NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	462.22
Volume:	447.469
LogP:	-1.026
LogD:	0.405
LogS:	-3.31
# Rotatable Bonds:	10
TPSA:	200.64
# H-Bond Aceptor:	12
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.183
Synthetic Accessibility Score:	5.121
Fsp3:	0.273
Lipinski Rule-of-5:	Rejected
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:	-5.912
MDCK Permeability:	3.1053409657033626e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.343
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.543
Plasma Protein Binding (PPB):	29.952392578125%
Volume Distribution (VD):	0.671
Pgp-substrate:	40.5653076171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.598
CYP2C19-inhibitor:	0.331
CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.086

ADMET: Excretion

Clearance (CL):	3.101
Half-life (T1/2):	0.978

ADMET: Toxicity

hERG Blockers:	0.857
Human Hepatotoxicity (H-HT):	0.998
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.456
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.474
Carcinogencity:	0.118
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC476527

Natural Product ID:	NPC476527
*Common Name:**	Debromosceptrin
IUPAC Name:	N-[[(1R,2S,3S,4R)-2,3-bis(2-amino-1H-imidazol-5-yl)-4-[(1H-pyrrole-2-carbonylamino)methyl]cyclobutyl]methyl]-1H-pyrrole-2-carboxamide
Synonyms:	Debromosceptrin
Standard InCHIKey:	DAVDNNXCCMUSGM-WUYIMCQSSA-N
Standard InCHI:	InChI=1S/C22H26N10O2.2ClH/c23-21-29-9-15(31-21)17-11(7-27-19(33)13-3-1-5-25-13)12(18(17)16-10-30-22(24)32-16)8-28-20(34)14-4-2-6-26-14;;/h1-6,9-12,17-18,25-26H,7-8H2,(H,27,33)(H,28,34)(H3,23,29,31)(H3,24,30,32);2*1H/t11-,12-,17-,18-;;/m1../s1
SMILES:	c1cc(C(=O)NC[C@@H]2[C@@H](CNC(=O)c3ccc[nH]3)[C@H](c3c[nH]c(=N)[nH]3)[C@H]2c2c[nH]c(=N)[nH]2)[nH]c1.Cl.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509019
PubChem CID:	44584043
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0000475] Carboxylic acid amides [CHEMONTID:0004817] 2-heteroaryl carboxamides

*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
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	at a depth of 14 m near the island of Ambon (Seram Seilale), Indonesia	1997-AUG	PMID[10514317]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14677933]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[26083682]
NPO28241	Agelas conifera	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784176]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	papua new guinean	n.a.	PMID[9784179]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28241	Agelas conifera	Species	Agelasidae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	IZ	=	10.0	mm	PMID[488230]

☑ 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 NPC476527 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	1001
0.1-0.2	15326
0.2-0.3	18867
0.3-0.4	2959
0.4-0.5	2543
0.5-0.6	1565
0.6-0.7	381
0.7-0.8	36
0.8-0.85	6
0.85-0.9	9
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9425	High Similarity	NPC476526
0.9425	High Similarity	NPC48117
0.9425	High Similarity	NPC329765
0.9153	High Similarity	NPC475286
0.9153	High Similarity	NPC174281
0.905	High Similarity	NPC19696
0.905	High Similarity	NPC136957
0.8667	High Similarity	NPC19342
0.8596	High Similarity	NPC310633
0.8539	High Similarity	NPC111566
0.8466	Intermediate Similarity	NPC476525
0.8466	Intermediate Similarity	NPC476524
0.8436	Intermediate Similarity	NPC63571
0.8265	Intermediate Similarity	NPC469717
0.8229	Intermediate Similarity	NPC54214
0.8056	Intermediate Similarity	NPC40530
0.8056	Intermediate Similarity	NPC314281
0.8053	Intermediate Similarity	NPC9635
0.7861	Intermediate Similarity	NPC210123
0.7857	Intermediate Similarity	NPC16659
0.7845	Intermediate Similarity	NPC240088
0.7845	Intermediate Similarity	NPC473380
0.7841	Intermediate Similarity	NPC206148
0.7802	Intermediate Similarity	NPC265710
0.7697	Intermediate Similarity	NPC233380
0.7688	Intermediate Similarity	NPC472260
0.7676	Intermediate Similarity	NPC270834
0.7551	Intermediate Similarity	NPC469716
0.7527	Intermediate Similarity	NPC469976
0.7487	Intermediate Similarity	NPC476460
0.7447	Intermediate Similarity	NPC477003
0.7433	Intermediate Similarity	NPC472861
0.7433	Intermediate Similarity	NPC184932
0.7424	Intermediate Similarity	NPC317701
0.7381	Intermediate Similarity	NPC291517
0.7348	Intermediate Similarity	NPC73687
0.732	Intermediate Similarity	NPC188821
0.732	Intermediate Similarity	NPC474180
0.73	Intermediate Similarity	NPC473376
0.7278	Intermediate Similarity	NPC23215
0.7277	Intermediate Similarity	NPC116555
0.7259	Intermediate Similarity	NPC474389
0.7243	Intermediate Similarity	NPC476421
0.7243	Intermediate Similarity	NPC227489
0.7243	Intermediate Similarity	NPC28096
0.7225	Intermediate Similarity	NPC99939
0.7225	Intermediate Similarity	NPC308931
0.7219	Intermediate Similarity	NPC136441
0.7181	Intermediate Similarity	NPC284775
0.7172	Intermediate Similarity	NPC171317
0.7166	Intermediate Similarity	NPC37268
0.7163	Intermediate Similarity	NPC267811
0.7158	Intermediate Similarity	NPC476418
0.7151	Intermediate Similarity	NPC226835
0.7135	Intermediate Similarity	NPC471655
0.7105	Intermediate Similarity	NPC477042
0.7087	Intermediate Similarity	NPC320968
0.7062	Intermediate Similarity	NPC17059
0.7056	Intermediate Similarity	NPC304203
0.7056	Intermediate Similarity	NPC326422
0.7053	Intermediate Similarity	NPC470702
0.7053	Intermediate Similarity	NPC473218
0.7037	Intermediate Similarity	NPC69843
0.7026	Intermediate Similarity	NPC213629
0.7022	Intermediate Similarity	NPC66642
0.7019	Intermediate Similarity	NPC470703
0.7019	Intermediate Similarity	NPC54744
0.7019	Intermediate Similarity	NPC282247
0.701	Intermediate Similarity	NPC94752
0.6995	Remote Similarity	NPC228835
0.6965	Remote Similarity	NPC477004
0.6963	Remote Similarity	NPC11126
0.6959	Remote Similarity	NPC133003
0.6943	Remote Similarity	NPC470205
0.6939	Remote Similarity	NPC473666
0.6931	Remote Similarity	NPC271927
0.6923	Remote Similarity	NPC477815
0.6919	Remote Similarity	NPC470203
0.6904	Remote Similarity	NPC324091
0.6902	Remote Similarity	NPC474492
0.6897	Remote Similarity	NPC472288
0.6895	Remote Similarity	NPC97106
0.6895	Remote Similarity	NPC469529
0.6891	Remote Similarity	NPC191415
0.689	Remote Similarity	NPC471193
0.689	Remote Similarity	NPC471194
0.6865	Remote Similarity	NPC473706
0.6865	Remote Similarity	NPC470204
0.6856	Remote Similarity	NPC102755
0.6856	Remote Similarity	NPC117027
0.6853	Remote Similarity	NPC209917
0.6845	Remote Similarity	NPC2414
0.6842	Remote Similarity	NPC72956
0.6842	Remote Similarity	NPC161861
0.6842	Remote Similarity	NPC54981
0.6842	Remote Similarity	NPC80528
0.6836	Remote Similarity	NPC58268
0.6836	Remote Similarity	NPC101130
0.6836	Remote Similarity	NPC114033
0.6836	Remote Similarity	NPC129412
0.6832	Remote Similarity	NPC131887
0.6821	Remote Similarity	NPC469814
0.6816	Remote Similarity	NPC467188
0.6812	Remote Similarity	NPC54420
0.681	Remote Similarity	NPC6865
0.681	Remote Similarity	NPC153980
0.6809	Remote Similarity	NPC49217
0.68	Remote Similarity	NPC476414
0.6792	Remote Similarity	NPC470731
0.6792	Remote Similarity	NPC470732
0.6791	Remote Similarity	NPC162268
0.6789	Remote Similarity	NPC262338
0.6782	Remote Similarity	NPC167710
0.6774	Remote Similarity	NPC100104
0.6774	Remote Similarity	NPC470680
0.6773	Remote Similarity	NPC470323
0.6761	Remote Similarity	NPC104049
0.6755	Remote Similarity	NPC42372
0.6751	Remote Similarity	NPC135601
0.6751	Remote Similarity	NPC141612
0.6751	Remote Similarity	NPC17273
0.675	Remote Similarity	NPC476413
0.6749	Remote Similarity	NPC473640
0.6746	Remote Similarity	NPC223791
0.6746	Remote Similarity	NPC162860
0.6746	Remote Similarity	NPC107077
0.6744	Remote Similarity	NPC474195
0.6742	Remote Similarity	NPC267078
0.6742	Remote Similarity	NPC935
0.674	Remote Similarity	NPC105811
0.674	Remote Similarity	NPC100726
0.6739	Remote Similarity	NPC33229
0.6735	Remote Similarity	NPC21429
0.6732	Remote Similarity	NPC475506
0.6729	Remote Similarity	NPC475736
0.6728	Remote Similarity	NPC476817
0.6722	Remote Similarity	NPC260041
0.672	Remote Similarity	NPC474696
0.6716	Remote Similarity	NPC220797
0.6716	Remote Similarity	NPC474318
0.6716	Remote Similarity	NPC100321
0.6716	Remote Similarity	NPC201266
0.6716	Remote Similarity	NPC153123
0.6716	Remote Similarity	NPC475914
0.6716	Remote Similarity	NPC293917
0.6716	Remote Similarity	NPC268744
0.6714	Remote Similarity	NPC471192
0.6712	Remote Similarity	NPC474357
0.6699	Remote Similarity	NPC71238
0.6699	Remote Similarity	NPC155143
0.6697	Remote Similarity	NPC474196
0.6686	Remote Similarity	NPC71236
0.6685	Remote Similarity	NPC143872
0.6685	Remote Similarity	NPC251391
0.6683	Remote Similarity	NPC321708
0.6683	Remote Similarity	NPC166209
0.6683	Remote Similarity	NPC77241
0.6683	Remote Similarity	NPC13456
0.6683	Remote Similarity	NPC269203
0.6667	Remote Similarity	NPC112489
0.6667	Remote Similarity	NPC53947
0.6667	Remote Similarity	NPC46022
0.6667	Remote Similarity	NPC20021
0.6651	Remote Similarity	NPC64216
0.665	Remote Similarity	NPC79356
0.665	Remote Similarity	NPC102592
0.6649	Remote Similarity	NPC471943
0.6649	Remote Similarity	NPC209362
0.6648	Remote Similarity	NPC195704
0.6648	Remote Similarity	NPC292434
0.6648	Remote Similarity	NPC167200
0.6648	Remote Similarity	NPC14448
0.6648	Remote Similarity	NPC138596
0.6648	Remote Similarity	NPC200397
0.6648	Remote Similarity	NPC98156
0.6648	Remote Similarity	NPC64661
0.6632	Remote Similarity	NPC293216
0.6631	Remote Similarity	NPC92796
0.6631	Remote Similarity	NPC135141
0.6618	Remote Similarity	NPC476073
0.6615	Remote Similarity	NPC141377
0.6606	Remote Similarity	NPC156003
0.6601	Remote Similarity	NPC294693
0.6598	Remote Similarity	NPC151635
0.6596	Remote Similarity	NPC122141
0.6595	Remote Similarity	NPC200214
0.6593	Remote Similarity	NPC288838
0.6592	Remote Similarity	NPC302717
0.6592	Remote Similarity	NPC129753
0.6592	Remote Similarity	NPC77582
0.6592	Remote Similarity	NPC3698
0.6592	Remote Similarity	NPC244087
0.6592	Remote Similarity	NPC48171
0.6592	Remote Similarity	NPC59839
0.6592	Remote Similarity	NPC169308
0.6592	Remote Similarity	NPC209281
0.6592	Remote Similarity	NPC205604
0.6592	Remote Similarity	NPC74928
0.6592	Remote Similarity	NPC12831
0.6592	Remote Similarity	NPC97230

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 NPC476527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	1068
0.2-0.3	1653
0.3-0.4	2195
0.4-0.5	2063
0.5-0.6	1451
0.6-0.7	349
0.7-0.8	28
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
0.7617	Intermediate Similarity	NPD7459	Phase 2
0.7435	Intermediate Similarity	NPD5686	Approved
0.7435	Intermediate Similarity	NPD5685	Approved
0.7327	Intermediate Similarity	NPD7704	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2443	Approved
0.7277	Intermediate Similarity	NPD2442	Approved
0.7264	Intermediate Similarity	NPD2008	Discontinued
0.7231	Intermediate Similarity	NPD460	Discontinued
0.7177	Intermediate Similarity	NPD5199	Approved
0.7177	Intermediate Similarity	NPD5198	Approved
0.7157	Intermediate Similarity	NPD1600	Suspended
0.7143	Intermediate Similarity	NPD1506	Discontinued
0.7136	Intermediate Similarity	NPD2411	Approved
0.7136	Intermediate Similarity	NPD2405	Phase 3
0.7128	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD1982	Phase 1
0.7073	Intermediate Similarity	NPD2408	Discontinued
0.7044	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2880	Discontinued
0.7	Intermediate Similarity	NPD5643	Phase 2
0.7	Intermediate Similarity	NPD8256	Approved
0.7	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8257	Approved
0.6986	Remote Similarity	NPD7970	Approved
0.6986	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5017	Discontinued
0.6878	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5446	Phase 2
0.685	Remote Similarity	NPD5853	Phase 3
0.685	Remote Similarity	NPD5855	Phase 3
0.6808	Remote Similarity	NPD6470	Phase 3
0.6804	Remote Similarity	NPD3178	Discontinued
0.6804	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5854	Approved
0.6798	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6664	Approved
0.6779	Remote Similarity	NPD6459	Phase 2
0.6763	Remote Similarity	NPD3967	Approved
0.6757	Remote Similarity	NPD6465	Phase 2
0.6744	Remote Similarity	NPD6210	Phase 3
0.6735	Remote Similarity	NPD1096	Discontinued
0.6735	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3891	Phase 2
0.6732	Remote Similarity	NPD3890	Phase 2
0.6731	Remote Similarity	NPD3410	Approved
0.6731	Remote Similarity	NPD3411	Phase 2
0.6725	Remote Similarity	NPD1031	Discontinued
0.6717	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.67	Remote Similarity	NPD1952	Discontinued
0.6683	Remote Similarity	NPD7618	Phase 3
0.6683	Remote Similarity	NPD7619	Phase 3
0.6682	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4922	Phase 2
0.6667	Remote Similarity	NPD3968	Approved
0.665	Remote Similarity	NPD2290	Phase 3
0.665	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.665	Remote Similarity	NPD2289	Phase 3
0.6636	Remote Similarity	NPD6165	Phase 2
0.6636	Remote Similarity	NPD6164	Phase 2
0.6635	Remote Similarity	NPD4299	Phase 1
0.6635	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5426	Phase 3
0.6633	Remote Similarity	NPD1895	Discontinued
0.6632	Remote Similarity	NPD4883	Approved
0.6622	Remote Similarity	NPD8317	Phase 2
0.6622	Remote Similarity	NPD8316	Phase 2
0.6618	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2881	Approved
0.6618	Remote Similarity	NPD2879	Approved
0.6618	Remote Similarity	NPD6268	Phase 1
0.6617	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD3583	Phase 2
0.6605	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3915	Approved
0.6603	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7175	Phase 1
0.6598	Remote Similarity	NPD4075	Phase 2
0.659	Remote Similarity	NPD6579	Phase 2
0.6588	Remote Similarity	NPD5510	Approved
0.6583	Remote Similarity	NPD7026	Phase 2
0.6582	Remote Similarity	NPD3927	Phase 2
0.6579	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3917	Approved
0.6573	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3918	Approved
0.6571	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7027	Phase 3
0.6562	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD2061	Approved
0.6558	Remote Similarity	NPD3353	Approved
0.6555	Remote Similarity	NPD7209	Approved
0.6555	Remote Similarity	NPD7208	Approved
0.6555	Remote Similarity	NPD7207	Approved
0.655	Remote Similarity	NPD4988	Discontinued
0.655	Remote Similarity	NPD3961	Discontinued
0.6541	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1658	Discontinued
0.6526	Remote Similarity	NPD4863	Approved
0.6515	Remote Similarity	NPD3319	Phase 1
0.6515	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3320	Approved
0.6515	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3318	Approved
0.6514	Remote Similarity	NPD803	Phase 1
0.6512	Remote Similarity	NPD4395	Phase 1
0.65	Remote Similarity	NPD6849	Phase 2
0.65	Remote Similarity	NPD6850	Phase 2
0.65	Remote Similarity	NPD6217	Discontinued
0.6497	Remote Similarity	NPD272	Approved
0.6495	Remote Similarity	NPD7657	Approved
0.6495	Remote Similarity	NPD7656	Approved
0.6493	Remote Similarity	NPD3905	Phase 3
0.6488	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2172	Phase 1
0.6482	Remote Similarity	NPD7564	Discontinued
0.648	Remote Similarity	NPD4181	Approved
0.6479	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD8169	Discontinued
0.6474	Remote Similarity	NPD6771	Discontinued
0.6471	Remote Similarity	NPD3460	Discontinued
0.6465	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD1707	Approved
0.6465	Remote Similarity	NPD1708	Approved
0.6464	Remote Similarity	NPD1722	Approved
0.6462	Remote Similarity	NPD4128	Approved
0.6462	Remote Similarity	NPD482	Approved
0.6461	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5611	Phase 2
0.6457	Remote Similarity	NPD7887	Approved
0.6457	Remote Similarity	NPD7888	Approved
0.6447	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD5489	Phase 1
0.6445	Remote Similarity	NPD5491	Phase 3
0.6444	Remote Similarity	NPD786	Approved
0.6444	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4558	Phase 2
0.6436	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD2095	Phase 2
0.6432	Remote Similarity	NPD2094	Phase 2
0.6432	Remote Similarity	NPD6986	Phase 1
0.6432	Remote Similarity	NPD2092	Phase 2
0.6429	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6044	Discontinued
0.6425	Remote Similarity	NPD6752	Phase 1
0.6425	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6753	Phase 1
0.6422	Remote Similarity	NPD5973	Phase 2
0.6422	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5974	Approved
0.6419	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2793	Discontinued
0.6414	Remote Similarity	NPD5508	Phase 1
0.6414	Remote Similarity	NPD2481	Approved
0.6414	Remote Similarity	NPD6595	Phase 3
0.6414	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD2479	Phase 3
0.6409	Remote Similarity	NPD9599	Approved
0.6408	Remote Similarity	NPD6226	Phase 3
0.6408	Remote Similarity	NPD4848	Phase 1
0.6404	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2096	Phase 2
0.64	Remote Similarity	NPD2091	Phase 2
0.6398	Remote Similarity	NPD8272	Phase 2
0.6396	Remote Similarity	NPD5986	Approved
0.6396	Remote Similarity	NPD5987	Approved
0.6396	Remote Similarity	NPD3041	Approved
0.6394	Remote Similarity	NPD6999	Discontinued
0.6394	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.639	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2363	Discontinued
0.6382	Remote Similarity	NPD3038	Discontinued
0.638	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3517	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD8641	Approved
0.6355	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.635	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4364	Phase 1
0.6346	Remote Similarity	NPD1249	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7402	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD7594	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data