NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.09
Volume:	214.871
LogP:	2.867
LogD:	1.787
LogS:	-2.526
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	2.295
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.74
MDCK Permeability:	1.6634152416372672e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.126
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.296
Plasma Protein Binding (PPB):	96.8366470336914%
Volume Distribution (VD):	0.548
Pgp-substrate:	2.8851418495178223%

ADMET: Metabolism

CYP1A2-inhibitor:	0.914
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.733
CYP2C9-inhibitor:	0.193
CYP2C9-substrate:	0.675
CYP2D6-inhibitor:	0.1
CYP2D6-substrate:	0.378
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	14.399
Half-life (T1/2):	0.818

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.338
AMES Toxicity:	0.103
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.408
Skin Sensitization:	0.664
Carcinogencity:	0.066
Eye Corrosion:	0.336
Eye Irritation:	0.949
Respiratory Toxicity:	0.208

Download Data

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

Natural Product: NPC296158

Natural Product ID:	NPC296158
*Common Name:**	Methyl 2,4-Dihydroxy-3,5,6-Trimethylbenzoate
IUPAC Name:	methyl 2,4-dihydroxy-3,5,6-trimethylbenzoate
Synonyms:
Standard InCHIKey:	DMSHNIHYQFQGGG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O4/c1-5-6(2)9(12)7(3)10(13)8(5)11(14)15-4/h12-13H,1-4H3
SMILES:	Cc1c(C)c(c(C)c(c1C(=O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507391
PubChem CID:	591722
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004701] p-Hydroxybenzoic acid esters [CHEMONTID:0004702] p-Hydroxybenzoic acid alkyl esters

*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
NPO33294	mortierella vinacea	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075797]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	IZ	=	30.0	mm	PMID[522486]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.0	mm	PMID[522486]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	10.0	mm	PMID[522486]

☑ 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 NPC296158 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	330
0.1-0.2	1692
0.2-0.3	4224
0.3-0.4	10025
0.4-0.5	9282
0.5-0.6	5087
0.6-0.7	7076
0.7-0.8	4474
0.8-0.85	378
0.85-0.9	109
0.9-0.95	17
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC158481
0.9531	High Similarity	NPC475645
0.9462	High Similarity	NPC245058
0.9385	High Similarity	NPC472599
0.9385	High Similarity	NPC156967
0.9248	High Similarity	NPC99441
0.9248	High Similarity	NPC165172
0.9179	High Similarity	NPC37530
0.9167	High Similarity	NPC194579
0.9147	High Similarity	NPC219892
0.9147	High Similarity	NPC189823
0.9091	High Similarity	NPC50455
0.9044	High Similarity	NPC159721
0.903	High Similarity	NPC275356
0.903	High Similarity	NPC88269
0.9008	High Similarity	NPC153783
0.8978	High Similarity	NPC151607
0.8978	High Similarity	NPC42540
0.8963	High Similarity	NPC472601
0.8963	High Similarity	NPC187690
0.8963	High Similarity	NPC472600
0.8913	High Similarity	NPC75694
0.8905	High Similarity	NPC471731
0.8897	High Similarity	NPC472603
0.8897	High Similarity	NPC472604
0.8897	High Similarity	NPC472605
0.8881	High Similarity	NPC70380
0.8872	High Similarity	NPC180905
0.8872	High Similarity	NPC278375
0.8872	High Similarity	NPC182496
0.8864	High Similarity	NPC180261
0.8864	High Similarity	NPC37299
0.8864	High Similarity	NPC48036
0.8849	High Similarity	NPC225173
0.8849	High Similarity	NPC163846
0.8832	High Similarity	NPC82913
0.8832	High Similarity	NPC471733
0.8824	High Similarity	NPC168471
0.8815	High Similarity	NPC212693
0.8815	High Similarity	NPC94248
0.8815	High Similarity	NPC191835
0.8806	High Similarity	NPC471690
0.8806	High Similarity	NPC235115
0.8797	High Similarity	NPC175943
0.8786	High Similarity	NPC125801
0.8786	High Similarity	NPC8817
0.8786	High Similarity	NPC166583
0.8786	High Similarity	NPC137296
0.8786	High Similarity	NPC53362
0.8768	High Similarity	NPC472610
0.875	High Similarity	NPC105456
0.875	High Similarity	NPC139634
0.8741	High Similarity	NPC135837
0.8731	High Similarity	NPC290803
0.8723	High Similarity	NPC470359
0.8714	High Similarity	NPC470357
0.8696	High Similarity	NPC182255
0.8696	High Similarity	NPC94076
0.8696	High Similarity	NPC322112
0.8692	High Similarity	NPC83572
0.8682	High Similarity	NPC262671
0.8682	High Similarity	NPC201728
0.8676	High Similarity	NPC33144
0.8676	High Similarity	NPC221104
0.8676	High Similarity	NPC478200
0.8676	High Similarity	NPC472602
0.8667	High Similarity	NPC118919
0.8667	High Similarity	NPC291454
0.8662	High Similarity	NPC233267
0.8662	High Similarity	NPC291049
0.8657	High Similarity	NPC474394
0.8652	High Similarity	NPC471734
0.8643	High Similarity	NPC473692
0.8643	High Similarity	NPC471689
0.8636	High Similarity	NPC62219
0.8633	High Similarity	NPC84266
0.8623	High Similarity	NPC67650
0.8623	High Similarity	NPC478217
0.8623	High Similarity	NPC313123
0.8623	High Similarity	NPC1704
0.8623	High Similarity	NPC53649
0.8613	High Similarity	NPC92655
0.8613	High Similarity	NPC32360
0.8613	High Similarity	NPC268052
0.8613	High Similarity	NPC52358
0.8613	High Similarity	NPC471819
0.8603	High Similarity	NPC71256
0.8601	High Similarity	NPC119929
0.8592	High Similarity	NPC105415
0.8592	High Similarity	NPC37139
0.8582	High Similarity	NPC260946
0.8582	High Similarity	NPC471735
0.8582	High Similarity	NPC470988
0.8582	High Similarity	NPC473023
0.8561	High Similarity	NPC250755
0.8551	High Similarity	NPC155205
0.8551	High Similarity	NPC158472
0.8542	High Similarity	NPC133856
0.8519	High Similarity	NPC470984
0.8519	High Similarity	NPC474519
0.8511	High Similarity	NPC28632
0.85	High Similarity	NPC469542
0.85	High Similarity	NPC478202
0.85	High Similarity	NPC472006
0.85	High Similarity	NPC51106
0.8496	Intermediate Similarity	NPC247477
0.8496	Intermediate Similarity	NPC21378
0.8496	Intermediate Similarity	NPC17840
0.8496	Intermediate Similarity	NPC470987
0.8489	Intermediate Similarity	NPC90411
0.8489	Intermediate Similarity	NPC472035
0.8489	Intermediate Similarity	NPC475730
0.8489	Intermediate Similarity	NPC158634
0.8489	Intermediate Similarity	NPC470842
0.8489	Intermediate Similarity	NPC149533
0.8489	Intermediate Similarity	NPC244923
0.8489	Intermediate Similarity	NPC478201
0.8485	Intermediate Similarity	NPC41263
0.8483	Intermediate Similarity	NPC175978
0.8483	Intermediate Similarity	NPC271681
0.8483	Intermediate Similarity	NPC273483
0.8478	Intermediate Similarity	NPC247409
0.8473	Intermediate Similarity	NPC95309
0.8472	Intermediate Similarity	NPC158866
0.8472	Intermediate Similarity	NPC150928
0.8467	Intermediate Similarity	NPC178467
0.8467	Intermediate Similarity	NPC474771
0.8467	Intermediate Similarity	NPC149372
0.8467	Intermediate Similarity	NPC65837
0.8467	Intermediate Similarity	NPC474849
0.8462	Intermediate Similarity	NPC172329
0.8462	Intermediate Similarity	NPC2569
0.8444	Intermediate Similarity	NPC267205
0.844	Intermediate Similarity	NPC21599
0.844	Intermediate Similarity	NPC193703
0.844	Intermediate Similarity	NPC48762
0.8429	Intermediate Similarity	NPC314271
0.8429	Intermediate Similarity	NPC474385
0.8425	Intermediate Similarity	NPC471695
0.8425	Intermediate Similarity	NPC472799
0.8421	Intermediate Similarity	NPC230818
0.8406	Intermediate Similarity	NPC475974
0.8403	Intermediate Similarity	NPC198927
0.8392	Intermediate Similarity	NPC126767
0.8392	Intermediate Similarity	NPC22005
0.8392	Intermediate Similarity	NPC190648
0.8392	Intermediate Similarity	NPC312929
0.8392	Intermediate Similarity	NPC34802
0.8392	Intermediate Similarity	NPC7943
0.8392	Intermediate Similarity	NPC245584
0.8392	Intermediate Similarity	NPC289042
0.8392	Intermediate Similarity	NPC118027
0.8392	Intermediate Similarity	NPC56433
0.8392	Intermediate Similarity	NPC123202
0.838	Intermediate Similarity	NPC83272
0.838	Intermediate Similarity	NPC134621
0.838	Intermediate Similarity	NPC34482
0.837	Intermediate Similarity	NPC27490
0.837	Intermediate Similarity	NPC185624
0.8367	Intermediate Similarity	NPC149618
0.8367	Intermediate Similarity	NPC89625
0.8358	Intermediate Similarity	NPC84772
0.8358	Intermediate Similarity	NPC186628
0.8357	Intermediate Similarity	NPC220106
0.8356	Intermediate Similarity	NPC217447
0.8346	Intermediate Similarity	NPC293453
0.8345	Intermediate Similarity	NPC205766
0.8345	Intermediate Similarity	NPC325983
0.8345	Intermediate Similarity	NPC179178
0.8345	Intermediate Similarity	NPC474655
0.8333	Intermediate Similarity	NPC470985
0.8333	Intermediate Similarity	NPC261292
0.8333	Intermediate Similarity	NPC256672
0.8333	Intermediate Similarity	NPC27221
0.8333	Intermediate Similarity	NPC7025
0.8333	Intermediate Similarity	NPC470982
0.8333	Intermediate Similarity	NPC301915
0.8333	Intermediate Similarity	NPC470983
0.8333	Intermediate Similarity	NPC470989
0.8322	Intermediate Similarity	NPC107625
0.8322	Intermediate Similarity	NPC237208
0.8322	Intermediate Similarity	NPC267509
0.8322	Intermediate Similarity	NPC138978
0.8322	Intermediate Similarity	NPC470570
0.8321	Intermediate Similarity	NPC142027
0.8321	Intermediate Similarity	NPC27407
0.8311	Intermediate Similarity	NPC146211
0.831	Intermediate Similarity	NPC210966
0.831	Intermediate Similarity	NPC126882
0.831	Intermediate Similarity	NPC280404
0.831	Intermediate Similarity	NPC86373
0.831	Intermediate Similarity	NPC19896
0.831	Intermediate Similarity	NPC478203
0.831	Intermediate Similarity	NPC66404
0.831	Intermediate Similarity	NPC277426
0.831	Intermediate Similarity	NPC210425
0.831	Intermediate Similarity	NPC95123
0.8309	Intermediate Similarity	NPC285054
0.8308	Intermediate Similarity	NPC218333
0.8298	Intermediate Similarity	NPC469579

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 NPC296158 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	1146
0.2-0.3	2073
0.3-0.4	2790
0.4-0.5	1674
0.5-0.6	843
0.6-0.7	252
0.7-0.8	64
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8913	High Similarity	NPD2534	Approved
0.8913	High Similarity	NPD2533	Approved
0.8913	High Similarity	NPD2532	Approved
0.8613	High Similarity	NPD970	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD6651	Approved
0.8039	Intermediate Similarity	NPD5710	Approved
0.8039	Intermediate Similarity	NPD5711	Approved
0.8039	Intermediate Similarity	NPD6232	Discontinued
0.7986	Intermediate Similarity	NPD1607	Approved
0.7933	Intermediate Similarity	NPD7819	Suspended
0.7902	Intermediate Similarity	NPD2800	Approved
0.7885	Intermediate Similarity	NPD7473	Discontinued
0.7842	Intermediate Similarity	NPD1240	Approved
0.7817	Intermediate Similarity	NPD5408	Approved
0.7817	Intermediate Similarity	NPD5405	Approved
0.7817	Intermediate Similarity	NPD5404	Approved
0.7817	Intermediate Similarity	NPD5406	Approved
0.7808	Intermediate Similarity	NPD7390	Discontinued
0.7786	Intermediate Similarity	NPD230	Phase 1
0.7746	Intermediate Similarity	NPD1510	Phase 2
0.7742	Intermediate Similarity	NPD6959	Discontinued
0.7698	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7635	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD9493	Approved
0.7569	Intermediate Similarity	NPD1551	Phase 2
0.7519	Intermediate Similarity	NPD9545	Approved
0.7517	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3750	Approved
0.7468	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1549	Phase 2
0.7465	Intermediate Similarity	NPD943	Approved
0.7451	Intermediate Similarity	NPD7411	Suspended
0.7436	Intermediate Similarity	NPD7075	Discontinued
0.7434	Intermediate Similarity	NPD3226	Approved
0.7426	Intermediate Similarity	NPD1201	Approved
0.7415	Intermediate Similarity	NPD1243	Approved
0.74	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2346	Discontinued
0.7386	Intermediate Similarity	NPD6599	Discontinued
0.7372	Intermediate Similarity	NPD7768	Phase 2
0.7365	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5844	Phase 1
0.7338	Intermediate Similarity	NPD1470	Approved
0.7338	Intermediate Similarity	NPD1164	Approved
0.7333	Intermediate Similarity	NPD1511	Approved
0.7325	Intermediate Similarity	NPD3749	Approved
0.7308	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD920	Approved
0.729	Intermediate Similarity	NPD1934	Approved
0.729	Intermediate Similarity	NPD6801	Discontinued
0.7279	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD4380	Phase 2
0.7267	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1283	Approved
0.7246	Intermediate Similarity	NPD9269	Phase 2
0.7244	Intermediate Similarity	NPD1465	Phase 2
0.7237	Intermediate Similarity	NPD1512	Approved
0.7219	Intermediate Similarity	NPD6799	Approved
0.7206	Intermediate Similarity	NPD9268	Approved
0.7203	Intermediate Similarity	NPD411	Approved
0.7203	Intermediate Similarity	NPD3764	Approved
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3748	Approved
0.7134	Intermediate Similarity	NPD2801	Approved
0.7122	Intermediate Similarity	NPD9717	Approved
0.7095	Intermediate Similarity	NPD6100	Approved
0.7095	Intermediate Similarity	NPD2796	Approved
0.7095	Intermediate Similarity	NPD6099	Approved
0.7089	Intermediate Similarity	NPD3817	Phase 2
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD919	Approved
0.7059	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1281	Approved
0.7044	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3882	Suspended
0.7027	Intermediate Similarity	NPD2799	Discontinued
0.7023	Intermediate Similarity	NPD9266	Approved
0.7023	Intermediate Similarity	NPD74	Approved
0.702	Intermediate Similarity	NPD4628	Phase 3
0.702	Intermediate Similarity	NPD7003	Approved
0.7006	Intermediate Similarity	NPD6559	Discontinued
0.6985	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1203	Approved
0.6957	Remote Similarity	NPD5691	Approved
0.6957	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD9264	Approved
0.6947	Remote Similarity	NPD9267	Approved
0.6947	Remote Similarity	NPD9263	Approved
0.6946	Remote Similarity	NPD5953	Discontinued
0.6939	Remote Similarity	NPD447	Suspended
0.6936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD422	Phase 1
0.6928	Remote Similarity	NPD7286	Phase 2
0.6901	Remote Similarity	NPD8150	Discontinued
0.6894	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1608	Approved
0.6855	Remote Similarity	NPD37	Approved
0.6849	Remote Similarity	NPD2313	Discontinued
0.6848	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6166	Phase 2
0.6842	Remote Similarity	NPD2654	Approved
0.6826	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5124	Phase 1
0.6824	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5494	Approved
0.6786	Remote Similarity	NPD7074	Phase 3
0.6781	Remote Similarity	NPD4625	Phase 3
0.6772	Remote Similarity	NPD7458	Discontinued
0.6766	Remote Similarity	NPD3818	Discontinued
0.6752	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6234	Discontinued
0.6731	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4966	Approved
0.6728	Remote Similarity	NPD4965	Approved
0.6728	Remote Similarity	NPD4967	Phase 2
0.6727	Remote Similarity	NPD7229	Phase 3
0.6726	Remote Similarity	NPD7054	Approved
0.6724	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD4750	Phase 3
0.6715	Remote Similarity	NPD9281	Approved
0.6714	Remote Similarity	NPD1651	Approved
0.6711	Remote Similarity	NPD2344	Approved
0.669	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4308	Phase 3
0.6686	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD6535	Approved
0.6667	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD4288	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8151	Discontinued
0.6647	Remote Similarity	NPD6797	Phase 2
0.6646	Remote Similarity	NPD5403	Approved
0.6644	Remote Similarity	NPD2979	Phase 3
0.6642	Remote Similarity	NPD1398	Phase 1
0.6641	Remote Similarity	NPD9261	Approved
0.6628	Remote Similarity	NPD8312	Approved
0.6628	Remote Similarity	NPD8313	Approved
0.6624	Remote Similarity	NPD5401	Approved
0.6622	Remote Similarity	NPD1296	Phase 2
0.6608	Remote Similarity	NPD7251	Discontinued
0.66	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6832	Phase 2
0.6597	Remote Similarity	NPD4749	Approved
0.6575	Remote Similarity	NPD1019	Discontinued
0.6575	Remote Similarity	NPD2798	Approved
0.657	Remote Similarity	NPD7808	Phase 3
0.6566	Remote Similarity	NPD7199	Phase 2
0.6565	Remote Similarity	NPD940	Approved
0.6565	Remote Similarity	NPD846	Approved
0.6561	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7435	Discontinued
0.6556	Remote Similarity	NPD7700	Phase 2
0.6556	Remote Similarity	NPD7699	Phase 2
0.6554	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2309	Approved
0.6536	Remote Similarity	NPD2438	Suspended
0.6534	Remote Similarity	NPD4287	Approved
0.6533	Remote Similarity	NPD4060	Phase 1
0.6531	Remote Similarity	NPD9494	Approved
0.6529	Remote Similarity	NPD6020	Phase 2
0.6528	Remote Similarity	NPD3972	Approved
0.6522	Remote Similarity	NPD8320	Phase 1
0.6522	Remote Similarity	NPD8319	Approved
0.651	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.651	Remote Similarity	NPD3268	Approved
0.651	Remote Similarity	NPD7985	Registered
0.651	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2797	Approved
0.65	Remote Similarity	NPD7340	Approved
0.6497	Remote Similarity	NPD3300	Phase 2
0.6494	Remote Similarity	NPD1471	Phase 3
0.6494	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6005	Phase 3
0.6494	Remote Similarity	NPD6002	Phase 3
0.6494	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6004	Phase 3
0.6491	Remote Similarity	NPD1729	Discontinued
0.6488	Remote Similarity	NPD3926	Phase 2
0.6488	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6779	Approved
0.6484	Remote Similarity	NPD6782	Approved
0.6484	Remote Similarity	NPD6778	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