NPASS Compound

Structure

CID15801 OpenBabel06191715342D 32 36 0 0 0 0 0 0 0 0999 V2000 1.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4826 0.4598 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 2.9921 -3.8781 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 2.1261 -4.3781 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 -2.9190 -4.1840 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 -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 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 -0.0000 -1.6180 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 0.5878 -0.8090 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 1.5878 -0.8090 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 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 -0.4817 -5.2132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 O 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 2.0878 0.0570 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 31 1 0 0 0 0 2 32 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 2 0 0 0 0 6 17 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 18 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 25 1 0 0 0 0 11 16 2 0 0 0 0 11 26 1 0 0 0 0 12 28 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 20 22 2 0 0 0 0 21 23 1 0 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 22 27 1 0 0 0 0 23 29 2 0 0 0 0 23 31 1 0 0 0 0 24 30 2 0 0 0 0 24 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	429.13
Volume:	426.182
LogP:	3.781
LogD:	2.897
LogS:	-5.218
# Rotatable Bonds:	6
TPSA:	120.2
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	2.788
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.633
MDCK Permeability:	5.956668701401213e-06
Pgp-inhibitor:	0.11
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.087

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	94.83184051513672%
Volume Distribution (VD):	0.548
Pgp-substrate:	3.684134006500244%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.379
CYP2C19-inhibitor:	0.974
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.918
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.935
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	6.632
Half-life (T1/2):	0.538

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.962
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.506
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.116
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.155
Respiratory Toxicity:	0.705

Download Data

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

Natural Product: NPC15801

Natural Product ID:	NPC15801
*Common Name:**	Lycogarubin B
IUPAC Name:	dimethyl 3-(5-hydroxy-1H-indol-3-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylate
Synonyms:
Standard InCHIKey:	SZBJDRXMLSSPCV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H19N3O5/c1-31-23(29)21-19(15-10-25-17-6-4-3-5-13(15)17)20(22(27-21)24(30)32-2)16-11-26-18-8-7-12(28)9-14(16)18/h3-11,25-28H,1-2H3
SMILES:	COC(=O)c1c(c2c[nH]c3ccccc23)c(c2c[nH]c3ccc(cc23)O)c(C(=O)OC)[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL439675
PubChem CID:	11441783
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004162] Hydroxyindoles

*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
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15911254]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	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	3
Others	17

Activity Type	# Activity
Cell Line	2
Individual Protein	13
Protein Family	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	18.0	ug.mL-1	PMID[485207]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	Inhibition	<	50.0	%	PMID[485207]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	Inhibition	<	50.0	%	PMID[485207]
NPT301	Individual Protein	Vascular endothelial growth factor receptor 1	Homo sapiens	Inhibition	<	50.0	%	PMID[485207]
NPT301	Individual Protein	Vascular endothelial growth factor receptor 1	Homo sapiens	Inhibition	=	50.0	%	PMID[485207]
NPT1178	Cell Line	KB 3-1	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[485207]
NPT1344	Individual Protein	Serine/threonine-protein kinase EEF2K	Homo sapiens	Inhibition	<	50.0	%	PMID[485207]
NPT1345	Individual Protein	Transcription factor HES-1	Mus musculus	IC50	=	16500.0	nM	PMID[485208]
NPT321	Protein Family	cAMP-dependent protein kinase (PKA)	Homo sapiens	Inhibition	<	50.0	%	PMID[485207]
NPT316	Protein Family	Protein kinase C (PKC)	Homo sapiens	Inhibition	<	50.0	%	PMID[485207]

☑ 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 NPC15801 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	416
0.1-0.2	2878
0.2-0.3	13374
0.3-0.4	6175
0.4-0.5	14577
0.5-0.6	2498
0.6-0.7	2108
0.7-0.8	632
0.8-0.85	33
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9139	High Similarity	NPC36405
0.8947	High Similarity	NPC82370
0.8618	High Similarity	NPC276657
0.8604	High Similarity	NPC267853
0.8565	High Similarity	NPC244897
0.8489	Intermediate Similarity	NPC316411
0.84	Intermediate Similarity	NPC207686
0.8386	Intermediate Similarity	NPC192712
0.8381	Intermediate Similarity	NPC213308
0.8381	Intermediate Similarity	NPC315491
0.8381	Intermediate Similarity	NPC45459
0.8356	Intermediate Similarity	NPC315062
0.8318	Intermediate Similarity	NPC321428
0.8318	Intermediate Similarity	NPC74360
0.8277	Intermediate Similarity	NPC74619
0.8273	Intermediate Similarity	NPC264285
0.8251	Intermediate Similarity	NPC229893
0.824	Intermediate Similarity	NPC178858
0.8178	Intermediate Similarity	NPC476098
0.8166	Intermediate Similarity	NPC182222
0.8152	Intermediate Similarity	NPC156704
0.8148	Intermediate Similarity	NPC88008
0.8145	Intermediate Similarity	NPC472285
0.8128	Intermediate Similarity	NPC118940
0.8125	Intermediate Similarity	NPC16352
0.8113	Intermediate Similarity	NPC67288
0.8095	Intermediate Similarity	NPC104712
0.8065	Intermediate Similarity	NPC270918
0.8054	Intermediate Similarity	NPC118228
0.8042	Intermediate Similarity	NPC53534
0.8035	Intermediate Similarity	NPC260434
0.8034	Intermediate Similarity	NPC295452
0.8034	Intermediate Similarity	NPC171393
0.8017	Intermediate Similarity	NPC91868
0.8017	Intermediate Similarity	NPC63971
0.7992	Intermediate Similarity	NPC152620
0.7983	Intermediate Similarity	NPC101350
0.7964	Intermediate Similarity	NPC110182
0.7964	Intermediate Similarity	NPC219087
0.7962	Intermediate Similarity	NPC99666
0.7946	Intermediate Similarity	NPC184408
0.7945	Intermediate Similarity	NPC171787
0.7944	Intermediate Similarity	NPC131887
0.794	Intermediate Similarity	NPC235685
0.7939	Intermediate Similarity	NPC24370
0.7939	Intermediate Similarity	NPC319232
0.7936	Intermediate Similarity	NPC300156
0.7931	Intermediate Similarity	NPC39370
0.7931	Intermediate Similarity	NPC325976
0.793	Intermediate Similarity	NPC51388
0.7922	Intermediate Similarity	NPC473186
0.7902	Intermediate Similarity	NPC312645
0.7897	Intermediate Similarity	NPC77555
0.789	Intermediate Similarity	NPC78609
0.7887	Intermediate Similarity	NPC276517
0.7873	Intermediate Similarity	NPC5145
0.787	Intermediate Similarity	NPC194740
0.7864	Intermediate Similarity	NPC39679
0.7864	Intermediate Similarity	NPC266249
0.786	Intermediate Similarity	NPC258048
0.7854	Intermediate Similarity	NPC175602
0.7848	Intermediate Similarity	NPC89508
0.7848	Intermediate Similarity	NPC266931
0.7847	Intermediate Similarity	NPC314002
0.7841	Intermediate Similarity	NPC60621
0.784	Intermediate Similarity	NPC307963
0.7839	Intermediate Similarity	NPC148889
0.7832	Intermediate Similarity	NPC269270
0.7828	Intermediate Similarity	NPC61038
0.782	Intermediate Similarity	NPC321708
0.7817	Intermediate Similarity	NPC125597
0.7814	Intermediate Similarity	NPC227582
0.7812	Intermediate Similarity	NPC474412
0.7811	Intermediate Similarity	NPC323752
0.781	Intermediate Similarity	NPC171171
0.7799	Intermediate Similarity	NPC204717
0.7797	Intermediate Similarity	NPC14686
0.7793	Intermediate Similarity	NPC123839
0.7792	Intermediate Similarity	NPC274640
0.7778	Intermediate Similarity	NPC469928
0.7768	Intermediate Similarity	NPC39500
0.7768	Intermediate Similarity	NPC196718
0.7767	Intermediate Similarity	NPC251090
0.7763	Intermediate Similarity	NPC475774
0.7763	Intermediate Similarity	NPC473317
0.7759	Intermediate Similarity	NPC326363
0.7758	Intermediate Similarity	NPC9894
0.7758	Intermediate Similarity	NPC294375
0.7751	Intermediate Similarity	NPC220765
0.7748	Intermediate Similarity	NPC325297
0.7745	Intermediate Similarity	NPC477549
0.7743	Intermediate Similarity	NPC27041
0.7742	Intermediate Similarity	NPC74413
0.7733	Intermediate Similarity	NPC477979
0.7727	Intermediate Similarity	NPC475070
0.7727	Intermediate Similarity	NPC473800
0.7717	Intermediate Similarity	NPC57398
0.7717	Intermediate Similarity	NPC260900
0.7713	Intermediate Similarity	NPC309845
0.7706	Intermediate Similarity	NPC252338
0.7702	Intermediate Similarity	NPC97902
0.77	Intermediate Similarity	NPC76748
0.7696	Intermediate Similarity	NPC122436
0.7692	Intermediate Similarity	NPC45190
0.7692	Intermediate Similarity	NPC102593
0.7689	Intermediate Similarity	NPC207866
0.7689	Intermediate Similarity	NPC477610
0.7683	Intermediate Similarity	NPC478006
0.7683	Intermediate Similarity	NPC216369
0.7679	Intermediate Similarity	NPC87413
0.7665	Intermediate Similarity	NPC304926
0.7665	Intermediate Similarity	NPC476041
0.7664	Intermediate Similarity	NPC92111
0.7658	Intermediate Similarity	NPC193238
0.7655	Intermediate Similarity	NPC478157
0.7653	Intermediate Similarity	NPC296527
0.7652	Intermediate Similarity	NPC144452
0.765	Intermediate Similarity	NPC474701
0.765	Intermediate Similarity	NPC141454
0.7647	Intermediate Similarity	NPC132539
0.7626	Intermediate Similarity	NPC314222
0.7626	Intermediate Similarity	NPC196449
0.7621	Intermediate Similarity	NPC3207
0.7617	Intermediate Similarity	NPC83111
0.7615	Intermediate Similarity	NPC306376
0.7613	Intermediate Similarity	NPC165964
0.7609	Intermediate Similarity	NPC280799
0.7602	Intermediate Similarity	NPC165599
0.7593	Intermediate Similarity	NPC208522
0.7592	Intermediate Similarity	NPC314882
0.7589	Intermediate Similarity	NPC478158
0.7586	Intermediate Similarity	NPC476818
0.7585	Intermediate Similarity	NPC220852
0.7585	Intermediate Similarity	NPC70155
0.7581	Intermediate Similarity	NPC138370
0.7578	Intermediate Similarity	NPC283117
0.7578	Intermediate Similarity	NPC183777
0.7578	Intermediate Similarity	NPC244741
0.7571	Intermediate Similarity	NPC63109
0.7565	Intermediate Similarity	NPC132642
0.7564	Intermediate Similarity	NPC477607
0.7564	Intermediate Similarity	NPC477608
0.7563	Intermediate Similarity	NPC28945
0.7563	Intermediate Similarity	NPC184225
0.7563	Intermediate Similarity	NPC285343
0.756	Intermediate Similarity	NPC184964
0.7559	Intermediate Similarity	NPC235684
0.7557	Intermediate Similarity	NPC193761
0.7555	Intermediate Similarity	NPC96321
0.7555	Intermediate Similarity	NPC303658
0.7551	Intermediate Similarity	NPC153400
0.7545	Intermediate Similarity	NPC176538
0.7544	Intermediate Similarity	NPC322064
0.7531	Intermediate Similarity	NPC41679
0.7524	Intermediate Similarity	NPC248041
0.7524	Intermediate Similarity	NPC283219
0.7524	Intermediate Similarity	NPC126709
0.7522	Intermediate Similarity	NPC208284
0.7522	Intermediate Similarity	NPC187501
0.7521	Intermediate Similarity	NPC478078
0.752	Intermediate Similarity	NPC329982
0.7512	Intermediate Similarity	NPC230403
0.7511	Intermediate Similarity	NPC179287
0.7511	Intermediate Similarity	NPC293151
0.75	Intermediate Similarity	NPC4687
0.7489	Intermediate Similarity	NPC316981
0.7489	Intermediate Similarity	NPC94157
0.7489	Intermediate Similarity	NPC174760
0.7489	Intermediate Similarity	NPC74153
0.7489	Intermediate Similarity	NPC472099
0.7489	Intermediate Similarity	NPC207020
0.7478	Intermediate Similarity	NPC477609
0.7477	Intermediate Similarity	NPC476874
0.7477	Intermediate Similarity	NPC160381
0.7477	Intermediate Similarity	NPC476073
0.7476	Intermediate Similarity	NPC111275
0.747	Intermediate Similarity	NPC478009
0.747	Intermediate Similarity	NPC478010
0.7469	Intermediate Similarity	NPC26543
0.7469	Intermediate Similarity	NPC475844
0.7468	Intermediate Similarity	NPC474192
0.7468	Intermediate Similarity	NPC469554
0.7468	Intermediate Similarity	NPC475720
0.7467	Intermediate Similarity	NPC170114
0.746	Intermediate Similarity	NPC314056
0.7456	Intermediate Similarity	NPC229348
0.7456	Intermediate Similarity	NPC476287
0.7455	Intermediate Similarity	NPC472286
0.7455	Intermediate Similarity	NPC472287
0.7448	Intermediate Similarity	NPC473187
0.7447	Intermediate Similarity	NPC473185
0.7446	Intermediate Similarity	NPC193267
0.7446	Intermediate Similarity	NPC213530
0.7444	Intermediate Similarity	NPC223427
0.7444	Intermediate Similarity	NPC315499
0.7442	Intermediate Similarity	NPC278434
0.7442	Intermediate Similarity	NPC46580
0.7431	Intermediate Similarity	NPC315467
0.743	Intermediate Similarity	NPC475746
0.7429	Intermediate Similarity	NPC267885

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 NPC15801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	636
0.2-0.3	896
0.3-0.4	1396
0.4-0.5	2878
0.5-0.6	2023
0.6-0.7	939
0.7-0.8	141
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8596	High Similarity	NPD5483	Clinical (unspecified phase)
0.8381	Intermediate Similarity	NPD484	Approved
0.8182	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD5482	Discontinued
0.8117	Intermediate Similarity	NPD6242	Discontinued
0.8082	Intermediate Similarity	NPD7470	Discontinued
0.7965	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.789	Intermediate Similarity	NPD5901	Discontinued
0.7857	Intermediate Similarity	NPD5612	Discontinued
0.7854	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1038	Approved
0.784	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD7603	Discontinued
0.7745	Intermediate Similarity	NPD3006	Discontinued
0.7742	Intermediate Similarity	NPD5450	Discontinued
0.7709	Intermediate Similarity	NPD3354	Phase 2
0.7703	Intermediate Similarity	NPD2510	Approved
0.7703	Intermediate Similarity	NPD2509	Approved
0.7692	Intermediate Similarity	NPD7001	Phase 3
0.7682	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD4845	Discontinued
0.765	Intermediate Similarity	NPD7948	Phase 1
0.7645	Intermediate Similarity	NPD4558	Phase 2
0.7632	Intermediate Similarity	NPD4429	Discontinued
0.7632	Intermediate Similarity	NPD5632	Approved
0.7619	Intermediate Similarity	NPD3178	Discontinued
0.7581	Intermediate Similarity	NPD6531	Approved
0.7581	Intermediate Similarity	NPD6530	Approved
0.7532	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2094	Phase 2
0.75	Intermediate Similarity	NPD2095	Phase 2
0.75	Intermediate Similarity	NPD2092	Phase 2
0.749	Intermediate Similarity	NPD8349	Phase 1
0.7489	Intermediate Similarity	NPD5003	Discontinued
0.7489	Intermediate Similarity	NPD5426	Phase 3
0.7478	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD8101	Phase 3
0.7465	Intermediate Similarity	NPD2091	Phase 2
0.7465	Intermediate Similarity	NPD2096	Phase 2
0.7458	Intermediate Similarity	NPD5022	Discontinued
0.7455	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD3258	Approved
0.7445	Intermediate Similarity	NPD5416	Discontinued
0.743	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7688	Phase 1
0.7421	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6999	Discontinued
0.7391	Intermediate Similarity	NPD8284	Discontinued
0.7391	Intermediate Similarity	NPD3389	Approved
0.7391	Intermediate Similarity	NPD3393	Approved
0.7391	Intermediate Similarity	NPD3394	Approved
0.7381	Intermediate Similarity	NPD482	Approved
0.7368	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8100	Phase 3
0.7342	Intermediate Similarity	NPD8395	Approved
0.7342	Intermediate Similarity	NPD8396	Approved
0.7336	Intermediate Similarity	NPD8097	Phase 3
0.7336	Intermediate Similarity	NPD8096	Phase 3
0.7333	Intermediate Similarity	NPD3947	Discontinued
0.7322	Intermediate Similarity	NPD4885	Approved
0.7322	Intermediate Similarity	NPD3746	Discontinued
0.7319	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8358	Approved
0.7311	Intermediate Similarity	NPD5479	Discontinued
0.7309	Intermediate Similarity	NPD8463	Approved
0.7304	Intermediate Similarity	NPD3243	Approved
0.7303	Intermediate Similarity	NPD4454	Phase 2
0.7303	Intermediate Similarity	NPD7853	Phase 2
0.73	Intermediate Similarity	NPD7994	Phase 2
0.7273	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3257	Approved
0.7269	Intermediate Similarity	NPD7452	Approved
0.7269	Intermediate Similarity	NPD7222	Phase 2
0.7269	Intermediate Similarity	NPD7453	Approved
0.7269	Intermediate Similarity	NPD5559	Phase 2
0.7265	Intermediate Similarity	NPD3825	Phase 3
0.7261	Intermediate Similarity	NPD5866	Approved
0.7257	Intermediate Similarity	NPD8098	Approved
0.7256	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7395	Discontinued
0.725	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6595	Phase 3
0.7241	Intermediate Similarity	NPD8160	Phase 2
0.7241	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD4418	Discontinued
0.7237	Intermediate Similarity	NPD2189	Approved
0.7237	Intermediate Similarity	NPD7666	Phase 3
0.7237	Intermediate Similarity	NPD6376	Discontinued
0.7237	Intermediate Similarity	NPD2187	Approved
0.7237	Intermediate Similarity	NPD7665	Phase 2
0.7227	Intermediate Similarity	NPD3259	Approved
0.722	Intermediate Similarity	NPD7558	Phase 2
0.722	Intermediate Similarity	NPD4373	Phase 2
0.7215	Intermediate Similarity	NPD2564	Approved
0.7215	Intermediate Similarity	NPD2565	Phase 2
0.7203	Intermediate Similarity	NPD6995	Phase 1
0.7202	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2951	Discontinued
0.7181	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD8364	Approved
0.7171	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD8363	Approved
0.717	Intermediate Similarity	NPD750	Phase 2
0.7167	Intermediate Similarity	NPD4952	Phase 3
0.7162	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD4328	Approved
0.7154	Intermediate Similarity	NPD8091	Phase 3
0.7154	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5067	Phase 2
0.7143	Intermediate Similarity	NPD5066	Phase 2
0.7143	Intermediate Similarity	NPD7946	Pre-registration
0.7143	Intermediate Similarity	NPD5475	Discontinued
0.7137	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1996	Discontinued
0.7118	Intermediate Similarity	NPD1392	Approved
0.7117	Intermediate Similarity	NPD802	Phase 2
0.7115	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3263	Phase 3
0.7113	Intermediate Similarity	NPD8289	Discontinued
0.7112	Intermediate Similarity	NPD4852	Phase 2
0.7111	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD2844	Phase 3
0.7106	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8283	Approved
0.7105	Intermediate Similarity	NPD56	Approved
0.7105	Intermediate Similarity	NPD8282	Approved
0.7094	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4442	Phase 2
0.7088	Intermediate Similarity	NPD5018	Phase 3
0.7087	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6716	Phase 1
0.7083	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD6456	Discontinued
0.7076	Intermediate Similarity	NPD6770	Approved
0.7074	Intermediate Similarity	NPD3003	Approved
0.7059	Intermediate Similarity	NPD8356	Approved
0.7059	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5512	Phase 3
0.7051	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5902	Approved
0.7051	Intermediate Similarity	NPD5903	Approved
0.7045	Intermediate Similarity	NPD7417	Discontinued
0.7045	Intermediate Similarity	NPD6790	Phase 1
0.7045	Intermediate Similarity	NPD4948	Discontinued
0.7043	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6276	Discontinued
0.7039	Intermediate Similarity	NPD7069	Discontinued
0.7039	Intermediate Similarity	NPD8093	Discontinued
0.7031	Intermediate Similarity	NPD6987	Phase 1
0.7031	Intermediate Similarity	NPD4795	Phase 2
0.7026	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7181	Phase 3
0.7013	Intermediate Similarity	NPD5658	Approved
0.7012	Intermediate Similarity	NPD6164	Phase 2
0.7012	Intermediate Similarity	NPD6165	Phase 2
0.7012	Intermediate Similarity	NPD8102	Discontinued
0.7012	Intermediate Similarity	NPD8430	Approved
0.7009	Intermediate Similarity	NPD3794	Approved
0.7009	Intermediate Similarity	NPD3795	Approved
0.7008	Intermediate Similarity	NPD7951	Approved
0.7008	Intermediate Similarity	NPD7953	Approved
0.7008	Intermediate Similarity	NPD8428	Approved
0.7008	Intermediate Similarity	NPD8467	Approved
0.7008	Intermediate Similarity	NPD8427	Approved
0.7008	Intermediate Similarity	NPD7789	Approved
0.7008	Intermediate Similarity	NPD8465	Approved
0.7008	Intermediate Similarity	NPD7790	Approved
0.7008	Intermediate Similarity	NPD7952	Approved
0.7008	Intermediate Similarity	NPD8429	Approved
0.7008	Intermediate Similarity	NPD7950	Approved
0.7008	Intermediate Similarity	NPD8466	Approved
0.7008	Intermediate Similarity	NPD7791	Approved
0.7	Intermediate Similarity	NPD5488	Discontinued
0.6991	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7689	Approved
0.6979	Remote Similarity	NPD4897	Phase 2
0.6977	Remote Similarity	NPD5065	Approved
0.697	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5429	Discontinued
0.6969	Remote Similarity	NPD5532	Phase 2
0.6966	Remote Similarity	NPD3330	Phase 1
0.6966	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD6228	Discontinued
0.6957	Remote Similarity	NPD4038	Approved
0.6957	Remote Similarity	NPD4035	Approved
0.6957	Remote Similarity	NPD4037	Approved
0.6957	Remote Similarity	NPD4033	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