NPASS Compound

Structure

NPC475376 OpenBabel07101718302D 41 48 0 0 1 0 0 0 0 0999 V2000 -1.1573 -2.0090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5076 -0.2354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4746 1.1619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5017 1.1777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1501 -0.1684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6732 0.2706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7077 -2.0455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7447 1.1728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 1.1137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9837 -0.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2228 -1.3075 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0558 0.9259 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3673 0.7881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1534 -1.7836 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5987 -1.1167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3710 0.3856 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0398 -0.2167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5987 -0.2167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8192 -1.5667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1505 -0.3629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9467 1.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2362 -0.6827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0398 -1.1167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6801 -0.5895 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8192 0.2334 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4547 0.0615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8799 -0.7575 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1704 -0.8837 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4146 1.5576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1258 1.2726 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8192 -2.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4286 -1.2189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8836 1.9663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3493 -2.4953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7527 0.3059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7557 0.6742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1084 -0.0473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4547 -1.3948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7370 1.2078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2237 -1.1393 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 2 24 1 0 0 0 0 3 35 1 0 0 0 0 4 36 1 0 0 0 0 5 6 2 0 0 0 0 5 27 1 0 0 0 0 6 37 1 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 39 1 0 0 0 0 10 26 1 0 0 0 0 10 38 1 0 0 0 0 11 24 1 1 0 0 0 11 27 1 0 0 0 0 12 25 1 6 0 0 0 12 29 1 0 0 0 0 13 26 1 6 0 0 0 13 30 1 0 0 0 0 14 28 1 1 0 0 0 14 40 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 15 38 1 6 0 0 0 16 17 1 0 0 0 0 16 20 1 6 0 0 0 16 39 1 0 0 0 0 17 23 1 1 0 0 0 17 25 1 0 0 0 0 18 25 1 1 0 0 0 18 26 1 0 0 0 0 19 23 1 6 0 0 0 19 31 1 0 0 0 0 20 32 2 0 0 0 0 20 35 1 0 0 0 0 21 33 2 0 0 0 0 21 36 1 0 0 0 0 22 27 1 6 0 0 0 22 37 1 0 0 0 0 22 40 1 0 0 0 0 23 1 1 1 0 0 0 23 28 1 0 0 0 0 24 28 1 6 0 0 0 24 41 1 0 0 0 0 25 9 1 1 0 0 0 26 21 1 1 0 0 0 27 34 1 1 0 0 0 28 41 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.22
Volume:	530.756
LogP:	0.812
LogD:	-0.14
LogS:	-5.007
# Rotatable Bonds:	5
TPSA:	182.97
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.221
Synthetic Accessibility Score:	7.465
Fsp3:	0.857
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:	-5.632
MDCK Permeability:	0.00010435097647132352
Pgp-inhibitor:	0.013
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	21.516735076904297%
Volume Distribution (VD):	0.736
Pgp-substrate:	63.00088882446289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.991
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.597
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.311
CYP3A4-substrate:	0.336

ADMET: Excretion

Clearance (CL):	2.188
Half-life (T1/2):	0.425

ADMET: Toxicity

hERG Blockers:	0.234
Human Hepatotoxicity (H-HT):	0.78
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.348
Rat Oral Acute Toxicity:	0.495
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.26
Carcinogencity:	0.978
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC475376

Natural Product ID:	NPC475376
*Common Name:**	Azadirachtol
IUPAC Name:	n.a.
Synonyms:	Azadirachtol
Standard InCHIKey:	KPVJTWLSYIGGCU-KZBRQISASA-N
Standard InCHI:	InChI=1S/C28H36O13/c1-23(28-14-7-11(24(28,2)41-28)27(34)5-6-37-22(27)40-14)17-16(20(32)35-3)39-9-25(17)12(29)8-13(30)26(21(33)36-4)10-38-15(18(25)26)19(23)31/h5-6,11-19,22,29-31,34H,7-10H2,1-4H3/t11-,12+,13-,14+,15-,16+,17+,18-,19-,22+,23+,24+,25-,26+,27+,28+/m1/s1
SMILES:	C[C@@]1([C@@H]2[C@@H](C(=O)OC)OC[C@]32[C@H](C[C@H]([C@]2(CO[C@H]([C@H]32)[C@H]1O)C(=O)OC)O)O)[C@@]12[C@@H]3C[C@H]([C@]1(C)O2)[C@]1(C=CO[C@H]1O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504505
PubChem CID:	23256847
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
NPO1837	Azadirachta excelsa	Species	Meliaceae	Eukaryota	seed kernels	n.a.	n.a.	PMID[16038546]
NPO40792	Azaridachta indica	Species	n.a.	n.a.	Leaves	n.a.	n.a.	PMID[24499352]
NPO1837	Azadirachta excelsa	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
LD50	4
Others	1

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT849	Organism	Plutella xylostella	Plutella xylostella	LD50	=	4.88	mg.kg-1	PMID[530539]
NPT849	Organism	Plutella xylostella	Plutella xylostella	LD50	=	3.28	mg.kg-1	PMID[530539]
NPT849	Organism	Plutella xylostella	Plutella xylostella	LD50	=	2.35	mg.kg-1	PMID[530539]
NPT849	Organism	Plutella xylostella	Plutella xylostella	LD50	=	1.78	mg.kg-1	PMID[530539]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	AFI	=	6.1	%	PMID[530540]

☑ 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 NPC475376 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	375
0.1-0.2	2563
0.2-0.3	6555
0.3-0.4	11984
0.4-0.5	10371
0.5-0.6	6244
0.6-0.7	3951
0.7-0.8	619
0.8-0.85	22
0.85-0.9	1
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC219058
0.9919	High Similarity	NPC256618
0.9675	High Similarity	NPC42206
0.9365	High Similarity	NPC470117
0.9242	High Similarity	NPC48813
0.9242	High Similarity	NPC194854
0.9173	High Similarity	NPC16729
0.9173	High Similarity	NPC475462
0.9023	High Similarity	NPC471172
0.9015	High Similarity	NPC5153
0.9015	High Similarity	NPC48414
0.8806	High Similarity	NPC471171
0.8306	Intermediate Similarity	NPC470115
0.8306	Intermediate Similarity	NPC470116
0.8226	Intermediate Similarity	NPC285086
0.8209	Intermediate Similarity	NPC471234
0.813	Intermediate Similarity	NPC86217
0.8049	Intermediate Similarity	NPC305939
0.8	Intermediate Similarity	NPC88668
0.8	Intermediate Similarity	NPC65858
0.7984	Intermediate Similarity	NPC130302
0.7984	Intermediate Similarity	NPC98633
0.7955	Intermediate Similarity	NPC273962
0.7953	Intermediate Similarity	NPC475490
0.7939	Intermediate Similarity	NPC135038
0.7939	Intermediate Similarity	NPC267822
0.7939	Intermediate Similarity	NPC43252
0.791	Intermediate Similarity	NPC470880
0.7879	Intermediate Similarity	NPC169818
0.7852	Intermediate Similarity	NPC475389
0.7852	Intermediate Similarity	NPC473838
0.7846	Intermediate Similarity	NPC317635
0.7846	Intermediate Similarity	NPC329008
0.7846	Intermediate Similarity	NPC142882
0.784	Intermediate Similarity	NPC255655
0.7795	Intermediate Similarity	NPC102619
0.7778	Intermediate Similarity	NPC471251
0.7778	Intermediate Similarity	NPC56025
0.7761	Intermediate Similarity	NPC473265
0.7761	Intermediate Similarity	NPC117702
0.7761	Intermediate Similarity	NPC473253
0.7761	Intermediate Similarity	NPC146456
0.7761	Intermediate Similarity	NPC469757
0.7761	Intermediate Similarity	NPC470882
0.7761	Intermediate Similarity	NPC471357
0.7761	Intermediate Similarity	NPC305496
0.7744	Intermediate Similarity	NPC473255
0.7744	Intermediate Similarity	NPC475194
0.7734	Intermediate Similarity	NPC79193
0.771	Intermediate Similarity	NPC471406
0.7704	Intermediate Similarity	NPC168899
0.7704	Intermediate Similarity	NPC476091
0.7704	Intermediate Similarity	NPC475636
0.7704	Intermediate Similarity	NPC473620
0.7704	Intermediate Similarity	NPC293623
0.7704	Intermediate Similarity	NPC476078
0.7704	Intermediate Similarity	NPC311534
0.7704	Intermediate Similarity	NPC69273
0.7704	Intermediate Similarity	NPC295220
0.7698	Intermediate Similarity	NPC124053
0.7698	Intermediate Similarity	NPC477236
0.7687	Intermediate Similarity	NPC174367
0.7687	Intermediate Similarity	NPC47113
0.7674	Intermediate Similarity	NPC88945
0.7669	Intermediate Similarity	NPC227397
0.7664	Intermediate Similarity	NPC473805
0.7664	Intermediate Similarity	NPC471855
0.7664	Intermediate Similarity	NPC473519
0.7661	Intermediate Similarity	NPC285927
0.7661	Intermediate Similarity	NPC166079
0.7661	Intermediate Similarity	NPC291414
0.7647	Intermediate Similarity	NPC86159
0.7647	Intermediate Similarity	NPC471352
0.7647	Intermediate Similarity	NPC469754
0.7647	Intermediate Similarity	NPC471359
0.7647	Intermediate Similarity	NPC180079
0.7647	Intermediate Similarity	NPC9499
0.7647	Intermediate Similarity	NPC284406
0.7647	Intermediate Similarity	NPC469752
0.7647	Intermediate Similarity	NPC309096
0.7647	Intermediate Similarity	NPC10823
0.7647	Intermediate Similarity	NPC219085
0.7647	Intermediate Similarity	NPC476851
0.7647	Intermediate Similarity	NPC470851
0.7647	Intermediate Similarity	NPC251866
0.7647	Intermediate Similarity	NPC17896
0.7647	Intermediate Similarity	NPC89514
0.7647	Intermediate Similarity	NPC70542
0.7647	Intermediate Similarity	NPC6108
0.7647	Intermediate Similarity	NPC469753
0.7647	Intermediate Similarity	NPC54614
0.7647	Intermediate Similarity	NPC197707
0.7647	Intermediate Similarity	NPC471358
0.7647	Intermediate Similarity	NPC469755
0.7647	Intermediate Similarity	NPC469751
0.7647	Intermediate Similarity	NPC471360
0.7647	Intermediate Similarity	NPC471361
0.7638	Intermediate Similarity	NPC157476
0.7638	Intermediate Similarity	NPC473062
0.7638	Intermediate Similarity	NPC272242
0.763	Intermediate Similarity	NPC470780
0.763	Intermediate Similarity	NPC2757
0.7626	Intermediate Similarity	NPC171619
0.7619	Intermediate Similarity	NPC471250
0.7615	Intermediate Similarity	NPC179429
0.7615	Intermediate Similarity	NPC470171
0.7615	Intermediate Similarity	NPC473304
0.7609	Intermediate Similarity	NPC475487
0.7609	Intermediate Similarity	NPC102015
0.7609	Intermediate Similarity	NPC225385
0.7609	Intermediate Similarity	NPC157817
0.7609	Intermediate Similarity	NPC298783
0.7609	Intermediate Similarity	NPC104585
0.7594	Intermediate Similarity	NPC222688
0.7591	Intermediate Similarity	NPC476852
0.7591	Intermediate Similarity	NPC241008
0.7589	Intermediate Similarity	NPC75616
0.7581	Intermediate Similarity	NPC100078
0.7581	Intermediate Similarity	NPC88469
0.7574	Intermediate Similarity	NPC470850
0.7574	Intermediate Similarity	NPC188291
0.7574	Intermediate Similarity	NPC473888
0.7571	Intermediate Similarity	NPC251998
0.7559	Intermediate Similarity	NPC106760
0.7557	Intermediate Similarity	NPC470776
0.7556	Intermediate Similarity	NPC93368
0.7556	Intermediate Similarity	NPC87662
0.7554	Intermediate Similarity	NPC477234
0.7554	Intermediate Similarity	NPC478072
0.754	Intermediate Similarity	NPC208461
0.754	Intermediate Similarity	NPC289702
0.7538	Intermediate Similarity	NPC470628
0.7538	Intermediate Similarity	NPC474046
0.7538	Intermediate Similarity	NPC474734
0.7538	Intermediate Similarity	NPC259306
0.7537	Intermediate Similarity	NPC27363
0.7536	Intermediate Similarity	NPC254614
0.7536	Intermediate Similarity	NPC6274
0.7536	Intermediate Similarity	NPC19124
0.7536	Intermediate Similarity	NPC42670
0.7536	Intermediate Similarity	NPC254146
0.7536	Intermediate Similarity	NPC33378
0.7536	Intermediate Similarity	NPC100390
0.7536	Intermediate Similarity	NPC93416
0.752	Intermediate Similarity	NPC306776
0.7519	Intermediate Similarity	NPC470478
0.7519	Intermediate Similarity	NPC275675
0.7519	Intermediate Similarity	NPC97002
0.7519	Intermediate Similarity	NPC477046
0.7519	Intermediate Similarity	NPC102822
0.7519	Intermediate Similarity	NPC132668
0.7518	Intermediate Similarity	NPC295885
0.7518	Intermediate Similarity	NPC140045
0.7518	Intermediate Similarity	NPC471407
0.7518	Intermediate Similarity	NPC596
0.7518	Intermediate Similarity	NPC473593
0.75	Intermediate Similarity	NPC477071
0.75	Intermediate Similarity	NPC319570
0.75	Intermediate Similarity	NPC19028
0.75	Intermediate Similarity	NPC473203
0.75	Intermediate Similarity	NPC42399
0.75	Intermediate Similarity	NPC287423
0.75	Intermediate Similarity	NPC262813
0.75	Intermediate Similarity	NPC152091
0.75	Intermediate Similarity	NPC179412
0.75	Intermediate Similarity	NPC471356
0.75	Intermediate Similarity	NPC9674
0.7482	Intermediate Similarity	NPC116075
0.7482	Intermediate Similarity	NPC247190
0.7482	Intermediate Similarity	NPC469749
0.7482	Intermediate Similarity	NPC146857
0.7482	Intermediate Similarity	NPC142756
0.7482	Intermediate Similarity	NPC32793
0.7481	Intermediate Similarity	NPC470775
0.7481	Intermediate Similarity	NPC130229
0.7481	Intermediate Similarity	NPC176513
0.7465	Intermediate Similarity	NPC79250
0.7465	Intermediate Similarity	NPC477233
0.7465	Intermediate Similarity	NPC290746
0.7465	Intermediate Similarity	NPC477232
0.7464	Intermediate Similarity	NPC159338
0.7464	Intermediate Similarity	NPC213634
0.7464	Intermediate Similarity	NPC16569
0.7464	Intermediate Similarity	NPC253456
0.7464	Intermediate Similarity	NPC173347
0.7463	Intermediate Similarity	NPC28532
0.7462	Intermediate Similarity	NPC469877
0.7462	Intermediate Similarity	NPC470919
0.7447	Intermediate Similarity	NPC141215
0.7447	Intermediate Similarity	NPC59288
0.7447	Intermediate Similarity	NPC289700
0.7447	Intermediate Similarity	NPC62172
0.7447	Intermediate Similarity	NPC190065
0.7447	Intermediate Similarity	NPC471089
0.7445	Intermediate Similarity	NPC476859
0.7444	Intermediate Similarity	NPC472004
0.7444	Intermediate Similarity	NPC241192
0.7444	Intermediate Similarity	NPC112038
0.7442	Intermediate Similarity	NPC477489
0.7442	Intermediate Similarity	NPC471244

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 NPC475376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	2760
0.2-0.3	3901
0.3-0.4	1349
0.4-0.5	461
0.5-0.6	237
0.6-0.7	75
0.7-0.8	16
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
0.7727	Intermediate Similarity	NPD6370	Approved
0.7704	Intermediate Similarity	NPD7736	Approved
0.7647	Intermediate Similarity	NPD7319	Approved
0.763	Intermediate Similarity	NPD8293	Discontinued
0.763	Intermediate Similarity	NPD7078	Approved
0.7612	Intermediate Similarity	NPD7492	Approved
0.7576	Intermediate Similarity	NPD6054	Approved
0.7556	Intermediate Similarity	NPD6616	Approved
0.754	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD1700	Approved
0.7444	Intermediate Similarity	NPD6059	Approved
0.7426	Intermediate Similarity	NPD7507	Approved
0.7388	Intermediate Similarity	NPD6016	Approved
0.7388	Intermediate Similarity	NPD6015	Approved
0.7333	Intermediate Similarity	NPD5988	Approved
0.7313	Intermediate Similarity	NPD6319	Approved
0.7218	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7516	Approved
0.7045	Intermediate Similarity	NPD6882	Approved
0.7037	Intermediate Similarity	NPD7327	Approved
0.7037	Intermediate Similarity	NPD7328	Approved
0.7029	Intermediate Similarity	NPD8328	Phase 3
0.7007	Intermediate Similarity	NPD8033	Approved
0.7007	Intermediate Similarity	NPD6921	Approved
0.6992	Remote Similarity	NPD8133	Approved
0.6963	Remote Similarity	NPD6009	Approved
0.695	Remote Similarity	NPD6033	Approved
0.6917	Remote Similarity	NPD8297	Approved
0.6899	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8296	Approved
0.6884	Remote Similarity	NPD8335	Approved
0.6884	Remote Similarity	NPD8380	Approved
0.6884	Remote Similarity	NPD8378	Approved
0.6884	Remote Similarity	NPD8379	Approved
0.6842	Remote Similarity	NPD6649	Approved
0.6842	Remote Similarity	NPD6650	Approved
0.6818	Remote Similarity	NPD6373	Approved
0.6818	Remote Similarity	NPD6372	Approved
0.6812	Remote Similarity	NPD8294	Approved
0.6812	Remote Similarity	NPD8377	Approved
0.6763	Remote Similarity	NPD8515	Approved
0.6763	Remote Similarity	NPD8513	Phase 3
0.6763	Remote Similarity	NPD7503	Approved
0.6763	Remote Similarity	NPD8516	Approved
0.6763	Remote Similarity	NPD8517	Approved
0.6742	Remote Similarity	NPD6899	Approved
0.6742	Remote Similarity	NPD6881	Approved
0.6742	Remote Similarity	NPD7320	Approved
0.6741	Remote Similarity	NPD4632	Approved
0.6718	Remote Similarity	NPD5739	Approved
0.6718	Remote Similarity	NPD6675	Approved
0.6718	Remote Similarity	NPD6008	Approved
0.6718	Remote Similarity	NPD7128	Approved
0.6718	Remote Similarity	NPD6402	Approved
0.6715	Remote Similarity	NPD7115	Discovery
0.6692	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6642	Remote Similarity	NPD7102	Approved
0.6642	Remote Similarity	NPD6883	Approved
0.6642	Remote Similarity	NPD7290	Approved
0.6642	Remote Similarity	NPD4634	Approved
0.6617	Remote Similarity	NPD6686	Approved
0.6593	Remote Similarity	NPD6847	Approved
0.6593	Remote Similarity	NPD6869	Approved
0.6593	Remote Similarity	NPD6617	Approved
0.6593	Remote Similarity	NPD8130	Phase 1
0.6567	Remote Similarity	NPD6014	Approved
0.6567	Remote Similarity	NPD6012	Approved
0.6567	Remote Similarity	NPD6013	Approved
0.6541	Remote Similarity	NPD5701	Approved
0.6525	Remote Similarity	NPD5983	Phase 2
0.6493	Remote Similarity	NPD6011	Approved
0.6458	Remote Similarity	NPD6336	Discontinued
0.6444	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5956	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.635	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD6067	Discontinued
0.6304	Remote Similarity	NPD6053	Discontinued
0.6301	Remote Similarity	NPD8074	Phase 3
0.6269	Remote Similarity	NPD5141	Approved
0.6268	Remote Similarity	NPD7100	Approved
0.6268	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD8171	Discontinued
0.6232	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD7799	Discontinued
0.6212	Remote Similarity	NPD5286	Approved
0.6212	Remote Similarity	NPD4696	Approved
0.6212	Remote Similarity	NPD5285	Approved
0.6197	Remote Similarity	NPD6335	Approved
0.6183	Remote Similarity	NPD6083	Phase 2
0.6183	Remote Similarity	NPD6084	Phase 2
0.6183	Remote Similarity	NPD4755	Approved
0.6181	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6274	Approved
0.6127	Remote Similarity	NPD6317	Approved
0.6119	Remote Similarity	NPD5224	Approved
0.6119	Remote Similarity	NPD5225	Approved
0.6119	Remote Similarity	NPD5226	Approved
0.6119	Remote Similarity	NPD4633	Approved
0.609	Remote Similarity	NPD7639	Approved
0.609	Remote Similarity	NPD4700	Approved
0.609	Remote Similarity	NPD7640	Approved
0.6084	Remote Similarity	NPD6313	Approved
0.6084	Remote Similarity	NPD6314	Approved
0.6074	Remote Similarity	NPD5175	Approved
0.6074	Remote Similarity	NPD5174	Approved
0.6069	Remote Similarity	NPD6909	Approved
0.6069	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD6908	Approved
0.6058	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD8035	Phase 2
0.6047	Remote Similarity	NPD8034	Phase 2
0.6045	Remote Similarity	NPD5223	Approved
0.6027	Remote Similarity	NPD8080	Discontinued
0.6015	Remote Similarity	NPD7638	Approved
0.6015	Remote Similarity	NPD5696	Approved
0.6015	Remote Similarity	NPD4225	Approved
0.6014	Remote Similarity	NPD4729	Approved
0.6014	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD6333	Approved
0.6	Remote Similarity	NPD6334	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5985	Remote Similarity	NPD4767	Approved
0.5985	Remote Similarity	NPD4768	Approved
0.5984	Remote Similarity	NPD4251	Approved
0.5984	Remote Similarity	NPD4250	Approved
0.5954	Remote Similarity	NPD5282	Discontinued
0.5929	Remote Similarity	NPD5248	Approved
0.5929	Remote Similarity	NPD5247	Approved
0.5929	Remote Similarity	NPD5249	Phase 3
0.5929	Remote Similarity	NPD6371	Approved
0.5929	Remote Similarity	NPD5250	Approved
0.5929	Remote Similarity	NPD5251	Approved
0.5923	Remote Similarity	NPD7637	Suspended
0.5909	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5695	Phase 3
0.5906	Remote Similarity	NPD4249	Approved
0.5903	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD7625	Phase 1
0.5882	Remote Similarity	NPD8338	Approved
0.5839	Remote Similarity	NPD8342	Approved
0.5839	Remote Similarity	NPD8340	Approved
0.5839	Remote Similarity	NPD8341	Approved
0.5839	Remote Similarity	NPD8299	Approved
0.5839	Remote Similarity	NPD4754	Approved
0.5833	Remote Similarity	NPD6940	Discontinued
0.5833	Remote Similarity	NPD6868	Approved
0.5827	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5817	Remote Similarity	NPD7260	Phase 2
0.5809	Remote Similarity	NPD5344	Discontinued
0.5806	Remote Similarity	NPD6928	Phase 2
0.5802	Remote Similarity	NPD7983	Approved
0.5802	Remote Similarity	NPD6411	Approved
0.5786	Remote Similarity	NPD5128	Approved
0.5779	Remote Similarity	NPD6845	Suspended
0.5775	Remote Similarity	NPD5215	Approved
0.5775	Remote Similarity	NPD5216	Approved
0.5775	Remote Similarity	NPD5217	Approved
0.5772	Remote Similarity	NPD6118	Approved
0.5772	Remote Similarity	NPD6114	Approved
0.5772	Remote Similarity	NPD6697	Approved
0.5772	Remote Similarity	NPD7642	Approved
0.5772	Remote Similarity	NPD6115	Approved
0.5766	Remote Similarity	NPD7632	Discontinued
0.5758	Remote Similarity	NPD5778	Approved
0.5758	Remote Similarity	NPD5779	Approved
0.5746	Remote Similarity	NPD5222	Approved
0.5746	Remote Similarity	NPD4697	Phase 3
0.5746	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD5221	Approved
0.5743	Remote Similarity	NPD8268	Approved
0.5743	Remote Similarity	NPD8266	Approved
0.5743	Remote Similarity	NPD8269	Approved
0.5743	Remote Similarity	NPD8267	Approved
0.5736	Remote Similarity	NPD7524	Approved
0.5732	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4522	Approved
0.5704	Remote Similarity	NPD5135	Approved
0.5704	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5704	Remote Similarity	NPD5173	Approved
0.5704	Remote Similarity	NPD5169	Approved
0.5695	Remote Similarity	NPD8451	Approved
0.5691	Remote Similarity	NPD6116	Phase 1
0.5682	Remote Similarity	NPD6079	Approved
0.5673	Remote Similarity	NPD5761	Phase 2
0.5673	Remote Similarity	NPD5760	Phase 2
0.5672	Remote Similarity	NPD5210	Approved
0.5672	Remote Similarity	NPD4629	Approved
0.5669	Remote Similarity	NPD3669	Approved
0.5669	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7829	Approved
0.5667	Remote Similarity	NPD7830	Approved
0.5664	Remote Similarity	NPD5127	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