NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	134.11
Volume:	165.05
LogP:	4.11
LogD:	3.832
LogS:	-4.226
# Rotatable Bonds:	0
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.511
Synthetic Accessibility Score:	1.302
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.631
MDCK Permeability:	1.952526690729428e-05
Pgp-inhibitor:	0.079
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.899
Plasma Protein Binding (PPB):	92.27924346923828%
Volume Distribution (VD):	0.914
Pgp-substrate:	6.032665252685547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.762
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.603
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.717
CYP2D6-inhibitor:	0.302
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.523

ADMET: Excretion

Clearance (CL):	9.843
Half-life (T1/2):	0.429

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.068
AMES Toxicity:	0.221
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.619
Skin Sensitization:	0.249
Carcinogencity:	0.656
Eye Corrosion:	0.961
Eye Irritation:	0.996
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC289915

Natural Product ID:	NPC289915
*Common Name:**	1,2,4,5-Tetramethylbenzene
IUPAC Name:	1,2,4,5-tetramethylbenzene
Synonyms:	1,2,4,5-Tetramethylbenzene
Standard InCHIKey:	SQNZJJAZBFDUTD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3
SMILES:	Cc1cc(C)c(C)cc1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797134
PubChem CID:	7269
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives

*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
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	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
Others	1
Potency	6

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.	LogP	=	4.738	n.a.	PMID[539106]
NPT2	Others	Unspecified	Potency	n.a.	69008.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	24706.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	38570.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	48854.2	nM	PubChem BioAssay data set

☑ 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 NPC289915 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	1025
0.1-0.2	3400
0.2-0.3	14989
0.3-0.4	16600
0.4-0.5	5288
0.5-0.6	1032
0.6-0.7	242
0.7-0.8	64
0.8-0.85	17
0.85-0.9	25
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC113837
0.9839	High Similarity	NPC6107
0.9242	High Similarity	NPC280135
0.9242	High Similarity	NPC39799
0.9242	High Similarity	NPC158028
0.9242	High Similarity	NPC226999
0.9242	High Similarity	NPC193578
0.9242	High Similarity	NPC135433
0.9242	High Similarity	NPC1008
0.9242	High Similarity	NPC87099
0.9104	High Similarity	NPC54269
0.9048	High Similarity	NPC45756
0.9048	High Similarity	NPC88566
0.9032	High Similarity	NPC310758
0.9032	High Similarity	NPC150196
0.9032	High Similarity	NPC54368
0.9032	High Similarity	NPC238023
0.9032	High Similarity	NPC248705
0.9016	High Similarity	NPC64270
0.8939	High Similarity	NPC246822
0.8939	High Similarity	NPC139416
0.8939	High Similarity	NPC213570
0.8906	High Similarity	NPC32312
0.8906	High Similarity	NPC155172
0.8906	High Similarity	NPC198023
0.8871	High Similarity	NPC147062
0.8841	High Similarity	NPC307195
0.8769	High Similarity	NPC178527
0.873	High Similarity	NPC135924
0.8714	High Similarity	NPC110264
0.871	High Similarity	NPC8235
0.8696	High Similarity	NPC96835
0.8696	High Similarity	NPC258492
0.8636	High Similarity	NPC267443
0.8594	High Similarity	NPC71009
0.8594	High Similarity	NPC66517
0.8594	High Similarity	NPC29680
0.8592	High Similarity	NPC249018
0.8592	High Similarity	NPC3190
0.8548	High Similarity	NPC65873
0.8548	High Similarity	NPC300345
0.8548	High Similarity	NPC212114
0.8548	High Similarity	NPC120441
0.8529	High Similarity	NPC72670
0.8529	High Similarity	NPC251490
0.8462	Intermediate Similarity	NPC21211
0.8438	Intermediate Similarity	NPC210849
0.8387	Intermediate Similarity	NPC198841
0.8387	Intermediate Similarity	NPC269586
0.8356	Intermediate Similarity	NPC159661
0.8333	Intermediate Similarity	NPC291066
0.8286	Intermediate Similarity	NPC1901
0.8243	Intermediate Similarity	NPC315216
0.8226	Intermediate Similarity	NPC277704
0.8226	Intermediate Similarity	NPC149436
0.8219	Intermediate Similarity	NPC66270
0.8219	Intermediate Similarity	NPC245896
0.8182	Intermediate Similarity	NPC113670
0.8154	Intermediate Similarity	NPC246588
0.8133	Intermediate Similarity	NPC242628
0.8	Intermediate Similarity	NPC169110
0.8	Intermediate Similarity	NPC50063
0.8	Intermediate Similarity	NPC263385
0.7857	Intermediate Similarity	NPC200936
0.7846	Intermediate Similarity	NPC114327
0.7846	Intermediate Similarity	NPC36357
0.7821	Intermediate Similarity	NPC267704
0.7761	Intermediate Similarity	NPC22786
0.7733	Intermediate Similarity	NPC255345
0.7625	Intermediate Similarity	NPC160339
0.7625	Intermediate Similarity	NPC164526
0.7625	Intermediate Similarity	NPC307
0.7606	Intermediate Similarity	NPC473206
0.7568	Intermediate Similarity	NPC276699
0.7536	Intermediate Similarity	NPC264470
0.7534	Intermediate Similarity	NPC212463
0.7531	Intermediate Similarity	NPC60408
0.75	Intermediate Similarity	NPC200745
0.75	Intermediate Similarity	NPC103488
0.7465	Intermediate Similarity	NPC22760
0.7439	Intermediate Similarity	NPC153308
0.7391	Intermediate Similarity	NPC50266
0.7368	Intermediate Similarity	NPC290638
0.7361	Intermediate Similarity	NPC297358
0.7353	Intermediate Similarity	NPC45255
0.7349	Intermediate Similarity	NPC298115
0.7308	Intermediate Similarity	NPC17408
0.7308	Intermediate Similarity	NPC157055
0.7308	Intermediate Similarity	NPC285716
0.7262	Intermediate Similarity	NPC277277
0.7262	Intermediate Similarity	NPC173413
0.7262	Intermediate Similarity	NPC26224
0.7222	Intermediate Similarity	NPC311343
0.7206	Intermediate Similarity	NPC147578
0.7183	Intermediate Similarity	NPC36440
0.7176	Intermediate Similarity	NPC133461
0.7176	Intermediate Similarity	NPC125226
0.7176	Intermediate Similarity	NPC220596
0.7162	Intermediate Similarity	NPC74458
0.7143	Intermediate Similarity	NPC298023
0.7125	Intermediate Similarity	NPC230068
0.7123	Intermediate Similarity	NPC98880
0.7105	Intermediate Similarity	NPC189371
0.7101	Intermediate Similarity	NPC200624
0.7093	Intermediate Similarity	NPC155232
0.7093	Intermediate Similarity	NPC314690
0.7093	Intermediate Similarity	NPC323420
0.7093	Intermediate Similarity	NPC153885
0.7067	Intermediate Similarity	NPC285679
0.7051	Intermediate Similarity	NPC224544
0.7027	Intermediate Similarity	NPC95289
0.7027	Intermediate Similarity	NPC229235
0.7024	Intermediate Similarity	NPC157778
0.7011	Intermediate Similarity	NPC238219
0.7011	Intermediate Similarity	NPC289883
0.7	Intermediate Similarity	NPC145053
0.6986	Remote Similarity	NPC78954
0.6986	Remote Similarity	NPC82770
0.6986	Remote Similarity	NPC239931
0.6977	Remote Similarity	NPC103346
0.6974	Remote Similarity	NPC112609
0.6974	Remote Similarity	NPC122327
0.6974	Remote Similarity	NPC113000
0.6951	Remote Similarity	NPC133162
0.6951	Remote Similarity	NPC168855
0.6933	Remote Similarity	NPC326200
0.6933	Remote Similarity	NPC208302
0.6932	Remote Similarity	NPC260233
0.6905	Remote Similarity	NPC43945
0.6897	Remote Similarity	NPC128645
0.6892	Remote Similarity	NPC16190
0.6892	Remote Similarity	NPC235059
0.6892	Remote Similarity	NPC5324
0.6892	Remote Similarity	NPC169222
0.6875	Remote Similarity	NPC328178
0.6867	Remote Similarity	NPC252067
0.6867	Remote Similarity	NPC474354
0.6854	Remote Similarity	NPC219573
0.6854	Remote Similarity	NPC185208
0.6849	Remote Similarity	NPC52330
0.6842	Remote Similarity	NPC271437
0.6842	Remote Similarity	NPC244738
0.6835	Remote Similarity	NPC50192
0.6829	Remote Similarity	NPC39600
0.6829	Remote Similarity	NPC104070
0.6829	Remote Similarity	NPC172984
0.6829	Remote Similarity	NPC197581
0.6824	Remote Similarity	NPC267262
0.6795	Remote Similarity	NPC139658
0.679	Remote Similarity	NPC133050
0.6786	Remote Similarity	NPC474211
0.6786	Remote Similarity	NPC243166
0.6786	Remote Similarity	NPC93843
0.6782	Remote Similarity	NPC284475
0.6778	Remote Similarity	NPC226041
0.6778	Remote Similarity	NPC324602
0.6778	Remote Similarity	NPC239185
0.6778	Remote Similarity	NPC265220
0.6774	Remote Similarity	NPC11150
0.6753	Remote Similarity	NPC208075
0.6753	Remote Similarity	NPC108218
0.6744	Remote Similarity	NPC325709
0.6744	Remote Similarity	NPC418308
0.6744	Remote Similarity	NPC199567
0.6711	Remote Similarity	NPC155429
0.6709	Remote Similarity	NPC9796
0.6709	Remote Similarity	NPC325662
0.6709	Remote Similarity	NPC98269
0.6705	Remote Similarity	NPC1682
0.6705	Remote Similarity	NPC188844
0.6705	Remote Similarity	NPC59677
0.6703	Remote Similarity	NPC49994
0.6703	Remote Similarity	NPC75724
0.6703	Remote Similarity	NPC134882
0.6667	Remote Similarity	NPC98976
0.6667	Remote Similarity	NPC19256
0.6667	Remote Similarity	NPC190567
0.663	Remote Similarity	NPC221825
0.6625	Remote Similarity	NPC36342
0.6625	Remote Similarity	NPC76455
0.6625	Remote Similarity	NPC2785
0.6625	Remote Similarity	NPC285470
0.6625	Remote Similarity	NPC137847
0.6591	Remote Similarity	NPC475059
0.6591	Remote Similarity	NPC475023
0.6585	Remote Similarity	NPC231986
0.6585	Remote Similarity	NPC100039
0.6582	Remote Similarity	NPC271642
0.6582	Remote Similarity	NPC175393
0.6579	Remote Similarity	NPC219246
0.6559	Remote Similarity	NPC469481
0.6559	Remote Similarity	NPC245927
0.6559	Remote Similarity	NPC476993
0.6559	Remote Similarity	NPC289117
0.6559	Remote Similarity	NPC128248
0.6559	Remote Similarity	NPC109514
0.6559	Remote Similarity	NPC136810
0.6559	Remote Similarity	NPC225079
0.6559	Remote Similarity	NPC133809
0.6556	Remote Similarity	NPC472880

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 NPC289915 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	880
0.1-0.2	813
0.2-0.3	2886
0.3-0.4	3011
0.4-0.5	1082
0.5-0.6	338
0.6-0.7	124
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD675	Discontinued
0.7857	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3099	Discontinued
0.7536	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD292	Approved
0.7397	Intermediate Similarity	NPD294	Approved
0.7375	Intermediate Similarity	NPD4544	Approved
0.7361	Intermediate Similarity	NPD1673	Approved
0.7308	Intermediate Similarity	NPD3981	Approved
0.7308	Intermediate Similarity	NPD3904	Approved
0.7308	Intermediate Similarity	NPD3979	Approved
0.7308	Intermediate Similarity	NPD3903	Approved
0.7037	Intermediate Similarity	NPD4635	Approved
0.6974	Remote Similarity	NPD9589	Approved
0.6974	Remote Similarity	NPD9594	Approved
0.6974	Remote Similarity	NPD9593	Approved
0.6974	Remote Similarity	NPD80	Approved
0.6974	Remote Similarity	NPD9592	Approved
0.6974	Remote Similarity	NPD9591	Approved
0.6974	Remote Similarity	NPD9590	Approved
0.6974	Remote Similarity	NPD9588	Approved
0.6951	Remote Similarity	NPD3427	Approved
0.6951	Remote Similarity	NPD3429	Approved
0.6932	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6049	Phase 2
0.6905	Remote Similarity	NPD650	Approved
0.6875	Remote Similarity	NPD260	Discontinued
0.6867	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3093	Approved
0.6842	Remote Similarity	NPD9728	Phase 1
0.6835	Remote Similarity	NPD9564	Approved
0.6835	Remote Similarity	NPD79	Approved
0.6835	Remote Similarity	NPD9563	Approved
0.6829	Remote Similarity	NPD3971	Phase 1
0.6829	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3035	Approved
0.6786	Remote Similarity	NPD4406	Approved
0.6786	Remote Similarity	NPD4409	Approved
0.6782	Remote Similarity	NPD7609	Phase 3
0.6778	Remote Similarity	NPD3495	Discontinued
0.6778	Remote Similarity	NPD5598	Approved
0.6778	Remote Similarity	NPD5597	Approved
0.6753	Remote Similarity	NPD505	Clinical (unspecified phase)
0.675	Remote Similarity	NPD589	Approved
0.675	Remote Similarity	NPD590	Approved
0.675	Remote Similarity	NPD1475	Approved
0.6709	Remote Similarity	NPD4144	Approved
0.6709	Remote Similarity	NPD4147	Approved
0.6707	Remote Similarity	NPD4170	Approved
0.6707	Remote Similarity	NPD4169	Approved
0.6707	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD1087	Approved
0.6706	Remote Similarity	NPD3428	Approved
0.6706	Remote Similarity	NPD3426	Approved
0.6705	Remote Similarity	NPD7631	Approved
0.6705	Remote Similarity	NPD4407	Approved
0.6705	Remote Similarity	NPD4405	Approved
0.6705	Remote Similarity	NPD4408	Approved
0.6667	Remote Similarity	NPD1617	Discontinued
0.6629	Remote Similarity	NPD4542	Approved
0.6629	Remote Similarity	NPD4545	Approved
0.6629	Remote Similarity	NPD2878	Approved
0.6629	Remote Similarity	NPD3980	Approved
0.6629	Remote Similarity	NPD3982	Approved
0.6628	Remote Similarity	NPD1101	Approved
0.6628	Remote Similarity	NPD3345	Approved
0.6627	Remote Similarity	NPD2001	Discontinued
0.6627	Remote Similarity	NPD4000	Phase 3
0.6625	Remote Similarity	NPD293	Approved
0.6625	Remote Similarity	NPD296	Approved
0.6625	Remote Similarity	NPD295	Approved
0.6593	Remote Similarity	NPD713	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4027	Approved
0.6585	Remote Similarity	NPD4026	Approved
0.6559	Remote Similarity	NPD6354	Discontinued
0.6552	Remote Similarity	NPD771	Phase 3
0.6543	Remote Similarity	NPD1053	Approved
0.6543	Remote Similarity	NPD1052	Approved
0.6543	Remote Similarity	NPD1051	Approved
0.6522	Remote Similarity	NPD5832	Phase 3
0.6512	Remote Similarity	NPD781	Approved
0.6512	Remote Similarity	NPD782	Approved
0.6512	Remote Similarity	NPD780	Approved
0.6512	Remote Similarity	NPD783	Approved
0.65	Remote Similarity	NPD603	Approved
0.6477	Remote Similarity	NPD1086	Approved
0.6477	Remote Similarity	NPD1089	Approved
0.6477	Remote Similarity	NPD3344	Approved
0.6477	Remote Similarity	NPD3346	Approved
0.6477	Remote Similarity	NPD1090	Approved
0.6471	Remote Similarity	NPD2208	Approved
0.6471	Remote Similarity	NPD2205	Approved
0.6471	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5371	Approved
0.6463	Remote Similarity	NPD914	Suspended
0.6463	Remote Similarity	NPD5372	Approved
0.6456	Remote Similarity	NPD9716	Approved
0.6429	Remote Similarity	NPD1185	Approved
0.6429	Remote Similarity	NPD423	Phase 3
0.6429	Remote Similarity	NPD262	Approved
0.6429	Remote Similarity	NPD263	Approved
0.6421	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.642	Remote Similarity	NPD225	Approved
0.642	Remote Similarity	NPD9397	Approved
0.642	Remote Similarity	NPD227	Approved
0.642	Remote Similarity	NPD9393	Approved
0.6404	Remote Similarity	NPD517	Discontinued
0.6395	Remote Similarity	NPD4636	Approved
0.6386	Remote Similarity	NPD472	Approved
0.6386	Remote Similarity	NPD942	Approved
0.6374	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD800	Approved
0.6353	Remote Similarity	NPD5178	Approved
0.6341	Remote Similarity	NPD508	Approved
0.6341	Remote Similarity	NPD507	Approved
0.6333	Remote Similarity	NPD1088	Approved
0.6322	Remote Similarity	NPD4145	Approved
0.6322	Remote Similarity	NPD4146	Approved
0.6322	Remote Similarity	NPD2002	Discontinued
0.6316	Remote Similarity	NPD4321	Approved
0.6304	Remote Similarity	NPD6472	Discontinued
0.6304	Remote Similarity	NPD2895	Discontinued
0.6279	Remote Similarity	NPD5916	Discontinued
0.6264	Remote Similarity	NPD845	Approved
0.6264	Remote Similarity	NPD1563	Approved
0.6264	Remote Similarity	NPD1409	Phase 3
0.625	Remote Similarity	NPD5675	Discontinued
0.6237	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD830	Approved
0.6235	Remote Similarity	NPD831	Approved
0.6222	Remote Similarity	NPD1239	Approved
0.6196	Remote Similarity	NPD1693	Approved
0.6196	Remote Similarity	NPD4814	Discontinued
0.619	Remote Similarity	NPD226	Approved
0.618	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD2539	Approved
0.6163	Remote Similarity	NPD2538	Approved
0.6163	Remote Similarity	NPD9395	Approved
0.6163	Remote Similarity	NPD785	Approved
0.6162	Remote Similarity	NPD2206	Approved
0.6162	Remote Similarity	NPD2207	Approved
0.6154	Remote Similarity	NPD1508	Approved
0.6145	Remote Similarity	NPD9490	Approved
0.6129	Remote Similarity	NPD3458	Approved
0.6129	Remote Similarity	NPD1738	Approved
0.6129	Remote Similarity	NPD2005	Discontinued
0.6129	Remote Similarity	NPD3456	Approved
0.6129	Remote Similarity	NPD1989	Approved
0.6129	Remote Similarity	NPD1809	Phase 2
0.6129	Remote Similarity	NPD3457	Approved
0.6111	Remote Similarity	NPD3673	Approved
0.6111	Remote Similarity	NPD5915	Approved
0.6111	Remote Similarity	NPD3672	Approved
0.6098	Remote Similarity	NPD9294	Approved
0.6087	Remote Similarity	NPD3719	Approved
0.6087	Remote Similarity	NPD3718	Approved
0.6067	Remote Similarity	NPD531	Approved
0.6064	Remote Similarity	NPD288	Approved
0.6064	Remote Similarity	NPD1566	Phase 3
0.6064	Remote Similarity	NPD1564	Approved
0.6064	Remote Similarity	NPD1565	Approved
0.6061	Remote Similarity	NPD7170	Discontinued
0.6047	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD9491	Approved
0.6044	Remote Similarity	NPD530	Approved
0.6044	Remote Similarity	NPD4543	Discontinued
0.6023	Remote Similarity	NPD1697	Approved
0.6023	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4936	Approved
0.602	Remote Similarity	NPD179	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4937	Approved
0.6	Remote Similarity	NPD5346	Phase 2
0.6	Remote Similarity	NPD5347	Phase 2
0.6	Remote Similarity	NPD2342	Discontinued
0.6	Remote Similarity	NPD4813	Approved
0.6	Remote Similarity	NPD4263	Approved
0.598	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD538	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD9361	Approved
0.5978	Remote Similarity	NPD752	Approved
0.5957	Remote Similarity	NPD1843	Approved
0.5957	Remote Similarity	NPD844	Approved
0.5955	Remote Similarity	NPD4793	Discontinued
0.5955	Remote Similarity	NPD506	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD2066	Phase 3
0.5938	Remote Similarity	NPD4737	Phase 2
0.5938	Remote Similarity	NPD523	Approved
0.5938	Remote Similarity	NPD524	Approved
0.5934	Remote Similarity	NPD4728	Approved
0.5934	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD736	Approved
0.5914	Remote Similarity	NPD8	Approved
0.5914	Remote Similarity	NPD720	Approved
0.5914	Remote Similarity	NPD735	Approved
0.5914	Remote Similarity	NPD243	Approved
0.5914	Remote Similarity	NPD719	Approved
0.5914	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD9072	Clinical (unspecified phase)

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