NPASS Compound

Structure

NPC471736 OpenBabel07101718222D 25 28 0 0 1 0 0 0 0 0999 V2000 5.2437 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2437 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2437 -0.0933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -1.0933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2514 1.4476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9757 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5759 2.5227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5522 2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 20 1 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 18 2 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 24 1 0 0 0 0 12 7 1 6 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 15 16 1 0 0 0 0 15 22 1 1 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 24 1 1 0 0 0 17 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.1
Volume:	324.642
LogP:	1.094
LogD:	1.119
LogS:	-2.846
# Rotatable Bonds:	3
TPSA:	125.16
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	3.574
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.055
MDCK Permeability:	6.017559371684911e-06
Pgp-inhibitor:	0.011
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.645
20% Bioavailability (F20%):	0.813
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.343
Plasma Protein Binding (PPB):	94.80436706542969%
Volume Distribution (VD):	0.613
Pgp-substrate:	6.355963706970215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.296
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.284
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.285
CYP2D6-inhibitor:	0.223
CYP2D6-substrate:	0.408
CYP3A4-inhibitor:	0.085
CYP3A4-substrate:	0.188

ADMET: Excretion

Clearance (CL):	9.292
Half-life (T1/2):	0.788

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.506
AMES Toxicity:	0.626
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.332
Carcinogencity:	0.619
Eye Corrosion:	0.003
Eye Irritation:	0.149
Respiratory Toxicity:	0.261

Download Data

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

Natural Product: NPC471736

Natural Product ID:	NPC471736
*Common Name:**	FVOWQABXUMZLHH-VZEFYGNVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FVOWQABXUMZLHH-VZEFYGNVSA-N
Standard InCHI:	InChI=1S/C17H16N2O6/c20-7-12-15(22)16(23)17(25-12)24-11-6-2-4-9-14(11)19-8-3-1-5-10(21)13(8)18-9/h1-6,12,15-17,20-23H,7H2/t12-,15-,16+,17+/m1/s1
SMILES:	OC[C@H]1O[C@@H]([C@H]([C@@H]1O)O)Oc1cccc2c1nc1cccc(c1n2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109318
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24460410]
NPO33034	nannocystis pusilla	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24460410]
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4585	Organism	Mycobacterium diernhoferi	Mycobacterium diernhoferi	MIC	=	66.6	ug.mL-1	PMID[467804]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	33.3	ug.mL-1	PMID[467804]

☑ 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 NPC471736 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	650
0.1-0.2	4949
0.2-0.3	12303
0.3-0.4	10298
0.4-0.5	11297
0.5-0.6	2594
0.6-0.7	551
0.7-0.8	50
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9365	High Similarity	NPC308392
0.8865	High Similarity	NPC110741
0.8541	High Similarity	NPC118776
0.8251	Intermediate Similarity	NPC1527
0.8165	Intermediate Similarity	NPC291609
0.8132	Intermediate Similarity	NPC79911
0.8119	Intermediate Similarity	NPC124300
0.8077	Intermediate Similarity	NPC120798
0.8009	Intermediate Similarity	NPC310618
0.7884	Intermediate Similarity	NPC95898
0.7822	Intermediate Similarity	NPC470586
0.7688	Intermediate Similarity	NPC285635
0.7684	Intermediate Similarity	NPC258773
0.7614	Intermediate Similarity	NPC314573
0.7536	Intermediate Similarity	NPC203168
0.7514	Intermediate Similarity	NPC36168
0.7441	Intermediate Similarity	NPC219664
0.7434	Intermediate Similarity	NPC99891
0.743	Intermediate Similarity	NPC288349
0.7412	Intermediate Similarity	NPC472434
0.7389	Intermediate Similarity	NPC79293
0.7389	Intermediate Similarity	NPC226202
0.7389	Intermediate Similarity	NPC279401
0.736	Intermediate Similarity	NPC478023
0.7327	Intermediate Similarity	NPC148409
0.7299	Intermediate Similarity	NPC474595
0.7281	Intermediate Similarity	NPC197141
0.7273	Intermediate Similarity	NPC66815
0.725	Intermediate Similarity	NPC227824
0.7214	Intermediate Similarity	NPC42591
0.7161	Intermediate Similarity	NPC472435
0.715	Intermediate Similarity	NPC219963
0.7097	Intermediate Similarity	NPC474594
0.7085	Intermediate Similarity	NPC283152
0.7079	Intermediate Similarity	NPC62069
0.7071	Intermediate Similarity	NPC472436
0.707	Intermediate Similarity	NPC469589
0.7035	Intermediate Similarity	NPC194724
0.698	Remote Similarity	NPC161887
0.698	Remote Similarity	NPC266551
0.6978	Remote Similarity	NPC200888
0.6968	Remote Similarity	NPC469594
0.6967	Remote Similarity	NPC18487
0.6961	Remote Similarity	NPC20249
0.6955	Remote Similarity	NPC470799
0.6955	Remote Similarity	NPC8022
0.6943	Remote Similarity	NPC70549
0.6941	Remote Similarity	NPC471080
0.6941	Remote Similarity	NPC469592
0.6931	Remote Similarity	NPC478032
0.6927	Remote Similarity	NPC204385
0.6915	Remote Similarity	NPC470395
0.6912	Remote Similarity	NPC320394
0.6912	Remote Similarity	NPC209769
0.6898	Remote Similarity	NPC470404
0.6898	Remote Similarity	NPC470403
0.6898	Remote Similarity	NPC470394
0.6895	Remote Similarity	NPC244856
0.6887	Remote Similarity	NPC128823
0.6866	Remote Similarity	NPC288943
0.6852	Remote Similarity	NPC472111
0.6852	Remote Similarity	NPC476106
0.6837	Remote Similarity	NPC223427
0.682	Remote Similarity	NPC473800
0.6818	Remote Similarity	NPC26679
0.6814	Remote Similarity	NPC206201
0.6812	Remote Similarity	NPC66083
0.6806	Remote Similarity	NPC164374
0.6806	Remote Similarity	NPC137929
0.6804	Remote Similarity	NPC112766
0.6787	Remote Similarity	NPC250448
0.6787	Remote Similarity	NPC306644
0.6787	Remote Similarity	NPC236424
0.6786	Remote Similarity	NPC473179
0.6778	Remote Similarity	NPC165964
0.6774	Remote Similarity	NPC304183
0.6774	Remote Similarity	NPC475841
0.6774	Remote Similarity	NPC474145
0.6769	Remote Similarity	NPC476997
0.6757	Remote Similarity	NPC274842
0.6756	Remote Similarity	NPC128115
0.6753	Remote Similarity	NPC469554
0.6739	Remote Similarity	NPC476998
0.6739	Remote Similarity	NPC476996
0.6728	Remote Similarity	NPC470930
0.6725	Remote Similarity	NPC110151
0.6717	Remote Similarity	NPC118511
0.6714	Remote Similarity	NPC474188
0.6714	Remote Similarity	NPC469390
0.6714	Remote Similarity	NPC267928
0.6713	Remote Similarity	NPC291535
0.6713	Remote Similarity	NPC475085
0.6713	Remote Similarity	NPC475112
0.6712	Remote Similarity	NPC470931
0.6696	Remote Similarity	NPC476994
0.6684	Remote Similarity	NPC26850
0.6682	Remote Similarity	NPC185782
0.6682	Remote Similarity	NPC153452
0.6667	Remote Similarity	NPC220560
0.6667	Remote Similarity	NPC57453
0.6653	Remote Similarity	NPC58209
0.6652	Remote Similarity	NPC473182
0.6649	Remote Similarity	NPC153769
0.6637	Remote Similarity	NPC193267
0.6637	Remote Similarity	NPC213530
0.6637	Remote Similarity	NPC476287
0.6636	Remote Similarity	NPC243834
0.6636	Remote Similarity	NPC70956
0.6634	Remote Similarity	NPC121658
0.6634	Remote Similarity	NPC14651
0.6625	Remote Similarity	NPC472068
0.6618	Remote Similarity	NPC290069
0.6608	Remote Similarity	NPC132642
0.6606	Remote Similarity	NPC476138
0.6606	Remote Similarity	NPC469440
0.6606	Remote Similarity	NPC245816
0.6606	Remote Similarity	NPC475774
0.6603	Remote Similarity	NPC61350
0.6584	Remote Similarity	NPC476518
0.658	Remote Similarity	NPC473185
0.6579	Remote Similarity	NPC90019
0.6577	Remote Similarity	NPC5145
0.657	Remote Similarity	NPC472031
0.657	Remote Similarity	NPC472067
0.657	Remote Similarity	NPC472066
0.657	Remote Similarity	NPC314394
0.6569	Remote Similarity	NPC160100
0.6568	Remote Similarity	NPC476995
0.6568	Remote Similarity	NPC473183
0.6564	Remote Similarity	NPC284348
0.656	Remote Similarity	NPC135887
0.656	Remote Similarity	NPC199277
0.6553	Remote Similarity	NPC473184
0.6548	Remote Similarity	NPC101312
0.6544	Remote Similarity	NPC19872
0.6538	Remote Similarity	NPC101543
0.6537	Remote Similarity	NPC202503
0.6531	Remote Similarity	NPC26872
0.6528	Remote Similarity	NPC72211
0.6526	Remote Similarity	NPC114335
0.6526	Remote Similarity	NPC280964
0.6526	Remote Similarity	NPC141915
0.6522	Remote Similarity	NPC473987
0.652	Remote Similarity	NPC473822
0.652	Remote Similarity	NPC173080
0.6518	Remote Similarity	NPC296482
0.6518	Remote Similarity	NPC202768
0.6518	Remote Similarity	NPC53069
0.6515	Remote Similarity	NPC116573
0.6507	Remote Similarity	NPC477532
0.6507	Remote Similarity	NPC310118
0.65	Remote Similarity	NPC477805
0.65	Remote Similarity	NPC470500
0.65	Remote Similarity	NPC477796
0.65	Remote Similarity	NPC477795
0.65	Remote Similarity	NPC177404
0.65	Remote Similarity	NPC208364
0.65	Remote Similarity	NPC477806
0.6495	Remote Similarity	NPC475190
0.6494	Remote Similarity	NPC212766
0.6494	Remote Similarity	NPC289423
0.6488	Remote Similarity	NPC312872
0.6486	Remote Similarity	NPC475910
0.6486	Remote Similarity	NPC287208
0.6485	Remote Similarity	NPC475844
0.6484	Remote Similarity	NPC311357
0.6478	Remote Similarity	NPC258048
0.6477	Remote Similarity	NPC473769
0.6476	Remote Similarity	NPC314552
0.6473	Remote Similarity	NPC472168
0.6468	Remote Similarity	NPC234197
0.6462	Remote Similarity	NPC242928
0.6456	Remote Similarity	NPC286195
0.6455	Remote Similarity	NPC317572
0.6452	Remote Similarity	NPC192315
0.645	Remote Similarity	NPC25899
0.645	Remote Similarity	NPC205372
0.6444	Remote Similarity	NPC48353
0.6444	Remote Similarity	NPC112206
0.6444	Remote Similarity	NPC96405
0.6444	Remote Similarity	NPC171409
0.6444	Remote Similarity	NPC202605
0.6443	Remote Similarity	NPC220523
0.6443	Remote Similarity	NPC161292
0.6441	Remote Similarity	NPC313189
0.6439	Remote Similarity	NPC111624
0.6438	Remote Similarity	NPC232727
0.6435	Remote Similarity	NPC70259
0.6429	Remote Similarity	NPC123976
0.6429	Remote Similarity	NPC167860
0.6429	Remote Similarity	NPC184680
0.6422	Remote Similarity	NPC97746
0.6422	Remote Similarity	NPC187558
0.6422	Remote Similarity	NPC179287
0.6422	Remote Similarity	NPC476167
0.6419	Remote Similarity	NPC84853
0.6419	Remote Similarity	NPC289786
0.6418	Remote Similarity	NPC48192
0.6411	Remote Similarity	NPC474798
0.641	Remote Similarity	NPC257142

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 NPC471736 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	731
0.2-0.3	1198
0.3-0.4	2242
0.4-0.5	3041
0.5-0.6	1367
0.6-0.7	246
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7387	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD8116	Phase 3
0.71	Intermediate Similarity	NPD8117	Approved
0.7098	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2772	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2314	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7194	Discontinued
0.7089	Intermediate Similarity	NPD3003	Approved
0.7064	Intermediate Similarity	NPD5903	Approved
0.7064	Intermediate Similarity	NPD5902	Approved
0.7059	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4502	Phase 2
0.6986	Remote Similarity	NPD774	Phase 3
0.6968	Remote Similarity	NPD6985	Discontinued
0.6967	Remote Similarity	NPD1768	Approved
0.6952	Remote Similarity	NPD1622	Discontinued
0.6949	Remote Similarity	NPD8324	Phase 2
0.6943	Remote Similarity	NPD7558	Phase 2
0.6909	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6550	Discontinued
0.6898	Remote Similarity	NPD7222	Phase 2
0.6897	Remote Similarity	NPD4203	Approved
0.6897	Remote Similarity	NPD4204	Approved
0.6878	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3875	Discontinued
0.6857	Remote Similarity	NPD6590	Discontinued
0.6849	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4131	Phase 3
0.6845	Remote Similarity	NPD5256	Discontinued
0.6825	Remote Similarity	NPD5512	Phase 3
0.68	Remote Similarity	NPD6298	Discontinued
0.6774	Remote Similarity	NPD5530	Phase 1
0.6769	Remote Similarity	NPD8104	Phase 3
0.6762	Remote Similarity	NPD4372	Phase 1
0.6756	Remote Similarity	NPD5930	Phase 3
0.6754	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7426	Phase 1
0.6754	Remote Similarity	NPD7674	Phase 3
0.6754	Remote Similarity	NPD7675	Phase 3
0.6743	Remote Similarity	NPD7452	Approved
0.6743	Remote Similarity	NPD7453	Approved
0.6743	Remote Similarity	NPD1392	Approved
0.6731	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1034	Phase 3
0.6696	Remote Similarity	NPD1744	Approved
0.6695	Remote Similarity	NPD3838	Phase 3
0.6682	Remote Similarity	NPD6569	Phase 2
0.6681	Remote Similarity	NPD5640	Discontinued
0.6667	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD565	Phase 2
0.6667	Remote Similarity	NPD6290	Phase 2
0.6652	Remote Similarity	NPD6494	Phase 2
0.6638	Remote Similarity	NPD6246	Approved
0.6636	Remote Similarity	NPD6988	Phase 1
0.6622	Remote Similarity	NPD3570	Phase 2
0.6621	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6669	Phase 2
0.6597	Remote Similarity	NPD6716	Phase 1
0.6594	Remote Similarity	NPD6306	Phase 2
0.6593	Remote Similarity	NPD5632	Approved
0.6593	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4080	Discontinued
0.6579	Remote Similarity	NPD7726	Phase 1
0.6578	Remote Similarity	NPD5612	Discontinued
0.657	Remote Similarity	NPD5482	Discontinued
0.6568	Remote Similarity	NPD4368	Phase 2
0.6567	Remote Similarity	NPD1505	Phase 2
0.6564	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5658	Approved
0.6558	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8370	Discontinued
0.6553	Remote Similarity	NPD3074	Discontinued
0.655	Remote Similarity	NPD861	Approved
0.655	Remote Similarity	NPD863	Approved
0.655	Remote Similarity	NPD862	Approved
0.6547	Remote Similarity	NPD5416	Discontinued
0.6543	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD1603	Discontinued
0.6531	Remote Similarity	NPD789	Phase 2
0.6528	Remote Similarity	NPD772	Phase 3
0.6524	Remote Similarity	NPD8512	Phase 3
0.6518	Remote Similarity	NPD3815	Phase 1
0.6518	Remote Similarity	NPD3816	Phase 1
0.6518	Remote Similarity	NPD4927	Discontinued
0.6512	Remote Similarity	NPD3477	Phase 2
0.6512	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6159	Phase 2
0.6504	Remote Similarity	NPD5101	Discontinued
0.6483	Remote Similarity	NPD2951	Discontinued
0.6476	Remote Similarity	NPD5164	Discontinued
0.6476	Remote Similarity	NPD5059	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD3370	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5067	Phase 2
0.6473	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD3920	Phase 2
0.6473	Remote Similarity	NPD5066	Phase 2
0.6465	Remote Similarity	NPD1602	Discontinued
0.6465	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD4021	Phase 2
0.6446	Remote Similarity	NPD8359	Phase 2
0.6444	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5429	Discontinued
0.6437	Remote Similarity	NPD8244	Phase 2
0.6434	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7068	Approved
0.6432	Remote Similarity	NPD6643	Discontinued
0.6432	Remote Similarity	NPD7067	Approved
0.6426	Remote Similarity	NPD6962	Phase 2
0.6422	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD2176	Approved
0.6422	Remote Similarity	NPD2177	Approved
0.6422	Remote Similarity	NPD2175	Phase 3
0.6416	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD3945	Discontinued
0.6416	Remote Similarity	NPD5944	Phase 1
0.6416	Remote Similarity	NPD5945	Phase 1
0.6408	Remote Similarity	NPD5875	Approved
0.6408	Remote Similarity	NPD5878	Approved
0.6407	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD6736	Discontinued
0.6407	Remote Similarity	NPD1856	Discontinued
0.6406	Remote Similarity	NPD4605	Approved
0.6406	Remote Similarity	NPD4604	Approved
0.6406	Remote Similarity	NPD2476	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5939	Approved
0.64	Remote Similarity	NPD6220	Phase 3
0.64	Remote Similarity	NPD5936	Approved
0.64	Remote Similarity	NPD3939	Suspended
0.6397	Remote Similarity	NPD8442	Discontinued
0.6395	Remote Similarity	NPD1273	Discontinued
0.6393	Remote Similarity	NPD1740	Approved
0.6393	Remote Similarity	NPD1838	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD1739	Approved
0.639	Remote Similarity	NPD7022	Phase 2
0.6388	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4454	Phase 2
0.6383	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD6743	Phase 2
0.6382	Remote Similarity	NPD6742	Phase 2
0.6379	Remote Similarity	NPD983	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD7395	Discontinued
0.6376	Remote Similarity	NPD6877	Discontinued
0.6372	Remote Similarity	NPD7069	Discontinued
0.6371	Remote Similarity	NPD8255	Phase 2
0.6364	Remote Similarity	NPD1941	Approved
0.6359	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5420	Discontinued
0.6355	Remote Similarity	NPD8063	Discontinued
0.6351	Remote Similarity	NPD4035	Approved
0.6351	Remote Similarity	NPD4034	Approved
0.6351	Remote Similarity	NPD4795	Phase 2
0.6351	Remote Similarity	NPD31	Approved
0.6351	Remote Similarity	NPD4038	Approved
0.6351	Remote Similarity	NPD4036	Approved
0.6351	Remote Similarity	NPD4039	Approved
0.6351	Remote Similarity	NPD4122	Approved
0.6351	Remote Similarity	NPD4037	Approved
0.6351	Remote Similarity	NPD32	Approved
0.6351	Remote Similarity	NPD4033	Approved
0.6348	Remote Similarity	NPD6974	Phase 3
0.6338	Remote Similarity	NPD2383	Phase 1
0.6337	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.633	Remote Similarity	NPD1229	Phase 2
0.6329	Remote Similarity	NPD5938	Phase 3
0.6327	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD3263	Phase 3
0.6324	Remote Similarity	NPD3343	Phase 3
0.6324	Remote Similarity	NPD5450	Discontinued
0.632	Remote Similarity	NPD5850	Phase 3
0.632	Remote Similarity	NPD7180	Phase 3
0.6318	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD3602	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD5022	Discontinued
0.6313	Remote Similarity	NPD4418	Discontinued
0.6313	Remote Similarity	NPD6251	Discontinued
0.6308	Remote Similarity	NPD6814	Phase 3
0.6307	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD4086	Phase 1
0.6298	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6573	Phase 3
0.6296	Remote Similarity	NPD6572	Phase 2
0.6293	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3328	Phase 2
0.6281	Remote Similarity	NPD7417	Discontinued
0.6279	Remote Similarity	NPD5316	Approved
0.6278	Remote Similarity	NPD3946	Clinical (unspecified phase)

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