NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.17
Volume:	289.511
LogP:	2.083
LogD:	1.283
LogS:	-2.393
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.862
Synthetic Accessibility Score:	5.253
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.434
MDCK Permeability:	4.122145037399605e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.119
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.105

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.929
Plasma Protein Binding (PPB):	29.231773376464844%
Volume Distribution (VD):	0.458
Pgp-substrate:	63.61693572998047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.431
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.472
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.174
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.074

ADMET: Excretion

Clearance (CL):	8.948
Half-life (T1/2):	0.263

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.175
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.8
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.058
Carcinogencity:	0.589
Eye Corrosion:	0.451
Eye Irritation:	0.092
Respiratory Toxicity:	0.901

Download Data

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

Natural Product: NPC169389

Natural Product ID:	NPC169389
*Common Name:**	ZSKXGGRFBGTYFO-OSHAPPAQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZSKXGGRFBGTYFO-OSHAPPAQSA-N
Standard InCHI:	InChI=1S/C16H24O4/c1-15(2)8-16-10(14(18)19)5-4-9(15)11(16)6-13(17)12(16)7-20-3/h9-12H,4-8H2,1-3H3,(H,18,19)/t9-,10+,11-,12-,16-/m0/s1
SMILES:	COC[C@H]1C(=O)C[C@@H]2[C@]31CC([C@H]2CC[C@@H]3C(=O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511399
PubChem CID:	21574199
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	from the rhizosphere of Opuntia versicolor of the Sonoran Desert	n.a.	PMID[14695798]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124769]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271552]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22360613]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24534845]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25671343]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2921224]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30207465]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32163285]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32897070]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984154]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	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	3
Others	3

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	19400.0	nM	PMID[462994]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	20600.0	nM	PMID[462994]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	21400.0	nM	PMID[462994]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	44.3	%	PMID[462994]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	21.4	%	PMID[462994]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	34.3	%	PMID[462994]

☑ 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 NPC169389 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	324
0.1-0.2	3367
0.2-0.3	12935
0.3-0.4	11103
0.4-0.5	7173
0.5-0.6	6115
0.6-0.7	1520
0.7-0.8	155
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC132064
0.8649	High Similarity	NPC248567
0.8421	Intermediate Similarity	NPC472311
0.8205	Intermediate Similarity	NPC477918
0.8125	Intermediate Similarity	NPC1882
0.8049	Intermediate Similarity	NPC472847
0.8026	Intermediate Similarity	NPC472309
0.7952	Intermediate Similarity	NPC473336
0.7952	Intermediate Similarity	NPC471044
0.7949	Intermediate Similarity	NPC477934
0.7945	Intermediate Similarity	NPC469791
0.7907	Intermediate Similarity	NPC200580
0.7857	Intermediate Similarity	NPC473350
0.7848	Intermediate Similarity	NPC477932
0.7848	Intermediate Similarity	NPC477933
0.7821	Intermediate Similarity	NPC477930
0.7821	Intermediate Similarity	NPC477867
0.7792	Intermediate Similarity	NPC469940
0.7778	Intermediate Similarity	NPC472310
0.775	Intermediate Similarity	NPC74685
0.775	Intermediate Similarity	NPC475932
0.7738	Intermediate Similarity	NPC25802
0.7738	Intermediate Similarity	NPC51135
0.7738	Intermediate Similarity	NPC82492
0.7738	Intermediate Similarity	NPC101138
0.7711	Intermediate Similarity	NPC30583
0.7662	Intermediate Similarity	NPC477929
0.7654	Intermediate Similarity	NPC185465
0.7632	Intermediate Similarity	NPC470956
0.76	Intermediate Similarity	NPC477931
0.76	Intermediate Similarity	NPC268736
0.7568	Intermediate Similarity	NPC128608
0.7564	Intermediate Similarity	NPC473267
0.7561	Intermediate Similarity	NPC201276
0.7561	Intermediate Similarity	NPC320144
0.7561	Intermediate Similarity	NPC80891
0.7532	Intermediate Similarity	NPC319671
0.7532	Intermediate Similarity	NPC252032
0.7532	Intermediate Similarity	NPC64466
0.7532	Intermediate Similarity	NPC469941
0.7532	Intermediate Similarity	NPC476734
0.7531	Intermediate Similarity	NPC471151
0.7529	Intermediate Similarity	NPC477434
0.7529	Intermediate Similarity	NPC319909
0.75	Intermediate Similarity	NPC311642
0.75	Intermediate Similarity	NPC100366
0.75	Intermediate Similarity	NPC477935
0.75	Intermediate Similarity	NPC289486
0.75	Intermediate Similarity	NPC155441
0.75	Intermediate Similarity	NPC102156
0.75	Intermediate Similarity	NPC61107
0.75	Intermediate Similarity	NPC242771
0.75	Intermediate Similarity	NPC148740
0.75	Intermediate Similarity	NPC477936
0.75	Intermediate Similarity	NPC164289
0.747	Intermediate Similarity	NPC472853
0.7444	Intermediate Similarity	NPC472237
0.7444	Intermediate Similarity	NPC472238
0.7444	Intermediate Similarity	NPC476189
0.7439	Intermediate Similarity	NPC476732
0.7439	Intermediate Similarity	NPC34046
0.7439	Intermediate Similarity	NPC324700
0.7439	Intermediate Similarity	NPC80089
0.7439	Intermediate Similarity	NPC224802
0.7439	Intermediate Similarity	NPC199965
0.7439	Intermediate Similarity	NPC171426
0.7436	Intermediate Similarity	NPC477850
0.7436	Intermediate Similarity	NPC476731
0.7436	Intermediate Similarity	NPC108131
0.7412	Intermediate Similarity	NPC292458
0.7412	Intermediate Similarity	NPC217559
0.7412	Intermediate Similarity	NPC268578
0.7407	Intermediate Similarity	NPC4209
0.7391	Intermediate Similarity	NPC193785
0.7391	Intermediate Similarity	NPC470387
0.7386	Intermediate Similarity	NPC191221
0.7375	Intermediate Similarity	NPC133922
0.7375	Intermediate Similarity	NPC280026
0.7375	Intermediate Similarity	NPC167702
0.7368	Intermediate Similarity	NPC42060
0.7356	Intermediate Similarity	NPC302111
0.7326	Intermediate Similarity	NPC219535
0.7326	Intermediate Similarity	NPC237938
0.7317	Intermediate Similarity	NPC474404
0.7317	Intermediate Similarity	NPC180199
0.7317	Intermediate Similarity	NPC207010
0.7317	Intermediate Similarity	NPC317913
0.7317	Intermediate Similarity	NPC477919
0.7308	Intermediate Similarity	NPC474962
0.7308	Intermediate Similarity	NPC196197
0.7303	Intermediate Similarity	NPC61688
0.7284	Intermediate Similarity	NPC212733
0.7284	Intermediate Similarity	NPC179922
0.7284	Intermediate Similarity	NPC179858
0.7283	Intermediate Similarity	NPC62407
0.7283	Intermediate Similarity	NPC287354
0.7273	Intermediate Similarity	NPC130459
0.7273	Intermediate Similarity	NPC478180
0.7273	Intermediate Similarity	NPC239938
0.7273	Intermediate Similarity	NPC474221
0.7263	Intermediate Similarity	NPC478181
0.7262	Intermediate Similarity	NPC261616
0.7262	Intermediate Similarity	NPC477851
0.7241	Intermediate Similarity	NPC477205
0.7241	Intermediate Similarity	NPC201655
0.7229	Intermediate Similarity	NPC329117
0.7209	Intermediate Similarity	NPC15821
0.7195	Intermediate Similarity	NPC474020
0.7195	Intermediate Similarity	NPC471046
0.7191	Intermediate Similarity	NPC226491
0.7191	Intermediate Similarity	NPC477614
0.7191	Intermediate Similarity	NPC183374
0.7191	Intermediate Similarity	NPC56413
0.7191	Intermediate Similarity	NPC90676
0.7191	Intermediate Similarity	NPC211162
0.7179	Intermediate Similarity	NPC319007
0.7176	Intermediate Similarity	NPC58631
0.7176	Intermediate Similarity	NPC254123
0.7174	Intermediate Similarity	NPC470385
0.7174	Intermediate Similarity	NPC470386
0.7174	Intermediate Similarity	NPC470424
0.7174	Intermediate Similarity	NPC475118
0.716	Intermediate Similarity	NPC215030
0.716	Intermediate Similarity	NPC317212
0.7159	Intermediate Similarity	NPC92139
0.7159	Intermediate Similarity	NPC83242
0.7159	Intermediate Similarity	NPC120395
0.7143	Intermediate Similarity	NPC245029
0.7143	Intermediate Similarity	NPC31302
0.7143	Intermediate Similarity	NPC52951
0.7143	Intermediate Similarity	NPC52756
0.7126	Intermediate Similarity	NPC50438
0.7125	Intermediate Similarity	NPC58057
0.7125	Intermediate Similarity	NPC197701
0.7125	Intermediate Similarity	NPC151018
0.7125	Intermediate Similarity	NPC311102
0.7125	Intermediate Similarity	NPC156277
0.7125	Intermediate Similarity	NPC320549
0.7125	Intermediate Similarity	NPC478227
0.7125	Intermediate Similarity	NPC470243
0.7111	Intermediate Similarity	NPC67653
0.7111	Intermediate Similarity	NPC474570
0.7111	Intermediate Similarity	NPC116146
0.7111	Intermediate Similarity	NPC56962
0.7111	Intermediate Similarity	NPC477443
0.7111	Intermediate Similarity	NPC471459
0.7111	Intermediate Similarity	NPC24705
0.7111	Intermediate Similarity	NPC24772
0.7111	Intermediate Similarity	NPC477440
0.7108	Intermediate Similarity	NPC298168
0.7108	Intermediate Similarity	NPC143133
0.7097	Intermediate Similarity	NPC470232
0.7097	Intermediate Similarity	NPC470229
0.7097	Intermediate Similarity	NPC266431
0.7093	Intermediate Similarity	NPC121121
0.7093	Intermediate Similarity	NPC13494
0.7089	Intermediate Similarity	NPC321732
0.7089	Intermediate Similarity	NPC131892
0.7089	Intermediate Similarity	NPC324607
0.7089	Intermediate Similarity	NPC213178
0.7089	Intermediate Similarity	NPC6120
0.7089	Intermediate Similarity	NPC98711
0.7089	Intermediate Similarity	NPC327728
0.7079	Intermediate Similarity	NPC134197
0.7079	Intermediate Similarity	NPC96496
0.7079	Intermediate Similarity	NPC252714
0.7073	Intermediate Similarity	NPC21220
0.7073	Intermediate Similarity	NPC125767
0.7073	Intermediate Similarity	NPC159789
0.7059	Intermediate Similarity	NPC279667
0.7051	Intermediate Similarity	NPC41542
0.7045	Intermediate Similarity	NPC473038
0.7045	Intermediate Similarity	NPC142649
0.7045	Intermediate Similarity	NPC62572
0.7042	Intermediate Similarity	NPC319589
0.7037	Intermediate Similarity	NPC232112
0.7037	Intermediate Similarity	NPC310766
0.7037	Intermediate Similarity	NPC177826
0.7037	Intermediate Similarity	NPC474755
0.7033	Intermediate Similarity	NPC77756
0.7033	Intermediate Similarity	NPC477442
0.7033	Intermediate Similarity	NPC477433
0.7033	Intermediate Similarity	NPC476296
0.7033	Intermediate Similarity	NPC477444
0.7021	Intermediate Similarity	NPC329910
0.7021	Intermediate Similarity	NPC116683
0.7013	Intermediate Similarity	NPC476330
0.7011	Intermediate Similarity	NPC259173
0.7011	Intermediate Similarity	NPC477373
0.7011	Intermediate Similarity	NPC157328
0.7	Intermediate Similarity	NPC3032
0.7	Intermediate Similarity	NPC131104
0.7	Intermediate Similarity	NPC229407
0.7	Intermediate Similarity	NPC236459
0.7	Intermediate Similarity	NPC471221
0.7	Intermediate Similarity	NPC33398
0.7	Intermediate Similarity	NPC48824
0.7	Intermediate Similarity	NPC473319
0.7	Intermediate Similarity	NPC469508
0.7	Intermediate Similarity	NPC254572

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 NPC169389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	3698
0.2-0.3	3427
0.3-0.4	913
0.4-0.5	373
0.5-0.6	262
0.6-0.7	43
0.7-0.8	9
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
0.8026	Intermediate Similarity	NPD6081	Approved
0.7722	Intermediate Similarity	NPD3702	Approved
0.7703	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4224	Phase 2
0.7439	Intermediate Similarity	NPD6697	Approved
0.7439	Intermediate Similarity	NPD6115	Approved
0.7439	Intermediate Similarity	NPD6118	Approved
0.7439	Intermediate Similarity	NPD6114	Approved
0.7407	Intermediate Similarity	NPD6117	Approved
0.7375	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6116	Phase 1
0.7215	Intermediate Similarity	NPD4789	Approved
0.7125	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5777	Approved
0.7125	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3698	Phase 2
0.7089	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3703	Phase 2
0.7	Intermediate Similarity	NPD4244	Approved
0.7	Intermediate Similarity	NPD4245	Approved
0.6962	Remote Similarity	NPD5360	Phase 3
0.6962	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4238	Approved
0.6824	Remote Similarity	NPD4802	Phase 2
0.6735	Remote Similarity	NPD1700	Approved
0.6707	Remote Similarity	NPD4758	Discontinued
0.6579	Remote Similarity	NPD3198	Approved
0.6575	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5696	Approved
0.6526	Remote Similarity	NPD6399	Phase 3
0.6484	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7909	Approved
0.6437	Remote Similarity	NPD3671	Phase 1
0.6437	Remote Similarity	NPD5364	Discontinued
0.6421	Remote Similarity	NPD8035	Phase 2
0.6421	Remote Similarity	NPD8034	Phase 2
0.6392	Remote Similarity	NPD5695	Phase 3
0.6351	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6672	Approved
0.6277	Remote Similarity	NPD5737	Approved
0.6277	Remote Similarity	NPD6903	Approved
0.6264	Remote Similarity	NPD4788	Approved
0.6263	Remote Similarity	NPD6083	Phase 2
0.6263	Remote Similarity	NPD6084	Phase 2
0.6214	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4786	Approved
0.619	Remote Similarity	NPD7320	Approved
0.6154	Remote Similarity	NPD3667	Approved
0.6145	Remote Similarity	NPD229	Approved
0.6105	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5281	Approved
0.6082	Remote Similarity	NPD5284	Approved
0.6067	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3617	Approved
0.6064	Remote Similarity	NPD7146	Approved
0.6064	Remote Similarity	NPD6684	Approved
0.6064	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5330	Approved
0.6064	Remote Similarity	NPD7521	Approved
0.6064	Remote Similarity	NPD6409	Approved
0.6064	Remote Similarity	NPD7334	Approved
0.6061	Remote Similarity	NPD4629	Approved
0.6061	Remote Similarity	NPD5210	Approved
0.6056	Remote Similarity	NPD345	Approved
0.6056	Remote Similarity	NPD344	Approved
0.6056	Remote Similarity	NPD343	Approved
0.6044	Remote Similarity	NPD4139	Approved
0.6044	Remote Similarity	NPD5369	Approved
0.6044	Remote Similarity	NPD4692	Approved
0.6042	Remote Similarity	NPD4753	Phase 2
0.6042	Remote Similarity	NPD5328	Approved
0.6022	Remote Similarity	NPD3666	Approved
0.6022	Remote Similarity	NPD3133	Approved
0.6022	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.598	Remote Similarity	NPD8418	Phase 2
0.5978	Remote Similarity	NPD4223	Phase 3
0.5978	Remote Similarity	NPD4221	Approved
0.5972	Remote Similarity	NPD2266	Phase 2
0.5943	Remote Similarity	NPD5697	Approved
0.5943	Remote Similarity	NPD5701	Approved
0.5938	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD6928	Phase 2
0.5918	Remote Similarity	NPD6079	Approved
0.5915	Remote Similarity	NPD634	Phase 3
0.5909	Remote Similarity	NPD4632	Approved
0.5904	Remote Similarity	NPD375	Phase 2
0.59	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5786	Approved
0.5895	Remote Similarity	NPD3618	Phase 1
0.5895	Remote Similarity	NPD6098	Approved
0.5895	Remote Similarity	NPD5279	Phase 3
0.5888	Remote Similarity	NPD6881	Approved
0.5888	Remote Similarity	NPD6011	Approved
0.5888	Remote Similarity	NPD6899	Approved
0.5888	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7638	Approved
0.5882	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6319	Approved
0.5876	Remote Similarity	NPD6904	Approved
0.5876	Remote Similarity	NPD6080	Approved
0.5876	Remote Similarity	NPD6673	Approved
0.587	Remote Similarity	NPD1780	Approved
0.587	Remote Similarity	NPD1779	Approved
0.5851	Remote Similarity	NPD4197	Approved
0.5851	Remote Similarity	NPD3668	Phase 3
0.5847	Remote Similarity	NPD7078	Approved
0.5842	Remote Similarity	NPD5222	Approved
0.5842	Remote Similarity	NPD4697	Phase 3
0.5842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5221	Approved
0.5833	Remote Similarity	NPD6013	Approved
0.5833	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD6014	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD6372	Approved
0.5825	Remote Similarity	NPD7639	Approved
0.5825	Remote Similarity	NPD7640	Approved
0.5816	Remote Similarity	NPD5785	Approved
0.5816	Remote Similarity	NPD5692	Phase 3
0.5816	Remote Similarity	NPD5207	Approved
0.5812	Remote Similarity	NPD7492	Approved
0.5806	Remote Similarity	NPD6435	Approved
0.5806	Remote Similarity	NPD4269	Approved
0.5806	Remote Similarity	NPD4270	Approved
0.58	Remote Similarity	NPD7748	Approved
0.5789	Remote Similarity	NPD5329	Approved
0.5784	Remote Similarity	NPD4755	Approved
0.5784	Remote Similarity	NPD5173	Approved
0.5783	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6883	Approved
0.578	Remote Similarity	NPD7102	Approved
0.578	Remote Similarity	NPD7290	Approved
0.5773	Remote Similarity	NPD5208	Approved
0.5763	Remote Similarity	NPD6616	Approved
0.5761	Remote Similarity	NPD5368	Approved
0.5758	Remote Similarity	NPD7637	Suspended
0.5758	Remote Similarity	NPD5693	Phase 1
0.5758	Remote Similarity	NPD7515	Phase 2
0.5758	Remote Similarity	NPD5694	Approved
0.5758	Remote Similarity	NPD6411	Approved
0.5758	Remote Similarity	NPD6050	Approved
0.5752	Remote Similarity	NPD6009	Approved
0.5745	Remote Similarity	NPD3669	Approved
0.5745	Remote Similarity	NPD5362	Discontinued
0.5745	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6054	Approved
0.5739	Remote Similarity	NPD6059	Approved
0.5733	Remote Similarity	NPD9638	Phase 2
0.573	Remote Similarity	NPD2257	Approved
0.5729	Remote Similarity	NPD5205	Approved
0.5729	Remote Similarity	NPD4138	Approved
0.5729	Remote Similarity	NPD4694	Approved
0.5729	Remote Similarity	NPD5280	Approved
0.5729	Remote Similarity	NPD5690	Phase 2
0.5729	Remote Similarity	NPD4689	Approved
0.5729	Remote Similarity	NPD4688	Approved
0.5729	Remote Similarity	NPD4693	Phase 3
0.5729	Remote Similarity	NPD4690	Approved
0.5727	Remote Similarity	NPD6649	Approved
0.5727	Remote Similarity	NPD6617	Approved
0.5727	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD8130	Phase 1
0.5727	Remote Similarity	NPD6869	Approved
0.5727	Remote Similarity	NPD6847	Approved
0.5727	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD7632	Discontinued
0.5714	Remote Similarity	NPD8293	Discontinued
0.5701	Remote Similarity	NPD6920	Discontinued
0.57	Remote Similarity	NPD4202	Approved
0.569	Remote Similarity	NPD6015	Approved
0.569	Remote Similarity	NPD6016	Approved
0.5686	Remote Similarity	NPD7614	Phase 1
0.5676	Remote Similarity	NPD6053	Discontinued
0.5676	Remote Similarity	NPD8297	Approved
0.5676	Remote Similarity	NPD6882	Approved
0.5673	Remote Similarity	NPD5285	Approved
0.5673	Remote Similarity	NPD4700	Approved
0.5673	Remote Similarity	NPD5286	Approved
0.5673	Remote Similarity	NPD4696	Approved
0.5667	Remote Similarity	NPD7736	Approved
0.5658	Remote Similarity	NPD3186	Phase 1
0.5648	Remote Similarity	NPD6412	Phase 2
0.5644	Remote Similarity	NPD5282	Discontinued
0.5644	Remote Similarity	NPD6001	Approved
0.5641	Remote Similarity	NPD5988	Approved
0.5641	Remote Similarity	NPD6370	Approved
0.5638	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD4634	Approved
0.5632	Remote Similarity	NPD4787	Phase 1
0.5631	Remote Similarity	NPD7902	Approved
0.5625	Remote Similarity	NPD5363	Approved
0.5619	Remote Similarity	NPD5223	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