NPASS Compound

Structure

NPC475852 OpenBabel07101719512D 24 25 0 0 0 0 0 0 0 0999 V2000 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 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 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 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 5.1962 -3.0000 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 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 Si 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 18 1 0 0 0 0 9 20 2 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 19 2 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 21 24 1 0 0 0 0 23 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.2
Volume:	38792739.224
LogP:	6.23
LogD:	4.999
LogS:	-6.993
# Rotatable Bonds:	7
TPSA:	18.46
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	2.0
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.559
MDCK Permeability:	9.154127837973647e-06
Pgp-inhibitor:	0.93
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.42
30% Bioavailability (F30%):	0.801

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	101.7195816040039%
Volume Distribution (VD):	4.109
Pgp-substrate:	0.48731547594070435%

ADMET: Metabolism

CYP1A2-inhibitor:	0.711
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.917
CYP2C19-substrate:	0.828
CYP2C9-inhibitor:	0.93
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.408
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.862
CYP3A4-substrate:	0.656

ADMET: Excretion

Clearance (CL):	5.027
Half-life (T1/2):	0.217

ADMET: Toxicity

hERG Blockers:	0.488
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.643
Skin Sensitization:	0.396
Carcinogencity:	0.06
Eye Corrosion:	0.35
Eye Irritation:	0.978
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC475852

Natural Product ID:	NPC475852
*Common Name:**	4-(Tert-Butyldimethylsiloxy)-3'-Methoxybibenzyl
IUPAC Name:	tert-butyl-[4-[2-(3-methoxyphenyl)ethyl]phenoxy]-dimethylsilane
Synonyms:
Standard InCHIKey:	PLDZORXCNMFWQE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H30O2Si/c1-21(2,3)24(5,6)23-19-14-12-17(13-15-19)10-11-18-8-7-9-20(16-18)22-4/h7-9,12-16H,10-11H2,1-6H3
SMILES:	CC(C)(C)[Si](C)(C)OC1=CC=C(C=C1)CCC2=CC(=CC=C2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517356
PubChem CID:	10066004
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO33038	plagiochila stephensoniana	Species	Plagiochilaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[8254344]

☑ 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
MIC	2
Others	2

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[573727]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	1000.0	ug.mL-1	PMID[573727]
NPT20	Organism	Candida albicans	Candida albicans	MFC	>	1000.0	ug ml-1	PMID[573727]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	1000.0	ug.mL-1	PMID[573727]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MFC	>	1000.0	ug ml-1	PMID[573727]

☑ 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 NPC475852 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	451
0.1-0.2	2089
0.2-0.3	6967
0.3-0.4	12423
0.4-0.5	4175
0.5-0.6	9671
0.6-0.7	5425
0.7-0.8	1425
0.8-0.85	64
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8879	High Similarity	NPC75440
0.8846	High Similarity	NPC300166
0.8738	High Similarity	NPC470161
0.8692	High Similarity	NPC113457
0.8679	High Similarity	NPC241224
0.8649	High Similarity	NPC165106
0.8545	High Similarity	NPC2682
0.8532	High Similarity	NPC201959
0.8505	High Similarity	NPC474603
0.8505	High Similarity	NPC12987
0.8496	Intermediate Similarity	NPC47194
0.8496	Intermediate Similarity	NPC475815
0.8496	Intermediate Similarity	NPC473264
0.8455	Intermediate Similarity	NPC82016
0.8455	Intermediate Similarity	NPC474272
0.8431	Intermediate Similarity	NPC321956
0.8421	Intermediate Similarity	NPC81067
0.8421	Intermediate Similarity	NPC9341
0.8348	Intermediate Similarity	NPC474933
0.8333	Intermediate Similarity	NPC292792
0.8333	Intermediate Similarity	NPC71853
0.8319	Intermediate Similarity	NPC35344
0.8319	Intermediate Similarity	NPC141003
0.8276	Intermediate Similarity	NPC474040
0.8276	Intermediate Similarity	NPC474214
0.8276	Intermediate Similarity	NPC470626
0.8273	Intermediate Similarity	NPC35543
0.8269	Intermediate Similarity	NPC471581
0.8261	Intermediate Similarity	NPC141090
0.8241	Intermediate Similarity	NPC24327
0.8241	Intermediate Similarity	NPC12870
0.8235	Intermediate Similarity	NPC8002
0.8235	Intermediate Similarity	NPC99886
0.8235	Intermediate Similarity	NPC177844
0.8235	Intermediate Similarity	NPC259134
0.8214	Intermediate Similarity	NPC303521
0.8205	Intermediate Similarity	NPC310338
0.8205	Intermediate Similarity	NPC281298
0.8205	Intermediate Similarity	NPC254625
0.8205	Intermediate Similarity	NPC474320
0.8205	Intermediate Similarity	NPC475961
0.8198	Intermediate Similarity	NPC245115
0.819	Intermediate Similarity	NPC25648
0.819	Intermediate Similarity	NPC293619
0.8174	Intermediate Similarity	NPC283169
0.8174	Intermediate Similarity	NPC53906
0.8148	Intermediate Similarity	NPC12714
0.8148	Intermediate Similarity	NPC310905
0.8142	Intermediate Similarity	NPC470723
0.8136	Intermediate Similarity	NPC242885
0.8136	Intermediate Similarity	NPC344161
0.8136	Intermediate Similarity	NPC165133
0.8136	Intermediate Similarity	NPC103916
0.8136	Intermediate Similarity	NPC95614
0.8136	Intermediate Similarity	NPC117780
0.8136	Intermediate Similarity	NPC56214
0.8136	Intermediate Similarity	NPC232316
0.8136	Intermediate Similarity	NPC227217
0.8131	Intermediate Similarity	NPC100870
0.8103	Intermediate Similarity	NPC312105
0.8103	Intermediate Similarity	NPC33900
0.8091	Intermediate Similarity	NPC470393
0.8087	Intermediate Similarity	NPC22610
0.8087	Intermediate Similarity	NPC276737
0.8087	Intermediate Similarity	NPC180508
0.8087	Intermediate Similarity	NPC228287
0.8067	Intermediate Similarity	NPC129176
0.8067	Intermediate Similarity	NPC207613
0.8053	Intermediate Similarity	NPC137685
0.8051	Intermediate Similarity	NPC15805
0.8034	Intermediate Similarity	NPC33270
0.8034	Intermediate Similarity	NPC195466
0.8034	Intermediate Similarity	NPC470759
0.8034	Intermediate Similarity	NPC69261
0.8034	Intermediate Similarity	NPC15860
0.8034	Intermediate Similarity	NPC127894
0.8034	Intermediate Similarity	NPC219070
0.8018	Intermediate Similarity	NPC326801
0.8018	Intermediate Similarity	NPC30416
0.8017	Intermediate Similarity	NPC808
0.8	Intermediate Similarity	NPC126935
0.8	Intermediate Similarity	NPC113865
0.8	Intermediate Similarity	NPC312675
0.8	Intermediate Similarity	NPC108875
0.8	Intermediate Similarity	NPC172676
0.8	Intermediate Similarity	NPC54872
0.8	Intermediate Similarity	NPC312713
0.8	Intermediate Similarity	NPC262156
0.8	Intermediate Similarity	NPC38079
0.8	Intermediate Similarity	NPC473853
0.8	Intermediate Similarity	NPC470212
0.8	Intermediate Similarity	NPC160380
0.8	Intermediate Similarity	NPC324571
0.8	Intermediate Similarity	NPC301641
0.8	Intermediate Similarity	NPC184651
0.8	Intermediate Similarity	NPC476633
0.8	Intermediate Similarity	NPC57268
0.8	Intermediate Similarity	NPC477886
0.8	Intermediate Similarity	NPC38996
0.8	Intermediate Similarity	NPC65933
0.8	Intermediate Similarity	NPC216929
0.8	Intermediate Similarity	NPC80241
0.8	Intermediate Similarity	NPC343720
0.7982	Intermediate Similarity	NPC90520
0.7982	Intermediate Similarity	NPC296920
0.7966	Intermediate Similarity	NPC190514
0.7963	Intermediate Similarity	NPC471576
0.7949	Intermediate Similarity	NPC54507
0.7949	Intermediate Similarity	NPC123948
0.7949	Intermediate Similarity	NPC229147
0.7949	Intermediate Similarity	NPC85292
0.7949	Intermediate Similarity	NPC150624
0.7949	Intermediate Similarity	NPC114064
0.7946	Intermediate Similarity	NPC258171
0.7946	Intermediate Similarity	NPC233320
0.7934	Intermediate Similarity	NPC30462
0.7934	Intermediate Similarity	NPC85488
0.7928	Intermediate Similarity	NPC154899
0.7928	Intermediate Similarity	NPC473855
0.7928	Intermediate Similarity	NPC233396
0.7917	Intermediate Similarity	NPC472596
0.7917	Intermediate Similarity	NPC102639
0.7913	Intermediate Similarity	NPC280606
0.7909	Intermediate Similarity	NPC298224
0.7909	Intermediate Similarity	NPC192596
0.7899	Intermediate Similarity	NPC184302
0.7895	Intermediate Similarity	NPC473809
0.7881	Intermediate Similarity	NPC280001
0.7881	Intermediate Similarity	NPC86947
0.7881	Intermediate Similarity	NPC164386
0.7881	Intermediate Similarity	NPC185738
0.7881	Intermediate Similarity	NPC469954
0.787	Intermediate Similarity	NPC175298
0.7869	Intermediate Similarity	NPC282496
0.7869	Intermediate Similarity	NPC136319
0.7869	Intermediate Similarity	NPC31344
0.7869	Intermediate Similarity	NPC317769
0.7869	Intermediate Similarity	NPC280704
0.7869	Intermediate Similarity	NPC471693
0.7869	Intermediate Similarity	NPC249788
0.7869	Intermediate Similarity	NPC233526
0.7869	Intermediate Similarity	NPC470887
0.7863	Intermediate Similarity	NPC464
0.7863	Intermediate Similarity	NPC185541
0.7863	Intermediate Similarity	NPC167934
0.7857	Intermediate Similarity	NPC135464
0.7857	Intermediate Similarity	NPC92623
0.7851	Intermediate Similarity	NPC127389
0.7851	Intermediate Similarity	NPC290451
0.785	Intermediate Similarity	NPC274678
0.785	Intermediate Similarity	NPC26244
0.7845	Intermediate Similarity	NPC204120
0.7838	Intermediate Similarity	NPC38209
0.7826	Intermediate Similarity	NPC173746
0.7826	Intermediate Similarity	NPC275627
0.7826	Intermediate Similarity	NPC257124
0.7826	Intermediate Similarity	NPC156840
0.7826	Intermediate Similarity	NPC8547
0.7818	Intermediate Similarity	NPC51633
0.7815	Intermediate Similarity	NPC277460
0.7815	Intermediate Similarity	NPC131118
0.7805	Intermediate Similarity	NPC18449
0.7805	Intermediate Similarity	NPC34902
0.7805	Intermediate Similarity	NPC121783
0.7797	Intermediate Similarity	NPC203113
0.7797	Intermediate Similarity	NPC19290
0.7788	Intermediate Similarity	NPC227894
0.7787	Intermediate Similarity	NPC41562
0.7787	Intermediate Similarity	NPC152946
0.7787	Intermediate Similarity	NPC71090
0.7787	Intermediate Similarity	NPC261661
0.7778	Intermediate Similarity	NPC473388
0.7769	Intermediate Similarity	NPC131868
0.7769	Intermediate Similarity	NPC212559
0.7759	Intermediate Similarity	NPC165646
0.7757	Intermediate Similarity	NPC151715
0.7757	Intermediate Similarity	NPC76938
0.775	Intermediate Similarity	NPC172253
0.775	Intermediate Similarity	NPC59561
0.775	Intermediate Similarity	NPC24474
0.775	Intermediate Similarity	NPC311595
0.7748	Intermediate Similarity	NPC305205
0.7742	Intermediate Similarity	NPC17348
0.7742	Intermediate Similarity	NPC148627
0.7742	Intermediate Similarity	NPC208950
0.7742	Intermediate Similarity	NPC472093
0.7742	Intermediate Similarity	NPC228771
0.7742	Intermediate Similarity	NPC298757
0.7742	Intermediate Similarity	NPC116907
0.7742	Intermediate Similarity	NPC203133
0.7742	Intermediate Similarity	NPC193544
0.7742	Intermediate Similarity	NPC53305
0.7742	Intermediate Similarity	NPC266705
0.7742	Intermediate Similarity	NPC251855
0.7742	Intermediate Similarity	NPC257589
0.7742	Intermediate Similarity	NPC233410
0.7742	Intermediate Similarity	NPC9067
0.7742	Intermediate Similarity	NPC57490
0.7742	Intermediate Similarity	NPC105031
0.7742	Intermediate Similarity	NPC113495

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 NPC475852 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	1086
0.2-0.3	1370
0.3-0.4	2746
0.4-0.5	1853
0.5-0.6	1087
0.6-0.7	508
0.7-0.8	106
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8649	High Similarity	NPD5283	Phase 1
0.8455	Intermediate Similarity	NPD5451	Approved
0.807	Intermediate Similarity	NPD5535	Approved
0.8051	Intermediate Similarity	NPD1651	Approved
0.8036	Intermediate Similarity	NPD2684	Approved
0.7881	Intermediate Similarity	NPD5536	Phase 2
0.7869	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD2859	Approved
0.785	Intermediate Similarity	NPD2860	Approved
0.7826	Intermediate Similarity	NPD228	Approved
0.7798	Intermediate Similarity	NPD3020	Approved
0.7797	Intermediate Similarity	NPD3596	Phase 2
0.7759	Intermediate Similarity	NPD7843	Approved
0.7757	Intermediate Similarity	NPD2933	Approved
0.7757	Intermediate Similarity	NPD2934	Approved
0.775	Intermediate Similarity	NPD5691	Approved
0.7724	Intermediate Similarity	NPD5327	Phase 3
0.7724	Intermediate Similarity	NPD1669	Approved
0.7712	Intermediate Similarity	NPD7157	Approved
0.7712	Intermediate Similarity	NPD6671	Approved
0.7705	Intermediate Similarity	NPD1281	Approved
0.7699	Intermediate Similarity	NPD3134	Approved
0.7686	Intermediate Similarity	NPD2667	Approved
0.7686	Intermediate Similarity	NPD2668	Approved
0.7686	Intermediate Similarity	NPD4626	Approved
0.768	Intermediate Similarity	NPD6584	Phase 3
0.7667	Intermediate Similarity	NPD6581	Approved
0.7667	Intermediate Similarity	NPD6580	Approved
0.7623	Intermediate Similarity	NPD3847	Discontinued
0.7603	Intermediate Similarity	NPD5585	Approved
0.7603	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD2557	Approved
0.7563	Intermediate Similarity	NPD709	Approved
0.7544	Intermediate Similarity	NPD968	Approved
0.7541	Intermediate Similarity	NPD6516	Phase 2
0.7541	Intermediate Similarity	NPD5846	Approved
0.754	Intermediate Similarity	NPD4624	Approved
0.7521	Intermediate Similarity	NPD1182	Approved
0.752	Intermediate Similarity	NPD1283	Approved
0.75	Intermediate Similarity	NPD2232	Approved
0.75	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD2981	Phase 2
0.75	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD2230	Approved
0.75	Intermediate Similarity	NPD2233	Approved
0.75	Intermediate Similarity	NPD3022	Approved
0.748	Intermediate Similarity	NPD2861	Phase 2
0.7478	Intermediate Similarity	NPD1358	Approved
0.7459	Intermediate Similarity	NPD3445	Approved
0.7459	Intermediate Similarity	NPD3443	Approved
0.7459	Intermediate Similarity	NPD3444	Approved
0.7458	Intermediate Similarity	NPD821	Approved
0.7442	Intermediate Similarity	NPD5111	Phase 2
0.7442	Intermediate Similarity	NPD5109	Approved
0.7442	Intermediate Similarity	NPD5110	Phase 2
0.744	Intermediate Similarity	NPD6583	Phase 3
0.744	Intermediate Similarity	NPD2983	Phase 2
0.744	Intermediate Similarity	NPD6582	Phase 2
0.744	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2982	Phase 2
0.7422	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6387	Discontinued
0.7411	Intermediate Similarity	NPD3028	Approved
0.7402	Intermediate Similarity	NPD7905	Discontinued
0.7398	Intermediate Similarity	NPD17	Approved
0.7398	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD1241	Discontinued
0.7381	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1876	Approved
0.7364	Intermediate Similarity	NPD7095	Approved
0.736	Intermediate Similarity	NPD1840	Phase 2
0.7344	Intermediate Similarity	NPD3018	Phase 2
0.7328	Intermediate Similarity	NPD4060	Phase 1
0.7328	Intermediate Similarity	NPD2979	Phase 3
0.7317	Intermediate Similarity	NPD3049	Approved
0.7308	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5718	Phase 2
0.7302	Intermediate Similarity	NPD6543	Approved
0.7302	Intermediate Similarity	NPD4359	Approved
0.7302	Intermediate Similarity	NPD6540	Phase 3
0.7302	Intermediate Similarity	NPD6542	Approved
0.7302	Intermediate Similarity	NPD6539	Approved
0.7287	Intermediate Similarity	NPD4908	Phase 1
0.728	Intermediate Similarity	NPD1610	Phase 2
0.728	Intermediate Similarity	NPD1611	Approved
0.728	Intermediate Similarity	NPD3705	Approved
0.7273	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6538	Approved
0.7244	Intermediate Similarity	NPD2922	Phase 1
0.7244	Intermediate Similarity	NPD6541	Approved
0.7236	Intermediate Similarity	NPD1894	Discontinued
0.7236	Intermediate Similarity	NPD1548	Phase 1
0.7227	Intermediate Similarity	NPD1137	Approved
0.7227	Intermediate Similarity	NPD1139	Approved
0.7222	Intermediate Similarity	NPD2231	Phase 2
0.7222	Intermediate Similarity	NPD2235	Phase 2
0.7222	Intermediate Similarity	NPD1608	Approved
0.7218	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD844	Approved
0.72	Intermediate Similarity	NPD3496	Discontinued
0.7197	Intermediate Similarity	NPD4140	Approved
0.7179	Intermediate Similarity	NPD290	Approved
0.7177	Intermediate Similarity	NPD1357	Approved
0.7176	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1138	Approved
0.7165	Intermediate Similarity	NPD2428	Approved
0.7165	Intermediate Similarity	NPD2429	Approved
0.7164	Intermediate Similarity	NPD6895	Approved
0.7164	Intermediate Similarity	NPD6896	Approved
0.7143	Intermediate Similarity	NPD5735	Approved
0.7132	Intermediate Similarity	NPD7018	Phase 2
0.7121	Intermediate Similarity	NPD8032	Phase 2
0.712	Intermediate Similarity	NPD2554	Approved
0.712	Intermediate Similarity	NPD2556	Approved
0.7111	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4108	Discontinued
0.7105	Intermediate Similarity	NPD1242	Phase 1
0.7099	Intermediate Similarity	NPD4625	Phase 3
0.7097	Intermediate Similarity	NPD2486	Discontinued
0.709	Intermediate Similarity	NPD4097	Suspended
0.709	Intermediate Similarity	NPD6353	Approved
0.7087	Intermediate Similarity	NPD1244	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3620	Phase 2
0.7068	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3110	Approved
0.7068	Intermediate Similarity	NPD3109	Approved
0.7068	Intermediate Similarity	NPD2238	Phase 2
0.7068	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2438	Suspended
0.7059	Intermediate Similarity	NPD2935	Discontinued
0.7059	Intermediate Similarity	NPD2531	Phase 2
0.7054	Intermediate Similarity	NPD4098	Discontinued
0.7045	Intermediate Similarity	NPD6798	Discontinued
0.7045	Intermediate Similarity	NPD1039	Discontinued
0.704	Intermediate Similarity	NPD6382	Discontinued
0.7031	Intermediate Similarity	NPD4749	Approved
0.7031	Intermediate Similarity	NPD3685	Discontinued
0.7031	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6355	Discontinued
0.7015	Intermediate Similarity	NPD3657	Discovery
0.7009	Intermediate Similarity	NPD9697	Approved
0.7	Intermediate Similarity	NPD3691	Phase 2
0.7	Intermediate Similarity	NPD2798	Approved
0.7	Intermediate Similarity	NPD3690	Phase 2
0.7	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7265	Discontinued
0.6992	Remote Similarity	NPD4870	Approved
0.6991	Remote Similarity	NPD288	Approved
0.6984	Remote Similarity	NPD1778	Approved
0.6977	Remote Similarity	NPD8651	Approved
0.697	Remote Similarity	NPD6179	Discontinued
0.697	Remote Similarity	NPD5163	Phase 2
0.696	Remote Similarity	NPD3091	Approved
0.6957	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2808	Discontinued
0.6947	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1613	Approved
0.6929	Remote Similarity	NPD3294	Phase 2
0.6923	Remote Similarity	NPD2797	Approved
0.6917	Remote Similarity	NPD7294	Phase 1
0.6917	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD111	Approved
0.6912	Remote Similarity	NPD4536	Approved
0.6912	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4538	Approved
0.6911	Remote Similarity	NPD595	Approved
0.6911	Remote Similarity	NPD593	Approved
0.6906	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2594	Approved
0.6905	Remote Similarity	NPD2595	Approved
0.6899	Remote Similarity	NPD4129	Approved
0.6897	Remote Similarity	NPD940	Approved
0.6897	Remote Similarity	NPD846	Approved
0.6885	Remote Similarity	NPD7635	Approved
0.6875	Remote Similarity	NPD1535	Discovery
0.6875	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2674	Phase 3
0.6866	Remote Similarity	NPD4474	Approved
0.6866	Remote Similarity	NPD4062	Phase 3
0.6866	Remote Similarity	NPD4475	Approved
0.6866	Remote Similarity	NPD6233	Phase 2
0.6857	Remote Similarity	NPD6331	Phase 2
0.6857	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3095	Discontinued
0.6842	Remote Similarity	NPD1024	Discontinued
0.6842	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2157	Approved
0.6835	Remote Similarity	NPD7037	Approved
0.6829	Remote Similarity	NPD2234	Approved
0.6829	Remote Similarity	NPD2229	Approved
0.6829	Remote Similarity	NPD592	Approved
0.6829	Remote Similarity	NPD594	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