
0.7857	Intermediate Similarity	NPD6784	Approved
0.7486	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7075	Discontinued
0.7418	Intermediate Similarity	NPD7799	Discontinued
0.738	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6599	Discontinued
0.7209	Intermediate Similarity	NPD7236	Approved
0.7191	Intermediate Similarity	NPD7819	Suspended
0.7171	Intermediate Similarity	NPD8404	Phase 2
0.7166	Intermediate Similarity	NPD6559	Discontinued
0.7151	Intermediate Similarity	NPD3817	Phase 2
0.7135	Intermediate Similarity	NPD6801	Discontinued
0.7127	Intermediate Similarity	NPD919	Approved
0.7102	Intermediate Similarity	NPD7239	Suspended
0.7098	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7497	Discontinued
0.7074	Intermediate Similarity	NPD7685	Pre-registration
0.7069	Intermediate Similarity	NPD6799	Approved
0.7065	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3882	Suspended
0.6995	Remote Similarity	NPD5494	Approved
0.6994	Remote Similarity	NPD4628	Phase 3
0.6961	Remote Similarity	NPD5402	Approved
0.6957	Remote Similarity	NPD8127	Discontinued
0.6957	Remote Similarity	NPD1247	Approved
0.6949	Remote Similarity	NPD920	Approved
0.6923	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5762	Approved
0.6919	Remote Similarity	NPD5763	Approved
0.6915	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7473	Discontinued
0.6897	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6273	Approved
0.6891	Remote Similarity	NPD8150	Discontinued
0.6885	Remote Similarity	NPD3749	Approved
0.6875	Remote Similarity	NPD8407	Phase 2
0.6865	Remote Similarity	NPD7199	Phase 2
0.6862	Remote Similarity	NPD3818	Discontinued
0.6862	Remote Similarity	NPD3751	Discontinued
0.6859	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5403	Approved
0.6851	Remote Similarity	NPD1934	Approved
0.6845	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6166	Phase 2
0.6836	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD5401	Approved
0.6833	Remote Similarity	NPD4380	Phase 2
0.6825	Remote Similarity	NPD5844	Phase 1
0.6806	Remote Similarity	NPD7251	Discontinued
0.6806	Remote Similarity	NPD8368	Discontinued
0.6796	Remote Similarity	NPD7411	Suspended
0.6793	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7907	Approved
0.6776	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7808	Phase 3
0.6754	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6797	Phase 2
0.6749	Remote Similarity	NPD7435	Discontinued
0.6742	Remote Similarity	NPD2532	Approved
0.6742	Remote Similarity	NPD2534	Approved
0.6742	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2533	Approved
0.6742	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7057	Phase 3
0.6739	Remote Similarity	NPD7058	Phase 2
0.6738	Remote Similarity	NPD6232	Discontinued
0.6738	Remote Similarity	NPD3787	Discontinued
0.6736	Remote Similarity	NPD8313	Approved
0.6736	Remote Similarity	NPD8312	Approved
0.6725	Remote Similarity	NPD6355	Discontinued
0.6724	Remote Similarity	NPD6005	Phase 3
0.6724	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6002	Phase 3
0.6724	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1471	Phase 3
0.6724	Remote Similarity	NPD6004	Phase 3
0.6723	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7074	Phase 3
0.6702	Remote Similarity	NPD3926	Phase 2
0.6685	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6651	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4965	Approved
0.6649	Remote Similarity	NPD7054	Approved
0.6649	Remote Similarity	NPD4966	Approved
0.6649	Remote Similarity	NPD4967	Phase 2
0.6648	Remote Similarity	NPD2800	Approved
0.6648	Remote Similarity	NPD7028	Phase 2
0.663	Remote Similarity	NPD2801	Approved
0.6629	Remote Similarity	NPD2346	Discontinued
0.662	Remote Similarity	NPD4111	Phase 1
0.662	Remote Similarity	NPD4665	Approved
0.6615	Remote Similarity	NPD7472	Approved
0.6601	Remote Similarity	NPD4107	Approved
0.6597	Remote Similarity	NPD7228	Approved
0.6596	Remote Similarity	NPD6959	Discontinued
0.6591	Remote Similarity	NPD1549	Phase 2
0.6579	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD37	Approved
0.6571	Remote Similarity	NPD6099	Approved
0.6571	Remote Similarity	NPD6100	Approved
0.6571	Remote Similarity	NPD2796	Approved
0.6566	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8435	Approved
0.6555	Remote Similarity	NPD7874	Approved
0.6555	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1243	Approved
0.6541	Remote Similarity	NPD1465	Phase 2
0.6537	Remote Similarity	NPD3057	Approved
0.6534	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5735	Approved
0.6527	Remote Similarity	NPD7078	Approved
0.652	Remote Similarity	NPD6781	Approved
0.652	Remote Similarity	NPD6782	Approved
0.652	Remote Similarity	NPD6780	Approved
0.652	Remote Similarity	NPD6778	Approved
0.652	Remote Similarity	NPD6776	Approved
0.652	Remote Similarity	NPD6779	Approved
0.652	Remote Similarity	NPD6777	Approved
0.6519	Remote Similarity	NPD1512	Approved
0.6517	Remote Similarity	NPD3750	Approved
0.6514	Remote Similarity	NPD2799	Discontinued
0.6509	Remote Similarity	NPD5647	Approved
0.6503	Remote Similarity	NPD7458	Discontinued
0.6497	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6653	Approved
0.6492	Remote Similarity	NPD2403	Approved
0.6488	Remote Similarity	NPD4482	Phase 3
0.6484	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD8360	Approved
0.6482	Remote Similarity	NPD8361	Approved
0.648	Remote Similarity	NPD6190	Approved
0.6477	Remote Similarity	NPD1551	Phase 2
0.6474	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD8320	Phase 1
0.6473	Remote Similarity	NPD8319	Approved
0.6471	Remote Similarity	NPD7768	Phase 2
0.6464	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6319	Approved
0.6462	Remote Similarity	NPD7240	Approved
0.6456	Remote Similarity	NPD2972	Approved
0.6456	Remote Similarity	NPD3533	Approved
0.6425	Remote Similarity	NPD7697	Approved
0.6425	Remote Similarity	NPD7696	Phase 3
0.6425	Remote Similarity	NPD7698	Approved
0.6425	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7033	Discontinued
0.642	Remote Similarity	NPD3748	Approved
0.6413	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD1511	Approved
0.6407	Remote Similarity	NPD7492	Approved
0.64	Remote Similarity	NPD7048	Phase 3
0.6395	Remote Similarity	NPD7095	Approved
0.6394	Remote Similarity	NPD7870	Phase 2
0.6394	Remote Similarity	NPD7871	Phase 2
0.6392	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7315	Approved
0.6387	Remote Similarity	NPD7229	Phase 3
0.6387	Remote Similarity	NPD5711	Approved
0.6387	Remote Similarity	NPD5710	Approved
0.6382	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7701	Phase 2
0.6379	Remote Similarity	NPD4140	Approved
0.6373	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD8485	Approved
0.6369	Remote Similarity	NPD6616	Approved
0.6368	Remote Similarity	NPD7801	Approved
0.6364	Remote Similarity	NPD6054	Approved
0.6358	Remote Similarity	NPD2313	Discontinued
0.6358	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6798	Discontinued
0.6353	Remote Similarity	NPD7319	Approved
0.6353	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD2344	Approved
0.6343	Remote Similarity	NPD447	Suspended
0.6338	Remote Similarity	NPD8462	Phase 1
0.6337	Remote Similarity	NPD6832	Phase 2
0.6333	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4110	Phase 3
0.6328	Remote Similarity	NPD1510	Phase 2
0.6322	Remote Similarity	NPD6233	Phase 2
0.6322	Remote Similarity	NPD6663	Approved
0.6322	Remote Similarity	NPD8032	Phase 2
0.6319	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD6353	Approved
0.6307	Remote Similarity	NPD6651	Approved
0.6298	Remote Similarity	NPD3887	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