NPASS Compound

Structure

CID192712 OpenBabel06191715582D 29 33 0 0 0 0 0 0 0 0999 V2000 3.4826 -0.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1759 4.8531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 4.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9190 4.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 2.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 3.5659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 3.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7111 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2248 4.5441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 2.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7111 3.2058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 2.3781 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.4817 5.2132 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 4.1871 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2989 2.3968 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 1.6555 -1.2733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6736 0.1280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 8 25 1 0 0 0 0 9 16 2 0 0 0 0 9 26 1 0 0 0 0 10 17 2 0 0 0 0 10 27 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 18 2 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 21 2 0 0 0 0 21 22 1 0 0 0 0 21 27 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	423.05
Volume:	398.278
LogP:	5.74
LogD:	3.926
LogS:	-5.868
# Rotatable Bonds:	4
TPSA:	73.67
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	2.738
Fsp3:	0.045
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:	-5.305
MDCK Permeability:	4.106600499653723e-06
Pgp-inhibitor:	0.973
Pgp-substrate:	0.68
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	100.27800750732422%
Volume Distribution (VD):	1.514
Pgp-substrate:	0.8594314455986023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.187
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.91
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.82
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.944
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	5.866
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.529
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.166
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.097

Download Data

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

Natural Product: NPC192712

Natural Product ID:	NPC192712
*Common Name:**	Lynamicin A
IUPAC Name:	methyl 3,4-bis(5-chloro-1H-indol-3-yl)-1H-pyrrole-2-carboxylate
Synonyms:
Standard InCHIKey:	ADBVWUJBUGOHJH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H15Cl2N3O2/c1-29-22(28)21-20(16-9-26-19-5-3-12(24)7-14(16)19)17(10-27-21)15-8-25-18-4-2-11(23)6-13(15)18/h2-10,25-27H,1H3
SMILES:	COC(=O)c1c(c2c[nH]c3ccc(cc23)Cl)c(c[nH]1)c1c[nH]c2ccc(cc12)Cl
Synthetic Gene Cluster:	BGC0001782;
ChEMBL Identifier:	CHEMBL491626
PubChem CID:	11304789
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO33622	actinomycete sp. NPS12745	Species	n.a.	n.a.	isolated from a marine sediment sample	Mission Bay, San Diego, CA	n.a.	PMID[18842058]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
MIC	11

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4300.0	nM	PMID[473232]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4700.0	nM	PMID[473232]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	9500.0	nM	PMID[473232]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	57000.0	nM	PMID[473232]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	19000.0	nM	PMID[473232]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	19000.0	nM	PMID[473232]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	38000.0	nM	PMID[473232]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	28000.0	nM	PMID[473232]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	16000.0	nM	PMID[473232]
NPT2665	Organism	unidentified herpesvirus	unidentified herpesvirus	IC50	=	17.2	ug.mL-1	PMID[473232]

☑ 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 NPC192712 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	613
0.1-0.2	4543
0.2-0.3	13107
0.3-0.4	17271
0.4-0.5	3235
0.5-0.6	2128
0.6-0.7	1615
0.7-0.8	171
0.8-0.85	6
0.85-0.9	1
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9853	High Similarity	NPC315062
0.9805	High Similarity	NPC244897
0.9756	High Similarity	NPC267853
0.971	High Similarity	NPC316411
0.9617	High Similarity	NPC104712
0.9122	High Similarity	NPC36405
0.8654	High Similarity	NPC82370
0.8386	Intermediate Similarity	NPC15801
0.8263	Intermediate Similarity	NPC118940
0.8164	Intermediate Similarity	NPC67288
0.816	Intermediate Similarity	NPC266249
0.8084	Intermediate Similarity	NPC123839
0.7973	Intermediate Similarity	NPC229893
0.7788	Intermediate Similarity	NPC138370
0.7778	Intermediate Similarity	NPC321708
0.7692	Intermediate Similarity	NPC477979
0.7685	Intermediate Similarity	NPC132539
0.7653	Intermediate Similarity	NPC131887
0.7623	Intermediate Similarity	NPC472285
0.7617	Intermediate Similarity	NPC74413
0.7609	Intermediate Similarity	NPC260434
0.7598	Intermediate Similarity	NPC145885
0.7598	Intermediate Similarity	NPC14113
0.7598	Intermediate Similarity	NPC84827
0.7597	Intermediate Similarity	NPC240384
0.7596	Intermediate Similarity	NPC160381
0.7561	Intermediate Similarity	NPC248041
0.7561	Intermediate Similarity	NPC126709
0.7534	Intermediate Similarity	NPC474412
0.7524	Intermediate Similarity	NPC314919
0.7523	Intermediate Similarity	NPC227582
0.7521	Intermediate Similarity	NPC235685
0.7512	Intermediate Similarity	NPC260900
0.7512	Intermediate Similarity	NPC57398
0.7489	Intermediate Similarity	NPC101350
0.7476	Intermediate Similarity	NPC283219
0.7463	Intermediate Similarity	NPC267885
0.7455	Intermediate Similarity	NPC478157
0.7442	Intermediate Similarity	NPC141454
0.7419	Intermediate Similarity	NPC252338
0.7415	Intermediate Similarity	NPC149155
0.7415	Intermediate Similarity	NPC203468
0.7415	Intermediate Similarity	NPC110500
0.7411	Intermediate Similarity	NPC89508
0.7406	Intermediate Similarity	NPC83111
0.7389	Intermediate Similarity	NPC312645
0.7387	Intermediate Similarity	NPC478158
0.7383	Intermediate Similarity	NPC304203
0.7362	Intermediate Similarity	NPC182222
0.7352	Intermediate Similarity	NPC193761
0.7346	Intermediate Similarity	NPC235684
0.7343	Intermediate Similarity	NPC284775
0.7333	Intermediate Similarity	NPC284678
0.733	Intermediate Similarity	NPC82053
0.7318	Intermediate Similarity	NPC165599
0.7311	Intermediate Similarity	NPC278434
0.7304	Intermediate Similarity	NPC78020
0.7299	Intermediate Similarity	NPC282103
0.7293	Intermediate Similarity	NPC276657
0.729	Intermediate Similarity	NPC476460
0.7286	Intermediate Similarity	NPC83381
0.7284	Intermediate Similarity	NPC472762
0.7281	Intermediate Similarity	NPC264285
0.7277	Intermediate Similarity	NPC196718
0.7276	Intermediate Similarity	NPC53534
0.7273	Intermediate Similarity	NPC122436
0.7273	Intermediate Similarity	NPC476073
0.7273	Intermediate Similarity	NPC469896
0.726	Intermediate Similarity	NPC214428
0.726	Intermediate Similarity	NPC111275
0.7222	Intermediate Similarity	NPC326422
0.722	Intermediate Similarity	NPC54420
0.7215	Intermediate Similarity	NPC123395
0.7203	Intermediate Similarity	NPC207686
0.7203	Intermediate Similarity	NPC102593
0.7195	Intermediate Similarity	NPC476874
0.7182	Intermediate Similarity	NPC315491
0.7182	Intermediate Similarity	NPC45459
0.7176	Intermediate Similarity	NPC315617
0.7176	Intermediate Similarity	NPC316359
0.7174	Intermediate Similarity	NPC74360
0.7172	Intermediate Similarity	NPC91868
0.7172	Intermediate Similarity	NPC63971
0.7171	Intermediate Similarity	NPC152620
0.7169	Intermediate Similarity	NPC171317
0.7162	Intermediate Similarity	NPC317701
0.7156	Intermediate Similarity	NPC162860
0.7155	Intermediate Similarity	NPC16352
0.7149	Intermediate Similarity	NPC471944
0.7143	Intermediate Similarity	NPC472210
0.7143	Intermediate Similarity	NPC81802
0.7143	Intermediate Similarity	NPC244741
0.7143	Intermediate Similarity	NPC269886
0.7143	Intermediate Similarity	NPC213468
0.7143	Intermediate Similarity	NPC472295
0.7143	Intermediate Similarity	NPC39370
0.7143	Intermediate Similarity	NPC55772
0.7143	Intermediate Similarity	NPC247735
0.7137	Intermediate Similarity	NPC207020
0.7136	Intermediate Similarity	NPC103361
0.7131	Intermediate Similarity	NPC473186
0.7119	Intermediate Similarity	NPC472844
0.7108	Intermediate Similarity	NPC258048
0.7105	Intermediate Similarity	NPC39500
0.7105	Intermediate Similarity	NPC229348
0.7103	Intermediate Similarity	NPC315555
0.7101	Intermediate Similarity	NPC70155
0.7098	Intermediate Similarity	NPC175602
0.7097	Intermediate Similarity	NPC316018
0.7097	Intermediate Similarity	NPC314058
0.7097	Intermediate Similarity	NPC55493
0.7097	Intermediate Similarity	NPC472292
0.7095	Intermediate Similarity	NPC59269
0.7094	Intermediate Similarity	NPC476818
0.708	Intermediate Similarity	NPC61038
0.7078	Intermediate Similarity	NPC179701
0.7078	Intermediate Similarity	NPC79356
0.7078	Intermediate Similarity	NPC102592
0.707	Intermediate Similarity	NPC17059
0.7067	Intermediate Similarity	NPC321428
0.7066	Intermediate Similarity	NPC148889
0.7064	Intermediate Similarity	NPC88315
0.7062	Intermediate Similarity	NPC219336
0.7061	Intermediate Similarity	NPC318299
0.7061	Intermediate Similarity	NPC110182
0.7061	Intermediate Similarity	NPC75634
0.7056	Intermediate Similarity	NPC280290
0.7054	Intermediate Similarity	NPC473376
0.7054	Intermediate Similarity	NPC327592
0.7045	Intermediate Similarity	NPC262898
0.7039	Intermediate Similarity	NPC60621
0.7031	Intermediate Similarity	NPC54744
0.7031	Intermediate Similarity	NPC317752
0.7027	Intermediate Similarity	NPC213308
0.7023	Intermediate Similarity	NPC62749
0.7022	Intermediate Similarity	NPC277350
0.7022	Intermediate Similarity	NPC317373
0.7022	Intermediate Similarity	NPC300156
0.7014	Intermediate Similarity	NPC15573
0.7014	Intermediate Similarity	NPC183662
0.7014	Intermediate Similarity	NPC474916
0.7014	Intermediate Similarity	NPC217372
0.7013	Intermediate Similarity	NPC27041
0.7012	Intermediate Similarity	NPC74619
0.7009	Intermediate Similarity	NPC207851
0.7005	Intermediate Similarity	NPC154339
0.7005	Intermediate Similarity	NPC469489
0.7004	Intermediate Similarity	NPC194740
0.7	Intermediate Similarity	NPC472293
0.7	Intermediate Similarity	NPC118228
0.7	Intermediate Similarity	NPC325976
0.6995	Remote Similarity	NPC191415
0.6995	Remote Similarity	NPC71037
0.6992	Remote Similarity	NPC24370
0.6992	Remote Similarity	NPC319232
0.6991	Remote Similarity	NPC4687
0.699	Remote Similarity	NPC8104
0.6987	Remote Similarity	NPC473493
0.6986	Remote Similarity	NPC267343
0.6983	Remote Similarity	NPC281049
0.6983	Remote Similarity	NPC184408
0.6977	Remote Similarity	NPC15102
0.6963	Remote Similarity	NPC102755
0.696	Remote Similarity	NPC39679
0.6959	Remote Similarity	NPC213629
0.6957	Remote Similarity	NPC207866
0.6955	Remote Similarity	NPC202812
0.6955	Remote Similarity	NPC135950
0.6951	Remote Similarity	NPC178858
0.6949	Remote Similarity	NPC125597
0.6944	Remote Similarity	NPC94752
0.6936	Remote Similarity	NPC144452
0.6933	Remote Similarity	NPC475774
0.6927	Remote Similarity	NPC329858
0.6927	Remote Similarity	NPC135141
0.6927	Remote Similarity	NPC92796
0.6923	Remote Similarity	NPC41717
0.6923	Remote Similarity	NPC323969
0.6913	Remote Similarity	NPC471194
0.6913	Remote Similarity	NPC471193
0.6911	Remote Similarity	NPC78609
0.691	Remote Similarity	NPC477714
0.6909	Remote Similarity	NPC198673
0.6906	Remote Similarity	NPC293917
0.6906	Remote Similarity	NPC472297
0.6906	Remote Similarity	NPC472296
0.6898	Remote Similarity	NPC308931
0.6898	Remote Similarity	NPC473189
0.6898	Remote Similarity	NPC99939
0.6897	Remote Similarity	NPC170114
0.6897	Remote Similarity	NPC85702
0.6894	Remote Similarity	NPC473317
0.689	Remote Similarity	NPC63751
0.6888	Remote Similarity	NPC323198
0.6888	Remote Similarity	NPC323752
0.6887	Remote Similarity	NPC84347
0.6884	Remote Similarity	NPC48938
0.6884	Remote Similarity	NPC469358
0.6883	Remote Similarity	NPC221100
0.6883	Remote Similarity	NPC234078

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 NPC192712 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	674
0.2-0.3	887
0.3-0.4	2052
0.4-0.5	2611
0.5-0.6	1978
0.6-0.7	580
0.7-0.8	45
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
0.7963	Intermediate Similarity	NPD7470	Discontinued
0.7936	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7804	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2510	Approved
0.7742	Intermediate Similarity	NPD2509	Approved
0.7705	Intermediate Similarity	NPD5450	Discontinued
0.765	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5901	Discontinued
0.7553	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD3178	Discontinued
0.7463	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7441	Intermediate Similarity	NPD1534	Approved
0.7427	Intermediate Similarity	NPD5482	Discontinued
0.7422	Intermediate Similarity	NPD3389	Approved
0.7422	Intermediate Similarity	NPD3393	Approved
0.7422	Intermediate Similarity	NPD3394	Approved
0.7415	Intermediate Similarity	NPD482	Approved
0.7354	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5475	Discontinued
0.7308	Intermediate Similarity	NPD7688	Phase 1
0.7293	Intermediate Similarity	NPD1996	Discontinued
0.7293	Intermediate Similarity	NPD6242	Discontinued
0.7286	Intermediate Similarity	NPD2095	Phase 2
0.7286	Intermediate Similarity	NPD2092	Phase 2
0.7286	Intermediate Similarity	NPD2094	Phase 2
0.7257	Intermediate Similarity	NPD3243	Approved
0.7252	Intermediate Similarity	NPD7001	Phase 3
0.7251	Intermediate Similarity	NPD2091	Phase 2
0.7251	Intermediate Similarity	NPD2096	Phase 2
0.7244	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD3280	Approved
0.7207	Intermediate Similarity	NPD3947	Discontinued
0.7207	Intermediate Similarity	NPD5426	Phase 3
0.7203	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5003	Discontinued
0.7198	Intermediate Similarity	NPD750	Phase 2
0.719	Intermediate Similarity	NPD6595	Phase 3
0.7185	Intermediate Similarity	NPD4454	Phase 2
0.7182	Intermediate Similarity	NPD484	Approved
0.7179	Intermediate Similarity	NPD3259	Approved
0.7154	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD7576	Discontinued
0.7124	Intermediate Similarity	NPD3222	Phase 2
0.7123	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3006	Discontinued
0.7091	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4848	Phase 1
0.7059	Intermediate Similarity	NPD6999	Discontinued
0.7059	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5632	Approved
0.7054	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6735	Approved
0.7031	Intermediate Similarity	NPD2823	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2305	Discontinued
0.7017	Intermediate Similarity	NPD8238	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6176	Phase 1
0.7	Intermediate Similarity	NPD3257	Approved
0.697	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7404	Approved
0.6953	Remote Similarity	NPD6770	Approved
0.6947	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7010	Phase 3
0.6944	Remote Similarity	NPD6217	Discontinued
0.694	Remote Similarity	NPD5818	Discontinued
0.6936	Remote Similarity	NPD6995	Phase 1
0.6927	Remote Similarity	NPD2564	Approved
0.6927	Remote Similarity	NPD2565	Phase 2
0.6919	Remote Similarity	NPD1586	Approved
0.6914	Remote Similarity	NPD6154	Approved
0.6913	Remote Similarity	NPD8096	Phase 3
0.6913	Remote Similarity	NPD8097	Phase 3
0.6912	Remote Similarity	NPD4948	Discontinued
0.691	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4429	Discontinued
0.6909	Remote Similarity	NPD4528	Approved
0.6909	Remote Similarity	NPD4529	Approved
0.6909	Remote Similarity	NPD4526	Approved
0.6906	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4845	Discontinued
0.6886	Remote Similarity	NPD7666	Phase 3
0.6886	Remote Similarity	NPD7665	Phase 2
0.6883	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.688	Remote Similarity	NPD3258	Approved
0.6875	Remote Similarity	NPD1867	Approved
0.6872	Remote Similarity	NPD2076	Approved
0.6872	Remote Similarity	NPD2077	Approved
0.6866	Remote Similarity	NPD8349	Phase 1
0.6861	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.686	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4499	Approved
0.6849	Remote Similarity	NPD8289	Discontinued
0.6847	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.684	Remote Similarity	NPD5065	Approved
0.684	Remote Similarity	NPD8093	Discontinued
0.6833	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1038	Approved
0.683	Remote Similarity	NPD1499	Phase 3
0.6829	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8098	Approved
0.6826	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8160	Phase 2
0.6822	Remote Similarity	NPD1587	Approved
0.682	Remote Similarity	NPD7994	Phase 2
0.6812	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3795	Approved
0.681	Remote Similarity	NPD3794	Approved
0.6808	Remote Similarity	NPD5471	Phase 3
0.6795	Remote Similarity	NPD6710	Phase 3
0.6792	Remote Similarity	NPD1580	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8072	Approved
0.6783	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7603	Discontinued
0.6776	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7548	Discontinued
0.6763	Remote Similarity	NPD5479	Discontinued
0.6762	Remote Similarity	NPD5891	Approved
0.676	Remote Similarity	NPD4558	Phase 2
0.6759	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD56	Approved
0.6754	Remote Similarity	NPD8282	Approved
0.6754	Remote Similarity	NPD8283	Approved
0.6749	Remote Similarity	NPD7952	Approved
0.6749	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7790	Approved
0.6749	Remote Similarity	NPD7953	Approved
0.6749	Remote Similarity	NPD7951	Approved
0.6749	Remote Similarity	NPD7950	Approved
0.6749	Remote Similarity	NPD7791	Approved
0.6749	Remote Similarity	NPD7789	Approved
0.6742	Remote Similarity	NPD4699	Discontinued
0.6742	Remote Similarity	NPD5913	Phase 3
0.6742	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7948	Phase 1
0.674	Remote Similarity	NPD8073	Approved
0.6735	Remote Similarity	NPD4343	Phase 1
0.6735	Remote Similarity	NPD4344	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2844	Phase 3
0.6726	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7957	Phase 1
0.6724	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7780	Approved
0.6722	Remote Similarity	NPD7781	Approved
0.6721	Remote Similarity	NPD6130	Phase 1
0.6719	Remote Similarity	NPD8463	Approved
0.671	Remote Similarity	NPD4506	Discontinued
0.6709	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD2144	Approved
0.6698	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4852	Phase 2
0.6694	Remote Similarity	NPD5449	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD944	Approved
0.6681	Remote Similarity	NPD6987	Phase 1
0.668	Remote Similarity	NPD6165	Phase 2
0.668	Remote Similarity	NPD7730	Approved
0.668	Remote Similarity	NPD7731	Approved
0.668	Remote Similarity	NPD6164	Phase 2
0.668	Remote Similarity	NPD4328	Approved
0.6667	Remote Similarity	NPD8094	Discontinued
0.6667	Remote Similarity	NPD7271	Approved
0.6667	Remote Similarity	NPD1466	Phase 3
0.6667	Remote Similarity	NPD1467	Approved
0.6652	Remote Similarity	NPD6479	Discontinued
0.6652	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7711	Discontinued
0.6638	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD2920	Discontinued
0.6637	Remote Similarity	NPD4376	Phase 3
0.6637	Remote Similarity	NPD7946	Pre-registration
0.6636	Remote Similarity	NPD6452	Discontinued
0.6626	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7824	Approved
0.6626	Remote Similarity	NPD5022	Discontinued
0.6626	Remote Similarity	NPD7853	Phase 2
0.6624	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD3354	Phase 2
0.6623	Remote Similarity	NPD5017	Discontinued
0.6623	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1096	Discontinued
0.6611	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5612	Discontinued
0.6608	Remote Similarity	NPD3825	Phase 3

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