NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	273.98
Volume:	216.859
LogP:	2.281
LogD:	2.086
LogS:	-2.524
# Rotatable Bonds:	4
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.856
Synthetic Accessibility Score:	2.186
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.531
MDCK Permeability:	1.5420584531966597e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.045

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.85
Plasma Protein Binding (PPB):	74.85027313232422%
Volume Distribution (VD):	0.612
Pgp-substrate:	10.652758598327637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.712
CYP2C19-substrate:	0.75
CYP2C9-inhibitor:	0.293
CYP2C9-substrate:	0.772
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.534
CYP3A4-inhibitor:	0.348
CYP3A4-substrate:	0.392

ADMET: Excretion

Clearance (CL):	5.392
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.388
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.218
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.293
Carcinogencity:	0.126
Eye Corrosion:	0.138
Eye Irritation:	0.758
Respiratory Toxicity:	0.248

Download Data

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

Natural Product: NPC184632

Natural Product ID:	NPC184632
*Common Name:**	Methyl 2-(3-Bromo-5-Hydroxy-4-Methoxyphenyl)Acetate
IUPAC Name:	methyl 2-(3-bromo-5-hydroxy-4-methoxyphenyl)acetate
Synonyms:
Standard InCHIKey:	QABMWYHERQJVHT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H11BrO4/c1-14-9(13)5-6-3-7(11)10(15-2)8(12)4-6/h3-4,12H,5H2,1-2H3
SMILES:	COC(=O)Cc1cc(O)c(c(c1)Br)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471276
PubChem CID:	11219575
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO14137	Rhodomela confervoides	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217289]
NPO14137	Rhodomela confervoides	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921411]
NPO14137	Rhodomela confervoides	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499317]
NPO14137	Rhodomela confervoides	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	5
MIC	3

Activity Type	# Activity
Cell Line	5
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[534515]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[534515]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[534515]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[534515]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[534515]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[534515]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[534515]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[534515]

☑ 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 NPC184632 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	370
0.1-0.2	1878
0.2-0.3	5809
0.3-0.4	13147
0.4-0.5	4256
0.5-0.6	7106
0.6-0.7	9000
0.7-0.8	1103
0.8-0.85	22
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9362	High Similarity	NPC178097
0.9054	High Similarity	NPC475697
0.8986	High Similarity	NPC474535
0.8815	High Similarity	NPC281020
0.8671	High Similarity	NPC250597
0.844	Intermediate Similarity	NPC307006
0.844	Intermediate Similarity	NPC129889
0.837	Intermediate Similarity	NPC177291
0.837	Intermediate Similarity	NPC194416
0.831	Intermediate Similarity	NPC283823
0.831	Intermediate Similarity	NPC159418
0.8309	Intermediate Similarity	NPC229213
0.8267	Intermediate Similarity	NPC473608
0.8248	Intermediate Similarity	NPC474169
0.8248	Intermediate Similarity	NPC473572
0.8239	Intermediate Similarity	NPC111888
0.8182	Intermediate Similarity	NPC471328
0.8175	Intermediate Similarity	NPC116562
0.8129	Intermediate Similarity	NPC280767
0.8099	Intermediate Similarity	NPC285776
0.8095	Intermediate Similarity	NPC203351
0.8082	Intermediate Similarity	NPC125417
0.8082	Intermediate Similarity	NPC95679
0.8082	Intermediate Similarity	NPC112068
0.8082	Intermediate Similarity	NPC25305
0.8082	Intermediate Similarity	NPC110899
0.8077	Intermediate Similarity	NPC305490
0.8074	Intermediate Similarity	NPC205502
0.8015	Intermediate Similarity	NPC299406
0.8	Intermediate Similarity	NPC173608
0.7945	Intermediate Similarity	NPC208760
0.7945	Intermediate Similarity	NPC139519
0.7943	Intermediate Similarity	NPC43706
0.7919	Intermediate Similarity	NPC326065
0.7902	Intermediate Similarity	NPC85049
0.7887	Intermediate Similarity	NPC16651
0.7887	Intermediate Similarity	NPC32163
0.7887	Intermediate Similarity	NPC158654
0.7887	Intermediate Similarity	NPC474147
0.7887	Intermediate Similarity	NPC473708
0.7881	Intermediate Similarity	NPC469615
0.7877	Intermediate Similarity	NPC155098
0.7857	Intermediate Similarity	NPC163083
0.7852	Intermediate Similarity	NPC322358
0.7852	Intermediate Similarity	NPC4665
0.7847	Intermediate Similarity	NPC142985
0.7847	Intermediate Similarity	NPC226493
0.7847	Intermediate Similarity	NPC160081
0.7842	Intermediate Similarity	NPC201777
0.7842	Intermediate Similarity	NPC136543
0.7832	Intermediate Similarity	NPC214553
0.7829	Intermediate Similarity	NPC469683
0.7823	Intermediate Similarity	NPC470990
0.7817	Intermediate Similarity	NPC154275
0.7793	Intermediate Similarity	NPC469480
0.7786	Intermediate Similarity	NPC114298
0.7785	Intermediate Similarity	NPC325625
0.7785	Intermediate Similarity	NPC284409
0.7778	Intermediate Similarity	NPC226855
0.7778	Intermediate Similarity	NPC241354
0.7771	Intermediate Similarity	NPC294870
0.7746	Intermediate Similarity	NPC53305
0.7746	Intermediate Similarity	NPC257589
0.774	Intermediate Similarity	NPC50763
0.7733	Intermediate Similarity	NPC288452
0.7733	Intermediate Similarity	NPC147379
0.7733	Intermediate Similarity	NPC4796
0.7733	Intermediate Similarity	NPC289690
0.773	Intermediate Similarity	NPC257976
0.773	Intermediate Similarity	NPC242372
0.773	Intermediate Similarity	NPC4181
0.773	Intermediate Similarity	NPC164778
0.7724	Intermediate Similarity	NPC195292
0.7724	Intermediate Similarity	NPC66905
0.7712	Intermediate Similarity	NPC113397
0.7704	Intermediate Similarity	NPC148969
0.7703	Intermediate Similarity	NPC274613
0.7698	Intermediate Similarity	NPC180207
0.7692	Intermediate Similarity	NPC90128
0.7692	Intermediate Similarity	NPC127937
0.7692	Intermediate Similarity	NPC92207
0.7692	Intermediate Similarity	NPC303680
0.7692	Intermediate Similarity	NPC84076
0.7687	Intermediate Similarity	NPC239855
0.7687	Intermediate Similarity	NPC475468
0.7682	Intermediate Similarity	NPC470991
0.7681	Intermediate Similarity	NPC164706
0.7681	Intermediate Similarity	NPC107588
0.7681	Intermediate Similarity	NPC137537
0.7681	Intermediate Similarity	NPC70744
0.7681	Intermediate Similarity	NPC255675
0.7681	Intermediate Similarity	NPC272471
0.7677	Intermediate Similarity	NPC472969
0.7676	Intermediate Similarity	NPC85565
0.7676	Intermediate Similarity	NPC312404
0.7676	Intermediate Similarity	NPC273686
0.7671	Intermediate Similarity	NPC264145
0.7667	Intermediate Similarity	NPC160932
0.7664	Intermediate Similarity	NPC221049
0.7664	Intermediate Similarity	NPC79844
0.7655	Intermediate Similarity	NPC153547
0.7647	Intermediate Similarity	NPC473090
0.7643	Intermediate Similarity	NPC158949
0.7639	Intermediate Similarity	NPC20287
0.7639	Intermediate Similarity	NPC122359
0.7639	Intermediate Similarity	NPC123228
0.7639	Intermediate Similarity	NPC203719
0.7639	Intermediate Similarity	NPC12022
0.7639	Intermediate Similarity	NPC123722
0.7639	Intermediate Similarity	NPC159987
0.7639	Intermediate Similarity	NPC78061
0.7639	Intermediate Similarity	NPC151167
0.7639	Intermediate Similarity	NPC20404
0.7639	Intermediate Similarity	NPC117237
0.7639	Intermediate Similarity	NPC276466
0.7639	Intermediate Similarity	NPC5018
0.7639	Intermediate Similarity	NPC293641
0.7635	Intermediate Similarity	NPC5310
0.7635	Intermediate Similarity	NPC245386
0.7635	Intermediate Similarity	NPC300776
0.7635	Intermediate Similarity	NPC176814
0.7635	Intermediate Similarity	NPC45404
0.7635	Intermediate Similarity	NPC68779
0.7635	Intermediate Similarity	NPC471110
0.7635	Intermediate Similarity	NPC4982
0.7635	Intermediate Similarity	NPC237330
0.7632	Intermediate Similarity	NPC31751
0.7632	Intermediate Similarity	NPC110419
0.7632	Intermediate Similarity	NPC253481
0.7632	Intermediate Similarity	NPC253722
0.7628	Intermediate Similarity	NPC98809
0.7628	Intermediate Similarity	NPC476394
0.7626	Intermediate Similarity	NPC181969
0.7626	Intermediate Similarity	NPC38483
0.7626	Intermediate Similarity	NPC117759
0.7626	Intermediate Similarity	NPC320987
0.7622	Intermediate Similarity	NPC300326
0.7622	Intermediate Similarity	NPC58279
0.7613	Intermediate Similarity	NPC58752
0.7603	Intermediate Similarity	NPC299010
0.76	Intermediate Similarity	NPC156356
0.7595	Intermediate Similarity	NPC135103
0.7586	Intermediate Similarity	NPC226661
0.7586	Intermediate Similarity	NPC278308
0.7584	Intermediate Similarity	NPC113295
0.7584	Intermediate Similarity	NPC152209
0.7582	Intermediate Similarity	NPC477697
0.7582	Intermediate Similarity	NPC470811
0.7582	Intermediate Similarity	NPC273657
0.7582	Intermediate Similarity	NPC106920
0.7582	Intermediate Similarity	NPC312256
0.7582	Intermediate Similarity	NPC477696
0.7571	Intermediate Similarity	NPC202474
0.7571	Intermediate Similarity	NPC148615
0.7571	Intermediate Similarity	NPC2058
0.7571	Intermediate Similarity	NPC177475
0.7571	Intermediate Similarity	NPC35071
0.7569	Intermediate Similarity	NPC179777
0.7568	Intermediate Similarity	NPC1321
0.7568	Intermediate Similarity	NPC156124
0.7568	Intermediate Similarity	NPC304929
0.7566	Intermediate Similarity	NPC89341
0.7566	Intermediate Similarity	NPC50823
0.7566	Intermediate Similarity	NPC100675
0.7564	Intermediate Similarity	NPC98009
0.7564	Intermediate Similarity	NPC470757
0.7556	Intermediate Similarity	NPC173746
0.7556	Intermediate Similarity	NPC8547
0.7556	Intermediate Similarity	NPC257124
0.7556	Intermediate Similarity	NPC156840
0.7552	Intermediate Similarity	NPC20443
0.7552	Intermediate Similarity	NPC146886
0.7552	Intermediate Similarity	NPC137117
0.7552	Intermediate Similarity	NPC60517
0.755	Intermediate Similarity	NPC207516
0.7548	Intermediate Similarity	NPC287275
0.7548	Intermediate Similarity	NPC98356
0.7534	Intermediate Similarity	NPC304622
0.7534	Intermediate Similarity	NPC94810
0.7533	Intermediate Similarity	NPC156892
0.7533	Intermediate Similarity	NPC475111
0.7533	Intermediate Similarity	NPC90431
0.7533	Intermediate Similarity	NPC156307
0.7532	Intermediate Similarity	NPC258307
0.7532	Intermediate Similarity	NPC46161
0.7532	Intermediate Similarity	NPC239608
0.7532	Intermediate Similarity	NPC134975
0.7532	Intermediate Similarity	NPC50954
0.7532	Intermediate Similarity	NPC243891
0.7532	Intermediate Similarity	NPC96501
0.7532	Intermediate Similarity	NPC27159
0.7518	Intermediate Similarity	NPC204466
0.7516	Intermediate Similarity	NPC152947
0.75	Intermediate Similarity	NPC20674
0.75	Intermediate Similarity	NPC474135
0.75	Intermediate Similarity	NPC32058
0.75	Intermediate Similarity	NPC85734
0.75	Intermediate Similarity	NPC474784
0.75	Intermediate Similarity	NPC138978
0.75	Intermediate Similarity	NPC61779

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 NPC184632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	1072
0.2-0.3	2123
0.3-0.4	2798
0.4-0.5	1572
0.5-0.6	976
0.6-0.7	267
0.7-0.8	12
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
0.7639	Intermediate Similarity	NPD9494	Approved
0.7568	Intermediate Similarity	NPD230	Phase 1
0.7556	Intermediate Similarity	NPD228	Approved
0.7484	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1608	Approved
0.7241	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD9545	Approved
0.7161	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1934	Approved
0.7091	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD17	Approved
0.7073	Intermediate Similarity	NPD2801	Approved
0.707	Intermediate Similarity	NPD4628	Phase 3
0.7067	Intermediate Similarity	NPD3027	Phase 3
0.7055	Intermediate Similarity	NPD9269	Phase 2
0.7044	Intermediate Similarity	NPD1511	Approved
0.703	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3146	Approved
0.6993	Remote Similarity	NPD447	Suspended
0.6988	Remote Similarity	NPD3882	Suspended
0.697	Remote Similarity	NPD1465	Phase 2
0.6959	Remote Similarity	NPD1283	Approved
0.6957	Remote Similarity	NPD1512	Approved
0.6928	Remote Similarity	NPD3817	Phase 2
0.6918	Remote Similarity	NPD6190	Approved
0.6914	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6234	Discontinued
0.6882	Remote Similarity	NPD6232	Discontinued
0.6867	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4110	Phase 3
0.6849	Remote Similarity	NPD1778	Approved
0.6826	Remote Similarity	NPD2296	Approved
0.6824	Remote Similarity	NPD1481	Phase 2
0.6821	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD37	Approved
0.6781	Remote Similarity	NPD9268	Approved
0.6776	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7473	Discontinued
0.6759	Remote Similarity	NPD5536	Phase 2
0.6757	Remote Similarity	NPD3705	Approved
0.6757	Remote Similarity	NPD1535	Discovery
0.6757	Remote Similarity	NPD1281	Approved
0.6755	Remote Similarity	NPD258	Approved
0.6755	Remote Similarity	NPD257	Approved
0.6753	Remote Similarity	NPD259	Phase 1
0.6747	Remote Similarity	NPD6386	Approved
0.6747	Remote Similarity	NPD6385	Approved
0.6732	Remote Similarity	NPD9718	Approved
0.6725	Remote Similarity	NPD7199	Phase 2
0.6713	Remote Similarity	NPD5283	Phase 1
0.671	Remote Similarity	NPD1558	Phase 1
0.671	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1240	Approved
0.671	Remote Similarity	NPD826	Approved
0.671	Remote Similarity	NPD1613	Approved
0.671	Remote Similarity	NPD825	Approved
0.6709	Remote Similarity	NPD2935	Discontinued
0.6705	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6166	Phase 2
0.6688	Remote Similarity	NPD6798	Discontinued
0.6687	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7054	Approved
0.6686	Remote Similarity	NPD4966	Approved
0.6686	Remote Similarity	NPD4965	Approved
0.6686	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD555	Phase 2
0.6667	Remote Similarity	NPD1357	Approved
0.6667	Remote Similarity	NPD7685	Pre-registration
0.6648	Remote Similarity	NPD7074	Phase 3
0.6648	Remote Similarity	NPD7472	Approved
0.6647	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1510	Phase 2
0.6645	Remote Similarity	NPD6233	Phase 2
0.6645	Remote Similarity	NPD4062	Phase 3
0.6643	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3818	Discontinued
0.6629	Remote Similarity	NPD7228	Approved
0.6629	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD824	Approved
0.6626	Remote Similarity	NPD6799	Approved
0.6624	Remote Similarity	NPD1607	Approved
0.6623	Remote Similarity	NPD7095	Approved
0.6611	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4060	Phase 1
0.6603	Remote Similarity	NPD943	Approved
0.6601	Remote Similarity	NPD9569	Approved
0.6599	Remote Similarity	NPD1894	Discontinued
0.6591	Remote Similarity	NPD5844	Phase 1
0.659	Remote Similarity	NPD4010	Discontinued
0.6585	Remote Similarity	NPD2533	Approved
0.6585	Remote Similarity	NPD2534	Approved
0.6585	Remote Similarity	NPD2532	Approved
0.6577	Remote Similarity	NPD3847	Discontinued
0.6568	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3687	Approved
0.6566	Remote Similarity	NPD1653	Approved
0.6566	Remote Similarity	NPD3686	Approved
0.6562	Remote Similarity	NPD7266	Discontinued
0.655	Remote Similarity	NPD7075	Discontinued
0.6543	Remote Similarity	NPD8166	Discontinued
0.6538	Remote Similarity	NPD2674	Phase 3
0.6533	Remote Similarity	NPD422	Phase 1
0.6529	Remote Similarity	NPD5353	Approved
0.6527	Remote Similarity	NPD3455	Phase 2
0.6525	Remote Similarity	NPD1358	Approved
0.6519	Remote Similarity	NPD6653	Approved
0.6517	Remote Similarity	NPD6797	Phase 2
0.6516	Remote Similarity	NPD9537	Phase 1
0.6516	Remote Similarity	NPD9536	Phase 1
0.6512	Remote Similarity	NPD919	Approved
0.651	Remote Similarity	NPD4626	Approved
0.6503	Remote Similarity	NPD4287	Approved
0.65	Remote Similarity	NPD9570	Approved
0.6497	Remote Similarity	NPD3620	Phase 2
0.6497	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.649	Remote Similarity	NPD9717	Approved
0.6485	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD1241	Discontinued
0.648	Remote Similarity	NPD7251	Discontinued
0.6474	Remote Similarity	NPD3764	Approved
0.6471	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD9493	Approved
0.646	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD275	Approved
0.6456	Remote Similarity	NPD274	Approved
0.6447	Remote Similarity	NPD2983	Phase 2
0.6447	Remote Similarity	NPD2982	Phase 2
0.6444	Remote Similarity	NPD9296	Approved
0.6444	Remote Similarity	NPD7808	Phase 3
0.6443	Remote Similarity	NPD1651	Approved
0.6442	Remote Similarity	NPD3750	Approved
0.6442	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7033	Discontinued
0.6438	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD3022	Approved
0.6434	Remote Similarity	NPD3021	Approved
0.6429	Remote Similarity	NPD5647	Approved
0.642	Remote Similarity	NPD1549	Phase 2
0.6413	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD196	Phase 1
0.6402	Remote Similarity	NPD2354	Approved
0.6398	Remote Similarity	NPD2438	Suspended
0.6398	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD1551	Phase 2
0.6398	Remote Similarity	NPD6100	Approved
0.6398	Remote Similarity	NPD6099	Approved
0.6392	Remote Similarity	NPD2979	Phase 3
0.6391	Remote Similarity	NPD6599	Discontinued
0.6391	Remote Similarity	NPD4380	Phase 2
0.6389	Remote Similarity	NPD1298	Discontinued
0.6387	Remote Similarity	NPD3018	Phase 2
0.6387	Remote Similarity	NPD454	Approved
0.6386	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2981	Phase 2
0.6374	Remote Similarity	NPD7819	Suspended
0.6374	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD3145	Approved
0.6369	Remote Similarity	NPD3144	Approved
0.6369	Remote Similarity	NPD411	Approved
0.6364	Remote Similarity	NPD5242	Approved
0.6364	Remote Similarity	NPD987	Approved
0.6364	Remote Similarity	NPD2684	Approved
0.6364	Remote Similarity	NPD1203	Approved
0.6358	Remote Similarity	NPD3496	Discontinued
0.6352	Remote Similarity	NPD1933	Approved
0.6346	Remote Similarity	NPD2614	Approved
0.6343	Remote Similarity	NPD8127	Discontinued
0.6331	Remote Similarity	NPD7458	Discontinued
0.6325	Remote Similarity	NPD4357	Discontinued
0.6319	Remote Similarity	NPD4534	Discontinued
0.6316	Remote Similarity	NPD6801	Discontinued
0.6312	Remote Similarity	NPD2653	Approved
0.631	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD2219	Phase 1
0.6301	Remote Similarity	NPD7843	Approved
0.6299	Remote Similarity	NPD3225	Approved
0.6298	Remote Similarity	NPD7038	Approved
0.6298	Remote Similarity	NPD7039	Approved
0.6296	Remote Similarity	NPD2239	Approved
0.6296	Remote Similarity	NPD2240	Approved
0.6294	Remote Similarity	NPD7028	Phase 2
0.6284	Remote Similarity	NPD7157	Approved
0.628	Remote Similarity	NPD3060	Approved
0.6275	Remote Similarity	NPD3972	Approved
0.6266	Remote Similarity	NPD3268	Approved
0.6264	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD6005	Phase 3
0.6258	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD6002	Phase 3
0.6258	Remote Similarity	NPD2797	Approved
0.6258	Remote Similarity	NPD6004	Phase 3
0.6258	Remote Similarity	NPD6006	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