NPASS Compound

Structure

NPC474814 OpenBabel07101719512D 29 31 0 0 0 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 14 1 0 0 0 0 2 5 1 0 0 0 0 2 15 2 0 0 0 0 3 6 1 0 0 0 0 3 16 2 0 0 0 0 4 20 1 0 0 0 0 5 18 2 0 0 0 0 6 19 2 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 28 2 0 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	397.12
Volume:	392.267
LogP:	3.498
LogD:	1.986
LogS:	-3.27
# Rotatable Bonds:	6
TPSA:	141.69
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.349
Synthetic Accessibility Score:	2.56
Fsp3:	0.095
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.131
MDCK Permeability:	4.553058715828229e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.049
Human Intestinal Absorption (HIA):	0.885
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	97.37454986572266%
Volume Distribution (VD):	0.398
Pgp-substrate:	3.1897928714752197%

ADMET: Metabolism

CYP1A2-inhibitor:	0.457
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.544
CYP2C9-substrate:	0.189
CYP2D6-inhibitor:	0.453
CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.035

ADMET: Excretion

Clearance (CL):	17.306
Half-life (T1/2):	0.972

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.366
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.225
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.936
Carcinogencity:	0.098
Eye Corrosion:	0.003
Eye Irritation:	0.881
Respiratory Toxicity:	0.054

Download Data

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

Natural Product: NPC474814

Natural Product ID:	NPC474814
*Common Name:**	5-(Bis(2,5-Dihydroxybenzyl)Amino)-2-Hydroxybenzoic Acid
IUPAC Name:	5-[bis[(2,5-dihydroxyphenyl)methyl]amino]-2-hydroxybenzoic acid
Synonyms:
Standard InCHIKey:	ZQWHNKZTMMWBHH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H19NO7/c23-15-2-5-18(25)12(7-15)10-22(11-13-8-16(24)3-6-19(13)26)14-1-4-20(27)17(9-14)21(28)29/h1-9,23-27H,10-11H2,(H,28,29)
SMILES:	C1=CC(=C(C=C1N(CC2=C(C=CC(=C2)O)O)CC3=C(C=CC(=C3)O)O)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483830
PubChem CID:	44593598
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000185] Phenylmethylamines [CHEMONTID:0004204] Phenylbenzamines

*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
NPO17163	Streptomyces griseolavendus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2614420]

☑ 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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	=	0.01	ug.mL-1	PMID[513161]
NPT1556	Individual Protein	Epidermal growth factor receptor erbB1	Mus musculus	IC50	=	0.011	ug.mL-1	PMID[513162]

☑ 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 NPC474814 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	341
0.1-0.2	2287
0.2-0.3	9561
0.3-0.4	7158
0.4-0.5	9351
0.5-0.6	13071
0.6-0.7	913
0.7-0.8	7
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC112336
0.961	High Similarity	NPC199737
0.9308	High Similarity	NPC471778
0.8855	High Similarity	NPC474815
0.8642	High Similarity	NPC475983
0.8113	Intermediate Similarity	NPC323798
0.7962	Intermediate Similarity	NPC316574
0.7616	Intermediate Similarity	NPC204867
0.7553	Intermediate Similarity	NPC317727
0.7531	Intermediate Similarity	NPC181526
0.744	Intermediate Similarity	NPC144691
0.7348	Intermediate Similarity	NPC298320
0.7299	Intermediate Similarity	NPC93653
0.7229	Intermediate Similarity	NPC301702
0.7211	Intermediate Similarity	NPC170333
0.7207	Intermediate Similarity	NPC469671
0.7207	Intermediate Similarity	NPC126676
0.7179	Intermediate Similarity	NPC133156
0.7102	Intermediate Similarity	NPC27904
0.7097	Intermediate Similarity	NPC132751
0.7059	Intermediate Similarity	NPC288854
0.705	Intermediate Similarity	NPC295479
0.705	Intermediate Similarity	NPC220241
0.7037	Intermediate Similarity	NPC314098
0.7018	Intermediate Similarity	NPC315829
0.7	Intermediate Similarity	NPC70340
0.699	Remote Similarity	NPC118189
0.6989	Remote Similarity	NPC470317
0.6964	Remote Similarity	NPC43477
0.6963	Remote Similarity	NPC206109
0.6963	Remote Similarity	NPC114039
0.6959	Remote Similarity	NPC146370
0.6947	Remote Similarity	NPC474059
0.6935	Remote Similarity	NPC288305
0.6911	Remote Similarity	NPC1820
0.6909	Remote Similarity	NPC253476
0.6908	Remote Similarity	NPC76478
0.6905	Remote Similarity	NPC314252
0.6903	Remote Similarity	NPC312800
0.6902	Remote Similarity	NPC471743
0.6895	Remote Similarity	NPC18890
0.6886	Remote Similarity	NPC43218
0.6878	Remote Similarity	NPC150308
0.6865	Remote Similarity	NPC477187
0.6859	Remote Similarity	NPC5630
0.6859	Remote Similarity	NPC313293
0.685	Remote Similarity	NPC198160
0.685	Remote Similarity	NPC212123
0.6845	Remote Similarity	NPC182853
0.6845	Remote Similarity	NPC134702
0.6842	Remote Similarity	NPC297322
0.6837	Remote Similarity	NPC17160
0.6837	Remote Similarity	NPC313720
0.6833	Remote Similarity	NPC292143
0.6833	Remote Similarity	NPC139506
0.6824	Remote Similarity	NPC13696
0.6823	Remote Similarity	NPC92803
0.6821	Remote Similarity	NPC90229
0.6818	Remote Similarity	NPC15987
0.6816	Remote Similarity	NPC100573
0.6816	Remote Similarity	NPC207873
0.6815	Remote Similarity	NPC229353
0.6814	Remote Similarity	NPC268223
0.6813	Remote Similarity	NPC244351
0.6788	Remote Similarity	NPC31539
0.678	Remote Similarity	NPC148391
0.677	Remote Similarity	NPC477153
0.6765	Remote Similarity	NPC116178
0.6758	Remote Similarity	NPC182131
0.675	Remote Similarity	NPC198336
0.6743	Remote Similarity	NPC241392
0.6732	Remote Similarity	NPC114468
0.6732	Remote Similarity	NPC217903
0.6732	Remote Similarity	NPC321166
0.6727	Remote Similarity	NPC120251
0.6708	Remote Similarity	NPC283514
0.6706	Remote Similarity	NPC204156
0.6703	Remote Similarity	NPC477185
0.6702	Remote Similarity	NPC85613
0.6701	Remote Similarity	NPC17677
0.6701	Remote Similarity	NPC226708
0.6699	Remote Similarity	NPC2905
0.6684	Remote Similarity	NPC9475
0.6683	Remote Similarity	NPC305542
0.6667	Remote Similarity	NPC7560
0.6667	Remote Similarity	NPC184579
0.6667	Remote Similarity	NPC280714
0.6667	Remote Similarity	NPC473360
0.6667	Remote Similarity	NPC233165
0.665	Remote Similarity	NPC30749
0.665	Remote Similarity	NPC90185
0.6646	Remote Similarity	NPC96915
0.6646	Remote Similarity	NPC269414
0.6626	Remote Similarity	NPC472244
0.6626	Remote Similarity	NPC470343
0.662	Remote Similarity	NPC285254
0.6619	Remote Similarity	NPC157983
0.6619	Remote Similarity	NPC118154
0.6615	Remote Similarity	NPC262725
0.6614	Remote Similarity	NPC5167
0.6612	Remote Similarity	NPC299582
0.6608	Remote Similarity	NPC62272
0.6608	Remote Similarity	NPC242933
0.6606	Remote Similarity	NPC71525
0.6601	Remote Similarity	NPC478075
0.66	Remote Similarity	NPC232600
0.6598	Remote Similarity	NPC144381
0.6597	Remote Similarity	NPC471742
0.6593	Remote Similarity	NPC289776
0.6593	Remote Similarity	NPC133470
0.6593	Remote Similarity	NPC191863
0.6584	Remote Similarity	NPC272454
0.6584	Remote Similarity	NPC301987
0.6584	Remote Similarity	NPC115188
0.6584	Remote Similarity	NPC244994
0.6584	Remote Similarity	NPC179092
0.6584	Remote Similarity	NPC26433
0.6584	Remote Similarity	NPC292665
0.6584	Remote Similarity	NPC178395
0.6584	Remote Similarity	NPC159760
0.6584	Remote Similarity	NPC35856
0.6584	Remote Similarity	NPC222876
0.658	Remote Similarity	NPC21425
0.6578	Remote Similarity	NPC470548
0.6578	Remote Similarity	NPC95412
0.6578	Remote Similarity	NPC303225
0.6575	Remote Similarity	NPC301163
0.6571	Remote Similarity	NPC478039
0.6566	Remote Similarity	NPC95537
0.6566	Remote Similarity	NPC316282
0.6559	Remote Similarity	NPC83241
0.6548	Remote Similarity	NPC469815
0.6548	Remote Similarity	NPC469816
0.6541	Remote Similarity	NPC125252
0.6535	Remote Similarity	NPC207971
0.6535	Remote Similarity	NPC317572
0.6533	Remote Similarity	NPC234933
0.6531	Remote Similarity	NPC56170
0.6524	Remote Similarity	NPC236189
0.6524	Remote Similarity	NPC73280
0.6524	Remote Similarity	NPC195120
0.6524	Remote Similarity	NPC87560
0.6522	Remote Similarity	NPC233282
0.6522	Remote Similarity	NPC260837
0.652	Remote Similarity	NPC308943
0.6519	Remote Similarity	NPC222982
0.6519	Remote Similarity	NPC240163
0.6517	Remote Similarity	NPC471489
0.6515	Remote Similarity	NPC303214
0.6515	Remote Similarity	NPC125924
0.6512	Remote Similarity	NPC238108
0.6512	Remote Similarity	NPC245923
0.6512	Remote Similarity	NPC472243
0.6512	Remote Similarity	NPC13249
0.651	Remote Similarity	NPC203635
0.6509	Remote Similarity	NPC99724
0.6509	Remote Similarity	NPC329830
0.6508	Remote Similarity	NPC127082
0.6507	Remote Similarity	NPC234772
0.6505	Remote Similarity	NPC474366
0.6505	Remote Similarity	NPC309845
0.6502	Remote Similarity	NPC268077
0.65	Remote Similarity	NPC5374
0.6495	Remote Similarity	NPC473815
0.6494	Remote Similarity	NPC100551
0.6494	Remote Similarity	NPC225243
0.6492	Remote Similarity	NPC73555
0.6492	Remote Similarity	NPC327005
0.6485	Remote Similarity	NPC167055
0.6485	Remote Similarity	NPC240744
0.6485	Remote Similarity	NPC288759
0.6481	Remote Similarity	NPC165197
0.648	Remote Similarity	NPC28510
0.648	Remote Similarity	NPC68967
0.648	Remote Similarity	NPC203628
0.6479	Remote Similarity	NPC148124
0.6479	Remote Similarity	NPC251071
0.6474	Remote Similarity	NPC256268
0.6474	Remote Similarity	NPC4214
0.6474	Remote Similarity	NPC474041
0.6474	Remote Similarity	NPC228609
0.6473	Remote Similarity	NPC9894
0.6471	Remote Similarity	NPC173295
0.6467	Remote Similarity	NPC189116
0.6467	Remote Similarity	NPC48248
0.6465	Remote Similarity	NPC198401
0.6465	Remote Similarity	NPC146724
0.6463	Remote Similarity	NPC375356
0.6462	Remote Similarity	NPC183805
0.6459	Remote Similarity	NPC298449
0.6458	Remote Similarity	NPC243058
0.6458	Remote Similarity	NPC469973
0.6458	Remote Similarity	NPC99723
0.6457	Remote Similarity	NPC314186
0.6453	Remote Similarity	NPC472308
0.6453	Remote Similarity	NPC474813
0.6453	Remote Similarity	NPC155211
0.6453	Remote Similarity	NPC471316
0.6453	Remote Similarity	NPC238412
0.6453	Remote Similarity	NPC272268

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 NPC474814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	683
0.2-0.3	1022
0.3-0.4	1252
0.4-0.5	3120
0.5-0.6	2480
0.6-0.7	350
0.7-0.8	30
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8443	Intermediate Similarity	NPD1913	Phase 1
0.8383	Intermediate Similarity	NPD1839	Phase 1
0.8344	Intermediate Similarity	NPD1196	Approved
0.828	Intermediate Similarity	NPD1195	Approved
0.8187	Intermediate Similarity	NPD2361	Approved
0.8187	Intermediate Similarity	NPD1543	Discontinued
0.8129	Intermediate Similarity	NPD2359	Approved
0.7962	Intermediate Similarity	NPD9279	Approved
0.7889	Intermediate Similarity	NPD5928	Phase 1
0.7654	Intermediate Similarity	NPD3253	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3229	Phase 2
0.7614	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5608	Approved
0.7553	Intermediate Similarity	NPD5609	Approved
0.75	Intermediate Similarity	NPD5194	Approved
0.75	Intermediate Similarity	NPD5196	Approved
0.75	Intermediate Similarity	NPD5197	Approved
0.746	Intermediate Similarity	NPD6874	Approved
0.7448	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD2366	Approved
0.7407	Intermediate Similarity	NPD4668	Phase 2
0.7287	Intermediate Similarity	NPD5610	Approved
0.7273	Intermediate Similarity	NPD5871	Discontinued
0.7263	Intermediate Similarity	NPD5195	Discontinued
0.7253	Intermediate Similarity	NPD5445	Approved
0.7245	Intermediate Similarity	NPD7300	Phase 3
0.7245	Intermediate Similarity	NPD7302	Phase 3
0.7229	Intermediate Similarity	NPD75	Approved
0.7229	Intermediate Similarity	NPD9277	Approved
0.7175	Intermediate Similarity	NPD1168	Approved
0.7169	Intermediate Similarity	NPD9278	Suspended
0.7169	Intermediate Similarity	NPD9275	Approved
0.7169	Intermediate Similarity	NPD9276	Approved
0.7169	Intermediate Similarity	NPD9274	Approved
0.716	Intermediate Similarity	NPD3141	Discontinued
0.7126	Intermediate Similarity	NPD2672	Discontinued
0.71	Intermediate Similarity	NPD7301	Phase 3
0.7097	Intermediate Similarity	NPD8167	Discontinued
0.7083	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4888	Discontinued
0.7059	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5637	Discontinued
0.7026	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1189	Approved
0.7022	Intermediate Similarity	NPD955	Approved
0.7011	Intermediate Similarity	NPD5086	Approved
0.6982	Remote Similarity	NPD1625	Approved
0.6961	Remote Similarity	NPD1161	Approved
0.6949	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7324	Discontinued
0.6927	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6161	Approved
0.6907	Remote Similarity	NPD6162	Approved
0.6904	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD1544	Phase 1
0.6893	Remote Similarity	NPD2899	Discontinued
0.6882	Remote Similarity	NPD2820	Phase 3
0.6882	Remote Similarity	NPD6184	Discontinued
0.6878	Remote Similarity	NPD3154	Approved
0.6878	Remote Similarity	NPD3153	Approved
0.6875	Remote Similarity	NPD5937	Approved
0.6868	Remote Similarity	NPD5847	Phase 1
0.6865	Remote Similarity	NPD5498	Phase 2
0.6865	Remote Similarity	NPD1170	Approved
0.6859	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5823	Approved
0.6845	Remote Similarity	NPD7292	Approved
0.6834	Remote Similarity	NPD1294	Discontinued
0.6833	Remote Similarity	NPD3453	Discontinued
0.6824	Remote Similarity	NPD2365	Approved
0.6818	Remote Similarity	NPD5488	Discontinued
0.6813	Remote Similarity	NPD2821	Approved
0.6798	Remote Similarity	NPD6844	Discontinued
0.6793	Remote Similarity	NPD2246	Approved
0.6793	Remote Similarity	NPD2248	Approved
0.6792	Remote Similarity	NPD2761	Approved
0.6784	Remote Similarity	NPD4430	Phase 2
0.678	Remote Similarity	NPD4679	Discontinued
0.678	Remote Similarity	NPD3684	Discontinued
0.6771	Remote Similarity	NPD4259	Approved
0.6771	Remote Similarity	NPD4258	Approved
0.6766	Remote Similarity	NPD2791	Discontinued
0.6757	Remote Similarity	NPD5466	Approved
0.6753	Remote Similarity	NPD4539	Phase 1
0.675	Remote Similarity	NPD4465	Phase 2
0.675	Remote Similarity	NPD4467	Phase 2
0.6747	Remote Similarity	NPD520	Approved
0.6746	Remote Similarity	NPD1626	Approved
0.6743	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6457	Approved
0.6719	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6807	Phase 3
0.6714	Remote Similarity	NPD7654	Discontinued
0.6706	Remote Similarity	NPD3391	Approved
0.6706	Remote Similarity	NPD2935	Discontinued
0.6702	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7569	Approved
0.6701	Remote Similarity	NPD7570	Approved
0.67	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6636	Phase 3
0.6686	Remote Similarity	NPD4161	Discontinued
0.6684	Remote Similarity	NPD7546	Discontinued
0.6667	Remote Similarity	NPD6283	Phase 2
0.6667	Remote Similarity	NPD5860	Discontinued
0.6667	Remote Similarity	NPD6250	Discontinued
0.665	Remote Similarity	NPD956	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7626	Approved
0.665	Remote Similarity	NPD7627	Approved
0.6648	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2836	Approved
0.6617	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5430	Discontinued
0.6612	Remote Similarity	NPD3252	Approved
0.6611	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD5404	Approved
0.6608	Remote Similarity	NPD5406	Approved
0.6608	Remote Similarity	NPD5405	Approved
0.6608	Remote Similarity	NPD5408	Approved
0.6601	Remote Similarity	NPD7043	Discontinued
0.6601	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2434	Approved
0.6596	Remote Similarity	NPD3793	Phase 3
0.6596	Remote Similarity	NPD6020	Phase 2
0.6595	Remote Similarity	NPD5186	Approved
0.6595	Remote Similarity	NPD5183	Approved
0.6588	Remote Similarity	NPD2670	Approved
0.6578	Remote Similarity	NPD3446	Phase 1
0.6566	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7996	Phase 2
0.6559	Remote Similarity	NPD3975	Discontinued
0.6546	Remote Similarity	NPD1898	Discontinued
0.6545	Remote Similarity	NPD2802	Phase 3
0.6543	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2247	Approved
0.6541	Remote Similarity	NPD2681	Approved
0.6541	Remote Similarity	NPD2680	Approved
0.6541	Remote Similarity	NPD2249	Approved
0.654	Remote Similarity	NPD3437	Discontinued
0.6538	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD1220	Phase 1
0.6517	Remote Similarity	NPD1230	Approved
0.6516	Remote Similarity	NPD4561	Discontinued
0.6516	Remote Similarity	NPD9376	Approved
0.6514	Remote Similarity	NPD3301	Approved
0.6512	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6484	Approved
0.6495	Remote Similarity	NPD6483	Approved
0.6494	Remote Similarity	NPD9266	Approved
0.6494	Remote Similarity	NPD74	Approved
0.6489	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2514	Approved
0.6485	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5026	Approved
0.6458	Remote Similarity	NPD4955	Approved
0.6458	Remote Similarity	NPD36	Approved
0.6458	Remote Similarity	NPD4954	Approved
0.6458	Remote Similarity	NPD5034	Approved
0.6458	Remote Similarity	NPD5028	Approved
0.6453	Remote Similarity	NPD3170	Approved
0.6453	Remote Similarity	NPD13	Approved
0.6453	Remote Similarity	NPD697	Approved
0.6453	Remote Similarity	NPD699	Approved
0.6453	Remote Similarity	NPD12	Approved
0.6453	Remote Similarity	NPD700	Approved
0.645	Remote Similarity	NPD1527	Phase 2
0.645	Remote Similarity	NPD5071	Phase 2
0.6449	Remote Similarity	NPD3912	Discontinued
0.6447	Remote Similarity	NPD5968	Phase 3
0.6445	Remote Similarity	NPD7293	Approved
0.6441	Remote Similarity	NPD2114	Discontinued
0.644	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6604	Discontinued
0.6432	Remote Similarity	NPD5507	Approved
0.6432	Remote Similarity	NPD5506	Approved
0.6432	Remote Similarity	NPD5548	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD9263	Approved
0.6429	Remote Similarity	NPD9264	Approved
0.6429	Remote Similarity	NPD9267	Approved
0.6425	Remote Similarity	NPD5923	Phase 1
0.6425	Remote Similarity	NPD1670	Discontinued
0.6424	Remote Similarity	NPD6320	Approved
0.6421	Remote Similarity	NPD1221	Approved
0.6421	Remote Similarity	NPD3965	Phase 1
0.6415	Remote Similarity	NPD5496	Approved
0.6413	Remote Similarity	NPD7417	Discontinued
0.6413	Remote Similarity	NPD1210	Approved
0.6408	Remote Similarity	NPD4082	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