NPASS Compound

Structure

CID315552 OpenBabel06191716132D 30 30 0 0 1 0 0 0 0 0999 V2000 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 9 1 0 0 0 0 2 10 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 29 1 0 0 0 0 9 19 2 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 13 2 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 21 23 2 0 0 0 0 21 25 1 0 0 0 0 22 25 1 0 0 0 0 22 26 2 0 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 25 28 2 0 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.28
Volume:	466.401
LogP:	4.495
LogD:	4.462
LogS:	-4.592
# Rotatable Bonds:	10
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.384
Synthetic Accessibility Score:	4.449
Fsp3:	0.5
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:	-4.561
MDCK Permeability:	1.69E-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.067
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.058

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	95.02%
Volume Distribution (VD):	2.748
Pgp-substrate:	3.79%

ADMET: Metabolism

CYP1A2-inhibitor:	0.618
CYP1A2-substrate:	0.917
CYP2C19-inhibitor:	0.731
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.844
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.692
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	4.549
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.981
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.591
Skin Sensitization:	0.172
Carcinogencity:	0.223
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.234

Download Data

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

Natural Product: NPC315552

Natural Product ID:	NPC315552
*Common Name:**	5-Ethyl-2-[(1E,5E,7E,11E)-10-Hydroxy-3,7,9,11-Tetramethyltrideca-1,5,7,11-Tetraenyl]-6-Methoxy-3-Methylpyran-4-One
IUPAC Name:	5-ethyl-2-[(1E,5E,7E,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-1,5,7,11-tetraenyl]-6-methoxy-3-methylpyran-4-one
Synonyms:
Standard InCHIKey:	RZWLIPXWCCRKLN-PADIHOPFSA-N
Standard InCHI:	InChI=1S/C26H38O4/c1-9-19(5)24(27)20(6)16-18(4)13-11-12-17(3)14-15-23-21(7)25(28)22(10-2)26(29-8)30-23/h9,11,13-17,20,24,27H,10,12H2,1-8H3/b13-11+,15-14+,18-16+,19-9+
SMILES:	CCC1=C(OC(=C(C1=O)C)C=CC(C)CC=CC(=CC(C)C(C(=CC)C)O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1817966
PubChem CID:	53387349
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
NPO24126	Streptomyces albus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18648803]
NPO24126	Streptomyces albus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19246195]
NPO24126.17	Streptomyces albus POR-04-15-053	Subspecies	Streptomycetaceae	Bacteria	isolated from a suspension of marine sediment	a depth 25 m at Punta Sagres (Portugal)	2004-AUG	PMID[21718029]
NPO24126	Streptomyces albus	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21718029]
NPO24126	Streptomyces albus	Species	Streptomycetaceae	Bacteria	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
GI50	3
Others	6

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	>	22000.0	nM	PMID[549849]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	TGI	>	22000.0	nM	PMID[549849]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	LC50	>	22000.0	nM	PMID[549849]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	21500.0	nM	PMID[549849]
NPT139	Cell Line	HT-29	Homo sapiens	TGI	>	22000.0	nM	PMID[549849]
NPT139	Cell Line	HT-29	Homo sapiens	LC50	>	22000.0	nM	PMID[549849]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	18600.0	nM	PMID[549849]
NPT81	Cell Line	A549	Homo sapiens	TGI	>	22000.0	nM	PMID[549849]
NPT81	Cell Line	A549	Homo sapiens	LC50	>	22000.0	nM	PMID[549849]

☑ 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 NPC315552 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	274
0.1-0.2	1289
0.2-0.3	4057
0.3-0.4	9473
0.4-0.5	10245
0.5-0.6	6065
0.6-0.7	9181
0.7-0.8	2080
0.8-0.85	24
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.971	High Similarity	NPC316851
0.8696	High Similarity	NPC7940
0.8611	High Similarity	NPC59558
0.7816	Intermediate Similarity	NPC320552
0.7791	Intermediate Similarity	NPC327253
0.7763	Intermediate Similarity	NPC316185
0.759	Intermediate Similarity	NPC16488
0.7564	Intermediate Similarity	NPC315843
0.7529	Intermediate Similarity	NPC315395
0.7529	Intermediate Similarity	NPC316426
0.75	Intermediate Similarity	NPC315394
0.7471	Intermediate Similarity	NPC471054
0.7442	Intermediate Similarity	NPC241054
0.7432	Intermediate Similarity	NPC471566
0.7368	Intermediate Similarity	NPC238223
0.7356	Intermediate Similarity	NPC106051
0.7356	Intermediate Similarity	NPC472011
0.7342	Intermediate Similarity	NPC107654
0.7342	Intermediate Similarity	NPC470686
0.7308	Intermediate Similarity	NPC178575
0.7294	Intermediate Similarity	NPC161670
0.7273	Intermediate Similarity	NPC151481
0.7241	Intermediate Similarity	NPC313658
0.7241	Intermediate Similarity	NPC45409
0.7241	Intermediate Similarity	NPC316138
0.7237	Intermediate Similarity	NPC132286
0.7222	Intermediate Similarity	NPC282644
0.7222	Intermediate Similarity	NPC29798
0.72	Intermediate Similarity	NPC471556
0.72	Intermediate Similarity	NPC471565
0.7191	Intermediate Similarity	NPC475879
0.7179	Intermediate Similarity	NPC473361
0.7179	Intermediate Similarity	NPC329904
0.7162	Intermediate Similarity	NPC2328
0.7159	Intermediate Similarity	NPC60765
0.7126	Intermediate Similarity	NPC47220
0.7126	Intermediate Similarity	NPC186332
0.7111	Intermediate Similarity	NPC472010
0.7105	Intermediate Similarity	NPC315115
0.7105	Intermediate Similarity	NPC470033
0.7105	Intermediate Similarity	NPC146811
0.7093	Intermediate Similarity	NPC475706
0.7079	Intermediate Similarity	NPC307092
0.7079	Intermediate Similarity	NPC51358
0.7059	Intermediate Similarity	NPC474028
0.7059	Intermediate Similarity	NPC474439
0.7051	Intermediate Similarity	NPC473277
0.7045	Intermediate Similarity	NPC300779
0.7037	Intermediate Similarity	NPC260396
0.7033	Intermediate Similarity	NPC475098
0.7033	Intermediate Similarity	NPC189651
0.7011	Intermediate Similarity	NPC474424
0.7011	Intermediate Similarity	NPC67081
0.7011	Intermediate Similarity	NPC471223
0.7011	Intermediate Similarity	NPC242233
0.7	Intermediate Similarity	NPC475995
0.7	Intermediate Similarity	NPC284006
0.7	Intermediate Similarity	NPC474098
0.6988	Remote Similarity	NPC279532
0.6977	Remote Similarity	NPC475714
0.6977	Remote Similarity	NPC475083
0.6974	Remote Similarity	NPC273600
0.6966	Remote Similarity	NPC473658
0.6966	Remote Similarity	NPC26078
0.6962	Remote Similarity	NPC315285
0.6962	Remote Similarity	NPC315597
0.6941	Remote Similarity	NPC112868
0.6932	Remote Similarity	NPC211892
0.6923	Remote Similarity	NPC471059
0.6923	Remote Similarity	NPC32552
0.6923	Remote Similarity	NPC313444
0.6905	Remote Similarity	NPC321728
0.6892	Remote Similarity	NPC476585
0.6889	Remote Similarity	NPC295448
0.6883	Remote Similarity	NPC475675
0.6883	Remote Similarity	NPC475555
0.6882	Remote Similarity	NPC170204
0.6875	Remote Similarity	NPC293114
0.6867	Remote Similarity	NPC316324
0.686	Remote Similarity	NPC324170
0.6854	Remote Similarity	NPC113370
0.6854	Remote Similarity	NPC103743
0.6854	Remote Similarity	NPC476079
0.6849	Remote Similarity	NPC254095
0.6849	Remote Similarity	NPC223679
0.6848	Remote Similarity	NPC242069
0.6842	Remote Similarity	NPC477456
0.6842	Remote Similarity	NPC477457
0.6842	Remote Similarity	NPC203627
0.6842	Remote Similarity	NPC475618
0.6835	Remote Similarity	NPC236208
0.6829	Remote Similarity	NPC478193
0.6829	Remote Similarity	NPC478196
0.6829	Remote Similarity	NPC478194
0.6829	Remote Similarity	NPC478195
0.6829	Remote Similarity	NPC478192
0.6829	Remote Similarity	NPC478191
0.6818	Remote Similarity	NPC163606
0.6818	Remote Similarity	NPC471494
0.6806	Remote Similarity	NPC51846
0.6806	Remote Similarity	NPC221763
0.68	Remote Similarity	NPC55376
0.6795	Remote Similarity	NPC106613
0.679	Remote Similarity	NPC12815
0.679	Remote Similarity	NPC215745
0.679	Remote Similarity	NPC238948
0.6786	Remote Similarity	NPC315765
0.6786	Remote Similarity	NPC326753
0.6786	Remote Similarity	NPC264391
0.6782	Remote Similarity	NPC44261
0.6778	Remote Similarity	NPC475739
0.6774	Remote Similarity	NPC470521
0.6757	Remote Similarity	NPC322186
0.6753	Remote Similarity	NPC282760
0.6753	Remote Similarity	NPC96414
0.6753	Remote Similarity	NPC476586
0.675	Remote Similarity	NPC316029
0.675	Remote Similarity	NPC203819
0.675	Remote Similarity	NPC476037
0.675	Remote Similarity	NPC4299
0.6747	Remote Similarity	NPC470705
0.6747	Remote Similarity	NPC203277
0.6744	Remote Similarity	NPC315731
0.6744	Remote Similarity	NPC474980
0.6742	Remote Similarity	NPC311163
0.6739	Remote Similarity	NPC470520
0.6712	Remote Similarity	NPC135863
0.6712	Remote Similarity	NPC249850
0.6712	Remote Similarity	NPC283502
0.6712	Remote Similarity	NPC293437
0.6712	Remote Similarity	NPC129150
0.6712	Remote Similarity	NPC268185
0.6712	Remote Similarity	NPC71755
0.6711	Remote Similarity	NPC476584
0.6711	Remote Similarity	NPC473737
0.6709	Remote Similarity	NPC474823
0.6707	Remote Similarity	NPC476590
0.6707	Remote Similarity	NPC114727
0.6707	Remote Similarity	NPC227396
0.6706	Remote Similarity	NPC139712
0.6706	Remote Similarity	NPC271632
0.6705	Remote Similarity	NPC126518
0.6705	Remote Similarity	NPC475035
0.6705	Remote Similarity	NPC266718
0.6705	Remote Similarity	NPC31086
0.6703	Remote Similarity	NPC212598
0.6701	Remote Similarity	NPC20673
0.6701	Remote Similarity	NPC219038
0.6701	Remote Similarity	NPC175531
0.6667	Remote Similarity	NPC329686
0.6667	Remote Similarity	NPC201356
0.6667	Remote Similarity	NPC309408
0.6667	Remote Similarity	NPC67076
0.6667	Remote Similarity	NPC469939
0.6667	Remote Similarity	NPC319163
0.6667	Remote Similarity	NPC82666
0.6667	Remote Similarity	NPC313677
0.6667	Remote Similarity	NPC98519
0.6667	Remote Similarity	NPC26624
0.6667	Remote Similarity	NPC477086
0.6667	Remote Similarity	NPC471056
0.6667	Remote Similarity	NPC97173
0.6667	Remote Similarity	NPC10080
0.6667	Remote Similarity	NPC471225
0.6667	Remote Similarity	NPC61201
0.6667	Remote Similarity	NPC95863
0.6667	Remote Similarity	NPC130953
0.6667	Remote Similarity	NPC471296
0.6667	Remote Similarity	NPC471055
0.6667	Remote Similarity	NPC323251
0.6667	Remote Similarity	NPC123908
0.6667	Remote Similarity	NPC477087
0.6667	Remote Similarity	NPC59646
0.6667	Remote Similarity	NPC37382
0.6633	Remote Similarity	NPC471599
0.6632	Remote Similarity	NPC288350
0.6632	Remote Similarity	NPC173329
0.663	Remote Similarity	NPC3436
0.663	Remote Similarity	NPC145666
0.6629	Remote Similarity	NPC471060
0.6629	Remote Similarity	NPC474860
0.6629	Remote Similarity	NPC307112
0.6629	Remote Similarity	NPC471300
0.6629	Remote Similarity	NPC329630
0.6628	Remote Similarity	NPC160582
0.6628	Remote Similarity	NPC162741
0.6628	Remote Similarity	NPC91332
0.6627	Remote Similarity	NPC210258
0.6627	Remote Similarity	NPC206507
0.6627	Remote Similarity	NPC147621
0.6625	Remote Similarity	NPC475004
0.6625	Remote Similarity	NPC475982
0.6625	Remote Similarity	NPC101622
0.6625	Remote Similarity	NPC470693
0.6623	Remote Similarity	NPC471611
0.6598	Remote Similarity	NPC472012
0.6598	Remote Similarity	NPC244878
0.6593	Remote Similarity	NPC470137
0.6591	Remote Similarity	NPC473315
0.6591	Remote Similarity	NPC315559

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 NPC315552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	890
0.2-0.3	1925
0.3-0.4	2792
0.4-0.5	1936
0.5-0.6	1009
0.6-0.7	316
0.7-0.8	45
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
0.6842	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6110	Phase 1
0.6471	Remote Similarity	NPD4756	Discovery
0.6447	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7154	Phase 3
0.6375	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5785	Approved
0.6277	Remote Similarity	NPD7838	Discovery
0.625	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7839	Suspended
0.6111	Remote Similarity	NPD5209	Approved
0.6105	Remote Similarity	NPD6698	Approved
0.6105	Remote Similarity	NPD46	Approved
0.6087	Remote Similarity	NPD5363	Approved
0.6067	Remote Similarity	NPD4252	Approved
0.6067	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD4220	Pre-registration
0.6053	Remote Similarity	NPD8779	Phase 3
0.6044	Remote Similarity	NPD5362	Discontinued
0.6042	Remote Similarity	NPD7637	Suspended
0.6023	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4271	Approved
0.6023	Remote Similarity	NPD4268	Approved
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5779	Approved
0.5979	Remote Similarity	NPD5778	Approved
0.5957	Remote Similarity	NPD4251	Approved
0.5957	Remote Similarity	NPD4250	Approved
0.5949	Remote Similarity	NPD4191	Approved
0.5949	Remote Similarity	NPD4192	Approved
0.5949	Remote Similarity	NPD4194	Approved
0.5949	Remote Similarity	NPD4193	Approved
0.5934	Remote Similarity	NPD4269	Approved
0.5934	Remote Similarity	NPD4270	Approved
0.589	Remote Similarity	NPD6927	Phase 3
0.5889	Remote Similarity	NPD4821	Approved
0.5889	Remote Similarity	NPD4819	Approved
0.5889	Remote Similarity	NPD4820	Approved
0.5889	Remote Similarity	NPD4822	Approved
0.5876	Remote Similarity	NPD7983	Approved
0.587	Remote Similarity	NPD5331	Approved
0.587	Remote Similarity	NPD5332	Approved
0.5862	Remote Similarity	NPD8264	Approved
0.5854	Remote Similarity	NPD3704	Approved
0.5851	Remote Similarity	NPD5786	Approved
0.5851	Remote Similarity	NPD4249	Approved
0.5841	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD4790	Discontinued
0.5769	Remote Similarity	NPD6647	Phase 2
0.5745	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7500	Approved
0.5714	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4219	Approved
0.5688	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD4225	Approved
0.5682	Remote Similarity	NPD8039	Approved
0.567	Remote Similarity	NPD6101	Approved
0.567	Remote Similarity	NPD5370	Suspended
0.567	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5369	Approved
0.5634	Remote Similarity	NPD4265	Approved
0.5632	Remote Similarity	NPD4732	Discontinued
0.5631	Remote Similarity	NPD7639	Approved
0.5631	Remote Similarity	NPD6648	Approved
0.5631	Remote Similarity	NPD7640	Approved
0.5603	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD7623	Phase 3

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