NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.09
Volume:	267.226
LogP:	0.817
LogD:	1.122
LogS:	-2.695
# Rotatable Bonds:	3
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.84
Synthetic Accessibility Score:	3.622
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.646
MDCK Permeability:	2.5753610316314735e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.14

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.812
Plasma Protein Binding (PPB):	35.77454376220703%
Volume Distribution (VD):	0.886
Pgp-substrate:	49.58900451660156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.876
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.416
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.42
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.498

ADMET: Excretion

Clearance (CL):	11.881
Half-life (T1/2):	0.702

ADMET: Toxicity

hERG Blockers:	0.222
Human Hepatotoxicity (H-HT):	0.373
Drug-inuced Liver Injury (DILI):	0.428
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.308
Skin Sensitization:	0.935
Carcinogencity:	0.24
Eye Corrosion:	0.051
Eye Irritation:	0.772
Respiratory Toxicity:	0.433

Download Data

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

Natural Product: NPC27159

Natural Product ID:	NPC27159
*Common Name:**	(+)-Glaberide I
IUPAC Name:	(3S,3aR,6aR)-3-(4-hydroxy-3,5-dimethoxyphenyl)-3,3a,4,6a-tetrahydro-1H-furo[3,4-c]furan-6-one
Synonyms:	(+)-Glaberide I
Standard InCHIKey:	AUXYOVQIZNPKSO-MWODSPESSA-N
Standard InCHI:	InChI=1S/C14H16O6/c1-17-10-3-7(4-11(18-2)12(10)15)13-8-5-20-14(16)9(8)6-19-13/h3-4,8-9,13,15H,5-6H2,1-2H3/t8-,9-,13+/m0/s1
SMILES:	COc1cc(cc(c1O)OC)[C@@H]1[C@H]2COC(=O)[C@H]2CO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461277
PubChem CID:	192547
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones

*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
NPO17126	Callicarpa pilosissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19193025]
NPO17126	Callicarpa pilosissima	Species	Lamiaceae	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	1
MIC	1

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	>	10.0	ug.mL-1	PMID[556061]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	257100.0	nM	PMID[556062]

☑ 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 NPC27159 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	313
0.1-0.2	1216
0.2-0.3	3229
0.3-0.4	7496
0.4-0.5	11089
0.5-0.6	4820
0.6-0.7	8018
0.7-0.8	6076
0.8-0.85	340
0.85-0.9	83
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9645	High Similarity	NPC125570
0.9493	High Similarity	NPC470991
0.9485	High Similarity	NPC209229
0.9379	High Similarity	NPC473236
0.9362	High Similarity	NPC223185
0.9315	High Similarity	NPC136757
0.931	High Similarity	NPC477699
0.922	High Similarity	NPC273657
0.922	High Similarity	NPC470811
0.922	High Similarity	NPC106920
0.922	High Similarity	NPC477697
0.922	High Similarity	NPC477696
0.9143	High Similarity	NPC203351
0.9143	High Similarity	NPC147379
0.913	High Similarity	NPC470990
0.9103	High Similarity	NPC174512
0.9103	High Similarity	NPC216223
0.9103	High Similarity	NPC293757
0.9103	High Similarity	NPC474965
0.9103	High Similarity	NPC477695
0.9103	High Similarity	NPC668
0.9103	High Similarity	NPC145569
0.9048	High Similarity	NPC56184
0.898	High Similarity	NPC477700
0.8973	High Similarity	NPC477698
0.8944	High Similarity	NPC100675
0.8919	High Similarity	NPC476434
0.8867	High Similarity	NPC199926
0.8867	High Similarity	NPC79998
0.8865	High Similarity	NPC308976
0.8859	High Similarity	NPC65591
0.8859	High Similarity	NPC178574
0.8851	High Similarity	NPC32079
0.8851	High Similarity	NPC164082
0.8851	High Similarity	NPC96501
0.8841	High Similarity	NPC469480
0.8828	High Similarity	NPC477702
0.8808	High Similarity	NPC150227
0.88	High Similarity	NPC30009
0.88	High Similarity	NPC103197
0.8768	High Similarity	NPC142985
0.8767	High Similarity	NPC212890
0.8758	High Similarity	NPC150943
0.8758	High Similarity	NPC268718
0.8758	High Similarity	NPC91634
0.875	High Similarity	NPC190020
0.875	High Similarity	NPC31751
0.875	High Similarity	NPC77679
0.875	High Similarity	NPC84935
0.875	High Similarity	NPC253481
0.875	High Similarity	NPC253722
0.8732	High Similarity	NPC281780
0.8723	High Similarity	NPC44245
0.8723	High Similarity	NPC211386
0.8723	High Similarity	NPC24490
0.8723	High Similarity	NPC126409
0.8723	High Similarity	NPC165155
0.8723	High Similarity	NPC34103
0.8723	High Similarity	NPC72796
0.8723	High Similarity	NPC141765
0.8723	High Similarity	NPC99572
0.8707	High Similarity	NPC32058
0.8707	High Similarity	NPC85734
0.8684	High Similarity	NPC478055
0.8676	High Similarity	NPC173608
0.8675	High Similarity	NPC281477
0.8675	High Similarity	NPC25127
0.8675	High Similarity	NPC287504
0.8667	High Similarity	NPC246566
0.8667	High Similarity	NPC95498
0.8652	High Similarity	NPC4982
0.8652	High Similarity	NPC176814
0.8652	High Similarity	NPC68779
0.8652	High Similarity	NPC300776
0.8652	High Similarity	NPC5310
0.8652	High Similarity	NPC67247
0.8645	High Similarity	NPC76687
0.8643	High Similarity	NPC175067
0.8643	High Similarity	NPC204215
0.8633	High Similarity	NPC195292
0.8627	High Similarity	NPC163527
0.8627	High Similarity	NPC115281
0.8627	High Similarity	NPC181168
0.8621	High Similarity	NPC151423
0.8621	High Similarity	NPC210354
0.8621	High Similarity	NPC40237
0.8621	High Similarity	NPC176586
0.8618	High Similarity	NPC82592
0.8618	High Similarity	NPC476642
0.8618	High Similarity	NPC16082
0.8611	High Similarity	NPC177868
0.8601	High Similarity	NPC14022
0.859	High Similarity	NPC14294
0.859	High Similarity	NPC116759
0.8582	High Similarity	NPC158331
0.8571	High Similarity	NPC76211
0.8562	High Similarity	NPC32373
0.8562	High Similarity	NPC237946
0.8552	High Similarity	NPC282291
0.8552	High Similarity	NPC166137
0.8544	High Similarity	NPC215802
0.8544	High Similarity	NPC167231
0.8543	High Similarity	NPC151425
0.8531	High Similarity	NPC471988
0.8521	High Similarity	NPC244983
0.8521	High Similarity	NPC326095
0.8521	High Similarity	NPC287745
0.8514	High Similarity	NPC3982
0.8506	High Similarity	NPC19947
0.8506	High Similarity	NPC207584
0.8503	High Similarity	NPC258307
0.8503	High Similarity	NPC92693
0.8503	High Similarity	NPC218841
0.8503	High Similarity	NPC177644
0.8503	High Similarity	NPC475000
0.8503	High Similarity	NPC191158
0.8497	Intermediate Similarity	NPC238834
0.8493	Intermediate Similarity	NPC287124
0.8493	Intermediate Similarity	NPC307287
0.8472	Intermediate Similarity	NPC125417
0.8472	Intermediate Similarity	NPC95679
0.8472	Intermediate Similarity	NPC25305
0.8472	Intermediate Similarity	NPC112068
0.8472	Intermediate Similarity	NPC110899
0.8462	Intermediate Similarity	NPC113295
0.8456	Intermediate Similarity	NPC208507
0.8456	Intermediate Similarity	NPC30720
0.8456	Intermediate Similarity	NPC472333
0.8446	Intermediate Similarity	NPC27106
0.844	Intermediate Similarity	NPC27843
0.844	Intermediate Similarity	NPC7171
0.844	Intermediate Similarity	NPC228346
0.844	Intermediate Similarity	NPC158079
0.844	Intermediate Similarity	NPC161557
0.844	Intermediate Similarity	NPC115207
0.844	Intermediate Similarity	NPC40432
0.8438	Intermediate Similarity	NPC91043
0.8435	Intermediate Similarity	NPC255566
0.8435	Intermediate Similarity	NPC298317
0.8435	Intermediate Similarity	NPC12728
0.8435	Intermediate Similarity	NPC185071
0.8435	Intermediate Similarity	NPC474288
0.8428	Intermediate Similarity	NPC185498
0.8421	Intermediate Similarity	NPC200773
0.8421	Intermediate Similarity	NPC240768
0.8406	Intermediate Similarity	NPC280767
0.8403	Intermediate Similarity	NPC90431
0.84	Intermediate Similarity	NPC1580
0.84	Intermediate Similarity	NPC102934
0.84	Intermediate Similarity	NPC252402
0.8397	Intermediate Similarity	NPC119910
0.8394	Intermediate Similarity	NPC220598
0.8394	Intermediate Similarity	NPC165375
0.8389	Intermediate Similarity	NPC472560
0.8389	Intermediate Similarity	NPC193779
0.838	Intermediate Similarity	NPC181049
0.838	Intermediate Similarity	NPC207400
0.8378	Intermediate Similarity	NPC477701
0.8378	Intermediate Similarity	NPC166884
0.8378	Intermediate Similarity	NPC87883
0.8378	Intermediate Similarity	NPC141569
0.8377	Intermediate Similarity	NPC186316
0.8367	Intermediate Similarity	NPC46180
0.8367	Intermediate Similarity	NPC52664
0.8366	Intermediate Similarity	NPC474606
0.8366	Intermediate Similarity	NPC245615
0.8366	Intermediate Similarity	NPC199773
0.8366	Intermediate Similarity	NPC299706
0.8366	Intermediate Similarity	NPC61604
0.8366	Intermediate Similarity	NPC115466
0.8366	Intermediate Similarity	NPC245948
0.8357	Intermediate Similarity	NPC109275
0.8356	Intermediate Similarity	NPC4796
0.8355	Intermediate Similarity	NPC210642
0.8355	Intermediate Similarity	NPC475756
0.8355	Intermediate Similarity	NPC62354
0.8355	Intermediate Similarity	NPC179178
0.8355	Intermediate Similarity	NPC303519
0.8355	Intermediate Similarity	NPC13985
0.8345	Intermediate Similarity	NPC474039
0.8344	Intermediate Similarity	NPC288149
0.8344	Intermediate Similarity	NPC100465
0.8344	Intermediate Similarity	NPC474903
0.8344	Intermediate Similarity	NPC152424
0.8344	Intermediate Similarity	NPC115624
0.8333	Intermediate Similarity	NPC104024
0.8333	Intermediate Similarity	NPC80230
0.8333	Intermediate Similarity	NPC221383
0.8333	Intermediate Similarity	NPC65574
0.8333	Intermediate Similarity	NPC304687
0.8333	Intermediate Similarity	NPC299090
0.8333	Intermediate Similarity	NPC143892
0.8333	Intermediate Similarity	NPC101755
0.8333	Intermediate Similarity	NPC283081
0.8323	Intermediate Similarity	NPC227062
0.8323	Intermediate Similarity	NPC179240
0.8322	Intermediate Similarity	NPC129889
0.8322	Intermediate Similarity	NPC307006
0.8322	Intermediate Similarity	NPC474982
0.8312	Intermediate Similarity	NPC238672

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 NPC27159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	793
0.2-0.3	1956
0.3-0.4	2655
0.4-0.5	1898
0.5-0.6	1034
0.6-0.7	461
0.7-0.8	84
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8816	High Similarity	NPD6234	Discontinued
0.8562	High Similarity	NPD4966	Approved
0.8562	High Similarity	NPD4967	Phase 2
0.8562	High Similarity	NPD4965	Approved
0.8428	Intermediate Similarity	NPD7228	Approved
0.8366	Intermediate Similarity	NPD37	Approved
0.8194	Intermediate Similarity	NPD230	Phase 1
0.8169	Intermediate Similarity	NPD3027	Phase 3
0.8013	Intermediate Similarity	NPD1934	Approved
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3882	Suspended
0.7908	Intermediate Similarity	NPD2532	Approved
0.7908	Intermediate Similarity	NPD2534	Approved
0.7908	Intermediate Similarity	NPD2533	Approved
0.7892	Intermediate Similarity	NPD7240	Approved
0.7888	Intermediate Similarity	NPD7199	Phase 2
0.7867	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD3818	Discontinued
0.7857	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2801	Approved
0.7791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1613	Approved
0.7755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6232	Discontinued
0.7727	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7473	Discontinued
0.7688	Intermediate Similarity	NPD3817	Phase 2
0.7655	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4110	Phase 3
0.7647	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6166	Phase 2
0.7625	Intermediate Similarity	NPD1465	Phase 2
0.7613	Intermediate Similarity	NPD1511	Approved
0.7607	Intermediate Similarity	NPD5494	Approved
0.7603	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD447	Suspended
0.756	Intermediate Similarity	NPD7074	Phase 3
0.7532	Intermediate Similarity	NPD1653	Approved
0.7529	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1512	Approved
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7054	Approved
0.7484	Intermediate Similarity	NPD6190	Approved
0.7483	Intermediate Similarity	NPD3705	Approved
0.7468	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6355	Discontinued
0.7466	Intermediate Similarity	NPD5647	Approved
0.7456	Intermediate Similarity	NPD7472	Approved
0.7451	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6004	Phase 3
0.7451	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6005	Phase 3
0.7451	Intermediate Similarity	NPD6002	Phase 3
0.7445	Intermediate Similarity	NPD228	Approved
0.7431	Intermediate Similarity	NPD9269	Phase 2
0.7419	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6653	Approved
0.7415	Intermediate Similarity	NPD9494	Approved
0.7412	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7383	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7075	Discontinued
0.7363	Intermediate Similarity	NPD7680	Approved
0.7362	Intermediate Similarity	NPD5353	Approved
0.7333	Intermediate Similarity	NPD919	Approved
0.7329	Intermediate Similarity	NPD4380	Phase 2
0.731	Intermediate Similarity	NPD6797	Phase 2
0.731	Intermediate Similarity	NPD1608	Approved
0.7308	Intermediate Similarity	NPD4628	Phase 3
0.7301	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7296	Approved
0.7278	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD2935	Discontinued
0.7267	Intermediate Similarity	NPD7685	Pre-registration
0.7267	Intermediate Similarity	NPD7251	Discontinued
0.7267	Intermediate Similarity	NPD6559	Discontinued
0.726	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5402	Approved
0.7226	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7808	Phase 3
0.7222	Intermediate Similarity	NPD6599	Discontinued
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7208	Intermediate Similarity	NPD1510	Phase 2
0.7202	Intermediate Similarity	NPD5710	Approved
0.7202	Intermediate Similarity	NPD5711	Approved
0.7202	Intermediate Similarity	NPD7229	Phase 3
0.7197	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7819	Suspended
0.7179	Intermediate Similarity	NPD1549	Phase 2
0.7178	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3620	Phase 2
0.7171	Intermediate Similarity	NPD4060	Phase 1
0.7171	Intermediate Similarity	NPD943	Approved
0.7171	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1240	Approved
0.7169	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1551	Phase 2
0.7161	Intermediate Similarity	NPD6099	Approved
0.7161	Intermediate Similarity	NPD6100	Approved
0.716	Intermediate Similarity	NPD5242	Approved
0.7153	Intermediate Similarity	NPD9268	Approved
0.7153	Intermediate Similarity	NPD1357	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD1247	Approved
0.7134	Intermediate Similarity	NPD2800	Approved
0.7134	Intermediate Similarity	NPD6801	Discontinued
0.7133	Intermediate Similarity	NPD4908	Phase 1
0.7125	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1610	Phase 2
0.7123	Intermediate Similarity	NPD422	Phase 1
0.7115	Intermediate Similarity	NPD7266	Discontinued
0.7108	Intermediate Similarity	NPD7768	Phase 2
0.7103	Intermediate Similarity	NPD17	Approved
0.7097	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7033	Discontinued
0.7095	Intermediate Similarity	NPD1283	Approved
0.7092	Intermediate Similarity	NPD5283	Phase 1
0.7089	Intermediate Similarity	NPD8166	Discontinued
0.7089	Intermediate Similarity	NPD3750	Approved
0.7079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1607	Approved
0.7063	Intermediate Similarity	NPD4357	Discontinued
0.7059	Intermediate Similarity	NPD826	Approved
0.7059	Intermediate Similarity	NPD3926	Phase 2
0.7059	Intermediate Similarity	NPD825	Approved
0.7051	Intermediate Similarity	NPD2438	Suspended
0.7051	Intermediate Similarity	NPD9570	Approved
0.7048	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD920	Approved
0.7037	Intermediate Similarity	NPD5403	Approved
0.7027	Intermediate Similarity	NPD4749	Approved
0.7027	Intermediate Similarity	NPD2982	Phase 2
0.7027	Intermediate Similarity	NPD2983	Phase 2
0.7025	Intermediate Similarity	NPD1652	Phase 2
0.7	Intermediate Similarity	NPD3787	Discontinued
0.6994	Remote Similarity	NPD3687	Approved
0.6994	Remote Similarity	NPD3686	Approved
0.6993	Remote Similarity	NPD4062	Phase 3
0.6986	Remote Similarity	NPD1778	Approved
0.6974	Remote Similarity	NPD7095	Approved
0.697	Remote Similarity	NPD7411	Suspended
0.6966	Remote Similarity	NPD9545	Approved
0.6964	Remote Similarity	NPD3749	Approved
0.6962	Remote Similarity	NPD5958	Discontinued
0.6959	Remote Similarity	NPD2981	Phase 2
0.6954	Remote Similarity	NPD3018	Phase 2
0.6954	Remote Similarity	NPD2861	Phase 2
0.6948	Remote Similarity	NPD2979	Phase 3
0.6943	Remote Similarity	NPD2796	Approved
0.6941	Remote Similarity	NPD6959	Discontinued
0.6937	Remote Similarity	NPD2219	Phase 1
0.6933	Remote Similarity	NPD2797	Approved
0.6928	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1243	Approved
0.6914	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5401	Approved
0.6914	Remote Similarity	NPD3146	Approved
0.6914	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7028	Phase 2
0.6903	Remote Similarity	NPD5124	Phase 1
0.6903	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7315	Approved
0.6899	Remote Similarity	NPD5763	Approved
0.6899	Remote Similarity	NPD5762	Approved
0.6899	Remote Similarity	NPD1375	Discontinued
0.6897	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1535	Discovery
0.6892	Remote Similarity	NPD1281	Approved
0.6887	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6663	Approved
0.6879	Remote Similarity	NPD2799	Discontinued
0.6875	Remote Similarity	NPD7827	Phase 1
0.6872	Remote Similarity	NPD8434	Phase 2
0.6867	Remote Similarity	NPD6385	Approved
0.6867	Remote Similarity	NPD6386	Approved
0.6855	Remote Similarity	NPD4534	Discontinued
0.6849	Remote Similarity	NPD1548	Phase 1
0.6846	Remote Similarity	NPD1481	Phase 2
0.6846	Remote Similarity	NPD9717	Approved
0.6845	Remote Similarity	NPD5006	Approved
0.6845	Remote Similarity	NPD5005	Approved
0.6839	Remote Similarity	NPD3751	Discontinued
0.6832	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6362	Approved
0.6821	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3268	Approved
0.6818	Remote Similarity	NPD1296	Phase 2
0.6815	Remote Similarity	NPD7097	Phase 1
0.6815	Remote Similarity	NPD6111	Discontinued
0.6813	Remote Similarity	NPD6674	Discontinued

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