NPASS Compound

Structure

CID167340 OpenBabel06191715542D 39 45 0 0 1 0 0 0 0 0999 V2000 0.7300 -4.2812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6254 -4.7990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3385 -1.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3397 0.9855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7325 -0.4241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3855 -0.6963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6858 -0.0671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1904 -1.6169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7911 -0.3584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2956 -1.9082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2575 -0.9432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2558 -3.7649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1930 1.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2566 -2.8244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2580 -0.0022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3887 2.8969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8125 -2.3529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8761 2.7384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5960 -1.2789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2581 1.8795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4428 -1.4129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6271 -2.8239 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4406 -4.2349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8130 -1.4120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4439 1.4098 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6299 1.8798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8152 1.4100 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7013 -1.5702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6263 -3.7644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4423 -2.3539 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4434 0.4688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6282 -0.9420 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6287 -0.0010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4402 -5.2523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6305 2.8798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5062 -2.4907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5748 3.3672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0016 -0.9410 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 29 1 0 0 0 0 2 29 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 23 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 37 1 0 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 37 1 0 0 0 0 19 28 1 0 0 0 0 20 25 1 0 0 0 0 21 30 1 6 0 0 0 21 32 1 0 0 0 0 22 29 1 0 0 0 0 22 30 1 6 0 0 0 23 29 1 0 0 0 0 23 34 2 0 0 0 0 24 32 1 1 0 0 0 24 38 1 0 0 0 0 25 26 1 0 0 0 0 25 31 1 1 0 0 0 26 27 1 0 0 0 0 26 35 2 0 0 0 0 27 33 1 1 0 0 0 27 39 1 0 0 0 0 28 36 2 0 0 0 0 28 38 1 0 0 0 0 30 3 1 6 0 0 0 31 33 1 1 0 0 0 32 33 1 1 0 0 0 33 39 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.25
Volume:	548.442
LogP:	5.072
LogD:	3.166
LogS:	-4.021
# Rotatable Bonds:	4
TPSA:	86.11
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	5.501
Fsp3:	0.545
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:	-5.319
MDCK Permeability:	2.173674147343263e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	99.06169128417969%
Volume Distribution (VD):	2.577
Pgp-substrate:	4.7971391677856445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.269
CYP2C19-inhibitor:	0.603
CYP2C19-substrate:	0.753
CYP2C9-inhibitor:	0.919
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.665
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.906
CYP3A4-substrate:	0.854

ADMET: Excretion

Clearance (CL):	10.042
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.249
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.623
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.225
Carcinogencity:	0.117
Eye Corrosion:	0.023
Eye Irritation:	0.223
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC167340

Natural Product ID:	NPC167340
*Common Name:**	NHRKCWIDMHBOOY-CRMKCTJSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NHRKCWIDMHBOOY-CRMKCTJSSA-N
Standard InCHI:	InChI=1S/C33H36O6/c1-29(2)22-17-24(38-28(36)19-9-7-6-8-10-19)32(5)21(30(22,3)14-12-23(29)34)11-15-31(4)25(20-13-16-37-18-20)26(35)27-33(31,32)39-27/h6-10,12-14,16,18,21-22,24-25,27H,11,15,17H2,1-5H3/t21-,22+,24-,25-,27-,30-,31+,32+,33-/m1/s1
SMILES:	O=C(c1ccccc1)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@@]2([C@@H]2[C@]1(C)[C@@]13O[C@@H]1C(=O)[C@H]([C@@]3(CC2)C)c1ccoc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774391
PubChem CID:	52951893
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193038]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593280]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816111]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20669933]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607354]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614419]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26339153]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28493718]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	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	6
Others	9

Activity Type	# Activity
Cell Line	12
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3100.0	nM	PMID[509405]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[509405]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[509405]
NPT116	Cell Line	HL-60	Homo sapiens	Ratio IC50	=	5.19	n.a.	PMID[509405]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	1.4	%	PMID[509405]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	56.9	%	PMID[509405]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	3.0	%	PMID[509405]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	38.7	%	PMID[509405]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	4.5	%	PMID[509405]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	28.2	%	PMID[509405]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	15.5	%	PMID[509405]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	51.8	%	PMID[509405]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8400.0	nM	PMID[509405]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[509405]
NPT27	Others	Unspecified		IC50	=	16100.0	nM	PMID[509405]

☑ 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 NPC167340 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	479
0.1-0.2	1716
0.2-0.3	3109
0.3-0.4	6772
0.4-0.5	11495
0.5-0.6	8364
0.6-0.7	8777
0.7-0.8	1695
0.8-0.85	239
0.85-0.9	49
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9379	High Similarity	NPC197596
0.9157	High Similarity	NPC302392
0.9048	High Similarity	NPC469848
0.9036	High Similarity	NPC473766
0.9036	High Similarity	NPC473753
0.8951	High Similarity	NPC25351
0.8902	High Similarity	NPC473368
0.8788	High Similarity	NPC474932
0.8743	High Similarity	NPC224394
0.8743	High Similarity	NPC663
0.872	High Similarity	NPC469850
0.8683	High Similarity	NPC471167
0.8683	High Similarity	NPC471003
0.8683	High Similarity	NPC471166
0.8683	High Similarity	NPC470939
0.8667	High Similarity	NPC60973
0.8667	High Similarity	NPC209364
0.8667	High Similarity	NPC107646
0.8631	High Similarity	NPC476035
0.8631	High Similarity	NPC475039
0.8631	High Similarity	NPC14499
0.8614	High Similarity	NPC472283
0.8614	High Similarity	NPC286722
0.8588	High Similarity	NPC478179
0.8571	High Similarity	NPC6326
0.8563	High Similarity	NPC473473
0.8563	High Similarity	NPC475295
0.8554	High Similarity	NPC41880
0.8554	High Similarity	NPC104736
0.8545	High Similarity	NPC471863
0.8531	High Similarity	NPC247563
0.8531	High Similarity	NPC105395
0.8531	High Similarity	NPC242068
0.8529	High Similarity	NPC478178
0.8529	High Similarity	NPC475779
0.8521	High Similarity	NPC469846
0.8521	High Similarity	NPC471168
0.8521	High Similarity	NPC472669
0.8512	High Similarity	NPC305016
0.8512	High Similarity	NPC287559
0.8512	High Similarity	NPC475381
0.8503	High Similarity	NPC81405
0.8503	High Similarity	NPC304692
0.8488	Intermediate Similarity	NPC88593
0.8485	Intermediate Similarity	NPC246164
0.848	Intermediate Similarity	NPC472282
0.848	Intermediate Similarity	NPC476224
0.848	Intermediate Similarity	NPC472784
0.8476	Intermediate Similarity	NPC477404
0.8476	Intermediate Similarity	NPC159927
0.8476	Intermediate Similarity	NPC469335
0.8476	Intermediate Similarity	NPC196864
0.8466	Intermediate Similarity	NPC19747
0.8462	Intermediate Similarity	NPC472668
0.8462	Intermediate Similarity	NPC5079
0.8457	Intermediate Similarity	NPC471292
0.8452	Intermediate Similarity	NPC140952
0.8452	Intermediate Similarity	NPC237155
0.8452	Intermediate Similarity	NPC472823
0.8452	Intermediate Similarity	NPC474611
0.8443	Intermediate Similarity	NPC204663
0.8443	Intermediate Similarity	NPC263265
0.8439	Intermediate Similarity	NPC475237
0.8439	Intermediate Similarity	NPC475641
0.843	Intermediate Similarity	NPC160651
0.843	Intermediate Similarity	NPC327922
0.843	Intermediate Similarity	NPC296558
0.8424	Intermediate Similarity	NPC272590
0.8421	Intermediate Similarity	NPC121995
0.8412	Intermediate Similarity	NPC51568
0.8412	Intermediate Similarity	NPC234660
0.8412	Intermediate Similarity	NPC476197
0.8405	Intermediate Similarity	NPC224418
0.8402	Intermediate Similarity	NPC335761
0.8402	Intermediate Similarity	NPC333139
0.8402	Intermediate Similarity	NPC191828
0.8402	Intermediate Similarity	NPC25255
0.8393	Intermediate Similarity	NPC195131
0.8383	Intermediate Similarity	NPC75310
0.8382	Intermediate Similarity	NPC470995
0.8372	Intermediate Similarity	NPC270312
0.8372	Intermediate Similarity	NPC476850
0.8372	Intermediate Similarity	NPC173516
0.8372	Intermediate Similarity	NPC476861
0.8364	Intermediate Similarity	NPC156189
0.8364	Intermediate Similarity	NPC212257
0.8363	Intermediate Similarity	NPC56358
0.8363	Intermediate Similarity	NPC472664
0.8363	Intermediate Similarity	NPC476856
0.8363	Intermediate Similarity	NPC61967
0.8363	Intermediate Similarity	NPC261184
0.8363	Intermediate Similarity	NPC27541
0.8363	Intermediate Similarity	NPC126984
0.8363	Intermediate Similarity	NPC62692
0.8363	Intermediate Similarity	NPC476858
0.8363	Intermediate Similarity	NPC476857
0.8363	Intermediate Similarity	NPC469849
0.8363	Intermediate Similarity	NPC123088
0.8363	Intermediate Similarity	NPC276735
0.8353	Intermediate Similarity	NPC18986
0.8353	Intermediate Similarity	NPC68848
0.8353	Intermediate Similarity	NPC193798
0.8352	Intermediate Similarity	NPC478177
0.8344	Intermediate Similarity	NPC233763
0.8344	Intermediate Similarity	NPC62799
0.8333	Intermediate Similarity	NPC126723
0.8333	Intermediate Similarity	NPC285227
0.8333	Intermediate Similarity	NPC238843
0.8333	Intermediate Similarity	NPC199044
0.8333	Intermediate Similarity	NPC175964
0.8333	Intermediate Similarity	NPC471169
0.8324	Intermediate Similarity	NPC471397
0.8324	Intermediate Similarity	NPC242334
0.8324	Intermediate Similarity	NPC186746
0.8323	Intermediate Similarity	NPC178932
0.8314	Intermediate Similarity	NPC470875
0.8314	Intermediate Similarity	NPC149945
0.8304	Intermediate Similarity	NPC165218
0.8304	Intermediate Similarity	NPC283209
0.8304	Intermediate Similarity	NPC292389
0.8304	Intermediate Similarity	NPC472780
0.8304	Intermediate Similarity	NPC134254
0.8304	Intermediate Similarity	NPC39986
0.8304	Intermediate Similarity	NPC469338
0.8304	Intermediate Similarity	NPC472783
0.8304	Intermediate Similarity	NPC302369
0.8304	Intermediate Similarity	NPC285567
0.8303	Intermediate Similarity	NPC470790
0.8303	Intermediate Similarity	NPC470791
0.8294	Intermediate Similarity	NPC8389
0.8294	Intermediate Similarity	NPC472653
0.8293	Intermediate Similarity	NPC221809
0.8293	Intermediate Similarity	NPC71821
0.8284	Intermediate Similarity	NPC7059
0.8284	Intermediate Similarity	NPC469847
0.8276	Intermediate Similarity	NPC44602
0.8274	Intermediate Similarity	NPC471175
0.8274	Intermediate Similarity	NPC469336
0.8274	Intermediate Similarity	NPC472785
0.8266	Intermediate Similarity	NPC476853
0.8263	Intermediate Similarity	NPC475777
0.8263	Intermediate Similarity	NPC75906
0.8256	Intermediate Similarity	NPC470940
0.8256	Intermediate Similarity	NPC276551
0.8256	Intermediate Similarity	NPC476860
0.8249	Intermediate Similarity	NPC472665
0.8246	Intermediate Similarity	NPC79571
0.8246	Intermediate Similarity	NPC188649
0.8246	Intermediate Similarity	NPC329938
0.8246	Intermediate Similarity	NPC69028
0.8246	Intermediate Similarity	NPC472781
0.8246	Intermediate Similarity	NPC472767
0.8246	Intermediate Similarity	NPC472782
0.8239	Intermediate Similarity	NPC471437
0.8239	Intermediate Similarity	NPC94763
0.8239	Intermediate Similarity	NPC236004
0.8235	Intermediate Similarity	NPC477403
0.8232	Intermediate Similarity	NPC262198
0.8229	Intermediate Similarity	NPC159232
0.8229	Intermediate Similarity	NPC294512
0.8218	Intermediate Similarity	NPC271235
0.8214	Intermediate Similarity	NPC114880
0.8208	Intermediate Similarity	NPC23387
0.8208	Intermediate Similarity	NPC277618
0.8204	Intermediate Similarity	NPC18135
0.8202	Intermediate Similarity	NPC295914
0.8198	Intermediate Similarity	NPC477405
0.8198	Intermediate Similarity	NPC88841
0.8198	Intermediate Similarity	NPC288602
0.8193	Intermediate Similarity	NPC472654
0.8193	Intermediate Similarity	NPC192069
0.8193	Intermediate Similarity	NPC329180
0.8193	Intermediate Similarity	NPC211625
0.8192	Intermediate Similarity	NPC176413
0.8192	Intermediate Similarity	NPC56953
0.8192	Intermediate Similarity	NPC469633
0.8176	Intermediate Similarity	NPC195954
0.8176	Intermediate Similarity	NPC167142
0.8176	Intermediate Similarity	NPC88007
0.8176	Intermediate Similarity	NPC249021
0.8176	Intermediate Similarity	NPC194499
0.8171	Intermediate Similarity	NPC245522
0.8171	Intermediate Similarity	NPC56731
0.8171	Intermediate Similarity	NPC114513
0.8171	Intermediate Similarity	NPC118086
0.8171	Intermediate Similarity	NPC472659
0.8166	Intermediate Similarity	NPC472786
0.8166	Intermediate Similarity	NPC92979
0.8161	Intermediate Similarity	NPC310572
0.8144	Intermediate Similarity	NPC476122
0.8144	Intermediate Similarity	NPC46551
0.814	Intermediate Similarity	NPC263432
0.814	Intermediate Similarity	NPC290400
0.814	Intermediate Similarity	NPC96443
0.814	Intermediate Similarity	NPC117986
0.8136	Intermediate Similarity	NPC469576
0.8136	Intermediate Similarity	NPC471632
0.8129	Intermediate Similarity	NPC116639
0.8114	Intermediate Similarity	NPC472652
0.8111	Intermediate Similarity	NPC254588

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 NPC167340 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	933
0.2-0.3	1729
0.3-0.4	2836
0.4-0.5	2065
0.5-0.6	903
0.6-0.7	281
0.7-0.8	16
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8402	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8371	Intermediate Similarity	NPD8434	Phase 2
0.8274	Intermediate Similarity	NPD5761	Phase 2
0.8274	Intermediate Similarity	NPD5760	Phase 2
0.8192	Intermediate Similarity	NPD6765	Approved
0.8192	Intermediate Similarity	NPD6764	Approved
0.8011	Intermediate Similarity	NPD6785	Approved
0.8011	Intermediate Similarity	NPD6784	Approved
0.7805	Intermediate Similarity	NPD1471	Phase 3
0.7784	Intermediate Similarity	NPD7236	Approved
0.7667	Intermediate Similarity	NPD7799	Discontinued
0.7558	Intermediate Similarity	NPD7239	Suspended
0.7544	Intermediate Similarity	NPD6273	Approved
0.7473	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3226	Approved
0.7399	Intermediate Similarity	NPD920	Approved
0.7371	Intermediate Similarity	NPD6599	Discontinued
0.7345	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7819	Suspended
0.7303	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1247	Approved
0.7283	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD919	Approved
0.724	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5494	Approved
0.7232	Intermediate Similarity	NPD7411	Suspended
0.7222	Intermediate Similarity	NPD3749	Approved
0.7222	Intermediate Similarity	NPD7075	Discontinued
0.722	Intermediate Similarity	NPD8404	Phase 2
0.7198	Intermediate Similarity	NPD8127	Discontinued
0.7184	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD8032	Phase 2
0.7168	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7057	Phase 3
0.7167	Intermediate Similarity	NPD7058	Phase 2
0.7151	Intermediate Similarity	NPD4628	Phase 3
0.7128	Intermediate Similarity	NPD7685	Pre-registration
0.7126	Intermediate Similarity	NPD6799	Approved
0.7118	Intermediate Similarity	NPD2796	Approved
0.7107	Intermediate Similarity	NPD8285	Discontinued
0.7097	Intermediate Similarity	NPD3751	Discontinued
0.7095	Intermediate Similarity	NPD6801	Discontinued
0.7081	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6808	Phase 2
0.7059	Intermediate Similarity	NPD3748	Approved
0.7017	Intermediate Similarity	NPD5402	Approved
0.7017	Intermediate Similarity	NPD3817	Phase 2
0.6994	Remote Similarity	NPD1243	Approved
0.6989	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7768	Phase 2
0.6977	Remote Similarity	NPD5762	Approved
0.6977	Remote Similarity	NPD2346	Discontinued
0.6977	Remote Similarity	NPD5763	Approved
0.6963	Remote Similarity	NPD8312	Approved
0.6963	Remote Similarity	NPD8313	Approved
0.6959	Remote Similarity	NPD2799	Discontinued
0.6952	Remote Similarity	NPD7473	Discontinued
0.6947	Remote Similarity	NPD6559	Discontinued
0.6943	Remote Similarity	NPD8150	Discontinued
0.6935	Remote Similarity	NPD3926	Phase 2
0.6935	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7458	Discontinued
0.691	Remote Similarity	NPD5403	Approved
0.6893	Remote Similarity	NPD5401	Approved
0.6886	Remote Similarity	NPD6832	Phase 2
0.6885	Remote Similarity	NPD3882	Suspended
0.6882	Remote Similarity	NPD6355	Discontinued
0.6882	Remote Similarity	NPD3787	Discontinued
0.6881	Remote Similarity	NPD7497	Discontinued
0.6879	Remote Similarity	NPD6004	Phase 3
0.6879	Remote Similarity	NPD2344	Approved
0.6879	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6002	Phase 3
0.6879	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6005	Phase 3
0.6878	Remote Similarity	NPD5844	Phase 1
0.6878	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7961	Discontinued
0.686	Remote Similarity	NPD7033	Discontinued
0.6857	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3750	Approved
0.6848	Remote Similarity	NPD1876	Approved
0.6833	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6959	Discontinued
0.6824	Remote Similarity	NPD4140	Approved
0.6818	Remote Similarity	NPD3887	Approved
0.6816	Remote Similarity	NPD4107	Approved
0.681	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3267	Approved
0.6807	Remote Similarity	NPD3266	Approved
0.6805	Remote Similarity	NPD2313	Discontinued
0.6798	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7435	Discontinued
0.6798	Remote Similarity	NPD2534	Approved
0.6798	Remote Similarity	NPD2532	Approved
0.6798	Remote Similarity	NPD2533	Approved
0.6796	Remote Similarity	NPD7028	Phase 2
0.6793	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6232	Discontinued
0.6788	Remote Similarity	NPD5327	Phase 3
0.6786	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7003	Approved
0.6753	Remote Similarity	NPD8407	Phase 2
0.6748	Remote Similarity	NPD17	Approved
0.6743	Remote Similarity	NPD1549	Phase 2
0.6739	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7199	Phase 2
0.6727	Remote Similarity	NPD3972	Approved
0.6724	Remote Similarity	NPD1551	Phase 2
0.6723	Remote Similarity	NPD2309	Approved
0.6722	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2403	Approved
0.672	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6166	Phase 2
0.672	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3268	Approved
0.6706	Remote Similarity	NPD3764	Approved
0.6705	Remote Similarity	NPD2800	Approved
0.6703	Remote Similarity	NPD4380	Phase 2
0.6702	Remote Similarity	NPD7229	Phase 3
0.6701	Remote Similarity	NPD8435	Approved
0.67	Remote Similarity	NPD4482	Phase 3
0.6686	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8368	Discontinued
0.6683	Remote Similarity	NPD7874	Approved
0.6683	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7808	Phase 3
0.6649	Remote Similarity	NPD3818	Discontinued
0.6647	Remote Similarity	NPD6353	Approved
0.6647	Remote Similarity	NPD7095	Approved
0.6634	Remote Similarity	NPD7698	Approved
0.6634	Remote Similarity	NPD7697	Approved
0.6634	Remote Similarity	NPD7696	Phase 3
0.6632	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6280	Approved
0.663	Remote Similarity	NPD6279	Approved
0.663	Remote Similarity	NPD1934	Approved
0.6629	Remote Similarity	NPD6100	Approved
0.6629	Remote Similarity	NPD2935	Discontinued
0.6629	Remote Similarity	NPD6099	Approved
0.6628	Remote Similarity	NPD4307	Phase 2
0.6627	Remote Similarity	NPD1608	Approved
0.6616	Remote Similarity	NPD8360	Approved
0.6616	Remote Similarity	NPD8361	Approved
0.6613	Remote Similarity	NPD4966	Approved
0.6613	Remote Similarity	NPD4965	Approved
0.6613	Remote Similarity	NPD4967	Phase 2
0.6608	Remote Similarity	NPD6798	Discontinued
0.6608	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7871	Phase 2
0.6602	Remote Similarity	NPD7870	Phase 2
0.6602	Remote Similarity	NPD8319	Approved
0.6602	Remote Similarity	NPD8320	Phase 1
0.6598	Remote Similarity	NPD7251	Discontinued
0.6591	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2353	Approved
0.659	Remote Similarity	NPD5735	Approved
0.6585	Remote Similarity	NPD5585	Approved
0.6576	Remote Similarity	NPD5890	Approved
0.6576	Remote Similarity	NPD5889	Approved
0.6575	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8166	Discontinued
0.6571	Remote Similarity	NPD1510	Phase 2
0.657	Remote Similarity	NPD6233	Phase 2
0.6569	Remote Similarity	NPD6777	Approved
0.6569	Remote Similarity	NPD6781	Approved
0.6569	Remote Similarity	NPD6776	Approved
0.6569	Remote Similarity	NPD6779	Approved
0.6569	Remote Similarity	NPD6780	Approved
0.6569	Remote Similarity	NPD6782	Approved
0.6569	Remote Similarity	NPD6778	Approved
0.6568	Remote Similarity	NPD2798	Approved
0.6562	Remote Similarity	NPD7177	Discontinued
0.6556	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD6797	Phase 2
0.6545	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6234	Discontinued
0.6541	Remote Similarity	NPD37	Approved
0.6532	Remote Similarity	NPD2979	Phase 3
0.6532	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5736	Approved
0.6528	Remote Similarity	NPD7907	Approved
0.6522	Remote Similarity	NPD6585	Discontinued
0.6514	Remote Similarity	NPD7097	Phase 1
0.6509	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7701	Phase 2

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