NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.09
Volume:	252.879
LogP:	3.897
LogD:	2.8
LogS:	-3.401
# Rotatable Bonds:	0
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.689
Synthetic Accessibility Score:	3.556
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.884
MDCK Permeability:	7.041169737931341e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.203
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	96.16854095458984%
Volume Distribution (VD):	0.764
Pgp-substrate:	5.713848114013672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.719
CYP2C19-inhibitor:	0.111
CYP2C19-substrate:	0.245
CYP2C9-inhibitor:	0.399
CYP2C9-substrate:	0.55
CYP2D6-inhibitor:	0.238
CYP2D6-substrate:	0.409
CYP3A4-inhibitor:	0.112
CYP3A4-substrate:	0.186

ADMET: Excretion

Clearance (CL):	10.653
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.928
AMES Toxicity:	0.688
Rat Oral Acute Toxicity:	0.747
Maximum Recommended Daily Dose:	0.434
Skin Sensitization:	0.899
Carcinogencity:	0.821
Eye Corrosion:	0.01
Eye Irritation:	0.918
Respiratory Toxicity:	0.525

Download Data

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

Natural Product: NPC135730

Natural Product ID:	NPC135730
*Common Name:**	Mansonone E
IUPAC Name:	n.a.
Synonyms:	Mansonone E
Standard InCHIKey:	SYWTYRLIJCHSLJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O3/c1-7-4-5-10-8(2)6-18-15-9(3)13(16)14(17)11(7)12(10)15/h4-5,8H,6H2,1-3H3
SMILES:	Cc1ccc2C(C)COC3=C(C)C(=O)C(=O)c1c23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL362672
PubChem CID:	94303
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18553924]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23734721]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19367	Thespesia populnea	Species	Malvaceae	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	13
MIC	6
Others	9

Activity Type	# Activity
Cell Line	8
Individual Protein	1
NON-MOLECULAR	10
Organism	6
Others	2
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.05	ug.mL-1	PMID[519990]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	0.55	ug.mL-1	PMID[519990]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	0.18	ug.mL-1	PMID[519990]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.4	ug.mL-1	PMID[519990]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	15720.0	nM	PMID[519992]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	12230.0	nM	PMID[519992]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	10630.0	nM	PMID[519992]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	17510.0	nM	PMID[519992]
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	18600.0	nM	PMID[519992]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC50	=	8.0	ug.mL-1	PMID[519988]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC90	=	16.0	ug.mL-1	PMID[519988]
NPT35	Others	n.a.		Activity	=	66.0	microM/min	PMID[519989]
NPT35	Others	n.a.		Activity	=	276.0	microM/min	PMID[519989]
NPT1266	Organism	Leptomonas seymouri	Leptomonas seymouri	IC50	=	400.0	nM	PMID[519989]
NPT1267	Organism	Crithidia fasciculata	Crithidia fasciculata	IC50	=	600.0	nM	PMID[519989]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.69	ug.mL-1	PMID[519990]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	45700.0	nM	PMID[519991]
NPT3494	Organism	Coxsackievirus	Coxsackievirus	IC50	=	4700.0	nM	PMID[519991]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	20.3	mm	PMID[519993]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	19.7	mm	PMID[519993]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	16.7	mm	PMID[519993]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	13.5	mm	PMID[519993]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	11.6	mm	PMID[519993]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	31250.0	nM	PMID[519993]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	3900.0	nM	PMID[519993]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	15600.0	nM	PMID[519993]

☑ 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 NPC135730 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	290
0.1-0.2	1392
0.2-0.3	2873
0.3-0.4	8106
0.4-0.5	11955
0.5-0.6	9200
0.6-0.7	7953
0.7-0.8	855
0.8-0.85	55
0.85-0.9	6
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9537	High Similarity	NPC13784
0.9381	High Similarity	NPC988
0.9381	High Similarity	NPC289432
0.9364	High Similarity	NPC228936
0.9298	High Similarity	NPC144547
0.9211	High Similarity	NPC238861
0.9211	High Similarity	NPC77000
0.9189	High Similarity	NPC474095
0.9099	High Similarity	NPC196075
0.8929	High Similarity	NPC477411
0.8919	High Similarity	NPC212415
0.8898	High Similarity	NPC51079
0.8879	High Similarity	NPC232958
0.8829	High Similarity	NPC210089
0.8772	High Similarity	NPC226093
0.8522	High Similarity	NPC470764
0.8421	Intermediate Similarity	NPC79496
0.8393	Intermediate Similarity	NPC470391
0.8362	Intermediate Similarity	NPC474408
0.8346	Intermediate Similarity	NPC59459
0.8333	Intermediate Similarity	NPC474057
0.8333	Intermediate Similarity	NPC291799
0.8333	Intermediate Similarity	NPC167504
0.8214	Intermediate Similarity	NPC209632
0.8203	Intermediate Similarity	NPC310662
0.8174	Intermediate Similarity	NPC474157
0.8174	Intermediate Similarity	NPC137315
0.8158	Intermediate Similarity	NPC83628
0.8158	Intermediate Similarity	NPC265407
0.8151	Intermediate Similarity	NPC228318
0.8142	Intermediate Similarity	NPC30594
0.8142	Intermediate Similarity	NPC37622
0.8125	Intermediate Similarity	NPC114594
0.812	Intermediate Similarity	NPC241851
0.812	Intermediate Similarity	NPC196673
0.812	Intermediate Similarity	NPC326664
0.807	Intermediate Similarity	NPC203732
0.8065	Intermediate Similarity	NPC295664
0.8051	Intermediate Similarity	NPC210092
0.8051	Intermediate Similarity	NPC306740
0.8047	Intermediate Similarity	NPC279596
0.8036	Intermediate Similarity	NPC60679
0.8034	Intermediate Similarity	NPC128368
0.8034	Intermediate Similarity	NPC272524
0.8018	Intermediate Similarity	NPC70624
0.8016	Intermediate Similarity	NPC428300
0.8	Intermediate Similarity	NPC99846
0.8	Intermediate Similarity	NPC192577
0.8	Intermediate Similarity	NPC269023
0.7984	Intermediate Similarity	NPC183103
0.7984	Intermediate Similarity	NPC228739
0.7982	Intermediate Similarity	NPC119271
0.7966	Intermediate Similarity	NPC308744
0.7966	Intermediate Similarity	NPC307651
0.7966	Intermediate Similarity	NPC67377
0.7949	Intermediate Similarity	NPC82899
0.7949	Intermediate Similarity	NPC270699
0.7939	Intermediate Similarity	NPC309056
0.7937	Intermediate Similarity	NPC177925
0.7937	Intermediate Similarity	NPC474737
0.7937	Intermediate Similarity	NPC51292
0.7934	Intermediate Similarity	NPC318173
0.7931	Intermediate Similarity	NPC196246
0.7931	Intermediate Similarity	NPC214067
0.7931	Intermediate Similarity	NPC273837
0.7917	Intermediate Similarity	NPC190298
0.7913	Intermediate Similarity	NPC56493
0.7907	Intermediate Similarity	NPC239134
0.7903	Intermediate Similarity	NPC223351
0.7899	Intermediate Similarity	NPC474685
0.7895	Intermediate Similarity	NPC172483
0.7891	Intermediate Similarity	NPC471832
0.7891	Intermediate Similarity	NPC57552
0.7886	Intermediate Similarity	NPC472981
0.7876	Intermediate Similarity	NPC89886
0.7874	Intermediate Similarity	NPC115797
0.7874	Intermediate Similarity	NPC51448
0.7869	Intermediate Similarity	NPC204784
0.7863	Intermediate Similarity	NPC212207
0.7863	Intermediate Similarity	NPC305912
0.7863	Intermediate Similarity	NPC1082
0.7857	Intermediate Similarity	NPC112552
0.7857	Intermediate Similarity	NPC236405
0.7851	Intermediate Similarity	NPC323440
0.7851	Intermediate Similarity	NPC45794
0.7851	Intermediate Similarity	NPC222968
0.7851	Intermediate Similarity	NPC80605
0.7845	Intermediate Similarity	NPC17417
0.7845	Intermediate Similarity	NPC10251
0.784	Intermediate Similarity	NPC182646
0.784	Intermediate Similarity	NPC328107
0.784	Intermediate Similarity	NPC318067
0.7838	Intermediate Similarity	NPC225060
0.7833	Intermediate Similarity	NPC149691
0.7807	Intermediate Similarity	NPC31786
0.7797	Intermediate Similarity	NPC292834
0.7788	Intermediate Similarity	NPC188895
0.7778	Intermediate Similarity	NPC251854
0.7778	Intermediate Similarity	NPC93084
0.7778	Intermediate Similarity	NPC174099
0.7769	Intermediate Similarity	NPC477412
0.7769	Intermediate Similarity	NPC164295
0.7768	Intermediate Similarity	NPC203925
0.7768	Intermediate Similarity	NPC146351
0.776	Intermediate Similarity	NPC65627
0.7752	Intermediate Similarity	NPC82712
0.775	Intermediate Similarity	NPC221275
0.7748	Intermediate Similarity	NPC276775
0.7748	Intermediate Similarity	NPC92754
0.7748	Intermediate Similarity	NPC249912
0.7742	Intermediate Similarity	NPC50872
0.7731	Intermediate Similarity	NPC143768
0.7727	Intermediate Similarity	NPC23894
0.7727	Intermediate Similarity	NPC5472
0.7719	Intermediate Similarity	NPC301943
0.7719	Intermediate Similarity	NPC274443
0.7719	Intermediate Similarity	NPC247976
0.7719	Intermediate Similarity	NPC474365
0.7717	Intermediate Similarity	NPC476599
0.7712	Intermediate Similarity	NPC260818
0.7712	Intermediate Similarity	NPC265513
0.771	Intermediate Similarity	NPC477407
0.771	Intermediate Similarity	NPC476644
0.771	Intermediate Similarity	NPC477406
0.7705	Intermediate Similarity	NPC61651
0.7699	Intermediate Similarity	NPC42211
0.7698	Intermediate Similarity	NPC85511
0.7686	Intermediate Similarity	NPC100353
0.7686	Intermediate Similarity	NPC471616
0.7679	Intermediate Similarity	NPC78701
0.7679	Intermediate Similarity	NPC35448
0.7672	Intermediate Similarity	NPC83409
0.7672	Intermediate Similarity	NPC185763
0.7669	Intermediate Similarity	NPC217914
0.7667	Intermediate Similarity	NPC153053
0.7661	Intermediate Similarity	NPC473243
0.7661	Intermediate Similarity	NPC476225
0.7661	Intermediate Similarity	NPC105709
0.7652	Intermediate Similarity	NPC470406
0.7652	Intermediate Similarity	NPC263817
0.7647	Intermediate Similarity	NPC280789
0.7647	Intermediate Similarity	NPC471188
0.7647	Intermediate Similarity	NPC66208
0.7647	Intermediate Similarity	NPC321852
0.7638	Intermediate Similarity	NPC75432
0.7634	Intermediate Similarity	NPC472394
0.7632	Intermediate Similarity	NPC45613
0.7632	Intermediate Similarity	NPC244427
0.7632	Intermediate Similarity	NPC222390
0.7623	Intermediate Similarity	NPC158157
0.7615	Intermediate Similarity	NPC133461
0.7615	Intermediate Similarity	NPC262819
0.7612	Intermediate Similarity	NPC471670
0.7612	Intermediate Similarity	NPC232996
0.7611	Intermediate Similarity	NPC476042
0.7611	Intermediate Similarity	NPC118343
0.7609	Intermediate Similarity	NPC117674
0.7607	Intermediate Similarity	NPC211439
0.7603	Intermediate Similarity	NPC186933
0.7603	Intermediate Similarity	NPC476357
0.7603	Intermediate Similarity	NPC274839
0.7597	Intermediate Similarity	NPC45537
0.7594	Intermediate Similarity	NPC1249
0.7594	Intermediate Similarity	NPC474659
0.7586	Intermediate Similarity	NPC134120
0.7583	Intermediate Similarity	NPC161611
0.7583	Intermediate Similarity	NPC470253
0.7581	Intermediate Similarity	NPC202015
0.7578	Intermediate Similarity	NPC470765
0.7578	Intermediate Similarity	NPC470858
0.7574	Intermediate Similarity	NPC470407
0.7568	Intermediate Similarity	NPC130398
0.7568	Intermediate Similarity	NPC260233
0.7563	Intermediate Similarity	NPC243355
0.7559	Intermediate Similarity	NPC141252
0.7559	Intermediate Similarity	NPC11799
0.7557	Intermediate Similarity	NPC27659
0.7556	Intermediate Similarity	NPC119542
0.7556	Intermediate Similarity	NPC186647
0.7556	Intermediate Similarity	NPC284184
0.7556	Intermediate Similarity	NPC301341
0.7545	Intermediate Similarity	NPC153885
0.7542	Intermediate Similarity	NPC474364
0.7542	Intermediate Similarity	NPC469636
0.7542	Intermediate Similarity	NPC85493
0.7542	Intermediate Similarity	NPC318327
0.7541	Intermediate Similarity	NPC260886
0.754	Intermediate Similarity	NPC167323
0.754	Intermediate Similarity	NPC269923
0.7538	Intermediate Similarity	NPC59502
0.7537	Intermediate Similarity	NPC22644
0.7537	Intermediate Similarity	NPC89504
0.7537	Intermediate Similarity	NPC95485
0.7537	Intermediate Similarity	NPC88065
0.7523	Intermediate Similarity	NPC173413
0.7521	Intermediate Similarity	NPC100767
0.752	Intermediate Similarity	NPC133302
0.7519	Intermediate Similarity	NPC81135
0.7519	Intermediate Similarity	NPC473220
0.7519	Intermediate Similarity	NPC203486

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 NPC135730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	975
0.2-0.3	1094
0.3-0.4	2637
0.4-0.5	2419
0.5-0.6	1307
0.6-0.7	405
0.7-0.8	37
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9211	High Similarity	NPD3412	Clinical (unspecified phase)
0.8919	High Similarity	NPD1609	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD2182	Approved
0.7807	Intermediate Similarity	NPD164	Approved
0.7615	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD1238	Approved
0.76	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD1651	Approved
0.7563	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD1281	Approved
0.7521	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1876	Approved
0.7481	Intermediate Similarity	NPD7008	Discontinued
0.748	Intermediate Similarity	NPD3972	Approved
0.7459	Intermediate Similarity	NPD5951	Approved
0.7434	Intermediate Similarity	NPD3495	Discontinued
0.7402	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1283	Approved
0.7266	Intermediate Similarity	NPD6287	Discontinued
0.7265	Intermediate Similarity	NPD1930	Approved
0.7265	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD1929	Approved
0.7258	Intermediate Similarity	NPD3317	Approved
0.7248	Intermediate Similarity	NPD650	Approved
0.7244	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7631	Approved
0.7209	Intermediate Similarity	NPD4878	Approved
0.7203	Intermediate Similarity	NPD1237	Approved
0.7203	Intermediate Similarity	NPD5909	Discontinued
0.7185	Intermediate Similarity	NPD2979	Phase 3
0.7177	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5691	Approved
0.7143	Intermediate Similarity	NPD7609	Phase 3
0.7122	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1471	Phase 3
0.7121	Intermediate Similarity	NPD2798	Approved
0.7111	Intermediate Similarity	NPD7713	Phase 3
0.7107	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7003	Approved
0.7049	Intermediate Similarity	NPD2067	Discontinued
0.7043	Intermediate Similarity	NPD1989	Approved
0.7037	Intermediate Similarity	NPD2313	Discontinued
0.7016	Intermediate Similarity	NPD6858	Approved
0.7016	Intermediate Similarity	NPD7094	Approved
0.7009	Intermediate Similarity	NPD2066	Phase 3
0.7	Intermediate Similarity	NPD1201	Approved
0.6993	Remote Similarity	NPD7236	Approved
0.6978	Remote Similarity	NPD2799	Discontinued
0.6977	Remote Similarity	NPD17	Approved
0.6963	Remote Similarity	NPD6039	Approved
0.6953	Remote Similarity	NPD9545	Approved
0.6939	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3226	Approved
0.6937	Remote Similarity	NPD1087	Approved
0.6929	Remote Similarity	NPD2531	Phase 2
0.6929	Remote Similarity	NPD2438	Suspended
0.6929	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3266	Approved
0.6917	Remote Similarity	NPD1470	Approved
0.6917	Remote Similarity	NPD3267	Approved
0.6912	Remote Similarity	NPD3764	Approved
0.6891	Remote Similarity	NPD1932	Approved
0.6871	Remote Similarity	NPD7239	Suspended
0.687	Remote Similarity	NPD1202	Approved
0.6866	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD8032	Phase 2
0.6857	Remote Similarity	NPD3748	Approved
0.6849	Remote Similarity	NPD6273	Approved
0.6847	Remote Similarity	NPD9259	Approved
0.6847	Remote Similarity	NPD9257	Approved
0.6846	Remote Similarity	NPD4626	Approved
0.6846	Remote Similarity	NPD2932	Approved
0.6829	Remote Similarity	NPD2329	Discontinued
0.6825	Remote Similarity	NPD6010	Discontinued
0.6824	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7458	Discontinued
0.6818	Remote Similarity	NPD1608	Approved
0.6812	Remote Similarity	NPD3142	Approved
0.6812	Remote Similarity	NPD4307	Phase 2
0.6812	Remote Similarity	NPD3140	Approved
0.681	Remote Similarity	NPD688	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1693	Approved
0.6809	Remote Similarity	NPD2796	Approved
0.6794	Remote Similarity	NPD4879	Approved
0.6783	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2629	Approved
0.6769	Remote Similarity	NPD3024	Approved
0.6769	Remote Similarity	NPD3025	Approved
0.6761	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7819	Suspended
0.6754	Remote Similarity	NPD1089	Approved
0.6754	Remote Similarity	NPD1086	Approved
0.6754	Remote Similarity	NPD1090	Approved
0.6742	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4628	Phase 3
0.6724	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1563	Approved
0.6719	Remote Similarity	NPD4198	Discontinued
0.6718	Remote Similarity	NPD3019	Approved
0.6718	Remote Similarity	NPD5126	Approved
0.6718	Remote Similarity	NPD5125	Phase 3
0.6714	Remote Similarity	NPD1607	Approved
0.6711	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7009	Phase 2
0.669	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3026	Approved
0.6667	Remote Similarity	NPD800	Approved
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD9493	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD3023	Approved
0.6643	Remote Similarity	NPD4622	Approved
0.6643	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2344	Approved
0.6643	Remote Similarity	NPD4618	Approved
0.6643	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7055	Discontinued
0.6642	Remote Similarity	NPD6832	Phase 2
0.6641	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD1088	Approved
0.6638	Remote Similarity	NPD1508	Approved
0.6637	Remote Similarity	NPD1282	Approved
0.6621	Remote Similarity	NPD8166	Discontinued
0.6621	Remote Similarity	NPD3750	Approved
0.662	Remote Similarity	NPD4308	Phase 3
0.662	Remote Similarity	NPD1510	Phase 2
0.6618	Remote Similarity	NPD6085	Phase 2
0.6618	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD1611	Approved
0.6615	Remote Similarity	NPD7610	Discontinued
0.6609	Remote Similarity	NPD3672	Approved
0.6609	Remote Similarity	NPD3673	Approved
0.6609	Remote Similarity	NPD9258	Approved
0.6609	Remote Similarity	NPD9256	Approved
0.6601	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1549	Phase 2
0.6593	Remote Similarity	NPD5667	Approved
0.6573	Remote Similarity	NPD4476	Approved
0.6573	Remote Similarity	NPD6099	Approved
0.6573	Remote Similarity	NPD4477	Approved
0.6573	Remote Similarity	NPD6100	Approved
0.6571	Remote Similarity	NPD1240	Approved
0.6569	Remote Similarity	NPD9494	Approved
0.6567	Remote Similarity	NPD6637	Approved
0.6565	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD1564	Approved
0.6555	Remote Similarity	NPD1566	Phase 3
0.6555	Remote Similarity	NPD1565	Approved
0.6554	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1239	Approved
0.6549	Remote Similarity	NPD5688	Approved
0.6549	Remote Similarity	NPD5689	Approved
0.6545	Remote Similarity	NPD942	Approved
0.6538	Remote Similarity	NPD5494	Approved
0.6532	Remote Similarity	NPD3134	Approved
0.6519	Remote Similarity	NPD5159	Phase 2
0.6519	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5157	Phase 1
0.6519	Remote Similarity	NPD5327	Phase 3
0.6515	Remote Similarity	NPD5585	Approved
0.6508	Remote Similarity	NPD1317	Discontinued
0.6507	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD3048	Approved
0.6504	Remote Similarity	NPD3046	Approved
0.6504	Remote Similarity	NPD3047	Approved
0.65	Remote Similarity	NPD9495	Approved
0.65	Remote Similarity	NPD6663	Approved
0.65	Remote Similarity	NPD7961	Discontinued
0.6497	Remote Similarity	NPD6959	Discontinued
0.6496	Remote Similarity	NPD2788	Approved
0.6496	Remote Similarity	NPD1019	Discontinued
0.6494	Remote Similarity	NPD5978	Approved
0.6494	Remote Similarity	NPD5977	Approved
0.6483	Remote Similarity	NPD2897	Discontinued
0.6479	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2198	Approved
0.6471	Remote Similarity	NPD2199	Approved
0.6471	Remote Similarity	NPD1843	Approved
0.6467	Remote Similarity	NPD920	Approved
0.6466	Remote Similarity	NPD1778	Approved
0.6463	Remote Similarity	NPD2309	Approved
0.6458	Remote Similarity	NPD2935	Discontinued
0.6457	Remote Similarity	NPD2201	Approved
0.6454	Remote Similarity	NPD3373	Approved
0.6452	Remote Similarity	NPD7058	Phase 2
0.6452	Remote Similarity	NPD7057	Phase 3
0.6449	Remote Similarity	NPD5736	Approved
0.6447	Remote Similarity	NPD4380	Phase 2
0.6444	Remote Similarity	NPD9717	Approved
0.6443	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7422	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