NPASS Compound

Structure

CID12727 OpenBabel06191715342D 29 31 0 0 1 0 0 0 0 0999 V2000 7.0132 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 -5.0064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 -3.1043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -3.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 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 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -3.3090 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 6 1 0 0 0 0 2 7 1 0 0 0 0 4 13 1 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 11 28 1 0 0 0 0 12 3 1 1 0 0 0 13 20 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 18 1 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 21 23 1 0 0 0 0 21 26 2 0 0 0 0 22 27 2 0 0 0 0 22 29 1 0 0 0 0 23 5 1 1 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.12
Volume:	416.129
LogP:	4.354
LogD:	3.246
LogS:	-5.304
# Rotatable Bonds:	5
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.373
Synthetic Accessibility Score:	4.769
Fsp3:	0.348
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:	-4.791
MDCK Permeability:	1.8511222151573747e-05
Pgp-inhibitor:	0.859
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.48
30% Bioavailability (F30%):	0.498

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.255
Plasma Protein Binding (PPB):	81.79581451416016%
Volume Distribution (VD):	2.251
Pgp-substrate:	8.916816711425781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.68
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.252
CYP2C9-inhibitor:	0.942
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.97
CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.97
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	3.075
Half-life (T1/2):	0.196

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.906
Rat Oral Acute Toxicity:	0.951
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.946
Carcinogencity:	0.943
Eye Corrosion:	0.003
Eye Irritation:	0.049
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC12727

Natural Product ID:	NPC12727
*Common Name:**	Chaetoviridin E
IUPAC Name:	(6aS)-5-chloro-6a-methyl-9-[(E)-2-methylbut-2-enoyl]-3-[(E,3S)-3-methylpent-1-enyl]furo[2,3-h]isochromene-6,8-dione
Synonyms:	Chaetoviridin E; Chaetoviridine E
Standard InCHIKey:	XEBNYZYYHZZSJR-IIWQDEIUSA-N
Standard InCHI:	InChI=1S/C23H23ClO5/c1-6-12(3)8-9-14-10-15-16(11-28-14)18-17(20(25)13(4)7-2)22(27)29-23(18,5)21(26)19(15)24/h7-12H,6H2,1-5H3/b9-8+,13-7+/t12-,23-/m0/s1
SMILES:	CC[C@@H](/C=C/C1=CC2=C(Cl)C(=O)[C@@]3(C(=C(C(=O)O3)C(=O)/C(=C/C)/C)C2=CO1)C)C
Synthetic Gene Cluster:	BGC0001405;
ChEMBL Identifier:	CHEMBL1802154
PubChem CID:	25108108
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	n.a.	n.a.	n.a.	PMID[19246197]
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[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]
NPO41091	Chaetomium globosum MP4-S01-7	Strain	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32193933]
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
MIC	1

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	40600.0	nM	PMID[566440]
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	>	10000.0	nM	PMID[566441]
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	10000.0	nM	PMID[566441]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	50.0	ug.mL-1	PMID[566439]

☑ 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 NPC12727 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	224
0.1-0.2	1599
0.2-0.3	7019
0.3-0.4	16550
0.4-0.5	12287
0.5-0.6	4296
0.6-0.7	631
0.7-0.8	69
0.8-0.85	8
0.85-0.9	9
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC143210
0.9545	High Similarity	NPC224270
0.9091	High Similarity	NPC291712
0.8977	High Similarity	NPC281172
0.8804	High Similarity	NPC193396
0.8804	High Similarity	NPC32944
0.8788	High Similarity	NPC232969
0.8788	High Similarity	NPC199107
0.8602	High Similarity	NPC166110
0.8587	High Similarity	NPC95364
0.8587	High Similarity	NPC142159
0.8511	High Similarity	NPC248193
0.8404	Intermediate Similarity	NPC32552
0.84	Intermediate Similarity	NPC272528
0.81	Intermediate Similarity	NPC469851
0.7921	Intermediate Similarity	NPC224172
0.78	Intermediate Similarity	NPC134083
0.7788	Intermediate Similarity	NPC469852
0.7767	Intermediate Similarity	NPC271059
0.7767	Intermediate Similarity	NPC25666
0.7755	Intermediate Similarity	NPC29798
0.7755	Intermediate Similarity	NPC282644
0.7727	Intermediate Similarity	NPC243298
0.77	Intermediate Similarity	NPC318082
0.7647	Intermediate Similarity	NPC215253
0.7647	Intermediate Similarity	NPC185253
0.76	Intermediate Similarity	NPC471698
0.7596	Intermediate Similarity	NPC297281
0.7596	Intermediate Similarity	NPC473144
0.7589	Intermediate Similarity	NPC245320
0.7549	Intermediate Similarity	NPC166770
0.7547	Intermediate Similarity	NPC469853
0.7522	Intermediate Similarity	NPC31641
0.7522	Intermediate Similarity	NPC476815
0.7522	Intermediate Similarity	NPC473145
0.7455	Intermediate Similarity	NPC321496
0.7426	Intermediate Similarity	NPC31021
0.7283	Intermediate Similarity	NPC471225
0.7273	Intermediate Similarity	NPC470693
0.7222	Intermediate Similarity	NPC287878
0.7188	Intermediate Similarity	NPC16488
0.7156	Intermediate Similarity	NPC327106
0.7087	Intermediate Similarity	NPC295347
0.7075	Intermediate Similarity	NPC471699
0.7041	Intermediate Similarity	NPC130030
0.7037	Intermediate Similarity	NPC9436
0.701	Intermediate Similarity	NPC118423
0.701	Intermediate Similarity	NPC288281
0.7	Intermediate Similarity	NPC475902
0.697	Remote Similarity	NPC315395
0.697	Remote Similarity	NPC316426
0.697	Remote Similarity	NPC168248
0.6952	Remote Similarity	NPC208094
0.6932	Remote Similarity	NPC191233
0.6931	Remote Similarity	NPC280833
0.6915	Remote Similarity	NPC473825
0.6907	Remote Similarity	NPC268122
0.69	Remote Similarity	NPC103743
0.69	Remote Similarity	NPC476079
0.69	Remote Similarity	NPC113370
0.6869	Remote Similarity	NPC307112
0.6857	Remote Similarity	NPC299396
0.6857	Remote Similarity	NPC172998
0.6857	Remote Similarity	NPC301596
0.6842	Remote Similarity	NPC99182
0.6837	Remote Similarity	NPC475083
0.6832	Remote Similarity	NPC469653
0.6832	Remote Similarity	NPC471047
0.6832	Remote Similarity	NPC469628
0.6832	Remote Similarity	NPC475906
0.6832	Remote Similarity	NPC469631
0.6818	Remote Similarity	NPC220766
0.6818	Remote Similarity	NPC470688
0.6804	Remote Similarity	NPC42470
0.68	Remote Similarity	NPC472863
0.68	Remote Similarity	NPC261721
0.68	Remote Similarity	NPC38576
0.68	Remote Similarity	NPC279859
0.6792	Remote Similarity	NPC245521
0.6774	Remote Similarity	NPC470686
0.6774	Remote Similarity	NPC122244
0.6771	Remote Similarity	NPC473981
0.6771	Remote Similarity	NPC473980
0.6762	Remote Similarity	NPC209355
0.6762	Remote Similarity	NPC234339
0.6762	Remote Similarity	NPC273197
0.6737	Remote Similarity	NPC180290
0.6737	Remote Similarity	NPC68156
0.6735	Remote Similarity	NPC94200
0.6735	Remote Similarity	NPC471326
0.6735	Remote Similarity	NPC221231
0.6735	Remote Similarity	NPC475690
0.6733	Remote Similarity	NPC125925
0.6731	Remote Similarity	NPC1108
0.67	Remote Similarity	NPC189311
0.67	Remote Similarity	NPC67081
0.67	Remote Similarity	NPC471223
0.6699	Remote Similarity	NPC213636
0.6699	Remote Similarity	NPC469372
0.6699	Remote Similarity	NPC280592
0.6699	Remote Similarity	NPC253177
0.6699	Remote Similarity	NPC475879
0.6696	Remote Similarity	NPC326264
0.6667	Remote Similarity	NPC54705
0.6667	Remote Similarity	NPC475699
0.6667	Remote Similarity	NPC241507
0.6667	Remote Similarity	NPC215745
0.6667	Remote Similarity	NPC26078
0.6667	Remote Similarity	NPC238948
0.6667	Remote Similarity	NPC196407
0.6667	Remote Similarity	NPC38830
0.6667	Remote Similarity	NPC12815
0.6667	Remote Similarity	NPC473658
0.6667	Remote Similarity	NPC476596
0.6667	Remote Similarity	NPC203335
0.6667	Remote Similarity	NPC472302
0.6637	Remote Similarity	NPC228477
0.6637	Remote Similarity	NPC23497
0.6637	Remote Similarity	NPC137911
0.6635	Remote Similarity	NPC45579
0.6635	Remote Similarity	NPC471329
0.6635	Remote Similarity	NPC296114
0.6634	Remote Similarity	NPC234038
0.6633	Remote Similarity	NPC275507
0.6632	Remote Similarity	NPC123360
0.6632	Remote Similarity	NPC27205
0.6609	Remote Similarity	NPC66108
0.6607	Remote Similarity	NPC266514
0.6606	Remote Similarity	NPC194028
0.6606	Remote Similarity	NPC168319
0.6602	Remote Similarity	NPC51358
0.6602	Remote Similarity	NPC307092
0.6602	Remote Similarity	NPC284561
0.6602	Remote Similarity	NPC474844
0.66	Remote Similarity	NPC30486
0.6598	Remote Similarity	NPC471299
0.6598	Remote Similarity	NPC178277
0.6596	Remote Similarity	NPC294434
0.6596	Remote Similarity	NPC476355
0.6596	Remote Similarity	NPC474758
0.6596	Remote Similarity	NPC15499
0.6596	Remote Similarity	NPC259599
0.6596	Remote Similarity	NPC117746
0.6593	Remote Similarity	NPC470256
0.6579	Remote Similarity	NPC89408
0.6574	Remote Similarity	NPC264378
0.6571	Remote Similarity	NPC476598
0.6571	Remote Similarity	NPC469939
0.6571	Remote Similarity	NPC476597
0.6571	Remote Similarity	NPC165383
0.6569	Remote Similarity	NPC75315
0.6569	Remote Similarity	NPC163016
0.6569	Remote Similarity	NPC478145
0.6569	Remote Similarity	NPC266957
0.6566	Remote Similarity	NPC85772
0.6562	Remote Similarity	NPC316324
0.6562	Remote Similarity	NPC57744
0.6559	Remote Similarity	NPC133098
0.6549	Remote Similarity	NPC264819
0.6545	Remote Similarity	NPC140591
0.6545	Remote Similarity	NPC197835
0.6545	Remote Similarity	NPC291500
0.6545	Remote Similarity	NPC303653
0.6545	Remote Similarity	NPC189609
0.6538	Remote Similarity	NPC212679
0.6538	Remote Similarity	NPC220454
0.6538	Remote Similarity	NPC469595
0.6535	Remote Similarity	NPC470177
0.6535	Remote Similarity	NPC155873
0.6526	Remote Similarity	NPC469414
0.6526	Remote Similarity	NPC329826
0.6522	Remote Similarity	NPC232812
0.6514	Remote Similarity	NPC476299
0.6514	Remote Similarity	NPC474012
0.6514	Remote Similarity	NPC469551
0.6509	Remote Similarity	NPC477130
0.6509	Remote Similarity	NPC469632
0.6509	Remote Similarity	NPC477241
0.6509	Remote Similarity	NPC477129
0.6509	Remote Similarity	NPC470697
0.6505	Remote Similarity	NPC260343
0.65	Remote Similarity	NPC193198
0.6495	Remote Similarity	NPC315765
0.6495	Remote Similarity	NPC264391
0.6495	Remote Similarity	NPC469510
0.6495	Remote Similarity	NPC471220
0.6495	Remote Similarity	NPC128276
0.6491	Remote Similarity	NPC38154
0.6489	Remote Similarity	NPC276336
0.6486	Remote Similarity	NPC118902
0.6486	Remote Similarity	NPC104161
0.6486	Remote Similarity	NPC469980
0.6484	Remote Similarity	NPC194871
0.6484	Remote Similarity	NPC21998
0.6481	Remote Similarity	NPC239895
0.6481	Remote Similarity	NPC84335
0.6481	Remote Similarity	NPC53844
0.6481	Remote Similarity	NPC38530
0.6481	Remote Similarity	NPC202705
0.6481	Remote Similarity	NPC2049

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 NPC12727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1637
0.2-0.3	4209
0.3-0.4	2311
0.4-0.5	652
0.5-0.6	140
0.6-0.7	6
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
0.6735	Remote Similarity	NPD5209	Approved
0.6562	Remote Similarity	NPD4756	Discovery
0.6449	Remote Similarity	NPD5654	Approved
0.633	Remote Similarity	NPD5959	Approved
0.6238	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD1694	Approved
0.6174	Remote Similarity	NPD6614	Approved
0.6168	Remote Similarity	NPD5694	Approved
0.6168	Remote Similarity	NPD5693	Phase 1
0.6075	Remote Similarity	NPD5692	Phase 3
0.6066	Remote Similarity	NPD6314	Approved
0.6066	Remote Similarity	NPD6313	Approved
0.6066	Remote Similarity	NPD6335	Approved
0.6038	Remote Similarity	NPD5737	Approved
0.6038	Remote Similarity	NPD6672	Approved
0.6022	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.602	Remote Similarity	NPD8039	Approved
0.6019	Remote Similarity	NPD6050	Approved
0.5984	Remote Similarity	NPD7115	Discovery
0.5926	Remote Similarity	NPD5785	Approved
0.5902	Remote Similarity	NPD6868	Approved
0.5887	Remote Similarity	NPD7100	Approved
0.5887	Remote Similarity	NPD7101	Approved
0.5882	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2067	Discontinued
0.5856	Remote Similarity	NPD5695	Phase 3
0.5833	Remote Similarity	NPD6904	Approved
0.5833	Remote Similarity	NPD6673	Approved
0.5833	Remote Similarity	NPD6080	Approved
0.5818	Remote Similarity	NPD5779	Approved
0.5818	Remote Similarity	NPD5778	Approved
0.581	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5282	Discontinued
0.5763	Remote Similarity	NPD5697	Approved
0.5755	Remote Similarity	NPD5363	Approved
0.5752	Remote Similarity	NPD6084	Phase 2
0.5752	Remote Similarity	NPD6083	Phase 2
0.5745	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7154	Phase 3
0.5714	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD6899	Approved
0.5714	Remote Similarity	NPD6881	Approved
0.5702	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4225	Approved
0.5702	Remote Similarity	NPD5696	Approved
0.5688	Remote Similarity	NPD6101	Approved
0.5688	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD5983	Phase 2
0.5667	Remote Similarity	NPD6013	Approved
0.5667	Remote Similarity	NPD6012	Approved
0.5667	Remote Similarity	NPD8779	Phase 3
0.5667	Remote Similarity	NPD6014	Approved
0.5664	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6053	Discontinued
0.5648	Remote Similarity	NPD3573	Approved
0.5638	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD5207	Approved
0.563	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.562	Remote Similarity	NPD7290	Approved
0.562	Remote Similarity	NPD6883	Approved
0.562	Remote Similarity	NPD5169	Approved
0.562	Remote Similarity	NPD7102	Approved
0.5615	Remote Similarity	NPD6336	Discontinued
0.5607	Remote Similarity	NPD1696	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