NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	258.152
LogP:	3.023
LogD:	3.029
LogS:	-3.804
# Rotatable Bonds:	1
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.713
Synthetic Accessibility Score:	4.885
Fsp3:	0.533
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:	-4.533
MDCK Permeability:	2.48631949943956e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.514
Plasma Protein Binding (PPB):	87.02604675292969%
Volume Distribution (VD):	2.047
Pgp-substrate:	20.791006088256836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.374
CYP2C19-inhibitor:	0.847
CYP2C19-substrate:	0.279
CYP2C9-inhibitor:	0.699
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.607
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.263

ADMET: Excretion

Clearance (CL):	13.685
Half-life (T1/2):	0.609

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.754
Drug-inuced Liver Injury (DILI):	0.215
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.761
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.56
Carcinogencity:	0.821
Eye Corrosion:	0.005
Eye Irritation:	0.082
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC188377

Natural Product ID:	NPC188377
*Common Name:**	Caprariolide B
IUPAC Name:	(3R,5S,9R)-7-(furan-3-yl)-3,9-dimethyl-1-oxaspiro[4.5]dec-6-en-2-one
Synonyms:
Standard InCHIKey:	YDUFVPKWFQXSAZ-HFAKWTLXSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-10-5-13(12-3-4-17-9-12)8-15(6-10)7-11(2)14(16)18-15/h3-4,8-11H,5-7H2,1-2H3/t10-,11-,15+/m1/s1
SMILES:	C[C@@H]1CC(=C[C@]2(C1)C[C@@H](C)C(=O)O2)c1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488191
PubChem CID:	10610434
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO8493	Capraria biflora	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087595]
NPO8493	Capraria biflora	Species	Scrophulariaceae	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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5479	Organism	Cylas formicarius	Cylas formicarius	LD50	=	1.102	mg	PMID[483321]

☑ 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 NPC188377 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	273
0.1-0.2	1444
0.2-0.3	3616
0.3-0.4	9465
0.4-0.5	10822
0.5-0.6	9867
0.6-0.7	6393
0.7-0.8	720
0.8-0.85	78
0.85-0.9	16
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC65735
0.8819	High Similarity	NPC298190
0.88	High Similarity	NPC95567
0.88	High Similarity	NPC319140
0.876	High Similarity	NPC473969
0.864	High Similarity	NPC473885
0.864	High Similarity	NPC471074
0.8629	High Similarity	NPC16922
0.8595	High Similarity	NPC144745
0.8595	High Similarity	NPC208906
0.8595	High Similarity	NPC131801
0.8583	High Similarity	NPC28054
0.8583	High Similarity	NPC205523
0.8583	High Similarity	NPC474438
0.8583	High Similarity	NPC474279
0.856	High Similarity	NPC118853
0.8559	High Similarity	NPC105249
0.855	High Similarity	NPC92941
0.8538	High Similarity	NPC470740
0.8525	High Similarity	NPC243704
0.8504	High Similarity	NPC83178
0.8504	High Similarity	NPC137570
0.8504	High Similarity	NPC476016
0.8492	Intermediate Similarity	NPC71274
0.8492	Intermediate Similarity	NPC75557
0.8492	Intermediate Similarity	NPC179354
0.8485	Intermediate Similarity	NPC146872
0.8455	Intermediate Similarity	NPC4898
0.845	Intermediate Similarity	NPC21460
0.8443	Intermediate Similarity	NPC312525
0.8443	Intermediate Similarity	NPC217180
0.8438	Intermediate Similarity	NPC112706
0.8438	Intermediate Similarity	NPC207294
0.843	Intermediate Similarity	NPC150895
0.8425	Intermediate Similarity	NPC138139
0.8425	Intermediate Similarity	NPC46536
0.8425	Intermediate Similarity	NPC329922
0.8425	Intermediate Similarity	NPC74612
0.8425	Intermediate Similarity	NPC474260
0.8425	Intermediate Similarity	NPC329694
0.8425	Intermediate Similarity	NPC81912
0.8421	Intermediate Similarity	NPC470742
0.8421	Intermediate Similarity	NPC170604
0.8421	Intermediate Similarity	NPC307401
0.8421	Intermediate Similarity	NPC215109
0.8413	Intermediate Similarity	NPC243269
0.8372	Intermediate Similarity	NPC208389
0.8372	Intermediate Similarity	NPC59502
0.8361	Intermediate Similarity	NPC45536
0.8358	Intermediate Similarity	NPC236532
0.8346	Intermediate Similarity	NPC474829
0.8333	Intermediate Similarity	NPC476351
0.8305	Intermediate Similarity	NPC471521
0.8305	Intermediate Similarity	NPC473356
0.8296	Intermediate Similarity	NPC90953
0.8293	Intermediate Similarity	NPC227660
0.8258	Intermediate Similarity	NPC471006
0.8254	Intermediate Similarity	NPC477967
0.8254	Intermediate Similarity	NPC289911
0.8254	Intermediate Similarity	NPC317217
0.8254	Intermediate Similarity	NPC283284
0.8244	Intermediate Similarity	NPC17681
0.8244	Intermediate Similarity	NPC136340
0.8244	Intermediate Similarity	NPC475092
0.8226	Intermediate Similarity	NPC21831
0.8226	Intermediate Similarity	NPC187547
0.8217	Intermediate Similarity	NPC474830
0.8203	Intermediate Similarity	NPC471559
0.8189	Intermediate Similarity	NPC475818
0.8188	Intermediate Similarity	NPC80635
0.8182	Intermediate Similarity	NPC473982
0.8182	Intermediate Similarity	NPC97740
0.8182	Intermediate Similarity	NPC471817
0.8182	Intermediate Similarity	NPC45358
0.8175	Intermediate Similarity	NPC474136
0.8175	Intermediate Similarity	NPC1848
0.8175	Intermediate Similarity	NPC97566
0.8162	Intermediate Similarity	NPC202260
0.816	Intermediate Similarity	NPC137710
0.8154	Intermediate Similarity	NPC279877
0.8148	Intermediate Similarity	NPC310830
0.8148	Intermediate Similarity	NPC186626
0.814	Intermediate Similarity	NPC23086
0.814	Intermediate Similarity	NPC216810
0.8125	Intermediate Similarity	NPC477965
0.8125	Intermediate Similarity	NPC477038
0.812	Intermediate Similarity	NPC474407
0.812	Intermediate Similarity	NPC474425
0.812	Intermediate Similarity	NPC293253
0.812	Intermediate Similarity	NPC474426
0.8106	Intermediate Similarity	NPC89133
0.8102	Intermediate Similarity	NPC148374
0.8088	Intermediate Similarity	NPC472376
0.8088	Intermediate Similarity	NPC220094
0.808	Intermediate Similarity	NPC87466
0.8077	Intermediate Similarity	NPC141059
0.8077	Intermediate Similarity	NPC246392
0.8077	Intermediate Similarity	NPC290955
0.8071	Intermediate Similarity	NPC56731
0.8065	Intermediate Similarity	NPC476031
0.8065	Intermediate Similarity	NPC59035
0.8065	Intermediate Similarity	NPC79202
0.8065	Intermediate Similarity	NPC476014
0.806	Intermediate Similarity	NPC106247
0.8058	Intermediate Similarity	NPC223415
0.8058	Intermediate Similarity	NPC470741
0.8045	Intermediate Similarity	NPC196979
0.8045	Intermediate Similarity	NPC470977
0.8045	Intermediate Similarity	NPC470976
0.8033	Intermediate Similarity	NPC22678
0.8033	Intermediate Similarity	NPC1811
0.8033	Intermediate Similarity	NPC26157
0.8031	Intermediate Similarity	NPC115859
0.8031	Intermediate Similarity	NPC79557
0.803	Intermediate Similarity	NPC170546
0.803	Intermediate Similarity	NPC66246
0.8029	Intermediate Similarity	NPC474722
0.8015	Intermediate Similarity	NPC26532
0.8015	Intermediate Similarity	NPC477123
0.8015	Intermediate Similarity	NPC477039
0.8015	Intermediate Similarity	NPC42400
0.8015	Intermediate Similarity	NPC477966
0.8014	Intermediate Similarity	NPC346
0.8014	Intermediate Similarity	NPC276676
0.8	Intermediate Similarity	NPC251865
0.8	Intermediate Similarity	NPC159786
0.8	Intermediate Similarity	NPC83301
0.8	Intermediate Similarity	NPC470858
0.8	Intermediate Similarity	NPC84479
0.7983	Intermediate Similarity	NPC42471
0.7971	Intermediate Similarity	NPC56197
0.797	Intermediate Similarity	NPC61788
0.797	Intermediate Similarity	NPC282230
0.797	Intermediate Similarity	NPC183348
0.7969	Intermediate Similarity	NPC473379
0.7969	Intermediate Similarity	NPC36255
0.7969	Intermediate Similarity	NPC471549
0.7956	Intermediate Similarity	NPC476943
0.7953	Intermediate Similarity	NPC474817
0.7939	Intermediate Similarity	NPC473355
0.7939	Intermediate Similarity	NPC471554
0.7939	Intermediate Similarity	NPC471501
0.7939	Intermediate Similarity	NPC471573
0.7937	Intermediate Similarity	NPC206007
0.7937	Intermediate Similarity	NPC293424
0.7929	Intermediate Similarity	NPC267632
0.7914	Intermediate Similarity	NPC20500
0.791	Intermediate Similarity	NPC15083
0.7903	Intermediate Similarity	NPC292036
0.7902	Intermediate Similarity	NPC93666
0.7887	Intermediate Similarity	NPC475864
0.7883	Intermediate Similarity	NPC286130
0.7883	Intermediate Similarity	NPC473268
0.7879	Intermediate Similarity	NPC476917
0.7879	Intermediate Similarity	NPC329707
0.7879	Intermediate Similarity	NPC327527
0.7879	Intermediate Similarity	NPC477040
0.7872	Intermediate Similarity	NPC199044
0.7872	Intermediate Similarity	NPC267004
0.7872	Intermediate Similarity	NPC218712
0.7872	Intermediate Similarity	NPC238843
0.7872	Intermediate Similarity	NPC307346
0.7872	Intermediate Similarity	NPC261733
0.7868	Intermediate Similarity	NPC158525
0.7868	Intermediate Similarity	NPC209858
0.7852	Intermediate Similarity	NPC218838
0.7846	Intermediate Similarity	NPC11799
0.7846	Intermediate Similarity	NPC130275
0.7846	Intermediate Similarity	NPC141252
0.7846	Intermediate Similarity	NPC83115
0.7846	Intermediate Similarity	NPC178382
0.7836	Intermediate Similarity	NPC477645
0.7832	Intermediate Similarity	NPC476938
0.7832	Intermediate Similarity	NPC476937
0.7832	Intermediate Similarity	NPC10088
0.7832	Intermediate Similarity	NPC221809
0.7832	Intermediate Similarity	NPC224418
0.7832	Intermediate Similarity	NPC250228
0.782	Intermediate Similarity	NPC50583
0.7817	Intermediate Similarity	NPC195920
0.781	Intermediate Similarity	NPC303217
0.7808	Intermediate Similarity	NPC246164
0.7805	Intermediate Similarity	NPC54626
0.7795	Intermediate Similarity	NPC254958
0.7795	Intermediate Similarity	NPC291619
0.7787	Intermediate Similarity	NPC177331
0.7786	Intermediate Similarity	NPC230979
0.7778	Intermediate Similarity	NPC474255
0.7778	Intermediate Similarity	NPC471618
0.7778	Intermediate Similarity	NPC316062
0.7778	Intermediate Similarity	NPC476942
0.7778	Intermediate Similarity	NPC474220
0.7778	Intermediate Similarity	NPC476941
0.777	Intermediate Similarity	NPC233707
0.777	Intermediate Similarity	NPC474615
0.777	Intermediate Similarity	NPC104736
0.7762	Intermediate Similarity	NPC233763
0.7762	Intermediate Similarity	NPC471292
0.7761	Intermediate Similarity	NPC476925
0.776	Intermediate Similarity	NPC252004

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 NPC188377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	962
0.2-0.3	1695
0.3-0.4	2718
0.4-0.5	2135
0.5-0.6	1063
0.6-0.7	300
0.7-0.8	19
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
0.8029	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD1241	Discontinued
0.744	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6832	Phase 2
0.7415	Intermediate Similarity	NPD920	Approved
0.7397	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD2799	Discontinued
0.7293	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1019	Discontinued
0.7273	Intermediate Similarity	NPD17	Approved
0.7258	Intermediate Similarity	NPD3134	Approved
0.7239	Intermediate Similarity	NPD9717	Approved
0.7214	Intermediate Similarity	NPD4307	Phase 2
0.7194	Intermediate Similarity	NPD2313	Discontinued
0.7172	Intermediate Similarity	NPD1243	Approved
0.7153	Intermediate Similarity	NPD1471	Phase 3
0.7132	Intermediate Similarity	NPD1876	Approved
0.7114	Intermediate Similarity	NPD6273	Approved
0.7111	Intermediate Similarity	NPD1608	Approved
0.708	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2797	Approved
0.7068	Intermediate Similarity	NPD5585	Approved
0.7063	Intermediate Similarity	NPD1358	Approved
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1281	Approved
0.7034	Intermediate Similarity	NPD2344	Approved
0.7029	Intermediate Similarity	NPD2798	Approved
0.7014	Intermediate Similarity	NPD4308	Phase 3
0.7013	Intermediate Similarity	NPD5760	Phase 2
0.7013	Intermediate Similarity	NPD5761	Phase 2
0.7008	Intermediate Similarity	NPD2182	Approved
0.7007	Intermediate Similarity	NPD4628	Phase 3
0.6992	Remote Similarity	NPD9545	Approved
0.6985	Remote Similarity	NPD3972	Approved
0.6968	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1551	Phase 2
0.6959	Remote Similarity	NPD3887	Approved
0.6957	Remote Similarity	NPD1203	Approved
0.6957	Remote Similarity	NPD3266	Approved
0.6957	Remote Similarity	NPD3267	Approved
0.6943	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD919	Approved
0.694	Remote Similarity	NPD5691	Approved
0.6923	Remote Similarity	NPD6355	Discontinued
0.6923	Remote Similarity	NPD4618	Approved
0.6923	Remote Similarity	NPD447	Suspended
0.6923	Remote Similarity	NPD4622	Approved
0.6918	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6005	Phase 3
0.6918	Remote Similarity	NPD2346	Discontinued
0.6918	Remote Similarity	NPD6004	Phase 3
0.6918	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6002	Phase 3
0.6911	Remote Similarity	NPD1238	Approved
0.6905	Remote Similarity	NPD9697	Approved
0.6901	Remote Similarity	NPD8032	Phase 2
0.6897	Remote Similarity	NPD3748	Approved
0.689	Remote Similarity	NPD6765	Approved
0.689	Remote Similarity	NPD6764	Approved
0.6889	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1778	Approved
0.6884	Remote Similarity	NPD1283	Approved
0.6866	Remote Similarity	NPD1894	Discontinued
0.6857	Remote Similarity	NPD9494	Approved
0.6853	Remote Similarity	NPD2979	Phase 3
0.6853	Remote Similarity	NPD3140	Approved
0.6853	Remote Similarity	NPD3142	Approved
0.6849	Remote Similarity	NPD2796	Approved
0.6849	Remote Similarity	NPD2935	Discontinued
0.6846	Remote Similarity	NPD2309	Approved
0.6846	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9493	Approved
0.6838	Remote Similarity	NPD3496	Discontinued
0.6831	Remote Similarity	NPD3268	Approved
0.6831	Remote Similarity	NPD411	Approved
0.6831	Remote Similarity	NPD3764	Approved
0.6828	Remote Similarity	NPD5689	Approved
0.6828	Remote Similarity	NPD5688	Approved
0.6825	Remote Similarity	NPD164	Approved
0.6812	Remote Similarity	NPD4359	Approved
0.6806	Remote Similarity	NPD1933	Approved
0.6803	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2353	Approved
0.6794	Remote Similarity	NPD5535	Approved
0.6786	Remote Similarity	NPD8434	Phase 2
0.6786	Remote Similarity	NPD5647	Approved
0.6779	Remote Similarity	NPD7003	Approved
0.6779	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4477	Approved
0.6735	Remote Similarity	NPD4476	Approved
0.6732	Remote Similarity	NPD3869	Phase 3
0.6732	Remote Similarity	NPD3873	Phase 3
0.6731	Remote Similarity	NPD6279	Approved
0.6731	Remote Similarity	NPD6280	Approved
0.6726	Remote Similarity	NPD6784	Approved
0.6726	Remote Similarity	NPD6785	Approved
0.6713	Remote Similarity	NPD6798	Discontinued
0.6708	Remote Similarity	NPD6808	Phase 2
0.6692	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2067	Discontinued
0.6691	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6646	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1247	Approved
0.6645	Remote Similarity	NPD6799	Approved
0.6642	Remote Similarity	NPD4626	Approved
0.6623	Remote Similarity	NPD2354	Approved
0.6622	Remote Similarity	NPD2438	Suspended
0.6622	Remote Similarity	NPD2531	Phase 2
0.662	Remote Similarity	NPD454	Approved
0.6619	Remote Similarity	NPD1481	Phase 2
0.6615	Remote Similarity	NPD2684	Approved
0.6599	Remote Similarity	NPD7097	Phase 1
0.6597	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6362	Approved
0.6582	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7819	Suspended
0.6579	Remote Similarity	NPD7440	Discontinued
0.6573	Remote Similarity	NPD2614	Approved
0.6562	Remote Similarity	NPD3749	Approved
0.6561	Remote Similarity	NPD7411	Suspended
0.6558	Remote Similarity	NPD5049	Phase 3
0.6556	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4110	Phase 3
0.6556	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7033	Discontinued
0.6552	Remote Similarity	NPD4062	Phase 3
0.6552	Remote Similarity	NPD6233	Phase 2
0.6552	Remote Similarity	NPD4870	Approved
0.6549	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD1535	Discovery
0.6544	Remote Similarity	NPD9092	Discovery
0.6538	Remote Similarity	NPD3226	Approved
0.6538	Remote Similarity	NPD7458	Discontinued
0.6536	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD5958	Discontinued
0.6533	Remote Similarity	NPD2897	Discontinued
0.6531	Remote Similarity	NPD6653	Approved
0.6528	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4140	Approved
0.6503	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7768	Phase 2
0.6497	Remote Similarity	NPD6599	Discontinued
0.6494	Remote Similarity	NPD2532	Approved
0.6494	Remote Similarity	NPD2534	Approved
0.6494	Remote Similarity	NPD2533	Approved
0.6488	Remote Similarity	NPD6559	Discontinued
0.6484	Remote Similarity	NPD9261	Approved
0.6483	Remote Similarity	NPD1296	Phase 2
0.6481	Remote Similarity	NPD5494	Approved
0.6479	Remote Similarity	NPD987	Approved
0.6478	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD3847	Discontinued
0.6475	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7075	Discontinued
0.6456	Remote Similarity	NPD5889	Approved
0.6456	Remote Similarity	NPD5890	Approved
0.6452	Remote Similarity	NPD2186	Approved
0.6429	Remote Similarity	NPD1611	Approved
0.6429	Remote Similarity	NPD6287	Discontinued
0.6424	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD4534	Discontinued
0.6424	Remote Similarity	NPD2424	Discontinued
0.6424	Remote Similarity	NPD1549	Phase 2
0.6418	Remote Similarity	NPD7843	Approved
0.6415	Remote Similarity	NPD6801	Discontinued
0.6414	Remote Similarity	NPD7095	Approved
0.641	Remote Similarity	NPD5403	Approved
0.6397	Remote Similarity	NPD7157	Approved
0.6395	Remote Similarity	NPD1240	Approved
0.6395	Remote Similarity	NPD4060	Phase 1
0.6392	Remote Similarity	NPD6585	Discontinued
0.6389	Remote Similarity	NPD2237	Approved
0.6387	Remote Similarity	NPD4662	Approved
0.6387	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4661	Approved
0.6387	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5401	Approved
0.637	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD957	Approved
0.6364	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD6386	Approved
0.6352	Remote Similarity	NPD6873	Phase 2
0.6352	Remote Similarity	NPD6385	Approved
0.6351	Remote Similarity	NPD230	Phase 1
0.6338	Remote Similarity	NPD5327	Phase 3
0.6335	Remote Similarity	NPD5402	Approved
0.6335	Remote Similarity	NPD2296	Approved
0.6333	Remote Similarity	NPD1510	Phase 2
0.6333	Remote Similarity	NPD9257	Approved
0.6333	Remote Similarity	NPD9259	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