NPASS Compound

Structure

NPC134083 OpenBabel07101718332D 27 28 0 0 1 0 0 0 0 0999 V2000 6.9282 -0.0000 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 6.0622 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 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 6.0622 1.5000 0.0000 C 0 0 1 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 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -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 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 4 14 1 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 12 27 1 0 0 0 0 13 3 1 1 0 0 0 14 19 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 18 22 1 6 0 0 0 19 24 2 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 21 25 2 0 0 0 0 22 5 1 1 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.16
Volume:	403.872
LogP:	4.319
LogD:	3.952
LogS:	-4.873
# Rotatable Bonds:	6
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.664
Synthetic Accessibility Score:	4.932
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.593
MDCK Permeability:	1.8634675143403e-05
Pgp-inhibitor:	0.153
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	81.3003921508789%
Volume Distribution (VD):	1.671
Pgp-substrate:	12.034419059753418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.427
CYP2C19-inhibitor:	0.944
CYP2C19-substrate:	0.673
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.925
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.949
CYP3A4-substrate:	0.426

ADMET: Excretion

Clearance (CL):	5.007
Half-life (T1/2):	0.197

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.913
Drug-inuced Liver Injury (DILI):	0.419
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.889
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.946
Carcinogencity:	0.949
Eye Corrosion:	0.065
Eye Irritation:	0.306
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC134083

Natural Product ID:	NPC134083
*Common Name:**	Chaetomugilin J
IUPAC Name:	(7S,8S)-5-chloro-7-hydroxy-7-methyl-8-[(E)-3-methyl-2-oxopent-3-enyl]-3-[(E,3S)-3-methylpent-1-enyl]-8H-isochromen-6-one
Synonyms:
Standard InCHIKey:	DIBDMIBWFDRKHK-ODXBHRCKSA-N
Standard InCHI:	InChI=1S/C22H27ClO4/c1-6-13(3)8-9-15-10-16-17(12-27-15)18(11-19(24)14(4)7-2)22(5,26)21(25)20(16)23/h7-10,12-13,18,26H,6,11H2,1-5H3/b9-8+,14-7+/t13-,18-,22-/m0/s1
SMILES:	CC[C@@H](/C=C/C1=CC2=C(Cl)C(=O)[C@@]([C@H](C2=CO1)CC(=O)/C(=C/C)/C)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3621756
PubChem CID:	44250065
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	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
IC50	3
Others	4

Activity Type	# Activity
Cell Line	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	83.4	%	PMID[528300]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	99.9	%	PMID[528300]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	36.2	%	PMID[528300]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	4200.0	nM	PMID[528300]
NPT2	Others	Unspecified		Inhibition	=	74.2	%	PMID[528300]
NPT2	Others	Unspecified		IC50	=	7600.0	nM	PMID[528300]

☑ 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 NPC134083 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	200
0.1-0.2	1228
0.2-0.3	5250
0.3-0.4	12724
0.4-0.5	15928
0.5-0.6	6194
0.6-0.7	1097
0.7-0.8	64
0.8-0.85	5
0.85-0.9	0
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC185253
0.9783	High Similarity	NPC215253
0.9674	High Similarity	NPC166770
0.9271	High Similarity	NPC473144
0.9271	High Similarity	NPC297281
0.8478	Intermediate Similarity	NPC203795
0.8125	Intermediate Similarity	NPC224270
0.8091	Intermediate Similarity	NPC245320
0.8058	Intermediate Similarity	NPC272528
0.8018	Intermediate Similarity	NPC473145
0.8018	Intermediate Similarity	NPC476815
0.8018	Intermediate Similarity	NPC31641
0.7941	Intermediate Similarity	NPC224172
0.78	Intermediate Similarity	NPC12727
0.7748	Intermediate Similarity	NPC243298
0.77	Intermediate Similarity	NPC143210
0.7619	Intermediate Similarity	NPC25666
0.7619	Intermediate Similarity	NPC271059
0.757	Intermediate Similarity	NPC232969
0.757	Intermediate Similarity	NPC199107
0.7453	Intermediate Similarity	NPC320294
0.7451	Intermediate Similarity	NPC295347
0.7429	Intermediate Similarity	NPC469851
0.7327	Intermediate Similarity	NPC166110
0.7327	Intermediate Similarity	NPC32944
0.7327	Intermediate Similarity	NPC193396
0.7327	Intermediate Similarity	NPC32552
0.7308	Intermediate Similarity	NPC471694
0.7308	Intermediate Similarity	NPC208094
0.7282	Intermediate Similarity	NPC31021
0.7255	Intermediate Similarity	NPC242637
0.7255	Intermediate Similarity	NPC248193
0.7248	Intermediate Similarity	NPC469853
0.7216	Intermediate Similarity	NPC288281
0.72	Intermediate Similarity	NPC473658
0.72	Intermediate Similarity	NPC26078
0.7156	Intermediate Similarity	NPC469852
0.7156	Intermediate Similarity	NPC85529
0.7156	Intermediate Similarity	NPC32006
0.7129	Intermediate Similarity	NPC95364
0.7129	Intermediate Similarity	NPC118011
0.7129	Intermediate Similarity	NPC307092
0.7129	Intermediate Similarity	NPC36668
0.7129	Intermediate Similarity	NPC210216
0.7129	Intermediate Similarity	NPC142159
0.7129	Intermediate Similarity	NPC51358
0.7117	Intermediate Similarity	NPC137911
0.7117	Intermediate Similarity	NPC228477
0.7103	Intermediate Similarity	NPC472637
0.71	Intermediate Similarity	NPC103743
0.71	Intermediate Similarity	NPC476079
0.71	Intermediate Similarity	NPC113370
0.7071	Intermediate Similarity	NPC307112
0.7071	Intermediate Similarity	NPC32037
0.7071	Intermediate Similarity	NPC132228
0.7071	Intermediate Similarity	NPC8518
0.7071	Intermediate Similarity	NPC263997
0.7071	Intermediate Similarity	NPC6185
0.7071	Intermediate Similarity	NPC241512
0.7059	Intermediate Similarity	NPC38952
0.7059	Intermediate Similarity	NPC212369
0.7059	Intermediate Similarity	NPC474209
0.7059	Intermediate Similarity	NPC475823
0.7053	Intermediate Similarity	NPC478122
0.7048	Intermediate Similarity	NPC318082
0.703	Intermediate Similarity	NPC60765
0.7	Intermediate Similarity	NPC234038
0.7	Intermediate Similarity	NPC291712
0.7	Intermediate Similarity	NPC478052
0.7	Intermediate Similarity	NPC477125
0.699	Remote Similarity	NPC45579
0.6979	Remote Similarity	NPC475681
0.6979	Remote Similarity	NPC27817
0.6964	Remote Similarity	NPC23497
0.6961	Remote Similarity	NPC474918
0.6947	Remote Similarity	NPC97173
0.6944	Remote Similarity	NPC471699
0.6931	Remote Similarity	NPC181327
0.693	Remote Similarity	NPC66108
0.6923	Remote Similarity	NPC474060
0.69	Remote Similarity	NPC281172
0.69	Remote Similarity	NPC187529
0.6893	Remote Similarity	NPC131864
0.6893	Remote Similarity	NPC253177
0.6893	Remote Similarity	NPC469372
0.6893	Remote Similarity	NPC280592
0.6893	Remote Similarity	NPC213636
0.6893	Remote Similarity	NPC476369
0.6893	Remote Similarity	NPC476437
0.6875	Remote Similarity	NPC231739
0.687	Remote Similarity	NPC321496
0.687	Remote Similarity	NPC326264
0.6869	Remote Similarity	NPC475083
0.6869	Remote Similarity	NPC297398
0.6869	Remote Similarity	NPC16488
0.6863	Remote Similarity	NPC307298
0.6857	Remote Similarity	NPC38830
0.6852	Remote Similarity	NPC46761
0.6847	Remote Similarity	NPC189863
0.6847	Remote Similarity	NPC266570
0.6842	Remote Similarity	NPC151622
0.6842	Remote Similarity	NPC7629
0.6842	Remote Similarity	NPC26504
0.6842	Remote Similarity	NPC110725
0.6837	Remote Similarity	NPC55869
0.6837	Remote Similarity	NPC99308
0.6837	Remote Similarity	NPC275766
0.6837	Remote Similarity	NPC225515
0.6832	Remote Similarity	NPC316426
0.6832	Remote Similarity	NPC315395
0.6832	Remote Similarity	NPC94666
0.6827	Remote Similarity	NPC471329
0.6827	Remote Similarity	NPC296114
0.6827	Remote Similarity	NPC303697
0.6822	Remote Similarity	NPC202705
0.6822	Remote Similarity	NPC239895
0.6818	Remote Similarity	NPC473624
0.6814	Remote Similarity	NPC300026
0.6809	Remote Similarity	NPC122244
0.6809	Remote Similarity	NPC147438
0.6804	Remote Similarity	NPC19900
0.68	Remote Similarity	NPC196487
0.68	Remote Similarity	NPC14575
0.6796	Remote Similarity	NPC5509
0.6796	Remote Similarity	NPC212598
0.6796	Remote Similarity	NPC284561
0.6792	Remote Similarity	NPC209355
0.6792	Remote Similarity	NPC471698
0.6792	Remote Similarity	NPC476245
0.6792	Remote Similarity	NPC91408
0.6789	Remote Similarity	NPC115862
0.6789	Remote Similarity	NPC469657
0.6789	Remote Similarity	NPC244456
0.6786	Remote Similarity	NPC185
0.678	Remote Similarity	NPC146786
0.6771	Remote Similarity	NPC316324
0.6771	Remote Similarity	NPC82666
0.6768	Remote Similarity	NPC471326
0.6768	Remote Similarity	NPC103486
0.6768	Remote Similarity	NPC221231
0.6762	Remote Similarity	NPC1108
0.6759	Remote Similarity	NPC57079
0.6759	Remote Similarity	NPC35717
0.6759	Remote Similarity	NPC108368
0.6757	Remote Similarity	NPC472868
0.6739	Remote Similarity	NPC262673
0.6735	Remote Similarity	NPC108955
0.6735	Remote Similarity	NPC160582
0.6733	Remote Similarity	NPC474680
0.6733	Remote Similarity	NPC471060
0.6733	Remote Similarity	NPC470177
0.6733	Remote Similarity	NPC255174
0.6731	Remote Similarity	NPC212679
0.6731	Remote Similarity	NPC265856
0.6731	Remote Similarity	NPC220454
0.6731	Remote Similarity	NPC469595
0.6731	Remote Similarity	NPC113393
0.6727	Remote Similarity	NPC469606
0.6727	Remote Similarity	NPC273005
0.6727	Remote Similarity	NPC31058
0.6726	Remote Similarity	NPC168883
0.6724	Remote Similarity	NPC474271
0.6701	Remote Similarity	NPC189485
0.6701	Remote Similarity	NPC475994
0.67	Remote Similarity	NPC477785
0.67	Remote Similarity	NPC118423
0.67	Remote Similarity	NPC477786
0.67	Remote Similarity	NPC477784
0.6699	Remote Similarity	NPC478260
0.6699	Remote Similarity	NPC53454
0.6699	Remote Similarity	NPC229612
0.6699	Remote Similarity	NPC478259
0.6699	Remote Similarity	NPC478261
0.6699	Remote Similarity	NPC7280
0.6698	Remote Similarity	NPC477241
0.6698	Remote Similarity	NPC477129
0.6698	Remote Similarity	NPC477130
0.6698	Remote Similarity	NPC78159
0.6698	Remote Similarity	NPC476415
0.6698	Remote Similarity	NPC474882
0.6698	Remote Similarity	NPC299100
0.6697	Remote Similarity	NPC54705
0.6696	Remote Similarity	NPC179798
0.6696	Remote Similarity	NPC474315
0.6696	Remote Similarity	NPC304180
0.6667	Remote Similarity	NPC1254
0.6667	Remote Similarity	NPC111323
0.6667	Remote Similarity	NPC186554
0.6667	Remote Similarity	NPC472305
0.6667	Remote Similarity	NPC121984
0.6667	Remote Similarity	NPC20066
0.6667	Remote Similarity	NPC476848
0.6667	Remote Similarity	NPC291062
0.6667	Remote Similarity	NPC473161
0.6667	Remote Similarity	NPC469538
0.6667	Remote Similarity	NPC474085
0.6667	Remote Similarity	NPC168248
0.6667	Remote Similarity	NPC76966
0.6667	Remote Similarity	NPC94743
0.6667	Remote Similarity	NPC170131

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 NPC134083 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1423
0.2-0.3	3706
0.3-0.4	2739
0.4-0.5	818
0.5-0.6	256
0.6-0.7	24
0.7-0.8	0
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
0.7037	Intermediate Similarity	NPD5091	Approved
0.6792	Remote Similarity	NPD4629	Approved
0.6792	Remote Similarity	NPD5210	Approved
0.6771	Remote Similarity	NPD4756	Discovery
0.6735	Remote Similarity	NPD4695	Discontinued
0.6609	Remote Similarity	NPD5169	Approved
0.6604	Remote Similarity	NPD5133	Approved
0.6569	Remote Similarity	NPD1696	Phase 3
0.6566	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5127	Approved
0.6491	Remote Similarity	NPD6614	Approved
0.6455	Remote Similarity	NPD5696	Approved
0.6435	Remote Similarity	NPD5128	Approved
0.6435	Remote Similarity	NPD5168	Approved
0.641	Remote Similarity	NPD5216	Approved
0.641	Remote Similarity	NPD5215	Approved
0.641	Remote Similarity	NPD5217	Approved
0.6389	Remote Similarity	NPD5282	Discontinued
0.6387	Remote Similarity	NPD5167	Approved
0.6364	Remote Similarity	NPD6335	Approved
0.6364	Remote Similarity	NPD6313	Approved
0.6364	Remote Similarity	NPD6314	Approved
0.6346	Remote Similarity	NPD5279	Phase 3
0.6346	Remote Similarity	NPD4694	Approved
0.6346	Remote Similarity	NPD5280	Approved
0.6346	Remote Similarity	NPD5690	Phase 2
0.633	Remote Similarity	NPD5654	Approved
0.6321	Remote Similarity	NPD4753	Phase 2
0.6321	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5211	Phase 2
0.6281	Remote Similarity	NPD7115	Discovery
0.6273	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5221	Approved
0.6273	Remote Similarity	NPD5222	Approved
0.6264	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5785	Approved
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD1694	Approved
0.625	Remote Similarity	NPD4696	Approved
0.6237	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3704	Approved
0.6216	Remote Similarity	NPD5959	Approved
0.6216	Remote Similarity	NPD5173	Approved
0.6214	Remote Similarity	NPD6110	Phase 1
0.6204	Remote Similarity	NPD5281	Approved
0.6204	Remote Similarity	NPD5284	Approved
0.6198	Remote Similarity	NPD6868	Approved
0.6195	Remote Similarity	NPD5223	Approved
0.619	Remote Similarity	NPD3618	Phase 1
0.619	Remote Similarity	NPD4519	Discontinued
0.619	Remote Similarity	NPD4623	Approved
0.6182	Remote Similarity	NPD5695	Phase 3
0.6179	Remote Similarity	NPD7100	Approved
0.6179	Remote Similarity	NPD7101	Approved
0.6174	Remote Similarity	NPD5141	Approved
0.6154	Remote Similarity	NPD7260	Phase 2
0.6154	Remote Similarity	NPD4197	Approved
0.614	Remote Similarity	NPD5225	Approved
0.614	Remote Similarity	NPD4633	Approved
0.614	Remote Similarity	NPD5224	Approved
0.614	Remote Similarity	NPD5226	Approved
0.6126	Remote Similarity	NPD4697	Phase 3
0.6117	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD3667	Approved
0.6095	Remote Similarity	NPD5329	Approved
0.6095	Remote Similarity	NPD5363	Approved
0.6087	Remote Similarity	NPD5175	Approved
0.6087	Remote Similarity	NPD5174	Approved
0.6083	Remote Similarity	NPD6053	Discontinued
0.6071	Remote Similarity	NPD6084	Phase 2
0.6071	Remote Similarity	NPD4755	Approved
0.6071	Remote Similarity	NPD6083	Phase 2
0.6068	Remote Similarity	NPD5697	Approved
0.6064	Remote Similarity	NPD7331	Phase 2
0.6055	Remote Similarity	NPD6079	Approved
0.6055	Remote Similarity	NPD5694	Approved
0.6055	Remote Similarity	NPD5693	Phase 1
0.604	Remote Similarity	NPD3617	Approved
0.6038	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD4632	Approved
0.6018	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6011	Approved
0.6017	Remote Similarity	NPD6899	Approved
0.6017	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD4786	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5966	Remote Similarity	NPD6013	Approved
0.5966	Remote Similarity	NPD6014	Approved
0.5966	Remote Similarity	NPD6012	Approved
0.5965	Remote Similarity	NPD4700	Approved
0.5963	Remote Similarity	NPD5692	Phase 3
0.5962	Remote Similarity	NPD4223	Phase 3
0.5962	Remote Similarity	NPD4221	Approved
0.5962	Remote Similarity	NPD5209	Approved
0.596	Remote Similarity	NPD4058	Approved
0.5952	Remote Similarity	NPD5983	Phase 2
0.5946	Remote Similarity	NPD7748	Approved
0.5929	Remote Similarity	NPD7902	Approved
0.5926	Remote Similarity	NPD4518	Approved
0.5926	Remote Similarity	NPD6672	Approved
0.5926	Remote Similarity	NPD5737	Approved
0.592	Remote Similarity	NPD4522	Approved
0.5917	Remote Similarity	NPD6883	Approved
0.5917	Remote Similarity	NPD7102	Approved
0.5917	Remote Similarity	NPD7290	Approved
0.5909	Remote Similarity	NPD6050	Approved
0.5909	Remote Similarity	NPD7515	Phase 2
0.5905	Remote Similarity	NPD7154	Phase 3
0.59	Remote Similarity	NPD8264	Approved
0.59	Remote Similarity	NPD8039	Approved
0.5893	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD6336	Discontinued
0.5887	Remote Similarity	NPD6009	Approved
0.5882	Remote Similarity	NPD4730	Approved
0.5882	Remote Similarity	NPD4729	Approved
0.5877	Remote Similarity	NPD4225	Approved
0.5873	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5328	Approved
0.5872	Remote Similarity	NPD6101	Approved
0.5868	Remote Similarity	NPD8130	Phase 1
0.5868	Remote Similarity	NPD6617	Approved
0.5868	Remote Similarity	NPD6847	Approved
0.5868	Remote Similarity	NPD6869	Approved
0.5865	Remote Similarity	NPD5369	Approved
0.5856	Remote Similarity	NPD4202	Approved
0.5849	Remote Similarity	NPD3668	Phase 3
0.5847	Remote Similarity	NPD6402	Approved
0.5847	Remote Similarity	NPD6675	Approved
0.5847	Remote Similarity	NPD7128	Approved
0.5847	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD3573	Approved
0.5833	Remote Similarity	NPD6372	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.582	Remote Similarity	NPD8297	Approved
0.582	Remote Similarity	NPD6882	Approved
0.5818	Remote Similarity	NPD6698	Approved
0.5818	Remote Similarity	NPD46	Approved
0.5818	Remote Similarity	NPD5207	Approved
0.5812	Remote Similarity	NPD4754	Approved
0.581	Remote Similarity	NPD4269	Approved
0.581	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.581	Remote Similarity	NPD4270	Approved
0.58	Remote Similarity	NPD4687	Approved
0.5798	Remote Similarity	NPD5701	Approved
0.5798	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7341	Phase 2
0.5785	Remote Similarity	NPD5248	Approved
0.5785	Remote Similarity	NPD5247	Approved
0.5785	Remote Similarity	NPD5249	Phase 3
0.5785	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD5250	Approved
0.5785	Remote Similarity	NPD5251	Approved
0.5785	Remote Similarity	NPD5135	Approved
0.5785	Remote Similarity	NPD4634	Approved
0.5769	Remote Similarity	NPD4252	Approved
0.5766	Remote Similarity	NPD6411	Approved
0.5755	Remote Similarity	NPD5362	Discontinued
0.575	Remote Similarity	NPD7320	Approved
0.5746	Remote Similarity	NPD6845	Suspended
0.5741	Remote Similarity	NPD4693	Phase 3
0.5741	Remote Similarity	NPD4690	Approved
0.5741	Remote Similarity	NPD4138	Approved
0.5741	Remote Similarity	NPD5786	Approved
0.5741	Remote Similarity	NPD4689	Approved
0.5741	Remote Similarity	NPD5205	Approved
0.5741	Remote Similarity	NPD4688	Approved
0.5739	Remote Similarity	NPD7638	Approved
0.5738	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6673	Approved
0.5727	Remote Similarity	NPD6080	Approved
0.5727	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD4768	Approved
0.5703	Remote Similarity	NPD8513	Phase 3
0.569	Remote Similarity	NPD7640	Approved
0.569	Remote Similarity	NPD7639	Approved
0.5682	Remote Similarity	NPD6033	Approved
0.5676	Remote Similarity	NPD7838	Discovery
0.5676	Remote Similarity	NPD4096	Approved
0.5673	Remote Similarity	NPD4195	Approved
0.5664	Remote Similarity	NPD7900	Approved
0.5664	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4691	Approved
0.5644	Remote Similarity	NPD5733	Approved
0.5635	Remote Similarity	NPD6317	Approved
0.563	Remote Similarity	NPD5909	Discontinued
0.5615	Remote Similarity	NPD4879	Approved
0.561	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.561	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.561	Remote Similarity	NPD8413	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