NPASS Compound

Structure

CID254146 OpenBabel06191716052D 38 46 0 0 1 0 0 0 0 0999 V2000 -0.4332 1.0321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8128 0.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5964 -2.4102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2253 2.2245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2253 1.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4383 0.2563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5190 2.6322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2687 -0.5414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4004 2.2245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0853 -0.8411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9295 1.2432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1066 1.0012 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4004 1.4090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2037 0.4671 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5190 1.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1066 2.6322 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8403 -1.4869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6699 -0.1951 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9442 0.5810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9592 -0.1789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5876 -1.9480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2668 0.1360 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8128 1.4090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0964 -1.8180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6627 -1.0870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8128 2.2245 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5894 1.3237 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8517 -1.1723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5190 0.0075 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9365 0.6336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8185 0.1248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4018 -2.5178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2322 -0.2727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1867 1.5980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7773 -1.1558 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8128 3.0399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8045 -2.3135 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 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 7 1 0 0 0 0 5 15 1 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 8 25 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 34 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 1 0 0 0 13 27 1 6 0 0 0 14 20 1 0 0 0 0 14 22 1 6 0 0 0 15 23 1 0 0 0 0 15 29 2 0 0 0 0 16 26 1 1 0 0 0 16 36 1 0 0 0 0 17 24 1 6 0 0 0 17 35 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 0 0 0 0 19 30 2 0 0 0 0 20 31 2 0 0 0 0 20 35 1 0 0 0 0 21 25 1 0 0 0 0 21 32 2 0 0 0 0 21 37 1 0 0 0 0 22 1 1 1 0 0 0 23 26 1 1 0 0 0 24 28 1 6 0 0 0 24 37 1 0 0 0 0 25 28 1 1 0 0 0 25 33 1 0 0 0 0 26 7 1 1 0 0 0 26 36 1 0 0 0 0 27 19 1 6 0 0 0 27 34 1 0 0 0 0 27 38 1 0 0 0 0 28 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.18
Volume:	490.556
LogP:	2.173
LogD:	0.996
LogS:	-4.743
# Rotatable Bonds:	0
TPSA:	137.96
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	3.255
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
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:	-5.382
MDCK Permeability:	3.976252628490329e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.912

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.678
Plasma Protein Binding (PPB):	25.396106719970703%
Volume Distribution (VD):	0.533
Pgp-substrate:	58.741920471191406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.633
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.715
CYP3A4-substrate:	0.802

ADMET: Excretion

Clearance (CL):	7.976
Half-life (T1/2):	0.189

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.528
AMES Toxicity:	0.857
Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.516
Carcinogencity:	0.972
Eye Corrosion:	0.011
Eye Irritation:	0.022
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC254146

Natural Product ID:	NPC254146
*Common Name:**	Physalin J
IUPAC Name:	n.a.
Synonyms:	Physalin J
Standard InCHIKey:	VSLWNSSUMFSGFF-LRODIAEASA-N
Standard InCHI:	InChI=1S/C28H30O10/c1-22-10-17-24(3)28-18(22)19(30)27(38-28,34-11-14(22)20(31)35-17)13-9-16-26(36-16)7-4-5-15(29)23(26,2)12(13)6-8-25(28,33)21(32)37-24/h4-5,12-14,16-18,33H,6-11H2,1-3H3/t12-,13+,14-,16-,17+,18?,22+,23-,24-,25+,26-,27-,28-/m0/s1
SMILES:	C[C@@]12C[C@@H]3[C@@]4(C)[C@@]56C2C(=O)[C@@]([C@@H]2C[C@H]7[C@]8(CC=CC(=O)[C@]8(C)[C@H]2CC[C@]5(C(=O)O4)O)O7)(OC[C@H]1C(=O)O3)O6
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387781
PubChem CID:	44426449
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001671] Physalins and derivatives

*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
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17580910]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954931]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23270478]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25396337]
NPO1680	Physalis angulata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27295506]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1680	Physalis angulata	Species	Solanaceae	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
IC50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT762	Cell Line	A-431	Homo sapiens	EC50	=	17.0	ug.mL-1	PMID[510307]
NPT2601	Individual Protein	NF-kappaB inhibitor alpha	Homo sapiens	IC50	>	50000.0	nM	PMID[510308]
NPT2	Others	Unspecified		IC50	=	36200.0	nM	PMID[510308]

☑ 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 NPC254146 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	339
0.1-0.2	2050
0.2-0.3	6045
0.3-0.4	9760
0.4-0.5	12025
0.5-0.6	7100
0.6-0.7	4414
0.7-0.8	908
0.8-0.85	40
0.85-0.9	6
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC33378
1.0	High Similarity	NPC6274
0.9672	High Similarity	NPC254614
0.9672	High Similarity	NPC100390
0.9508	High Similarity	NPC264192
0.9268	High Similarity	NPC188291
0.9213	High Similarity	NPC243014
0.8906	High Similarity	NPC242486
0.8906	High Similarity	NPC15215
0.8898	High Similarity	NPC102316
0.8828	High Similarity	NPC168879
0.878	High Similarity	NPC477046
0.878	High Similarity	NPC102822
0.877	High Similarity	NPC469488
0.8689	High Similarity	NPC17772
0.8618	High Similarity	NPC470777
0.8537	High Similarity	NPC297179
0.8537	High Similarity	NPC188667
0.8537	High Similarity	NPC204552
0.8455	Intermediate Similarity	NPC474654
0.8455	Intermediate Similarity	NPC122033
0.8455	Intermediate Similarity	NPC97908
0.8455	Intermediate Similarity	NPC470854
0.8455	Intermediate Similarity	NPC287343
0.8425	Intermediate Similarity	NPC24651
0.84	Intermediate Similarity	NPC112038
0.8374	Intermediate Similarity	NPC251236
0.8374	Intermediate Similarity	NPC207217
0.8374	Intermediate Similarity	NPC40632
0.8374	Intermediate Similarity	NPC134869
0.8374	Intermediate Similarity	NPC96312
0.8374	Intermediate Similarity	NPC235539
0.8374	Intermediate Similarity	NPC152199
0.8374	Intermediate Similarity	NPC328374
0.8372	Intermediate Similarity	NPC295220
0.8372	Intermediate Similarity	NPC475636
0.8361	Intermediate Similarity	NPC49451
0.8359	Intermediate Similarity	NPC225049
0.8308	Intermediate Similarity	NPC54614
0.8308	Intermediate Similarity	NPC309096
0.8293	Intermediate Similarity	NPC268238
0.8293	Intermediate Similarity	NPC143268
0.8293	Intermediate Similarity	NPC45218
0.8293	Intermediate Similarity	NPC473798
0.8293	Intermediate Similarity	NPC18547
0.8293	Intermediate Similarity	NPC323821
0.8293	Intermediate Similarity	NPC474906
0.8281	Intermediate Similarity	NPC470922
0.8279	Intermediate Similarity	NPC474516
0.8279	Intermediate Similarity	NPC11252
0.8279	Intermediate Similarity	NPC289312
0.8268	Intermediate Similarity	NPC312833
0.824	Intermediate Similarity	NPC470776
0.8226	Intermediate Similarity	NPC16081
0.8226	Intermediate Similarity	NPC173686
0.8226	Intermediate Similarity	NPC270478
0.8211	Intermediate Similarity	NPC208998
0.8211	Intermediate Similarity	NPC7921
0.8203	Intermediate Similarity	NPC227397
0.8203	Intermediate Similarity	NPC67251
0.8203	Intermediate Similarity	NPC105926
0.8203	Intermediate Similarity	NPC91693
0.8203	Intermediate Similarity	NPC18945
0.8203	Intermediate Similarity	NPC265557
0.8197	Intermediate Similarity	NPC201992
0.8182	Intermediate Similarity	NPC474242
0.8175	Intermediate Similarity	NPC268958
0.8148	Intermediate Similarity	NPC596
0.814	Intermediate Similarity	NPC473255
0.814	Intermediate Similarity	NPC476729
0.8115	Intermediate Similarity	NPC474567
0.811	Intermediate Similarity	NPC107338
0.811	Intermediate Similarity	NPC109607
0.8106	Intermediate Similarity	NPC476855
0.8106	Intermediate Similarity	NPC476862
0.8106	Intermediate Similarity	NPC476852
0.8106	Intermediate Similarity	NPC476863
0.8095	Intermediate Similarity	NPC251310
0.8092	Intermediate Similarity	NPC473620
0.8077	Intermediate Similarity	NPC181999
0.8077	Intermediate Similarity	NPC87662
0.8074	Intermediate Similarity	NPC471089
0.8074	Intermediate Similarity	NPC190065
0.8074	Intermediate Similarity	NPC141215
0.8065	Intermediate Similarity	NPC51978
0.8065	Intermediate Similarity	NPC198539
0.8049	Intermediate Similarity	NPC146945
0.8049	Intermediate Similarity	NPC171888
0.8047	Intermediate Similarity	NPC470779
0.8047	Intermediate Similarity	NPC275675
0.8045	Intermediate Similarity	NPC180902
0.8045	Intermediate Similarity	NPC475139
0.8031	Intermediate Similarity	NPC473203
0.8031	Intermediate Similarity	NPC476529
0.8031	Intermediate Similarity	NPC475775
0.803	Intermediate Similarity	NPC470880
0.803	Intermediate Similarity	NPC476854
0.803	Intermediate Similarity	NPC476851
0.8016	Intermediate Similarity	NPC176513
0.8016	Intermediate Similarity	NPC27999
0.8016	Intermediate Similarity	NPC477116
0.8016	Intermediate Similarity	NPC470775
0.8015	Intermediate Similarity	NPC295885
0.8015	Intermediate Similarity	NPC140045
0.8015	Intermediate Similarity	NPC476008
0.8015	Intermediate Similarity	NPC305496
0.8015	Intermediate Similarity	NPC470882
0.8015	Intermediate Similarity	NPC473253
0.8	Intermediate Similarity	NPC243354
0.8	Intermediate Similarity	NPC262813
0.7984	Intermediate Similarity	NPC205534
0.7955	Intermediate Similarity	NPC476859
0.7951	Intermediate Similarity	NPC293850
0.7941	Intermediate Similarity	NPC251998
0.7939	Intermediate Similarity	NPC285091
0.7939	Intermediate Similarity	NPC217901
0.7939	Intermediate Similarity	NPC477745
0.7939	Intermediate Similarity	NPC473635
0.7937	Intermediate Similarity	NPC259306
0.7937	Intermediate Similarity	NPC474734
0.7937	Intermediate Similarity	NPC474046
0.7937	Intermediate Similarity	NPC470628
0.7926	Intermediate Similarity	NPC100017
0.7926	Intermediate Similarity	NPC471136
0.7926	Intermediate Similarity	NPC475500
0.7926	Intermediate Similarity	NPC182266
0.7926	Intermediate Similarity	NPC473548
0.7926	Intermediate Similarity	NPC223356
0.7926	Intermediate Similarity	NPC475154
0.7926	Intermediate Similarity	NPC471137
0.7923	Intermediate Similarity	NPC120724
0.792	Intermediate Similarity	NPC194273
0.792	Intermediate Similarity	NPC320118
0.7903	Intermediate Similarity	NPC474229
0.7903	Intermediate Similarity	NPC471243
0.7895	Intermediate Similarity	NPC162495
0.7891	Intermediate Similarity	NPC127530
0.7891	Intermediate Similarity	NPC473920
0.7891	Intermediate Similarity	NPC279143
0.7879	Intermediate Similarity	NPC287423
0.7879	Intermediate Similarity	NPC473265
0.7879	Intermediate Similarity	NPC470780
0.7879	Intermediate Similarity	NPC168849
0.7879	Intermediate Similarity	NPC475273
0.7874	Intermediate Similarity	NPC473590
0.7874	Intermediate Similarity	NPC309433
0.7869	Intermediate Similarity	NPC3316
0.7869	Intermediate Similarity	NPC144854
0.7857	Intermediate Similarity	NPC469877
0.7857	Intermediate Similarity	NPC470919
0.7857	Intermediate Similarity	NPC299849
0.7857	Intermediate Similarity	NPC117712
0.7852	Intermediate Similarity	NPC478151
0.7846	Intermediate Similarity	NPC471965
0.7846	Intermediate Similarity	NPC170538
0.784	Intermediate Similarity	NPC90769
0.784	Intermediate Similarity	NPC302146
0.7836	Intermediate Similarity	NPC251564
0.7836	Intermediate Similarity	NPC477189
0.7836	Intermediate Similarity	NPC475314
0.7836	Intermediate Similarity	NPC475606
0.7829	Intermediate Similarity	NPC241192
0.7812	Intermediate Similarity	NPC473720
0.7812	Intermediate Similarity	NPC106644
0.7812	Intermediate Similarity	NPC318751
0.781	Intermediate Similarity	NPC68282
0.7805	Intermediate Similarity	NPC154608
0.7805	Intermediate Similarity	NPC192813
0.7805	Intermediate Similarity	NPC277017
0.7803	Intermediate Similarity	NPC293112
0.7803	Intermediate Similarity	NPC47113
0.7803	Intermediate Similarity	NPC174367
0.7795	Intermediate Similarity	NPC190185
0.7795	Intermediate Similarity	NPC477509
0.7795	Intermediate Similarity	NPC179626
0.7795	Intermediate Similarity	NPC213084
0.7787	Intermediate Similarity	NPC181357
0.7786	Intermediate Similarity	NPC202666
0.7786	Intermediate Similarity	NPC267822
0.7786	Intermediate Similarity	NPC11895
0.7786	Intermediate Similarity	NPC471961
0.7786	Intermediate Similarity	NPC478066
0.7786	Intermediate Similarity	NPC471964
0.7786	Intermediate Similarity	NPC262199
0.7786	Intermediate Similarity	NPC14617
0.7778	Intermediate Similarity	NPC471855
0.7778	Intermediate Similarity	NPC473485
0.7778	Intermediate Similarity	NPC478150
0.7778	Intermediate Similarity	NPC477126
0.7778	Intermediate Similarity	NPC477266
0.7778	Intermediate Similarity	NPC474508
0.7778	Intermediate Similarity	NPC478153
0.7778	Intermediate Similarity	NPC478154
0.7778	Intermediate Similarity	NPC478152
0.7769	Intermediate Similarity	NPC75417
0.7769	Intermediate Similarity	NPC470921
0.7761	Intermediate Similarity	NPC473593
0.7752	Intermediate Similarity	NPC319570
0.7752	Intermediate Similarity	NPC161065
0.7744	Intermediate Similarity	NPC42399

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 NPC254146 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	2265
0.2-0.3	4056
0.3-0.4	1652
0.4-0.5	536
0.5-0.6	216
0.6-0.7	125
0.7-0.8	20
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
0.7863	Intermediate Similarity	NPD7492	Approved
0.7829	Intermediate Similarity	NPD6054	Approved
0.782	Intermediate Similarity	NPD7736	Approved
0.7803	Intermediate Similarity	NPD6616	Approved
0.7786	Intermediate Similarity	NPD8328	Phase 3
0.7769	Intermediate Similarity	NPD6016	Approved
0.7769	Intermediate Similarity	NPD6015	Approved
0.7744	Intermediate Similarity	NPD7078	Approved
0.771	Intermediate Similarity	NPD6370	Approved
0.771	Intermediate Similarity	NPD5988	Approved
0.7692	Intermediate Similarity	NPD6319	Approved
0.7557	Intermediate Similarity	NPD6059	Approved
0.7481	Intermediate Similarity	NPD8293	Discontinued
0.7462	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD6009	Approved
0.7422	Intermediate Similarity	NPD6882	Approved
0.7381	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8297	Approved
0.7246	Intermediate Similarity	NPD7319	Approved
0.7231	Intermediate Similarity	NPD4632	Approved
0.7222	Intermediate Similarity	NPD6008	Approved
0.7209	Intermediate Similarity	NPD6649	Approved
0.7209	Intermediate Similarity	NPD6650	Approved
0.7197	Intermediate Similarity	NPD7115	Discovery
0.7165	Intermediate Similarity	NPD5697	Approved
0.7109	Intermediate Similarity	NPD6899	Approved
0.7109	Intermediate Similarity	NPD6881	Approved
0.7054	Intermediate Similarity	NPD6012	Approved
0.7054	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6013	Approved
0.7054	Intermediate Similarity	NPD6372	Approved
0.7054	Intermediate Similarity	NPD6014	Approved
0.7054	Intermediate Similarity	NPD6373	Approved
0.705	Intermediate Similarity	NPD6033	Approved
0.7029	Intermediate Similarity	NPD7507	Approved
0.7007	Intermediate Similarity	NPD7604	Phase 2
0.7	Intermediate Similarity	NPD4634	Approved
0.7	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6883	Approved
0.6985	Remote Similarity	NPD5983	Phase 2
0.6977	Remote Similarity	NPD7320	Approved
0.6977	Remote Similarity	NPD6011	Approved
0.6953	Remote Similarity	NPD6402	Approved
0.6953	Remote Similarity	NPD5739	Approved
0.6953	Remote Similarity	NPD6675	Approved
0.6953	Remote Similarity	NPD7128	Approved
0.6947	Remote Similarity	NPD8130	Phase 1
0.6947	Remote Similarity	NPD6869	Approved
0.6947	Remote Similarity	NPD6617	Approved
0.6947	Remote Similarity	NPD6847	Approved
0.6923	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5701	Approved
0.6899	Remote Similarity	NPD6412	Phase 2
0.6861	Remote Similarity	NPD8513	Phase 3
0.6861	Remote Similarity	NPD8515	Approved
0.6861	Remote Similarity	NPD8517	Approved
0.6861	Remote Similarity	NPD8516	Approved
0.6861	Remote Similarity	NPD6921	Approved
0.6846	Remote Similarity	NPD6686	Approved
0.6786	Remote Similarity	NPD6336	Discontinued
0.6769	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5696	Approved
0.6715	Remote Similarity	NPD7516	Approved
0.6713	Remote Similarity	NPD5956	Approved
0.6694	Remote Similarity	NPD5282	Discontinued
0.6693	Remote Similarity	NPD5286	Approved
0.6693	Remote Similarity	NPD5285	Approved
0.6693	Remote Similarity	NPD4696	Approved
0.6642	Remote Similarity	NPD7327	Approved
0.6642	Remote Similarity	NPD7328	Approved
0.6641	Remote Similarity	NPD1700	Approved
0.6619	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6274	Approved
0.6614	Remote Similarity	NPD4225	Approved
0.6612	Remote Similarity	NPD3573	Approved
0.6594	Remote Similarity	NPD7101	Approved
0.6594	Remote Similarity	NPD7100	Approved
0.6589	Remote Similarity	NPD5224	Approved
0.6589	Remote Similarity	NPD5225	Approved
0.6589	Remote Similarity	NPD5211	Phase 2
0.6589	Remote Similarity	NPD4633	Approved
0.6589	Remote Similarity	NPD5226	Approved
0.6569	Remote Similarity	NPD6317	Approved
0.6567	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7260	Phase 2
0.6538	Remote Similarity	NPD5175	Approved
0.6538	Remote Similarity	NPD5174	Approved
0.6535	Remote Similarity	NPD7902	Approved
0.6535	Remote Similarity	NPD4755	Approved
0.6522	Remote Similarity	NPD6314	Approved
0.6522	Remote Similarity	NPD6313	Approved
0.6522	Remote Similarity	NPD6335	Approved
0.6515	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5223	Approved
0.6503	Remote Similarity	NPD8074	Phase 3
0.65	Remote Similarity	NPD7503	Approved
0.65	Remote Similarity	NPD8380	Approved
0.65	Remote Similarity	NPD8033	Approved
0.65	Remote Similarity	NPD8379	Approved
0.65	Remote Similarity	NPD8378	Approved
0.65	Remote Similarity	NPD8296	Approved
0.65	Remote Similarity	NPD8335	Approved
0.6489	Remote Similarity	NPD5141	Approved
0.6466	Remote Similarity	NPD4730	Approved
0.6466	Remote Similarity	NPD4729	Approved
0.6457	Remote Similarity	NPD5221	Approved
0.6457	Remote Similarity	NPD5222	Approved
0.6457	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4700	Approved
0.6429	Remote Similarity	NPD7748	Approved
0.6429	Remote Similarity	NPD8294	Approved
0.6429	Remote Similarity	NPD8377	Approved
0.6406	Remote Similarity	NPD6084	Phase 2
0.6406	Remote Similarity	NPD5173	Approved
0.6406	Remote Similarity	NPD6083	Phase 2
0.6395	Remote Similarity	NPD6845	Suspended
0.6395	Remote Similarity	NPD8338	Approved
0.6378	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4629	Approved
0.6378	Remote Similarity	NPD5695	Phase 3
0.6378	Remote Similarity	NPD5210	Approved
0.6377	Remote Similarity	NPD6868	Approved
0.637	Remote Similarity	NPD5251	Approved
0.637	Remote Similarity	NPD5248	Approved
0.637	Remote Similarity	NPD5250	Approved
0.637	Remote Similarity	NPD5249	Phase 3
0.637	Remote Similarity	NPD5247	Approved
0.635	Remote Similarity	NPD8133	Approved
0.6349	Remote Similarity	NPD6399	Phase 3
0.6333	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD4697	Phase 3
0.6316	Remote Similarity	NPD4767	Approved
0.6316	Remote Similarity	NPD4768	Approved
0.6299	Remote Similarity	NPD7900	Approved
0.6299	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6067	Discontinued
0.6291	Remote Similarity	NPD6334	Approved
0.6291	Remote Similarity	NPD6333	Approved
0.627	Remote Similarity	NPD6079	Approved
0.627	Remote Similarity	NPD6411	Approved
0.627	Remote Similarity	NPD7515	Phase 2
0.6268	Remote Similarity	NPD6908	Approved
0.6268	Remote Similarity	NPD6909	Approved
0.626	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD6371	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD8407	Phase 2
0.6222	Remote Similarity	NPD5128	Approved
0.6204	Remote Similarity	NPD5217	Approved
0.6204	Remote Similarity	NPD5216	Approved
0.6204	Remote Similarity	NPD5215	Approved
0.6199	Remote Similarity	NPD7799	Discontinued
0.6165	Remote Similarity	NPD4754	Approved
0.616	Remote Similarity	NPD6672	Approved
0.616	Remote Similarity	NPD5737	Approved
0.6159	Remote Similarity	NPD6053	Discontinued
0.6149	Remote Similarity	NPD8368	Discontinued
0.6131	Remote Similarity	NPD5135	Approved
0.6131	Remote Similarity	NPD5169	Approved
0.6131	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3618	Phase 1
0.6122	Remote Similarity	NPD8337	Approved
0.6122	Remote Similarity	NPD8336	Approved
0.6119	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6101	Approved
0.6111	Remote Similarity	NPD5328	Approved
0.6107	Remote Similarity	NPD7638	Approved
0.6087	Remote Similarity	NPD5127	Approved
0.6069	Remote Similarity	NPD7642	Approved
0.6063	Remote Similarity	NPD6698	Approved
0.6063	Remote Similarity	NPD46	Approved
0.6061	Remote Similarity	NPD6648	Approved
0.6061	Remote Similarity	NPD7639	Approved
0.6061	Remote Similarity	NPD7640	Approved
0.6047	Remote Similarity	NPD6001	Approved
0.6014	Remote Similarity	NPD4522	Approved
0.6	Remote Similarity	NPD8080	Discontinued
0.5985	Remote Similarity	NPD5168	Approved
0.5984	Remote Similarity	NPD6080	Approved
0.5984	Remote Similarity	NPD6904	Approved
0.5984	Remote Similarity	NPD4753	Phase 2
0.5984	Remote Similarity	NPD6673	Approved
0.5969	Remote Similarity	NPD5779	Approved
0.5969	Remote Similarity	NPD5778	Approved
0.5969	Remote Similarity	NPD4202	Approved
0.5959	Remote Similarity	NPD7829	Approved
0.5959	Remote Similarity	NPD7830	Approved
0.5957	Remote Similarity	NPD5167	Approved
0.5922	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.592	Remote Similarity	NPD1694	Approved
0.5912	Remote Similarity	NPD8435	Approved
0.5912	Remote Similarity	NPD6614	Approved
0.5906	Remote Similarity	NPD6903	Approved
0.5906	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD4695	Discontinued

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