NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	156.09
Volume:	185.813
LogP:	4.329
LogD:	3.808
LogS:	-4.908
# Rotatable Bonds:	0
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.548
Synthetic Accessibility Score:	1.448
Fsp3:	0.167
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:	-4.462
MDCK Permeability:	2.0998089894419536e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.204
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.677
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.765
Plasma Protein Binding (PPB):	95.90885162353516%
Volume Distribution (VD):	0.983
Pgp-substrate:	2.5669894218444824%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.822
CYP2C19-substrate:	0.683
CYP2C9-inhibitor:	0.468
CYP2C9-substrate:	0.827
CYP2D6-inhibitor:	0.679
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.432
CYP3A4-substrate:	0.381

ADMET: Excretion

Clearance (CL):	9.635
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.497
AMES Toxicity:	0.765
Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.558
Skin Sensitization:	0.833
Carcinogencity:	0.847
Eye Corrosion:	0.902
Eye Irritation:	0.998
Respiratory Toxicity:	0.266

Download Data

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

Natural Product: NPC1008

Natural Product ID:	NPC1008
*Common Name:**	1,4-Dimethylnaphthalene
IUPAC Name:	1,4-dimethylnaphthalene
Synonyms:	1,4-Dimethyl-Naphthalene; 1,4-Dimethylnaphthalene
Standard InCHIKey:	APQSQLNWAIULLK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H12/c1-9-7-8-10(2)12-6-4-3-5-11(9)12/h3-8H,1-2H3
SMILES:	Cc1ccc(C)c2ccccc12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL362076
PubChem CID:	11304
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO29105	Meconopsis punicea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29105	Meconopsis punicea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29105	Meconopsis punicea	Species	Papaveraceae	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	1
Others	1
Potency	2

Activity Type	# Activity
Individual Protein	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	3600.0	nM	PMID[505327]
NPT35	Others	n.a.		LogP	=	4.614	n.a.	PMID[505328]
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43641.2	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 NPC1008 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	1325
0.1-0.2	3590
0.2-0.3	13673
0.3-0.4	16037
0.4-0.5	6577
0.5-0.6	1132
0.6-0.7	244
0.7-0.8	56
0.8-0.85	25
0.85-0.9	13
0.9-0.95	14
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC87099
1.0	High Similarity	NPC280135
1.0	High Similarity	NPC226999
1.0	High Similarity	NPC39799
1.0	High Similarity	NPC135433
1.0	High Similarity	NPC158028
1.0	High Similarity	NPC193578
0.9697	High Similarity	NPC213570
0.9697	High Similarity	NPC139416
0.9697	High Similarity	NPC246822
0.9565	High Similarity	NPC307195
0.942	High Similarity	NPC96835
0.942	High Similarity	NPC258492
0.9394	High Similarity	NPC267443
0.9394	High Similarity	NPC6107
0.9275	High Similarity	NPC54269
0.9265	High Similarity	NPC72670
0.9265	High Similarity	NPC251490
0.9242	High Similarity	NPC113837
0.9242	High Similarity	NPC289915
0.9091	High Similarity	NPC291066
0.9041	High Similarity	NPC159661
0.9	High Similarity	NPC1901
0.8939	High Similarity	NPC113670
0.8919	High Similarity	NPC315216
0.8904	High Similarity	NPC245896
0.8904	High Similarity	NPC66270
0.8788	High Similarity	NPC71009
0.8767	High Similarity	NPC3190
0.8767	High Similarity	NPC249018
0.8714	High Similarity	NPC263385
0.8667	High Similarity	NPC50063
0.8657	High Similarity	NPC88566
0.8636	High Similarity	NPC248705
0.8636	High Similarity	NPC238023
0.8636	High Similarity	NPC310758
0.8636	High Similarity	NPC246588
0.8636	High Similarity	NPC54368
0.8636	High Similarity	NPC150196
0.8529	High Similarity	NPC198023
0.8529	High Similarity	NPC32312
0.8529	High Similarity	NPC155172
0.8485	Intermediate Similarity	NPC147062
0.8406	Intermediate Similarity	NPC178527
0.84	Intermediate Similarity	NPC255345
0.8382	Intermediate Similarity	NPC45756
0.8378	Intermediate Similarity	NPC110264
0.8358	Intermediate Similarity	NPC135924
0.8333	Intermediate Similarity	NPC36357
0.8333	Intermediate Similarity	NPC64270
0.8333	Intermediate Similarity	NPC114327
0.8333	Intermediate Similarity	NPC8235
0.831	Intermediate Similarity	NPC473206
0.8235	Intermediate Similarity	NPC22786
0.8235	Intermediate Similarity	NPC66517
0.8235	Intermediate Similarity	NPC29680
0.8182	Intermediate Similarity	NPC212114
0.8182	Intermediate Similarity	NPC300345
0.8182	Intermediate Similarity	NPC65873
0.8182	Intermediate Similarity	NPC120441
0.8116	Intermediate Similarity	NPC21211
0.8088	Intermediate Similarity	NPC210849
0.803	Intermediate Similarity	NPC198841
0.803	Intermediate Similarity	NPC269586
0.7971	Intermediate Similarity	NPC200745
0.7879	Intermediate Similarity	NPC149436
0.7879	Intermediate Similarity	NPC277704
0.7857	Intermediate Similarity	NPC277277
0.7848	Intermediate Similarity	NPC242628
0.7746	Intermediate Similarity	NPC264470
0.7711	Intermediate Similarity	NPC60408
0.7681	Intermediate Similarity	NPC169110
0.7671	Intermediate Similarity	NPC22760
0.7639	Intermediate Similarity	NPC36440
0.7568	Intermediate Similarity	NPC297358
0.7568	Intermediate Similarity	NPC200936
0.7561	Intermediate Similarity	NPC267704
0.7558	Intermediate Similarity	NPC103346
0.7529	Intermediate Similarity	NPC298115
0.7471	Intermediate Similarity	NPC128645
0.7442	Intermediate Similarity	NPC26224
0.7386	Intermediate Similarity	NPC289883
0.7381	Intermediate Similarity	NPC307
0.7381	Intermediate Similarity	NPC160339
0.7356	Intermediate Similarity	NPC125226
0.7356	Intermediate Similarity	NPC220596
0.7349	Intermediate Similarity	NPC133162
0.7333	Intermediate Similarity	NPC5324
0.7326	Intermediate Similarity	NPC418308
0.7326	Intermediate Similarity	NPC199567
0.7326	Intermediate Similarity	NPC325709
0.7308	Intermediate Similarity	NPC276699
0.7273	Intermediate Similarity	NPC212463
0.7253	Intermediate Similarity	NPC49994
0.725	Intermediate Similarity	NPC103488
0.7241	Intermediate Similarity	NPC173413
0.7209	Intermediate Similarity	NPC153308
0.7209	Intermediate Similarity	NPC267262
0.7176	Intermediate Similarity	NPC164526
0.7159	Intermediate Similarity	NPC133461
0.7125	Intermediate Similarity	NPC290638
0.7125	Intermediate Similarity	NPC9796
0.7123	Intermediate Similarity	NPC50266
0.7111	Intermediate Similarity	NPC472880
0.7083	Intermediate Similarity	NPC45255
0.7079	Intermediate Similarity	NPC153885
0.7079	Intermediate Similarity	NPC323420
0.7079	Intermediate Similarity	NPC155232
0.7073	Intermediate Similarity	NPC285716
0.7073	Intermediate Similarity	NPC157055
0.7073	Intermediate Similarity	NPC17408
0.7045	Intermediate Similarity	NPC19256
0.7033	Intermediate Similarity	NPC185208
0.7033	Intermediate Similarity	NPC219573
0.7011	Intermediate Similarity	NPC157778
0.7	Intermediate Similarity	NPC238219
0.6974	Remote Similarity	NPC311343
0.6957	Remote Similarity	NPC239185
0.6957	Remote Similarity	NPC324602
0.6957	Remote Similarity	NPC226041
0.6951	Remote Similarity	NPC272260
0.6944	Remote Similarity	NPC147578
0.6941	Remote Similarity	NPC95429
0.6932	Remote Similarity	NPC113307
0.6923	Remote Similarity	NPC172925
0.6923	Remote Similarity	NPC260233
0.6923	Remote Similarity	NPC74458
0.6915	Remote Similarity	NPC472879
0.6914	Remote Similarity	NPC298023
0.6905	Remote Similarity	NPC230068
0.6897	Remote Similarity	NPC69057
0.6897	Remote Similarity	NPC43945
0.6889	Remote Similarity	NPC314690
0.6889	Remote Similarity	NPC59677
0.6883	Remote Similarity	NPC98880
0.6882	Remote Similarity	NPC134882
0.6875	Remote Similarity	NPC189371
0.6875	Remote Similarity	NPC238696
0.6867	Remote Similarity	NPC164449
0.6867	Remote Similarity	NPC95868
0.6867	Remote Similarity	NPC184030
0.6849	Remote Similarity	NPC200624
0.6842	Remote Similarity	NPC239854
0.6835	Remote Similarity	NPC285679
0.6829	Remote Similarity	NPC224544
0.6824	Remote Similarity	NPC104070
0.6809	Remote Similarity	NPC221825
0.6795	Remote Similarity	NPC95289
0.6795	Remote Similarity	NPC229235
0.6786	Remote Similarity	NPC273033
0.6786	Remote Similarity	NPC145053
0.6786	Remote Similarity	NPC12936
0.6782	Remote Similarity	NPC148231
0.6778	Remote Similarity	NPC284475
0.6778	Remote Similarity	NPC470926
0.6774	Remote Similarity	NPC265220
0.6753	Remote Similarity	NPC82770
0.6753	Remote Similarity	NPC78954
0.6753	Remote Similarity	NPC239931
0.675	Remote Similarity	NPC113000
0.675	Remote Similarity	NPC122327
0.675	Remote Similarity	NPC112609
0.6747	Remote Similarity	NPC151405
0.6747	Remote Similarity	NPC139901
0.6744	Remote Similarity	NPC168855
0.6737	Remote Similarity	NPC128248
0.6737	Remote Similarity	NPC476993
0.6737	Remote Similarity	NPC136810
0.6737	Remote Similarity	NPC109514
0.6737	Remote Similarity	NPC225079
0.6737	Remote Similarity	NPC133809
0.6709	Remote Similarity	NPC326200
0.6709	Remote Similarity	NPC208302
0.6707	Remote Similarity	NPC179726
0.6706	Remote Similarity	NPC73637
0.6706	Remote Similarity	NPC121478
0.6703	Remote Similarity	NPC1682
0.6703	Remote Similarity	NPC188844
0.6702	Remote Similarity	NPC75724
0.6667	Remote Similarity	NPC235059
0.6667	Remote Similarity	NPC477703
0.6667	Remote Similarity	NPC475710
0.6667	Remote Similarity	NPC169222
0.6667	Remote Similarity	NPC328178
0.6667	Remote Similarity	NPC474354
0.6667	Remote Similarity	NPC252067
0.6667	Remote Similarity	NPC71664
0.6667	Remote Similarity	NPC16190
0.6628	Remote Similarity	NPC197581
0.6628	Remote Similarity	NPC172984
0.6628	Remote Similarity	NPC39600
0.6628	Remote Similarity	NPC273758
0.6628	Remote Similarity	NPC119677
0.6627	Remote Similarity	NPC50192
0.6625	Remote Similarity	NPC271437
0.6625	Remote Similarity	NPC244738
0.6623	Remote Similarity	NPC52330
0.6598	Remote Similarity	NPC19856
0.6593	Remote Similarity	NPC475059
0.6593	Remote Similarity	NPC475023

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 NPC1008 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	990
0.1-0.2	679
0.2-0.3	2463
0.3-0.4	3210
0.4-0.5	1289
0.5-0.6	369
0.6-0.7	121
0.7-0.8	28
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8939	High Similarity	NPD675	Discontinued
0.7778	Intermediate Similarity	NPD4544	Approved
0.7722	Intermediate Similarity	NPD3903	Approved
0.7722	Intermediate Similarity	NPD3979	Approved
0.7722	Intermediate Similarity	NPD3904	Approved
0.7722	Intermediate Similarity	NPD3981	Approved
0.7568	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1673	Approved
0.7439	Intermediate Similarity	NPD4635	Approved
0.7416	Intermediate Similarity	NPD3093	Approved
0.7381	Intermediate Similarity	NPD3099	Discontinued
0.7349	Intermediate Similarity	NPD3429	Approved
0.7349	Intermediate Similarity	NPD3427	Approved
0.7333	Intermediate Similarity	NPD5598	Approved
0.7333	Intermediate Similarity	NPD5597	Approved
0.7273	Intermediate Similarity	NPD4408	Approved
0.7273	Intermediate Similarity	NPD4405	Approved
0.7273	Intermediate Similarity	NPD4407	Approved
0.726	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3035	Approved
0.7191	Intermediate Similarity	NPD4545	Approved
0.7191	Intermediate Similarity	NPD4542	Approved
0.7176	Intermediate Similarity	NPD4406	Approved
0.7176	Intermediate Similarity	NPD4409	Approved
0.716	Intermediate Similarity	NPD1475	Approved
0.7143	Intermediate Similarity	NPD292	Approved
0.7143	Intermediate Similarity	NPD294	Approved
0.7125	Intermediate Similarity	NPD4144	Approved
0.7125	Intermediate Similarity	NPD4147	Approved
0.7111	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6049	Phase 2
0.7108	Intermediate Similarity	NPD4170	Approved
0.7108	Intermediate Similarity	NPD4701	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4169	Approved
0.7093	Intermediate Similarity	NPD3428	Approved
0.7093	Intermediate Similarity	NPD3426	Approved
0.7073	Intermediate Similarity	NPD1617	Discontinued
0.7073	Intermediate Similarity	NPD914	Suspended
0.7065	Intermediate Similarity	NPD5832	Phase 3
0.7024	Intermediate Similarity	NPD2001	Discontinued
0.7024	Intermediate Similarity	NPD5288	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3971	Phase 1
0.7024	Intermediate Similarity	NPD423	Phase 3
0.7011	Intermediate Similarity	NPD3345	Approved
0.7	Intermediate Similarity	NPD3980	Approved
0.7	Intermediate Similarity	NPD2878	Approved
0.7	Intermediate Similarity	NPD3982	Approved
0.6988	Remote Similarity	NPD4026	Approved
0.6988	Remote Similarity	NPD4027	Approved
0.6957	Remote Similarity	NPD3495	Discontinued
0.6947	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6354	Discontinued
0.6897	Remote Similarity	NPD650	Approved
0.6867	Remote Similarity	NPD260	Discontinued
0.6867	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3346	Approved
0.6854	Remote Similarity	NPD3344	Approved
0.6848	Remote Similarity	NPD6472	Discontinued
0.6842	Remote Similarity	NPD4321	Approved
0.6824	Remote Similarity	NPD1185	Approved
0.6813	Remote Similarity	NPD1563	Approved
0.6786	Remote Similarity	NPD942	Approved
0.6782	Remote Similarity	NPD4636	Approved
0.6778	Remote Similarity	NPD1239	Approved
0.6778	Remote Similarity	NPD7609	Phase 3
0.6774	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.675	Remote Similarity	NPD9588	Approved
0.675	Remote Similarity	NPD9592	Approved
0.675	Remote Similarity	NPD9591	Approved
0.675	Remote Similarity	NPD80	Approved
0.675	Remote Similarity	NPD9590	Approved
0.675	Remote Similarity	NPD9594	Approved
0.675	Remote Similarity	NPD9593	Approved
0.675	Remote Similarity	NPD9589	Approved
0.6744	Remote Similarity	NPD5178	Approved
0.6705	Remote Similarity	NPD2002	Discontinued
0.6705	Remote Similarity	NPD4146	Approved
0.6705	Remote Similarity	NPD4145	Approved
0.6703	Remote Similarity	NPD7631	Approved
0.6667	Remote Similarity	NPD1989	Approved
0.6667	Remote Similarity	NPD2895	Discontinued
0.6667	Remote Similarity	NPD5916	Discontinued
0.6667	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5675	Discontinued
0.6628	Remote Similarity	NPD4000	Phase 3
0.6627	Remote Similarity	NPD79	Approved
0.6627	Remote Similarity	NPD9564	Approved
0.6627	Remote Similarity	NPD9563	Approved
0.6625	Remote Similarity	NPD9728	Phase 1
0.6596	Remote Similarity	NPD1564	Approved
0.6596	Remote Similarity	NPD713	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1565	Approved
0.6596	Remote Similarity	NPD1566	Phase 3
0.6566	Remote Similarity	NPD7170	Discontinued
0.6556	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2539	Approved
0.6552	Remote Similarity	NPD2538	Approved
0.6548	Remote Similarity	NPD590	Approved
0.6548	Remote Similarity	NPD589	Approved
0.6543	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4936	Approved
0.6531	Remote Similarity	NPD4937	Approved
0.6522	Remote Similarity	NPD1508	Approved
0.6517	Remote Similarity	NPD1087	Approved
0.65	Remote Similarity	NPD2342	Discontinued
0.6489	Remote Similarity	NPD3457	Approved
0.6489	Remote Similarity	NPD2005	Discontinued
0.6489	Remote Similarity	NPD3458	Approved
0.6489	Remote Similarity	NPD3456	Approved
0.6484	Remote Similarity	NPD5915	Approved
0.6458	Remote Similarity	NPD4737	Phase 2
0.6444	Remote Similarity	NPD1101	Approved
0.6429	Remote Similarity	NPD296	Approved
0.6429	Remote Similarity	NPD295	Approved
0.6429	Remote Similarity	NPD293	Approved
0.6413	Remote Similarity	NPD517	Discontinued
0.6413	Remote Similarity	NPD4543	Discontinued
0.6404	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD1616	Discontinued
0.6374	Remote Similarity	NPD771	Phase 3
0.6353	Remote Similarity	NPD1051	Approved
0.6353	Remote Similarity	NPD1052	Approved
0.6353	Remote Similarity	NPD1053	Approved
0.6346	Remote Similarity	NPD7635	Approved
0.6333	Remote Similarity	NPD782	Approved
0.6333	Remote Similarity	NPD780	Approved
0.6333	Remote Similarity	NPD783	Approved
0.6333	Remote Similarity	NPD781	Approved
0.6316	Remote Similarity	NPD1843	Approved
0.631	Remote Similarity	NPD603	Approved
0.6304	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD1090	Approved
0.6304	Remote Similarity	NPD1086	Approved
0.6304	Remote Similarity	NPD4728	Approved
0.6304	Remote Similarity	NPD1089	Approved
0.63	Remote Similarity	NPD1268	Approved
0.63	Remote Similarity	NPD1269	Approved
0.6292	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD2208	Approved
0.6292	Remote Similarity	NPD2205	Approved
0.6289	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD498	Approved
0.6286	Remote Similarity	NPD495	Approved
0.6286	Remote Similarity	NPD496	Approved
0.6279	Remote Similarity	NPD5372	Approved
0.6279	Remote Similarity	NPD5371	Approved
0.6265	Remote Similarity	NPD9716	Approved
0.625	Remote Similarity	NPD262	Approved
0.625	Remote Similarity	NPD263	Approved
0.6237	Remote Similarity	NPD2998	Approved
0.6237	Remote Similarity	NPD3000	Approved
0.6237	Remote Similarity	NPD2997	Approved
0.6235	Remote Similarity	NPD9393	Approved
0.6235	Remote Similarity	NPD227	Approved
0.6235	Remote Similarity	NPD225	Approved
0.6235	Remote Similarity	NPD9397	Approved
0.6226	Remote Similarity	NPD2508	Discontinued
0.6226	Remote Similarity	NPD497	Approved
0.6224	Remote Similarity	NPD5630	Phase 1
0.6222	Remote Similarity	NPD1697	Approved
0.6211	Remote Similarity	NPD4094	Approved
0.6211	Remote Similarity	NPD5554	Approved
0.6207	Remote Similarity	NPD472	Approved
0.6196	Remote Similarity	NPD1629	Approved
0.6196	Remote Similarity	NPD800	Approved
0.6196	Remote Similarity	NPD1628	Approved
0.617	Remote Similarity	NPD1088	Approved
0.6163	Remote Similarity	NPD508	Approved
0.6163	Remote Similarity	NPD507	Approved
0.6162	Remote Similarity	NPD4734	Approved
0.6162	Remote Similarity	NPD4735	Approved
0.6162	Remote Similarity	NPD2841	Approved
0.6162	Remote Similarity	NPD1932	Approved
0.6154	Remote Similarity	NPD2384	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5963	Phase 2
0.6146	Remote Similarity	NPD5964	Phase 2
0.6132	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD2066	Phase 3
0.6105	Remote Similarity	NPD1409	Phase 3
0.6105	Remote Similarity	NPD845	Approved
0.61	Remote Similarity	NPD1929	Approved
0.61	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.61	Remote Similarity	NPD1930	Approved
0.6082	Remote Similarity	NPD4657	Approved
0.6082	Remote Similarity	NPD4655	Approved
0.6075	Remote Similarity	NPD5951	Approved
0.6067	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD830	Approved
0.6067	Remote Similarity	NPD831	Approved
0.6061	Remote Similarity	NPD1916	Discontinued
0.6042	Remote Similarity	NPD4814	Discontinued
0.6042	Remote Similarity	NPD1693	Approved
0.6042	Remote Similarity	NPD3772	Phase 3
0.604	Remote Similarity	NPD179	Clinical (unspecified phase)
0.604	Remote Similarity	NPD3046	Approved
0.604	Remote Similarity	NPD3047	Approved
0.604	Remote Similarity	NPD3048	Approved
0.6023	Remote Similarity	NPD226	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