NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	845.7
Volume:	926.47
LogP:	10.202
LogD:	5.067
LogS:	-2.077
# Rotatable Bonds:	42
TPSA:	189.17
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	1
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.022
Synthetic Accessibility Score:	4.982
Fsp3:	0.979
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.724
MDCK Permeability:	2.1308539999154164e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.108
Human Intestinal Absorption (HIA):	0.665
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	99.84700012207031%
Volume Distribution (VD):	0.762
Pgp-substrate:	1.8644468784332275%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.991
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	3.124
Half-life (T1/2):	0.08

ADMET: Toxicity

hERG Blockers:	0.88
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.244
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.964
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC476523

Natural Product ID:	NPC476523
*Common Name:**	(2R)-N-[(2S,3S,4R)-3,4-dihydroxy-16-methyl-1-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptadecan-2-yl]-2-hydroxytetracosanamide
IUPAC Name:	(2R)-N-[(2S,3S,4R)-3,4-dihydroxy-16-methyl-1-[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptadecan-2-yl]-2-hydroxytetracosanamide
Synonyms:
Standard InCHIKey:	ZFKNVPCSUNCEDZ-YEQGVTFHSA-N
Standard InCHI:	InChI=1S/C48H95NO10/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-26-29-32-35-41(52)47(57)49-39(37-58-48-46(56)45(55)44(54)42(36-50)59-48)43(53)40(51)34-31-28-25-23-20-21-24-27-30-33-38(2)3/h38-46,48,50-56H,4-37H2,1-3H3,(H,49,57)/t39-,40+,41+,42-,43-,44-,45-,46-,48-/m0/s1
SMILES:	CCCCCCCCCCCCCCCCCCCCCC[C@H](C(=O)N[C@@H](CO[C@@H]1[C@H]([C@H]([C@H]([C@@H](O1)CO)O)O)O)[C@@H]([C@@H](CCCCCCCCCCCC(C)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	73355898
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO33620	Agelas mauritianus	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7783149]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	27.6	day	DOI[10.1016/0960-894X(95)00098-E]
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	27	day	DOI[10.1016/0960-894X(95)00098-E]
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	11.3	day	DOI[10.1016/0960-894X(95)00098-E]

☑ 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 NPC476523 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	118
0.1-0.2	3274
0.2-0.3	19862
0.3-0.4	13596
0.4-0.5	4767
0.5-0.6	846
0.6-0.7	145
0.7-0.8	76
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC470284
0.8539	High Similarity	NPC470283
0.8315	Intermediate Similarity	NPC208537
0.8315	Intermediate Similarity	NPC270005
0.8298	Intermediate Similarity	NPC477198
0.8111	Intermediate Similarity	NPC61894
0.8111	Intermediate Similarity	NPC475603
0.8068	Intermediate Similarity	NPC470282
0.7949	Intermediate Similarity	NPC195165
0.7857	Intermediate Similarity	NPC316807
0.7766	Intermediate Similarity	NPC189629
0.7708	Intermediate Similarity	NPC206711
0.7708	Intermediate Similarity	NPC255175
0.7708	Intermediate Similarity	NPC225978
0.7708	Intermediate Similarity	NPC271207
0.7654	Intermediate Similarity	NPC477200
0.7553	Intermediate Similarity	NPC192066
0.7553	Intermediate Similarity	NPC256570
0.7553	Intermediate Similarity	NPC17290
0.7553	Intermediate Similarity	NPC3568
0.7531	Intermediate Similarity	NPC327486
0.7531	Intermediate Similarity	NPC327753
0.7531	Intermediate Similarity	NPC223174
0.7527	Intermediate Similarity	NPC111567
0.7527	Intermediate Similarity	NPC263545
0.7527	Intermediate Similarity	NPC473581
0.7527	Intermediate Similarity	NPC15851
0.7527	Intermediate Similarity	NPC186840
0.7527	Intermediate Similarity	NPC473950
0.7527	Intermediate Similarity	NPC309898
0.7527	Intermediate Similarity	NPC473604
0.7527	Intermediate Similarity	NPC475125
0.7471	Intermediate Similarity	NPC471420
0.7419	Intermediate Similarity	NPC139782
0.7419	Intermediate Similarity	NPC242503
0.7419	Intermediate Similarity	NPC43074
0.7419	Intermediate Similarity	NPC209047
0.7419	Intermediate Similarity	NPC74672
0.7396	Intermediate Similarity	NPC8098
0.7396	Intermediate Similarity	NPC197294
0.7396	Intermediate Similarity	NPC183449
0.7375	Intermediate Similarity	NPC477764
0.7375	Intermediate Similarity	NPC477756
0.7375	Intermediate Similarity	NPC477752
0.7375	Intermediate Similarity	NPC477751
0.7368	Intermediate Similarity	NPC158445
0.7368	Intermediate Similarity	NPC156782
0.7368	Intermediate Similarity	NPC282088
0.7368	Intermediate Similarity	NPC157353
0.7368	Intermediate Similarity	NPC35269
0.7368	Intermediate Similarity	NPC262312
0.7368	Intermediate Similarity	NPC23454
0.7368	Intermediate Similarity	NPC54961
0.7368	Intermediate Similarity	NPC70323
0.734	Intermediate Similarity	NPC282705
0.734	Intermediate Similarity	NPC182632
0.7327	Intermediate Similarity	NPC475918
0.7308	Intermediate Similarity	NPC145627
0.7284	Intermediate Similarity	NPC477760
0.7284	Intermediate Similarity	NPC477754
0.7284	Intermediate Similarity	NPC477761
0.7284	Intermediate Similarity	NPC477758
0.7284	Intermediate Similarity	NPC477759
0.7241	Intermediate Similarity	NPC150557
0.7216	Intermediate Similarity	NPC45313
0.7143	Intermediate Similarity	NPC253975
0.7143	Intermediate Similarity	NPC125253
0.7143	Intermediate Similarity	NPC192025
0.7037	Intermediate Similarity	NPC474402
0.6941	Remote Similarity	NPC474403
0.6939	Remote Similarity	NPC330590
0.6931	Remote Similarity	NPC42320
0.6931	Remote Similarity	NPC188453
0.6882	Remote Similarity	NPC83839
0.6863	Remote Similarity	NPC227622
0.6813	Remote Similarity	NPC271772
0.6813	Remote Similarity	NPC36927
0.6809	Remote Similarity	NPC306838
0.6809	Remote Similarity	NPC477728
0.6782	Remote Similarity	NPC86064
0.6778	Remote Similarity	NPC318258
0.6774	Remote Similarity	NPC227051
0.6762	Remote Similarity	NPC59589
0.6762	Remote Similarity	NPC317534
0.675	Remote Similarity	NPC477753
0.675	Remote Similarity	NPC477763
0.675	Remote Similarity	NPC477762
0.675	Remote Similarity	NPC477757
0.675	Remote Similarity	NPC477755
0.675	Remote Similarity	NPC477750
0.6739	Remote Similarity	NPC165119
0.67	Remote Similarity	NPC475503
0.67	Remote Similarity	NPC313821
0.6667	Remote Similarity	NPC95478
0.6667	Remote Similarity	NPC155670
0.6667	Remote Similarity	NPC292345
0.6667	Remote Similarity	NPC201128
0.6667	Remote Similarity	NPC43219
0.6667	Remote Similarity	NPC148424
0.6667	Remote Similarity	NPC145748
0.6634	Remote Similarity	NPC475646
0.6604	Remote Similarity	NPC137453
0.6598	Remote Similarity	NPC477729
0.6596	Remote Similarity	NPC477199
0.6593	Remote Similarity	NPC70574
0.6593	Remote Similarity	NPC83248
0.6593	Remote Similarity	NPC100204
0.6569	Remote Similarity	NPC474952
0.6556	Remote Similarity	NPC314772
0.6556	Remote Similarity	NPC314968
0.6543	Remote Similarity	NPC472026
0.6522	Remote Similarity	NPC469943
0.6505	Remote Similarity	NPC471628
0.6505	Remote Similarity	NPC56298
0.6484	Remote Similarity	NPC98750
0.6484	Remote Similarity	NPC473984
0.6465	Remote Similarity	NPC328646
0.6437	Remote Similarity	NPC471879
0.6429	Remote Similarity	NPC190418
0.6429	Remote Similarity	NPC471760
0.6429	Remote Similarity	NPC471761
0.6404	Remote Similarity	NPC308489
0.6404	Remote Similarity	NPC138273
0.6404	Remote Similarity	NPC166250
0.6383	Remote Similarity	NPC477730
0.6375	Remote Similarity	NPC472025
0.6353	Remote Similarity	NPC129100
0.6353	Remote Similarity	NPC322801
0.6353	Remote Similarity	NPC291650
0.6346	Remote Similarity	NPC315036
0.6333	Remote Similarity	NPC217095
0.6333	Remote Similarity	NPC476130
0.6333	Remote Similarity	NPC264417
0.6333	Remote Similarity	NPC476324
0.6322	Remote Similarity	NPC476285
0.6316	Remote Similarity	NPC320936
0.6304	Remote Similarity	NPC272841
0.6292	Remote Similarity	NPC308096
0.6292	Remote Similarity	NPC291228
0.6292	Remote Similarity	NPC138435
0.6289	Remote Similarity	NPC313552
0.6282	Remote Similarity	NPC270041
0.6264	Remote Similarity	NPC279575
0.623	Remote Similarity	NPC475472
0.6224	Remote Similarity	NPC314408
0.6224	Remote Similarity	NPC214376
0.6224	Remote Similarity	NPC43850
0.6224	Remote Similarity	NPC123746
0.6224	Remote Similarity	NPC314007
0.6224	Remote Similarity	NPC477060
0.622	Remote Similarity	NPC143326
0.6216	Remote Similarity	NPC29501
0.6207	Remote Similarity	NPC473985
0.6207	Remote Similarity	NPC28348
0.6207	Remote Similarity	NPC474299
0.6207	Remote Similarity	NPC475808
0.6207	Remote Similarity	NPC67099
0.6207	Remote Similarity	NPC474298
0.6196	Remote Similarity	NPC188793
0.618	Remote Similarity	NPC185419
0.618	Remote Similarity	NPC184550
0.618	Remote Similarity	NPC141325
0.6179	Remote Similarity	NPC73829
0.6179	Remote Similarity	NPC119794
0.6173	Remote Similarity	NPC219040
0.6136	Remote Similarity	NPC476291
0.6136	Remote Similarity	NPC478256
0.6136	Remote Similarity	NPC211428
0.6129	Remote Similarity	NPC76999
0.6129	Remote Similarity	NPC477072
0.6129	Remote Similarity	NPC315535
0.6129	Remote Similarity	NPC478017
0.6129	Remote Similarity	NPC315131
0.6129	Remote Similarity	NPC177343
0.6121	Remote Similarity	NPC477237
0.6111	Remote Similarity	NPC74035
0.6105	Remote Similarity	NPC315969
0.61	Remote Similarity	NPC176381
0.61	Remote Similarity	NPC39290
0.61	Remote Similarity	NPC195969
0.61	Remote Similarity	NPC159369
0.6098	Remote Similarity	NPC139585
0.6092	Remote Similarity	NPC179823
0.6092	Remote Similarity	NPC206601
0.6091	Remote Similarity	NPC475150
0.608	Remote Similarity	NPC75318
0.608	Remote Similarity	NPC280941
0.608	Remote Similarity	NPC235772
0.6075	Remote Similarity	NPC314387
0.6071	Remote Similarity	NPC17455
0.6067	Remote Similarity	NPC53760
0.6067	Remote Similarity	NPC476694
0.6067	Remote Similarity	NPC52268
0.6067	Remote Similarity	NPC476696
0.6067	Remote Similarity	NPC476695
0.6064	Remote Similarity	NPC477346
0.6064	Remote Similarity	NPC22742
0.6064	Remote Similarity	NPC146992
0.6064	Remote Similarity	NPC85759
0.6064	Remote Similarity	NPC170595

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 NPC476523 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	80
0.1-0.2	2186
0.2-0.3	4819
0.3-0.4	1576
0.4-0.5	293
0.5-0.6	138
0.6-0.7	53
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7531	Intermediate Similarity	NPD9445	Approved
0.7525	Intermediate Similarity	NPD8174	Phase 2
0.7419	Intermediate Similarity	NPD8522	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4759	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3187	Discontinued
0.7128	Intermediate Similarity	NPD3716	Discontinued
0.7115	Intermediate Similarity	NPD8306	Approved
0.7115	Intermediate Similarity	NPD8305	Approved
0.7041	Intermediate Similarity	NPD6428	Approved
0.699	Remote Similarity	NPD5376	Approved
0.6961	Remote Similarity	NPD8276	Approved
0.6961	Remote Similarity	NPD8275	Approved
0.6939	Remote Similarity	NPD5381	Approved
0.6939	Remote Similarity	NPD5378	Approved
0.6939	Remote Similarity	NPD5377	Approved
0.6863	Remote Similarity	NPD8084	Approved
0.6863	Remote Similarity	NPD8082	Approved
0.6863	Remote Similarity	NPD8086	Approved
0.6863	Remote Similarity	NPD8083	Approved
0.6863	Remote Similarity	NPD8139	Approved
0.6863	Remote Similarity	NPD8085	Approved
0.6863	Remote Similarity	NPD8138	Approved
0.6827	Remote Similarity	NPD8393	Approved
0.6796	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7844	Discontinued
0.6762	Remote Similarity	NPD8307	Discontinued
0.6762	Remote Similarity	NPD8140	Approved
0.6731	Remote Similarity	NPD8081	Approved
0.67	Remote Similarity	NPD3191	Approved
0.67	Remote Similarity	NPD3190	Approved
0.67	Remote Similarity	NPD3189	Approved
0.6667	Remote Similarity	NPD618	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD8087	Discontinued
0.6566	Remote Similarity	NPD1447	Phase 3
0.6566	Remote Similarity	NPD1446	Phase 3
0.6556	Remote Similarity	NPD9435	Approved
0.6556	Remote Similarity	NPD9434	Approved
0.6505	Remote Similarity	NPD4836	Approved
0.6505	Remote Similarity	NPD4837	Approved
0.6505	Remote Similarity	NPD4838	Approved
0.6505	Remote Similarity	NPD4835	Approved
0.6481	Remote Similarity	NPD6941	Approved
0.6408	Remote Similarity	NPD2255	Approved
0.6381	Remote Similarity	NPD7139	Approved
0.6381	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7140	Approved
0.6353	Remote Similarity	NPD9033	Approved
0.6353	Remote Similarity	NPD9030	Approved
0.6353	Remote Similarity	NPD9031	Approved
0.6353	Remote Similarity	NPD9032	Approved
0.6337	Remote Similarity	NPD8394	Approved
0.6311	Remote Similarity	NPD4282	Approved
0.6289	Remote Similarity	NPD3200	Clinical (unspecified phase)
0.625	Remote Similarity	NPD361	Discontinued
0.6226	Remote Similarity	NPD8300	Approved
0.6226	Remote Similarity	NPD8301	Approved
0.6224	Remote Similarity	NPD3208	Approved
0.6224	Remote Similarity	NPD3202	Approved
0.6224	Remote Similarity	NPD3201	Approved
0.6224	Remote Similarity	NPD2698	Approved
0.6224	Remote Similarity	NPD3207	Approved
0.6224	Remote Similarity	NPD3209	Approved
0.6224	Remote Similarity	NPD3203	Approved
0.6207	Remote Similarity	NPD8347	Approved
0.6207	Remote Similarity	NPD8346	Approved
0.6207	Remote Similarity	NPD8345	Approved
0.6163	Remote Similarity	NPD5380	Approved
0.6154	Remote Similarity	NPD2269	Approved
0.6129	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6421	Discontinued
0.6118	Remote Similarity	NPD1457	Discontinued
0.6118	Remote Similarity	NPD1831	Phase 3
0.6111	Remote Similarity	NPD67	Phase 2
0.6111	Remote Similarity	NPD9034	Approved
0.6102	Remote Similarity	NPD6436	Phase 3
0.61	Remote Similarity	NPD5794	Approved
0.61	Remote Similarity	NPD5798	Approved
0.61	Remote Similarity	NPD5797	Approved
0.61	Remote Similarity	NPD5795	Approved
0.61	Remote Similarity	NPD5796	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD3182	Approved
0.6075	Remote Similarity	NPD3183	Approved
0.6075	Remote Similarity	NPD3184	Approved
0.6075	Remote Similarity	NPD3185	Approved
0.6067	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7345	Approved
0.6042	Remote Similarity	NPD882	Phase 2
0.6042	Remote Similarity	NPD883	Phase 2
0.6026	Remote Similarity	NPD904	Phase 3
0.6026	Remote Similarity	NPD905	Approved
0.6022	Remote Similarity	NPD3160	Suspended
0.5978	Remote Similarity	NPD1453	Phase 1
0.5914	Remote Similarity	NPD372	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD2689	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5357	Phase 1
0.5897	Remote Similarity	NPD7641	Discontinued
0.5882	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD892	Phase 3
0.5875	Remote Similarity	NPD895	Approved
0.5875	Remote Similarity	NPD891	Phase 3
0.5875	Remote Similarity	NPD894	Approved
0.5875	Remote Similarity	NPD889	Approved
0.5875	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD887	Approved
0.5875	Remote Similarity	NPD893	Approved
0.5875	Remote Similarity	NPD888	Phase 3
0.5872	Remote Similarity	NPD1407	Approved
0.5868	Remote Similarity	NPD8341	Approved
0.5868	Remote Similarity	NPD8340	Approved
0.5868	Remote Similarity	NPD8299	Approved
0.5868	Remote Similarity	NPD8342	Approved
0.5854	Remote Similarity	NPD2267	Suspended
0.5843	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD3188	Approved
0.5841	Remote Similarity	NPD35	Approved
0.5841	Remote Similarity	NPD4833	Approved
0.5833	Remote Similarity	NPD8080	Discontinued
0.5824	Remote Similarity	NPD6704	Discontinued
0.582	Remote Similarity	NPD8451	Approved
0.5818	Remote Similarity	NPD2700	Approved
0.5806	Remote Similarity	NPD2257	Approved
0.5776	Remote Similarity	NPD7915	Approved
0.5776	Remote Similarity	NPD7916	Approved
0.5772	Remote Similarity	NPD8448	Approved
0.5765	Remote Similarity	NPD6123	Approved
0.5765	Remote Similarity	NPD393	Approved
0.575	Remote Similarity	NPD8444	Approved
0.5739	Remote Similarity	NPD6430	Approved
0.5739	Remote Similarity	NPD6429	Approved
0.5656	Remote Similarity	NPD7642	Approved
0.5656	Remote Similarity	NPD7830	Approved
0.5656	Remote Similarity	NPD7829	Approved
0.5647	Remote Similarity	NPD9455	Approved
0.5635	Remote Similarity	NPD8391	Approved
0.5635	Remote Similarity	NPD8390	Approved
0.5635	Remote Similarity	NPD8392	Approved
0.5619	Remote Similarity	NPD8171	Discontinued
0.5612	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD2691	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