NPASS Compound

Structure

CID33382 OpenBabel06191715362D 21 23 0 0 1 0 0 0 0 0999 V2000 -3.4553 -2.6736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7916 -2.0350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9941 1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7861 -1.9305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9941 -0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8601 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1244 -3.4168 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7261 -0.9523 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8601 0.5477 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 0.5477 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6418 0.4307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1160 -1.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2319 -2.5772 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 5 1 0 0 0 0 1 13 3 0 0 0 0 2 5 2 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 15 2 0 0 0 0 4 16 1 0 0 0 0 5 7 1 0 0 0 0 6 3 1 6 0 0 0 6 8 1 0 0 0 0 6 21 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 1 0 0 0 9 12 1 0 0 0 0 9 20 1 1 0 0 0 10 14 1 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 17 1 6 0 0 0 12 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	291.1
Volume:	264.765
LogP:	-1.689
LogD:	-0.946
LogS:	-1.039
# Rotatable Bonds:	2
TPSA:	151.17
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	4.385
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.698
MDCK Permeability:	4.1460793909209315e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.908
Human Intestinal Absorption (HIA):	0.952
20% Bioavailability (F20%):	0.78
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.425
Plasma Protein Binding (PPB):	17.722766876220703%
Volume Distribution (VD):	1.05
Pgp-substrate:	75.69740295410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.127
CYP1A2-substrate:	0.559
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.101
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.055

ADMET: Excretion

Clearance (CL):	4.703
Half-life (T1/2):	0.912

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.271
Rat Oral Acute Toxicity:	0.445
Maximum Recommended Daily Dose:	0.078
Skin Sensitization:	0.099
Carcinogencity:	0.15
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.192

Download Data

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

Natural Product: NPC33382

Natural Product ID:	NPC33382
*Common Name:**	Toyocamycin
IUPAC Name:	4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
Synonyms:
Standard InCHIKey:	XOKJUSAYZUAMGJ-WOUKDFQISA-N
Standard InCHI:	InChI=1S/C12H13N5O4/c13-1-5-2-17(11-7(5)10(14)15-4-16-11)12-9(20)8(19)6(3-18)21-12/h2,4,6,8-9,12,18-20H,3H2,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1
SMILES:	C(#N)c1cn(c2c1c(N)ncn2)[C@H]1[C@@H]([C@@H]([C@@H](CO)O1)O)O
Synthetic Gene Cluster:	BGC0000879;BGC0000881;
ChEMBL Identifier:	CHEMBL99668
PubChem CID:	11824
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0002306] Pyrrolopyrimidine nucleosides and nucleotides

*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
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.tet.2007.03.162]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.tet.2008.05.037]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.tet.2008.10.076]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075778]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10344559]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10344578]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10348041]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10604756]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10695669]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10724004]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10994816]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11099231]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11132958]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374972]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473415]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14738393]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Australian	n.a.	PMID[15497950]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15813185]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15844966]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15974616]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16180833]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1666120]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724845]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16830891]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16872146]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125235]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17315965]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17551212]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17608531]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17844998]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17887721]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17917237]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18044841]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Indonesian	n.a.	PMID[18081255]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18081255]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18205372]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Northwest Territories, Canada	1995	PMID[18327911]
NPO32842	jaspis spp.	Species	Ancorinidae	Eukaryota	n.a.	east coast of Malaysia	1994	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18666798]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18776684]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19007176]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19129624]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19191549]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19856955]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19883065]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20092333]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20545334]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20836523]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028889]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028891]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21090727]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	Fiji (S 1822.28', E 17758.87')	2000-FEB	PMID[21241058]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21241058]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21314175]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21639131]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21728289]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	latex	n.a.	PMID[21751787]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21807523]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21873059]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	latex	n.a.	PMID[21879726]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[22145663]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22574670]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22583058]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22591466]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22758660]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22775474]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23387796]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23662937]
NPO18708	Streptomyces diastatochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23775805]
NPO33669	Jaspis johnstoni	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24020843]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24592993]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24754815]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24878306]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24964393]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25211234]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25455147]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25495422]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25537064]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25918793]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25934225]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26035239]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26465675]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26798949]
NPO11484	Jaspis splendens	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26883470]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26905826]
NPO33669	Jaspis johnstoni	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2693614]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31013087]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31298537]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31894983]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32298122]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8501018]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[8784423]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8931733]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8982334]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9031666]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9031676]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9066767]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9066768]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9186568]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9531983]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[9711246]
NPO18708	Streptomyces diastatochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11484	Jaspis splendens	Species	Ancorinidae	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	3
IC50	33
Kd	2
MIC	11
Others	33

Activity Type	# Activity
Cell Line	24
Individual Protein	8
NON-MOLECULAR	2
Organism	42
Others	5
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	MCC	>	0.4	ug.mL-1	PMID[521824]
NPT189	Cell Line	Vero	Chlorocebus aethiops	MCC	=	0.04	ug.mL-1	PMID[521824]
NPT137	Cell Line	L1210	Mus musculus	ID50	=	0.006	ug ml-1	PMID[521824]
NPT165	Cell Line	HeLa	Homo sapiens	MTC	=	0.4	ug ml-1	PMID[521825]
NPT189	Cell Line	Vero	Chlorocebus aethiops	MTC	=	0.04	ug ml-1	PMID[521825]
NPT137	Cell Line	L1210	Mus musculus	MIC50	=	0.006	ug.mL-1	PMID[521825]
NPT137	Cell Line	L1210	Mus musculus	MIC50	=	38.0	ug.mL-1	PMID[521825]
NPT137	Cell Line	L1210	Mus musculus	MIC50	=	0.071	ug.mL-1	PMID[521825]
NPT137	Cell Line	L1210	Mus musculus	MIC50	=	0.039	ug.mL-1	PMID[521825]
NPT2603	Individual Protein	Adenosine kinase	Homo sapiens	IC50	=	310.0	nM	PMID[521826]
NPT2603	Individual Protein	Adenosine kinase	Homo sapiens	IC50	=	3228494121.71	nM	PMID[521826]
NPT319	Cell Line	B16	Mus musculus	EC50	=	5.0	nM	PMID[521827]
NPT859	Cell Line	HFF	Homo sapiens	IC50	=	8000.0	nM	PMID[521828]
NPT859	Cell Line	HFF	Homo sapiens	IC50	<	10.0	nM	PMID[521829]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	30.0	nM	PMID[521829]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	4.0	nM	PMID[521830]
NPT2603	Individual Protein	Adenosine kinase	Homo sapiens	IC50	=	3235936569.3	nM	PMID[521831]
NPT859	Cell Line	HFF	Homo sapiens	IC50	=	30.0	nM	PMID[521832]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	30.0	nM	PMID[521832]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	4.0	nM	PMID[521832]
NPT859	Cell Line	HFF	Homo sapiens	IC50	=	8000.0	nM	PMID[521833]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	17000.0	nM	PMID[521833]
NPT859	Cell Line	HFF	Homo sapiens	IC50	=	300.0	nM	PMID[521834]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	100.0	nM	PMID[521834]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	100.0	nM	PMID[521834]
NPT2603	Individual Protein	Adenosine kinase	Homo sapiens	IC50	=	310.0	nM	PMID[521835]
NPT168	Cell Line	P388	Mus musculus	Activity	=	0.0023	ug ml-1	PMID[521836]
NPT2603	Individual Protein	Adenosine kinase	Homo sapiens	log(10'3/IC50)	=	3.51	n.a.	PMID[521838]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.0026	ug.mL-1	PMID[521839]
NPT2604	Individual Protein	Heat shock cognate 71 kDa protein	Homo sapiens	Kd	=	91201.08	nM	PMID[521843]
NPT2604	Individual Protein	Heat shock cognate 71 kDa protein	Homo sapiens	Kd	=	90000.0	nM	PMID[521843]
NPT6098	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-79 specific	Homo sapiens	IC50	=	44000.0	nM	PMID[521845]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	MIC	=	0.07	ug.mL-1	PMID[521824]
NPT335	Organism	Human coxsackievirus B4	Human coxsackievirus B4	MIC	>	0.01	ug.mL-1	PMID[521824]
NPT1106	Organism	Human poliovirus 1	Human poliovirus 1	MIC	>	0.01	ug.mL-1	PMID[521824]
NPT3878	Organism	Mammalian orthoreovirus 1	Mammalian orthoreovirus 1	MIC	>	0.01	ug.mL-1	PMID[521824]
NPT336	Organism	Human parainfluenza virus 3	Human parainfluenza virus 3	MIC	>	0.01	ug.mL-1	PMID[521824]
NPT338	Organism	Sindbis virus	Sindbis virus	MIC	>	0.01	ug.mL-1	PMID[521824]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	MCC	>	0.04	ug.mL-1	PMID[521824]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MIC	>	0.04	ug.mL-1	PMID[521824]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	MIC	=	0.07	ug.mL-1	PMID[521824]
NPT334	Organism	Vaccinia virus	Vaccinia virus	MIC	>	0.01	ug.mL-1	PMID[521824]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	MIC	>	1.0	ug.mL-1	PMID[521824]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	MTC	=	0.04	ug ml-1	PMID[521825]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MIC50	>	0.04	ug.mL-1	PMID[521825]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	MIC50	>	0.04	ug.mL-1	PMID[521825]
NPT334	Organism	Vaccinia virus	Vaccinia virus	MIC50	>	0.04	ug.mL-1	PMID[521825]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	MIC50	>	0.04	ug.mL-1	PMID[521825]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	MIC50	=	0.07	ug.mL-1	PMID[521825]
NPT335	Organism	Human coxsackievirus B4	Human coxsackievirus B4	MIC50	>	0.4	ug.mL-1	PMID[521825]
NPT1106	Organism	Human poliovirus 1	Human poliovirus 1	MIC50	>	0.4	ug.mL-1	PMID[521825]
NPT3878	Organism	Mammalian orthoreovirus 1	Mammalian orthoreovirus 1	MIC50	>	0.04	ug.mL-1	PMID[521825]
NPT336	Organism	Human parainfluenza virus 3	Human parainfluenza virus 3	MIC50	>	0.04	ug.mL-1	PMID[521825]
NPT338	Organism	Sindbis virus	Sindbis virus	MIC50	>	0.04	ug.mL-1	PMID[521825]
NPT335	Organism	Human coxsackievirus B4	Human coxsackievirus B4	MIC50	>	0.04	ug.mL-1	PMID[521825]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	12.0	nM	PMID[521827]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	4.0	nM	PMID[521827]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	1700.0	nM	PMID[521828]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC90	=	14000.0	nM	PMID[521828]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	29000.0	nM	PMID[521828]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC90	=	3500.0	nM	PMID[521828]
NPT27	Others	Unspecified		IC50	=	46000.0	nM	PMID[521828]
NPT27	Others	Unspecified		IC50	=	17000.0	nM	PMID[521828]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	50.0	nM	PMID[521829]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	50.0	nM	PMID[521830]
NPT27	Others	Unspecified		IC50	=	30.0	nM	PMID[521830]
NPT27	Others	Unspecified		IC50	=	40.0	nM	PMID[521830]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	100.0	nM	PMID[521832]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	1700.0	nM	PMID[521833]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	29000.0	nM	PMID[521833]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC90	=	14000.0	nM	PMID[521833]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	300.0	nM	PMID[521834]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	400.0	nM	PMID[521834]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC90	=	300.0	nM	PMID[521834]
NPT2	Others	Unspecified		IC50	=	3.3	ug.mL-1	PMID[521837]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	13.0	mm	PMID[521839]
NPT1047	Organism	Simplexvirus	Simplexvirus	IC50	=	38000.0	nM	PMID[521841]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	13.77	%	PMID[521844]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	14.22	%	PMID[521846]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	11.99	%	PMID[521847]

☑ 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 NPC33382 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	404
0.1-0.2	13407
0.2-0.3	22004
0.3-0.4	4150
0.4-0.5	2367
0.5-0.6	203
0.6-0.7	116
0.7-0.8	40
0.8-0.85	1
0.85-0.9	1
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9177	High Similarity	NPC222174
0.9172	High Similarity	NPC125659
0.9172	High Similarity	NPC168702
0.7516	Intermediate Similarity	NPC21448
0.7516	Intermediate Similarity	NPC156461
0.7516	Intermediate Similarity	NPC107374
0.7515	Intermediate Similarity	NPC207633
0.7469	Intermediate Similarity	NPC189068
0.7469	Intermediate Similarity	NPC164665
0.744	Intermediate Similarity	NPC239737
0.7423	Intermediate Similarity	NPC269827
0.7423	Intermediate Similarity	NPC219313
0.7423	Intermediate Similarity	NPC309832
0.7412	Intermediate Similarity	NPC321393
0.7391	Intermediate Similarity	NPC229974
0.7267	Intermediate Similarity	NPC161659
0.7267	Intermediate Similarity	NPC209525
0.7246	Intermediate Similarity	NPC185991
0.7246	Intermediate Similarity	NPC85689
0.7246	Intermediate Similarity	NPC211025
0.7202	Intermediate Similarity	NPC472816
0.7202	Intermediate Similarity	NPC321814
0.7186	Intermediate Similarity	NPC150853
0.7178	Intermediate Similarity	NPC314152
0.716	Intermediate Similarity	NPC317821
0.716	Intermediate Similarity	NPC164952
0.716	Intermediate Similarity	NPC130586
0.716	Intermediate Similarity	NPC212551
0.716	Intermediate Similarity	NPC302778
0.7118	Intermediate Similarity	NPC174802
0.7099	Intermediate Similarity	NPC129756
0.7076	Intermediate Similarity	NPC224076
0.7066	Intermediate Similarity	NPC121222
0.7035	Intermediate Similarity	NPC226245
0.7035	Intermediate Similarity	NPC316618
0.6941	Remote Similarity	NPC161224
0.6875	Remote Similarity	NPC107160
0.6839	Remote Similarity	NPC313754
0.6839	Remote Similarity	NPC311197
0.6839	Remote Similarity	NPC54320
0.6836	Remote Similarity	NPC323091
0.6829	Remote Similarity	NPC33996
0.6824	Remote Similarity	NPC136349
0.681	Remote Similarity	NPC320818
0.6782	Remote Similarity	NPC52238
0.6705	Remote Similarity	NPC328479
0.6685	Remote Similarity	NPC189261
0.6648	Remote Similarity	NPC93365
0.6618	Remote Similarity	NPC250178
0.6575	Remote Similarity	NPC261595
0.6545	Remote Similarity	NPC327941
0.6541	Remote Similarity	NPC326529
0.6538	Remote Similarity	NPC324033
0.6538	Remote Similarity	NPC321458
0.6517	Remote Similarity	NPC195140
0.6505	Remote Similarity	NPC324198
0.6505	Remote Similarity	NPC319100
0.648	Remote Similarity	NPC138018
0.6471	Remote Similarity	NPC315642
0.6471	Remote Similarity	NPC74306
0.6467	Remote Similarity	NPC314646
0.6452	Remote Similarity	NPC158055
0.6429	Remote Similarity	NPC324484
0.6429	Remote Similarity	NPC62151
0.6413	Remote Similarity	NPC290959
0.6413	Remote Similarity	NPC326082
0.6407	Remote Similarity	NPC61198
0.6393	Remote Similarity	NPC325906
0.6364	Remote Similarity	NPC313897
0.6347	Remote Similarity	NPC262926
0.6328	Remote Similarity	NPC321052
0.63	Remote Similarity	NPC474767
0.6289	Remote Similarity	NPC313514
0.6239	Remote Similarity	NPC160666
0.6239	Remote Similarity	NPC21461
0.6237	Remote Similarity	NPC319456
0.6235	Remote Similarity	NPC30326
0.6207	Remote Similarity	NPC89147
0.6207	Remote Similarity	NPC274384
0.619	Remote Similarity	NPC319221
0.6149	Remote Similarity	NPC211820
0.6149	Remote Similarity	NPC251233
0.6131	Remote Similarity	NPC324009
0.6127	Remote Similarity	NPC186619
0.6114	Remote Similarity	NPC177169
0.6098	Remote Similarity	NPC103388
0.608	Remote Similarity	NPC64705
0.608	Remote Similarity	NPC232408
0.6057	Remote Similarity	NPC318590
0.6051	Remote Similarity	NPC24589
0.6041	Remote Similarity	NPC282458
0.6041	Remote Similarity	NPC78941
0.6034	Remote Similarity	NPC326694
0.6023	Remote Similarity	NPC317746
0.6	Remote Similarity	NPC276373
0.599	Remote Similarity	NPC292361
0.5971	Remote Similarity	NPC5802
0.5942	Remote Similarity	NPC157821
0.5859	Remote Similarity	NPC62510
0.5851	Remote Similarity	NPC71079
0.5833	Remote Similarity	NPC89562
0.582	Remote Similarity	NPC474217
0.5798	Remote Similarity	NPC14590
0.5789	Remote Similarity	NPC85918
0.5773	Remote Similarity	NPC317054
0.5771	Remote Similarity	NPC75544
0.5771	Remote Similarity	NPC472289
0.5759	Remote Similarity	NPC127730
0.5759	Remote Similarity	NPC278366
0.5736	Remote Similarity	NPC317010
0.5707	Remote Similarity	NPC41333
0.5676	Remote Similarity	NPC130570
0.5657	Remote Similarity	NPC314491
0.5635	Remote Similarity	NPC197068

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 NPC33382 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1112
0.2-0.3	2920
0.3-0.4	2299
0.4-0.5	2045
0.5-0.6	434
0.6-0.7	136
0.7-0.8	38
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8841	High Similarity	NPD1046	Clinical (unspecified phase)
0.8529	High Similarity	NPD1063	Phase 2
0.8395	Intermediate Similarity	NPD527	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD250	Approved
0.7516	Intermediate Similarity	NPD249	Approved
0.7423	Intermediate Similarity	NPD186	Discovery
0.7423	Intermediate Similarity	NPD195	Approved
0.7407	Intermediate Similarity	NPD5486	Discontinued
0.7292	Intermediate Similarity	NPD5458	Discontinued
0.7246	Intermediate Similarity	NPD283	Approved
0.7178	Intermediate Similarity	NPD185	Approved
0.716	Intermediate Similarity	NPD1369	Phase 2
0.716	Intermediate Similarity	NPD242	Approved
0.716	Intermediate Similarity	NPD3107	Discontinued
0.716	Intermediate Similarity	NPD1750	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD338	Approved
0.715	Intermediate Similarity	NPD2965	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD339	Approved
0.7091	Intermediate Similarity	NPD166	Approved
0.7076	Intermediate Similarity	NPD169	Phase 2
0.7055	Intermediate Similarity	NPD193	Suspended
0.7035	Intermediate Similarity	NPD2646	Discontinued
0.7035	Intermediate Similarity	NPD2624	Phase 2
0.7035	Intermediate Similarity	NPD1732	Phase 3
0.7026	Intermediate Similarity	NPD2876	Phase 3
0.7026	Intermediate Similarity	NPD2877	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1692	Approved
0.7006	Intermediate Similarity	NPD2647	Phase 3
0.7	Intermediate Similarity	NPD231	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD536	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2824	Phase 2
0.694	Remote Similarity	NPD4716	Approved
0.6902	Remote Similarity	NPD4744	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD219	Phase 3
0.6839	Remote Similarity	NPD220	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD217	Approved
0.6839	Remote Similarity	NPD216	Approved
0.6839	Remote Similarity	NPD218	Approved
0.6824	Remote Similarity	NPD548	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD516	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5666	Phase 2
0.6667	Remote Similarity	NPD214	Approved
0.6667	Remote Similarity	NPD213	Clinical (unspecified phase)
0.665	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.665	Remote Similarity	NPD2902	Phase 2
0.6648	Remote Similarity	NPD546	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4563	Phase 2
0.6597	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD247	Clinical (unspecified phase)
0.651	Remote Similarity	NPD207	Discontinued
0.6505	Remote Similarity	NPD4171	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD9632	Phase 3
0.6502	Remote Similarity	NPD6351	Discovery
0.6484	Remote Similarity	NPD7988	Suspended
0.6471	Remote Similarity	NPD1412	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD582	Approved
0.6457	Remote Similarity	NPD8250	Phase 2
0.6452	Remote Similarity	NPD6840	Approved
0.6407	Remote Similarity	NPD252	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5683	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6417	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5684	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5682	Phase 3
0.6402	Remote Similarity	NPD248	Discontinued
0.64	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4458	Phase 2
0.6393	Remote Similarity	NPD1777	Approved
0.6393	Remote Similarity	NPD1776	Approved
0.6393	Remote Similarity	NPD2134	Approved
0.6393	Remote Similarity	NPD2136	Approved
0.6393	Remote Similarity	NPD2135	Approved
0.6324	Remote Similarity	NPD796	Phase 2
0.6319	Remote Similarity	NPD3083	Approved
0.629	Remote Similarity	NPD5172	Phase 2
0.6289	Remote Similarity	NPD7138	Phase 2
0.6286	Remote Similarity	NPD5080	Phase 2
0.6257	Remote Similarity	NPD549	Approved
0.6244	Remote Similarity	NPD1234	Discontinued
0.6238	Remote Similarity	NPD5079	Phase 2
0.6232	Remote Similarity	NPD4495	Phase 1
0.6227	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD534	Phase 2
0.6226	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD537	Phase 2
0.6224	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD870	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD2630	Approved
0.6173	Remote Similarity	NPD2632	Approved
0.6173	Remote Similarity	NPD2631	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD2127	Suspended
0.6154	Remote Similarity	NPD2872	Phase 2
0.6154	Remote Similarity	NPD194	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD3593	Approved
0.6087	Remote Similarity	NPD4533	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4612	Discontinued
0.598	Remote Similarity	NPD4054	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD1915	Phase 1
0.5913	Remote Similarity	NPD4683	Phase 3
0.5909	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD9582	Phase 3
0.5892	Remote Similarity	NPD1709	Phase 1
0.5892	Remote Similarity	NPD4074	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD2457	Phase 2
0.5888	Remote Similarity	NPD2456	Phase 2
0.5872	Remote Similarity	NPD4187	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5171	Clinical (unspecified phase)
0.5858	Remote Similarity	NPD9633	Phase 3
0.5857	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD3085	Phase 1
0.5851	Remote Similarity	NPD4239	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD3013	Phase 3
0.5849	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD7158	Phase 1
0.5829	Remote Similarity	NPD1367	Phase 2
0.5824	Remote Similarity	NPD3086	Phase 3
0.5814	Remote Similarity	NPD6528	Phase 1
0.5805	Remote Similarity	NPD6112	Approved
0.5805	Remote Similarity	NPD691	Discontinued
0.5803	Remote Similarity	NPD4089	Clinical (unspecified phase)
0.5799	Remote Similarity	NPD6381	Phase 2
0.5797	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3849	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD6772	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD1197	Approved
0.5778	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD5627	Approved
0.5776	Remote Similarity	NPD8375	Approved
0.5774	Remote Similarity	NPD9408	Phase 3
0.5773	Remote Similarity	NPD2928	Phase 2
0.5769	Remote Similarity	NPD3708	Phase 2
0.5764	Remote Similarity	NPD4615	Phase 2
0.575	Remote Similarity	NPD2591	Phase 2
0.5746	Remote Similarity	NPD775	Approved
0.5746	Remote Similarity	NPD8409	Suspended
0.5737	Remote Similarity	NPD5925	Phase 1
0.5735	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD5584	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.5707	Remote Similarity	NPD1675	Phase 1
0.5707	Remote Similarity	NPD9605	Phase 3
0.5707	Remote Similarity	NPD1674	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4654	Phase 1
0.5693	Remote Similarity	NPD7504	Discontinued
0.5682	Remote Similarity	NPD245	Suspended
0.5665	Remote Similarity	NPD545	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD2446	Approved
0.5659	Remote Similarity	NPD2362	Approved
0.5659	Remote Similarity	NPD2445	Approved
0.5657	Remote Similarity	NPD5508	Phase 1
0.5646	Remote Similarity	NPD2536	Discontinued
0.5641	Remote Similarity	NPD5324	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.5637	Remote Similarity	NPD1286	Suspended
0.5631	Remote Similarity	NPD1912	Approved
0.5628	Remote Similarity	NPD8321	Discontinued
0.5625	Remote Similarity	NPD3287	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD7183	Phase 2
0.5608	Remote Similarity	NPD1335	Approved
0.5606	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD1167	Phase 3

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