NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.1
Volume:	258.385
LogP:	2.849
LogD:	2.855
LogS:	-4.487
# Rotatable Bonds:	0
TPSA:	51.97
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	5.798
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.691
MDCK Permeability:	2.688405947992578e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.424
Plasma Protein Binding (PPB):	90.63257598876953%
Volume Distribution (VD):	1.521
Pgp-substrate:	6.808581829071045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.653
CYP2C19-inhibitor:	0.709
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.177
CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.722
CYP3A4-inhibitor:	0.602
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	13.541
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.661
Drug-inuced Liver Injury (DILI):	0.82
AMES Toxicity:	0.829
Rat Oral Acute Toxicity:	0.909
Maximum Recommended Daily Dose:	0.151
Skin Sensitization:	0.593
Carcinogencity:	0.707
Eye Corrosion:	0.079
Eye Irritation:	0.043
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC248795

Natural Product ID:	NPC248795
*Common Name:**	Linderane
IUPAC Name:	n.a.
Synonyms:	Linderane
Standard InCHIKey:	KBMSVODXFLAQNJ-DXGHHDSJSA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-8-4-3-5-15-13(19-15)12(18-14(15)16)11-9(2)7-17-10(11)6-8/h4,7,12-13H,3,5-6H2,1-2H3/b8-4+/t12-,13-,15-/m0/s1
SMILES:	C/C/1=CCC[C@]23[C@H]([C@H](c4c(C)coc4C1)OC2=O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079723
PubChem CID:	6915739
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000368] Dioxanes [CHEMONTID:0001313] 1,4-dioxanes

*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
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13346	Lindera strichnifolia	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4682	Lindera aggregata	Species	Lauraceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	EC50	=	167000.0	nM	PMID[560008]

☑ 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 NPC248795 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	384
0.1-0.2	1599
0.2-0.3	4271
0.3-0.4	9918
0.4-0.5	10063
0.5-0.6	7347
0.6-0.7	8255
0.7-0.8	818
0.8-0.85	16
0.85-0.9	20
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9407	High Similarity	NPC286130
0.9085	High Similarity	NPC475864
0.9065	High Similarity	NPC282973
0.9044	High Similarity	NPC200718
0.9028	High Similarity	NPC475904
0.9028	High Similarity	NPC474270
0.9014	High Similarity	NPC195920
0.8958	High Similarity	NPC474255
0.8958	High Similarity	NPC474220
0.8958	High Similarity	NPC471618
0.8889	High Similarity	NPC474317
0.8881	High Similarity	NPC37488
0.8873	High Similarity	NPC110305
0.8716	High Similarity	NPC474219
0.8716	High Similarity	NPC474378
0.8593	High Similarity	NPC216810
0.8592	High Similarity	NPC474615
0.8478	Intermediate Similarity	NPC45947
0.8425	Intermediate Similarity	NPC86935
0.8356	Intermediate Similarity	NPC22248
0.8344	Intermediate Similarity	NPC470380
0.8322	Intermediate Similarity	NPC19747
0.8299	Intermediate Similarity	NPC84479
0.8231	Intermediate Similarity	NPC205071
0.8207	Intermediate Similarity	NPC107571
0.8129	Intermediate Similarity	NPC184391
0.8129	Intermediate Similarity	NPC137570
0.8113	Intermediate Similarity	NPC473766
0.8113	Intermediate Similarity	NPC473753
0.8112	Intermediate Similarity	NPC106247
0.8108	Intermediate Similarity	NPC254198
0.8077	Intermediate Similarity	NPC473368
0.8067	Intermediate Similarity	NPC104924
0.8067	Intermediate Similarity	NPC62799
0.806	Intermediate Similarity	NPC227660
0.8052	Intermediate Similarity	NPC114880
0.8028	Intermediate Similarity	NPC136340
0.8026	Intermediate Similarity	NPC211625
0.8025	Intermediate Similarity	NPC305016
0.8012	Intermediate Similarity	NPC302392
0.8	Intermediate Similarity	NPC75310
0.8	Intermediate Similarity	NPC303217
0.7987	Intermediate Similarity	NPC261184
0.7987	Intermediate Similarity	NPC475777
0.7958	Intermediate Similarity	NPC21460
0.7949	Intermediate Similarity	NPC107646
0.7949	Intermediate Similarity	NPC209364
0.7949	Intermediate Similarity	NPC60973
0.7949	Intermediate Similarity	NPC263265
0.7945	Intermediate Similarity	NPC473268
0.7922	Intermediate Similarity	NPC18135
0.7911	Intermediate Similarity	NPC333139
0.7898	Intermediate Similarity	NPC286722
0.7898	Intermediate Similarity	NPC187149
0.7895	Intermediate Similarity	NPC221809
0.7875	Intermediate Similarity	NPC123088
0.7848	Intermediate Similarity	NPC473473
0.7848	Intermediate Similarity	NPC475295
0.7848	Intermediate Similarity	NPC237155
0.7847	Intermediate Similarity	NPC45358
0.7834	Intermediate Similarity	NPC278010
0.7834	Intermediate Similarity	NPC295608
0.7834	Intermediate Similarity	NPC126723
0.7834	Intermediate Similarity	NPC250769
0.7829	Intermediate Similarity	NPC97904
0.782	Intermediate Similarity	NPC22678
0.7815	Intermediate Similarity	NPC261733
0.7815	Intermediate Similarity	NPC267004
0.7815	Intermediate Similarity	NPC218712
0.7815	Intermediate Similarity	NPC137295
0.7815	Intermediate Similarity	NPC307346
0.7812	Intermediate Similarity	NPC469846
0.7808	Intermediate Similarity	NPC159786
0.7799	Intermediate Similarity	NPC475381
0.7799	Intermediate Similarity	NPC191828
0.7799	Intermediate Similarity	NPC25255
0.7793	Intermediate Similarity	NPC474426
0.7793	Intermediate Similarity	NPC474407
0.7793	Intermediate Similarity	NPC474425
0.7778	Intermediate Similarity	NPC476861
0.7778	Intermediate Similarity	NPC476850
0.7778	Intermediate Similarity	NPC279768
0.7778	Intermediate Similarity	NPC17681
0.7771	Intermediate Similarity	NPC131725
0.7771	Intermediate Similarity	NPC214541
0.7771	Intermediate Similarity	NPC44675
0.7756	Intermediate Similarity	NPC75906
0.775	Intermediate Similarity	NPC5079
0.775	Intermediate Similarity	NPC193798
0.775	Intermediate Similarity	NPC470939
0.7748	Intermediate Similarity	NPC223415
0.7748	Intermediate Similarity	NPC470741
0.7746	Intermediate Similarity	NPC319140
0.7746	Intermediate Similarity	NPC95567
0.7736	Intermediate Similarity	NPC116639
0.773	Intermediate Similarity	NPC472895
0.7724	Intermediate Similarity	NPC471545
0.7724	Intermediate Similarity	NPC471544
0.7724	Intermediate Similarity	NPC97740
0.7724	Intermediate Similarity	NPC473344
0.7722	Intermediate Similarity	NPC474542
0.7716	Intermediate Similarity	NPC132054
0.7703	Intermediate Similarity	NPC186626
0.7702	Intermediate Similarity	NPC476035
0.7702	Intermediate Similarity	NPC234660
0.7702	Intermediate Similarity	NPC475039
0.7702	Intermediate Similarity	NPC51568
0.7702	Intermediate Similarity	NPC14499
0.7697	Intermediate Similarity	NPC144288
0.7688	Intermediate Similarity	NPC335761
0.7688	Intermediate Similarity	NPC472653
0.7682	Intermediate Similarity	NPC473152
0.7673	Intermediate Similarity	NPC36655
0.7673	Intermediate Similarity	NPC261597
0.7673	Intermediate Similarity	NPC299038
0.7673	Intermediate Similarity	NPC470625
0.7671	Intermediate Similarity	NPC293253
0.7671	Intermediate Similarity	NPC214097
0.7669	Intermediate Similarity	NPC472651
0.7669	Intermediate Similarity	NPC179015
0.7669	Intermediate Similarity	NPC173149
0.7667	Intermediate Similarity	NPC473681
0.7667	Intermediate Similarity	NPC61157
0.7667	Intermediate Similarity	NPC218204
0.766	Intermediate Similarity	NPC188377
0.766	Intermediate Similarity	NPC65735
0.7658	Intermediate Similarity	NPC472785
0.7658	Intermediate Similarity	NPC301233
0.7654	Intermediate Similarity	NPC476857
0.7654	Intermediate Similarity	NPC476856
0.7654	Intermediate Similarity	NPC476858
0.7654	Intermediate Similarity	NPC476860
0.7647	Intermediate Similarity	NPC76657
0.7647	Intermediate Similarity	NPC105381
0.7647	Intermediate Similarity	NPC10302
0.7643	Intermediate Similarity	NPC323118
0.7643	Intermediate Similarity	NPC44577
0.764	Intermediate Similarity	NPC188649
0.764	Intermediate Similarity	NPC117986
0.7636	Intermediate Similarity	NPC159232
0.7632	Intermediate Similarity	NPC64568
0.7632	Intermediate Similarity	NPC80635
0.7625	Intermediate Similarity	NPC477403
0.7625	Intermediate Similarity	NPC475967
0.7622	Intermediate Similarity	NPC298071
0.7622	Intermediate Similarity	NPC271235
0.7622	Intermediate Similarity	NPC472652
0.761	Intermediate Similarity	NPC104736
0.761	Intermediate Similarity	NPC469485
0.7607	Intermediate Similarity	NPC23387
0.7605	Intermediate Similarity	NPC167340
0.7597	Intermediate Similarity	NPC316535
0.7595	Intermediate Similarity	NPC57998
0.7593	Intermediate Similarity	NPC88841
0.7593	Intermediate Similarity	NPC134254
0.7593	Intermediate Similarity	NPC472783
0.7593	Intermediate Similarity	NPC14822
0.7593	Intermediate Similarity	NPC39986
0.7593	Intermediate Similarity	NPC288602
0.7593	Intermediate Similarity	NPC472780
0.7593	Intermediate Similarity	NPC302369
0.7593	Intermediate Similarity	NPC285567
0.7593	Intermediate Similarity	NPC283209
0.7582	Intermediate Similarity	NPC476310
0.7582	Intermediate Similarity	NPC476164
0.758	Intermediate Similarity	NPC191104
0.7578	Intermediate Similarity	NPC287559
0.7571	Intermediate Similarity	NPC1848
0.7568	Intermediate Similarity	NPC92941
0.7566	Intermediate Similarity	NPC470856
0.7564	Intermediate Similarity	NPC329180
0.7562	Intermediate Similarity	NPC173544
0.7562	Intermediate Similarity	NPC304692
0.7562	Intermediate Similarity	NPC472283
0.7561	Intermediate Similarity	NPC476853
0.7552	Intermediate Similarity	NPC52035
0.7551	Intermediate Similarity	NPC470859
0.7548	Intermediate Similarity	NPC250228
0.7548	Intermediate Similarity	NPC71821
0.7548	Intermediate Similarity	NPC471346
0.7546	Intermediate Similarity	NPC276735
0.7533	Intermediate Similarity	NPC177262
0.7533	Intermediate Similarity	NPC476943
0.7533	Intermediate Similarity	NPC220094
0.7532	Intermediate Similarity	NPC268905
0.7531	Intermediate Similarity	NPC49009
0.7531	Intermediate Similarity	NPC18986
0.7531	Intermediate Similarity	NPC18347
0.7531	Intermediate Similarity	NPC472781
0.7531	Intermediate Similarity	NPC239270
0.7531	Intermediate Similarity	NPC197596
0.7531	Intermediate Similarity	NPC149896
0.7531	Intermediate Similarity	NPC95472
0.7531	Intermediate Similarity	NPC303210
0.7531	Intermediate Similarity	NPC472782
0.7516	Intermediate Similarity	NPC474611
0.7516	Intermediate Similarity	NPC46551
0.7516	Intermediate Similarity	NPC88445
0.7515	Intermediate Similarity	NPC155264
0.7515	Intermediate Similarity	NPC296558

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 NPC248795 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	1060
0.2-0.3	2211
0.3-0.4	2791
0.4-0.5	1823
0.5-0.6	715
0.6-0.7	218
0.7-0.8	3
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7911	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD920	Approved
0.7469	Intermediate Similarity	NPD919	Approved
0.7372	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD1247	Approved
0.725	Intermediate Similarity	NPD6599	Discontinued
0.7244	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8434	Phase 2
0.7161	Intermediate Similarity	NPD1243	Approved
0.7091	Intermediate Similarity	NPD7075	Discontinued
0.7073	Intermediate Similarity	NPD3817	Phase 2
0.7055	Intermediate Similarity	NPD6801	Discontinued
0.7044	Intermediate Similarity	NPD2532	Approved
0.7044	Intermediate Similarity	NPD2534	Approved
0.7044	Intermediate Similarity	NPD2533	Approved
0.7032	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1471	Phase 3
0.7006	Intermediate Similarity	NPD4628	Phase 3
0.6994	Remote Similarity	NPD6765	Approved
0.6994	Remote Similarity	NPD6764	Approved
0.697	Remote Similarity	NPD5402	Approved
0.6968	Remote Similarity	NPD2796	Approved
0.6962	Remote Similarity	NPD3887	Approved
0.6959	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5403	Approved
0.6937	Remote Similarity	NPD5401	Approved
0.6928	Remote Similarity	NPD3882	Suspended
0.6909	Remote Similarity	NPD5761	Phase 2
0.6909	Remote Similarity	NPD5760	Phase 2
0.6905	Remote Similarity	NPD5494	Approved
0.6882	Remote Similarity	NPD3926	Phase 2
0.6842	Remote Similarity	NPD2403	Approved
0.6836	Remote Similarity	NPD6784	Approved
0.6836	Remote Similarity	NPD6785	Approved
0.6835	Remote Similarity	NPD2800	Approved
0.6832	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6832	Phase 2
0.68	Remote Similarity	NPD1019	Discontinued
0.6786	Remote Similarity	NPD3749	Approved
0.6781	Remote Similarity	NPD17	Approved
0.6776	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1551	Phase 2
0.6732	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2067	Discontinued
0.671	Remote Similarity	NPD447	Suspended
0.671	Remote Similarity	NPD6355	Discontinued
0.6709	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6002	Phase 3
0.6709	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6004	Phase 3
0.6709	Remote Similarity	NPD2353	Approved
0.6709	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6005	Phase 3
0.6709	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7819	Suspended
0.6705	Remote Similarity	NPD6559	Discontinued
0.669	Remote Similarity	NPD9092	Discovery
0.6688	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1934	Approved
0.6646	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD9717	Approved
0.6644	Remote Similarity	NPD1608	Approved
0.6629	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6808	Phase 2
0.6628	Remote Similarity	NPD3787	Discontinued
0.6627	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2313	Discontinued
0.6607	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD2344	Approved
0.6603	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7411	Suspended
0.6582	Remote Similarity	NPD3748	Approved
0.6582	Remote Similarity	NPD2799	Discontinued
0.6581	Remote Similarity	NPD6233	Phase 2
0.6579	Remote Similarity	NPD5647	Approved
0.6577	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3818	Discontinued
0.6571	Remote Similarity	NPD3751	Discontinued
0.6552	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6166	Phase 2
0.6552	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2354	Approved
0.6538	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD4380	Phase 2
0.6516	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6798	Discontinued
0.6513	Remote Similarity	NPD3267	Approved
0.6513	Remote Similarity	NPD3266	Approved
0.6509	Remote Similarity	NPD2801	Approved
0.65	Remote Similarity	NPD2346	Discontinued
0.6497	Remote Similarity	NPD1933	Approved
0.6497	Remote Similarity	NPD230	Phase 1
0.6485	Remote Similarity	NPD1512	Approved
0.6481	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD1510	Phase 2
0.6471	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3226	Approved
0.6463	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6797	Phase 2
0.6457	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD2309	Approved
0.6437	Remote Similarity	NPD5711	Approved
0.6437	Remote Similarity	NPD5710	Approved
0.6433	Remote Similarity	NPD4307	Phase 2
0.6433	Remote Similarity	NPD1240	Approved
0.6425	Remote Similarity	NPD7251	Discontinued
0.6424	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD3146	Approved
0.6424	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2654	Approved
0.6419	Remote Similarity	NPD9545	Approved
0.6414	Remote Similarity	NPD1241	Discontinued
0.641	Remote Similarity	NPD3268	Approved
0.6405	Remote Similarity	NPD1203	Approved
0.64	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7808	Phase 3
0.6384	Remote Similarity	NPD2163	Approved
0.638	Remote Similarity	NPD3750	Approved
0.6374	Remote Similarity	NPD5353	Approved
0.6374	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD4062	Phase 3
0.6364	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1511	Approved
0.6364	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2897	Discontinued
0.6353	Remote Similarity	NPD6279	Approved
0.6353	Remote Similarity	NPD6280	Approved
0.6352	Remote Similarity	NPD1607	Approved
0.6349	Remote Similarity	NPD8285	Discontinued
0.6348	Remote Similarity	NPD5844	Phase 1
0.6343	Remote Similarity	NPD6232	Discontinued
0.6337	Remote Similarity	NPD7768	Phase 2
0.6337	Remote Similarity	NPD4967	Phase 2
0.6337	Remote Similarity	NPD4966	Approved
0.6337	Remote Similarity	NPD4965	Approved
0.6335	Remote Similarity	NPD2935	Discontinued
0.6328	Remote Similarity	NPD7473	Discontinued
0.6316	Remote Similarity	NPD3972	Approved
0.6313	Remote Similarity	NPD7074	Phase 3
0.631	Remote Similarity	NPD957	Approved
0.6307	Remote Similarity	NPD5242	Approved
0.6306	Remote Similarity	NPD411	Approved
0.6306	Remote Similarity	NPD3764	Approved
0.6299	Remote Similarity	NPD2797	Approved
0.6294	Remote Similarity	NPD2182	Approved
0.6294	Remote Similarity	NPD6385	Approved
0.6294	Remote Similarity	NPD6386	Approved
0.6287	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD5049	Phase 3
0.6286	Remote Similarity	NPD6959	Discontinued
0.628	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4308	Phase 3
0.6267	Remote Similarity	NPD5585	Approved
0.6264	Remote Similarity	NPD6234	Discontinued
0.6258	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD2424	Discontinued
0.6258	Remote Similarity	NPD5958	Discontinued
0.6258	Remote Similarity	NPD2798	Approved
0.6258	Remote Similarity	NPD4534	Discontinued
0.6257	Remote Similarity	NPD7054	Approved
0.625	Remote Similarity	NPD8404	Phase 2
0.625	Remote Similarity	NPD6653	Approved
0.6243	Remote Similarity	NPD7685	Pre-registration
0.6242	Remote Similarity	NPD7095	Approved
0.6242	Remote Similarity	NPD6190	Approved
0.6225	Remote Similarity	NPD1778	Approved
0.6224	Remote Similarity	NPD1358	Approved
0.6222	Remote Similarity	NPD7472	Approved
0.6221	Remote Similarity	NPD7972	Discontinued
0.6221	Remote Similarity	NPD1465	Phase 2
0.6218	Remote Similarity	NPD9494	Approved
0.6205	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD1296	Phase 2
0.6201	Remote Similarity	NPD7799	Discontinued
0.6199	Remote Similarity	NPD5890	Approved
0.6199	Remote Similarity	NPD5889	Approved
0.6199	Remote Similarity	NPD958	Approved
0.6196	Remote Similarity	NPD5763	Approved
0.6196	Remote Similarity	NPD5762	Approved
0.6194	Remote Similarity	NPD987	Approved
0.6193	Remote Similarity	NPD7199	Phase 2
0.6188	Remote Similarity	NPD5953	Discontinued
0.6175	Remote Similarity	NPD8312	Approved
0.6175	Remote Similarity	NPD8313	Approved
0.6174	Remote Similarity	NPD9493	Approved
0.6167	Remote Similarity	NPD7286	Phase 2

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