NPASS Compound

Structure

CID14499 OpenBabel06191715342D 41 45 0 0 1 0 0 0 0 0999 V2000 1.6002 -1.0130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5891 -4.0476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0334 -4.5437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3242 1.6844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3779 1.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9062 -2.0195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3310 -2.5338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4985 -3.1198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2397 -1.5199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2658 1.1984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5748 -2.6919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3160 -1.0920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8825 0.8635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7028 0.9374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7298 -2.5335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2810 -0.1709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7298 -1.5156 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7186 -4.5502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9038 -4.0412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4835 -1.6780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7077 0.6704 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0826 0.3954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1518 -3.0425 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9811 -1.1437 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2145 -0.4324 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0334 -2.5335 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5598 -1.2501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5604 -0.4785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6924 0.7463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0334 -1.5156 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1518 -1.0066 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7186 -5.5553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7743 -4.5437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4685 -0.2362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8084 -0.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5896 0.4411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1518 -4.0476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9038 -3.0361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7274 -1.8361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5876 -0.7786 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 10 13 1 0 0 0 0 10 14 2 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 22 2 0 0 0 0 14 36 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 31 1 6 0 0 0 18 32 2 0 0 0 0 18 37 1 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 27 1 0 0 0 0 21 16 1 1 0 0 0 21 25 1 0 0 0 0 21 29 1 0 0 0 0 22 28 1 0 0 0 0 22 36 1 0 0 0 0 23 26 1 0 0 0 0 23 37 1 6 0 0 0 24 30 1 1 0 0 0 24 39 1 0 0 0 0 25 31 1 6 0 0 0 25 40 1 0 0 0 0 26 30 1 6 0 0 0 26 38 1 0 0 0 0 27 34 2 0 0 0 0 27 39 1 0 0 0 0 28 35 2 0 0 0 0 28 40 1 0 0 0 0 29 41 1 0 0 0 0 30 31 1 6 0 0 0 31 41 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.23
Volume:	566.124
LogP:	4.435
LogD:	3.052
LogS:	-4.659
# Rotatable Bonds:	10
TPSA:	127.57
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	5.79
Fsp3:	0.548
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:	-5.11
MDCK Permeability:	3.7533332942985e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	87.41716766357422%
Volume Distribution (VD):	2.668
Pgp-substrate:	6.666521072387695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.438
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.298
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.545
CYP3A4-substrate:	0.438

ADMET: Excretion

Clearance (CL):	6.667
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.711
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.395
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.069
Carcinogencity:	0.147
Eye Corrosion:	0.004
Eye Irritation:	0.371
Respiratory Toxicity:	0.846

Download Data

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

Natural Product: NPC14499

Natural Product ID:	NPC14499
*Common Name:**	Orbiculin E
IUPAC Name:	n.a.
Synonyms:	Orbiculin E
Standard InCHIKey:	CEKCSANPFZSVKO-ICWAWGCGSA-N
Standard InCHI:	InChI=1S/C31H36O10/c1-17-15-23(37-18(2)32)26(38-19(3)33)30(6)24(39-27(34)20-11-8-7-9-12-20)16-21-25(31(17,30)41-29(21,4)5)40-28(35)22-13-10-14-36-22/h7-14,17,21,23-26H,15-16H2,1-6H3/t17-,21-,23+,24+,25-,26+,30-,31-/m1/s1
SMILES:	CC(=O)O[C@H]1[C@@H](OC(=O)C)C[C@H]([C@@]23[C@]1(C)[C@@H](OC(=O)c1ccccc1)C[C@H]([C@H]3OC(=O)c1ccco1)C(O2)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500858
PubChem CID:	10745604
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	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	5
Others	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	300000.0	nM	PMID[470922]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	28300.0	nM	PMID[470923]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	33100.0	nM	PMID[470923]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	500.0	nM	PMID[470923]
NPT2	Others	Unspecified		Ratio IC50	=	66.2	n.a.	PMID[470923]
NPT2	Others	Unspecified		Ratio IC50	=	1.8	n.a.	PMID[470923]
NPT2	Others	Unspecified		Ratio IC50	=	1.6	n.a.	PMID[470923]
NPT2	Others	Unspecified		Ratio IC50	=	2.6	n.a.	PMID[470923]

☑ 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 NPC14499 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	419
0.1-0.2	1488
0.2-0.3	2813
0.3-0.4	6071
0.4-0.5	11240
0.5-0.6	7716
0.6-0.7	9266
0.7-0.8	3171
0.8-0.85	433
0.85-0.9	52
0.9-0.95	17
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475039
1.0	High Similarity	NPC476035
0.9682	High Similarity	NPC88593
0.9355	High Similarity	NPC246841
0.9355	High Similarity	NPC1408
0.9231	High Similarity	NPC195954
0.9182	High Similarity	NPC276735
0.9119	High Similarity	NPC285567
0.9108	High Similarity	NPC88007
0.9062	High Similarity	NPC27541
0.9062	High Similarity	NPC62692
0.9062	High Similarity	NPC126984
0.9062	High Similarity	NPC61967
0.9062	High Similarity	NPC159520
0.9057	High Similarity	NPC68848
0.902	High Similarity	NPC71821
0.9	High Similarity	NPC283209
0.8994	High Similarity	NPC8389
0.8987	High Similarity	NPC194499
0.8938	High Similarity	NPC79571
0.8924	High Similarity	NPC41880
0.8924	High Similarity	NPC104736
0.8902	High Similarity	NPC294512
0.8868	High Similarity	NPC304692
0.8868	High Similarity	NPC7059
0.8846	High Similarity	NPC212257
0.8841	High Similarity	NPC118086
0.8841	High Similarity	NPC302392
0.8834	High Similarity	NPC270312
0.8834	High Similarity	NPC473766
0.8834	High Similarity	NPC473753
0.882	High Similarity	NPC188649
0.882	High Similarity	NPC471003
0.8788	High Similarity	NPC475641
0.8788	High Similarity	NPC475237
0.878	High Similarity	NPC296558
0.878	High Similarity	NPC291742
0.8773	High Similarity	NPC121995
0.8773	High Similarity	NPC277618
0.8773	High Similarity	NPC86800
0.8765	High Similarity	NPC88841
0.8765	High Similarity	NPC469846
0.8765	High Similarity	NPC288602
0.875	High Similarity	NPC469847
0.8743	High Similarity	NPC56953
0.8743	High Similarity	NPC176413
0.8734	High Similarity	NPC294511
0.8734	High Similarity	NPC121615
0.8726	High Similarity	NPC228842
0.872	High Similarity	NPC310572
0.8712	High Similarity	NPC56358
0.8704	High Similarity	NPC470939
0.8704	High Similarity	NPC18986
0.8659	High Similarity	NPC308156
0.8654	High Similarity	NPC255414
0.8642	High Similarity	NPC287559
0.8642	High Similarity	NPC191828
0.8631	High Similarity	NPC167340
0.8623	High Similarity	NPC469848
0.8606	High Similarity	NPC476861
0.8606	High Similarity	NPC476850
0.858	High Similarity	NPC475295
0.858	High Similarity	NPC473368
0.858	High Similarity	NPC473473
0.8571	High Similarity	NPC107646
0.8554	High Similarity	NPC271235
0.8553	High Similarity	NPC18135
0.8545	High Similarity	NPC475779
0.8544	High Similarity	NPC125182
0.8544	High Similarity	NPC69647
0.8537	High Similarity	NPC471168
0.8529	High Similarity	NPC11062
0.8528	High Similarity	NPC305016
0.8528	High Similarity	NPC475381
0.8519	High Similarity	NPC286722
0.8519	High Similarity	NPC472283
0.8519	High Similarity	NPC167142
0.8516	High Similarity	NPC470231
0.8509	High Similarity	NPC476262
0.85	High Similarity	NPC182427
0.85	High Similarity	NPC476201
0.85	High Similarity	NPC268905
0.85	High Similarity	NPC472672
0.85	High Similarity	NPC29695
0.85	High Similarity	NPC308205
0.85	High Similarity	NPC322546
0.8494	Intermediate Similarity	NPC472774
0.8494	Intermediate Similarity	NPC472775
0.8487	Intermediate Similarity	NPC307401
0.8485	Intermediate Similarity	NPC476857
0.8485	Intermediate Similarity	NPC476856
0.8485	Intermediate Similarity	NPC123088
0.8485	Intermediate Similarity	NPC476858
0.8476	Intermediate Similarity	NPC82851
0.8476	Intermediate Similarity	NPC471166
0.8476	Intermediate Similarity	NPC471167
0.8471	Intermediate Similarity	NPC472665
0.8466	Intermediate Similarity	NPC474611
0.8466	Intermediate Similarity	NPC475967
0.8466	Intermediate Similarity	NPC237155
0.8462	Intermediate Similarity	NPC471107
0.8462	Intermediate Similarity	NPC471100
0.8457	Intermediate Similarity	NPC209364
0.8457	Intermediate Similarity	NPC126723
0.8447	Intermediate Similarity	NPC302054
0.8447	Intermediate Similarity	NPC34421
0.8447	Intermediate Similarity	NPC253201
0.8447	Intermediate Similarity	NPC237259
0.8447	Intermediate Similarity	NPC98206
0.8443	Intermediate Similarity	NPC160651
0.8443	Intermediate Similarity	NPC255787
0.8438	Intermediate Similarity	NPC116717
0.8428	Intermediate Similarity	NPC471001
0.8424	Intermediate Similarity	NPC469338
0.8424	Intermediate Similarity	NPC39986
0.8424	Intermediate Similarity	NPC292389
0.8424	Intermediate Similarity	NPC476197
0.8424	Intermediate Similarity	NPC134254
0.8424	Intermediate Similarity	NPC302369
0.8415	Intermediate Similarity	NPC25255
0.8415	Intermediate Similarity	NPC472653
0.8405	Intermediate Similarity	NPC81405
0.8395	Intermediate Similarity	NPC25351
0.8395	Intermediate Similarity	NPC75310
0.8393	Intermediate Similarity	NPC470995
0.8385	Intermediate Similarity	NPC246164
0.8383	Intermediate Similarity	NPC476853
0.8383	Intermediate Similarity	NPC472651
0.8383	Intermediate Similarity	NPC173516
0.8375	Intermediate Similarity	NPC476122
0.8373	Intermediate Similarity	NPC476860
0.8373	Intermediate Similarity	NPC469849
0.8373	Intermediate Similarity	NPC276551
0.8373	Intermediate Similarity	NPC470940
0.8365	Intermediate Similarity	NPC19747
0.8365	Intermediate Similarity	NPC254558
0.8364	Intermediate Similarity	NPC193798
0.8364	Intermediate Similarity	NPC470792
0.8364	Intermediate Similarity	NPC472771
0.8364	Intermediate Similarity	NPC472668
0.8364	Intermediate Similarity	NPC329938
0.8355	Intermediate Similarity	NPC291638
0.8355	Intermediate Similarity	NPC17877
0.8355	Intermediate Similarity	NPC472577
0.8355	Intermediate Similarity	NPC66761
0.8355	Intermediate Similarity	NPC195647
0.8354	Intermediate Similarity	NPC477403
0.8354	Intermediate Similarity	NPC140952
0.8354	Intermediate Similarity	NPC62799
0.8354	Intermediate Similarity	NPC472823
0.8354	Intermediate Similarity	NPC123153
0.8344	Intermediate Similarity	NPC84479
0.8344	Intermediate Similarity	NPC263265
0.8344	Intermediate Similarity	NPC60973
0.8344	Intermediate Similarity	NPC251865
0.8333	Intermediate Similarity	NPC471397
0.8333	Intermediate Similarity	NPC472652
0.8333	Intermediate Similarity	NPC121158
0.8333	Intermediate Similarity	NPC105395
0.8333	Intermediate Similarity	NPC263337
0.8323	Intermediate Similarity	NPC472141
0.8323	Intermediate Similarity	NPC23387
0.8323	Intermediate Similarity	NPC470875
0.8313	Intermediate Similarity	NPC472669
0.8313	Intermediate Similarity	NPC234660
0.8313	Intermediate Similarity	NPC477405
0.8313	Intermediate Similarity	NPC211625
0.8313	Intermediate Similarity	NPC51568
0.8313	Intermediate Similarity	NPC472773
0.8303	Intermediate Similarity	NPC335761
0.8302	Intermediate Similarity	NPC221809
0.8293	Intermediate Similarity	NPC470118
0.8293	Intermediate Similarity	NPC475066
0.8293	Intermediate Similarity	NPC472776
0.8293	Intermediate Similarity	NPC472778
0.8293	Intermediate Similarity	NPC472777
0.8293	Intermediate Similarity	NPC470119
0.8293	Intermediate Similarity	NPC261597
0.8293	Intermediate Similarity	NPC249021
0.8293	Intermediate Similarity	NPC36655
0.8293	Intermediate Similarity	NPC214495
0.8293	Intermediate Similarity	NPC299038
0.8291	Intermediate Similarity	NPC34056
0.8291	Intermediate Similarity	NPC5676
0.8289	Intermediate Similarity	NPC474608
0.8282	Intermediate Similarity	NPC471175
0.8282	Intermediate Similarity	NPC214541
0.8282	Intermediate Similarity	NPC44675
0.828	Intermediate Similarity	NPC205071
0.8274	Intermediate Similarity	NPC472784
0.8274	Intermediate Similarity	NPC476224
0.8274	Intermediate Similarity	NPC472282
0.8274	Intermediate Similarity	NPC41689
0.8272	Intermediate Similarity	NPC475777
0.8263	Intermediate Similarity	NPC261184
0.8261	Intermediate Similarity	NPC469335
0.8261	Intermediate Similarity	NPC196864
0.8261	Intermediate Similarity	NPC159927
0.8261	Intermediate Similarity	NPC156189
0.8261	Intermediate Similarity	NPC477404

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 NPC14499 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	829
0.2-0.3	1601
0.3-0.4	2701
0.4-0.5	2152
0.5-0.6	1082
0.6-0.7	374
0.7-0.8	57
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8706	High Similarity	NPD8434	Phase 2
0.8193	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6764	Approved
0.8092	Intermediate Similarity	NPD6765	Approved
0.791	Intermediate Similarity	NPD6785	Approved
0.791	Intermediate Similarity	NPD6784	Approved
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6599	Discontinued
0.7765	Intermediate Similarity	NPD919	Approved
0.7738	Intermediate Similarity	NPD5761	Phase 2
0.7738	Intermediate Similarity	NPD5760	Phase 2
0.7738	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7075	Discontinued
0.7674	Intermediate Similarity	NPD1247	Approved
0.7654	Intermediate Similarity	NPD4628	Phase 3
0.7616	Intermediate Similarity	NPD5494	Approved
0.7588	Intermediate Similarity	NPD3817	Phase 2
0.7578	Intermediate Similarity	NPD1471	Phase 3
0.7574	Intermediate Similarity	NPD6801	Discontinued
0.7529	Intermediate Similarity	NPD7819	Suspended
0.7515	Intermediate Similarity	NPD6799	Approved
0.7514	Intermediate Similarity	NPD5844	Phase 1
0.7486	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5402	Approved
0.7485	Intermediate Similarity	NPD920	Approved
0.7485	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8127	Discontinued
0.7469	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD8404	Phase 2
0.7442	Intermediate Similarity	NPD4966	Approved
0.7442	Intermediate Similarity	NPD4965	Approved
0.7442	Intermediate Similarity	NPD4967	Phase 2
0.7425	Intermediate Similarity	NPD6273	Approved
0.7405	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3226	Approved
0.7386	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5403	Approved
0.7375	Intermediate Similarity	NPD6355	Discontinued
0.7365	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5401	Approved
0.7356	Intermediate Similarity	NPD6234	Discontinued
0.7349	Intermediate Similarity	NPD7236	Approved
0.7349	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3748	Approved
0.7341	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7411	Suspended
0.7303	Intermediate Similarity	NPD7473	Discontinued
0.7301	Intermediate Similarity	NPD2796	Approved
0.7294	Intermediate Similarity	NPD7458	Discontinued
0.7289	Intermediate Similarity	NPD3887	Approved
0.7288	Intermediate Similarity	NPD3926	Phase 2
0.7283	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD37	Approved
0.7263	Intermediate Similarity	NPD7799	Discontinued
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6233	Phase 2
0.725	Intermediate Similarity	NPD8032	Phase 2
0.7241	Intermediate Similarity	NPD3882	Suspended
0.7235	Intermediate Similarity	NPD7239	Suspended
0.7233	Intermediate Similarity	NPD7095	Approved
0.7229	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3749	Approved
0.7188	Intermediate Similarity	NPD6798	Discontinued
0.7186	Intermediate Similarity	NPD6190	Approved
0.7175	Intermediate Similarity	NPD7199	Phase 2
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7169	Intermediate Similarity	NPD1243	Approved
0.7167	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7228	Approved
0.716	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6166	Phase 2
0.7151	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6232	Discontinued
0.7135	Intermediate Similarity	NPD4107	Approved
0.7127	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3750	Approved
0.7126	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8312	Approved
0.712	Intermediate Similarity	NPD8313	Approved
0.7101	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8150	Discontinued
0.7093	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2438	Suspended
0.7089	Intermediate Similarity	NPD3267	Approved
0.7089	Intermediate Similarity	NPD3266	Approved
0.7086	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8407	Phase 2
0.7072	Intermediate Similarity	NPD3818	Discontinued
0.7072	Intermediate Similarity	NPD3751	Discontinued
0.7069	Intermediate Similarity	NPD1934	Approved
0.7065	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4380	Phase 2
0.7048	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2353	Approved
0.7048	Intermediate Similarity	NPD2346	Discontinued
0.7048	Intermediate Similarity	NPD5762	Approved
0.7048	Intermediate Similarity	NPD5763	Approved
0.7045	Intermediate Similarity	NPD7768	Phase 2
0.7039	Intermediate Similarity	NPD3787	Discontinued
0.7032	Intermediate Similarity	NPD17	Approved
0.703	Intermediate Similarity	NPD2799	Discontinued
0.7026	Intermediate Similarity	NPD7435	Discontinued
0.7026	Intermediate Similarity	NPD7497	Discontinued
0.7024	Intermediate Similarity	NPD7003	Approved
0.7021	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7251	Discontinued
0.7011	Intermediate Similarity	NPD8368	Discontinued
0.7011	Intermediate Similarity	NPD7240	Approved
0.701	Intermediate Similarity	NPD4482	Phase 3
0.7006	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3972	Approved
0.6994	Remote Similarity	NPD4307	Phase 2
0.6988	Remote Similarity	NPD1551	Phase 2
0.6988	Remote Similarity	NPD6100	Approved
0.6988	Remote Similarity	NPD6099	Approved
0.6983	Remote Similarity	NPD6959	Discontinued
0.6981	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3764	Approved
0.6975	Remote Similarity	NPD3268	Approved
0.6973	Remote Similarity	NPD7808	Phase 3
0.6961	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6797	Phase 2
0.6944	Remote Similarity	NPD7229	Phase 3
0.6932	Remote Similarity	NPD2801	Approved
0.6932	Remote Similarity	NPD8455	Phase 2
0.6931	Remote Similarity	NPD8435	Approved
0.6923	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4110	Phase 3
0.6914	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2897	Discontinued
0.6905	Remote Similarity	NPD1549	Phase 2
0.6902	Remote Similarity	NPD7074	Phase 3
0.6899	Remote Similarity	NPD1608	Approved
0.689	Remote Similarity	NPD4060	Phase 1
0.689	Remote Similarity	NPD2979	Phase 3
0.6886	Remote Similarity	NPD2935	Discontinued
0.6882	Remote Similarity	NPD2354	Approved
0.6871	Remote Similarity	NPD2313	Discontinued
0.6868	Remote Similarity	NPD2403	Approved
0.6867	Remote Similarity	NPD7097	Phase 1
0.686	Remote Similarity	NPD2533	Approved
0.686	Remote Similarity	NPD2534	Approved
0.686	Remote Similarity	NPD2532	Approved
0.6859	Remote Similarity	NPD5585	Approved
0.6854	Remote Similarity	NPD7058	Phase 2
0.6854	Remote Similarity	NPD7057	Phase 3
0.6851	Remote Similarity	NPD6808	Phase 2
0.6848	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1933	Approved
0.6848	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7054	Approved
0.6845	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6002	Phase 3
0.6845	Remote Similarity	NPD6004	Phase 3
0.6845	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6005	Phase 3
0.6845	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8361	Approved
0.6842	Remote Similarity	NPD8360	Approved
0.6836	Remote Similarity	NPD1465	Phase 2
0.6835	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7685	Pre-registration
0.6826	Remote Similarity	NPD4308	Phase 3
0.6826	Remote Similarity	NPD7033	Discontinued
0.6825	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8166	Discontinued
0.6821	Remote Similarity	NPD1512	Approved
0.6821	Remote Similarity	NPD8285	Discontinued
0.6821	Remote Similarity	NPD5049	Phase 3
0.6818	Remote Similarity	NPD6386	Approved
0.6818	Remote Similarity	NPD6385	Approved
0.6816	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7874	Approved
0.6813	Remote Similarity	NPD1876	Approved
0.6811	Remote Similarity	NPD7472	Approved
0.6805	Remote Similarity	NPD4534	Discontinued
0.6793	Remote Similarity	NPD2163	Approved
0.6788	Remote Similarity	NPD4140	Approved
0.6786	Remote Similarity	NPD6780	Approved
0.6786	Remote Similarity	NPD6777	Approved
0.6786	Remote Similarity	NPD6781	Approved
0.6786	Remote Similarity	NPD6779	Approved
0.6786	Remote Similarity	NPD6782	Approved
0.6786	Remote Similarity	NPD6776	Approved
0.6786	Remote Similarity	NPD6778	Approved
0.677	Remote Similarity	NPD2797	Approved
0.6768	Remote Similarity	NPD7698	Approved
0.6768	Remote Similarity	NPD7696	Phase 3
0.6768	Remote Similarity	NPD7697	Approved
0.6763	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7028	Phase 2
0.6755	Remote Similarity	NPD2968	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