NPASS Compound

Structure

NPC17837 OpenBabel07101719252D 33 36 0 0 0 0 0 0 0 0999 V2000 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 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 6.9282 1.0000 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 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 6.9282 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 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 4.0000 0.0000 O 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 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 25 2 0 0 0 0 7 27 2 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 21 2 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 17 2 0 0 0 0 14 24 1 0 0 0 0 15 26 2 0 0 0 0 16 26 1 0 0 0 0 17 28 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 20 29 1 0 0 0 0 25 30 1 0 0 0 0 26 33 1 0 0 0 0 27 32 1 0 0 0 0 28 29 2 0 0 0 0 28 31 1 0 0 0 0 29 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.2
Volume:	479.438
LogP:	6.167
LogD:	4.536
LogS:	-5.037
# Rotatable Bonds:	9
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.313
Synthetic Accessibility Score:	2.141
Fsp3:	0.172
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.376
MDCK Permeability:	8.177409654308576e-06
Pgp-inhibitor:	0.999
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	100.58806610107422%
Volume Distribution (VD):	0.449
Pgp-substrate:	0.7577266097068787%

ADMET: Metabolism

CYP1A2-inhibitor:	0.782
CYP1A2-substrate:	0.529
CYP2C19-inhibitor:	0.947
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.845
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.778
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.573
CYP3A4-substrate:	0.605

ADMET: Excretion

Clearance (CL):	10.442
Half-life (T1/2):	0.533

ADMET: Toxicity

hERG Blockers:	0.68
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.165
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.963
Carcinogencity:	0.263
Eye Corrosion:	0.003
Eye Irritation:	0.892
Respiratory Toxicity:	0.251

Download Data

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

Natural Product: NPC17837

Natural Product ID:	NPC17837
*Common Name:**	Perrottetin E 11'-Methyl Ether
IUPAC Name:	2-[4-[2-(3-hydroxyphenyl)ethyl]phenoxy]-4-[2-(3-methoxyphenyl)ethyl]phenol
Synonyms:	Perrottetin E 11'-Methyl Ether; Perrottetin E-11'-Methyl Ether
Standard InCHIKey:	NZWFFDGHEUMZNF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H28O4/c1-32-27-7-3-5-23(19-27)10-11-24-14-17-28(31)29(20-24)33-26-15-12-21(13-16-26)8-9-22-4-2-6-25(30)18-22/h2-7,12-20,30-31H,8-11H2,1H3
SMILES:	COc1cccc(CCc2ccc(c(c2)Oc2ccc(CCc3cccc(c3)O)cc2)O)c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458919
PubChem CID:	14841123
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO33046	liverworts	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16378374]
NPO33046	liverworts	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21652215]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	49850.0	nM	PMID[469960]

☑ 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 NPC17837 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	399
0.1-0.2	1835
0.2-0.3	5452
0.3-0.4	13670
0.4-0.5	3746
0.5-0.6	5239
0.6-0.7	8186
0.7-0.8	3311
0.8-0.85	667
0.85-0.9	174
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304630
0.9669	High Similarity	NPC134431
0.9669	High Similarity	NPC156854
0.9435	High Similarity	NPC210655
0.937	High Similarity	NPC141023
0.9244	High Similarity	NPC470626
0.9213	High Similarity	NPC189482
0.9213	High Similarity	NPC474134
0.9213	High Similarity	NPC131128
0.9213	High Similarity	NPC73656
0.916	High Similarity	NPC86947
0.916	High Similarity	NPC293619
0.9098	High Similarity	NPC127389
0.9098	High Similarity	NPC290451
0.9091	High Similarity	NPC242885
0.9091	High Similarity	NPC56214
0.9091	High Similarity	NPC227217
0.9091	High Similarity	NPC95614
0.9091	High Similarity	NPC165133
0.9091	High Similarity	NPC117780
0.9091	High Similarity	NPC232316
0.9084	High Similarity	NPC55947
0.907	High Similarity	NPC66840
0.907	High Similarity	NPC256307
0.9016	High Similarity	NPC207613
0.9015	High Similarity	NPC22317
0.9008	High Similarity	NPC474390
0.9008	High Similarity	NPC310338
0.9008	High Similarity	NPC281298
0.896	High Similarity	NPC228771
0.896	High Similarity	NPC194519
0.896	High Similarity	NPC266705
0.896	High Similarity	NPC29008
0.8952	High Similarity	NPC317769
0.8952	High Similarity	NPC31344
0.8947	High Similarity	NPC470372
0.8943	High Similarity	NPC54872
0.8943	High Similarity	NPC324571
0.8943	High Similarity	NPC38996
0.8943	High Similarity	NPC262156
0.8943	High Similarity	NPC343720
0.8943	High Similarity	NPC312675
0.8943	High Similarity	NPC473853
0.8943	High Similarity	NPC160380
0.8943	High Similarity	NPC113865
0.8943	High Similarity	NPC470212
0.8943	High Similarity	NPC184651
0.8898	High Similarity	NPC226661
0.8889	High Similarity	NPC58607
0.8889	High Similarity	NPC178284
0.8889	High Similarity	NPC191037
0.888	High Similarity	NPC293701
0.888	High Similarity	NPC48990
0.888	High Similarity	NPC114901
0.8872	High Similarity	NPC262189
0.8871	High Similarity	NPC85488
0.8828	High Similarity	NPC86030
0.8828	High Similarity	NPC5851
0.8819	High Similarity	NPC147821
0.8819	High Similarity	NPC210355
0.8819	High Similarity	NPC118787
0.8819	High Similarity	NPC183181
0.8819	High Similarity	NPC41706
0.8819	High Similarity	NPC319625
0.8819	High Similarity	NPC163332
0.8819	High Similarity	NPC292056
0.8819	High Similarity	NPC111247
0.881	High Similarity	NPC9067
0.88	High Similarity	NPC280704
0.88	High Similarity	NPC471693
0.8797	High Similarity	NPC260842
0.8788	High Similarity	NPC77861
0.875	High Similarity	NPC474178
0.875	High Similarity	NPC277458
0.875	High Similarity	NPC307050
0.875	High Similarity	NPC72529
0.875	High Similarity	NPC245826
0.875	High Similarity	NPC252307
0.8731	High Similarity	NPC106055
0.8731	High Similarity	NPC110699
0.873	High Similarity	NPC74478
0.873	High Similarity	NPC94276
0.873	High Similarity	NPC109822
0.872	High Similarity	NPC71090
0.8699	High Similarity	NPC24474
0.8699	High Similarity	NPC311595
0.8689	High Similarity	NPC164386
0.8682	High Similarity	NPC474227
0.8672	High Similarity	NPC470699
0.8661	High Similarity	NPC472093
0.8661	High Similarity	NPC17943
0.8661	High Similarity	NPC257589
0.8661	High Similarity	NPC251855
0.8661	High Similarity	NPC116907
0.8661	High Similarity	NPC233410
0.8661	High Similarity	NPC87113
0.8661	High Similarity	NPC3221
0.8661	High Similarity	NPC298757
0.8661	High Similarity	NPC221077
0.8661	High Similarity	NPC57490
0.8661	High Similarity	NPC53305
0.8661	High Similarity	NPC193544
0.8661	High Similarity	NPC117214
0.8661	High Similarity	NPC208950
0.8661	High Similarity	NPC148627
0.8661	High Similarity	NPC203133
0.8661	High Similarity	NPC475169
0.8657	High Similarity	NPC22517
0.8655	High Similarity	NPC173746
0.8655	High Similarity	NPC8547
0.8655	High Similarity	NPC156840
0.8655	High Similarity	NPC257124
0.8651	High Similarity	NPC228922
0.8651	High Similarity	NPC197757
0.8636	High Similarity	NPC478085
0.8636	High Similarity	NPC317380
0.8626	High Similarity	NPC127624
0.8626	High Similarity	NPC86655
0.8626	High Similarity	NPC202762
0.8626	High Similarity	NPC303144
0.8618	High Similarity	NPC474040
0.8618	High Similarity	NPC474214
0.8615	High Similarity	NPC472338
0.8613	High Similarity	NPC171932
0.8613	High Similarity	NPC28440
0.8605	High Similarity	NPC184733
0.8605	High Similarity	NPC45774
0.8605	High Similarity	NPC282703
0.8605	High Similarity	NPC11258
0.8605	High Similarity	NPC21867
0.8605	High Similarity	NPC129570
0.8605	High Similarity	NPC128208
0.8594	High Similarity	NPC274356
0.8594	High Similarity	NPC92207
0.8594	High Similarity	NPC213552
0.8594	High Similarity	NPC120225
0.8594	High Similarity	NPC181361
0.8594	High Similarity	NPC127937
0.8593	High Similarity	NPC472090
0.8593	High Similarity	NPC472092
0.8593	High Similarity	NPC266197
0.8593	High Similarity	NPC55793
0.8593	High Similarity	NPC291101
0.8593	High Similarity	NPC472091
0.8583	High Similarity	NPC122792
0.8583	High Similarity	NPC228972
0.8582	High Similarity	NPC211549
0.8571	High Similarity	NPC112246
0.8571	High Similarity	NPC93783
0.8571	High Similarity	NPC470356
0.8571	High Similarity	NPC41562
0.8571	High Similarity	NPC474206
0.8571	High Similarity	NPC112939
0.8571	High Similarity	NPC94750
0.8571	High Similarity	NPC121812
0.8571	High Similarity	NPC30462
0.8561	High Similarity	NPC168059
0.8561	High Similarity	NPC475840
0.8561	High Similarity	NPC229442
0.856	High Similarity	NPC189844
0.856	High Similarity	NPC109083
0.856	High Similarity	NPC269843
0.856	High Similarity	NPC224814
0.856	High Similarity	NPC14007
0.856	High Similarity	NPC60962
0.8551	High Similarity	NPC274960
0.8551	High Similarity	NPC143120
0.8551	High Similarity	NPC473909
0.855	High Similarity	NPC474238
0.855	High Similarity	NPC472597
0.8548	High Similarity	NPC474320
0.8538	High Similarity	NPC475875
0.8538	High Similarity	NPC241354
0.8529	High Similarity	NPC472089
0.8527	High Similarity	NPC159968
0.8527	High Similarity	NPC293054
0.8527	High Similarity	NPC124452
0.8527	High Similarity	NPC5428
0.8527	High Similarity	NPC106511
0.8527	High Similarity	NPC169474
0.8527	High Similarity	NPC118533
0.8527	High Similarity	NPC21563
0.8527	High Similarity	NPC74817
0.8527	High Similarity	NPC324112
0.8527	High Similarity	NPC246620
0.8527	High Similarity	NPC165045
0.8527	High Similarity	NPC282000
0.8527	High Similarity	NPC82679
0.8527	High Similarity	NPC236791
0.8527	High Similarity	NPC127587
0.8525	High Similarity	NPC47194
0.8516	High Similarity	NPC289459
0.8516	High Similarity	NPC28476
0.8516	High Similarity	NPC133407
0.8512	High Similarity	NPC165106
0.8507	High Similarity	NPC248727
0.8507	High Similarity	NPC227503
0.8507	High Similarity	NPC265433
0.8507	High Similarity	NPC162659
0.8507	High Similarity	NPC16435

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 NPC17837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	1013
0.2-0.3	1528
0.3-0.4	2703
0.4-0.5	1757
0.5-0.6	973
0.6-0.7	687
0.7-0.8	121
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8655	High Similarity	NPD228	Approved
0.8512	High Similarity	NPD5283	Phase 1
0.8397	Intermediate Similarity	NPD3027	Phase 3
0.8359	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1613	Approved
0.8182	Intermediate Similarity	NPD3021	Approved
0.8182	Intermediate Similarity	NPD3022	Approved
0.8168	Intermediate Similarity	NPD6584	Phase 3
0.8099	Intermediate Similarity	NPD2684	Approved
0.8074	Intermediate Similarity	NPD3620	Phase 2
0.8074	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6516	Phase 2
0.8047	Intermediate Similarity	NPD5846	Approved
0.8045	Intermediate Similarity	NPD4908	Phase 1
0.7985	Intermediate Similarity	NPD7095	Approved
0.7984	Intermediate Similarity	NPD7843	Approved
0.7941	Intermediate Similarity	NPD4060	Phase 1
0.7941	Intermediate Similarity	NPD1558	Phase 1
0.7939	Intermediate Similarity	NPD6582	Phase 2
0.7939	Intermediate Similarity	NPD6583	Phase 3
0.7937	Intermediate Similarity	NPD7157	Approved
0.7926	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD5535	Approved
0.7812	Intermediate Similarity	NPD5536	Phase 2
0.7795	Intermediate Similarity	NPD6671	Approved
0.7794	Intermediate Similarity	NPD6798	Discontinued
0.7742	Intermediate Similarity	NPD5451	Approved
0.7704	Intermediate Similarity	NPD2861	Phase 2
0.7681	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD968	Approved
0.7609	Intermediate Similarity	NPD6233	Phase 2
0.7609	Intermediate Similarity	NPD2674	Phase 3
0.7589	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6331	Phase 2
0.7557	Intermediate Similarity	NPD1357	Approved
0.7552	Intermediate Similarity	NPD7037	Approved
0.7537	Intermediate Similarity	NPD2982	Phase 2
0.7537	Intermediate Similarity	NPD2983	Phase 2
0.7519	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD5735	Approved
0.75	Intermediate Similarity	NPD6674	Discontinued
0.75	Intermediate Similarity	NPD4162	Approved
0.7483	Intermediate Similarity	NPD1934	Approved
0.7481	Intermediate Similarity	NPD1548	Phase 1
0.7481	Intermediate Similarity	NPD6581	Approved
0.7481	Intermediate Similarity	NPD6580	Approved
0.7479	Intermediate Similarity	NPD2859	Approved
0.7479	Intermediate Similarity	NPD2860	Approved
0.7463	Intermediate Similarity	NPD2981	Phase 2
0.7452	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6166	Phase 2
0.7452	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4110	Phase 3
0.7445	Intermediate Similarity	NPD3018	Phase 2
0.744	Intermediate Similarity	NPD290	Approved
0.7438	Intermediate Similarity	NPD3020	Approved
0.7434	Intermediate Similarity	NPD2801	Approved
0.7424	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5110	Phase 2
0.741	Intermediate Similarity	NPD5109	Approved
0.741	Intermediate Similarity	NPD3145	Approved
0.741	Intermediate Similarity	NPD3144	Approved
0.741	Intermediate Similarity	NPD5111	Phase 2
0.7407	Intermediate Similarity	NPD5327	Phase 3
0.7403	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7831	Phase 2
0.7403	Intermediate Similarity	NPD7833	Phase 2
0.7395	Intermediate Similarity	NPD2933	Approved
0.7395	Intermediate Similarity	NPD9296	Approved
0.7395	Intermediate Similarity	NPD2934	Approved
0.7394	Intermediate Similarity	NPD4536	Approved
0.7394	Intermediate Similarity	NPD7097	Phase 1
0.7394	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4538	Approved
0.7388	Intermediate Similarity	NPD3705	Approved
0.7379	Intermediate Similarity	NPD3060	Approved
0.7376	Intermediate Similarity	NPD6355	Discontinued
0.7361	Intermediate Similarity	NPD7266	Discontinued
0.7357	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8651	Approved
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7329	Intermediate Similarity	NPD8166	Discontinued
0.7329	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD9494	Approved
0.7317	Intermediate Similarity	NPD291	Approved
0.7305	Intermediate Similarity	NPD4140	Approved
0.7292	Intermediate Similarity	NPD2161	Phase 2
0.7287	Intermediate Similarity	NPD821	Approved
0.7286	Intermediate Similarity	NPD5718	Phase 2
0.7279	Intermediate Similarity	NPD5241	Discontinued
0.7279	Intermediate Similarity	NPD4749	Approved
0.726	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD8054	Approved
0.7256	Intermediate Similarity	NPD8053	Approved
0.7255	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3657	Discovery
0.7248	Intermediate Similarity	NPD4123	Phase 3
0.7248	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4624	Approved
0.7234	Intermediate Similarity	NPD4062	Phase 3
0.7226	Intermediate Similarity	NPD2922	Phase 1
0.7226	Intermediate Similarity	NPD3882	Suspended
0.7222	Intermediate Similarity	NPD5960	Phase 3
0.7222	Intermediate Similarity	NPD5588	Approved
0.7206	Intermediate Similarity	NPD2235	Phase 2
0.7206	Intermediate Similarity	NPD2231	Phase 2
0.7203	Intermediate Similarity	NPD6353	Approved
0.72	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3596	Phase 2
0.7185	Intermediate Similarity	NPD3847	Discontinued
0.7185	Intermediate Similarity	NPD3496	Discontinued
0.7181	Intermediate Similarity	NPD1511	Approved
0.7153	Intermediate Similarity	NPD6895	Approved
0.7153	Intermediate Similarity	NPD6543	Approved
0.7153	Intermediate Similarity	NPD6540	Phase 3
0.7153	Intermediate Similarity	NPD6896	Approved
0.7153	Intermediate Similarity	NPD6542	Approved
0.7153	Intermediate Similarity	NPD6539	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD4237	Approved
0.7143	Intermediate Similarity	NPD5177	Phase 3
0.7143	Intermediate Similarity	NPD4236	Phase 3
0.7134	Intermediate Similarity	NPD6234	Discontinued
0.7133	Intermediate Similarity	NPD7447	Phase 1
0.7133	Intermediate Similarity	NPD4340	Discontinued
0.7132	Intermediate Similarity	NPD1535	Discovery
0.7123	Intermediate Similarity	NPD1375	Discontinued
0.7123	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7265	Discontinued
0.7111	Intermediate Similarity	NPD4626	Approved
0.7111	Intermediate Similarity	NPD2668	Approved
0.7111	Intermediate Similarity	NPD2667	Approved
0.7105	Intermediate Similarity	NPD1653	Approved
0.7101	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6538	Approved
0.7101	Intermediate Similarity	NPD6541	Approved
0.7097	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4628	Phase 3
0.7095	Intermediate Similarity	NPD4535	Phase 3
0.7092	Intermediate Similarity	NPD6179	Discontinued
0.709	Intermediate Similarity	NPD1894	Discontinued
0.709	Intermediate Similarity	NPD1182	Approved
0.7086	Intermediate Similarity	NPD1512	Approved
0.708	Intermediate Similarity	NPD1608	Approved
0.708	Intermediate Similarity	NPD2232	Approved
0.708	Intermediate Similarity	NPD2233	Approved
0.708	Intermediate Similarity	NPD2230	Approved
0.708	Intermediate Similarity	NPD1481	Phase 2
0.7075	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7153	Discontinued
0.7067	Intermediate Similarity	NPD7041	Phase 2
0.7067	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7213	Phase 3
0.7067	Intermediate Similarity	NPD7212	Phase 2
0.7063	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7074	Phase 3
0.7055	Intermediate Similarity	NPD6032	Approved
0.705	Intermediate Similarity	NPD2797	Approved
0.7044	Intermediate Similarity	NPD8127	Discontinued
0.7042	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5585	Approved
0.7037	Intermediate Similarity	NPD1651	Approved
0.7032	Intermediate Similarity	NPD5722	Discontinued
0.7031	Intermediate Similarity	NPD1358	Approved
0.7029	Intermediate Similarity	NPD1669	Approved
0.7029	Intermediate Similarity	NPD3685	Discontinued
0.7027	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2489	Approved
0.7019	Intermediate Similarity	NPD27	Approved
0.7013	Intermediate Similarity	NPD4678	Approved
0.7013	Intermediate Similarity	NPD4675	Approved
0.7007	Intermediate Similarity	NPD3092	Approved
0.7007	Intermediate Similarity	NPD5763	Approved
0.7007	Intermediate Similarity	NPD1091	Approved
0.7007	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5058	Phase 3
0.7	Intermediate Similarity	NPD7018	Phase 2
0.6994	Remote Similarity	NPD7054	Approved
0.6994	Remote Similarity	NPD5844	Phase 1
0.6993	Remote Similarity	NPD3530	Approved
0.6993	Remote Similarity	NPD3532	Approved
0.6993	Remote Similarity	NPD3531	Approved
0.6993	Remote Similarity	NPD7477	Discontinued
0.6992	Remote Similarity	NPD2557	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