NPASS Compound

Structure

CID242294 OpenBabel06191716042D 23 24 0 0 0 0 0 0 0 0999 V2000 -6.0622 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 1.0000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -1.7321 -0.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 7 1 0 0 0 0 4 12 2 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 17 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.12
Volume:	325.631
LogP:	3.496
LogD:	3.322
LogS:	-5.34
# Rotatable Bonds:	6
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.654
Synthetic Accessibility Score:	2.045
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.814
MDCK Permeability:	1.7667232896201313e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.534
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.633

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	95.2402572631836%
Volume Distribution (VD):	0.502
Pgp-substrate:	2.862855911254883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.917
CYP2C19-substrate:	0.248
CYP2C9-inhibitor:	0.677
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.56
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.4

ADMET: Excretion

Clearance (CL):	10.73
Half-life (T1/2):	0.346

ADMET: Toxicity

hERG Blockers:	0.179
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.877
AMES Toxicity:	0.525
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.338
Skin Sensitization:	0.878
Carcinogencity:	0.61
Eye Corrosion:	0.017
Eye Irritation:	0.98
Respiratory Toxicity:	0.776

Download Data

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

Natural Product: NPC242294

Natural Product ID:	NPC242294
*Common Name:**	Flavokawain A
IUPAC Name:	(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	CGIBCVBDFUTMPT-RMKNXTFCSA-N
Standard InCHI:	InChI=1S/C18H18O5/c1-21-13-7-4-12(5-8-13)6-9-15(19)18-16(20)10-14(22-2)11-17(18)23-3/h4-11,20H,1-3H3/b9-6+
SMILES:	COc1ccc(cc1)/C=C/C(=O)c1c(O)cc(cc1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL243829
PubChem CID:	5355469
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO30669	Gnaphalium affine	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10820110]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11830162]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12809361]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	root	n.a.	n.a.	PMID[25597012]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30669	Gnaphalium affine	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO583	Goniothalamus gardneri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO583	Goniothalamus gardneri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO583	Goniothalamus gardneri	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	1
GI50	8
IC50	10
MIC	1
Others	29

Activity Type	# Activity
Cell Line	19
Individual Protein	7
NON-MOLECULAR	3
Organism	5
Others	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT384	Cell Line	TK-10	Homo sapiens	Activity	=	71.0	%	PMID[551737]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	60.0	%	PMID[551737]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	20500.0	nM	PMID[551738]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	15200.0	nM	PMID[551738]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	45300.0	nM	PMID[551738]
NPT387	Cell Line	M14	Homo sapiens	GI50	=	22500.0	nM	PMID[551738]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	17500.0	nM	PMID[551738]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	30800.0	nM	PMID[551738]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	24100.0	nM	PMID[551738]
NPT886	Cell Line	NIH3T3	Mus musculus	GI50	=	17200.0	nM	PMID[551738]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	5830.0	nM	PMID[551745]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	IC50	=	3000.0	nM	PMID[551745]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-6.03	%	PMID[551747]
NPT1229	Cell Line	Huh-7	Homo sapiens	Survival	=	50.0	%	PMID[551750]
NPT492	Cell Line	Caco-2	Homo sapiens	Survival	=	32.0	%	PMID[551750]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Survival	=	58.0	%	PMID[551750]
NPT393	Cell Line	HCT-116	Homo sapiens	Survival	=	20.0	%	PMID[551750]
NPT306	Cell Line	PC-3	Homo sapiens	Survival	=	43.0	%	PMID[551750]
NPT2378	Cell Line	NCI-H727	Homo sapiens	Survival	=	40.0	%	PMID[551750]
NPT941	Cell Line	HaCaT	Homo sapiens	Survival	=	35.0	%	PMID[551750]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	10600.0	nM	PMID[551751]
NPT3114	Individual Protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	Inhibition	=	90.0	%	PMID[551752]
NPT1612	Individual Protein	MAP kinase-activated protein kinase 5	Homo sapiens	Inhibition	=	91.0	%	PMID[551752]
NPT1433	Individual Protein	Serine/threonine-protein kinase Aurora-B	Homo sapiens	Inhibition	=	84.0	%	PMID[551752]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	79.5	%	PMID[551754]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	25000.0	nM	PMID[551738]
NPT2	Others	Unspecified		IC50	>	20000.0	nM	PMID[551739]
NPT2	Others	Unspecified		IC50	=	11.6	ug.mL-1	PMID[551740]
NPT27	Others	Unspecified		IC50	=	13.8	ug.mL-1	PMID[551740]
NPT1	Others	Radical scavenging activity		Activity	=	0.0	%	PMID[551741]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	456000.0	nM	PMID[551741]
NPT2	Others	Unspecified		Inhibition	=	2.3	%	PMID[551741]
NPT1	Others	Radical scavenging activity		Activity	=	6.3	%	PMID[551741]
NPT1	Others	Radical scavenging activity		Activity	=	40.8	%	PMID[551741]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	50.0	%	PMID[551741]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	78.7	%	PMID[551741]
NPT35	Others	n.a.		Inhibition	=	80.9	%	PMID[551741]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	17200.0	nM	PMID[551742]
NPT2	Others	Unspecified		IC50	=	11000.0	nM	PMID[551743]
NPT27	Others	Unspecified		Activity	<	5.0	%	PMID[551743]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	800000.0	nM	PMID[551744]
NPT2	Others	Unspecified		AbsAC35_uM	n.a.	3.21	uM	PMID[551746]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-9.95	%	PMID[551747]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	pED50	=	5.05	n.a.	PMID[551748]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	ED50	=	9.0	10'-7mol/cm2	PMID[551748]
NPT2	Others	Unspecified		Survival	=	67.0	%	PMID[551750]
NPT2	Others	Unspecified		Imax	=	13.0	%	PMID[551753]
NPT2	Others	Unspecified		Imax	=	19.0	%	PMID[551753]

☑ 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 NPC242294 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	336
0.1-0.2	1675
0.2-0.3	4572
0.3-0.4	11265
0.4-0.5	6395
0.5-0.6	3924
0.6-0.7	5937
0.7-0.8	5369
0.8-0.85	1949
0.85-0.9	870
0.9-0.95	314
0.95-1	91

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC263670
1.0	High Similarity	NPC56031
1.0	High Similarity	NPC188646
1.0	High Similarity	NPC175098
1.0	High Similarity	NPC337373
1.0	High Similarity	NPC139813
1.0	High Similarity	NPC312318
1.0	High Similarity	NPC472365
1.0	High Similarity	NPC192304
0.9922	High Similarity	NPC286336
0.9921	High Similarity	NPC257756
0.9921	High Similarity	NPC212631
0.9921	High Similarity	NPC205468
0.9921	High Similarity	NPC87231
0.9921	High Similarity	NPC129132
0.9844	High Similarity	NPC18877
0.9844	High Similarity	NPC20560
0.9844	High Similarity	NPC159623
0.9844	High Similarity	NPC144051
0.9844	High Similarity	NPC28753
0.9844	High Similarity	NPC294593
0.9844	High Similarity	NPC204960
0.9844	High Similarity	NPC82225
0.9843	High Similarity	NPC64359
0.9843	High Similarity	NPC308037
0.9843	High Similarity	NPC262359
0.9769	High Similarity	NPC168105
0.9769	High Similarity	NPC477242
0.9769	High Similarity	NPC66349
0.9769	High Similarity	NPC472367
0.9769	High Similarity	NPC476333
0.9769	High Similarity	NPC473391
0.9769	High Similarity	NPC98115
0.9769	High Similarity	NPC472364
0.9769	High Similarity	NPC150399
0.9769	High Similarity	NPC249606
0.9769	High Similarity	NPC12165
0.9769	High Similarity	NPC186838
0.9769	High Similarity	NPC41461
0.9769	High Similarity	NPC25287
0.9769	High Similarity	NPC477243
0.9769	High Similarity	NPC1486
0.9769	High Similarity	NPC274109
0.9769	High Similarity	NPC477244
0.9695	High Similarity	NPC472419
0.9695	High Similarity	NPC153979
0.9695	High Similarity	NPC188879
0.9695	High Similarity	NPC317119
0.9692	High Similarity	NPC131039
0.9692	High Similarity	NPC13575
0.9692	High Similarity	NPC156092
0.9688	High Similarity	NPC475008
0.9688	High Similarity	NPC309717
0.9688	High Similarity	NPC186097
0.9688	High Similarity	NPC128348
0.9688	High Similarity	NPC313618
0.9688	High Similarity	NPC66384
0.9688	High Similarity	NPC112192
0.9688	High Similarity	NPC164236
0.9688	High Similarity	NPC189106
0.9688	High Similarity	NPC475009
0.9685	High Similarity	NPC247779
0.9621	High Similarity	NPC21350
0.9621	High Similarity	NPC124269
0.9621	High Similarity	NPC472368
0.9618	High Similarity	NPC240593
0.9618	High Similarity	NPC213603
0.9615	High Similarity	NPC103842
0.9606	High Similarity	NPC211120
0.9549	High Similarity	NPC470211
0.9549	High Similarity	NPC472366
0.9549	High Similarity	NPC477956
0.9545	High Similarity	NPC266597
0.9545	High Similarity	NPC116632
0.9545	High Similarity	NPC303644
0.9545	High Similarity	NPC162680
0.9545	High Similarity	NPC7013
0.9545	High Similarity	NPC209560
0.9545	High Similarity	NPC250266
0.9545	High Similarity	NPC181124
0.9545	High Similarity	NPC294409
0.9538	High Similarity	NPC27643
0.9528	High Similarity	NPC80694
0.9528	High Similarity	NPC186098
0.9478	High Similarity	NPC172250
0.9478	High Similarity	NPC215311
0.9478	High Similarity	NPC213659
0.9478	High Similarity	NPC48624
0.9478	High Similarity	NPC11056
0.9478	High Similarity	NPC259166
0.9478	High Similarity	NPC219917
0.9478	High Similarity	NPC326109
0.9478	High Similarity	NPC204985
0.9478	High Similarity	NPC144118
0.9478	High Similarity	NPC80962
0.9474	High Similarity	NPC471620
0.9474	High Similarity	NPC90665
0.9474	High Similarity	NPC251681
0.9474	High Similarity	NPC279668
0.9474	High Similarity	NPC278323
0.9474	High Similarity	NPC99333
0.9474	High Similarity	NPC309154
0.9474	High Similarity	NPC243528
0.9474	High Similarity	NPC55162
0.9474	High Similarity	NPC12175
0.9474	High Similarity	NPC188947
0.9474	High Similarity	NPC280284
0.947	High Similarity	NPC473887
0.947	High Similarity	NPC231772
0.947	High Similarity	NPC29353
0.947	High Similarity	NPC124784
0.947	High Similarity	NPC127447
0.947	High Similarity	NPC13408
0.947	High Similarity	NPC194281
0.947	High Similarity	NPC234133
0.947	High Similarity	NPC47815
0.9449	High Similarity	NPC305518
0.9449	High Similarity	NPC128428
0.9407	High Similarity	NPC55832
0.9407	High Similarity	NPC26051
0.9407	High Similarity	NPC268204
0.9407	High Similarity	NPC469404
0.9407	High Similarity	NPC470087
0.9407	High Similarity	NPC470089
0.9407	High Similarity	NPC321980
0.9407	High Similarity	NPC52789
0.9407	High Similarity	NPC110969
0.9407	High Similarity	NPC49108
0.9403	High Similarity	NPC109232
0.9403	High Similarity	NPC283429
0.9403	High Similarity	NPC295384
0.9398	High Similarity	NPC290291
0.9398	High Similarity	NPC275055
0.9394	High Similarity	NPC39426
0.9394	High Similarity	NPC234560
0.938	High Similarity	NPC185497
0.9338	High Similarity	NPC11561
0.9338	High Similarity	NPC471417
0.9338	High Similarity	NPC119663
0.9338	High Similarity	NPC226636
0.9333	High Similarity	NPC129853
0.9333	High Similarity	NPC253822
0.9333	High Similarity	NPC188243
0.9333	High Similarity	NPC110228
0.9333	High Similarity	NPC6407
0.9333	High Similarity	NPC76445
0.9333	High Similarity	NPC159275
0.9333	High Similarity	NPC69769
0.9333	High Similarity	NPC269652
0.9333	High Similarity	NPC172986
0.9333	High Similarity	NPC270883
0.9333	High Similarity	NPC241100
0.9333	High Similarity	NPC101366
0.9333	High Similarity	NPC265178
0.9333	High Similarity	NPC284550
0.9333	High Similarity	NPC281207
0.9333	High Similarity	NPC261227
0.9323	High Similarity	NPC24394
0.9323	High Similarity	NPC87545
0.9323	High Similarity	NPC235428
0.9318	High Similarity	NPC172262
0.9318	High Similarity	NPC164136
0.9313	High Similarity	NPC15834
0.9313	High Similarity	NPC203817
0.9313	High Similarity	NPC215875
0.9313	High Similarity	NPC10971
0.9302	High Similarity	NPC69235
0.9302	High Similarity	NPC212379
0.9302	High Similarity	NPC60558
0.9291	High Similarity	NPC65041
0.927	High Similarity	NPC149026
0.927	High Similarity	NPC18585
0.927	High Similarity	NPC475705
0.927	High Similarity	NPC117836
0.927	High Similarity	NPC301751
0.927	High Similarity	NPC166138
0.927	High Similarity	NPC175504
0.927	High Similarity	NPC91560
0.927	High Similarity	NPC39329
0.927	High Similarity	NPC75049
0.927	High Similarity	NPC106985
0.927	High Similarity	NPC143896
0.927	High Similarity	NPC257097
0.927	High Similarity	NPC245482
0.927	High Similarity	NPC169591
0.927	High Similarity	NPC51887
0.927	High Similarity	NPC68104
0.927	High Similarity	NPC150408
0.927	High Similarity	NPC310130
0.927	High Similarity	NPC164980
0.927	High Similarity	NPC476178
0.927	High Similarity	NPC221432
0.9265	High Similarity	NPC126534
0.9265	High Similarity	NPC90582
0.9265	High Similarity	NPC3188
0.9265	High Similarity	NPC262094
0.9265	High Similarity	NPC147688
0.9265	High Similarity	NPC232021
0.9265	High Similarity	NPC64908
0.9265	High Similarity	NPC26238

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 NPC242294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	986
0.2-0.3	1483
0.3-0.4	2635
0.4-0.5	1904
0.5-0.6	1217
0.6-0.7	415
0.7-0.8	141
0.8-0.85	40
0.85-0.9	9
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9688	High Similarity	NPD1240	Approved
0.9538	High Similarity	NPD1607	Approved
0.9394	High Similarity	NPD1510	Phase 2
0.9185	High Similarity	NPD1549	Phase 2
0.9111	High Similarity	NPD1550	Clinical (unspecified phase)
0.9111	High Similarity	NPD1552	Clinical (unspecified phase)
0.9065	High Similarity	NPD4378	Clinical (unspecified phase)
0.8929	High Similarity	NPD7410	Clinical (unspecified phase)
0.8897	High Similarity	NPD2796	Approved
0.8857	High Similarity	NPD6799	Approved
0.875	High Similarity	NPD4380	Phase 2
0.869	High Similarity	NPD7411	Suspended
0.8633	High Similarity	NPD970	Clinical (unspecified phase)
0.8592	High Similarity	NPD1511	Approved
0.8581	High Similarity	NPD3882	Suspended
0.8571	High Similarity	NPD2801	Approved
0.8571	High Similarity	NPD2393	Clinical (unspecified phase)
0.854	High Similarity	NPD6651	Approved
0.8523	High Similarity	NPD7075	Discontinued
0.8519	High Similarity	NPD6859	Clinical (unspecified phase)
0.8514	High Similarity	NPD8443	Clinical (unspecified phase)
0.8511	High Similarity	NPD1878	Clinical (unspecified phase)
0.8503	High Similarity	NPD1934	Approved
0.8493	Intermediate Similarity	NPD6599	Discontinued
0.8489	Intermediate Similarity	NPD1551	Phase 2
0.8489	Intermediate Similarity	NPD2935	Discontinued
0.8472	Intermediate Similarity	NPD1512	Approved
0.8446	Intermediate Similarity	NPD7819	Suspended
0.8446	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD3750	Approved
0.8378	Intermediate Similarity	NPD6801	Discontinued
0.831	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD1203	Approved
0.8261	Intermediate Similarity	NPD943	Approved
0.8212	Intermediate Similarity	NPD7768	Phase 2
0.8194	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2800	Approved
0.8182	Intermediate Similarity	NPD2654	Approved
0.8169	Intermediate Similarity	NPD2344	Approved
0.8163	Intermediate Similarity	NPD5403	Approved
0.8158	Intermediate Similarity	NPD3749	Approved
0.8146	Intermediate Similarity	NPD3817	Phase 2
0.8102	Intermediate Similarity	NPD6832	Phase 2
0.8088	Intermediate Similarity	NPD2798	Approved
0.8077	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6166	Phase 2
0.8077	Intermediate Similarity	NPD9493	Approved
0.8065	Intermediate Similarity	NPD6232	Discontinued
0.806	Intermediate Similarity	NPD3972	Approved
0.806	Intermediate Similarity	NPD9717	Approved
0.8056	Intermediate Similarity	NPD1243	Approved
0.8028	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD3748	Approved
0.8028	Intermediate Similarity	NPD2799	Discontinued
0.8027	Intermediate Similarity	NPD5401	Approved
0.8027	Intermediate Similarity	NPD2532	Approved
0.8027	Intermediate Similarity	NPD2534	Approved
0.8027	Intermediate Similarity	NPD2533	Approved
0.8025	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7975	Intermediate Similarity	NPD3818	Discontinued
0.7955	Intermediate Similarity	NPD9545	Approved
0.7945	Intermediate Similarity	NPD2309	Approved
0.7937	Intermediate Similarity	NPD5953	Discontinued
0.7925	Intermediate Similarity	NPD7286	Phase 2
0.7925	Intermediate Similarity	NPD7054	Approved
0.7925	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD920	Approved
0.7891	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4628	Phase 3
0.7875	Intermediate Similarity	NPD7074	Phase 3
0.7875	Intermediate Similarity	NPD7472	Approved
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD422	Phase 1
0.7852	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6797	Phase 2
0.7821	Intermediate Similarity	NPD5494	Approved
0.782	Intermediate Similarity	NPD1548	Phase 1
0.78	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD5402	Approved
0.7785	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.773	Intermediate Similarity	NPD7808	Phase 3
0.773	Intermediate Similarity	NPD3268	Approved
0.773	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2313	Discontinued
0.7724	Intermediate Similarity	NPD6100	Approved
0.7724	Intermediate Similarity	NPD6099	Approved
0.7718	Intermediate Similarity	NPD7390	Discontinued
0.7714	Intermediate Similarity	NPD4908	Phase 1
0.7692	Intermediate Similarity	NPD230	Phase 1
0.7673	Intermediate Similarity	NPD3926	Phase 2
0.7669	Intermediate Similarity	NPD6559	Discontinued
0.7655	Intermediate Similarity	NPD7033	Discontinued
0.7655	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD2797	Approved
0.7622	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1610	Phase 2
0.7582	Intermediate Similarity	NPD3226	Approved
0.7576	Intermediate Similarity	NPD1241	Discontinued
0.7569	Intermediate Similarity	NPD1933	Approved
0.7569	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD3225	Approved
0.7554	Intermediate Similarity	NPD1876	Approved
0.7534	Intermediate Similarity	NPD4308	Phase 3
0.7532	Intermediate Similarity	NPD919	Approved
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD1164	Approved
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7483	Intermediate Similarity	NPD3764	Approved
0.7483	Intermediate Similarity	NPD411	Approved
0.7482	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7458	Discontinued
0.7464	Intermediate Similarity	NPD1201	Approved
0.7462	Intermediate Similarity	NPD9266	Approved
0.7462	Intermediate Similarity	NPD74	Approved
0.7448	Intermediate Similarity	NPD447	Suspended
0.7447	Intermediate Similarity	NPD1019	Discontinued
0.7439	Intermediate Similarity	NPD1729	Discontinued
0.7438	Intermediate Similarity	NPD1247	Approved
0.7432	Intermediate Similarity	NPD2346	Discontinued
0.7413	Intermediate Similarity	NPD3027	Phase 3
0.741	Intermediate Similarity	NPD1608	Approved
0.74	Intermediate Similarity	NPD7003	Approved
0.7394	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD9494	Approved
0.7391	Intermediate Similarity	NPD5711	Approved
0.7391	Intermediate Similarity	NPD5710	Approved
0.7389	Intermediate Similarity	NPD1465	Phase 2
0.7385	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD9263	Approved
0.7385	Intermediate Similarity	NPD9264	Approved
0.7385	Intermediate Similarity	NPD9267	Approved
0.7376	Intermediate Similarity	NPD3267	Approved
0.7376	Intermediate Similarity	NPD3266	Approved
0.7372	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5408	Approved
0.7365	Intermediate Similarity	NPD5404	Approved
0.7365	Intermediate Similarity	NPD5405	Approved
0.7365	Intermediate Similarity	NPD5406	Approved
0.7361	Intermediate Similarity	NPD1296	Phase 2
0.7349	Intermediate Similarity	NPD6104	Discontinued
0.7342	Intermediate Similarity	NPD4288	Approved
0.7342	Intermediate Similarity	NPD2296	Approved
0.7299	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1481	Phase 2
0.7283	Intermediate Similarity	NPD4363	Phase 3
0.7283	Intermediate Similarity	NPD4360	Phase 2
0.7279	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD846	Approved
0.7266	Intermediate Similarity	NPD940	Approved
0.7266	Intermediate Similarity	NPD3847	Discontinued
0.7261	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3140	Approved
0.726	Intermediate Similarity	NPD4307	Phase 2
0.726	Intermediate Similarity	NPD3142	Approved
0.7241	Intermediate Similarity	NPD4361	Phase 2
0.7241	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6798	Discontinued
0.7237	Intermediate Similarity	NPD2354	Approved
0.7226	Intermediate Similarity	NPD5536	Phase 2
0.7222	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1535	Discovery
0.7211	Intermediate Similarity	NPD5124	Phase 1
0.7211	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4662	Approved
0.7208	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4661	Approved
0.72	Intermediate Similarity	NPD1471	Phase 3
0.7195	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD17	Approved
0.7174	Intermediate Similarity	NPD1894	Discontinued
0.7172	Intermediate Similarity	NPD4625	Phase 3
0.7168	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD9269	Phase 2
0.7153	Intermediate Similarity	NPD3018	Phase 2
0.7153	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD6971	Discontinued
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4357	Discontinued
0.7132	Intermediate Similarity	NPD9281	Approved
0.7124	Intermediate Similarity	NPD3887	Approved
0.7122	Intermediate Similarity	NPD9268	Approved
0.7122	Intermediate Similarity	NPD1651	Approved
0.7113	Intermediate Similarity	NPD4749	Approved
0.7108	Intermediate Similarity	NPD3751	Discontinued
0.7107	Intermediate Similarity	NPD6844	Discontinued
0.7107	Intermediate Similarity	NPD6280	Approved
0.7107	Intermediate Similarity	NPD6279	Approved
0.7103	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6355	Discontinued
0.7091	Intermediate Similarity	NPD2403	Approved
0.7086	Intermediate Similarity	NPD2355	Clinical (unspecified phase)

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