NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	326.0
Volume:	243.682
LogP:	0.49
LogD:	1.149
LogS:	-1.934
# Rotatable Bonds:	0
TPSA:	95.39
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	5.019
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.942
MDCK Permeability:	3.087624645559117e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.798
Human Intestinal Absorption (HIA):	0.14
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.408

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.889
Plasma Protein Binding (PPB):	57.77603530883789%
Volume Distribution (VD):	0.474
Pgp-substrate:	53.063880920410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.143
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.089

ADMET: Excretion

Clearance (CL):	5.057
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.154
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.097
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.223
Carcinogencity:	0.643
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.104

Download Data

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

Natural Product: NPC46022

Natural Product ID:	NPC46022
*Common Name:**	Agelastatin D
IUPAC Name:	n.a.
Synonyms:	(-)-Agelastatin A; Agelastatin D
Standard InCHIKey:	AMKORUFKJJIBRU-GIDNPQMSSA-N
Standard InCHI:	InChI=1S/C11H11BrN4O3/c12-6-2-1-4-9(17)13-7-5(16(4)6)3-11(19)8(7)14-10(18)15-11/h1-2,5,7-8,19H,3H2,(H,13,17)(H2,14,15,18)/t5-,7-,8+,11+/m1/s1
SMILES:	OC1=N[C@@H]2[C@@](N1)(O)C[C@@H]1[C@H]2NC(=O)c2n1c(Br)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517037
PubChem CID:	177418
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
NPO32698	cymbastela sp.	Species	Axinellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[10479320]
NPO19163	Agelas dendromorpha	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20166736]
NPO32698	cymbastela sp.	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461668]
NPO19163	Agelas dendromorpha	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
EC50	4
Others	5

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	3
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	EC50	=	13700.0	nM	PMID[493133]
NPT6451	Organism	Artemia franciscana	Artemia franciscana	LC50	=	1.7	ppm	PMID[493131]
NPT2779	Organism	Spodoptera exigua	Spodoptera exigua	LC50	=	26.0	ug.mL-1	PMID[493131]
NPT2779	Organism	Spodoptera exigua	Spodoptera exigua	LC50	=	20.3	ug.mL-1	PMID[493131]
NPT3061	Organism	Diabrotica undecimpunctata	Diabrotica undecimpunctata	LC50	=	37.0	ug.mL-1	PMID[493131]
NPT3061	Organism	Diabrotica undecimpunctata	Diabrotica undecimpunctata	LC50	=	32.0	ug.mL-1	PMID[493131]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	13200.0	nM	PMID[493133]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	29000.0	nM	PMID[493133]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	91100.0	nM	PMID[493133]

☑ 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 NPC46022 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	840
0.1-0.2	15082
0.2-0.3	18476
0.3-0.4	3256
0.4-0.5	3359
0.5-0.6	1491
0.6-0.7	144
0.7-0.8	38
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.988	High Similarity	NPC112489
0.948	High Similarity	NPC46811
0.858	High Similarity	NPC476418
0.8506	High Similarity	NPC136441
0.8343	Intermediate Similarity	NPC97106
0.8324	Intermediate Similarity	NPC469814
0.8314	Intermediate Similarity	NPC474383
0.8023	Intermediate Similarity	NPC27296
0.8023	Intermediate Similarity	NPC28096
0.8023	Intermediate Similarity	NPC476421
0.8023	Intermediate Similarity	NPC227489
0.8012	Intermediate Similarity	NPC474236
0.7921	Intermediate Similarity	NPC226835
0.7914	Intermediate Similarity	NPC476413
0.7877	Intermediate Similarity	NPC80528
0.7872	Intermediate Similarity	NPC476414
0.7841	Intermediate Similarity	NPC206148
0.7637	Intermediate Similarity	NPC37268
0.7627	Intermediate Similarity	NPC473706
0.7624	Intermediate Similarity	NPC54214
0.7527	Intermediate Similarity	NPC184932
0.7527	Intermediate Similarity	NPC472861
0.75	Intermediate Similarity	NPC9635
0.746	Intermediate Similarity	NPC63571
0.7444	Intermediate Similarity	NPC306160
0.7421	Intermediate Similarity	NPC310633
0.7407	Intermediate Similarity	NPC476423
0.7399	Intermediate Similarity	NPC260041
0.7368	Intermediate Similarity	NPC111566
0.7262	Intermediate Similarity	NPC20021
0.7231	Intermediate Similarity	NPC19342
0.7216	Intermediate Similarity	NPC210123
0.7158	Intermediate Similarity	NPC73687
0.7136	Intermediate Similarity	NPC19696
0.7136	Intermediate Similarity	NPC136957
0.7129	Intermediate Similarity	NPC469717
0.7118	Intermediate Similarity	NPC150592
0.7114	Intermediate Similarity	NPC469716
0.7108	Intermediate Similarity	NPC476524
0.7035	Intermediate Similarity	NPC174281
0.7035	Intermediate Similarity	NPC475286
0.7027	Intermediate Similarity	NPC2414
0.7021	Intermediate Similarity	NPC271927
0.7016	Intermediate Similarity	NPC40530
0.7016	Intermediate Similarity	NPC314281
0.6906	Remote Similarity	NPC109158
0.69	Remote Similarity	NPC476526
0.69	Remote Similarity	NPC329765
0.69	Remote Similarity	NPC48117
0.6898	Remote Similarity	NPC474696
0.6878	Remote Similarity	NPC469976
0.686	Remote Similarity	NPC476525
0.6813	Remote Similarity	NPC472260
0.681	Remote Similarity	NPC469715
0.6769	Remote Similarity	NPC270834
0.6758	Remote Similarity	NPC52110
0.6733	Remote Similarity	NPC77061
0.6684	Remote Similarity	NPC476419
0.6667	Remote Similarity	NPC476527
0.658	Remote Similarity	NPC66642
0.6559	Remote Similarity	NPC298288
0.6517	Remote Similarity	NPC472288
0.6492	Remote Similarity	NPC233380
0.6471	Remote Similarity	NPC33229
0.6453	Remote Similarity	NPC243716
0.6436	Remote Similarity	NPC142688
0.6422	Remote Similarity	NPC475736
0.6419	Remote Similarity	NPC473218
0.6419	Remote Similarity	NPC470702
0.6419	Remote Similarity	NPC471193
0.6419	Remote Similarity	NPC471194
0.6404	Remote Similarity	NPC291517
0.6389	Remote Similarity	NPC470703
0.6316	Remote Similarity	NPC477004
0.6313	Remote Similarity	NPC23215
0.6296	Remote Similarity	NPC72956
0.6291	Remote Similarity	NPC471191
0.6287	Remote Similarity	NPC133003
0.6284	Remote Similarity	NPC50562
0.6268	Remote Similarity	NPC474389
0.6267	Remote Similarity	NPC6865
0.6267	Remote Similarity	NPC153980
0.6256	Remote Similarity	NPC67658
0.6238	Remote Similarity	NPC21429
0.6238	Remote Similarity	NPC474767
0.6232	Remote Similarity	NPC188821
0.6232	Remote Similarity	NPC474180
0.6215	Remote Similarity	NPC71236
0.6211	Remote Similarity	NPC209362
0.6182	Remote Similarity	NPC177996
0.6182	Remote Similarity	NPC147983
0.6182	Remote Similarity	NPC471192
0.6178	Remote Similarity	NPC74357
0.617	Remote Similarity	NPC13432
0.6169	Remote Similarity	NPC91179
0.6167	Remote Similarity	NPC156003
0.6146	Remote Similarity	NPC213914
0.6146	Remote Similarity	NPC17059
0.6143	Remote Similarity	NPC474195
0.6131	Remote Similarity	NPC469529
0.6127	Remote Similarity	NPC311282
0.6114	Remote Similarity	NPC171317
0.6111	Remote Similarity	NPC270918
0.6108	Remote Similarity	NPC470205
0.6099	Remote Similarity	NPC168209
0.6098	Remote Similarity	NPC94752
0.6096	Remote Similarity	NPC467188
0.6095	Remote Similarity	NPC179701
0.6095	Remote Similarity	NPC292361
0.6093	Remote Similarity	NPC473376
0.6089	Remote Similarity	NPC243633
0.6089	Remote Similarity	NPC175150
0.6087	Remote Similarity	NPC324091
0.6078	Remote Similarity	NPC477003
0.6078	Remote Similarity	NPC228835
0.6071	Remote Similarity	NPC272174
0.607	Remote Similarity	NPC15573
0.607	Remote Similarity	NPC183662
0.607	Remote Similarity	NPC217372
0.6066	Remote Similarity	NPC262898
0.6064	Remote Similarity	NPC302159
0.6062	Remote Similarity	NPC476817
0.6053	Remote Similarity	NPC473878
0.605	Remote Similarity	NPC186068
0.604	Remote Similarity	NPC219336
0.604	Remote Similarity	NPC265710
0.604	Remote Similarity	NPC11126
0.6039	Remote Similarity	NPC213629
0.6035	Remote Similarity	NPC474196
0.6032	Remote Similarity	NPC105811
0.6032	Remote Similarity	NPC100726
0.6029	Remote Similarity	NPC159125
0.6028	Remote Similarity	NPC471944
0.6011	Remote Similarity	NPC292434
0.6011	Remote Similarity	NPC167200
0.6011	Remote Similarity	NPC138596
0.6011	Remote Similarity	NPC200397
0.6011	Remote Similarity	NPC64661
0.6011	Remote Similarity	NPC14448
0.6011	Remote Similarity	NPC195704
0.6011	Remote Similarity	NPC98156
0.601	Remote Similarity	NPC16659
0.6	Remote Similarity	NPC161861
0.6	Remote Similarity	NPC320968
0.5991	Remote Similarity	NPC64216
0.599	Remote Similarity	NPC473380
0.599	Remote Similarity	NPC240088
0.5979	Remote Similarity	NPC212742
0.5978	Remote Similarity	NPC313823
0.5973	Remote Similarity	NPC474896
0.5972	Remote Similarity	NPC317701
0.5969	Remote Similarity	NPC471655
0.5969	Remote Similarity	NPC253687
0.5968	Remote Similarity	NPC12831
0.5968	Remote Similarity	NPC244087
0.5968	Remote Similarity	NPC286529
0.5968	Remote Similarity	NPC74928
0.5968	Remote Similarity	NPC3698
0.5968	Remote Similarity	NPC209281
0.5968	Remote Similarity	NPC302717
0.5968	Remote Similarity	NPC59839
0.5968	Remote Similarity	NPC97230
0.5968	Remote Similarity	NPC205604
0.5968	Remote Similarity	NPC169308
0.5968	Remote Similarity	NPC129753
0.5968	Remote Similarity	NPC48171
0.5968	Remote Similarity	NPC77582
0.5949	Remote Similarity	NPC474492
0.5947	Remote Similarity	NPC220851
0.5947	Remote Similarity	NPC31097
0.5946	Remote Similarity	NPC54744
0.5946	Remote Similarity	NPC282247
0.5941	Remote Similarity	NPC151635
0.5939	Remote Similarity	NPC274981
0.5939	Remote Similarity	NPC162268
0.5935	Remote Similarity	NPC268744
0.5935	Remote Similarity	NPC293917
0.5935	Remote Similarity	NPC201266
0.5935	Remote Similarity	NPC237414
0.5935	Remote Similarity	NPC220797
0.5935	Remote Similarity	NPC474318
0.5935	Remote Similarity	NPC475914
0.5935	Remote Similarity	NPC153123
0.5931	Remote Similarity	NPC69843
0.592	Remote Similarity	NPC288074
0.5918	Remote Similarity	NPC470680
0.5918	Remote Similarity	NPC100104
0.5914	Remote Similarity	NPC85443
0.5913	Remote Similarity	NPC473946
0.5907	Remote Similarity	NPC77241
0.5907	Remote Similarity	NPC269203
0.5907	Remote Similarity	NPC251391
0.5907	Remote Similarity	NPC312860
0.5907	Remote Similarity	NPC166209
0.5907	Remote Similarity	NPC13456
0.5894	Remote Similarity	NPC474258
0.5894	Remote Similarity	NPC241025
0.5885	Remote Similarity	NPC209917
0.588	Remote Similarity	NPC89987
0.588	Remote Similarity	NPC475506

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 NPC46022 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	987
0.2-0.3	1615
0.3-0.4	2341
0.4-0.5	2873
0.5-0.6	1038
0.6-0.7	36
0.7-0.8	2
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
0.7157	Intermediate Similarity	NPD2289	Phase 3
0.7157	Intermediate Similarity	NPD2290	Phase 3
0.6818	Remote Similarity	NPD5686	Approved
0.6818	Remote Similarity	NPD5685	Approved
0.6749	Remote Similarity	NPD7459	Phase 2
0.6732	Remote Similarity	NPD7817	Phase 1
0.6633	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.663	Remote Similarity	NPD510	Phase 1
0.6566	Remote Similarity	NPD1096	Discontinued
0.6541	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5017	Discontinued
0.6453	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8169	Discontinued
0.6378	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3968	Approved
0.6338	Remote Similarity	NPD3411	Phase 2
0.6338	Remote Similarity	NPD3410	Approved
0.6333	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD1573	Approved
0.6308	Remote Similarity	NPD1575	Approved
0.6291	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7727	Phase 2
0.6244	Remote Similarity	NPD8114	Approved
0.6244	Remote Similarity	NPD8115	Approved
0.6226	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD3967	Approved
0.6205	Remote Similarity	NPD7716	Approved
0.6205	Remote Similarity	NPD7717	Approved
0.6186	Remote Similarity	NPD1631	Approved
0.6182	Remote Similarity	NPD3353	Approved
0.6179	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD460	Discontinued
0.6154	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5643	Phase 2
0.61	Remote Similarity	NPD2367	Phase 2
0.6098	Remote Similarity	NPD7026	Phase 2
0.6096	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD1618	Phase 2
0.6083	Remote Similarity	NPD7232	Discontinued
0.6065	Remote Similarity	NPD7568	Phase 1
0.6062	Remote Similarity	NPD6173	Approved
0.6055	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5510	Approved
0.6054	Remote Similarity	NPD1623	Approved
0.6044	Remote Similarity	NPD272	Approved
0.604	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD1630	Approved
0.6028	Remote Similarity	NPD4963	Approved
0.6028	Remote Similarity	NPD4962	Approved
0.6026	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD4959	Approved
0.6009	Remote Similarity	NPD4960	Approved
0.6009	Remote Similarity	NPD2442	Approved
0.6009	Remote Similarity	NPD2443	Approved
0.6	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6210	Phase 3
0.5991	Remote Similarity	NPD6753	Phase 1
0.5991	Remote Similarity	NPD2547	Discontinued
0.5991	Remote Similarity	NPD1952	Discontinued
0.5991	Remote Similarity	NPD6752	Phase 1
0.599	Remote Similarity	NPD3246	Discontinued
0.5982	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD1600	Suspended
0.5981	Remote Similarity	NPD4961	Approved
0.5981	Remote Similarity	NPD1658	Discontinued
0.598	Remote Similarity	NPD3178	Discontinued
0.5978	Remote Similarity	NPD1031	Discontinued
0.5972	Remote Similarity	NPD7619	Phase 3
0.5972	Remote Similarity	NPD7618	Phase 3
0.5971	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.597	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD1506	Discontinued
0.5962	Remote Similarity	NPD5016	Approved
0.5961	Remote Similarity	NPD3079	Approved
0.5961	Remote Similarity	NPD3077	Approved
0.5961	Remote Similarity	NPD3076	Approved
0.5961	Remote Similarity	NPD3078	Approved
0.596	Remote Similarity	NPD438	Approved
0.596	Remote Similarity	NPD439	Approved
0.5956	Remote Similarity	NPD5199	Approved
0.5956	Remote Similarity	NPD5198	Approved
0.5953	Remote Similarity	NPD5333	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD2130	Discontinued
0.5945	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD5809	Phase 3
0.5939	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD6486	Approved
0.5936	Remote Similarity	NPD6487	Approved
0.5935	Remote Similarity	NPD7308	Discontinued
0.5935	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6579	Phase 2
0.5926	Remote Similarity	NPD3773	Approved
0.5926	Remote Similarity	NPD3775	Approved
0.5926	Remote Similarity	NPD3774	Approved
0.5922	Remote Similarity	NPD7482	Phase 2
0.5922	Remote Similarity	NPD7483	Phase 2
0.592	Remote Similarity	NPD750	Phase 2
0.592	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.5919	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.5919	Remote Similarity	NPD7970	Approved
0.5915	Remote Similarity	NPD1174	Phase 2
0.5915	Remote Similarity	NPD6664	Approved
0.5913	Remote Similarity	NPD4988	Discontinued
0.5913	Remote Similarity	NPD6165	Phase 2
0.5913	Remote Similarity	NPD6164	Phase 2
0.5909	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD180	Clinical (unspecified phase)
0.589	Remote Similarity	NPD4415	Approved
0.589	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD6369	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD9599	Approved
0.5882	Remote Similarity	NPD1587	Approved
0.5877	Remote Similarity	NPD6665	Discontinued
0.5877	Remote Similarity	NPD5973	Phase 2
0.5877	Remote Similarity	NPD5974	Approved
0.5876	Remote Similarity	NPD2061	Approved
0.587	Remote Similarity	NPD8289	Discontinued
0.5869	Remote Similarity	NPD7027	Phase 3
0.5867	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD7665	Phase 2
0.5864	Remote Similarity	NPD7666	Phase 3
0.5856	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3989	Phase 3
0.5854	Remote Similarity	NPD1643	Phase 3
0.5853	Remote Similarity	NPD6268	Phase 1
0.5853	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD9598	Discontinued
0.5845	Remote Similarity	NPD721	Approved
0.5841	Remote Similarity	NPD6470	Phase 3
0.5837	Remote Similarity	NPD2408	Discontinued
0.5837	Remote Similarity	NPD5935	Discontinued
0.5837	Remote Similarity	NPD4520	Approved
0.5837	Remote Similarity	NPD3856	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3041	Approved
0.5833	Remote Similarity	NPD2912	Approved
0.5833	Remote Similarity	NPD2911	Approved
0.5825	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD3990	Phase 3
0.5822	Remote Similarity	NPD7543	Phase 2
0.5819	Remote Similarity	NPD1571	Phase 2
0.5818	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.5813	Remote Similarity	NPD4883	Approved
0.5813	Remote Similarity	NPD482	Approved
0.5811	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.581	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.5808	Remote Similarity	NPD6209	Approved
0.5806	Remote Similarity	NPD201	Phase 2
0.5806	Remote Similarity	NPD200	Phase 2
0.5803	Remote Similarity	NPD971	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.5799	Remote Similarity	NPD5426	Phase 3
0.5798	Remote Similarity	NPD2222	Discontinued
0.5796	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD645	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD6249	Phase 2
0.5787	Remote Similarity	NPD2405	Phase 3
0.5787	Remote Similarity	NPD6248	Phase 2
0.5787	Remote Similarity	NPD6999	Discontinued
0.5787	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD979	Approved
0.5775	Remote Similarity	NPD1173	Approved
0.5773	Remote Similarity	NPD6271	Approved
0.5773	Remote Similarity	NPD2128	Phase 1
0.5769	Remote Similarity	NPD8106	Phase 2
0.5767	Remote Similarity	NPD5446	Phase 2
0.5761	Remote Similarity	NPD4887	Discontinued
0.576	Remote Similarity	NPD5461	Discontinued
0.5759	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.5751	Remote Similarity	NPD7887	Approved
0.5751	Remote Similarity	NPD7888	Approved
0.5748	Remote Similarity	NPD5853	Phase 3
0.5748	Remote Similarity	NPD5855	Phase 3
0.5745	Remote Similarity	NPD1572	Phase 2
0.5743	Remote Similarity	NPD4024	Phase 3
0.5742	Remote Similarity	NPD6557	Phase 2
0.5741	Remote Similarity	NPD772	Phase 3
0.5741	Remote Similarity	NPD1982	Phase 1
0.5735	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD1586	Approved
0.5735	Remote Similarity	NPD1657	Approved
0.5735	Remote Similarity	NPD4334	Discontinued
0.5734	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.5734	Remote Similarity	NPD4458	Phase 2
0.5733	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6771	Discontinued
0.5728	Remote Similarity	NPD4376	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