NPASS Compound

Structure

CID316851 OpenBabel06191716132D 29 29 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 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 -2.5981 0.5000 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 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 2 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 1 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 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 28 1 0 0 0 0 9 18 2 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 18 23 1 0 0 0 0 19 5 1 6 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 20 24 1 0 0 0 0 21 24 1 0 0 0 0 21 25 2 0 0 0 0 22 29 1 0 0 0 0 23 26 1 1 0 0 0 24 27 2 0 0 0 0 25 28 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.26
Volume:	449.105
LogP:	4.278
LogD:	3.876
LogS:	-4.494
# Rotatable Bonds:	9
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.432
Synthetic Accessibility Score:	4.436
Fsp3:	0.48
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:	-4.576
MDCK Permeability:	1.4330298654385842e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.181
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	95.89057159423828%
Volume Distribution (VD):	1.585
Pgp-substrate:	6.206393241882324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.645
CYP1A2-substrate:	0.92
CYP2C19-inhibitor:	0.906
CYP2C19-substrate:	0.884
CYP2C9-inhibitor:	0.842
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.635
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.903
CYP3A4-substrate:	0.53

ADMET: Excretion

Clearance (CL):	5.178
Half-life (T1/2):	0.226

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.973
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.894
Carcinogencity:	0.065
Eye Corrosion:	0.004
Eye Irritation:	0.043
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC316851

Natural Product ID:	NPC316851
*Common Name:**	2-[(1E,5E,7E,9R,10R,11E)-10-Hydroxy-3,7,9,11-Tetramethyltrideca-1,5,7,11-Tetraenyl]-6-Methoxy-3,5-Dimethylpyran-4-One
IUPAC Name:	2-[(1E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-1,5,7,11-tetraenyl]-6-methoxy-3,5-dimethylpyran-4-one
Synonyms:
Standard InCHIKey:	PIYNCLUPGLBENL-FJPKWDFVSA-N
Standard InCHI:	InChI=1S/C25H36O4/c1-9-18(4)23(26)19(5)15-17(3)12-10-11-16(2)13-14-22-20(6)24(27)21(7)25(28-8)29-22/h9-10,12-16,19,23,26H,11H2,1-8H3/b12-10+,14-13+,17-15+,18-9+/t16?,19-,23+/m1/s1
SMILES:	CC=C(C)C(C(C)C=C(C)C=CCC(C)C=CC1=C(C(=O)C(=C(O1)OC)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1817965
PubChem CID:	53466759
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
IC50	3
Others	6

Activity Type	# Activity
Cell Line	9
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	10500.0	nM	PMID[542014]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	TGI	>	22000.0	nM	PMID[542014]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	LC50	>	22000.0	nM	PMID[542014]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	10800.0	nM	PMID[542014]
NPT139	Cell Line	HT-29	Homo sapiens	TGI	=	10800.0	nM	PMID[542014]
NPT139	Cell Line	HT-29	Homo sapiens	LC50	=	11500.0	nM	PMID[542014]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	5000.0	nM	PMID[542014]
NPT81	Cell Line	A549	Homo sapiens	TGI	=	13500.0	nM	PMID[542014]
NPT81	Cell Line	A549	Homo sapiens	LC50	>	22000.0	nM	PMID[542014]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	<	7.0	nM	PMID[542014]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	=	470.0	nM	PMID[542014]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	=	660.0	nM	PMID[542014]

☑ 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 NPC316851 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	1376
0.2-0.3	4312
0.3-0.4	9905
0.4-0.5	9773
0.5-0.6	6364
0.6-0.7	9008
0.7-0.8	1659
0.8-0.85	17
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	NPC315552
0.8955	High Similarity	NPC7940
0.8857	High Similarity	NPC59558
0.7765	Intermediate Similarity	NPC327253
0.7733	Intermediate Similarity	NPC316185
0.7639	Intermediate Similarity	NPC471566
0.7586	Intermediate Similarity	NPC320552
0.7532	Intermediate Similarity	NPC315843
0.75	Intermediate Similarity	NPC178575
0.7468	Intermediate Similarity	NPC315394
0.7397	Intermediate Similarity	NPC471565
0.7349	Intermediate Similarity	NPC16488
0.7333	Intermediate Similarity	NPC238223
0.7308	Intermediate Similarity	NPC470686
0.7308	Intermediate Similarity	NPC107654
0.7297	Intermediate Similarity	NPC470033
0.7294	Intermediate Similarity	NPC316426
0.7294	Intermediate Similarity	NPC315395
0.7262	Intermediate Similarity	NPC161670
0.7241	Intermediate Similarity	NPC471054
0.7237	Intermediate Similarity	NPC151481
0.7209	Intermediate Similarity	NPC316138
0.7209	Intermediate Similarity	NPC241054
0.7209	Intermediate Similarity	NPC313658
0.72	Intermediate Similarity	NPC132286
0.7162	Intermediate Similarity	NPC471556
0.7162	Intermediate Similarity	NPC273600
0.7143	Intermediate Similarity	NPC473361
0.7143	Intermediate Similarity	NPC329904
0.7126	Intermediate Similarity	NPC106051
0.7126	Intermediate Similarity	NPC60765
0.7126	Intermediate Similarity	NPC472011
0.7123	Intermediate Similarity	NPC2328
0.7083	Intermediate Similarity	NPC476585
0.7067	Intermediate Similarity	NPC475675
0.7067	Intermediate Similarity	NPC315115
0.7067	Intermediate Similarity	NPC146811
0.7067	Intermediate Similarity	NPC475555
0.7059	Intermediate Similarity	NPC475706
0.7042	Intermediate Similarity	NPC223679
0.7042	Intermediate Similarity	NPC254095
0.7027	Intermediate Similarity	NPC475618
0.7024	Intermediate Similarity	NPC474439
0.7024	Intermediate Similarity	NPC474028
0.7011	Intermediate Similarity	NPC45409
0.7	Intermediate Similarity	NPC475098
0.7	Intermediate Similarity	NPC51846
0.7	Intermediate Similarity	NPC29798
0.7	Intermediate Similarity	NPC282644
0.7	Intermediate Similarity	NPC189651
0.7	Intermediate Similarity	NPC221763
0.6986	Remote Similarity	NPC55376
0.6977	Remote Similarity	NPC471223
0.6977	Remote Similarity	NPC67081
0.6966	Remote Similarity	NPC475879
0.6951	Remote Similarity	NPC279532
0.6941	Remote Similarity	NPC475714
0.6933	Remote Similarity	NPC282760
0.6933	Remote Similarity	NPC476586
0.6923	Remote Similarity	NPC315285
0.6923	Remote Similarity	NPC315597
0.6914	Remote Similarity	NPC203277
0.6905	Remote Similarity	NPC112868
0.6901	Remote Similarity	NPC71755
0.6901	Remote Similarity	NPC129150
0.6901	Remote Similarity	NPC293437
0.6901	Remote Similarity	NPC135863
0.6901	Remote Similarity	NPC249850
0.6897	Remote Similarity	NPC47220
0.6897	Remote Similarity	NPC186332
0.6892	Remote Similarity	NPC473737
0.6892	Remote Similarity	NPC476584
0.6889	Remote Similarity	NPC472010
0.6883	Remote Similarity	NPC313444
0.6854	Remote Similarity	NPC51358
0.6854	Remote Similarity	NPC307092
0.6849	Remote Similarity	NPC98519
0.6849	Remote Similarity	NPC130953
0.6835	Remote Similarity	NPC293114
0.6824	Remote Similarity	NPC324170
0.6818	Remote Similarity	NPC300779
0.68	Remote Similarity	NPC477457
0.68	Remote Similarity	NPC471611
0.68	Remote Similarity	NPC477456
0.6795	Remote Similarity	NPC473277
0.679	Remote Similarity	NPC478194
0.679	Remote Similarity	NPC206507
0.679	Remote Similarity	NPC210258
0.679	Remote Similarity	NPC478193
0.679	Remote Similarity	NPC260396
0.679	Remote Similarity	NPC478195
0.679	Remote Similarity	NPC478192
0.679	Remote Similarity	NPC478191
0.679	Remote Similarity	NPC478196
0.679	Remote Similarity	NPC147621
0.6782	Remote Similarity	NPC242233
0.6782	Remote Similarity	NPC163606
0.6782	Remote Similarity	NPC474424
0.6782	Remote Similarity	NPC471494
0.6778	Remote Similarity	NPC474098
0.6778	Remote Similarity	NPC475995
0.6761	Remote Similarity	NPC150717
0.675	Remote Similarity	NPC284006
0.6747	Remote Similarity	NPC326753
0.6744	Remote Similarity	NPC475083
0.6744	Remote Similarity	NPC44261
0.6742	Remote Similarity	NPC473658
0.6742	Remote Similarity	NPC26078
0.6739	Remote Similarity	NPC470521
0.6714	Remote Similarity	NPC218486
0.6712	Remote Similarity	NPC322186
0.6712	Remote Similarity	NPC82465
0.6711	Remote Similarity	NPC96414
0.6709	Remote Similarity	NPC316029
0.6709	Remote Similarity	NPC476037
0.6709	Remote Similarity	NPC4299
0.6707	Remote Similarity	NPC470705
0.6706	Remote Similarity	NPC315731
0.6705	Remote Similarity	NPC311163
0.6705	Remote Similarity	NPC211892
0.6703	Remote Similarity	NPC32552
0.6703	Remote Similarity	NPC471059
0.6703	Remote Similarity	NPC470520
0.6667	Remote Similarity	NPC126518
0.6667	Remote Similarity	NPC268185
0.6667	Remote Similarity	NPC321728
0.6667	Remote Similarity	NPC476590
0.6667	Remote Similarity	NPC477117
0.6667	Remote Similarity	NPC170204
0.6667	Remote Similarity	NPC266718
0.6667	Remote Similarity	NPC294938
0.6667	Remote Similarity	NPC175531
0.6667	Remote Similarity	NPC475035
0.6667	Remote Similarity	NPC474823
0.6667	Remote Similarity	NPC295448
0.6667	Remote Similarity	NPC114727
0.6667	Remote Similarity	NPC139712
0.6667	Remote Similarity	NPC271632
0.6632	Remote Similarity	NPC203627
0.663	Remote Similarity	NPC242069
0.663	Remote Similarity	NPC59646
0.6629	Remote Similarity	NPC471055
0.6629	Remote Similarity	NPC113370
0.6629	Remote Similarity	NPC471056
0.6629	Remote Similarity	NPC476079
0.6629	Remote Similarity	NPC103743
0.6628	Remote Similarity	NPC323251
0.6628	Remote Similarity	NPC313677
0.6627	Remote Similarity	NPC471225
0.6627	Remote Similarity	NPC316324
0.6625	Remote Similarity	NPC477087
0.6625	Remote Similarity	NPC477086
0.6625	Remote Similarity	NPC95863
0.6623	Remote Similarity	NPC201356
0.6623	Remote Similarity	NPC37382
0.6622	Remote Similarity	NPC309408
0.662	Remote Similarity	NPC329686
0.6596	Remote Similarity	NPC288350
0.6596	Remote Similarity	NPC173329
0.6593	Remote Similarity	NPC3436
0.6591	Remote Similarity	NPC329630
0.6582	Remote Similarity	NPC236208
0.6582	Remote Similarity	NPC470693
0.6582	Remote Similarity	NPC101622
0.6582	Remote Similarity	NPC475004
0.6575	Remote Similarity	NPC189700
0.6575	Remote Similarity	NPC21946
0.6556	Remote Similarity	NPC475739
0.6552	Remote Similarity	NPC315559
0.6552	Remote Similarity	NPC142111
0.6552	Remote Similarity	NPC161045
0.6552	Remote Similarity	NPC473315
0.6548	Remote Similarity	NPC315765
0.6548	Remote Similarity	NPC474816
0.6548	Remote Similarity	NPC209135
0.6548	Remote Similarity	NPC264391
0.6543	Remote Similarity	NPC477085
0.6543	Remote Similarity	NPC215745
0.6543	Remote Similarity	NPC12815
0.6543	Remote Similarity	NPC329890
0.6543	Remote Similarity	NPC238948
0.6538	Remote Similarity	NPC122627
0.6538	Remote Similarity	NPC106613
0.6533	Remote Similarity	NPC26810
0.6533	Remote Similarity	NPC15193
0.6512	Remote Similarity	NPC8538
0.6512	Remote Similarity	NPC474980
0.6512	Remote Similarity	NPC184208
0.65	Remote Similarity	NPC202011
0.65	Remote Similarity	NPC476012
0.65	Remote Similarity	NPC203819
0.6495	Remote Similarity	NPC219038
0.6495	Remote Similarity	NPC20673
0.6494	Remote Similarity	NPC220766
0.6486	Remote Similarity	NPC302564
0.6484	Remote Similarity	NPC225283
0.6484	Remote Similarity	NPC212598
0.6479	Remote Similarity	NPC478120
0.6477	Remote Similarity	NPC473308
0.6477	Remote Similarity	NPC31086

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 NPC316851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	928
0.2-0.3	1965
0.3-0.4	2827
0.4-0.5	1888
0.5-0.6	984
0.6-0.7	281
0.7-0.8	39
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
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6110	Phase 1
0.6237	Remote Similarity	NPD7838	Discovery
0.6235	Remote Similarity	NPD4756	Discovery
0.6232	Remote Similarity	NPD4220	Pre-registration
0.6184	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.618	Remote Similarity	NPD7154	Phase 3
0.6125	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5785	Approved
0.6023	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8779	Phase 3
0.5949	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD7839	Suspended
0.5897	Remote Similarity	NPD4192	Approved
0.5897	Remote Similarity	NPD4194	Approved
0.5897	Remote Similarity	NPD4193	Approved
0.5897	Remote Similarity	NPD4191	Approved
0.5895	Remote Similarity	NPD6698	Approved
0.5895	Remote Similarity	NPD46	Approved
0.5889	Remote Similarity	NPD5209	Approved
0.587	Remote Similarity	NPD5363	Approved
0.5843	Remote Similarity	NPD4252	Approved
0.5843	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6927	Phase 3
0.5833	Remote Similarity	NPD7637	Suspended
0.5824	Remote Similarity	NPD5362	Discontinued
0.5814	Remote Similarity	NPD8264	Approved
0.5797	Remote Similarity	NPD4265	Approved
0.5795	Remote Similarity	NPD4271	Approved
0.5795	Remote Similarity	NPD4268	Approved
0.5795	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5779	Approved
0.5773	Remote Similarity	NPD5778	Approved
0.5745	Remote Similarity	NPD4250	Approved
0.5745	Remote Similarity	NPD4251	Approved
0.5714	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4269	Approved
0.5714	Remote Similarity	NPD4270	Approved
0.5679	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.567	Remote Similarity	NPD7983	Approved
0.5667	Remote Similarity	NPD4822	Approved
0.5667	Remote Similarity	NPD4821	Approved
0.5667	Remote Similarity	NPD4820	Approved
0.5667	Remote Similarity	NPD4819	Approved
0.5664	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD4219	Approved
0.5652	Remote Similarity	NPD5331	Approved
0.5652	Remote Similarity	NPD5332	Approved
0.5638	Remote Similarity	NPD5786	Approved
0.5638	Remote Similarity	NPD4249	Approved
0.5618	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.561	Remote Similarity	NPD3704	Approved
0.5604	Remote Similarity	NPD4790	Discontinued
0.56	Remote Similarity	NPD539	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