NPASS Compound

Structure

NPC273830 OpenBabel07101719152D 31 33 0 0 0 0 0 0 0 0999 V2000 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 23 2 0 0 0 0 14 24 2 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 27 2 3 0 0 0 25 30 1 0 0 0 0 26 28 2 3 0 0 0 26 29 1 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	415.23
Volume:	454.152
LogP:	3.537
LogD:	3.882
LogS:	-3.636
# Rotatable Bonds:	13
TPSA:	70.23
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	1.895
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.092
MDCK Permeability:	4.3882999307243153e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.77
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.515
Plasma Protein Binding (PPB):	97.42475128173828%
Volume Distribution (VD):	1.983
Pgp-substrate:	1.076829433441162%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.978
CYP2C19-substrate:	0.152
CYP2C9-inhibitor:	0.95
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.95
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.464

ADMET: Excretion

Clearance (CL):	6.365
Half-life (T1/2):	0.541

ADMET: Toxicity

hERG Blockers:	0.664
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.25
AMES Toxicity:	0.406
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.667
Skin Sensitization:	0.433
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.004

Download Data

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

Natural Product: NPC273830

Natural Product ID:	NPC273830
*Common Name:**	Molleurea A
IUPAC Name:	N-(2-phenylethyl)-2-[2-(2-phenylethylcarbamoylamino)ethyl]benzamide
Synonyms:	Molleurea A
Standard InCHIKey:	SNAKABCKSJEIFP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H29N3O2/c30-25(27-18-15-21-9-3-1-4-10-21)24-14-8-7-13-23(24)17-20-29-26(31)28-19-16-22-11-5-2-6-12-22/h1-14H,15-20H2,(H,27,30)(H2,28,29,31)
SMILES:	OC(=NCCc1ccccc1)NCCc1ccccc1C(=NCCc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087234
PubChem CID:	66553500
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0000178] Benzamides

*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
NPO8208	Didemnum molle	Species	Didemnidae	Eukaryota	n.a.	indonesian	n.a.	PMID[18543965]
NPO8208	Didemnum molle	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22845329]
NPO8208	Didemnum molle	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28574260]
NPO8208	Didemnum molle	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1114	Organism	Human immunodeficiency virus	Human immunodeficiency virus	IC50	=	60000.0	nM	PMID[517632]

☑ 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 NPC273830 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	231
0.1-0.2	1898
0.2-0.3	10952
0.3-0.4	11326
0.4-0.5	14516
0.5-0.6	3375
0.6-0.7	375
0.7-0.8	18
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.7807	Intermediate Similarity	NPC33168
0.7647	Intermediate Similarity	NPC211551
0.763	Intermediate Similarity	NPC267237
0.741	Intermediate Similarity	NPC214988
0.7281	Intermediate Similarity	NPC172128
0.7197	Intermediate Similarity	NPC109151
0.7179	Intermediate Similarity	NPC108339
0.7177	Intermediate Similarity	NPC153690
0.7111	Intermediate Similarity	NPC477937
0.7107	Intermediate Similarity	NPC327226
0.7107	Intermediate Similarity	NPC318154
0.7063	Intermediate Similarity	NPC168861
0.7059	Intermediate Similarity	NPC311242
0.7045	Intermediate Similarity	NPC326232
0.704	Intermediate Similarity	NPC96224
0.704	Intermediate Similarity	NPC24101
0.7037	Intermediate Similarity	NPC4974
0.7018	Intermediate Similarity	NPC198747
0.7009	Intermediate Similarity	NPC265521
0.7	Intermediate Similarity	NPC82963
0.6992	Remote Similarity	NPC226778
0.6992	Remote Similarity	NPC147000
0.6992	Remote Similarity	NPC150254
0.6992	Remote Similarity	NPC304761
0.6975	Remote Similarity	NPC471320
0.6975	Remote Similarity	NPC471319
0.6947	Remote Similarity	NPC311737
0.6947	Remote Similarity	NPC38458
0.6934	Remote Similarity	NPC199738
0.6934	Remote Similarity	NPC210950
0.693	Remote Similarity	NPC203076
0.6923	Remote Similarity	NPC48202
0.6891	Remote Similarity	NPC20142
0.6891	Remote Similarity	NPC215351
0.685	Remote Similarity	NPC65855
0.685	Remote Similarity	NPC292758
0.6842	Remote Similarity	NPC43275
0.6842	Remote Similarity	NPC283760
0.6835	Remote Similarity	NPC271808
0.6833	Remote Similarity	NPC3371
0.6814	Remote Similarity	NPC146703
0.6797	Remote Similarity	NPC319579
0.6795	Remote Similarity	NPC223207
0.6781	Remote Similarity	NPC326241
0.6763	Remote Similarity	NPC311753
0.6761	Remote Similarity	NPC132847
0.6759	Remote Similarity	NPC170170
0.6759	Remote Similarity	NPC211468
0.6759	Remote Similarity	NPC219233
0.6757	Remote Similarity	NPC311658
0.6752	Remote Similarity	NPC290755
0.6752	Remote Similarity	NPC471771
0.6752	Remote Similarity	NPC304074
0.6746	Remote Similarity	NPC231705
0.6738	Remote Similarity	NPC476685
0.6738	Remote Similarity	NPC476689
0.6738	Remote Similarity	NPC476687
0.6721	Remote Similarity	NPC108606
0.6721	Remote Similarity	NPC290515
0.6721	Remote Similarity	NPC164514
0.6721	Remote Similarity	NPC226096
0.6721	Remote Similarity	NPC303611
0.6719	Remote Similarity	NPC258056
0.6714	Remote Similarity	NPC471321
0.6714	Remote Similarity	NPC325651
0.6714	Remote Similarity	NPC471306
0.6712	Remote Similarity	NPC323123
0.6693	Remote Similarity	NPC142297
0.6692	Remote Similarity	NPC137096
0.669	Remote Similarity	NPC3202
0.669	Remote Similarity	NPC149379
0.6689	Remote Similarity	NPC314114
0.6667	Remote Similarity	NPC196243
0.6667	Remote Similarity	NPC474149
0.6642	Remote Similarity	NPC85276
0.664	Remote Similarity	NPC68055
0.6639	Remote Similarity	NPC226438
0.6621	Remote Similarity	NPC132636
0.662	Remote Similarity	NPC326966
0.6619	Remote Similarity	NPC318965
0.6618	Remote Similarity	NPC71684
0.6613	Remote Similarity	NPC228400
0.6613	Remote Similarity	NPC469457
0.6613	Remote Similarity	NPC214200
0.6612	Remote Similarity	NPC161972
0.6612	Remote Similarity	NPC58674
0.6612	Remote Similarity	NPC303045
0.661	Remote Similarity	NPC470877
0.6603	Remote Similarity	NPC469243
0.6597	Remote Similarity	NPC314835
0.6593	Remote Similarity	NPC268572
0.6591	Remote Similarity	NPC118202
0.6581	Remote Similarity	NPC471638
0.6575	Remote Similarity	NPC153007
0.6567	Remote Similarity	NPC283468
0.6557	Remote Similarity	NPC25565
0.6555	Remote Similarity	NPC209764
0.6555	Remote Similarity	NPC74936
0.6555	Remote Similarity	NPC159178
0.6555	Remote Similarity	NPC78041
0.6555	Remote Similarity	NPC471307
0.6555	Remote Similarity	NPC141139
0.6555	Remote Similarity	NPC121872
0.6552	Remote Similarity	NPC237227
0.6541	Remote Similarity	NPC213
0.6541	Remote Similarity	NPC10286
0.6541	Remote Similarity	NPC317254
0.6532	Remote Similarity	NPC125732
0.6529	Remote Similarity	NPC7067
0.6528	Remote Similarity	NPC474473
0.6525	Remote Similarity	NPC111428
0.6522	Remote Similarity	NPC198254
0.6522	Remote Similarity	NPC274198
0.6519	Remote Similarity	NPC122009
0.6515	Remote Similarity	NPC474544
0.6515	Remote Similarity	NPC1986
0.6508	Remote Similarity	NPC178902
0.6504	Remote Similarity	NPC473501
0.6504	Remote Similarity	NPC475439
0.65	Remote Similarity	NPC29477
0.6497	Remote Similarity	NPC475544
0.6496	Remote Similarity	NPC284078
0.6489	Remote Similarity	NPC275410
0.6484	Remote Similarity	NPC327481
0.6463	Remote Similarity	NPC197045
0.6458	Remote Similarity	NPC244866
0.6441	Remote Similarity	NPC473031
0.6434	Remote Similarity	NPC37584
0.6429	Remote Similarity	NPC474479
0.642	Remote Similarity	NPC276506
0.6404	Remote Similarity	NPC192623
0.6402	Remote Similarity	NPC165285
0.64	Remote Similarity	NPC473922
0.6393	Remote Similarity	NPC471309
0.6382	Remote Similarity	NPC5462
0.637	Remote Similarity	NPC147957
0.6369	Remote Similarity	NPC93343
0.6364	Remote Similarity	NPC226662
0.6357	Remote Similarity	NPC45033
0.6357	Remote Similarity	NPC191215
0.6357	Remote Similarity	NPC274089
0.6349	Remote Similarity	NPC289381
0.6349	Remote Similarity	NPC155847
0.6346	Remote Similarity	NPC473580
0.6345	Remote Similarity	NPC300020
0.6345	Remote Similarity	NPC33338
0.6345	Remote Similarity	NPC302171
0.6341	Remote Similarity	NPC475532
0.6341	Remote Similarity	NPC329430
0.634	Remote Similarity	NPC254798
0.6336	Remote Similarity	NPC145638
0.6336	Remote Similarity	NPC290566
0.6336	Remote Similarity	NPC24777
0.6333	Remote Similarity	NPC199567
0.6325	Remote Similarity	NPC133162
0.6323	Remote Similarity	NPC207824
0.6323	Remote Similarity	NPC60538
0.632	Remote Similarity	NPC107619
0.6319	Remote Similarity	NPC89769
0.6319	Remote Similarity	NPC259665
0.6319	Remote Similarity	NPC126859
0.6316	Remote Similarity	NPC119569
0.6316	Remote Similarity	NPC474584
0.6316	Remote Similarity	NPC146422
0.6312	Remote Similarity	NPC95733
0.6312	Remote Similarity	NPC22014
0.6312	Remote Similarity	NPC62101
0.6309	Remote Similarity	NPC476989
0.6304	Remote Similarity	NPC263835
0.6303	Remote Similarity	NPC17698
0.6294	Remote Similarity	NPC477839
0.6293	Remote Similarity	NPC14326
0.6289	Remote Similarity	NPC29647
0.6287	Remote Similarity	NPC119652
0.6287	Remote Similarity	NPC97526
0.6286	Remote Similarity	NPC471314
0.6286	Remote Similarity	NPC471315
0.6281	Remote Similarity	NPC316108
0.6281	Remote Similarity	NPC258627
0.6276	Remote Similarity	NPC246913
0.6271	Remote Similarity	NPC3210
0.6267	Remote Similarity	NPC33011
0.6258	Remote Similarity	NPC280022
0.625	Remote Similarity	NPC12429
0.625	Remote Similarity	NPC79328
0.625	Remote Similarity	NPC19856
0.625	Remote Similarity	NPC164859
0.625	Remote Similarity	NPC470544
0.625	Remote Similarity	NPC262393
0.625	Remote Similarity	NPC473804
0.625	Remote Similarity	NPC153554
0.625	Remote Similarity	NPC124802
0.6242	Remote Similarity	NPC76213
0.6242	Remote Similarity	NPC277669
0.6241	Remote Similarity	NPC329011
0.6241	Remote Similarity	NPC307020
0.6241	Remote Similarity	NPC211218
0.6239	Remote Similarity	NPC172984
0.623	Remote Similarity	NPC245259
0.6224	Remote Similarity	NPC322366

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 NPC273830 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	500
0.2-0.3	1065
0.3-0.4	1293
0.4-0.5	3759
0.5-0.6	2005
0.6-0.7	365
0.7-0.8	23
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
0.781	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD8011	Discontinued
0.7643	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2173	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4032	Approved
0.746	Intermediate Similarity	NPD4031	Approved
0.7338	Intermediate Similarity	NPD8154	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4119	Approved
0.7231	Intermediate Similarity	NPD1922	Discontinued
0.719	Intermediate Similarity	NPD4656	Approved
0.719	Intermediate Similarity	NPD4658	Approved
0.7185	Intermediate Similarity	NPD7451	Discontinued
0.7154	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1710	Approved
0.7083	Intermediate Similarity	NPD2211	Approved
0.7083	Intermediate Similarity	NPD2209	Approved
0.7073	Intermediate Similarity	NPD5717	Approved
0.7071	Intermediate Similarity	NPD6086	Phase 2
0.7071	Intermediate Similarity	NPD3851	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4229	Approved
0.7049	Intermediate Similarity	NPD4231	Approved
0.7049	Intermediate Similarity	NPD5103	Approved
0.7037	Intermediate Similarity	NPD5311	Approved
0.7037	Intermediate Similarity	NPD5310	Approved
0.7	Intermediate Similarity	NPD4117	Approved
0.6993	Remote Similarity	NPD1884	Approved
0.6992	Remote Similarity	NPD10	Approved
0.6992	Remote Similarity	NPD314	Approved
0.6992	Remote Similarity	NPD315	Approved
0.6992	Remote Similarity	NPD311	Approved
0.6992	Remote Similarity	NPD309	Approved
0.6992	Remote Similarity	NPD310	Approved
0.6978	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD8019	Approved
0.6972	Remote Similarity	NPD8147	Approved
0.6972	Remote Similarity	NPD8148	Approved
0.6967	Remote Similarity	NPD4818	Approved
0.6967	Remote Similarity	NPD4817	Approved
0.696	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4254	Approved
0.6929	Remote Similarity	NPD4253	Approved
0.6918	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1542	Approved
0.6911	Remote Similarity	NPD3682	Approved
0.6911	Remote Similarity	NPD3680	Approved
0.6875	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5500	Discontinued
0.687	Remote Similarity	NPD9538	Approved
0.6864	Remote Similarity	NPD1812	Approved
0.6864	Remote Similarity	NPD1814	Approved
0.6863	Remote Similarity	NPD7495	Discontinued
0.6861	Remote Similarity	NPD3055	Approved
0.6861	Remote Similarity	NPD3053	Approved
0.6855	Remote Similarity	NPD1026	Approved
0.6855	Remote Similarity	NPD1028	Approved
0.6853	Remote Similarity	NPD3555	Approved
0.6853	Remote Similarity	NPD3553	Approved
0.6853	Remote Similarity	NPD3552	Approved
0.6853	Remote Similarity	NPD3554	Approved
0.6842	Remote Similarity	NPD4093	Discontinued
0.6829	Remote Similarity	NPD1540	Approved
0.6829	Remote Similarity	NPD5716	Approved
0.68	Remote Similarity	NPD1268	Approved
0.68	Remote Similarity	NPD1269	Approved
0.6797	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7342	Discontinued
0.678	Remote Similarity	NPD530	Approved
0.6777	Remote Similarity	NPD1875	Phase 1
0.6777	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3681	Approved
0.6774	Remote Similarity	NPD3683	Approved
0.6767	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2561	Approved
0.6765	Remote Similarity	NPD2562	Approved
0.6755	Remote Similarity	NPD6819	Phase 2
0.675	Remote Similarity	NPD3772	Phase 3
0.6742	Remote Similarity	NPD3123	Discovery
0.6721	Remote Similarity	NPD9609	Approved
0.6721	Remote Similarity	NPD9611	Approved
0.6721	Remote Similarity	NPD9612	Approved
0.6716	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7554	Discontinued
0.6711	Remote Similarity	NPD3845	Phase 1
0.6692	Remote Similarity	NPD9613	Approved
0.6692	Remote Similarity	NPD9616	Approved
0.6692	Remote Similarity	NPD9615	Approved
0.6691	Remote Similarity	NPD3381	Discontinued
0.669	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7508	Discontinued
0.6667	Remote Similarity	NPD9712	Approved
0.6667	Remote Similarity	NPD6320	Approved
0.6667	Remote Similarity	NPD7725	Approved
0.6667	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4857	Phase 1
0.6644	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7450	Phase 2
0.6644	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD316	Approved
0.6641	Remote Similarity	NPD2228	Approved
0.6641	Remote Similarity	NPD2234	Approved
0.6641	Remote Similarity	NPD2229	Approved
0.6618	Remote Similarity	NPD1980	Approved
0.6618	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD1983	Approved
0.6618	Remote Similarity	NPD1981	Approved
0.6618	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5162	Approved
0.6615	Remote Similarity	NPD2500	Approved
0.6615	Remote Similarity	NPD2499	Approved
0.6605	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD1792	Phase 2
0.6585	Remote Similarity	NPD9711	Approved
0.6585	Remote Similarity	NPD9710	Approved
0.6583	Remote Similarity	NPD752	Approved
0.6583	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6222	Approved
0.6579	Remote Similarity	NPD6221	Approved
0.6567	Remote Similarity	NPD16	Approved
0.6567	Remote Similarity	NPD856	Approved
0.656	Remote Similarity	NPD855	Approved
0.656	Remote Similarity	NPD854	Approved
0.656	Remote Similarity	NPD2841	Approved
0.6557	Remote Similarity	NPD2895	Discontinued
0.6557	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5915	Approved
0.6554	Remote Similarity	NPD4256	Phase 2
0.6554	Remote Similarity	NPD4257	Approved
0.6552	Remote Similarity	NPD5314	Approved
0.6547	Remote Similarity	NPD3125	Approved
0.6538	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7523	Phase 3
0.6531	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD197	Approved
0.6529	Remote Similarity	NPD199	Approved
0.6528	Remote Similarity	NPD3061	Approved
0.6528	Remote Similarity	NPD3059	Approved
0.6528	Remote Similarity	NPD3062	Approved
0.6522	Remote Similarity	NPD7250	Approved
0.6522	Remote Similarity	NPD7249	Approved
0.6519	Remote Similarity	NPD5304	Approved
0.6519	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5303	Approved
0.6512	Remote Similarity	NPD4717	Approved
0.6512	Remote Similarity	NPD4720	Approved
0.6512	Remote Similarity	NPD4718	Approved
0.651	Remote Similarity	NPD3638	Discontinued
0.651	Remote Similarity	NPD6301	Phase 2
0.6508	Remote Similarity	NPD5655	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1330	Phase 2
0.6493	Remote Similarity	NPD1841	Clinical (unspecified phase)
0.649	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2551	Approved
0.6484	Remote Similarity	NPD2559	Approved
0.648	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7253	Phase 3
0.6457	Remote Similarity	NPD9608	Approved
0.6457	Remote Similarity	NPD9610	Approved
0.6452	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4323	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6690	Approved
0.6444	Remote Similarity	NPD1837	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD317	Approved
0.6444	Remote Similarity	NPD828	Approved
0.6444	Remote Similarity	NPD318	Approved
0.6441	Remote Similarity	NPD3428	Approved
0.6441	Remote Similarity	NPD3426	Approved
0.6438	Remote Similarity	NPD2568	Approved
0.6434	Remote Similarity	NPD2372	Approved
0.6434	Remote Similarity	NPD2206	Approved
0.6434	Remote Similarity	NPD2207	Approved
0.6429	Remote Similarity	NPD4719	Phase 2
0.6424	Remote Similarity	NPD3692	Discontinued
0.6423	Remote Similarity	NPD5723	Approved
0.6419	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD3156	Discontinued
0.6414	Remote Similarity	NPD6346	Approved
0.6412	Remote Similarity	NPD2583	Phase 2
0.641	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD7019	Approved
0.6405	Remote Similarity	NPD7020	Approved
0.6403	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD6624	Discontinued
0.64	Remote Similarity	NPD2458	Approved
0.64	Remote Similarity	NPD2459	Approved
0.64	Remote Similarity	NPD2460	Phase 3
0.6397	Remote Similarity	NPD5511	Discontinued
0.6393	Remote Similarity	NPD3982	Approved
0.6393	Remote Similarity	NPD3980	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