NPASS Compound

Structure

CID238843 OpenBabel06191716042D 33 37 0 0 1 0 0 0 0 0999 V2000 3.5242 -2.8276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0947 0.9569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0948 1.9668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6571 1.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8748 0.5051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6877 -1.0098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8442 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3755 2.9236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6135 -0.3020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5316 2.4367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1861 0.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3760 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6878 0.9729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4223 -1.8582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8436 -1.4611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6878 0.9751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3760 0.9751 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8436 -0.4871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2196 2.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5319 -0.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8441 -0.4874 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2199 1.4620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5319 1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6878 0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2109 -1.2853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7121 -1.9629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0881 2.9380 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6140 1.2735 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5319 -1.4617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 7 10 1 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 8 22 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 27 1 0 0 0 0 11 26 1 0 0 0 0 12 32 1 0 0 0 0 13 18 1 0 0 0 0 13 21 2 0 0 0 0 14 20 1 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 32 1 0 0 0 0 16 29 2 0 0 0 0 16 33 1 0 0 0 0 17 24 1 0 0 0 0 18 24 1 0 0 0 0 18 30 2 0 0 0 0 19 26 1 6 0 0 0 19 28 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 6 0 0 0 21 27 1 0 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 31 2 0 0 0 0 23 28 1 1 0 0 0 23 33 1 0 0 0 0 24 27 1 6 0 0 0 26 4 1 6 0 0 0 27 5 1 1 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.24
Volume:	475.558
LogP:	3.625
LogD:	3.07
LogS:	-4.785
# Rotatable Bonds:	3
TPSA:	73.58
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.563
Synthetic Accessibility Score:	4.973
Fsp3:	0.607
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.24
MDCK Permeability:	3.9816695789340883e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.904
30% Bioavailability (F30%):	0.904

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	92.49396514892578%
Volume Distribution (VD):	2.055
Pgp-substrate:	8.874319076538086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.261
CYP2C19-inhibitor:	0.354
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.708
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.148
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.86
CYP3A4-substrate:	0.847

ADMET: Excretion

Clearance (CL):	4.675
Half-life (T1/2):	0.344

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.208
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.537
Carcinogencity:	0.163
Eye Corrosion:	0.004
Eye Irritation:	0.033
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC238843

Natural Product ID:	NPC238843
*Common Name:**	17-Epiazadiradione
IUPAC Name:	[(5R,7R,8R,9R,10R,13S,17S)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate
Synonyms:	17-Epiazadiradione
Standard InCHIKey:	KWAMDQVQFVBEAU-ZRCRZKIJSA-N
Standard InCHI:	InChI=1S/C28H34O5/c1-16(29)33-23-14-20-25(2,3)22(31)8-11-26(20,4)19-7-10-27(5)21(28(19,23)6)13-18(30)24(27)17-9-12-32-15-17/h8-9,11-13,15,19-20,23-24H,7,10,14H2,1-6H3/t19-,20+,23-,24+,26-,27-,28-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@]3(C)C(=CC(=O)[C@@H]3c3ccoc3)[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774392
PubChem CID:	12308716
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.	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.	bark	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	5
Others	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	12600.0	nM	PMID[507706]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[507706]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[507706]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[507706]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	87.0	%	PMID[507707]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	86.5	%	PMID[507707]
NPT847	Organism	Reticulitermes speratus	Reticulitermes speratus	Survival	=	85.5	%	PMID[507707]

☑ 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 NPC238843 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	352
0.1-0.2	1473
0.2-0.3	2919
0.3-0.4	6405
0.4-0.5	11692
0.5-0.6	10525
0.6-0.7	8159
0.7-0.8	830
0.8-0.85	237
0.85-0.9	90
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC199044
0.9855	High Similarity	NPC471292
0.9706	High Similarity	NPC56197
0.951	High Similarity	NPC272590
0.95	High Similarity	NPC185456
0.9315	High Similarity	NPC25351
0.9236	High Similarity	NPC234494
0.9236	High Similarity	NPC471001
0.9231	High Similarity	NPC471174
0.9231	High Similarity	NPC302987
0.9184	High Similarity	NPC92979
0.9172	High Similarity	NPC470997
0.9097	High Similarity	NPC216755
0.9048	High Similarity	NPC246164
0.9048	High Similarity	NPC33938
0.9028	High Similarity	NPC470999
0.898	High Similarity	NPC116717
0.898	High Similarity	NPC291150
0.8958	High Similarity	NPC34056
0.8947	High Similarity	NPC224394
0.8947	High Similarity	NPC663
0.8933	High Similarity	NPC469847
0.8926	High Similarity	NPC155939
0.8926	High Similarity	NPC296807
0.8926	High Similarity	NPC141538
0.8919	High Similarity	NPC471002
0.8912	High Similarity	NPC5180
0.8912	High Similarity	NPC469335
0.8912	High Similarity	NPC156189
0.8912	High Similarity	NPC159927
0.8889	High Similarity	NPC142113
0.8882	High Similarity	NPC197596
0.8851	High Similarity	NPC471000
0.8844	High Similarity	NPC470998
0.8844	High Similarity	NPC472654
0.8794	High Similarity	NPC42400
0.8792	High Similarity	NPC470996
0.8784	High Similarity	NPC196846
0.8784	High Similarity	NPC477404
0.8784	High Similarity	NPC196864
0.8777	High Similarity	NPC471006
0.8768	High Similarity	NPC298190
0.8767	High Similarity	NPC233763
0.8767	High Similarity	NPC262198
0.8733	High Similarity	NPC178932
0.8732	High Similarity	NPC236532
0.8732	High Similarity	NPC476943
0.8723	High Similarity	NPC146872
0.8716	High Similarity	NPC470790
0.8716	High Similarity	NPC470791
0.8707	High Similarity	NPC224418
0.8705	High Similarity	NPC471817
0.8699	High Similarity	NPC56731
0.869	High Similarity	NPC267632
0.8684	High Similarity	NPC197137
0.8675	High Similarity	NPC469850
0.8675	High Similarity	NPC469336
0.8662	High Similarity	NPC310830
0.8636	High Similarity	NPC471003
0.863	High Similarity	NPC251865
0.8623	High Similarity	NPC198904
0.8621	High Similarity	NPC121158
0.8603	High Similarity	NPC179354
0.8601	High Similarity	NPC220094
0.8581	High Similarity	NPC71821
0.8562	High Similarity	NPC470118
0.8562	High Similarity	NPC472283
0.854	High Similarity	NPC74612
0.8533	High Similarity	NPC46551
0.8531	High Similarity	NPC310043
0.8531	High Similarity	NPC307401
0.8531	High Similarity	NPC470742
0.8523	High Similarity	NPC93666
0.8514	High Similarity	NPC346
0.8506	High Similarity	NPC474932
0.8503	High Similarity	NPC476944
0.8497	Intermediate Similarity	NPC41880
0.8497	Intermediate Similarity	NPC204663
0.8497	Intermediate Similarity	NPC104736
0.8487	Intermediate Similarity	NPC30222
0.8487	Intermediate Similarity	NPC471863
0.8462	Intermediate Similarity	NPC214572
0.8456	Intermediate Similarity	NPC16922
0.8456	Intermediate Similarity	NPC221809
0.8442	Intermediate Similarity	NPC195131
0.8442	Intermediate Similarity	NPC167142
0.8442	Intermediate Similarity	NPC472772
0.8442	Intermediate Similarity	NPC304692
0.8435	Intermediate Similarity	NPC80635
0.8435	Intermediate Similarity	NPC223415
0.8431	Intermediate Similarity	NPC35000
0.8431	Intermediate Similarity	NPC264943
0.8425	Intermediate Similarity	NPC20500
0.8421	Intermediate Similarity	NPC469503
0.8421	Intermediate Similarity	NPC182427
0.8421	Intermediate Similarity	NPC75906
0.8421	Intermediate Similarity	NPC472672
0.8421	Intermediate Similarity	NPC322546
0.8421	Intermediate Similarity	NPC308205
0.8421	Intermediate Similarity	NPC29695
0.8414	Intermediate Similarity	NPC202260
0.8411	Intermediate Similarity	NPC212257
0.8411	Intermediate Similarity	NPC476122
0.8397	Intermediate Similarity	NPC471167
0.8397	Intermediate Similarity	NPC69028
0.8397	Intermediate Similarity	NPC471166
0.8397	Intermediate Similarity	NPC470792
0.8392	Intermediate Similarity	NPC92941
0.838	Intermediate Similarity	NPC470740
0.8377	Intermediate Similarity	NPC60973
0.8377	Intermediate Similarity	NPC209364
0.8369	Intermediate Similarity	NPC61788
0.8366	Intermediate Similarity	NPC237259
0.8366	Intermediate Similarity	NPC302054
0.8366	Intermediate Similarity	NPC98206
0.8366	Intermediate Similarity	NPC34421
0.8366	Intermediate Similarity	NPC253201
0.8356	Intermediate Similarity	NPC67003
0.8355	Intermediate Similarity	NPC18135
0.8344	Intermediate Similarity	NPC292389
0.8344	Intermediate Similarity	NPC195325
0.8344	Intermediate Similarity	NPC329180
0.8344	Intermediate Similarity	NPC471168
0.8344	Intermediate Similarity	NPC469338
0.8344	Intermediate Similarity	NPC165218
0.8333	Intermediate Similarity	NPC191828
0.8333	Intermediate Similarity	NPC167340
0.8333	Intermediate Similarity	NPC287559
0.8333	Intermediate Similarity	NPC10088
0.8333	Intermediate Similarity	NPC470941
0.8333	Intermediate Similarity	NPC255414
0.8323	Intermediate Similarity	NPC81405
0.8323	Intermediate Similarity	NPC286722
0.8323	Intermediate Similarity	NPC469848
0.8312	Intermediate Similarity	NPC471175
0.8312	Intermediate Similarity	NPC281258
0.8311	Intermediate Similarity	NPC243577
0.8311	Intermediate Similarity	NPC470741
0.8302	Intermediate Similarity	NPC478179
0.8301	Intermediate Similarity	NPC121615
0.8301	Intermediate Similarity	NPC476201
0.8301	Intermediate Similarity	NPC294511
0.8299	Intermediate Similarity	NPC205765
0.8291	Intermediate Similarity	NPC470940
0.8291	Intermediate Similarity	NPC469849
0.8291	Intermediate Similarity	NPC276551
0.8288	Intermediate Similarity	NPC90953
0.8288	Intermediate Similarity	NPC474722
0.8286	Intermediate Similarity	NPC327527
0.8286	Intermediate Similarity	NPC112706
0.8286	Intermediate Similarity	NPC207294
0.8286	Intermediate Similarity	NPC476917
0.828	Intermediate Similarity	NPC470939
0.828	Intermediate Similarity	NPC472771
0.828	Intermediate Similarity	NPC472668
0.828	Intermediate Similarity	NPC6326
0.828	Intermediate Similarity	NPC329938
0.828	Intermediate Similarity	NPC68848
0.828	Intermediate Similarity	NPC472767
0.8278	Intermediate Similarity	NPC471007
0.8273	Intermediate Similarity	NPC138139
0.8273	Intermediate Similarity	NPC46536
0.8269	Intermediate Similarity	NPC140952
0.8269	Intermediate Similarity	NPC475295
0.8269	Intermediate Similarity	NPC475226
0.8269	Intermediate Similarity	NPC477403
0.8269	Intermediate Similarity	NPC307383
0.8269	Intermediate Similarity	NPC84349
0.8269	Intermediate Similarity	NPC237155
0.8269	Intermediate Similarity	NPC473473
0.8267	Intermediate Similarity	NPC62799
0.8264	Intermediate Similarity	NPC476947
0.8261	Intermediate Similarity	NPC285227
0.8258	Intermediate Similarity	NPC175964
0.8258	Intermediate Similarity	NPC471169
0.8258	Intermediate Similarity	NPC263265
0.8258	Intermediate Similarity	NPC107646
0.8252	Intermediate Similarity	NPC218838
0.8248	Intermediate Similarity	NPC36255
0.8247	Intermediate Similarity	NPC282445
0.8247	Intermediate Similarity	NPC10429
0.8247	Intermediate Similarity	NPC57998
0.8243	Intermediate Similarity	NPC473152
0.8243	Intermediate Similarity	NPC52412
0.8239	Intermediate Similarity	NPC89133
0.8239	Intermediate Similarity	NPC478178
0.8239	Intermediate Similarity	NPC470875
0.8235	Intermediate Similarity	NPC144010
0.8231	Intermediate Similarity	NPC148374
0.8228	Intermediate Similarity	NPC476197
0.8228	Intermediate Similarity	NPC283209
0.8228	Intermediate Similarity	NPC419
0.8228	Intermediate Similarity	NPC285567
0.8228	Intermediate Similarity	NPC477405
0.8228	Intermediate Similarity	NPC472773
0.8228	Intermediate Similarity	NPC472669
0.8227	Intermediate Similarity	NPC59502
0.8224	Intermediate Similarity	NPC125182
0.8224	Intermediate Similarity	NPC69647
0.8217	Intermediate Similarity	NPC305016

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 NPC238843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	1011
0.2-0.3	1859
0.3-0.4	2715
0.4-0.5	2006
0.5-0.6	995
0.6-0.7	252
0.7-0.8	19
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
0.8194	Intermediate Similarity	NPD5760	Phase 2
0.8194	Intermediate Similarity	NPD5761	Phase 2
0.7875	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6765	Approved
0.7784	Intermediate Similarity	NPD6764	Approved
0.7682	Intermediate Similarity	NPD1471	Phase 3
0.7661	Intermediate Similarity	NPD8434	Phase 2
0.7602	Intermediate Similarity	NPD6784	Approved
0.7602	Intermediate Similarity	NPD6785	Approved
0.7566	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6273	Approved
0.7333	Intermediate Similarity	NPD8032	Phase 2
0.7244	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4628	Phase 3
0.7107	Intermediate Similarity	NPD7236	Approved
0.7101	Intermediate Similarity	NPD6808	Phase 2
0.7097	Intermediate Similarity	NPD2799	Discontinued
0.7095	Intermediate Similarity	NPD1876	Approved
0.7075	Intermediate Similarity	NPD3972	Approved
0.7055	Intermediate Similarity	NPD3226	Approved
0.7055	Intermediate Similarity	NPD7458	Discontinued
0.7047	Intermediate Similarity	NPD3267	Approved
0.7047	Intermediate Similarity	NPD3266	Approved
0.7037	Intermediate Similarity	NPD920	Approved
0.7006	Intermediate Similarity	NPD2346	Discontinued
0.7006	Intermediate Similarity	NPD2344	Approved
0.6988	Remote Similarity	NPD7819	Suspended
0.6986	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8127	Discontinued
0.6928	Remote Similarity	NPD3268	Approved
0.6914	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6832	Phase 2
0.6894	Remote Similarity	NPD643	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7239	Suspended
0.6879	Remote Similarity	NPD3748	Approved
0.6875	Remote Similarity	NPD7003	Approved
0.6848	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4140	Approved
0.6835	Remote Similarity	NPD2796	Approved
0.6832	Remote Similarity	NPD2309	Approved
0.6818	Remote Similarity	NPD2313	Discontinued
0.681	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6599	Discontinued
0.68	Remote Similarity	NPD5327	Phase 3
0.6795	Remote Similarity	NPD6355	Discontinued
0.6786	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5494	Approved
0.6779	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7411	Suspended
0.6757	Remote Similarity	NPD17	Approved
0.6746	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1241	Discontinued
0.6731	Remote Similarity	NPD2979	Phase 3
0.6731	Remote Similarity	NPD4307	Phase 2
0.6728	Remote Similarity	NPD3887	Approved
0.6726	Remote Similarity	NPD6279	Approved
0.6726	Remote Similarity	NPD6280	Approved
0.6725	Remote Similarity	NPD919	Approved
0.6722	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1243	Approved
0.6707	Remote Similarity	NPD7028	Phase 2
0.6689	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD1281	Approved
0.6667	Remote Similarity	NPD2798	Approved
0.6647	Remote Similarity	NPD1247	Approved
0.6643	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2438	Suspended
0.6623	Remote Similarity	NPD1608	Approved
0.6601	Remote Similarity	NPD2797	Approved
0.6592	Remote Similarity	NPD6559	Discontinued
0.6584	Remote Similarity	NPD5762	Approved
0.6584	Remote Similarity	NPD5763	Approved
0.6582	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5691	Approved
0.6566	Remote Similarity	NPD8404	Phase 2
0.6562	Remote Similarity	NPD4308	Phase 3
0.6561	Remote Similarity	NPD4107	Approved
0.6545	Remote Similarity	NPD6799	Approved
0.6541	Remote Similarity	NPD6353	Approved
0.6538	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1283	Approved
0.6534	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6801	Discontinued
0.6527	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6099	Approved
0.6522	Remote Similarity	NPD6100	Approved
0.6522	Remote Similarity	NPD2935	Discontinued
0.6522	Remote Similarity	NPD2531	Phase 2
0.6517	Remote Similarity	NPD5844	Phase 1
0.6516	Remote Similarity	NPD5736	Approved
0.6512	Remote Similarity	NPD7058	Phase 2
0.6512	Remote Similarity	NPD7057	Phase 3
0.6506	Remote Similarity	NPD2533	Approved
0.6506	Remote Similarity	NPD2532	Approved
0.6506	Remote Similarity	NPD2534	Approved
0.65	Remote Similarity	NPD7097	Phase 1
0.6497	Remote Similarity	NPD3764	Approved
0.6497	Remote Similarity	NPD7473	Discontinued
0.6497	Remote Similarity	NPD6798	Discontinued
0.6497	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6004	Phase 3
0.6481	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6005	Phase 3
0.6481	Remote Similarity	NPD6002	Phase 3
0.6481	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD2353	Approved
0.6481	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4622	Approved
0.6478	Remote Similarity	NPD4618	Approved
0.6478	Remote Similarity	NPD5735	Approved
0.6477	Remote Similarity	NPD3926	Phase 2
0.6471	Remote Similarity	NPD5890	Approved
0.6471	Remote Similarity	NPD5889	Approved
0.6471	Remote Similarity	NPD4359	Approved
0.6467	Remote Similarity	NPD1651	Approved
0.6461	Remote Similarity	NPD7799	Discontinued
0.6457	Remote Similarity	NPD7199	Phase 2
0.6446	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD1549	Phase 2
0.644	Remote Similarity	NPD4482	Phase 3
0.6433	Remote Similarity	NPD7095	Approved
0.6424	Remote Similarity	NPD1778	Approved
0.642	Remote Similarity	NPD1551	Phase 2
0.642	Remote Similarity	NPD4477	Approved
0.642	Remote Similarity	NPD4476	Approved
0.642	Remote Similarity	NPD7229	Phase 3
0.6416	Remote Similarity	NPD7768	Phase 2
0.6416	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3142	Approved
0.6415	Remote Similarity	NPD3140	Approved
0.6407	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD2800	Approved
0.6398	Remote Similarity	NPD5688	Approved
0.6398	Remote Similarity	NPD5689	Approved
0.6395	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2182	Approved
0.6387	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.638	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.638	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD1933	Approved
0.6374	Remote Similarity	NPD6873	Phase 2
0.6369	Remote Similarity	NPD7177	Discontinued
0.6358	Remote Similarity	NPD7033	Discontinued
0.6358	Remote Similarity	NPD2296	Approved
0.6358	Remote Similarity	NPD5977	Approved
0.6358	Remote Similarity	NPD3024	Approved
0.6358	Remote Similarity	NPD3817	Phase 2
0.6358	Remote Similarity	NPD3025	Approved
0.6358	Remote Similarity	NPD5978	Approved
0.6352	Remote Similarity	NPD7961	Discontinued
0.6352	Remote Similarity	NPD4870	Approved
0.6346	Remote Similarity	NPD5647	Approved
0.6346	Remote Similarity	NPD1019	Discontinued
0.6341	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2897	Discontinued
0.6339	Remote Similarity	NPD8312	Approved
0.6339	Remote Similarity	NPD8313	Approved
0.6328	Remote Similarity	NPD6232	Discontinued
0.6327	Remote Similarity	NPD7094	Approved
0.6327	Remote Similarity	NPD5535	Approved
0.6327	Remote Similarity	NPD6858	Approved
0.6325	Remote Similarity	NPD2354	Approved
0.6322	Remote Similarity	NPD4966	Approved
0.6322	Remote Similarity	NPD3882	Suspended
0.6322	Remote Similarity	NPD4967	Phase 2
0.6322	Remote Similarity	NPD4965	Approved
0.6316	Remote Similarity	NPD6585	Discontinued
0.6316	Remote Similarity	NPD2932	Approved
0.6316	Remote Similarity	NPD4626	Approved
0.6312	Remote Similarity	NPD4060	Phase 1
0.6299	Remote Similarity	NPD9717	Approved
0.629	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7497	Discontinued
0.6287	Remote Similarity	NPD7440	Discontinued
0.6282	Remote Similarity	NPD1203	Approved
0.6279	Remote Similarity	NPD6385	Approved
0.6279	Remote Similarity	NPD6677	Suspended
0.6279	Remote Similarity	NPD6386	Approved
0.6278	Remote Similarity	NPD3818	Discontinued
0.6277	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3496	Discontinued
0.6275	Remote Similarity	NPD3026	Approved
0.6275	Remote Similarity	NPD3023	Approved
0.6271	Remote Similarity	NPD6959	Discontinued
0.6264	Remote Similarity	NPD5402	Approved
0.6258	Remote Similarity	NPD1510	Phase 2
0.6257	Remote Similarity	NPD2651	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