NPASS Compound

Structure

NPC152947 OpenBabel07101718292D 23 24 0 0 0 0 0 0 0 0999 V2000 4.1569 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3255 -1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3255 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1569 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3255 0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9600 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 2.4942 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 -1.4400 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.9883 0.9600 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -0.9600 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 -2.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 -2.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3255 1.9200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -1.4400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 0.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 8 1 0 0 0 0 2 6 2 0 0 0 0 2 7 1 0 0 0 0 3 5 1 0 0 0 0 3 18 1 0 0 0 0 4 6 1 0 0 0 0 4 19 1 0 0 0 0 5 9 1 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	511.81
Volume:	328.361
LogP:	3.225
LogD:	1.561
LogS:	-3.208
# Rotatable Bonds:	4
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	3.181
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.078
MDCK Permeability:	1.2932540812471416e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.961
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	100.06207275390625%
Volume Distribution (VD):	0.306
Pgp-substrate:	2.0358996391296387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.817
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.12
CYP2D6-inhibitor:	0.135
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.116

ADMET: Excretion

Clearance (CL):	0.991
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.153
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.203
AMES Toxicity:	0.121
Rat Oral Acute Toxicity:	0.43
Maximum Recommended Daily Dose:	0.69
Skin Sensitization:	0.954
Carcinogencity:	0.207
Eye Corrosion:	0.003
Eye Irritation:	0.834
Respiratory Toxicity:	0.069

Download Data

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

Natural Product: NPC152947

Natural Product ID:	NPC152947
*Common Name:**	6-Bromo-3-[2,5-Dibromo-6-Hydroxy-3-(Hydroxymethyl)Phenoxy]-4-(Hydroxymethyl)Benzene-1,2-Diol
IUPAC Name:	6-bromo-3-[2,5-dibromo-6-hydroxy-3-(hydroxymethyl)phenoxy]-4-(hydroxymethyl)benzene-1,2-diol
Synonyms:
Standard InCHIKey:	VROPXEOEAVUYAZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H11Br3O6/c15-7-2-6(4-19)13(12(22)10(7)20)23-14-9(17)5(3-18)1-8(16)11(14)21/h1-2,18-22H,3-4H2
SMILES:	OCc1cc(Br)c(c(c1Oc1c(O)c(Br)cc(c1Br)CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491351
PubChem CID:	10553876
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
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395508]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18053715]
NPO4939	Odonthalia corymbifera	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	25000.0	nM	PMID[528320]

☑ 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 NPC152947 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	709
0.1-0.2	2935
0.2-0.3	11026
0.3-0.4	9286
0.4-0.5	4587
0.5-0.6	7460
0.6-0.7	5644
0.7-0.8	1028
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8483	Intermediate Similarity	NPC245386
0.8435	Intermediate Similarity	NPC271942
0.838	Intermediate Similarity	NPC474147
0.838	Intermediate Similarity	NPC473708
0.831	Intermediate Similarity	NPC43706
0.8288	Intermediate Similarity	NPC244890
0.8219	Intermediate Similarity	NPC303011
0.8207	Intermediate Similarity	NPC226493
0.8207	Intermediate Similarity	NPC160081
0.8146	Intermediate Similarity	NPC89341
0.8138	Intermediate Similarity	NPC85049
0.8133	Intermediate Similarity	NPC160932
0.8117	Intermediate Similarity	NPC113862
0.8105	Intermediate Similarity	NPC109346
0.8067	Intermediate Similarity	NPC156356
0.8027	Intermediate Similarity	NPC220825
0.8027	Intermediate Similarity	NPC42760
0.8027	Intermediate Similarity	NPC268266
0.8027	Intermediate Similarity	NPC268342
0.8014	Intermediate Similarity	NPC45824
0.8012	Intermediate Similarity	NPC38980
0.7973	Intermediate Similarity	NPC61477
0.7973	Intermediate Similarity	NPC15658
0.7973	Intermediate Similarity	NPC185604
0.7973	Intermediate Similarity	NPC219876
0.7973	Intermediate Similarity	NPC261619
0.7973	Intermediate Similarity	NPC78770
0.7973	Intermediate Similarity	NPC126029
0.7972	Intermediate Similarity	NPC473572
0.7972	Intermediate Similarity	NPC474169
0.7959	Intermediate Similarity	NPC214860
0.7959	Intermediate Similarity	NPC91291
0.7943	Intermediate Similarity	NPC474146
0.7933	Intermediate Similarity	NPC472337
0.7933	Intermediate Similarity	NPC260898
0.7933	Intermediate Similarity	NPC234333
0.7933	Intermediate Similarity	NPC47398
0.7919	Intermediate Similarity	NPC168059
0.7919	Intermediate Similarity	NPC229442
0.7919	Intermediate Similarity	NPC475840
0.7919	Intermediate Similarity	NPC163560
0.7908	Intermediate Similarity	NPC118794
0.7905	Intermediate Similarity	NPC309787
0.7905	Intermediate Similarity	NPC472597
0.7902	Intermediate Similarity	NPC229213
0.7891	Intermediate Similarity	NPC474614
0.7881	Intermediate Similarity	NPC16435
0.7881	Intermediate Similarity	NPC302701
0.7881	Intermediate Similarity	NPC472334
0.7881	Intermediate Similarity	NPC269091
0.7881	Intermediate Similarity	NPC472336
0.7881	Intermediate Similarity	NPC306441
0.7877	Intermediate Similarity	NPC5447
0.7877	Intermediate Similarity	NPC250432
0.7877	Intermediate Similarity	NPC216836
0.7852	Intermediate Similarity	NPC35932
0.7852	Intermediate Similarity	NPC86655
0.7852	Intermediate Similarity	NPC160991
0.7852	Intermediate Similarity	NPC16208
0.7852	Intermediate Similarity	NPC184447
0.7852	Intermediate Similarity	NPC127624
0.7852	Intermediate Similarity	NPC202762
0.7852	Intermediate Similarity	NPC470752
0.7852	Intermediate Similarity	NPC7903
0.7838	Intermediate Similarity	NPC472338
0.7832	Intermediate Similarity	NPC145780
0.7829	Intermediate Similarity	NPC168680
0.7823	Intermediate Similarity	NPC46274
0.7823	Intermediate Similarity	NPC226331
0.7815	Intermediate Similarity	NPC470356
0.7815	Intermediate Similarity	NPC61946
0.7815	Intermediate Similarity	NPC112939
0.7815	Intermediate Similarity	NPC474206
0.7815	Intermediate Similarity	NPC94750
0.7815	Intermediate Similarity	NPC121812
0.7815	Intermediate Similarity	NPC112246
0.7815	Intermediate Similarity	NPC164787
0.7808	Intermediate Similarity	NPC45728
0.7808	Intermediate Similarity	NPC134219
0.7793	Intermediate Similarity	NPC137117
0.7778	Intermediate Similarity	NPC47790
0.777	Intermediate Similarity	NPC3439
0.777	Intermediate Similarity	NPC210623
0.777	Intermediate Similarity	NPC190629
0.777	Intermediate Similarity	NPC470258
0.777	Intermediate Similarity	NPC222004
0.777	Intermediate Similarity	NPC273295
0.777	Intermediate Similarity	NPC226788
0.777	Intermediate Similarity	NPC285339
0.777	Intermediate Similarity	NPC218856
0.777	Intermediate Similarity	NPC202582
0.7763	Intermediate Similarity	NPC227503
0.7763	Intermediate Similarity	NPC230734
0.7763	Intermediate Similarity	NPC162659
0.7763	Intermediate Similarity	NPC270456
0.7763	Intermediate Similarity	NPC470802
0.7763	Intermediate Similarity	NPC248727
0.7763	Intermediate Similarity	NPC265433
0.7763	Intermediate Similarity	NPC474639
0.7755	Intermediate Similarity	NPC210355
0.7748	Intermediate Similarity	NPC310854
0.7748	Intermediate Similarity	NPC317380
0.7748	Intermediate Similarity	NPC106215
0.7748	Intermediate Similarity	NPC170694
0.774	Intermediate Similarity	NPC299584
0.774	Intermediate Similarity	NPC265483
0.774	Intermediate Similarity	NPC82483
0.7733	Intermediate Similarity	NPC300678
0.773	Intermediate Similarity	NPC475697
0.7718	Intermediate Similarity	NPC469612
0.7718	Intermediate Similarity	NPC469614
0.7718	Intermediate Similarity	NPC178301
0.7712	Intermediate Similarity	NPC276490
0.7712	Intermediate Similarity	NPC326797
0.7712	Intermediate Similarity	NPC102904
0.7712	Intermediate Similarity	NPC176051
0.7712	Intermediate Similarity	NPC211549
0.7712	Intermediate Similarity	NPC474282
0.7712	Intermediate Similarity	NPC103976
0.7712	Intermediate Similarity	NPC107551
0.7697	Intermediate Similarity	NPC151224
0.7687	Intermediate Similarity	NPC18924
0.7687	Intermediate Similarity	NPC214406
0.7687	Intermediate Similarity	NPC44748
0.7687	Intermediate Similarity	NPC223136
0.7687	Intermediate Similarity	NPC78974
0.7687	Intermediate Similarity	NPC28730
0.7687	Intermediate Similarity	NPC103823
0.7687	Intermediate Similarity	NPC181361
0.7682	Intermediate Similarity	NPC11060
0.7682	Intermediate Similarity	NPC36661
0.7682	Intermediate Similarity	NPC263064
0.7677	Intermediate Similarity	NPC471389
0.7677	Intermediate Similarity	NPC311530
0.7677	Intermediate Similarity	NPC263261
0.7677	Intermediate Similarity	NPC87725
0.7671	Intermediate Similarity	NPC122792
0.7671	Intermediate Similarity	NPC228972
0.7669	Intermediate Similarity	NPC474535
0.7667	Intermediate Similarity	NPC469613
0.7667	Intermediate Similarity	NPC469625
0.7667	Intermediate Similarity	NPC470096
0.7667	Intermediate Similarity	NPC30043
0.7667	Intermediate Similarity	NPC470095
0.7662	Intermediate Similarity	NPC236306
0.7662	Intermediate Similarity	NPC127218
0.7662	Intermediate Similarity	NPC25966
0.7662	Intermediate Similarity	NPC473739
0.7662	Intermediate Similarity	NPC70682
0.7662	Intermediate Similarity	NPC319647
0.7662	Intermediate Similarity	NPC232164
0.7662	Intermediate Similarity	NPC245207
0.7662	Intermediate Similarity	NPC260741
0.7651	Intermediate Similarity	NPC212015
0.7651	Intermediate Similarity	NPC206183
0.7651	Intermediate Similarity	NPC58164
0.7651	Intermediate Similarity	NPC222684
0.7651	Intermediate Similarity	NPC170844
0.7651	Intermediate Similarity	NPC476968
0.7651	Intermediate Similarity	NPC10225
0.7635	Intermediate Similarity	NPC293054
0.7635	Intermediate Similarity	NPC118787
0.7635	Intermediate Similarity	NPC236791
0.7635	Intermediate Similarity	NPC82679
0.7635	Intermediate Similarity	NPC124452
0.7635	Intermediate Similarity	NPC266555
0.7635	Intermediate Similarity	NPC169474
0.7635	Intermediate Similarity	NPC282000
0.7635	Intermediate Similarity	NPC246620
0.7635	Intermediate Similarity	NPC292056
0.7635	Intermediate Similarity	NPC147821
0.7635	Intermediate Similarity	NPC183181
0.7635	Intermediate Similarity	NPC319625
0.7635	Intermediate Similarity	NPC13004
0.7635	Intermediate Similarity	NPC111247
0.7635	Intermediate Similarity	NPC74817
0.7635	Intermediate Similarity	NPC474119
0.7635	Intermediate Similarity	NPC163332
0.7635	Intermediate Similarity	NPC470699
0.7635	Intermediate Similarity	NPC41706
0.7635	Intermediate Similarity	NPC324112
0.7635	Intermediate Similarity	NPC159968
0.7628	Intermediate Similarity	NPC475084
0.7622	Intermediate Similarity	NPC305490
0.7619	Intermediate Similarity	NPC234400
0.7619	Intermediate Similarity	NPC220311
0.7619	Intermediate Similarity	NPC60885
0.7616	Intermediate Similarity	NPC253105
0.7616	Intermediate Similarity	NPC161203
0.7616	Intermediate Similarity	NPC201587
0.7613	Intermediate Similarity	NPC160283
0.7613	Intermediate Similarity	NPC259519
0.7613	Intermediate Similarity	NPC309124
0.7613	Intermediate Similarity	NPC184797
0.7613	Intermediate Similarity	NPC22317
0.7613	Intermediate Similarity	NPC254759
0.7603	Intermediate Similarity	NPC95168
0.7603	Intermediate Similarity	NPC165375
0.7603	Intermediate Similarity	NPC220598
0.76	Intermediate Similarity	NPC299221

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 NPC152947 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	565
0.1-0.2	1156
0.2-0.3	2991
0.3-0.4	2356
0.4-0.5	1180
0.5-0.6	772
0.6-0.7	125
0.7-0.8	5
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
0.7973	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1613	Approved
0.7877	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3027	Phase 3
0.7192	Intermediate Similarity	NPD1548	Phase 1
0.7114	Intermediate Similarity	NPD1610	Phase 2
0.7091	Intermediate Similarity	NPD1653	Approved
0.7041	Intermediate Similarity	NPD4288	Approved
0.7024	Intermediate Similarity	NPD1934	Approved
0.6951	Remote Similarity	NPD1511	Approved
0.6948	Remote Similarity	NPD3018	Phase 2
0.6903	Remote Similarity	NPD4908	Phase 1
0.6882	Remote Similarity	NPD2801	Approved
0.6867	Remote Similarity	NPD1512	Approved
0.6828	Remote Similarity	NPD228	Approved
0.6815	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3882	Suspended
0.6797	Remote Similarity	NPD2982	Phase 2
0.6797	Remote Similarity	NPD2983	Phase 2
0.6784	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1091	Approved
0.6772	Remote Similarity	NPD8095	Phase 1
0.6732	Remote Similarity	NPD2981	Phase 2
0.673	Remote Similarity	NPD1558	Phase 1
0.6723	Remote Similarity	NPD6166	Phase 2
0.6723	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4010	Discontinued
0.6648	Remote Similarity	NPD3818	Discontinued
0.6624	Remote Similarity	NPD2861	Phase 2
0.6611	Remote Similarity	NPD7054	Approved
0.6608	Remote Similarity	NPD4678	Approved
0.6608	Remote Similarity	NPD4675	Approved
0.6604	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.659	Remote Similarity	NPD1465	Phase 2
0.6581	Remote Similarity	NPD4749	Approved
0.6581	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7074	Phase 3
0.6575	Remote Similarity	NPD7472	Approved
0.6558	Remote Similarity	NPD422	Phase 1
0.6552	Remote Similarity	NPD290	Approved
0.6552	Remote Similarity	NPD3817	Phase 2
0.6541	Remote Similarity	NPD4625	Phase 3
0.6534	Remote Similarity	NPD6234	Discontinued
0.6506	Remote Similarity	NPD6674	Discontinued
0.65	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD3540	Phase 1
0.6483	Remote Similarity	NPD968	Approved
0.6481	Remote Similarity	NPD230	Phase 1
0.6471	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7199	Phase 2
0.6448	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD6797	Phase 2
0.6437	Remote Similarity	NPD37	Approved
0.6436	Remote Similarity	NPD4287	Approved
0.6424	Remote Similarity	NPD3539	Phase 1
0.642	Remote Similarity	NPD4967	Phase 2
0.642	Remote Similarity	NPD4965	Approved
0.642	Remote Similarity	NPD4060	Phase 1
0.642	Remote Similarity	NPD4966	Approved
0.6413	Remote Similarity	NPD7251	Discontinued
0.6407	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD1652	Phase 2
0.64	Remote Similarity	NPD5283	Phase 1
0.6386	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7808	Phase 3
0.6374	Remote Similarity	NPD7228	Approved
0.6374	Remote Similarity	NPD2183	Approved
0.6374	Remote Similarity	NPD2184	Approved
0.6364	Remote Similarity	NPD1242	Phase 1
0.6364	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD1549	Phase 2
0.6346	Remote Similarity	NPD3705	Approved
0.6339	Remote Similarity	NPD5844	Phase 1
0.6331	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD1551	Phase 2
0.6322	Remote Similarity	NPD4380	Phase 2
0.6319	Remote Similarity	NPD3620	Phase 2
0.6319	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4123	Phase 3
0.6298	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7266	Discontinued
0.6284	Remote Similarity	NPD2684	Approved
0.6272	Remote Similarity	NPD3892	Phase 2
0.6265	Remote Similarity	NPD1510	Phase 2
0.6264	Remote Similarity	NPD4005	Discontinued
0.6264	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD1357	Approved
0.6257	Remote Similarity	NPD4357	Discontinued
0.6235	Remote Similarity	NPD2219	Phase 1
0.6235	Remote Similarity	NPD6190	Approved
0.6235	Remote Similarity	NPD2677	Approved
0.6233	Remote Similarity	NPD9244	Approved
0.6226	Remote Similarity	NPD8651	Approved
0.6225	Remote Similarity	NPD7843	Approved
0.6221	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD7447	Phase 1
0.6213	Remote Similarity	NPD3060	Approved
0.6209	Remote Similarity	NPD7157	Approved
0.6209	Remote Similarity	NPD6671	Approved
0.6207	Remote Similarity	NPD291	Approved
0.6205	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD4536	Approved
0.6205	Remote Similarity	NPD4538	Approved
0.619	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD447	Suspended
0.6182	Remote Similarity	NPD5124	Phase 1
0.618	Remote Similarity	NPD2296	Approved
0.618	Remote Similarity	NPD5402	Approved
0.6176	Remote Similarity	NPD3750	Approved
0.6168	Remote Similarity	NPD5588	Approved
0.6168	Remote Similarity	NPD5960	Phase 3
0.6163	Remote Similarity	NPD1774	Approved
0.6163	Remote Similarity	NPD6799	Approved
0.6163	Remote Similarity	NPD7213	Phase 3
0.6163	Remote Similarity	NPD7212	Phase 2
0.6154	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6232	Discontinued
0.6138	Remote Similarity	NPD8054	Approved
0.6138	Remote Similarity	NPD8053	Approved
0.6133	Remote Similarity	NPD3022	Approved
0.6133	Remote Similarity	NPD5494	Approved
0.6133	Remote Similarity	NPD3021	Approved
0.6131	Remote Similarity	NPD6100	Approved
0.6131	Remote Similarity	NPD6099	Approved
0.6129	Remote Similarity	NPD5536	Phase 2
0.6121	Remote Similarity	NPD943	Approved
0.6121	Remote Similarity	NPD1240	Approved
0.612	Remote Similarity	NPD6688	Approved
0.612	Remote Similarity	NPD6687	Approved
0.6118	Remote Similarity	NPD5177	Phase 3
0.6118	Remote Similarity	NPD4237	Approved
0.6118	Remote Similarity	NPD4236	Phase 3
0.6118	Remote Similarity	NPD4162	Approved
0.6117	Remote Similarity	NPD7549	Discontinued
0.6115	Remote Similarity	NPD6516	Phase 2
0.6115	Remote Similarity	NPD5846	Approved
0.6111	Remote Similarity	NPD7075	Discontinued
0.6111	Remote Similarity	NPD9494	Approved
0.6095	Remote Similarity	NPD1375	Discontinued
0.609	Remote Similarity	NPD1182	Approved
0.6074	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD3787	Discontinued
0.6064	Remote Similarity	NPD6559	Discontinued
0.6062	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD5403	Approved
0.6054	Remote Similarity	NPD7473	Discontinued
0.6049	Remote Similarity	NPD6584	Phase 3
0.6048	Remote Similarity	NPD1607	Approved
0.6034	Remote Similarity	NPD2978	Approved
0.6034	Remote Similarity	NPD5401	Approved
0.6034	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD2977	Approved
0.6025	Remote Similarity	NPD3225	Approved
0.6023	Remote Similarity	NPD3686	Approved
0.6023	Remote Similarity	NPD3687	Approved
0.6022	Remote Similarity	NPD3751	Discontinued
0.6013	Remote Similarity	NPD1778	Approved
0.6012	Remote Similarity	NPD7124	Phase 2
0.6012	Remote Similarity	NPD5058	Phase 3
0.6011	Remote Similarity	NPD1247	Approved
0.6	Remote Similarity	NPD2563	Approved
0.6	Remote Similarity	NPD2231	Phase 2
0.6	Remote Similarity	NPD5762	Approved
0.6	Remote Similarity	NPD2560	Approved
0.6	Remote Similarity	NPD6798	Discontinued
0.6	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5763	Approved
0.6	Remote Similarity	NPD2235	Phase 2
0.599	Remote Similarity	NPD4663	Approved
0.5989	Remote Similarity	NPD919	Approved
0.5989	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD4340	Discontinued
0.5988	Remote Similarity	NPD4628	Phase 3
0.5988	Remote Similarity	NPD6355	Discontinued
0.5988	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD846	Approved
0.5986	Remote Similarity	NPD940	Approved
0.5979	Remote Similarity	NPD7240	Approved
0.5978	Remote Similarity	NPD6801	Discontinued
0.5977	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.5975	Remote Similarity	NPD3496	Discontinued
0.5966	Remote Similarity	NPD2122	Discontinued
0.5965	Remote Similarity	NPD2424	Discontinued
0.5964	Remote Similarity	NPD6233	Phase 2
0.5964	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD2674	Phase 3
0.5955	Remote Similarity	NPD6599	Discontinued
0.5944	Remote Similarity	NPD5772	Approved
0.5944	Remote Similarity	NPD7819	Suspended

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