NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	254.868
LogP:	2.865
LogD:	2.571
LogS:	-3.717
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.617
Synthetic Accessibility Score:	5.728
Fsp3:	0.867
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:	-4.897
MDCK Permeability:	3.0033688744879328e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.984
Plasma Protein Binding (PPB):	41.47647476196289%
Volume Distribution (VD):	0.827
Pgp-substrate:	72.93058776855469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.329
CYP2C19-inhibitor:	0.187
CYP2C19-substrate:	0.755
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.589
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	15.919
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.234
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.265
Skin Sensitization:	0.176
Carcinogencity:	0.267
Eye Corrosion:	0.76
Eye Irritation:	0.163
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC248567

Natural Product ID:	NPC248567
*Common Name:**	Quadrone
IUPAC Name:	n.a.
Synonyms:	Quadrone
Standard InCHIKey:	BBIDMUQZCCGABN-UXSWQMMLSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-14(2)7-15-9-4-3-8(14)10(15)5-12(16)11(15)6-18-13(9)17/h8-11H,3-7H2,1-2H3/t8-,9+,10-,11+,15-/m0/s1
SMILES:	CC1(C)C[C@]23[C@@H]4CC[C@H]1[C@@H]2CC(=O)[C@H]3COC4=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509106
PubChem CID:	442299
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
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
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]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984154]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26589	Artemisia annua L.	Strain	Asteraceae	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	=	12400.0	nM	PMID[511248]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	14300.0	nM	PMID[511248]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	16900.0	nM	PMID[511248]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	38.8	%	PMID[511248]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	6.3	%	PMID[511248]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	54.8	%	PMID[511248]

☑ 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 NPC248567 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	354
0.1-0.2	4378
0.2-0.3	15246
0.3-0.4	9305
0.4-0.5	7129
0.5-0.6	4977
0.6-0.7	1128
0.7-0.8	169
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8649	High Similarity	NPC169389
0.863	High Similarity	NPC132064
0.8312	Intermediate Similarity	NPC1882
0.7922	Intermediate Similarity	NPC477918
0.7922	Intermediate Similarity	NPC475932
0.7922	Intermediate Similarity	NPC471151
0.7901	Intermediate Similarity	NPC101138
0.7901	Intermediate Similarity	NPC51135
0.7901	Intermediate Similarity	NPC82492
0.7901	Intermediate Similarity	NPC25802
0.7895	Intermediate Similarity	NPC472311
0.7778	Intermediate Similarity	NPC472847
0.7733	Intermediate Similarity	NPC197701
0.7714	Intermediate Similarity	NPC306750
0.7662	Intermediate Similarity	NPC477934
0.7632	Intermediate Similarity	NPC474755
0.7564	Intermediate Similarity	NPC477933
0.7564	Intermediate Similarity	NPC471046
0.7564	Intermediate Similarity	NPC477932
0.7532	Intermediate Similarity	NPC477867
0.75	Intermediate Similarity	NPC469940
0.75	Intermediate Similarity	NPC472309
0.7468	Intermediate Similarity	NPC74685
0.7467	Intermediate Similarity	NPC295788
0.7463	Intermediate Similarity	NPC319589
0.7442	Intermediate Similarity	NPC200580
0.7439	Intermediate Similarity	NPC13494
0.7397	Intermediate Similarity	NPC157518
0.7397	Intermediate Similarity	NPC469791
0.7368	Intermediate Similarity	NPC477929
0.7349	Intermediate Similarity	NPC15821
0.7324	Intermediate Similarity	NPC84218
0.7308	Intermediate Similarity	NPC477930
0.7284	Intermediate Similarity	NPC472310
0.7273	Intermediate Similarity	NPC473267
0.7273	Intermediate Similarity	NPC470243
0.7273	Intermediate Similarity	NPC478227
0.7262	Intermediate Similarity	NPC473336
0.7262	Intermediate Similarity	NPC109512
0.7262	Intermediate Similarity	NPC319909
0.7262	Intermediate Similarity	NPC471044
0.726	Intermediate Similarity	NPC128608
0.725	Intermediate Similarity	NPC474404
0.7237	Intermediate Similarity	NPC469941
0.7237	Intermediate Similarity	NPC64466
0.7237	Intermediate Similarity	NPC319671
0.7237	Intermediate Similarity	NPC252032
0.7237	Intermediate Similarity	NPC476734
0.7229	Intermediate Similarity	NPC30583
0.7229	Intermediate Similarity	NPC477936
0.7229	Intermediate Similarity	NPC477935
0.7229	Intermediate Similarity	NPC289486
0.7229	Intermediate Similarity	NPC61107
0.7222	Intermediate Similarity	NPC83088
0.7195	Intermediate Similarity	NPC472853
0.7195	Intermediate Similarity	NPC170038
0.7191	Intermediate Similarity	NPC472238
0.7191	Intermediate Similarity	NPC472237
0.7179	Intermediate Similarity	NPC474123
0.7176	Intermediate Similarity	NPC473350
0.716	Intermediate Similarity	NPC185465
0.7143	Intermediate Similarity	NPC108131
0.7143	Intermediate Similarity	NPC477850
0.7143	Intermediate Similarity	NPC476731
0.7126	Intermediate Similarity	NPC90676
0.7126	Intermediate Similarity	NPC56413
0.7108	Intermediate Similarity	NPC58631
0.7105	Intermediate Similarity	NPC470956
0.7093	Intermediate Similarity	NPC120395
0.7089	Intermediate Similarity	NPC280026
0.7089	Intermediate Similarity	NPC167702
0.7089	Intermediate Similarity	NPC133922
0.7083	Intermediate Similarity	NPC478126
0.7083	Intermediate Similarity	NPC66145
0.7073	Intermediate Similarity	NPC474754
0.7073	Intermediate Similarity	NPC320144
0.7073	Intermediate Similarity	NPC118987
0.7073	Intermediate Similarity	NPC471475
0.7067	Intermediate Similarity	NPC42060
0.7067	Intermediate Similarity	NPC477931
0.7067	Intermediate Similarity	NPC268736
0.7067	Intermediate Similarity	NPC84562
0.7045	Intermediate Similarity	NPC11611
0.7024	Intermediate Similarity	NPC100366
0.7024	Intermediate Similarity	NPC311642
0.7024	Intermediate Similarity	NPC164289
0.7024	Intermediate Similarity	NPC271163
0.7024	Intermediate Similarity	NPC242771
0.7024	Intermediate Similarity	NPC102156
0.7024	Intermediate Similarity	NPC148740
0.7024	Intermediate Similarity	NPC24556
0.7015	Intermediate Similarity	NPC274182
0.7013	Intermediate Similarity	NPC178541
0.7013	Intermediate Similarity	NPC474962
0.7013	Intermediate Similarity	NPC196197
0.7	Intermediate Similarity	NPC179858
0.7	Intermediate Similarity	NPC179922
0.7	Intermediate Similarity	NPC212733
0.7	Intermediate Similarity	NPC155441
0.6988	Remote Similarity	NPC261616
0.6977	Remote Similarity	NPC470223
0.6974	Remote Similarity	NPC474221
0.6974	Remote Similarity	NPC478180
0.6974	Remote Similarity	NPC130459
0.6962	Remote Similarity	NPC475230
0.6962	Remote Similarity	NPC109510
0.6957	Remote Similarity	NPC193785
0.6951	Remote Similarity	NPC63020
0.6951	Remote Similarity	NPC476732
0.6951	Remote Similarity	NPC199965
0.6944	Remote Similarity	NPC9880
0.6944	Remote Similarity	NPC230070
0.6944	Remote Similarity	NPC87828
0.6941	Remote Similarity	NPC217559
0.6941	Remote Similarity	NPC268578
0.6941	Remote Similarity	NPC271784
0.6941	Remote Similarity	NPC292458
0.6923	Remote Similarity	NPC56525
0.6923	Remote Similarity	NPC41649
0.6914	Remote Similarity	NPC4209
0.6905	Remote Similarity	NPC472229
0.6905	Remote Similarity	NPC472230
0.6905	Remote Similarity	NPC282293
0.6897	Remote Similarity	NPC92139
0.6875	Remote Similarity	NPC55508
0.6875	Remote Similarity	NPC317212
0.6867	Remote Similarity	NPC28319
0.6867	Remote Similarity	NPC245029
0.6867	Remote Similarity	NPC201276
0.6867	Remote Similarity	NPC31302
0.6867	Remote Similarity	NPC80891
0.686	Remote Similarity	NPC469407
0.686	Remote Similarity	NPC100391
0.686	Remote Similarity	NPC477434
0.6854	Remote Similarity	NPC473039
0.6854	Remote Similarity	NPC474570
0.6842	Remote Similarity	NPC478181
0.6835	Remote Similarity	NPC156277
0.6835	Remote Similarity	NPC320549
0.6835	Remote Similarity	NPC151018
0.6835	Remote Similarity	NPC58057
0.6829	Remote Similarity	NPC143133
0.6829	Remote Similarity	NPC477919
0.6829	Remote Similarity	NPC180199
0.6829	Remote Similarity	NPC143250
0.6829	Remote Similarity	NPC207010
0.6829	Remote Similarity	NPC317913
0.6829	Remote Similarity	NPC298168
0.6813	Remote Similarity	NPC228700
0.6813	Remote Similarity	NPC476189
0.6795	Remote Similarity	NPC98711
0.6795	Remote Similarity	NPC131892
0.6795	Remote Similarity	NPC327728
0.6795	Remote Similarity	NPC321732
0.6795	Remote Similarity	NPC324607
0.6795	Remote Similarity	NPC213178
0.6795	Remote Similarity	NPC6120
0.679	Remote Similarity	NPC125767
0.679	Remote Similarity	NPC21220
0.6786	Remote Similarity	NPC134227
0.6786	Remote Similarity	NPC125366
0.6786	Remote Similarity	NPC477851
0.6782	Remote Similarity	NPC474971
0.6782	Remote Similarity	NPC201655
0.6782	Remote Similarity	NPC62572
0.6782	Remote Similarity	NPC477205
0.6753	Remote Similarity	NPC41542
0.675	Remote Similarity	NPC232112
0.675	Remote Similarity	NPC279241
0.675	Remote Similarity	NPC177826
0.675	Remote Similarity	NPC310766
0.6747	Remote Similarity	NPC34046
0.6747	Remote Similarity	NPC171426
0.6747	Remote Similarity	NPC324700
0.6747	Remote Similarity	NPC80089
0.6747	Remote Similarity	NPC329117
0.6747	Remote Similarity	NPC224802
0.6744	Remote Similarity	NPC469561
0.6744	Remote Similarity	NPC259173
0.6742	Remote Similarity	NPC33398
0.6742	Remote Similarity	NPC28227
0.6742	Remote Similarity	NPC183374
0.6742	Remote Similarity	NPC191221
0.6742	Remote Similarity	NPC80335
0.6742	Remote Similarity	NPC211162
0.6739	Remote Similarity	NPC247877
0.6739	Remote Similarity	NPC309127
0.6739	Remote Similarity	NPC206878
0.6716	Remote Similarity	NPC247786
0.6716	Remote Similarity	NPC293343
0.6716	Remote Similarity	NPC258672
0.6711	Remote Similarity	NPC306805
0.6711	Remote Similarity	NPC215987
0.6707	Remote Similarity	NPC472487
0.6707	Remote Similarity	NPC92489
0.6707	Remote Similarity	NPC5767
0.6707	Remote Similarity	NPC474020
0.6707	Remote Similarity	NPC475742
0.6707	Remote Similarity	NPC472486
0.6706	Remote Similarity	NPC232625

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 NPC248567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	3948
0.2-0.3	3430
0.3-0.4	802
0.4-0.5	283
0.5-0.6	228
0.6-0.7	60
0.7-0.8	7
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
0.7895	Intermediate Similarity	NPD3702	Approved
0.7733	Intermediate Similarity	NPD5777	Approved
0.75	Intermediate Similarity	NPD6081	Approved
0.7397	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4224	Phase 2
0.7089	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4789	Approved
0.6914	Remote Similarity	NPD6117	Approved
0.6835	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6116	Phase 1
0.6795	Remote Similarity	NPD3698	Phase 2
0.6795	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6114	Approved
0.6747	Remote Similarity	NPD6115	Approved
0.6747	Remote Similarity	NPD6697	Approved
0.6747	Remote Similarity	NPD6118	Approved
0.6742	Remote Similarity	NPD6903	Approved
0.6709	Remote Similarity	NPD4245	Approved
0.6709	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3703	Phase 2
0.6556	Remote Similarity	NPD5737	Approved
0.6556	Remote Similarity	NPD6672	Approved
0.6517	Remote Similarity	NPD7334	Approved
0.6517	Remote Similarity	NPD6409	Approved
0.6517	Remote Similarity	NPD7146	Approved
0.6517	Remote Similarity	NPD5330	Approved
0.6517	Remote Similarity	NPD6684	Approved
0.6517	Remote Similarity	NPD7521	Approved
0.6456	Remote Similarity	NPD229	Approved
0.642	Remote Similarity	NPD4758	Discontinued
0.6418	Remote Similarity	NPD343	Approved
0.6418	Remote Similarity	NPD345	Approved
0.6418	Remote Similarity	NPD344	Approved
0.6374	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4802	Phase 2
0.6353	Remote Similarity	NPD4238	Approved
0.6333	Remote Similarity	NPD6098	Approved
0.6289	Remote Similarity	NPD5696	Approved
0.6277	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5207	Approved
0.6222	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5208	Approved
0.617	Remote Similarity	NPD8034	Phase 2
0.617	Remote Similarity	NPD8035	Phase 2
0.6163	Remote Similarity	NPD3671	Phase 1
0.6162	Remote Similarity	NPD1700	Approved
0.6146	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5695	Phase 3
0.6136	Remote Similarity	NPD1780	Approved
0.6136	Remote Similarity	NPD1779	Approved
0.6129	Remote Similarity	NPD6904	Approved
0.6129	Remote Similarity	NPD6080	Approved
0.6129	Remote Similarity	NPD6673	Approved
0.6076	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5692	Phase 3
0.6053	Remote Similarity	NPD3198	Approved
0.6042	Remote Similarity	NPD6001	Approved
0.602	Remote Similarity	NPD6084	Phase 2
0.602	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD5694	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD4788	Approved
0.6	Remote Similarity	NPD5693	Phase 1
0.5977	Remote Similarity	NPD5364	Discontinued
0.5976	Remote Similarity	NPD3725	Approved
0.5976	Remote Similarity	NPD3726	Approved
0.5962	Remote Similarity	NPD7320	Approved
0.5934	Remote Similarity	NPD4786	Approved
0.5922	Remote Similarity	NPD6008	Approved
0.5914	Remote Similarity	NPD3573	Approved
0.5889	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD3667	Approved
0.587	Remote Similarity	NPD1694	Approved
0.5825	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5654	Approved
0.5795	Remote Similarity	NPD3617	Approved
0.5789	Remote Similarity	NPD5328	Approved
0.5778	Remote Similarity	NPD4139	Approved
0.5778	Remote Similarity	NPD4692	Approved
0.5769	Remote Similarity	NPD5739	Approved
0.5769	Remote Similarity	NPD7128	Approved
0.5769	Remote Similarity	NPD6402	Approved
0.5769	Remote Similarity	NPD6675	Approved
0.5761	Remote Similarity	NPD3665	Phase 1
0.5761	Remote Similarity	NPD3133	Approved
0.5761	Remote Similarity	NPD3668	Phase 3
0.5761	Remote Similarity	NPD3666	Approved
0.5714	Remote Similarity	NPD4221	Approved
0.5714	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD4223	Phase 3
0.5714	Remote Similarity	NPD5701	Approved
0.57	Remote Similarity	NPD5959	Approved
0.567	Remote Similarity	NPD5281	Approved
0.567	Remote Similarity	NPD5284	Approved
0.567	Remote Similarity	NPD6079	Approved
0.567	Remote Similarity	NPD6411	Approved
0.5667	Remote Similarity	NPD6928	Phase 2
0.566	Remote Similarity	NPD6011	Approved
0.566	Remote Similarity	NPD6899	Approved
0.566	Remote Similarity	NPD6881	Approved
0.5657	Remote Similarity	NPD4629	Approved
0.5657	Remote Similarity	NPD5210	Approved
0.5638	Remote Similarity	NPD3618	Phase 1
0.5638	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD5279	Phase 3
0.5625	Remote Similarity	NPD4753	Phase 2
0.5619	Remote Similarity	NPD6920	Discontinued
0.561	Remote Similarity	NPD375	Phase 2
0.5607	Remote Similarity	NPD6014	Approved
0.5607	Remote Similarity	NPD6372	Approved
0.5607	Remote Similarity	NPD6373	Approved
0.5607	Remote Similarity	NPD6013	Approved
0.5607	Remote Similarity	NPD6012	Approved
0.56	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7732	Phase 3

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