NPASS Compound

Structure

CID124207 OpenBabel06191715482D 35 39 0 0 1 0 0 0 0 0999 V2000 -4.1161 6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7633 5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0766 -2.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -0.4135 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 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7852 5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4980 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1017 -2.3565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 -1.6235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8289 5.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3802 1.1828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3964 -3.3121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8733 -2.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1906 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 28 1 0 0 0 0 11 12 1 0 0 0 0 11 27 1 0 0 0 0 12 29 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 24 1 0 0 0 0 16 29 1 0 0 0 0 16 30 1 0 0 0 0 17 26 1 0 0 0 0 17 35 1 0 0 0 0 19 3 1 6 0 0 0 19 21 1 0 0 0 0 20 31 2 0 0 0 0 21 27 1 6 0 0 0 22 26 1 6 0 0 0 22 30 1 0 0 0 0 23 28 1 1 0 0 0 23 29 1 0 0 0 0 24 32 2 0 0 0 0 24 35 1 0 0 0 0 25 26 1 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 4 1 6 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.32
Volume:	518.059
LogP:	5.808
LogD:	4.296
LogS:	-4.947
# Rotatable Bonds:	5
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.371
Synthetic Accessibility Score:	5.815
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.518
MDCK Permeability:	1.2207319741719402e-05
Pgp-inhibitor:	0.296
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.22
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	87.7830581665039%
Volume Distribution (VD):	0.601
Pgp-substrate:	4.08532190322876%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.803
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.193
CYP2C9-substrate:	0.128
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.785
CYP3A4-substrate:	0.629

ADMET: Excretion

Clearance (CL):	2.202
Half-life (T1/2):	0.358

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.692
Drug-inuced Liver Injury (DILI):	0.192
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.697
Skin Sensitization:	0.92
Carcinogencity:	0.795
Eye Corrosion:	0.292
Eye Irritation:	0.055
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC124207

Natural Product ID:	NPC124207
*Common Name:**	Beddomeilactone
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PGXOUBODVZDNTD-WPVJURGTSA-N
Standard InCHI:	InChI=1S/C30H44O5/c1-18(2)13-20(31)14-19(3)21-9-10-28(6)23-8-7-22-26(4,25(33)34)17-35-24(32)15-30(22)16-29(23,30)12-11-27(21,28)5/h13,19,21-23H,7-12,14-17H2,1-6H3,(H,33,34)/t19-,21-,22+,23+,26-,27-,28+,29+,30-/m1/s1
SMILES:	CC(=CC(=O)C[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@@](C)(COC(=O)C[C@]54C[C@@]35CC[C@]12C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2270130
PubChem CID:	76319653
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO27821	Pochonia chlamydosporia	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.tetlet.2008.10.099]
NPO18304	Jaborosa integrifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO27821	Pochonia chlamydosporia	Species	Clavicipitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20000774]
NPO15090	Zanthoxylum leprieurii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20413315]
NPO17952	Dahlia australis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9513	Lecidea aspidula	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18304	Jaborosa integrifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13578	Arcyria nutans	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18514	Heliopsis scabra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25251	[arthrographis] pinicola	Species	Eremascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16288	Youngia denticulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18167	Antiphiona fragrans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15090	Zanthoxylum leprieurii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27821	Pochonia chlamydosporia	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15352	Spiraea hypericifolia	Species	Rosaceae	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
Others	15

Activity Type	# Activity
Organism	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	80.0	%	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	0.87	cm2	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	8.97	cm2	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	13.6	mg	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	10.2	mg	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	7.2	mg	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	12.1	mg	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	TIME	=	892.8	hr	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	TIME	=	940.8	hr	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	TIME	=	1159.2	hr	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	39.0	%	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	19.0	%	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	3.0	%	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	60.0	%	PMID[534690]
NPT846	Organism	Cnaphalocrocis medinalis	Cnaphalocrocis medinalis	Activity	=	83.0	%	PMID[534690]

☑ 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 NPC124207 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	186
0.1-0.2	1208
0.2-0.3	5706
0.3-0.4	13827
0.4-0.5	7892
0.5-0.6	6782
0.6-0.7	5816
0.7-0.8	1225
0.8-0.85	49
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC474570
0.883	High Similarity	NPC156546
0.8723	High Similarity	NPC29152
0.8723	High Similarity	NPC327788
0.8696	High Similarity	NPC470113
0.8667	High Similarity	NPC96496
0.8526	High Similarity	NPC471153
0.8495	Intermediate Similarity	NPC476187
0.8478	Intermediate Similarity	NPC66344
0.8454	Intermediate Similarity	NPC477521
0.8454	Intermediate Similarity	NPC35751
0.8444	Intermediate Similarity	NPC283733
0.8427	Intermediate Similarity	NPC477373
0.8421	Intermediate Similarity	NPC88310
0.8421	Intermediate Similarity	NPC476174
0.8421	Intermediate Similarity	NPC293052
0.8409	Intermediate Similarity	NPC477372
0.8391	Intermediate Similarity	NPC158846
0.8387	Intermediate Similarity	NPC472866
0.8384	Intermediate Similarity	NPC312900
0.837	Intermediate Similarity	NPC117122
0.8352	Intermediate Similarity	NPC186975
0.8351	Intermediate Similarity	NPC98868
0.8333	Intermediate Similarity	NPC476038
0.8333	Intermediate Similarity	NPC194937
0.8316	Intermediate Similarity	NPC471078
0.8316	Intermediate Similarity	NPC473435
0.8316	Intermediate Similarity	NPC473280
0.8316	Intermediate Similarity	NPC473431
0.8315	Intermediate Similarity	NPC320514
0.8298	Intermediate Similarity	NPC23217
0.8261	Intermediate Similarity	NPC167877
0.8261	Intermediate Similarity	NPC136948
0.8261	Intermediate Similarity	NPC236618
0.8242	Intermediate Similarity	NPC29447
0.8202	Intermediate Similarity	NPC147066
0.82	Intermediate Similarity	NPC72151
0.8191	Intermediate Similarity	NPC51486
0.8191	Intermediate Similarity	NPC471896
0.8182	Intermediate Similarity	NPC477371
0.8172	Intermediate Similarity	NPC472870
0.8172	Intermediate Similarity	NPC80335
0.8152	Intermediate Similarity	NPC195640
0.8144	Intermediate Similarity	NPC106425
0.8144	Intermediate Similarity	NPC122324
0.8144	Intermediate Similarity	NPC151725
0.8137	Intermediate Similarity	NPC220974
0.8132	Intermediate Similarity	NPC214043
0.8132	Intermediate Similarity	NPC85774
0.8119	Intermediate Similarity	NPC235889
0.8111	Intermediate Similarity	NPC133391
0.8105	Intermediate Similarity	NPC473986
0.8105	Intermediate Similarity	NPC474018
0.8105	Intermediate Similarity	NPC154101
0.81	Intermediate Similarity	NPC320447
0.81	Intermediate Similarity	NPC22388
0.8085	Intermediate Similarity	NPC31985
0.8085	Intermediate Similarity	NPC174342
0.8085	Intermediate Similarity	NPC262043
0.8085	Intermediate Similarity	NPC474700
0.8085	Intermediate Similarity	NPC1015
0.8085	Intermediate Similarity	NPC474704
0.8085	Intermediate Similarity	NPC128496
0.8085	Intermediate Similarity	NPC475921
0.8081	Intermediate Similarity	NPC476303
0.8065	Intermediate Similarity	NPC134197
0.8065	Intermediate Similarity	NPC128644
0.8061	Intermediate Similarity	NPC89225
0.8061	Intermediate Similarity	NPC26413
0.8046	Intermediate Similarity	NPC20466
0.8043	Intermediate Similarity	NPC469948
0.8043	Intermediate Similarity	NPC76333
0.8043	Intermediate Similarity	NPC470223
0.8043	Intermediate Similarity	NPC323765
0.8043	Intermediate Similarity	NPC201655
0.8043	Intermediate Similarity	NPC142649
0.8041	Intermediate Similarity	NPC469599
0.8041	Intermediate Similarity	NPC205173
0.8041	Intermediate Similarity	NPC33473
0.8039	Intermediate Similarity	NPC181265
0.8022	Intermediate Similarity	NPC470015
0.8022	Intermediate Similarity	NPC168188
0.8021	Intermediate Similarity	NPC474807
0.802	Intermediate Similarity	NPC176883
0.802	Intermediate Similarity	NPC475526
0.802	Intermediate Similarity	NPC473283
0.802	Intermediate Similarity	NPC329345
0.8	Intermediate Similarity	NPC118174
0.8	Intermediate Similarity	NPC327002
0.8	Intermediate Similarity	NPC474842
0.8	Intermediate Similarity	NPC115899
0.8	Intermediate Similarity	NPC111585
0.8	Intermediate Similarity	NPC90055
0.8	Intermediate Similarity	NPC473514
0.8	Intermediate Similarity	NPC175628
0.8	Intermediate Similarity	NPC282524
0.8	Intermediate Similarity	NPC148414
0.8	Intermediate Similarity	NPC201912
0.8	Intermediate Similarity	NPC161638
0.8	Intermediate Similarity	NPC477149
0.8	Intermediate Similarity	NPC38350
0.8	Intermediate Similarity	NPC475965
0.8	Intermediate Similarity	NPC477147
0.8	Intermediate Similarity	NPC278459
0.798	Intermediate Similarity	NPC252295
0.7979	Intermediate Similarity	NPC146937
0.7979	Intermediate Similarity	NPC56413
0.7978	Intermediate Similarity	NPC327674
0.7961	Intermediate Similarity	NPC91034
0.7961	Intermediate Similarity	NPC473284
0.7959	Intermediate Similarity	NPC472806
0.7959	Intermediate Similarity	NPC114743
0.7959	Intermediate Similarity	NPC195366
0.7959	Intermediate Similarity	NPC120708
0.7959	Intermediate Similarity	NPC98874
0.7959	Intermediate Similarity	NPC167193
0.7957	Intermediate Similarity	NPC31564
0.7957	Intermediate Similarity	NPC474733
0.7957	Intermediate Similarity	NPC155011
0.7957	Intermediate Similarity	NPC70661
0.7957	Intermediate Similarity	NPC474732
0.7957	Intermediate Similarity	NPC145879
0.7957	Intermediate Similarity	NPC472869
0.7957	Intermediate Similarity	NPC474778
0.7941	Intermediate Similarity	NPC13385
0.7938	Intermediate Similarity	NPC67831
0.7938	Intermediate Similarity	NPC294266
0.7938	Intermediate Similarity	NPC174051
0.7938	Intermediate Similarity	NPC159410
0.7935	Intermediate Similarity	NPC19849
0.7935	Intermediate Similarity	NPC237712
0.7935	Intermediate Similarity	NPC164577
0.7935	Intermediate Similarity	NPC473246
0.7935	Intermediate Similarity	NPC100391
0.7935	Intermediate Similarity	NPC156981
0.7935	Intermediate Similarity	NPC165064
0.7935	Intermediate Similarity	NPC472864
0.7921	Intermediate Similarity	NPC193934
0.7921	Intermediate Similarity	NPC32577
0.7921	Intermediate Similarity	NPC155332
0.7921	Intermediate Similarity	NPC114540
0.7921	Intermediate Similarity	NPC271980
0.7917	Intermediate Similarity	NPC177037
0.7917	Intermediate Similarity	NPC472814
0.7917	Intermediate Similarity	NPC26888
0.7917	Intermediate Similarity	NPC471901
0.7917	Intermediate Similarity	NPC218301
0.7917	Intermediate Similarity	NPC262870
0.7912	Intermediate Similarity	NPC327969
0.7912	Intermediate Similarity	NPC240302
0.7912	Intermediate Similarity	NPC321289
0.7912	Intermediate Similarity	NPC260956
0.7912	Intermediate Similarity	NPC100297
0.79	Intermediate Similarity	NPC266955
0.79	Intermediate Similarity	NPC476274
0.79	Intermediate Similarity	NPC167974
0.7895	Intermediate Similarity	NPC214387
0.7895	Intermediate Similarity	NPC215029
0.7895	Intermediate Similarity	NPC476733
0.7895	Intermediate Similarity	NPC474889
0.7895	Intermediate Similarity	NPC471342
0.7895	Intermediate Similarity	NPC477943
0.7895	Intermediate Similarity	NPC5509
0.7895	Intermediate Similarity	NPC310010
0.7895	Intermediate Similarity	NPC305039
0.7895	Intermediate Similarity	NPC326627
0.7895	Intermediate Similarity	NPC469866
0.7885	Intermediate Similarity	NPC473482
0.7885	Intermediate Similarity	NPC220155
0.7885	Intermediate Similarity	NPC475418
0.7885	Intermediate Similarity	NPC318363
0.7879	Intermediate Similarity	NPC475894
0.7879	Intermediate Similarity	NPC108078
0.7879	Intermediate Similarity	NPC2049
0.7872	Intermediate Similarity	NPC142361
0.7872	Intermediate Similarity	NPC158141
0.7872	Intermediate Similarity	NPC93778
0.7872	Intermediate Similarity	NPC173089
0.7872	Intermediate Similarity	NPC474684
0.7872	Intermediate Similarity	NPC475740
0.7872	Intermediate Similarity	NPC90652
0.7872	Intermediate Similarity	NPC58063
0.7865	Intermediate Similarity	NPC321514
0.7865	Intermediate Similarity	NPC321690
0.7864	Intermediate Similarity	NPC472935
0.7857	Intermediate Similarity	NPC473648
0.7857	Intermediate Similarity	NPC148523
0.7857	Intermediate Similarity	NPC171395
0.7857	Intermediate Similarity	NPC279974
0.7857	Intermediate Similarity	NPC317586
0.7857	Intermediate Similarity	NPC470016
0.7857	Intermediate Similarity	NPC266431
0.7857	Intermediate Similarity	NPC209355
0.7857	Intermediate Similarity	NPC263347
0.7857	Intermediate Similarity	NPC210214
0.785	Intermediate Similarity	NPC122056
0.7849	Intermediate Similarity	NPC94531
0.7849	Intermediate Similarity	NPC329738
0.7849	Intermediate Similarity	NPC65661
0.7849	Intermediate Similarity	NPC269638

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 NPC124207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1515
0.2-0.3	4055
0.3-0.4	2355
0.4-0.5	582
0.5-0.6	194
0.6-0.7	192
0.7-0.8	99
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8438	Intermediate Similarity	NPD6083	Phase 2
0.8438	Intermediate Similarity	NPD6084	Phase 2
0.837	Intermediate Similarity	NPD6672	Approved
0.837	Intermediate Similarity	NPD5737	Approved
0.8229	Intermediate Similarity	NPD5695	Phase 3
0.8211	Intermediate Similarity	NPD6399	Phase 3
0.8163	Intermediate Similarity	NPD5696	Approved
0.8152	Intermediate Similarity	NPD6684	Approved
0.8152	Intermediate Similarity	NPD7521	Approved
0.8152	Intermediate Similarity	NPD6409	Approved
0.8152	Intermediate Similarity	NPD7146	Approved
0.8152	Intermediate Similarity	NPD5330	Approved
0.8152	Intermediate Similarity	NPD7334	Approved
0.8041	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD6903	Approved
0.7895	Intermediate Similarity	NPD4753	Phase 2
0.7895	Intermediate Similarity	NPD6080	Approved
0.7895	Intermediate Similarity	NPD6904	Approved
0.7895	Intermediate Similarity	NPD6673	Approved
0.7864	Intermediate Similarity	NPD6675	Approved
0.7864	Intermediate Similarity	NPD6402	Approved
0.7864	Intermediate Similarity	NPD7128	Approved
0.7864	Intermediate Similarity	NPD5739	Approved
0.7755	Intermediate Similarity	NPD7748	Approved
0.7742	Intermediate Similarity	NPD3133	Approved
0.7742	Intermediate Similarity	NPD3665	Phase 1
0.7742	Intermediate Similarity	NPD4786	Approved
0.7742	Intermediate Similarity	NPD3666	Approved
0.7717	Intermediate Similarity	NPD4221	Approved
0.7717	Intermediate Similarity	NPD4223	Phase 3
0.7714	Intermediate Similarity	NPD6899	Approved
0.7714	Intermediate Similarity	NPD7320	Approved
0.7714	Intermediate Similarity	NPD6881	Approved
0.7708	Intermediate Similarity	NPD5328	Approved
0.766	Intermediate Similarity	NPD5329	Approved
0.7642	Intermediate Similarity	NPD6372	Approved
0.7642	Intermediate Similarity	NPD6373	Approved
0.7636	Intermediate Similarity	NPD7115	Discovery
0.7619	Intermediate Similarity	NPD5701	Approved
0.7619	Intermediate Similarity	NPD5697	Approved
0.7604	Intermediate Similarity	NPD5208	Approved
0.7579	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6098	Approved
0.7579	Intermediate Similarity	NPD3618	Phase 1
0.7576	Intermediate Similarity	NPD6001	Approved
0.757	Intermediate Similarity	NPD6883	Approved
0.757	Intermediate Similarity	NPD7102	Approved
0.757	Intermediate Similarity	NPD7290	Approved
0.7553	Intermediate Similarity	NPD4197	Approved
0.7551	Intermediate Similarity	NPD5693	Phase 1
0.7551	Intermediate Similarity	NPD6050	Approved
0.7551	Intermediate Similarity	NPD6079	Approved
0.7551	Intermediate Similarity	NPD7515	Phase 2
0.7551	Intermediate Similarity	NPD5281	Approved
0.7551	Intermediate Similarity	NPD5284	Approved
0.7527	Intermediate Similarity	NPD3667	Approved
0.7527	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD5210	Approved
0.7477	Intermediate Similarity	NPD6012	Approved
0.7477	Intermediate Similarity	NPD6013	Approved
0.7477	Intermediate Similarity	NPD6014	Approved
0.7451	Intermediate Similarity	NPD7638	Approved
0.7449	Intermediate Similarity	NPD5692	Phase 3
0.7431	Intermediate Similarity	NPD8297	Approved
0.7431	Intermediate Similarity	NPD6882	Approved
0.7396	Intermediate Similarity	NPD4688	Approved
0.7396	Intermediate Similarity	NPD4693	Phase 3
0.7396	Intermediate Similarity	NPD5205	Approved
0.7396	Intermediate Similarity	NPD5279	Phase 3
0.7396	Intermediate Similarity	NPD4138	Approved
0.7396	Intermediate Similarity	NPD4690	Approved
0.7396	Intermediate Similarity	NPD4689	Approved
0.7383	Intermediate Similarity	NPD6011	Approved
0.7379	Intermediate Similarity	NPD7639	Approved
0.7379	Intermediate Similarity	NPD7640	Approved
0.7374	Intermediate Similarity	NPD8035	Phase 2
0.7374	Intermediate Similarity	NPD5694	Approved
0.7374	Intermediate Similarity	NPD7637	Suspended
0.7374	Intermediate Similarity	NPD8034	Phase 2
0.7353	Intermediate Similarity	NPD4755	Approved
0.7339	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD4202	Approved
0.7292	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6412	Phase 2
0.7283	Intermediate Similarity	NPD3617	Approved
0.7273	Intermediate Similarity	NPD5207	Approved
0.7263	Intermediate Similarity	NPD4788	Approved
0.7255	Intermediate Similarity	NPD4697	Phase 3
0.7255	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5221	Approved
0.7255	Intermediate Similarity	NPD5222	Approved
0.7228	Intermediate Similarity	NPD7900	Approved
0.7228	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4694	Approved
0.7216	Intermediate Similarity	NPD5280	Approved
0.7216	Intermediate Similarity	NPD5690	Phase 2
0.7212	Intermediate Similarity	NPD5286	Approved
0.7212	Intermediate Similarity	NPD5285	Approved
0.7212	Intermediate Similarity	NPD4700	Approved
0.7212	Intermediate Similarity	NPD4696	Approved
0.72	Intermediate Similarity	NPD6411	Approved
0.7196	Intermediate Similarity	NPD6008	Approved
0.7188	Intermediate Similarity	NPD3668	Phase 3
0.7184	Intermediate Similarity	NPD5173	Approved
0.7184	Intermediate Similarity	NPD5959	Approved
0.7172	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6319	Approved
0.7128	Intermediate Similarity	NPD4695	Discontinued
0.7115	Intermediate Similarity	NPD4225	Approved
0.71	Intermediate Similarity	NPD5785	Approved
0.7097	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6274	Approved
0.708	Intermediate Similarity	NPD6868	Approved
0.7079	Intermediate Similarity	NPD4747	Approved
0.7075	Intermediate Similarity	NPD4633	Approved
0.7075	Intermediate Similarity	NPD5211	Phase 2
0.7075	Intermediate Similarity	NPD5225	Approved
0.7075	Intermediate Similarity	NPD5226	Approved
0.7075	Intermediate Similarity	NPD5224	Approved
0.7053	Intermediate Similarity	NPD5369	Approved
0.7043	Intermediate Similarity	NPD7101	Approved
0.7043	Intermediate Similarity	NPD7100	Approved
0.7034	Intermediate Similarity	NPD7492	Approved
0.7021	Intermediate Similarity	NPD4195	Approved
0.7009	Intermediate Similarity	NPD6052	Approved
0.7009	Intermediate Similarity	NPD5174	Approved
0.7009	Intermediate Similarity	NPD5175	Approved
0.7	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.699	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5654	Approved
0.6983	Remote Similarity	NPD6054	Approved
0.6983	Remote Similarity	NPD6059	Approved
0.6981	Remote Similarity	NPD5223	Approved
0.6979	Remote Similarity	NPD6435	Approved
0.6975	Remote Similarity	NPD6616	Approved
0.697	Remote Similarity	NPD3573	Approved
0.6966	Remote Similarity	NPD4137	Phase 3
0.6964	Remote Similarity	NPD6053	Discontinued
0.6961	Remote Similarity	NPD5133	Approved
0.6957	Remote Similarity	NPD6335	Approved
0.6949	Remote Similarity	NPD7604	Phase 2
0.6944	Remote Similarity	NPD5141	Approved
0.6939	Remote Similarity	NPD5363	Approved
0.6937	Remote Similarity	NPD6371	Approved
0.6937	Remote Similarity	NPD4634	Approved
0.6923	Remote Similarity	NPD6909	Approved
0.6923	Remote Similarity	NPD6908	Approved
0.6917	Remote Similarity	NPD8293	Discontinued
0.6917	Remote Similarity	NPD7078	Approved
0.6909	Remote Similarity	NPD6686	Approved
0.6903	Remote Similarity	NPD4632	Approved
0.6889	Remote Similarity	NPD4691	Approved
0.6881	Remote Similarity	NPD4768	Approved
0.6881	Remote Similarity	NPD4767	Approved
0.687	Remote Similarity	NPD6317	Approved
0.6869	Remote Similarity	NPD4623	Approved
0.6869	Remote Similarity	NPD4519	Discontinued
0.6864	Remote Similarity	NPD6370	Approved
0.686	Remote Similarity	NPD7736	Approved
0.6852	Remote Similarity	NPD4754	Approved
0.6848	Remote Similarity	NPD5733	Approved
0.6832	Remote Similarity	NPD6051	Approved
0.6818	Remote Similarity	NPD6614	Approved
0.6813	Remote Similarity	NPD6081	Approved
0.681	Remote Similarity	NPD6313	Approved
0.681	Remote Similarity	NPD6314	Approved
0.6804	Remote Similarity	NPD4269	Approved
0.6804	Remote Similarity	NPD4270	Approved
0.6796	Remote Similarity	NPD5779	Approved
0.6796	Remote Similarity	NPD5778	Approved
0.678	Remote Similarity	NPD6015	Approved
0.678	Remote Similarity	NPD6016	Approved
0.6774	Remote Similarity	NPD6942	Approved
0.6774	Remote Similarity	NPD3702	Approved
0.6774	Remote Similarity	NPD7339	Approved
0.6771	Remote Similarity	NPD5368	Approved
0.6771	Remote Similarity	NPD7525	Registered
0.6768	Remote Similarity	NPD1694	Approved
0.6765	Remote Similarity	NPD4096	Approved
0.6762	Remote Similarity	NPD7614	Phase 1
0.6759	Remote Similarity	NPD7632	Discontinued
0.6757	Remote Similarity	NPD4730	Approved
0.6757	Remote Similarity	NPD4729	Approved
0.6757	Remote Similarity	NPD5128	Approved
0.6735	Remote Similarity	NPD5362	Discontinued
0.6735	Remote Similarity	NPD6695	Phase 3
0.6731	Remote Similarity	NPD5282	Discontinued
0.6729	Remote Similarity	NPD6404	Discontinued
0.6724	Remote Similarity	NPD6009	Approved
0.6723	Remote Similarity	NPD5988	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