NPASS Compound

Structure

NPC244456 OpenBabel07101719242D 21 24 0 0 1 0 0 0 0 0999 V2000 3.0154 -1.9041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2514 -2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7422 0.2151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3689 -1.2446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0785 0.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4583 -0.1703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6034 -0.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9892 -0.7189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5296 -3.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9306 -1.0562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8440 0.0812 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 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 15 1 0 0 0 0 5 8 2 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 9 15 1 0 0 0 0 10 5 1 6 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 6 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 6 0 0 0 13 16 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 1 1 6 0 0 0 16 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	281.835
LogP:	1.676
LogD:	1.19
LogS:	-3.607
# Rotatable Bonds:	0
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	5.306
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.23
MDCK Permeability:	2.465683064656332e-05
Pgp-inhibitor:	0.275
Pgp-substrate:	0.25
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.102

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.969
Plasma Protein Binding (PPB):	62.818939208984375%
Volume Distribution (VD):	0.502
Pgp-substrate:	58.38120651245117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.38
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.347
CYP3A4-substrate:	0.587

ADMET: Excretion

Clearance (CL):	7.961
Half-life (T1/2):	0.865

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.458
AMES Toxicity:	0.215
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.941
Carcinogencity:	0.474
Eye Corrosion:	0.902
Eye Irritation:	0.887
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC244456

Natural Product ID:	NPC244456
*Common Name:**	HBGYEPXELMLLBL-PDGPNTQRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HBGYEPXELMLLBL-PDGPNTQRSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-15-4-3-11(17)16(2)13(15)10(21-14(16)19)5-8-7-20-12(18)6-9(8)15/h3-6,10-11,13,17H,7H2,1-2H3/t10-,11+,13-,15-,16+/m1/s1
SMILES:	O=C1OCC2=C[C@@H]3[C@@H]4[C@](C2=C1)(C)C=C[C@@H]([C@]4(C)C(=O)O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011693
PubChem CID:	60151312
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO32742	aspergillus wentii en-48	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22283451]

☑ 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	5
MIC	1

Activity Type	# Activity
Cell Line	5
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	63000.0	nM	PMID[456480]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	38000.0	nM	PMID[456480]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	42000.0	nM	PMID[456480]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	42000.0	nM	PMID[456480]
NPT1312	Cell Line	SW1990	Homo sapiens	IC50	=	63000.0	nM	PMID[456480]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	16.0	ug.mL-1	PMID[456480]

☑ 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 NPC244456 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	193
0.1-0.2	912
0.2-0.3	3473
0.3-0.4	7470
0.4-0.5	14950
0.5-0.6	8154
0.6-0.7	5672
0.7-0.8	1768
0.8-0.85	98
0.85-0.9	3
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469657
0.9082	High Similarity	NPC235369
0.9032	High Similarity	NPC469372
0.8725	High Similarity	NPC91034
0.87	High Similarity	NPC273005
0.87	High Similarity	NPC31058
0.87	High Similarity	NPC469606
0.8641	High Similarity	NPC220155
0.8632	High Similarity	NPC212679
0.8632	High Similarity	NPC469595
0.8632	High Similarity	NPC220454
0.8571	High Similarity	NPC474315
0.85	High Similarity	NPC476299
0.85	High Similarity	NPC474012
0.8454	Intermediate Similarity	NPC115021
0.8447	Intermediate Similarity	NPC469607
0.8381	Intermediate Similarity	NPC137911
0.8381	Intermediate Similarity	NPC228477
0.8367	Intermediate Similarity	NPC53685
0.8367	Intermediate Similarity	NPC477130
0.8367	Intermediate Similarity	NPC477129
0.8316	Intermediate Similarity	NPC312561
0.8302	Intermediate Similarity	NPC29133
0.83	Intermediate Similarity	NPC53844
0.83	Intermediate Similarity	NPC208094
0.8283	Intermediate Similarity	NPC209355
0.8273	Intermediate Similarity	NPC284707
0.8269	Intermediate Similarity	NPC477125
0.8257	Intermediate Similarity	NPC64318
0.8247	Intermediate Similarity	NPC232426
0.8247	Intermediate Similarity	NPC281942
0.8224	Intermediate Similarity	NPC470961
0.8218	Intermediate Similarity	NPC141191
0.8218	Intermediate Similarity	NPC316598
0.82	Intermediate Similarity	NPC112654
0.8182	Intermediate Similarity	NPC469684
0.8182	Intermediate Similarity	NPC98249
0.8182	Intermediate Similarity	NPC53396
0.8173	Intermediate Similarity	NPC296950
0.8173	Intermediate Similarity	NPC309190
0.8173	Intermediate Similarity	NPC146731
0.8163	Intermediate Similarity	NPC472814
0.8163	Intermediate Similarity	NPC177037
0.8163	Intermediate Similarity	NPC141831
0.8148	Intermediate Similarity	NPC191620
0.8144	Intermediate Similarity	NPC218927
0.8144	Intermediate Similarity	NPC168131
0.8144	Intermediate Similarity	NPC206001
0.8131	Intermediate Similarity	NPC478209
0.8119	Intermediate Similarity	NPC169205
0.8119	Intermediate Similarity	NPC202705
0.8108	Intermediate Similarity	NPC186525
0.81	Intermediate Similarity	NPC183012
0.81	Intermediate Similarity	NPC295347
0.8073	Intermediate Similarity	NPC469496
0.8073	Intermediate Similarity	NPC469454
0.8073	Intermediate Similarity	NPC469463
0.8073	Intermediate Similarity	NPC122056
0.8061	Intermediate Similarity	NPC469368
0.8058	Intermediate Similarity	NPC472637
0.8056	Intermediate Similarity	NPC304180
0.8056	Intermediate Similarity	NPC179798
0.8041	Intermediate Similarity	NPC477128
0.8041	Intermediate Similarity	NPC476805
0.8041	Intermediate Similarity	NPC477302
0.8041	Intermediate Similarity	NPC136879
0.8041	Intermediate Similarity	NPC24816
0.8039	Intermediate Similarity	NPC23364
0.8021	Intermediate Similarity	NPC305475
0.8021	Intermediate Similarity	NPC475461
0.802	Intermediate Similarity	NPC185553
0.802	Intermediate Similarity	NPC242848
0.8019	Intermediate Similarity	NPC469853
0.8	Intermediate Similarity	NPC147912
0.8	Intermediate Similarity	NPC167219
0.8	Intermediate Similarity	NPC67259
0.7982	Intermediate Similarity	NPC236217
0.7981	Intermediate Similarity	NPC475320
0.7981	Intermediate Similarity	NPC114540
0.7981	Intermediate Similarity	NPC155332
0.7981	Intermediate Similarity	NPC32577
0.798	Intermediate Similarity	NPC36491
0.798	Intermediate Similarity	NPC186363
0.798	Intermediate Similarity	NPC233345
0.7963	Intermediate Similarity	NPC37116
0.7963	Intermediate Similarity	NPC5103
0.7963	Intermediate Similarity	NPC235014
0.7961	Intermediate Similarity	NPC477720
0.7959	Intermediate Similarity	NPC5509
0.7959	Intermediate Similarity	NPC284561
0.7946	Intermediate Similarity	NPC50774
0.7946	Intermediate Similarity	NPC709
0.7941	Intermediate Similarity	NPC70145
0.7941	Intermediate Similarity	NPC91695
0.7941	Intermediate Similarity	NPC475709
0.7941	Intermediate Similarity	NPC474343
0.7925	Intermediate Similarity	NPC478208
0.7925	Intermediate Similarity	NPC266570
0.7921	Intermediate Similarity	NPC193645
0.7921	Intermediate Similarity	NPC20546
0.7921	Intermediate Similarity	NPC48803
0.7921	Intermediate Similarity	NPC275960
0.7921	Intermediate Similarity	NPC90121
0.7917	Intermediate Similarity	NPC147921
0.7917	Intermediate Similarity	NPC470755
0.7917	Intermediate Similarity	NPC255307
0.7909	Intermediate Similarity	NPC478212
0.7909	Intermediate Similarity	NPC56448
0.7909	Intermediate Similarity	NPC25909
0.7905	Intermediate Similarity	NPC159533
0.7905	Intermediate Similarity	NPC475526
0.7905	Intermediate Similarity	NPC183570
0.7905	Intermediate Similarity	NPC329345
0.7905	Intermediate Similarity	NPC473283
0.79	Intermediate Similarity	NPC271652
0.79	Intermediate Similarity	NPC166346
0.789	Intermediate Similarity	NPC188738
0.789	Intermediate Similarity	NPC324683
0.7885	Intermediate Similarity	NPC99411
0.7885	Intermediate Similarity	NPC115899
0.7885	Intermediate Similarity	NPC63249
0.7885	Intermediate Similarity	NPC146822
0.7879	Intermediate Similarity	NPC51486
0.7879	Intermediate Similarity	NPC472307
0.7879	Intermediate Similarity	NPC15059
0.787	Intermediate Similarity	NPC475065
0.7864	Intermediate Similarity	NPC98868
0.7864	Intermediate Similarity	NPC124512
0.7864	Intermediate Similarity	NPC166745
0.7864	Intermediate Similarity	NPC478056
0.7864	Intermediate Similarity	NPC159763
0.7864	Intermediate Similarity	NPC278386
0.7864	Intermediate Similarity	NPC216478
0.7864	Intermediate Similarity	NPC471717
0.7864	Intermediate Similarity	NPC235464
0.7857	Intermediate Similarity	NPC72397
0.7857	Intermediate Similarity	NPC312824
0.7857	Intermediate Similarity	NPC167606
0.7857	Intermediate Similarity	NPC470493
0.7857	Intermediate Similarity	NPC476803
0.7857	Intermediate Similarity	NPC183580
0.7857	Intermediate Similarity	NPC226863
0.7857	Intermediate Similarity	NPC140055
0.7857	Intermediate Similarity	NPC470492
0.7857	Intermediate Similarity	NPC286528
0.7857	Intermediate Similarity	NPC20302
0.785	Intermediate Similarity	NPC473284
0.785	Intermediate Similarity	NPC330011
0.785	Intermediate Similarity	NPC329048
0.7843	Intermediate Similarity	NPC240673
0.7843	Intermediate Similarity	NPC17578
0.7838	Intermediate Similarity	NPC474181
0.7835	Intermediate Similarity	NPC316426
0.7835	Intermediate Similarity	NPC315395
0.783	Intermediate Similarity	NPC475676
0.783	Intermediate Similarity	NPC220964
0.7826	Intermediate Similarity	NPC287236
0.7822	Intermediate Similarity	NPC470697
0.7822	Intermediate Similarity	NPC474555
0.7822	Intermediate Similarity	NPC7165
0.7822	Intermediate Similarity	NPC298973
0.7822	Intermediate Similarity	NPC104925
0.7818	Intermediate Similarity	NPC69291
0.7818	Intermediate Similarity	NPC269530
0.7812	Intermediate Similarity	NPC114979
0.7812	Intermediate Similarity	NPC158756
0.7812	Intermediate Similarity	NPC476804
0.7812	Intermediate Similarity	NPC191476
0.781	Intermediate Similarity	NPC476081
0.781	Intermediate Similarity	NPC134077
0.781	Intermediate Similarity	NPC476890
0.781	Intermediate Similarity	NPC164551
0.7807	Intermediate Similarity	NPC474370
0.7807	Intermediate Similarity	NPC31641
0.7807	Intermediate Similarity	NPC473145
0.78	Intermediate Similarity	NPC72845
0.78	Intermediate Similarity	NPC300312
0.78	Intermediate Similarity	NPC45269
0.78	Intermediate Similarity	NPC252433
0.78	Intermediate Similarity	NPC111114
0.78	Intermediate Similarity	NPC303697
0.78	Intermediate Similarity	NPC261607
0.7798	Intermediate Similarity	NPC478211
0.7789	Intermediate Similarity	NPC89555
0.7788	Intermediate Similarity	NPC117685
0.7788	Intermediate Similarity	NPC469864
0.7788	Intermediate Similarity	NPC54705
0.7788	Intermediate Similarity	NPC47024
0.7788	Intermediate Similarity	NPC469872
0.7788	Intermediate Similarity	NPC227865
0.7788	Intermediate Similarity	NPC108581
0.7788	Intermediate Similarity	NPC478206
0.7788	Intermediate Similarity	NPC266955
0.7788	Intermediate Similarity	NPC475913
0.7788	Intermediate Similarity	NPC478205
0.7778	Intermediate Similarity	NPC50488
0.7778	Intermediate Similarity	NPC275539
0.7778	Intermediate Similarity	NPC118011
0.7778	Intermediate Similarity	NPC97577
0.7778	Intermediate Similarity	NPC474396

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 NPC244456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1205
0.2-0.3	3349
0.3-0.4	2758
0.4-0.5	1079
0.5-0.6	378
0.6-0.7	186
0.7-0.8	31
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.798	Intermediate Similarity	NPD6411	Approved
0.7921	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD5779	Approved
0.79	Intermediate Similarity	NPD5778	Approved
0.7864	Intermediate Similarity	NPD4225	Approved
0.7857	Intermediate Similarity	NPD7115	Discovery
0.7778	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6101	Approved
0.77	Intermediate Similarity	NPD5785	Approved
0.7551	Intermediate Similarity	NPD1694	Approved
0.7451	Intermediate Similarity	NPD5281	Approved
0.7451	Intermediate Similarity	NPD5284	Approved
0.7379	Intermediate Similarity	NPD6399	Phase 3
0.729	Intermediate Similarity	NPD7640	Approved
0.729	Intermediate Similarity	NPD7639	Approved
0.7288	Intermediate Similarity	NPD8513	Phase 3
0.7282	Intermediate Similarity	NPD7637	Suspended
0.7245	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5695	Phase 3
0.72	Intermediate Similarity	NPD5363	Approved
0.7196	Intermediate Similarity	NPD7638	Approved
0.7193	Intermediate Similarity	NPD6053	Discontinued
0.7184	Intermediate Similarity	NPD5207	Approved
0.7168	Intermediate Similarity	NPD6371	Approved
0.7143	Intermediate Similarity	NPD5282	Discontinued
0.7143	Intermediate Similarity	NPD8515	Approved
0.7143	Intermediate Similarity	NPD8517	Approved
0.7143	Intermediate Similarity	NPD8516	Approved
0.7143	Intermediate Similarity	NPD6686	Approved
0.7129	Intermediate Similarity	NPD5279	Phase 3
0.7115	Intermediate Similarity	NPD7983	Approved
0.7103	Intermediate Similarity	NPD6083	Phase 2
0.7103	Intermediate Similarity	NPD6084	Phase 2
0.7103	Intermediate Similarity	NPD7902	Approved
0.71	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4270	Approved
0.7071	Intermediate Similarity	NPD5209	Approved
0.7071	Intermediate Similarity	NPD4269	Approved
0.7054	Intermediate Similarity	NPD5697	Approved
0.7037	Intermediate Similarity	NPD5696	Approved
0.7019	Intermediate Similarity	NPD46	Approved
0.7019	Intermediate Similarity	NPD6698	Approved
0.7	Intermediate Similarity	NPD7154	Phase 3
0.6991	Remote Similarity	NPD6899	Approved
0.6991	Remote Similarity	NPD6881	Approved
0.6981	Remote Similarity	NPD7748	Approved
0.6964	Remote Similarity	NPD5739	Approved
0.6964	Remote Similarity	NPD7128	Approved
0.6964	Remote Similarity	NPD6675	Approved
0.6964	Remote Similarity	NPD6402	Approved
0.6961	Remote Similarity	NPD3618	Phase 1
0.6961	Remote Similarity	NPD5330	Approved
0.6961	Remote Similarity	NPD5786	Approved
0.6961	Remote Similarity	NPD7146	Approved
0.6961	Remote Similarity	NPD6684	Approved
0.6961	Remote Similarity	NPD7334	Approved
0.6961	Remote Similarity	NPD7521	Approved
0.6961	Remote Similarity	NPD6409	Approved
0.6957	Remote Similarity	NPD6650	Approved
0.6957	Remote Similarity	NPD6649	Approved
0.6957	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5694	Approved
0.6952	Remote Similarity	NPD7515	Phase 2
0.6931	Remote Similarity	NPD3133	Approved
0.6931	Remote Similarity	NPD3666	Approved
0.6931	Remote Similarity	NPD3665	Phase 1
0.693	Remote Similarity	NPD6372	Approved
0.693	Remote Similarity	NPD6012	Approved
0.693	Remote Similarity	NPD6373	Approved
0.693	Remote Similarity	NPD6014	Approved
0.693	Remote Similarity	NPD6013	Approved
0.693	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5701	Approved
0.6903	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3667	Approved
0.6881	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8039	Approved
0.687	Remote Similarity	NPD6883	Approved
0.687	Remote Similarity	NPD7290	Approved
0.687	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7102	Approved
0.6869	Remote Similarity	NPD4252	Approved
0.6869	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5692	Phase 3
0.6857	Remote Similarity	NPD7838	Discovery
0.6855	Remote Similarity	NPD8074	Phase 3
0.6852	Remote Similarity	NPD7839	Suspended
0.6847	Remote Similarity	NPD5211	Phase 2
0.6842	Remote Similarity	NPD7320	Approved
0.6842	Remote Similarity	NPD6011	Approved
0.6837	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5362	Discontinued
0.6827	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5737	Approved
0.6827	Remote Similarity	NPD6903	Approved
0.6827	Remote Similarity	NPD6672	Approved
0.6822	Remote Similarity	NPD7900	Approved
0.6822	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6869	Approved
0.681	Remote Similarity	NPD6847	Approved
0.681	Remote Similarity	NPD8130	Phase 1
0.681	Remote Similarity	NPD6617	Approved
0.68	Remote Similarity	NPD5369	Approved
0.6796	Remote Similarity	NPD4519	Discontinued
0.6796	Remote Similarity	NPD4623	Approved
0.6792	Remote Similarity	NPD6050	Approved
0.6792	Remote Similarity	NPD5693	Phase 1
0.6772	Remote Similarity	NPD7260	Phase 2
0.6765	Remote Similarity	NPD4786	Approved
0.6762	Remote Similarity	NPD4753	Phase 2
0.6759	Remote Similarity	NPD5210	Approved
0.6759	Remote Similarity	NPD4629	Approved
0.6752	Remote Similarity	NPD6882	Approved
0.6752	Remote Similarity	NPD8297	Approved
0.6726	Remote Similarity	NPD5141	Approved
0.67	Remote Similarity	NPD4819	Approved
0.67	Remote Similarity	NPD4820	Approved
0.67	Remote Similarity	NPD4821	Approved
0.67	Remote Similarity	NPD4822	Approved
0.6696	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6639	Remote Similarity	NPD6319	Approved
0.6636	Remote Similarity	NPD4755	Approved
0.6636	Remote Similarity	NPD6079	Approved
0.6635	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5280	Approved
0.6635	Remote Similarity	NPD4249	Approved
0.6635	Remote Similarity	NPD4694	Approved
0.6609	Remote Similarity	NPD6412	Phase 2
0.6609	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5328	Approved
0.6585	Remote Similarity	NPD7503	Approved
0.6574	Remote Similarity	NPD4202	Approved
0.6571	Remote Similarity	NPD4250	Approved
0.6571	Remote Similarity	NPD4251	Approved
0.6569	Remote Similarity	NPD6435	Approved
0.656	Remote Similarity	NPD7492	Approved
0.6552	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5226	Approved
0.6549	Remote Similarity	NPD5225	Approved
0.6549	Remote Similarity	NPD5224	Approved
0.6549	Remote Similarity	NPD4633	Approved
0.6545	Remote Similarity	NPD5222	Approved
0.6545	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4697	Phase 3
0.6545	Remote Similarity	NPD5221	Approved
0.6538	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4695	Discontinued
0.6531	Remote Similarity	NPD8264	Approved
0.6525	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4700	Approved
0.6509	Remote Similarity	NPD4518	Approved
0.6508	Remote Similarity	NPD6616	Approved
0.6504	Remote Similarity	NPD6054	Approved
0.6491	Remote Similarity	NPD5175	Approved
0.6491	Remote Similarity	NPD5174	Approved
0.6486	Remote Similarity	NPD5173	Approved
0.6484	Remote Similarity	NPD7319	Approved
0.6481	Remote Similarity	NPD8034	Phase 2
0.6481	Remote Similarity	NPD8035	Phase 2
0.6476	Remote Similarity	NPD5690	Phase 2
0.6462	Remote Similarity	NPD6845	Suspended
0.646	Remote Similarity	NPD5223	Approved
0.6457	Remote Similarity	NPD7078	Approved
0.6455	Remote Similarity	NPD5654	Approved
0.6452	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6015	Approved
0.6452	Remote Similarity	NPD6016	Approved
0.6449	Remote Similarity	NPD6673	Approved
0.6449	Remote Similarity	NPD1695	Approved
0.6449	Remote Similarity	NPD6080	Approved
0.6449	Remote Similarity	NPD6051	Approved
0.6449	Remote Similarity	NPD6904	Approved
0.6446	Remote Similarity	NPD6274	Approved
0.6442	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3668	Phase 3
0.6441	Remote Similarity	NPD4634	Approved
0.6423	Remote Similarity	NPD7101	Approved
0.6423	Remote Similarity	NPD7100	Approved
0.6417	Remote Similarity	NPD4632	Approved
0.6415	Remote Similarity	NPD3573	Approved
0.6408	Remote Similarity	NPD4223	Phase 3
0.6408	Remote Similarity	NPD4221	Approved
0.6406	Remote Similarity	NPD7736	Approved
0.64	Remote Similarity	NPD4756	Discovery
0.64	Remote Similarity	NPD5988	Approved
0.64	Remote Similarity	NPD6370	Approved
0.6393	Remote Similarity	NPD6317	Approved
0.6381	Remote Similarity	NPD1696	Phase 3
0.6378	Remote Similarity	NPD7507	Approved
0.6373	Remote Similarity	NPD5368	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