NPASS Compound

Structure

NPC471842 OpenBabel07101718242D 30 34 0 0 1 0 0 0 0 0999 V2000 -0.6000 2.5768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2183 -0.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3255 -0.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2183 -2.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7413 -2.2007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7045 1.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 -1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0844 -1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2765 -0.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0844 -2.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4844 -1.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 -2.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7902 -1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8135 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6180 1.1756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9504 -0.8271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0197 0.1157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9504 -2.8271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4355 -1.8406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.7045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -2.6361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9242 -2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 2 10 2 0 0 0 0 3 9 1 0 0 0 0 3 11 2 0 0 0 0 4 12 2 0 0 0 0 4 14 1 0 0 0 0 5 13 2 0 0 0 0 5 15 1 0 0 0 0 6 7 1 0 0 0 0 6 21 1 0 0 0 0 7 22 2 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 21 1 0 0 0 0 20 27 2 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.06
Volume:	381.737
LogP:	2.056
LogD:	2.058
LogS:	-3.64
# Rotatable Bonds:	2
TPSA:	161.57
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.313
Synthetic Accessibility Score:	3.802
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.723
MDCK Permeability:	1.1709096725098789e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.668
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.85

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	87.75090026855469%
Volume Distribution (VD):	0.643
Pgp-substrate:	15.385270118713379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.907
CYP1A2-substrate:	0.74
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.456
CYP2C9-substrate:	0.384
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.358
CYP3A4-substrate:	0.124

ADMET: Excretion

Clearance (CL):	10.208
Half-life (T1/2):	0.841

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.401
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.627
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.785
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.785
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC471842

Natural Product ID:	NPC471842
*Common Name:**	YOKUNGSJWHUOJL-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YOKUNGSJWHUOJL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H14O9/c1-7(22)6-21(28)17-9-3-11(24)13(26)5-15(9)30-19(17)18-16(20(21)27)8-2-10(23)12(25)4-14(8)29-18/h2-5,23-26,28H,6H2,1H3
SMILES:	CC(=O)CC1(C2=C(C3=C(C1=O)C4=CC(=C(C=C4O3)O)O)OC5=CC(=C(C=C52)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3236670
PubChem CID:	90655410
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO7806	Polyozellus multiplex	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24601669]
NPO7806	Polyozellus multiplex	Species	Thelephoraceae	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

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	IC50	=	52000.0	nM	PMID[527315]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	21400.0	nM	PMID[527315]

☑ 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 NPC471842 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	497
0.1-0.2	2229
0.2-0.3	4900
0.3-0.4	11586
0.4-0.5	6250
0.5-0.6	4370
0.6-0.7	5607
0.7-0.8	5140
0.8-0.85	1433
0.85-0.9	652
0.9-0.95	30
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.976	High Similarity	NPC471841
0.9641	High Similarity	NPC117450
0.9477	High Similarity	NPC71260
0.9298	High Similarity	NPC24258
0.9209	High Similarity	NPC60848
0.9123	High Similarity	NPC230619
0.9123	High Similarity	NPC54098
0.9118	High Similarity	NPC202470
0.9075	High Similarity	NPC8127
0.9075	High Similarity	NPC49667
0.907	High Similarity	NPC82217
0.907	High Similarity	NPC476640
0.907	High Similarity	NPC216842
0.9064	High Similarity	NPC28042
0.9059	High Similarity	NPC470704
0.9045	High Similarity	NPC295436
0.9023	High Similarity	NPC98546
0.9017	High Similarity	NPC289244
0.9017	High Similarity	NPC287243
0.896	High Similarity	NPC30550
0.896	High Similarity	NPC65885
0.896	High Similarity	NPC277510
0.8953	High Similarity	NPC476641
0.8941	High Similarity	NPC45449
0.8935	High Similarity	NPC238995
0.892	High Similarity	NPC47883
0.8914	High Similarity	NPC23553
0.8914	High Similarity	NPC77179
0.8914	High Similarity	NPC297807
0.8882	High Similarity	NPC263092
0.8882	High Similarity	NPC1755
0.8882	High Similarity	NPC1706
0.8882	High Similarity	NPC59295
0.8882	High Similarity	NPC39305
0.887	High Similarity	NPC240508
0.8864	High Similarity	NPC476273
0.8851	High Similarity	NPC149846
0.8851	High Similarity	NPC473834
0.8837	High Similarity	NPC95715
0.8837	High Similarity	NPC50394
0.883	High Similarity	NPC36320
0.8814	High Similarity	NPC475996
0.8807	High Similarity	NPC221820
0.88	High Similarity	NPC245975
0.8786	High Similarity	NPC247136
0.8772	High Similarity	NPC133065
0.8765	High Similarity	NPC188486
0.8764	High Similarity	NPC246153
0.8764	High Similarity	NPC228209
0.8757	High Similarity	NPC196879
0.875	High Similarity	NPC156955
0.8743	High Similarity	NPC37606
0.8722	High Similarity	NPC248315
0.8721	High Similarity	NPC39306
0.8715	High Similarity	NPC476170
0.8713	High Similarity	NPC84515
0.8713	High Similarity	NPC272722
0.8713	High Similarity	NPC312056
0.8693	High Similarity	NPC227906
0.8686	High Similarity	NPC28589
0.8686	High Similarity	NPC248593
0.8686	High Similarity	NPC174700
0.8667	High Similarity	NPC304322
0.8667	High Similarity	NPC226725
0.8659	High Similarity	NPC8927
0.8647	High Similarity	NPC16935
0.8639	High Similarity	NPC45131
0.8639	High Similarity	NPC472461
0.8636	High Similarity	NPC310794
0.8629	High Similarity	NPC218533
0.8629	High Similarity	NPC78830
0.8621	High Similarity	NPC247973
0.8621	High Similarity	NPC86477
0.8619	High Similarity	NPC139683
0.8619	High Similarity	NPC73929
0.8619	High Similarity	NPC240808
0.8619	High Similarity	NPC47905
0.8613	High Similarity	NPC37183
0.8613	High Similarity	NPC291110
0.8613	High Similarity	NPC29411
0.8611	High Similarity	NPC154527
0.8596	High Similarity	NPC246877
0.8571	High Similarity	NPC125300
0.8563	High Similarity	NPC277480
0.8556	High Similarity	NPC182693
0.8555	High Similarity	NPC41301
0.8547	High Similarity	NPC183843
0.8547	High Similarity	NPC231758
0.8547	High Similarity	NPC104682
0.8539	High Similarity	NPC164384
0.8538	High Similarity	NPC193842
0.8538	High Similarity	NPC195832
0.8531	High Similarity	NPC261471
0.8529	High Similarity	NPC268161
0.8514	High Similarity	NPC241820
0.8497	Intermediate Similarity	NPC294965
0.8488	Intermediate Similarity	NPC246478
0.8488	Intermediate Similarity	NPC84571
0.8483	Intermediate Similarity	NPC290304
0.8483	Intermediate Similarity	NPC236327
0.848	Intermediate Similarity	NPC78302
0.848	Intermediate Similarity	NPC176665
0.848	Intermediate Similarity	NPC163524
0.848	Intermediate Similarity	NPC7973
0.848	Intermediate Similarity	NPC305663
0.848	Intermediate Similarity	NPC472438
0.848	Intermediate Similarity	NPC235215
0.848	Intermediate Similarity	NPC29841
0.848	Intermediate Similarity	NPC287979
0.8475	Intermediate Similarity	NPC158226
0.8475	Intermediate Similarity	NPC292794
0.8466	Intermediate Similarity	NPC163130
0.8466	Intermediate Similarity	NPC242395
0.8466	Intermediate Similarity	NPC211309
0.8466	Intermediate Similarity	NPC165979
0.8457	Intermediate Similarity	NPC170245
0.8457	Intermediate Similarity	NPC272560
0.8448	Intermediate Similarity	NPC472582
0.8448	Intermediate Similarity	NPC475985
0.8448	Intermediate Similarity	NPC470459
0.8448	Intermediate Similarity	NPC270837
0.8439	Intermediate Similarity	NPC311740
0.8439	Intermediate Similarity	NPC61010
0.8439	Intermediate Similarity	NPC258331
0.843	Intermediate Similarity	NPC25495
0.843	Intermediate Similarity	NPC4481
0.843	Intermediate Similarity	NPC22472
0.843	Intermediate Similarity	NPC204854
0.843	Intermediate Similarity	NPC261004
0.843	Intermediate Similarity	NPC176300
0.843	Intermediate Similarity	NPC55738
0.843	Intermediate Similarity	NPC19687
0.843	Intermediate Similarity	NPC18607
0.843	Intermediate Similarity	NPC288669
0.843	Intermediate Similarity	NPC9609
0.843	Intermediate Similarity	NPC300943
0.843	Intermediate Similarity	NPC476242
0.843	Intermediate Similarity	NPC253634
0.843	Intermediate Similarity	NPC115798
0.843	Intermediate Similarity	NPC191459
0.843	Intermediate Similarity	NPC7846
0.843	Intermediate Similarity	NPC100123
0.843	Intermediate Similarity	NPC143828
0.843	Intermediate Similarity	NPC130894
0.843	Intermediate Similarity	NPC105242
0.843	Intermediate Similarity	NPC18772
0.843	Intermediate Similarity	NPC152166
0.8421	Intermediate Similarity	NPC100916
0.8421	Intermediate Similarity	NPC98661
0.8421	Intermediate Similarity	NPC138243
0.8421	Intermediate Similarity	NPC55619
0.8421	Intermediate Similarity	NPC43243
0.8421	Intermediate Similarity	NPC266960
0.8421	Intermediate Similarity	NPC200388
0.8421	Intermediate Similarity	NPC274730
0.8421	Intermediate Similarity	NPC247017
0.8421	Intermediate Similarity	NPC245546
0.8421	Intermediate Similarity	NPC474520
0.8418	Intermediate Similarity	NPC131866
0.8409	Intermediate Similarity	NPC126204
0.8409	Intermediate Similarity	NPC158761
0.8409	Intermediate Similarity	NPC186392
0.8402	Intermediate Similarity	NPC171010
0.84	Intermediate Similarity	NPC187923
0.84	Intermediate Similarity	NPC38914
0.84	Intermediate Similarity	NPC326520
0.84	Intermediate Similarity	NPC300053
0.84	Intermediate Similarity	NPC470457
0.8398	Intermediate Similarity	NPC97523
0.8391	Intermediate Similarity	NPC25152
0.8391	Intermediate Similarity	NPC219861
0.8391	Intermediate Similarity	NPC81679
0.8389	Intermediate Similarity	NPC207467
0.8389	Intermediate Similarity	NPC475783
0.8382	Intermediate Similarity	NPC220582
0.8382	Intermediate Similarity	NPC228785
0.8382	Intermediate Similarity	NPC320359
0.8382	Intermediate Similarity	NPC200746
0.8382	Intermediate Similarity	NPC56085
0.8382	Intermediate Similarity	NPC304839
0.8382	Intermediate Similarity	NPC139036
0.8382	Intermediate Similarity	NPC14353
0.8382	Intermediate Similarity	NPC476980
0.838	Intermediate Similarity	NPC99591
0.8372	Intermediate Similarity	NPC227192
0.8372	Intermediate Similarity	NPC93376
0.8372	Intermediate Similarity	NPC203891
0.8372	Intermediate Similarity	NPC101830
0.8372	Intermediate Similarity	NPC241904
0.8372	Intermediate Similarity	NPC300727
0.8372	Intermediate Similarity	NPC224137
0.8372	Intermediate Similarity	NPC75215
0.8372	Intermediate Similarity	NPC110070
0.8372	Intermediate Similarity	NPC36852
0.8372	Intermediate Similarity	NPC189179
0.8372	Intermediate Similarity	NPC185526
0.8372	Intermediate Similarity	NPC262286
0.8371	Intermediate Similarity	NPC121333
0.8371	Intermediate Similarity	NPC307286
0.8363	Intermediate Similarity	NPC208197

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 NPC471842 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	440
0.1-0.2	1087
0.2-0.3	2047
0.3-0.4	2820
0.4-0.5	1603
0.5-0.6	782
0.6-0.7	248
0.7-0.8	102
0.8-0.85	16
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8314	Intermediate Similarity	NPD3882	Suspended
0.8229	Intermediate Similarity	NPD1247	Approved
0.8198	Intermediate Similarity	NPD2801	Approved
0.8136	Intermediate Similarity	NPD3926	Phase 2
0.809	Intermediate Similarity	NPD6166	Phase 2
0.809	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD6232	Discontinued
0.8045	Intermediate Similarity	NPD7473	Discontinued
0.8035	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD1512	Approved
0.7955	Intermediate Similarity	NPD3749	Approved
0.7901	Intermediate Similarity	NPD3818	Discontinued
0.7886	Intermediate Similarity	NPD1465	Phase 2
0.7886	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD1511	Approved
0.7865	Intermediate Similarity	NPD5494	Approved
0.7841	Intermediate Similarity	NPD3817	Phase 2
0.7821	Intermediate Similarity	NPD6959	Discontinued
0.7797	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD5844	Phase 1
0.7709	Intermediate Similarity	NPD919	Approved
0.7676	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7075	Discontinued
0.7634	Intermediate Similarity	NPD6559	Discontinued
0.7633	Intermediate Similarity	NPD2344	Approved
0.763	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6797	Phase 2
0.7566	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3226	Approved
0.7544	Intermediate Similarity	NPD2800	Approved
0.7542	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD7251	Discontinued
0.7539	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1471	Phase 3
0.7528	Intermediate Similarity	NPD6801	Discontinued
0.7527	Intermediate Similarity	NPD7074	Phase 3
0.7526	Intermediate Similarity	NPD8434	Phase 2
0.7514	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7054	Approved
0.7472	Intermediate Similarity	NPD7411	Suspended
0.7461	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD2309	Approved
0.7446	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5402	Approved
0.7433	Intermediate Similarity	NPD7472	Approved
0.7419	Intermediate Similarity	NPD3751	Discontinued
0.7416	Intermediate Similarity	NPD6599	Discontinued
0.7416	Intermediate Similarity	NPD4380	Phase 2
0.7389	Intermediate Similarity	NPD7819	Suspended
0.7371	Intermediate Similarity	NPD6799	Approved
0.731	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4967	Phase 2
0.7308	Intermediate Similarity	NPD4965	Approved
0.7308	Intermediate Similarity	NPD4966	Approved
0.7287	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1549	Phase 2
0.7278	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7268	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD920	Approved
0.7247	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7199	Phase 2
0.7241	Intermediate Similarity	NPD1243	Approved
0.7234	Intermediate Similarity	NPD7228	Approved
0.7232	Intermediate Similarity	NPD2532	Approved
0.7232	Intermediate Similarity	NPD2534	Approved
0.7232	Intermediate Similarity	NPD2533	Approved
0.7228	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7768	Phase 2
0.7209	Intermediate Similarity	NPD1510	Phase 2
0.7209	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1607	Approved
0.7176	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD37	Approved
0.7128	Intermediate Similarity	NPD2403	Approved
0.7114	Intermediate Similarity	NPD6781	Approved
0.7114	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6778	Approved
0.7114	Intermediate Similarity	NPD6782	Approved
0.7114	Intermediate Similarity	NPD6780	Approved
0.7114	Intermediate Similarity	NPD6776	Approved
0.7114	Intermediate Similarity	NPD6779	Approved
0.7114	Intermediate Similarity	NPD6777	Approved
0.7112	Intermediate Similarity	NPD3787	Discontinued
0.7102	Intermediate Similarity	NPD3750	Approved
0.7094	Intermediate Similarity	NPD7435	Discontinued
0.7092	Intermediate Similarity	NPD4287	Approved
0.7086	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2796	Approved
0.7062	Intermediate Similarity	NPD6190	Approved
0.7056	Intermediate Similarity	NPD5403	Approved
0.7045	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5401	Approved
0.7039	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD7871	Phase 2
0.6976	Remote Similarity	NPD7870	Phase 2
0.6973	Remote Similarity	NPD2296	Approved
0.6971	Remote Similarity	NPD2935	Discontinued
0.6971	Remote Similarity	NPD6100	Approved
0.6971	Remote Similarity	NPD6099	Approved
0.6963	Remote Similarity	NPD7907	Approved
0.6941	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD230	Phase 1
0.6936	Remote Similarity	NPD447	Suspended
0.6932	Remote Similarity	NPD2346	Discontinued
0.6927	Remote Similarity	NPD7698	Approved
0.6927	Remote Similarity	NPD7697	Approved
0.6927	Remote Similarity	NPD7696	Phase 3
0.6927	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8312	Approved
0.6923	Remote Similarity	NPD8151	Discontinued
0.6923	Remote Similarity	NPD8313	Approved
0.6904	Remote Similarity	NPD8150	Discontinued
0.689	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7874	Approved
0.6875	Remote Similarity	NPD7701	Phase 2
0.6875	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6534	Approved
0.6866	Remote Similarity	NPD6535	Approved
0.6828	Remote Similarity	NPD5760	Phase 2
0.6828	Remote Similarity	NPD5761	Phase 2
0.6821	Remote Similarity	NPD7240	Approved
0.6818	Remote Similarity	NPD3748	Approved
0.6816	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6651	Approved
0.6798	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4111	Phase 1
0.6791	Remote Similarity	NPD4665	Approved
0.6788	Remote Similarity	NPD2163	Approved
0.6782	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1613	Approved
0.678	Remote Similarity	NPD1551	Phase 2
0.6777	Remote Similarity	NPD7801	Approved
0.6777	Remote Similarity	NPD7783	Phase 2
0.6777	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5953	Discontinued
0.6765	Remote Similarity	NPD7699	Phase 2
0.6765	Remote Similarity	NPD1470	Approved
0.6765	Remote Similarity	NPD7700	Phase 2
0.6763	Remote Similarity	NPD3764	Approved
0.6754	Remote Similarity	NPD5711	Approved
0.6754	Remote Similarity	NPD5710	Approved
0.6754	Remote Similarity	NPD7229	Phase 3
0.6748	Remote Similarity	NPD2494	Approved
0.6748	Remote Similarity	NPD2493	Approved
0.6742	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2799	Discontinued
0.6722	Remote Similarity	NPD4628	Phase 3
0.6717	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5408	Approved
0.6685	Remote Similarity	NPD5404	Approved
0.6685	Remote Similarity	NPD5405	Approved
0.6685	Remote Similarity	NPD5406	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD3452	Approved
0.6667	Remote Similarity	NPD3450	Approved
0.6667	Remote Similarity	NPD6808	Phase 2
0.6667	Remote Similarity	NPD7286	Phase 2
0.6651	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4583	Approved
0.6651	Remote Similarity	NPD4582	Approved
0.665	Remote Similarity	NPD7685	Pre-registration
0.6649	Remote Similarity	NPD1653	Approved
0.6635	Remote Similarity	NPD6823	Phase 2
0.663	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3027	Phase 3
0.6609	Remote Similarity	NPD4625	Phase 3
0.6603	Remote Similarity	NPD4004	Approved
0.6603	Remote Similarity	NPD4002	Approved
0.6603	Remote Similarity	NPD7680	Approved
0.6596	Remote Similarity	NPD6279	Approved
0.6596	Remote Similarity	NPD6280	Approved
0.659	Remote Similarity	NPD9494	Approved
0.6576	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8320	Phase 1
0.6571	Remote Similarity	NPD8319	Approved
0.657	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6765	Approved
0.6566	Remote Similarity	NPD6764	Approved
0.6554	Remote Similarity	NPD1933	Approved
0.6553	Remote Similarity	NPD2973	Approved
0.6553	Remote Similarity	NPD2974	Approved
0.6553	Remote Similarity	NPD2975	Approved
0.655	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD8404	Phase 2
0.6534	Remote Similarity	NPD6233	Phase 2
0.6529	Remote Similarity	NPD1201	Approved
0.6528	Remote Similarity	NPD8127	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