NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	229.96
Volume:	173.476
LogP:	1.702
LogD:	1.387
LogS:	-2.983
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	2.116
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.563
MDCK Permeability:	1.7330439732177183e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.903
Plasma Protein Binding (PPB):	94.36750030517578%
Volume Distribution (VD):	0.504
Pgp-substrate:	7.6752028465271%

ADMET: Metabolism

CYP1A2-inhibitor:	0.916
CYP1A2-substrate:	0.763
CYP2C19-inhibitor:	0.128
CYP2C19-substrate:	0.444
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.511
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.4
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	3.289
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.144
Skin Sensitization:	0.449
Carcinogencity:	0.123
Eye Corrosion:	0.965
Eye Irritation:	0.989
Respiratory Toxicity:	0.848

Download Data

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

Natural Product: NPC250597

Natural Product ID:	NPC250597
*Common Name:**	5-Bromovanillin
IUPAC Name:	3-bromo-4-hydroxy-5-methoxybenzaldehyde
Synonyms:	5-Bromovanillin
Standard InCHIKey:	KLSHZDPXXKAHIJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H7BrO3/c1-12-7-3-5(4-10)2-6(9)8(7)11/h2-4,11H,1H3
SMILES:	COc1cc(C=O)cc(c1O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467332
PubChem CID:	18099
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
NPO32930	polysiphonia lanosa	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387639]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	>	200000.0	nM	PMID[461290]

☑ 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 NPC250597 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	420
0.1-0.2	2805
0.2-0.3	8058
0.3-0.4	11534
0.4-0.5	3669
0.5-0.6	8693
0.6-0.7	7023
0.7-0.8	470
0.8-0.85	15
0.85-0.9	6
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC473608
0.9155	High Similarity	NPC178097
0.9098	High Similarity	NPC214553
0.8741	High Similarity	NPC117237
0.8741	High Similarity	NPC203719
0.8696	High Similarity	NPC474135
0.8671	High Similarity	NPC184632
0.8643	High Similarity	NPC199089
0.8551	High Similarity	NPC298268
0.8333	Intermediate Similarity	NPC32163
0.8333	Intermediate Similarity	NPC16651
0.831	Intermediate Similarity	NPC237330
0.8252	Intermediate Similarity	NPC274613
0.8222	Intermediate Similarity	NPC295317
0.8182	Intermediate Similarity	NPC144662
0.817	Intermediate Similarity	NPC294870
0.8169	Intermediate Similarity	NPC50763
0.8085	Intermediate Similarity	NPC261759
0.8042	Intermediate Similarity	NPC111888
0.8028	Intermediate Similarity	NPC66905
0.8	Intermediate Similarity	NPC139519
0.7986	Intermediate Similarity	NPC159418
0.7986	Intermediate Similarity	NPC283823
0.7949	Intermediate Similarity	NPC474535
0.7941	Intermediate Similarity	NPC117759
0.7941	Intermediate Similarity	NPC100395
0.7929	Intermediate Similarity	NPC473626
0.7926	Intermediate Similarity	NPC39793
0.791	Intermediate Similarity	NPC278102
0.7898	Intermediate Similarity	NPC475697
0.7877	Intermediate Similarity	NPC208760
0.7871	Intermediate Similarity	NPC135103
0.7867	Intermediate Similarity	NPC299154
0.7847	Intermediate Similarity	NPC110800
0.7842	Intermediate Similarity	NPC114298
0.7842	Intermediate Similarity	NPC229213
0.7838	Intermediate Similarity	NPC325625
0.7826	Intermediate Similarity	NPC225245
0.7801	Intermediate Similarity	NPC120066
0.7786	Intermediate Similarity	NPC242372
0.7786	Intermediate Similarity	NPC474169
0.7786	Intermediate Similarity	NPC164778
0.7786	Intermediate Similarity	NPC4181
0.7786	Intermediate Similarity	NPC473572
0.7786	Intermediate Similarity	NPC257976
0.7785	Intermediate Similarity	NPC305490
0.7785	Intermediate Similarity	NPC4796
0.7778	Intermediate Similarity	NPC285776
0.777	Intermediate Similarity	NPC110899
0.777	Intermediate Similarity	NPC125417
0.777	Intermediate Similarity	NPC95679
0.777	Intermediate Similarity	NPC112068
0.777	Intermediate Similarity	NPC25305
0.7763	Intermediate Similarity	NPC275278
0.7762	Intermediate Similarity	NPC304747
0.773	Intermediate Similarity	NPC273686
0.773	Intermediate Similarity	NPC312404
0.7712	Intermediate Similarity	NPC287495
0.7712	Intermediate Similarity	NPC9370
0.7698	Intermediate Similarity	NPC158949
0.7681	Intermediate Similarity	NPC299406
0.766	Intermediate Similarity	NPC474691
0.7622	Intermediate Similarity	NPC179777
0.7616	Intermediate Similarity	NPC908
0.7616	Intermediate Similarity	NPC138438
0.7616	Intermediate Similarity	NPC326065
0.7609	Intermediate Similarity	NPC212743
0.7606	Intermediate Similarity	NPC30216
0.7586	Intermediate Similarity	NPC226855
0.7582	Intermediate Similarity	NPC469615
0.7582	Intermediate Similarity	NPC239608
0.7582	Intermediate Similarity	NPC46161
0.7569	Intermediate Similarity	NPC281020
0.7569	Intermediate Similarity	NPC276466
0.7569	Intermediate Similarity	NPC123228
0.7569	Intermediate Similarity	NPC151167
0.7569	Intermediate Similarity	NPC158654
0.7569	Intermediate Similarity	NPC123722
0.7569	Intermediate Similarity	NPC5018
0.7568	Intermediate Similarity	NPC155098
0.7566	Intermediate Similarity	NPC84273
0.7552	Intermediate Similarity	NPC142776
0.7536	Intermediate Similarity	NPC150919
0.7532	Intermediate Similarity	NPC469683
0.7518	Intermediate Similarity	NPC177291
0.7518	Intermediate Similarity	NPC194416
0.7518	Intermediate Similarity	NPC201777
0.7517	Intermediate Similarity	NPC204592
0.7516	Intermediate Similarity	NPC169214
0.7516	Intermediate Similarity	NPC192597
0.7516	Intermediate Similarity	NPC312256
0.7516	Intermediate Similarity	NPC176030
0.7516	Intermediate Similarity	NPC229218
0.7516	Intermediate Similarity	NPC141817
0.75	Intermediate Similarity	NPC90128
0.75	Intermediate Similarity	NPC303680
0.75	Intermediate Similarity	NPC50823
0.75	Intermediate Similarity	NPC276014
0.75	Intermediate Similarity	NPC154275
0.75	Intermediate Similarity	NPC43706
0.75	Intermediate Similarity	NPC84076
0.75	Intermediate Similarity	NPC202474
0.7483	Intermediate Similarity	NPC284409
0.7482	Intermediate Similarity	NPC137537
0.7482	Intermediate Similarity	NPC164706
0.7482	Intermediate Similarity	NPC272471
0.7482	Intermediate Similarity	NPC70744
0.7482	Intermediate Similarity	NPC107588
0.7481	Intermediate Similarity	NPC54626
0.7481	Intermediate Similarity	NPC57879
0.7468	Intermediate Similarity	NPC50954
0.7468	Intermediate Similarity	NPC46880
0.7467	Intermediate Similarity	NPC324929
0.7466	Intermediate Similarity	NPC304622
0.7466	Intermediate Similarity	NPC85049
0.7465	Intermediate Similarity	NPC116562
0.7465	Intermediate Similarity	NPC286573
0.7464	Intermediate Similarity	NPC79844
0.7451	Intermediate Similarity	NPC110419
0.745	Intermediate Similarity	NPC45404
0.7448	Intermediate Similarity	NPC473708
0.7448	Intermediate Similarity	NPC474147
0.7448	Intermediate Similarity	NPC286683
0.7447	Intermediate Similarity	NPC204466
0.7431	Intermediate Similarity	NPC271985
0.7431	Intermediate Similarity	NPC280767
0.7419	Intermediate Similarity	NPC91694
0.7419	Intermediate Similarity	NPC300603
0.7419	Intermediate Similarity	NPC113397
0.7419	Intermediate Similarity	NPC142165
0.7419	Intermediate Similarity	NPC207732
0.7415	Intermediate Similarity	NPC160081
0.7415	Intermediate Similarity	NPC226493
0.7415	Intermediate Similarity	NPC172673
0.7413	Intermediate Similarity	NPC106659
0.7413	Intermediate Similarity	NPC163083
0.7413	Intermediate Similarity	NPC229084
0.7413	Intermediate Similarity	NPC160900
0.7413	Intermediate Similarity	NPC18984
0.7407	Intermediate Similarity	NPC179309
0.74	Intermediate Similarity	NPC38101
0.7394	Intermediate Similarity	NPC70752
0.7389	Intermediate Similarity	NPC472969
0.7386	Intermediate Similarity	NPC78987
0.7386	Intermediate Similarity	NPC82336
0.7383	Intermediate Similarity	NPC307006
0.7383	Intermediate Similarity	NPC129889
0.7383	Intermediate Similarity	NPC156124
0.7383	Intermediate Similarity	NPC471328
0.7383	Intermediate Similarity	NPC475468
0.7383	Intermediate Similarity	NPC304929
0.7383	Intermediate Similarity	NPC1321
0.7383	Intermediate Similarity	NPC327410
0.7375	Intermediate Similarity	NPC131121
0.7372	Intermediate Similarity	NPC160777
0.7372	Intermediate Similarity	NPC73416
0.7365	Intermediate Similarity	NPC264145
0.7361	Intermediate Similarity	NPC4012
0.7355	Intermediate Similarity	NPC254659
0.7355	Intermediate Similarity	NPC473090
0.7353	Intermediate Similarity	NPC139617
0.7353	Intermediate Similarity	NPC78918
0.7351	Intermediate Similarity	NPC90431
0.7342	Intermediate Similarity	NPC474903
0.7342	Intermediate Similarity	NPC476394
0.7342	Intermediate Similarity	NPC98809
0.7333	Intermediate Similarity	NPC471110
0.7333	Intermediate Similarity	NPC7097
0.7333	Intermediate Similarity	NPC36108
0.7333	Intermediate Similarity	NPC246358
0.7333	Intermediate Similarity	NPC233731
0.7329	Intermediate Similarity	NPC473787
0.7329	Intermediate Similarity	NPC20287
0.7329	Intermediate Similarity	NPC293641
0.7329	Intermediate Similarity	NPC20404
0.7329	Intermediate Similarity	NPC12022
0.7325	Intermediate Similarity	NPC39361
0.7325	Intermediate Similarity	NPC165389
0.7325	Intermediate Similarity	NPC143903
0.7325	Intermediate Similarity	NPC226987
0.7324	Intermediate Similarity	NPC109083
0.7324	Intermediate Similarity	NPC269843
0.7324	Intermediate Similarity	NPC14007
0.7324	Intermediate Similarity	NPC189844
0.7324	Intermediate Similarity	NPC60962
0.7324	Intermediate Similarity	NPC224814
0.732	Intermediate Similarity	NPC474784
0.7319	Intermediate Similarity	NPC252004
0.7315	Intermediate Similarity	NPC239302
0.7312	Intermediate Similarity	NPC289438
0.7312	Intermediate Similarity	NPC75377
0.731	Intermediate Similarity	NPC257589
0.731	Intermediate Similarity	NPC53305
0.731	Intermediate Similarity	NPC87113
0.7308	Intermediate Similarity	NPC196941
0.7308	Intermediate Similarity	NPC309169
0.7303	Intermediate Similarity	NPC157944
0.7303	Intermediate Similarity	NPC197766
0.7303	Intermediate Similarity	NPC471236
0.7303	Intermediate Similarity	NPC474274

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 NPC250597 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	1204
0.2-0.3	2217
0.3-0.4	2818
0.4-0.5	1500
0.5-0.6	814
0.6-0.7	164
0.7-0.8	6
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8741	High Similarity	NPD9494	Approved
0.7413	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD230	Phase 1
0.7226	Intermediate Similarity	NPD228	Approved
0.7188	Intermediate Similarity	NPD824	Approved
0.7178	Intermediate Similarity	NPD2296	Approved
0.7039	Intermediate Similarity	NPD447	Suspended
0.703	Intermediate Similarity	NPD3882	Suspended
0.6993	Remote Similarity	NPD9545	Approved
0.6986	Remote Similarity	NPD9269	Phase 2
0.6951	Remote Similarity	NPD1934	Approved
0.6923	Remote Similarity	NPD5536	Phase 2
0.6909	Remote Similarity	NPD2801	Approved
0.6826	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1511	Approved
0.6712	Remote Similarity	NPD9268	Approved
0.6707	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1465	Phase 2
0.6687	Remote Similarity	NPD1512	Approved
0.6687	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1240	Approved
0.6645	Remote Similarity	NPD943	Approved
0.6643	Remote Similarity	NPD1241	Discontinued
0.6599	Remote Similarity	NPD1357	Approved
0.6582	Remote Similarity	NPD1510	Phase 2
0.6571	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3818	Discontinued
0.6568	Remote Similarity	NPD4288	Approved
0.6562	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1607	Approved
0.6552	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6166	Phase 2
0.6545	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6190	Approved
0.6541	Remote Similarity	NPD2935	Discontinued
0.6533	Remote Similarity	NPD3972	Approved
0.6517	Remote Similarity	NPD7685	Pre-registration
0.6509	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD9493	Approved
0.65	Remote Similarity	NPD2344	Approved
0.6488	Remote Similarity	NPD6386	Approved
0.6488	Remote Similarity	NPD6385	Approved
0.6478	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3817	Phase 2
0.6467	Remote Similarity	NPD3455	Phase 2
0.6454	Remote Similarity	NPD1358	Approved
0.6452	Remote Similarity	NPD3027	Phase 3
0.6446	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7054	Approved
0.6437	Remote Similarity	NPD6232	Discontinued
0.6429	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD1298	Discontinued
0.6424	Remote Similarity	NPD9717	Approved
0.641	Remote Similarity	NPD411	Approved
0.6404	Remote Similarity	NPD7074	Phase 3
0.6404	Remote Similarity	NPD7472	Approved
0.6379	Remote Similarity	NPD1247	Approved
0.6374	Remote Similarity	NPD5353	Approved
0.637	Remote Similarity	NPD9296	Approved
0.6369	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD919	Approved
0.6358	Remote Similarity	NPD1549	Phase 2
0.6341	Remote Similarity	NPD2309	Approved
0.634	Remote Similarity	NPD1283	Approved
0.634	Remote Similarity	NPD1876	Approved
0.6335	Remote Similarity	NPD1551	Phase 2
0.6331	Remote Similarity	NPD4380	Phase 2
0.6329	Remote Similarity	NPD3620	Phase 2
0.6329	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7473	Discontinued
0.6319	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1608	Approved
0.6306	Remote Similarity	NPD3144	Approved
0.6306	Remote Similarity	NPD3145	Approved
0.6301	Remote Similarity	NPD5283	Phase 1
0.6299	Remote Similarity	NPD1203	Approved
0.6298	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.629	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD1933	Approved
0.6284	Remote Similarity	NPD405	Clinical (unspecified phase)
0.628	Remote Similarity	NPD8166	Discontinued
0.628	Remote Similarity	NPD4110	Phase 3
0.628	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5978	Approved
0.6279	Remote Similarity	NPD5977	Approved
0.6278	Remote Similarity	NPD6797	Phase 2
0.6272	Remote Similarity	NPD7458	Discontinued
0.627	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD3134	Approved
0.6266	Remote Similarity	NPD2674	Phase 3
0.6265	Remote Similarity	NPD4357	Discontinued
0.6265	Remote Similarity	NPD6799	Approved
0.6257	Remote Similarity	NPD5844	Phase 1
0.625	Remote Similarity	NPD4010	Discontinued
0.6243	Remote Similarity	NPD7251	Discontinued
0.6242	Remote Similarity	NPD2354	Approved
0.6229	Remote Similarity	NPD5494	Approved
0.6228	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD2533	Approved
0.6228	Remote Similarity	NPD2532	Approved
0.6228	Remote Similarity	NPD2534	Approved
0.6226	Remote Similarity	NPD3140	Approved
0.6226	Remote Similarity	NPD3142	Approved
0.6225	Remote Similarity	NPD1778	Approved
0.6209	Remote Similarity	NPD7808	Phase 3
0.6207	Remote Similarity	NPD7075	Discontinued
0.6196	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD2821	Approved
0.6183	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD4287	Approved
0.6182	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD2684	Approved
0.6173	Remote Similarity	NPD2799	Discontinued
0.6171	Remote Similarity	NPD6234	Discontinued
0.6159	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD1651	Approved
0.6154	Remote Similarity	NPD2798	Approved
0.6144	Remote Similarity	NPD1281	Approved
0.6144	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD9718	Approved
0.6135	Remote Similarity	NPD2796	Approved
0.6133	Remote Similarity	NPD9092	Discovery
0.6131	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD3146	Approved
0.6131	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD9244	Approved
0.6125	Remote Similarity	NPD825	Approved
0.6125	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD1613	Approved
0.6125	Remote Similarity	NPD826	Approved
0.6125	Remote Similarity	NPD1558	Phase 1
0.6124	Remote Similarity	NPD5242	Approved
0.6118	Remote Similarity	NPD4626	Approved
0.6118	Remote Similarity	NPD1653	Approved
0.6118	Remote Similarity	NPD17	Approved
0.6115	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD290	Approved
0.6105	Remote Similarity	NPD6873	Phase 2
0.6104	Remote Similarity	NPD1481	Phase 2
0.6101	Remote Similarity	NPD3764	Approved
0.6101	Remote Similarity	NPD6798	Discontinued
0.6095	Remote Similarity	NPD6273	Approved
0.6093	Remote Similarity	NPD1894	Discontinued
0.6087	Remote Similarity	NPD6355	Discontinued
0.6087	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD555	Phase 2
0.6084	Remote Similarity	NPD7003	Approved
0.6082	Remote Similarity	NPD2651	Approved
0.6082	Remote Similarity	NPD2649	Approved
0.6076	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD74	Approved
0.6069	Remote Similarity	NPD9266	Approved
0.6069	Remote Similarity	NPD37	Approved
0.6062	Remote Similarity	NPD4062	Phase 3
0.6062	Remote Similarity	NPD6233	Phase 2
0.6062	Remote Similarity	NPD259	Phase 1
0.6051	Remote Similarity	NPD258	Approved
0.6051	Remote Similarity	NPD257	Approved
0.6051	Remote Similarity	NPD1019	Discontinued
0.6051	Remote Similarity	NPD5647	Approved
0.6048	Remote Similarity	NPD3887	Approved
0.6047	Remote Similarity	NPD6599	Discontinued
0.6047	Remote Similarity	NPD7028	Phase 2
0.6039	Remote Similarity	NPD3705	Approved
0.6039	Remote Similarity	NPD1535	Discovery
0.6036	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD3926	Phase 2
0.6034	Remote Similarity	NPD7819	Suspended
0.6027	Remote Similarity	NPD3021	Approved
0.6027	Remote Similarity	NPD3022	Approved
0.6025	Remote Similarity	NPD4060	Phase 1
0.6022	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD2163	Approved
0.6014	Remote Similarity	NPD7843	Approved
0.6012	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD743	Approved
0.6012	Remote Similarity	NPD958	Approved
0.6	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9267	Approved
0.6	Remote Similarity	NPD2353	Approved
0.6	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2313	Discontinued
0.6	Remote Similarity	NPD7266	Discontinued
0.6	Remote Similarity	NPD7157	Approved
0.6	Remote Similarity	NPD2346	Discontinued
0.6	Remote Similarity	NPD9263	Approved
0.6	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9264	Approved
0.5988	Remote Similarity	NPD3750	Approved
0.5986	Remote Similarity	NPD291	Approved
0.5978	Remote Similarity	NPD6559	Discontinued
0.5978	Remote Similarity	NPD7039	Approved
0.5978	Remote Similarity	NPD7038	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