NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.09
Volume:	252.879
LogP:	3.388
LogD:	2.97
LogS:	-5.187
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	3.599
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.921
MDCK Permeability:	2.0432491510291584e-05
Pgp-inhibitor:	0.108
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.284

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	97.9280014038086%
Volume Distribution (VD):	0.584
Pgp-substrate:	1.4972124099731445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.785
CYP2C19-substrate:	0.578
CYP2C9-inhibitor:	0.767
CYP2C9-substrate:	0.643
CYP2D6-inhibitor:	0.699
CYP2D6-substrate:	0.48
CYP3A4-inhibitor:	0.502
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	4.084
Half-life (T1/2):	0.115

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.185
Drug-inuced Liver Injury (DILI):	0.549
AMES Toxicity:	0.943
Rat Oral Acute Toxicity:	0.712
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.865
Carcinogencity:	0.919
Eye Corrosion:	0.006
Eye Irritation:	0.92
Respiratory Toxicity:	0.506

Download Data

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

Natural Product: NPC279596

Natural Product ID:	NPC279596
*Common Name:**	Mansonone D
IUPAC Name:	1,5,8-trimethyl-1,2-dihydrobenzo[e][1]benzofuran-6,7-dione
Synonyms:	Mansonone D
Standard InCHIKey:	LTOSSAVPMIKCBC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O3/c1-7-5-11-12(9(3)6-18-11)10-4-8(2)14(16)15(17)13(7)10/h4-5,9H,6H2,1-3H3
SMILES:	Cc1cc2c(C(C)CO2)c2C=C(C)C(=O)C(=O)c12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513280
PubChem CID:	3083888
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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]
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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	4
MIC	1

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[528485]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2.8	ug.mL-1	PMID[528485]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[528485]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	4.9	ug.mL-1	PMID[528485]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	2.34	ug.mL-1	PMID[528485]

☑ 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 NPC279596 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	402
0.1-0.2	1617
0.2-0.3	3728
0.3-0.4	10306
0.4-0.5	8452
0.5-0.6	4140
0.6-0.7	8576
0.7-0.8	5245
0.8-0.85	192
0.85-0.9	29
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC474737
0.916	High Similarity	NPC209858
0.9077	High Similarity	NPC239134
0.9055	High Similarity	NPC470858
0.9048	High Similarity	NPC141252
0.9048	High Similarity	NPC11799
0.903	High Similarity	NPC233707
0.9015	High Similarity	NPC324117
0.9008	High Similarity	NPC183103
0.8931	High Similarity	NPC164295
0.8806	High Similarity	NPC217914
0.8741	High Similarity	NPC471670
0.8667	High Similarity	NPC22644
0.8657	High Similarity	NPC59459
0.8647	High Similarity	NPC196979
0.8647	High Similarity	NPC470976
0.8647	High Similarity	NPC470977
0.8636	High Similarity	NPC170546
0.8636	High Similarity	NPC939
0.8636	High Similarity	NPC66246
0.8582	High Similarity	NPC312560
0.8571	High Similarity	NPC183348
0.8571	High Similarity	NPC282230
0.8571	High Similarity	NPC158871
0.8561	High Similarity	NPC59502
0.855	High Similarity	NPC177925
0.854	High Similarity	NPC186647
0.8519	High Similarity	NPC263817
0.8511	High Similarity	NPC290038
0.8511	High Similarity	NPC308006
0.8507	High Similarity	NPC477412
0.8507	High Similarity	NPC15083
0.8462	Intermediate Similarity	NPC182646
0.8444	Intermediate Similarity	NPC470859
0.8421	Intermediate Similarity	NPC50583
0.8409	Intermediate Similarity	NPC237868
0.8397	Intermediate Similarity	NPC75432
0.8385	Intermediate Similarity	NPC282577
0.8382	Intermediate Similarity	NPC470406
0.838	Intermediate Similarity	NPC471451
0.8346	Intermediate Similarity	NPC428300
0.8333	Intermediate Similarity	NPC232996
0.8321	Intermediate Similarity	NPC247743
0.831	Intermediate Similarity	NPC117674
0.8299	Intermediate Similarity	NPC10429
0.8296	Intermediate Similarity	NPC470725
0.8286	Intermediate Similarity	NPC470407
0.8281	Intermediate Similarity	NPC171023
0.8276	Intermediate Similarity	NPC95526
0.8276	Intermediate Similarity	NPC472839
0.8273	Intermediate Similarity	NPC290601
0.8271	Intermediate Similarity	NPC474264
0.8264	Intermediate Similarity	NPC471346
0.8261	Intermediate Similarity	NPC470844
0.8258	Intermediate Similarity	NPC30216
0.8252	Intermediate Similarity	NPC189650
0.8235	Intermediate Similarity	NPC301717
0.8227	Intermediate Similarity	NPC109007
0.8222	Intermediate Similarity	NPC57552
0.8219	Intermediate Similarity	NPC472298
0.8209	Intermediate Similarity	NPC45537
0.8195	Intermediate Similarity	NPC165556
0.8195	Intermediate Similarity	NPC123506
0.8188	Intermediate Similarity	NPC478161
0.8188	Intermediate Similarity	NPC478159
0.8182	Intermediate Similarity	NPC178382
0.8182	Intermediate Similarity	NPC215451
0.8182	Intermediate Similarity	NPC277369
0.8176	Intermediate Similarity	NPC27615
0.8175	Intermediate Similarity	NPC477407
0.8162	Intermediate Similarity	NPC253488
0.816	Intermediate Similarity	NPC23332
0.8143	Intermediate Similarity	NPC119542
0.8143	Intermediate Similarity	NPC284184
0.8143	Intermediate Similarity	NPC301341
0.8138	Intermediate Similarity	NPC286038
0.8138	Intermediate Similarity	NPC473927
0.8129	Intermediate Similarity	NPC95485
0.8129	Intermediate Similarity	NPC89504
0.8129	Intermediate Similarity	NPC88065
0.8125	Intermediate Similarity	NPC79202
0.8125	Intermediate Similarity	NPC472836
0.8125	Intermediate Similarity	NPC93241
0.8125	Intermediate Similarity	NPC245522
0.8125	Intermediate Similarity	NPC114513
0.8125	Intermediate Similarity	NPC471305
0.8125	Intermediate Similarity	NPC59035
0.8125	Intermediate Similarity	NPC469385
0.8125	Intermediate Similarity	NPC27798
0.812	Intermediate Similarity	NPC199273
0.8112	Intermediate Similarity	NPC27220
0.8112	Intermediate Similarity	NPC297985
0.8112	Intermediate Similarity	NPC11314
0.811	Intermediate Similarity	NPC252004
0.8102	Intermediate Similarity	NPC205360
0.8095	Intermediate Similarity	NPC228906
0.8095	Intermediate Similarity	NPC471348
0.8095	Intermediate Similarity	NPC469416
0.8092	Intermediate Similarity	NPC313368
0.8085	Intermediate Similarity	NPC62735
0.8085	Intermediate Similarity	NPC265181
0.8082	Intermediate Similarity	NPC478163
0.8082	Intermediate Similarity	NPC66991
0.8082	Intermediate Similarity	NPC123202
0.8082	Intermediate Similarity	NPC7943
0.8082	Intermediate Similarity	NPC22005
0.808	Intermediate Similarity	NPC183648
0.8074	Intermediate Similarity	NPC37512
0.8074	Intermediate Similarity	NPC72667
0.8071	Intermediate Similarity	NPC163029
0.8071	Intermediate Similarity	NPC307401
0.8069	Intermediate Similarity	NPC49282
0.8069	Intermediate Similarity	NPC225351
0.8062	Intermediate Similarity	NPC469954
0.806	Intermediate Similarity	NPC224657
0.8058	Intermediate Similarity	NPC265793
0.8058	Intermediate Similarity	NPC274876
0.8058	Intermediate Similarity	NPC1249
0.8056	Intermediate Similarity	NPC472840
0.8056	Intermediate Similarity	NPC167663
0.8054	Intermediate Similarity	NPC271681
0.8054	Intermediate Similarity	NPC154683
0.8054	Intermediate Similarity	NPC40356
0.8054	Intermediate Similarity	NPC44606
0.8054	Intermediate Similarity	NPC87708
0.8047	Intermediate Similarity	NPC135730
0.8045	Intermediate Similarity	NPC474691
0.8043	Intermediate Similarity	NPC477406
0.8042	Intermediate Similarity	NPC263337
0.8041	Intermediate Similarity	NPC13282
0.8041	Intermediate Similarity	NPC202595
0.8041	Intermediate Similarity	NPC474660
0.8029	Intermediate Similarity	NPC245395
0.8029	Intermediate Similarity	NPC109778
0.8028	Intermediate Similarity	NPC223336
0.8027	Intermediate Similarity	NPC474107
0.8027	Intermediate Similarity	NPC256672
0.8027	Intermediate Similarity	NPC27221
0.8027	Intermediate Similarity	NPC219560
0.8027	Intermediate Similarity	NPC7025
0.8026	Intermediate Similarity	NPC472299
0.8016	Intermediate Similarity	NPC470723
0.8015	Intermediate Similarity	NPC96024
0.8015	Intermediate Similarity	NPC246214
0.8015	Intermediate Similarity	NPC3009
0.8015	Intermediate Similarity	NPC125887
0.8014	Intermediate Similarity	NPC29638
0.8014	Intermediate Similarity	NPC281398
0.8013	Intermediate Similarity	NPC180924
0.8	Intermediate Similarity	NPC316262
0.8	Intermediate Similarity	NPC254492
0.8	Intermediate Similarity	NPC314653
0.8	Intermediate Similarity	NPC472799
0.8	Intermediate Similarity	NPC196941
0.8	Intermediate Similarity	NPC184702
0.8	Intermediate Similarity	NPC309169
0.7987	Intermediate Similarity	NPC72958
0.7987	Intermediate Similarity	NPC149526
0.7987	Intermediate Similarity	NPC474417
0.7987	Intermediate Similarity	NPC478148
0.7987	Intermediate Similarity	NPC115869
0.7987	Intermediate Similarity	NPC258249
0.7987	Intermediate Similarity	NPC230848
0.7987	Intermediate Similarity	NPC232645
0.7986	Intermediate Similarity	NPC201297
0.7986	Intermediate Similarity	NPC229646
0.7986	Intermediate Similarity	NPC86455
0.7986	Intermediate Similarity	NPC94076
0.7986	Intermediate Similarity	NPC182255
0.7986	Intermediate Similarity	NPC137920
0.7986	Intermediate Similarity	NPC125134
0.7985	Intermediate Similarity	NPC56332
0.7985	Intermediate Similarity	NPC471074
0.7985	Intermediate Similarity	NPC107846
0.7985	Intermediate Similarity	NPC111088
0.7985	Intermediate Similarity	NPC473885
0.7984	Intermediate Similarity	NPC470860
0.7973	Intermediate Similarity	NPC288036
0.7973	Intermediate Similarity	NPC100985
0.7973	Intermediate Similarity	NPC97028
0.7973	Intermediate Similarity	NPC97029
0.7973	Intermediate Similarity	NPC474305
0.7973	Intermediate Similarity	NPC65589
0.7973	Intermediate Similarity	NPC472837
0.7973	Intermediate Similarity	NPC158338
0.7972	Intermediate Similarity	NPC137009
0.7972	Intermediate Similarity	NPC37206
0.7971	Intermediate Similarity	NPC471851
0.7971	Intermediate Similarity	NPC324488
0.7961	Intermediate Similarity	NPC123153
0.7961	Intermediate Similarity	NPC164110
0.7961	Intermediate Similarity	NPC212967
0.7961	Intermediate Similarity	NPC246647
0.7961	Intermediate Similarity	NPC96342
0.7959	Intermediate Similarity	NPC469425
0.7959	Intermediate Similarity	NPC17101
0.7959	Intermediate Similarity	NPC252208
0.7959	Intermediate Similarity	NPC77903
0.7958	Intermediate Similarity	NPC202260
0.7956	Intermediate Similarity	NPC473019

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 NPC279596 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	1034
0.2-0.3	1396
0.3-0.4	2554
0.4-0.5	2004
0.5-0.6	1096
0.6-0.7	564
0.7-0.8	143
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.832	Intermediate Similarity	NPD1241	Discontinued
0.8217	Intermediate Similarity	NPD1651	Approved
0.8168	Intermediate Similarity	NPD1281	Approved
0.812	Intermediate Similarity	NPD1876	Approved
0.8106	Intermediate Similarity	NPD3972	Approved
0.8085	Intermediate Similarity	NPD1471	Phase 3
0.8077	Intermediate Similarity	NPD5691	Approved
0.7985	Intermediate Similarity	NPD1283	Approved
0.7958	Intermediate Similarity	NPD2346	Discontinued
0.7895	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1243	Approved
0.7832	Intermediate Similarity	NPD2344	Approved
0.7832	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD2799	Discontinued
0.7786	Intermediate Similarity	NPD2979	Phase 3
0.777	Intermediate Similarity	NPD6273	Approved
0.7763	Intermediate Similarity	NPD7819	Suspended
0.7762	Intermediate Similarity	NPD2796	Approved
0.7744	Intermediate Similarity	NPD17	Approved
0.7744	Intermediate Similarity	NPD4626	Approved
0.7744	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD8032	Phase 2
0.7712	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2533	Approved
0.7703	Intermediate Similarity	NPD2534	Approved
0.7703	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD3748	Approved
0.7687	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD7003	Approved
0.7655	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5494	Approved
0.7619	Intermediate Similarity	NPD2309	Approved
0.7616	Intermediate Similarity	NPD3226	Approved
0.7616	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD920	Approved
0.7597	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1608	Approved
0.7552	Intermediate Similarity	NPD1607	Approved
0.7551	Intermediate Similarity	NPD4628	Phase 3
0.7535	Intermediate Similarity	NPD3140	Approved
0.7535	Intermediate Similarity	NPD3142	Approved
0.7517	Intermediate Similarity	NPD2531	Phase 2
0.7517	Intermediate Similarity	NPD2438	Suspended
0.75	Intermediate Similarity	NPD1611	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD2800	Approved
0.7482	Intermediate Similarity	NPD2798	Approved
0.7468	Intermediate Similarity	NPD6959	Discontinued
0.7452	Intermediate Similarity	NPD919	Approved
0.7432	Intermediate Similarity	NPD3750	Approved
0.7415	Intermediate Similarity	NPD1549	Phase 2
0.7413	Intermediate Similarity	NPD4307	Phase 2
0.7413	Intermediate Similarity	NPD1240	Approved
0.741	Intermediate Similarity	NPD3267	Approved
0.741	Intermediate Similarity	NPD3266	Approved
0.7397	Intermediate Similarity	NPD4477	Approved
0.7397	Intermediate Similarity	NPD6099	Approved
0.7397	Intermediate Similarity	NPD2935	Discontinued
0.7397	Intermediate Similarity	NPD4476	Approved
0.7397	Intermediate Similarity	NPD6100	Approved
0.7394	Intermediate Similarity	NPD2313	Discontinued
0.7391	Intermediate Similarity	NPD5327	Phase 3
0.7376	Intermediate Similarity	NPD6832	Phase 2
0.7361	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1247	Approved
0.7355	Intermediate Similarity	NPD6279	Approved
0.7355	Intermediate Similarity	NPD6280	Approved
0.7353	Intermediate Similarity	NPD1778	Approved
0.7351	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6599	Discontinued
0.7329	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1510	Phase 2
0.7315	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD9494	Approved
0.7301	Intermediate Similarity	NPD5844	Phase 1
0.7292	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6355	Discontinued
0.7239	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1019	Discontinued
0.7215	Intermediate Similarity	NPD3882	Suspended
0.7211	Intermediate Similarity	NPD4308	Phase 3
0.7206	Intermediate Similarity	NPD9545	Approved
0.7197	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD9717	Approved
0.7188	Intermediate Similarity	NPD710	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7411	Suspended
0.7172	Intermediate Similarity	NPD4140	Approved
0.7171	Intermediate Similarity	NPD6799	Approved
0.7163	Intermediate Similarity	NPD2797	Approved
0.7161	Intermediate Similarity	NPD2651	Approved
0.7161	Intermediate Similarity	NPD2649	Approved
0.7153	Intermediate Similarity	NPD3268	Approved
0.7153	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5585	Approved
0.7152	Intermediate Similarity	NPD3887	Approved
0.7134	Intermediate Similarity	NPD1934	Approved
0.7134	Intermediate Similarity	NPD7177	Discontinued
0.7132	Intermediate Similarity	NPD7644	Approved
0.7124	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1201	Approved
0.7121	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2353	Approved
0.7114	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2932	Approved
0.7099	Intermediate Similarity	NPD5711	Approved
0.7099	Intermediate Similarity	NPD5710	Approved
0.7092	Intermediate Similarity	NPD6696	Suspended
0.7077	Intermediate Similarity	NPD3134	Approved
0.7075	Intermediate Similarity	NPD2157	Approved
0.7073	Intermediate Similarity	NPD7473	Discontinued
0.7063	Intermediate Similarity	NPD7075	Discontinued
0.7063	Intermediate Similarity	NPD3749	Approved
0.7059	Intermediate Similarity	NPD1511	Approved
0.7055	Intermediate Similarity	NPD3926	Phase 2
0.7047	Intermediate Similarity	NPD1551	Phase 2
0.7044	Intermediate Similarity	NPD2296	Approved
0.7044	Intermediate Similarity	NPD5978	Approved
0.7044	Intermediate Similarity	NPD5977	Approved
0.7042	Intermediate Similarity	NPD1470	Approved
0.7042	Intermediate Similarity	NPD1203	Approved
0.7034	Intermediate Similarity	NPD3764	Approved
0.7034	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3024	Approved
0.7029	Intermediate Similarity	NPD3025	Approved
0.7025	Intermediate Similarity	NPD6801	Discontinued
0.7021	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5536	Phase 2
0.7007	Intermediate Similarity	NPD447	Suspended
0.7006	Intermediate Similarity	NPD4380	Phase 2
0.7	Intermediate Similarity	NPD9697	Approved
0.6994	Remote Similarity	NPD6808	Phase 2
0.6994	Remote Similarity	NPD6232	Discontinued
0.6994	Remote Similarity	NPD7229	Phase 3
0.6978	Remote Similarity	NPD3019	Approved
0.6974	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4110	Phase 3
0.6968	Remote Similarity	NPD1512	Approved
0.6964	Remote Similarity	NPD6559	Discontinued
0.6963	Remote Similarity	NPD1398	Phase 1
0.6959	Remote Similarity	NPD6651	Approved
0.6957	Remote Similarity	NPD1894	Discontinued
0.6954	Remote Similarity	NPD2424	Discontinued
0.695	Remote Similarity	NPD1840	Phase 2
0.6944	Remote Similarity	NPD1712	Approved
0.6944	Remote Similarity	NPD2237	Approved
0.6937	Remote Similarity	NPD3817	Phase 2
0.6934	Remote Similarity	NPD7340	Approved
0.6929	Remote Similarity	NPD3023	Approved
0.6929	Remote Similarity	NPD3496	Discontinued
0.6929	Remote Similarity	NPD3026	Approved
0.6928	Remote Similarity	NPD2354	Approved
0.6923	Remote Similarity	NPD3873	Phase 3
0.6923	Remote Similarity	NPD7427	Discontinued
0.6923	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3869	Phase 3
0.6918	Remote Similarity	NPD7985	Registered
0.6918	Remote Similarity	NPD6798	Discontinued
0.6918	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7577	Discontinued
0.6918	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2654	Approved
0.6901	Remote Similarity	NPD4749	Approved
0.6901	Remote Similarity	NPD4359	Approved
0.6899	Remote Similarity	NPD7028	Phase 2
0.6894	Remote Similarity	NPD1358	Approved
0.6894	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7768	Phase 2
0.6892	Remote Similarity	NPD4618	Approved
0.6892	Remote Similarity	NPD1933	Approved
0.6892	Remote Similarity	NPD4622	Approved
0.6892	Remote Similarity	NPD5735	Approved
0.6887	Remote Similarity	NPD6005	Phase 3
0.6887	Remote Similarity	NPD6002	Phase 3
0.6887	Remote Similarity	NPD5762	Approved
0.6887	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6004	Phase 3
0.6887	Remote Similarity	NPD5763	Approved
0.6875	Remote Similarity	NPD1465	Phase 2
0.6875	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2801	Approved
0.6863	Remote Similarity	NPD8166	Discontinued
0.6859	Remote Similarity	NPD5049	Phase 3
0.6849	Remote Similarity	NPD4625	Phase 3
0.6849	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4097	Suspended
0.6846	Remote Similarity	NPD6353	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