NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.1
Volume:	240.957
LogP:	3.015
LogD:	0.844
LogS:	-2.683
# Rotatable Bonds:	3
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	3.405
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.703
MDCK Permeability:	3.4581294130475726e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.149

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	95.11437225341797%
Volume Distribution (VD):	0.472
Pgp-substrate:	4.4554314613342285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.435
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.125
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.059

ADMET: Excretion

Clearance (CL):	1.701
Half-life (T1/2):	0.865

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.485
Drug-inuced Liver Injury (DILI):	0.908
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.126
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.09
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.233
Respiratory Toxicity:	0.611

Download Data

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

Natural Product: NPC474394

Natural Product ID:	NPC474394
*Common Name:**	Phenol A Acid
IUPAC Name:	2,6-dihydroxy-4-[(2S,3R)-3-hydroxybutan-2-yl]-3-methylbenzoic acid
Synonyms:	Phenol A Acid
Standard InCHIKey:	UHEOCPAMGZSLMB-IYSWYEEDSA-N
Standard InCHI:	InChI=1S/C12H16O5/c1-5(7(3)13)8-4-9(14)10(12(16)17)11(15)6(8)2/h4-5,7,13-15H,1-3H3,(H,16,17)/t5-,7-/m1/s1
SMILES:	C[C@@H](c1cc(O)c(c(c1C)O)C(=O)O)[C@H](O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465874
PubChem CID:	15200541
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO32513	Penicillium citrinum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18281952]
NPO41450	Penicillium citrinum + Aspergillus sydowii	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[31953204]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	795800.0	nM	PMID[559564]

☑ 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 NPC474394 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	302
0.1-0.2	1315
0.2-0.3	3270
0.3-0.4	8305
0.4-0.5	11195
0.5-0.6	4686
0.6-0.7	8534
0.7-0.8	4433
0.8-0.85	487
0.85-0.9	148
0.9-0.95	21
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9318	High Similarity	NPC278375
0.9318	High Similarity	NPC290803
0.9313	High Similarity	NPC37299
0.9313	High Similarity	NPC180261
0.9197	High Similarity	NPC471731
0.9167	High Similarity	NPC48036
0.9124	High Similarity	NPC471733
0.9104	High Similarity	NPC158481
0.9104	High Similarity	NPC118919
0.9084	High Similarity	NPC62219
0.9058	High Similarity	NPC159721
0.8993	High Similarity	NPC151607
0.8993	High Similarity	NPC42540
0.8992	High Similarity	NPC201728
0.8992	High Similarity	NPC262671
0.8978	High Similarity	NPC99441
0.8971	High Similarity	NPC94248
0.8971	High Similarity	NPC212693
0.8971	High Similarity	NPC475974
0.8955	High Similarity	NPC474519
0.8939	High Similarity	NPC17840
0.8939	High Similarity	NPC247477
0.8936	High Similarity	NPC471734
0.8913	High Similarity	NPC37530
0.8913	High Similarity	NPC472605
0.8913	High Similarity	NPC472604
0.8905	High Similarity	NPC88269
0.8905	High Similarity	NPC139634
0.8905	High Similarity	NPC105456
0.8905	High Similarity	NPC162939
0.8905	High Similarity	NPC474655
0.8897	High Similarity	NPC474849
0.8897	High Similarity	NPC70380
0.8897	High Similarity	NPC178467
0.8897	High Similarity	NPC149372
0.8897	High Similarity	NPC474771
0.8897	High Similarity	NPC65837
0.8897	High Similarity	NPC71256
0.8897	High Similarity	NPC194579
0.8865	High Similarity	NPC471735
0.8849	High Similarity	NPC474961
0.8849	High Similarity	NPC135524
0.8846	High Similarity	NPC240744
0.8846	High Similarity	NPC167055
0.8841	High Similarity	NPC472601
0.8841	High Similarity	NPC472600
0.8841	High Similarity	NPC165172
0.8832	High Similarity	NPC472403
0.8832	High Similarity	NPC191835
0.8824	High Similarity	NPC156967
0.8803	High Similarity	NPC166583
0.8803	High Similarity	NPC53362
0.8788	High Similarity	NPC41263
0.8777	High Similarity	NPC305845
0.8777	High Similarity	NPC204045
0.8777	High Similarity	NPC472603
0.8768	High Similarity	NPC32360
0.875	High Similarity	NPC161632
0.8741	High Similarity	NPC267205
0.8741	High Similarity	NPC153783
0.8732	High Similarity	NPC473023
0.8731	High Similarity	NPC219892
0.8731	High Similarity	NPC189823
0.8712	High Similarity	NPC209959
0.8705	High Similarity	NPC158472
0.8705	High Similarity	NPC168471
0.8702	High Similarity	NPC477454
0.8696	High Similarity	NPC33144
0.8696	High Similarity	NPC478200
0.8696	High Similarity	NPC9121
0.8696	High Similarity	NPC177307
0.8696	High Similarity	NPC472602
0.8686	High Similarity	NPC235115
0.8686	High Similarity	NPC472599
0.8686	High Similarity	NPC191976
0.8657	High Similarity	NPC296158
0.8657	High Similarity	NPC147757
0.8652	High Similarity	NPC51106
0.8652	High Similarity	NPC469542
0.8652	High Similarity	NPC472610
0.8643	High Similarity	NPC187843
0.8643	High Similarity	NPC67650
0.8643	High Similarity	NPC244923
0.8643	High Similarity	NPC1704
0.8643	High Similarity	NPC313123
0.8643	High Similarity	NPC53649
0.8643	High Similarity	NPC158634
0.8643	High Similarity	NPC478217
0.8636	High Similarity	NPC473691
0.8633	High Similarity	NPC268052
0.8633	High Similarity	NPC190457
0.8633	High Similarity	NPC275356
0.8623	High Similarity	NPC471452
0.8623	High Similarity	NPC245058
0.8603	High Similarity	NPC314048
0.8601	High Similarity	NPC163846
0.8601	High Similarity	NPC225173
0.8593	High Similarity	NPC41847
0.8592	High Similarity	NPC244691
0.8592	High Similarity	NPC471906
0.8582	High Similarity	NPC474385
0.8582	High Similarity	NPC82913
0.8571	High Similarity	NPC181560
0.8571	High Similarity	NPC169452
0.8571	High Similarity	NPC183345
0.8561	High Similarity	NPC472592
0.8561	High Similarity	NPC475733
0.8552	High Similarity	NPC477221
0.8551	High Similarity	NPC50455
0.8551	High Similarity	NPC254847
0.8551	High Similarity	NPC291454
0.855	High Similarity	NPC65761
0.855	High Similarity	NPC472029
0.8542	High Similarity	NPC125801
0.8542	High Similarity	NPC8817
0.854	High Similarity	NPC282780
0.854	High Similarity	NPC166480
0.8538	High Similarity	NPC215392
0.8531	High Similarity	NPC34482
0.8531	High Similarity	NPC83272
0.8529	High Similarity	NPC478190
0.8527	High Similarity	NPC294964
0.8521	High Similarity	NPC472006
0.8521	High Similarity	NPC478202
0.8521	High Similarity	NPC354984
0.8511	High Similarity	NPC478201
0.8511	High Similarity	NPC472035
0.8511	High Similarity	NPC290550
0.8511	High Similarity	NPC475730
0.8511	High Similarity	NPC106519
0.8511	High Similarity	NPC91019
0.8503	High Similarity	NPC273483
0.85	High Similarity	NPC242994
0.85	High Similarity	NPC138099
0.8489	Intermediate Similarity	NPC135837
0.8489	Intermediate Similarity	NPC53206
0.8489	Intermediate Similarity	NPC53414
0.8489	Intermediate Similarity	NPC471905
0.8485	Intermediate Similarity	NPC68756
0.8485	Intermediate Similarity	NPC117794
0.8485	Intermediate Similarity	NPC152525
0.8478	Intermediate Similarity	NPC142027
0.8478	Intermediate Similarity	NPC182496
0.8478	Intermediate Similarity	NPC180905
0.8473	Intermediate Similarity	NPC91105
0.8473	Intermediate Similarity	NPC283514
0.8472	Intermediate Similarity	NPC470570
0.8472	Intermediate Similarity	NPC470357
0.8467	Intermediate Similarity	NPC213485
0.8467	Intermediate Similarity	NPC40524
0.8467	Intermediate Similarity	NPC139074
0.8462	Intermediate Similarity	NPC280404
0.8462	Intermediate Similarity	NPC159760
0.8462	Intermediate Similarity	NPC301987
0.8462	Intermediate Similarity	NPC292665
0.8462	Intermediate Similarity	NPC179092
0.8462	Intermediate Similarity	NPC115188
0.8462	Intermediate Similarity	NPC146642
0.8462	Intermediate Similarity	NPC86373
0.8462	Intermediate Similarity	NPC178395
0.8462	Intermediate Similarity	NPC48762
0.8462	Intermediate Similarity	NPC244994
0.8462	Intermediate Similarity	NPC277426
0.8462	Intermediate Similarity	NPC210425
0.8462	Intermediate Similarity	NPC35856
0.8462	Intermediate Similarity	NPC26433
0.8462	Intermediate Similarity	NPC222876
0.8462	Intermediate Similarity	NPC272454
0.8456	Intermediate Similarity	NPC475042
0.8451	Intermediate Similarity	NPC193555
0.8451	Intermediate Similarity	NPC469579
0.845	Intermediate Similarity	NPC184579
0.845	Intermediate Similarity	NPC233165
0.8446	Intermediate Similarity	NPC472799
0.8446	Intermediate Similarity	NPC470102
0.8444	Intermediate Similarity	NPC92624
0.8444	Intermediate Similarity	NPC474546
0.844	Intermediate Similarity	NPC155205
0.8438	Intermediate Similarity	NPC125252
0.8429	Intermediate Similarity	NPC221104
0.8425	Intermediate Similarity	NPC291049
0.8425	Intermediate Similarity	NPC233267
0.8417	Intermediate Similarity	NPC223836
0.8417	Intermediate Similarity	NPC315275
0.8414	Intermediate Similarity	NPC290194
0.8406	Intermediate Similarity	NPC175943
0.8403	Intermediate Similarity	NPC473692
0.8403	Intermediate Similarity	NPC75694
0.8403	Intermediate Similarity	NPC257558
0.8397	Intermediate Similarity	NPC198336
0.8394	Intermediate Similarity	NPC175738
0.8392	Intermediate Similarity	NPC295712
0.8392	Intermediate Similarity	NPC313047
0.8392	Intermediate Similarity	NPC474203
0.8392	Intermediate Similarity	NPC451542
0.8392	Intermediate Similarity	NPC174905
0.8392	Intermediate Similarity	NPC84266
0.8392	Intermediate Similarity	NPC293545
0.8385	Intermediate Similarity	NPC294037
0.8382	Intermediate Similarity	NPC259942

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 NPC474394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	944
0.2-0.3	1718
0.3-0.4	2682
0.4-0.5	1980
0.5-0.6	1059
0.6-0.7	410
0.7-0.8	91
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8551	High Similarity	NPD1509	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD2532	Approved
0.8403	Intermediate Similarity	NPD2534	Approved
0.8403	Intermediate Similarity	NPD2533	Approved
0.8369	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD5404	Approved
0.8357	Intermediate Similarity	NPD5406	Approved
0.8357	Intermediate Similarity	NPD5408	Approved
0.8357	Intermediate Similarity	NPD5405	Approved
0.8207	Intermediate Similarity	NPD7390	Discontinued
0.7985	Intermediate Similarity	NPD1201	Approved
0.7883	Intermediate Similarity	NPD1164	Approved
0.7883	Intermediate Similarity	NPD1470	Approved
0.7847	Intermediate Similarity	NPD2935	Discontinued
0.7843	Intermediate Similarity	NPD7819	Suspended
0.7834	Intermediate Similarity	NPD6232	Discontinued
0.7799	Intermediate Similarity	NPD7473	Discontinued
0.7785	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD943	Approved
0.7669	Intermediate Similarity	NPD9493	Approved
0.7658	Intermediate Similarity	NPD6959	Discontinued
0.7639	Intermediate Similarity	NPD1607	Approved
0.761	Intermediate Similarity	NPD5711	Approved
0.761	Intermediate Similarity	NPD5710	Approved
0.7603	Intermediate Similarity	NPD1551	Phase 2
0.7597	Intermediate Similarity	NPD9266	Approved
0.7597	Intermediate Similarity	NPD74	Approved
0.7569	Intermediate Similarity	NPD230	Phase 1
0.7538	Intermediate Similarity	NPD4750	Phase 3
0.7537	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD9269	Phase 2
0.7534	Intermediate Similarity	NPD1510	Phase 2
0.7519	Intermediate Similarity	NPD9267	Approved
0.7519	Intermediate Similarity	NPD9263	Approved
0.7519	Intermediate Similarity	NPD9264	Approved
0.7517	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9268	Approved
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7468	Intermediate Similarity	NPD7075	Discontinued
0.7468	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD4626	Approved
0.7434	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1283	Approved
0.7419	Intermediate Similarity	NPD4380	Phase 2
0.74	Intermediate Similarity	NPD3750	Approved
0.7389	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1549	Phase 2
0.7372	Intermediate Similarity	NPD7411	Suspended
0.7349	Intermediate Similarity	NPD6559	Discontinued
0.7325	Intermediate Similarity	NPD6801	Discontinued
0.7325	Intermediate Similarity	NPD37	Approved
0.7315	Intermediate Similarity	NPD2346	Discontinued
0.731	Intermediate Similarity	NPD6663	Approved
0.7308	Intermediate Similarity	NPD6599	Discontinued
0.7299	Intermediate Similarity	NPD9545	Approved
0.7297	Intermediate Similarity	NPD2799	Discontinued
0.7285	Intermediate Similarity	NPD7003	Approved
0.7279	Intermediate Similarity	NPD6651	Approved
0.7273	Intermediate Similarity	NPD5736	Approved
0.7266	Intermediate Similarity	NPD846	Approved
0.7266	Intermediate Similarity	NPD940	Approved
0.7259	Intermediate Similarity	NPD9281	Approved
0.7252	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5691	Approved
0.7246	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3226	Approved
0.7241	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD411	Approved
0.7215	Intermediate Similarity	NPD1934	Approved
0.7214	Intermediate Similarity	NPD1281	Approved
0.7209	Intermediate Similarity	NPD9261	Approved
0.7195	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2932	Approved
0.7194	Intermediate Similarity	NPD3019	Approved
0.7188	Intermediate Similarity	NPD4967	Phase 2
0.7188	Intermediate Similarity	NPD4966	Approved
0.7188	Intermediate Similarity	NPD4965	Approved
0.7171	Intermediate Similarity	NPD3400	Discontinued
0.7171	Intermediate Similarity	NPD4628	Phase 3
0.7163	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD6799	Approved
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7133	Intermediate Similarity	NPD2796	Approved
0.7123	Intermediate Similarity	NPD3764	Approved
0.7105	Intermediate Similarity	NPD2800	Approved
0.7105	Intermediate Similarity	NPD1243	Approved
0.7099	Intermediate Similarity	NPD6234	Discontinued
0.7097	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3300	Phase 2
0.7069	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3748	Approved
0.7059	Intermediate Similarity	NPD8313	Approved
0.7059	Intermediate Similarity	NPD8312	Approved
0.7051	Intermediate Similarity	NPD6273	Approved
0.7037	Intermediate Similarity	NPD3749	Approved
0.7037	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1511	Approved
0.7027	Intermediate Similarity	NPD2979	Phase 3
0.702	Intermediate Similarity	NPD6100	Approved
0.702	Intermediate Similarity	NPD2438	Suspended
0.702	Intermediate Similarity	NPD6099	Approved
0.7019	Intermediate Similarity	NPD5402	Approved
0.7019	Intermediate Similarity	NPD3817	Phase 2
0.7014	Intermediate Similarity	NPD1203	Approved
0.7007	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5951	Approved
0.7006	Intermediate Similarity	NPD920	Approved
0.7006	Intermediate Similarity	NPD5403	Approved
0.6993	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6166	Phase 2
0.6988	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.698	Remote Similarity	NPD447	Suspended
0.698	Remote Similarity	NPD5124	Phase 1
0.6975	Remote Similarity	NPD3882	Suspended
0.6968	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6020	Phase 2
0.6964	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD520	Approved
0.6957	Remote Similarity	NPD2801	Approved
0.6954	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD288	Approved
0.6951	Remote Similarity	NPD5494	Approved
0.6948	Remote Similarity	NPD8166	Discontinued
0.6943	Remote Similarity	NPD1512	Approved
0.6929	Remote Similarity	NPD3091	Approved
0.6923	Remote Similarity	NPD7074	Phase 3
0.6918	Remote Similarity	NPD7458	Discontinued
0.6914	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4060	Phase 1
0.6905	Remote Similarity	NPD7228	Approved
0.6905	Remote Similarity	NPD3818	Discontinued
0.6897	Remote Similarity	NPD3094	Phase 2
0.6892	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.689	Remote Similarity	NPD919	Approved
0.6882	Remote Similarity	NPD5953	Discontinued
0.6879	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1651	Approved
0.6879	Remote Similarity	NPD5401	Approved
0.6875	Remote Similarity	NPD844	Approved
0.6871	Remote Similarity	NPD6832	Phase 2
0.6864	Remote Similarity	NPD7054	Approved
0.6863	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6005	Phase 3
0.6863	Remote Similarity	NPD6004	Phase 3
0.6863	Remote Similarity	NPD6002	Phase 3
0.6861	Remote Similarity	NPD7635	Approved
0.6857	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3092	Approved
0.6853	Remote Similarity	NPD422	Phase 1
0.6852	Remote Similarity	NPD1465	Phase 2
0.6849	Remote Similarity	NPD2798	Approved
0.6838	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7472	Approved
0.6824	Remote Similarity	NPD4625	Phase 3
0.6815	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD9570	Approved
0.6797	Remote Similarity	NPD2531	Phase 2
0.6794	Remote Similarity	NPD1242	Phase 1
0.6784	Remote Similarity	NPD6797	Phase 2
0.6783	Remote Similarity	NPD3023	Approved
0.6783	Remote Similarity	NPD3026	Approved
0.6781	Remote Similarity	NPD2797	Approved
0.6779	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2313	Discontinued
0.6774	Remote Similarity	NPD8151	Discontinued
0.6766	Remote Similarity	NPD7229	Phase 3
0.6765	Remote Similarity	NPD7286	Phase 2
0.6761	Remote Similarity	NPD3024	Approved
0.6761	Remote Similarity	NPD3025	Approved
0.6759	Remote Similarity	NPD4749	Approved
0.6755	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7251	Discontinued
0.6744	Remote Similarity	NPD1809	Phase 2
0.6739	Remote Similarity	NPD8320	Phase 1
0.6739	Remote Similarity	NPD8319	Approved
0.6735	Remote Similarity	NPD1019	Discontinued
0.6732	Remote Similarity	NPD4308	Phase 3
0.6728	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD845	Approved
0.6713	Remote Similarity	NPD3095	Discontinued
0.6713	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1778	Approved
0.6711	Remote Similarity	NPD7008	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