NPASS Compound

Structure

NPC6815 OpenBabel07101719132D 45 49 0 0 1 0 0 0 0 0999 V2000 1.4986 -3.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2728 -3.6744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2728 -4.1643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4243 1.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4243 1.7147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4041 -1.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6112 0.8209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0165 0.3363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3085 1.7528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6722 1.0645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1214 0.2450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4243 -2.2046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0258 0.8209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2238 1.7093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1129 -2.6105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7522 -3.0497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4243 -4.1643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1214 -3.6744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8185 0.2450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1214 0.7349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2728 0.7349 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4243 -2.6946 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1214 -0.7349 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4243 0.2450 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2728 -2.2046 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8185 -0.7349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2728 0.2450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4243 0.7349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4243 -1.2248 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2728 -1.2248 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4243 -0.7349 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6986 -2.7961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4243 -5.1441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9700 -4.1643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6671 -1.2248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2728 -0.7349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9142 -0.3762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3286 1.7528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1823 1.9131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0593 -2.3569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4243 -3.6744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1214 -2.6946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9700 -1.2248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4243 0.7349 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 16 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 9 2 0 0 0 0 7 19 1 0 0 0 0 8 10 2 0 0 0 0 8 20 1 0 0 0 0 9 38 1 0 0 0 0 10 39 1 0 0 0 0 11 23 1 0 0 0 0 12 22 1 0 0 0 0 12 29 1 0 0 0 0 13 19 2 0 0 0 0 13 38 1 0 0 0 0 14 20 2 0 0 0 0 14 39 1 0 0 0 0 15 30 1 0 0 0 0 15 40 1 0 0 0 0 16 32 2 0 0 0 0 16 40 1 0 0 0 0 17 33 2 0 0 0 0 17 41 1 0 0 0 0 18 34 2 0 0 0 0 18 42 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 11 1 1 0 0 0 21 24 1 0 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 41 1 6 0 0 0 23 30 1 1 0 0 0 23 43 1 0 0 0 0 24 31 1 1 0 0 0 24 44 1 0 0 0 0 25 30 1 6 0 0 0 25 42 1 0 0 0 0 26 35 2 0 0 0 0 26 43 1 0 0 0 0 27 36 2 0 0 0 0 27 44 1 0 0 0 0 28 45 1 0 0 0 0 29 31 1 6 0 0 0 29 37 1 0 0 0 0 30 31 1 1 0 0 0 31 45 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	632.21
Volume:	601.285
LogP:	3.025
LogD:	1.871
LogS:	-3.837
# Rotatable Bonds:	13
TPSA:	187.24
# H-Bond Aceptor:	14
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	6.257
Fsp3:	0.581
Lipinski Rule-of-5:	Rejected
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:	-5.349
MDCK Permeability:	5.973959559923969e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.939
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.426
Plasma Protein Binding (PPB):	80.01985931396484%
Volume Distribution (VD):	1.8
Pgp-substrate:	11.189920425415039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.544
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.565
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	5.743
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.67
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.754
Skin Sensitization:	0.046
Carcinogencity:	0.886
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC6815

Natural Product ID:	NPC6815
*Common Name:**	FBFCHVYQDYUGKU-NNTMNUMBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FBFCHVYQDYUGKU-NNTMNUMBSA-N
Standard InCHI:	InChI=1S/C31H36O14/c1-16(32)40-15-30-23(43-26(35)19-7-9-38-13-19)11-21-24(44-27(36)20-8-10-39-14-20)31(30,45-28(21,4)5)29(6,37)12-22(41-17(2)33)25(30)42-18(3)34/h7-10,13-14,21-25,37H,11-12,15H2,1-6H3/t21-,22+,23+,24-,25+,29+,30-,31+/m1/s1
SMILES:	CC(=O)OC[C@@]12[C@H](C[C@@H]3[C@H]([C@@]2([C@](C)(C[C@@H]([C@@H]1OC(=O)C)OC(=O)C)O)OC3(C)C)OC(=O)c1ccoc1)OC(=O)c1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1829521
PubChem CID:	56670474
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*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
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20146433]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	fruits	n.a.	n.a.	PMID[21856049]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27541714]
NPO26437	Maytenus jelskii	Species	Celastraceae	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
Ki	1
Others	10

Activity Type	# Activity
Cell Line	2
Individual Protein	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell Line	NIH3T3	Mus musculus	Activity	=	91.98	%	PMID[448170]
NPT886	Cell Line	NIH3T3	Mus musculus	Activity	=	82.86	%	PMID[448170]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Inhibition	=	70.0	%	PMID[448170]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ki	=	510.0	nM	PMID[448170]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Imax	>	90.0	%	PMID[448170]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	2.72	n.a.	PMID[448170]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	4.37	n.a.	PMID[448170]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	14.63	n.a.	PMID[448170]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	3.58	n.a.	PMID[448170]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	18.85	n.a.	PMID[448170]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	65.64	n.a.	PMID[448170]

☑ 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 NPC6815 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	313
0.1-0.2	1487
0.2-0.3	3747
0.3-0.4	6538
0.4-0.5	11898
0.5-0.6	10726
0.6-0.7	7252
0.7-0.8	636
0.8-0.85	73
0.85-0.9	9
0.9-0.95	1
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC294803
0.993	High Similarity	NPC147340
0.993	High Similarity	NPC271460
0.9296	High Similarity	NPC156077
0.8926	High Similarity	NPC243165
0.8854	High Similarity	NPC86800
0.8634	High Similarity	NPC294512
0.8627	High Similarity	NPC240214
0.8616	High Similarity	NPC472141
0.8476	Intermediate Similarity	NPC56953
0.8476	Intermediate Similarity	NPC176413
0.8438	Intermediate Similarity	NPC276735
0.84	Intermediate Similarity	NPC475519
0.8375	Intermediate Similarity	NPC472139
0.8354	Intermediate Similarity	NPC299038
0.8333	Intermediate Similarity	NPC268905
0.8313	Intermediate Similarity	NPC200782
0.8302	Intermediate Similarity	NPC475967
0.8302	Intermediate Similarity	NPC475226
0.8269	Intermediate Similarity	NPC18135
0.8258	Intermediate Similarity	NPC69647
0.8258	Intermediate Similarity	NPC195325
0.8258	Intermediate Similarity	NPC125182
0.8247	Intermediate Similarity	NPC255414
0.8239	Intermediate Similarity	NPC472778
0.8239	Intermediate Similarity	NPC472777
0.8239	Intermediate Similarity	NPC472776
0.8171	Intermediate Similarity	NPC271235
0.8165	Intermediate Similarity	NPC34421
0.8165	Intermediate Similarity	NPC98206
0.8165	Intermediate Similarity	NPC237259
0.8148	Intermediate Similarity	NPC472773
0.8137	Intermediate Similarity	NPC191828
0.8125	Intermediate Similarity	NPC261597
0.8125	Intermediate Similarity	NPC470119
0.8125	Intermediate Similarity	NPC470118
0.8125	Intermediate Similarity	NPC36655
0.8125	Intermediate Similarity	NPC214495
0.8113	Intermediate Similarity	NPC44675
0.8113	Intermediate Similarity	NPC476262
0.8113	Intermediate Similarity	NPC214541
0.811	Intermediate Similarity	NPC472774
0.811	Intermediate Similarity	NPC270312
0.811	Intermediate Similarity	NPC472775
0.811	Intermediate Similarity	NPC472651
0.8101	Intermediate Similarity	NPC476201
0.8098	Intermediate Similarity	NPC470182
0.8086	Intermediate Similarity	NPC82851
0.8086	Intermediate Similarity	NPC472771
0.8086	Intermediate Similarity	NPC470792
0.8086	Intermediate Similarity	NPC188649
0.8075	Intermediate Similarity	NPC472671
0.8061	Intermediate Similarity	NPC472652
0.8052	Intermediate Similarity	NPC251865
0.805	Intermediate Similarity	NPC282445
0.805	Intermediate Similarity	NPC302054
0.805	Intermediate Similarity	NPC253201
0.8049	Intermediate Similarity	NPC97574
0.8049	Intermediate Similarity	NPC93172
0.8037	Intermediate Similarity	NPC88841
0.8037	Intermediate Similarity	NPC288602
0.8037	Intermediate Similarity	NPC285567
0.8037	Intermediate Similarity	NPC419
0.8037	Intermediate Similarity	NPC292389
0.8037	Intermediate Similarity	NPC469338
0.8025	Intermediate Similarity	NPC472653
0.8013	Intermediate Similarity	NPC221809
0.8012	Intermediate Similarity	NPC475066
0.8012	Intermediate Similarity	NPC1408
0.8012	Intermediate Similarity	NPC246841
0.8012	Intermediate Similarity	NPC82602
0.8012	Intermediate Similarity	NPC187149
0.8	Intermediate Similarity	NPC476850
0.8	Intermediate Similarity	NPC470938
0.8	Intermediate Similarity	NPC5676
0.8	Intermediate Similarity	NPC476861
0.8	Intermediate Similarity	NPC173516
0.8	Intermediate Similarity	NPC264943
0.7988	Intermediate Similarity	NPC276551
0.7988	Intermediate Similarity	NPC271657
0.7988	Intermediate Similarity	NPC470940
0.7988	Intermediate Similarity	NPC56358
0.7988	Intermediate Similarity	NPC469849
0.7987	Intermediate Similarity	NPC469503
0.7987	Intermediate Similarity	NPC322546
0.7987	Intermediate Similarity	NPC476946
0.7987	Intermediate Similarity	NPC472672
0.7987	Intermediate Similarity	NPC308205
0.7975	Intermediate Similarity	NPC149896
0.7975	Intermediate Similarity	NPC476122
0.7975	Intermediate Similarity	NPC68848
0.7975	Intermediate Similarity	NPC329938
0.7975	Intermediate Similarity	NPC18347
0.7964	Intermediate Similarity	NPC475237
0.7964	Intermediate Similarity	NPC475641
0.7952	Intermediate Similarity	NPC296558
0.7952	Intermediate Similarity	NPC160651
0.7952	Intermediate Similarity	NPC471397
0.7939	Intermediate Similarity	NPC121995
0.7939	Intermediate Similarity	NPC470875
0.7937	Intermediate Similarity	NPC57998
0.7927	Intermediate Similarity	NPC477405
0.7927	Intermediate Similarity	NPC283209
0.7927	Intermediate Similarity	NPC471168
0.7927	Intermediate Similarity	NPC469846
0.7927	Intermediate Similarity	NPC302369
0.7927	Intermediate Similarity	NPC134254
0.7927	Intermediate Similarity	NPC39986
0.7922	Intermediate Similarity	NPC52412
0.7922	Intermediate Similarity	NPC121158
0.7914	Intermediate Similarity	NPC470789
0.7911	Intermediate Similarity	NPC472654
0.7901	Intermediate Similarity	NPC469847
0.7901	Intermediate Similarity	NPC197137
0.7901	Intermediate Similarity	NPC249021
0.7901	Intermediate Similarity	NPC195954
0.7901	Intermediate Similarity	NPC167142
0.7901	Intermediate Similarity	NPC45101
0.7901	Intermediate Similarity	NPC88007
0.7901	Intermediate Similarity	NPC472772
0.7888	Intermediate Similarity	NPC155939
0.7888	Intermediate Similarity	NPC296807
0.7888	Intermediate Similarity	NPC141538
0.7879	Intermediate Similarity	NPC476858
0.7879	Intermediate Similarity	NPC476856
0.7879	Intermediate Similarity	NPC123088
0.7879	Intermediate Similarity	NPC476857
0.7875	Intermediate Similarity	NPC75906
0.7875	Intermediate Similarity	NPC182427
0.7875	Intermediate Similarity	NPC29695
0.787	Intermediate Similarity	NPC94763
0.787	Intermediate Similarity	NPC236004
0.7866	Intermediate Similarity	NPC69028
0.7866	Intermediate Similarity	NPC472668
0.7866	Intermediate Similarity	NPC263432
0.7857	Intermediate Similarity	NPC169299
0.7857	Intermediate Similarity	NPC285227
0.7857	Intermediate Similarity	NPC160818
0.7857	Intermediate Similarity	NPC20500
0.7853	Intermediate Similarity	NPC307383
0.7848	Intermediate Similarity	NPC471007
0.7844	Intermediate Similarity	NPC472766
0.7844	Intermediate Similarity	NPC472765
0.7831	Intermediate Similarity	NPC472670
0.7831	Intermediate Similarity	NPC307781
0.7818	Intermediate Similarity	NPC51568
0.7818	Intermediate Similarity	NPC165218
0.7818	Intermediate Similarity	NPC472669
0.7818	Intermediate Similarity	NPC234660
0.7805	Intermediate Similarity	NPC477402
0.7805	Intermediate Similarity	NPC335761
0.7805	Intermediate Similarity	NPC287559
0.7805	Intermediate Similarity	NPC25255
0.7798	Intermediate Similarity	NPC88593
0.7798	Intermediate Similarity	NPC470995
0.7791	Intermediate Similarity	NPC194499
0.7784	Intermediate Similarity	NPC472282
0.7784	Intermediate Similarity	NPC100333
0.7784	Intermediate Similarity	NPC310572
0.7784	Intermediate Similarity	NPC472764
0.7784	Intermediate Similarity	NPC476853
0.7778	Intermediate Similarity	NPC478177
0.7778	Intermediate Similarity	NPC472665
0.7778	Intermediate Similarity	NPC469336
0.7771	Intermediate Similarity	NPC476860
0.7771	Intermediate Similarity	NPC159520
0.7765	Intermediate Similarity	NPC469576
0.7765	Intermediate Similarity	NPC471437
0.7764	Intermediate Similarity	NPC476939
0.7764	Intermediate Similarity	NPC476940
0.7759	Intermediate Similarity	NPC105395
0.7759	Intermediate Similarity	NPC242068
0.7759	Intermediate Similarity	NPC247563
0.7758	Intermediate Similarity	NPC5079
0.7758	Intermediate Similarity	NPC193798
0.7758	Intermediate Similarity	NPC18986
0.7758	Intermediate Similarity	NPC207978
0.7758	Intermediate Similarity	NPC471166
0.7758	Intermediate Similarity	NPC471167
0.7758	Intermediate Similarity	NPC211777
0.7756	Intermediate Similarity	NPC267632
0.7756	Intermediate Similarity	NPC223415
0.7756	Intermediate Similarity	NPC470741
0.7751	Intermediate Similarity	NPC159232
0.775	Intermediate Similarity	NPC156189
0.7744	Intermediate Similarity	NPC477403
0.7744	Intermediate Similarity	NPC475295
0.7744	Intermediate Similarity	NPC473473
0.7738	Intermediate Similarity	NPC472673
0.773	Intermediate Similarity	NPC469485
0.773	Intermediate Similarity	NPC126723
0.773	Intermediate Similarity	NPC41880
0.773	Intermediate Similarity	NPC104736
0.7725	Intermediate Similarity	NPC478178
0.7725	Intermediate Similarity	NPC23387
0.7722	Intermediate Similarity	NPC346
0.7719	Intermediate Similarity	NPC469633
0.7716	Intermediate Similarity	NPC178932
0.7716	Intermediate Similarity	NPC30222
0.7711	Intermediate Similarity	NPC663

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 NPC6815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	1162
0.2-0.3	2730
0.3-0.4	2698
0.4-0.5	1603
0.5-0.6	553
0.6-0.7	133
0.7-0.8	3
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
0.7701	Intermediate Similarity	NPD8434	Phase 2
0.7561	Intermediate Similarity	NPD5761	Phase 2
0.7561	Intermediate Similarity	NPD5760	Phase 2
0.7076	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6559	Discontinued
0.6765	Remote Similarity	NPD6599	Discontinued
0.6744	Remote Similarity	NPD7819	Suspended
0.6744	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4628	Phase 3
0.6724	Remote Similarity	NPD7075	Discontinued
0.67	Remote Similarity	NPD8404	Phase 2
0.6648	Remote Similarity	NPD5494	Approved
0.6648	Remote Similarity	NPD6765	Approved
0.6648	Remote Similarity	NPD7473	Discontinued
0.6648	Remote Similarity	NPD6764	Approved
0.6646	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5402	Approved
0.6596	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6234	Discontinued
0.6588	Remote Similarity	NPD920	Approved
0.6573	Remote Similarity	NPD6232	Discontinued
0.6571	Remote Similarity	NPD4965	Approved
0.6571	Remote Similarity	NPD4967	Phase 2
0.6571	Remote Similarity	NPD4966	Approved
0.6519	Remote Similarity	NPD3818	Discontinued
0.6514	Remote Similarity	NPD3817	Phase 2
0.6512	Remote Similarity	NPD3226	Approved
0.6509	Remote Similarity	NPD6799	Approved
0.6505	Remote Similarity	NPD6784	Approved
0.6505	Remote Similarity	NPD6785	Approved
0.6497	Remote Similarity	NPD919	Approved
0.6494	Remote Similarity	NPD6801	Discontinued
0.6486	Remote Similarity	NPD8312	Approved
0.6486	Remote Similarity	NPD8313	Approved
0.6485	Remote Similarity	NPD1551	Phase 2
0.6484	Remote Similarity	NPD5844	Phase 1
0.6477	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3882	Suspended
0.6471	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3926	Phase 2
0.6441	Remote Similarity	NPD3749	Approved
0.6429	Remote Similarity	NPD7228	Approved
0.6425	Remote Similarity	NPD1247	Approved
0.6425	Remote Similarity	NPD8127	Discontinued
0.6424	Remote Similarity	NPD2799	Discontinued
0.64	Remote Similarity	NPD37	Approved
0.64	Remote Similarity	NPD1934	Approved
0.6395	Remote Similarity	NPD5403	Approved
0.6386	Remote Similarity	NPD2935	Discontinued
0.6384	Remote Similarity	NPD7768	Phase 2
0.6379	Remote Similarity	NPD4380	Phase 2
0.6374	Remote Similarity	NPD2532	Approved
0.6374	Remote Similarity	NPD2533	Approved
0.6374	Remote Similarity	NPD2534	Approved
0.6374	Remote Similarity	NPD5401	Approved
0.6364	Remote Similarity	NPD2801	Approved
0.6353	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD2346	Discontinued
0.6347	Remote Similarity	NPD1471	Phase 3
0.6343	Remote Similarity	NPD7411	Suspended
0.6339	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6273	Approved
0.6337	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD6832	Phase 2
0.6331	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8150	Discontinued
0.629	Remote Similarity	NPD7240	Approved
0.627	Remote Similarity	NPD7074	Phase 3
0.6265	Remote Similarity	NPD7097	Phase 1
0.6263	Remote Similarity	NPD7435	Discontinued
0.6257	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5762	Approved
0.625	Remote Similarity	NPD2344	Approved
0.625	Remote Similarity	NPD5763	Approved
0.6243	Remote Similarity	NPD7199	Phase 2
0.6242	Remote Similarity	NPD6355	Discontinued
0.623	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6166	Phase 2
0.6216	Remote Similarity	NPD7054	Approved
0.6216	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7095	Approved
0.619	Remote Similarity	NPD2796	Approved
0.6185	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD7472	Approved
0.6176	Remote Similarity	NPD2800	Approved
0.6176	Remote Similarity	NPD1243	Approved
0.6175	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD7047	Phase 3
0.6162	Remote Similarity	NPD3751	Discontinued
0.6159	Remote Similarity	NPD2313	Discontinued
0.6154	Remote Similarity	NPD6959	Discontinued
0.6145	Remote Similarity	NPD447	Suspended
0.6141	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.614	Remote Similarity	NPD3750	Approved
0.6136	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1549	Phase 2
0.6117	Remote Similarity	NPD7251	Discontinued
0.6111	Remote Similarity	NPD6778	Approved
0.6111	Remote Similarity	NPD6779	Approved
0.6111	Remote Similarity	NPD6776	Approved
0.6111	Remote Similarity	NPD6777	Approved
0.6111	Remote Similarity	NPD6781	Approved
0.6111	Remote Similarity	NPD6780	Approved
0.6111	Remote Similarity	NPD6782	Approved
0.6105	Remote Similarity	NPD2309	Approved
0.6105	Remote Similarity	NPD8407	Phase 2
0.61	Remote Similarity	NPD7497	Discontinued
0.6092	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD1465	Phase 2
0.6085	Remote Similarity	NPD7808	Phase 3
0.6084	Remote Similarity	NPD4060	Phase 1
0.6082	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7874	Approved
0.6078	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6797	Phase 2
0.6064	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5953	Discontinued
0.6061	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6823	Phase 2
0.6048	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4110	Phase 3
0.6047	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD7458	Discontinued
0.6036	Remote Similarity	NPD7033	Discontinued
0.6036	Remote Similarity	NPD3748	Approved
0.6034	Remote Similarity	NPD1511	Approved
0.6033	Remote Similarity	NPD7229	Phase 3
0.6033	Remote Similarity	NPD6808	Phase 2
0.6033	Remote Similarity	NPD3787	Discontinued
0.6032	Remote Similarity	NPD7685	Pre-registration
0.6032	Remote Similarity	NPD8368	Discontinued
0.6023	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD2424	Discontinued
0.602	Remote Similarity	NPD7698	Approved
0.602	Remote Similarity	NPD7696	Phase 3
0.602	Remote Similarity	NPD7697	Approved
0.602	Remote Similarity	NPD7680	Approved
0.6	Remote Similarity	NPD8455	Phase 2
0.599	Remote Similarity	NPD7870	Phase 2
0.599	Remote Similarity	NPD7871	Phase 2
0.5989	Remote Similarity	NPD7799	Discontinued
0.5988	Remote Similarity	NPD4140	Approved
0.598	Remote Similarity	NPD7701	Phase 2
0.5971	Remote Similarity	NPD7801	Approved
0.5971	Remote Similarity	NPD7783	Phase 2
0.5971	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD1512	Approved
0.5965	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6004	Phase 3
0.5965	Remote Similarity	NPD6002	Phase 3
0.5965	Remote Similarity	NPD6005	Phase 3
0.5964	Remote Similarity	NPD3764	Approved
0.5964	Remote Similarity	NPD7985	Registered
0.5964	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7286	Phase 2
0.5954	Remote Similarity	NPD7003	Approved
0.5952	Remote Similarity	NPD1933	Approved
0.5952	Remote Similarity	NPD5735	Approved
0.5951	Remote Similarity	NPD1203	Approved
0.5951	Remote Similarity	NPD8151	Discontinued
0.5946	Remote Similarity	NPD5711	Approved
0.5946	Remote Similarity	NPD5710	Approved
0.5943	Remote Similarity	NPD7907	Approved
0.5943	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD1510	Phase 2
0.5941	Remote Similarity	NPD4308	Phase 3
0.5928	Remote Similarity	NPD6233	Phase 2
0.592	Remote Similarity	NPD6190	Approved
0.5917	Remote Similarity	NPD1607	Approved
0.5917	Remote Similarity	NPD6653	Approved
0.5911	Remote Similarity	NPD8319	Approved
0.5911	Remote Similarity	NPD8320	Phase 1
0.5906	Remote Similarity	NPD6099	Approved
0.5906	Remote Similarity	NPD2438	Suspended
0.5906	Remote Similarity	NPD6100	Approved
0.5906	Remote Similarity	NPD6032	Approved
0.59	Remote Similarity	NPD8285	Discontinued
0.5899	Remote Similarity	NPD1653	Approved
0.5897	Remote Similarity	NPD8435	Approved
0.5897	Remote Similarity	NPD8360	Approved
0.5897	Remote Similarity	NPD8361	Approved
0.5893	Remote Similarity	NPD1240	Approved
0.5889	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6798	Discontinued
0.5868	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD9717	Approved
0.5864	Remote Similarity	NPD1608	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