NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	116.06
Volume:	136.562
LogP:	2.927
LogD:	2.698
LogS:	-3.157
# 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:	0.487
Synthetic Accessibility Score:	2.226
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.53
MDCK Permeability:	3.2316704164259136e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.879
Plasma Protein Binding (PPB):	94.97627258300781%
Volume Distribution (VD):	2.543
Pgp-substrate:	5.387722969055176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.861
CYP2C19-inhibitor:	0.682
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.138
CYP2C9-substrate:	0.828
CYP2D6-inhibitor:	0.104
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	11.406
Half-life (T1/2):	0.711

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.402
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.343
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.351
Skin Sensitization:	0.946
Carcinogencity:	0.341
Eye Corrosion:	0.577
Eye Irritation:	0.988
Respiratory Toxicity:	0.729

Download Data

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

Natural Product: NPC66517

Natural Product ID:	NPC66517
*Common Name:**	Indene
IUPAC Name:	1H-indene
Synonyms:	1H-Indene
Standard InCHIKey:	YBYIRNPNPLQARY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
SMILES:	c1ccc2CC=Cc2c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL192812
PubChem CID:	7219
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000021] Indenes and isoindenes

*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
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12126.1	Coix lacryma- jobi var. ma - yuen	Varieties	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18046	Mosla chinensis	Species	Lamiaceae	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
Kd	1
Others	1
Potency	4

Activity Type	# Activity
Individual Protein	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1066	Individual Protein	Lysozyme	Enterobacteria phage T4	Kd	=	193000.0	nM	PMID[522530]
NPT2	Others	Unspecified		log1/Ki	=	3.67	n.a.	PMID[522532]
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	5448.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24541.2	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 NPC66517 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	1321
0.1-0.2	4374
0.2-0.3	15930
0.3-0.4	15516
0.4-0.5	4317
0.5-0.6	888
0.6-0.7	226
0.7-0.8	60
0.8-0.85	30
0.85-0.9	24
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC21211
0.9492	High Similarity	NPC310758
0.9492	High Similarity	NPC238023
0.9333	High Similarity	NPC71009
0.9138	High Similarity	NPC198841
0.9032	High Similarity	NPC155172
0.9032	High Similarity	NPC291066
0.8983	High Similarity	NPC212114
0.8983	High Similarity	NPC65873
0.8983	High Similarity	NPC300345
0.8983	High Similarity	NPC120441
0.8966	High Similarity	NPC149436
0.8923	High Similarity	NPC251490
0.8852	High Similarity	NPC135924
0.8814	High Similarity	NPC269586
0.875	High Similarity	NPC6107
0.871	High Similarity	NPC29680
0.8644	High Similarity	NPC277704
0.8636	High Similarity	NPC263385
0.8594	High Similarity	NPC289915
0.8594	High Similarity	NPC113837
0.8571	High Similarity	NPC113670
0.8571	High Similarity	NPC88566
0.8548	High Similarity	NPC150196
0.8548	High Similarity	NPC54368
0.8548	High Similarity	NPC248705
0.8548	High Similarity	NPC210849
0.8548	High Similarity	NPC246588
0.8525	High Similarity	NPC8235
0.8525	High Similarity	NPC36357
0.8525	High Similarity	NPC114327
0.8485	Intermediate Similarity	NPC246822
0.8485	Intermediate Similarity	NPC139416
0.8485	Intermediate Similarity	NPC213570
0.8438	Intermediate Similarity	NPC32312
0.8438	Intermediate Similarity	NPC198023
0.8413	Intermediate Similarity	NPC22786
0.8387	Intermediate Similarity	NPC147062
0.8387	Intermediate Similarity	NPC169110
0.8382	Intermediate Similarity	NPC1901
0.8358	Intermediate Similarity	NPC72670
0.8308	Intermediate Similarity	NPC178527
0.8281	Intermediate Similarity	NPC45756
0.8235	Intermediate Similarity	NPC280135
0.8235	Intermediate Similarity	NPC158028
0.8235	Intermediate Similarity	NPC193578
0.8235	Intermediate Similarity	NPC87099
0.8235	Intermediate Similarity	NPC226999
0.8235	Intermediate Similarity	NPC1008
0.8235	Intermediate Similarity	NPC39799
0.8235	Intermediate Similarity	NPC135433
0.8226	Intermediate Similarity	NPC64270
0.8209	Intermediate Similarity	NPC200936
0.8209	Intermediate Similarity	NPC473206
0.8182	Intermediate Similarity	NPC267443
0.8154	Intermediate Similarity	NPC264470
0.8125	Intermediate Similarity	NPC200745
0.8116	Intermediate Similarity	NPC54269
0.8	Intermediate Similarity	NPC258492
0.8	Intermediate Similarity	NPC96835
0.8	Intermediate Similarity	NPC50266
0.7969	Intermediate Similarity	NPC45255
0.7887	Intermediate Similarity	NPC307195
0.7812	Intermediate Similarity	NPC147578
0.7808	Intermediate Similarity	NPC255345
0.7794	Intermediate Similarity	NPC22760
0.7778	Intermediate Similarity	NPC110264
0.7761	Intermediate Similarity	NPC36440
0.7692	Intermediate Similarity	NPC200624
0.7681	Intermediate Similarity	NPC297358
0.7671	Intermediate Similarity	NPC249018
0.7671	Intermediate Similarity	NPC3190
0.7606	Intermediate Similarity	NPC212463
0.7571	Intermediate Similarity	NPC229235
0.7568	Intermediate Similarity	NPC66270
0.7568	Intermediate Similarity	NPC245896
0.7536	Intermediate Similarity	NPC239931
0.7536	Intermediate Similarity	NPC311343
0.7536	Intermediate Similarity	NPC78954
0.7536	Intermediate Similarity	NPC82770
0.7467	Intermediate Similarity	NPC159661
0.7465	Intermediate Similarity	NPC74458
0.7465	Intermediate Similarity	NPC208302
0.7429	Intermediate Similarity	NPC16190
0.7429	Intermediate Similarity	NPC169222
0.7429	Intermediate Similarity	NPC5324
0.7429	Intermediate Similarity	NPC98880
0.7429	Intermediate Similarity	NPC235059
0.7414	Intermediate Similarity	NPC11150
0.7391	Intermediate Similarity	NPC52330
0.7368	Intermediate Similarity	NPC315216
0.7368	Intermediate Similarity	NPC50063
0.7361	Intermediate Similarity	NPC271437
0.7361	Intermediate Similarity	NPC244738
0.7361	Intermediate Similarity	NPC285679
0.7324	Intermediate Similarity	NPC95289
0.7273	Intermediate Similarity	NPC242628
0.726	Intermediate Similarity	NPC112609
0.726	Intermediate Similarity	NPC122327
0.726	Intermediate Similarity	NPC108218
0.726	Intermediate Similarity	NPC208075
0.726	Intermediate Similarity	NPC113000
0.7222	Intermediate Similarity	NPC155429
0.7222	Intermediate Similarity	NPC326200
0.72	Intermediate Similarity	NPC298023
0.7162	Intermediate Similarity	NPC276699
0.7162	Intermediate Similarity	NPC189371
0.7105	Intermediate Similarity	NPC103488
0.7105	Intermediate Similarity	NPC224544
0.7089	Intermediate Similarity	NPC172984
0.7089	Intermediate Similarity	NPC104070
0.7089	Intermediate Similarity	NPC39600
0.7083	Intermediate Similarity	NPC219246
0.7067	Intermediate Similarity	NPC139658
0.7042	Intermediate Similarity	NPC181786
0.7	Intermediate Similarity	NPC267704
0.7	Intermediate Similarity	NPC133162
0.6974	Remote Similarity	NPC245966
0.6974	Remote Similarity	NPC290638
0.6974	Remote Similarity	NPC98269
0.6974	Remote Similarity	NPC325662
0.6974	Remote Similarity	NPC9796
0.6933	Remote Similarity	NPC206800
0.6933	Remote Similarity	NPC98976
0.6933	Remote Similarity	NPC32203
0.6923	Remote Similarity	NPC285716
0.6923	Remote Similarity	NPC328178
0.6923	Remote Similarity	NPC157055
0.6923	Remote Similarity	NPC17408
0.6883	Remote Similarity	NPC137847
0.6883	Remote Similarity	NPC2785
0.6883	Remote Similarity	NPC285470
0.6883	Remote Similarity	NPC76455
0.6883	Remote Similarity	NPC36342
0.6875	Remote Similarity	NPC215008
0.6842	Remote Similarity	NPC175393
0.6842	Remote Similarity	NPC271642
0.6835	Remote Similarity	NPC133050
0.6835	Remote Similarity	NPC231986
0.6829	Remote Similarity	NPC307
0.6829	Remote Similarity	NPC160339
0.6829	Remote Similarity	NPC258046
0.68	Remote Similarity	NPC299134
0.6795	Remote Similarity	NPC300205
0.6795	Remote Similarity	NPC272260
0.6795	Remote Similarity	NPC139901
0.6795	Remote Similarity	NPC151405
0.6795	Remote Similarity	NPC170484
0.6786	Remote Similarity	NPC113307
0.6757	Remote Similarity	NPC121708
0.6757	Remote Similarity	NPC125144
0.6753	Remote Similarity	NPC287790
0.6753	Remote Similarity	NPC179726
0.6753	Remote Similarity	NPC329318
0.6753	Remote Similarity	NPC3672
0.675	Remote Similarity	NPC230068
0.6747	Remote Similarity	NPC60408
0.6747	Remote Similarity	NPC43945
0.6744	Remote Similarity	NPC314690
0.6709	Remote Similarity	NPC184030
0.6709	Remote Similarity	NPC477703
0.6709	Remote Similarity	NPC192623
0.6709	Remote Similarity	NPC121800
0.6709	Remote Similarity	NPC190567
0.6709	Remote Similarity	NPC95868
0.6709	Remote Similarity	NPC164449
0.6709	Remote Similarity	NPC309279
0.6709	Remote Similarity	NPC164086
0.6709	Remote Similarity	NPC71664
0.6709	Remote Similarity	NPC127343
0.6667	Remote Similarity	NPC176228
0.6667	Remote Similarity	NPC153308
0.6667	Remote Similarity	NPC50192
0.6667	Remote Similarity	NPC267262
0.6667	Remote Similarity	NPC12857
0.6667	Remote Similarity	NPC157778
0.6627	Remote Similarity	NPC164526
0.6627	Remote Similarity	NPC148231
0.6627	Remote Similarity	NPC243166
0.6625	Remote Similarity	NPC117180
0.6625	Remote Similarity	NPC12936
0.6625	Remote Similarity	NPC145053
0.6625	Remote Similarity	NPC273033
0.6623	Remote Similarity	NPC302129
0.6588	Remote Similarity	NPC418308
0.6588	Remote Similarity	NPC298115
0.6588	Remote Similarity	NPC199567
0.6588	Remote Similarity	NPC325709
0.6585	Remote Similarity	NPC95429
0.6585	Remote Similarity	NPC168855
0.6582	Remote Similarity	NPC78517
0.6582	Remote Similarity	NPC469894
0.6582	Remote Similarity	NPC167577
0.6543	Remote Similarity	NPC323103
0.6543	Remote Similarity	NPC329319
0.6543	Remote Similarity	NPC121478
0.6543	Remote Similarity	NPC103326
0.6543	Remote Similarity	NPC87299
0.6543	Remote Similarity	NPC283012
0.6543	Remote Similarity	NPC99394

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 NPC66517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	941
0.1-0.2	807
0.2-0.3	2972
0.3-0.4	2873
0.4-0.5	1094
0.5-0.6	325
0.6-0.7	117
0.7-0.8	17
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD675	Discontinued
0.8485	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD1673	Approved
0.7465	Intermediate Similarity	NPD294	Approved
0.7465	Intermediate Similarity	NPD292	Approved
0.7368	Intermediate Similarity	NPD3904	Approved
0.7368	Intermediate Similarity	NPD3979	Approved
0.7368	Intermediate Similarity	NPD3981	Approved
0.7368	Intermediate Similarity	NPD3903	Approved
0.7361	Intermediate Similarity	NPD9728	Phase 1
0.726	Intermediate Similarity	NPD9590	Approved
0.726	Intermediate Similarity	NPD9592	Approved
0.726	Intermediate Similarity	NPD9594	Approved
0.726	Intermediate Similarity	NPD80	Approved
0.726	Intermediate Similarity	NPD505	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD9593	Approved
0.726	Intermediate Similarity	NPD9588	Approved
0.726	Intermediate Similarity	NPD9591	Approved
0.726	Intermediate Similarity	NPD9589	Approved
0.7125	Intermediate Similarity	NPD9505	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD9563	Approved
0.7105	Intermediate Similarity	NPD79	Approved
0.7105	Intermediate Similarity	NPD9564	Approved
0.7089	Intermediate Similarity	NPD4635	Approved
0.7089	Intermediate Similarity	NPD3971	Phase 1
0.7013	Intermediate Similarity	NPD1475	Approved
0.7	Intermediate Similarity	NPD4544	Approved
0.7	Intermediate Similarity	NPD3429	Approved
0.7	Intermediate Similarity	NPD3427	Approved
0.6974	Remote Similarity	NPD4144	Approved
0.6974	Remote Similarity	NPD4147	Approved
0.6933	Remote Similarity	NPD9716	Approved
0.6923	Remote Similarity	NPD1617	Discontinued
0.6923	Remote Similarity	NPD260	Discontinued
0.6905	Remote Similarity	NPD3344	Approved
0.6905	Remote Similarity	NPD3346	Approved
0.6883	Remote Similarity	NPD293	Approved
0.6883	Remote Similarity	NPD295	Approved
0.6883	Remote Similarity	NPD227	Approved
0.6883	Remote Similarity	NPD9397	Approved
0.6883	Remote Similarity	NPD225	Approved
0.6883	Remote Similarity	NPD9393	Approved
0.6883	Remote Similarity	NPD296	Approved
0.6875	Remote Similarity	NPD423	Phase 3
0.6835	Remote Similarity	NPD3035	Approved
0.6829	Remote Similarity	NPD4406	Approved
0.6829	Remote Similarity	NPD3099	Discontinued
0.6829	Remote Similarity	NPD4409	Approved
0.6795	Remote Similarity	NPD589	Approved
0.6795	Remote Similarity	NPD1051	Approved
0.6795	Remote Similarity	NPD1053	Approved
0.6795	Remote Similarity	NPD1052	Approved
0.6795	Remote Similarity	NPD590	Approved
0.6753	Remote Similarity	NPD603	Approved
0.675	Remote Similarity	NPD4169	Approved
0.675	Remote Similarity	NPD4170	Approved
0.675	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3428	Approved
0.6747	Remote Similarity	NPD3426	Approved
0.6747	Remote Similarity	NPD650	Approved
0.6709	Remote Similarity	NPD5371	Approved
0.6709	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5372	Approved
0.6709	Remote Similarity	NPD914	Suspended
0.6667	Remote Similarity	NPD4000	Phase 3
0.6667	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3345	Approved
0.6667	Remote Similarity	NPD1185	Approved
0.6667	Remote Similarity	NPD2001	Discontinued
0.6625	Remote Similarity	NPD942	Approved
0.6625	Remote Similarity	NPD4026	Approved
0.6625	Remote Similarity	NPD4027	Approved
0.6625	Remote Similarity	NPD472	Approved
0.6625	Remote Similarity	NPD226	Approved
0.6585	Remote Similarity	NPD5178	Approved
0.6582	Remote Similarity	NPD9490	Approved
0.6582	Remote Similarity	NPD507	Approved
0.6582	Remote Similarity	NPD508	Approved
0.6552	Remote Similarity	NPD1508	Approved
0.6538	Remote Similarity	NPD9294	Approved
0.6506	Remote Similarity	NPD2208	Approved
0.6506	Remote Similarity	NPD2205	Approved
0.6506	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD736	Approved
0.6477	Remote Similarity	NPD735	Approved
0.6463	Remote Similarity	NPD830	Approved
0.6463	Remote Similarity	NPD831	Approved
0.6463	Remote Similarity	NPD9491	Approved
0.6463	Remote Similarity	NPD262	Approved
0.6463	Remote Similarity	NPD263	Approved
0.6437	Remote Similarity	NPD7609	Phase 3
0.6437	Remote Similarity	NPD517	Discontinued
0.6437	Remote Similarity	NPD4543	Discontinued
0.6429	Remote Similarity	NPD4636	Approved
0.6406	Remote Similarity	NPD9072	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD771	Phase 3
0.6386	Remote Similarity	NPD785	Approved
0.6386	Remote Similarity	NPD2538	Approved
0.6386	Remote Similarity	NPD9395	Approved
0.6386	Remote Similarity	NPD2539	Approved
0.6364	Remote Similarity	NPD4407	Approved
0.6364	Remote Similarity	NPD9361	Approved
0.6364	Remote Similarity	NPD4408	Approved
0.6364	Remote Similarity	NPD4405	Approved
0.6364	Remote Similarity	NPD7631	Approved
0.6353	Remote Similarity	NPD4146	Approved
0.6353	Remote Similarity	NPD2002	Discontinued
0.6353	Remote Similarity	NPD1087	Approved
0.6353	Remote Similarity	NPD4145	Approved
0.6333	Remote Similarity	NPD1843	Approved
0.6322	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5916	Discontinued
0.6292	Remote Similarity	NPD243	Approved
0.6292	Remote Similarity	NPD3982	Approved
0.6292	Remote Similarity	NPD4545	Approved
0.6292	Remote Similarity	NPD2878	Approved
0.6292	Remote Similarity	NPD3980	Approved
0.6292	Remote Similarity	NPD8	Approved
0.6292	Remote Similarity	NPD4542	Approved
0.6279	Remote Similarity	NPD1101	Approved
0.6279	Remote Similarity	NPD531	Approved
0.6279	Remote Similarity	NPD5675	Discontinued
0.6265	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD713	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD1697	Approved
0.6235	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD305	Approved
0.6235	Remote Similarity	NPD304	Approved
0.6222	Remote Similarity	NPD6049	Phase 2
0.6222	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD688	Clinical (unspecified phase)
0.622	Remote Similarity	NPD9250	Approved
0.6207	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD782	Approved
0.6163	Remote Similarity	NPD783	Approved
0.6163	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD9538	Approved
0.6163	Remote Similarity	NPD781	Approved
0.6163	Remote Similarity	NPD780	Approved
0.6163	Remote Similarity	NPD4793	Discontinued
0.6154	Remote Similarity	NPD2005	Discontinued
0.6154	Remote Similarity	NPD3457	Approved
0.6154	Remote Similarity	NPD3458	Approved
0.6154	Remote Similarity	NPD3093	Approved
0.6154	Remote Similarity	NPD2895	Discontinued
0.6154	Remote Similarity	NPD1738	Approved
0.6154	Remote Similarity	NPD3456	Approved
0.6136	Remote Similarity	NPD3672	Approved
0.6136	Remote Similarity	NPD3673	Approved
0.6136	Remote Similarity	NPD1090	Approved
0.6136	Remote Similarity	NPD1089	Approved
0.6136	Remote Similarity	NPD1086	Approved
0.6136	Remote Similarity	NPD5915	Approved
0.6129	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5597	Approved
0.6087	Remote Similarity	NPD9488	Approved
0.6087	Remote Similarity	NPD3495	Discontinued
0.6087	Remote Similarity	NPD5598	Approved
0.6087	Remote Similarity	NPD9489	Approved
0.6087	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD530	Approved
0.6067	Remote Similarity	NPD1239	Approved
0.6044	Remote Similarity	NPD1693	Approved
0.6023	Remote Similarity	NPD800	Approved
0.6023	Remote Similarity	NPD1628	Approved
0.6023	Remote Similarity	NPD1629	Approved
0.6023	Remote Similarity	NPD689	Discontinued
0.6023	Remote Similarity	NPD5346	Phase 2
0.6023	Remote Similarity	NPD5347	Phase 2
0.6022	Remote Similarity	NPD5832	Phase 3
0.6	Remote Similarity	NPD752	Approved
0.6	Remote Similarity	NPD1088	Approved
0.6	Remote Similarity	NPD538	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3832	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD5963	Phase 2
0.5978	Remote Similarity	NPD5964	Phase 2
0.5977	Remote Similarity	NPD187	Approved
0.5977	Remote Similarity	NPD1282	Approved
0.5957	Remote Similarity	NPD524	Approved
0.5957	Remote Similarity	NPD523	Approved
0.5955	Remote Similarity	NPD4728	Approved
0.5938	Remote Similarity	NPD3357	Discontinued
0.5934	Remote Similarity	NPD1563	Approved
0.5934	Remote Similarity	NPD719	Approved
0.5934	Remote Similarity	NPD845	Approved
0.5934	Remote Similarity	NPD720	Approved
0.5934	Remote Similarity	NPD199	Approved
0.5934	Remote Similarity	NPD1409	Phase 3
0.5934	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD197	Approved
0.593	Remote Similarity	NPD111	Approved
0.5909	Remote Similarity	NPD588	Approved
0.5909	Remote Similarity	NPD587	Approved
0.5895	Remote Similarity	NPD1916	Discontinued
0.5895	Remote Similarity	NPD6354	Discontinued
0.5895	Remote Similarity	NPD5630	Phase 1
0.5889	Remote Similarity	NPD3000	Approved
0.5889	Remote Similarity	NPD2998	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