NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.06
Volume:	171.489
LogP:	2.142
LogD:	1.319
LogS:	-1.737
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	2.632
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.668
MDCK Permeability:	8.5242545537767e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.542
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.337
Plasma Protein Binding (PPB):	92.00269317626953%
Volume Distribution (VD):	0.63
Pgp-substrate:	5.091502666473389%

ADMET: Metabolism

CYP1A2-inhibitor:	0.821
CYP1A2-substrate:	0.822
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.268
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.617
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.33
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	12.239
Half-life (T1/2):	0.845

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.023
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.287
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.893
Carcinogencity:	0.137
Eye Corrosion:	0.953
Eye Irritation:	0.976
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC62219

Natural Product ID:	NPC62219
*Common Name:**	3,6-Dimethyl-Beta-Resorcylaldehyde
IUPAC Name:	2,4-dihydroxy-3,6-dimethylbenzaldehyde
Synonyms:
Standard InCHIKey:	XOAAGSCMGLMPKG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O3/c1-5-3-8(11)6(2)9(12)7(5)4-10/h3-4,11-12H,1-2H3
SMILES:	O=Cc1c(C)cc(c(c1O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448641
PubChem CID:	596811
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004208] Xylenes [CHEMONTID:0004212] Xylenols [CHEMONTID:0004215] p-Xylenols

*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
NPO33104	sepedonium chrysospermum	Species	Hypocreaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[17067166]
NPO33104	sepedonium chrysospermum	Species	Hypocreaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[18702471]
NPO13627	Sphaeria macula	n.a.	n.a.	n.a.	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	126000.0	nM	PMID[488224]

☑ 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 NPC62219 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	363
0.1-0.2	1743
0.2-0.3	4219
0.3-0.4	12256
0.4-0.5	6826
0.5-0.6	5615
0.6-0.7	6943
0.7-0.8	4078
0.8-0.85	498
0.85-0.9	134
0.9-0.95	16
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9685	High Similarity	NPC474519
0.9609	High Similarity	NPC278375
0.9318	High Similarity	NPC162939
0.9248	High Similarity	NPC99441
0.9179	High Similarity	NPC37530
0.9154	High Similarity	NPC180261
0.9154	High Similarity	NPC267205
0.9154	High Similarity	NPC48036
0.9154	High Similarity	NPC37299
0.9147	High Similarity	NPC41847
0.9127	High Similarity	NPC477454
0.9106	High Similarity	NPC294964
0.9091	High Similarity	NPC158481
0.9084	High Similarity	NPC474394
0.9055	High Similarity	NPC473691
0.9015	High Similarity	NPC290803
0.8976	High Similarity	NPC201728
0.8976	High Similarity	NPC262671
0.8971	High Similarity	NPC73061
0.8947	High Similarity	NPC118919
0.8947	High Similarity	NPC254847
0.8947	High Similarity	NPC191976
0.8897	High Similarity	NPC187843
0.8897	High Similarity	NPC204045
0.8897	High Similarity	NPC305845
0.8889	High Similarity	NPC190457
0.8881	High Similarity	NPC53414
0.8881	High Similarity	NPC53206
0.8881	High Similarity	NPC471905
0.8846	High Similarity	NPC92624
0.8832	High Similarity	NPC474961
0.8832	High Similarity	NPC135524
0.8824	High Similarity	NPC165172
0.881	High Similarity	NPC215392
0.8806	High Similarity	NPC86524
0.8797	High Similarity	NPC282780
0.8797	High Similarity	NPC166480
0.8779	High Similarity	NPC17840
0.8779	High Similarity	NPC247477
0.8779	High Similarity	NPC259942
0.8779	High Similarity	NPC147757
0.8769	High Similarity	NPC41263
0.8768	High Similarity	NPC159721
0.876	High Similarity	NPC160499
0.8759	High Similarity	NPC110810
0.875	High Similarity	NPC143438
0.875	High Similarity	NPC242994
0.875	High Similarity	NPC138099
0.8741	High Similarity	NPC194579
0.874	High Similarity	NPC91105
0.874	High Similarity	NPC309765
0.873	High Similarity	NPC146642
0.8722	High Similarity	NPC153783
0.8712	High Similarity	NPC219892
0.8712	High Similarity	NPC189823
0.871	High Similarity	NPC230349
0.8705	High Similarity	NPC151607
0.8705	High Similarity	NPC21599
0.8705	High Similarity	NPC42540
0.8705	High Similarity	NPC244691
0.8705	High Similarity	NPC471906
0.8705	High Similarity	NPC48762
0.8705	High Similarity	NPC193703
0.8702	High Similarity	NPC476119
0.8696	High Similarity	NPC182255
0.8696	High Similarity	NPC94076
0.8692	High Similarity	NPC83572
0.8686	High Similarity	NPC169452
0.8686	High Similarity	NPC183345
0.8686	High Similarity	NPC181560
0.8682	High Similarity	NPC475733
0.8682	High Similarity	NPC131799
0.8672	High Similarity	NPC65761
0.8672	High Similarity	NPC472029
0.8661	High Similarity	NPC226275
0.8661	High Similarity	NPC303737
0.8657	High Similarity	NPC44437
0.8651	High Similarity	NPC294037
0.8647	High Similarity	NPC478190
0.8643	High Similarity	NPC34482
0.864	High Similarity	NPC283844
0.864	High Similarity	NPC209486
0.864	High Similarity	NPC40649
0.8636	High Similarity	NPC296158
0.8633	High Similarity	NPC471731
0.8633	High Similarity	NPC84266
0.8626	High Similarity	NPC3009
0.8623	High Similarity	NPC246638
0.8615	High Similarity	NPC295202
0.8615	High Similarity	NPC49647
0.8615	High Similarity	NPC136342
0.8615	High Similarity	NPC227741
0.8613	High Similarity	NPC88269
0.8613	High Similarity	NPC275356
0.8603	High Similarity	NPC178467
0.8603	High Similarity	NPC70380
0.8603	High Similarity	NPC71256
0.8603	High Similarity	NPC53001
0.8603	High Similarity	NPC474849
0.8603	High Similarity	NPC65837
0.8603	High Similarity	NPC149372
0.8603	High Similarity	NPC474771
0.8594	High Similarity	NPC218333
0.8583	High Similarity	NPC149246
0.8582	High Similarity	NPC470570
0.8571	High Similarity	NPC161617
0.8571	High Similarity	NPC275504
0.8571	High Similarity	NPC85342
0.8561	High Similarity	NPC471733
0.8561	High Similarity	NPC193555
0.8551	High Similarity	NPC156872
0.8551	High Similarity	NPC472601
0.8551	High Similarity	NPC472600
0.854	High Similarity	NPC87723
0.854	High Similarity	NPC94248
0.854	High Similarity	NPC191835
0.854	High Similarity	NPC475974
0.854	High Similarity	NPC212693
0.8538	High Similarity	NPC10926
0.8529	High Similarity	NPC50455
0.8529	High Similarity	NPC315275
0.8529	High Similarity	NPC291454
0.8529	High Similarity	NPC235115
0.8527	High Similarity	NPC306288
0.8521	High Similarity	NPC53362
0.8521	High Similarity	NPC166583
0.8521	High Similarity	NPC290194
0.8519	High Similarity	NPC12070
0.8507	High Similarity	NPC175738
0.85	High Similarity	NPC313047
0.85	High Similarity	NPC474203
0.85	High Similarity	NPC174905
0.85	High Similarity	NPC295712
0.85	High Similarity	NPC293545
0.85	High Similarity	NPC451542
0.8489	Intermediate Similarity	NPC472603
0.8489	Intermediate Similarity	NPC472605
0.8489	Intermediate Similarity	NPC472604
0.8489	Intermediate Similarity	NPC470842
0.8489	Intermediate Similarity	NPC290550
0.8485	Intermediate Similarity	NPC179898
0.8478	Intermediate Similarity	NPC474655
0.8478	Intermediate Similarity	NPC105456
0.8478	Intermediate Similarity	NPC139634
0.8473	Intermediate Similarity	NPC62952
0.8473	Intermediate Similarity	NPC267846
0.8473	Intermediate Similarity	NPC8745
0.8467	Intermediate Similarity	NPC135837
0.8467	Intermediate Similarity	NPC471452
0.8462	Intermediate Similarity	NPC13238
0.8462	Intermediate Similarity	NPC173978
0.8462	Intermediate Similarity	NPC152525
0.8462	Intermediate Similarity	NPC68756
0.8456	Intermediate Similarity	NPC475917
0.8456	Intermediate Similarity	NPC182496
0.8456	Intermediate Similarity	NPC249272
0.8456	Intermediate Similarity	NPC180905
0.8456	Intermediate Similarity	NPC161632
0.8451	Intermediate Similarity	NPC225173
0.8451	Intermediate Similarity	NPC163846
0.845	Intermediate Similarity	NPC282577
0.8444	Intermediate Similarity	NPC213485
0.8444	Intermediate Similarity	NPC114183
0.8444	Intermediate Similarity	NPC139074
0.8444	Intermediate Similarity	NPC40524
0.8444	Intermediate Similarity	NPC314048
0.844	Intermediate Similarity	NPC227841
0.8433	Intermediate Similarity	NPC475042
0.8429	Intermediate Similarity	NPC82913
0.8425	Intermediate Similarity	NPC208806
0.8421	Intermediate Similarity	NPC474546
0.8421	Intermediate Similarity	NPC474998
0.8421	Intermediate Similarity	NPC109123
0.8417	Intermediate Similarity	NPC168471
0.8409	Intermediate Similarity	NPC30501
0.8409	Intermediate Similarity	NPC190043
0.8409	Intermediate Similarity	NPC266689
0.8409	Intermediate Similarity	NPC98254
0.8409	Intermediate Similarity	NPC169250
0.8409	Intermediate Similarity	NPC162612
0.8409	Intermediate Similarity	NPC116513
0.8409	Intermediate Similarity	NPC72158
0.8409	Intermediate Similarity	NPC23126
0.8409	Intermediate Similarity	NPC103356
0.8409	Intermediate Similarity	NPC100067
0.8409	Intermediate Similarity	NPC105157
0.8406	Intermediate Similarity	NPC123714
0.8406	Intermediate Similarity	NPC33144
0.8406	Intermediate Similarity	NPC478200
0.8406	Intermediate Similarity	NPC472602
0.8406	Intermediate Similarity	NPC9121
0.8406	Intermediate Similarity	NPC141368
0.8406	Intermediate Similarity	NPC472403
0.8406	Intermediate Similarity	NPC177307
0.8403	Intermediate Similarity	NPC477221
0.8394	Intermediate Similarity	NPC471690
0.8394	Intermediate Similarity	NPC223836
0.8392	Intermediate Similarity	NPC126767
0.8392	Intermediate Similarity	NPC125801
0.8392	Intermediate Similarity	NPC471734

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 NPC62219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	1025
0.2-0.3	1760
0.3-0.4	2994
0.4-0.5	1709
0.5-0.6	930
0.6-0.7	290
0.7-0.8	66
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD1509	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD7390	Discontinued
0.8252	Intermediate Similarity	NPD2533	Approved
0.8252	Intermediate Similarity	NPD2534	Approved
0.8252	Intermediate Similarity	NPD2532	Approved
0.8231	Intermediate Similarity	NPD1201	Approved
0.8214	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD1607	Approved
0.8102	Intermediate Similarity	NPD943	Approved
0.7985	Intermediate Similarity	NPD1470	Approved
0.7971	Intermediate Similarity	NPD1240	Approved
0.7943	Intermediate Similarity	NPD5405	Approved
0.7943	Intermediate Similarity	NPD5404	Approved
0.7943	Intermediate Similarity	NPD5406	Approved
0.7943	Intermediate Similarity	NPD5408	Approved
0.7877	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1510	Phase 2
0.7769	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6959	Discontinued
0.7721	Intermediate Similarity	NPD1164	Approved
0.7697	Intermediate Similarity	NPD7819	Suspended
0.7692	Intermediate Similarity	NPD6232	Discontinued
0.7639	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1549	Phase 2
0.7582	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1551	Phase 2
0.7547	Intermediate Similarity	NPD7473	Discontinued
0.7535	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD9493	Approved
0.75	Intermediate Similarity	NPD9269	Phase 2
0.7468	Intermediate Similarity	NPD5711	Approved
0.7468	Intermediate Similarity	NPD5710	Approved
0.7463	Intermediate Similarity	NPD9268	Approved
0.7448	Intermediate Similarity	NPD2935	Discontinued
0.7422	Intermediate Similarity	NPD74	Approved
0.7422	Intermediate Similarity	NPD9266	Approved
0.7419	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2800	Approved
0.7403	Intermediate Similarity	NPD1934	Approved
0.7388	Intermediate Similarity	NPD9545	Approved
0.7386	Intermediate Similarity	NPD4380	Phase 2
0.7361	Intermediate Similarity	NPD6651	Approved
0.736	Intermediate Similarity	NPD940	Approved
0.736	Intermediate Similarity	NPD846	Approved
0.7344	Intermediate Similarity	NPD9267	Approved
0.7344	Intermediate Similarity	NPD9263	Approved
0.7344	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD9264	Approved
0.7333	Intermediate Similarity	NPD1511	Approved
0.7329	Intermediate Similarity	NPD2796	Approved
0.7285	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1512	Approved
0.7226	Intermediate Similarity	NPD7411	Suspended
0.7215	Intermediate Similarity	NPD7075	Discontinued
0.7211	Intermediate Similarity	NPD6099	Approved
0.7211	Intermediate Similarity	NPD6100	Approved
0.719	Intermediate Similarity	NPD920	Approved
0.7181	Intermediate Similarity	NPD1243	Approved
0.7171	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6599	Discontinued
0.7153	Intermediate Similarity	NPD3019	Approved
0.7153	Intermediate Similarity	NPD4626	Approved
0.7153	Intermediate Similarity	NPD2932	Approved
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD7768	Phase 2
0.7143	Intermediate Similarity	NPD1283	Approved
0.7134	Intermediate Similarity	NPD6020	Phase 2
0.7134	Intermediate Similarity	NPD2801	Approved
0.7134	Intermediate Similarity	NPD5844	Phase 1
0.7134	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3750	Approved
0.7113	Intermediate Similarity	NPD9494	Approved
0.7108	Intermediate Similarity	NPD6559	Discontinued
0.7097	Intermediate Similarity	NPD3226	Approved
0.7063	Intermediate Similarity	NPD919	Approved
0.7055	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2346	Discontinued
0.704	Intermediate Similarity	NPD288	Approved
0.7039	Intermediate Similarity	NPD3300	Phase 2
0.7031	Intermediate Similarity	NPD9261	Approved
0.702	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1242	Phase 1
0.7	Intermediate Similarity	NPD3749	Approved
0.6993	Remote Similarity	NPD6799	Approved
0.6975	Remote Similarity	NPD1247	Approved
0.6966	Remote Similarity	NPD411	Approved
0.6963	Remote Similarity	NPD9281	Approved
0.6962	Remote Similarity	NPD6801	Discontinued
0.696	Remote Similarity	NPD844	Approved
0.6957	Remote Similarity	NPD5691	Approved
0.6957	Remote Similarity	NPD1651	Approved
0.6951	Remote Similarity	NPD6166	Phase 2
0.6951	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2344	Approved
0.6929	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5494	Approved
0.6908	Remote Similarity	NPD7003	Approved
0.6897	Remote Similarity	NPD4625	Phase 3
0.6894	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9717	Approved
0.6875	Remote Similarity	NPD3817	Phase 2
0.6849	Remote Similarity	NPD3764	Approved
0.6849	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2654	Approved
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1809	Phase 2
0.6818	Remote Similarity	NPD2342	Discontinued
0.6815	Remote Similarity	NPD7635	Approved
0.6813	Remote Similarity	NPD1465	Phase 2
0.6803	Remote Similarity	NPD6663	Approved
0.68	Remote Similarity	NPD2799	Discontinued
0.68	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3748	Approved
0.6797	Remote Similarity	NPD4628	Phase 3
0.6786	Remote Similarity	NPD7074	Phase 3
0.6772	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3818	Discontinued
0.6765	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3972	Approved
0.6759	Remote Similarity	NPD5736	Approved
0.6753	Remote Similarity	NPD2309	Approved
0.6746	Remote Similarity	NPD5953	Discontinued
0.6744	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1203	Approved
0.6735	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7054	Approved
0.6715	Remote Similarity	NPD5951	Approved
0.6713	Remote Similarity	NPD4749	Approved
0.6711	Remote Similarity	NPD447	Suspended
0.6705	Remote Similarity	NPD8150	Discontinued
0.669	Remote Similarity	NPD2798	Approved
0.669	Remote Similarity	NPD422	Phase 1
0.669	Remote Similarity	NPD1610	Phase 2
0.6689	Remote Similarity	NPD520	Approved
0.6686	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD7458	Discontinued
0.6647	Remote Similarity	NPD6797	Phase 2
0.6646	Remote Similarity	NPD37	Approved
0.6643	Remote Similarity	NPD3091	Approved
0.6643	Remote Similarity	NPD1608	Approved
0.6627	Remote Similarity	NPD7286	Phase 2
0.6622	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3023	Approved
0.662	Remote Similarity	NPD3026	Approved
0.6614	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7251	Discontinued
0.6601	Remote Similarity	NPD1471	Phase 3
0.6597	Remote Similarity	NPD1755	Approved
0.6596	Remote Similarity	NPD3025	Approved
0.6596	Remote Similarity	NPD3024	Approved
0.6588	Remote Similarity	NPD1729	Discontinued
0.6581	Remote Similarity	NPD3400	Discontinued
0.6575	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3092	Approved
0.6573	Remote Similarity	NPD6535	Approved
0.6573	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6534	Approved
0.657	Remote Similarity	NPD7808	Phase 3
0.6552	Remote Similarity	NPD1876	Approved
0.6549	Remote Similarity	NPD1778	Approved
0.6545	Remote Similarity	NPD6234	Discontinued
0.6538	Remote Similarity	NPD3020	Approved
0.6534	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2979	Phase 3
0.6527	Remote Similarity	NPD7229	Phase 3
0.6525	Remote Similarity	NPD1548	Phase 1
0.6524	Remote Similarity	NPD4967	Phase 2
0.6524	Remote Similarity	NPD4965	Approved
0.6524	Remote Similarity	NPD4966	Approved
0.6519	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.651	Remote Similarity	NPD2313	Discontinued
0.6507	Remote Similarity	NPD3094	Phase 2
0.6496	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3926	Phase 2
0.6486	Remote Similarity	NPD6832	Phase 2
0.6486	Remote Similarity	NPD4908	Phase 1
0.6484	Remote Similarity	NPD6779	Approved
0.6484	Remote Similarity	NPD6782	Approved
0.6484	Remote Similarity	NPD6778	Approved
0.6484	Remote Similarity	NPD6777	Approved
0.6484	Remote Similarity	NPD6776	Approved
0.6484	Remote Similarity	NPD6780	Approved
0.6484	Remote Similarity	NPD6781	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