NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	402.93
Volume:	265.172
LogP:	1.721
LogD:	1.753
LogS:	-3.9
# Rotatable Bonds:	0
TPSA:	95.88
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	5.283
Fsp3:	0.455
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:	-5.26
MDCK Permeability:	1.7594717064639553e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.544
20% Bioavailability (F20%):	0.213
30% Bioavailability (F30%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.516
Plasma Protein Binding (PPB):	79.190185546875%
Volume Distribution (VD):	0.846
Pgp-substrate:	21.444820404052734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.234
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.433
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.695
CYP3A4-substrate:	0.938

ADMET: Excretion

Clearance (CL):	5.201
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.105
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.939
Rat Oral Acute Toxicity:	0.561
Maximum Recommended Daily Dose:	0.142
Skin Sensitization:	0.709
Carcinogencity:	0.998
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.802

Download Data

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

Natural Product: NPC469814

Natural Product ID:	NPC469814
*Common Name:**	Dibromohydroxyphakellin Hydrochloride
IUPAC Name:	n.a.
Synonyms:	Dibromohydroxyphakellin HCl
Standard InCHIKey:	FERJDEVTWKEULJ-VZXYPILPSA-N
Standard InCHI:	InChI=1S/C11H11Br2N5O2.ClH/c12-5-4-6-8(19)17-3-1-2-10(17)11(20,16-9(14)15-10)18(6)7(5)13;/h4,20H,1-3H2,(H3,14,15,16);1H/t10-,11+;/m0./s1
SMILES:	C1CC23C(N=C(N2)N)(N4C(=CC(=C4Br)Br)C(=O)N3C1)O.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1204016
PubChem CID:	49861328
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
NPO33334	agelas sponges	Species	Agelasidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[20061160]

☑ 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
MIC	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	112.8	%	PMID[497830]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	45000.0	nM	PMID[497830]

☑ 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 NPC469814 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	1030
0.1-0.2	16409
0.2-0.3	17549
0.3-0.4	3035
0.4-0.5	3341
0.5-0.6	1170
0.6-0.7	102
0.7-0.8	47
0.8-0.85	8
0.85-0.9	1
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9212	High Similarity	NPC28096
0.9212	High Similarity	NPC476421
0.9212	High Similarity	NPC226835
0.9212	High Similarity	NPC227489
0.9162	High Similarity	NPC136441
0.8398	Intermediate Similarity	NPC476413
0.8352	Intermediate Similarity	NPC476414
0.8333	Intermediate Similarity	NPC97106
0.8324	Intermediate Similarity	NPC46022
0.8246	Intermediate Similarity	NPC476418
0.8222	Intermediate Similarity	NPC112489
0.8214	Intermediate Similarity	NPC474236
0.814	Intermediate Similarity	NPC206148
0.8108	Intermediate Similarity	NPC46811
0.8092	Intermediate Similarity	NPC474383
0.8012	Intermediate Similarity	NPC27296
0.7826	Intermediate Similarity	NPC111566
0.7826	Intermediate Similarity	NPC63571
0.7784	Intermediate Similarity	NPC310633
0.7765	Intermediate Similarity	NPC80528
0.776	Intermediate Similarity	NPC9635
0.7714	Intermediate Similarity	NPC473706
0.7709	Intermediate Similarity	NPC54214
0.7705	Intermediate Similarity	NPC184932
0.7705	Intermediate Similarity	NPC472861
0.7672	Intermediate Similarity	NPC19342
0.7588	Intermediate Similarity	NPC260041
0.755	Intermediate Similarity	NPC469715
0.7538	Intermediate Similarity	NPC469716
0.7537	Intermediate Similarity	NPC469717
0.7528	Intermediate Similarity	NPC306160
0.7528	Intermediate Similarity	NPC73687
0.7525	Intermediate Similarity	NPC476524
0.7474	Intermediate Similarity	NPC19696
0.7474	Intermediate Similarity	NPC136957
0.7474	Intermediate Similarity	NPC210123
0.741	Intermediate Similarity	NPC150592
0.7377	Intermediate Similarity	NPC271927
0.7371	Intermediate Similarity	NPC174281
0.7371	Intermediate Similarity	NPC475286
0.7366	Intermediate Similarity	NPC40530
0.7366	Intermediate Similarity	NPC314281
0.7337	Intermediate Similarity	NPC37268
0.732	Intermediate Similarity	NPC329765
0.732	Intermediate Similarity	NPC48117
0.732	Intermediate Similarity	NPC476526
0.7302	Intermediate Similarity	NPC476423
0.7273	Intermediate Similarity	NPC109158
0.7264	Intermediate Similarity	NPC476525
0.7246	Intermediate Similarity	NPC20021
0.7228	Intermediate Similarity	NPC469976
0.7158	Intermediate Similarity	NPC474696
0.7119	Intermediate Similarity	NPC52110
0.7016	Intermediate Similarity	NPC270834
0.7009	Intermediate Similarity	NPC66642
0.6919	Remote Similarity	NPC2414
0.6906	Remote Similarity	NPC298288
0.6889	Remote Similarity	NPC472260
0.6872	Remote Similarity	NPC475736
0.6821	Remote Similarity	NPC476527
0.6776	Remote Similarity	NPC142688
0.67	Remote Similarity	NPC474180
0.67	Remote Similarity	NPC188821
0.665	Remote Similarity	NPC474389
0.6574	Remote Similarity	NPC474195
0.6552	Remote Similarity	NPC77061
0.6543	Remote Similarity	NPC253687
0.6455	Remote Similarity	NPC474196
0.6445	Remote Similarity	NPC71238
0.6436	Remote Similarity	NPC243716
0.6422	Remote Similarity	NPC272174
0.641	Remote Similarity	NPC476419
0.6404	Remote Similarity	NPC472288
0.6396	Remote Similarity	NPC91179
0.6393	Remote Similarity	NPC474896
0.6381	Remote Similarity	NPC473376
0.6378	Remote Similarity	NPC473380
0.6378	Remote Similarity	NPC240088
0.6364	Remote Similarity	NPC33229
0.6364	Remote Similarity	NPC31097
0.6355	Remote Similarity	NPC54981
0.6329	Remote Similarity	NPC171317
0.6295	Remote Similarity	NPC156003
0.6263	Remote Similarity	NPC265710
0.6237	Remote Similarity	NPC13432
0.6231	Remote Similarity	NPC16659
0.6218	Remote Similarity	NPC233380
0.6207	Remote Similarity	NPC201831
0.6207	Remote Similarity	NPC17059
0.6207	Remote Similarity	NPC17487
0.6197	Remote Similarity	NPC471191
0.6195	Remote Similarity	NPC69843
0.6193	Remote Similarity	NPC50562
0.6184	Remote Similarity	NPC474357
0.618	Remote Similarity	NPC477109
0.618	Remote Similarity	NPC477108
0.618	Remote Similarity	NPC477107
0.6175	Remote Similarity	NPC471193
0.6175	Remote Similarity	NPC471194
0.6167	Remote Similarity	NPC470323
0.6164	Remote Similarity	NPC470731
0.6164	Remote Similarity	NPC67658
0.6164	Remote Similarity	NPC470732
0.6158	Remote Similarity	NPC141612
0.6158	Remote Similarity	NPC135601
0.6158	Remote Similarity	NPC17273
0.6147	Remote Similarity	NPC54744
0.614	Remote Similarity	NPC935
0.614	Remote Similarity	NPC267078
0.6129	Remote Similarity	NPC320968
0.6123	Remote Similarity	NPC470730
0.6123	Remote Similarity	NPC477175
0.6123	Remote Similarity	NPC470729
0.6123	Remote Similarity	NPC477176
0.6116	Remote Similarity	NPC476817
0.6111	Remote Similarity	NPC23215
0.6111	Remote Similarity	NPC291517
0.6108	Remote Similarity	NPC133003
0.6102	Remote Similarity	NPC71236
0.6098	Remote Similarity	NPC213629
0.6096	Remote Similarity	NPC475859
0.6096	Remote Similarity	NPC475969
0.6096	Remote Similarity	NPC477177
0.6096	Remote Similarity	NPC474877
0.6091	Remote Similarity	NPC147983
0.6091	Remote Similarity	NPC177996
0.6089	Remote Similarity	NPC470205
0.6077	Remote Similarity	NPC179701
0.6073	Remote Similarity	NPC470703
0.6071	Remote Similarity	NPC327095
0.6071	Remote Similarity	NPC312942
0.607	Remote Similarity	NPC165743
0.6066	Remote Similarity	NPC477004
0.6066	Remote Similarity	NPC474767
0.6061	Remote Similarity	NPC161861
0.6059	Remote Similarity	NPC285923
0.6059	Remote Similarity	NPC21429
0.6055	Remote Similarity	NPC72956
0.605	Remote Similarity	NPC15573
0.605	Remote Similarity	NPC183662
0.605	Remote Similarity	NPC217372
0.6048	Remote Similarity	NPC262898
0.6048	Remote Similarity	NPC471199
0.6044	Remote Similarity	NPC40455
0.6043	Remote Similarity	NPC302159
0.6043	Remote Similarity	NPC63279
0.603	Remote Similarity	NPC186068
0.6027	Remote Similarity	NPC473218
0.6027	Remote Similarity	NPC6865
0.6027	Remote Similarity	NPC153980
0.6027	Remote Similarity	NPC470702
0.602	Remote Similarity	NPC219336
0.6019	Remote Similarity	NPC54420
0.6018	Remote Similarity	NPC19170
0.6017	Remote Similarity	NPC297642
0.601	Remote Similarity	NPC159125
0.601	Remote Similarity	NPC477167
0.601	Remote Similarity	NPC304187
0.601	Remote Similarity	NPC473342
0.601	Remote Similarity	NPC477166
0.6	Remote Similarity	NPC247987
0.6	Remote Similarity	NPC282247
0.5991	Remote Similarity	NPC116555
0.599	Remote Similarity	NPC74357
0.5989	Remote Similarity	NPC292434
0.5989	Remote Similarity	NPC14448
0.5989	Remote Similarity	NPC64661
0.5989	Remote Similarity	NPC138596
0.5989	Remote Similarity	NPC200397
0.5989	Remote Similarity	NPC98156
0.5989	Remote Similarity	NPC167200
0.5989	Remote Similarity	NPC195704
0.598	Remote Similarity	NPC288074
0.5978	Remote Similarity	NPC85443
0.5963	Remote Similarity	NPC162860
0.5959	Remote Similarity	NPC213914
0.5951	Remote Similarity	NPC311282
0.5946	Remote Similarity	NPC48171
0.5946	Remote Similarity	NPC59839
0.5946	Remote Similarity	NPC97230
0.5946	Remote Similarity	NPC205604
0.5946	Remote Similarity	NPC129753
0.5946	Remote Similarity	NPC77582
0.5946	Remote Similarity	NPC169308
0.5946	Remote Similarity	NPC244087
0.5946	Remote Similarity	NPC12831
0.5946	Remote Similarity	NPC74928
0.5946	Remote Similarity	NPC286529
0.5946	Remote Similarity	NPC3698
0.5946	Remote Similarity	NPC302717
0.5946	Remote Similarity	NPC209281
0.5946	Remote Similarity	NPC471192
0.5945	Remote Similarity	NPC270918
0.5939	Remote Similarity	NPC109447
0.5939	Remote Similarity	NPC297862
0.5938	Remote Similarity	NPC209362
0.5935	Remote Similarity	NPC471944
0.5931	Remote Similarity	NPC63031
0.5929	Remote Similarity	NPC175150
0.5929	Remote Similarity	NPC243633

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 NPC469814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	1077
0.2-0.3	1743
0.3-0.4	2323
0.4-0.5	2883
0.5-0.6	829
0.6-0.7	22
0.7-0.8	1
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
0.7245	Intermediate Similarity	NPD7459	Phase 2
0.6716	Remote Similarity	NPD2289	Phase 3
0.6716	Remote Similarity	NPD2290	Phase 3
0.6633	Remote Similarity	NPD5685	Approved
0.6633	Remote Similarity	NPD5686	Approved
0.6553	Remote Similarity	NPD5017	Discontinued
0.6465	Remote Similarity	NPD1096	Discontinued
0.6453	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD7716	Approved
0.6409	Remote Similarity	NPD7717	Approved
0.6364	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7817	Phase 1
0.6293	Remote Similarity	NPD460	Discontinued
0.6276	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD1600	Suspended
0.6256	Remote Similarity	NPD1623	Approved
0.625	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD2443	Approved
0.6215	Remote Similarity	NPD2442	Approved
0.621	Remote Similarity	NPD5643	Phase 2
0.6186	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD2367	Phase 2
0.6161	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6210	Phase 3
0.6122	Remote Similarity	NPD1573	Approved
0.6122	Remote Similarity	NPD1575	Approved
0.6121	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD7970	Approved
0.6119	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3968	Approved
0.6108	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD1506	Discontinued
0.6093	Remote Similarity	NPD3411	Phase 2
0.6093	Remote Similarity	NPD3410	Approved
0.6091	Remote Similarity	NPD3353	Approved
0.6085	Remote Similarity	NPD510	Phase 1
0.6085	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD2130	Discontinued
0.6065	Remote Similarity	NPD7232	Discontinued
0.6061	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD721	Approved
0.6058	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD1174	Phase 2
0.6047	Remote Similarity	NPD7568	Phase 1
0.6045	Remote Similarity	NPD2547	Discontinued
0.6045	Remote Similarity	NPD1031	Discontinued
0.6039	Remote Similarity	NPD1658	Discontinued
0.6037	Remote Similarity	NPD2408	Discontinued
0.6036	Remote Similarity	NPD6470	Phase 3
0.6	Remote Similarity	NPD2128	Phase 1
0.5991	Remote Similarity	NPD2405	Phase 3
0.599	Remote Similarity	NPD3989	Phase 3
0.5972	Remote Similarity	NPD3967	Approved
0.5972	Remote Similarity	NPD1952	Discontinued
0.5961	Remote Similarity	NPD3990	Phase 3
0.5961	Remote Similarity	NPD3178	Discontinued
0.5947	Remote Similarity	NPD971	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD2222	Discontinued
0.5942	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD1657	Approved
0.5939	Remote Similarity	NPD1571	Phase 2
0.5938	Remote Similarity	NPD5198	Approved
0.5938	Remote Similarity	NPD5199	Approved
0.5936	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7727	Phase 2
0.5929	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD8115	Approved
0.5926	Remote Similarity	NPD8114	Approved
0.5919	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD1631	Approved
0.5917	Remote Similarity	NPD6486	Approved
0.5917	Remote Similarity	NPD6487	Approved
0.5911	Remote Similarity	NPD6579	Phase 2
0.5907	Remote Similarity	NPD3774	Approved
0.5907	Remote Similarity	NPD3773	Approved
0.5907	Remote Similarity	NPD3775	Approved
0.5905	Remote Similarity	NPD1173	Approved
0.5896	Remote Similarity	NPD2880	Discontinued
0.5894	Remote Similarity	NPD3246	Discontinued
0.5893	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD4155	Approved
0.589	Remote Similarity	NPD5510	Approved
0.5888	Remote Similarity	NPD2911	Approved
0.5888	Remote Similarity	NPD2912	Approved
0.5865	Remote Similarity	NPD5016	Approved
0.5862	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD1572	Phase 2
0.586	Remote Similarity	NPD5333	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD439	Approved
0.5859	Remote Similarity	NPD438	Approved
0.5859	Remote Similarity	NPD5611	Phase 2
0.5856	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD2138	Approved
0.5854	Remote Similarity	NPD2137	Approved
0.5853	Remote Similarity	NPD8169	Discontinued
0.5853	Remote Similarity	NPD5000	Phase 2
0.5853	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD272	Approved
0.5845	Remote Similarity	NPD645	Clinical (unspecified phase)
0.5845	Remote Similarity	NPD5809	Phase 3
0.5845	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6753	Phase 1
0.5833	Remote Similarity	NPD6268	Phase 1
0.5833	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6173	Approved
0.5833	Remote Similarity	NPD6752	Phase 1
0.5826	Remote Similarity	NPD2008	Discontinued
0.5822	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD4520	Approved
0.5813	Remote Similarity	NPD3041	Approved
0.5801	Remote Similarity	NPD7887	Approved
0.5801	Remote Similarity	NPD7888	Approved
0.5794	Remote Similarity	NPD465	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD2363	Discontinued
0.5782	Remote Similarity	NPD3406	Suspended
0.578	Remote Similarity	NPD3380	Phase 3
0.578	Remote Similarity	NPD3379	Phase 2
0.5778	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD2813	Phase 3
0.5775	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD4940	Approved
0.5769	Remote Similarity	NPD3315	Phase 3
0.5769	Remote Similarity	NPD7026	Phase 2
0.5767	Remote Similarity	NPD3425	Discontinued
0.5766	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD1630	Approved
0.5764	Remote Similarity	NPD4091	Approved
0.5758	Remote Similarity	NPD6164	Phase 2
0.5758	Remote Similarity	NPD6165	Phase 2
0.5756	Remote Similarity	NPD1618	Phase 2
0.5753	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD6271	Approved
0.5749	Remote Similarity	NPD7483	Phase 2
0.5749	Remote Similarity	NPD7482	Phase 2
0.5748	Remote Similarity	NPD5446	Phase 2
0.5743	Remote Similarity	NPD5461	Discontinued
0.5743	Remote Similarity	NPD750	Phase 2
0.5742	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.574	Remote Similarity	NPD7656	Approved
0.574	Remote Similarity	NPD7657	Approved
0.574	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD3991	Approved
0.5735	Remote Similarity	NPD4092	Approved
0.5735	Remote Similarity	NPD3995	Approved
0.5735	Remote Similarity	NPD3996	Approved
0.5735	Remote Similarity	NPD3994	Approved
0.5735	Remote Similarity	NPD3993	Approved
0.5735	Remote Similarity	NPD3992	Approved
0.5733	Remote Similarity	NPD2401	Approved
0.5733	Remote Similarity	NPD2402	Approved
0.5727	Remote Similarity	NPD8322	Phase 2
0.5726	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD1982	Phase 1
0.5721	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4883	Approved
0.5714	Remote Similarity	NPD207	Discontinued
0.5714	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7297	Phase 2
0.5714	Remote Similarity	NPD4963	Approved
0.5714	Remote Similarity	NPD3522	Approved
0.5714	Remote Similarity	NPD4962	Approved
0.5708	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD4299	Phase 1
0.5708	Remote Similarity	NPD1591	Approved
0.5708	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD8256	Approved
0.5708	Remote Similarity	NPD5973	Phase 2
0.5708	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD8257	Approved
0.5708	Remote Similarity	NPD5974	Approved
0.5708	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD6665	Discontinued
0.5708	Remote Similarity	NPD5520	Phase 2
0.5707	Remote Similarity	NPD3999	Approved
0.5707	Remote Similarity	NPD3998	Approved
0.5707	Remote Similarity	NPD3997	Approved
0.5701	Remote Similarity	NPD4959	Approved
0.5701	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD4960	Approved
0.57	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD2803	Discontinued
0.5696	Remote Similarity	NPD6829	Phase 2
0.5695	Remote Similarity	NPD3915	Approved
0.5694	Remote Similarity	NPD6999	Discontinued
0.5694	Remote Similarity	NPD706	Phase 1

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