NPASS Compound

Structure

CID56413 OpenBabel06191715392D 24 27 0 0 1 0 0 0 0 0999 V2000 2.9799 -1.9820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8158 -0.6128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2664 -1.3933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5847 -2.7450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8045 -3.2508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -2.7864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3652 -2.2944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8043 -2.2944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6088 -1.8576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5848 -0.0415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8043 -0.4644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0732 -1.9820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6088 -2.7864 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.8576 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5848 -0.9426 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7332 -1.3931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8044 -0.4644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3652 -1.3932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8043 -1.3932 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8044 -1.3932 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3652 0.4091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1865 -0.6079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5848 -0.0138 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 12 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 9 13 1 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 19 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 5 1 6 0 0 0 14 19 1 1 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 1 0 0 0 16 20 1 0 0 0 0 16 22 2 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 19 8 1 1 0 0 0 20 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	347.502
LogP:	3.018
LogD:	2.91
LogS:	-4.469
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.455
Synthetic Accessibility Score:	6.089
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.106
MDCK Permeability:	2.70701311819721e-05
Pgp-inhibitor:	0.895
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.132
30% Bioavailability (F30%):	0.521

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.26
Plasma Protein Binding (PPB):	81.91913604736328%
Volume Distribution (VD):	0.958
Pgp-substrate:	17.285158157348633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.182
CYP2C19-substrate:	0.711
CYP2C9-inhibitor:	0.353
CYP2C9-substrate:	0.144
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.712
CYP3A4-substrate:	0.27

ADMET: Excretion

Clearance (CL):	6.092
Half-life (T1/2):	0.165

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.138
Rat Oral Acute Toxicity:	0.799
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.487
Carcinogencity:	0.403
Eye Corrosion:	0.009
Eye Irritation:	0.425
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC56413

Natural Product ID:	NPC56413
*Common Name:**	Sculponeatin N
IUPAC Name:	n.a.
Synonyms:	Sculponeatin N
Standard InCHIKey:	CRJKTSIXXJOHPU-PULXTJHUSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-12-13-5-6-14-19(8-4-7-18(2,3)15(19)10-21)11-24-17(23)20(14,9-13)16(12)22/h13-15,21H,1,4-11H2,2-3H3/t13-,14+,15-,19-,20+/m1/s1
SMILES:	C=C1[C@@H]2CC[C@H]3[C@@]4(CCCC(C)(C)[C@H]4CO)COC(=O)[C@]3(C2)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022475
PubChem CID:	49870969
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19099464]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19697926]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2421673]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	aerial parts	Muli County, Sichuan Province, China	2011-AUG	PMID[24219809]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9599286]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19768	Xylosalsola arbuscula	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20336	Arctotheca calendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20470	Elaeagnus orientalis	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16409	Quercus pedunculata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1558	Ozothamnus obcordatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16021	Boletus bovinus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20543	Psydrax livida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17240	Crematogaster brevis	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20115	Melampodium argophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19889	Cereus stellatus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21614	Urceolaria scruposa	Species	Trichodinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19763	Meloidogyne incognita	Species	Meloidogynidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17508	Danae racemosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	210.0	nM	PMID[460922]

☑ 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 NPC56413 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	190
0.1-0.2	1489
0.2-0.3	6349
0.3-0.4	13920
0.4-0.5	7051
0.5-0.6	6327
0.6-0.7	5255
0.7-0.8	1868
0.8-0.85	179
0.85-0.9	66
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9011	High Similarity	NPC26270
0.8977	High Similarity	NPC250753
0.8913	High Similarity	NPC267921
0.8817	High Similarity	NPC236585
0.8817	High Similarity	NPC148279
0.8804	High Similarity	NPC474793
0.8681	High Similarity	NPC470232
0.8632	High Similarity	NPC96217
0.8602	High Similarity	NPC471038
0.8587	High Similarity	NPC329910
0.8587	High Similarity	NPC13949
0.8571	High Similarity	NPC41649
0.8571	High Similarity	NPC475118
0.8571	High Similarity	NPC470385
0.8571	High Similarity	NPC47853
0.8571	High Similarity	NPC470386
0.8556	High Similarity	NPC198242
0.8556	High Similarity	NPC211403
0.8542	High Similarity	NPC101842
0.8506	High Similarity	NPC201655
0.8478	Intermediate Similarity	NPC98639
0.8478	Intermediate Similarity	NPC210214
0.8478	Intermediate Similarity	NPC470229
0.8462	Intermediate Similarity	NPC294263
0.8454	Intermediate Similarity	NPC103172
0.8454	Intermediate Similarity	NPC164600
0.8452	Intermediate Similarity	NPC471475
0.8438	Intermediate Similarity	NPC139347
0.8434	Intermediate Similarity	NPC212661
0.8434	Intermediate Similarity	NPC471035
0.8434	Intermediate Similarity	NPC106078
0.8427	Intermediate Similarity	NPC255176
0.8421	Intermediate Similarity	NPC46848
0.8404	Intermediate Similarity	NPC288
0.8404	Intermediate Similarity	NPC109059
0.8387	Intermediate Similarity	NPC200054
0.8387	Intermediate Similarity	NPC470387
0.8387	Intermediate Similarity	NPC29410
0.8367	Intermediate Similarity	NPC61071
0.8367	Intermediate Similarity	NPC96333
0.8367	Intermediate Similarity	NPC88833
0.8333	Intermediate Similarity	NPC275990
0.8333	Intermediate Similarity	NPC476810
0.8333	Intermediate Similarity	NPC474570
0.8316	Intermediate Similarity	NPC470388
0.8316	Intermediate Similarity	NPC287676
0.8315	Intermediate Similarity	NPC259009
0.8315	Intermediate Similarity	NPC96496
0.8315	Intermediate Similarity	NPC134197
0.8298	Intermediate Similarity	NPC10864
0.8283	Intermediate Similarity	NPC232133
0.8276	Intermediate Similarity	NPC471036
0.8276	Intermediate Similarity	NPC291320
0.8276	Intermediate Similarity	NPC471037
0.8265	Intermediate Similarity	NPC56656
0.8247	Intermediate Similarity	NPC209298
0.8247	Intermediate Similarity	NPC122811
0.8247	Intermediate Similarity	NPC87927
0.8247	Intermediate Similarity	NPC277074
0.8229	Intermediate Similarity	NPC52899
0.8229	Intermediate Similarity	NPC289148
0.8229	Intermediate Similarity	NPC163963
0.8229	Intermediate Similarity	NPC14634
0.8214	Intermediate Similarity	NPC238227
0.8211	Intermediate Similarity	NPC16911
0.8211	Intermediate Similarity	NPC78427
0.8211	Intermediate Similarity	NPC38471
0.8211	Intermediate Similarity	NPC162459
0.8211	Intermediate Similarity	NPC98837
0.8211	Intermediate Similarity	NPC20479
0.8211	Intermediate Similarity	NPC28864
0.8211	Intermediate Similarity	NPC38296
0.8211	Intermediate Similarity	NPC89099
0.8202	Intermediate Similarity	NPC471042
0.82	Intermediate Similarity	NPC469983
0.8191	Intermediate Similarity	NPC104568
0.8182	Intermediate Similarity	NPC471474
0.8182	Intermediate Similarity	NPC186054
0.8163	Intermediate Similarity	NPC474558
0.8163	Intermediate Similarity	NPC202793
0.8161	Intermediate Similarity	NPC474605
0.8161	Intermediate Similarity	NPC476292
0.8152	Intermediate Similarity	NPC278106
0.8152	Intermediate Similarity	NPC470230
0.8144	Intermediate Similarity	NPC286519
0.8144	Intermediate Similarity	NPC214946
0.8144	Intermediate Similarity	NPC88203
0.8144	Intermediate Similarity	NPC76866
0.8144	Intermediate Similarity	NPC304832
0.8144	Intermediate Similarity	NPC148628
0.8144	Intermediate Similarity	NPC246736
0.8132	Intermediate Similarity	NPC471043
0.8125	Intermediate Similarity	NPC293866
0.8119	Intermediate Similarity	NPC98069
0.8119	Intermediate Similarity	NPC49730
0.8105	Intermediate Similarity	NPC96839
0.81	Intermediate Similarity	NPC473410
0.81	Intermediate Similarity	NPC63841
0.81	Intermediate Similarity	NPC471094
0.81	Intermediate Similarity	NPC469984
0.809	Intermediate Similarity	NPC471034
0.809	Intermediate Similarity	NPC102292
0.809	Intermediate Similarity	NPC190704
0.8085	Intermediate Similarity	NPC205173
0.8081	Intermediate Similarity	NPC138908
0.8081	Intermediate Similarity	NPC200957
0.8081	Intermediate Similarity	NPC265127
0.8068	Intermediate Similarity	NPC118800
0.8065	Intermediate Similarity	NPC287118
0.8065	Intermediate Similarity	NPC59170
0.8065	Intermediate Similarity	NPC474807
0.8065	Intermediate Similarity	NPC473690
0.8065	Intermediate Similarity	NPC471902
0.8061	Intermediate Similarity	NPC470310
0.8061	Intermediate Similarity	NPC216114
0.8061	Intermediate Similarity	NPC159442
0.8043	Intermediate Similarity	NPC51486
0.8043	Intermediate Similarity	NPC80401
0.8043	Intermediate Similarity	NPC180849
0.8041	Intermediate Similarity	NPC252614
0.8041	Intermediate Similarity	NPC39683
0.8041	Intermediate Similarity	NPC81530
0.8022	Intermediate Similarity	NPC211162
0.8022	Intermediate Similarity	NPC183374
0.802	Intermediate Similarity	NPC131903
0.802	Intermediate Similarity	NPC102741
0.8	Intermediate Similarity	NPC176949
0.8	Intermediate Similarity	NPC185638
0.8	Intermediate Similarity	NPC201908
0.8	Intermediate Similarity	NPC70661
0.8	Intermediate Similarity	NPC472505
0.8	Intermediate Similarity	NPC29152
0.8	Intermediate Similarity	NPC166993
0.798	Intermediate Similarity	NPC98603
0.798	Intermediate Similarity	NPC96268
0.798	Intermediate Similarity	NPC84928
0.7979	Intermediate Similarity	NPC124207
0.7979	Intermediate Similarity	NPC191094
0.7979	Intermediate Similarity	NPC303863
0.7979	Intermediate Similarity	NPC302008
0.7979	Intermediate Similarity	NPC169751
0.7979	Intermediate Similarity	NPC272635
0.7978	Intermediate Similarity	NPC263974
0.7978	Intermediate Similarity	NPC146683
0.7959	Intermediate Similarity	NPC136289
0.7959	Intermediate Similarity	NPC309388
0.7959	Intermediate Similarity	NPC15396
0.7959	Intermediate Similarity	NPC475803
0.7957	Intermediate Similarity	NPC299185
0.7957	Intermediate Similarity	NPC475416
0.7957	Intermediate Similarity	NPC154101
0.7957	Intermediate Similarity	NPC471901
0.7957	Intermediate Similarity	NPC476168
0.7955	Intermediate Similarity	NPC170985
0.7955	Intermediate Similarity	NPC476935
0.7955	Intermediate Similarity	NPC46881
0.7955	Intermediate Similarity	NPC110780
0.7952	Intermediate Similarity	NPC161187
0.7952	Intermediate Similarity	NPC330659
0.7952	Intermediate Similarity	NPC244708
0.7941	Intermediate Similarity	NPC137104
0.7941	Intermediate Similarity	NPC320383
0.7941	Intermediate Similarity	NPC85391
0.7941	Intermediate Similarity	NPC474786
0.7941	Intermediate Similarity	NPC471093
0.7935	Intermediate Similarity	NPC213832
0.7935	Intermediate Similarity	NPC24772
0.7935	Intermediate Similarity	NPC116146
0.7935	Intermediate Similarity	NPC57954
0.7931	Intermediate Similarity	NPC274522
0.7931	Intermediate Similarity	NPC472478
0.7931	Intermediate Similarity	NPC476265
0.7921	Intermediate Similarity	NPC218123
0.7921	Intermediate Similarity	NPC231278
0.7921	Intermediate Similarity	NPC273155
0.7921	Intermediate Similarity	NPC112895
0.7921	Intermediate Similarity	NPC211224
0.7917	Intermediate Similarity	NPC156546
0.7917	Intermediate Similarity	NPC253586
0.7912	Intermediate Similarity	NPC153604
0.7912	Intermediate Similarity	NPC33768
0.7912	Intermediate Similarity	NPC165895
0.7912	Intermediate Similarity	NPC174619
0.79	Intermediate Similarity	NPC130511
0.79	Intermediate Similarity	NPC307660
0.7895	Intermediate Similarity	NPC29112
0.7895	Intermediate Similarity	NPC469599
0.7895	Intermediate Similarity	NPC138245
0.7895	Intermediate Similarity	NPC266431
0.7895	Intermediate Similarity	NPC84018
0.7895	Intermediate Similarity	NPC231060
0.7882	Intermediate Similarity	NPC246445
0.7882	Intermediate Similarity	NPC476601
0.7879	Intermediate Similarity	NPC469985
0.7872	Intermediate Similarity	NPC82138
0.7872	Intermediate Similarity	NPC144739
0.7872	Intermediate Similarity	NPC181594
0.7872	Intermediate Similarity	NPC199543
0.7872	Intermediate Similarity	NPC59350
0.7865	Intermediate Similarity	NPC245866

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 NPC56413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1905
0.2-0.3	4015
0.3-0.4	2081
0.4-0.5	506
0.5-0.6	199
0.6-0.7	163
0.7-0.8	112
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
0.7872	Intermediate Similarity	NPD6399	Phase 3
0.7865	Intermediate Similarity	NPD4788	Approved
0.7766	Intermediate Similarity	NPD8034	Phase 2
0.7766	Intermediate Similarity	NPD8035	Phase 2
0.7732	Intermediate Similarity	NPD6083	Phase 2
0.7732	Intermediate Similarity	NPD6084	Phase 2
0.7692	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5697	Approved
0.7634	Intermediate Similarity	NPD6672	Approved
0.7634	Intermediate Similarity	NPD5737	Approved
0.7573	Intermediate Similarity	NPD6011	Approved
0.7573	Intermediate Similarity	NPD6881	Approved
0.7573	Intermediate Similarity	NPD6899	Approved
0.7558	Intermediate Similarity	NPD3702	Approved
0.7549	Intermediate Similarity	NPD5739	Approved
0.7549	Intermediate Similarity	NPD6675	Approved
0.7549	Intermediate Similarity	NPD6402	Approved
0.7549	Intermediate Similarity	NPD7128	Approved
0.7526	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.7476	Intermediate Similarity	NPD5701	Approved
0.7475	Intermediate Similarity	NPD5696	Approved
0.7429	Intermediate Similarity	NPD7290	Approved
0.7429	Intermediate Similarity	NPD7102	Approved
0.7429	Intermediate Similarity	NPD6883	Approved
0.7419	Intermediate Similarity	NPD7146	Approved
0.7419	Intermediate Similarity	NPD7521	Approved
0.7419	Intermediate Similarity	NPD6684	Approved
0.7419	Intermediate Similarity	NPD5330	Approved
0.7419	Intermediate Similarity	NPD6409	Approved
0.7419	Intermediate Similarity	NPD7334	Approved
0.7404	Intermediate Similarity	NPD7320	Approved
0.7396	Intermediate Similarity	NPD6079	Approved
0.7391	Intermediate Similarity	NPD3133	Approved
0.7391	Intermediate Similarity	NPD3665	Phase 1
0.7391	Intermediate Similarity	NPD3666	Approved
0.7391	Intermediate Similarity	NPD4786	Approved
0.7368	Intermediate Similarity	NPD4753	Phase 2
0.7368	Intermediate Similarity	NPD5328	Approved
0.7363	Intermediate Similarity	NPD3667	Approved
0.7358	Intermediate Similarity	NPD8130	Phase 1
0.7358	Intermediate Similarity	NPD6617	Approved
0.7358	Intermediate Similarity	NPD6869	Approved
0.7358	Intermediate Similarity	NPD6650	Approved
0.7358	Intermediate Similarity	NPD6649	Approved
0.7358	Intermediate Similarity	NPD6847	Approved
0.7333	Intermediate Similarity	NPD6373	Approved
0.7333	Intermediate Similarity	NPD6372	Approved
0.729	Intermediate Similarity	NPD8297	Approved
0.729	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD5221	Approved
0.7273	Intermediate Similarity	NPD5222	Approved
0.7273	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6903	Approved
0.7245	Intermediate Similarity	NPD7748	Approved
0.7234	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3618	Phase 1
0.7229	Intermediate Similarity	NPD4224	Phase 2
0.7228	Intermediate Similarity	NPD5286	Approved
0.7228	Intermediate Similarity	NPD4696	Approved
0.7228	Intermediate Similarity	NPD5285	Approved
0.7216	Intermediate Similarity	NPD6411	Approved
0.7216	Intermediate Similarity	NPD5281	Approved
0.7216	Intermediate Similarity	NPD7515	Phase 2
0.7216	Intermediate Similarity	NPD5284	Approved
0.72	Intermediate Similarity	NPD7902	Approved
0.72	Intermediate Similarity	NPD5173	Approved
0.72	Intermediate Similarity	NPD4755	Approved
0.7196	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6116	Phase 1
0.7188	Intermediate Similarity	NPD6673	Approved
0.7188	Intermediate Similarity	NPD6080	Approved
0.7188	Intermediate Similarity	NPD6904	Approved
0.7174	Intermediate Similarity	NPD4221	Approved
0.7174	Intermediate Similarity	NPD4223	Phase 3
0.7174	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4629	Approved
0.7172	Intermediate Similarity	NPD5210	Approved
0.7158	Intermediate Similarity	NPD3573	Approved
0.7157	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD6319	Approved
0.7108	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4697	Phase 3
0.7091	Intermediate Similarity	NPD6274	Approved
0.7087	Intermediate Similarity	NPD5211	Phase 2
0.7087	Intermediate Similarity	NPD5226	Approved
0.7087	Intermediate Similarity	NPD5224	Approved
0.7087	Intermediate Similarity	NPD4633	Approved
0.7087	Intermediate Similarity	NPD5225	Approved
0.7083	Intermediate Similarity	NPD5208	Approved
0.7079	Intermediate Similarity	NPD6117	Approved
0.7064	Intermediate Similarity	NPD4632	Approved
0.7059	Intermediate Similarity	NPD4700	Approved
0.7053	Intermediate Similarity	NPD6098	Approved
0.7053	Intermediate Similarity	NPD5279	Phase 3
0.7045	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5693	Phase 1
0.7027	Intermediate Similarity	NPD6317	Approved
0.7027	Intermediate Similarity	NPD7115	Discovery
0.7021	Intermediate Similarity	NPD4197	Approved
0.7019	Intermediate Similarity	NPD5175	Approved
0.7019	Intermediate Similarity	NPD5174	Approved
0.7011	Intermediate Similarity	NPD6081	Approved
0.701	Intermediate Similarity	NPD6101	Approved
0.701	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6412	Phase 2
0.6964	Remote Similarity	NPD6313	Approved
0.6964	Remote Similarity	NPD6314	Approved
0.6964	Remote Similarity	NPD6335	Approved
0.6961	Remote Similarity	NPD7638	Approved
0.6957	Remote Similarity	NPD4695	Discontinued
0.6952	Remote Similarity	NPD5141	Approved
0.6947	Remote Similarity	NPD5329	Approved
0.6944	Remote Similarity	NPD4634	Approved
0.6939	Remote Similarity	NPD5692	Phase 3
0.6937	Remote Similarity	NPD6868	Approved
0.6923	Remote Similarity	NPD6697	Approved
0.6923	Remote Similarity	NPD6118	Approved
0.6923	Remote Similarity	NPD6115	Approved
0.6923	Remote Similarity	NPD3617	Approved
0.6923	Remote Similarity	NPD6114	Approved
0.6916	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6686	Approved
0.6903	Remote Similarity	NPD7100	Approved
0.6903	Remote Similarity	NPD7101	Approved
0.69	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7900	Approved
0.6897	Remote Similarity	NPD4789	Approved
0.6897	Remote Similarity	NPD7492	Approved
0.6893	Remote Similarity	NPD7640	Approved
0.6893	Remote Similarity	NPD7639	Approved
0.6887	Remote Similarity	NPD6008	Approved
0.6875	Remote Similarity	NPD5690	Phase 2
0.6875	Remote Similarity	NPD5205	Approved
0.6875	Remote Similarity	NPD4138	Approved
0.6875	Remote Similarity	NPD4690	Approved
0.6875	Remote Similarity	NPD4688	Approved
0.6875	Remote Similarity	NPD6009	Approved
0.6875	Remote Similarity	NPD4693	Phase 3
0.6875	Remote Similarity	NPD4689	Approved
0.6869	Remote Similarity	NPD5694	Approved
0.6869	Remote Similarity	NPD6050	Approved
0.6857	Remote Similarity	NPD4754	Approved
0.6842	Remote Similarity	NPD3668	Phase 3
0.6842	Remote Similarity	NPD6054	Approved
0.6838	Remote Similarity	NPD6616	Approved
0.6832	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5777	Approved
0.6818	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4225	Approved
0.6783	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5983	Phase 2
0.6783	Remote Similarity	NPD6015	Approved
0.6783	Remote Similarity	NPD6016	Approved
0.6782	Remote Similarity	NPD3698	Phase 2
0.6782	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7078	Approved
0.6768	Remote Similarity	NPD5207	Approved
0.6759	Remote Similarity	NPD4730	Approved
0.6759	Remote Similarity	NPD4729	Approved
0.6759	Remote Similarity	NPD5128	Approved
0.6757	Remote Similarity	NPD8133	Approved
0.6733	Remote Similarity	NPD6001	Approved
0.6729	Remote Similarity	NPD4767	Approved
0.6729	Remote Similarity	NPD4768	Approved
0.6724	Remote Similarity	NPD5988	Approved
0.6724	Remote Similarity	NPD6370	Approved
0.6723	Remote Similarity	NPD7736	Approved
0.6705	Remote Similarity	NPD4244	Approved
0.6705	Remote Similarity	NPD4245	Approved
0.6701	Remote Similarity	NPD5280	Approved
0.6701	Remote Similarity	NPD4694	Approved
0.67	Remote Similarity	NPD7637	Suspended
0.6696	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD4195	Approved
0.6639	Remote Similarity	NPD8293	Discontinued
0.6638	Remote Similarity	NPD6908	Approved
0.6638	Remote Similarity	NPD6909	Approved
0.6636	Remote Similarity	NPD5135	Approved
0.6636	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD5250	Approved
0.6636	Remote Similarity	NPD5248	Approved
0.6636	Remote Similarity	NPD5169	Approved
0.6636	Remote Similarity	NPD5251	Approved
0.6636	Remote Similarity	NPD5247	Approved
0.6636	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6435	Approved
0.6606	Remote Similarity	NPD5168	Approved
0.6602	Remote Similarity	NPD7614	Phase 1
0.66	Remote Similarity	NPD5785	Approved
0.6596	Remote Similarity	NPD7525	Registered

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