NPASS Compound

Structure

CID84853 OpenBabel06191715422D 24 26 0 0 0 0 0 0 0 0999 V2000 -6.6274 3.7791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8487 2.9411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0182 3.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1274 2.9131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6274 2.0471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6274 2.0471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 -0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1274 1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1280 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3305 0.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5396 0.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5396 1.9901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1274 1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5886 0.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 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 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4644 1.1303 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5886 1.6810 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3272 2.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 14 1 0 0 0 0 3 24 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 7 10 2 0 0 0 0 8 15 1 0 0 0 0 9 17 2 0 0 0 0 10 21 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 22 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	323.2
Volume:	352.132
LogP:	5.225
LogD:	4.727
LogS:	-4.595
# Rotatable Bonds:	7
TPSA:	56.6
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.574
Synthetic Accessibility Score:	3.397
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.298
MDCK Permeability:	8.729435649001971e-06
Pgp-inhibitor:	0.813
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.652
30% Bioavailability (F30%):	0.333

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.386
Plasma Protein Binding (PPB):	95.97838592529297%
Volume Distribution (VD):	1.905
Pgp-substrate:	3.9895682334899902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.888
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.831
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.545
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.916
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	5.106
Half-life (T1/2):	0.484

ADMET: Toxicity

hERG Blockers:	0.762
Human Hepatotoxicity (H-HT):	0.824
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.63
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.755
Carcinogencity:	0.259
Eye Corrosion:	0.008
Eye Irritation:	0.383
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC84853

Natural Product ID:	NPC84853
*Common Name:**	Prodigiosin
IUPAC Name:	n.a.
Synonyms:	Prodigiosin
Standard InCHIKey:	SZXDNGVQRDTJSD-VBKFSLOCSA-N
Standard InCHI:	InChI=1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12-
SMILES:	CCCCCC1=C/C(=C/c2c(cc(c3ccc[nH]3)[nH]2)OC)/N=C1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL275787
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002257] Substituted pyrroles [CHEMONTID:0002028] Dipyrrins

*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
NPO2567	Serratia marcescens	Species	Yersiniaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14325279]
NPO2567	Serratia marcescens	Species	Yersiniaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15853884]
NPO2567	Serratia marcescens	Species	Yersiniaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18313305]
NPO2567	Serratia marcescens	Species	Yersiniaceae	Bacteria	n.a.	n.a.	n.a.	PMID[783153]
NPO2567	Serratia marcescens	Species	Yersiniaceae	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
IC50	9
MIC	5
Others	5

Activity Type	# Activity
Cell Line	6
Individual Protein	1
NON-MOLECULAR	4
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	77.0	nM	PMID[494880]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	79.0	nM	PMID[494880]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	173.0	nM	PMID[494880]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	213.0	nM	PMID[494880]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	32.0	nM	PMID[494880]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	1300.0	nM	PMID[494881]
NPT3985	Individual Protein	Probable low molecular weight protein-tyrosine-phosphatase	Mycobacterium tuberculosis	IC50	=	8800.0	nM	PMID[494883]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8.0	nM	PMID[494882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	75000.0	nM	PMID[494884]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	28.0	%	PMID[494884]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	34.0	%	PMID[494884]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	5.6	%	PMID[494884]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1.0	ug.mL-1	PMID[494885]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32.0	ug.mL-1	PMID[494885]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2.0	ug.mL-1	PMID[494885]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[494885]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[494885]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Ratio	=	8.0	n.a.	PMID[494885]
NPT19	Organism	Escherichia coli	Escherichia coli	Ratio	=	2.0	n.a.	PMID[494885]

☑ 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 NPC84853 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	625
0.1-0.2	11741
0.2-0.3	7687
0.3-0.4	15145
0.4-0.5	3759
0.5-0.6	2664
0.6-0.7	972
0.7-0.8	96
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9494	High Similarity	NPC187558
0.871	High Similarity	NPC19872
0.8556	High Similarity	NPC18487
0.8187	Intermediate Similarity	NPC245816
0.8187	Intermediate Similarity	NPC476138
0.8158	Intermediate Similarity	NPC267928
0.8142	Intermediate Similarity	NPC161887
0.8131	Intermediate Similarity	NPC26679
0.8108	Intermediate Similarity	NPC20249
0.8107	Intermediate Similarity	NPC314954
0.8071	Intermediate Similarity	NPC185782
0.8031	Intermediate Similarity	NPC121772
0.8	Intermediate Similarity	NPC476518
0.799	Intermediate Similarity	NPC469554
0.799	Intermediate Similarity	NPC232727
0.799	Intermediate Similarity	NPC101543
0.7956	Intermediate Similarity	NPC121658
0.7956	Intermediate Similarity	NPC14651
0.7946	Intermediate Similarity	NPC266551
0.7946	Intermediate Similarity	NPC219963
0.7938	Intermediate Similarity	NPC176538
0.7937	Intermediate Similarity	NPC76748
0.7912	Intermediate Similarity	NPC111624
0.7895	Intermediate Similarity	NPC92111
0.7884	Intermediate Similarity	NPC296527
0.7841	Intermediate Similarity	NPC477815
0.7833	Intermediate Similarity	NPC470799
0.7833	Intermediate Similarity	NPC8022
0.7824	Intermediate Similarity	NPC13880
0.7812	Intermediate Similarity	NPC226202
0.7812	Intermediate Similarity	NPC307963
0.7766	Intermediate Similarity	NPC284678
0.7761	Intermediate Similarity	NPC167860
0.7761	Intermediate Similarity	NPC123976
0.775	Intermediate Similarity	NPC287208
0.7734	Intermediate Similarity	NPC476287
0.773	Intermediate Similarity	NPC224764
0.7696	Intermediate Similarity	NPC470549
0.7659	Intermediate Similarity	NPC170114
0.7656	Intermediate Similarity	NPC134079
0.7647	Intermediate Similarity	NPC42979
0.7644	Intermediate Similarity	NPC310118
0.7638	Intermediate Similarity	NPC475774
0.76	Intermediate Similarity	NPC285558
0.7576	Intermediate Similarity	NPC315957
0.757	Intermediate Similarity	NPC196718
0.7551	Intermediate Similarity	NPC251090
0.7548	Intermediate Similarity	NPC193267
0.7548	Intermediate Similarity	NPC292958
0.7548	Intermediate Similarity	NPC213530
0.7512	Intermediate Similarity	NPC94157
0.7488	Intermediate Similarity	NPC102593
0.7488	Intermediate Similarity	NPC288349
0.7465	Intermediate Similarity	NPC110151
0.7461	Intermediate Similarity	NPC206251
0.7461	Intermediate Similarity	NPC74382
0.7454	Intermediate Similarity	NPC180504
0.7437	Intermediate Similarity	NPC476167
0.7423	Intermediate Similarity	NPC224327
0.7411	Intermediate Similarity	NPC26543
0.7402	Intermediate Similarity	NPC476465
0.7399	Intermediate Similarity	NPC104049
0.7398	Intermediate Similarity	NPC324149
0.7393	Intermediate Similarity	NPC60621
0.7387	Intermediate Similarity	NPC192315
0.7377	Intermediate Similarity	NPC25899
0.7373	Intermediate Similarity	NPC141053
0.7361	Intermediate Similarity	NPC260434
0.734	Intermediate Similarity	NPC470500
0.733	Intermediate Similarity	NPC5145
0.7325	Intermediate Similarity	NPC53534
0.7318	Intermediate Similarity	NPC101350
0.7308	Intermediate Similarity	NPC469592
0.7308	Intermediate Similarity	NPC471080
0.7306	Intermediate Similarity	NPC84478
0.7295	Intermediate Similarity	NPC208284
0.7277	Intermediate Similarity	NPC141377
0.7273	Intermediate Similarity	NPC235685
0.7264	Intermediate Similarity	NPC132642
0.726	Intermediate Similarity	NPC316981
0.7254	Intermediate Similarity	NPC48938
0.7254	Intermediate Similarity	NPC176127
0.7245	Intermediate Similarity	NPC242928
0.7243	Intermediate Similarity	NPC48192
0.7243	Intermediate Similarity	NPC122436
0.7231	Intermediate Similarity	NPC171171
0.7225	Intermediate Similarity	NPC266931
0.7222	Intermediate Similarity	NPC473185
0.7216	Intermediate Similarity	NPC204717
0.7202	Intermediate Similarity	NPC118776
0.7198	Intermediate Similarity	NPC473181
0.7198	Intermediate Similarity	NPC174672
0.7194	Intermediate Similarity	NPC46580
0.7186	Intermediate Similarity	NPC106937
0.7182	Intermediate Similarity	NPC182222
0.7181	Intermediate Similarity	NPC1527
0.7179	Intermediate Similarity	NPC314002
0.7175	Intermediate Similarity	NPC148889
0.7171	Intermediate Similarity	NPC475070
0.717	Intermediate Similarity	NPC469594
0.7165	Intermediate Similarity	NPC220765
0.7164	Intermediate Similarity	NPC77555
0.7163	Intermediate Similarity	NPC199667
0.7163	Intermediate Similarity	NPC11464
0.7151	Intermediate Similarity	NPC177404
0.7137	Intermediate Similarity	NPC152620
0.7135	Intermediate Similarity	NPC184964
0.7135	Intermediate Similarity	NPC96890
0.7123	Intermediate Similarity	NPC475253
0.7122	Intermediate Similarity	NPC223427
0.7117	Intermediate Similarity	NPC240384
0.7115	Intermediate Similarity	NPC174758
0.7113	Intermediate Similarity	NPC474798
0.71	Intermediate Similarity	NPC198673
0.7097	Intermediate Similarity	NPC131718
0.7095	Intermediate Similarity	NPC473180
0.7093	Intermediate Similarity	NPC471891
0.7089	Intermediate Similarity	NPC303658
0.7073	Intermediate Similarity	NPC473761
0.7067	Intermediate Similarity	NPC82548
0.7059	Intermediate Similarity	NPC329747
0.7056	Intermediate Similarity	NPC473179
0.7054	Intermediate Similarity	NPC477861
0.705	Intermediate Similarity	NPC99666
0.7044	Intermediate Similarity	NPC168911
0.7042	Intermediate Similarity	NPC304926
0.7042	Intermediate Similarity	NPC476041
0.7021	Intermediate Similarity	NPC118511
0.7021	Intermediate Similarity	NPC102423
0.7018	Intermediate Similarity	NPC153467
0.7011	Intermediate Similarity	NPC26872
0.6996	Remote Similarity	NPC258048
0.6996	Remote Similarity	NPC295228
0.6987	Remote Similarity	NPC63971
0.6987	Remote Similarity	NPC91868
0.6986	Remote Similarity	NPC266249
0.6985	Remote Similarity	NPC110741
0.6979	Remote Similarity	NPC313791
0.6977	Remote Similarity	NPC168209
0.6976	Remote Similarity	NPC329793
0.6964	Remote Similarity	NPC15801
0.6964	Remote Similarity	NPC473183
0.6963	Remote Similarity	NPC305984
0.6961	Remote Similarity	NPC239954
0.696	Remote Similarity	NPC316756
0.6952	Remote Similarity	NPC469589
0.6946	Remote Similarity	NPC242209
0.6941	Remote Similarity	NPC227908
0.6937	Remote Similarity	NPC473186
0.6931	Remote Similarity	NPC311276
0.693	Remote Similarity	NPC472434
0.693	Remote Similarity	NPC264285
0.6927	Remote Similarity	NPC128823
0.6919	Remote Similarity	NPC15102
0.6919	Remote Similarity	NPC123839
0.6916	Remote Similarity	NPC274982
0.6915	Remote Similarity	NPC285635
0.6901	Remote Similarity	NPC162530
0.69	Remote Similarity	NPC32771
0.6898	Remote Similarity	NPC26850
0.6892	Remote Similarity	NPC476451
0.6881	Remote Similarity	NPC243633
0.6881	Remote Similarity	NPC175150
0.6875	Remote Similarity	NPC473184
0.6875	Remote Similarity	NPC39370
0.6866	Remote Similarity	NPC86078
0.6856	Remote Similarity	NPC78609
0.6842	Remote Similarity	NPC476118
0.6837	Remote Similarity	NPC152768
0.6837	Remote Similarity	NPC148183
0.6837	Remote Similarity	NPC472027
0.6837	Remote Similarity	NPC36405
0.6833	Remote Similarity	NPC6215
0.6829	Remote Similarity	NPC243834
0.6829	Remote Similarity	NPC70956
0.6829	Remote Similarity	NPC156704
0.6828	Remote Similarity	NPC259644
0.6828	Remote Similarity	NPC469765
0.6828	Remote Similarity	NPC73952
0.6828	Remote Similarity	NPC25008
0.6828	Remote Similarity	NPC469760
0.6828	Remote Similarity	NPC469763
0.6828	Remote Similarity	NPC469786
0.6825	Remote Similarity	NPC475910
0.6822	Remote Similarity	NPC478074
0.6814	Remote Similarity	NPC326634
0.6814	Remote Similarity	NPC131017
0.6809	Remote Similarity	NPC212742
0.6804	Remote Similarity	NPC16352
0.6804	Remote Similarity	NPC470501
0.6802	Remote Similarity	NPC194740
0.6796	Remote Similarity	NPC72211
0.6791	Remote Similarity	NPC211572
0.6791	Remote Similarity	NPC80597
0.6791	Remote Similarity	NPC75540
0.6791	Remote Similarity	NPC212376
0.6791	Remote Similarity	NPC70922
0.6789	Remote Similarity	NPC477533
0.6789	Remote Similarity	NPC323969
0.6784	Remote Similarity	NPC11408

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 NPC84853 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	988
0.2-0.3	608
0.3-0.4	2047
0.4-0.5	2611
0.5-0.6	2070
0.6-0.7	481
0.7-0.8	36
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD565	Phase 2
0.7812	Intermediate Similarity	NPD1038	Approved
0.7812	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD1392	Approved
0.7576	Intermediate Similarity	NPD1739	Approved
0.7576	Intermediate Similarity	NPD1740	Approved
0.7525	Intermediate Similarity	NPD3825	Phase 3
0.7525	Intermediate Similarity	NPD4548	Discontinued
0.7512	Intermediate Similarity	NPD4795	Phase 2
0.7477	Intermediate Similarity	NPD8512	Phase 3
0.7463	Intermediate Similarity	NPD5066	Phase 2
0.7463	Intermediate Similarity	NPD5067	Phase 2
0.7461	Intermediate Similarity	NPD1034	Phase 3
0.7461	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD2189	Approved
0.7402	Intermediate Similarity	NPD2187	Approved
0.7398	Intermediate Similarity	NPD4372	Phase 1
0.7389	Intermediate Similarity	NPD8403	Phase 1
0.7377	Intermediate Similarity	NPD1418	Phase 2
0.7374	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD3477	Phase 2
0.7364	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD9574	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD1768	Approved
0.7323	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD949	Phase 1
0.7238	Intermediate Similarity	NPD5612	Discontinued
0.7231	Intermediate Similarity	NPD5256	Discontinued
0.722	Intermediate Similarity	NPD3003	Approved
0.7217	Intermediate Similarity	NPD3402	Phase 1
0.7212	Intermediate Similarity	NPD4131	Phase 3
0.7188	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD802	Phase 2
0.7182	Intermediate Similarity	NPD3833	Phase 3
0.7182	Intermediate Similarity	NPD3835	Phase 3
0.7156	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3570	Phase 2
0.7117	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5559	Phase 2
0.7106	Intermediate Similarity	NPD3343	Phase 3
0.7105	Intermediate Similarity	NPD5482	Discontinued
0.7094	Intermediate Similarity	NPD5999	Phase 2
0.709	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3006	Discontinued
0.7067	Intermediate Similarity	NPD5658	Approved
0.7062	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7558	Phase 2
0.7048	Intermediate Similarity	NPD3939	Suspended
0.7047	Intermediate Similarity	NPD4072	Approved
0.7047	Intermediate Similarity	NPD4071	Approved
0.7035	Intermediate Similarity	NPD5802	Phase 2
0.7028	Intermediate Similarity	NPD5902	Approved
0.7028	Intermediate Similarity	NPD5903	Approved
0.7023	Intermediate Similarity	NPD6242	Discontinued
0.7016	Intermediate Similarity	NPD9548	Phase 2
0.7015	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6202	Discontinued
0.701	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5948	Phase 2
0.7005	Intermediate Similarity	NPD6306	Phase 2
0.7	Intermediate Similarity	NPD5018	Phase 3
0.6989	Remote Similarity	NPD2581	Approved
0.6989	Remote Similarity	NPD2582	Approved
0.6983	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2471	Approved
0.6982	Remote Similarity	NPD2472	Approved
0.698	Remote Similarity	NPD3395	Approved
0.698	Remote Similarity	NPD1951	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3396	Approved
0.6965	Remote Similarity	NPD6569	Phase 2
0.6963	Remote Similarity	NPD5319	Approved
0.6963	Remote Similarity	NPD5320	Approved
0.696	Remote Similarity	NPD1941	Approved
0.6957	Remote Similarity	NPD9595	Approved
0.6957	Remote Similarity	NPD9596	Approved
0.6941	Remote Similarity	NPD1273	Discontinued
0.693	Remote Similarity	NPD5632	Approved
0.693	Remote Similarity	NPD4429	Discontinued
0.6916	Remote Similarity	NPD6643	Discontinued
0.6915	Remote Similarity	NPD9705	Discontinued
0.6915	Remote Similarity	NPD112	Approved
0.6912	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD2952	Discontinued
0.6912	Remote Similarity	NPD7948	Phase 1
0.6895	Remote Similarity	NPD1258	Discontinued
0.6892	Remote Similarity	NPD2062	Phase 2
0.6884	Remote Similarity	NPD4921	Phase 3
0.6884	Remote Similarity	NPD706	Phase 1
0.6884	Remote Similarity	NPD4919	Phase 3
0.6884	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD1856	Discontinued
0.6872	Remote Similarity	NPD2144	Approved
0.6869	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7603	Discontinued
0.6853	Remote Similarity	NPD3386	Phase 2
0.6849	Remote Similarity	NPD5045	Phase 2
0.6844	Remote Similarity	NPD1259	Discontinued
0.6842	Remote Similarity	NPD862	Approved
0.6842	Remote Similarity	NPD5140	Approved
0.6842	Remote Similarity	NPD861	Approved
0.6842	Remote Similarity	NPD5138	Approved
0.6842	Remote Similarity	NPD3397	Phase 2
0.6842	Remote Similarity	NPD863	Approved
0.6837	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2510	Approved
0.6825	Remote Similarity	NPD2509	Approved
0.682	Remote Similarity	NPD7194	Discontinued
0.682	Remote Similarity	NPD537	Phase 2
0.682	Remote Similarity	NPD534	Phase 2
0.682	Remote Similarity	NPD8284	Discontinued
0.6818	Remote Similarity	NPD2955	Approved
0.6818	Remote Similarity	NPD4890	Phase 2
0.6818	Remote Similarity	NPD2954	Approved
0.6814	Remote Similarity	NPD4344	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4343	Phase 1
0.6812	Remote Similarity	NPD7067	Approved
0.6812	Remote Similarity	NPD7068	Approved
0.6794	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2547	Discontinued
0.6786	Remote Similarity	NPD1032	Phase 2
0.6779	Remote Similarity	NPD5259	Phase 3
0.6777	Remote Similarity	NPD796	Phase 2
0.6776	Remote Similarity	NPD3330	Phase 1
0.6774	Remote Similarity	NPD6985	Discontinued
0.6771	Remote Similarity	NPD424	Approved
0.6771	Remote Similarity	NPD425	Approved
0.677	Remote Similarity	NPD4454	Phase 2
0.677	Remote Similarity	NPD4654	Phase 1
0.6769	Remote Similarity	NPD6473	Phase 1
0.6769	Remote Similarity	NPD5065	Approved
0.6768	Remote Similarity	NPD3038	Discontinued
0.6766	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2151	Approved
0.6762	Remote Similarity	NPD4037	Approved
0.6762	Remote Similarity	NPD4039	Approved
0.6762	Remote Similarity	NPD4034	Approved
0.6762	Remote Similarity	NPD4033	Approved
0.6762	Remote Similarity	NPD31	Approved
0.6762	Remote Similarity	NPD4122	Approved
0.6762	Remote Similarity	NPD32	Approved
0.6762	Remote Similarity	NPD4036	Approved
0.6762	Remote Similarity	NPD4038	Approved
0.6762	Remote Similarity	NPD4035	Approved
0.6756	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5450	Discontinued
0.675	Remote Similarity	NPD4889	Approved
0.6749	Remote Similarity	NPD4148	Approved
0.6745	Remote Similarity	NPD5529	Phase 1
0.6745	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3938	Phase 1
0.6734	Remote Similarity	NPD5596	Phase 2
0.6733	Remote Similarity	NPD4021	Phase 2
0.6732	Remote Similarity	NPD978	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD484	Approved
0.673	Remote Similarity	NPD5601	Phase 2
0.6728	Remote Similarity	NPD1744	Approved
0.6728	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD2601	Approved
0.6717	Remote Similarity	NPD6595	Phase 3
0.6717	Remote Similarity	NPD2600	Approved
0.6717	Remote Similarity	NPD2599	Approved
0.6716	Remote Similarity	NPD3922	Approved
0.6716	Remote Similarity	NPD3924	Approved
0.6716	Remote Similarity	NPD3923	Approved
0.6716	Remote Similarity	NPD3921	Approved
0.6714	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6856	Discontinued
0.6711	Remote Similarity	NPD3331	Phase 3
0.67	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD774	Phase 3
0.6698	Remote Similarity	NPD2848	Discontinued
0.6696	Remote Similarity	NPD6969	Phase 2
0.6696	Remote Similarity	NPD6968	Phase 2
0.6696	Remote Similarity	NPD5479	Discontinued
0.6695	Remote Similarity	NPD8442	Discontinued
0.6695	Remote Similarity	NPD4558	Phase 2
0.6695	Remote Similarity	NPD5644	Phase 1
0.6683	Remote Similarity	NPD4203	Approved
0.6683	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4204	Approved
0.6682	Remote Similarity	NPD1910	Approved
0.6682	Remote Similarity	NPD1911	Approved
0.6667	Remote Similarity	NPD2334	Discontinued
0.6667	Remote Similarity	NPD1286	Suspended
0.6667	Remote Similarity	NPD3875	Discontinued
0.6667	Remote Similarity	NPD1622	Discontinued
0.6667	Remote Similarity	NPD6961	Discontinued
0.6667	Remote Similarity	NPD2314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2894	Phase 2
0.6667	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2772	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7219	Approved
0.6652	Remote Similarity	NPD7221	Approved
0.6651	Remote Similarity	NPD7470	Discontinued

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