NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	289.98
Volume:	225.649
LogP:	2.921
LogD:	1.788
LogS:	-2.626
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.658
Synthetic Accessibility Score:	2.303
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:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.762
MDCK Permeability:	1.8362638002145104e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.351
Plasma Protein Binding (PPB):	97.45263671875%
Volume Distribution (VD):	0.556
Pgp-substrate:	2.9318268299102783%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.754
CYP2C19-inhibitor:	0.306
CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.48
CYP2C9-substrate:	0.691
CYP2D6-inhibitor:	0.414
CYP2D6-substrate:	0.311
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	2.525
Half-life (T1/2):	0.797

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.028
Drug-inuced Liver Injury (DILI):	0.389
AMES Toxicity:	0.205
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.767
Carcinogencity:	0.132
Eye Corrosion:	0.027
Eye Irritation:	0.947
Respiratory Toxicity:	0.167

Download Data

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

Natural Product: NPC305490

Natural Product ID:	NPC305490
*Common Name:**	Ceratinophenol A
IUPAC Name:	ethyl 5-bromo-2,3-dihydroxy-6-methoxybenzoate
Synonyms:
Standard InCHIKey:	RBPFPIQYTCTEBN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H11BrO5/c1-3-16-10(14)7-8(13)6(12)4-5(11)9(7)15-2/h4,12-13H,3H2,1-2H3
SMILES:	CCOC(=O)c1c(c(cc(c1OC)Br)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466797
PubChem CID:	25016408
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002344] Methoxybenzoic acids and derivatives [CHEMONTID:0002345] O-methoxybenzoic acids and derivatives

*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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	7.0	mm	PMID[489849]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	4.0	mm	PMID[489849]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	3.0	mm	PMID[489849]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	2.0	mm	PMID[489849]

☑ 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 NPC305490 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	407
0.1-0.2	2150
0.2-0.3	7085
0.3-0.4	12409
0.4-0.5	4373
0.5-0.6	6081
0.6-0.7	8226
0.7-0.8	1959
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	NPC294870
0.8397	Intermediate Similarity	NPC178097
0.8077	Intermediate Similarity	NPC184632
0.8075	Intermediate Similarity	NPC225129
0.7963	Intermediate Similarity	NPC96501
0.7963	Intermediate Similarity	NPC213382
0.7963	Intermediate Similarity	NPC164527
0.7937	Intermediate Similarity	NPC143903
0.7937	Intermediate Similarity	NPC226987
0.7901	Intermediate Similarity	NPC285527
0.7901	Intermediate Similarity	NPC106334
0.7888	Intermediate Similarity	NPC61871
0.7888	Intermediate Similarity	NPC30647
0.7888	Intermediate Similarity	NPC55557
0.7875	Intermediate Similarity	NPC472917
0.7866	Intermediate Similarity	NPC289968
0.7862	Intermediate Similarity	NPC258307
0.7834	Intermediate Similarity	NPC471819
0.7826	Intermediate Similarity	NPC32058
0.7826	Intermediate Similarity	NPC85734
0.7821	Intermediate Similarity	NPC25305
0.7821	Intermediate Similarity	NPC110899
0.7821	Intermediate Similarity	NPC125417
0.7821	Intermediate Similarity	NPC95679
0.7821	Intermediate Similarity	NPC112068
0.7818	Intermediate Similarity	NPC281477
0.7805	Intermediate Similarity	NPC475076
0.7805	Intermediate Similarity	NPC204350
0.7799	Intermediate Similarity	NPC299154
0.7792	Intermediate Similarity	NPC304929
0.7792	Intermediate Similarity	NPC156124
0.7792	Intermediate Similarity	NPC1321
0.7791	Intermediate Similarity	NPC200221
0.7791	Intermediate Similarity	NPC294502
0.7785	Intermediate Similarity	NPC50823
0.7785	Intermediate Similarity	NPC250597
0.7771	Intermediate Similarity	NPC199926
0.7771	Intermediate Similarity	NPC82592
0.7771	Intermediate Similarity	NPC79998
0.7771	Intermediate Similarity	NPC16082
0.7758	Intermediate Similarity	NPC199773
0.7751	Intermediate Similarity	NPC217950
0.7748	Intermediate Similarity	NPC71525
0.7744	Intermediate Similarity	NPC184136
0.7744	Intermediate Similarity	NPC62042
0.7744	Intermediate Similarity	NPC10467
0.7736	Intermediate Similarity	NPC90411
0.773	Intermediate Similarity	NPC218490
0.773	Intermediate Similarity	NPC287395
0.773	Intermediate Similarity	NPC183655
0.7725	Intermediate Similarity	NPC150227
0.7716	Intermediate Similarity	NPC138978
0.7712	Intermediate Similarity	NPC12694
0.7711	Intermediate Similarity	NPC298802
0.7707	Intermediate Similarity	NPC135837
0.7697	Intermediate Similarity	NPC204515
0.7697	Intermediate Similarity	NPC171010
0.7697	Intermediate Similarity	NPC45291
0.7697	Intermediate Similarity	NPC19980
0.7692	Intermediate Similarity	NPC18646
0.7683	Intermediate Similarity	NPC92722
0.7683	Intermediate Similarity	NPC102003
0.7679	Intermediate Similarity	NPC190020
0.7679	Intermediate Similarity	NPC77679
0.7679	Intermediate Similarity	NPC84935
0.7677	Intermediate Similarity	NPC157478
0.7677	Intermediate Similarity	NPC295406
0.7677	Intermediate Similarity	NPC289572
0.7677	Intermediate Similarity	NPC200422
0.7669	Intermediate Similarity	NPC207729
0.7669	Intermediate Similarity	NPC46941
0.7669	Intermediate Similarity	NPC130230
0.7669	Intermediate Similarity	NPC275772
0.7669	Intermediate Similarity	NPC239312
0.7669	Intermediate Similarity	NPC473608
0.7667	Intermediate Similarity	NPC6888
0.7667	Intermediate Similarity	NPC145134
0.7665	Intermediate Similarity	NPC286052
0.7665	Intermediate Similarity	NPC213622
0.7665	Intermediate Similarity	NPC18954
0.7665	Intermediate Similarity	NPC2928
0.7662	Intermediate Similarity	NPC264145
0.7661	Intermediate Similarity	NPC327809
0.7651	Intermediate Similarity	NPC293183
0.7651	Intermediate Similarity	NPC161277
0.7651	Intermediate Similarity	NPC142540
0.7651	Intermediate Similarity	NPC35763
0.7651	Intermediate Similarity	NPC187498
0.7651	Intermediate Similarity	NPC57030
0.7651	Intermediate Similarity	NPC275722
0.7651	Intermediate Similarity	NPC180234
0.7651	Intermediate Similarity	NPC199100
0.7651	Intermediate Similarity	NPC245382
0.7651	Intermediate Similarity	NPC25270
0.7651	Intermediate Similarity	NPC256283
0.7651	Intermediate Similarity	NPC39007
0.7651	Intermediate Similarity	NPC209487
0.7651	Intermediate Similarity	NPC120537
0.7651	Intermediate Similarity	NPC101996
0.7651	Intermediate Similarity	NPC121522
0.7651	Intermediate Similarity	NPC100971
0.7651	Intermediate Similarity	NPC212678
0.7651	Intermediate Similarity	NPC269451
0.7651	Intermediate Similarity	NPC291802
0.7651	Intermediate Similarity	NPC156222
0.7651	Intermediate Similarity	NPC162313
0.7651	Intermediate Similarity	NPC120163
0.7651	Intermediate Similarity	NPC71334
0.7651	Intermediate Similarity	NPC222830
0.7651	Intermediate Similarity	NPC131624
0.7651	Intermediate Similarity	NPC83508
0.7651	Intermediate Similarity	NPC131266
0.7651	Intermediate Similarity	NPC198826
0.7651	Intermediate Similarity	NPC216769
0.7651	Intermediate Similarity	NPC241498
0.7651	Intermediate Similarity	NPC301323
0.7651	Intermediate Similarity	NPC275836
0.7651	Intermediate Similarity	NPC100263
0.7651	Intermediate Similarity	NPC188203
0.7651	Intermediate Similarity	NPC100887
0.7651	Intermediate Similarity	NPC181209
0.7651	Intermediate Similarity	NPC239128
0.7643	Intermediate Similarity	NPC156892
0.764	Intermediate Similarity	NPC287722
0.7636	Intermediate Similarity	NPC103509
0.7633	Intermediate Similarity	NPC45846
0.7633	Intermediate Similarity	NPC238381
0.7633	Intermediate Similarity	NPC168616
0.7633	Intermediate Similarity	NPC83763
0.7628	Intermediate Similarity	NPC155098
0.7622	Intermediate Similarity	NPC194856
0.7622	Intermediate Similarity	NPC12367
0.7622	Intermediate Similarity	NPC131451
0.7622	Intermediate Similarity	NPC118726
0.7622	Intermediate Similarity	NPC152947
0.7622	Intermediate Similarity	NPC276930
0.7622	Intermediate Similarity	NPC107636
0.7622	Intermediate Similarity	NPC15329
0.7619	Intermediate Similarity	NPC475697
0.7619	Intermediate Similarity	NPC235165
0.7619	Intermediate Similarity	NPC227062
0.7619	Intermediate Similarity	NPC472916
0.7619	Intermediate Similarity	NPC317383
0.7619	Intermediate Similarity	NPC54928
0.7619	Intermediate Similarity	NPC255106
0.761	Intermediate Similarity	NPC4796
0.7607	Intermediate Similarity	NPC209278
0.7607	Intermediate Similarity	NPC260946
0.7605	Intermediate Similarity	NPC69394
0.7605	Intermediate Similarity	NPC124714
0.7605	Intermediate Similarity	NPC271779
0.7605	Intermediate Similarity	NPC176775
0.7605	Intermediate Similarity	NPC47781
0.7605	Intermediate Similarity	NPC183878
0.7605	Intermediate Similarity	NPC250822
0.7605	Intermediate Similarity	NPC250557
0.7605	Intermediate Similarity	NPC75279
0.7605	Intermediate Similarity	NPC274327
0.7605	Intermediate Similarity	NPC231018
0.7605	Intermediate Similarity	NPC22519
0.7605	Intermediate Similarity	NPC167091
0.7605	Intermediate Similarity	NPC88645
0.7605	Intermediate Similarity	NPC276409
0.7605	Intermediate Similarity	NPC145379
0.7605	Intermediate Similarity	NPC255350
0.7605	Intermediate Similarity	NPC206238
0.7605	Intermediate Similarity	NPC160951
0.7605	Intermediate Similarity	NPC292214
0.7595	Intermediate Similarity	NPC276328
0.7595	Intermediate Similarity	NPC474274
0.7595	Intermediate Similarity	NPC157944
0.7593	Intermediate Similarity	NPC210425
0.7593	Intermediate Similarity	NPC86373
0.7593	Intermediate Similarity	NPC277426
0.7593	Intermediate Similarity	NPC280404
0.759	Intermediate Similarity	NPC288316
0.759	Intermediate Similarity	NPC202157
0.7588	Intermediate Similarity	NPC200594
0.7582	Intermediate Similarity	NPC293453
0.758	Intermediate Similarity	NPC143649
0.758	Intermediate Similarity	NPC176102
0.758	Intermediate Similarity	NPC29317
0.758	Intermediate Similarity	NPC180905
0.758	Intermediate Similarity	NPC182496
0.758	Intermediate Similarity	NPC267539
0.758	Intermediate Similarity	NPC71108
0.758	Intermediate Similarity	NPC254832
0.758	Intermediate Similarity	NPC204257
0.758	Intermediate Similarity	NPC229638
0.7578	Intermediate Similarity	NPC301178
0.7578	Intermediate Similarity	NPC284556
0.7576	Intermediate Similarity	NPC17286
0.7576	Intermediate Similarity	NPC296197
0.7576	Intermediate Similarity	NPC216318
0.7576	Intermediate Similarity	NPC259713
0.7576	Intermediate Similarity	NPC195351
0.7574	Intermediate Similarity	NPC474836
0.7574	Intermediate Similarity	NPC162869
0.7574	Intermediate Similarity	NPC472914
0.7574	Intermediate Similarity	NPC472910

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 NPC305490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	1243
0.2-0.3	2486
0.3-0.4	2654
0.4-0.5	1508
0.5-0.6	675
0.6-0.7	183
0.7-0.8	25
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
0.7792	Intermediate Similarity	NPD230	Phase 1
0.7605	Intermediate Similarity	NPD2801	Approved
0.7564	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1511	Approved
0.7456	Intermediate Similarity	NPD4288	Approved
0.744	Intermediate Similarity	NPD1934	Approved
0.7396	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1512	Approved
0.7375	Intermediate Similarity	NPD1551	Phase 2
0.731	Intermediate Similarity	NPD3882	Suspended
0.731	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3817	Phase 2
0.7251	Intermediate Similarity	NPD5402	Approved
0.7229	Intermediate Similarity	NPD2533	Approved
0.7229	Intermediate Similarity	NPD2534	Approved
0.7229	Intermediate Similarity	NPD2532	Approved
0.7222	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2935	Discontinued
0.7102	Intermediate Similarity	NPD6232	Discontinued
0.7093	Intermediate Similarity	NPD1465	Phase 2
0.7081	Intermediate Similarity	NPD4287	Approved
0.7078	Intermediate Similarity	NPD9269	Phase 2
0.7078	Intermediate Similarity	NPD9717	Approved
0.7039	Intermediate Similarity	NPD3818	Discontinued
0.7022	Intermediate Similarity	NPD6166	Phase 2
0.7022	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7054	Approved
0.6994	Remote Similarity	NPD1510	Phase 2
0.6983	Remote Similarity	NPD7473	Discontinued
0.6964	Remote Similarity	NPD6799	Approved
0.6961	Remote Similarity	NPD7472	Approved
0.6961	Remote Similarity	NPD7074	Phase 3
0.6957	Remote Similarity	NPD1240	Approved
0.6957	Remote Similarity	NPD943	Approved
0.6954	Remote Similarity	NPD9493	Approved
0.6943	Remote Similarity	NPD1203	Approved
0.6937	Remote Similarity	NPD411	Approved
0.6923	Remote Similarity	NPD6797	Phase 2
0.6909	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1653	Approved
0.689	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7251	Discontinued
0.6875	Remote Similarity	NPD7075	Discontinued
0.6871	Remote Similarity	NPD1607	Approved
0.6867	Remote Similarity	NPD1549	Phase 2
0.6855	Remote Similarity	NPD9494	Approved
0.6842	Remote Similarity	NPD5403	Approved
0.6831	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5401	Approved
0.6824	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4380	Phase 2
0.6818	Remote Similarity	NPD9268	Approved
0.6813	Remote Similarity	NPD5844	Phase 1
0.681	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7819	Suspended
0.6798	Remote Similarity	NPD5494	Approved
0.6792	Remote Similarity	NPD1019	Discontinued
0.6761	Remote Similarity	NPD2296	Approved
0.676	Remote Similarity	NPD1247	Approved
0.6757	Remote Similarity	NPD7808	Phase 3
0.6744	Remote Similarity	NPD920	Approved
0.6743	Remote Similarity	NPD6801	Discontinued
0.6742	Remote Similarity	NPD6234	Discontinued
0.6742	Remote Similarity	NPD919	Approved
0.6726	Remote Similarity	NPD2800	Approved
0.6724	Remote Similarity	NPD6599	Discontinued
0.6723	Remote Similarity	NPD7768	Phase 2
0.6707	Remote Similarity	NPD1933	Approved
0.6686	Remote Similarity	NPD3750	Approved
0.6686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7411	Suspended
0.6685	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6190	Approved
0.6646	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1613	Approved
0.6645	Remote Similarity	NPD9545	Approved
0.6632	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5710	Approved
0.663	Remote Similarity	NPD5711	Approved
0.6626	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6559	Discontinued
0.6605	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6832	Phase 2
0.6582	Remote Similarity	NPD422	Phase 1
0.6575	Remote Similarity	NPD6959	Discontinued
0.6573	Remote Similarity	NPD5353	Approved
0.6571	Remote Similarity	NPD3226	Approved
0.6564	Remote Similarity	NPD3027	Phase 3
0.6554	Remote Similarity	NPD37	Approved
0.6548	Remote Similarity	NPD2796	Approved
0.6536	Remote Similarity	NPD4967	Phase 2
0.6536	Remote Similarity	NPD4966	Approved
0.6536	Remote Similarity	NPD4965	Approved
0.6532	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD1243	Approved
0.6524	Remote Similarity	NPD2313	Discontinued
0.6524	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD1298	Discontinued
0.6519	Remote Similarity	NPD3496	Discontinued
0.6509	Remote Similarity	NPD2346	Discontinued
0.65	Remote Similarity	NPD3749	Approved
0.6486	Remote Similarity	NPD7228	Approved
0.648	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6651	Approved
0.6467	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1778	Approved
0.6452	Remote Similarity	NPD7286	Phase 2
0.6452	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD9266	Approved
0.6424	Remote Similarity	NPD74	Approved
0.6416	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4628	Phase 3
0.6391	Remote Similarity	NPD2799	Discontinued
0.6391	Remote Similarity	NPD3748	Approved
0.6383	Remote Similarity	NPD5953	Discontinued
0.6379	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD9264	Approved
0.6358	Remote Similarity	NPD9267	Approved
0.6358	Remote Similarity	NPD9263	Approved
0.6349	Remote Similarity	NPD7685	Pre-registration
0.6337	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD1608	Approved
0.6324	Remote Similarity	NPD3926	Phase 2
0.6324	Remote Similarity	NPD5242	Approved
0.631	Remote Similarity	NPD3751	Discontinued
0.6307	Remote Similarity	NPD2183	Approved
0.6307	Remote Similarity	NPD2184	Approved
0.6304	Remote Similarity	NPD7199	Phase 2
0.6302	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4308	Phase 3
0.6283	Remote Similarity	NPD8313	Approved
0.6283	Remote Similarity	NPD8312	Approved
0.6258	Remote Similarity	NPD3225	Approved
0.6257	Remote Similarity	NPD6099	Approved
0.6257	Remote Similarity	NPD6100	Approved
0.625	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD1652	Phase 2
0.6243	Remote Similarity	NPD2654	Approved
0.6237	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD1481	Phase 2
0.6228	Remote Similarity	NPD1296	Phase 2
0.6222	Remote Similarity	NPD6385	Approved
0.6222	Remote Similarity	NPD6386	Approved
0.622	Remote Similarity	NPD2797	Approved
0.6199	Remote Similarity	NPD7033	Discontinued
0.6194	Remote Similarity	NPD228	Approved
0.619	Remote Similarity	NPD520	Approved
0.619	Remote Similarity	NPD6233	Phase 2
0.6188	Remote Similarity	NPD6844	Discontinued
0.6186	Remote Similarity	NPD8150	Discontinued
0.6183	Remote Similarity	NPD3787	Discontinued
0.6182	Remote Similarity	NPD2798	Approved
0.6178	Remote Similarity	NPD9281	Approved
0.6173	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD1535	Discovery
0.6158	Remote Similarity	NPD7435	Discontinued
0.6158	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD17	Approved
0.6133	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD3268	Approved
0.6131	Remote Similarity	NPD3764	Approved
0.6127	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD6004	Phase 3
0.6127	Remote Similarity	NPD6005	Phase 3
0.6127	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD6002	Phase 3
0.6127	Remote Similarity	NPD2344	Approved
0.6127	Remote Similarity	NPD7266	Discontinued
0.6125	Remote Similarity	NPD1548	Phase 1
0.6121	Remote Similarity	NPD1470	Approved
0.6111	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3455	Phase 2
0.6103	Remote Similarity	NPD8434	Phase 2
0.6102	Remote Similarity	NPD4357	Discontinued
0.6101	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD4749	Approved
0.6094	Remote Similarity	NPD7240	Approved
0.6093	Remote Similarity	NPD9261	Approved
0.6089	Remote Similarity	NPD6776	Approved
0.6089	Remote Similarity	NPD6781	Approved
0.6089	Remote Similarity	NPD6778	Approved
0.6089	Remote Similarity	NPD6777	Approved
0.6089	Remote Similarity	NPD6779	Approved
0.6089	Remote Similarity	NPD6780	Approved
0.6089	Remote Similarity	NPD6782	Approved
0.6087	Remote Similarity	NPD8151	Discontinued
0.6084	Remote Similarity	NPD5647	Approved
0.6082	Remote Similarity	NPD6653	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