NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	118.08
Volume:	139.198
LogP:	3.22
LogD:	2.933
LogS:	-3.491
# 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:	0.489
Synthetic Accessibility Score:	1.414
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.361
MDCK Permeability:	2.1086298147565685e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.797
30% Bioavailability (F30%):	0.633

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	92.6657943725586%
Volume Distribution (VD):	2.604
Pgp-substrate:	6.965086460113525%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.778
CYP2C19-inhibitor:	0.716
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.196
CYP2C9-substrate:	0.654
CYP2D6-inhibitor:	0.232
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	8.264
Half-life (T1/2):	0.464

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.104
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.126
Skin Sensitization:	0.708
Carcinogencity:	0.468
Eye Corrosion:	0.945
Eye Irritation:	0.994
Respiratory Toxicity:	0.102

Download Data

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

Natural Product: NPC21211

Natural Product ID:	NPC21211
*Common Name:**	Indan
IUPAC Name:	2,3-dihydro-1H-indene
Synonyms:
Standard InCHIKey:	PQNFLJBBNBOBRQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2
SMILES:	c1ccc2CCCc2c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL370687
PubChem CID:	10326
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000027] Indanes

*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

☑ 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

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	550000.0	nM	PMID[492359]
NPT35	Others	n.a.		LogP	=	3.33	n.a.	PMID[492361]

☑ 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 NPC21211 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	1342
0.1-0.2	4214
0.2-0.3	16148
0.3-0.4	15602
0.4-0.5	4204
0.5-0.6	858
0.6-0.7	215
0.7-0.8	50
0.8-0.85	42
0.85-0.9	16
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC66517
0.9333	High Similarity	NPC238023
0.9333	High Similarity	NPC310758
0.918	High Similarity	NPC71009
0.9077	High Similarity	NPC263385
0.8983	High Similarity	NPC198841
0.8889	High Similarity	NPC291066
0.8889	High Similarity	NPC155172
0.8833	High Similarity	NPC65873
0.8833	High Similarity	NPC120441
0.8833	High Similarity	NPC300345
0.8833	High Similarity	NPC212114
0.8814	High Similarity	NPC149436
0.8806	High Similarity	NPC1901
0.871	High Similarity	NPC135924
0.8667	High Similarity	NPC269586
0.8615	High Similarity	NPC6107
0.8594	High Similarity	NPC264470
0.8571	High Similarity	NPC29680
0.8507	High Similarity	NPC251490
0.85	High Similarity	NPC277704
0.8462	Intermediate Similarity	NPC289915
0.8462	Intermediate Similarity	NPC113837
0.8438	Intermediate Similarity	NPC88566
0.8438	Intermediate Similarity	NPC113670
0.8413	Intermediate Similarity	NPC248705
0.8413	Intermediate Similarity	NPC210849
0.8413	Intermediate Similarity	NPC54368
0.8413	Intermediate Similarity	NPC246588
0.8413	Intermediate Similarity	NPC150196
0.8387	Intermediate Similarity	NPC36357
0.8387	Intermediate Similarity	NPC8235
0.8387	Intermediate Similarity	NPC114327
0.8358	Intermediate Similarity	NPC246822
0.8358	Intermediate Similarity	NPC139416
0.8358	Intermediate Similarity	NPC213570
0.8308	Intermediate Similarity	NPC32312
0.8308	Intermediate Similarity	NPC198023
0.8281	Intermediate Similarity	NPC22786
0.8254	Intermediate Similarity	NPC147062
0.8254	Intermediate Similarity	NPC169110
0.8235	Intermediate Similarity	NPC72670
0.8209	Intermediate Similarity	NPC22760
0.8194	Intermediate Similarity	NPC255345
0.8182	Intermediate Similarity	NPC178527
0.8154	Intermediate Similarity	NPC45756
0.8116	Intermediate Similarity	NPC87099
0.8116	Intermediate Similarity	NPC226999
0.8116	Intermediate Similarity	NPC280135
0.8116	Intermediate Similarity	NPC193578
0.8116	Intermediate Similarity	NPC39799
0.8116	Intermediate Similarity	NPC1008
0.8116	Intermediate Similarity	NPC158028
0.8116	Intermediate Similarity	NPC135433
0.8095	Intermediate Similarity	NPC64270
0.8088	Intermediate Similarity	NPC297358
0.8088	Intermediate Similarity	NPC200936
0.8088	Intermediate Similarity	NPC473206
0.806	Intermediate Similarity	NPC267443
0.8	Intermediate Similarity	NPC200745
0.8	Intermediate Similarity	NPC54269
0.7887	Intermediate Similarity	NPC258492
0.7887	Intermediate Similarity	NPC96835
0.7879	Intermediate Similarity	NPC50266
0.7846	Intermediate Similarity	NPC45255
0.7778	Intermediate Similarity	NPC307195
0.7692	Intermediate Similarity	NPC147578
0.7671	Intermediate Similarity	NPC110264
0.7647	Intermediate Similarity	NPC36440
0.7576	Intermediate Similarity	NPC200624
0.7568	Intermediate Similarity	NPC249018
0.7568	Intermediate Similarity	NPC3190
0.75	Intermediate Similarity	NPC212463
0.7467	Intermediate Similarity	NPC245896
0.7467	Intermediate Similarity	NPC66270
0.7465	Intermediate Similarity	NPC229235
0.7429	Intermediate Similarity	NPC82770
0.7429	Intermediate Similarity	NPC239931
0.7429	Intermediate Similarity	NPC311343
0.7429	Intermediate Similarity	NPC78954
0.7368	Intermediate Similarity	NPC159661
0.7361	Intermediate Similarity	NPC74458
0.7361	Intermediate Similarity	NPC208302
0.7324	Intermediate Similarity	NPC98880
0.7324	Intermediate Similarity	NPC16190
0.7324	Intermediate Similarity	NPC5324
0.7324	Intermediate Similarity	NPC235059
0.7324	Intermediate Similarity	NPC169222
0.7288	Intermediate Similarity	NPC11150
0.7286	Intermediate Similarity	NPC52330
0.7273	Intermediate Similarity	NPC315216
0.7273	Intermediate Similarity	NPC50063
0.726	Intermediate Similarity	NPC271437
0.726	Intermediate Similarity	NPC244738
0.726	Intermediate Similarity	NPC285679
0.7222	Intermediate Similarity	NPC95289
0.7179	Intermediate Similarity	NPC242628
0.7162	Intermediate Similarity	NPC108218
0.7162	Intermediate Similarity	NPC122327
0.7162	Intermediate Similarity	NPC112609
0.7162	Intermediate Similarity	NPC208075
0.7162	Intermediate Similarity	NPC113000
0.7123	Intermediate Similarity	NPC155429
0.7123	Intermediate Similarity	NPC326200
0.7108	Intermediate Similarity	NPC113307
0.7105	Intermediate Similarity	NPC298023
0.7067	Intermediate Similarity	NPC189371
0.7067	Intermediate Similarity	NPC276699
0.7013	Intermediate Similarity	NPC103488
0.7013	Intermediate Similarity	NPC224544
0.7	Intermediate Similarity	NPC39600
0.7	Intermediate Similarity	NPC172984
0.7	Intermediate Similarity	NPC104070
0.6986	Remote Similarity	NPC219246
0.6974	Remote Similarity	NPC139658
0.6944	Remote Similarity	NPC181786
0.6914	Remote Similarity	NPC133162
0.6914	Remote Similarity	NPC267704
0.6883	Remote Similarity	NPC290638
0.6883	Remote Similarity	NPC9796
0.6883	Remote Similarity	NPC245966
0.6883	Remote Similarity	NPC325662
0.6883	Remote Similarity	NPC98269
0.6842	Remote Similarity	NPC206800
0.6842	Remote Similarity	NPC98976
0.6842	Remote Similarity	NPC32203
0.6835	Remote Similarity	NPC157055
0.6835	Remote Similarity	NPC285716
0.6835	Remote Similarity	NPC17408
0.6835	Remote Similarity	NPC328178
0.6795	Remote Similarity	NPC2785
0.6795	Remote Similarity	NPC36342
0.6795	Remote Similarity	NPC285470
0.6795	Remote Similarity	NPC76455
0.6795	Remote Similarity	NPC137847
0.679	Remote Similarity	NPC215008
0.6753	Remote Similarity	NPC271642
0.6753	Remote Similarity	NPC175393
0.675	Remote Similarity	NPC231986
0.675	Remote Similarity	NPC133050
0.6747	Remote Similarity	NPC160339
0.6747	Remote Similarity	NPC307
0.6747	Remote Similarity	NPC258046
0.6747	Remote Similarity	NPC243166
0.6744	Remote Similarity	NPC475059
0.6744	Remote Similarity	NPC475023
0.6711	Remote Similarity	NPC299134
0.6709	Remote Similarity	NPC300205
0.6709	Remote Similarity	NPC272260
0.6709	Remote Similarity	NPC139901
0.6709	Remote Similarity	NPC170484
0.6709	Remote Similarity	NPC151405
0.6667	Remote Similarity	NPC60408
0.6667	Remote Similarity	NPC179726
0.6667	Remote Similarity	NPC475057
0.6667	Remote Similarity	NPC287790
0.6667	Remote Similarity	NPC125144
0.6667	Remote Similarity	NPC121708
0.6667	Remote Similarity	NPC329318
0.6667	Remote Similarity	NPC3672
0.6667	Remote Similarity	NPC230068
0.6667	Remote Similarity	NPC43945
0.6667	Remote Similarity	NPC314690
0.6629	Remote Similarity	NPC21959
0.6625	Remote Similarity	NPC309279
0.6625	Remote Similarity	NPC184030
0.6625	Remote Similarity	NPC127343
0.6625	Remote Similarity	NPC477703
0.6625	Remote Similarity	NPC121800
0.6625	Remote Similarity	NPC164449
0.6625	Remote Similarity	NPC164086
0.6625	Remote Similarity	NPC190567
0.6625	Remote Similarity	NPC95868
0.6625	Remote Similarity	NPC192623
0.6625	Remote Similarity	NPC71664
0.6588	Remote Similarity	NPC157778
0.6588	Remote Similarity	NPC267262
0.6588	Remote Similarity	NPC153308
0.6582	Remote Similarity	NPC12857
0.6582	Remote Similarity	NPC50192
0.6582	Remote Similarity	NPC176228
0.6556	Remote Similarity	NPC202986
0.6548	Remote Similarity	NPC148231
0.6548	Remote Similarity	NPC164526
0.6543	Remote Similarity	NPC273033
0.6543	Remote Similarity	NPC12936
0.6543	Remote Similarity	NPC117180
0.6543	Remote Similarity	NPC145053
0.6538	Remote Similarity	NPC302129
0.6512	Remote Similarity	NPC418308
0.6512	Remote Similarity	NPC199567
0.6512	Remote Similarity	NPC325709
0.6512	Remote Similarity	NPC298115
0.6506	Remote Similarity	NPC95429
0.6506	Remote Similarity	NPC168855
0.65	Remote Similarity	NPC167577
0.65	Remote Similarity	NPC469894
0.65	Remote Similarity	NPC78517
0.6463	Remote Similarity	NPC329319
0.6463	Remote Similarity	NPC103387

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 NPC21211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	955
0.1-0.2	797
0.2-0.3	3009
0.3-0.4	2893
0.4-0.5	1050
0.5-0.6	323
0.6-0.7	105
0.7-0.8	15
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8438	Intermediate Similarity	NPD675	Discontinued
0.8358	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD1673	Approved
0.803	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD292	Approved
0.7361	Intermediate Similarity	NPD294	Approved
0.7273	Intermediate Similarity	NPD3903	Approved
0.7273	Intermediate Similarity	NPD3981	Approved
0.7273	Intermediate Similarity	NPD3979	Approved
0.7273	Intermediate Similarity	NPD3904	Approved
0.726	Intermediate Similarity	NPD9728	Phase 1
0.7162	Intermediate Similarity	NPD9592	Approved
0.7162	Intermediate Similarity	NPD9593	Approved
0.7162	Intermediate Similarity	NPD9588	Approved
0.7162	Intermediate Similarity	NPD9591	Approved
0.7162	Intermediate Similarity	NPD9589	Approved
0.7162	Intermediate Similarity	NPD9594	Approved
0.7162	Intermediate Similarity	NPD9590	Approved
0.7162	Intermediate Similarity	NPD505	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD80	Approved
0.7037	Intermediate Similarity	NPD9505	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD9564	Approved
0.7013	Intermediate Similarity	NPD79	Approved
0.7013	Intermediate Similarity	NPD9563	Approved
0.7	Intermediate Similarity	NPD3971	Phase 1
0.7	Intermediate Similarity	NPD4635	Approved
0.6923	Remote Similarity	NPD1475	Approved
0.6914	Remote Similarity	NPD4544	Approved
0.6914	Remote Similarity	NPD3429	Approved
0.6914	Remote Similarity	NPD3427	Approved
0.6883	Remote Similarity	NPD4147	Approved
0.6883	Remote Similarity	NPD4144	Approved
0.686	Remote Similarity	NPD1508	Approved
0.6842	Remote Similarity	NPD9716	Approved
0.6835	Remote Similarity	NPD260	Discontinued
0.6835	Remote Similarity	NPD1617	Discontinued
0.6824	Remote Similarity	NPD3344	Approved
0.6824	Remote Similarity	NPD3346	Approved
0.6795	Remote Similarity	NPD225	Approved
0.6795	Remote Similarity	NPD293	Approved
0.6795	Remote Similarity	NPD296	Approved
0.6795	Remote Similarity	NPD295	Approved
0.6795	Remote Similarity	NPD9393	Approved
0.6795	Remote Similarity	NPD227	Approved
0.6795	Remote Similarity	NPD9397	Approved
0.679	Remote Similarity	NPD423	Phase 3
0.6782	Remote Similarity	NPD735	Approved
0.6782	Remote Similarity	NPD736	Approved
0.675	Remote Similarity	NPD3035	Approved
0.6747	Remote Similarity	NPD4409	Approved
0.6747	Remote Similarity	NPD4406	Approved
0.6747	Remote Similarity	NPD3099	Discontinued
0.6709	Remote Similarity	NPD1052	Approved
0.6709	Remote Similarity	NPD589	Approved
0.6709	Remote Similarity	NPD590	Approved
0.6709	Remote Similarity	NPD1053	Approved
0.6709	Remote Similarity	NPD1051	Approved
0.6667	Remote Similarity	NPD4169	Approved
0.6667	Remote Similarity	NPD4170	Approved
0.6667	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3426	Approved
0.6667	Remote Similarity	NPD603	Approved
0.6667	Remote Similarity	NPD3428	Approved
0.6667	Remote Similarity	NPD650	Approved
0.6629	Remote Similarity	NPD1843	Approved
0.6625	Remote Similarity	NPD5372	Approved
0.6625	Remote Similarity	NPD914	Suspended
0.6625	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD5371	Approved
0.6588	Remote Similarity	NPD3345	Approved
0.6585	Remote Similarity	NPD1185	Approved
0.6585	Remote Similarity	NPD2001	Discontinued
0.6585	Remote Similarity	NPD4000	Phase 3
0.6585	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD713	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD1697	Approved
0.6543	Remote Similarity	NPD4027	Approved
0.6543	Remote Similarity	NPD472	Approved
0.6543	Remote Similarity	NPD4026	Approved
0.6543	Remote Similarity	NPD942	Approved
0.6543	Remote Similarity	NPD226	Approved
0.6506	Remote Similarity	NPD5178	Approved
0.65	Remote Similarity	NPD9490	Approved
0.65	Remote Similarity	NPD508	Approved
0.65	Remote Similarity	NPD507	Approved
0.6456	Remote Similarity	NPD9294	Approved
0.6444	Remote Similarity	NPD1738	Approved
0.6429	Remote Similarity	NPD2205	Approved
0.6429	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2208	Approved
0.6386	Remote Similarity	NPD831	Approved
0.6386	Remote Similarity	NPD9491	Approved
0.6386	Remote Similarity	NPD830	Approved
0.6386	Remote Similarity	NPD262	Approved
0.6386	Remote Similarity	NPD263	Approved
0.6364	Remote Similarity	NPD517	Discontinued
0.6364	Remote Similarity	NPD7609	Phase 3
0.6353	Remote Similarity	NPD4636	Approved
0.6322	Remote Similarity	NPD771	Phase 3
0.631	Remote Similarity	NPD9395	Approved
0.631	Remote Similarity	NPD2538	Approved
0.631	Remote Similarity	NPD785	Approved
0.631	Remote Similarity	NPD2539	Approved
0.6308	Remote Similarity	NPD9072	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4407	Approved
0.6292	Remote Similarity	NPD4405	Approved
0.6292	Remote Similarity	NPD4408	Approved
0.6292	Remote Similarity	NPD9361	Approved
0.6292	Remote Similarity	NPD7631	Approved
0.6279	Remote Similarity	NPD2002	Discontinued
0.6279	Remote Similarity	NPD1087	Approved
0.6279	Remote Similarity	NPD4145	Approved
0.6279	Remote Similarity	NPD4146	Approved
0.6277	Remote Similarity	NPD538	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5916	Discontinued
0.6222	Remote Similarity	NPD3980	Approved
0.6222	Remote Similarity	NPD4545	Approved
0.6222	Remote Similarity	NPD4542	Approved
0.6222	Remote Similarity	NPD2878	Approved
0.6222	Remote Similarity	NPD8	Approved
0.6222	Remote Similarity	NPD243	Approved
0.6222	Remote Similarity	NPD3982	Approved
0.6207	Remote Similarity	NPD1101	Approved
0.6207	Remote Similarity	NPD531	Approved
0.6207	Remote Similarity	NPD5675	Discontinued
0.619	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4543	Discontinued
0.6163	Remote Similarity	NPD305	Approved
0.6163	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD304	Approved
0.6154	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6049	Phase 2
0.6154	Remote Similarity	NPD1693	Approved
0.6154	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD9250	Approved
0.6136	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD782	Approved
0.6092	Remote Similarity	NPD780	Approved
0.6092	Remote Similarity	NPD783	Approved
0.6092	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD781	Approved
0.6092	Remote Similarity	NPD9538	Approved
0.6092	Remote Similarity	NPD4793	Discontinued
0.6087	Remote Similarity	NPD3457	Approved
0.6087	Remote Similarity	NPD3458	Approved
0.6087	Remote Similarity	NPD2005	Discontinued
0.6087	Remote Similarity	NPD2895	Discontinued
0.6087	Remote Similarity	NPD3456	Approved
0.6087	Remote Similarity	NPD3093	Approved
0.6067	Remote Similarity	NPD1086	Approved
0.6067	Remote Similarity	NPD5915	Approved
0.6067	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD1090	Approved
0.6067	Remote Similarity	NPD1089	Approved
0.6067	Remote Similarity	NPD3673	Approved
0.6067	Remote Similarity	NPD3672	Approved
0.6064	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD9488	Approved
0.6022	Remote Similarity	NPD3495	Discontinued
0.6022	Remote Similarity	NPD5597	Approved
0.6022	Remote Similarity	NPD5598	Approved
0.6022	Remote Similarity	NPD9489	Approved
0.6	Remote Similarity	NPD530	Approved
0.6	Remote Similarity	NPD1239	Approved
0.596	Remote Similarity	NPD5253	Approved
0.5957	Remote Similarity	NPD5832	Phase 3
0.5955	Remote Similarity	NPD1628	Approved
0.5955	Remote Similarity	NPD689	Discontinued
0.5955	Remote Similarity	NPD800	Approved
0.5955	Remote Similarity	NPD1629	Approved
0.5955	Remote Similarity	NPD5346	Phase 2
0.5955	Remote Similarity	NPD5347	Phase 2
0.5934	Remote Similarity	NPD752	Approved
0.5934	Remote Similarity	NPD1088	Approved
0.5914	Remote Similarity	NPD5963	Phase 2
0.5914	Remote Similarity	NPD5964	Phase 2
0.5909	Remote Similarity	NPD1282	Approved
0.5909	Remote Similarity	NPD187	Approved
0.59	Remote Similarity	NPD8010	Approved
0.59	Remote Similarity	NPD8009	Approved
0.5895	Remote Similarity	NPD524	Approved
0.5895	Remote Similarity	NPD523	Approved
0.5889	Remote Similarity	NPD4728	Approved
0.5876	Remote Similarity	NPD5765	Approved
0.5876	Remote Similarity	NPD3357	Discontinued
0.5876	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.587	Remote Similarity	NPD1409	Phase 3
0.587	Remote Similarity	NPD1563	Approved
0.587	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.587	Remote Similarity	NPD719	Approved
0.587	Remote Similarity	NPD720	Approved
0.587	Remote Similarity	NPD197	Approved
0.587	Remote Similarity	NPD845	Approved
0.587	Remote Similarity	NPD199	Approved
0.5862	Remote Similarity	NPD111	Approved
0.5843	Remote Similarity	NPD588	Approved
0.5843	Remote Similarity	NPD587	Approved
0.5833	Remote Similarity	NPD1916	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data