NPASS Compound

Structure

CID215364 OpenBabel06191716002D 26 28 0 0 1 0 0 0 0 0999 V2000 1.9970 0.7552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2959 1.7370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9966 3.0613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6655 2.3055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6626 1.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3309 1.9214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6626 1.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3314 -0.3844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6623 -0.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6652 0.7684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9969 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 1.0060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 1.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6654 0.0001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3279 0.7684 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3281 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5103 0.3845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3328 0.5762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9965 2.3057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2789 0.3847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1013 0.5761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3422 3.4391 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 4.0589 -0.2372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3422 2.6835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 2 0 0 0 0 4 5 1 0 0 0 0 4 7 2 0 0 0 0 5 14 1 0 0 0 0 6 8 1 0 0 0 0 7 20 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 10 12 2 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 9 1 1 0 0 0 15 24 1 0 0 0 0 16 6 1 6 0 0 0 16 17 1 0 0 0 0 17 10 1 1 0 0 0 17 25 1 0 0 0 0 18 21 2 0 0 0 0 18 25 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 3 1 6 0 0 0 20 26 1 0 0 0 0 23 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.16
Volume:	365.729
LogP:	1.773
LogD:	1.916
LogS:	-3.545
# Rotatable Bonds:	1
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.261
Synthetic Accessibility Score:	6.055
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.092
MDCK Permeability:	1.3664624930243008e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.837
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	88.78034210205078%
Volume Distribution (VD):	0.356
Pgp-substrate:	2.6518614292144775%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.648
CYP2C19-inhibitor:	0.155
CYP2C19-substrate:	0.185
CYP2C9-inhibitor:	0.497
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.353
CYP3A4-inhibitor:	0.643
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	3.259
Half-life (T1/2):	0.783

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.597
Drug-inuced Liver Injury (DILI):	0.511
AMES Toxicity:	0.595
Rat Oral Acute Toxicity:	0.898
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.55
Carcinogencity:	0.696
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC215364

Natural Product ID:	NPC215364
*Common Name:**	WSXLFQQZQWNCIS-OPOAMCISSA-N
IUPAC Name:	n.a.
Synonyms:	4alpha-Hydroperoxy-5-enovatodiolide
Standard InCHIKey:	WSXLFQQZQWNCIS-OPOAMCISSA-N
Standard InCHI:	InChI=1S/C20H24O6/c1-12-9-15-11-14(19(22)24-15)5-4-7-20(3,26-23)8-6-16-13(2)18(21)25-17(16)10-12/h4,7,10-11,15-17,23H,2,5-6,8-9H2,1,3H3/b7-4+,12-10+/t15-,16-,17+,20-/m1/s1
SMILES:	C/C/1=C[C@H]2[C@H](CC[C@@](C)(/C=C/CC3=C[C@@H](C1)OC3=O)OO)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512307
PubChem CID:	24970923
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	heartwood	n.a.	n.a.	PMID[16643064]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18547115]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19099464]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
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]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	roots	Khon Kaen, Thailand	2009-DEC	PMID[25537111]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9599286]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9613	Anisomeles indica	Species	Lamiaceae	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]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20115	Melampodium argophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19889	Cereus stellatus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21614	Urceolaria scruposa	Species	Trichodinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19763	Meloidogyne incognita	Species	Meloidogynidae	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]
NPO20336	Arctotheca calendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	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]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	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	9

Activity Type	# Activity
Cell Line	4
CELL-LINE	2
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1200.0	nM	PMID[568414]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1550.0	nM	PMID[568414]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	900.0	nM	PMID[568414]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	30300.0	nM	PMID[568415]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	11900.0	nM	PMID[568413]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	>	100000.0	nM	PMID[568413]
NPT610	Others	Molecular identity unknown		IC50	=	7600.0	nM	PMID[568415]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	17900.0	nM	PMID[568415]
NPT27	Others	Unspecified		IC50	>	55600.0	nM	PMID[568415]

☑ 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 NPC215364 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	1236
0.2-0.3	5196
0.3-0.4	12545
0.4-0.5	12203
0.5-0.6	6821
0.6-0.7	3409
0.7-0.8	952
0.8-0.85	134
0.85-0.9	10
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC160138
0.939	High Similarity	NPC284902
0.9048	High Similarity	NPC475703
0.9024	High Similarity	NPC250315
0.8861	High Similarity	NPC123360
0.8837	High Similarity	NPC295312
0.8736	High Similarity	NPC144133
0.8736	High Similarity	NPC179394
0.8736	High Similarity	NPC475855
0.8608	High Similarity	NPC476355
0.8571	High Similarity	NPC471462
0.8556	High Similarity	NPC304886
0.8554	High Similarity	NPC325031
0.8488	Intermediate Similarity	NPC50637
0.8452	Intermediate Similarity	NPC173609
0.8444	Intermediate Similarity	NPC477131
0.8444	Intermediate Similarity	NPC473330
0.8444	Intermediate Similarity	NPC473316
0.8444	Intermediate Similarity	NPC474338
0.8444	Intermediate Similarity	NPC140543
0.8415	Intermediate Similarity	NPC93763
0.8415	Intermediate Similarity	NPC267231
0.8415	Intermediate Similarity	NPC108816
0.8409	Intermediate Similarity	NPC166919
0.8391	Intermediate Similarity	NPC231889
0.8375	Intermediate Similarity	NPC140287
0.8372	Intermediate Similarity	NPC235792
0.8354	Intermediate Similarity	NPC163003
0.8353	Intermediate Similarity	NPC170286
0.8353	Intermediate Similarity	NPC272814
0.8353	Intermediate Similarity	NPC318468
0.8352	Intermediate Similarity	NPC474947
0.8333	Intermediate Similarity	NPC42470
0.8333	Intermediate Similarity	NPC125674
0.8333	Intermediate Similarity	NPC475657
0.8333	Intermediate Similarity	NPC141810
0.8333	Intermediate Similarity	NPC81419
0.8333	Intermediate Similarity	NPC179746
0.8333	Intermediate Similarity	NPC475838
0.8333	Intermediate Similarity	NPC228451
0.8315	Intermediate Similarity	NPC62815
0.8315	Intermediate Similarity	NPC51004
0.8315	Intermediate Similarity	NPC312042
0.8313	Intermediate Similarity	NPC178277
0.8295	Intermediate Similarity	NPC202672
0.8293	Intermediate Similarity	NPC57744
0.8293	Intermediate Similarity	NPC476794
0.8293	Intermediate Similarity	NPC470240
0.8276	Intermediate Similarity	NPC64153
0.8261	Intermediate Similarity	NPC172998
0.8261	Intermediate Similarity	NPC299396
0.8261	Intermediate Similarity	NPC301596
0.8242	Intermediate Similarity	NPC476267
0.8242	Intermediate Similarity	NPC474247
0.8222	Intermediate Similarity	NPC30515
0.8222	Intermediate Similarity	NPC12172
0.8222	Intermediate Similarity	NPC208886
0.8222	Intermediate Similarity	NPC133698
0.8202	Intermediate Similarity	NPC307411
0.8193	Intermediate Similarity	NPC128276
0.8171	Intermediate Similarity	NPC235906
0.8161	Intermediate Similarity	NPC474547
0.8152	Intermediate Similarity	NPC234339
0.8152	Intermediate Similarity	NPC273197
0.8152	Intermediate Similarity	NPC67584
0.814	Intermediate Similarity	NPC475947
0.8132	Intermediate Similarity	NPC135776
0.8132	Intermediate Similarity	NPC475912
0.8132	Intermediate Similarity	NPC476300
0.8118	Intermediate Similarity	NPC301477
0.8118	Intermediate Similarity	NPC281949
0.8118	Intermediate Similarity	NPC25684
0.8118	Intermediate Similarity	NPC471325
0.8111	Intermediate Similarity	NPC476004
0.8111	Intermediate Similarity	NPC473448
0.8111	Intermediate Similarity	NPC474761
0.8111	Intermediate Similarity	NPC37607
0.8111	Intermediate Similarity	NPC301969
0.8111	Intermediate Similarity	NPC475748
0.8095	Intermediate Similarity	NPC617
0.8095	Intermediate Similarity	NPC270126
0.809	Intermediate Similarity	NPC91248
0.8085	Intermediate Similarity	NPC187268
0.8085	Intermediate Similarity	NPC473326
0.8072	Intermediate Similarity	NPC7563
0.8072	Intermediate Similarity	NPC141789
0.8072	Intermediate Similarity	NPC41780
0.8072	Intermediate Similarity	NPC116177
0.8072	Intermediate Similarity	NPC187568
0.8072	Intermediate Similarity	NPC320630
0.8072	Intermediate Similarity	NPC65603
0.8072	Intermediate Similarity	NPC171204
0.8072	Intermediate Similarity	NPC476028
0.8072	Intermediate Similarity	NPC97516
0.8068	Intermediate Similarity	NPC107787
0.8068	Intermediate Similarity	NPC67493
0.8068	Intermediate Similarity	NPC305475
0.8068	Intermediate Similarity	NPC475461
0.8065	Intermediate Similarity	NPC279621
0.8065	Intermediate Similarity	NPC230800
0.8065	Intermediate Similarity	NPC213078
0.8046	Intermediate Similarity	NPC115786
0.8043	Intermediate Similarity	NPC81386
0.8043	Intermediate Similarity	NPC198853
0.8043	Intermediate Similarity	NPC474035
0.8043	Intermediate Similarity	NPC262133
0.8043	Intermediate Similarity	NPC470013
0.8043	Intermediate Similarity	NPC127019
0.8043	Intermediate Similarity	NPC470010
0.8043	Intermediate Similarity	NPC323008
0.8025	Intermediate Similarity	NPC269206
0.8025	Intermediate Similarity	NPC58956
0.8025	Intermediate Similarity	NPC295633
0.8022	Intermediate Similarity	NPC300312
0.8022	Intermediate Similarity	NPC184463
0.8022	Intermediate Similarity	NPC131209
0.8022	Intermediate Similarity	NPC20713
0.8022	Intermediate Similarity	NPC111114
0.8022	Intermediate Similarity	NPC261607
0.8021	Intermediate Similarity	NPC189609
0.8021	Intermediate Similarity	NPC140591
0.8021	Intermediate Similarity	NPC197835
0.8021	Intermediate Similarity	NPC303653
0.8021	Intermediate Similarity	NPC291500
0.8	Intermediate Similarity	NPC281132
0.8	Intermediate Similarity	NPC474032
0.8	Intermediate Similarity	NPC151770
0.8	Intermediate Similarity	NPC302426
0.7979	Intermediate Similarity	NPC161493
0.7978	Intermediate Similarity	NPC72513
0.7957	Intermediate Similarity	NPC471141
0.7957	Intermediate Similarity	NPC14961
0.7957	Intermediate Similarity	NPC36954
0.7957	Intermediate Similarity	NPC52044
0.7957	Intermediate Similarity	NPC270013
0.7957	Intermediate Similarity	NPC213698
0.7955	Intermediate Similarity	NPC21469
0.7955	Intermediate Similarity	NPC78089
0.7955	Intermediate Similarity	NPC255307
0.7935	Intermediate Similarity	NPC476049
0.7935	Intermediate Similarity	NPC212486
0.7931	Intermediate Similarity	NPC473390
0.7931	Intermediate Similarity	NPC169575
0.7931	Intermediate Similarity	NPC131669
0.7931	Intermediate Similarity	NPC40746
0.7931	Intermediate Similarity	NPC170377
0.7931	Intermediate Similarity	NPC39588
0.7927	Intermediate Similarity	NPC474758
0.7927	Intermediate Similarity	NPC259599
0.7927	Intermediate Similarity	NPC117746
0.7927	Intermediate Similarity	NPC294434
0.7927	Intermediate Similarity	NPC15499
0.7917	Intermediate Similarity	NPC150923
0.7917	Intermediate Similarity	NPC474742
0.7912	Intermediate Similarity	NPC329857
0.7912	Intermediate Similarity	NPC80875
0.7912	Intermediate Similarity	NPC469718
0.7912	Intermediate Similarity	NPC473619
0.7912	Intermediate Similarity	NPC106510
0.7912	Intermediate Similarity	NPC71533
0.7895	Intermediate Similarity	NPC208233
0.7895	Intermediate Similarity	NPC279561
0.7889	Intermediate Similarity	NPC469653
0.7889	Intermediate Similarity	NPC226863
0.7889	Intermediate Similarity	NPC471047
0.7889	Intermediate Similarity	NPC469631
0.7889	Intermediate Similarity	NPC469628
0.7889	Intermediate Similarity	NPC475906
0.7882	Intermediate Similarity	NPC63649
0.7882	Intermediate Similarity	NPC470239
0.7882	Intermediate Similarity	NPC472965
0.7882	Intermediate Similarity	NPC182550
0.7882	Intermediate Similarity	NPC264227
0.7882	Intermediate Similarity	NPC470244
0.7875	Intermediate Similarity	NPC265574
0.7872	Intermediate Similarity	NPC476315
0.7872	Intermediate Similarity	NPC35498
0.7865	Intermediate Similarity	NPC38576
0.7865	Intermediate Similarity	NPC162071
0.7865	Intermediate Similarity	NPC114694
0.7865	Intermediate Similarity	NPC261253
0.7865	Intermediate Similarity	NPC142117
0.7865	Intermediate Similarity	NPC261721
0.7865	Intermediate Similarity	NPC279267
0.7865	Intermediate Similarity	NPC62118
0.7865	Intermediate Similarity	NPC231096
0.7865	Intermediate Similarity	NPC240695
0.7865	Intermediate Similarity	NPC150755
0.7865	Intermediate Similarity	NPC232555
0.7865	Intermediate Similarity	NPC107717
0.7865	Intermediate Similarity	NPC69082
0.7865	Intermediate Similarity	NPC122502
0.7865	Intermediate Similarity	NPC279859
0.7865	Intermediate Similarity	NPC475581
0.7865	Intermediate Similarity	NPC171174
0.7865	Intermediate Similarity	NPC474045
0.7849	Intermediate Similarity	NPC167219
0.7848	Intermediate Similarity	NPC194871
0.7841	Intermediate Similarity	NPC191476
0.7841	Intermediate Similarity	NPC476804

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 NPC215364 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1733
0.2-0.3	3881
0.3-0.4	2284
0.4-0.5	697
0.5-0.6	312
0.6-0.7	65
0.7-0.8	9
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
0.7802	Intermediate Similarity	NPD1695	Approved
0.7753	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD1694	Approved
0.734	Intermediate Similarity	NPD46	Approved
0.734	Intermediate Similarity	NPD6698	Approved
0.7158	Intermediate Similarity	NPD7838	Discovery
0.7158	Intermediate Similarity	NPD5785	Approved
0.7113	Intermediate Similarity	NPD5282	Discontinued
0.7	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5363	Approved
0.6981	Remote Similarity	NPD6371	Approved
0.6957	Remote Similarity	NPD5362	Discontinued
0.6957	Remote Similarity	NPD7154	Phase 3
0.6951	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4249	Approved
0.6848	Remote Similarity	NPD5209	Approved
0.6842	Remote Similarity	NPD4250	Approved
0.6842	Remote Similarity	NPD4251	Approved
0.6792	Remote Similarity	NPD6686	Approved
0.6759	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5369	Approved
0.6735	Remote Similarity	NPD7983	Approved
0.6697	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6632	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8039	Approved
0.6604	Remote Similarity	NPD6008	Approved
0.6602	Remote Similarity	NPD7640	Approved
0.6602	Remote Similarity	NPD7639	Approved
0.6602	Remote Similarity	NPD6648	Approved
0.6562	Remote Similarity	NPD5786	Approved
0.6538	Remote Similarity	NPD5344	Discontinued
0.6452	Remote Similarity	NPD4822	Approved
0.6452	Remote Similarity	NPD4821	Approved
0.6452	Remote Similarity	NPD4252	Approved
0.6452	Remote Similarity	NPD4819	Approved
0.6452	Remote Similarity	NPD4820	Approved
0.6452	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5332	Approved
0.6421	Remote Similarity	NPD5331	Approved
0.6413	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4790	Discontinued
0.6364	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6435	Approved
0.6316	Remote Similarity	NPD7115	Discovery
0.6311	Remote Similarity	NPD7839	Suspended
0.63	Remote Similarity	NPD5207	Approved
0.6273	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6903	Approved
0.6238	Remote Similarity	NPD5693	Phase 1
0.6237	Remote Similarity	NPD4271	Approved
0.6237	Remote Similarity	NPD4268	Approved
0.6224	Remote Similarity	NPD7334	Approved
0.6224	Remote Similarity	NPD6684	Approved
0.6224	Remote Similarity	NPD6409	Approved
0.6224	Remote Similarity	NPD7146	Approved
0.6224	Remote Similarity	NPD5330	Approved
0.6224	Remote Similarity	NPD7521	Approved
0.6214	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6101	Approved
0.62	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6399	Phase 3
0.6129	Remote Similarity	NPD4756	Discovery
0.6105	Remote Similarity	NPD5368	Approved
0.6102	Remote Similarity	NPD8513	Phase 3
0.6102	Remote Similarity	NPD8517	Approved
0.6102	Remote Similarity	NPD8515	Approved
0.6102	Remote Similarity	NPD8516	Approved
0.61	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5737	Approved
0.61	Remote Similarity	NPD6672	Approved
0.6078	Remote Similarity	NPD6411	Approved
0.6078	Remote Similarity	NPD7637	Suspended
0.6071	Remote Similarity	NPD2067	Discontinued
0.6058	Remote Similarity	NPD5695	Phase 3
0.604	Remote Similarity	NPD5370	Suspended
0.6038	Remote Similarity	NPD5696	Approved
0.6033	Remote Similarity	NPD7507	Approved
0.6023	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7632	Discontinued
0.6018	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3573	Approved
0.5962	Remote Similarity	NPD6001	Approved
0.5962	Remote Similarity	NPD7748	Approved
0.5962	Remote Similarity	NPD7900	Approved
0.5962	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5697	Approved
0.5943	Remote Similarity	NPD6084	Phase 2
0.5943	Remote Similarity	NPD6083	Phase 2
0.5943	Remote Similarity	NPD7902	Approved
0.5922	Remote Similarity	NPD5284	Approved
0.5922	Remote Similarity	NPD5281	Approved
0.5922	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5694	Approved
0.592	Remote Similarity	NPD7260	Phase 2
0.5918	Remote Similarity	NPD6110	Phase 1
0.5913	Remote Similarity	NPD4632	Approved
0.5909	Remote Similarity	NPD7331	Phase 2
0.59	Remote Similarity	NPD6422	Discontinued
0.5893	Remote Similarity	NPD6011	Approved
0.5893	Remote Similarity	NPD6881	Approved
0.5893	Remote Similarity	NPD6899	Approved
0.5887	Remote Similarity	NPD7319	Approved
0.5882	Remote Similarity	NPD6673	Approved
0.5882	Remote Similarity	NPD6051	Approved
0.5882	Remote Similarity	NPD6904	Approved
0.5882	Remote Similarity	NPD6080	Approved
0.5877	Remote Similarity	NPD6650	Approved
0.5877	Remote Similarity	NPD2204	Approved
0.5877	Remote Similarity	NPD6649	Approved
0.5868	Remote Similarity	NPD7642	Approved
0.5854	Remote Similarity	NPD8074	Phase 3
0.5841	Remote Similarity	NPD6013	Approved
0.5841	Remote Similarity	NPD6014	Approved
0.5841	Remote Similarity	NPD6012	Approved
0.5825	Remote Similarity	NPD5692	Phase 3
0.582	Remote Similarity	NPD7492	Approved
0.5814	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD7341	Phase 2
0.5789	Remote Similarity	NPD6883	Approved
0.5789	Remote Similarity	NPD7290	Approved
0.5789	Remote Similarity	NPD7102	Approved
0.5784	Remote Similarity	NPD5208	Approved
0.5773	Remote Similarity	NPD4695	Discontinued
0.5772	Remote Similarity	NPD6616	Approved
0.5769	Remote Similarity	NPD6050	Approved
0.5769	Remote Similarity	NPD7515	Phase 2
0.5763	Remote Similarity	NPD7500	Approved
0.5763	Remote Similarity	NPD6009	Approved
0.5755	Remote Similarity	NPD4629	Approved
0.5755	Remote Similarity	NPD5210	Approved
0.5752	Remote Similarity	NPD7320	Approved
0.575	Remote Similarity	NPD6927	Phase 3
0.575	Remote Similarity	NPD6054	Approved
0.575	Remote Similarity	NPD6319	Approved
0.5748	Remote Similarity	NPD6845	Suspended
0.5743	Remote Similarity	NPD3618	Phase 1
0.5743	Remote Similarity	NPD4519	Discontinued
0.5743	Remote Similarity	NPD4623	Approved
0.5739	Remote Similarity	NPD6847	Approved
0.5739	Remote Similarity	NPD6617	Approved
0.5739	Remote Similarity	NPD8130	Phase 1
0.5739	Remote Similarity	NPD6869	Approved
0.5738	Remote Similarity	NPD7830	Approved
0.5738	Remote Similarity	NPD7829	Approved
0.573	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD7328	Approved
0.5714	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD4211	Phase 1
0.5714	Remote Similarity	NPD7327	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD7641	Discontinued
0.5714	Remote Similarity	NPD6402	Approved
0.5702	Remote Similarity	NPD6372	Approved
0.5702	Remote Similarity	NPD8033	Approved
0.5702	Remote Similarity	NPD5983	Phase 2
0.5702	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6016	Approved
0.5702	Remote Similarity	NPD6015	Approved
0.5702	Remote Similarity	NPD6373	Approved
0.5701	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.57	Remote Similarity	NPD3666	Approved
0.57	Remote Similarity	NPD3668	Phase 3
0.57	Remote Similarity	NPD3665	Phase 1
0.57	Remote Similarity	NPD3133	Approved
0.5698	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.569	Remote Similarity	NPD8297	Approved
0.569	Remote Similarity	NPD6882	Approved
0.5682	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD3197	Phase 1
0.568	Remote Similarity	NPD7736	Approved
0.5676	Remote Similarity	NPD6052	Approved
0.5676	Remote Similarity	NPD6647	Phase 2
0.5667	Remote Similarity	NPD7516	Approved
0.5664	Remote Similarity	NPD5701	Approved
0.5664	Remote Similarity	NPD6412	Phase 2
0.5657	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD3667	Approved
0.5656	Remote Similarity	NPD6370	Approved
0.5656	Remote Similarity	NPD5988	Approved
0.5652	Remote Similarity	NPD6420	Discontinued
0.5645	Remote Similarity	NPD8273	Phase 1
0.5645	Remote Similarity	NPD8451	Approved
0.562	Remote Similarity	NPD8294	Approved
0.562	Remote Similarity	NPD8377	Approved
0.5619	Remote Similarity	NPD6079	Approved
0.5614	Remote Similarity	NPD5345	Clinical (unspecified phase)

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