NPASS Compound

Structure

CID324243 OpenBabel06191716172D 36 38 0 0 1 0 0 0 0 0999 V2000 2.8660 -8.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -8.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -4.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -4.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7614 -3.9131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4479 -0.7288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -6.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -6.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -7.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -5.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -5.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0878 -4.0411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -4.0981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 -6.6962 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 -4.9641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0388 -3.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0878 -2.4230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0000 -7.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -4.9641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0000 -5.8301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5000 -2.5000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 1.5000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8479 -4.3198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 -1.4720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0388 -2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -1.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1.8655 2.3195 0.0000 Na 0 3 0 0 0 15 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 5 31 1 0 0 0 0 6 32 1 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 25 1 0 0 0 0 14 27 1 0 0 0 0 15 26 1 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 17 33 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 20 26 1 6 0 0 0 21 25 1 0 0 0 0 21 27 1 1 0 0 0 22 26 1 1 0 0 0 22 27 1 0 0 0 0 23 31 1 1 0 0 0 23 34 1 0 0 0 0 24 32 1 1 0 0 0 24 34 1 0 0 0 0 26 3 1 6 0 0 0 27 4 1 1 0 0 0 28 35 1 0 0 0 0 29 35 2 0 0 0 0 30 35 2 0 0 0 0 33 35 1 0 0 0 0 M CHG 2 28 -1 36 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	511.27
Volume:	514.772
LogP:	4.135
LogD:	3.47
LogS:	-5.571
# Rotatable Bonds:	7
TPSA:	94.12
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	5.405
Fsp3:	0.852
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:	-4.864
MDCK Permeability:	1.740282095852308e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.322

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	97.39386749267578%
Volume Distribution (VD):	2.206
Pgp-substrate:	1.3643921613693237%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.916
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.252
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.408
CYP3A4-inhibitor:	0.357
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	1.966
Half-life (T1/2):	0.019

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.769
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.589
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.664
Carcinogencity:	0.986
Eye Corrosion:	0.004
Eye Irritation:	0.041
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC324243

Natural Product ID:	NPC324243
*Common Name:**	Sodium(E)-((1R,4As,4Bs,8As,10As)-1-(2-((2S,5R)-2,5-Dimethoxy-2,5-Dihydrofuran-3-Yl)Ethyl)-4B,8,8,10A-Tetramethyldecahydrophenanthren-2(1H,3H,4Bh)-Ylidene)Methyl Sulfate
IUPAC Name:	sodium;[(E)-[(1R,4aR,4bS,8aS,10aS)-1-[2-[(2S,5R)-2,5-dimethoxy-2,5-dihydrofuran-3-yl]ethyl]-4b,8,8,10a-tetramethyl-1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthren-2-ylidene]methyl] sulfate
Synonyms:
Standard InCHIKey:	KATFIEDZWYBENH-IBBDOYIQSA-M
Standard InCHI:	InChI=1S/C27H44O7S.Na/c1-25(2)13-7-14-27(4)21(25)12-15-26(3)20(10-8-18-16-23(31-5)34-24(18)32-6)19(9-11-22(26)27)17-33-35(28,29)30;/h16-17,20-24H,7-15H2,1-6H3,(H,28,29,30);/q;+1/p-1/b19-17+;/t20-,21-,22-,23+,24-,26+,27-;/m0./s1
SMILES:	CC1(CCCC2(C1CCC3(C2CCC(=COS(=O)(=O)[O-])C3CCC4=CC(OC4OC)OC)C)C)C.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1818104
PubChem CID:	53494119
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002881] Cheilanthane sesterterpenoids

*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
NPO30318	Coscinoderma	Genus	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21827183]

☑ 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	3
MIC	10
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	10
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	49000.0	nM	PMID[566613]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	200000.0	nM	PMID[566613]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	87000.0	nM	PMID[566613]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	14000.0	nM	PMID[566613]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[566613]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[566613]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[566613]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[566613]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[566613]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[566613]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[566613]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	100.0	ug.mL-1	PMID[566613]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	100.0	ug.mL-1	PMID[566613]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[566613]

☑ 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 NPC324243 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	227
0.1-0.2	1940
0.2-0.3	7156
0.3-0.4	16713
0.4-0.5	8597
0.5-0.6	6230
0.6-0.7	1719
0.7-0.8	109
0.8-0.85	1
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8675	High Similarity	NPC318515
0.8652	High Similarity	NPC325960
0.8652	High Similarity	NPC319692
0.8636	High Similarity	NPC324078
0.8333	Intermediate Similarity	NPC472440
0.8256	Intermediate Similarity	NPC173917
0.814	Intermediate Similarity	NPC472442
0.8046	Intermediate Similarity	NPC118266
0.8022	Intermediate Similarity	NPC477722
0.8	Intermediate Similarity	NPC477122
0.7978	Intermediate Similarity	NPC293044
0.7949	Intermediate Similarity	NPC476945
0.7907	Intermediate Similarity	NPC477124
0.7727	Intermediate Similarity	NPC474013
0.7667	Intermediate Similarity	NPC144069
0.766	Intermediate Similarity	NPC8954
0.766	Intermediate Similarity	NPC94905
0.7647	Intermediate Similarity	NPC17550
0.7634	Intermediate Similarity	NPC469697
0.7609	Intermediate Similarity	NPC329842
0.7604	Intermediate Similarity	NPC477721
0.7604	Intermediate Similarity	NPC477716
0.7579	Intermediate Similarity	NPC204054
0.7579	Intermediate Similarity	NPC477719
0.7579	Intermediate Similarity	NPC257726
0.7579	Intermediate Similarity	NPC477718
0.7553	Intermediate Similarity	NPC477969
0.7553	Intermediate Similarity	NPC477970
0.7553	Intermediate Similarity	NPC135224
0.7553	Intermediate Similarity	NPC100892
0.7528	Intermediate Similarity	NPC42586
0.7528	Intermediate Similarity	NPC473251
0.7526	Intermediate Similarity	NPC477717
0.7474	Intermediate Similarity	NPC162346
0.7473	Intermediate Similarity	NPC319030
0.7473	Intermediate Similarity	NPC472810
0.7473	Intermediate Similarity	NPC472809
0.7447	Intermediate Similarity	NPC104925
0.7447	Intermediate Similarity	NPC298973
0.7447	Intermediate Similarity	NPC189513
0.7423	Intermediate Similarity	NPC477720
0.7416	Intermediate Similarity	NPC71626
0.7412	Intermediate Similarity	NPC470751
0.7412	Intermediate Similarity	NPC470750
0.7396	Intermediate Similarity	NPC476768
0.7391	Intermediate Similarity	NPC470819
0.7391	Intermediate Similarity	NPC470734
0.7356	Intermediate Similarity	NPC473685
0.7349	Intermediate Similarity	NPC12680
0.734	Intermediate Similarity	NPC246860
0.734	Intermediate Similarity	NPC163902
0.7312	Intermediate Similarity	NPC470817
0.7312	Intermediate Similarity	NPC477782
0.73	Intermediate Similarity	NPC476764
0.73	Intermediate Similarity	NPC476763
0.7283	Intermediate Similarity	NPC474629
0.7283	Intermediate Similarity	NPC324405
0.7273	Intermediate Similarity	NPC134077
0.7263	Intermediate Similarity	NPC88507
0.7245	Intermediate Similarity	NPC219285
0.7245	Intermediate Similarity	NPC228251
0.7245	Intermediate Similarity	NPC477972
0.7245	Intermediate Similarity	NPC477971
0.7245	Intermediate Similarity	NPC161527
0.7245	Intermediate Similarity	NPC477968
0.7245	Intermediate Similarity	NPC20113
0.7234	Intermediate Similarity	NPC472811
0.7234	Intermediate Similarity	NPC65513
0.7234	Intermediate Similarity	NPC477783
0.7228	Intermediate Similarity	NPC476761
0.7228	Intermediate Similarity	NPC476760
0.7228	Intermediate Similarity	NPC476762
0.7216	Intermediate Similarity	NPC76266
0.7204	Intermediate Similarity	NPC251528
0.7204	Intermediate Similarity	NPC473058
0.7191	Intermediate Similarity	NPC109938
0.7191	Intermediate Similarity	NPC471218
0.7191	Intermediate Similarity	NPC122945
0.7191	Intermediate Similarity	NPC200513
0.7188	Intermediate Similarity	NPC471362
0.7188	Intermediate Similarity	NPC471372
0.7188	Intermediate Similarity	NPC472189
0.7188	Intermediate Similarity	NPC472441
0.7174	Intermediate Similarity	NPC288952
0.7172	Intermediate Similarity	NPC285231
0.7172	Intermediate Similarity	NPC21568
0.7172	Intermediate Similarity	NPC63249
0.7159	Intermediate Similarity	NPC469802
0.7158	Intermediate Similarity	NPC472812
0.7158	Intermediate Similarity	NPC474792
0.7158	Intermediate Similarity	NPC91654
0.7158	Intermediate Similarity	NPC67398
0.7158	Intermediate Similarity	NPC267266
0.7158	Intermediate Similarity	NPC472303
0.7158	Intermediate Similarity	NPC277721
0.7143	Intermediate Similarity	NPC119001
0.7143	Intermediate Similarity	NPC476489
0.7143	Intermediate Similarity	NPC30984
0.7143	Intermediate Similarity	NPC474743
0.7143	Intermediate Similarity	NPC476490
0.7128	Intermediate Similarity	NPC159876
0.7128	Intermediate Similarity	NPC471433
0.7128	Intermediate Similarity	NPC471432
0.7126	Intermediate Similarity	NPC475337
0.7113	Intermediate Similarity	NPC73858
0.7113	Intermediate Similarity	NPC311166
0.7113	Intermediate Similarity	NPC171598
0.7113	Intermediate Similarity	NPC164750
0.7113	Intermediate Similarity	NPC112654
0.7111	Intermediate Similarity	NPC469
0.71	Intermediate Similarity	NPC476769
0.7097	Intermediate Similarity	NPC472302
0.7097	Intermediate Similarity	NPC93411
0.7083	Intermediate Similarity	NPC470255
0.7079	Intermediate Similarity	NPC82986
0.7079	Intermediate Similarity	NPC474731
0.7079	Intermediate Similarity	NPC474759
0.7079	Intermediate Similarity	NPC14203
0.7079	Intermediate Similarity	NPC474683
0.7079	Intermediate Similarity	NPC474752
0.7079	Intermediate Similarity	NPC7505
0.7079	Intermediate Similarity	NPC229584
0.7071	Intermediate Similarity	NPC324841
0.7065	Intermediate Similarity	NPC286153
0.7065	Intermediate Similarity	NPC323209
0.7059	Intermediate Similarity	NPC127790
0.7053	Intermediate Similarity	NPC120539
0.7053	Intermediate Similarity	NPC302584
0.7053	Intermediate Similarity	NPC289479
0.7045	Intermediate Similarity	NPC242767
0.7041	Intermediate Similarity	NPC98112
0.7041	Intermediate Similarity	NPC472188
0.7041	Intermediate Similarity	NPC97867
0.7033	Intermediate Similarity	NPC96055
0.7033	Intermediate Similarity	NPC471302
0.7033	Intermediate Similarity	NPC319238
0.7033	Intermediate Similarity	NPC46320
0.703	Intermediate Similarity	NPC281378
0.703	Intermediate Similarity	NPC473123
0.703	Intermediate Similarity	NPC45897
0.703	Intermediate Similarity	NPC476770
0.703	Intermediate Similarity	NPC471885
0.703	Intermediate Similarity	NPC471886
0.703	Intermediate Similarity	NPC120009
0.703	Intermediate Similarity	NPC471888
0.703	Intermediate Similarity	NPC473124
0.703	Intermediate Similarity	NPC471887
0.7021	Intermediate Similarity	NPC177141
0.7021	Intermediate Similarity	NPC174342
0.7021	Intermediate Similarity	NPC477917
0.7019	Intermediate Similarity	NPC476759
0.7	Intermediate Similarity	NPC304285
0.7	Intermediate Similarity	NPC470049
0.7	Intermediate Similarity	NPC155521
0.6989	Remote Similarity	NPC166857
0.6989	Remote Similarity	NPC478104
0.6981	Remote Similarity	NPC475354
0.6979	Remote Similarity	NPC470656
0.697	Remote Similarity	NPC474440
0.697	Remote Similarity	NPC472186
0.697	Remote Similarity	NPC471366
0.697	Remote Similarity	NPC318917
0.697	Remote Similarity	NPC473154
0.697	Remote Similarity	NPC476800
0.6966	Remote Similarity	NPC233332
0.6966	Remote Similarity	NPC206062
0.6961	Remote Similarity	NPC203354
0.6961	Remote Similarity	NPC110656
0.6961	Remote Similarity	NPC473127
0.6961	Remote Similarity	NPC222161
0.6961	Remote Similarity	NPC93352
0.6957	Remote Similarity	NPC65661
0.6957	Remote Similarity	NPC189311
0.6957	Remote Similarity	NPC329630
0.6957	Remote Similarity	NPC266511
0.6951	Remote Similarity	NPC69649
0.6951	Remote Similarity	NPC68703
0.6947	Remote Similarity	NPC78973
0.6947	Remote Similarity	NPC302280
0.6947	Remote Similarity	NPC159748
0.6947	Remote Similarity	NPC8062
0.6947	Remote Similarity	NPC253186
0.6947	Remote Similarity	NPC469403
0.6947	Remote Similarity	NPC101651
0.6939	Remote Similarity	NPC90583
0.6931	Remote Similarity	NPC471482
0.6931	Remote Similarity	NPC300399
0.6931	Remote Similarity	NPC37207
0.6923	Remote Similarity	NPC470046
0.6923	Remote Similarity	NPC470558
0.6923	Remote Similarity	NPC30502
0.6923	Remote Similarity	NPC470047
0.6923	Remote Similarity	NPC311070
0.6915	Remote Similarity	NPC106332
0.6915	Remote Similarity	NPC473879
0.6907	Remote Similarity	NPC128488
0.6907	Remote Similarity	NPC84893
0.6907	Remote Similarity	NPC304968
0.69	Remote Similarity	NPC476767
0.69	Remote Similarity	NPC473204

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 NPC324243 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1921
0.2-0.3	4333
0.3-0.4	2065
0.4-0.5	406
0.5-0.6	212
0.6-0.7	34
0.7-0.8	1
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
0.7191	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6051	Approved
0.6762	Remote Similarity	NPD6686	Approved
0.6634	Remote Similarity	NPD7638	Approved
0.6593	Remote Similarity	NPD7525	Registered
0.6569	Remote Similarity	NPD7639	Approved
0.6569	Remote Similarity	NPD7640	Approved
0.6518	Remote Similarity	NPD7328	Approved
0.6518	Remote Similarity	NPD7327	Approved
0.6489	Remote Similarity	NPD3668	Phase 3
0.6489	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7645	Phase 2
0.646	Remote Similarity	NPD7516	Approved
0.6404	Remote Similarity	NPD6942	Approved
0.6404	Remote Similarity	NPD8294	Approved
0.6404	Remote Similarity	NPD7339	Approved
0.6404	Remote Similarity	NPD8377	Approved
0.6392	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5737	Approved
0.6392	Remote Similarity	NPD6672	Approved
0.6354	Remote Similarity	NPD7334	Approved
0.6354	Remote Similarity	NPD6409	Approved
0.6354	Remote Similarity	NPD5330	Approved
0.6354	Remote Similarity	NPD6684	Approved
0.6354	Remote Similarity	NPD7146	Approved
0.6354	Remote Similarity	NPD7521	Approved
0.6348	Remote Similarity	NPD8033	Approved
0.6348	Remote Similarity	NPD8296	Approved
0.6348	Remote Similarity	NPD8380	Approved
0.6348	Remote Similarity	NPD8335	Approved
0.6348	Remote Similarity	NPD8379	Approved
0.6348	Remote Similarity	NPD8378	Approved
0.6333	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4243	Approved
0.6224	Remote Similarity	NPD6903	Approved
0.6211	Remote Similarity	NPD6695	Phase 3
0.6207	Remote Similarity	NPD7503	Approved
0.6204	Remote Similarity	NPD6412	Phase 2
0.62	Remote Similarity	NPD5693	Phase 1
0.6146	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6399	Phase 3
0.6134	Remote Similarity	NPD7507	Approved
0.6111	Remote Similarity	NPD6924	Approved
0.6111	Remote Similarity	NPD4785	Approved
0.6111	Remote Similarity	NPD6926	Approved
0.6111	Remote Similarity	NPD4784	Approved
0.6078	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7748	Approved
0.6078	Remote Similarity	NPD7900	Approved
0.6044	Remote Similarity	NPD8039	Approved
0.6024	Remote Similarity	NPD1145	Discontinued
0.602	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4225	Approved
0.5984	Remote Similarity	NPD7319	Approved
0.5981	Remote Similarity	NPD7632	Discontinued
0.5979	Remote Similarity	NPD4786	Approved
0.5978	Remote Similarity	NPD6933	Approved
0.596	Remote Similarity	NPD7524	Approved
0.596	Remote Similarity	NPD7750	Discontinued
0.596	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6929	Approved
0.5938	Remote Similarity	NPD3667	Approved
0.5918	Remote Similarity	NPD1694	Approved
0.5905	Remote Similarity	NPD7902	Approved
0.5905	Remote Similarity	NPD6083	Phase 2
0.5905	Remote Similarity	NPD6084	Phase 2
0.5895	Remote Similarity	NPD6931	Approved
0.5895	Remote Similarity	NPD6930	Phase 2
0.5882	Remote Similarity	NPD7515	Phase 2
0.5877	Remote Similarity	NPD8133	Approved
0.587	Remote Similarity	NPD5275	Approved
0.587	Remote Similarity	NPD4190	Phase 3
0.5865	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6922	Approved
0.5843	Remote Similarity	NPD6923	Approved
0.5816	Remote Similarity	NPD3666	Approved
0.5816	Remote Similarity	NPD3133	Approved
0.5816	Remote Similarity	NPD3665	Phase 1
0.5789	Remote Similarity	NPD4195	Approved
0.5778	Remote Similarity	NPD7143	Approved
0.5778	Remote Similarity	NPD7144	Approved
0.5745	Remote Similarity	NPD6925	Approved
0.5745	Remote Similarity	NPD5776	Phase 2
0.5743	Remote Similarity	NPD5208	Approved
0.5729	Remote Similarity	NPD7514	Phase 3
0.5729	Remote Similarity	NPD7332	Phase 2
0.5729	Remote Similarity	NPD7509	Discontinued
0.5729	Remote Similarity	NPD4695	Discontinued
0.5728	Remote Similarity	NPD8035	Phase 2
0.5728	Remote Similarity	NPD7637	Suspended
0.5728	Remote Similarity	NPD6050	Approved
0.5728	Remote Similarity	NPD7087	Discontinued
0.5728	Remote Similarity	NPD8034	Phase 2
0.5714	Remote Similarity	NPD7150	Approved
0.5714	Remote Similarity	NPD4788	Approved
0.5714	Remote Similarity	NPD7152	Approved
0.5714	Remote Similarity	NPD5695	Phase 3
0.5714	Remote Similarity	NPD7151	Approved
0.5701	Remote Similarity	NPD5696	Approved
0.57	Remote Similarity	NPD4519	Discontinued
0.57	Remote Similarity	NPD3618	Phase 1
0.57	Remote Similarity	NPD4623	Approved
0.5699	Remote Similarity	NPD8264	Approved
0.5686	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD5328	Approved
0.5686	Remote Similarity	NPD4753	Phase 2
0.5684	Remote Similarity	NPD7145	Approved
0.567	Remote Similarity	NPD6902	Approved
0.5652	Remote Similarity	NPD6882	Approved
0.5644	Remote Similarity	NPD3573	Approved
0.5631	Remote Similarity	NPD5692	Phase 3
0.5625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD4223	Phase 3
0.5612	Remote Similarity	NPD4221	Approved
0.56	Remote Similarity	NPD5329	Approved
0.56	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6893	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