NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	386.93
Volume:	256.382
LogP:	1.323
LogD:	1.454
LogS:	-2.743
# Rotatable Bonds:	0
TPSA:	75.65
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	4.922
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:	-5.216
MDCK Permeability:	1.812471600715071e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.253
20% Bioavailability (F20%):	0.044
30% Bioavailability (F30%):	0.355

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.614
Plasma Protein Binding (PPB):	80.74636840820312%
Volume Distribution (VD):	0.892
Pgp-substrate:	30.17064666748047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.369
CYP1A2-substrate:	0.447
CYP2C19-inhibitor:	0.488
CYP2C19-substrate:	0.121
CYP2C9-inhibitor:	0.435
CYP2C9-substrate:	0.254
CYP2D6-inhibitor:	0.438
CYP2D6-substrate:	0.283
CYP3A4-inhibitor:	0.824
CYP3A4-substrate:	0.368

ADMET: Excretion

Clearance (CL):	3.237
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.802
AMES Toxicity:	0.411
Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.34
Carcinogencity:	0.982
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.875

Download Data

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

Natural Product: NPC28096

Natural Product ID:	NPC28096
*Common Name:**	Dibromophakellin
IUPAC Name:	n.a.
Synonyms:	(+/-)-Dibromophakellin; (-)-Dibromophakellin; Dibromophakellin
Standard InCHIKey:	MKCFBJDWCJAOTN-GXSJLCMTSA-N
Standard InCHI:	InChI=1S/C11H11Br2N5O/c12-5-4-6-8(19)17-3-1-2-11(17)9(15-10(14)16-11)18(6)7(5)13/h4,9H,1-3H2,(H3,14,15,16)/t9-,11+/m0/s1
SMILES:	N=C1N[C@@H]2[C@@]3(N1)CCCN3C(=O)c1n2c(Br)c(c1)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447696
PubChem CID:	42636938 11417878
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
NPO27831	Phakellia flabellata	Species	Bubaridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00445a028]
NPO8786	Acanthella costata	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19243956]
NPO8786	Acanthella costata	Species	Melastomataceae	Eukaryota	n.a.	(25 m) at Sykes Reef (Capricorn-Bunker Group Great Barrier Reef), Australia	n.a.	PMID[19243956]
NPO32942	phakellia mauritiana	Species	Bubaridae	Eukaryota	n.a.	Indian ocean	n.a.	PMID[9051914]
NPO27831	Phakellia flabellata	Species	Bubaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8786	Acanthella costata	Species	Melastomataceae	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	1
ED50	6
IC50	4

Activity Type	# Activity
Cell Line	6
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT377	Cell Line	OVCAR-3	Homo sapiens	ED50	=	15.7	ug ml-1	PMID[475461]
NPT399	Cell Line	SF-295	Homo sapiens	ED50	=	18.8	ug ml-1	PMID[475461]
NPT376	Cell Line	A498	Homo sapiens	ED50	=	17.8	ug ml-1	PMID[475461]
NPT397	Cell Line	NCI-H460	Homo sapiens	ED50	=	22.0	ug ml-1	PMID[475461]
NPT575	Cell Line	KM-20L2	Homo sapiens	ED50	=	20.1	ug ml-1	PMID[475461]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	ED50	=	17.0	ug ml-1	PMID[475461]
NPT223	Individual Protein	Alpha-2b adrenergic receptor	Homo sapiens	EC50	=	4200.0	nM	PMID[475462]
NPT2	Others	Unspecified		IC50	=	25300.0	nM	PMID[475463]
NPT2	Others	Unspecified		IC50	=	27100.0	nM	PMID[475463]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[475463]
NPT2	Others	Unspecified		IC50	=	18700.0	nM	PMID[475463]

☑ 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 NPC28096 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	2408
0.1-0.2	19514
0.2-0.3	13988
0.3-0.4	2951
0.4-0.5	2721
0.5-0.6	916
0.6-0.7	124
0.7-0.8	56
0.8-0.85	13
0.85-0.9	0
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476421
1.0	High Similarity	NPC227489
0.9871	High Similarity	NPC226835
0.9317	High Similarity	NPC136441
0.9212	High Similarity	NPC469814
0.8704	High Similarity	NPC206148
0.8589	High Similarity	NPC476418
0.8452	Intermediate Similarity	NPC97106
0.8333	Intermediate Similarity	NPC474236
0.8333	Intermediate Similarity	NPC54214
0.8229	Intermediate Similarity	NPC111566
0.8229	Intermediate Similarity	NPC63571
0.8204	Intermediate Similarity	NPC474383
0.8182	Intermediate Similarity	NPC310633
0.8121	Intermediate Similarity	NPC27296
0.8056	Intermediate Similarity	NPC19342
0.8036	Intermediate Similarity	NPC73687
0.8023	Intermediate Similarity	NPC46022
0.8023	Intermediate Similarity	NPC112489
0.8	Intermediate Similarity	NPC476413
0.7956	Intermediate Similarity	NPC476414
0.7935	Intermediate Similarity	NPC19696
0.7935	Intermediate Similarity	NPC136957
0.7929	Intermediate Similarity	NPC306160
0.7901	Intermediate Similarity	NPC260041
0.7834	Intermediate Similarity	NPC150592
0.7826	Intermediate Similarity	NPC475286
0.7826	Intermediate Similarity	NPC174281
0.7811	Intermediate Similarity	NPC473706
0.7807	Intermediate Similarity	NPC469716
0.7772	Intermediate Similarity	NPC48117
0.7772	Intermediate Similarity	NPC329765
0.7772	Intermediate Similarity	NPC476526
0.7759	Intermediate Similarity	NPC80528
0.7717	Intermediate Similarity	NPC46811
0.7701	Intermediate Similarity	NPC469976
0.7697	Intermediate Similarity	NPC472861
0.7697	Intermediate Similarity	NPC184932
0.766	Intermediate Similarity	NPC9635
0.7658	Intermediate Similarity	NPC20021
0.7444	Intermediate Similarity	NPC40530
0.7444	Intermediate Similarity	NPC314281
0.7416	Intermediate Similarity	NPC37268
0.736	Intermediate Similarity	NPC271927
0.7333	Intermediate Similarity	NPC476524
0.7333	Intermediate Similarity	NPC476525
0.7283	Intermediate Similarity	NPC476423
0.7273	Intermediate Similarity	NPC2414
0.7268	Intermediate Similarity	NPC270834
0.7264	Intermediate Similarity	NPC469717
0.7251	Intermediate Similarity	NPC472260
0.7243	Intermediate Similarity	NPC476527
0.7196	Intermediate Similarity	NPC188821
0.7196	Intermediate Similarity	NPC474180
0.7181	Intermediate Similarity	NPC210123
0.7135	Intermediate Similarity	NPC474696
0.7135	Intermediate Similarity	NPC474389
0.71	Intermediate Similarity	NPC469715
0.6966	Remote Similarity	NPC253687
0.6865	Remote Similarity	NPC240088
0.6865	Remote Similarity	NPC473380
0.6761	Remote Similarity	NPC109158
0.6738	Remote Similarity	NPC265710
0.6702	Remote Similarity	NPC16659
0.6685	Remote Similarity	NPC298288
0.6627	Remote Similarity	NPC23215
0.6627	Remote Similarity	NPC291517
0.6612	Remote Similarity	NPC233380
0.661	Remote Similarity	NPC52110
0.6607	Remote Similarity	NPC66642
0.659	Remote Similarity	NPC474357
0.6574	Remote Similarity	NPC470323
0.6556	Remote Similarity	NPC142688
0.655	Remote Similarity	NPC472288
0.6544	Remote Similarity	NPC267078
0.6544	Remote Similarity	NPC935
0.6527	Remote Similarity	NPC71236
0.6524	Remote Similarity	NPC475736
0.649	Remote Similarity	NPC470703
0.6462	Remote Similarity	NPC474195
0.6443	Remote Similarity	NPC141612
0.6443	Remote Similarity	NPC17273
0.6443	Remote Similarity	NPC135601
0.6442	Remote Similarity	NPC473218
0.6442	Remote Similarity	NPC470702
0.6418	Remote Similarity	NPC477004
0.6408	Remote Similarity	NPC116555
0.6392	Remote Similarity	NPC133003
0.6378	Remote Similarity	NPC247987
0.6374	Remote Similarity	NPC74357
0.6373	Remote Similarity	NPC470205
0.6343	Remote Similarity	NPC474196
0.634	Remote Similarity	NPC21429
0.6316	Remote Similarity	NPC186068
0.6305	Remote Similarity	NPC77241
0.6305	Remote Similarity	NPC269203
0.6305	Remote Similarity	NPC166209
0.6305	Remote Similarity	NPC13456
0.6303	Remote Similarity	NPC50562
0.6301	Remote Similarity	NPC200397
0.6301	Remote Similarity	NPC167200
0.6301	Remote Similarity	NPC292434
0.6301	Remote Similarity	NPC14448
0.6301	Remote Similarity	NPC64661
0.6301	Remote Similarity	NPC138596
0.6301	Remote Similarity	NPC98156
0.6301	Remote Similarity	NPC195704
0.6292	Remote Similarity	NPC467188
0.6274	Remote Similarity	NPC67658
0.6272	Remote Similarity	NPC313823
0.6269	Remote Similarity	NPC77061
0.6263	Remote Similarity	NPC161861
0.6256	Remote Similarity	NPC268744
0.6256	Remote Similarity	NPC475914
0.6256	Remote Similarity	NPC220797
0.6256	Remote Similarity	NPC201266
0.6256	Remote Similarity	NPC474318
0.6256	Remote Similarity	NPC153123
0.625	Remote Similarity	NPC169308
0.625	Remote Similarity	NPC3698
0.625	Remote Similarity	NPC129753
0.625	Remote Similarity	NPC302717
0.625	Remote Similarity	NPC12831
0.625	Remote Similarity	NPC97230
0.625	Remote Similarity	NPC205604
0.625	Remote Similarity	NPC286529
0.625	Remote Similarity	NPC48171
0.625	Remote Similarity	NPC74928
0.625	Remote Similarity	NPC244087
0.625	Remote Similarity	NPC59839
0.625	Remote Similarity	NPC209281
0.625	Remote Similarity	NPC77582
0.6244	Remote Similarity	NPC267811
0.6243	Remote Similarity	NPC473878
0.6222	Remote Similarity	NPC100726
0.6214	Remote Similarity	NPC317701
0.6198	Remote Similarity	NPC476419
0.6181	Remote Similarity	NPC324091
0.6176	Remote Similarity	NPC237414
0.6157	Remote Similarity	NPC272174
0.6154	Remote Similarity	NPC471655
0.6133	Remote Similarity	NPC105811
0.6124	Remote Similarity	NPC129412
0.6124	Remote Similarity	NPC58268
0.6124	Remote Similarity	NPC114033
0.6124	Remote Similarity	NPC101130
0.6121	Remote Similarity	NPC470731
0.6121	Remote Similarity	NPC470732
0.6117	Remote Similarity	NPC274981
0.6111	Remote Similarity	NPC470440
0.6109	Remote Similarity	NPC156003
0.6103	Remote Similarity	NPC182940
0.6101	Remote Similarity	NPC175150
0.6101	Remote Similarity	NPC243633
0.6095	Remote Similarity	NPC71238
0.6091	Remote Similarity	NPC477003
0.6091	Remote Similarity	NPC108011
0.6087	Remote Similarity	NPC232798
0.6087	Remote Similarity	NPC251391
0.6073	Remote Similarity	NPC471943
0.6073	Remote Similarity	NPC476817
0.6071	Remote Similarity	NPC307191
0.607	Remote Similarity	NPC476460
0.6062	Remote Similarity	NPC469529
0.6055	Remote Similarity	NPC474896
0.6054	Remote Similarity	NPC33229
0.6054	Remote Similarity	NPC75135
0.6054	Remote Similarity	NPC209362
0.6043	Remote Similarity	NPC474492
0.6037	Remote Similarity	NPC168209
0.6031	Remote Similarity	NPC151635
0.6029	Remote Similarity	NPC473376
0.6027	Remote Similarity	NPC312942
0.6027	Remote Similarity	NPC31097
0.6027	Remote Similarity	NPC327095
0.6022	Remote Similarity	NPC204141
0.6011	Remote Similarity	NPC123906
0.6011	Remote Similarity	NPC100104
0.6011	Remote Similarity	NPC470680
0.601	Remote Similarity	NPC110158
0.601	Remote Similarity	NPC326422
0.6009	Remote Similarity	NPC54981
0.6	Remote Similarity	NPC284775
0.6	Remote Similarity	NPC40455
0.5989	Remote Similarity	NPC213914
0.598	Remote Similarity	NPC474258
0.5973	Remote Similarity	NPC19170
0.5971	Remote Similarity	NPC171317
0.5952	Remote Similarity	NPC88115
0.5951	Remote Similarity	NPC102592
0.5951	Remote Similarity	NPC79356
0.5946	Remote Similarity	NPC470679
0.5946	Remote Similarity	NPC70406
0.5946	Remote Similarity	NPC217021
0.5939	Remote Similarity	NPC234403
0.5933	Remote Similarity	NPC106757
0.5931	Remote Similarity	NPC304203
0.5928	Remote Similarity	NPC252572
0.592	Remote Similarity	NPC473946
0.5916	Remote Similarity	NPC195507

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 NPC28096 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	1226
0.2-0.3	1941
0.3-0.4	2334
0.4-0.5	2429
0.5-0.6	791
0.6-0.7	38
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
0.75	Intermediate Similarity	NPD7459	Phase 2
0.7128	Intermediate Similarity	NPD5686	Approved
0.7128	Intermediate Similarity	NPD5685	Approved
0.6857	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2289	Phase 3
0.6684	Remote Similarity	NPD2290	Phase 3
0.665	Remote Similarity	NPD2443	Approved
0.665	Remote Similarity	NPD2442	Approved
0.6555	Remote Similarity	NPD5643	Phase 2
0.6537	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.652	Remote Similarity	NPD1506	Discontinued
0.6517	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1031	Discontinued
0.6456	Remote Similarity	NPD2408	Discontinued
0.6443	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD1658	Discontinued
0.6343	Remote Similarity	NPD2222	Discontinued
0.6333	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD460	Discontinued
0.6318	Remote Similarity	NPD2880	Discontinued
0.631	Remote Similarity	NPD438	Approved
0.631	Remote Similarity	NPD439	Approved
0.6302	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD1600	Suspended
0.6294	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD6470	Phase 3
0.6286	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD2367	Phase 2
0.628	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5198	Approved
0.6262	Remote Similarity	NPD5199	Approved
0.6256	Remote Similarity	NPD2405	Phase 3
0.6243	Remote Similarity	NPD272	Approved
0.6238	Remote Similarity	NPD1952	Discontinued
0.6233	Remote Similarity	NPD6579	Phase 2
0.6233	Remote Similarity	NPD6210	Phase 3
0.6232	Remote Similarity	NPD2008	Discontinued
0.6166	Remote Similarity	NPD3041	Approved
0.6162	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3246	Discontinued
0.6158	Remote Similarity	NPD5446	Phase 2
0.6154	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD1982	Phase 1
0.6117	Remote Similarity	NPD5017	Discontinued
0.6111	Remote Similarity	NPD645	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD1096	Discontinued
0.6091	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD6271	Approved
0.6069	Remote Similarity	NPD809	Discontinued
0.6067	Remote Similarity	NPD9599	Approved
0.6065	Remote Similarity	NPD1623	Approved
0.6059	Remote Similarity	NPD5853	Phase 3
0.6059	Remote Similarity	NPD5855	Phase 3
0.6056	Remote Similarity	NPD2411	Approved
0.6051	Remote Similarity	NPD3078	Approved
0.6051	Remote Similarity	NPD3077	Approved
0.6051	Remote Similarity	NPD3079	Approved
0.6051	Remote Similarity	NPD3076	Approved
0.6049	Remote Similarity	NPD465	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5974	Approved
0.604	Remote Similarity	NPD5973	Phase 2
0.6039	Remote Similarity	NPD7817	Phase 1
0.6035	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD2128	Phase 1
0.6029	Remote Similarity	NPD4299	Phase 1
0.6029	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD2927	Phase 3
0.6022	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5854	Approved
0.6011	Remote Similarity	NPD174	Discontinued
0.601	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.601	Remote Similarity	NPD6268	Phase 1
0.6	Remote Similarity	NPD3967	Approved
0.6	Remote Similarity	NPD2547	Discontinued
0.6	Remote Similarity	NPD1174	Phase 2
0.5991	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.599	Remote Similarity	NPD1573	Approved
0.599	Remote Similarity	NPD1575	Approved
0.598	Remote Similarity	NPD7406	Phase 2
0.5979	Remote Similarity	NPD1016	Phase 2
0.5979	Remote Similarity	NPD1015	Phase 2
0.5977	Remote Similarity	NPD803	Phase 1
0.5972	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.597	Remote Similarity	NPD5016	Approved
0.597	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.597	Remote Similarity	NPD7175	Phase 1
0.5964	Remote Similarity	NPD7887	Approved
0.5964	Remote Similarity	NPD7888	Approved
0.5962	Remote Similarity	NPD3891	Phase 2
0.5962	Remote Similarity	NPD3890	Phase 2
0.5961	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.5953	Remote Similarity	NPD2363	Discontinued
0.5952	Remote Similarity	NPD2130	Discontinued
0.5952	Remote Similarity	NPD7208	Approved
0.5952	Remote Similarity	NPD7209	Approved
0.5952	Remote Similarity	NPD7207	Approved
0.5952	Remote Similarity	NPD9598	Discontinued
0.5947	Remote Similarity	NPD6986	Phase 1
0.5939	Remote Similarity	NPD3927	Phase 2
0.5938	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD2150	Discontinued
0.5935	Remote Similarity	NPD4863	Approved
0.5933	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD7716	Approved
0.5928	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD7717	Approved
0.5924	Remote Similarity	NPD7568	Phase 1
0.5916	Remote Similarity	NPD509	Phase 3
0.5916	Remote Similarity	NPD1333	Phase 3
0.5916	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD3968	Approved
0.5911	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.5911	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD7656	Approved
0.5907	Remote Similarity	NPD7657	Approved
0.5899	Remote Similarity	NPD3353	Approved
0.5899	Remote Similarity	NPD200	Phase 2
0.5899	Remote Similarity	NPD201	Phase 2
0.5897	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD3410	Approved
0.5896	Remote Similarity	NPD3411	Phase 2
0.5893	Remote Similarity	NPD4811	Discontinued
0.5885	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4436	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD1003	Phase 2
0.5882	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD1630	Approved
0.5871	Remote Similarity	NPD7026	Phase 2
0.5871	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5869	Remote Similarity	NPD6459	Phase 2
0.5867	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5508	Phase 1
0.5852	Remote Similarity	NPD9100	Approved
0.5849	Remote Similarity	NPD5489	Phase 1
0.5849	Remote Similarity	NPD5491	Phase 3
0.5842	Remote Similarity	NPD4988	Discontinued
0.5838	Remote Similarity	NPD4155	Approved
0.5833	Remote Similarity	NPD6465	Phase 2
0.5824	Remote Similarity	NPD5787	Discontinued
0.5822	Remote Similarity	NPD3905	Phase 3
0.5821	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7297	Phase 2
0.5816	Remote Similarity	NPD4883	Approved
0.5812	Remote Similarity	NPD6771	Discontinued
0.5808	Remote Similarity	NPD9396	Approved
0.5808	Remote Similarity	NPD9392	Approved
0.5806	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD3430	Approved
0.5805	Remote Similarity	NPD3431	Approved
0.5803	Remote Similarity	NPD1215	Discontinued
0.5803	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.58	Remote Similarity	NPD3318	Approved
0.58	Remote Similarity	NPD3320	Approved
0.58	Remote Similarity	NPD3319	Phase 1
0.5799	Remote Similarity	NPD8257	Approved
0.5799	Remote Similarity	NPD8256	Approved
0.5799	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD7027	Phase 3
0.5795	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD5809	Phase 3
0.5792	Remote Similarity	NPD4940	Approved
0.5782	Remote Similarity	NPD6802	Phase 3
0.5782	Remote Similarity	NPD2881	Approved
0.5782	Remote Similarity	NPD2879	Approved
0.5781	Remote Similarity	NPD1631	Approved
0.578	Remote Similarity	NPD7970	Approved
0.578	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.5779	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.5777	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.5777	Remote Similarity	NPD3460	Discontinued
0.5775	Remote Similarity	NPD2660	Approved
0.5775	Remote Similarity	NPD3248	Phase 1
0.5775	Remote Similarity	NPD2662	Approved
0.5771	Remote Similarity	NPD7564	Discontinued
0.5759	Remote Similarity	NPD5986	Approved
0.5759	Remote Similarity	NPD5987	Approved
0.5756	Remote Similarity	NPD3517	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD2401	Approved
0.5753	Remote Similarity	NPD2402	Approved
0.5751	Remote Similarity	NPD1313	Approved
0.5745	Remote Similarity	NPD180	Clinical (unspecified phase)
0.5744	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD264	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD5333	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5000	Phase 2
0.5728	Remote Similarity	NPD6229	Phase 2
0.5728	Remote Similarity	NPD4922	Phase 2
0.5727	Remote Similarity	NPD1591	Approved
0.5727	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD5611	Phase 2
0.5721	Remote Similarity	NPD7232	Discontinued
0.5721	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6827	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