NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.14
Volume:	281.368
LogP:	3.197
LogD:	3.249
LogS:	-2.728
# Rotatable Bonds:	4
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	4.518
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.738
MDCK Permeability:	3.999128966825083e-05
Pgp-inhibitor:	0.046
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.332
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.37
Plasma Protein Binding (PPB):	74.54263305664062%
Volume Distribution (VD):	1.474
Pgp-substrate:	41.3023681640625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.406
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.408
CYP2C19-substrate:	0.44
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.195
CYP2D6-substrate:	0.35
CYP3A4-inhibitor:	0.77
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	6.541
Half-life (T1/2):	0.575

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.338
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.519
Maximum Recommended Daily Dose:	0.109
Skin Sensitization:	0.537
Carcinogencity:	0.742
Eye Corrosion:	0.351
Eye Irritation:	0.295
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC293253

Natural Product ID:	NPC293253
*Common Name:**	1-((5R,6S)-3,6-Dimethyl-6-Vinyl-4,5,6,7-Tetrahydrobenzofuran-5-Yl)Vinyl Acetate
IUPAC Name:	1-[(5R,6S)-6-ethenyl-3,6-dimethyl-5,7-dihydro-4H-1-benzofuran-5-yl]ethenyl acetate
Synonyms:
Standard InCHIKey:	VORODINTVKJTQN-GOEBONIOSA-N
Standard InCHI:	InChI=1S/C16H20O3/c1-6-16(5)8-15-13(10(2)9-18-15)7-14(16)11(3)19-12(4)17/h6,9,14H,1,3,7-8H2,2,4-5H3/t14-,16+/m0/s1
SMILES:	C=C[C@]1(C)Cc2occ(c2C[C@H]1C(=C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513801
PubChem CID:	44559112
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO28209	Muricea austera	Species	Plexauridae	Eukaryota	n.a.	Pacific coast of Panama	n.a.	PMID[17067146]
NPO28209	Muricea austera	Species	Plexauridae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	42000.0	nM	PMID[571500]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	173000.0	nM	PMID[571500]

☑ 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 NPC293253 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	314
0.1-0.2	1491
0.2-0.3	3123
0.3-0.4	7139
0.4-0.5	12219
0.5-0.6	7094
0.6-0.7	9263
0.7-0.8	1948
0.8-0.85	84
0.85-0.9	21
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9098	High Similarity	NPC307401
0.9051	High Similarity	NPC84479
0.904	High Similarity	NPC97566
0.8993	High Similarity	NPC71821
0.8976	High Similarity	NPC178382
0.8963	High Similarity	NPC202260
0.8923	High Similarity	NPC59502
0.8921	High Similarity	NPC62799
0.8905	High Similarity	NPC263337
0.8897	High Similarity	NPC148374
0.8841	High Similarity	NPC205071
0.8803	High Similarity	NPC228842
0.8803	High Similarity	NPC212257
0.8794	High Similarity	NPC19747
0.8732	High Similarity	NPC211625
0.8702	High Similarity	NPC329707
0.8681	High Similarity	NPC294511
0.8681	High Similarity	NPC121615
0.864	High Similarity	NPC59035
0.864	High Similarity	NPC79202
0.8613	High Similarity	NPC177262
0.8603	High Similarity	NPC214572
0.854	High Similarity	NPC310043
0.8521	High Similarity	NPC233763
0.8503	High Similarity	NPC104736
0.8503	High Similarity	NPC41880
0.85	High Similarity	NPC121158
0.8496	Intermediate Similarity	NPC198904
0.8493	Intermediate Similarity	NPC114880
0.8473	Intermediate Similarity	NPC473885
0.8473	Intermediate Similarity	NPC471074
0.8473	Intermediate Similarity	NPC230979
0.8473	Intermediate Similarity	NPC179354
0.8467	Intermediate Similarity	NPC46896
0.8462	Intermediate Similarity	NPC224418
0.8462	Intermediate Similarity	NPC16922
0.8451	Intermediate Similarity	NPC56731
0.8451	Intermediate Similarity	NPC290038
0.8446	Intermediate Similarity	NPC7059
0.8446	Intermediate Similarity	NPC88007
0.8446	Intermediate Similarity	NPC195954
0.8446	Intermediate Similarity	NPC194499
0.8446	Intermediate Similarity	NPC304692
0.844	Intermediate Similarity	NPC64568
0.8435	Intermediate Similarity	NPC75310
0.8425	Intermediate Similarity	NPC246164
0.8425	Intermediate Similarity	NPC475777
0.8425	Intermediate Similarity	NPC227660
0.8409	Intermediate Similarity	NPC74612
0.8406	Intermediate Similarity	NPC170604
0.8406	Intermediate Similarity	NPC215109
0.8394	Intermediate Similarity	NPC158525
0.8389	Intermediate Similarity	NPC474611
0.8385	Intermediate Similarity	NPC36255
0.838	Intermediate Similarity	NPC251865
0.837	Intermediate Similarity	NPC298190
0.8367	Intermediate Similarity	NPC10429
0.8358	Intermediate Similarity	NPC208389
0.8357	Intermediate Similarity	NPC56197
0.8333	Intermediate Similarity	NPC471174
0.8333	Intermediate Similarity	NPC216755
0.8333	Intermediate Similarity	NPC287559
0.8333	Intermediate Similarity	NPC8389
0.8322	Intermediate Similarity	NPC81405
0.8309	Intermediate Similarity	NPC473982
0.8284	Intermediate Similarity	NPC207294
0.8284	Intermediate Similarity	NPC112706
0.8278	Intermediate Similarity	NPC18986
0.8278	Intermediate Similarity	NPC68848
0.8278	Intermediate Similarity	NPC471003
0.8278	Intermediate Similarity	NPC79571
0.8276	Intermediate Similarity	NPC93666
0.8271	Intermediate Similarity	NPC138139
0.8271	Intermediate Similarity	NPC46536
0.8267	Intermediate Similarity	NPC140952
0.8264	Intermediate Similarity	NPC97904
0.8261	Intermediate Similarity	NPC209858
0.8258	Intermediate Similarity	NPC83115
0.8258	Intermediate Similarity	NPC130275
0.8235	Intermediate Similarity	NPC89133
0.8235	Intermediate Similarity	NPC61788
0.8227	Intermediate Similarity	NPC67003
0.8224	Intermediate Similarity	NPC475039
0.8224	Intermediate Similarity	NPC285567
0.8224	Intermediate Similarity	NPC14499
0.8224	Intermediate Similarity	NPC283209
0.8224	Intermediate Similarity	NPC476035
0.8222	Intermediate Similarity	NPC120836
0.8222	Intermediate Similarity	NPC223063
0.8219	Intermediate Similarity	NPC95526
0.8219	Intermediate Similarity	NPC471001
0.8214	Intermediate Similarity	NPC471996
0.8212	Intermediate Similarity	NPC472299
0.8209	Intermediate Similarity	NPC83178
0.8207	Intermediate Similarity	NPC286038
0.8207	Intermediate Similarity	NPC255414
0.8207	Intermediate Similarity	NPC221809
0.8194	Intermediate Similarity	NPC34056
0.8188	Intermediate Similarity	NPC25351
0.8182	Intermediate Similarity	NPC243577
0.8182	Intermediate Similarity	NPC223415
0.8175	Intermediate Similarity	NPC470976
0.8175	Intermediate Similarity	NPC470977
0.8175	Intermediate Similarity	NPC196979
0.8175	Intermediate Similarity	NPC471817
0.8163	Intermediate Similarity	NPC469335
0.8163	Intermediate Similarity	NPC156189
0.8163	Intermediate Similarity	NPC477404
0.8163	Intermediate Similarity	NPC196864
0.8163	Intermediate Similarity	NPC472298
0.8163	Intermediate Similarity	NPC159927
0.8163	Intermediate Similarity	NPC5180
0.8158	Intermediate Similarity	NPC188649
0.8156	Intermediate Similarity	NPC90953
0.8156	Intermediate Similarity	NPC474722
0.8151	Intermediate Similarity	NPC66991
0.8146	Intermediate Similarity	NPC84349
0.8146	Intermediate Similarity	NPC123153
0.8143	Intermediate Similarity	NPC4764
0.814	Intermediate Similarity	NPC212918
0.8138	Intermediate Similarity	NPC478166
0.8129	Intermediate Similarity	NPC324117
0.8125	Intermediate Similarity	NPC150895
0.8125	Intermediate Similarity	NPC238843
0.8125	Intermediate Similarity	NPC199044
0.812	Intermediate Similarity	NPC118853
0.812	Intermediate Similarity	NPC188377
0.812	Intermediate Similarity	NPC65735
0.8117	Intermediate Similarity	NPC121995
0.8117	Intermediate Similarity	NPC277618
0.8116	Intermediate Similarity	NPC218838
0.8116	Intermediate Similarity	NPC470740
0.8108	Intermediate Similarity	NPC291150
0.8108	Intermediate Similarity	NPC144010
0.8108	Intermediate Similarity	NPC116717
0.8105	Intermediate Similarity	NPC88841
0.8105	Intermediate Similarity	NPC288602
0.8102	Intermediate Similarity	NPC282230
0.8102	Intermediate Similarity	NPC183348
0.8099	Intermediate Similarity	NPC90296
0.8095	Intermediate Similarity	NPC195325
0.8095	Intermediate Similarity	NPC470790
0.8095	Intermediate Similarity	NPC472654
0.8095	Intermediate Similarity	NPC470791
0.8095	Intermediate Similarity	NPC69647
0.8095	Intermediate Similarity	NPC125182
0.8095	Intermediate Similarity	NPC266743
0.8085	Intermediate Similarity	NPC476943
0.8085	Intermediate Similarity	NPC236532
0.8082	Intermediate Similarity	NPC470941
0.8077	Intermediate Similarity	NPC87466
0.8077	Intermediate Similarity	NPC243704
0.8074	Intermediate Similarity	NPC246392
0.8074	Intermediate Similarity	NPC290955
0.8071	Intermediate Similarity	NPC146872
0.8069	Intermediate Similarity	NPC41182
0.8069	Intermediate Similarity	NPC114513
0.8069	Intermediate Similarity	NPC245522
0.8065	Intermediate Similarity	NPC473766
0.8065	Intermediate Similarity	NPC473753
0.8058	Intermediate Similarity	NPC471998
0.8056	Intermediate Similarity	NPC470741
0.8054	Intermediate Similarity	NPC471002
0.8052	Intermediate Similarity	NPC61967
0.8052	Intermediate Similarity	NPC126984
0.8052	Intermediate Similarity	NPC62692
0.8052	Intermediate Similarity	NPC56358
0.8052	Intermediate Similarity	NPC472664
0.8052	Intermediate Similarity	NPC27541
0.8045	Intermediate Similarity	NPC272899
0.8043	Intermediate Similarity	NPC471995
0.8043	Intermediate Similarity	NPC15083
0.8042	Intermediate Similarity	NPC20500
0.8041	Intermediate Similarity	NPC476122
0.8031	Intermediate Similarity	NPC22678
0.8029	Intermediate Similarity	NPC66246
0.8029	Intermediate Similarity	NPC170546
0.8028	Intermediate Similarity	NPC233707
0.8026	Intermediate Similarity	NPC473368
0.8015	Intermediate Similarity	NPC26532
0.8015	Intermediate Similarity	NPC279877
0.8015	Intermediate Similarity	NPC37512
0.8014	Intermediate Similarity	NPC470742
0.8014	Intermediate Similarity	NPC470999
0.8014	Intermediate Similarity	NPC310830
0.8014	Intermediate Similarity	NPC471292
0.8014	Intermediate Similarity	NPC42400
0.8013	Intermediate Similarity	NPC296558
0.8	Intermediate Similarity	NPC475779
0.8	Intermediate Similarity	NPC30222
0.8	Intermediate Similarity	NPC44606
0.8	Intermediate Similarity	NPC476947
0.8	Intermediate Similarity	NPC23086
0.8	Intermediate Similarity	NPC178932
0.8	Intermediate Similarity	NPC470858
0.7987	Intermediate Similarity	NPC18135
0.7987	Intermediate Similarity	NPC272590
0.7986	Intermediate Similarity	NPC471006
0.7985	Intermediate Similarity	NPC243269
0.7984	Intermediate Similarity	NPC205523

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 NPC293253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	1024
0.2-0.3	1658
0.3-0.4	2650
0.4-0.5	2023
0.5-0.6	1123
0.6-0.7	328
0.7-0.8	60
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
0.8028	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD4628	Phase 3
0.7687	Intermediate Similarity	NPD17	Approved
0.7667	Intermediate Similarity	NPD920	Approved
0.766	Intermediate Similarity	NPD8032	Phase 2
0.7651	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6273	Approved
0.7556	Intermediate Similarity	NPD1778	Approved
0.7551	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1243	Approved
0.7546	Intermediate Similarity	NPD6765	Approved
0.7546	Intermediate Similarity	NPD6764	Approved
0.7534	Intermediate Similarity	NPD1471	Phase 3
0.7533	Intermediate Similarity	NPD2534	Approved
0.7533	Intermediate Similarity	NPD2533	Approved
0.7533	Intermediate Similarity	NPD2532	Approved
0.753	Intermediate Similarity	NPD8434	Phase 2
0.7518	Intermediate Similarity	NPD3972	Approved
0.7518	Intermediate Similarity	NPD1608	Approved
0.7484	Intermediate Similarity	NPD5761	Phase 2
0.7484	Intermediate Similarity	NPD5760	Phase 2
0.7481	Intermediate Similarity	NPD5691	Approved
0.7426	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD919	Approved
0.7403	Intermediate Similarity	NPD6599	Discontinued
0.7397	Intermediate Similarity	NPD3748	Approved
0.7397	Intermediate Similarity	NPD2799	Discontinued
0.7372	Intermediate Similarity	NPD7819	Suspended
0.7365	Intermediate Similarity	NPD6784	Approved
0.7365	Intermediate Similarity	NPD6785	Approved
0.7353	Intermediate Similarity	NPD5585	Approved
0.7347	Intermediate Similarity	NPD2796	Approved
0.7328	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1281	Approved
0.7303	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6004	Phase 3
0.7297	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6002	Phase 3
0.7297	Intermediate Similarity	NPD2346	Discontinued
0.7297	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6005	Phase 3
0.7293	Intermediate Similarity	NPD1241	Discontinued
0.7286	Intermediate Similarity	NPD1876	Approved
0.7267	Intermediate Similarity	NPD7003	Approved
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2979	Phase 3
0.7234	Intermediate Similarity	NPD3266	Approved
0.7234	Intermediate Similarity	NPD3267	Approved
0.7226	Intermediate Similarity	NPD3226	Approved
0.7222	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6832	Phase 2
0.72	Intermediate Similarity	NPD2800	Approved
0.7195	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2344	Approved
0.7174	Intermediate Similarity	NPD4626	Approved
0.7163	Intermediate Similarity	NPD1283	Approved
0.7153	Intermediate Similarity	NPD9545	Approved
0.7152	Intermediate Similarity	NPD3750	Approved
0.7133	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6799	Approved
0.7123	Intermediate Similarity	NPD4140	Approved
0.7115	Intermediate Similarity	NPD7458	Discontinued
0.7114	Intermediate Similarity	NPD6099	Approved
0.7114	Intermediate Similarity	NPD1551	Phase 2
0.7114	Intermediate Similarity	NPD6100	Approved
0.7113	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2797	Approved
0.7103	Intermediate Similarity	NPD3268	Approved
0.7103	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2313	Discontinued
0.7101	Intermediate Similarity	NPD1651	Approved
0.7092	Intermediate Similarity	NPD4359	Approved
0.7075	Intermediate Similarity	NPD6355	Discontinued
0.7071	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2798	Approved
0.7044	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4110	Phase 3
0.7037	Intermediate Similarity	NPD5494	Approved
0.7025	Intermediate Similarity	NPD7411	Suspended
0.7024	Intermediate Similarity	NPD6559	Discontinued
0.7023	Intermediate Similarity	NPD3134	Approved
0.7019	Intermediate Similarity	NPD3749	Approved
0.7007	Intermediate Similarity	NPD4307	Phase 2
0.7006	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2531	Phase 2
0.7	Intermediate Similarity	NPD4477	Approved
0.7	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD3496	Discontinued
0.7	Intermediate Similarity	NPD4476	Approved
0.6994	Remote Similarity	NPD1247	Approved
0.6994	Remote Similarity	NPD8127	Discontinued
0.6993	Remote Similarity	NPD2309	Approved
0.6987	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3764	Approved
0.6972	Remote Similarity	NPD5327	Phase 3
0.6968	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1019	Discontinued
0.6918	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2182	Approved
0.6914	Remote Similarity	NPD7075	Discontinued
0.6906	Remote Similarity	NPD1894	Discontinued
0.6903	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD9717	Approved
0.6894	Remote Similarity	NPD3817	Phase 2
0.6894	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3142	Approved
0.6892	Remote Similarity	NPD3140	Approved
0.6887	Remote Similarity	NPD2935	Discontinued
0.6883	Remote Similarity	NPD3887	Approved
0.6875	Remote Similarity	NPD6279	Approved
0.6875	Remote Similarity	NPD6280	Approved
0.6875	Remote Similarity	NPD6801	Discontinued
0.6872	Remote Similarity	NPD4107	Approved
0.6852	Remote Similarity	NPD7768	Phase 2
0.6848	Remote Similarity	NPD6808	Phase 2
0.6848	Remote Similarity	NPD5710	Approved
0.6848	Remote Similarity	NPD5711	Approved
0.6846	Remote Similarity	NPD4618	Approved
0.6846	Remote Similarity	NPD4622	Approved
0.6845	Remote Similarity	NPD5844	Phase 1
0.6842	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5763	Approved
0.6842	Remote Similarity	NPD5762	Approved
0.6839	Remote Similarity	NPD7236	Approved
0.6832	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4870	Approved
0.6821	Remote Similarity	NPD7033	Discontinued
0.6821	Remote Similarity	NPD4308	Phase 3
0.6807	Remote Similarity	NPD3926	Phase 2
0.6806	Remote Similarity	NPD6696	Suspended
0.68	Remote Similarity	NPD6651	Approved
0.68	Remote Similarity	NPD1607	Approved
0.6797	Remote Similarity	NPD1549	Phase 2
0.6786	Remote Similarity	NPD7177	Discontinued
0.6779	Remote Similarity	NPD4060	Phase 1
0.6779	Remote Similarity	NPD1240	Approved
0.6766	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD411	Approved
0.6757	Remote Similarity	NPD1296	Phase 2
0.6757	Remote Similarity	NPD6798	Discontinued
0.6755	Remote Similarity	NPD5688	Approved
0.6755	Remote Similarity	NPD5689	Approved
0.6752	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3882	Suspended
0.6747	Remote Similarity	NPD7229	Phase 3
0.674	Remote Similarity	NPD4482	Phase 3
0.6733	Remote Similarity	NPD5124	Phase 1
0.6733	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2353	Approved
0.6732	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7473	Discontinued
0.6716	Remote Similarity	NPD1358	Approved
0.6715	Remote Similarity	NPD5535	Approved
0.6714	Remote Similarity	NPD7644	Approved
0.6713	Remote Similarity	NPD1611	Approved
0.6713	Remote Similarity	NPD6287	Discontinued
0.6712	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5647	Approved
0.6711	Remote Similarity	NPD6663	Approved
0.6711	Remote Similarity	NPD1510	Phase 2
0.671	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.671	Remote Similarity	NPD8166	Discontinued
0.6709	Remote Similarity	NPD2186	Approved
0.6691	Remote Similarity	NPD7157	Approved
0.6689	Remote Similarity	NPD7095	Approved
0.6688	Remote Similarity	NPD4534	Discontinued
0.6688	Remote Similarity	NPD2897	Discontinued
0.6687	Remote Similarity	NPD7199	Phase 2
0.6687	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD3873	Phase 3
0.6667	Remote Similarity	NPD3869	Phase 3
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD37	Approved
0.6667	Remote Similarity	NPD2237	Approved
0.6647	Remote Similarity	NPD6232	Discontinued
0.6646	Remote Similarity	NPD5401	Approved
0.6646	Remote Similarity	NPD4965	Approved
0.6646	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7028	Phase 2
0.6646	Remote Similarity	NPD4966	Approved
0.6646	Remote Similarity	NPD3146	Approved
0.6646	Remote Similarity	NPD4967	Phase 2
0.6645	Remote Similarity	NPD2654	Approved
0.6644	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1203	Approved
0.6643	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7239	Suspended

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