NPASS Compound

Structure

NPC472843 OpenBabel07101718332D 39 45 0 0 1 0 0 0 0 0999 V2000 0.6688 6.2656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3136 -2.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9905 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9905 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3704 3.2395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1245 2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4193 3.5485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5783 2.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1245 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0181 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2584 2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 2.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8352 1.5922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2584 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3074 2.7749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6817 2.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9006 3.6884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0939 3.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7196 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8841 1.9013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2749 2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -1.1756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7226 -0.1810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7045 -1.5823 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3074 4.6020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3018 4.7711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0431 0.6141 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.3074 1.1568 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5642 5.2711 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0181 1.4013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1226 -2.3958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4271 -1.7634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6361 0.2257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2855 4.8099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2153 5.1778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6000 -2.5768 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 31 1 0 0 0 0 2 38 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 9 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 11 2 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 14 2 0 0 0 0 10 33 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 21 2 0 0 0 0 13 21 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 10 1 6 0 0 0 15 25 1 0 0 0 0 15 39 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 22 2 0 0 0 0 20 30 1 0 0 0 0 21 32 1 0 0 0 0 22 32 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 23 34 1 6 0 0 0 24 28 1 0 0 0 0 24 35 1 1 0 0 0 25 38 1 1 0 0 0 26 31 1 0 0 0 0 26 36 2 0 0 0 0 27 31 1 0 0 0 0 27 37 2 0 0 0 0 28 32 1 6 0 0 0 28 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	549.13
Volume:	513.681
LogP:	3.54
LogD:	2.72
LogS:	-6.922
# Rotatable Bonds:	3
TPSA:	137.25
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	4.257
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.813
MDCK Permeability:	6.527148343593581e-06
Pgp-inhibitor:	0.229
Pgp-substrate:	0.946
Human Intestinal Absorption (HIA):	0.92
20% Bioavailability (F20%):	0.42
30% Bioavailability (F30%):	0.545

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	92.94995880126953%
Volume Distribution (VD):	0.961
Pgp-substrate:	2.6474437713623047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.792
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.177
CYP2C19-substrate:	0.381
CYP2C9-inhibitor:	0.71
CYP2C9-substrate:	0.182
CYP2D6-inhibitor:	0.566
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.396
CYP3A4-substrate:	0.491

ADMET: Excretion

Clearance (CL):	4.843
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.196
Human Hepatotoxicity (H-HT):	0.76
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.382
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.717
Skin Sensitization:	0.506
Carcinogencity:	0.911
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.659

Download Data

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

Natural Product: NPC472843

Natural Product ID:	NPC472843
*Common Name:**	DBYKGSYMCOHYFG-IJKWSERMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DBYKGSYMCOHYFG-IJKWSERMSA-N
Standard InCHI:	InChI=1S/C28H24ClN3O7/c1-31-26(36)18-16-11-6-3-4-9-14(11)30-20(16)22-17(19(18)27(31)37)12-7-5-8-13(29)21(12)32(22)28-24(35)23(34)25(38-2)15(10-33)39-28/h3-9,15,23-25,28,30,33-35H,10H2,1-2H3/t15-,23-,24-,25-,28-/m1/s1
SMILES:	CN1C(=O)C2=C3C4=C(C(=CC=C4)Cl)N(C3=C5C(=C2C1=O)C6=CC=CC=C6N5)C7C(C(C(C(O7)CO)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3589060
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles [CHEMONTID:0001865] Pyrrolocarbazoles [CHEMONTID:0001866] Indolocarbazoles

*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
NPO33195	actinomadura melliaura atcc 39691	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26091285]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	Activity	=	47.4	%	PMID[454401]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	69.0	%	PMID[454401]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	40.5	%	PMID[454401]

☑ 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 NPC472843 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	443
0.1-0.2	2481
0.2-0.3	15516
0.3-0.4	17279
0.4-0.5	3434
0.5-0.6	2643
0.6-0.7	875
0.7-0.8	19
0.8-0.85	0
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9378	High Similarity	NPC472207
0.9336	High Similarity	NPC472845
0.8996	High Similarity	NPC1203
0.8755	High Similarity	NPC472846
0.8622	High Similarity	NPC472842
0.8571	High Similarity	NPC107836
0.7983	Intermediate Similarity	NPC472844
0.7395	Intermediate Similarity	NPC31700
0.7361	Intermediate Similarity	NPC45048
0.7323	Intermediate Similarity	NPC279589
0.7306	Intermediate Similarity	NPC313884
0.7306	Intermediate Similarity	NPC98371
0.7211	Intermediate Similarity	NPC94428
0.7211	Intermediate Similarity	NPC263937
0.7131	Intermediate Similarity	NPC132329
0.7095	Intermediate Similarity	NPC204303
0.7012	Intermediate Similarity	NPC191382
0.7012	Intermediate Similarity	NPC56109
0.7012	Intermediate Similarity	NPC162860
0.6988	Remote Similarity	NPC160898
0.6939	Remote Similarity	NPC478157
0.6929	Remote Similarity	NPC54420
0.69	Remote Similarity	NPC470205
0.688	Remote Similarity	NPC155444
0.6878	Remote Similarity	NPC149708
0.6875	Remote Similarity	NPC316411
0.6872	Remote Similarity	NPC478158
0.6855	Remote Similarity	NPC174788
0.6824	Remote Similarity	NPC267853
0.6824	Remote Similarity	NPC315062
0.6815	Remote Similarity	NPC312645
0.6815	Remote Similarity	NPC472285
0.6812	Remote Similarity	NPC91179
0.6797	Remote Similarity	NPC244897
0.6789	Remote Similarity	NPC75634
0.6787	Remote Similarity	NPC477714
0.6787	Remote Similarity	NPC281049
0.6772	Remote Similarity	NPC476491
0.6758	Remote Similarity	NPC475859
0.6758	Remote Similarity	NPC475969
0.6751	Remote Similarity	NPC195314
0.6747	Remote Similarity	NPC477715
0.6745	Remote Similarity	NPC33949
0.6735	Remote Similarity	NPC477548
0.6723	Remote Similarity	NPC324091
0.6721	Remote Similarity	NPC244741
0.6719	Remote Similarity	NPC477175
0.6719	Remote Similarity	NPC470730
0.6718	Remote Similarity	NPC57453
0.6707	Remote Similarity	NPC234999
0.6706	Remote Similarity	NPC476492
0.6706	Remote Similarity	NPC192712
0.6705	Remote Similarity	NPC70155
0.6694	Remote Similarity	NPC89508
0.6693	Remote Similarity	NPC52254
0.6693	Remote Similarity	NPC474877
0.668	Remote Similarity	NPC313985
0.668	Remote Similarity	NPC249150
0.668	Remote Similarity	NPC79129
0.668	Remote Similarity	NPC195461
0.668	Remote Similarity	NPC49196
0.668	Remote Similarity	NPC81654
0.6667	Remote Similarity	NPC165743
0.6667	Remote Similarity	NPC477979
0.6667	Remote Similarity	NPC314058
0.6667	Remote Similarity	NPC316018
0.6667	Remote Similarity	NPC14812
0.6667	Remote Similarity	NPC317701
0.6654	Remote Similarity	NPC471564
0.6654	Remote Similarity	NPC477176
0.6654	Remote Similarity	NPC470729
0.6653	Remote Similarity	NPC475778
0.6641	Remote Similarity	NPC63279
0.6641	Remote Similarity	NPC323198
0.6641	Remote Similarity	NPC475258
0.6628	Remote Similarity	NPC477177
0.6627	Remote Similarity	NPC476818
0.6626	Remote Similarity	NPC476073
0.6625	Remote Similarity	NPC227582
0.6615	Remote Similarity	NPC325976
0.6615	Remote Similarity	NPC297642
0.6612	Remote Similarity	NPC277350
0.6611	Remote Similarity	NPC181502
0.6611	Remote Similarity	NPC85066
0.6605	Remote Similarity	NPC476514
0.6603	Remote Similarity	NPC478029
0.6602	Remote Similarity	NPC89987
0.6599	Remote Similarity	NPC223791
0.6599	Remote Similarity	NPC107077
0.6598	Remote Similarity	NPC131887
0.6598	Remote Similarity	NPC165599
0.6598	Remote Similarity	NPC50503
0.6597	Remote Similarity	NPC316359
0.6597	Remote Similarity	NPC315617
0.659	Remote Similarity	NPC478028
0.6588	Remote Similarity	NPC475271
0.6587	Remote Similarity	NPC82070
0.6585	Remote Similarity	NPC477065
0.658	Remote Similarity	NPC476493
0.6575	Remote Similarity	NPC471506
0.6574	Remote Similarity	NPC476114
0.657	Remote Similarity	NPC74413
0.657	Remote Similarity	NPC474767
0.6568	Remote Similarity	NPC17059
0.656	Remote Similarity	NPC234078
0.656	Remote Similarity	NPC54744
0.656	Remote Similarity	NPC221100
0.6557	Remote Similarity	NPC155143
0.6553	Remote Similarity	NPC133003
0.6552	Remote Similarity	NPC475094
0.6552	Remote Similarity	NPC39370
0.6543	Remote Similarity	NPC252338
0.654	Remote Similarity	NPC175474
0.6538	Remote Similarity	NPC63031
0.6538	Remote Similarity	NPC473186
0.6537	Remote Similarity	NPC475424
0.6537	Remote Similarity	NPC79107
0.6537	Remote Similarity	NPC909
0.6537	Remote Similarity	NPC475338
0.6535	Remote Similarity	NPC272174
0.6529	Remote Similarity	NPC171317
0.6527	Remote Similarity	NPC472113
0.6523	Remote Similarity	NPC229893
0.6522	Remote Similarity	NPC473310
0.652	Remote Similarity	NPC294620
0.6516	Remote Similarity	NPC475506
0.651	Remote Similarity	NPC474896
0.6508	Remote Similarity	NPC471192
0.6508	Remote Similarity	NPC322064
0.6508	Remote Similarity	NPC470731
0.6506	Remote Similarity	NPC314834
0.6506	Remote Similarity	NPC475422
0.6504	Remote Similarity	NPC314648
0.6502	Remote Similarity	NPC104712
0.6496	Remote Similarity	NPC89549
0.6494	Remote Similarity	NPC472291
0.6492	Remote Similarity	NPC87755
0.649	Remote Similarity	NPC476874
0.649	Remote Similarity	NPC162730
0.649	Remote Similarity	NPC260900
0.649	Remote Similarity	NPC193761
0.6485	Remote Similarity	NPC476460
0.6484	Remote Similarity	NPC31097
0.6482	Remote Similarity	NPC249428
0.6481	Remote Similarity	NPC473800
0.648	Remote Similarity	NPC82370
0.648	Remote Similarity	NPC320968
0.6478	Remote Similarity	NPC314855
0.6478	Remote Similarity	NPC313345
0.6478	Remote Similarity	NPC313796
0.6478	Remote Similarity	NPC315638
0.6475	Remote Similarity	NPC478009
0.6475	Remote Similarity	NPC478010
0.6468	Remote Similarity	NPC472108
0.6468	Remote Similarity	NPC19679
0.6468	Remote Similarity	NPC139291
0.6466	Remote Similarity	NPC469743
0.6462	Remote Similarity	NPC326363
0.6461	Remote Similarity	NPC52557
0.646	Remote Similarity	NPC478006
0.6456	Remote Similarity	NPC478077
0.6456	Remote Similarity	NPC62749
0.6454	Remote Similarity	NPC6865
0.6454	Remote Similarity	NPC153980
0.6453	Remote Similarity	NPC9482
0.6452	Remote Similarity	NPC314297
0.6452	Remote Similarity	NPC315545
0.645	Remote Similarity	NPC161861
0.6449	Remote Similarity	NPC300183
0.6446	Remote Similarity	NPC231342
0.6446	Remote Similarity	NPC292361
0.6446	Remote Similarity	NPC102592
0.6446	Remote Similarity	NPC79356
0.6444	Remote Similarity	NPC472112
0.6443	Remote Similarity	NPC470732
0.6443	Remote Similarity	NPC36405
0.6439	Remote Similarity	NPC184680
0.6434	Remote Similarity	NPC100321
0.6434	Remote Similarity	NPC32200
0.6434	Remote Similarity	NPC293917
0.6432	Remote Similarity	NPC304203
0.6429	Remote Similarity	NPC475844
0.6429	Remote Similarity	NPC229348
0.6426	Remote Similarity	NPC314957
0.6423	Remote Similarity	NPC194740
0.6423	Remote Similarity	NPC474116
0.642	Remote Similarity	NPC134657
0.6417	Remote Similarity	NPC79386
0.6415	Remote Similarity	NPC470784
0.6415	Remote Similarity	NPC470785
0.6414	Remote Similarity	NPC62510
0.6414	Remote Similarity	NPC72956
0.6414	Remote Similarity	NPC308931
0.6414	Remote Similarity	NPC99939
0.6411	Remote Similarity	NPC471191
0.6411	Remote Similarity	NPC18661
0.6408	Remote Similarity	NPC128265
0.6408	Remote Similarity	NPC294909
0.6408	Remote Similarity	NPC254240
0.6408	Remote Similarity	NPC312870

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 NPC472843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	616
0.2-0.3	1095
0.3-0.4	2405
0.4-0.5	2762
0.5-0.6	1717
0.6-0.7	309
0.7-0.8	11
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9651	High Similarity	NPD7772	Phase 3
0.8101	Intermediate Similarity	NPD7181	Phase 3
0.7843	Intermediate Similarity	NPD6456	Discontinued
0.7742	Intermediate Similarity	NPD7921	Approved
0.751	Intermediate Similarity	NPD6995	Phase 1
0.7388	Intermediate Similarity	NPD6978	Phase 2
0.7388	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6455	Phase 3
0.7306	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7688	Phase 1
0.7093	Intermediate Similarity	NPD5807	Phase 2
0.7045	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7036	Intermediate Similarity	NPD7950	Approved
0.7036	Intermediate Similarity	NPD7953	Approved
0.7036	Intermediate Similarity	NPD7951	Approved
0.7036	Intermediate Similarity	NPD7790	Approved
0.7036	Intermediate Similarity	NPD7791	Approved
0.7036	Intermediate Similarity	NPD7952	Approved
0.7036	Intermediate Similarity	NPD7789	Approved
0.7012	Intermediate Similarity	NPD7781	Approved
0.7012	Intermediate Similarity	NPD7780	Approved
0.7004	Intermediate Similarity	NPD7576	Discontinued
0.6958	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3746	Discontinued
0.6929	Remote Similarity	NPD8322	Phase 2
0.6914	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7731	Approved
0.6905	Remote Similarity	NPD7730	Approved
0.6892	Remote Similarity	NPD7271	Approved
0.6882	Remote Similarity	NPD7769	Phase 3
0.687	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7824	Approved
0.6818	Remote Similarity	NPD7001	Phase 3
0.6789	Remote Similarity	NPD7454	Approved
0.6789	Remote Similarity	NPD7455	Approved
0.6786	Remote Similarity	NPD7717	Approved
0.6786	Remote Similarity	NPD7716	Approved
0.6777	Remote Similarity	NPD5426	Phase 3
0.6747	Remote Similarity	NPD7185	Discontinued
0.6721	Remote Similarity	NPD8093	Discontinued
0.6718	Remote Similarity	NPD7770	Phase 3
0.6708	Remote Similarity	NPD8114	Approved
0.6708	Remote Similarity	NPD8115	Approved
0.6694	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD1534	Approved
0.668	Remote Similarity	NPD4600	Approved
0.668	Remote Similarity	NPD4601	Approved
0.6653	Remote Similarity	NPD7878	Phase 2
0.6642	Remote Similarity	NPD5450	Discontinued
0.6641	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8463	Approved
0.6611	Remote Similarity	NPD7944	Discontinued
0.6609	Remote Similarity	NPD3319	Phase 1
0.6609	Remote Similarity	NPD3320	Approved
0.6609	Remote Similarity	NPD3318	Approved
0.6608	Remote Similarity	NPD5021	Discontinued
0.66	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6142	Phase 3
0.655	Remote Similarity	NPD7767	Approved
0.6548	Remote Similarity	NPD6710	Phase 3
0.6526	Remote Similarity	NPD8046	Discontinued
0.6525	Remote Similarity	NPD5809	Phase 3
0.6516	Remote Similarity	NPD7817	Phase 1
0.6516	Remote Similarity	NPD7727	Phase 2
0.6511	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7787	Discontinued
0.6504	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6999	Discontinued
0.6502	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8317	Phase 2
0.65	Remote Similarity	NPD8316	Phase 2
0.6494	Remote Similarity	NPD6787	Phase 2
0.6492	Remote Similarity	NPD7665	Phase 2
0.6492	Remote Similarity	NPD7666	Phase 3
0.6489	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7888	Approved
0.6486	Remote Similarity	NPD7887	Approved
0.6467	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6716	Phase 1
0.6464	Remote Similarity	NPD6986	Phase 1
0.6455	Remote Similarity	NPD5488	Discontinued
0.6454	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5017	Discontinued
0.6446	Remote Similarity	NPD4848	Phase 1
0.6443	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6987	Phase 1
0.6436	Remote Similarity	NPD6531	Approved
0.6436	Remote Similarity	NPD6530	Approved
0.6434	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8094	Discontinued
0.642	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6218	Discontinued
0.6414	Remote Similarity	NPD7470	Discontinued
0.6409	Remote Similarity	NPD8289	Discontinued
0.6408	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4500	Approved
0.6408	Remote Similarity	NPD4501	Approved
0.6407	Remote Similarity	NPD7397	Approved
0.6407	Remote Similarity	NPD7398	Approved
0.6406	Remote Similarity	NPD3280	Approved
0.6404	Remote Similarity	NPD5821	Approved
0.64	Remote Similarity	NPD5835	Phase 3
0.64	Remote Similarity	NPD5834	Phase 3
0.6398	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7656	Approved
0.6389	Remote Similarity	NPD7657	Approved
0.6386	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5901	Discontinued
0.6368	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6361	Remote Similarity	NPD8524	Approved
0.636	Remote Similarity	NPD6483	Approved
0.636	Remote Similarity	NPD6484	Approved
0.636	Remote Similarity	NPD2443	Approved
0.636	Remote Similarity	NPD2442	Approved
0.6357	Remote Similarity	NPD8349	Phase 1
0.6356	Remote Similarity	NPD7187	Phase 2
0.6353	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD6664	Approved
0.6352	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD8102	Discontinued
0.6345	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD8460	Approved
0.6341	Remote Similarity	NPD8459	Approved
0.6337	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4602	Approved
0.6335	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD6176	Phase 1
0.6324	Remote Similarity	NPD2411	Approved
0.6324	Remote Similarity	NPD5482	Discontinued
0.6322	Remote Similarity	NPD4328	Approved
0.632	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD5473	Discontinued
0.6311	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.631	Remote Similarity	NPD8250	Phase 2
0.631	Remote Similarity	NPD4051	Discontinued
0.6304	Remote Similarity	NPD6770	Approved
0.6301	Remote Similarity	NPD6248	Phase 2
0.6301	Remote Similarity	NPD6249	Phase 2
0.6299	Remote Similarity	NPD3243	Approved
0.6299	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD2509	Approved
0.6295	Remote Similarity	NPD2510	Approved
0.6292	Remote Similarity	NPD8431	Approved
0.6288	Remote Similarity	NPD8119	Discontinued
0.6287	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.628	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6210	Phase 3
0.6277	Remote Similarity	NPD8363	Approved
0.6277	Remote Similarity	NPD8364	Approved
0.6269	Remote Similarity	NPD7548	Discontinued
0.626	Remote Similarity	NPD4852	Phase 2
0.626	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD8465	Approved
0.6259	Remote Similarity	NPD8467	Approved
0.6259	Remote Similarity	NPD8466	Approved
0.6255	Remote Similarity	NPD4854	Phase 3
0.625	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6217	Discontinued
0.6245	Remote Similarity	NPD7776	Approved
0.6241	Remote Similarity	NPD6840	Approved
0.624	Remote Similarity	NPD5012	Phase 2
0.624	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.624	Remote Similarity	NPD3258	Approved
0.6234	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5421	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6376	Discontinued
0.6229	Remote Similarity	NPD6745	Discontinued
0.6224	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5003	Discontinued
0.622	Remote Similarity	NPD2880	Discontinued
0.6215	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD7957	Phase 1
0.6206	Remote Similarity	NPD2408	Discontinued
0.6204	Remote Similarity	NPD7619	Phase 3
0.6204	Remote Similarity	NPD7618	Phase 3
0.6204	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4079	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