NPASS Compound

Structure

NPC474424 OpenBabel07101718302D 31 32 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 -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 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 -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 -1.7213 -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 16 1 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 21 2 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 18 3 1 6 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 21 30 1 0 0 0 0 22 26 1 0 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 24 28 2 0 0 0 0 24 30 1 0 0 0 0 25 29 2 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.24
Volume:	458.129
LogP:	4.989
LogD:	4.08
LogS:	-3.762
# Rotatable Bonds:	11
TPSA:	107.2
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	3.84
Fsp3:	0.44
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:	-5.158
MDCK Permeability:	2.0603454686352052e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.698
Human Intestinal Absorption (HIA):	0.505
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	96.98308563232422%
Volume Distribution (VD):	0.634
Pgp-substrate:	1.1794482469558716%

ADMET: Metabolism

CYP1A2-inhibitor:	0.301
CYP1A2-substrate:	0.64
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.726
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.769
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	3.743
Half-life (T1/2):	0.912

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.505
Drug-inuced Liver Injury (DILI):	0.63
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.92
Carcinogencity:	0.089
Eye Corrosion:	0.004
Eye Irritation:	0.763
Respiratory Toxicity:	0.197

Download Data

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

Natural Product: NPC474424

Natural Product ID:	NPC474424
*Common Name:**	(5Z)-4-Hydroxy-5-[(2R,6E,10E)-13-(2-Hydroxy-5-Oxo-2H-Furan-4-Yl)-2,6,10-Trimethyltrideca-6,10-Dienylidene]-3-Methylfuran-2-One
IUPAC Name:	(5Z)-4-hydroxy-5-[(2R,6E,10E)-13-(2-hydroxy-5-oxo-2H-furan-4-yl)-2,6,10-trimethyltrideca-6,10-dienylidene]-3-methylfuran-2-one
Synonyms:
Standard InCHIKey:	FIOHAOSLSHPVIU-GHUWAEOFSA-N
Standard InCHI:	InChI=1S/C25H34O6/c1-16(10-6-12-18(3)14-21-23(27)19(4)24(28)30-21)8-5-9-17(2)11-7-13-20-15-22(26)31-25(20)29/h8,11,14-15,18,22,26-27H,5-7,9-10,12-13H2,1-4H3/b16-8+,17-11+,21-14-/t18-,22?/m1/s1
SMILES:	CC1=C(C(=CC(C)CCCC(=CCCC(=CCCC2=CC(OC2=O)O)C)C)OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468012
PubChem CID:	54729896
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	=	12.5	ug.mL-1	PMID[507059]
NPT111	Cell Line	K562	Homo sapiens	LC50	>	100.0	ug.mL-1	PMID[507059]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	50.0	ug.mL-1	PMID[507059]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[507059]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[507059]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[507059]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[507059]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[507059]

☑ 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 NPC474424 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	185
0.1-0.2	1261
0.2-0.3	6119
0.3-0.4	15995
0.4-0.5	12569
0.5-0.6	5021
0.6-0.7	1453
0.7-0.8	85
0.8-0.85	3
0.85-0.9	1
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9398	High Similarity	NPC475739
0.9375	High Similarity	NPC474439
0.9375	High Similarity	NPC474028
0.9146	High Similarity	NPC475706
0.9024	High Similarity	NPC475714
0.8523	High Similarity	NPC475995
0.8523	High Similarity	NPC474098
0.8391	Intermediate Similarity	NPC45409
0.7912	Intermediate Similarity	NPC475879
0.7816	Intermediate Similarity	NPC471296
0.7711	Intermediate Similarity	NPC470686
0.7619	Intermediate Similarity	NPC478193
0.7619	Intermediate Similarity	NPC478191
0.7619	Intermediate Similarity	NPC478192
0.7619	Intermediate Similarity	NPC478194
0.7619	Intermediate Similarity	NPC478195
0.7619	Intermediate Similarity	NPC478196
0.7561	Intermediate Similarity	NPC329904
0.7561	Intermediate Similarity	NPC473361
0.7556	Intermediate Similarity	NPC474860
0.7556	Intermediate Similarity	NPC471300
0.75	Intermediate Similarity	NPC107654
0.75	Intermediate Similarity	NPC315843
0.7473	Intermediate Similarity	NPC211892
0.7444	Intermediate Similarity	NPC161670
0.7442	Intermediate Similarity	NPC68156
0.7416	Intermediate Similarity	NPC324170
0.7391	Intermediate Similarity	NPC475678
0.7368	Intermediate Similarity	NPC59646
0.7342	Intermediate Similarity	NPC155849
0.7333	Intermediate Similarity	NPC229799
0.7333	Intermediate Similarity	NPC286770
0.7333	Intermediate Similarity	NPC284472
0.7294	Intermediate Similarity	NPC474758
0.7292	Intermediate Similarity	NPC470521
0.7273	Intermediate Similarity	NPC99651
0.7262	Intermediate Similarity	NPC316185
0.7241	Intermediate Similarity	NPC473756
0.7241	Intermediate Similarity	NPC315394
0.7234	Intermediate Similarity	NPC139418
0.7229	Intermediate Similarity	NPC470693
0.7222	Intermediate Similarity	NPC473780
0.7222	Intermediate Similarity	NPC471298
0.7222	Intermediate Similarity	NPC94875
0.7222	Intermediate Similarity	NPC310450
0.7222	Intermediate Similarity	NPC180363
0.7222	Intermediate Similarity	NPC329829
0.7222	Intermediate Similarity	NPC473529
0.7222	Intermediate Similarity	NPC65930
0.7222	Intermediate Similarity	NPC11383
0.7222	Intermediate Similarity	NPC475159
0.7222	Intermediate Similarity	NPC474959
0.7222	Intermediate Similarity	NPC11332
0.7222	Intermediate Similarity	NPC323251
0.7222	Intermediate Similarity	NPC73310
0.7222	Intermediate Similarity	NPC145914
0.7222	Intermediate Similarity	NPC473712
0.7222	Intermediate Similarity	NPC475046
0.7222	Intermediate Similarity	NPC131002
0.7209	Intermediate Similarity	NPC329852
0.7188	Intermediate Similarity	NPC472196
0.7188	Intermediate Similarity	NPC472195
0.7188	Intermediate Similarity	NPC469939
0.7188	Intermediate Similarity	NPC29798
0.7188	Intermediate Similarity	NPC238090
0.7188	Intermediate Similarity	NPC282644
0.7158	Intermediate Similarity	NPC3436
0.7158	Intermediate Similarity	NPC473904
0.7158	Intermediate Similarity	NPC473448
0.7143	Intermediate Similarity	NPC64234
0.7143	Intermediate Similarity	NPC144415
0.7143	Intermediate Similarity	NPC471297
0.7143	Intermediate Similarity	NPC16488
0.7143	Intermediate Similarity	NPC253801
0.7143	Intermediate Similarity	NPC473333
0.7143	Intermediate Similarity	NPC37929
0.7143	Intermediate Similarity	NPC475947
0.7129	Intermediate Similarity	NPC471599
0.7125	Intermediate Similarity	NPC68110
0.7113	Intermediate Similarity	NPC159698
0.7108	Intermediate Similarity	NPC313444
0.7108	Intermediate Similarity	NPC287705
0.7097	Intermediate Similarity	NPC469483
0.7097	Intermediate Similarity	NPC315395
0.7097	Intermediate Similarity	NPC316426
0.7097	Intermediate Similarity	NPC164393
0.7093	Intermediate Similarity	NPC117746
0.7093	Intermediate Similarity	NPC294434
0.7093	Intermediate Similarity	NPC259599
0.7093	Intermediate Similarity	NPC15499
0.7083	Intermediate Similarity	NPC175842
0.7083	Intermediate Similarity	NPC470520
0.7083	Intermediate Similarity	NPC32494
0.7083	Intermediate Similarity	NPC477749
0.7083	Intermediate Similarity	NPC477783
0.7079	Intermediate Similarity	NPC321728
0.7073	Intermediate Similarity	NPC191233
0.7071	Intermediate Similarity	NPC471490
0.7071	Intermediate Similarity	NPC2666
0.7065	Intermediate Similarity	NPC126518
0.7065	Intermediate Similarity	NPC474865
0.7065	Intermediate Similarity	NPC243618
0.7065	Intermediate Similarity	NPC266718
0.7065	Intermediate Similarity	NPC475035
0.7065	Intermediate Similarity	NPC471301
0.7065	Intermediate Similarity	NPC156804
0.7065	Intermediate Similarity	NPC471302
0.7065	Intermediate Similarity	NPC70424
0.7065	Intermediate Similarity	NPC163093
0.7059	Intermediate Similarity	NPC84038
0.7053	Intermediate Similarity	NPC251528
0.7053	Intermediate Similarity	NPC225283
0.7045	Intermediate Similarity	NPC474818
0.7045	Intermediate Similarity	NPC125365
0.7045	Intermediate Similarity	NPC316324
0.7045	Intermediate Similarity	NPC10572
0.7045	Intermediate Similarity	NPC176329
0.7045	Intermediate Similarity	NPC51809
0.7045	Intermediate Similarity	NPC49302
0.7041	Intermediate Similarity	NPC476488
0.7041	Intermediate Similarity	NPC476487
0.7041	Intermediate Similarity	NPC170204
0.7033	Intermediate Similarity	NPC474291
0.703	Intermediate Similarity	NPC20673
0.703	Intermediate Similarity	NPC219038
0.7024	Intermediate Similarity	NPC232812
0.7024	Intermediate Similarity	NPC151481
0.7021	Intermediate Similarity	NPC300779
0.7019	Intermediate Similarity	NPC254538
0.7019	Intermediate Similarity	NPC474285
0.7011	Intermediate Similarity	NPC315552
0.701	Intermediate Similarity	NPC473723
0.701	Intermediate Similarity	NPC473561
0.701	Intermediate Similarity	NPC242069
0.701	Intermediate Similarity	NPC475173
0.701	Intermediate Similarity	NPC11456
0.701	Intermediate Similarity	NPC473520
0.701	Intermediate Similarity	NPC473663
0.701	Intermediate Similarity	NPC320552
0.7	Intermediate Similarity	NPC203627
0.7	Intermediate Similarity	NPC187268
0.699	Remote Similarity	NPC86095
0.6989	Remote Similarity	NPC77871
0.6989	Remote Similarity	NPC223871
0.6989	Remote Similarity	NPC25764
0.6989	Remote Similarity	NPC132496
0.6989	Remote Similarity	NPC473651
0.6989	Remote Similarity	NPC9678
0.6989	Remote Similarity	NPC231009
0.6989	Remote Similarity	NPC110710
0.6989	Remote Similarity	NPC322529
0.6989	Remote Similarity	NPC329838
0.6989	Remote Similarity	NPC21469
0.6989	Remote Similarity	NPC66346
0.6989	Remote Similarity	NPC292809
0.6989	Remote Similarity	NPC477018
0.6989	Remote Similarity	NPC470400
0.6989	Remote Similarity	NPC235809
0.6989	Remote Similarity	NPC329615
0.6989	Remote Similarity	NPC283085
0.6989	Remote Similarity	NPC471567
0.6989	Remote Similarity	NPC202055
0.6989	Remote Similarity	NPC473478
0.6989	Remote Similarity	NPC475034
0.6989	Remote Similarity	NPC477014
0.6989	Remote Similarity	NPC82795
0.6989	Remote Similarity	NPC100921
0.6989	Remote Similarity	NPC103284
0.6989	Remote Similarity	NPC471494
0.6989	Remote Similarity	NPC163606
0.6989	Remote Similarity	NPC1083
0.6989	Remote Similarity	NPC286338
0.6989	Remote Similarity	NPC473671
0.6989	Remote Similarity	NPC475268
0.6989	Remote Similarity	NPC477013
0.6989	Remote Similarity	NPC107986
0.6989	Remote Similarity	NPC319036
0.6989	Remote Similarity	NPC39279
0.6989	Remote Similarity	NPC120398
0.6989	Remote Similarity	NPC39167
0.6989	Remote Similarity	NPC473669
0.6989	Remote Similarity	NPC473156
0.6979	Remote Similarity	NPC476004
0.6979	Remote Similarity	NPC327253
0.6979	Remote Similarity	NPC474761
0.6979	Remote Similarity	NPC6414
0.6979	Remote Similarity	NPC477782
0.6979	Remote Similarity	NPC118078
0.6979	Remote Similarity	NPC166554
0.6979	Remote Similarity	NPC303451
0.6977	Remote Similarity	NPC474705
0.6966	Remote Similarity	NPC279214
0.6966	Remote Similarity	NPC93763
0.6966	Remote Similarity	NPC473471
0.6966	Remote Similarity	NPC108816
0.6966	Remote Similarity	NPC221095
0.6957	Remote Similarity	NPC161045
0.6951	Remote Similarity	NPC220766
0.6947	Remote Similarity	NPC260343
0.6947	Remote Similarity	NPC474629

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 NPC474424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1789
0.2-0.3	4205
0.3-0.4	2277
0.4-0.5	585
0.5-0.6	127
0.6-0.7	12
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
0.7065	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7838	Discovery
0.6792	Remote Similarity	NPD6686	Approved
0.6633	Remote Similarity	NPD6698	Approved
0.6633	Remote Similarity	NPD46	Approved
0.6596	Remote Similarity	NPD7154	Phase 3
0.6489	Remote Similarity	NPD5209	Approved
0.64	Remote Similarity	NPD7983	Approved
0.6346	Remote Similarity	NPD4225	Approved
0.6316	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4756	Discovery
0.63	Remote Similarity	NPD5785	Approved
0.6289	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6110	Phase 1
0.625	Remote Similarity	NPD5362	Discontinued
0.6163	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4251	Approved
0.6162	Remote Similarity	NPD4250	Approved
0.6122	Remote Similarity	NPD5363	Approved
0.6105	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7503	Approved
0.6091	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8039	Approved
0.6082	Remote Similarity	NPD5332	Approved
0.6082	Remote Similarity	NPD5331	Approved
0.6071	Remote Similarity	NPD6371	Approved
0.6064	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4249	Approved
0.6042	Remote Similarity	NPD4790	Discontinued
0.6018	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7839	Suspended
0.5981	Remote Similarity	NPD7639	Approved
0.5981	Remote Similarity	NPD6648	Approved
0.5981	Remote Similarity	NPD7640	Approved
0.5966	Remote Similarity	NPD8517	Approved
0.5966	Remote Similarity	NPD8513	Phase 3
0.5966	Remote Similarity	NPD8515	Approved
0.5966	Remote Similarity	NPD8516	Approved
0.5949	Remote Similarity	NPD6927	Phase 3
0.5938	Remote Similarity	NPD4819	Approved
0.5938	Remote Similarity	NPD4821	Approved
0.5938	Remote Similarity	NPD4820	Approved
0.5938	Remote Similarity	NPD4822	Approved
0.5926	Remote Similarity	NPD5344	Discontinued
0.5922	Remote Similarity	NPD7637	Suspended
0.5905	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD7507	Approved
0.5897	Remote Similarity	NPD7505	Discontinued
0.5895	Remote Similarity	NPD4271	Approved
0.5895	Remote Similarity	NPD4268	Approved
0.5888	Remote Similarity	NPD7638	Approved
0.5877	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD7830	Approved
0.5868	Remote Similarity	NPD7829	Approved
0.5865	Remote Similarity	NPD5779	Approved
0.5865	Remote Similarity	NPD5778	Approved
0.5862	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD7328	Approved
0.5847	Remote Similarity	NPD7327	Approved
0.5843	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6647	Phase 2
0.5816	Remote Similarity	NPD4269	Approved
0.5816	Remote Similarity	NPD4270	Approved
0.58	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD7516	Approved
0.5773	Remote Similarity	NPD4252	Approved
0.5763	Remote Similarity	NPD7115	Discovery
0.576	Remote Similarity	NPD7319	Approved
0.575	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.575	Remote Similarity	NPD8294	Approved
0.575	Remote Similarity	NPD8377	Approved
0.5743	Remote Similarity	NPD5786	Approved
0.5714	Remote Similarity	NPD7641	Discontinued
0.5702	Remote Similarity	NPD8033	Approved
0.5702	Remote Similarity	NPD8380	Approved
0.5702	Remote Similarity	NPD8296	Approved
0.5702	Remote Similarity	NPD8379	Approved
0.5702	Remote Similarity	NPD8378	Approved
0.5702	Remote Similarity	NPD8335	Approved
0.569	Remote Similarity	NPD6053	Discontinued
0.5664	Remote Similarity	NPD6412	Phase 2
0.5657	Remote Similarity	NPD6435	Approved
0.5652	Remote Similarity	NPD2067	Discontinued
0.5647	Remote Similarity	NPD6109	Phase 1
0.5644	Remote Similarity	NPD1694	Approved
0.5632	Remote Similarity	NPD4192	Approved
0.5632	Remote Similarity	NPD4194	Approved
0.5632	Remote Similarity	NPD4191	Approved
0.5632	Remote Similarity	NPD4193	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