NPASS Compound

Structure

NPC178301 OpenBabel07101718192D 21 22 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 2 0 0 0 0 2 5 1 0 0 0 0 3 7 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 14 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 21 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	605.63
Volume:	323.261
LogP:	6.25
LogD:	3.209
LogS:	-7.242
# Rotatable Bonds:	3
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	2.7
Fsp3:	0.077
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.685
MDCK Permeability:	1.621585943212267e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.966
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.272
Plasma Protein Binding (PPB):	102.10919952392578%
Volume Distribution (VD):	4.806
Pgp-substrate:	8.261055946350098%

ADMET: Metabolism

CYP1A2-inhibitor:	0.927
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.746
CYP2C19-substrate:	0.349
CYP2C9-inhibitor:	0.931
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.654
CYP3A4-inhibitor:	0.132
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	0.711
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.766
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.867
Skin Sensitization:	0.827
Carcinogencity:	0.065
Eye Corrosion:	0.165
Eye Irritation:	0.956
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC178301

Natural Product ID:	NPC178301
*Common Name:**	3,4,5-Tribromo-2-(2,4-Dibromophenoxy)-6-Methoxyphenol
IUPAC Name:	3,4,5-tribromo-2-(2,4-dibromophenoxy)-6-methoxyphenol
Synonyms:
Standard InCHIKey:	QHLGNSNAZCEPSX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H7Br5O3/c1-20-12-9(17)8(16)10(18)13(11(12)19)21-7-3-2-5(14)4-6(7)15/h2-4,19H,1H3
SMILES:	COc1c(c(c(c(c1O)Oc1ccc(cc1Br)Br)Br)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256756
PubChem CID:	24799159
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers [CHEMONTID:0001845] Bromodiphenyl ethers

*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
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921404]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593283]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18198840]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	at 1020 m depth from Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[18824352]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20230038]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26551342]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26863083]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27336796]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32243140]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[7494145]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748373]

☑ 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
Others	4

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8690.0	nM	PMID[483277]
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	12.0	mm	PMID[483277]
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	11.0	mm	PMID[483277]
NPT447	Organism	Streptomyces	Streptomyces	IZ	=	10.0	mm	PMID[483277]

☑ 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 NPC178301 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	854
0.1-0.2	5673
0.2-0.3	14699
0.3-0.4	4781
0.4-0.5	7002
0.5-0.6	8091
0.6-0.7	1500
0.7-0.8	47
0.8-0.85	4
0.85-0.9	16
0.9-0.95	27
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC222684
0.96	High Similarity	NPC206183
0.936	High Similarity	NPC45728
0.9268	High Similarity	NPC173511
0.9268	High Similarity	NPC88733
0.92	High Similarity	NPC163019
0.92	High Similarity	NPC1744
0.9187	High Similarity	NPC226737
0.9187	High Similarity	NPC153580
0.9187	High Similarity	NPC299939
0.912	High Similarity	NPC197576
0.912	High Similarity	NPC81149
0.912	High Similarity	NPC230013
0.912	High Similarity	NPC68350
0.912	High Similarity	NPC131940
0.9106	High Similarity	NPC63317
0.9106	High Similarity	NPC41232
0.904	High Similarity	NPC25134
0.904	High Similarity	NPC295879
0.904	High Similarity	NPC175520
0.904	High Similarity	NPC159866
0.904	High Similarity	NPC64130
0.904	High Similarity	NPC97157
0.9032	High Similarity	NPC170824
0.9024	High Similarity	NPC44270
0.9024	High Similarity	NPC86007
0.896	High Similarity	NPC40302
0.896	High Similarity	NPC137922
0.896	High Similarity	NPC474375
0.896	High Similarity	NPC235166
0.8943	High Similarity	NPC191194
0.8943	High Similarity	NPC104124
0.888	High Similarity	NPC47769
0.888	High Similarity	NPC196371
0.8686	High Similarity	NPC8577
0.8629	High Similarity	NPC264379
0.8548	High Similarity	NPC162294
0.8492	Intermediate Similarity	NPC71186
0.8468	Intermediate Similarity	NPC221301
0.7902	Intermediate Similarity	NPC286337
0.7742	Intermediate Similarity	NPC307875
0.7724	Intermediate Similarity	NPC319933
0.7718	Intermediate Similarity	NPC152947
0.748	Intermediate Similarity	NPC124712
0.7444	Intermediate Similarity	NPC151617
0.7444	Intermediate Similarity	NPC76915
0.7361	Intermediate Similarity	NPC245386
0.7333	Intermediate Similarity	NPC214289
0.7329	Intermediate Similarity	NPC271942
0.7299	Intermediate Similarity	NPC145780
0.7266	Intermediate Similarity	NPC232654
0.7234	Intermediate Similarity	NPC210355
0.7226	Intermediate Similarity	NPC205850
0.7203	Intermediate Similarity	NPC226493
0.7203	Intermediate Similarity	NPC160081
0.72	Intermediate Similarity	NPC314803
0.7153	Intermediate Similarity	NPC232084
0.7153	Intermediate Similarity	NPC247364
0.7153	Intermediate Similarity	NPC61516
0.7153	Intermediate Similarity	NPC10932
0.7143	Intermediate Similarity	NPC228972
0.7143	Intermediate Similarity	NPC122792
0.7143	Intermediate Similarity	NPC221090
0.7133	Intermediate Similarity	NPC85049
0.7122	Intermediate Similarity	NPC126216
0.7122	Intermediate Similarity	NPC71579
0.7122	Intermediate Similarity	NPC473411
0.7122	Intermediate Similarity	NPC228875
0.7122	Intermediate Similarity	NPC105147
0.7122	Intermediate Similarity	NPC262253
0.7113	Intermediate Similarity	NPC216836
0.7083	Intermediate Similarity	NPC472338
0.708	Intermediate Similarity	NPC226629
0.7071	Intermediate Similarity	NPC192810
0.7071	Intermediate Similarity	NPC95168
0.7067	Intermediate Similarity	NPC89341
0.7059	Intermediate Similarity	NPC259638
0.7055	Intermediate Similarity	NPC244890
0.7047	Intermediate Similarity	NPC160932
0.7034	Intermediate Similarity	NPC472597
0.7021	Intermediate Similarity	NPC5796
0.7021	Intermediate Similarity	NPC206487
0.7016	Intermediate Similarity	NPC16649
0.7016	Intermediate Similarity	NPC114325
0.7014	Intermediate Similarity	NPC45824
0.7	Intermediate Similarity	NPC41562
0.7	Intermediate Similarity	NPC152722
0.7	Intermediate Similarity	NPC473653
0.6993	Remote Similarity	NPC470699
0.6993	Remote Similarity	NPC37074
0.6986	Remote Similarity	NPC184447
0.6986	Remote Similarity	NPC35932
0.6986	Remote Similarity	NPC202762
0.6986	Remote Similarity	NPC86655
0.6986	Remote Similarity	NPC7903
0.6986	Remote Similarity	NPC16208
0.6986	Remote Similarity	NPC160991
0.6986	Remote Similarity	NPC303011
0.6986	Remote Similarity	NPC161203
0.6985	Remote Similarity	NPC193067
0.6978	Remote Similarity	NPC166759
0.6972	Remote Similarity	NPC475169
0.6972	Remote Similarity	NPC60885
0.6972	Remote Similarity	NPC193544
0.6972	Remote Similarity	NPC57490
0.6972	Remote Similarity	NPC298757
0.6972	Remote Similarity	NPC17943
0.6972	Remote Similarity	NPC203133
0.6972	Remote Similarity	NPC251855
0.6972	Remote Similarity	NPC221077
0.6972	Remote Similarity	NPC233410
0.6972	Remote Similarity	NPC208950
0.6972	Remote Similarity	NPC234400
0.6972	Remote Similarity	NPC472093
0.6972	Remote Similarity	NPC82483
0.6972	Remote Similarity	NPC117214
0.6972	Remote Similarity	NPC299584
0.6972	Remote Similarity	NPC116907
0.6972	Remote Similarity	NPC265483
0.6966	Remote Similarity	NPC91291
0.6966	Remote Similarity	NPC214860
0.6957	Remote Similarity	NPC20674
0.695	Remote Similarity	NPC473572
0.695	Remote Similarity	NPC228922
0.695	Remote Similarity	NPC474169
0.695	Remote Similarity	NPC121115
0.695	Remote Similarity	NPC197757
0.6944	Remote Similarity	NPC63179
0.6939	Remote Similarity	NPC229442
0.6939	Remote Similarity	NPC168059
0.6939	Remote Similarity	NPC37196
0.6939	Remote Similarity	NPC475840
0.6939	Remote Similarity	NPC94236
0.6939	Remote Similarity	NPC36661
0.6937	Remote Similarity	NPC475697
0.6934	Remote Similarity	NPC9248
0.6929	Remote Similarity	NPC75713
0.6928	Remote Similarity	NPC109346
0.6923	Remote Similarity	NPC28730
0.6923	Remote Similarity	NPC189589
0.6923	Remote Similarity	NPC214406
0.6923	Remote Similarity	NPC469622
0.6923	Remote Similarity	NPC110677
0.6923	Remote Similarity	NPC78974
0.6923	Remote Similarity	NPC18924
0.6923	Remote Similarity	NPC44748
0.6923	Remote Similarity	NPC223136
0.6923	Remote Similarity	NPC298845
0.6923	Remote Similarity	NPC103823
0.6923	Remote Similarity	NPC181361
0.6917	Remote Similarity	NPC247871
0.6906	Remote Similarity	NPC474565
0.6906	Remote Similarity	NPC229401
0.6897	Remote Similarity	NPC273295
0.6897	Remote Similarity	NPC3439
0.6897	Remote Similarity	NPC470258
0.6897	Remote Similarity	NPC285339
0.6897	Remote Similarity	NPC222004
0.6897	Remote Similarity	NPC190629
0.6897	Remote Similarity	NPC210623
0.6897	Remote Similarity	NPC202582
0.6897	Remote Similarity	NPC218856
0.6897	Remote Similarity	NPC226788
0.6892	Remote Similarity	NPC106215
0.6892	Remote Similarity	NPC111635
0.6892	Remote Similarity	NPC317380
0.6892	Remote Similarity	NPC170694
0.6892	Remote Similarity	NPC310854
0.688	Remote Similarity	NPC475466
0.6879	Remote Similarity	NPC229213
0.6875	Remote Similarity	NPC236791
0.6875	Remote Similarity	NPC74817
0.6875	Remote Similarity	NPC293054
0.6875	Remote Similarity	NPC236760
0.6875	Remote Similarity	NPC124452
0.6875	Remote Similarity	NPC474119
0.6875	Remote Similarity	NPC159968
0.6875	Remote Similarity	NPC282000
0.6875	Remote Similarity	NPC127587
0.6875	Remote Similarity	NPC266555
0.6875	Remote Similarity	NPC82679
0.6875	Remote Similarity	NPC324112
0.6875	Remote Similarity	NPC246620
0.6875	Remote Similarity	NPC169474
0.6875	Remote Similarity	NPC50368
0.6875	Remote Similarity	NPC474535
0.6871	Remote Similarity	NPC470752
0.6871	Remote Similarity	NPC127624
0.6866	Remote Similarity	NPC255068
0.6857	Remote Similarity	NPC276195
0.6849	Remote Similarity	NPC229231
0.6846	Remote Similarity	NPC112939
0.6846	Remote Similarity	NPC470356
0.6846	Remote Similarity	NPC94750
0.6846	Remote Similarity	NPC112246
0.6846	Remote Similarity	NPC474206
0.6846	Remote Similarity	NPC121812
0.6846	Remote Similarity	NPC134968
0.6846	Remote Similarity	NPC201357
0.6846	Remote Similarity	NPC472337

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 NPC178301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	630
0.1-0.2	1535
0.2-0.3	3287
0.3-0.4	2153
0.4-0.5	1151
0.5-0.6	361
0.6-0.7	32
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
0.7016	Intermediate Similarity	NPD9296	Approved
0.6953	Remote Similarity	NPD291	Approved
0.6828	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3027	Phase 3
0.6759	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1613	Approved
0.6757	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9094	Approved
0.6643	Remote Similarity	NPD1548	Phase 1
0.6525	Remote Similarity	NPD7534	Approved
0.6525	Remote Similarity	NPD7533	Approved
0.6508	Remote Similarity	NPD9365	Approved
0.6471	Remote Similarity	NPD556	Approved
0.6458	Remote Similarity	NPD1610	Phase 2
0.6389	Remote Similarity	NPD915	Approved
0.6377	Remote Similarity	NPD228	Approved
0.6376	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.637	Remote Similarity	NPD2982	Phase 2
0.637	Remote Similarity	NPD2983	Phase 2
0.6316	Remote Similarity	NPD1558	Phase 1
0.6301	Remote Similarity	NPD2981	Phase 2
0.6267	Remote Similarity	NPD4908	Phase 1
0.6265	Remote Similarity	NPD4288	Approved
0.625	Remote Similarity	NPD968	Approved
0.6233	Remote Similarity	NPD422	Phase 1
0.622	Remote Similarity	NPD9295	Approved
0.6204	Remote Similarity	NPD290	Approved
0.62	Remote Similarity	NPD3018	Phase 2
0.6184	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD9089	Approved
0.6149	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD1934	Approved
0.6127	Remote Similarity	NPD9299	Approved
0.6122	Remote Similarity	NPD1091	Approved
0.6118	Remote Similarity	NPD4625	Phase 3
0.6108	Remote Similarity	NPD2801	Approved
0.6098	Remote Similarity	NPD9093	Approved
0.6087	Remote Similarity	NPD9552	Approved
0.6074	Remote Similarity	NPD2183	Approved
0.6074	Remote Similarity	NPD2184	Approved
0.6049	Remote Similarity	NPD1511	Approved
0.604	Remote Similarity	NPD4749	Approved
0.6036	Remote Similarity	NPD3882	Suspended
0.6	Remote Similarity	NPD1653	Approved
0.5985	Remote Similarity	NPD9501	Approved
0.5985	Remote Similarity	NPD9244	Approved
0.5976	Remote Similarity	NPD1512	Approved
0.5974	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD4010	Discontinued
0.5929	Remote Similarity	NPD2684	Approved
0.5928	Remote Similarity	NPD4675	Approved
0.5928	Remote Similarity	NPD4678	Approved
0.5918	Remote Similarity	NPD1797	Approved
0.5918	Remote Similarity	NPD1798	Approved
0.5917	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD3454	Phase 3
0.5902	Remote Similarity	NPD4287	Approved
0.5882	Remote Similarity	NPD1242	Phase 1
0.5871	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4357	Discontinued
0.5833	Remote Similarity	NPD5283	Phase 1
0.582	Remote Similarity	NPD8095	Phase 1
0.5813	Remote Similarity	NPD1551	Phase 2
0.5796	Remote Similarity	NPD1240	Approved
0.5795	Remote Similarity	NPD6166	Phase 2
0.5795	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD2296	Approved
0.5782	Remote Similarity	NPD1102	Approved
0.5782	Remote Similarity	NPD1103	Approved
0.5776	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD3540	Phase 1
0.5764	Remote Similarity	NPD7843	Approved
0.5756	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD1549	Phase 2
0.5731	Remote Similarity	NPD1465	Phase 2
0.5723	Remote Similarity	NPD1607	Approved
0.5714	Remote Similarity	NPD3539	Phase 1
0.5714	Remote Similarity	NPD1469	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD1652	Phase 2
0.5705	Remote Similarity	NPD1357	Approved
0.5698	Remote Similarity	NPD3817	Phase 2
0.5698	Remote Similarity	NPD7054	Approved
0.569	Remote Similarity	NPD6234	Discontinued
0.5686	Remote Similarity	NPD3225	Approved
0.5677	Remote Similarity	NPD9494	Approved
0.5677	Remote Similarity	NPD2861	Phase 2
0.5676	Remote Similarity	NPD5536	Phase 2
0.5667	Remote Similarity	NPD7074	Phase 3
0.5667	Remote Similarity	NPD5846	Approved
0.5667	Remote Similarity	NPD6516	Phase 2
0.5667	Remote Similarity	NPD7472	Approved
0.5663	Remote Similarity	NPD7212	Phase 2
0.5663	Remote Similarity	NPD6799	Approved
0.5663	Remote Similarity	NPD7213	Phase 3
0.566	Remote Similarity	NPD230	Phase 1
0.5658	Remote Similarity	NPD1608	Approved
0.5646	Remote Similarity	NPD7157	Approved
0.5646	Remote Similarity	NPD191	Approved
0.5646	Remote Similarity	NPD6671	Approved
0.5642	Remote Similarity	NPD3818	Discontinued
0.5636	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.5629	Remote Similarity	NPD4123	Phase 3
0.5629	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.5629	Remote Similarity	NPD7447	Phase 1
0.5625	Remote Similarity	NPD7199	Phase 2
0.5621	Remote Similarity	NPD6582	Phase 2
0.5621	Remote Similarity	NPD6583	Phase 3
0.5617	Remote Similarity	NPD6099	Approved
0.5617	Remote Similarity	NPD6100	Approved
0.5613	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD846	Approved
0.5612	Remote Similarity	NPD940	Approved

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