NPASS Compound

Structure

CID312561 OpenBabel06191716122D 23 25 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 0.9945 -0.1045 0.0000 C 0 0 2 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 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 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 20 1 0 0 0 0 4 20 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 14 6 1 6 0 0 0 14 20 1 0 0 0 0 15 21 1 1 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 11 1 6 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	4.681
LogD:	3.989
LogS:	-4.708
# Rotatable Bonds:	0
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.697
Synthetic Accessibility Score:	5.68
Fsp3:	0.6
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:	-4.893
MDCK Permeability:	1.713194251351524e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.074

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.503
Plasma Protein Binding (PPB):	93.52603149414062%
Volume Distribution (VD):	0.662
Pgp-substrate:	5.884791374206543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.105
CYP1A2-substrate:	0.647
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.708
CYP2C9-inhibitor:	0.243
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	8.732
Half-life (T1/2):	0.311

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.694
Drug-inuced Liver Injury (DILI):	0.663
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.917
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.412
Carcinogencity:	0.65
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC312561

Natural Product ID:	NPC312561
*Common Name:**	Cespitularin O
IUPAC Name:	n.a.
Synonyms:	Cespitularin O
Standard InCHIKey:	WAXTXFVEXSJBJW-CZIVKBJPSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-12-5-6-14-7-8-16-18(20(14,3)4)17(23-19(16)22)11-13(2)10-15(21)9-12/h10,14-15,17,21H,1,5-9,11H2,2-4H3/b13-10+/t14-,15+,17-/m1/s1
SMILES:	C=C1CC[C@@H]2CCC3=C(C2(C)C)[C@@H](C/C(=C/[C@H](C1)O)/C)OC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495856
PubChem CID:	16083141
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]
NPO19210	Quercus lusitanica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25061	Lactarius glyciosmus	Species	Russulaceae	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]
NPO25205	Thymus borgiae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3706	Hedypnois rhagadioloides	Species	Asteraceae	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]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24435	Beschorneria bracteata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25684	Fagus dombeyi	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25606	Aster patagonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25631	Picris kamtschatica	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]
NPO25427	Solanum vespertilio	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24482	Phyllanthus oxyphyllus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25516	Dahlia sherffii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25452	Crucigenia apiculata	Species	Scenedesmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28702	Cyclolepis genistoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23333	Michelia excelsa	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25485	Agathosma lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20428	Debregeasia salicifolia	Species	Urticaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.4	ug ml-1	PMID[478976]

☑ 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 NPC312561 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	181
0.1-0.2	1010
0.2-0.3	4393
0.3-0.4	11288
0.4-0.5	12225
0.5-0.6	6519
0.6-0.7	5215
0.7-0.8	1731
0.8-0.85	113
0.85-0.9	16
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC281942
0.9643	High Similarity	NPC232426
0.9529	High Similarity	NPC141831
0.9268	High Similarity	NPC193198
0.9195	High Similarity	NPC115021
0.9091	High Similarity	NPC53685
0.907	High Similarity	NPC5509
0.8864	High Similarity	NPC472814
0.8864	High Similarity	NPC177037
0.8824	High Similarity	NPC86316
0.8824	High Similarity	NPC106416
0.881	High Similarity	NPC472377
0.8791	High Similarity	NPC208094
0.8791	High Similarity	NPC53844
0.8706	High Similarity	NPC31086
0.8636	High Similarity	NPC168131
0.8636	High Similarity	NPC174342
0.8605	High Similarity	NPC65661
0.8605	High Similarity	NPC189311
0.8605	High Similarity	NPC471795
0.8602	High Similarity	NPC476299
0.8602	High Similarity	NPC474012
0.8588	High Similarity	NPC311070
0.8571	High Similarity	NPC325031
0.8571	High Similarity	NPC295347
0.8571	High Similarity	NPC183012
0.8556	High Similarity	NPC139692
0.8539	High Similarity	NPC51486
0.8539	High Similarity	NPC477782
0.8523	High Similarity	NPC226863
0.8523	High Similarity	NPC472378
0.8506	High Similarity	NPC474062
0.8495	Intermediate Similarity	NPC23364
0.8495	Intermediate Similarity	NPC222303
0.8488	Intermediate Similarity	NPC82297
0.8478	Intermediate Similarity	NPC134072
0.8478	Intermediate Similarity	NPC242848
0.8478	Intermediate Similarity	NPC234993
0.8462	Intermediate Similarity	NPC474554
0.8452	Intermediate Similarity	NPC271104
0.8444	Intermediate Similarity	NPC186363
0.8444	Intermediate Similarity	NPC233345
0.8444	Intermediate Similarity	NPC477783
0.8444	Intermediate Similarity	NPC303697
0.8434	Intermediate Similarity	NPC475994
0.8434	Intermediate Similarity	NPC471220
0.8427	Intermediate Similarity	NPC474396
0.8427	Intermediate Similarity	NPC470734
0.8427	Intermediate Similarity	NPC50488
0.8427	Intermediate Similarity	NPC251528
0.8404	Intermediate Similarity	NPC472644
0.8391	Intermediate Similarity	NPC52628
0.8391	Intermediate Similarity	NPC179006
0.8391	Intermediate Similarity	NPC42586
0.8391	Intermediate Similarity	NPC473251
0.8391	Intermediate Similarity	NPC474853
0.8387	Intermediate Similarity	NPC474343
0.8387	Intermediate Similarity	NPC69385
0.8387	Intermediate Similarity	NPC475709
0.8372	Intermediate Similarity	NPC42476
0.8372	Intermediate Similarity	NPC22611
0.8372	Intermediate Similarity	NPC474809
0.837	Intermediate Similarity	NPC209355
0.8353	Intermediate Similarity	NPC475944
0.8352	Intermediate Similarity	NPC472303
0.8352	Intermediate Similarity	NPC475657
0.8352	Intermediate Similarity	NPC166346
0.8333	Intermediate Similarity	NPC78973
0.8333	Intermediate Similarity	NPC477147
0.8333	Intermediate Similarity	NPC242767
0.8333	Intermediate Similarity	NPC477149
0.8333	Intermediate Similarity	NPC220454
0.8333	Intermediate Similarity	NPC221111
0.8333	Intermediate Similarity	NPC469595
0.8333	Intermediate Similarity	NPC280149
0.8333	Intermediate Similarity	NPC182136
0.8333	Intermediate Similarity	NPC212679
0.8316	Intermediate Similarity	NPC303559
0.8316	Intermediate Similarity	NPC472643
0.8316	Intermediate Similarity	NPC469657
0.8316	Intermediate Similarity	NPC244456
0.8315	Intermediate Similarity	NPC24816
0.8313	Intermediate Similarity	NPC316500
0.8313	Intermediate Similarity	NPC262747
0.8298	Intermediate Similarity	NPC222011
0.8298	Intermediate Similarity	NPC316598
0.8295	Intermediate Similarity	NPC471219
0.8295	Intermediate Similarity	NPC473226
0.8295	Intermediate Similarity	NPC329692
0.8295	Intermediate Similarity	NPC220478
0.8295	Intermediate Similarity	NPC82979
0.828	Intermediate Similarity	NPC470801
0.828	Intermediate Similarity	NPC240673
0.828	Intermediate Similarity	NPC154526
0.828	Intermediate Similarity	NPC472362
0.828	Intermediate Similarity	NPC472363
0.828	Intermediate Similarity	NPC17578
0.8276	Intermediate Similarity	NPC165064
0.8276	Intermediate Similarity	NPC30486
0.8276	Intermediate Similarity	NPC472326
0.8276	Intermediate Similarity	NPC474865
0.8261	Intermediate Similarity	NPC104925
0.8261	Intermediate Similarity	NPC250075
0.8261	Intermediate Similarity	NPC298973
0.8261	Intermediate Similarity	NPC474555
0.8256	Intermediate Similarity	NPC200513
0.8242	Intermediate Similarity	NPC289479
0.8235	Intermediate Similarity	NPC195424
0.8229	Intermediate Similarity	NPC273005
0.8229	Intermediate Similarity	NPC31058
0.8229	Intermediate Similarity	NPC476081
0.8229	Intermediate Similarity	NPC469606
0.8222	Intermediate Similarity	NPC218927
0.8222	Intermediate Similarity	NPC206001
0.8222	Intermediate Similarity	NPC214387
0.8214	Intermediate Similarity	NPC474816
0.8214	Intermediate Similarity	NPC209135
0.8211	Intermediate Similarity	NPC477720
0.8211	Intermediate Similarity	NPC201406
0.8211	Intermediate Similarity	NPC117685
0.8211	Intermediate Similarity	NPC476767
0.8211	Intermediate Similarity	NPC54705
0.8202	Intermediate Similarity	NPC475678
0.8202	Intermediate Similarity	NPC471796
0.8191	Intermediate Similarity	NPC121402
0.8191	Intermediate Similarity	NPC202705
0.8191	Intermediate Similarity	NPC175351
0.8191	Intermediate Similarity	NPC151681
0.8191	Intermediate Similarity	NPC224356
0.8191	Intermediate Similarity	NPC132753
0.8191	Intermediate Similarity	NPC253826
0.8182	Intermediate Similarity	NPC474860
0.8182	Intermediate Similarity	NPC471300
0.8161	Intermediate Similarity	NPC12283
0.8161	Intermediate Similarity	NPC474193
0.8161	Intermediate Similarity	NPC470948
0.8152	Intermediate Similarity	NPC476598
0.8152	Intermediate Similarity	NPC242069
0.8152	Intermediate Similarity	NPC476597
0.8144	Intermediate Similarity	NPC120321
0.814	Intermediate Similarity	NPC40228
0.814	Intermediate Similarity	NPC473420
0.814	Intermediate Similarity	NPC14203
0.814	Intermediate Similarity	NPC282293
0.814	Intermediate Similarity	NPC229584
0.8132	Intermediate Similarity	NPC469372
0.8132	Intermediate Similarity	NPC158488
0.8132	Intermediate Similarity	NPC469368
0.8132	Intermediate Similarity	NPC8062
0.8132	Intermediate Similarity	NPC310479
0.8125	Intermediate Similarity	NPC471412
0.8118	Intermediate Similarity	NPC89128
0.8118	Intermediate Similarity	NPC308038
0.8118	Intermediate Similarity	NPC471299
0.8111	Intermediate Similarity	NPC136879
0.8111	Intermediate Similarity	NPC277771
0.8111	Intermediate Similarity	NPC472809
0.8111	Intermediate Similarity	NPC477128
0.8111	Intermediate Similarity	NPC472810
0.8111	Intermediate Similarity	NPC477302
0.8111	Intermediate Similarity	NPC472302
0.8111	Intermediate Similarity	NPC215831
0.8111	Intermediate Similarity	NPC193843
0.8111	Intermediate Similarity	NPC249889
0.8105	Intermediate Similarity	NPC98868
0.8105	Intermediate Similarity	NPC478056
0.81	Intermediate Similarity	NPC137911
0.81	Intermediate Similarity	NPC228477
0.8095	Intermediate Similarity	NPC7563
0.8095	Intermediate Similarity	NPC187568
0.8095	Intermediate Similarity	NPC41780
0.8095	Intermediate Similarity	NPC320630
0.8095	Intermediate Similarity	NPC116177
0.809	Intermediate Similarity	NPC261721
0.809	Intermediate Similarity	NPC322159
0.809	Intermediate Similarity	NPC305475
0.809	Intermediate Similarity	NPC131813
0.809	Intermediate Similarity	NPC6979
0.809	Intermediate Similarity	NPC475461
0.809	Intermediate Similarity	NPC202394
0.809	Intermediate Similarity	NPC250981
0.809	Intermediate Similarity	NPC194417
0.8085	Intermediate Similarity	NPC29952
0.8085	Intermediate Similarity	NPC202833
0.8085	Intermediate Similarity	NPC328371
0.8081	Intermediate Similarity	NPC91034
0.8081	Intermediate Similarity	NPC187435
0.8081	Intermediate Similarity	NPC67321
0.8068	Intermediate Similarity	NPC475100
0.8068	Intermediate Similarity	NPC295799
0.8068	Intermediate Similarity	NPC474359
0.8068	Intermediate Similarity	NPC149869
0.8065	Intermediate Similarity	NPC475572
0.8065	Intermediate Similarity	NPC477130
0.8065	Intermediate Similarity	NPC469697
0.8065	Intermediate Similarity	NPC476596
0.8065	Intermediate Similarity	NPC477129
0.8065	Intermediate Similarity	NPC57117
0.8046	Intermediate Similarity	NPC471298
0.8046	Intermediate Similarity	NPC178676

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 NPC312561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1529
0.2-0.3	3647
0.3-0.4	2472
0.4-0.5	812
0.5-0.6	344
0.6-0.7	161
0.7-0.8	22
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
0.8256	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD7640	Approved
0.7835	Intermediate Similarity	NPD7639	Approved
0.7778	Intermediate Similarity	NPD1694	Approved
0.7742	Intermediate Similarity	NPD5785	Approved
0.7732	Intermediate Similarity	NPD4225	Approved
0.7732	Intermediate Similarity	NPD7638	Approved
0.7692	Intermediate Similarity	NPD6684	Approved
0.7692	Intermediate Similarity	NPD7146	Approved
0.7692	Intermediate Similarity	NPD6409	Approved
0.7692	Intermediate Similarity	NPD5330	Approved
0.7692	Intermediate Similarity	NPD7521	Approved
0.7692	Intermediate Similarity	NPD7334	Approved
0.7667	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3133	Approved
0.7667	Intermediate Similarity	NPD3665	Phase 1
0.7667	Intermediate Similarity	NPD3666	Approved
0.764	Intermediate Similarity	NPD3667	Approved
0.7579	Intermediate Similarity	NPD6399	Phase 3
0.7527	Intermediate Similarity	NPD6903	Approved
0.7527	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD3618	Phase 1
0.7476	Intermediate Similarity	NPD6686	Approved
0.7474	Intermediate Similarity	NPD7515	Phase 2
0.7473	Intermediate Similarity	NPD4786	Approved
0.7449	Intermediate Similarity	NPD6084	Phase 2
0.7449	Intermediate Similarity	NPD6083	Phase 2
0.7442	Intermediate Similarity	NPD8039	Approved
0.7423	Intermediate Similarity	NPD5695	Phase 3
0.7423	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7115	Discovery
0.7396	Intermediate Similarity	NPD5778	Approved
0.7396	Intermediate Similarity	NPD5779	Approved
0.7386	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD46	Approved
0.7368	Intermediate Similarity	NPD6698	Approved
0.7363	Intermediate Similarity	NPD7154	Phase 3
0.7363	Intermediate Similarity	NPD5362	Discontinued
0.734	Intermediate Similarity	NPD6672	Approved
0.734	Intermediate Similarity	NPD5737	Approved
0.7312	Intermediate Similarity	NPD4623	Approved
0.7312	Intermediate Similarity	NPD4519	Discontinued
0.7312	Intermediate Similarity	NPD5279	Phase 3
0.7292	Intermediate Similarity	NPD5693	Phase 1
0.7292	Intermediate Similarity	NPD6411	Approved
0.7273	Intermediate Similarity	NPD7902	Approved
0.7263	Intermediate Similarity	NPD5328	Approved
0.7238	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5363	Approved
0.72	Intermediate Similarity	NPD5696	Approved
0.7196	Intermediate Similarity	NPD6053	Discontinued
0.7157	Intermediate Similarity	NPD7632	Discontinued
0.7115	Intermediate Similarity	NPD7128	Approved
0.7115	Intermediate Similarity	NPD6675	Approved
0.7115	Intermediate Similarity	NPD5739	Approved
0.7115	Intermediate Similarity	NPD6402	Approved
0.7113	Intermediate Similarity	NPD6079	Approved
0.7083	Intermediate Similarity	NPD4753	Phase 2
0.7083	Intermediate Similarity	NPD6101	Approved
0.7083	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4221	Approved
0.7065	Intermediate Similarity	NPD4270	Approved
0.7065	Intermediate Similarity	NPD4223	Phase 3
0.7065	Intermediate Similarity	NPD4269	Approved
0.7048	Intermediate Similarity	NPD5701	Approved
0.7048	Intermediate Similarity	NPD5697	Approved
0.7041	Intermediate Similarity	NPD4202	Approved
0.7033	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4695	Discontinued
0.7021	Intermediate Similarity	NPD1696	Phase 3
0.7009	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6371	Approved
0.6981	Remote Similarity	NPD6011	Approved
0.6981	Remote Similarity	NPD6899	Approved
0.6981	Remote Similarity	NPD7320	Approved
0.6981	Remote Similarity	NPD6881	Approved
0.6979	Remote Similarity	NPD5208	Approved
0.697	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7900	Approved
0.6947	Remote Similarity	NPD5786	Approved
0.6939	Remote Similarity	NPD5281	Approved
0.6939	Remote Similarity	NPD7637	Suspended
0.6939	Remote Similarity	NPD5284	Approved
0.6916	Remote Similarity	NPD6373	Approved
0.6916	Remote Similarity	NPD6372	Approved
0.6916	Remote Similarity	NPD6013	Approved
0.6916	Remote Similarity	NPD6014	Approved
0.6916	Remote Similarity	NPD6012	Approved
0.6915	Remote Similarity	NPD3668	Phase 3
0.6915	Remote Similarity	NPD4197	Approved
0.6907	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6673	Approved
0.6907	Remote Similarity	NPD6080	Approved
0.6907	Remote Similarity	NPD6051	Approved
0.6907	Remote Similarity	NPD6904	Approved
0.6882	Remote Similarity	NPD5209	Approved
0.6875	Remote Similarity	NPD3573	Approved
0.6852	Remote Similarity	NPD6883	Approved
0.6852	Remote Similarity	NPD7290	Approved
0.6852	Remote Similarity	NPD7102	Approved
0.6848	Remote Similarity	NPD4822	Approved
0.6848	Remote Similarity	NPD4252	Approved
0.6848	Remote Similarity	NPD4821	Approved
0.6848	Remote Similarity	NPD4820	Approved
0.6848	Remote Similarity	NPD4819	Approved
0.6842	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5329	Approved
0.6837	Remote Similarity	NPD5207	Approved
0.6837	Remote Similarity	NPD5692	Phase 3
0.6832	Remote Similarity	NPD5222	Approved
0.6832	Remote Similarity	NPD4697	Phase 3
0.6832	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5221	Approved
0.6827	Remote Similarity	NPD5211	Phase 2
0.6813	Remote Similarity	NPD4268	Approved
0.6813	Remote Similarity	NPD4271	Approved
0.6813	Remote Similarity	NPD3617	Approved
0.6809	Remote Similarity	NPD5332	Approved
0.6809	Remote Similarity	NPD5331	Approved
0.6796	Remote Similarity	NPD6404	Discontinued
0.6789	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8130	Phase 1
0.6789	Remote Similarity	NPD6847	Approved
0.6789	Remote Similarity	NPD6649	Approved
0.6789	Remote Similarity	NPD6650	Approved
0.6789	Remote Similarity	NPD6869	Approved
0.6789	Remote Similarity	NPD6617	Approved
0.6786	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4790	Discontinued
0.6774	Remote Similarity	NPD5369	Approved
0.6771	Remote Similarity	NPD4138	Approved
0.6771	Remote Similarity	NPD5690	Phase 2
0.6771	Remote Similarity	NPD4688	Approved
0.6771	Remote Similarity	NPD5280	Approved
0.6771	Remote Similarity	NPD6098	Approved
0.6771	Remote Similarity	NPD4690	Approved
0.6771	Remote Similarity	NPD4694	Approved
0.6771	Remote Similarity	NPD5205	Approved
0.6771	Remote Similarity	NPD4693	Phase 3
0.6771	Remote Similarity	NPD4689	Approved
0.6768	Remote Similarity	NPD6050	Approved
0.6768	Remote Similarity	NPD5694	Approved
0.6765	Remote Similarity	NPD5173	Approved
0.6765	Remote Similarity	NPD4755	Approved
0.6733	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5210	Approved
0.6733	Remote Similarity	NPD4629	Approved
0.6729	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6412	Phase 2
0.6727	Remote Similarity	NPD8297	Approved
0.6727	Remote Similarity	NPD6882	Approved
0.6703	Remote Similarity	NPD4756	Discovery
0.6702	Remote Similarity	NPD6435	Approved
0.6698	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD8264	Approved
0.6636	Remote Similarity	NPD6008	Approved
0.6635	Remote Similarity	NPD4696	Approved
0.6635	Remote Similarity	NPD5285	Approved
0.6635	Remote Similarity	NPD5286	Approved
0.6635	Remote Similarity	NPD4700	Approved
0.6634	Remote Similarity	NPD6001	Approved
0.6634	Remote Similarity	NPD5282	Discontinued
0.661	Remote Similarity	NPD7507	Approved
0.66	Remote Similarity	NPD8034	Phase 2
0.66	Remote Similarity	NPD8035	Phase 2
0.66	Remote Similarity	NPD7983	Approved
0.6598	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4249	Approved
0.6574	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5223	Approved
0.6571	Remote Similarity	NPD5344	Discontinued
0.6566	Remote Similarity	NPD1695	Approved
0.6549	Remote Similarity	NPD6274	Approved
0.6549	Remote Similarity	NPD6868	Approved
0.6538	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4251	Approved
0.6531	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4250	Approved
0.6518	Remote Similarity	NPD4632	Approved
0.6512	Remote Similarity	NPD7331	Phase 2
0.6509	Remote Similarity	NPD5226	Approved
0.6509	Remote Similarity	NPD5225	Approved
0.6509	Remote Similarity	NPD4633	Approved
0.6509	Remote Similarity	NPD5224	Approved
0.6505	Remote Similarity	NPD7839	Suspended
0.6495	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6317	Approved
0.6489	Remote Similarity	NPD5368	Approved
0.6489	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4137	Phase 3
0.6471	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4518	Approved
0.6458	Remote Similarity	NPD4788	Approved
0.6458	Remote Similarity	NPD6695	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