NPASS Compound

Structure

NPC48813 OpenBabel07101719132D 50 57 0 0 1 0 0 0 0 0999 V2000 2.1294 -4.2414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1346 -2.8686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3422 -2.6301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1769 2.0430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5331 0.2394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7116 -0.1208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6119 -1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2471 -3.9979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1695 0.1712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6846 -0.2752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7197 2.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7912 -1.1927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6598 -1.1326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0512 0.6780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0168 -3.1121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1546 -2.2085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2435 1.3296 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0906 -0.9416 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4243 -0.8014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1560 1.8138 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6427 1.1356 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3772 -0.3921 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0574 0.2203 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6427 0.2203 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8501 1.5932 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6689 -2.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2039 0.3691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0305 -1.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2402 0.6942 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0574 1.1356 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6916 0.5995 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8501 -0.2373 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5132 -0.0625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8949 0.7703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1733 0.8987 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9259 -2.7012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8501 2.5085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5512 -2.7133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4867 1.2396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9663 -1.9996 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3721 2.5376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8163 -0.3111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8532 -0.6856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1103 0.0481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5132 1.4184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7495 -1.2283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1957 -1.2942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4386 -1.5839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2275 1.1586 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 8 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 31 1 0 0 0 0 6 42 1 0 0 0 0 7 43 1 0 0 0 0 8 15 2 0 0 0 0 9 10 2 0 0 0 0 9 34 1 0 0 0 0 10 44 1 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 46 1 0 0 0 0 14 33 1 0 0 0 0 14 45 1 0 0 0 0 15 26 1 0 0 0 0 16 36 2 0 0 0 0 16 47 1 0 0 0 0 17 31 1 1 0 0 0 17 34 1 0 0 0 0 18 32 1 6 0 0 0 18 48 1 0 0 0 0 19 33 1 6 0 0 0 19 47 1 0 0 0 0 20 35 1 1 0 0 0 20 49 1 0 0 0 0 21 24 1 0 0 0 0 21 25 1 0 0 0 0 21 45 1 6 0 0 0 22 23 1 0 0 0 0 22 27 1 6 0 0 0 22 46 1 0 0 0 0 23 30 1 1 0 0 0 23 32 1 0 0 0 0 24 32 1 1 0 0 0 24 33 1 0 0 0 0 25 30 1 6 0 0 0 25 37 1 0 0 0 0 26 38 2 0 0 0 0 26 48 1 0 0 0 0 27 39 2 0 0 0 0 27 42 1 0 0 0 0 28 40 2 0 0 0 0 28 43 1 0 0 0 0 29 34 1 6 0 0 0 29 44 1 0 0 0 0 29 49 1 0 0 0 0 30 4 1 1 0 0 0 30 35 1 0 0 0 0 31 35 1 6 0 0 0 31 50 1 0 0 0 0 32 13 1 1 0 0 0 33 28 1 1 0 0 0 34 41 1 1 0 0 0 35 50 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	704.27
Volume:	661.499
LogP:	2.063
LogD:	1.062
LogS:	-4.965
# Rotatable Bonds:	10
TPSA:	195.11
# H-Bond Aceptor:	15
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.168
Synthetic Accessibility Score:	7.546
Fsp3:	0.771
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:	-5.39
MDCK Permeability:	0.00020601916185114533
Pgp-inhibitor:	0.959
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.077
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	27.21533203125%
Volume Distribution (VD):	1.339
Pgp-substrate:	42.296260833740234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.351
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.832
CYP3A4-substrate:	0.58

ADMET: Excretion

Clearance (CL):	2.81
Half-life (T1/2):	0.392

ADMET: Toxicity

hERG Blockers:	0.687
Human Hepatotoxicity (H-HT):	0.901
Drug-inuced Liver Injury (DILI):	0.317
AMES Toxicity:	0.823
Rat Oral Acute Toxicity:	0.906
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.297
Carcinogencity:	0.977
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC48813

Natural Product ID:	NPC48813
*Common Name:**	Azadirachtin M
IUPAC Name:	n.a.
Synonyms:	Azadirachtin M
Standard InCHIKey:	FNNQCONAJPWRKB-WJBGISAESA-N
Standard InCHI:	InChI=1S/C35H44O15/c1-8-15(2)26(38)48-18-12-19(47-16(3)36)33(28(40)43-7)14-45-21-24(33)32(18)13-46-22(27(39)42-6)23(32)30(4,25(21)37)35-20-11-17(31(35,5)50-35)34(41)9-10-44-29(34)49-20/h8-10,17-25,29,37,41H,11-14H2,1-7H3/b15-8+/t17-,18+,19-,20+,21-,22+,23+,24-,25-,29+,30+,31+,32-,33+,34+,35+/m1/s1
SMILES:	COC(=O)[C@H]1OC[C@]23[C@@H]1[C@@](C)([C@@H]([C@H]1[C@H]3[C@@]([C@@H](C[C@@H]2OC(=O)/C(=C/C)/C)OC(=O)C)(CO1)C(=O)OC)O)[C@@]12O[C@@]2(C)[C@H]2C[C@@H]1O[C@H]1[C@]2(O)C=CO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508913
PubChem CID:	10723437
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]
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

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT849	Organism	Plutella xylostella	Plutella xylostella	LD50	=	8.46	mg.kg-1	PMID[554337]
NPT849	Organism	Plutella xylostella	Plutella xylostella	LD50	=	4.84	mg.kg-1	PMID[554337]
NPT849	Organism	Plutella xylostella	Plutella xylostella	LD50	=	4.23	mg.kg-1	PMID[554337]
NPT849	Organism	Plutella xylostella	Plutella xylostella	LD50	=	1.3	mg.kg-1	PMID[554337]

☑ 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 NPC48813 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	380
0.1-0.2	2162
0.2-0.3	5512
0.3-0.4	8890
0.4-0.5	12433
0.5-0.6	7842
0.6-0.7	4292
0.7-0.8	1155
0.8-0.85	14
0.85-0.9	5
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC194854
0.9925	High Similarity	NPC475462
0.9925	High Similarity	NPC16729
0.9774	High Similarity	NPC471172
0.9773	High Similarity	NPC48414
0.9773	High Similarity	NPC5153
0.9552	High Similarity	NPC471171
0.9318	High Similarity	NPC256618
0.9318	High Similarity	NPC219058
0.9242	High Similarity	NPC475376
0.9091	High Similarity	NPC42206
0.8815	High Similarity	NPC471234
0.8815	High Similarity	NPC470117
0.8467	Intermediate Similarity	NPC88668
0.8394	Intermediate Similarity	NPC471855
0.8248	Intermediate Similarity	NPC471407
0.8248	Intermediate Similarity	NPC470851
0.8235	Intermediate Similarity	NPC42399
0.8235	Intermediate Similarity	NPC471357
0.8235	Intermediate Similarity	NPC117702
0.8235	Intermediate Similarity	NPC146456
0.8235	Intermediate Similarity	NPC469757
0.8227	Intermediate Similarity	NPC295885
0.8227	Intermediate Similarity	NPC140045
0.8227	Intermediate Similarity	NPC596
0.8188	Intermediate Similarity	NPC473838
0.8188	Intermediate Similarity	NPC213634
0.8188	Intermediate Similarity	NPC476852
0.8188	Intermediate Similarity	NPC475389
0.8175	Intermediate Similarity	NPC470850
0.8175	Intermediate Similarity	NPC473620
0.8175	Intermediate Similarity	NPC311534
0.8169	Intermediate Similarity	NPC75616
0.8156	Intermediate Similarity	NPC251998
0.8156	Intermediate Similarity	NPC141215
0.8156	Intermediate Similarity	NPC190065
0.8156	Intermediate Similarity	NPC471089
0.8143	Intermediate Similarity	NPC478072
0.8129	Intermediate Similarity	NPC180902
0.8129	Intermediate Similarity	NPC472769
0.8129	Intermediate Similarity	NPC231240
0.8129	Intermediate Similarity	NPC475139
0.8116	Intermediate Similarity	NPC6108
0.8116	Intermediate Similarity	NPC470880
0.8116	Intermediate Similarity	NPC469755
0.8116	Intermediate Similarity	NPC70542
0.8116	Intermediate Similarity	NPC471359
0.8116	Intermediate Similarity	NPC219085
0.8116	Intermediate Similarity	NPC473593
0.8116	Intermediate Similarity	NPC251866
0.8116	Intermediate Similarity	NPC471352
0.8116	Intermediate Similarity	NPC476851
0.8116	Intermediate Similarity	NPC17896
0.8116	Intermediate Similarity	NPC469751
0.8116	Intermediate Similarity	NPC284406
0.8116	Intermediate Similarity	NPC86159
0.8116	Intermediate Similarity	NPC197707
0.8116	Intermediate Similarity	NPC180079
0.8116	Intermediate Similarity	NPC469753
0.8116	Intermediate Similarity	NPC471358
0.8116	Intermediate Similarity	NPC469754
0.8116	Intermediate Similarity	NPC471361
0.8116	Intermediate Similarity	NPC89514
0.8116	Intermediate Similarity	NPC469752
0.8116	Intermediate Similarity	NPC9499
0.8116	Intermediate Similarity	NPC471360
0.8116	Intermediate Similarity	NPC10823
0.8102	Intermediate Similarity	NPC298841
0.8102	Intermediate Similarity	NPC287423
0.8085	Intermediate Similarity	NPC171619
0.8085	Intermediate Similarity	NPC262813
0.8071	Intermediate Similarity	NPC104585
0.8071	Intermediate Similarity	NPC157817
0.8071	Intermediate Similarity	NPC225385
0.8071	Intermediate Similarity	NPC469749
0.8071	Intermediate Similarity	NPC247190
0.8071	Intermediate Similarity	NPC298783
0.8071	Intermediate Similarity	NPC142756
0.8071	Intermediate Similarity	NPC316915
0.8071	Intermediate Similarity	NPC116075
0.8071	Intermediate Similarity	NPC32793
0.8071	Intermediate Similarity	NPC146857
0.8058	Intermediate Similarity	NPC173347
0.8058	Intermediate Similarity	NPC471170
0.8056	Intermediate Similarity	NPC25887
0.8043	Intermediate Similarity	NPC114306
0.8043	Intermediate Similarity	NPC476078
0.8043	Intermediate Similarity	NPC477490
0.8043	Intermediate Similarity	NPC476091
0.8043	Intermediate Similarity	NPC476859
0.8042	Intermediate Similarity	NPC290746
0.8042	Intermediate Similarity	NPC79250
0.8028	Intermediate Similarity	NPC62172
0.8028	Intermediate Similarity	NPC289700
0.8028	Intermediate Similarity	NPC59288
0.8015	Intermediate Similarity	NPC27363
0.8014	Intermediate Similarity	NPC223356
0.8014	Intermediate Similarity	NPC473548
0.8014	Intermediate Similarity	NPC471136
0.8014	Intermediate Similarity	NPC329636
0.8014	Intermediate Similarity	NPC475500
0.8014	Intermediate Similarity	NPC100017
0.8014	Intermediate Similarity	NPC182266
0.8014	Intermediate Similarity	NPC475154
0.8014	Intermediate Similarity	NPC471137
0.8014	Intermediate Similarity	NPC476823
0.8	Intermediate Similarity	NPC19124
0.8	Intermediate Similarity	NPC42670
0.8	Intermediate Similarity	NPC470426
0.8	Intermediate Similarity	NPC93416
0.7986	Intermediate Similarity	NPC472770
0.7986	Intermediate Similarity	NPC231529
0.7986	Intermediate Similarity	NPC475371
0.7986	Intermediate Similarity	NPC104382
0.7986	Intermediate Similarity	NPC162495
0.7986	Intermediate Similarity	NPC175186
0.7986	Intermediate Similarity	NPC476966
0.7985	Intermediate Similarity	NPC9674
0.7985	Intermediate Similarity	NPC19028
0.7971	Intermediate Similarity	NPC473265
0.7971	Intermediate Similarity	NPC473253
0.7971	Intermediate Similarity	NPC152091
0.7971	Intermediate Similarity	NPC471356
0.7971	Intermediate Similarity	NPC240070
0.7971	Intermediate Similarity	NPC179412
0.7971	Intermediate Similarity	NPC470882
0.7971	Intermediate Similarity	NPC329784
0.7958	Intermediate Similarity	NPC158350
0.7958	Intermediate Similarity	NPC194716
0.7956	Intermediate Similarity	NPC475194
0.7956	Intermediate Similarity	NPC86346
0.7956	Intermediate Similarity	NPC470922
0.7956	Intermediate Similarity	NPC75856
0.7956	Intermediate Similarity	NPC469379
0.7943	Intermediate Similarity	NPC478151
0.7943	Intermediate Similarity	NPC469673
0.7943	Intermediate Similarity	NPC477709
0.7943	Intermediate Similarity	NPC476221
0.7943	Intermediate Similarity	NPC58029
0.7929	Intermediate Similarity	NPC476863
0.7929	Intermediate Similarity	NPC253456
0.7929	Intermediate Similarity	NPC477493
0.7929	Intermediate Similarity	NPC196921
0.7929	Intermediate Similarity	NPC16569
0.7929	Intermediate Similarity	NPC159338
0.7929	Intermediate Similarity	NPC220757
0.7929	Intermediate Similarity	NPC476862
0.7929	Intermediate Similarity	NPC476855
0.7926	Intermediate Similarity	NPC281840
0.7926	Intermediate Similarity	NPC472004
0.7914	Intermediate Similarity	NPC69273
0.7914	Intermediate Similarity	NPC293623
0.7914	Intermediate Similarity	NPC473888
0.7914	Intermediate Similarity	NPC168899
0.7902	Intermediate Similarity	NPC68282
0.7902	Intermediate Similarity	NPC329675
0.7899	Intermediate Similarity	NPC250556
0.7899	Intermediate Similarity	NPC469750
0.7899	Intermediate Similarity	NPC293112
0.7899	Intermediate Similarity	NPC47113
0.7899	Intermediate Similarity	NPC93368
0.7899	Intermediate Similarity	NPC473635
0.7899	Intermediate Similarity	NPC174367
0.7883	Intermediate Similarity	NPC469382
0.7883	Intermediate Similarity	NPC67251
0.7879	Intermediate Similarity	NPC285086
0.7879	Intermediate Similarity	NPC477126
0.7872	Intermediate Similarity	NPC34963
0.7872	Intermediate Similarity	NPC478152
0.7872	Intermediate Similarity	NPC473485
0.7872	Intermediate Similarity	NPC478150
0.7872	Intermediate Similarity	NPC478154
0.7872	Intermediate Similarity	NPC478153
0.7872	Intermediate Similarity	NPC474508
0.7862	Intermediate Similarity	NPC476825
0.7857	Intermediate Similarity	NPC35109
0.7857	Intermediate Similarity	NPC140092
0.7857	Intermediate Similarity	NPC276838
0.7857	Intermediate Similarity	NPC188234
0.7857	Intermediate Similarity	NPC232785
0.7857	Intermediate Similarity	NPC91
0.7857	Intermediate Similarity	NPC125077
0.7857	Intermediate Similarity	NPC476854
0.7857	Intermediate Similarity	NPC329986
0.7842	Intermediate Similarity	NPC475273
0.7842	Intermediate Similarity	NPC168849
0.7842	Intermediate Similarity	NPC476008
0.7842	Intermediate Similarity	NPC470780
0.7842	Intermediate Similarity	NPC305496
0.7826	Intermediate Similarity	NPC172154
0.7826	Intermediate Similarity	NPC81736
0.7826	Intermediate Similarity	NPC8369
0.7826	Intermediate Similarity	NPC476729
0.7826	Intermediate Similarity	NPC473255
0.7826	Intermediate Similarity	NPC24651
0.782	Intermediate Similarity	NPC470116
0.782	Intermediate Similarity	NPC470115
0.7817	Intermediate Similarity	NPC475487
0.7817	Intermediate Similarity	NPC168879
0.781	Intermediate Similarity	NPC222688

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 NPC48813 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	2298
0.2-0.3	3862
0.3-0.4	1729
0.4-0.5	522
0.5-0.6	256
0.6-0.7	101
0.7-0.8	25
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8116	Intermediate Similarity	NPD7319	Approved
0.8043	Intermediate Similarity	NPD7736	Approved
0.7941	Intermediate Similarity	NPD6370	Approved
0.7899	Intermediate Similarity	NPD7507	Approved
0.7842	Intermediate Similarity	NPD8293	Discontinued
0.7842	Intermediate Similarity	NPD7078	Approved
0.7826	Intermediate Similarity	NPD7492	Approved
0.7794	Intermediate Similarity	NPD6054	Approved
0.777	Intermediate Similarity	NPD6616	Approved
0.7609	Intermediate Similarity	NPD6016	Approved
0.7609	Intermediate Similarity	NPD8033	Approved
0.7609	Intermediate Similarity	NPD6015	Approved
0.7591	Intermediate Similarity	NPD7516	Approved
0.7554	Intermediate Similarity	NPD5988	Approved
0.7536	Intermediate Similarity	NPD6319	Approved
0.7536	Intermediate Similarity	NPD6059	Approved
0.7518	Intermediate Similarity	NPD7328	Approved
0.7518	Intermediate Similarity	NPD7327	Approved
0.7482	Intermediate Similarity	NPD8380	Approved
0.7482	Intermediate Similarity	NPD8296	Approved
0.7482	Intermediate Similarity	NPD8379	Approved
0.7482	Intermediate Similarity	NPD8335	Approved
0.7482	Intermediate Similarity	NPD8378	Approved
0.741	Intermediate Similarity	NPD8294	Approved
0.741	Intermediate Similarity	NPD8377	Approved
0.7357	Intermediate Similarity	NPD7503	Approved
0.7319	Intermediate Similarity	NPD7115	Discovery
0.7279	Intermediate Similarity	NPD6882	Approved
0.7279	Intermediate Similarity	NPD8297	Approved
0.7254	Intermediate Similarity	NPD8328	Phase 3
0.7239	Intermediate Similarity	NPD6686	Approved
0.7239	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6009	Approved
0.7113	Intermediate Similarity	NPD8517	Approved
0.7113	Intermediate Similarity	NPD8516	Approved
0.7113	Intermediate Similarity	NPD8515	Approved
0.7113	Intermediate Similarity	NPD8513	Phase 3
0.7101	Intermediate Similarity	NPD8133	Approved
0.708	Intermediate Similarity	NPD6649	Approved
0.708	Intermediate Similarity	NPD6650	Approved
0.7071	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6033	Approved
0.6985	Remote Similarity	NPD6881	Approved
0.6985	Remote Similarity	NPD6899	Approved
0.6978	Remote Similarity	NPD4632	Approved
0.6957	Remote Similarity	NPD8130	Phase 1
0.6934	Remote Similarity	NPD6373	Approved
0.6934	Remote Similarity	NPD6372	Approved
0.6917	Remote Similarity	NPD1700	Approved
0.6912	Remote Similarity	NPD5697	Approved
0.6897	Remote Similarity	NPD7604	Phase 2
0.6884	Remote Similarity	NPD4634	Approved
0.6884	Remote Similarity	NPD7102	Approved
0.6884	Remote Similarity	NPD6883	Approved
0.6884	Remote Similarity	NPD7290	Approved
0.6861	Remote Similarity	NPD7320	Approved
0.6838	Remote Similarity	NPD6675	Approved
0.6838	Remote Similarity	NPD7128	Approved
0.6838	Remote Similarity	NPD6402	Approved
0.6838	Remote Similarity	NPD6008	Approved
0.6838	Remote Similarity	NPD5739	Approved
0.6835	Remote Similarity	NPD6847	Approved
0.6835	Remote Similarity	NPD6869	Approved
0.6835	Remote Similarity	NPD6617	Approved
0.6812	Remote Similarity	NPD6012	Approved
0.6812	Remote Similarity	NPD6014	Approved
0.6812	Remote Similarity	NPD6013	Approved
0.6812	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7799	Discontinued
0.6788	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6412	Phase 2
0.6786	Remote Similarity	NPD6053	Discontinued
0.6763	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6921	Approved
0.6759	Remote Similarity	NPD5983	Phase 2
0.6739	Remote Similarity	NPD6011	Approved
0.6689	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5701	Approved
0.6644	Remote Similarity	NPD8074	Phase 3
0.6642	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4225	Approved
0.6623	Remote Similarity	NPD5956	Approved
0.6618	Remote Similarity	NPD5211	Phase 2
0.6596	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7639	Approved
0.6593	Remote Similarity	NPD7640	Approved
0.6571	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6371	Approved
0.6522	Remote Similarity	NPD5141	Approved
0.6522	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7638	Approved
0.6507	Remote Similarity	NPD7100	Approved
0.6507	Remote Similarity	NPD7101	Approved
0.6479	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5286	Approved
0.6471	Remote Similarity	NPD5285	Approved
0.6471	Remote Similarity	NPD4696	Approved
0.6443	Remote Similarity	NPD6067	Discontinued
0.6438	Remote Similarity	NPD6335	Approved
0.6423	Remote Similarity	NPD5344	Discontinued
0.6419	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6274	Approved
0.6377	Remote Similarity	NPD4633	Approved
0.6377	Remote Similarity	NPD5225	Approved
0.6377	Remote Similarity	NPD5224	Approved
0.6377	Remote Similarity	NPD5226	Approved
0.637	Remote Similarity	NPD6317	Approved
0.6369	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7260	Phase 2
0.6331	Remote Similarity	NPD5174	Approved
0.6331	Remote Similarity	NPD5175	Approved
0.6327	Remote Similarity	NPD6313	Approved
0.6327	Remote Similarity	NPD6314	Approved
0.6324	Remote Similarity	NPD6084	Phase 2
0.6324	Remote Similarity	NPD4755	Approved
0.6324	Remote Similarity	NPD6083	Phase 2
0.6319	Remote Similarity	NPD7625	Phase 1
0.6304	Remote Similarity	NPD5223	Approved
0.6268	Remote Similarity	NPD4730	Approved
0.6268	Remote Similarity	NPD4729	Approved
0.6232	Remote Similarity	NPD4700	Approved
0.6226	Remote Similarity	NPD6334	Approved
0.6226	Remote Similarity	NPD6333	Approved
0.6225	Remote Similarity	NPD7829	Approved
0.6225	Remote Similarity	NPD7830	Approved
0.6218	Remote Similarity	NPD8338	Approved
0.6218	Remote Similarity	NPD6845	Suspended
0.62	Remote Similarity	NPD6909	Approved
0.62	Remote Similarity	NPD6908	Approved
0.6188	Remote Similarity	NPD7685	Pre-registration
0.6181	Remote Similarity	NPD5249	Phase 3
0.6181	Remote Similarity	NPD5248	Approved
0.6181	Remote Similarity	NPD5247	Approved
0.6181	Remote Similarity	NPD5250	Approved
0.6181	Remote Similarity	NPD5251	Approved
0.6163	Remote Similarity	NPD5761	Phase 2
0.6163	Remote Similarity	NPD5760	Phase 2
0.6159	Remote Similarity	NPD5696	Approved
0.6159	Remote Similarity	NPD8080	Discontinued
0.6159	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD7632	Discontinued
0.6141	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD4768	Approved
0.6127	Remote Similarity	NPD4767	Approved
0.6119	Remote Similarity	NPD46	Approved
0.6119	Remote Similarity	NPD6698	Approved
0.6118	Remote Similarity	NPD7642	Approved
0.6115	Remote Similarity	NPD6648	Approved
0.6103	Remote Similarity	NPD5282	Discontinued
0.6087	Remote Similarity	NPD8407	Phase 2
0.6081	Remote Similarity	NPD6868	Approved
0.6058	Remote Similarity	NPD5695	Phase 3
0.6058	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5128	Approved
0.6027	Remote Similarity	NPD5217	Approved
0.6027	Remote Similarity	NPD5216	Approved
0.6027	Remote Similarity	NPD5215	Approved
0.6014	Remote Similarity	NPD5222	Approved
0.6014	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD5221	Approved
0.6011	Remote Similarity	NPD8368	Discontinued
0.6	Remote Similarity	NPD5785	Approved
0.5987	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD4754	Approved
0.5971	Remote Similarity	NPD5173	Approved
0.5962	Remote Similarity	NPD8337	Approved
0.5962	Remote Similarity	NPD8336	Approved
0.596	Remote Similarity	NPD4522	Approved
0.5959	Remote Similarity	NPD5169	Approved
0.5959	Remote Similarity	NPD5135	Approved
0.5959	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD7637	Suspended
0.5956	Remote Similarity	NPD5693	Phase 1
0.5956	Remote Similarity	NPD6079	Approved
0.5956	Remote Similarity	NPD8035	Phase 2
0.5956	Remote Similarity	NPD8034	Phase 2
0.5956	Remote Similarity	NPD7983	Approved
0.5952	Remote Similarity	NPD7236	Approved
0.5942	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD5210	Approved
0.5942	Remote Similarity	NPD4629	Approved
0.5936	Remote Similarity	NPD8434	Phase 2
0.5935	Remote Similarity	NPD8451	Approved
0.5918	Remote Similarity	NPD5127	Approved
0.5912	Remote Similarity	NPD8171	Discontinued
0.5912	Remote Similarity	NPD6399	Phase 3
0.5901	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD4697	Phase 3
0.5897	Remote Similarity	NPD8448	Approved
0.5896	Remote Similarity	NPD4250	Approved
0.5896	Remote Similarity	NPD4251	Approved
0.5895	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.5886	Remote Similarity	NPD8392	Approved
0.5886	Remote Similarity	NPD8390	Approved
0.5886	Remote Similarity	NPD8391	Approved
0.5882	Remote Similarity	NPD8266	Approved
0.5882	Remote Similarity	NPD8268	Approved
0.5882	Remote Similarity	NPD8267	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