NPASS Compound

Structure

NPC474439 OpenBabel07101718182D 33 34 0 0 1 0 0 0 0 0999 V2000 -5.3364 -5.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -4.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6843 -4.4025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8841 0.9013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3364 -5.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3364 -3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8364 -4.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3364 -5.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3364 -3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3364 -3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3364 -3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8364 -4.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8364 -4.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8364 -2.4487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.8752 -3.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3364 -3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -9.9242 -4.1237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8752 -2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -9.6152 -5.0748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6843 -2.2269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9242 -2.5057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 4 21 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 18 2 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 23 2 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 20 3 1 6 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 25 1 0 0 0 0 23 32 1 0 0 0 0 24 30 1 0 0 0 0 24 33 1 0 0 0 0 25 28 1 0 0 0 0 26 29 2 0 0 0 0 26 32 1 0 0 0 0 27 31 1 0 0 0 0 27 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.28
Volume:	495.358
LogP:	4.435
LogD:	3.582
LogS:	-4.672
# Rotatable Bonds:	13
TPSA:	81.29
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	4.664
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.745
MDCK Permeability:	2.599066101538483e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.778
Human Intestinal Absorption (HIA):	0.779
20% Bioavailability (F20%):	0.647
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	96.32576751708984%
Volume Distribution (VD):	0.873
Pgp-substrate:	1.4156244993209839%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.657
CYP2C19-inhibitor:	0.18
CYP2C19-substrate:	0.739
CYP2C9-inhibitor:	0.783
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.768
CYP2D6-substrate:	0.856
CYP3A4-inhibitor:	0.178
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	1.638
Half-life (T1/2):	0.552

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.762
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.909
Carcinogencity:	0.6
Eye Corrosion:	0.003
Eye Irritation:	0.163
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC474439

Natural Product ID:	NPC474439
*Common Name:**	5-((R,6E,10E)-13-(2,5-Dimethoxy-2,5-Dihydrofuran-3-Yl)-2,6,10-Trimethyltrideca-6,10-Dienylidene)-4-Hydroxy-3-Methylfuran-2(5H)-One
IUPAC Name:	(5Z)-5-[(2R,6E,10E)-13-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)-2,6,10-trimethyltrideca-6,10-dienylidene]-4-hydroxy-3-methylfuran-2-one
Synonyms:
Standard InCHIKey:	NOHWRIRNNOPMMP-UGGUYPQDSA-N
Standard InCHI:	InChI=1S/C27H40O6/c1-18(12-8-14-20(3)16-23-25(28)21(4)26(29)32-23)10-7-11-19(2)13-9-15-22-17-24(30-5)33-27(22)31-6/h10,13,16-17,20,24,27-28H,7-9,11-12,14-15H2,1-6H3/b18-10+,19-13+,23-16-/t20-,24?,27?/m1/s1
SMILES:	CC1=C(C(=CC(C)CCCC(=CCCC(=CCCC2=CC(OC2OC)OC)C)C)OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468563
PubChem CID:	54729895
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene 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
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678655]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350153]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341287]

☑ 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	9
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	42.1	ug.mL-1	PMID[471268]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	80.0	ug.mL-1	PMID[471268]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	50.0	ug.mL-1	PMID[471268]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100.0	ug.mL-1	PMID[471268]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	PMID[471268]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[471268]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[471268]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	100.0	ug.mL-1	PMID[471268]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[471268]

☑ 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 NPC474439 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	180
0.1-0.2	1389
0.2-0.3	6582
0.3-0.4	17630
0.4-0.5	11642
0.5-0.6	4215
0.6-0.7	993
0.7-0.8	58
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474028
0.9615	High Similarity	NPC475714
0.9375	High Similarity	NPC474424
0.925	High Similarity	NPC475706
0.881	High Similarity	NPC475739
0.8391	Intermediate Similarity	NPC475995
0.8391	Intermediate Similarity	NPC474098
0.8046	Intermediate Similarity	NPC45409
0.7778	Intermediate Similarity	NPC470686
0.7625	Intermediate Similarity	NPC329904
0.7625	Intermediate Similarity	NPC473361
0.7582	Intermediate Similarity	NPC475879
0.7471	Intermediate Similarity	NPC324170
0.7471	Intermediate Similarity	NPC471296
0.7407	Intermediate Similarity	NPC37929
0.7407	Intermediate Similarity	NPC64234
0.7375	Intermediate Similarity	NPC313444
0.7349	Intermediate Similarity	NPC315843
0.7349	Intermediate Similarity	NPC107654
0.7342	Intermediate Similarity	NPC191233
0.734	Intermediate Similarity	NPC470521
0.7312	Intermediate Similarity	NPC470520
0.7303	Intermediate Similarity	NPC161670
0.7294	Intermediate Similarity	NPC315394
0.7294	Intermediate Similarity	NPC473756
0.7284	Intermediate Similarity	NPC470693
0.7284	Intermediate Similarity	NPC232812
0.7273	Intermediate Similarity	NPC323251
0.7273	Intermediate Similarity	NPC471298
0.7245	Intermediate Similarity	NPC219038
0.7234	Intermediate Similarity	NPC472196
0.7234	Intermediate Similarity	NPC472195
0.7234	Intermediate Similarity	NPC59646
0.7234	Intermediate Similarity	NPC238090
0.7229	Intermediate Similarity	NPC476490
0.7229	Intermediate Similarity	NPC476489
0.7222	Intermediate Similarity	NPC474860
0.7222	Intermediate Similarity	NPC471300
0.7222	Intermediate Similarity	NPC163606
0.7215	Intermediate Similarity	NPC220766
0.7204	Intermediate Similarity	NPC327253
0.7204	Intermediate Similarity	NPC3436
0.7204	Intermediate Similarity	NPC118078
0.7195	Intermediate Similarity	NPC316029
0.7195	Intermediate Similarity	NPC315285
0.7195	Intermediate Similarity	NPC315597
0.7191	Intermediate Similarity	NPC471297
0.7188	Intermediate Similarity	NPC473333
0.7179	Intermediate Similarity	NPC475073
0.7172	Intermediate Similarity	NPC471599
0.7158	Intermediate Similarity	NPC159698
0.7128	Intermediate Similarity	NPC32494
0.7128	Intermediate Similarity	NPC175842
0.7128	Intermediate Similarity	NPC477749
0.7125	Intermediate Similarity	NPC315115
0.7113	Intermediate Similarity	NPC471490
0.7113	Intermediate Similarity	NPC2666
0.7111	Intermediate Similarity	NPC266718
0.7111	Intermediate Similarity	NPC471301
0.7111	Intermediate Similarity	NPC475035
0.7111	Intermediate Similarity	NPC126518
0.7111	Intermediate Similarity	NPC471302
0.7108	Intermediate Similarity	NPC316185
0.7097	Intermediate Similarity	NPC225283
0.7097	Intermediate Similarity	NPC242877
0.7097	Intermediate Similarity	NPC64913
0.7097	Intermediate Similarity	NPC477748
0.7093	Intermediate Similarity	NPC68156
0.7083	Intermediate Similarity	NPC471492
0.7079	Intermediate Similarity	NPC16321
0.7073	Intermediate Similarity	NPC151481
0.7071	Intermediate Similarity	NPC20673
0.7059	Intermediate Similarity	NPC478192
0.7059	Intermediate Similarity	NPC478196
0.7059	Intermediate Similarity	NPC478194
0.7059	Intermediate Similarity	NPC315552
0.7059	Intermediate Similarity	NPC478193
0.7059	Intermediate Similarity	NPC478195
0.7059	Intermediate Similarity	NPC478191
0.7053	Intermediate Similarity	NPC29798
0.7053	Intermediate Similarity	NPC320552
0.7053	Intermediate Similarity	NPC282644
0.7041	Intermediate Similarity	NPC151093
0.7037	Intermediate Similarity	NPC472266
0.7033	Intermediate Similarity	NPC471494
0.7024	Intermediate Similarity	NPC316851
0.7021	Intermediate Similarity	NPC202886
0.7	Intermediate Similarity	NPC286770
0.7	Intermediate Similarity	NPC471556
0.7	Intermediate Similarity	NPC284472
0.7	Intermediate Similarity	NPC229799
0.6989	Remote Similarity	NPC260343
0.6989	Remote Similarity	NPC474629
0.6988	Remote Similarity	NPC59558
0.697	Remote Similarity	NPC244878
0.6962	Remote Similarity	NPC155849
0.6957	Remote Similarity	NPC311163
0.6957	Remote Similarity	NPC211892
0.6951	Remote Similarity	NPC310210
0.6941	Remote Similarity	NPC474758
0.6939	Remote Similarity	NPC52820
0.6932	Remote Similarity	NPC271632
0.6932	Remote Similarity	NPC99651
0.6932	Remote Similarity	NPC471537
0.6923	Remote Similarity	NPC473308
0.69	Remote Similarity	NPC4637
0.69	Remote Similarity	NPC98859
0.6897	Remote Similarity	NPC316324
0.6897	Remote Similarity	NPC471225
0.6897	Remote Similarity	NPC473825
0.6897	Remote Similarity	NPC10572
0.6889	Remote Similarity	NPC475046
0.6889	Remote Similarity	NPC310450
0.6889	Remote Similarity	NPC474959
0.6889	Remote Similarity	NPC11383
0.6882	Remote Similarity	NPC316138
0.6882	Remote Similarity	NPC475037
0.6882	Remote Similarity	NPC475186
0.6882	Remote Similarity	NPC118077
0.6882	Remote Similarity	NPC475678
0.6882	Remote Similarity	NPC313658
0.6875	Remote Similarity	NPC189651
0.6875	Remote Similarity	NPC156553
0.6875	Remote Similarity	NPC475098
0.6869	Remote Similarity	NPC124181
0.6869	Remote Similarity	NPC203627
0.686	Remote Similarity	NPC329852
0.6848	Remote Similarity	NPC67081
0.6848	Remote Similarity	NPC475034
0.6848	Remote Similarity	NPC329630
0.6848	Remote Similarity	NPC472442
0.6848	Remote Similarity	NPC471223
0.6818	Remote Similarity	NPC474816
0.6818	Remote Similarity	NPC209135
0.6813	Remote Similarity	NPC473315
0.6813	Remote Similarity	NPC472440
0.6813	Remote Similarity	NPC142111
0.6813	Remote Similarity	NPC161045
0.6813	Remote Similarity	NPC475947
0.6809	Remote Similarity	NPC472809
0.6809	Remote Similarity	NPC472810
0.6804	Remote Similarity	NPC470255
0.6796	Remote Similarity	NPC239961
0.6796	Remote Similarity	NPC82251
0.679	Remote Similarity	NPC282760
0.679	Remote Similarity	NPC471566
0.6786	Remote Similarity	NPC4299
0.6778	Remote Similarity	NPC474894
0.6774	Remote Similarity	NPC469483
0.6774	Remote Similarity	NPC208473
0.6768	Remote Similarity	NPC153559
0.6765	Remote Similarity	NPC197736
0.675	Remote Similarity	NPC68110
0.6747	Remote Similarity	NPC474823
0.6747	Remote Similarity	NPC276290
0.6744	Remote Similarity	NPC294434
0.6744	Remote Similarity	NPC15499
0.6744	Remote Similarity	NPC259599
0.6744	Remote Similarity	NPC117746
0.6742	Remote Similarity	NPC321728
0.6739	Remote Similarity	NPC470800
0.6739	Remote Similarity	NPC41856
0.6737	Remote Similarity	NPC139418
0.6737	Remote Similarity	NPC470734
0.6737	Remote Similarity	NPC295448
0.6735	Remote Similarity	NPC476487
0.6735	Remote Similarity	NPC476488
0.6735	Remote Similarity	NPC170204
0.6733	Remote Similarity	NPC198992
0.6731	Remote Similarity	NPC254538
0.6731	Remote Similarity	NPC474285
0.6706	Remote Similarity	NPC84038
0.6706	Remote Similarity	NPC178575
0.6705	Remote Similarity	NPC51809
0.6705	Remote Similarity	NPC176329
0.6705	Remote Similarity	NPC262747
0.6705	Remote Similarity	NPC49302
0.6705	Remote Similarity	NPC125365
0.6705	Remote Similarity	NPC474818
0.6703	Remote Similarity	NPC11332
0.6703	Remote Similarity	NPC180363
0.6703	Remote Similarity	NPC65930
0.6703	Remote Similarity	NPC73310
0.6703	Remote Similarity	NPC473712
0.6703	Remote Similarity	NPC473780
0.6703	Remote Similarity	NPC145914
0.6703	Remote Similarity	NPC475159
0.6703	Remote Similarity	NPC131002
0.6703	Remote Similarity	NPC329829
0.6703	Remote Similarity	NPC251026
0.6703	Remote Similarity	NPC473529
0.6703	Remote Similarity	NPC94875
0.6702	Remote Similarity	NPC300779
0.6701	Remote Similarity	NPC473723
0.6701	Remote Similarity	NPC475173
0.6701	Remote Similarity	NPC473561
0.6701	Remote Similarity	NPC469939
0.6701	Remote Similarity	NPC473663
0.6701	Remote Similarity	NPC473520
0.6701	Remote Similarity	NPC242069

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 NPC474439 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1867
0.2-0.3	4328
0.3-0.4	2223
0.4-0.5	474
0.5-0.6	104
0.6-0.7	5
0.7-0.8	1
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
0.7111	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.67	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7838	Discovery
0.6509	Remote Similarity	NPD6686	Approved
0.6386	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6698	Approved
0.6327	Remote Similarity	NPD46	Approved
0.6277	Remote Similarity	NPD7154	Phase 3
0.617	Remote Similarity	NPD5209	Approved
0.6146	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7503	Approved
0.61	Remote Similarity	NPD7983	Approved
0.6071	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4225	Approved
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD7328	Approved
0.6	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4756	Discovery
0.5974	Remote Similarity	NPD6927	Phase 3
0.5948	Remote Similarity	NPD7516	Approved
0.5938	Remote Similarity	NPD6110	Phase 1
0.5938	Remote Similarity	NPD5362	Discontinued
0.5934	Remote Similarity	NPD8039	Approved
0.5913	Remote Similarity	NPD7505	Discontinued
0.5904	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD8294	Approved
0.5897	Remote Similarity	NPD8377	Approved
0.5859	Remote Similarity	NPD4251	Approved
0.5859	Remote Similarity	NPD4250	Approved
0.5847	Remote Similarity	NPD8335	Approved
0.5847	Remote Similarity	NPD8296	Approved
0.5847	Remote Similarity	NPD8379	Approved
0.5847	Remote Similarity	NPD8513	Phase 3
0.5847	Remote Similarity	NPD8515	Approved
0.5847	Remote Similarity	NPD8516	Approved
0.5847	Remote Similarity	NPD8517	Approved
0.5847	Remote Similarity	NPD8033	Approved
0.5847	Remote Similarity	NPD8380	Approved
0.5847	Remote Similarity	NPD8378	Approved
0.5842	Remote Similarity	NPD5785	Approved
0.5841	Remote Similarity	NPD969	Suspended
0.5833	Remote Similarity	NPD4191	Approved
0.5833	Remote Similarity	NPD4192	Approved
0.5833	Remote Similarity	NPD4193	Approved
0.5833	Remote Similarity	NPD4194	Approved
0.5818	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5344	Discontinued
0.5789	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7507	Approved
0.5784	Remote Similarity	NPD7637	Suspended
0.5773	Remote Similarity	NPD5331	Approved
0.5773	Remote Similarity	NPD5332	Approved
0.5758	Remote Similarity	NPD4249	Approved
0.5752	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4790	Discontinued
0.5714	Remote Similarity	NPD4220	Pre-registration
0.5714	Remote Similarity	NPD7839	Suspended
0.5701	Remote Similarity	NPD7640	Approved
0.5701	Remote Similarity	NPD7639	Approved
0.5664	Remote Similarity	NPD6371	Approved
0.5663	Remote Similarity	NPD6109	Phase 1
0.5657	Remote Similarity	NPD5363	Approved
0.5645	Remote Similarity	NPD7319	Approved
0.5625	Remote Similarity	NPD4822	Approved
0.5625	Remote Similarity	NPD4821	Approved
0.5625	Remote Similarity	NPD4819	Approved
0.5625	Remote Similarity	NPD4820	Approved
0.562	Remote Similarity	NPD7829	Approved
0.562	Remote Similarity	NPD7830	Approved
0.5614	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7638	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