NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	221.99
Volume:	187.251
LogP:	3.129
LogD:	2.159
LogS:	-2.656
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.719
Synthetic Accessibility Score:	2.68
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.797
MDCK Permeability:	2.8780626962543465e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.222
Plasma Protein Binding (PPB):	98.9152603149414%
Volume Distribution (VD):	1.646
Pgp-substrate:	1.903206706047058%

ADMET: Metabolism

CYP1A2-inhibitor:	0.897
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.709
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.08
CYP2D6-substrate:	0.354
CYP3A4-inhibitor:	0.137
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	12.629
Half-life (T1/2):	0.75

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.233
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.33
Maximum Recommended Daily Dose:	0.277
Skin Sensitization:	0.928
Carcinogencity:	0.249
Eye Corrosion:	0.053
Eye Irritation:	0.951
Respiratory Toxicity:	0.7

Download Data

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

Natural Product: NPC475423

Natural Product ID:	NPC475423
*Common Name:**	2,4-Dichloro-3,6-Dihydroxy-5-Methoxytoluene
IUPAC Name:	2,6-dichloro-3-methoxy-5-methylbenzene-1,4-diol
Synonyms:
Standard InCHIKey:	RMPNTWNXWLLVAD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8Cl2O3/c1-3-4(9)7(12)5(10)8(13-2)6(3)11/h11-12H,1-2H3
SMILES:	COc1c(O)c(C)c(c(c1Cl)O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505351
PubChem CID:	10799094
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO18110	Lilium maximowiczii	Species	Liliaceae	Eukaryota	diseased bulbs	n.a.	n.a.	PMID[9677274]
NPO18110	Lilium maximowiczii	Species	Liliaceae	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

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5063	Organism	Bipolaris leersiae	Bipolaris leersiae	Inhibition	=	80.0	%	PMID[447730]

☑ 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 NPC475423 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	669
0.1-0.2	4005
0.2-0.3	15340
0.3-0.4	5862
0.4-0.5	6865
0.5-0.6	8358
0.6-0.7	1509
0.7-0.8	87
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7806	Intermediate Similarity	NPC56379
0.7558	Intermediate Similarity	NPC39409
0.7529	Intermediate Similarity	NPC195675
0.7518	Intermediate Similarity	NPC183446
0.7517	Intermediate Similarity	NPC258837
0.7517	Intermediate Similarity	NPC72636
0.7517	Intermediate Similarity	NPC45134
0.75	Intermediate Similarity	NPC246967
0.75	Intermediate Similarity	NPC135414
0.7485	Intermediate Similarity	NPC471811
0.7485	Intermediate Similarity	NPC471809
0.7429	Intermediate Similarity	NPC285289
0.7427	Intermediate Similarity	NPC471808
0.7427	Intermediate Similarity	NPC471814
0.7413	Intermediate Similarity	NPC112596
0.7413	Intermediate Similarity	NPC245060
0.7376	Intermediate Similarity	NPC474864
0.7361	Intermediate Similarity	NPC216836
0.7356	Intermediate Similarity	NPC121100
0.7314	Intermediate Similarity	NPC471806
0.7314	Intermediate Similarity	NPC471810
0.731	Intermediate Similarity	NPC19694
0.731	Intermediate Similarity	NPC266691
0.7294	Intermediate Similarity	NPC28160
0.7286	Intermediate Similarity	NPC67791
0.726	Intermediate Similarity	NPC10225
0.726	Intermediate Similarity	NPC58164
0.726	Intermediate Similarity	NPC45824
0.7257	Intermediate Similarity	NPC471805
0.7257	Intermediate Similarity	NPC471813
0.7246	Intermediate Similarity	NPC193067
0.7235	Intermediate Similarity	NPC175804
0.723	Intermediate Similarity	NPC139335
0.7216	Intermediate Similarity	NPC471807
0.7214	Intermediate Similarity	NPC20674
0.7211	Intermediate Similarity	NPC51840
0.7211	Intermediate Similarity	NPC214860
0.7211	Intermediate Similarity	NPC299221
0.7211	Intermediate Similarity	NPC311680
0.7211	Intermediate Similarity	NPC220935
0.7211	Intermediate Similarity	NPC234488
0.7203	Intermediate Similarity	NPC95168
0.7194	Intermediate Similarity	NPC259638
0.7172	Intermediate Similarity	NPC8058
0.7162	Intermediate Similarity	NPC474356
0.7162	Intermediate Similarity	NPC12275
0.7162	Intermediate Similarity	NPC82503
0.7162	Intermediate Similarity	NPC45715
0.7143	Intermediate Similarity	NPC246991
0.7143	Intermediate Similarity	NPC158477
0.7133	Intermediate Similarity	NPC270326
0.7114	Intermediate Similarity	NPC161203
0.7114	Intermediate Similarity	NPC6451
0.7103	Intermediate Similarity	NPC265483
0.7103	Intermediate Similarity	NPC60885
0.7103	Intermediate Similarity	NPC82483
0.7103	Intermediate Similarity	NPC234400
0.7103	Intermediate Similarity	NPC299584
0.7102	Intermediate Similarity	NPC471803
0.7102	Intermediate Similarity	NPC471804
0.7102	Intermediate Similarity	NPC471812
0.7083	Intermediate Similarity	NPC121115
0.7083	Intermediate Similarity	NPC220598
0.7083	Intermediate Similarity	NPC165375
0.7075	Intermediate Similarity	NPC63179
0.7071	Intermediate Similarity	NPC304208
0.7071	Intermediate Similarity	NPC52464
0.7067	Intermediate Similarity	NPC26673
0.7067	Intermediate Similarity	NPC105554
0.7067	Intermediate Similarity	NPC94236
0.7067	Intermediate Similarity	NPC37196
0.7063	Intermediate Similarity	NPC75713
0.7063	Intermediate Similarity	NPC49341
0.7059	Intermediate Similarity	NPC188618
0.7059	Intermediate Similarity	NPC43411
0.7055	Intermediate Similarity	NPC223136
0.7055	Intermediate Similarity	NPC214406
0.7055	Intermediate Similarity	NPC44748
0.7055	Intermediate Similarity	NPC78974
0.7055	Intermediate Similarity	NPC476006
0.7055	Intermediate Similarity	NPC103823
0.7055	Intermediate Similarity	NPC18924
0.7055	Intermediate Similarity	NPC28730
0.7051	Intermediate Similarity	NPC200207
0.7047	Intermediate Similarity	NPC193334
0.7047	Intermediate Similarity	NPC232275
0.7042	Intermediate Similarity	NPC229401
0.7027	Intermediate Similarity	NPC190144
0.7021	Intermediate Similarity	NPC474612
0.702	Intermediate Similarity	NPC103967
0.702	Intermediate Similarity	NPC106215
0.7007	Intermediate Similarity	NPC324112
0.7007	Intermediate Similarity	NPC246620
0.7007	Intermediate Similarity	NPC266555
0.7007	Intermediate Similarity	NPC74817
0.7007	Intermediate Similarity	NPC236791
0.7007	Intermediate Similarity	NPC50368
0.7007	Intermediate Similarity	NPC282000
0.7007	Intermediate Similarity	NPC293054
0.7007	Intermediate Similarity	NPC169474
0.7007	Intermediate Similarity	NPC236760
0.7007	Intermediate Similarity	NPC124452
0.7007	Intermediate Similarity	NPC159968
0.7007	Intermediate Similarity	NPC82679
0.698	Remote Similarity	NPC192687
0.698	Remote Similarity	NPC224157
0.698	Remote Similarity	NPC229231
0.6974	Remote Similarity	NPC134968
0.6974	Remote Similarity	NPC281521
0.6974	Remote Similarity	NPC261873
0.6974	Remote Similarity	NPC472337
0.6974	Remote Similarity	NPC255147
0.6974	Remote Similarity	NPC283009
0.6974	Remote Similarity	NPC201357
0.6972	Remote Similarity	NPC308217
0.6959	Remote Similarity	NPC154866
0.6959	Remote Similarity	NPC28765
0.6954	Remote Similarity	NPC474810
0.6933	Remote Similarity	NPC147317
0.6928	Remote Similarity	NPC472334
0.6928	Remote Similarity	NPC472336
0.6928	Remote Similarity	NPC82271
0.6928	Remote Similarity	NPC126682
0.6923	Remote Similarity	NPC232084
0.6923	Remote Similarity	NPC247364
0.6923	Remote Similarity	NPC10932
0.6923	Remote Similarity	NPC61516
0.6918	Remote Similarity	NPC5796
0.6918	Remote Similarity	NPC33402
0.6918	Remote Similarity	NPC206487
0.6912	Remote Similarity	NPC187958
0.6897	Remote Similarity	NPC71579
0.6897	Remote Similarity	NPC262253
0.6897	Remote Similarity	NPC41562
0.6897	Remote Similarity	NPC473411
0.6892	Remote Similarity	NPC252131
0.6887	Remote Similarity	NPC86655
0.6887	Remote Similarity	NPC127624
0.6887	Remote Similarity	NPC202762
0.6887	Remote Similarity	NPC218884
0.6884	Remote Similarity	NPC195873
0.6883	Remote Similarity	NPC474282
0.6883	Remote Similarity	NPC20511
0.6883	Remote Similarity	NPC102904
0.6883	Remote Similarity	NPC103976
0.6883	Remote Similarity	NPC176051
0.6883	Remote Similarity	NPC276490
0.6883	Remote Similarity	NPC95162
0.6883	Remote Similarity	NPC139548
0.6883	Remote Similarity	NPC6262
0.6883	Remote Similarity	NPC52086
0.6883	Remote Similarity	NPC90615
0.6883	Remote Similarity	NPC76336
0.6883	Remote Similarity	NPC272157
0.6883	Remote Similarity	NPC148835
0.6883	Remote Similarity	NPC73535
0.6883	Remote Similarity	NPC201145
0.6883	Remote Similarity	NPC326797
0.6883	Remote Similarity	NPC107551
0.6883	Remote Similarity	NPC25111
0.6875	Remote Similarity	NPC205213
0.6871	Remote Similarity	NPC251855
0.6871	Remote Similarity	NPC17943
0.6871	Remote Similarity	NPC221077
0.6871	Remote Similarity	NPC208950
0.6871	Remote Similarity	NPC105925
0.6871	Remote Similarity	NPC472093
0.6871	Remote Similarity	NPC117214
0.6871	Remote Similarity	NPC116907
0.6871	Remote Similarity	NPC475169
0.6871	Remote Similarity	NPC193544
0.6871	Remote Similarity	NPC57490
0.6871	Remote Similarity	NPC233410
0.6871	Remote Similarity	NPC298757
0.6871	Remote Similarity	NPC203133
0.6867	Remote Similarity	NPC126836
0.6863	Remote Similarity	NPC252095
0.6853	Remote Similarity	NPC226629
0.6849	Remote Similarity	NPC197757
0.6849	Remote Similarity	NPC238810
0.6849	Remote Similarity	NPC228922
0.6842	Remote Similarity	NPC229442
0.6842	Remote Similarity	NPC168059
0.6842	Remote Similarity	NPC269528
0.6839	Remote Similarity	NPC245207
0.6839	Remote Similarity	NPC319647
0.6839	Remote Similarity	NPC108278
0.6839	Remote Similarity	NPC127218
0.6839	Remote Similarity	NPC30951
0.6839	Remote Similarity	NPC13067
0.6839	Remote Similarity	NPC6369
0.6839	Remote Similarity	NPC212942
0.6839	Remote Similarity	NPC19869
0.6839	Remote Similarity	NPC25966
0.6839	Remote Similarity	NPC29868
0.6839	Remote Similarity	NPC292882
0.6839	Remote Similarity	NPC79622
0.6828	Remote Similarity	NPC145780
0.6824	Remote Similarity	NPC76451
0.6824	Remote Similarity	NPC223953

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 NPC475423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	547
0.1-0.2	1630
0.2-0.3	3287
0.3-0.4	2134
0.4-0.5	1175
0.5-0.6	356
0.6-0.7	21
0.7-0.8	0
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
0.6875	Remote Similarity	NPD915	Approved
0.6813	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3027	Phase 3
0.6779	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1715	Phase 1
0.6748	Remote Similarity	NPD1714	Approved
0.6733	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1613	Approved
0.6667	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD228	Approved
0.6443	Remote Similarity	NPD1157	Approved
0.634	Remote Similarity	NPD3018	Phase 2
0.6329	Remote Similarity	NPD4538	Approved
0.6329	Remote Similarity	NPD4536	Approved
0.6329	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD1653	Approved
0.6325	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1184	Approved
0.6235	Remote Similarity	NPD2801	Approved
0.6188	Remote Similarity	NPD5960	Phase 3
0.6188	Remote Similarity	NPD5588	Approved
0.6187	Remote Similarity	NPD9500	Approved
0.6184	Remote Similarity	NPD4749	Approved
0.6184	Remote Similarity	NPD2983	Phase 2
0.6184	Remote Similarity	NPD2982	Phase 2
0.6121	Remote Similarity	NPD5058	Phase 3
0.6118	Remote Similarity	NPD2981	Phase 2
0.6107	Remote Similarity	NPD1548	Phase 1
0.6096	Remote Similarity	NPD1398	Phase 1
0.6082	Remote Similarity	NPD1934	Approved
0.6065	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD1610	Phase 2
0.6037	Remote Similarity	NPD1416	Approved
0.6014	Remote Similarity	NPD6671	Approved
0.6014	Remote Similarity	NPD290	Approved
0.6013	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD2403	Approved
0.6	Remote Similarity	NPD230	Phase 1
0.6	Remote Similarity	NPD1718	Discontinued
0.5988	Remote Similarity	NPD1511	Approved
0.5974	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD7340	Approved
0.5964	Remote Similarity	NPD2219	Phase 1
0.5949	Remote Similarity	NPD4625	Phase 3
0.5948	Remote Similarity	NPD422	Phase 1
0.5948	Remote Similarity	NPD1091	Approved
0.5938	Remote Similarity	NPD1558	Phase 1
0.5935	Remote Similarity	NPD6696	Suspended
0.5921	Remote Similarity	NPD4589	Approved
0.5917	Remote Similarity	NPD1512	Approved
0.5915	Remote Similarity	NPD3540	Phase 1
0.5912	Remote Similarity	NPD9296	Approved
0.5904	Remote Similarity	NPD4535	Phase 3
0.5903	Remote Similarity	NPD9552	Approved
0.5902	Remote Similarity	NPD3303	Discontinued
0.5886	Remote Similarity	NPD3882	Suspended
0.5886	Remote Similarity	NPD4908	Phase 1
0.5862	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.5858	Remote Similarity	NPD1578	Phase 2
0.5855	Remote Similarity	NPD1357	Approved
0.5854	Remote Similarity	NPD3539	Phase 1
0.5844	Remote Similarity	NPD3705	Approved
0.5839	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD968	Approved
0.5823	Remote Similarity	NPD9494	Approved
0.5823	Remote Similarity	NPD2861	Phase 2
0.5823	Remote Similarity	NPD454	Approved
0.5822	Remote Similarity	NPD4750	Phase 3
0.5819	Remote Similarity	NPD6234	Discontinued
0.5813	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD9501	Approved
0.5802	Remote Similarity	NPD447	Suspended
0.5795	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD2674	Phase 3
0.5775	Remote Similarity	NPD846	Approved
0.5775	Remote Similarity	NPD940	Approved
0.5772	Remote Similarity	NPD5283	Phase 1
0.5771	Remote Similarity	NPD1465	Phase 2
0.5758	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.5749	Remote Similarity	NPD6674	Discontinued
0.5747	Remote Similarity	NPD958	Approved
0.5746	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD6166	Phase 2
0.5746	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD3620	Phase 2
0.5741	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD4873	Discontinued
0.5732	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD6111	Discontinued
0.5729	Remote Similarity	NPD6312	Discontinued
0.5714	Remote Similarity	NPD37	Approved
0.5714	Remote Similarity	NPD3145	Approved
0.5714	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3144	Approved
0.5706	Remote Similarity	NPD4357	Discontinued
0.5704	Remote Similarity	NPD1242	Phase 1
0.5704	Remote Similarity	NPD289	Clinical (unspecified phase)
0.5695	Remote Similarity	NPD9685	Approved
0.569	Remote Similarity	NPD4678	Approved
0.569	Remote Similarity	NPD4675	Approved
0.5689	Remote Similarity	NPD970	Clinical (unspecified phase)
0.5687	Remote Similarity	NPD600	Approved
0.5687	Remote Similarity	NPD596	Approved
0.5677	Remote Similarity	NPD3496	Discontinued
0.5663	Remote Similarity	NPD6100	Approved
0.5663	Remote Similarity	NPD6099	Approved
0.5658	Remote Similarity	NPD694	Clinical (unspecified phase)
0.5655	Remote Similarity	NPD5177	Phase 3
0.5652	Remote Similarity	NPD7054	Approved
0.565	Remote Similarity	NPD3817	Phase 2
0.5644	Remote Similarity	NPD1555	Discontinued
0.5644	Remote Similarity	NPD1240	Approved
0.5635	Remote Similarity	NPD6232	Discontinued
0.5632	Remote Similarity	NPD6057	Approved
0.5632	Remote Similarity	NPD6056	Approved
0.5622	Remote Similarity	NPD7472	Approved
0.5622	Remote Similarity	NPD7074	Phase 3
0.5618	Remote Similarity	NPD4965	Approved
0.5618	Remote Similarity	NPD4967	Phase 2
0.5618	Remote Similarity	NPD4966	Approved
0.5615	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD7041	Phase 2
0.5614	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.5613	Remote Similarity	NPD1778	Approved
0.5611	Remote Similarity	NPD3365	Discontinued
0.56	Remote Similarity	NPD4972	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