NPASS Compound

Structure

CID242000 OpenBabel06191716042D 24 26 0 0 1 0 0 0 0 0999 V2000 0.8764 3.6566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7967 4.1049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0579 0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 1.7321 -3.0000 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 -1.3143 2.1730 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 -1.5731 1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0896 3.3978 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 -1.5000 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 -0.3484 2.4319 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3587 1.7247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 16 2 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	327.18
Volume:	350.355
LogP:	3.202
LogD:	2.823
LogS:	-3.263
# Rotatable Bonds:	4
TPSA:	48.3
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.861
Synthetic Accessibility Score:	3.199
Fsp3:	0.5
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:	-4.619
MDCK Permeability:	2.1131585526745766e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.417

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.952
Plasma Protein Binding (PPB):	95.22858428955078%
Volume Distribution (VD):	0.616
Pgp-substrate:	3.4292895793914795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.906
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.404
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.299
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.735
CYP3A4-inhibitor:	0.216
CYP3A4-substrate:	0.457

ADMET: Excretion

Clearance (CL):	5.423
Half-life (T1/2):	0.403

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.568
Drug-inuced Liver Injury (DILI):	0.283
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.474
Maximum Recommended Daily Dose:	0.072
Skin Sensitization:	0.055
Carcinogencity:	0.218
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC242000

Natural Product ID:	NPC242000
*Common Name:**	Huajiaosimuline
IUPAC Name:	2,6-dimethyl-2-(4-methyl-3-oxopentyl)-3,4-dihydropyrano[3,2-c]quinolin-5-one
Synonyms:	Huajiaosimuline
Standard InCHIKey:	JEYMMXXYHADRSB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H25NO3/c1-13(2)17(22)10-12-20(3)11-9-15-18(24-20)14-7-5-6-8-16(14)21(4)19(15)23/h5-8,13H,9-12H2,1-4H3
SMILES:	O=C(C(C)C)CCC1(C)CCc2c(O1)c1ccccc1n(c2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513567
PubChem CID:	44559731
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001291] Pyranoquinolines

*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
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26666037]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798955]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9760	Goniothalamus howii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9760	Goniothalamus howii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9760	Goniothalamus howii	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	13
Others	28

Activity Type	# Activity
Cell Line	34
NON-MOLECULAR	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	60.0	uM	PMID[474715]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	60.0	uM	PMID[474715]
NPT916	Cell Line	SK-MEL	Homo sapiens	ED50	=	36.6	uM	PMID[474715]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	>	60.0	uM	PMID[474715]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	46.4	uM	PMID[474715]
NPT168	Cell Line	P388	Mus musculus	ED50	=	9.8	uM	PMID[474715]
NPT762	Cell Line	A-431	Homo sapiens	ED50	>	60.0	uM	PMID[474715]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	60.0	ug ml-1	PMID[474715]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	11.1	ug ml-1	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	31.6	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	0.0	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	53.1	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	9.9	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	8.0	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	4.5	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	5.5	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	48.9	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	12.22	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	5.0	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	9.4	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	6.5	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	85.0	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	96.0	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	98.0	%	PMID[474715]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	97.0	%	PMID[474715]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	60.0	uM	PMID[474715]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.0	uM	PMID[474715]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	24.3	uM	PMID[474715]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	60.0	ug ml-1	PMID[474715]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	100.0	%	PMID[474715]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	83.9	%	PMID[474715]

☑ 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 NPC242000 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	505
0.1-0.2	3036
0.2-0.3	12368
0.3-0.4	5110
0.4-0.5	13148
0.5-0.6	6380
0.6-0.7	1855
0.7-0.8	272
0.8-0.85	17
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9638	High Similarity	NPC308197
0.8841	High Similarity	NPC231382
0.8662	High Similarity	NPC307640
0.8417	Intermediate Similarity	NPC250476
0.775	Intermediate Similarity	NPC301163
0.7669	Intermediate Similarity	NPC299582
0.7616	Intermediate Similarity	NPC262725
0.7593	Intermediate Similarity	NPC93653
0.7458	Intermediate Similarity	NPC471825
0.7457	Intermediate Similarity	NPC322621
0.7425	Intermediate Similarity	NPC469915
0.7403	Intermediate Similarity	NPC315051
0.7378	Intermediate Similarity	NPC320064
0.7356	Intermediate Similarity	NPC49184
0.7353	Intermediate Similarity	NPC129624
0.7337	Intermediate Similarity	NPC96901
0.7312	Intermediate Similarity	NPC144691
0.7305	Intermediate Similarity	NPC279527
0.7305	Intermediate Similarity	NPC214960
0.7267	Intermediate Similarity	NPC321211
0.7256	Intermediate Similarity	NPC113946
0.7247	Intermediate Similarity	NPC1820
0.7198	Intermediate Similarity	NPC100863
0.7198	Intermediate Similarity	NPC71124
0.7195	Intermediate Similarity	NPC29285
0.7191	Intermediate Similarity	NPC473569
0.7172	Intermediate Similarity	NPC177684
0.7172	Intermediate Similarity	NPC291962
0.7143	Intermediate Similarity	NPC173295
0.7126	Intermediate Similarity	NPC85613
0.7123	Intermediate Similarity	NPC161956
0.7123	Intermediate Similarity	NPC258531
0.7123	Intermediate Similarity	NPC112373
0.7111	Intermediate Similarity	NPC473004
0.711	Intermediate Similarity	NPC186669
0.7097	Intermediate Similarity	NPC41216
0.7095	Intermediate Similarity	NPC45389
0.7086	Intermediate Similarity	NPC122235
0.7083	Intermediate Similarity	NPC313757
0.7075	Intermediate Similarity	NPC257490
0.7072	Intermediate Similarity	NPC254957
0.7059	Intermediate Similarity	NPC268077
0.7029	Intermediate Similarity	NPC5167
0.7024	Intermediate Similarity	NPC293458
0.7024	Intermediate Similarity	NPC472117
0.7011	Intermediate Similarity	NPC234933
0.7006	Intermediate Similarity	NPC471122
0.7005	Intermediate Similarity	NPC207971
0.7	Intermediate Similarity	NPC472114
0.7	Intermediate Similarity	NPC472115
0.6973	Remote Similarity	NPC5374
0.6966	Remote Similarity	NPC473007
0.6964	Remote Similarity	NPC315368
0.6961	Remote Similarity	NPC22476
0.6946	Remote Similarity	NPC123241
0.6941	Remote Similarity	NPC471124
0.6936	Remote Similarity	NPC139085
0.6936	Remote Similarity	NPC251212
0.6936	Remote Similarity	NPC214626
0.6931	Remote Similarity	NPC477161
0.6923	Remote Similarity	NPC176983
0.6923	Remote Similarity	NPC476231
0.6914	Remote Similarity	NPC474081
0.691	Remote Similarity	NPC97584
0.6883	Remote Similarity	NPC314098
0.6882	Remote Similarity	NPC204867
0.6864	Remote Similarity	NPC474058
0.6864	Remote Similarity	NPC27904
0.6862	Remote Similarity	NPC15987
0.686	Remote Similarity	NPC167724
0.686	Remote Similarity	NPC224970
0.686	Remote Similarity	NPC223595
0.6859	Remote Similarity	NPC285192
0.6857	Remote Similarity	NPC264482
0.6857	Remote Similarity	NPC475607
0.6857	Remote Similarity	NPC203202
0.6855	Remote Similarity	NPC472243
0.6848	Remote Similarity	NPC230313
0.6845	Remote Similarity	NPC138830
0.6845	Remote Similarity	NPC67904
0.6842	Remote Similarity	NPC472106
0.6839	Remote Similarity	NPC181138
0.6839	Remote Similarity	NPC298851
0.6839	Remote Similarity	NPC293255
0.6839	Remote Similarity	NPC21752
0.6839	Remote Similarity	NPC210415
0.6839	Remote Similarity	NPC276993
0.6839	Remote Similarity	NPC73280
0.6826	Remote Similarity	NPC161827
0.6824	Remote Similarity	NPC286871
0.6824	Remote Similarity	NPC472101
0.6824	Remote Similarity	NPC472120
0.6813	Remote Similarity	NPC473008
0.681	Remote Similarity	NPC146370
0.6806	Remote Similarity	NPC308943
0.6805	Remote Similarity	NPC193410
0.68	Remote Similarity	NPC475594
0.68	Remote Similarity	NPC39818
0.6782	Remote Similarity	NPC471604
0.678	Remote Similarity	NPC475761
0.6779	Remote Similarity	NPC279385
0.6779	Remote Similarity	NPC179605
0.6776	Remote Similarity	NPC470343
0.6776	Remote Similarity	NPC203628
0.6776	Remote Similarity	NPC25401
0.6776	Remote Similarity	NPC325013
0.6776	Remote Similarity	NPC472244
0.6766	Remote Similarity	NPC473449
0.6765	Remote Similarity	NPC248117
0.6757	Remote Similarity	NPC243626
0.6757	Remote Similarity	NPC198401
0.6753	Remote Similarity	NPC81092
0.6753	Remote Similarity	NPC103605
0.6752	Remote Similarity	NPC253476
0.6752	Remote Similarity	NPC266425
0.6746	Remote Similarity	NPC61013
0.6744	Remote Similarity	NPC52059
0.6744	Remote Similarity	NPC470069
0.6742	Remote Similarity	NPC283810
0.674	Remote Similarity	NPC291759
0.6739	Remote Similarity	NPC114039
0.6739	Remote Similarity	NPC206109
0.6733	Remote Similarity	NPC103292
0.6725	Remote Similarity	NPC472121
0.6723	Remote Similarity	NPC260075
0.6721	Remote Similarity	NPC5630
0.6711	Remote Similarity	NPC226143
0.6711	Remote Similarity	NPC226794
0.6707	Remote Similarity	NPC122106
0.6706	Remote Similarity	NPC243673
0.6706	Remote Similarity	NPC63210
0.6706	Remote Similarity	NPC310403
0.6706	Remote Similarity	NPC148468
0.6706	Remote Similarity	NPC97380
0.6706	Remote Similarity	NPC263709
0.6705	Remote Similarity	NPC470548
0.6705	Remote Similarity	NPC278887
0.6703	Remote Similarity	NPC14994
0.6703	Remote Similarity	NPC103230
0.6703	Remote Similarity	NPC21425
0.6702	Remote Similarity	NPC241263
0.6702	Remote Similarity	NPC87714
0.6687	Remote Similarity	NPC469560
0.6687	Remote Similarity	NPC319645
0.6687	Remote Similarity	NPC473329
0.6686	Remote Similarity	NPC471648
0.6685	Remote Similarity	NPC474041
0.6685	Remote Similarity	NPC6974
0.6685	Remote Similarity	NPC218594
0.6685	Remote Similarity	NPC99043
0.6685	Remote Similarity	NPC133591
0.6684	Remote Similarity	NPC100573
0.6684	Remote Similarity	NPC207873
0.6667	Remote Similarity	NPC472241
0.6667	Remote Similarity	NPC472102
0.6667	Remote Similarity	NPC254798
0.6667	Remote Similarity	NPC159963
0.6667	Remote Similarity	NPC143457
0.6667	Remote Similarity	NPC15384
0.6667	Remote Similarity	NPC471132
0.6667	Remote Similarity	NPC244425
0.6667	Remote Similarity	NPC471197
0.6667	Remote Similarity	NPC309531
0.6667	Remote Similarity	NPC84347
0.6649	Remote Similarity	NPC112937
0.6648	Remote Similarity	NPC38823
0.6648	Remote Similarity	NPC39822
0.6648	Remote Similarity	NPC298320
0.6648	Remote Similarity	NPC207033
0.6647	Remote Similarity	NPC243756
0.6647	Remote Similarity	NPC471130
0.6646	Remote Similarity	NPC184437
0.6646	Remote Similarity	NPC242933
0.6645	Remote Similarity	NPC150863
0.6633	Remote Similarity	NPC248601
0.6633	Remote Similarity	NPC471198
0.6633	Remote Similarity	NPC10732
0.6632	Remote Similarity	NPC198160
0.6631	Remote Similarity	NPC303214
0.663	Remote Similarity	NPC22689
0.663	Remote Similarity	NPC471195
0.663	Remote Similarity	NPC474059
0.663	Remote Similarity	NPC105055
0.663	Remote Similarity	NPC471196
0.6628	Remote Similarity	NPC88970
0.6612	Remote Similarity	NPC473815
0.6611	Remote Similarity	NPC472163
0.6611	Remote Similarity	NPC116096
0.6603	Remote Similarity	NPC283079
0.6603	Remote Similarity	NPC280807
0.6603	Remote Similarity	NPC472245
0.6603	Remote Similarity	NPC314431
0.6597	Remote Similarity	NPC295898
0.6596	Remote Similarity	NPC472541
0.6596	Remote Similarity	NPC472542
0.6588	Remote Similarity	NPC63370
0.6588	Remote Similarity	NPC36836
0.6585	Remote Similarity	NPC190945
0.6575	Remote Similarity	NPC477159
0.6575	Remote Similarity	NPC314659

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 NPC242000 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	649
0.2-0.3	893
0.3-0.4	1206
0.4-0.5	2779
0.5-0.6	2319
0.6-0.7	848
0.7-0.8	116
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7838	Intermediate Similarity	NPD2791	Discontinued
0.7636	Intermediate Similarity	NPD5186	Approved
0.7636	Intermediate Similarity	NPD5183	Approved
0.7597	Intermediate Similarity	NPD4430	Phase 2
0.75	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3789	Approved
0.75	Intermediate Similarity	NPD2670	Approved
0.7412	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3278	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3277	Phase 3
0.716	Intermediate Similarity	NPD6457	Approved
0.7135	Intermediate Similarity	NPD5997	Discontinued
0.7126	Intermediate Similarity	NPD4871	Phase 2
0.711	Intermediate Similarity	NPD3793	Phase 3
0.7099	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5620	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3170	Approved
0.7	Intermediate Similarity	NPD5823	Approved
0.6975	Remote Similarity	NPD1802	Approved
0.6975	Remote Similarity	NPD1801	Approved
0.6966	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2820	Phase 3
0.6933	Remote Similarity	NPD7528	Approved
0.6919	Remote Similarity	NPD5071	Phase 2
0.6903	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7487	Discontinued
0.6887	Remote Similarity	NPD6320	Approved
0.6875	Remote Similarity	NPD2365	Approved
0.6875	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1064	Approved
0.6857	Remote Similarity	NPD1065	Approved
0.6836	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2335	Discontinued
0.6813	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4515	Suspended
0.679	Remote Similarity	NPD2387	Approved
0.6788	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7478	Approved
0.6766	Remote Similarity	NPD6357	Discontinued
0.6766	Remote Similarity	NPD3229	Phase 2
0.6737	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7082	Approved
0.672	Remote Similarity	NPD6321	Discontinued
0.6705	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3297	Approved
0.6701	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1109	Approved
0.6687	Remote Similarity	NPD1626	Approved
0.6687	Remote Similarity	NPD7259	Approved
0.6687	Remote Similarity	NPD1110	Approved
0.6684	Remote Similarity	NPD5515	Phase 2
0.6667	Remote Similarity	NPD5086	Approved
0.6648	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7606	Phase 3
0.6646	Remote Similarity	NPD7295	Approved
0.6644	Remote Similarity	NPD5180	Approved
0.6644	Remote Similarity	NPD5179	Approved
0.6644	Remote Similarity	NPD5181	Approved
0.6632	Remote Similarity	NPD6238	Discontinued
0.6632	Remote Similarity	NPD3416	Discontinued
0.663	Remote Similarity	NPD5928	Phase 1
0.6629	Remote Similarity	NPD5600	Discontinued
0.6629	Remote Similarity	NPD5847	Phase 1
0.6627	Remote Similarity	NPD5941	Approved
0.6627	Remote Similarity	NPD5942	Approved
0.6627	Remote Similarity	NPD4161	Discontinued
0.6627	Remote Similarity	NPD4888	Discontinued
0.6625	Remote Similarity	NPD743	Approved
0.6615	Remote Similarity	NPD3298	Approved
0.6612	Remote Similarity	NPD6891	Phase 2
0.6607	Remote Similarity	NPD3399	Approved
0.6606	Remote Similarity	NPD4041	Approved
0.6606	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3141	Discontinued
0.6591	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.659	Remote Similarity	NPD1309	Phase 2
0.659	Remote Similarity	NPD1307	Phase 2
0.6588	Remote Similarity	NPD6571	Approved
0.6588	Remote Similarity	NPD2836	Approved
0.6588	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6570	Approved
0.6588	Remote Similarity	NPD2672	Discontinued
0.6585	Remote Similarity	NPD2435	Approved
0.6585	Remote Similarity	NPD5918	Discontinued
0.658	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD518	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7244	Discontinued
0.657	Remote Similarity	NPD7600	Phase 2
0.6566	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6566	Discontinued
0.6562	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7570	Approved
0.6559	Remote Similarity	NPD7569	Approved
0.6552	Remote Similarity	NPD2201	Approved
0.6545	Remote Similarity	NPD6017	Discontinued
0.6536	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD1625	Approved
0.6524	Remote Similarity	NPD5024	Approved
0.6522	Remote Similarity	NPD6636	Phase 3
0.6517	Remote Similarity	NPD5466	Approved
0.6516	Remote Similarity	NPD9567	Approved
0.6516	Remote Similarity	NPD552	Approved
0.6516	Remote Similarity	NPD553	Approved
0.6512	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7599	Phase 2
0.6512	Remote Similarity	NPD3388	Phase 1
0.6512	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6659	Phase 2
0.6505	Remote Similarity	NPD5042	Phase 1
0.6503	Remote Similarity	NPD7752	Approved
0.6503	Remote Similarity	NPD7753	Approved
0.65	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD8007	Approved
0.6494	Remote Similarity	NPD8008	Approved
0.649	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD5235	Approved
0.6483	Remote Similarity	NPD5237	Approved
0.6483	Remote Similarity	NPD5239	Approved
0.6483	Remote Similarity	NPD5240	Approved
0.6483	Remote Similarity	NPD5236	Approved
0.648	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD2949	Approved
0.6478	Remote Similarity	NPD2950	Approved
0.6474	Remote Similarity	NPD850	Approved
0.6474	Remote Similarity	NPD848	Approved
0.6474	Remote Similarity	NPD849	Approved
0.6465	Remote Similarity	NPD7225	Discontinued
0.6464	Remote Similarity	NPD6878	Phase 2
0.6464	Remote Similarity	NPD6879	Phase 2
0.6463	Remote Similarity	NPD6768	Approved
0.6463	Remote Similarity	NPD2923	Approved
0.6461	Remote Similarity	NPD5858	Discontinued
0.6457	Remote Similarity	NPD5430	Discontinued
0.6457	Remote Similarity	NPD7035	Approved
0.6457	Remote Similarity	NPD7036	Phase 3
0.6456	Remote Similarity	NPD6039	Approved
0.6456	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD708	Approved
0.6453	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.645	Remote Similarity	NPD1670	Discontinued
0.6448	Remote Similarity	NPD5923	Phase 1
0.6446	Remote Similarity	NPD6185	Discontinued
0.6446	Remote Similarity	NPD3301	Approved
0.6444	Remote Similarity	NPD3449	Discontinued
0.644	Remote Similarity	NPD6874	Approved
0.6438	Remote Similarity	NPD5185	Approved
0.6438	Remote Similarity	NPD5182	Approved
0.6438	Remote Similarity	NPD5184	Approved
0.6436	Remote Similarity	NPD4539	Phase 1
0.6436	Remote Similarity	NPD5610	Approved
0.6432	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4942	Approved
0.6429	Remote Similarity	NPD4682	Phase 2
0.6429	Remote Similarity	NPD4082	Approved
0.6429	Remote Similarity	NPD1360	Approved
0.6425	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6342	Discontinued
0.6416	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1920	Approved
0.6415	Remote Similarity	NPD1919	Approved
0.641	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD7479	Phase 2
0.6409	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD4607	Approved
0.6404	Remote Similarity	NPD3437	Discontinued
0.6398	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4334	Discontinued
0.6395	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD8281	Discontinued
0.6392	Remote Similarity	NPD6445	Discontinued
0.6392	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5131	Approved
0.6392	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD2681	Approved
0.6384	Remote Similarity	NPD3983	Phase 3
0.6384	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7126	Discontinued
0.6384	Remote Similarity	NPD2680	Approved
0.6383	Remote Similarity	NPD5937	Approved
0.6379	Remote Similarity	NPD5977	Approved
0.6379	Remote Similarity	NPD5978	Approved
0.6379	Remote Similarity	NPD2506	Approved
0.6378	Remote Similarity	NPD5444	Phase 1
0.6375	Remote Similarity	NPD1527	Phase 2

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