NPASS Compound

Structure

CID316091 OpenBabel06191716132D 36 39 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 -5.1962 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 0.8660 -0.5000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 34 1 0 0 0 0 5 35 1 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 21 1 0 0 0 0 10 16 1 0 0 0 0 10 36 1 0 0 0 0 11 28 2 0 0 0 0 11 36 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 26 1 0 0 0 0 15 19 2 0 0 0 0 15 29 1 0 0 0 0 16 23 1 0 0 0 0 17 20 2 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 22 1 0 0 0 0 21 25 2 0 0 0 0 21 27 1 0 0 0 0 22 30 2 0 0 0 0 23 31 1 0 0 0 0 24 32 2 0 0 0 0 25 34 1 0 0 0 0 26 33 2 0 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.09
Volume:	486.712
LogP:	5.816
LogD:	2.397
LogS:	-3.638
# Rotatable Bonds:	6
TPSA:	142.75
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.095
Synthetic Accessibility Score:	3.441
Fsp3:	0.154
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.337
MDCK Permeability:	1.5796755178598687e-05
Pgp-inhibitor:	0.336
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.831
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	91.35071563720703%
Volume Distribution (VD):	0.603
Pgp-substrate:	13.356285095214844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.558
CYP1A2-substrate:	0.627
CYP2C19-inhibitor:	0.211
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.826
CYP2C9-substrate:	0.688
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	1.259
Half-life (T1/2):	0.428

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.018
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.252
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.869
Skin Sensitization:	0.74
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.883
Respiratory Toxicity:	0.142

Download Data

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

Natural Product: NPC316091

Natural Product ID:	NPC316091
*Common Name:**	Chlorocyclinone B
IUPAC Name:	methyl 9-(1-acetyloxyethyl)-2-chloro-6,8-dihydroxy-1-methoxy-3-methyl-7,12-dioxobenzo[a]anthracene-10-carboxylate
Synonyms:	chlorocyclinone B
Standard InCHIKey:	MFLXCCWOEBQIHW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H21ClO9/c1-9-6-12-7-15(29)19-20(17(12)25(34-4)21(9)27)22(30)13-8-14(26(33)35-5)16(10(2)36-11(3)28)23(31)18(13)24(19)32/h6-8,10,29,31H,1-5H3
SMILES:	Cc1cc2cc(c3c(c2c(c1Cl)OC)C(=O)c1cc(c(C(C)OC(=O)C)c(c1C3=O)O)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254814
PubChem CID:	24762580
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003415] Angucyclines

*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
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.	n.a.	n.a.	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Northwest Territories, Canada	1995	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]
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]
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]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26905826]
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]

☑ 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	1
IC50	2

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	IC50	=	100.0	nM	PMID[570255]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	EC50	=	160.0	nM	PMID[570255]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	IC50	=	1400.0	nM	PMID[570255]

☑ 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 NPC316091 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	448
0.1-0.2	1991
0.2-0.3	4737
0.3-0.4	10925
0.4-0.5	7853
0.5-0.6	5547
0.6-0.7	7221
0.7-0.8	3859
0.8-0.85	79
0.85-0.9	33
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9769	High Similarity	NPC313386
0.9661	High Similarity	NPC313541
0.9649	High Similarity	NPC306240
0.8966	High Similarity	NPC470562
0.8914	High Similarity	NPC470560
0.8857	High Similarity	NPC470565
0.8708	High Similarity	NPC264922
0.8701	High Similarity	NPC474857
0.8678	High Similarity	NPC470563
0.8644	High Similarity	NPC277865
0.8621	High Similarity	NPC470561
0.8579	High Similarity	NPC191606
0.8547	High Similarity	NPC470422
0.8531	High Similarity	NPC472032
0.8516	High Similarity	NPC151292
0.8391	Intermediate Similarity	NPC197326
0.8371	Intermediate Similarity	NPC477835
0.8343	Intermediate Similarity	NPC470559
0.8287	Intermediate Similarity	NPC477836
0.8286	Intermediate Similarity	NPC263483
0.8258	Intermediate Similarity	NPC470081
0.8251	Intermediate Similarity	NPC45072
0.8249	Intermediate Similarity	NPC298401
0.8239	Intermediate Similarity	NPC324736
0.8229	Intermediate Similarity	NPC470564
0.8212	Intermediate Similarity	NPC58653
0.8212	Intermediate Similarity	NPC173352
0.8202	Intermediate Similarity	NPC474096
0.8202	Intermediate Similarity	NPC473696
0.8187	Intermediate Similarity	NPC473113
0.8171	Intermediate Similarity	NPC66508
0.8171	Intermediate Similarity	NPC66029
0.8171	Intermediate Similarity	NPC226656
0.8167	Intermediate Similarity	NPC28669
0.815	Intermediate Similarity	NPC205766
0.8142	Intermediate Similarity	NPC472054
0.8135	Intermediate Similarity	NPC154720
0.8115	Intermediate Similarity	NPC214901
0.809	Intermediate Similarity	NPC472052
0.809	Intermediate Similarity	NPC472060
0.809	Intermediate Similarity	NPC470342
0.8081	Intermediate Similarity	NPC119767
0.8079	Intermediate Similarity	NPC472404
0.8066	Intermediate Similarity	NPC474061
0.8063	Intermediate Similarity	NPC221185
0.8063	Intermediate Similarity	NPC220369
0.8046	Intermediate Similarity	NPC470568
0.8045	Intermediate Similarity	NPC472261
0.8031	Intermediate Similarity	NPC198163
0.8023	Intermediate Similarity	NPC474360
0.8023	Intermediate Similarity	NPC147250
0.8023	Intermediate Similarity	NPC146211
0.8022	Intermediate Similarity	NPC324522
0.8022	Intermediate Similarity	NPC105414
0.8022	Intermediate Similarity	NPC470341
0.8022	Intermediate Similarity	NPC472058
0.8022	Intermediate Similarity	NPC76647
0.8022	Intermediate Similarity	NPC234497
0.8021	Intermediate Similarity	NPC247104
0.8011	Intermediate Similarity	NPC68850
0.8	Intermediate Similarity	NPC470569
0.7989	Intermediate Similarity	NPC284495
0.7978	Intermediate Similarity	NPC317580
0.7967	Intermediate Similarity	NPC30027
0.7966	Intermediate Similarity	NPC318270
0.7958	Intermediate Similarity	NPC470100
0.7958	Intermediate Similarity	NPC470099
0.7955	Intermediate Similarity	NPC154683
0.7955	Intermediate Similarity	NPC40356
0.7947	Intermediate Similarity	NPC474499
0.7944	Intermediate Similarity	NPC472405
0.7943	Intermediate Similarity	NPC147735
0.7937	Intermediate Similarity	NPC99937
0.7933	Intermediate Similarity	NPC326084
0.7931	Intermediate Similarity	NPC2569
0.7931	Intermediate Similarity	NPC172329
0.7921	Intermediate Similarity	NPC474861
0.7919	Intermediate Similarity	NPC314437
0.7914	Intermediate Similarity	NPC207467
0.7914	Intermediate Similarity	NPC471802
0.7912	Intermediate Similarity	NPC469664
0.791	Intermediate Similarity	NPC208806
0.791	Intermediate Similarity	NPC214632
0.7908	Intermediate Similarity	NPC108744
0.7903	Intermediate Similarity	NPC68381
0.7903	Intermediate Similarity	NPC477568
0.7901	Intermediate Similarity	NPC15374
0.7889	Intermediate Similarity	NPC475449
0.7889	Intermediate Similarity	NPC476506
0.7889	Intermediate Similarity	NPC186325
0.7887	Intermediate Similarity	NPC48822
0.7877	Intermediate Similarity	NPC67197
0.7874	Intermediate Similarity	NPC118027
0.7874	Intermediate Similarity	NPC289042
0.7874	Intermediate Similarity	NPC190648
0.7874	Intermediate Similarity	NPC245584
0.7874	Intermediate Similarity	NPC56433
0.7874	Intermediate Similarity	NPC312929
0.7874	Intermediate Similarity	NPC478018
0.7874	Intermediate Similarity	NPC126767
0.7872	Intermediate Similarity	NPC153578
0.7872	Intermediate Similarity	NPC277710
0.7872	Intermediate Similarity	NPC299149
0.7872	Intermediate Similarity	NPC473785
0.7872	Intermediate Similarity	NPC114257
0.7853	Intermediate Similarity	NPC175978
0.7849	Intermediate Similarity	NPC85368
0.7849	Intermediate Similarity	NPC66593
0.7846	Intermediate Similarity	NPC193676
0.7845	Intermediate Similarity	NPC18380
0.7845	Intermediate Similarity	NPC189552
0.7845	Intermediate Similarity	NPC273467
0.7841	Intermediate Similarity	NPC294646
0.7841	Intermediate Similarity	NPC315520
0.7841	Intermediate Similarity	NPC255641
0.7841	Intermediate Similarity	NPC290954
0.7841	Intermediate Similarity	NPC119929
0.7833	Intermediate Similarity	NPC177650
0.7831	Intermediate Similarity	NPC315221
0.7826	Intermediate Similarity	NPC473094
0.7816	Intermediate Similarity	NPC470570
0.7812	Intermediate Similarity	NPC471804
0.7812	Intermediate Similarity	NPC471812
0.7812	Intermediate Similarity	NPC471803
0.7809	Intermediate Similarity	NPC182921
0.7809	Intermediate Similarity	NPC470408
0.7809	Intermediate Similarity	NPC477691
0.7809	Intermediate Similarity	NPC474824
0.7809	Intermediate Similarity	NPC218870
0.7807	Intermediate Similarity	NPC477991
0.7807	Intermediate Similarity	NPC474345
0.7807	Intermediate Similarity	NPC477992
0.7802	Intermediate Similarity	NPC315772
0.7797	Intermediate Similarity	NPC133856
0.7797	Intermediate Similarity	NPC72958
0.7797	Intermediate Similarity	NPC232645
0.7797	Intermediate Similarity	NPC474417
0.7797	Intermediate Similarity	NPC149526
0.7796	Intermediate Similarity	NPC76128
0.7796	Intermediate Similarity	NPC5029
0.7796	Intermediate Similarity	NPC271385
0.7796	Intermediate Similarity	NPC111536
0.7796	Intermediate Similarity	NPC188618
0.7796	Intermediate Similarity	NPC30432
0.7791	Intermediate Similarity	NPC69755
0.779	Intermediate Similarity	NPC472055
0.779	Intermediate Similarity	NPC292863
0.779	Intermediate Similarity	NPC312993
0.779	Intermediate Similarity	NPC143050
0.779	Intermediate Similarity	NPC184326
0.7789	Intermediate Similarity	NPC313452
0.7784	Intermediate Similarity	NPC99613
0.7784	Intermediate Similarity	NPC49487
0.7784	Intermediate Similarity	NPC473095
0.7784	Intermediate Similarity	NPC473096
0.7778	Intermediate Similarity	NPC474637
0.7778	Intermediate Similarity	NPC201127
0.7778	Intermediate Similarity	NPC471801
0.7772	Intermediate Similarity	NPC125465
0.7772	Intermediate Similarity	NPC39409
0.7771	Intermediate Similarity	NPC34802
0.7765	Intermediate Similarity	NPC3898
0.7765	Intermediate Similarity	NPC89625
0.7765	Intermediate Similarity	NPC149618
0.776	Intermediate Similarity	NPC105591
0.7759	Intermediate Similarity	NPC34482
0.7759	Intermediate Similarity	NPC478019
0.7754	Intermediate Similarity	NPC203751
0.7754	Intermediate Similarity	NPC470333
0.7754	Intermediate Similarity	NPC229051
0.7754	Intermediate Similarity	NPC131862
0.7753	Intermediate Similarity	NPC273483
0.7753	Intermediate Similarity	NPC87708
0.7753	Intermediate Similarity	NPC477690
0.7753	Intermediate Similarity	NPC217447
0.7747	Intermediate Similarity	NPC24761
0.7747	Intermediate Similarity	NPC137232
0.7746	Intermediate Similarity	NPC53016
0.7742	Intermediate Similarity	NPC477571
0.7742	Intermediate Similarity	NPC298778
0.7742	Intermediate Similarity	NPC477573
0.7742	Intermediate Similarity	NPC313304
0.7742	Intermediate Similarity	NPC474004
0.7742	Intermediate Similarity	NPC477572
0.774	Intermediate Similarity	NPC474660
0.774	Intermediate Similarity	NPC477914
0.774	Intermediate Similarity	NPC473466
0.7737	Intermediate Similarity	NPC477860
0.7737	Intermediate Similarity	NPC475161
0.7737	Intermediate Similarity	NPC265795
0.7737	Intermediate Similarity	NPC208069
0.7735	Intermediate Similarity	NPC470339
0.7735	Intermediate Similarity	NPC51760
0.7735	Intermediate Similarity	NPC195167
0.7732	Intermediate Similarity	NPC471806
0.7732	Intermediate Similarity	NPC471807
0.7732	Intermediate Similarity	NPC471810
0.773	Intermediate Similarity	NPC107009
0.7727	Intermediate Similarity	NPC153417
0.7725	Intermediate Similarity	NPC28160

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 NPC316091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	1052
0.2-0.3	1913
0.3-0.4	2685
0.4-0.5	1937
0.5-0.6	827
0.6-0.7	277
0.7-0.8	69
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
0.7944	Intermediate Similarity	NPD6959	Discontinued
0.7901	Intermediate Similarity	NPD6232	Discontinued
0.7886	Intermediate Similarity	NPD3226	Approved
0.7869	Intermediate Similarity	NPD7473	Discontinued
0.7717	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7411	Suspended
0.7611	Intermediate Similarity	NPD7819	Suspended
0.7577	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD2532	Approved
0.7557	Intermediate Similarity	NPD2533	Approved
0.7557	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD5844	Phase 1
0.7471	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7768	Phase 2
0.7401	Intermediate Similarity	NPD7390	Discontinued
0.7399	Intermediate Similarity	NPD5405	Approved
0.7399	Intermediate Similarity	NPD5408	Approved
0.7399	Intermediate Similarity	NPD5406	Approved
0.7399	Intermediate Similarity	NPD5404	Approved
0.7396	Intermediate Similarity	NPD8313	Approved
0.7396	Intermediate Similarity	NPD8312	Approved
0.7348	Intermediate Similarity	NPD4380	Phase 2
0.7337	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2935	Discontinued
0.7297	Intermediate Similarity	NPD3749	Approved
0.7297	Intermediate Similarity	NPD7075	Discontinued
0.7293	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8151	Discontinued
0.7263	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD2346	Discontinued
0.7249	Intermediate Similarity	NPD2403	Approved
0.7241	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7003	Approved
0.7228	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7435	Discontinued
0.7202	Intermediate Similarity	NPD6559	Discontinued
0.7167	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4363	Phase 3
0.715	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD6782	Approved
0.7143	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD6779	Approved
0.7143	Intermediate Similarity	NPD6778	Approved
0.7143	Intermediate Similarity	NPD6781	Approved
0.7143	Intermediate Similarity	NPD6777	Approved
0.7135	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8150	Discontinued
0.7087	Intermediate Similarity	NPD7871	Phase 2
0.7087	Intermediate Similarity	NPD7870	Phase 2
0.7083	Intermediate Similarity	NPD7177	Discontinued
0.7081	Intermediate Similarity	NPD6801	Discontinued
0.7072	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6166	Phase 2
0.7068	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5710	Approved
0.7053	Intermediate Similarity	NPD5711	Approved
0.7045	Intermediate Similarity	NPD1510	Phase 2
0.7039	Intermediate Similarity	NPD7696	Phase 3
0.7039	Intermediate Similarity	NPD7698	Approved
0.7039	Intermediate Similarity	NPD3750	Approved
0.7039	Intermediate Similarity	NPD7697	Approved
0.7029	Intermediate Similarity	NPD1607	Approved
0.7022	Intermediate Similarity	NPD1549	Phase 2
0.7021	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7458	Discontinued
0.7	Intermediate Similarity	NPD7874	Approved
0.7	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1934	Approved
0.6973	Remote Similarity	NPD6599	Discontinued
0.6966	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD1465	Phase 2
0.6949	Remote Similarity	NPD2799	Discontinued
0.6947	Remote Similarity	NPD5494	Approved
0.6944	Remote Similarity	NPD4628	Phase 3
0.6915	Remote Similarity	NPD5402	Approved
0.6915	Remote Similarity	NPD3817	Phase 2
0.6914	Remote Similarity	NPD1240	Approved
0.691	Remote Similarity	NPD2796	Approved
0.6907	Remote Similarity	NPD3818	Discontinued
0.6906	Remote Similarity	NPD3887	Approved
0.6905	Remote Similarity	NPD7701	Phase 2
0.6897	Remote Similarity	NPD6534	Approved
0.6897	Remote Similarity	NPD6535	Approved
0.6888	Remote Similarity	NPD5953	Discontinued
0.6887	Remote Similarity	NPD7783	Phase 2
0.6887	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1578	Phase 2
0.6872	Remote Similarity	NPD2344	Approved
0.6872	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4361	Phase 2
0.6863	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD2801	Approved
0.6848	Remote Similarity	NPD6273	Approved
0.6845	Remote Similarity	NPD8285	Discontinued
0.6842	Remote Similarity	NPD8319	Approved
0.6842	Remote Similarity	NPD8320	Phase 1
0.6837	Remote Similarity	NPD7074	Phase 3
0.6831	Remote Similarity	NPD6799	Approved
0.6831	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7041	Phase 2
0.6827	Remote Similarity	NPD6823	Phase 2
0.6818	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD1551	Phase 2
0.6813	Remote Similarity	NPD2354	Approved
0.6811	Remote Similarity	NPD920	Approved
0.6809	Remote Similarity	NPD37	Approved
0.6808	Remote Similarity	NPD7801	Approved
0.6806	Remote Similarity	NPD6234	Discontinued
0.6802	Remote Similarity	NPD1470	Approved
0.68	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3764	Approved
0.68	Remote Similarity	NPD2313	Discontinued
0.6796	Remote Similarity	NPD7700	Phase 2
0.6796	Remote Similarity	NPD7699	Phase 2
0.6789	Remote Similarity	NPD4967	Phase 2
0.6789	Remote Similarity	NPD4965	Approved
0.6789	Remote Similarity	NPD3882	Suspended
0.6789	Remote Similarity	NPD4966	Approved
0.6788	Remote Similarity	NPD7229	Phase 3
0.6786	Remote Similarity	NPD7054	Approved
0.6766	Remote Similarity	NPD8434	Phase 2
0.6765	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6213	Phase 3
0.6765	Remote Similarity	NPD6212	Phase 3
0.676	Remote Similarity	NPD3748	Approved
0.6758	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD958	Approved
0.6751	Remote Similarity	NPD7472	Approved
0.6739	Remote Similarity	NPD1511	Approved
0.6737	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3751	Discontinued
0.6721	Remote Similarity	NPD2309	Approved
0.672	Remote Similarity	NPD5403	Approved
0.6717	Remote Similarity	NPD6797	Phase 2
0.6716	Remote Similarity	NPD6785	Approved
0.6716	Remote Similarity	NPD6784	Approved
0.6703	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1243	Approved
0.6703	Remote Similarity	NPD2800	Approved
0.6701	Remote Similarity	NPD7286	Phase 2
0.6685	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2353	Approved
0.6685	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8455	Phase 2
0.6684	Remote Similarity	NPD957	Approved
0.6683	Remote Similarity	NPD7251	Discontinued
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1512	Approved
0.665	Remote Similarity	NPD7808	Phase 3
0.665	Remote Similarity	NPD7228	Approved
0.6647	Remote Similarity	NPD1283	Approved
0.6631	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2438	Suspended
0.6629	Remote Similarity	NPD454	Approved
0.6629	Remote Similarity	NPD2979	Phase 3
0.6615	Remote Similarity	NPD3787	Discontinued
0.6615	Remote Similarity	NPD6808	Phase 2
0.6613	Remote Similarity	NPD5401	Approved
0.6611	Remote Similarity	NPD4538	Approved
0.6611	Remote Similarity	NPD4536	Approved
0.6611	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3268	Approved
0.6595	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1471	Phase 3
0.6591	Remote Similarity	NPD6832	Phase 2
0.6587	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3926	Phase 2
0.6578	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.657	Remote Similarity	NPD1201	Approved
0.6564	Remote Similarity	NPD1247	Approved
0.6559	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4534	Discontinued
0.6556	Remote Similarity	NPD6651	Approved
0.6548	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD919	Approved
0.6538	Remote Similarity	NPD6099	Approved
0.6538	Remote Similarity	NPD6100	Approved
0.6537	Remote Similarity	NPD4287	Approved
0.6517	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD1203	Approved
0.6505	Remote Similarity	NPD5058	Phase 3
0.65	Remote Similarity	NPD1184	Approved
0.65	Remote Similarity	NPD230	Phase 1

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