NPASS Compound

Structure

CID285086 OpenBabel06191716092D 27 32 0 0 1 0 0 0 0 0999 V2000 -0.2298 -2.9526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5950 -0.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2622 0.0282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9176 -0.3251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6448 -2.6060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2897 -1.4892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5888 -1.4203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0276 -2.2618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6448 -2.2337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.2337 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6448 -0.3723 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.4892 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3003 -1.4702 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3224 -1.6753 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3160 -2.2120 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6448 -0.3723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9333 -1.0669 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2897 -2.2337 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6448 -1.1169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6448 -1.1169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4376 -3.0638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5076 -1.6753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3636 0.0427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0871 -2.4640 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9715 -2.5654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6831 -2.6151 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 2 0 0 0 0 3 4 1 0 0 0 0 3 11 1 0 0 0 0 4 17 1 0 0 0 0 5 10 1 0 0 0 0 5 18 1 0 0 0 0 6 18 1 0 0 0 0 7 17 1 0 0 0 0 7 25 1 0 0 0 0 8 26 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 6 0 0 0 11 20 1 1 0 0 0 11 27 1 0 0 0 0 12 19 1 6 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 1 0 0 0 13 20 1 0 0 0 0 14 19 1 6 0 0 0 14 22 1 0 0 0 0 15 25 1 1 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 23 2 0 0 0 0 16 27 1 0 0 0 0 17 2 1 6 0 0 0 18 24 1 1 0 0 0 19 6 1 6 0 0 0 20 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.17
Volume:	359.396
LogP:	0.827
LogD:	0.494
LogS:	-4.569
# Rotatable Bonds:	0
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	7.141
Fsp3:	0.85
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:	-5.681
MDCK Permeability:	8.090479241218418e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.662

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.375
Plasma Protein Binding (PPB):	41.98573684692383%
Volume Distribution (VD):	0.982
Pgp-substrate:	60.9812126159668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.771
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.407
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	1.822
Half-life (T1/2):	0.209

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.405
Drug-inuced Liver Injury (DILI):	0.191
AMES Toxicity:	0.895
Rat Oral Acute Toxicity:	0.837
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.175
Carcinogencity:	0.886
Eye Corrosion:	0.005
Eye Irritation:	0.024
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC285086

Natural Product ID:	NPC285086
*Common Name:**	WNCXXTYZZHJBOB-FQCJEYDISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WNCXXTYZZHJBOB-FQCJEYDISA-N
Standard InCHI:	InChI=1S/C20H26O7/c1-9-14(22)19-6-18(9,24)5-10(21)12(19)20-8-26-15-13(20)17(2,7-25-15)4-3-11(20)27-16(19)23/h10-15,21-22,24H,1,3-8H2,2H3/t10-,11+,12-,13-,14-,15+,17+,18+,19+,20+/m1/s1
SMILES:	O[C@@H]1C[C@]2(O)C[C@]3([C@@H]1[C@]14CO[C@H]5[C@@H]4[C@](CC[C@@H]1OC3=O)(C)CO5)[C@@H](C2=C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3093770
PubChem CID:	72947649
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19099464]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19697926]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2421673]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	aerial parts	Muli County, Sichuan Province, China	2011-AUG	PMID[24219809]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9599286]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20115	Melampodium argophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19889	Cereus stellatus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19763	Meloidogyne incognita	Species	Meloidogynidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21614	Urceolaria scruposa	Species	Trichodinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17508	Danae racemosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19768	Xylosalsola arbuscula	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20336	Arctotheca calendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20470	Elaeagnus orientalis	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16409	Quercus pedunculata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1558	Ozothamnus obcordatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16021	Boletus bovinus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20543	Psydrax livida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17240	Crematogaster brevis	Species	Formicidae	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[487861]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[487861]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[487861]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[487861]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[487861]

☑ 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 NPC285086 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	290
0.1-0.2	2074
0.2-0.3	6531
0.3-0.4	12038
0.4-0.5	9160
0.5-0.6	6100
0.6-0.7	5030
0.7-0.8	1366
0.8-0.85	73
0.85-0.9	18
0.9-0.95	12
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9712	High Similarity	NPC98633
0.934	High Similarity	NPC255655
0.9327	High Similarity	NPC285927
0.9159	High Similarity	NPC130302
0.9159	High Similarity	NPC124053
0.9074	High Similarity	NPC471251
0.9065	High Similarity	NPC471250
0.8981	High Similarity	NPC49730
0.8981	High Similarity	NPC98069
0.8942	High Similarity	NPC39683
0.8704	High Similarity	NPC88833
0.8704	High Similarity	NPC61071
0.8704	High Similarity	NPC96333
0.8636	High Similarity	NPC42776
0.8611	High Similarity	NPC164600
0.8611	High Similarity	NPC103172
0.8611	High Similarity	NPC37600
0.8559	High Similarity	NPC56025
0.8519	High Similarity	NPC101842
0.8519	High Similarity	NPC244247
0.8411	Intermediate Similarity	NPC253886
0.8411	Intermediate Similarity	NPC121218
0.8407	Intermediate Similarity	NPC102619
0.8393	Intermediate Similarity	NPC329953
0.8378	Intermediate Similarity	NPC469983
0.8364	Intermediate Similarity	NPC471246
0.8361	Intermediate Similarity	NPC42206
0.8319	Intermediate Similarity	NPC40608
0.8318	Intermediate Similarity	NPC108371
0.8288	Intermediate Similarity	NPC469729
0.8288	Intermediate Similarity	NPC232133
0.8288	Intermediate Similarity	NPC469733
0.8273	Intermediate Similarity	NPC295366
0.8273	Intermediate Similarity	NPC12823
0.8257	Intermediate Similarity	NPC139347
0.8241	Intermediate Similarity	NPC295276
0.823	Intermediate Similarity	NPC270586
0.823	Intermediate Similarity	NPC470311
0.823	Intermediate Similarity	NPC272242
0.8226	Intermediate Similarity	NPC475376
0.8214	Intermediate Similarity	NPC469744
0.8198	Intermediate Similarity	NPC469746
0.8182	Intermediate Similarity	NPC202793
0.8182	Intermediate Similarity	NPC88469
0.8182	Intermediate Similarity	NPC13149
0.8182	Intermediate Similarity	NPC47281
0.8165	Intermediate Similarity	NPC170615
0.816	Intermediate Similarity	NPC219058
0.816	Intermediate Similarity	NPC256618
0.8148	Intermediate Similarity	NPC267921
0.8142	Intermediate Similarity	NPC106760
0.8131	Intermediate Similarity	NPC253586
0.8108	Intermediate Similarity	NPC50535
0.8108	Intermediate Similarity	NPC4115
0.8103	Intermediate Similarity	NPC88945
0.8103	Intermediate Similarity	NPC229752
0.8095	Intermediate Similarity	NPC477236
0.8091	Intermediate Similarity	NPC469985
0.8087	Intermediate Similarity	NPC132668
0.808	Intermediate Similarity	NPC470117
0.8073	Intermediate Similarity	NPC471790
0.8073	Intermediate Similarity	NPC46848
0.8073	Intermediate Similarity	NPC14634
0.807	Intermediate Similarity	NPC94650
0.807	Intermediate Similarity	NPC122339
0.807	Intermediate Similarity	NPC63244
0.8062	Intermediate Similarity	NPC5153
0.8062	Intermediate Similarity	NPC48414
0.8056	Intermediate Similarity	NPC474793
0.8037	Intermediate Similarity	NPC193785
0.8034	Intermediate Similarity	NPC473304
0.8034	Intermediate Similarity	NPC78836
0.8034	Intermediate Similarity	NPC470171
0.8033	Intermediate Similarity	NPC471357
0.8033	Intermediate Similarity	NPC146456
0.8033	Intermediate Similarity	NPC469757
0.8033	Intermediate Similarity	NPC117702
0.8018	Intermediate Similarity	NPC472228
0.8018	Intermediate Similarity	NPC472227
0.8	Intermediate Similarity	NPC124544
0.8	Intermediate Similarity	NPC88203
0.8	Intermediate Similarity	NPC475803
0.8	Intermediate Similarity	NPC286519
0.8	Intermediate Similarity	NPC304832
0.8	Intermediate Similarity	NPC76866
0.8	Intermediate Similarity	NPC275990
0.8	Intermediate Similarity	NPC214946
0.8	Intermediate Similarity	NPC473303
0.8	Intermediate Similarity	NPC471244
0.8	Intermediate Similarity	NPC148628
0.8	Intermediate Similarity	NPC243572
0.8	Intermediate Similarity	NPC471245
0.8	Intermediate Similarity	NPC309388
0.8	Intermediate Similarity	NPC246736
0.7982	Intermediate Similarity	NPC180733
0.7982	Intermediate Similarity	NPC473324
0.7982	Intermediate Similarity	NPC37047
0.7982	Intermediate Similarity	NPC471093
0.7982	Intermediate Similarity	NPC41971
0.7982	Intermediate Similarity	NPC471476
0.7982	Intermediate Similarity	NPC85391
0.7967	Intermediate Similarity	NPC473888
0.7966	Intermediate Similarity	NPC471249
0.7965	Intermediate Similarity	NPC224414
0.7965	Intermediate Similarity	NPC473410
0.7965	Intermediate Similarity	NPC471094
0.7965	Intermediate Similarity	NPC469984
0.7965	Intermediate Similarity	NPC63841
0.7951	Intermediate Similarity	NPC273962
0.7951	Intermediate Similarity	NPC47113
0.7951	Intermediate Similarity	NPC174367
0.7946	Intermediate Similarity	NPC28791
0.7937	Intermediate Similarity	NPC477234
0.7931	Intermediate Similarity	NPC9848
0.7931	Intermediate Similarity	NPC312017
0.7931	Intermediate Similarity	NPC94141
0.7928	Intermediate Similarity	NPC266
0.7928	Intermediate Similarity	NPC96217
0.7928	Intermediate Similarity	NPC87927
0.7925	Intermediate Similarity	NPC147272
0.7913	Intermediate Similarity	NPC29505
0.7913	Intermediate Similarity	NPC213320
0.7909	Intermediate Similarity	NPC75941
0.7909	Intermediate Similarity	NPC52899
0.7909	Intermediate Similarity	NPC236585
0.7909	Intermediate Similarity	NPC148279
0.7909	Intermediate Similarity	NPC289148
0.7909	Intermediate Similarity	NPC163963
0.7903	Intermediate Similarity	NPC10823
0.7903	Intermediate Similarity	NPC469753
0.7903	Intermediate Similarity	NPC197707
0.7903	Intermediate Similarity	NPC471358
0.7903	Intermediate Similarity	NPC17896
0.7903	Intermediate Similarity	NPC86159
0.7903	Intermediate Similarity	NPC6108
0.7903	Intermediate Similarity	NPC469752
0.7903	Intermediate Similarity	NPC9499
0.7903	Intermediate Similarity	NPC471360
0.7903	Intermediate Similarity	NPC471352
0.7903	Intermediate Similarity	NPC70542
0.7903	Intermediate Similarity	NPC471359
0.7903	Intermediate Similarity	NPC469751
0.7903	Intermediate Similarity	NPC251866
0.7903	Intermediate Similarity	NPC469755
0.7903	Intermediate Similarity	NPC469754
0.7903	Intermediate Similarity	NPC471361
0.7903	Intermediate Similarity	NPC180079
0.7903	Intermediate Similarity	NPC284406
0.7903	Intermediate Similarity	NPC219085
0.7903	Intermediate Similarity	NPC89514
0.7895	Intermediate Similarity	NPC102741
0.789	Intermediate Similarity	NPC20479
0.789	Intermediate Similarity	NPC38296
0.789	Intermediate Similarity	NPC162459
0.789	Intermediate Similarity	NPC98837
0.789	Intermediate Similarity	NPC471038
0.789	Intermediate Similarity	NPC89099
0.789	Intermediate Similarity	NPC28864
0.789	Intermediate Similarity	NPC38471
0.7879	Intermediate Similarity	NPC194854
0.7879	Intermediate Similarity	NPC48813
0.7876	Intermediate Similarity	NPC86852
0.7876	Intermediate Similarity	NPC471474
0.7876	Intermediate Similarity	NPC186054
0.7876	Intermediate Similarity	NPC251824
0.7863	Intermediate Similarity	NPC79193
0.7863	Intermediate Similarity	NPC117712
0.7863	Intermediate Similarity	NPC17165
0.7863	Intermediate Similarity	NPC471171
0.7857	Intermediate Similarity	NPC474558
0.7857	Intermediate Similarity	NPC84928
0.7857	Intermediate Similarity	NPC88668
0.785	Intermediate Similarity	NPC280804
0.7845	Intermediate Similarity	NPC157929
0.7845	Intermediate Similarity	NPC473352
0.7845	Intermediate Similarity	NPC126691
0.7845	Intermediate Similarity	NPC473397
0.7845	Intermediate Similarity	NPC145625
0.7845	Intermediate Similarity	NPC474927
0.7838	Intermediate Similarity	NPC244969
0.7838	Intermediate Similarity	NPC213528
0.7838	Intermediate Similarity	NPC164551
0.7833	Intermediate Similarity	NPC281840
0.783	Intermediate Similarity	NPC474065
0.783	Intermediate Similarity	NPC475878
0.7826	Intermediate Similarity	NPC474786
0.7826	Intermediate Similarity	NPC320383
0.7826	Intermediate Similarity	NPC101450
0.7826	Intermediate Similarity	NPC137104
0.7823	Intermediate Similarity	NPC311534
0.782	Intermediate Similarity	NPC475462
0.782	Intermediate Similarity	NPC16729
0.7818	Intermediate Similarity	NPC293866
0.7818	Intermediate Similarity	NPC94906
0.7818	Intermediate Similarity	NPC287676
0.781	Intermediate Similarity	NPC194642
0.7807	Intermediate Similarity	NPC55973
0.7807	Intermediate Similarity	NPC89860
0.7807	Intermediate Similarity	NPC218123
0.7807	Intermediate Similarity	NPC469845

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 NPC285086 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	2516
0.2-0.3	3972
0.3-0.4	1555
0.4-0.5	390
0.5-0.6	262
0.6-0.7	145
0.7-0.8	25
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
0.7903	Intermediate Similarity	NPD7319	Approved
0.7742	Intermediate Similarity	NPD8293	Discontinued
0.7705	Intermediate Similarity	NPD6370	Approved
0.768	Intermediate Similarity	NPD7736	Approved
0.7661	Intermediate Similarity	NPD7507	Approved
0.7627	Intermediate Similarity	NPD8133	Approved
0.76	Intermediate Similarity	NPD7078	Approved
0.7581	Intermediate Similarity	NPD7492	Approved
0.7541	Intermediate Similarity	NPD6054	Approved
0.7541	Intermediate Similarity	NPD6059	Approved
0.752	Intermediate Similarity	NPD6616	Approved
0.748	Intermediate Similarity	NPD6015	Approved
0.748	Intermediate Similarity	NPD6016	Approved
0.7419	Intermediate Similarity	NPD5988	Approved
0.735	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6008	Approved
0.7281	Intermediate Similarity	NPD1700	Approved
0.725	Intermediate Similarity	NPD6882	Approved
0.7236	Intermediate Similarity	NPD7327	Approved
0.7236	Intermediate Similarity	NPD7328	Approved
0.7203	Intermediate Similarity	NPD7320	Approved
0.7179	Intermediate Similarity	NPD7128	Approved
0.7179	Intermediate Similarity	NPD6675	Approved
0.7179	Intermediate Similarity	NPD5739	Approved
0.7179	Intermediate Similarity	NPD6402	Approved
0.7177	Intermediate Similarity	NPD7516	Approved
0.7154	Intermediate Similarity	NPD6009	Approved
0.7154	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.712	Intermediate Similarity	NPD6319	Approved
0.7119	Intermediate Similarity	NPD5697	Approved
0.7119	Intermediate Similarity	NPD6412	Phase 2
0.7119	Intermediate Similarity	NPD5701	Approved
0.7094	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8328	Phase 3
0.7063	Intermediate Similarity	NPD8335	Approved
0.7063	Intermediate Similarity	NPD8380	Approved
0.7063	Intermediate Similarity	NPD8378	Approved
0.7063	Intermediate Similarity	NPD8296	Approved
0.7063	Intermediate Similarity	NPD8379	Approved
0.7063	Intermediate Similarity	NPD8033	Approved
0.7059	Intermediate Similarity	NPD6899	Approved
0.7059	Intermediate Similarity	NPD6881	Approved
0.7027	Intermediate Similarity	NPD8035	Phase 2
0.7027	Intermediate Similarity	NPD8034	Phase 2
0.7025	Intermediate Similarity	NPD6650	Approved
0.7025	Intermediate Similarity	NPD6649	Approved
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6033	Approved
0.7	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.6984	Remote Similarity	NPD8377	Approved
0.6984	Remote Similarity	NPD8294	Approved
0.6942	Remote Similarity	NPD7290	Approved
0.6942	Remote Similarity	NPD6883	Approved
0.6942	Remote Similarity	NPD7102	Approved
0.6929	Remote Similarity	NPD8517	Approved
0.6929	Remote Similarity	NPD8516	Approved
0.6929	Remote Similarity	NPD8515	Approved
0.6929	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD5211	Phase 2
0.6917	Remote Similarity	NPD6686	Approved
0.6917	Remote Similarity	NPD6011	Approved
0.6911	Remote Similarity	NPD4632	Approved
0.6897	Remote Similarity	NPD7639	Approved
0.6897	Remote Similarity	NPD7640	Approved
0.6885	Remote Similarity	NPD8130	Phase 1
0.6885	Remote Similarity	NPD6847	Approved
0.6885	Remote Similarity	NPD6617	Approved
0.6885	Remote Similarity	NPD6869	Approved
0.687	Remote Similarity	NPD4755	Approved
0.6829	Remote Similarity	NPD8297	Approved
0.681	Remote Similarity	NPD7638	Approved
0.6807	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5141	Approved
0.6807	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4634	Approved
0.6789	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5285	Approved
0.6752	Remote Similarity	NPD4700	Approved
0.6752	Remote Similarity	NPD5286	Approved
0.6752	Remote Similarity	NPD4696	Approved
0.6748	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6053	Discontinued
0.6692	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5226	Approved
0.6639	Remote Similarity	NPD5224	Approved
0.6639	Remote Similarity	NPD5225	Approved
0.6639	Remote Similarity	NPD4633	Approved
0.6614	Remote Similarity	NPD7115	Discovery
0.6585	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5175	Approved
0.6583	Remote Similarity	NPD5174	Approved
0.6581	Remote Similarity	NPD6083	Phase 2
0.6581	Remote Similarity	NPD6084	Phase 2
0.6565	Remote Similarity	NPD7604	Phase 2
0.6555	Remote Similarity	NPD5223	Approved
0.6552	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5696	Approved
0.6525	Remote Similarity	NPD4225	Approved
0.6522	Remote Similarity	NPD4202	Approved
0.6512	Remote Similarity	NPD7100	Approved
0.6512	Remote Similarity	NPD7101	Approved
0.65	Remote Similarity	NPD7632	Discontinued
0.6484	Remote Similarity	NPD6317	Approved
0.6481	Remote Similarity	NPD6928	Phase 2
0.6476	Remote Similarity	NPD3702	Approved
0.6475	Remote Similarity	NPD4767	Approved
0.6475	Remote Similarity	NPD4768	Approved
0.6466	Remote Similarity	NPD6336	Discontinued
0.6449	Remote Similarity	NPD6114	Approved
0.6449	Remote Similarity	NPD6118	Approved
0.6449	Remote Similarity	NPD6115	Approved
0.6449	Remote Similarity	NPD6697	Approved
0.6446	Remote Similarity	NPD4754	Approved
0.6435	Remote Similarity	NPD7637	Suspended
0.6435	Remote Similarity	NPD6411	Approved
0.6434	Remote Similarity	NPD6314	Approved
0.6434	Remote Similarity	NPD6313	Approved
0.6434	Remote Similarity	NPD6335	Approved
0.6418	Remote Similarity	NPD8074	Phase 3
0.6412	Remote Similarity	NPD6909	Approved
0.6412	Remote Similarity	NPD6908	Approved
0.641	Remote Similarity	NPD5695	Phase 3
0.6404	Remote Similarity	NPD5328	Approved
0.6397	Remote Similarity	NPD5956	Approved
0.6379	Remote Similarity	NPD5778	Approved
0.6379	Remote Similarity	NPD5779	Approved
0.6379	Remote Similarity	NPD8171	Discontinued
0.6371	Remote Similarity	NPD5128	Approved
0.6371	Remote Similarity	NPD4730	Approved
0.6371	Remote Similarity	NPD4729	Approved
0.6356	Remote Similarity	NPD4697	Phase 3
0.6355	Remote Similarity	NPD6116	Phase 1
0.6325	Remote Similarity	NPD6001	Approved
0.6306	Remote Similarity	NPD4788	Approved
0.6303	Remote Similarity	NPD7902	Approved
0.6293	Remote Similarity	NPD6079	Approved
0.629	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD3618	Phase 1
0.6273	Remote Similarity	NPD1779	Approved
0.6273	Remote Similarity	NPD1780	Approved
0.627	Remote Similarity	NPD5251	Approved
0.627	Remote Similarity	NPD5250	Approved
0.627	Remote Similarity	NPD5248	Approved
0.627	Remote Similarity	NPD5249	Phase 3
0.627	Remote Similarity	NPD5247	Approved
0.6262	Remote Similarity	NPD6117	Approved
0.6261	Remote Similarity	NPD4753	Phase 2
0.6261	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6101	Approved
0.622	Remote Similarity	NPD5215	Approved
0.622	Remote Similarity	NPD5216	Approved
0.622	Remote Similarity	NPD5217	Approved
0.6218	Remote Similarity	NPD5221	Approved
0.6218	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5222	Approved
0.6197	Remote Similarity	NPD6334	Approved
0.6197	Remote Similarity	NPD6333	Approved
0.6186	Remote Similarity	NPD5282	Discontinued
0.6186	Remote Similarity	NPD7748	Approved
0.6174	Remote Similarity	NPD6903	Approved
0.6168	Remote Similarity	NPD3703	Phase 2
0.6167	Remote Similarity	NPD5173	Approved
0.6161	Remote Similarity	NPD3669	Approved
0.6161	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5281	Approved
0.6154	Remote Similarity	NPD5284	Approved
0.6154	Remote Similarity	NPD7515	Phase 2
0.6142	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6371	Approved
0.6142	Remote Similarity	NPD5135	Approved
0.6142	Remote Similarity	NPD5169	Approved
0.614	Remote Similarity	NPD5330	Approved
0.614	Remote Similarity	NPD7334	Approved
0.614	Remote Similarity	NPD6684	Approved
0.614	Remote Similarity	NPD7146	Approved
0.614	Remote Similarity	NPD4249	Approved
0.614	Remote Similarity	NPD6409	Approved
0.614	Remote Similarity	NPD7521	Approved
0.614	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD5210	Approved
0.6134	Remote Similarity	NPD4629	Approved
0.6134	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4786	Approved
0.6106	Remote Similarity	NPD3666	Approved
0.6106	Remote Similarity	NPD3665	Phase 1
0.6106	Remote Similarity	NPD3133	Approved
0.6106	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD5127	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