NPASS Compound

Structure

CID11250 OpenBabel06191715342D 22 24 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 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 1.7321 0.0000 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 -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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 0.8660 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 12 21 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 1 0 0 0 18 20 1 0 0 0 0 19 3 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.21
Volume:	335.841
LogP:	4.267
LogD:	4.064
LogS:	-4.704
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.802
Synthetic Accessibility Score:	3.845
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.921
MDCK Permeability:	1.7594215023564175e-05
Pgp-inhibitor:	0.754
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.415
Plasma Protein Binding (PPB):	81.22407531738281%
Volume Distribution (VD):	4.274
Pgp-substrate:	8.080217361450195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.148
CYP1A2-substrate:	0.749
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.861
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.609
CYP2D6-inhibitor:	0.939
CYP2D6-substrate:	0.286
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.596

ADMET: Excretion

Clearance (CL):	5.583
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.276
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.322
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.949
Carcinogencity:	0.066
Eye Corrosion:	0.067
Eye Irritation:	0.935
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC11250

Natural Product ID:	NPC11250
*Common Name:**	18-Oxoferruginol
IUPAC Name:	(1R,4aS,10aR)-6-hydroxy-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carbaldehyde
Synonyms:	18-Oxoferruginol
Standard InCHIKey:	BYISLTMARMJFNI-SLFFLAALSA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-13(2)15-10-14-6-7-18-19(3,12-21)8-5-9-20(18,4)16(14)11-17(15)22/h10-13,18,22H,5-9H2,1-4H3/t18-,19-,20+/m0/s1
SMILES:	O=C[C@]1(C)CCC[C@]2([C@H]1CCc1c2cc(c(c1)C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1277662
PubChem CID:	52946772
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO22372	Callicarpa bodinieri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29578342]
NPO22372	Callicarpa bodinieri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28466	Torreya nucifera	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
EC50	9
IC50	13
Others	13

Activity Type	# Activity
Cell Line	13
Individual Protein	4
NON-MOLECULAR	1
Organism	14
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	Inhibition	=	70.5	%	PMID[518306]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	IC50	=	163200.0	nM	PMID[518306]
NPT65	Cell Line	HepG2	Homo sapiens	EC50	>	25000.0	nM	PMID[518307]
NPT80	Cell Line	Raji	Homo sapiens	EC50	>	25000.0	nM	PMID[518307]
NPT1160	Cell Line	BJ	Homo sapiens	EC50	>	25000.0	nM	PMID[518307]
NPT71	Cell Line	HEK293	Homo sapiens	EC50	>	25000.0	nM	PMID[518307]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	60000.0	nM	PMID[518308]
NPT165	Cell Line	HeLa	Homo sapiens	Ratio IC50	=	1.5	n.a.	PMID[518308]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	21600.0	nM	PMID[518308]
NPT15	Cell Line	Jurkat	Homo sapiens	Ratio IC50	=	4.2	n.a.	PMID[518308]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Ratio IC50	=	2.7	n.a.	PMID[518308]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	90800.0	nM	PMID[518308]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	97800.0	nM	PMID[518308]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	52200.0	nM	PMID[518308]
NPT1440	Individual Protein	Tyrosine-protein kinase JAK3	Homo sapiens	IC50	>	100.0	nM	PMID[518309]
NPT3174	Individual Protein	Lysyl-tRNA synthetase	Homo sapiens	IC50	=	34.1	nM	PMID[518309]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	106500.0	nM	PMID[518310]
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	EC50	=	15000.0	nM	PMID[518307]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	EC50	=	15000.0	nM	PMID[518307]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	EC50	=	19600.0	nM	PMID[518308]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	EC50	=	16600.0	nM	PMID[518308]
NPT194	Organism	Dengue virus 2	Dengue virus 2	EC50	=	5000.0	nM	PMID[518308]
NPT2	Others	Unspecified		Ratio IC50/EC50	=	4.9	n.a.	PMID[518308]
NPT2	Others	Unspecified		Ratio IC50/EC50	=	10.4	n.a.	PMID[518308]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	Activity	=	68.2	%	PMID[518308]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC80	=	41700.0	nM	PMID[518308]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC80	=	83300.0	nM	PMID[518308]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	FC	=	1000.0	n.a.	PMID[518308]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	MNTD	=	41.7	uM	PMID[518308]
NPT2	Others	Unspecified		Ratio IC50/EC50	=	5.9	n.a.	PMID[518308]
NPT194	Organism	Dengue virus 2	Dengue virus 2	MNTD	=	41.7	uM	PMID[518308]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	33200.0	nM	PMID[518308]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	48700.0	nM	PMID[518310]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	63000.0	nM	PMID[518310]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	59500.0	nM	PMID[518310]

☑ 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 NPC11250 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	242
0.1-0.2	1366
0.2-0.3	2697
0.3-0.4	7900
0.4-0.5	10818
0.5-0.6	9073
0.6-0.7	8701
0.7-0.8	1665
0.8-0.85	152
0.85-0.9	59
0.9-0.95	20
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9746	High Similarity	NPC137750
0.9741	High Similarity	NPC253627
0.9576	High Similarity	NPC471187
0.9496	High Similarity	NPC181334
0.9407	High Similarity	NPC162935
0.9407	High Similarity	NPC249340
0.9322	High Similarity	NPC259703
0.9322	High Similarity	NPC32322
0.925	High Similarity	NPC198014
0.9244	High Similarity	NPC154696
0.9187	High Similarity	NPC3009
0.9167	High Similarity	NPC176208
0.9167	High Similarity	NPC121168
0.916	High Similarity	NPC241001
0.9138	High Similarity	NPC35797
0.9138	High Similarity	NPC192948
0.9127	High Similarity	NPC477139
0.912	High Similarity	NPC291001
0.9098	High Similarity	NPC87985
0.9076	High Similarity	NPC478121
0.906	High Similarity	NPC38893
0.906	High Similarity	NPC477137
0.906	High Similarity	NPC308311
0.8992	High Similarity	NPC42657
0.8983	High Similarity	NPC172219
0.8983	High Similarity	NPC304510
0.8968	High Similarity	NPC471851
0.8957	High Similarity	NPC176279
0.8957	High Similarity	NPC260323
0.8952	High Similarity	NPC78364
0.8952	High Similarity	NPC69424
0.8952	High Similarity	NPC176130
0.8952	High Similarity	NPC84672
0.8917	High Similarity	NPC318552
0.8917	High Similarity	NPC190501
0.8908	High Similarity	NPC471671
0.8898	High Similarity	NPC219112
0.8889	High Similarity	NPC268160
0.8871	High Similarity	NPC71610
0.8833	High Similarity	NPC469644
0.8828	High Similarity	NPC78307
0.8828	High Similarity	NPC49742
0.8824	High Similarity	NPC477136
0.8814	High Similarity	NPC147179
0.881	High Similarity	NPC276238
0.88	High Similarity	NPC72667
0.876	High Similarity	NPC202225
0.875	High Similarity	NPC165612
0.874	High Similarity	NPC108129
0.8739	High Similarity	NPC471668
0.8739	High Similarity	NPC92
0.8739	High Similarity	NPC469663
0.8739	High Similarity	NPC308828
0.8729	High Similarity	NPC195922
0.872	High Similarity	NPC254492
0.8718	High Similarity	NPC250323
0.871	High Similarity	NPC199273
0.8707	High Similarity	NPC141782
0.8672	High Similarity	NPC476847
0.8661	High Similarity	NPC206028
0.8661	High Similarity	NPC303910
0.8661	High Similarity	NPC171460
0.8651	High Similarity	NPC262936
0.8651	High Similarity	NPC30491
0.8609	High Similarity	NPC151477
0.8595	High Similarity	NPC469609
0.8595	High Similarity	NPC154030
0.8561	High Similarity	NPC475957
0.856	High Similarity	NPC15127
0.8559	High Similarity	NPC46940
0.8547	High Similarity	NPC13482
0.8547	High Similarity	NPC132720
0.8537	High Similarity	NPC164852
0.8527	High Similarity	NPC41847
0.8527	High Similarity	NPC85342
0.8525	High Similarity	NPC93071
0.8525	High Similarity	NPC31296
0.8525	High Similarity	NPC258366
0.8525	High Similarity	NPC126002
0.8525	High Similarity	NPC79933
0.8525	High Similarity	NPC473974
0.8516	High Similarity	NPC131684
0.8487	Intermediate Similarity	NPC715
0.8475	Intermediate Similarity	NPC95716
0.8455	Intermediate Similarity	NPC135467
0.8455	Intermediate Similarity	NPC260832
0.8443	Intermediate Similarity	NPC328694
0.8438	Intermediate Similarity	NPC96024
0.8435	Intermediate Similarity	NPC117115
0.8413	Intermediate Similarity	NPC75432
0.8409	Intermediate Similarity	NPC103082
0.8403	Intermediate Similarity	NPC228425
0.84	Intermediate Similarity	NPC478058
0.84	Intermediate Similarity	NPC282577
0.8397	Intermediate Similarity	NPC111845
0.8397	Intermediate Similarity	NPC476282
0.8385	Intermediate Similarity	NPC243305
0.8382	Intermediate Similarity	NPC477209
0.8376	Intermediate Similarity	NPC11554
0.837	Intermediate Similarity	NPC476534
0.8362	Intermediate Similarity	NPC21594
0.8361	Intermediate Similarity	NPC16030
0.8347	Intermediate Similarity	NPC469719
0.8346	Intermediate Similarity	NPC131799
0.8333	Intermediate Similarity	NPC273683
0.8333	Intermediate Similarity	NPC275145
0.8333	Intermediate Similarity	NPC293454
0.8333	Intermediate Similarity	NPC213122
0.8319	Intermediate Similarity	NPC471188
0.8319	Intermediate Similarity	NPC77772
0.8319	Intermediate Similarity	NPC322753
0.8319	Intermediate Similarity	NPC151537
0.8309	Intermediate Similarity	NPC272907
0.8309	Intermediate Similarity	NPC2681
0.8305	Intermediate Similarity	NPC58865
0.8293	Intermediate Similarity	NPC48342
0.8293	Intermediate Similarity	NPC164649
0.8291	Intermediate Similarity	NPC228737
0.8281	Intermediate Similarity	NPC325294
0.8281	Intermediate Similarity	NPC295202
0.8281	Intermediate Similarity	NPC269598
0.8281	Intermediate Similarity	NPC227741
0.8281	Intermediate Similarity	NPC49647
0.8281	Intermediate Similarity	NPC100414
0.8281	Intermediate Similarity	NPC136342
0.8281	Intermediate Similarity	NPC43000
0.8281	Intermediate Similarity	NPC321822
0.8271	Intermediate Similarity	NPC153088
0.8258	Intermediate Similarity	NPC138472
0.8254	Intermediate Similarity	NPC471794
0.825	Intermediate Similarity	NPC286222
0.8244	Intermediate Similarity	NPC258073
0.824	Intermediate Similarity	NPC21216
0.824	Intermediate Similarity	NPC328504
0.8235	Intermediate Similarity	NPC471853
0.8235	Intermediate Similarity	NPC3218
0.8226	Intermediate Similarity	NPC151197
0.8222	Intermediate Similarity	NPC477593
0.8217	Intermediate Similarity	NPC108164
0.8217	Intermediate Similarity	NPC471077
0.8211	Intermediate Similarity	NPC174087
0.8203	Intermediate Similarity	NPC137416
0.8203	Intermediate Similarity	NPC123506
0.8203	Intermediate Similarity	NPC124030
0.8195	Intermediate Similarity	NPC27394
0.8195	Intermediate Similarity	NPC194970
0.8188	Intermediate Similarity	NPC199936
0.8188	Intermediate Similarity	NPC100242
0.8182	Intermediate Similarity	NPC317869
0.8168	Intermediate Similarity	NPC470725
0.8168	Intermediate Similarity	NPC253488
0.8167	Intermediate Similarity	NPC266937
0.8167	Intermediate Similarity	NPC470770
0.8162	Intermediate Similarity	NPC76312
0.816	Intermediate Similarity	NPC133389
0.816	Intermediate Similarity	NPC183339
0.816	Intermediate Similarity	NPC234337
0.8154	Intermediate Similarity	NPC229894
0.8154	Intermediate Similarity	NPC48248
0.8151	Intermediate Similarity	NPC314187
0.8145	Intermediate Similarity	NPC206
0.8143	Intermediate Similarity	NPC477208
0.8134	Intermediate Similarity	NPC279463
0.813	Intermediate Similarity	NPC141001
0.813	Intermediate Similarity	NPC474387
0.813	Intermediate Similarity	NPC247858
0.813	Intermediate Similarity	NPC474358
0.813	Intermediate Similarity	NPC137496
0.813	Intermediate Similarity	NPC257540
0.813	Intermediate Similarity	NPC154511
0.8125	Intermediate Similarity	NPC152525
0.8125	Intermediate Similarity	NPC68756
0.8125	Intermediate Similarity	NPC173978
0.812	Intermediate Similarity	NPC475457
0.812	Intermediate Similarity	NPC18982
0.812	Intermediate Similarity	NPC475627
0.812	Intermediate Similarity	NPC314048
0.812	Intermediate Similarity	NPC475346
0.8116	Intermediate Similarity	NPC308572
0.8116	Intermediate Similarity	NPC248068
0.8115	Intermediate Similarity	NPC471534
0.811	Intermediate Similarity	NPC152946
0.811	Intermediate Similarity	NPC71094
0.8106	Intermediate Similarity	NPC164295
0.8106	Intermediate Similarity	NPC18798
0.8106	Intermediate Similarity	NPC93015
0.8106	Intermediate Similarity	NPC72669
0.8106	Intermediate Similarity	NPC474517
0.8099	Intermediate Similarity	NPC471179
0.8099	Intermediate Similarity	NPC228988
0.8099	Intermediate Similarity	NPC62867
0.8099	Intermediate Similarity	NPC177962
0.8095	Intermediate Similarity	NPC216216
0.8092	Intermediate Similarity	NPC117899
0.8092	Intermediate Similarity	NPC474546
0.8088	Intermediate Similarity	NPC141368
0.8088	Intermediate Similarity	NPC206207
0.8087	Intermediate Similarity	NPC211885
0.8083	Intermediate Similarity	NPC95126
0.8083	Intermediate Similarity	NPC475002

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 NPC11250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	945
0.2-0.3	1231
0.3-0.4	2608
0.4-0.5	2240
0.5-0.6	1327
0.6-0.7	467
0.7-0.8	75
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8917	High Similarity	NPD3019	Approved
0.876	High Similarity	NPD2932	Approved
0.8385	Intermediate Similarity	NPD6663	Approved
0.8359	Intermediate Similarity	NPD5736	Approved
0.8293	Intermediate Similarity	NPD3091	Approved
0.824	Intermediate Similarity	NPD3023	Approved
0.824	Intermediate Similarity	NPD3026	Approved
0.8226	Intermediate Similarity	NPD3025	Approved
0.8226	Intermediate Similarity	NPD3024	Approved
0.8031	Intermediate Similarity	NPD3092	Approved
0.7983	Intermediate Similarity	NPD2342	Discontinued
0.7951	Intermediate Similarity	NPD7635	Approved
0.7943	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1201	Approved
0.7874	Intermediate Similarity	NPD4059	Approved
0.7874	Intermediate Similarity	NPD3095	Discontinued
0.7846	Intermediate Similarity	NPD1283	Approved
0.7795	Intermediate Similarity	NPD1651	Approved
0.7786	Intermediate Similarity	NPD3094	Phase 2
0.7786	Intermediate Similarity	NPD7003	Approved
0.7739	Intermediate Similarity	NPD1809	Phase 2
0.773	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3020	Approved
0.7681	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD288	Approved
0.766	Intermediate Similarity	NPD8166	Discontinued
0.7656	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD1470	Approved
0.7626	Intermediate Similarity	NPD5404	Approved
0.7626	Intermediate Similarity	NPD5408	Approved
0.7626	Intermediate Similarity	NPD5405	Approved
0.7626	Intermediate Similarity	NPD5406	Approved
0.7615	Intermediate Similarity	NPD1281	Approved
0.7597	Intermediate Similarity	NPD4626	Approved
0.7586	Intermediate Similarity	NPD844	Approved
0.7561	Intermediate Similarity	NPD4750	Phase 3
0.7554	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD5951	Approved
0.7536	Intermediate Similarity	NPD4097	Suspended
0.75	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD6099	Approved
0.7479	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2286	Discontinued
0.7445	Intermediate Similarity	NPD8032	Phase 2
0.744	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2860	Approved
0.7436	Intermediate Similarity	NPD2859	Approved
0.7419	Intermediate Similarity	NPD3022	Approved
0.7419	Intermediate Similarity	NPD3021	Approved
0.7414	Intermediate Similarity	NPD845	Approved
0.7391	Intermediate Similarity	NPD2979	Phase 3
0.7391	Intermediate Similarity	NPD4060	Phase 1
0.7391	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3620	Phase 2
0.7391	Intermediate Similarity	NPD4140	Approved
0.7385	Intermediate Similarity	NPD5691	Approved
0.7385	Intermediate Similarity	NPD4093	Discontinued
0.735	Intermediate Similarity	NPD2933	Approved
0.735	Intermediate Similarity	NPD2934	Approved
0.7333	Intermediate Similarity	NPD4624	Approved
0.7328	Intermediate Similarity	NPD1751	Approved
0.7323	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6273	Approved
0.7248	Intermediate Similarity	NPD7458	Discontinued
0.7239	Intermediate Similarity	NPD5327	Phase 3
0.7226	Intermediate Similarity	NPD2606	Approved
0.7226	Intermediate Similarity	NPD2605	Approved
0.7206	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7742	Approved
0.7183	Intermediate Similarity	NPD7743	Approved
0.7174	Intermediate Similarity	NPD5156	Approved
0.7174	Intermediate Similarity	NPD5155	Approved
0.7172	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4208	Discontinued
0.7153	Intermediate Similarity	NPD3636	Approved
0.7153	Intermediate Similarity	NPD3635	Approved
0.7153	Intermediate Similarity	NPD3637	Approved
0.7133	Intermediate Similarity	NPD2531	Phase 2
0.7133	Intermediate Similarity	NPD4476	Approved
0.7133	Intermediate Similarity	NPD4477	Approved
0.7133	Intermediate Similarity	NPD2438	Suspended
0.7133	Intermediate Similarity	NPD2935	Discontinued
0.7133	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1164	Approved
0.7132	Intermediate Similarity	NPD2629	Approved
0.7122	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1755	Approved
0.7101	Intermediate Similarity	NPD3595	Approved
0.7101	Intermediate Similarity	NPD3594	Approved
0.7095	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5735	Approved
0.709	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2195	Approved
0.708	Intermediate Similarity	NPD2194	Approved
0.7073	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1778	Approved
0.7068	Intermediate Similarity	NPD4589	Approved
0.7068	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6696	Suspended
0.7054	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7008	Discontinued
0.705	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4625	Phase 3
0.7042	Intermediate Similarity	NPD6353	Approved
0.7037	Intermediate Similarity	NPD3972	Approved
0.7008	Intermediate Similarity	NPD1792	Phase 2
0.7007	Intermediate Similarity	NPD2797	Approved
0.7	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD497	Approved
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3764	Approved
0.6993	Remote Similarity	NPD37	Approved
0.6992	Remote Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD846	Approved
0.6986	Remote Similarity	NPD3638	Discontinued
0.6972	Remote Similarity	NPD6355	Discontinued
0.6966	Remote Similarity	NPD2346	Discontinued
0.6959	Remote Similarity	NPD3300	Phase 2
0.6939	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4110	Phase 3
0.6929	Remote Similarity	NPD7095	Approved
0.6923	Remote Similarity	NPD495	Approved
0.6923	Remote Similarity	NPD2228	Approved
0.6923	Remote Similarity	NPD498	Approved
0.6923	Remote Similarity	NPD496	Approved
0.6923	Remote Similarity	NPD2234	Approved
0.6923	Remote Similarity	NPD2229	Approved
0.6917	Remote Similarity	NPD5303	Approved
0.6917	Remote Similarity	NPD5304	Approved
0.6906	Remote Similarity	NPD2861	Phase 2
0.6899	Remote Similarity	NPD6959	Discontinued
0.6894	Remote Similarity	NPD7340	Approved
0.6887	Remote Similarity	NPD7427	Discontinued
0.6884	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6234	Discontinued
0.6871	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2533	Approved
0.6867	Remote Similarity	NPD2534	Approved
0.6867	Remote Similarity	NPD2532	Approved
0.6866	Remote Similarity	NPD5585	Approved
0.6861	Remote Similarity	NPD4749	Approved
0.6859	Remote Similarity	NPD4967	Phase 2
0.6859	Remote Similarity	NPD4966	Approved
0.6859	Remote Similarity	NPD4965	Approved
0.6857	Remote Similarity	NPD4908	Phase 1
0.6857	Remote Similarity	NPD4207	Discontinued
0.6855	Remote Similarity	NPD6232	Discontinued
0.6849	Remote Similarity	NPD4725	Approved
0.6849	Remote Similarity	NPD4726	Approved
0.6849	Remote Similarity	NPD4721	Approved
0.6835	Remote Similarity	NPD2798	Approved
0.6832	Remote Similarity	NPD7473	Discontinued
0.6828	Remote Similarity	NPD2799	Discontinued
0.6824	Remote Similarity	NPD4628	Phase 3
0.6824	Remote Similarity	NPD3400	Discontinued
0.6818	Remote Similarity	NPD255	Approved
0.6818	Remote Similarity	NPD3317	Approved
0.6818	Remote Similarity	NPD256	Approved
0.6818	Remote Similarity	NPD4198	Discontinued
0.6812	Remote Similarity	NPD1876	Approved
0.6806	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD970	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7041	Phase 2
0.68	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3226	Approved
0.6797	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1398	Phase 1
0.6791	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7330	Discontinued
0.6788	Remote Similarity	NPD1608	Approved
0.6774	Remote Similarity	NPD1242	Phase 1
0.6772	Remote Similarity	NPD1444	Approved
0.6772	Remote Similarity	NPD1445	Approved
0.6761	Remote Similarity	NPD3268	Approved
0.6757	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3645	Discontinued
0.6755	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7028	Phase 2
0.675	Remote Similarity	NPD1088	Approved
0.6741	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3657	Discovery
0.6735	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7819	Suspended
0.6724	Remote Similarity	NPD111	Approved
0.6716	Remote Similarity	NPD7610	Discontinued
0.6715	Remote Similarity	NPD1611	Approved
0.6715	Remote Similarity	NPD1610	Phase 2
0.6714	Remote Similarity	NPD6584	Phase 3
0.6694	Remote Similarity	NPD2066	Phase 3
0.6692	Remote Similarity	NPD6671	Approved
0.6692	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1607	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