NPASS Compound

Structure

CID232426 OpenBabel06191716032D 24 26 0 0 1 0 0 0 0 0999 V2000 4.8968 -1.7938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2642 1.6651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5307 -2.1493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8530 -2.5462 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 0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0047 -0.6998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0810 0.5138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5576 0.4430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9464 -1.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3106 0.6662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6925 0.0209 0.0000 C 0 0 1 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 1.2024 -1.0827 0.0000 C 0 0 0 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 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 4.4882 0.6265 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 1.5600 0.7203 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 12 2 0 0 0 0 2 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 14 6 1 6 0 0 0 14 19 1 0 0 0 0 15 21 1 1 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 20 23 1 6 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	3.709
LogD:	3.578
LogS:	-4.602
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	5.859
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.722
MDCK Permeability:	2.6362242351751775e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.08
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.744
30% Bioavailability (F30%):	0.316

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.758
Plasma Protein Binding (PPB):	81.20438385009766%
Volume Distribution (VD):	0.493
Pgp-substrate:	16.9720516204834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.63
CYP2C19-substrate:	0.616
CYP2C9-inhibitor:	0.74
CYP2C9-substrate:	0.182
CYP2D6-inhibitor:	0.2
CYP2D6-substrate:	0.267
CYP3A4-inhibitor:	0.417
CYP3A4-substrate:	0.441

ADMET: Excretion

Clearance (CL):	10.584
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.171
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.465
Carcinogencity:	0.644
Eye Corrosion:	0.004
Eye Irritation:	0.05
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC232426

Natural Product ID:	NPC232426
*Common Name:**	Cespihypotin V
IUPAC Name:	n.a.
Synonyms:	Cespihypotin V
Standard InCHIKey:	NAXRGDYBDAKNAZ-XBKCGROWSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-12-5-6-14-7-8-16-17(19(14,3)4)20(23,24-18(16)22)11-13(2)10-15(21)9-12/h10,14-15,21,23H,1,5-9,11H2,2-4H3/b13-10+/t14-,15+,20+/m1/s1
SMILES:	C=C1CC[C@@H]2CCC3=C(C2(C)C)[C@@](C/C(=C/[C@H](C1)O)/C)(O)OC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509616
PubChem CID:	25178967
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398538]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933873]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18484775]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061391]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21513294]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25516	Dahlia sherffii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25452	Crucigenia apiculata	Species	Scenedesmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23333	Michelia excelsa	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28702	Cyclolepis genistoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20428	Debregeasia salicifolia	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25485	Agathosma lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25061	Lactarius glyciosmus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19210	Quercus lusitanica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5278	Acacia cyperophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11177	0ctiluca scintillans	Species	0ctilucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24616	Ottonia vahlii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5543	Persicaria tomentosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3706	Hedypnois rhagadioloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25205	Thymus borgiae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25684	Fagus dombeyi	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24435	Beschorneria bracteata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25631	Picris kamtschatica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25606	Aster patagonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25314	Usnea ceratina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25655	Pseudocyphellaria granulata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23999	Rhipidothuria racowitzai	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2404	Heterophragma quadriloculare	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6639	Flagelloscypha pilatii	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24482	Phyllanthus oxyphyllus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25427	Solanum vespertilio	Species	Solanaceae	Eukaryota	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1184	Cell Line	Daoy	Homo sapiens	ED50	=	60.0	uM	PMID[546084]
NPT1183	Cell Line	WiDr	Homo sapiens	ED50	>	60.0	uM	PMID[546084]

☑ 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 NPC232426 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	187
0.1-0.2	1024
0.2-0.3	4310
0.3-0.4	10641
0.4-0.5	12698
0.5-0.6	6728
0.6-0.7	5420
0.7-0.8	1557
0.8-0.85	109
0.85-0.9	17
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC281942
0.9882	High Similarity	NPC141831
0.9643	High Similarity	NPC312561
0.9	High Similarity	NPC53685
0.8977	High Similarity	NPC5509
0.8941	High Similarity	NPC193198
0.8889	High Similarity	NPC115021
0.8876	High Similarity	NPC477782
0.8864	High Similarity	NPC472378
0.8791	High Similarity	NPC474554
0.8778	High Similarity	NPC477783
0.8764	High Similarity	NPC470734
0.8723	High Similarity	NPC472644
0.871	High Similarity	NPC475709
0.871	High Similarity	NPC208094
0.871	High Similarity	NPC53844
0.8681	High Similarity	NPC472303
0.8636	High Similarity	NPC474062
0.8632	High Similarity	NPC472643
0.8621	High Similarity	NPC31086
0.8602	High Similarity	NPC470801
0.8602	High Similarity	NPC17578
0.8602	High Similarity	NPC240673
0.8587	High Similarity	NPC104925
0.8587	High Similarity	NPC298973
0.8587	High Similarity	NPC474555
0.8571	High Similarity	NPC472814
0.8571	High Similarity	NPC177037
0.8571	High Similarity	NPC289479
0.8556	High Similarity	NPC174342
0.8556	High Similarity	NPC251528
0.8556	High Similarity	NPC168131
0.8526	High Similarity	NPC474012
0.8526	High Similarity	NPC477720
0.8526	High Similarity	NPC476767
0.8526	High Similarity	NPC476299
0.8523	High Similarity	NPC189311
0.8523	High Similarity	NPC474860
0.8523	High Similarity	NPC65661
0.8523	High Similarity	NPC471300
0.8523	High Similarity	NPC473251
0.8523	High Similarity	NPC42586
0.8523	High Similarity	NPC86316
0.8523	High Similarity	NPC106416
0.8506	High Similarity	NPC472377
0.8495	Intermediate Similarity	NPC295347
0.8495	Intermediate Similarity	NPC183012
0.8478	Intermediate Similarity	NPC139692
0.8478	Intermediate Similarity	NPC166346
0.8478	Intermediate Similarity	NPC242069
0.8462	Intermediate Similarity	NPC51486
0.8444	Intermediate Similarity	NPC472810
0.8444	Intermediate Similarity	NPC472809
0.8444	Intermediate Similarity	NPC226863
0.8421	Intermediate Similarity	NPC222303
0.8421	Intermediate Similarity	NPC23364
0.8404	Intermediate Similarity	NPC134072
0.8404	Intermediate Similarity	NPC242848
0.8404	Intermediate Similarity	NPC234993
0.8391	Intermediate Similarity	NPC471298
0.8387	Intermediate Similarity	NPC469697
0.8387	Intermediate Similarity	NPC475572
0.837	Intermediate Similarity	NPC472811
0.8333	Intermediate Similarity	NPC475678
0.8316	Intermediate Similarity	NPC69385
0.8316	Intermediate Similarity	NPC476253
0.8316	Intermediate Similarity	NPC474343
0.8315	Intermediate Similarity	NPC471795
0.8298	Intermediate Similarity	NPC209355
0.8295	Intermediate Similarity	NPC471297
0.8295	Intermediate Similarity	NPC474809
0.8295	Intermediate Similarity	NPC311070
0.828	Intermediate Similarity	NPC472812
0.828	Intermediate Similarity	NPC469939
0.828	Intermediate Similarity	NPC475657
0.8276	Intermediate Similarity	NPC325031
0.8276	Intermediate Similarity	NPC475944
0.8265	Intermediate Similarity	NPC471208
0.8261	Intermediate Similarity	NPC212679
0.8261	Intermediate Similarity	NPC469595
0.8261	Intermediate Similarity	NPC477147
0.8261	Intermediate Similarity	NPC78973
0.8261	Intermediate Similarity	NPC477149
0.8261	Intermediate Similarity	NPC220454
0.8247	Intermediate Similarity	NPC471075
0.8247	Intermediate Similarity	NPC303559
0.8247	Intermediate Similarity	NPC469657
0.8247	Intermediate Similarity	NPC244456
0.8247	Intermediate Similarity	NPC63249
0.8242	Intermediate Similarity	NPC474629
0.8229	Intermediate Similarity	NPC316598
0.8229	Intermediate Similarity	NPC222011
0.8222	Intermediate Similarity	NPC473226
0.8222	Intermediate Similarity	NPC220478
0.8211	Intermediate Similarity	NPC165632
0.8211	Intermediate Similarity	NPC112654
0.8211	Intermediate Similarity	NPC162346
0.8202	Intermediate Similarity	NPC71626
0.8202	Intermediate Similarity	NPC474865
0.8202	Intermediate Similarity	NPC471301
0.8202	Intermediate Similarity	NPC82297
0.8191	Intermediate Similarity	NPC470255
0.8182	Intermediate Similarity	NPC200513
0.8182	Intermediate Similarity	NPC323251
0.8182	Intermediate Similarity	NPC471296
0.8172	Intermediate Similarity	NPC233345
0.8172	Intermediate Similarity	NPC477122
0.8172	Intermediate Similarity	NPC165904
0.8172	Intermediate Similarity	NPC179517
0.8172	Intermediate Similarity	NPC186363
0.8172	Intermediate Similarity	NPC329842
0.8172	Intermediate Similarity	NPC303697
0.8172	Intermediate Similarity	NPC65513
0.8163	Intermediate Similarity	NPC469606
0.8163	Intermediate Similarity	NPC476081
0.8163	Intermediate Similarity	NPC273005
0.8163	Intermediate Similarity	NPC134077
0.8163	Intermediate Similarity	NPC58329
0.8163	Intermediate Similarity	NPC31058
0.8161	Intermediate Similarity	NPC271104
0.8152	Intermediate Similarity	NPC206001
0.8152	Intermediate Similarity	NPC50488
0.8152	Intermediate Similarity	NPC214387
0.8152	Intermediate Similarity	NPC218927
0.8152	Intermediate Similarity	NPC474396
0.8144	Intermediate Similarity	NPC117685
0.8144	Intermediate Similarity	NPC54705
0.814	Intermediate Similarity	NPC471220
0.814	Intermediate Similarity	NPC475994
0.814	Intermediate Similarity	NPC209135
0.814	Intermediate Similarity	NPC474816
0.8125	Intermediate Similarity	NPC132753
0.8125	Intermediate Similarity	NPC224356
0.8125	Intermediate Similarity	NPC253826
0.8125	Intermediate Similarity	NPC202705
0.8125	Intermediate Similarity	NPC151681
0.8125	Intermediate Similarity	NPC121402
0.8125	Intermediate Similarity	NPC175351
0.8111	Intermediate Similarity	NPC52628
0.8111	Intermediate Similarity	NPC474853
0.8111	Intermediate Similarity	NPC179006
0.8105	Intermediate Similarity	NPC476488
0.8105	Intermediate Similarity	NPC473369
0.8105	Intermediate Similarity	NPC476487
0.8105	Intermediate Similarity	NPC472441
0.81	Intermediate Similarity	NPC472645
0.809	Intermediate Similarity	NPC22611
0.809	Intermediate Similarity	NPC474193
0.809	Intermediate Similarity	NPC12283
0.809	Intermediate Similarity	NPC42476
0.8085	Intermediate Similarity	NPC476597
0.8085	Intermediate Similarity	NPC476598
0.8081	Intermediate Similarity	NPC120321
0.8068	Intermediate Similarity	NPC14203
0.8068	Intermediate Similarity	NPC40228
0.8068	Intermediate Similarity	NPC229584
0.8065	Intermediate Similarity	NPC469368
0.8065	Intermediate Similarity	NPC469372
0.8065	Intermediate Similarity	NPC182136
0.8065	Intermediate Similarity	NPC221111
0.8065	Intermediate Similarity	NPC280149
0.8061	Intermediate Similarity	NPC471412
0.8046	Intermediate Similarity	NPC242767
0.8046	Intermediate Similarity	NPC471299
0.8043	Intermediate Similarity	NPC472302
0.8043	Intermediate Similarity	NPC477128
0.8043	Intermediate Similarity	NPC477302
0.8043	Intermediate Similarity	NPC136879
0.8043	Intermediate Similarity	NPC24816
0.8041	Intermediate Similarity	NPC98868
0.8041	Intermediate Similarity	NPC478056
0.8039	Intermediate Similarity	NPC137911
0.8039	Intermediate Similarity	NPC228477
0.8023	Intermediate Similarity	NPC262747
0.8023	Intermediate Similarity	NPC316500
0.8022	Intermediate Similarity	NPC261721
0.8022	Intermediate Similarity	NPC471219
0.8022	Intermediate Similarity	NPC202394
0.8022	Intermediate Similarity	NPC305475
0.8022	Intermediate Similarity	NPC82979
0.8022	Intermediate Similarity	NPC475461
0.8022	Intermediate Similarity	NPC329692
0.8022	Intermediate Similarity	NPC322159
0.8022	Intermediate Similarity	NPC131813
0.8021	Intermediate Similarity	NPC472362
0.8021	Intermediate Similarity	NPC154526
0.8021	Intermediate Similarity	NPC202833
0.8021	Intermediate Similarity	NPC328371
0.8021	Intermediate Similarity	NPC472363
0.802	Intermediate Similarity	NPC91034
0.802	Intermediate Similarity	NPC67321
0.802	Intermediate Similarity	NPC187435
0.8	Intermediate Similarity	NPC476596
0.8	Intermediate Similarity	NPC126518
0.8	Intermediate Similarity	NPC471302
0.8	Intermediate Similarity	NPC165064
0.8	Intermediate Similarity	NPC472326
0.8	Intermediate Similarity	NPC30486
0.8	Intermediate Similarity	NPC295799
0.8	Intermediate Similarity	NPC477129

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 NPC232426 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	1561
0.2-0.3	3571
0.3-0.4	2531
0.4-0.5	819
0.5-0.6	333
0.6-0.7	153
0.7-0.8	21
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7640	Approved
0.7778	Intermediate Similarity	NPD7639	Approved
0.7767	Intermediate Similarity	NPD6686	Approved
0.7684	Intermediate Similarity	NPD5785	Approved
0.7677	Intermediate Similarity	NPD7638	Approved
0.7677	Intermediate Similarity	NPD4225	Approved
0.7527	Intermediate Similarity	NPD1694	Approved
0.7526	Intermediate Similarity	NPD6399	Phase 3
0.7449	Intermediate Similarity	NPD7748	Approved
0.7447	Intermediate Similarity	NPD6684	Approved
0.7447	Intermediate Similarity	NPD7334	Approved
0.7447	Intermediate Similarity	NPD7521	Approved
0.7447	Intermediate Similarity	NPD7146	Approved
0.7447	Intermediate Similarity	NPD6409	Approved
0.7447	Intermediate Similarity	NPD5330	Approved
0.7423	Intermediate Similarity	NPD7515	Phase 2
0.7419	Intermediate Similarity	NPD3665	Phase 1
0.7419	Intermediate Similarity	NPD3133	Approved
0.7419	Intermediate Similarity	NPD3666	Approved
0.74	Intermediate Similarity	NPD6083	Phase 2
0.74	Intermediate Similarity	NPD6084	Phase 2
0.7391	Intermediate Similarity	NPD3667	Approved
0.7374	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5695	Phase 3
0.7364	Intermediate Similarity	NPD7115	Discovery
0.7347	Intermediate Similarity	NPD5778	Approved
0.7347	Intermediate Similarity	NPD5779	Approved
0.7333	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6698	Approved
0.732	Intermediate Similarity	NPD46	Approved
0.7312	Intermediate Similarity	NPD7154	Phase 3
0.7312	Intermediate Similarity	NPD5362	Discontinued
0.7292	Intermediate Similarity	NPD6672	Approved
0.7292	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6903	Approved
0.7292	Intermediate Similarity	NPD5737	Approved
0.7263	Intermediate Similarity	NPD3618	Phase 1
0.7245	Intermediate Similarity	NPD6411	Approved
0.7245	Intermediate Similarity	NPD5693	Phase 1
0.7234	Intermediate Similarity	NPD4786	Approved
0.7228	Intermediate Similarity	NPD7902	Approved
0.7196	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8039	Approved
0.7158	Intermediate Similarity	NPD5363	Approved
0.7157	Intermediate Similarity	NPD5696	Approved
0.7156	Intermediate Similarity	NPD6053	Discontinued
0.7115	Intermediate Similarity	NPD7632	Discontinued
0.7083	Intermediate Similarity	NPD5279	Phase 3
0.7083	Intermediate Similarity	NPD4623	Approved
0.7083	Intermediate Similarity	NPD4519	Discontinued
0.7075	Intermediate Similarity	NPD6675	Approved
0.7075	Intermediate Similarity	NPD6402	Approved
0.7075	Intermediate Similarity	NPD7128	Approved
0.7075	Intermediate Similarity	NPD5739	Approved
0.7041	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5328	Approved
0.7041	Intermediate Similarity	NPD4753	Phase 2
0.7041	Intermediate Similarity	NPD6101	Approved
0.7021	Intermediate Similarity	NPD4269	Approved
0.7021	Intermediate Similarity	NPD4270	Approved
0.7009	Intermediate Similarity	NPD6412	Phase 2
0.7009	Intermediate Similarity	NPD5701	Approved
0.7009	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD6882	Approved
0.6989	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4695	Discontinued
0.6972	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6371	Approved
0.6944	Remote Similarity	NPD7320	Approved
0.6944	Remote Similarity	NPD6899	Approved
0.6944	Remote Similarity	NPD6881	Approved
0.6944	Remote Similarity	NPD6011	Approved
0.6931	Remote Similarity	NPD7900	Approved
0.6931	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5786	Approved
0.69	Remote Similarity	NPD6079	Approved
0.69	Remote Similarity	NPD5281	Approved
0.69	Remote Similarity	NPD7637	Suspended
0.69	Remote Similarity	NPD5284	Approved
0.6881	Remote Similarity	NPD6372	Approved
0.6881	Remote Similarity	NPD6373	Approved
0.6881	Remote Similarity	NPD6012	Approved
0.6881	Remote Similarity	NPD6014	Approved
0.6881	Remote Similarity	NPD6013	Approved
0.6875	Remote Similarity	NPD3668	Phase 3
0.6869	Remote Similarity	NPD6673	Approved
0.6869	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6051	Approved
0.6869	Remote Similarity	NPD6904	Approved
0.6869	Remote Similarity	NPD6080	Approved
0.6864	Remote Similarity	NPD7507	Approved
0.6842	Remote Similarity	NPD4223	Phase 3
0.6842	Remote Similarity	NPD4221	Approved
0.6842	Remote Similarity	NPD5209	Approved
0.6832	Remote Similarity	NPD4202	Approved
0.6827	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7102	Approved
0.6818	Remote Similarity	NPD6883	Approved
0.6818	Remote Similarity	NPD7290	Approved
0.6809	Remote Similarity	NPD4821	Approved
0.6809	Remote Similarity	NPD4819	Approved
0.6809	Remote Similarity	NPD4822	Approved
0.6809	Remote Similarity	NPD4252	Approved
0.6809	Remote Similarity	NPD4820	Approved
0.6804	Remote Similarity	NPD1696	Phase 3
0.6804	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5692	Phase 3
0.6796	Remote Similarity	NPD4697	Phase 3
0.6796	Remote Similarity	NPD5221	Approved
0.6796	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5222	Approved
0.6796	Remote Similarity	NPD7839	Suspended
0.6792	Remote Similarity	NPD5211	Phase 2
0.6774	Remote Similarity	NPD4271	Approved
0.6774	Remote Similarity	NPD4268	Approved
0.6771	Remote Similarity	NPD5332	Approved
0.6771	Remote Similarity	NPD5331	Approved
0.6768	Remote Similarity	NPD5208	Approved
0.6757	Remote Similarity	NPD6617	Approved
0.6757	Remote Similarity	NPD6869	Approved
0.6757	Remote Similarity	NPD6649	Approved
0.6757	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6650	Approved
0.6757	Remote Similarity	NPD6847	Approved
0.6757	Remote Similarity	NPD8130	Phase 1
0.6737	Remote Similarity	NPD4790	Discontinued
0.6737	Remote Similarity	NPD5369	Approved
0.6733	Remote Similarity	NPD5694	Approved
0.6733	Remote Similarity	NPD6050	Approved
0.6731	Remote Similarity	NPD5173	Approved
0.6731	Remote Similarity	NPD4755	Approved
0.6701	Remote Similarity	NPD4197	Approved
0.6699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5210	Approved
0.6699	Remote Similarity	NPD4629	Approved
0.6697	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8297	Approved
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD4756	Discovery
0.6634	Remote Similarity	NPD5207	Approved
0.6634	Remote Similarity	NPD7838	Discovery
0.6633	Remote Similarity	NPD5329	Approved
0.6633	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6009	Approved
0.6607	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6008	Approved
0.6604	Remote Similarity	NPD4700	Approved
0.6604	Remote Similarity	NPD5286	Approved
0.6604	Remote Similarity	NPD5285	Approved
0.6604	Remote Similarity	NPD4696	Approved
0.6604	Remote Similarity	NPD6404	Discontinued
0.6602	Remote Similarity	NPD5282	Discontinued
0.6596	Remote Similarity	NPD3617	Approved
0.6569	Remote Similarity	NPD8034	Phase 2
0.6569	Remote Similarity	NPD8035	Phase 2
0.6569	Remote Similarity	NPD7983	Approved
0.6566	Remote Similarity	NPD4689	Approved
0.6566	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6098	Approved
0.6566	Remote Similarity	NPD4688	Approved
0.6566	Remote Similarity	NPD4138	Approved
0.6566	Remote Similarity	NPD4690	Approved
0.6566	Remote Similarity	NPD4249	Approved
0.6566	Remote Similarity	NPD5280	Approved
0.6566	Remote Similarity	NPD5205	Approved
0.6566	Remote Similarity	NPD4693	Phase 3
0.6566	Remote Similarity	NPD4694	Approved
0.6566	Remote Similarity	NPD5690	Phase 2
0.6559	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7327	Approved
0.6552	Remote Similarity	NPD7328	Approved
0.6552	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5223	Approved
0.6542	Remote Similarity	NPD5344	Discontinued
0.6525	Remote Similarity	NPD8033	Approved
0.6522	Remote Similarity	NPD6274	Approved
0.6522	Remote Similarity	NPD6868	Approved
0.65	Remote Similarity	NPD4250	Approved
0.65	Remote Similarity	NPD4251	Approved
0.6496	Remote Similarity	NPD7516	Approved
0.6491	Remote Similarity	NPD4632	Approved
0.6481	Remote Similarity	NPD4633	Approved
0.6481	Remote Similarity	NPD5224	Approved
0.6481	Remote Similarity	NPD5225	Approved
0.6481	Remote Similarity	NPD5226	Approved
0.6466	Remote Similarity	NPD6317	Approved
0.6458	Remote Similarity	NPD5368	Approved
0.6458	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7339	Approved
0.6452	Remote Similarity	NPD8264	Approved
0.6452	Remote Similarity	NPD6942	Approved
0.6442	Remote Similarity	NPD6001	Approved
0.6441	Remote Similarity	NPD8377	Approved
0.6441	Remote Similarity	NPD8294	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