NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.15
Volume:	257.918
LogP:	4.439
LogD:	3.727
LogS:	-3.981
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.84
Synthetic Accessibility Score:	2.759
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.769
MDCK Permeability:	2.294646947120782e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	94.42339324951172%
Volume Distribution (VD):	0.268
Pgp-substrate:	7.049636363983154%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.778
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.652
CYP2C9-inhibitor:	0.17
CYP2C9-substrate:	0.311
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	1.516
Half-life (T1/2):	0.396

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.514
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.723
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.11
Carcinogencity:	0.074
Eye Corrosion:	0.036
Eye Irritation:	0.928
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC249811

Natural Product ID:	NPC249811
*Common Name:**	NZAJKPWIGPUDBG-OAHLLOKOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NZAJKPWIGPUDBG-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C15H20O2/c1-14(2)9-4-10-15(14,3)12-7-5-11(6-8-12)13(16)17/h5-8H,4,9-10H2,1-3H3,(H,16,17)/t15-/m1/s1
SMILES:	OC(=O)c1ccc(cc1)[C@@]1(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581624
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32768	basidiomycete deconica sp. 471	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25871540]

☑ 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
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[559414]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	MIC	=	67.0	ug.mL-1	PMID[559414]

☑ 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 NPC249811 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	201
0.1-0.2	1165
0.2-0.3	2384
0.3-0.4	8009
0.4-0.5	14171
0.5-0.6	12584
0.6-0.7	3597
0.7-0.8	556
0.8-0.85	18
0.85-0.9	10
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.93	High Similarity	NPC304873
0.9293	High Similarity	NPC217621
0.9109	High Similarity	NPC25458
0.9091	High Similarity	NPC253423
0.9029	High Similarity	NPC105899
0.8919	High Similarity	NPC472708
0.8812	High Similarity	NPC229242
0.88	High Similarity	NPC61944
0.8704	High Similarity	NPC66208
0.8654	High Similarity	NPC255676
0.8636	High Similarity	NPC476357
0.8598	High Similarity	NPC318327
0.8485	Intermediate Similarity	NPC62765
0.8468	Intermediate Similarity	NPC186933
0.8448	Intermediate Similarity	NPC472703
0.8411	Intermediate Similarity	NPC37914
0.8381	Intermediate Similarity	NPC284477
0.8376	Intermediate Similarity	NPC472704
0.8304	Intermediate Similarity	NPC274839
0.83	Intermediate Similarity	NPC86670
0.83	Intermediate Similarity	NPC70940
0.83	Intermediate Similarity	NPC274455
0.8286	Intermediate Similarity	NPC282895
0.8273	Intermediate Similarity	NPC474057
0.8205	Intermediate Similarity	NPC167323
0.8205	Intermediate Similarity	NPC269923
0.819	Intermediate Similarity	NPC228435
0.819	Intermediate Similarity	NPC203925
0.8167	Intermediate Similarity	NPC472706
0.8165	Intermediate Similarity	NPC112903
0.8113	Intermediate Similarity	NPC70624
0.8108	Intermediate Similarity	NPC95126
0.8108	Intermediate Similarity	NPC475002
0.8099	Intermediate Similarity	NPC472707
0.8091	Intermediate Similarity	NPC85493
0.8087	Intermediate Similarity	NPC160199
0.8081	Intermediate Similarity	NPC318107
0.8067	Intermediate Similarity	NPC85511
0.8037	Intermediate Similarity	NPC188895
0.8036	Intermediate Similarity	NPC321852
0.8	Intermediate Similarity	NPC322387
0.8	Intermediate Similarity	NPC158157
0.7981	Intermediate Similarity	NPC130398
0.7966	Intermediate Similarity	NPC165197
0.7963	Intermediate Similarity	NPC329556
0.7946	Intermediate Similarity	NPC260818
0.7928	Intermediate Similarity	NPC469636
0.7925	Intermediate Similarity	NPC78701
0.7925	Intermediate Similarity	NPC35448
0.7921	Intermediate Similarity	NPC329064
0.7909	Intermediate Similarity	NPC83409
0.7909	Intermediate Similarity	NPC185763
0.7905	Intermediate Similarity	NPC261947
0.7899	Intermediate Similarity	NPC25168
0.7895	Intermediate Similarity	NPC471721
0.7895	Intermediate Similarity	NPC153053
0.7885	Intermediate Similarity	NPC261181
0.7864	Intermediate Similarity	NPC110704
0.7864	Intermediate Similarity	NPC79917
0.785	Intermediate Similarity	NPC325497
0.785	Intermediate Similarity	NPC146351
0.7833	Intermediate Similarity	NPC297193
0.783	Intermediate Similarity	NPC276775
0.783	Intermediate Similarity	NPC92754
0.783	Intermediate Similarity	NPC249912
0.7826	Intermediate Similarity	NPC93181
0.7823	Intermediate Similarity	NPC82712
0.7815	Intermediate Similarity	NPC472981
0.7807	Intermediate Similarity	NPC128368
0.7807	Intermediate Similarity	NPC93287
0.7805	Intermediate Similarity	NPC51448
0.7805	Intermediate Similarity	NPC115797
0.7788	Intermediate Similarity	NPC476003
0.7778	Intermediate Similarity	NPC473325
0.7778	Intermediate Similarity	NPC264728
0.7778	Intermediate Similarity	NPC285773
0.7768	Intermediate Similarity	NPC265407
0.7768	Intermediate Similarity	NPC83628
0.776	Intermediate Similarity	NPC72915
0.7757	Intermediate Similarity	NPC225060
0.7748	Intermediate Similarity	NPC37622
0.7748	Intermediate Similarity	NPC30594
0.7739	Intermediate Similarity	NPC196673
0.7739	Intermediate Similarity	NPC307651
0.7731	Intermediate Similarity	NPC133302
0.7731	Intermediate Similarity	NPC470585
0.7727	Intermediate Similarity	NPC31786
0.7727	Intermediate Similarity	NPC249067
0.7727	Intermediate Similarity	NPC329282
0.7723	Intermediate Similarity	NPC474211
0.7706	Intermediate Similarity	NPC45613
0.7705	Intermediate Similarity	NPC117794
0.7699	Intermediate Similarity	NPC95172
0.7698	Intermediate Similarity	NPC233692
0.7692	Intermediate Similarity	NPC212891
0.7679	Intermediate Similarity	NPC56493
0.7679	Intermediate Similarity	NPC34715
0.7679	Intermediate Similarity	NPC211439
0.7672	Intermediate Similarity	NPC221275
0.7672	Intermediate Similarity	NPC306740
0.7664	Intermediate Similarity	NPC133135
0.7664	Intermediate Similarity	NPC251579
0.7658	Intermediate Similarity	NPC209632
0.7656	Intermediate Similarity	NPC477594
0.7652	Intermediate Similarity	NPC272524
0.7652	Intermediate Similarity	NPC242957
0.7652	Intermediate Similarity	NPC206414
0.7652	Intermediate Similarity	NPC306977
0.7652	Intermediate Similarity	NPC287055
0.7647	Intermediate Similarity	NPC204784
0.7642	Intermediate Similarity	NPC472592
0.7642	Intermediate Similarity	NPC470765
0.7642	Intermediate Similarity	NPC275576
0.7636	Intermediate Similarity	NPC89886
0.7636	Intermediate Similarity	NPC474365
0.7636	Intermediate Similarity	NPC291426
0.7636	Intermediate Similarity	NPC247976
0.7636	Intermediate Similarity	NPC301943
0.7624	Intermediate Similarity	NPC474354
0.7623	Intermediate Similarity	NPC275145
0.7615	Intermediate Similarity	NPC42211
0.7615	Intermediate Similarity	NPC469481
0.7615	Intermediate Similarity	NPC225079
0.7615	Intermediate Similarity	NPC136810
0.7615	Intermediate Similarity	NPC128248
0.7615	Intermediate Similarity	NPC133809
0.7615	Intermediate Similarity	NPC289117
0.7611	Intermediate Similarity	NPC17417
0.7611	Intermediate Similarity	NPC10251
0.7607	Intermediate Similarity	NPC161304
0.7603	Intermediate Similarity	NPC18785
0.76	Intermediate Similarity	NPC44830
0.7597	Intermediate Similarity	NPC477596
0.7596	Intermediate Similarity	NPC58872
0.7593	Intermediate Similarity	NPC120393
0.7593	Intermediate Similarity	NPC210529
0.7593	Intermediate Similarity	NPC175852
0.7593	Intermediate Similarity	NPC160548
0.7589	Intermediate Similarity	NPC142326
0.7589	Intermediate Similarity	NPC244933
0.7589	Intermediate Similarity	NPC187913
0.7589	Intermediate Similarity	NPC94751
0.7589	Intermediate Similarity	NPC119271
0.7589	Intermediate Similarity	NPC85560
0.7586	Intermediate Similarity	NPC211421
0.7586	Intermediate Similarity	NPC237366
0.7581	Intermediate Similarity	NPC169913
0.7581	Intermediate Similarity	NPC470753
0.7581	Intermediate Similarity	NPC473220
0.7578	Intermediate Similarity	NPC28836
0.7578	Intermediate Similarity	NPC311492
0.7578	Intermediate Similarity	NPC203486
0.757	Intermediate Similarity	NPC469893
0.7568	Intermediate Similarity	NPC472222
0.7568	Intermediate Similarity	NPC114594
0.7568	Intermediate Similarity	NPC324786
0.7568	Intermediate Similarity	NPC472221
0.7565	Intermediate Similarity	NPC158282
0.7565	Intermediate Similarity	NPC82899
0.7565	Intermediate Similarity	NPC270699
0.7565	Intermediate Similarity	NPC471188
0.7563	Intermediate Similarity	NPC474890
0.7563	Intermediate Similarity	NPC161943
0.7563	Intermediate Similarity	NPC273282
0.7561	Intermediate Similarity	NPC295664
0.7559	Intermediate Similarity	NPC233860
0.7559	Intermediate Similarity	NPC125153
0.7559	Intermediate Similarity	NPC239358
0.7545	Intermediate Similarity	NPC320891
0.7544	Intermediate Similarity	NPC174099
0.7544	Intermediate Similarity	NPC214067
0.7544	Intermediate Similarity	NPC196246
0.7544	Intermediate Similarity	NPC93084
0.7544	Intermediate Similarity	NPC251854
0.7542	Intermediate Similarity	NPC83718
0.754	Intermediate Similarity	NPC272946
0.754	Intermediate Similarity	NPC117899
0.7525	Intermediate Similarity	NPC168855
0.7524	Intermediate Similarity	NPC86987
0.7523	Intermediate Similarity	NPC118343
0.7522	Intermediate Similarity	NPC226699
0.7521	Intermediate Similarity	NPC26433
0.7521	Intermediate Similarity	NPC35856
0.7521	Intermediate Similarity	NPC292665
0.7521	Intermediate Similarity	NPC244994
0.7521	Intermediate Similarity	NPC159760
0.7521	Intermediate Similarity	NPC178395
0.7521	Intermediate Similarity	NPC301987
0.7521	Intermediate Similarity	NPC272454
0.7521	Intermediate Similarity	NPC115188
0.7521	Intermediate Similarity	NPC179092
0.7521	Intermediate Similarity	NPC81808
0.7521	Intermediate Similarity	NPC222876
0.7521	Intermediate Similarity	NPC50872
0.7519	Intermediate Similarity	NPC232888
0.7519	Intermediate Similarity	NPC477367
0.75	Intermediate Similarity	NPC469890
0.75	Intermediate Similarity	NPC472248
0.75	Intermediate Similarity	NPC1793
0.75	Intermediate Similarity	NPC184579

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 NPC249811 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	856
0.2-0.3	1244
0.3-0.4	2656
0.4-0.5	2636
0.5-0.6	1173
0.6-0.7	318
0.7-0.8	64
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8807	High Similarity	NPD5951	Approved
0.8598	High Similarity	NPD6831	Clinical (unspecified phase)
0.85	High Similarity	NPD1088	Approved
0.8485	Intermediate Similarity	NPD9258	Approved
0.8485	Intermediate Similarity	NPD9256	Approved
0.8348	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1693	Approved
0.83	Intermediate Similarity	NPD1086	Approved
0.83	Intermediate Similarity	NPD1089	Approved
0.83	Intermediate Similarity	NPD1090	Approved
0.82	Intermediate Similarity	NPD800	Approved
0.819	Intermediate Similarity	NPD2066	Phase 3
0.8081	Intermediate Similarity	NPD9259	Approved
0.8081	Intermediate Similarity	NPD9257	Approved
0.8	Intermediate Similarity	NPD1087	Approved
0.7963	Intermediate Similarity	NPD1929	Approved
0.7963	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD1930	Approved
0.7885	Intermediate Similarity	NPD1202	Approved
0.7876	Intermediate Similarity	NPD9508	Approved
0.787	Intermediate Similarity	NPD1932	Approved
0.7864	Intermediate Similarity	NPD1239	Approved
0.7823	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9491	Approved
0.7727	Intermediate Similarity	NPD1237	Approved
0.7727	Intermediate Similarity	NPD164	Approved
0.768	Intermediate Similarity	NPD7008	Discontinued
0.7664	Intermediate Similarity	NPD1564	Approved
0.7664	Intermediate Similarity	NPD1566	Phase 3
0.7664	Intermediate Similarity	NPD1565	Approved
0.7652	Intermediate Similarity	NPD5277	Phase 2
0.7623	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD2329	Discontinued
0.7611	Intermediate Similarity	NPD2182	Approved
0.7593	Intermediate Similarity	NPD9495	Approved
0.7583	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD226	Approved
0.7547	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD1317	Discontinued
0.7523	Intermediate Similarity	NPD1238	Approved
0.7521	Intermediate Similarity	NPD2629	Approved
0.7521	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD7610	Discontinued
0.7477	Intermediate Similarity	NPD9260	Approved
0.7477	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6287	Discontinued
0.744	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7009	Phase 2
0.7407	Intermediate Similarity	NPD1989	Approved
0.7383	Intermediate Similarity	NPD1563	Approved
0.7374	Intermediate Similarity	NPD9490	Approved
0.7368	Intermediate Similarity	NPD9267	Approved
0.7368	Intermediate Similarity	NPD9264	Approved
0.7368	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD9263	Approved
0.7355	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5347	Phase 2
0.7333	Intermediate Similarity	NPD5346	Phase 2
0.7321	Intermediate Similarity	NPD6647	Phase 2
0.7308	Intermediate Similarity	NPD4793	Discontinued
0.7304	Intermediate Similarity	NPD74	Approved
0.7304	Intermediate Similarity	NPD9266	Approved
0.7295	Intermediate Similarity	NPD2932	Approved
0.7295	Intermediate Similarity	NPD3019	Approved
0.7282	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD227	Approved
0.7273	Intermediate Similarity	NPD225	Approved
0.7266	Intermediate Similarity	NPD6966	Discovery
0.7257	Intermediate Similarity	NPD5909	Discontinued
0.725	Intermediate Similarity	NPD9493	Approved
0.7213	Intermediate Similarity	NPD1245	Approved
0.7179	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1104	Approved
0.7154	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD9545	Approved
0.7119	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1164	Approved
0.7083	Intermediate Similarity	NPD1246	Approved
0.7059	Intermediate Similarity	NPD7094	Approved
0.7059	Intermediate Similarity	NPD6858	Approved
0.7029	Intermediate Similarity	NPD7236	Approved
0.7027	Intermediate Similarity	NPD3495	Discontinued
0.7025	Intermediate Similarity	NPD4198	Discontinued
0.7023	Intermediate Similarity	NPD6663	Approved
0.7023	Intermediate Similarity	NPD7961	Discontinued
0.7018	Intermediate Similarity	NPD9261	Approved
0.7008	Intermediate Similarity	NPD1888	Phase 1
0.7007	Intermediate Similarity	NPD4628	Phase 3
0.7007	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6049	Phase 2
0.7	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3972	Approved
0.6984	Remote Similarity	NPD4878	Approved
0.6977	Remote Similarity	NPD5736	Approved
0.697	Remote Similarity	NPD9716	Approved
0.6967	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4234	Approved
0.6949	Remote Similarity	NPD4233	Approved
0.6947	Remote Similarity	NPD3764	Approved
0.6944	Remote Similarity	NPD3672	Approved
0.6944	Remote Similarity	NPD3673	Approved
0.6942	Remote Similarity	NPD9281	Approved
0.6942	Remote Similarity	NPD4766	Approved
0.6935	Remote Similarity	NPD4102	Approved
0.6935	Remote Similarity	NPD4105	Approved
0.6923	Remote Similarity	NPD3971	Phase 1
0.6912	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1201	Approved
0.6901	Remote Similarity	NPD7239	Suspended
0.6899	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6085	Phase 2
0.6894	Remote Similarity	NPD7714	Approved
0.6894	Remote Similarity	NPD7715	Approved
0.6881	Remote Similarity	NPD7609	Phase 3
0.688	Remote Similarity	NPD5306	Approved
0.688	Remote Similarity	NPD5305	Approved
0.688	Remote Similarity	NPD2345	Approved
0.6879	Remote Similarity	NPD6273	Approved
0.687	Remote Similarity	NPD5765	Approved
0.686	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2652	Approved
0.686	Remote Similarity	NPD2650	Approved
0.685	Remote Similarity	NPD9717	Approved
0.6838	Remote Similarity	NPD5405	Approved
0.6838	Remote Similarity	NPD5404	Approved
0.6838	Remote Similarity	NPD6685	Approved
0.6838	Remote Similarity	NPD5406	Approved
0.6838	Remote Similarity	NPD5408	Approved
0.6825	Remote Similarity	NPD4135	Approved
0.6825	Remote Similarity	NPD3026	Approved
0.6825	Remote Similarity	NPD3023	Approved
0.6825	Remote Similarity	NPD4106	Approved
0.6825	Remote Similarity	NPD4136	Approved
0.6822	Remote Similarity	NPD1470	Approved
0.6822	Remote Similarity	NPD650	Approved
0.6818	Remote Similarity	NPD7631	Approved
0.6818	Remote Similarity	NPD1508	Approved
0.6807	Remote Similarity	NPD2067	Discontinued
0.68	Remote Similarity	NPD3025	Approved
0.68	Remote Similarity	NPD3024	Approved
0.6797	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5157	Phase 1
0.6797	Remote Similarity	NPD5159	Phase 2
0.6786	Remote Similarity	NPD844	Approved
0.6772	Remote Similarity	NPD4807	Approved
0.6772	Remote Similarity	NPD4806	Approved
0.6769	Remote Similarity	NPD2798	Approved
0.6765	Remote Similarity	NPD4308	Phase 3
0.6765	Remote Similarity	NPD7305	Phase 1
0.6748	Remote Similarity	NPD256	Approved
0.6748	Remote Similarity	NPD255	Approved
0.6744	Remote Similarity	NPD1876	Approved
0.6744	Remote Similarity	NPD1283	Approved
0.6731	Remote Similarity	NPD942	Approved
0.6726	Remote Similarity	NPD288	Approved
0.6718	Remote Similarity	NPD3663	Approved
0.6718	Remote Similarity	NPD3661	Approved
0.6718	Remote Similarity	NPD3662	Phase 3
0.6718	Remote Similarity	NPD3664	Approved
0.6696	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1889	Phase 1
0.6692	Remote Similarity	NPD411	Approved
0.6692	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD1755	Approved
0.6667	Remote Similarity	NPD5278	Discontinued
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD1756	Approved
0.6667	Remote Similarity	NPD9294	Approved
0.6667	Remote Similarity	NPD1752	Approved
0.6667	Remote Similarity	NPD253	Approved
0.6642	Remote Similarity	NPD2799	Discontinued
0.6641	Remote Similarity	NPD4980	Approved
0.6641	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD1843	Approved
0.6637	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD1809	Phase 2
0.6621	Remote Similarity	NPD7458	Discontinued
0.6621	Remote Similarity	NPD5086	Approved
0.6614	Remote Similarity	NPD9272	Approved
0.6614	Remote Similarity	NPD4626	Approved
0.6614	Remote Similarity	NPD1778	Approved
0.6612	Remote Similarity	NPD3644	Approved
0.6612	Remote Similarity	NPD3643	Approved
0.6612	Remote Similarity	NPD3642	Approved
0.661	Remote Similarity	NPD5048	Discontinued
0.661	Remote Similarity	NPD1018	Approved
0.6609	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3020	Approved
0.6607	Remote Similarity	NPD845	Approved
0.6606	Remote Similarity	NPD1101	Approved
0.6594	Remote Similarity	NPD2935	Discontinued
0.6591	Remote Similarity	NPD5204	Approved
0.6589	Remote Similarity	NPD1608	Approved
0.6581	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD2313	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