NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	245.95
Volume:	182.267
LogP:	2.292
LogD:	1.39
LogS:	-2.56
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	2.746
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:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.806
MDCK Permeability:	1.4636804735346232e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	94.82776641845703%
Volume Distribution (VD):	0.551
Pgp-substrate:	3.923302173614502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.699
CYP1A2-substrate:	0.676
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.219
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.58
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.313
CYP3A4-inhibitor:	0.074
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	1.537
Half-life (T1/2):	0.817

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.246
Rat Oral Acute Toxicity:	0.37
Maximum Recommended Daily Dose:	0.123
Skin Sensitization:	0.793
Carcinogencity:	0.247
Eye Corrosion:	0.846
Eye Irritation:	0.966
Respiratory Toxicity:	0.836

Download Data

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

Natural Product: NPC294870

Natural Product ID:	NPC294870
*Common Name:**	5-Bromo-2,3-Dihydroxy-6-Methoxybenzaldehyde
IUPAC Name:	5-bromo-2,3-dihydroxy-6-methoxybenzaldehyde
Synonyms:
Standard InCHIKey:	AYYXPGPMLRMGTR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H7BrO4/c1-13-8-4(3-10)7(12)6(11)2-5(8)9/h2-3,11-12H,1H3
SMILES:	O=Cc1c(O)c(O)cc(c1OC)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454456
PubChem CID:	25033523
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
NPO733	Pseudoceratina arabica	Species	Pseudoceratinidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[18598078]
NPO733	Pseudoceratina arabica	Species	Pseudoceratinidae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	3.0	mm	PMID[455869]

☑ 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 NPC294870 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	478
0.1-0.2	2542
0.2-0.3	8660
0.3-0.4	11593
0.4-0.5	3843
0.5-0.6	6558
0.6-0.7	7696
0.7-0.8	1320
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9533	High Similarity	NPC305490
0.8205	Intermediate Similarity	NPC178097
0.817	Intermediate Similarity	NPC250597
0.8065	Intermediate Similarity	NPC299154
0.8038	Intermediate Similarity	NPC473608
0.7975	Intermediate Similarity	NPC143903
0.7975	Intermediate Similarity	NPC226987
0.7857	Intermediate Similarity	NPC157944
0.7857	Intermediate Similarity	NPC474274
0.7821	Intermediate Similarity	NPC50823
0.7812	Intermediate Similarity	NPC61871
0.7812	Intermediate Similarity	NPC55557
0.7812	Intermediate Similarity	NPC30647
0.7799	Intermediate Similarity	NPC472917
0.7778	Intermediate Similarity	NPC10467
0.7771	Intermediate Similarity	NPC184632
0.7764	Intermediate Similarity	NPC218490
0.7764	Intermediate Similarity	NPC183655
0.7764	Intermediate Similarity	NPC287395
0.773	Intermediate Similarity	NPC475076
0.773	Intermediate Similarity	NPC19980
0.773	Intermediate Similarity	NPC45291
0.7727	Intermediate Similarity	NPC274613
0.7716	Intermediate Similarity	NPC102003
0.7716	Intermediate Similarity	NPC294502
0.7716	Intermediate Similarity	NPC200221
0.7716	Intermediate Similarity	NPC92722
0.7683	Intermediate Similarity	NPC181209
0.7683	Intermediate Similarity	NPC291802
0.7683	Intermediate Similarity	NPC100263
0.7683	Intermediate Similarity	NPC269451
0.7683	Intermediate Similarity	NPC121522
0.7683	Intermediate Similarity	NPC209487
0.7683	Intermediate Similarity	NPC131266
0.7683	Intermediate Similarity	NPC100971
0.7683	Intermediate Similarity	NPC35763
0.7683	Intermediate Similarity	NPC245382
0.7683	Intermediate Similarity	NPC216769
0.7682	Intermediate Similarity	NPC261759
0.7673	Intermediate Similarity	NPC287722
0.7669	Intermediate Similarity	NPC184136
0.7669	Intermediate Similarity	NPC62042
0.7669	Intermediate Similarity	NPC103509
0.7669	Intermediate Similarity	NPC225129
0.7662	Intermediate Similarity	NPC237330
0.7654	Intermediate Similarity	NPC15329
0.7654	Intermediate Similarity	NPC131451
0.7643	Intermediate Similarity	NPC4796
0.7636	Intermediate Similarity	NPC124714
0.7636	Intermediate Similarity	NPC250557
0.7622	Intermediate Similarity	NPC204515
0.7622	Intermediate Similarity	NPC171010
0.7622	Intermediate Similarity	NPC288316
0.7616	Intermediate Similarity	NPC214553
0.7613	Intermediate Similarity	NPC143649
0.761	Intermediate Similarity	NPC284556
0.761	Intermediate Similarity	NPC301178
0.7593	Intermediate Similarity	NPC239312
0.7593	Intermediate Similarity	NPC130230
0.7593	Intermediate Similarity	NPC207729
0.7593	Intermediate Similarity	NPC275772
0.7593	Intermediate Similarity	NPC46941
0.7593	Intermediate Similarity	NPC119660
0.7593	Intermediate Similarity	NPC93034
0.759	Intermediate Similarity	NPC213622
0.759	Intermediate Similarity	NPC134287
0.759	Intermediate Similarity	NPC2928
0.759	Intermediate Similarity	NPC130589
0.759	Intermediate Similarity	NPC39184
0.7584	Intermediate Similarity	NPC4012
0.7576	Intermediate Similarity	NPC301323
0.7576	Intermediate Similarity	NPC188203
0.7576	Intermediate Similarity	NPC142540
0.7576	Intermediate Similarity	NPC39007
0.7576	Intermediate Similarity	NPC222830
0.7576	Intermediate Similarity	NPC162313
0.7576	Intermediate Similarity	NPC275722
0.7576	Intermediate Similarity	NPC161277
0.7576	Intermediate Similarity	NPC156222
0.7576	Intermediate Similarity	NPC241498
0.7576	Intermediate Similarity	NPC256283
0.7576	Intermediate Similarity	NPC239128
0.7576	Intermediate Similarity	NPC71334
0.7576	Intermediate Similarity	NPC57030
0.7576	Intermediate Similarity	NPC187498
0.7576	Intermediate Similarity	NPC101996
0.7576	Intermediate Similarity	NPC131624
0.7576	Intermediate Similarity	NPC100887
0.7576	Intermediate Similarity	NPC25270
0.7576	Intermediate Similarity	NPC180234
0.7576	Intermediate Similarity	NPC199100
0.7576	Intermediate Similarity	NPC275836
0.7576	Intermediate Similarity	NPC212678
0.7576	Intermediate Similarity	NPC293183
0.7576	Intermediate Similarity	NPC120537
0.7576	Intermediate Similarity	NPC83508
0.7576	Intermediate Similarity	NPC198826
0.7576	Intermediate Similarity	NPC120163
0.7562	Intermediate Similarity	NPC471417
0.7561	Intermediate Similarity	NPC213382
0.7561	Intermediate Similarity	NPC96501
0.7561	Intermediate Similarity	NPC239363
0.7561	Intermediate Similarity	NPC164527
0.7561	Intermediate Similarity	NPC156953
0.7558	Intermediate Similarity	NPC470566
0.7546	Intermediate Similarity	NPC118726
0.7546	Intermediate Similarity	NPC152947
0.7546	Intermediate Similarity	NPC12367
0.7546	Intermediate Similarity	NPC276930
0.7546	Intermediate Similarity	NPC194856
0.7545	Intermediate Similarity	NPC472916
0.7545	Intermediate Similarity	NPC317383
0.7545	Intermediate Similarity	NPC235165
0.7545	Intermediate Similarity	NPC255106
0.7532	Intermediate Similarity	NPC471819
0.7531	Intermediate Similarity	NPC165389
0.7531	Intermediate Similarity	NPC209278
0.753	Intermediate Similarity	NPC167091
0.753	Intermediate Similarity	NPC22519
0.753	Intermediate Similarity	NPC250822
0.753	Intermediate Similarity	NPC176775
0.753	Intermediate Similarity	NPC477048
0.753	Intermediate Similarity	NPC292214
0.753	Intermediate Similarity	NPC231018
0.753	Intermediate Similarity	NPC477047
0.753	Intermediate Similarity	NPC160951
0.753	Intermediate Similarity	NPC88645
0.753	Intermediate Similarity	NPC183878
0.753	Intermediate Similarity	NPC75279
0.753	Intermediate Similarity	NPC255350
0.753	Intermediate Similarity	NPC145379
0.753	Intermediate Similarity	NPC47781
0.753	Intermediate Similarity	NPC271779
0.753	Intermediate Similarity	NPC276409
0.753	Intermediate Similarity	NPC206238
0.753	Intermediate Similarity	NPC274327
0.753	Intermediate Similarity	NPC69394
0.7516	Intermediate Similarity	NPC276328
0.7516	Intermediate Similarity	NPC25305
0.7516	Intermediate Similarity	NPC112068
0.7516	Intermediate Similarity	NPC110899
0.7516	Intermediate Similarity	NPC242893
0.7516	Intermediate Similarity	NPC142165
0.7516	Intermediate Similarity	NPC38065
0.7516	Intermediate Similarity	NPC95679
0.7516	Intermediate Similarity	NPC125417
0.7515	Intermediate Similarity	NPC262623
0.7515	Intermediate Similarity	NPC99772
0.7515	Intermediate Similarity	NPC202157
0.7514	Intermediate Similarity	NPC470567
0.75	Intermediate Similarity	NPC48208
0.75	Intermediate Similarity	NPC264289
0.75	Intermediate Similarity	NPC195351
0.75	Intermediate Similarity	NPC200060
0.75	Intermediate Similarity	NPC139293
0.75	Intermediate Similarity	NPC472911
0.75	Intermediate Similarity	NPC216318
0.75	Intermediate Similarity	NPC285527
0.75	Intermediate Similarity	NPC210084
0.75	Intermediate Similarity	NPC17286
0.75	Intermediate Similarity	NPC69430
0.75	Intermediate Similarity	NPC156057
0.75	Intermediate Similarity	NPC106334
0.75	Intermediate Similarity	NPC469584
0.75	Intermediate Similarity	NPC333691
0.75	Intermediate Similarity	NPC199089
0.75	Intermediate Similarity	NPC259713
0.75	Intermediate Similarity	NPC195763
0.75	Intermediate Similarity	NPC179732
0.75	Intermediate Similarity	NPC472914
0.75	Intermediate Similarity	NPC162869
0.75	Intermediate Similarity	NPC245758
0.75	Intermediate Similarity	NPC208760
0.75	Intermediate Similarity	NPC264550
0.75	Intermediate Similarity	NPC99597
0.75	Intermediate Similarity	NPC96167
0.75	Intermediate Similarity	NPC222814
0.75	Intermediate Similarity	NPC470402
0.75	Intermediate Similarity	NPC296197
0.75	Intermediate Similarity	NPC40290
0.75	Intermediate Similarity	NPC142876
0.75	Intermediate Similarity	NPC474208
0.75	Intermediate Similarity	NPC475267
0.75	Intermediate Similarity	NPC472910
0.75	Intermediate Similarity	NPC78103
0.75	Intermediate Similarity	NPC472913
0.75	Intermediate Similarity	NPC474836
0.7485	Intermediate Similarity	NPC92659
0.7485	Intermediate Similarity	NPC201451
0.7485	Intermediate Similarity	NPC4455
0.7485	Intermediate Similarity	NPC128863
0.7485	Intermediate Similarity	NPC208197
0.7485	Intermediate Similarity	NPC44079
0.7485	Intermediate Similarity	NPC138360
0.7485	Intermediate Similarity	NPC256612
0.7485	Intermediate Similarity	NPC280339
0.7485	Intermediate Similarity	NPC113906
0.7485	Intermediate Similarity	NPC167815
0.7485	Intermediate Similarity	NPC18954
0.7485	Intermediate Similarity	NPC201136

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 NPC294870 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	464
0.1-0.2	1330
0.2-0.3	2621
0.3-0.4	2592
0.4-0.5	1419
0.5-0.6	574
0.6-0.7	134
0.7-0.8	16
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
0.753	Intermediate Similarity	NPD2801	Approved
0.7407	Intermediate Similarity	NPD1511	Approved
0.7372	Intermediate Similarity	NPD230	Phase 1
0.7365	Intermediate Similarity	NPD1934	Approved
0.7321	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1512	Approved
0.7235	Intermediate Similarity	NPD3882	Suspended
0.7188	Intermediate Similarity	NPD1551	Phase 2
0.7152	Intermediate Similarity	NPD447	Suspended
0.7099	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9494	Approved
0.7076	Intermediate Similarity	NPD4288	Approved
0.7019	Intermediate Similarity	NPD1510	Phase 2
0.7012	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1240	Approved
0.6981	Remote Similarity	NPD943	Approved
0.6949	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6166	Phase 2
0.6949	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1607	Approved
0.6883	Remote Similarity	NPD9269	Phase 2
0.6879	Remote Similarity	NPD3817	Phase 2
0.6879	Remote Similarity	NPD5402	Approved
0.6875	Remote Similarity	NPD1247	Approved
0.6872	Remote Similarity	NPD3818	Discontinued
0.6871	Remote Similarity	NPD2935	Discontinued
0.6868	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2534	Approved
0.6845	Remote Similarity	NPD2533	Approved
0.6845	Remote Similarity	NPD2532	Approved
0.6836	Remote Similarity	NPD6232	Discontinued
0.6833	Remote Similarity	NPD7054	Approved
0.6829	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1465	Phase 2
0.6796	Remote Similarity	NPD7074	Phase 3
0.6796	Remote Similarity	NPD7472	Approved
0.6788	Remote Similarity	NPD1549	Phase 2
0.6758	Remote Similarity	NPD6797	Phase 2
0.6746	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4380	Phase 2
0.6738	Remote Similarity	NPD4287	Approved
0.6723	Remote Similarity	NPD5494	Approved
0.6722	Remote Similarity	NPD7473	Discontinued
0.6721	Remote Similarity	NPD7251	Discontinued
0.6686	Remote Similarity	NPD2296	Approved
0.6667	Remote Similarity	NPD9717	Approved
0.6647	Remote Similarity	NPD2800	Approved
0.6646	Remote Similarity	NPD411	Approved
0.6645	Remote Similarity	NPD9493	Approved
0.6623	Remote Similarity	NPD9268	Approved
0.6595	Remote Similarity	NPD7808	Phase 3
0.6588	Remote Similarity	NPD6799	Approved
0.6584	Remote Similarity	NPD3027	Phase 3
0.6573	Remote Similarity	NPD919	Approved
0.657	Remote Similarity	NPD920	Approved
0.6564	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD1613	Approved
0.6562	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6559	Discontinued
0.6541	Remote Similarity	NPD1203	Approved
0.6532	Remote Similarity	NPD1653	Approved
0.6522	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7075	Discontinued
0.65	Remote Similarity	NPD6959	Discontinued
0.6486	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6651	Approved
0.6474	Remote Similarity	NPD5403	Approved
0.6467	Remote Similarity	NPD2796	Approved
0.6467	Remote Similarity	NPD5844	Phase 1
0.6453	Remote Similarity	NPD5401	Approved
0.6453	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1298	Discontinued
0.6441	Remote Similarity	NPD7819	Suspended
0.6441	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD1019	Discontinued
0.6389	Remote Similarity	NPD6234	Discontinued
0.6384	Remote Similarity	NPD6801	Discontinued
0.6369	Remote Similarity	NPD7768	Phase 2
0.6364	Remote Similarity	NPD6599	Discontinued
0.6358	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7411	Suspended
0.6325	Remote Similarity	NPD1933	Approved
0.6322	Remote Similarity	NPD2184	Approved
0.6322	Remote Similarity	NPD2183	Approved
0.6316	Remote Similarity	NPD3750	Approved
0.6316	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.631	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD37	Approved
0.629	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD5711	Approved
0.6284	Remote Similarity	NPD5710	Approved
0.6279	Remote Similarity	NPD6190	Approved
0.6257	Remote Similarity	NPD2654	Approved
0.625	Remote Similarity	NPD3926	Phase 2
0.6242	Remote Similarity	NPD9545	Approved
0.6242	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD74	Approved
0.6225	Remote Similarity	NPD9266	Approved
0.6222	Remote Similarity	NPD5353	Approved
0.622	Remote Similarity	NPD6832	Phase 2
0.6218	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD3226	Approved
0.6209	Remote Similarity	NPD228	Approved
0.6193	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD4966	Approved
0.6188	Remote Similarity	NPD4967	Phase 2
0.6188	Remote Similarity	NPD422	Phase 1
0.6188	Remote Similarity	NPD4965	Approved
0.6176	Remote Similarity	NPD6100	Approved
0.6176	Remote Similarity	NPD6099	Approved
0.6163	Remote Similarity	NPD1243	Approved
0.6159	Remote Similarity	NPD9264	Approved
0.6159	Remote Similarity	NPD9267	Approved
0.6159	Remote Similarity	NPD9263	Approved
0.6154	Remote Similarity	NPD3749	Approved
0.6154	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.615	Remote Similarity	NPD7228	Approved
0.615	Remote Similarity	NPD3751	Discontinued
0.6145	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD2313	Discontinued
0.614	Remote Similarity	NPD2346	Discontinued
0.6135	Remote Similarity	NPD1470	Approved
0.6129	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3496	Discontinued
0.6117	Remote Similarity	NPD7286	Phase 2
0.6114	Remote Similarity	NPD4357	Discontinued
0.6111	Remote Similarity	NPD6844	Discontinued
0.6098	Remote Similarity	NPD2798	Approved
0.6087	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD1201	Approved
0.6062	Remote Similarity	NPD1778	Approved
0.6061	Remote Similarity	NPD3018	Phase 2
0.6053	Remote Similarity	NPD5953	Discontinued
0.6047	Remote Similarity	NPD2344	Approved
0.6038	Remote Similarity	NPD1548	Phase 1
0.6034	Remote Similarity	NPD4628	Phase 3
0.6023	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD2799	Discontinued
0.6023	Remote Similarity	NPD7390	Discontinued
0.6023	Remote Similarity	NPD3748	Approved
0.6022	Remote Similarity	NPD3787	Discontinued
0.6021	Remote Similarity	NPD7685	Pre-registration
0.6012	Remote Similarity	NPD4749	Approved
0.6	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.599	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD5242	Approved
0.5988	Remote Similarity	NPD1610	Phase 2
0.5987	Remote Similarity	NPD9281	Approved
0.5979	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD7199	Phase 2
0.5959	Remote Similarity	NPD8312	Approved
0.5959	Remote Similarity	NPD8313	Approved
0.5957	Remote Similarity	NPD2403	Approved
0.5954	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD1608	Approved
0.5949	Remote Similarity	NPD8434	Phase 2
0.5944	Remote Similarity	NPD824	Approved
0.5941	Remote Similarity	NPD6780	Approved
0.5941	Remote Similarity	NPD6777	Approved
0.5941	Remote Similarity	NPD6779	Approved
0.5941	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6778	Approved
0.5941	Remote Similarity	NPD6781	Approved
0.5941	Remote Similarity	NPD6782	Approved
0.5941	Remote Similarity	NPD6776	Approved
0.593	Remote Similarity	NPD4308	Phase 3
0.5928	Remote Similarity	NPD4908	Phase 1
0.5915	Remote Similarity	NPD2982	Phase 2
0.5915	Remote Similarity	NPD2983	Phase 2
0.5909	Remote Similarity	NPD2219	Phase 1
0.5909	Remote Similarity	NPD2309	Approved
0.5907	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD9261	Approved
0.589	Remote Similarity	NPD1091	Approved
0.5886	Remote Similarity	NPD1652	Phase 2
0.5882	Remote Similarity	NPD6823	Phase 2
0.5879	Remote Similarity	NPD6386	Approved
0.5879	Remote Similarity	NPD3225	Approved
0.5879	Remote Similarity	NPD6385	Approved
0.5875	Remote Similarity	NPD5536	Phase 2
0.5867	Remote Similarity	NPD8150	Discontinued
0.5858	Remote Similarity	NPD1296	Phase 2
0.5858	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD9244	Approved
0.5854	Remote Similarity	NPD2981	Phase 2
0.5854	Remote Similarity	NPD1481	Phase 2

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