NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	400.91
Volume:	268.456
LogP:	0.797
LogD:	0.761
LogS:	-2.874
# Rotatable Bonds:	1
TPSA:	112.9
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	4.42
Fsp3:	0.182
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:	-5.462
MDCK Permeability:	1.0411716175440233e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.825
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	59.663177490234375%
Volume Distribution (VD):	1.329
Pgp-substrate:	48.934078216552734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.262
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	2.444
Half-life (T1/2):	0.575

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.544
Drug-inuced Liver Injury (DILI):	0.33
AMES Toxicity:	0.293
Rat Oral Acute Toxicity:	0.441
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.328
Carcinogencity:	0.45
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC271927

Natural Product ID:	NPC271927
*Common Name:**	(Z)-3-Bromohymenialdisine
IUPAC Name:	(4Z)-4-(2-amino-4-oxo-1H-imidazol-5-ylidene)-2,3-dibromo-1,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one
Synonyms:	(Z)-3-Bromohymenialdisine
Standard InCHIKey:	ZITKTAJHKVYGTC-UTCJRWHESA-N
Standard InCHI:	InChI=1S/C11H9Br2N5O2/c12-5-4-3(6-10(20)18-11(14)17-6)1-2-15-9(19)7(4)16-8(5)13/h16H,1-2H2,(H,15,19)(H3,14,17,18,20)/b6-3-
SMILES:	N=C1N=C(/C(=C/2CCNC(=O)c3c2c(Br)c([nH]3)Br)/N1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480350
PubChem CID:	10574178
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001990] Pyrroloazepines

*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
NPO7079	Stylissa massa	Species	Axinellidae	Eukaryota	n.a.	Philippine	n.a.	PMID[11784156]
NPO7079	Stylissa massa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12816422]
NPO7079	Stylissa massa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23684893]
NPO7079	Stylissa massa	Species	Axinellidae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1608	Individual Protein	Serine/threonine-protein kinase Chk1	Homo sapiens	IC50	=	100.0	nM	PMID[486045]

☑ 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 NPC271927 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	874
0.1-0.2	13276
0.2-0.3	20091
0.3-0.4	3864
0.4-0.5	3179
0.5-0.6	1222
0.6-0.7	148
0.7-0.8	36
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9742	High Similarity	NPC474696
0.9387	High Similarity	NPC184932
0.9387	High Similarity	NPC472861
0.9074	High Similarity	NPC469976
0.8963	High Similarity	NPC37268
0.8765	High Similarity	NPC73687
0.8129	Intermediate Similarity	NPC80528
0.8095	Intermediate Similarity	NPC206148
0.7836	Intermediate Similarity	NPC2414
0.7778	Intermediate Similarity	NPC476418
0.7717	Intermediate Similarity	NPC19342
0.768	Intermediate Similarity	NPC63571
0.768	Intermediate Similarity	NPC111566
0.7637	Intermediate Similarity	NPC310633
0.7571	Intermediate Similarity	NPC97106
0.7557	Intermediate Similarity	NPC54214
0.7528	Intermediate Similarity	NPC136441
0.7526	Intermediate Similarity	NPC9635
0.7513	Intermediate Similarity	NPC19696
0.7513	Intermediate Similarity	NPC136957
0.75	Intermediate Similarity	NPC469715
0.7487	Intermediate Similarity	NPC469717
0.7447	Intermediate Similarity	NPC476526
0.7447	Intermediate Similarity	NPC48117
0.7447	Intermediate Similarity	NPC329765
0.7407	Intermediate Similarity	NPC174281
0.7407	Intermediate Similarity	NPC475286
0.738	Intermediate Similarity	NPC476413
0.7377	Intermediate Similarity	NPC469814
0.736	Intermediate Similarity	NPC476421
0.736	Intermediate Similarity	NPC227489
0.736	Intermediate Similarity	NPC28096
0.734	Intermediate Similarity	NPC476414
0.7321	Intermediate Similarity	NPC260041
0.7296	Intermediate Similarity	NPC476524
0.7263	Intermediate Similarity	NPC226835
0.7225	Intermediate Similarity	NPC474236
0.7151	Intermediate Similarity	NPC474258
0.7143	Intermediate Similarity	NPC27296
0.7134	Intermediate Similarity	NPC150592
0.7128	Intermediate Similarity	NPC469716
0.7121	Intermediate Similarity	NPC476525
0.7045	Intermediate Similarity	NPC475870
0.7039	Intermediate Similarity	NPC233380
0.7021	Intermediate Similarity	NPC46022
0.7021	Intermediate Similarity	NPC112489
0.6995	Remote Similarity	NPC186068
0.6984	Remote Similarity	NPC473946
0.697	Remote Similarity	NPC20021
0.6968	Remote Similarity	NPC476423
0.6944	Remote Similarity	NPC474383
0.6931	Remote Similarity	NPC476527
0.6889	Remote Similarity	NPC306160
0.6856	Remote Similarity	NPC46811
0.6778	Remote Similarity	NPC473706
0.6761	Remote Similarity	NPC52110
0.6751	Remote Similarity	NPC474389
0.6633	Remote Similarity	NPC188821
0.6633	Remote Similarity	NPC474180
0.6615	Remote Similarity	NPC311282
0.6613	Remote Similarity	NPC302647
0.6612	Remote Similarity	NPC274981
0.6612	Remote Similarity	NPC162268
0.6598	Remote Similarity	NPC473628
0.6579	Remote Similarity	NPC314281
0.6579	Remote Similarity	NPC40530
0.6571	Remote Similarity	NPC475736
0.648	Remote Similarity	NPC475874
0.6468	Remote Similarity	NPC477004
0.6429	Remote Similarity	NPC142688
0.6429	Remote Similarity	NPC50562
0.6406	Remote Similarity	NPC234403
0.6398	Remote Similarity	NPC67658
0.6389	Remote Similarity	NPC471655
0.6381	Remote Similarity	NPC470703
0.6364	Remote Similarity	NPC210123
0.6359	Remote Similarity	NPC474492
0.6355	Remote Similarity	NPC474195
0.6354	Remote Similarity	NPC109158
0.6333	Remote Similarity	NPC473218
0.6333	Remote Similarity	NPC470702
0.6321	Remote Similarity	NPC79777
0.6304	Remote Similarity	NPC212742
0.6302	Remote Similarity	NPC473380
0.6302	Remote Similarity	NPC240088
0.6301	Remote Similarity	NPC156003
0.6288	Remote Similarity	NPC66642
0.6281	Remote Similarity	NPC243716
0.628	Remote Similarity	NPC471191
0.6277	Remote Similarity	NPC49217
0.6276	Remote Similarity	NPC133003
0.6257	Remote Similarity	NPC247987
0.625	Remote Similarity	NPC477166
0.625	Remote Similarity	NPC304187
0.6239	Remote Similarity	NPC474196
0.6237	Remote Similarity	NPC100104
0.6237	Remote Similarity	NPC470680
0.6232	Remote Similarity	NPC473376
0.6195	Remote Similarity	NPC77241
0.6195	Remote Similarity	NPC13456
0.6195	Remote Similarity	NPC269203
0.6195	Remote Similarity	NPC166209
0.6186	Remote Similarity	NPC265710
0.6186	Remote Similarity	NPC11126
0.6175	Remote Similarity	NPC472260
0.6165	Remote Similarity	NPC471944
0.6158	Remote Similarity	NPC77061
0.6154	Remote Similarity	NPC16659
0.6154	Remote Similarity	NPC182940
0.6154	Remote Similarity	NPC91179
0.615	Remote Similarity	NPC324091
0.6147	Remote Similarity	NPC175150
0.6147	Remote Similarity	NPC243633
0.6146	Remote Similarity	NPC201266
0.6146	Remote Similarity	NPC220797
0.6146	Remote Similarity	NPC474318
0.6146	Remote Similarity	NPC153123
0.6146	Remote Similarity	NPC475914
0.6146	Remote Similarity	NPC268744
0.6142	Remote Similarity	NPC21429
0.6142	Remote Similarity	NPC477003
0.6141	Remote Similarity	NPC232798
0.6129	Remote Similarity	NPC299594
0.6108	Remote Similarity	NPC33229
0.6105	Remote Similarity	NPC109447
0.6103	Remote Similarity	NPC471193
0.6103	Remote Similarity	NPC471194
0.6095	Remote Similarity	NPC270918
0.6094	Remote Similarity	NPC262338
0.6091	Remote Similarity	NPC470205
0.6083	Remote Similarity	NPC168209
0.6078	Remote Similarity	NPC179701
0.6073	Remote Similarity	NPC46359
0.6068	Remote Similarity	NPC237414
0.6066	Remote Similarity	NPC13432
0.6066	Remote Similarity	NPC143075
0.6062	Remote Similarity	NPC161861
0.6061	Remote Similarity	NPC228835
0.6059	Remote Similarity	NPC225622
0.6059	Remote Similarity	NPC221726
0.6059	Remote Similarity	NPC477414
0.605	Remote Similarity	NPC17059
0.6049	Remote Similarity	NPC262898
0.6044	Remote Similarity	NPC474357
0.6032	Remote Similarity	NPC26491
0.6027	Remote Similarity	NPC470323
0.6023	Remote Similarity	NPC291517
0.6022	Remote Similarity	NPC298288
0.6011	Remote Similarity	NPC100726
0.601	Remote Similarity	NPC477167
0.601	Remote Similarity	NPC270834
0.601	Remote Similarity	NPC473342
0.6	Remote Similarity	NPC135601
0.6	Remote Similarity	NPC17273
0.6	Remote Similarity	NPC58268
0.6	Remote Similarity	NPC141612
0.6	Remote Similarity	NPC54744
0.6	Remote Similarity	NPC151635
0.6	Remote Similarity	NPC114033
0.6	Remote Similarity	NPC129412
0.6	Remote Similarity	NPC94752
0.6	Remote Similarity	NPC101130
0.6	Remote Similarity	NPC271734
0.6	Remote Similarity	NPC935
0.6	Remote Similarity	NPC282247
0.6	Remote Similarity	NPC267078
0.6	Remote Similarity	NPC79356
0.6	Remote Similarity	NPC102592
0.5982	Remote Similarity	NPC272174
0.5981	Remote Similarity	NPC72956
0.598	Remote Similarity	NPC110158
0.5979	Remote Similarity	NPC64055
0.5978	Remote Similarity	NPC102664
0.5969	Remote Similarity	NPC217372
0.5969	Remote Similarity	NPC15573
0.5969	Remote Similarity	NPC183662
0.5961	Remote Similarity	NPC476460
0.5959	Remote Similarity	NPC471943
0.5953	Remote Similarity	NPC6865
0.5953	Remote Similarity	NPC153980
0.5952	Remote Similarity	NPC317701
0.5946	Remote Similarity	NPC473878
0.5945	Remote Similarity	NPC177996
0.5945	Remote Similarity	NPC470732
0.5945	Remote Similarity	NPC147983
0.5941	Remote Similarity	NPC209917
0.5939	Remote Similarity	NPC219336
0.5932	Remote Similarity	NPC23215
0.5918	Remote Similarity	NPC476419
0.5915	Remote Similarity	NPC116555
0.5909	Remote Similarity	NPC88110
0.5909	Remote Similarity	NPC477042
0.5907	Remote Similarity	NPC320968
0.5904	Remote Similarity	NPC74357
0.5902	Remote Similarity	NPC473821
0.5902	Remote Similarity	NPC204141
0.5902	Remote Similarity	NPC470440
0.5899	Remote Similarity	NPC167200
0.5899	Remote Similarity	NPC195704
0.5899	Remote Similarity	NPC14448

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 NPC271927 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	962
0.2-0.3	1523
0.3-0.4	2700
0.4-0.5	2912
0.5-0.6	766
0.6-0.7	23
0.7-0.8	0
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
0.6447	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7459	Phase 2
0.64	Remote Similarity	NPD2289	Phase 3
0.64	Remote Similarity	NPD2290	Phase 3
0.6373	Remote Similarity	NPD3178	Discontinued
0.6308	Remote Similarity	NPD1096	Discontinued
0.6205	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD2214	Approved
0.6183	Remote Similarity	NPD2213	Approved
0.6179	Remote Similarity	NPD3918	Approved
0.6179	Remote Similarity	NPD3917	Approved
0.6179	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD460	Discontinued
0.6132	Remote Similarity	NPD3915	Approved
0.6095	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1506	Discontinued
0.6091	Remote Similarity	NPD3318	Approved
0.6091	Remote Similarity	NPD3319	Phase 1
0.6091	Remote Similarity	NPD3320	Approved
0.6067	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD2443	Approved
0.6066	Remote Similarity	NPD2442	Approved
0.6038	Remote Similarity	NPD1600	Suspended
0.6038	Remote Similarity	NPD2408	Discontinued
0.6028	Remote Similarity	NPD7656	Approved
0.6028	Remote Similarity	NPD7657	Approved
0.6019	Remote Similarity	NPD465	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.601	Remote Similarity	NPD7817	Phase 1
0.6009	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD6376	Discontinued
0.599	Remote Similarity	NPD5685	Approved
0.599	Remote Similarity	NPD5686	Approved
0.5982	Remote Similarity	NPD1996	Discontinued
0.5972	Remote Similarity	NPD7970	Approved
0.5972	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD1952	Discontinued
0.597	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.596	Remote Similarity	NPD3990	Phase 3
0.5945	Remote Similarity	NPD3353	Approved
0.5943	Remote Similarity	NPD3411	Phase 2
0.5943	Remote Similarity	NPD3410	Approved
0.5936	Remote Similarity	NPD5199	Approved
0.5936	Remote Similarity	NPD5198	Approved
0.592	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD3989	Phase 3
0.5891	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD3968	Approved
0.5867	Remote Similarity	NPD4883	Approved
0.5867	Remote Similarity	NPD3522	Approved
0.5865	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.586	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.5845	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.5837	Remote Similarity	NPD2405	Phase 3
0.5833	Remote Similarity	NPD5140	Approved
0.5833	Remote Similarity	NPD5138	Approved
0.5829	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD2844	Phase 3
0.5825	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD3967	Approved
0.5822	Remote Similarity	NPD6164	Phase 2
0.5822	Remote Similarity	NPD6165	Phase 2
0.5814	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.5808	Remote Similarity	NPD4092	Approved
0.5805	Remote Similarity	NPD1658	Discontinued
0.5797	Remote Similarity	NPD7619	Phase 3
0.5797	Remote Similarity	NPD7618	Phase 3
0.5789	Remote Similarity	NPD1982	Phase 1
0.5787	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD5017	Discontinued
0.5782	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.5779	Remote Similarity	NPD3999	Approved
0.5779	Remote Similarity	NPD3998	Approved
0.5779	Remote Similarity	NPD3997	Approved
0.5777	Remote Similarity	NPD1896	Approved
0.5773	Remote Similarity	NPD5643	Phase 2
0.5773	Remote Similarity	NPD1591	Approved
0.5764	Remote Similarity	NPD706	Phase 1
0.576	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5759	Remote Similarity	NPD6753	Phase 1
0.5759	Remote Similarity	NPD7717	Approved
0.5759	Remote Similarity	NPD7716	Approved
0.5759	Remote Similarity	NPD6752	Phase 1
0.5758	Remote Similarity	NPD4091	Approved
0.5755	Remote Similarity	NPD6802	Phase 3
0.5748	Remote Similarity	NPD2008	Discontinued
0.5747	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD2880	Discontinued
0.5742	Remote Similarity	NPD6664	Approved
0.5741	Remote Similarity	NPD5510	Approved
0.5738	Remote Similarity	NPD1592	Phase 3
0.5735	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD3246	Discontinued
0.5729	Remote Similarity	NPD3992	Approved
0.5729	Remote Similarity	NPD3991	Approved
0.5729	Remote Similarity	NPD3996	Approved
0.5729	Remote Similarity	NPD3994	Approved
0.5729	Remote Similarity	NPD3993	Approved
0.5729	Remote Similarity	NPD3995	Approved
0.5729	Remote Similarity	NPD3041	Approved
0.5728	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD7727	Phase 2
0.5707	Remote Similarity	NPD1657	Approved
0.5707	Remote Similarity	NPD482	Approved
0.57	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4922	Phase 2
0.5695	Remote Similarity	NPD6210	Phase 3
0.5694	Remote Similarity	NPD1871	Approved
0.5694	Remote Similarity	NPD4959	Approved
0.5694	Remote Similarity	NPD4960	Approved
0.5691	Remote Similarity	NPD4462	Approved
0.5691	Remote Similarity	NPD4463	Approved
0.5688	Remote Similarity	NPD4863	Approved
0.5686	Remote Similarity	NPD7026	Phase 2
0.5682	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD749	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD2367	Phase 2
0.5676	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD1643	Phase 3
0.5661	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.5654	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.565	Remote Similarity	NPD4155	Approved
0.5648	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.5642	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD1575	Approved
0.5635	Remote Similarity	NPD1573	Approved
0.5628	Remote Similarity	NPD8115	Approved
0.5628	Remote Similarity	NPD8114	Approved
0.5628	Remote Similarity	NPD8098	Approved
0.5625	Remote Similarity	NPD6579	Phase 2
0.5622	Remote Similarity	NPD3077	Approved
0.5622	Remote Similarity	NPD3078	Approved
0.5622	Remote Similarity	NPD3079	Approved
0.5622	Remote Similarity	NPD3076	Approved
0.5622	Remote Similarity	NPD8386	Phase 2
0.5622	Remote Similarity	NPD7232	Discontinued
0.5613	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.561	Remote Similarity	NPD5809	Phase 3
0.561	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6268	Phase 1
0.5606	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD1043	Phase 3
0.5604	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.5602	Remote Similarity	NPD3405	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