NPASS Compound

Structure

CID242364 OpenBabel06191716042D 43 45 0 0 1 0 0 0 0 0999 V2000 -16.3917 6.8745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.2872 5.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.3737 5.4733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.5646 6.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6511 5.6543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8421 6.2421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5155 -1.6309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7065 -1.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9285 5.8354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4291 -1.2242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7930 -1.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1195 6.4232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2381 -1.8120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9840 -0.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2060 6.0164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1517 -1.4052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0704 -1.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3970 6.6042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2562 -0.4107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5129 4.7030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4177 1.6716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7208 3.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2098 2.6497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3479 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2614 -0.6810 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.4834 6.1975 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4472 0.1771 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3789 5.2030 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5517 1.1716 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7153 3.6203 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2153 2.7543 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3659 0.3135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6744 6.7853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5336 -0.2297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 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 -9.1220 4.5338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8085 1.8407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 27 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 23 1 0 0 0 0 21 32 1 0 0 0 0 22 24 1 0 0 0 0 22 33 1 0 0 0 0 25 27 1 0 0 0 0 25 28 2 0 0 0 0 26 28 1 0 0 0 0 26 29 1 0 0 0 0 27 41 1 0 0 0 0 28 36 1 0 0 0 0 29 37 1 0 0 0 0 30 38 1 1 0 0 0 31 39 1 6 0 0 0 32 30 1 6 0 0 0 32 42 1 0 0 0 0 33 31 1 6 0 0 0 33 43 1 0 0 0 0 34 23 1 1 0 0 0 34 35 1 0 0 0 0 34 42 1 0 0 0 0 35 24 1 1 0 0 0 35 43 1 0 0 0 0 36 40 2 0 0 0 0 36 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.47
Volume:	661.801
LogP:	8.654
LogD:	4.877
LogS:	-4.922
# Rotatable Bonds:	24
TPSA:	112.52
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.088
Synthetic Accessibility Score:	4.651
Fsp3:	0.889
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:	-5.056
MDCK Permeability:	9.874561328615528e-06
Pgp-inhibitor:	0.046
Pgp-substrate:	0.925
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.842

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	96.3199691772461%
Volume Distribution (VD):	1.659
Pgp-substrate:	3.0170369148254395%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.475
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.136
CYP3A4-substrate:	0.025

ADMET: Excretion

Clearance (CL):	6.862
Half-life (T1/2):	0.048

ADMET: Toxicity

hERG Blockers:	0.332
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.561
Skin Sensitization:	0.981
Carcinogencity:	0.065
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC242364

Natural Product ID:	NPC242364
*Common Name:**	Bullatacin
IUPAC Name:	4-[(12R)-2,12-dihydroxy-12-[(2S,5S)-5-[(2S,5S)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]dodecyl]-2-methyl-2H-furan-5-one
Synonyms:	Bullatacin; Rolliniastatin 2
Standard InCHIKey:	PJQMINRIJUCTIZ-FKONRUPGSA-N
Standard InCHI:	InChI=1S/C36H64O7/c1-3-4-5-6-7-10-13-16-19-30(38)32-21-23-34(42-32)35-24-22-33(43-35)31(39)20-17-14-11-8-9-12-15-18-29(37)26-28-25-27(2)41-36(28)40/h25,27,29-35,37-39H,3-24,26H2,1-2H3/t27?,29?,30-,31-,32+,33+,34+,35+/m1/s1
SMILES:	CCCCCCCCCC[C@H]([C@@H]1CC[C@@H]([C@@H]2CC[C@@H]([C@@H](CCCCCCCCCC(CC3=CC(C)OC3=O)O)O)O2)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1159657
PubChem CID:	46905041
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50053a043]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473425]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975482]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[17401878]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO26659	Annona bullata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778448]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7494150]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673926]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673935]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673936]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277309]
NPO26659	Annona bullata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350089]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[8946744]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8991944]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[9584396]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26659	Annona bullata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26659	Annona bullata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26659	Annona bullata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26234	Annona muricata	Species	Annonaceae	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
ED50	34
IC50	66
Others	117

Activity Type	# Activity
Cell Line	151
Individual Protein	1
NON-MOLECULAR	22
Organism	32
Others	8
Protein Complex	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	IC50	=	1080.0	ug.mL-1	PMID[476445]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	17.1	ug ml-1	PMID[476446]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	8.4	ug ml-1	PMID[476446]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	14.3	ug ml-1	PMID[476446]
NPT307	Cell Line	HOS	Homo sapiens	ED50	=	11.9	ug ml-1	PMID[476446]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	=	14.9	ug ml-1	PMID[476446]
NPT308	Cell Line	CAKI-1	Homo sapiens	ED50	=	16.8	ug ml-1	PMID[476446]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	13.3	ug ml-1	PMID[476446]
NPT309	Cell Line	1A9	Homo sapiens	Inhibition	=	55.0	%	PMID[476446]
NPT310	Cell Line	1A9/ptx-10	Homo sapiens	ED50	=	8.0	ug ml-1	PMID[476446]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	10.0	ug ml-1	PMID[476446]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	16.1	ug ml-1	PMID[476446]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.4	nM	PMID[476449]
NPT116	Cell Line	HL-60	Homo sapiens	IG	=	73.0	%	PMID[476450]
NPT116	Cell Line	HL-60	Homo sapiens	IG	=	7.0	%	PMID[476450]
NPT116	Cell Line	HL-60	Homo sapiens	IG	=	0.0	%	PMID[476450]
NPT111	Cell Line	K562	Homo sapiens	IG	=	53.0	%	PMID[476450]
NPT111	Cell Line	K562	Homo sapiens	IG	=	39.0	%	PMID[476450]
NPT111	Cell Line	K562	Homo sapiens	IG	=	27.0	%	PMID[476450]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	8.99	10'-12 ug/ml	PMID[476452]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[476452]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	<	1.0	10'-12 ug/ml	PMID[476452]
NPT137	Cell Line	L1210	Mus musculus	T/C	=	138.0	%	PMID[476454]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[476455]
NPT376	Cell Line	A498	Homo sapiens	ED50	=	4.85	10'-5 ug/ml	PMID[476455]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	0.000000001	ug ml-1	PMID[476455]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	=	0.000000001	ug ml-1	PMID[476455]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.0	10'-12 ug/ml	PMID[476456]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	<	1.0	10'-12 ug/ml	PMID[476456]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.25	10'-13 ug/ml	PMID[476456]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	2.44	10'-6 ug/ml	PMID[476455]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	6.96	10'-1 ug/ml	PMID[476455]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	1.4	nM	PMID[476457]
NPT137	Cell Line	L1210	Mus musculus	IZ	=	550.0	Zone units	PMID[476457]
NPT137	Cell Line	L1210	Mus musculus	IZ	=	200.0	Zone units	PMID[476457]
NPT137	Cell Line	L1210	Mus musculus	IZ	=	250.0	Zone units	PMID[476457]
NPT137	Cell Line	L1210	Mus musculus	IZ	=	150.0	Zone units	PMID[476457]
NPT730	Cell Line	MC-38	Mus musculus	IZ	=	1000.0	Zone units	PMID[476457]
NPT730	Cell Line	MC-38	Mus musculus	IZ	=	850.0	Zone units	PMID[476457]
NPT730	Cell Line	MC-38	Mus musculus	IZ	=	800.0	Zone units	PMID[476457]
NPT730	Cell Line	MC-38	Mus musculus	IZ	=	650.0	Zone units	PMID[476457]
NPT393	Cell Line	HCT-116	Homo sapiens	IZ	=	650.0	Zone units	PMID[476457]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IZ	=	100.0	Zone units	PMID[476457]
NPT168	Cell Line	P388	Mus musculus	ED50	<	1.0	10'-5 ug/ml	PMID[476458]
NPT81	Cell Line	A549	Homo sapiens	ED50	<	1.0	10'-5 ug/ml	PMID[476459]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.0	10'-3 ug/ml	PMID[476458]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.29	ug ml-1	PMID[476458]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	<	1.0	10'-3 ug/ml	PMID[476459]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	6.4	10'-1 ug/ml	PMID[476458]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	<	1.0	10'-5 ug/ml	PMID[476459]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.25	10'-13 ug/ml	PMID[476460]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.0	10'-12 ug/ml	PMID[476460]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	1.41	ug.mL-1	PMID[476460]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	0.000926	ug.mL-1	PMID[476460]
NPT111	Cell Line	K562	Homo sapiens	IC50	<	0.000926	ug.mL-1	PMID[476460]
NPT168	Cell Line	P388	Mus musculus	IC50	<	0.000926	ug.mL-1	PMID[476460]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	0.0000894	ug.mL-1	PMID[476460]
NPT168	Cell Line	P388	Mus musculus	IC50	>	0.0924	ug.mL-1	PMID[476460]
NPT455	Cell Line	NCI-H522	Homo sapiens	IC50	=	2.46	ug.mL-1	PMID[476460]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	0.0000287	ug.mL-1	PMID[476460]
NPT394	Cell Line	EKVX	Homo sapiens	IC50	=	0.000115	ug.mL-1	PMID[476460]
NPT379	Cell Line	HOP-62	Homo sapiens	IC50	<	0.000926	ug.mL-1	PMID[476460]
NPT1506	Cell Line	SK-MES-1	Homo sapiens	IC50	>	0.0924	ug.mL-1	PMID[476460]
NPT2198	Cell Line	NCI-H524	Homo sapiens	IC50	=	2.69	ug.mL-1	PMID[476460]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	0.00564	ug.mL-1	PMID[476460]
NPT1396	Cell Line	NCI-H69	Homo sapiens	IC50	=	2.44	ug.mL-1	PMID[476460]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	0.000915	ug.mL-1	PMID[476460]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	2.76	ug.mL-1	PMID[476460]
NPT391	Cell Line	HCC 2998	Homo sapiens	IC50	=	4.05	ug.mL-1	PMID[476460]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	0.0924	ug.mL-1	PMID[476460]
NPT672	Cell Line	TE-671	Homo sapiens	IC50	=	0.0000256	ug.mL-1	PMID[476460]
NPT380	Cell Line	U-251	Homo sapiens	IC50	<	0.00000924	ug.mL-1	PMID[476460]
NPT383	Cell Line	SNB-19	Homo sapiens	IC50	>	926.0	nM	PMID[476460]
NPT392	Cell Line	SNB-75	Homo sapiens	IC50	=	3.35	ug.mL-1	PMID[476460]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	IC50	<	0.000926	ug.mL-1	PMID[476460]
NPT1091	Cell Line	RPMI-7951	Homo sapiens	IC50	=	2.73	ug.mL-1	PMID[476460]
NPT375	Cell Line	Malme-3M	Homo sapiens	IC50	=	2.82	ug.mL-1	PMID[476460]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	<	3.25	ug.mL-1	PMID[476460]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	0.0000377	ug.mL-1	PMID[476460]
NPT381	Cell Line	OVCAR-8	Homo sapiens	IC50	=	2.57	ug.mL-1	PMID[476460]
NPT382	Cell Line	OVCAR-5	Homo sapiens	IC50	=	8.8	ug.mL-1	PMID[476460]
NPT456	Cell Line	OVCAR-4	Homo sapiens	IC50	>	0.0924	ug.mL-1	PMID[476460]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	>	0.0924	ug.mL-1	PMID[476460]
NPT376	Cell Line	A498	Homo sapiens	IC50	=	0.0000424	ug.mL-1	PMID[476460]
NPT2280	Cell Line	A704	Homo sapiens	IC50	=	1.36	ug.mL-1	PMID[476460]
NPT738	Cell Line	SN12K1	Homo sapiens	IC50	=	0.0000224	ug.mL-1	PMID[476460]
NPT371	Cell Line	UO-31	Homo sapiens	IC50	=	1.9	ug.mL-1	PMID[476460]
NPT308	Cell Line	CAKI-1	Homo sapiens	IC50	=	0.00394	ug.mL-1	PMID[476460]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.000504	ug.mL-1	PMID[476460]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	0.00384	ug.mL-1	PMID[476460]
NPT308	Cell Line	CAKI-1	Homo sapiens	IC90	>	0.0924	ug.mL-1	PMID[476460]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC90	=	4.72	ug.mL-1	PMID[476460]
NPT111	Cell Line	K562	Homo sapiens	IC90	=	4.5	ug.mL-1	PMID[476460]
NPT168	Cell Line	P388	Mus musculus	IC90	=	2.56	ug.mL-1	PMID[476460]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC90	=	0.0694	ug.mL-1	PMID[476460]
NPT168	Cell Line	P388	Mus musculus	IC90	>	0.0924	ug.mL-1	PMID[476460]
NPT455	Cell Line	NCI-H522	Homo sapiens	IC90	>	9.24	ug.mL-1	PMID[476460]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC90	=	0.000185	ug.mL-1	PMID[476460]
NPT394	Cell Line	EKVX	Homo sapiens	IC90	>	0.0926	ug.mL-1	PMID[476460]
NPT379	Cell Line	HOP-62	Homo sapiens	IC90	=	5.13	ug.mL-1	PMID[476460]
NPT1506	Cell Line	SK-MES-1	Homo sapiens	IC90	>	0.0924	ug.mL-1	PMID[476460]
NPT2198	Cell Line	NCI-H524	Homo sapiens	IC90	=	7.54	ug.mL-1	PMID[476460]
NPT1396	Cell Line	NCI-H69	Homo sapiens	IC90	=	7.52	ug.mL-1	PMID[476460]
NPT323	Cell Line	SW-620	Homo sapiens	IC90	=	5.66	ug.mL-1	PMID[476460]
NPT114	Cell Line	LoVo	Homo sapiens	IC90	=	4.69	ug.mL-1	PMID[476460]
NPT579	Cell Line	DLD-1	Homo sapiens	IC90	=	8.62	ug.mL-1	PMID[476460]
NPT391	Cell Line	HCC 2998	Homo sapiens	IC90	>	9.26	ug.mL-1	PMID[476460]
NPT83	Cell Line	MCF7	Homo sapiens	IC90	>	0.0924	ug.mL-1	PMID[476460]
NPT383	Cell Line	SNB-19	Homo sapiens	IC90	>	0.926	ug.mL-1	PMID[476460]
NPT380	Cell Line	U-251	Homo sapiens	IC90	=	0.0000437	ug.mL-1	PMID[476460]
NPT672	Cell Line	TE-671	Homo sapiens	IC90	=	0.00274	ug.mL-1	PMID[476460]
NPT392	Cell Line	SNB-75	Homo sapiens	IC90	>	9.26	ug.mL-1	PMID[476460]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	IC90	=	5.22	ug.mL-1	PMID[476460]
NPT1091	Cell Line	RPMI-7951	Homo sapiens	IC90	=	7.71	ug.mL-1	PMID[476460]
NPT375	Cell Line	Malme-3M	Homo sapiens	IC90	=	7.67	ug.mL-1	PMID[476460]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC90	=	8.64	ug.mL-1	PMID[476460]
NPT179	Cell Line	A2780	Homo sapiens	IC90	=	0.00065	ug.mL-1	PMID[476460]
NPT381	Cell Line	OVCAR-8	Homo sapiens	IC90	=	7.65	ug.mL-1	PMID[476460]
NPT382	Cell Line	OVCAR-5	Homo sapiens	IC90	>	9.26	ug.mL-1	PMID[476460]
NPT456	Cell Line	OVCAR-4	Homo sapiens	IC90	>	0.0924	ug.mL-1	PMID[476460]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC90	>	0.0924	ug.mL-1	PMID[476460]
NPT376	Cell Line	A498	Homo sapiens	IC90	=	0.00371	ug.mL-1	PMID[476460]
NPT2280	Cell Line	A704	Homo sapiens	IC90	=	8.0	ug.mL-1	PMID[476460]
NPT738	Cell Line	SN12K1	Homo sapiens	IC90	=	0.000287	ug.mL-1	PMID[476460]
NPT371	Cell Line	UO-31	Homo sapiens	IC90	>	9.26	ug.mL-1	PMID[476460]
NPT137	Cell Line	L1210	Mus musculus	T/C	=	138.0	%	PMID[476461]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	46.0	%	PMID[476461]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	98.0	%	PMID[476461]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	36.0	%	PMID[476461]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	75.0	%	PMID[476461]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	24.0	%	PMID[476461]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	74.0	%	PMID[476461]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	<	1.0	10'-13 ug/ml	PMID[476461]
NPT179	Cell Line	A2780	Homo sapiens	TGI	=	67.0	%	PMID[476461]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	125.0	%	PMID[476461]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	69.0	%	PMID[476461]
NPT168	Cell Line	P388	Mus musculus	IC50	>	0.0924	ug.mL-1	PMID[476461]
NPT168	Cell Line	P388	Mus musculus	IC50	>	0.000926	ug.mL-1	PMID[476461]
NPT5400	Cell Line	X5563	Mus musculus	TGI	=	66.0	%	PMID[476461]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.033	ug.mL-1	PMID[476462]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	0.034	ug.mL-1	PMID[476462]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.043	ug.mL-1	PMID[476462]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.032	ug.mL-1	PMID[476462]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	0.0048	ug.mL-1	PMID[476462]
NPT1097	Cell Line	MKN-45	Homo sapiens	IC50	=	0.053	ug.mL-1	PMID[476462]
NPT1317	Cell Line	CCRF S-180	Mus musculus	GI	=	65.8	%	PMID[476463]
NPT4515	Individual Protein	NADH-ubiquinone oxidoreductase chain 1	Bos taurus	IC50	=	0.8	nM	PMID[476464]
NPT137	Cell Line	L1210	Mus musculus	Ratio IC50	=	0.67	n.a.	PMID[476465]
NPT137	Cell Line	L1210	Mus musculus	Ratio IC50	=	21.09	n.a.	PMID[476465]
NPT4849	Cell Line	P815	Mus musculus	IC50	=	3480.0	nM	PMID[476465]
NPT3722	Cell Line	4T1	Mus musculus	IC50	=	110.0	nM	PMID[476465]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	2320.0	nM	PMID[476465]
NPT27	Others	Unspecified		Activity	=	0.97	n.a.	PMID[476445]
NPT27	Others	Unspecified		Bullatacin index	=	1.0	n.a.	PMID[476445]
NPT5098	Protein Complex	Mitochondrial complex I; NADH oxidoreductase	Bos taurus	IC50	=	0.9	nM	PMID[476447]
NPT5098	Protein Complex	Mitochondrial complex I; NADH oxidoreductase	Bos taurus	IC50	=	0.51	nM	PMID[476448]
NPT2	Others	Unspecified		IC50	=	0.61	nM	PMID[476448]
NPT2	Others	Unspecified		Ratio	=	1.2	n.a.	PMID[476448]
NPT5098	Protein Complex	Mitochondrial complex I; NADH oxidoreductase	Bos taurus	Relative potency	=	2.0	n.a.	PMID[476448]
NPT2	Others	Unspecified		Relative potency	=	49.0	n.a.	PMID[476448]
NPT2	Others	Unspecified		IC50	=	0.83	nM	PMID[476451]
NPT140	Organism	Artemia	Artemia	ED50	=	0.002	ug ml-1	PMID[476452]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.3	10'-4 ug/ml	PMID[476453]
NPT3063	Organism	Aphis gossypii	Aphis gossypii	Activity	=	90.0	%	PMID[476454]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	53.0	%	PMID[476454]
NPT3063	Organism	Aphis gossypii	Aphis gossypii	Activity	=	80.0	%	PMID[476454]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	Activity	=	0.0	%	PMID[476454]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	Activity	=	80.0	%	PMID[476454]
NPT3061	Organism	Diabrotica undecimpunctata	Diabrotica undecimpunctata	Activity	=	80.0	%	PMID[476454]
NPT3061	Organism	Diabrotica undecimpunctata	Diabrotica undecimpunctata	Activity	=	20.0	%	PMID[476454]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	20.0	%	PMID[476454]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	30.0	%	PMID[476454]
NPT140	Organism	Artemia	Artemia	LC50	=	0.00159	ppm	PMID[476454]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	8.0	10'-4ppm	PMID[476456]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.00159	ug.mL-1	PMID[476455]
NPT2	Others	Unspecified		IC50	=	2500.0	nM	PMID[476457]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	400.0	Zone units	PMID[476457]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	700.0	Zone units	PMID[476457]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	550.0	Zone units	PMID[476457]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	450.0	Zone units	PMID[476457]
NPT140	Organism	Artemia	Artemia	LC50	=	0.00159	ug.mL-1	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	6.188	10'-14 ug/ml	PMID[476460]
NPT2	Others	Unspecified		Activity	=	7.0	%	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.4	ug.mL-1	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.38	ug.mL-1	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	<	0.000926	ug.mL-1	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.99	ug.mL-1	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.75	ug.mL-1	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.42	ug.mL-1	PMID[476460]
NPT3063	Organism	Aphis gossypii	Aphis gossypii	Activity	=	80.0	%	PMID[476460]
NPT3063	Organism	Aphis gossypii	Aphis gossypii	Activity	=	90.0	%	PMID[476460]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	Activity	=	0.0	%	PMID[476460]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	Activity	=	80.0	%	PMID[476460]
NPT3062	Organism	Spodoptera eridania	Spodoptera eridania	Activity	=	0.0	%	PMID[476460]
NPT5399	Organism	Diabrotica undecimpunctata howardi	Diabrotica undecimpunctata howardi	Activity	=	20.0	%	PMID[476460]
NPT5399	Organism	Diabrotica undecimpunctata howardi	Diabrotica undecimpunctata howardi	Activity	=	80.0	%	PMID[476460]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	20.0	%	PMID[476460]
NPT350	Organism	Tetranychus urticae	Tetranychus urticae	Activity	=	30.0	%	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC90	>	9.26	ug.mL-1	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC90	=	9.21	ug.mL-1	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC90	>	7.14	ug.mL-1	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC90	=	3.76	ug.mL-1	PMID[476460]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	63.4	%	PMID[476463]

☑ 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 NPC242364 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	202
0.1-0.2	1446
0.2-0.3	5840
0.3-0.4	14569
0.4-0.5	10950
0.5-0.6	6593
0.6-0.7	2464
0.7-0.8	441
0.8-0.85	19
0.85-0.9	33
0.9-0.95	72
0.95-1	68

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC133730
1.0	High Similarity	NPC274446
1.0	High Similarity	NPC151403
1.0	High Similarity	NPC100454
1.0	High Similarity	NPC191929
1.0	High Similarity	NPC287164
1.0	High Similarity	NPC171135
1.0	High Similarity	NPC261952
1.0	High Similarity	NPC169511
1.0	High Similarity	NPC61257
1.0	High Similarity	NPC172821
1.0	High Similarity	NPC234077
1.0	High Similarity	NPC81045
1.0	High Similarity	NPC39754
1.0	High Similarity	NPC320569
0.988	High Similarity	NPC91067
0.988	High Similarity	NPC40066
0.988	High Similarity	NPC20621
0.988	High Similarity	NPC81778
0.988	High Similarity	NPC93794
0.988	High Similarity	NPC318963
0.988	High Similarity	NPC473504
0.988	High Similarity	NPC42598
0.9762	High Similarity	NPC239517
0.9756	High Similarity	NPC114694
0.9756	High Similarity	NPC142117
0.9756	High Similarity	NPC231096
0.9756	High Similarity	NPC475581
0.9756	High Similarity	NPC232555
0.9756	High Similarity	NPC241360
0.9756	High Similarity	NPC171174
0.9756	High Similarity	NPC107717
0.9756	High Similarity	NPC132940
0.9756	High Similarity	NPC62118
0.9756	High Similarity	NPC293136
0.9756	High Similarity	NPC240695
0.9639	High Similarity	NPC476583
0.9639	High Similarity	NPC20533
0.9639	High Similarity	NPC258068
0.9634	High Similarity	NPC283085
0.9634	High Similarity	NPC66346
0.9634	High Similarity	NPC103284
0.9634	High Similarity	NPC132496
0.9634	High Similarity	NPC1083
0.9634	High Similarity	NPC231009
0.9634	High Similarity	NPC39167
0.9634	High Similarity	NPC470400
0.9634	High Similarity	NPC25764
0.9634	High Similarity	NPC475268
0.9634	High Similarity	NPC473671
0.9634	High Similarity	NPC319036
0.9634	High Similarity	NPC235809
0.9634	High Similarity	NPC82795
0.9634	High Similarity	NPC473651
0.9634	High Similarity	NPC286338
0.9634	High Similarity	NPC223871
0.9634	High Similarity	NPC9678
0.9634	High Similarity	NPC473478
0.9634	High Similarity	NPC202055
0.9634	High Similarity	NPC107986
0.9634	High Similarity	NPC473156
0.9634	High Similarity	NPC77871
0.9634	High Similarity	NPC39279
0.9634	High Similarity	NPC110710
0.9634	High Similarity	NPC473669
0.9634	High Similarity	NPC292809
0.9524	High Similarity	NPC473905
0.9524	High Similarity	NPC233551
0.9524	High Similarity	NPC48338
0.9524	High Similarity	NPC320458
0.9524	High Similarity	NPC40376
0.9524	High Similarity	NPC21208
0.9524	High Similarity	NPC20339
0.9524	High Similarity	NPC280621
0.9518	High Similarity	NPC134807
0.9518	High Similarity	NPC204686
0.9518	High Similarity	NPC282815
0.9518	High Similarity	NPC279267
0.9518	High Similarity	NPC103523
0.9518	High Similarity	NPC219498
0.9518	High Similarity	NPC473840
0.9518	High Similarity	NPC134865
0.9518	High Similarity	NPC134885
0.9518	High Similarity	NPC473687
0.9518	High Similarity	NPC69082
0.9518	High Similarity	NPC219652
0.9518	High Similarity	NPC308412
0.9518	High Similarity	NPC25703
0.9518	High Similarity	NPC210218
0.9512	High Similarity	NPC156804
0.9412	High Similarity	NPC477011
0.9405	High Similarity	NPC470401
0.9405	High Similarity	NPC159750
0.9405	High Similarity	NPC154097
0.9405	High Similarity	NPC473995
0.9405	High Similarity	NPC473649
0.9405	High Similarity	NPC178215
0.9398	High Similarity	NPC329838
0.9398	High Similarity	NPC329615
0.9398	High Similarity	NPC120398
0.9398	High Similarity	NPC471567
0.9398	High Similarity	NPC322529
0.9302	High Similarity	NPC473904
0.9286	High Similarity	NPC47937
0.9286	High Similarity	NPC112685
0.9277	High Similarity	NPC163093
0.9268	High Similarity	NPC11332
0.9268	High Similarity	NPC473712
0.9268	High Similarity	NPC473529
0.9268	High Similarity	NPC145914
0.9268	High Similarity	NPC131002
0.9268	High Similarity	NPC73310
0.9268	High Similarity	NPC65930
0.9268	High Similarity	NPC180363
0.9268	High Similarity	NPC475159
0.9268	High Similarity	NPC329829
0.9268	High Similarity	NPC473780
0.9268	High Similarity	NPC94875
0.9186	High Similarity	NPC139418
0.9186	High Similarity	NPC14901
0.9186	High Similarity	NPC130359
0.9167	High Similarity	NPC182383
0.9167	High Similarity	NPC477014
0.9167	High Similarity	NPC477018
0.9167	High Similarity	NPC100921
0.9167	High Similarity	NPC477013
0.9157	High Similarity	NPC253801
0.9157	High Similarity	NPC144415
0.9091	High Similarity	NPC473723
0.9091	High Similarity	NPC473520
0.9091	High Similarity	NPC473663
0.9091	High Similarity	NPC475173
0.9091	High Similarity	NPC473561
0.907	High Similarity	NPC89001
0.9059	High Similarity	NPC309211
0.9059	High Similarity	NPC477010
0.9059	High Similarity	NPC477015
0.8977	High Similarity	NPC473707
0.8966	High Similarity	NPC280612
0.8966	High Similarity	NPC477016
0.8966	High Similarity	NPC477017
0.8876	High Similarity	NPC11456
0.8736	High Similarity	NPC477012
0.8462	Intermediate Similarity	NPC81419
0.8462	Intermediate Similarity	NPC179746
0.8352	Intermediate Similarity	NPC30515
0.8352	Intermediate Similarity	NPC208886
0.8352	Intermediate Similarity	NPC12172
0.8242	Intermediate Similarity	NPC51004
0.8242	Intermediate Similarity	NPC473619
0.8211	Intermediate Similarity	NPC187268
0.8152	Intermediate Similarity	NPC473321
0.8152	Intermediate Similarity	NPC184463
0.8144	Intermediate Similarity	NPC86077
0.8132	Intermediate Similarity	NPC295312
0.8132	Intermediate Similarity	NPC307411
0.809	Intermediate Similarity	NPC21469
0.8085	Intermediate Similarity	NPC36954
0.8065	Intermediate Similarity	NPC475912
0.8065	Intermediate Similarity	NPC288240
0.8065	Intermediate Similarity	NPC476300
0.8065	Intermediate Similarity	NPC162205
0.8065	Intermediate Similarity	NPC295204
0.8065	Intermediate Similarity	NPC273579
0.8043	Intermediate Similarity	NPC476004
0.8043	Intermediate Similarity	NPC474761
0.8022	Intermediate Similarity	NPC202672
0.8022	Intermediate Similarity	NPC58219
0.8022	Intermediate Similarity	NPC177629
0.8021	Intermediate Similarity	NPC473326
0.8	Intermediate Similarity	NPC475711
0.7979	Intermediate Similarity	NPC474035
0.7979	Intermediate Similarity	NPC81386
0.7935	Intermediate Similarity	NPC474032
0.7935	Intermediate Similarity	NPC92974
0.7912	Intermediate Similarity	NPC160138
0.7912	Intermediate Similarity	NPC186148
0.7895	Intermediate Similarity	NPC14961
0.7895	Intermediate Similarity	NPC270013
0.7872	Intermediate Similarity	NPC212486
0.7865	Intermediate Similarity	NPC229799
0.7865	Intermediate Similarity	NPC286770
0.7865	Intermediate Similarity	NPC284472
0.7849	Intermediate Similarity	NPC473448
0.7831	Intermediate Similarity	NPC84038
0.7826	Intermediate Similarity	NPC473715
0.7816	Intermediate Similarity	NPC470148
0.7816	Intermediate Similarity	NPC470149
0.7812	Intermediate Similarity	NPC476315
0.7812	Intermediate Similarity	NPC477921
0.7812	Intermediate Similarity	NPC279621
0.7802	Intermediate Similarity	NPC284902
0.7802	Intermediate Similarity	NPC469483
0.7789	Intermediate Similarity	NPC474338
0.7778	Intermediate Similarity	NPC41856
0.7778	Intermediate Similarity	NPC474251
0.7766	Intermediate Similarity	NPC327760
0.7753	Intermediate Similarity	NPC475046
0.7753	Intermediate Similarity	NPC11383
0.7753	Intermediate Similarity	NPC310450

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 NPC242364 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	2220
0.2-0.3	3919
0.3-0.4	2007
0.4-0.5	586
0.5-0.6	194
0.6-0.7	40
0.7-0.8	2
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
0.7849	Intermediate Similarity	NPD46	Approved
0.7849	Intermediate Similarity	NPD6698	Approved
0.7647	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7838	Discovery
0.7216	Intermediate Similarity	NPD7983	Approved
0.7129	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6371	Approved
0.7075	Intermediate Similarity	NPD6686	Approved
0.6947	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4251	Approved
0.6804	Remote Similarity	NPD4250	Approved
0.6768	Remote Similarity	NPD5785	Approved
0.6701	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD1695	Approved
0.6635	Remote Similarity	NPD4225	Approved
0.6598	Remote Similarity	NPD5363	Approved
0.6598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3197	Phase 1
0.6562	Remote Similarity	NPD7154	Phase 3
0.6562	Remote Similarity	NPD5362	Discontinued
0.6509	Remote Similarity	NPD5344	Discontinued
0.6452	Remote Similarity	NPD4756	Discovery
0.6421	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6053	Discontinued
0.6364	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD8513	Phase 3
0.6356	Remote Similarity	NPD8515	Approved
0.6356	Remote Similarity	NPD8517	Approved
0.6356	Remote Similarity	NPD8516	Approved
0.6321	Remote Similarity	NPD7638	Approved
0.6289	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4269	Approved
0.6289	Remote Similarity	NPD4270	Approved
0.6262	Remote Similarity	NPD7639	Approved
0.6262	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4252	Approved
0.625	Remote Similarity	NPD5282	Discontinued
0.6224	Remote Similarity	NPD6110	Phase 1
0.6211	Remote Similarity	NPD4268	Approved
0.6211	Remote Similarity	NPD4271	Approved
0.62	Remote Similarity	NPD5786	Approved
0.6186	Remote Similarity	NPD5369	Approved
0.6186	Remote Similarity	NPD4790	Discontinued
0.6162	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7115	Discovery
0.6154	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD5779	Approved
0.6148	Remote Similarity	NPD7507	Approved
0.6132	Remote Similarity	NPD7839	Suspended
0.6122	Remote Similarity	NPD6435	Approved
0.6116	Remote Similarity	NPD7830	Approved
0.6116	Remote Similarity	NPD7829	Approved
0.6111	Remote Similarity	NPD6648	Approved
0.61	Remote Similarity	NPD1694	Approved
0.6098	Remote Similarity	NPD8074	Phase 3
0.6082	Remote Similarity	NPD4820	Approved
0.6082	Remote Similarity	NPD4822	Approved
0.6082	Remote Similarity	NPD4821	Approved
0.6082	Remote Similarity	NPD4819	Approved
0.6064	Remote Similarity	NPD8039	Approved
0.6061	Remote Similarity	NPD5331	Approved
0.6061	Remote Similarity	NPD5332	Approved
0.6053	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7319	Approved
0.5984	Remote Similarity	NPD7642	Approved
0.5966	Remote Similarity	NPD7641	Discontinued
0.596	Remote Similarity	NPD5209	Approved
0.5955	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8033	Approved
0.5929	Remote Similarity	NPD6412	Phase 2
0.5923	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5368	Approved
0.5909	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD3730	Approved
0.5904	Remote Similarity	NPD3195	Phase 2
0.5904	Remote Similarity	NPD3728	Approved
0.5904	Remote Similarity	NPD4266	Approved
0.5904	Remote Similarity	NPD3194	Approved
0.5904	Remote Similarity	NPD3196	Approved
0.5889	Remote Similarity	NPD3704	Approved
0.5868	Remote Similarity	NPD8377	Approved
0.5868	Remote Similarity	NPD8294	Approved
0.5865	Remote Similarity	NPD5370	Suspended
0.5862	Remote Similarity	NPD2204	Approved
0.5849	Remote Similarity	NPD6399	Phase 3
0.5833	Remote Similarity	NPD7327	Approved
0.5833	Remote Similarity	NPD7328	Approved
0.582	Remote Similarity	NPD8378	Approved
0.582	Remote Similarity	NPD8444	Approved
0.582	Remote Similarity	NPD8335	Approved
0.582	Remote Similarity	NPD8379	Approved
0.582	Remote Similarity	NPD8380	Approved
0.582	Remote Similarity	NPD8296	Approved
0.5814	Remote Similarity	NPD6109	Phase 1
0.5814	Remote Similarity	NPD69	Approved
0.5814	Remote Similarity	NPD9119	Approved
0.5789	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7516	Approved
0.5783	Remote Similarity	NPD3172	Approved
0.5781	Remote Similarity	NPD7260	Phase 2
0.578	Remote Similarity	NPD7902	Approved
0.5776	Remote Similarity	NPD6421	Discontinued
0.5776	Remote Similarity	NPD2067	Discontinued
0.5763	Remote Similarity	NPD4632	Approved
0.576	Remote Similarity	NPD8273	Phase 1
0.576	Remote Similarity	NPD8451	Approved
0.5755	Remote Similarity	NPD7637	Suspended
0.5755	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7500	Approved
0.5736	Remote Similarity	NPD6845	Suspended
0.5732	Remote Similarity	NPD6927	Phase 3
0.5726	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7632	Discontinued
0.5714	Remote Similarity	NPD6101	Approved
0.5714	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6008	Approved
0.5698	Remote Similarity	NPD9118	Approved
0.5691	Remote Similarity	NPD8268	Approved
0.5691	Remote Similarity	NPD8266	Approved
0.5691	Remote Similarity	NPD8267	Approved
0.5691	Remote Similarity	NPD8269	Approved
0.5688	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.568	Remote Similarity	NPD7492	Approved
0.5678	Remote Similarity	NPD8297	Approved
0.5669	Remote Similarity	NPD7736	Approved
0.5648	Remote Similarity	NPD7748	Approved
0.5635	Remote Similarity	NPD6616	Approved
0.563	Remote Similarity	NPD8133	Approved
0.562	Remote Similarity	NPD7505	Discontinued
0.561	Remote Similarity	NPD6054	Approved
0.561	Remote Similarity	NPD6319	Approved
0.5607	Remote Similarity	NPD6411	Approved
0.5603	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.56	Remote Similarity	NPD8328	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