NPASS Compound

Structure

CID222307 OpenBabel06191716012D 39 43 0 0 1 0 0 0 0 0999 V2000 1.6701 5.0822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0564 3.4092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7969 1.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5283 3.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4123 4.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0805 2.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9370 4.4020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0917 2.8209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0470 3.4171 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1490 2.9888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6705 2.6353 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3051 1.7044 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3163 1.5553 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0441 4.5953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6928 2.3372 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5311 3.7219 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4011 4.4970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6593 2.7843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9286 0.9225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9510 0.6245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4645 5.5026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4640 3.3617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9972 2.0747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7040 2.1881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0581 3.2680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 15 2 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 27 1 0 0 0 0 9 15 1 0 0 0 0 9 26 1 0 0 0 0 10 29 1 0 0 0 0 11 15 1 0 0 0 0 11 37 1 0 0 0 0 12 23 1 0 0 0 0 13 28 1 6 0 0 0 14 30 2 0 0 0 0 14 39 1 0 0 0 0 16 22 1 0 0 0 0 16 28 1 6 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 17 38 1 0 0 0 0 18 26 1 1 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 19 31 1 6 0 0 0 20 21 1 0 0 0 0 20 32 1 1 0 0 0 21 24 1 0 0 0 0 21 33 1 6 0 0 0 22 25 1 0 0 0 0 22 27 1 6 0 0 0 23 26 1 0 0 0 0 23 34 2 0 0 0 0 24 37 1 1 0 0 0 24 38 1 0 0 0 0 25 27 1 0 0 0 0 26 35 1 1 0 0 0 27 39 1 6 0 0 0 28 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	552.26
Volume:	536.208
LogP:	1.194
LogD:	0.64
LogS:	-3.19
# Rotatable Bonds:	6
TPSA:	183.21
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	5.434
Fsp3:	0.786
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:	-5.944
MDCK Permeability:	7.132432074286044e-05
Pgp-inhibitor:	0.096
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.97
20% Bioavailability (F20%):	0.186
30% Bioavailability (F30%):	0.843

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	34.66407012939453%
Volume Distribution (VD):	0.516
Pgp-substrate:	43.385929107666016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.434
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.083

ADMET: Excretion

Clearance (CL):	1.135
Half-life (T1/2):	0.68

ADMET: Toxicity

hERG Blockers:	0.198
Human Hepatotoxicity (H-HT):	0.548
Drug-inuced Liver Injury (DILI):	0.584
AMES Toxicity:	0.228
Rat Oral Acute Toxicity:	0.819
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.274
Carcinogencity:	0.173
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC222307

Natural Product ID:	NPC222307
*Common Name:**	Fischerosides A
IUPAC Name:	n.a.
Synonyms:	Fischerosides A
Standard InCHIKey:	JMDGBSYRPFFZBO-WHDWRCRCSA-N
Standard InCHI:	InChI=1S/C28H40O11/c1-12-6-18-26(35,23(12)34)9-15(11-37-24-21(33)20(32)19(31)17(10-29)38-24)7-16-22-25(4,5)27(22,39-14(3)30)8-13(2)28(16,18)36/h6-7,13,16-22,24,29,31-33,35-36H,8-11H2,1-5H3/t13-,16+,17-,18-,19-,20+,21-,22-,24-,26-,27+,28-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OCC2=C[C@H]3[C@H]4[C@@](C4(C)C)(OC(=O)C)C[C@H]([C@@]3([C@H]3[C@@](C2)(O)C(=O)C(=C3)C)O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813581
PubChem CID:	53360347
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	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
EC50	1
MIC	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	360.0	nM	PMID[513205]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	170.0	nM	PMID[513205]
NPT27	Others	Unspecified		Ratio CC50/EC50	>	2.12	n.a.	PMID[513205]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	400.0	ug.mL-1	PMID[513206]

☑ 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 NPC222307 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	272
0.1-0.2	1599
0.2-0.3	4451
0.3-0.4	7283
0.4-0.5	12071
0.5-0.6	8732
0.6-0.7	5623
0.7-0.8	2407
0.8-0.85	175
0.85-0.9	82
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9829	High Similarity	NPC270109
0.9076	High Similarity	NPC162009
0.9076	High Similarity	NPC257017
0.9068	High Similarity	NPC471128
0.9068	High Similarity	NPC145182
0.9068	High Similarity	NPC471126
0.9068	High Similarity	NPC157252
0.8992	High Similarity	NPC52839
0.8966	High Similarity	NPC474872
0.8957	High Similarity	NPC475391
0.8898	High Similarity	NPC471125
0.8898	High Similarity	NPC472397
0.8898	High Similarity	NPC472758
0.8898	High Similarity	NPC171905
0.8879	High Similarity	NPC474937
0.8879	High Similarity	NPC71889
0.887	High Similarity	NPC260786
0.887	High Similarity	NPC474871
0.887	High Similarity	NPC174471
0.887	High Similarity	NPC96739
0.8843	High Similarity	NPC472399
0.8824	High Similarity	NPC255081
0.8824	High Similarity	NPC22628
0.8824	High Similarity	NPC471108
0.8824	High Similarity	NPC5989
0.8824	High Similarity	NPC275696
0.8824	High Similarity	NPC5991
0.8814	High Similarity	NPC156252
0.8793	High Similarity	NPC101825
0.8793	High Similarity	NPC170212
0.8793	High Similarity	NPC89227
0.8793	High Similarity	NPC151216
0.8793	High Similarity	NPC215643
0.8793	High Similarity	NPC17138
0.8793	High Similarity	NPC221511
0.8793	High Similarity	NPC265499
0.877	High Similarity	NPC145238
0.875	High Similarity	NPC185876
0.875	High Similarity	NPC19336
0.8739	High Similarity	NPC146280
0.8739	High Similarity	NPC124676
0.8729	High Similarity	NPC234858
0.8729	High Similarity	NPC471127
0.8729	High Similarity	NPC154363
0.8718	High Similarity	NPC477091
0.8707	High Similarity	NPC475937
0.8707	High Similarity	NPC158523
0.8678	High Similarity	NPC472401
0.8667	High Similarity	NPC180640
0.8655	High Similarity	NPC10721
0.8651	High Similarity	NPC471855
0.8651	High Similarity	NPC180902
0.8651	High Similarity	NPC475139
0.8644	High Similarity	NPC472400
0.864	High Similarity	NPC471407
0.8621	High Similarity	NPC153036
0.8607	High Similarity	NPC19464
0.8595	High Similarity	NPC48692
0.8595	High Similarity	NPC475885
0.8583	High Similarity	NPC472760
0.856	High Similarity	NPC236999
0.8559	High Similarity	NPC472757
0.8548	High Similarity	NPC217901
0.8516	High Similarity	NPC475154
0.8516	High Similarity	NPC100017
0.8516	High Similarity	NPC473548
0.8516	High Similarity	NPC182266
0.8516	High Similarity	NPC471137
0.8516	High Similarity	NPC223356
0.8516	High Similarity	NPC471136
0.8516	High Similarity	NPC475500
0.8512	High Similarity	NPC156745
0.8512	High Similarity	NPC236918
0.85	High Similarity	NPC153651
0.8492	Intermediate Similarity	NPC162495
0.848	Intermediate Similarity	NPC168849
0.848	Intermediate Similarity	NPC475273
0.8443	Intermediate Similarity	NPC329080
0.8443	Intermediate Similarity	NPC472759
0.8425	Intermediate Similarity	NPC477189
0.8425	Intermediate Similarity	NPC476855
0.8425	Intermediate Similarity	NPC251564
0.8425	Intermediate Similarity	NPC475606
0.8425	Intermediate Similarity	NPC475314
0.8417	Intermediate Similarity	NPC471816
0.8413	Intermediate Similarity	NPC476859
0.8403	Intermediate Similarity	NPC75167
0.8403	Intermediate Similarity	NPC311592
0.8387	Intermediate Similarity	NPC473802
0.8385	Intermediate Similarity	NPC68282
0.8361	Intermediate Similarity	NPC475775
0.8361	Intermediate Similarity	NPC476529
0.8359	Intermediate Similarity	NPC474508
0.8359	Intermediate Similarity	NPC473485
0.8346	Intermediate Similarity	NPC476854
0.8333	Intermediate Similarity	NPC181145
0.8333	Intermediate Similarity	NPC298841
0.832	Intermediate Similarity	NPC473709
0.832	Intermediate Similarity	NPC473919
0.8293	Intermediate Similarity	NPC107338
0.8293	Intermediate Similarity	NPC109607
0.8281	Intermediate Similarity	NPC476862
0.8281	Intermediate Similarity	NPC476863
0.8281	Intermediate Similarity	NPC476852
0.8281	Intermediate Similarity	NPC213634
0.8279	Intermediate Similarity	NPC234522
0.8268	Intermediate Similarity	NPC311534
0.8258	Intermediate Similarity	NPC79250
0.8258	Intermediate Similarity	NPC290746
0.8254	Intermediate Similarity	NPC471939
0.824	Intermediate Similarity	NPC27363
0.8231	Intermediate Similarity	NPC471234
0.8226	Intermediate Similarity	NPC202051
0.822	Intermediate Similarity	NPC163004
0.8217	Intermediate Similarity	NPC231240
0.8203	Intermediate Similarity	NPC476851
0.8203	Intermediate Similarity	NPC476966
0.8203	Intermediate Similarity	NPC104382
0.8197	Intermediate Similarity	NPC23046
0.8197	Intermediate Similarity	NPC474483
0.8189	Intermediate Similarity	NPC471940
0.8189	Intermediate Similarity	NPC470780
0.8189	Intermediate Similarity	NPC42399
0.8175	Intermediate Similarity	NPC470922
0.8167	Intermediate Similarity	NPC174836
0.8154	Intermediate Similarity	NPC316915
0.8151	Intermediate Similarity	NPC83005
0.8145	Intermediate Similarity	NPC471406
0.8145	Intermediate Similarity	NPC470312
0.814	Intermediate Similarity	NPC473838
0.814	Intermediate Similarity	NPC475389
0.814	Intermediate Similarity	NPC173347
0.8136	Intermediate Similarity	NPC392
0.8136	Intermediate Similarity	NPC177524
0.8136	Intermediate Similarity	NPC219900
0.813	Intermediate Similarity	NPC473828
0.813	Intermediate Similarity	NPC473617
0.8125	Intermediate Similarity	NPC245094
0.8125	Intermediate Similarity	NPC473620
0.8125	Intermediate Similarity	NPC470850
0.811	Intermediate Similarity	NPC15095
0.811	Intermediate Similarity	NPC250556
0.811	Intermediate Similarity	NPC469750
0.8099	Intermediate Similarity	NPC264153
0.808	Intermediate Similarity	NPC476204
0.808	Intermediate Similarity	NPC204731
0.808	Intermediate Similarity	NPC170084
0.8077	Intermediate Similarity	NPC34963
0.8065	Intermediate Similarity	NPC9674
0.8065	Intermediate Similarity	NPC19028
0.8065	Intermediate Similarity	NPC477071
0.8065	Intermediate Similarity	NPC472667
0.8062	Intermediate Similarity	NPC175186
0.8062	Intermediate Similarity	NPC35109
0.8062	Intermediate Similarity	NPC473593
0.8062	Intermediate Similarity	NPC470851
0.8062	Intermediate Similarity	NPC472770
0.8051	Intermediate Similarity	NPC293512
0.8049	Intermediate Similarity	NPC13713
0.8049	Intermediate Similarity	NPC473968
0.8049	Intermediate Similarity	NPC309433
0.8047	Intermediate Similarity	NPC469757
0.8047	Intermediate Similarity	NPC146456
0.8047	Intermediate Similarity	NPC117702
0.8047	Intermediate Similarity	NPC471357
0.8047	Intermediate Similarity	NPC471356
0.8047	Intermediate Similarity	NPC329784
0.8047	Intermediate Similarity	NPC240070
0.8047	Intermediate Similarity	NPC179412
0.8045	Intermediate Similarity	NPC596
0.8033	Intermediate Similarity	NPC472274
0.8033	Intermediate Similarity	NPC178289
0.8031	Intermediate Similarity	NPC75856
0.8031	Intermediate Similarity	NPC86346
0.8031	Intermediate Similarity	NPC469379
0.8017	Intermediate Similarity	NPC317687
0.8016	Intermediate Similarity	NPC28532
0.8015	Intermediate Similarity	NPC298783
0.8015	Intermediate Similarity	NPC88668
0.8015	Intermediate Similarity	NPC157817
0.8015	Intermediate Similarity	NPC104585
0.8015	Intermediate Similarity	NPC225385
0.8015	Intermediate Similarity	NPC478151
0.8015	Intermediate Similarity	NPC58029
0.8015	Intermediate Similarity	NPC469673
0.8	Intermediate Similarity	NPC475134
0.8	Intermediate Similarity	NPC471170
0.8	Intermediate Similarity	NPC159338
0.8	Intermediate Similarity	NPC196921
0.8	Intermediate Similarity	NPC220757
0.8	Intermediate Similarity	NPC477197
0.8	Intermediate Similarity	NPC235014
0.8	Intermediate Similarity	NPC16569
0.8	Intermediate Similarity	NPC241935
0.8	Intermediate Similarity	NPC281840
0.8	Intermediate Similarity	NPC253456
0.8	Intermediate Similarity	NPC472004
0.8	Intermediate Similarity	NPC476127
0.8	Intermediate Similarity	NPC477103
0.8	Intermediate Similarity	NPC475563

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 NPC222307 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	1834
0.2-0.3	3652
0.3-0.4	2182
0.4-0.5	742
0.5-0.6	292
0.6-0.7	163
0.7-0.8	39
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
0.8136	Intermediate Similarity	NPD6686	Approved
0.811	Intermediate Similarity	NPD7507	Approved
0.7923	Intermediate Similarity	NPD7319	Approved
0.7851	Intermediate Similarity	NPD6371	Approved
0.784	Intermediate Similarity	NPD7327	Approved
0.784	Intermediate Similarity	NPD7328	Approved
0.7778	Intermediate Similarity	NPD7516	Approved
0.7674	Intermediate Similarity	NPD8328	Phase 3
0.7656	Intermediate Similarity	NPD8033	Approved
0.7597	Intermediate Similarity	NPD6370	Approved
0.7581	Intermediate Similarity	NPD6882	Approved
0.7578	Intermediate Similarity	NPD8294	Approved
0.7578	Intermediate Similarity	NPD8377	Approved
0.7576	Intermediate Similarity	NPD7736	Approved
0.752	Intermediate Similarity	NPD8133	Approved
0.7519	Intermediate Similarity	NPD8378	Approved
0.7519	Intermediate Similarity	NPD8296	Approved
0.7519	Intermediate Similarity	NPD8380	Approved
0.7519	Intermediate Similarity	NPD8335	Approved
0.7519	Intermediate Similarity	NPD8379	Approved
0.7519	Intermediate Similarity	NPD7503	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7481	Intermediate Similarity	NPD7492	Approved
0.748	Intermediate Similarity	NPD7115	Discovery
0.748	Intermediate Similarity	NPD6009	Approved
0.7459	Intermediate Similarity	NPD6412	Phase 2
0.7442	Intermediate Similarity	NPD6319	Approved
0.7442	Intermediate Similarity	NPD6054	Approved
0.744	Intermediate Similarity	NPD8297	Approved
0.7424	Intermediate Similarity	NPD6616	Approved
0.7398	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4632	Approved
0.7368	Intermediate Similarity	NPD7078	Approved
0.736	Intermediate Similarity	NPD6649	Approved
0.736	Intermediate Similarity	NPD6650	Approved
0.7344	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6372	Approved
0.7339	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6059	Approved
0.728	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7604	Phase 2
0.7258	Intermediate Similarity	NPD6899	Approved
0.7258	Intermediate Similarity	NPD6881	Approved
0.7252	Intermediate Similarity	NPD8517	Approved
0.7252	Intermediate Similarity	NPD6016	Approved
0.7252	Intermediate Similarity	NPD6015	Approved
0.7252	Intermediate Similarity	NPD8513	Phase 3
0.7252	Intermediate Similarity	NPD8515	Approved
0.7252	Intermediate Similarity	NPD8516	Approved
0.7236	Intermediate Similarity	NPD5739	Approved
0.7236	Intermediate Similarity	NPD6402	Approved
0.7236	Intermediate Similarity	NPD7128	Approved
0.7236	Intermediate Similarity	NPD6675	Approved
0.7197	Intermediate Similarity	NPD5988	Approved
0.7177	Intermediate Similarity	NPD5697	Approved
0.7167	Intermediate Similarity	NPD7638	Approved
0.7167	Intermediate Similarity	NPD4225	Approved
0.7155	Intermediate Similarity	NPD46	Approved
0.7155	Intermediate Similarity	NPD6698	Approved
0.7143	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD7290	Approved
0.7143	Intermediate Similarity	NPD6883	Approved
0.712	Intermediate Similarity	NPD7320	Approved
0.7107	Intermediate Similarity	NPD7640	Approved
0.7107	Intermediate Similarity	NPD7639	Approved
0.7087	Intermediate Similarity	NPD8130	Phase 1
0.7087	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6617	Approved
0.7087	Intermediate Similarity	NPD6847	Approved
0.7087	Intermediate Similarity	NPD6869	Approved
0.7063	Intermediate Similarity	NPD6012	Approved
0.7063	Intermediate Similarity	NPD6014	Approved
0.7063	Intermediate Similarity	NPD6013	Approved
0.7049	Intermediate Similarity	NPD5344	Discontinued
0.704	Intermediate Similarity	NPD5701	Approved
0.704	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5983	Phase 2
0.6984	Remote Similarity	NPD6011	Approved
0.696	Remote Similarity	NPD6008	Approved
0.6912	Remote Similarity	NPD6336	Discontinued
0.6899	Remote Similarity	NPD6053	Discontinued
0.6885	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4634	Approved
0.6866	Remote Similarity	NPD6921	Approved
0.6855	Remote Similarity	NPD5211	Phase 2
0.6829	Remote Similarity	NPD5286	Approved
0.6829	Remote Similarity	NPD4696	Approved
0.6829	Remote Similarity	NPD5285	Approved
0.6822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6033	Approved
0.6803	Remote Similarity	NPD4755	Approved
0.6803	Remote Similarity	NPD6084	Phase 2
0.6803	Remote Similarity	NPD6083	Phase 2
0.6786	Remote Similarity	NPD7260	Phase 2
0.6746	Remote Similarity	NPD5141	Approved
0.6742	Remote Similarity	NPD6274	Approved
0.6739	Remote Similarity	NPD8074	Phase 3
0.672	Remote Similarity	NPD5226	Approved
0.672	Remote Similarity	NPD4633	Approved
0.672	Remote Similarity	NPD5225	Approved
0.672	Remote Similarity	NPD5224	Approved
0.6716	Remote Similarity	NPD7101	Approved
0.6716	Remote Similarity	NPD7100	Approved
0.6694	Remote Similarity	NPD4700	Approved
0.6694	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6642	Remote Similarity	NPD7642	Approved
0.6642	Remote Similarity	NPD6335	Approved
0.6642	Remote Similarity	NPD6067	Discontinued
0.664	Remote Similarity	NPD5223	Approved
0.6639	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5695	Phase 3
0.6613	Remote Similarity	NPD5696	Approved
0.6612	Remote Similarity	NPD6399	Phase 3
0.6589	Remote Similarity	NPD4730	Approved
0.6589	Remote Similarity	NPD4729	Approved
0.6587	Remote Similarity	NPD7632	Discontinued
0.6583	Remote Similarity	NPD7838	Discovery
0.6567	Remote Similarity	NPD6317	Approved
0.6562	Remote Similarity	NPD4767	Approved
0.6562	Remote Similarity	NPD4768	Approved
0.6557	Remote Similarity	NPD5282	Discontinued
0.6552	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7902	Approved
0.6522	Remote Similarity	NPD7830	Approved
0.6522	Remote Similarity	NPD7829	Approved
0.6519	Remote Similarity	NPD6314	Approved
0.6519	Remote Similarity	NPD6313	Approved
0.6504	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6845	Suspended
0.65	Remote Similarity	NPD1695	Approved
0.6496	Remote Similarity	NPD6909	Approved
0.6496	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6908	Approved
0.6489	Remote Similarity	NPD5248	Approved
0.6489	Remote Similarity	NPD5250	Approved
0.6489	Remote Similarity	NPD5249	Phase 3
0.6489	Remote Similarity	NPD5251	Approved
0.6489	Remote Similarity	NPD5247	Approved
0.6462	Remote Similarity	NPD5128	Approved
0.6452	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5221	Approved
0.6452	Remote Similarity	NPD4697	Phase 3
0.6452	Remote Similarity	NPD5222	Approved
0.6441	Remote Similarity	NPD1694	Approved
0.6423	Remote Similarity	NPD7748	Approved
0.6406	Remote Similarity	NPD4754	Approved
0.64	Remote Similarity	NPD5173	Approved
0.6397	Remote Similarity	NPD7641	Discontinued
0.6393	Remote Similarity	NPD7515	Phase 2
0.6393	Remote Similarity	NPD6079	Approved
0.6393	Remote Similarity	NPD5693	Phase 1
0.6389	Remote Similarity	NPD8338	Approved
0.6386	Remote Similarity	NPD7799	Discontinued
0.6371	Remote Similarity	NPD5210	Approved
0.6371	Remote Similarity	NPD4629	Approved
0.637	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD5328	Approved
0.6364	Remote Similarity	NPD5956	Approved
0.6364	Remote Similarity	NPD4753	Phase 2
0.6357	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4202	Approved
0.6338	Remote Similarity	NPD8336	Approved
0.6338	Remote Similarity	NPD8337	Approved
0.6331	Remote Similarity	NPD8080	Discontinued
0.6325	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5215	Approved
0.6316	Remote Similarity	NPD5217	Approved
0.6316	Remote Similarity	NPD5216	Approved
0.6312	Remote Similarity	NPD8451	Approved
0.6311	Remote Similarity	NPD5785	Approved
0.6303	Remote Similarity	NPD1696	Phase 3
0.629	Remote Similarity	NPD7900	Approved
0.629	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5737	Approved
0.6281	Remote Similarity	NPD6672	Approved
0.6279	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7625	Phase 1
0.6268	Remote Similarity	NPD8448	Approved
0.626	Remote Similarity	NPD7983	Approved
0.625	Remote Similarity	NPD3618	Phase 1
0.6241	Remote Similarity	NPD5169	Approved
0.6241	Remote Similarity	NPD5135	Approved
0.6241	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6904	Approved
0.623	Remote Similarity	NPD6673	Approved
0.623	Remote Similarity	NPD6080	Approved
0.6218	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5779	Approved
0.621	Remote Similarity	NPD5778	Approved
0.6198	Remote Similarity	NPD3573	Approved
0.6194	Remote Similarity	NPD5127	Approved
0.6167	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6001	Approved
0.6154	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD8444	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