NPASS Compound

Structure

NPC211920 OpenBabel07101718292D 42 47 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3660 2.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2218 2.8479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 20 2 0 0 0 0 3 31 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 34 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 17 33 1 0 0 0 0 18 22 2 0 0 0 0 18 34 1 0 0 0 0 19 33 1 0 0 0 0 19 39 1 0 0 0 0 20 30 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 6 0 0 0 23 31 1 0 0 0 0 24 31 1 1 0 0 0 24 40 1 0 0 0 0 25 35 2 0 0 0 0 25 39 1 0 0 0 0 26 27 1 0 0 0 0 26 32 1 1 0 0 0 26 36 1 0 0 0 0 27 30 1 6 0 0 0 27 41 1 0 0 0 0 28 37 2 0 0 0 0 28 41 1 0 0 0 0 29 38 2 0 0 0 0 29 40 1 0 0 0 0 30 2 1 6 0 0 0 31 32 1 6 0 0 0 32 4 1 6 0 0 0 32 42 1 0 0 0 0 33 16 1 1 0 0 0 33 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	575.25
Volume:	582.939
LogP:	3.751
LogD:	2.768
LogS:	-4.511
# Rotatable Bonds:	6
TPSA:	121.25
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	5.389
Fsp3:	0.515
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.391
MDCK Permeability:	3.2643329177517444e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.88
Plasma Protein Binding (PPB):	84.37376403808594%
Volume Distribution (VD):	1.502
Pgp-substrate:	9.83314037322998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.178
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.421
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.435
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.225
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.371

ADMET: Excretion

Clearance (CL):	12.411
Half-life (T1/2):	0.601

ADMET: Toxicity

hERG Blockers:	0.865
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.708
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.233
Carcinogencity:	0.174
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.878

Download Data

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

Natural Product: NPC211920

Natural Product ID:	NPC211920
*Common Name:**	Scutehenanine C
IUPAC Name:	[(1S,3S,4aR,5S,6R,6aR,10aS,10bS)-6-benzoyloxy-5-hydroxy-4a,6a,10b-trimethyl-7-methylidene-2'-oxospiro[1,2,5,6,8,9,10,10a-octahydrobenzo[f]chromene-3,4'-oxolane]-1-yl] pyridine-3-carboxylate
Synonyms:	Scutehenanine C
Standard InCHIKey:	GMMYKYNDSYLONO-GRTFKUIQSA-N
Standard InCHI:	InChI=1S/C33H37NO8/c1-20-10-8-14-23-30(20,2)27(41-28(37)21-11-6-5-7-12-21)26(36)32(4)31(23,3)24(16-33(42-32)17-25(35)39-19-33)40-29(38)22-13-9-15-34-18-22/h5-7,9,11-13,15,18,23-24,26-27,36H,1,8,10,14,16-17,19H2,2-4H3/t23-,24-,26-,27-,30-,31-,32-,33-/m0/s1
SMILES:	C=C1CCC[C@H]2[C@@]1(C)[C@H]([C@@H]([C@@]1(C)[C@]2(C)[C@H](C[C@@]2(CC(=O)OC2)O1)OC(=O)c1cccnc1)O)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077450
PubChem CID:	44556949
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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2900.0	nM	PMID[484997]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5300.0	nM	PMID[484997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3400.0	nM	PMID[484997]

☑ 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 NPC211920 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	350
0.1-0.2	1456
0.2-0.3	3135
0.3-0.4	9735
0.4-0.5	16937
0.5-0.6	8949
0.6-0.7	1835
0.7-0.8	115
0.8-0.85	51
0.85-0.9	53
0.9-0.95	63
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9901	High Similarity	NPC124029
0.9802	High Similarity	NPC477902
0.966	High Similarity	NPC477906
0.966	High Similarity	NPC150698
0.966	High Similarity	NPC96801
0.9559	High Similarity	NPC471980
0.9557	High Similarity	NPC477903
0.9554	High Similarity	NPC301368
0.9554	High Similarity	NPC84815
0.9512	High Similarity	NPC328154
0.951	High Similarity	NPC127026
0.951	High Similarity	NPC127720
0.9505	High Similarity	NPC294579
0.9505	High Similarity	NPC144779
0.9455	High Similarity	NPC6981
0.942	High Similarity	NPC475601
0.9417	High Similarity	NPC26881
0.9409	High Similarity	NPC62367
0.9363	High Similarity	NPC216428
0.936	High Similarity	NPC471016
0.936	High Similarity	NPC471014
0.936	High Similarity	NPC475408
0.9356	High Similarity	NPC264674
0.9356	High Similarity	NPC4421
0.9333	High Similarity	NPC469748
0.9324	High Similarity	NPC477900
0.9324	High Similarity	NPC477899
0.932	High Similarity	NPC235364
0.9314	High Similarity	NPC75600
0.9314	High Similarity	NPC158020
0.9314	High Similarity	NPC473115
0.9314	High Similarity	NPC6576
0.9314	High Similarity	NPC212768
0.9314	High Similarity	NPC473089
0.931	High Similarity	NPC42678
0.931	High Similarity	NPC470306
0.931	High Similarity	NPC477909
0.931	High Similarity	NPC477907
0.9282	High Similarity	NPC471190
0.9282	High Similarity	NPC470486
0.9282	High Similarity	NPC475644
0.9282	High Similarity	NPC471977
0.9272	High Similarity	NPC477912
0.9252	High Similarity	NPC253482
0.9242	High Similarity	NPC30456
0.9238	High Similarity	NPC91125
0.9234	High Similarity	NPC476110
0.9234	High Similarity	NPC477787
0.9234	High Similarity	NPC328186
0.9234	High Similarity	NPC228377
0.9234	High Similarity	NPC87152
0.9234	High Similarity	NPC475631
0.9234	High Similarity	NPC122968
0.9234	High Similarity	NPC475600
0.9223	High Similarity	NPC477901
0.9213	High Similarity	NPC475648
0.9194	High Similarity	NPC475303
0.9194	High Similarity	NPC316841
0.9194	High Similarity	NPC475596
0.9187	High Similarity	NPC473506
0.9175	High Similarity	NPC472555
0.9163	High Similarity	NPC472553
0.9155	High Similarity	NPC35208
0.9155	High Similarity	NPC327769
0.9139	High Similarity	NPC475498
0.9139	High Similarity	NPC475137
0.9139	High Similarity	NPC473850
0.9108	High Similarity	NPC237702
0.9104	High Similarity	NPC473689
0.9104	High Similarity	NPC292416
0.9095	High Similarity	NPC148860
0.9091	High Similarity	NPC76565
0.9091	High Similarity	NPC57797
0.9091	High Similarity	NPC250807
0.9078	High Similarity	NPC477908
0.9078	High Similarity	NPC206343
0.9065	High Similarity	NPC475426
0.9065	High Similarity	NPC475406
0.9061	High Similarity	NPC319880
0.9061	High Similarity	NPC320324
0.9061	High Similarity	NPC244839
0.9043	High Similarity	NPC477911
0.9043	High Similarity	NPC477788
0.9029	High Similarity	NPC477910
0.9023	High Similarity	NPC327904
0.9023	High Similarity	NPC38959
0.9015	High Similarity	NPC304179
0.9015	High Similarity	NPC48042
0.9015	High Similarity	NPC472550
0.9009	High Similarity	NPC475362
0.8981	High Similarity	NPC319128
0.8966	High Similarity	NPC63041
0.8962	High Similarity	NPC146824
0.8937	High Similarity	NPC30570
0.8889	High Similarity	NPC228331
0.8889	High Similarity	NPC170751
0.8843	High Similarity	NPC238278
0.8796	High Similarity	NPC213143
0.8792	High Similarity	NPC292517
0.8785	High Similarity	NPC285411
0.8785	High Similarity	NPC14116
0.8744	High Similarity	NPC311196
0.8744	High Similarity	NPC134384
0.8714	High Similarity	NPC162812
0.8702	High Similarity	NPC476467
0.8692	High Similarity	NPC233727
0.8647	High Similarity	NPC472752
0.8634	High Similarity	NPC471015
0.8571	High Similarity	NPC180668
0.8571	High Similarity	NPC148896
0.8571	High Similarity	NPC471013
0.8498	Intermediate Similarity	NPC187494
0.8496	Intermediate Similarity	NPC324619
0.8496	Intermediate Similarity	NPC475315
0.8491	Intermediate Similarity	NPC193361
0.8491	Intermediate Similarity	NPC62844
0.8454	Intermediate Similarity	NPC289086
0.8451	Intermediate Similarity	NPC475533
0.8448	Intermediate Similarity	NPC473833
0.8436	Intermediate Similarity	NPC323551
0.8436	Intermediate Similarity	NPC280473
0.8421	Intermediate Similarity	NPC10904
0.8396	Intermediate Similarity	NPC51008
0.8396	Intermediate Similarity	NPC41724
0.8373	Intermediate Similarity	NPC475835
0.8326	Intermediate Similarity	NPC319556
0.8302	Intermediate Similarity	NPC470189
0.8302	Intermediate Similarity	NPC40919
0.8298	Intermediate Similarity	NPC471978
0.8276	Intermediate Similarity	NPC475301
0.8276	Intermediate Similarity	NPC85879
0.8276	Intermediate Similarity	NPC326930
0.8276	Intermediate Similarity	NPC53255
0.8246	Intermediate Similarity	NPC470190
0.824	Intermediate Similarity	NPC13603
0.8233	Intermediate Similarity	NPC207531
0.8224	Intermediate Similarity	NPC165837
0.822	Intermediate Similarity	NPC328928
0.8166	Intermediate Similarity	NPC476090
0.8117	Intermediate Similarity	NPC471979
0.8086	Intermediate Similarity	NPC470279
0.8066	Intermediate Similarity	NPC309498
0.8045	Intermediate Similarity	NPC253314
0.7971	Intermediate Similarity	NPC103230
0.7885	Intermediate Similarity	NPC471004
0.7844	Intermediate Similarity	NPC111732
0.782	Intermediate Similarity	NPC324245
0.782	Intermediate Similarity	NPC320748
0.7793	Intermediate Similarity	NPC32451
0.7793	Intermediate Similarity	NPC328559
0.7746	Intermediate Similarity	NPC79223
0.7689	Intermediate Similarity	NPC329024
0.7615	Intermediate Similarity	NPC156044
0.757	Intermediate Similarity	NPC59033
0.757	Intermediate Similarity	NPC317672
0.7546	Intermediate Similarity	NPC155792
0.7523	Intermediate Similarity	NPC25442
0.7523	Intermediate Similarity	NPC12944
0.7521	Intermediate Similarity	NPC107123
0.7449	Intermediate Similarity	NPC478045
0.7441	Intermediate Similarity	NPC44354
0.7427	Intermediate Similarity	NPC476516
0.7426	Intermediate Similarity	NPC37473
0.7357	Intermediate Similarity	NPC141385
0.7356	Intermediate Similarity	NPC317010
0.7356	Intermediate Similarity	NPC471997
0.7328	Intermediate Similarity	NPC191489
0.7316	Intermediate Similarity	NPC141428
0.7315	Intermediate Similarity	NPC191193
0.7315	Intermediate Similarity	NPC321072
0.7315	Intermediate Similarity	NPC242662
0.7315	Intermediate Similarity	NPC215892
0.7304	Intermediate Similarity	NPC106593
0.7294	Intermediate Similarity	NPC50997
0.7294	Intermediate Similarity	NPC160127
0.729	Intermediate Similarity	NPC324251
0.729	Intermediate Similarity	NPC306001
0.729	Intermediate Similarity	NPC206211
0.729	Intermediate Similarity	NPC475336
0.729	Intermediate Similarity	NPC471629
0.729	Intermediate Similarity	NPC453583
0.729	Intermediate Similarity	NPC317882
0.729	Intermediate Similarity	NPC471754
0.729	Intermediate Similarity	NPC275170
0.729	Intermediate Similarity	NPC473300
0.729	Intermediate Similarity	NPC473400
0.7281	Intermediate Similarity	NPC471606
0.7281	Intermediate Similarity	NPC208553
0.7281	Intermediate Similarity	NPC181964
0.728	Intermediate Similarity	NPC88923
0.728	Intermediate Similarity	NPC100734
0.728	Intermediate Similarity	NPC315634
0.7277	Intermediate Similarity	NPC314834
0.7265	Intermediate Similarity	NPC131273
0.7265	Intermediate Similarity	NPC473441
0.7265	Intermediate Similarity	NPC470280
0.7256	Intermediate Similarity	NPC33372
0.7256	Intermediate Similarity	NPC67246
0.7254	Intermediate Similarity	NPC183537
0.7253	Intermediate Similarity	NPC57690

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 NPC211920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	536
0.2-0.3	704
0.3-0.4	1847
0.4-0.5	3358
0.5-0.6	2001
0.6-0.7	451
0.7-0.8	22
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
0.813	Intermediate Similarity	NPD8468	Phase 2
0.791	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD7396	Approved
0.7636	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1483	Discontinued
0.7467	Intermediate Similarity	NPD8325	Phase 3
0.7467	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD8326	Phase 3
0.7411	Intermediate Similarity	NPD3794	Approved
0.7411	Intermediate Similarity	NPD3795	Approved
0.7328	Intermediate Similarity	NPD7708	Approved
0.7281	Intermediate Similarity	NPD8485	Approved
0.728	Intermediate Similarity	NPD7803	Approved
0.7257	Intermediate Similarity	NPD5891	Approved
0.7238	Intermediate Similarity	NPD7886	Phase 2
0.7238	Intermediate Similarity	NPD7885	Phase 2
0.7214	Intermediate Similarity	NPD820	Phase 3
0.7195	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7778	Approved
0.7169	Intermediate Similarity	NPD53	Approved
0.7169	Intermediate Similarity	NPD7777	Approved
0.7143	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7878	Phase 2
0.7116	Intermediate Similarity	NPD7234	Approved
0.7116	Intermediate Similarity	NPD7233	Approved
0.7098	Intermediate Similarity	NPD7010	Phase 3
0.7083	Intermediate Similarity	NPD8435	Approved
0.7083	Intermediate Similarity	NPD8360	Approved
0.7083	Intermediate Similarity	NPD8361	Approved
0.708	Intermediate Similarity	NPD7955	Approved
0.708	Intermediate Similarity	NPD6529	Discontinued
0.708	Intermediate Similarity	NPD7956	Approved
0.7073	Intermediate Similarity	NPD6635	Approved
0.7069	Intermediate Similarity	NPD3280	Approved
0.7061	Intermediate Similarity	NPD7069	Discontinued
0.7043	Intermediate Similarity	NPD3393	Approved
0.7043	Intermediate Similarity	NPD3389	Approved
0.7043	Intermediate Similarity	NPD3394	Approved
0.7018	Intermediate Similarity	NPD4417	Approved
0.7014	Intermediate Similarity	NPD6641	Approved
0.7014	Intermediate Similarity	NPD6642	Approved
0.7012	Intermediate Similarity	NPD8409	Suspended
0.6996	Remote Similarity	NPD8479	Phase 2
0.6986	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3947	Discontinued
0.696	Remote Similarity	NPD2510	Approved
0.696	Remote Similarity	NPD2509	Approved
0.6946	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4506	Discontinued
0.6927	Remote Similarity	NPD8063	Discontinued
0.6912	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8091	Phase 3
0.6903	Remote Similarity	NPD6987	Phase 1
0.6895	Remote Similarity	NPD2336	Approved
0.6894	Remote Similarity	NPD4301	Approved
0.688	Remote Similarity	NPD6770	Approved
0.6867	Remote Similarity	NPD4989	Phase 2
0.6866	Remote Similarity	NPD9271	Approved
0.6858	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7707	Approved
0.684	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6026	Approved
0.6827	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2511	Approved
0.6797	Remote Similarity	NPD5475	Discontinued
0.6786	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD8289	Discontinued
0.6771	Remote Similarity	NPD2307	Discontinued
0.6763	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6791	Phase 2
0.6754	Remote Similarity	NPD2831	Approved
0.6754	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5088	Discontinued
0.6745	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8407	Phase 2
0.674	Remote Similarity	NPD7187	Phase 2
0.674	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7404	Approved
0.6732	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4600	Approved
0.6726	Remote Similarity	NPD4601	Approved
0.6726	Remote Similarity	NPD4427	Phase 2
0.6725	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD8370	Discontinued
0.6712	Remote Similarity	NPD4376	Phase 3
0.6705	Remote Similarity	NPD8465	Approved
0.6705	Remote Similarity	NPD8467	Approved
0.6705	Remote Similarity	NPD8466	Approved
0.6696	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1926	Approved
0.6694	Remote Similarity	NPD8412	Phase 1
0.6694	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD9075	Approved
0.6683	Remote Similarity	NPD9074	Approved
0.6682	Remote Similarity	NPD6361	Phase 2
0.668	Remote Similarity	NPD4086	Phase 1
0.6667	Remote Similarity	NPD6962	Phase 2
0.6667	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD8356	Approved
0.6653	Remote Similarity	NPD6790	Phase 1
0.6653	Remote Similarity	NPD7417	Discontinued
0.6653	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7957	Phase 1
0.6639	Remote Similarity	NPD7426	Phase 1
0.6638	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD3006	Discontinued
0.6624	Remote Similarity	NPD7395	Discontinued
0.6612	Remote Similarity	NPD4373	Phase 2
0.6609	Remote Similarity	NPD5901	Discontinued
0.6606	Remote Similarity	NPD8021	Approved
0.6606	Remote Similarity	NPD8368	Discontinued
0.6606	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8020	Approved
0.6606	Remote Similarity	NPD4948	Discontinued
0.6604	Remote Similarity	NPD8460	Approved
0.6604	Remote Similarity	NPD8426	Approved
0.6604	Remote Similarity	NPD8425	Approved
0.6604	Remote Similarity	NPD6446	Discontinued
0.6604	Remote Similarity	NPD8459	Approved
0.6603	Remote Similarity	NPD8363	Approved
0.6603	Remote Similarity	NPD8364	Approved
0.6598	Remote Similarity	NPD3925	Approved
0.6593	Remote Similarity	NPD5003	Discontinued
0.6582	Remote Similarity	NPD8404	Phase 2
0.6581	Remote Similarity	NPD7470	Discontinued
0.658	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8428	Approved
0.6579	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8427	Approved
0.6579	Remote Similarity	NPD8429	Approved
0.6567	Remote Similarity	NPD107	Approved
0.656	Remote Similarity	NPD6716	Phase 1
0.6557	Remote Similarity	NPD5022	Discontinued
0.6553	Remote Similarity	NPD8462	Phase 1
0.6553	Remote Similarity	NPD5866	Approved
0.6553	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7562	Approved
0.6547	Remote Similarity	NPD6281	Approved
0.6544	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD8430	Approved
0.6542	Remote Similarity	NPD6298	Discontinued
0.6542	Remote Similarity	NPD5147	Discontinued
0.654	Remote Similarity	NPD5490	Discontinued
0.6538	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5482	Discontinued
0.6533	Remote Similarity	NPD4529	Approved
0.6533	Remote Similarity	NPD4526	Approved
0.6533	Remote Similarity	NPD4528	Approved
0.653	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7191	Phase 2
0.6522	Remote Similarity	NPD6276	Discontinued
0.652	Remote Similarity	NPD7576	Discontinued
0.6518	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD4889	Approved
0.6515	Remote Similarity	NPD6995	Phase 1
0.6508	Remote Similarity	NPD7967	Discontinued
0.6507	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4500	Approved
0.6507	Remote Similarity	NPD4501	Approved
0.6502	Remote Similarity	NPD5640	Discontinued
0.649	Remote Similarity	NPD4952	Phase 3
0.6489	Remote Similarity	NPD6665	Discontinued
0.6484	Remote Similarity	NPD5898	Approved
0.6484	Remote Similarity	NPD5897	Approved
0.6484	Remote Similarity	NPD5899	Approved
0.6481	Remote Similarity	NPD3371	Approved
0.6478	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6226	Phase 3
0.6468	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD2896	Discontinued
0.6466	Remote Similarity	NPD5805	Approved
0.6463	Remote Similarity	NPD7688	Phase 1
0.6463	Remote Similarity	NPD6874	Approved
0.6461	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1270	Approved
0.6456	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7169	Suspended
0.6447	Remote Similarity	NPD6206	Phase 1
0.6444	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD7925	Phase 2
0.6439	Remote Similarity	NPD7924	Phase 2
0.6435	Remote Similarity	NPD6479	Discontinued
0.6432	Remote Similarity	NPD7944	Discontinued
0.6429	Remote Similarity	NPD4897	Phase 2
0.6422	Remote Similarity	NPD5513	Phase 2
0.6422	Remote Similarity	NPD6176	Phase 1
0.642	Remote Similarity	NPD7859	Phase 2
0.6417	Remote Similarity	NPD8375	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