NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.07
Volume:	273.743
LogP:	2.658
LogD:	1.629
LogS:	-3.036
# Rotatable Bonds:	4
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.742
Synthetic Accessibility Score:	2.039
Fsp3:	0.067
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:	-5.586
MDCK Permeability:	7.818013727955986e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.148
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.186

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	94.39940643310547%
Volume Distribution (VD):	0.272
Pgp-substrate:	3.9915993213653564%

ADMET: Metabolism

CYP1A2-inhibitor:	0.27
CYP1A2-substrate:	0.053
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.565
CYP2C9-substrate:	0.291
CYP2D6-inhibitor:	0.237
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.093
CYP3A4-substrate:	0.083

ADMET: Excretion

Clearance (CL):	4.698
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.432
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.255
Carcinogencity:	0.327
Eye Corrosion:	0.003
Eye Irritation:	0.377
Respiratory Toxicity:	0.185

Download Data

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

Natural Product: NPC95537

Natural Product ID:	NPC95537
*Common Name:**	2-Hydroxy-6-[2-(4-Hydroxyphenyl)-2-Oxoethyl]Benzoic Acid
IUPAC Name:	2-hydroxy-6-[2-(4-hydroxyphenyl)-2-oxoethyl]benzoic acid
Synonyms:
Standard InCHIKey:	YIGHIFUVVSYMFG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O5/c16-11-6-4-9(5-7-11)13(18)8-10-2-1-3-12(17)14(10)15(19)20/h1-7,16-17H,8H2,(H,19,20)
SMILES:	c1cc(CC(=O)c2ccc(cc2)O)c(c(c1)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813260
PubChem CID:	53359352
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	roots	Daba desert reserve (50 km South of Amman), Jordan	2009-APR	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	100000.0	nM	PMID[495751]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	100000.0	nM	PMID[495751]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	100000.0	nM	PMID[495751]

☑ 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 NPC95537 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	373
0.1-0.2	1706
0.2-0.3	4169
0.3-0.4	10512
0.4-0.5	8134
0.5-0.6	5491
0.6-0.7	7645
0.7-0.8	4150
0.8-0.85	394
0.85-0.9	115
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9504	High Similarity	NPC283514
0.9453	High Similarity	NPC72918
0.9421	High Similarity	NPC198336
0.9237	High Similarity	NPC4214
0.9055	High Similarity	NPC41263
0.9032	High Similarity	NPC244351
0.8898	High Similarity	NPC8745
0.8897	High Similarity	NPC66593
0.8889	High Similarity	NPC13238
0.8889	High Similarity	NPC290550
0.8889	High Similarity	NPC236189
0.8862	High Similarity	NPC184579
0.8862	High Similarity	NPC233165
0.8855	High Similarity	NPC48036
0.8852	High Similarity	NPC125252
0.8837	High Similarity	NPC92624
0.8819	High Similarity	NPC201728
0.8819	High Similarity	NPC262671
0.8819	High Similarity	NPC10926
0.8797	High Similarity	NPC118919
0.8788	High Similarity	NPC288089
0.8788	High Similarity	NPC44437
0.8788	High Similarity	NPC282780
0.8788	High Similarity	NPC166480
0.8769	High Similarity	NPC259942
0.8769	High Similarity	NPC31539
0.8769	High Similarity	NPC247477
0.8769	High Similarity	NPC17840
0.875	High Similarity	NPC160499
0.8731	High Similarity	NPC471452
0.8731	High Similarity	NPC261292
0.8731	High Similarity	NPC301915
0.873	High Similarity	NPC133909
0.873	High Similarity	NPC32032
0.872	High Similarity	NPC159760
0.872	High Similarity	NPC179092
0.872	High Similarity	NPC35856
0.872	High Similarity	NPC178395
0.872	High Similarity	NPC301987
0.872	High Similarity	NPC222876
0.872	High Similarity	NPC244994
0.872	High Similarity	NPC272454
0.872	High Similarity	NPC115188
0.872	High Similarity	NPC26433
0.872	High Similarity	NPC292665
0.8712	High Similarity	NPC43627
0.8705	High Similarity	NPC314437
0.8667	High Similarity	NPC9121
0.8667	High Similarity	NPC177307
0.8661	High Similarity	NPC375356
0.8657	High Similarity	NPC223836
0.8651	High Similarity	NPC267552
0.8651	High Similarity	NPC224273
0.8651	High Similarity	NPC242895
0.8651	High Similarity	NPC156139
0.8651	High Similarity	NPC143427
0.8651	High Similarity	NPC73532
0.8651	High Similarity	NPC19174
0.8651	High Similarity	NPC115159
0.8651	High Similarity	NPC45438
0.8647	High Similarity	NPC474097
0.8605	High Similarity	NPC473751
0.8603	High Similarity	NPC92655
0.8603	High Similarity	NPC26924
0.8593	High Similarity	NPC149372
0.8593	High Similarity	NPC474849
0.8593	High Similarity	NPC53206
0.8593	High Similarity	NPC53414
0.8593	High Similarity	NPC290030
0.8593	High Similarity	NPC178467
0.8593	High Similarity	NPC65837
0.8593	High Similarity	NPC474771
0.8583	High Similarity	NPC68167
0.8583	High Similarity	NPC300274
0.8583	High Similarity	NPC91478
0.8582	High Similarity	NPC80035
0.8582	High Similarity	NPC161632
0.8571	High Similarity	NPC248363
0.8571	High Similarity	NPC297186
0.8571	High Similarity	NPC53896
0.8571	High Similarity	NPC267205
0.8571	High Similarity	NPC294226
0.8571	High Similarity	NPC52407
0.8561	High Similarity	NPC93015
0.8551	High Similarity	NPC193555
0.8551	High Similarity	NPC73061
0.855	High Similarity	NPC99731
0.854	High Similarity	NPC183345
0.854	High Similarity	NPC155205
0.854	High Similarity	NPC315578
0.8529	High Similarity	NPC472403
0.8529	High Similarity	NPC475974
0.8529	High Similarity	NPC13715
0.8529	High Similarity	NPC221104
0.8527	High Similarity	NPC103540
0.8527	High Similarity	NPC477454
0.8527	High Similarity	NPC167055
0.8527	High Similarity	NPC240744
0.8519	High Similarity	NPC254847
0.8507	High Similarity	NPC50924
0.8504	High Similarity	NPC120545
0.8496	Intermediate Similarity	NPC135801
0.8492	Intermediate Similarity	NPC159525
0.8489	Intermediate Similarity	NPC478202
0.8485	Intermediate Similarity	NPC26697
0.8485	Intermediate Similarity	NPC233056
0.8485	Intermediate Similarity	NPC147757
0.8485	Intermediate Similarity	NPC31799
0.8478	Intermediate Similarity	NPC478217
0.8478	Intermediate Similarity	NPC478201
0.8478	Intermediate Similarity	NPC470842
0.8478	Intermediate Similarity	NPC313123
0.8478	Intermediate Similarity	NPC472035
0.8473	Intermediate Similarity	NPC179898
0.8468	Intermediate Similarity	NPC108288
0.8468	Intermediate Similarity	NPC477453
0.8467	Intermediate Similarity	NPC242994
0.8467	Intermediate Similarity	NPC472903
0.8467	Intermediate Similarity	NPC474655
0.8467	Intermediate Similarity	NPC138099
0.8462	Intermediate Similarity	NPC96915
0.8462	Intermediate Similarity	NPC473691
0.8456	Intermediate Similarity	NPC62272
0.8456	Intermediate Similarity	NPC471905
0.8451	Intermediate Similarity	NPC471907
0.845	Intermediate Similarity	NPC91475
0.845	Intermediate Similarity	NPC265910
0.8444	Intermediate Similarity	NPC290803
0.8444	Intermediate Similarity	NPC27407
0.8444	Intermediate Similarity	NPC278375
0.8443	Intermediate Similarity	NPC231717
0.8433	Intermediate Similarity	NPC37299
0.8433	Intermediate Similarity	NPC180261
0.8421	Intermediate Similarity	NPC244699
0.8421	Intermediate Similarity	NPC219892
0.8421	Intermediate Similarity	NPC189823
0.8421	Intermediate Similarity	NPC469526
0.8421	Intermediate Similarity	NPC34070
0.8417	Intermediate Similarity	NPC250755
0.8413	Intermediate Similarity	NPC158222
0.8409	Intermediate Similarity	NPC109123
0.8409	Intermediate Similarity	NPC474998
0.8406	Intermediate Similarity	NPC181560
0.8406	Intermediate Similarity	NPC168471
0.8406	Intermediate Similarity	NPC169452
0.8406	Intermediate Similarity	NPC203063
0.8397	Intermediate Similarity	NPC100067
0.8397	Intermediate Similarity	NPC169250
0.8397	Intermediate Similarity	NPC23126
0.8397	Intermediate Similarity	NPC103356
0.8397	Intermediate Similarity	NPC98254
0.8397	Intermediate Similarity	NPC72158
0.8397	Intermediate Similarity	NPC266689
0.8397	Intermediate Similarity	NPC190043
0.8397	Intermediate Similarity	NPC30501
0.8397	Intermediate Similarity	NPC162612
0.8397	Intermediate Similarity	NPC105157
0.8387	Intermediate Similarity	NPC322197
0.8382	Intermediate Similarity	NPC291454
0.8382	Intermediate Similarity	NPC191976
0.837	Intermediate Similarity	NPC474519
0.837	Intermediate Similarity	NPC175943
0.8359	Intermediate Similarity	NPC196976
0.8358	Intermediate Similarity	NPC175738
0.8358	Intermediate Similarity	NPC478190
0.8346	Intermediate Similarity	NPC136588
0.8346	Intermediate Similarity	NPC216297
0.8346	Intermediate Similarity	NPC199253
0.8346	Intermediate Similarity	NPC117609
0.8346	Intermediate Similarity	NPC285829
0.8346	Intermediate Similarity	NPC7151
0.8346	Intermediate Similarity	NPC206778
0.8346	Intermediate Similarity	NPC473662
0.8345	Intermediate Similarity	NPC472904
0.8333	Intermediate Similarity	NPC162939
0.8333	Intermediate Similarity	NPC21305
0.8333	Intermediate Similarity	NPC282923
0.8333	Intermediate Similarity	NPC48248
0.8333	Intermediate Similarity	NPC247250
0.8333	Intermediate Similarity	NPC190457
0.8333	Intermediate Similarity	NPC52358
0.8333	Intermediate Similarity	NPC473017
0.8333	Intermediate Similarity	NPC241089
0.8333	Intermediate Similarity	NPC143438
0.8333	Intermediate Similarity	NPC221777
0.8333	Intermediate Similarity	NPC767
0.8333	Intermediate Similarity	NPC96024
0.8321	Intermediate Similarity	NPC62952
0.8321	Intermediate Similarity	NPC62907
0.8321	Intermediate Similarity	NPC53001
0.8321	Intermediate Similarity	NPC231774
0.8321	Intermediate Similarity	NPC267846
0.8321	Intermediate Similarity	NPC3224
0.8321	Intermediate Similarity	NPC71256
0.832	Intermediate Similarity	NPC312800
0.8309	Intermediate Similarity	NPC142027
0.8309	Intermediate Similarity	NPC258502
0.8308	Intermediate Similarity	NPC173978
0.8308	Intermediate Similarity	NPC142956
0.8308	Intermediate Similarity	NPC310540

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 NPC95537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	970
0.2-0.3	1492
0.3-0.4	2720
0.4-0.5	2014
0.5-0.6	1111
0.6-0.7	383
0.7-0.8	102
0.8-0.85	9
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8672	High Similarity	NPD1164	Approved
0.8527	High Similarity	NPD1470	Approved
0.8519	High Similarity	NPD1509	Clinical (unspecified phase)
0.8504	High Similarity	NPD1201	Approved
0.8496	Intermediate Similarity	NPD943	Approved
0.8468	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD5404	Approved
0.8456	Intermediate Similarity	NPD5406	Approved
0.8456	Intermediate Similarity	NPD5408	Approved
0.8456	Intermediate Similarity	NPD5405	Approved
0.8264	Intermediate Similarity	NPD9266	Approved
0.8264	Intermediate Similarity	NPD74	Approved
0.8188	Intermediate Similarity	NPD2935	Discontinued
0.8182	Intermediate Similarity	NPD9264	Approved
0.8182	Intermediate Similarity	NPD9263	Approved
0.8182	Intermediate Similarity	NPD9267	Approved
0.8116	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD9493	Approved
0.7986	Intermediate Similarity	NPD1510	Phase 2
0.797	Intermediate Similarity	NPD1203	Approved
0.7956	Intermediate Similarity	NPD1240	Approved
0.7917	Intermediate Similarity	NPD7390	Discontinued
0.7886	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD9281	Approved
0.7851	Intermediate Similarity	NPD9261	Approved
0.7842	Intermediate Similarity	NPD1607	Approved
0.7832	Intermediate Similarity	NPD3750	Approved
0.781	Intermediate Similarity	NPD3764	Approved
0.78	Intermediate Similarity	NPD7819	Suspended
0.777	Intermediate Similarity	NPD3226	Approved
0.7746	Intermediate Similarity	NPD2346	Discontinued
0.773	Intermediate Similarity	NPD2799	Discontinued
0.7692	Intermediate Similarity	NPD1549	Phase 2
0.7647	Intermediate Similarity	NPD3749	Approved
0.7622	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2344	Approved
0.7612	Intermediate Similarity	NPD9269	Phase 2
0.7612	Intermediate Similarity	NPD9717	Approved
0.7576	Intermediate Similarity	NPD9268	Approved
0.7576	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD2313	Discontinued
0.7554	Intermediate Similarity	NPD3268	Approved
0.7551	Intermediate Similarity	NPD1511	Approved
0.755	Intermediate Similarity	NPD7411	Suspended
0.7518	Intermediate Similarity	NPD2798	Approved
0.7517	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9545	Approved
0.7483	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3748	Approved
0.7452	Intermediate Similarity	NPD6232	Discontinued
0.745	Intermediate Similarity	NPD1512	Approved
0.7431	Intermediate Similarity	NPD1551	Phase 2
0.7429	Intermediate Similarity	NPD411	Approved
0.7421	Intermediate Similarity	NPD7473	Discontinued
0.7415	Intermediate Similarity	NPD2309	Approved
0.7394	Intermediate Similarity	NPD447	Suspended
0.7388	Intermediate Similarity	NPD2932	Approved
0.7388	Intermediate Similarity	NPD3019	Approved
0.7383	Intermediate Similarity	NPD2534	Approved
0.7383	Intermediate Similarity	NPD2533	Approved
0.7383	Intermediate Similarity	NPD2532	Approved
0.7383	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1471	Phase 3
0.7376	Intermediate Similarity	NPD520	Approved
0.7372	Intermediate Similarity	NPD1283	Approved
0.7365	Intermediate Similarity	NPD3300	Phase 2
0.7358	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD3266	Approved
0.7319	Intermediate Similarity	NPD3267	Approved
0.7315	Intermediate Similarity	NPD6799	Approved
0.7308	Intermediate Similarity	NPD7075	Discontinued
0.729	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1934	Approved
0.7267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6599	Discontinued
0.7255	Intermediate Similarity	NPD4380	Phase 2
0.7241	Intermediate Similarity	NPD4308	Phase 3
0.723	Intermediate Similarity	NPD7003	Approved
0.723	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1608	Approved
0.7226	Intermediate Similarity	NPD1465	Phase 2
0.7226	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5951	Approved
0.7194	Intermediate Similarity	NPD2797	Approved
0.7192	Intermediate Similarity	NPD2796	Approved
0.719	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1243	Approved
0.7153	Intermediate Similarity	NPD1281	Approved
0.7153	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1929	Approved
0.7143	Intermediate Similarity	NPD1930	Approved
0.7134	Intermediate Similarity	NPD3882	Suspended
0.7134	Intermediate Similarity	NPD7768	Phase 2
0.7122	Intermediate Similarity	NPD1876	Approved
0.7115	Intermediate Similarity	NPD2801	Approved
0.7114	Intermediate Similarity	NPD1196	Approved
0.7114	Intermediate Similarity	NPD4628	Phase 3
0.7101	Intermediate Similarity	NPD3972	Approved
0.7089	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1237	Approved
0.7086	Intermediate Similarity	NPD1543	Discontinued
0.7078	Intermediate Similarity	NPD7458	Discontinued
0.707	Intermediate Similarity	NPD3817	Phase 2
0.7063	Intermediate Similarity	NPD6959	Discontinued
0.7051	Intermediate Similarity	NPD6801	Discontinued
0.7049	Intermediate Similarity	NPD1202	Approved
0.7047	Intermediate Similarity	NPD1195	Approved
0.704	Intermediate Similarity	NPD3020	Approved
0.7025	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6663	Approved
0.7007	Intermediate Similarity	NPD4626	Approved
0.7007	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD8166	Discontinued
0.7	Intermediate Similarity	NPD3225	Approved
0.7	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1759	Phase 1
0.6984	Remote Similarity	NPD1242	Phase 1
0.6978	Remote Similarity	NPD1481	Phase 2
0.6972	Remote Similarity	NPD5736	Approved
0.6966	Remote Similarity	NPD4307	Phase 2
0.6962	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3023	Approved
0.6957	Remote Similarity	NPD3026	Approved
0.6951	Remote Similarity	NPD3818	Discontinued
0.6948	Remote Similarity	NPD920	Approved
0.6947	Remote Similarity	NPD3022	Approved
0.6947	Remote Similarity	NPD3021	Approved
0.6944	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD9256	Approved
0.6942	Remote Similarity	NPD9258	Approved
0.6935	Remote Similarity	NPD2860	Approved
0.6935	Remote Similarity	NPD2859	Approved
0.6934	Remote Similarity	NPD3025	Approved
0.6934	Remote Similarity	NPD1651	Approved
0.6934	Remote Similarity	NPD3024	Approved
0.6933	Remote Similarity	NPD2800	Approved
0.6929	Remote Similarity	NPD1932	Approved
0.6929	Remote Similarity	NPD1755	Approved
0.6928	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2342	Discontinued
0.6918	Remote Similarity	NPD1933	Approved
0.6912	Remote Similarity	NPD1758	Phase 1
0.6909	Remote Similarity	NPD5844	Phase 1
0.6906	Remote Similarity	NPD1535	Discovery
0.6901	Remote Similarity	NPD1019	Discontinued
0.6889	Remote Similarity	NPD255	Approved
0.6889	Remote Similarity	NPD256	Approved
0.6887	Remote Similarity	NPD3400	Discontinued
0.6884	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6273	Approved
0.6882	Remote Similarity	NPD8150	Discontinued
0.688	Remote Similarity	NPD288	Approved
0.6855	Remote Similarity	NPD2296	Approved
0.6855	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2933	Approved
0.6855	Remote Similarity	NPD5402	Approved
0.6855	Remote Similarity	NPD2934	Approved
0.6855	Remote Similarity	NPD4288	Approved
0.6853	Remote Similarity	NPD9494	Approved
0.685	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4060	Phase 1
0.6842	Remote Similarity	NPD2354	Approved
0.6842	Remote Similarity	NPD6190	Approved
0.6839	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5403	Approved
0.6832	Remote Similarity	NPD919	Approved
0.6829	Remote Similarity	NPD6166	Phase 2
0.6829	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5953	Discontinued
0.6821	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5401	Approved
0.681	Remote Similarity	NPD6808	Phase 2
0.681	Remote Similarity	NPD5711	Approved
0.681	Remote Similarity	NPD5710	Approved
0.68	Remote Similarity	NPD844	Approved
0.68	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD940	Approved
0.6797	Remote Similarity	NPD846	Approved
0.6791	Remote Similarity	NPD7635	Approved
0.6783	Remote Similarity	NPD258	Approved
0.6783	Remote Similarity	NPD257	Approved
0.6776	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2066	Phase 3
0.6766	Remote Similarity	NPD7074	Phase 3
0.6757	Remote Similarity	NPD6651	Approved
0.6753	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4878	Approved
0.6735	Remote Similarity	NPD2979	Phase 3

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