NPASS Compound

Structure

CID199107 OpenBabel06191715592D 30 32 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 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 0.7202 5.0064 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 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 1 0 0 0 0 0 0 0 0 0 0.0511 4.2633 0.0000 C 0 0 2 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 -0.9271 4.4712 0.0000 O 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 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 29 1 0 0 0 0 11 2 1 6 0 0 0 12 3 1 6 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 4 1 6 0 0 0 13 25 1 0 0 0 0 14 29 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 26 2 0 0 0 0 21 23 1 0 0 0 0 21 27 2 0 0 0 0 22 28 2 0 0 0 0 22 30 1 0 0 0 0 23 5 1 6 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.13
Volume:	427.556
LogP:	3.936
LogD:	2.579
LogS:	-4.828
# Rotatable Bonds:	6
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	5.073
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.76
MDCK Permeability:	1.927803532453254e-05
Pgp-inhibitor:	0.361
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.906
30% Bioavailability (F30%):	0.9

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	80.5150146484375%
Volume Distribution (VD):	2.269
Pgp-substrate:	9.466207504272461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.688
CYP2C19-inhibitor:	0.935
CYP2C19-substrate:	0.571
CYP2C9-inhibitor:	0.914
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.94
CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	2.065
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.941
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.483
Rat Oral Acute Toxicity:	0.771
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.921
Carcinogencity:	0.931
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC199107

Natural Product ID:	NPC199107
*Common Name:**	Chaetoviridin A
IUPAC Name:	(6aS)-5-chloro-9-[(2S,3R)-3-hydroxy-2-methylbutanoyl]-6a-methyl-3-[(E,3S)-3-methylpent-1-enyl]furo[2,3-h]isochromene-6,8-dione
Synonyms:	Chaetoviridin A
Standard InCHIKey:	HWSQVPGTQUYLEQ-CCBHEJLASA-N
Standard InCHI:	InChI=1S/C23H25ClO6/c1-6-11(2)7-8-14-9-15-16(10-29-14)18-17(20(26)12(3)13(4)25)22(28)30-23(18,5)21(27)19(15)24/h7-13,25H,6H2,1-5H3/b8-7+/t11-,12-,13+,23-/m0/s1
SMILES:	CC[C@H](C)/C=C/C1=CC2=C(C(=O)[C@]3(C)C(=C(C(=O)[C@@H](C)[C@@H](C)O)C(=O)O3)C2=CO1)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1802150
PubChem CID:	6450533
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.	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.	mycelium	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	2
MIC	2

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	>	10000.0	nM	PMID[564481]
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	10000.0	nM	PMID[564481]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	1.23	ug.mL-1	PMID[564480]
NPT2527	Organism	Pythium ultimum	Pythium ultimum	MIC	=	33.3	ug.mL-1	PMID[564480]

☑ 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 NPC199107 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	210
0.1-0.2	1331
0.2-0.3	5429
0.3-0.4	10376
0.4-0.5	17039
0.5-0.6	6645
0.6-0.7	1528
0.7-0.8	115
0.8-0.85	18
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC232969
0.8878	High Similarity	NPC143210
0.8788	High Similarity	NPC12727
0.8407	Intermediate Similarity	NPC476815
0.8384	Intermediate Similarity	NPC224270
0.8365	Intermediate Similarity	NPC224172
0.8365	Intermediate Similarity	NPC469851
0.8364	Intermediate Similarity	NPC321496
0.83	Intermediate Similarity	NPC32552
0.8224	Intermediate Similarity	NPC469852
0.8131	Intermediate Similarity	NPC272528
0.8087	Intermediate Similarity	NPC31641
0.8061	Intermediate Similarity	NPC281172
0.8	Intermediate Similarity	NPC245320
0.798	Intermediate Similarity	NPC291712
0.7941	Intermediate Similarity	NPC32944
0.7941	Intermediate Similarity	NPC193396
0.7941	Intermediate Similarity	NPC166110
0.7931	Intermediate Similarity	NPC473145
0.7921	Intermediate Similarity	NPC95364
0.7921	Intermediate Similarity	NPC142159
0.787	Intermediate Similarity	NPC297281
0.787	Intermediate Similarity	NPC473144
0.7864	Intermediate Similarity	NPC282644
0.7864	Intermediate Similarity	NPC29798
0.7864	Intermediate Similarity	NPC248193
0.7757	Intermediate Similarity	NPC215253
0.7757	Intermediate Similarity	NPC185253
0.7672	Intermediate Similarity	NPC243298
0.7664	Intermediate Similarity	NPC166770
0.7658	Intermediate Similarity	NPC469853
0.7589	Intermediate Similarity	NPC327106
0.757	Intermediate Similarity	NPC134083
0.757	Intermediate Similarity	NPC245521
0.7565	Intermediate Similarity	NPC326264
0.7525	Intermediate Similarity	NPC67081
0.7525	Intermediate Similarity	NPC471223
0.75	Intermediate Similarity	NPC274075
0.7478	Intermediate Similarity	NPC66108
0.7387	Intermediate Similarity	NPC271059
0.7387	Intermediate Similarity	NPC25666
0.7383	Intermediate Similarity	NPC471698
0.7368	Intermediate Similarity	NPC38154
0.7273	Intermediate Similarity	NPC54705
0.7217	Intermediate Similarity	NPC23497
0.7193	Intermediate Similarity	NPC266514
0.7172	Intermediate Similarity	NPC264391
0.717	Intermediate Similarity	NPC316228
0.717	Intermediate Similarity	NPC473455
0.7157	Intermediate Similarity	NPC16488
0.7156	Intermediate Similarity	NPC318082
0.7143	Intermediate Similarity	NPC197835
0.7143	Intermediate Similarity	NPC235369
0.7143	Intermediate Similarity	NPC303653
0.7143	Intermediate Similarity	NPC291500
0.7143	Intermediate Similarity	NPC189609
0.7143	Intermediate Similarity	NPC140591
0.7094	Intermediate Similarity	NPC324683
0.7091	Intermediate Similarity	NPC208094
0.708	Intermediate Similarity	NPC320294
0.7075	Intermediate Similarity	NPC87306
0.7064	Intermediate Similarity	NPC31021
0.7064	Intermediate Similarity	NPC214694
0.7064	Intermediate Similarity	NPC295347
0.7054	Intermediate Similarity	NPC472753
0.7048	Intermediate Similarity	NPC113370
0.7048	Intermediate Similarity	NPC476079
0.7048	Intermediate Similarity	NPC473248
0.7048	Intermediate Similarity	NPC103743
0.7027	Intermediate Similarity	NPC35717
0.7027	Intermediate Similarity	NPC300584
0.7025	Intermediate Similarity	NPC21326
0.7019	Intermediate Similarity	NPC307112
0.7009	Intermediate Similarity	NPC89408
0.7009	Intermediate Similarity	NPC475879
0.7	Intermediate Similarity	NPC473291
0.6991	Remote Similarity	NPC472754
0.699	Remote Similarity	NPC475083
0.6983	Remote Similarity	NPC264819
0.6983	Remote Similarity	NPC322903
0.6981	Remote Similarity	NPC153570
0.6972	Remote Similarity	NPC477241
0.6972	Remote Similarity	NPC469632
0.6957	Remote Similarity	NPC469607
0.6952	Remote Similarity	NPC47220
0.6952	Remote Similarity	NPC261721
0.6952	Remote Similarity	NPC315395
0.6952	Remote Similarity	NPC186332
0.6952	Remote Similarity	NPC316426
0.6937	Remote Similarity	NPC239895
0.6937	Remote Similarity	NPC20066
0.693	Remote Similarity	NPC475945
0.693	Remote Similarity	NPC475871
0.693	Remote Similarity	NPC104161
0.693	Remote Similarity	NPC469980
0.693	Remote Similarity	NPC118902
0.6923	Remote Similarity	NPC474251
0.6923	Remote Similarity	NPC469884
0.6903	Remote Similarity	NPC474742
0.69	Remote Similarity	NPC471225
0.6897	Remote Similarity	NPC254538
0.6897	Remote Similarity	NPC474285
0.6881	Remote Similarity	NPC476049
0.6875	Remote Similarity	NPC221414
0.6875	Remote Similarity	NPC471144
0.6875	Remote Similarity	NPC161855
0.6864	Remote Similarity	NPC478209
0.6864	Remote Similarity	NPC206595
0.6857	Remote Similarity	NPC155873
0.6852	Remote Similarity	NPC131864
0.685	Remote Similarity	NPC476008
0.6847	Remote Similarity	NPC172998
0.6847	Remote Similarity	NPC301596
0.6847	Remote Similarity	NPC299396
0.6842	Remote Similarity	NPC273005
0.6842	Remote Similarity	NPC474747
0.6842	Remote Similarity	NPC31058
0.6842	Remote Similarity	NPC149371
0.6842	Remote Similarity	NPC469606
0.6838	Remote Similarity	NPC473807
0.6838	Remote Similarity	NPC89171
0.6838	Remote Similarity	NPC472507
0.6838	Remote Similarity	NPC476802
0.6833	Remote Similarity	NPC469463
0.6833	Remote Similarity	NPC469454
0.6833	Remote Similarity	NPC474271
0.6833	Remote Similarity	NPC469496
0.6822	Remote Similarity	NPC472008
0.6822	Remote Similarity	NPC475902
0.6818	Remote Similarity	NPC475832
0.6818	Remote Similarity	NPC475927
0.6814	Remote Similarity	NPC472972
0.6814	Remote Similarity	NPC475949
0.6814	Remote Similarity	NPC469551
0.681	Remote Similarity	NPC478208
0.6807	Remote Similarity	NPC317107
0.6807	Remote Similarity	NPC179798
0.6807	Remote Similarity	NPC304180
0.6803	Remote Similarity	NPC471145
0.6792	Remote Similarity	NPC122502
0.6792	Remote Similarity	NPC164393
0.6789	Remote Similarity	NPC327760
0.6789	Remote Similarity	NPC142838
0.6789	Remote Similarity	NPC45579
0.6789	Remote Similarity	NPC472705
0.6789	Remote Similarity	NPC303230
0.6789	Remote Similarity	NPC20713
0.6789	Remote Similarity	NPC6099
0.6789	Remote Similarity	NPC114345
0.6786	Remote Similarity	NPC53844
0.6783	Remote Similarity	NPC472755
0.6783	Remote Similarity	NPC472750
0.6783	Remote Similarity	NPC472747
0.678	Remote Similarity	NPC137911
0.678	Remote Similarity	NPC20192
0.678	Remote Similarity	NPC228477
0.6772	Remote Similarity	NPC477745
0.6768	Remote Similarity	NPC470686
0.6762	Remote Similarity	NPC38569
0.6762	Remote Similarity	NPC163615
0.6762	Remote Similarity	NPC219966
0.6759	Remote Similarity	NPC295312
0.6759	Remote Similarity	NPC51358
0.6759	Remote Similarity	NPC307092
0.6759	Remote Similarity	NPC78008
0.6757	Remote Similarity	NPC209355
0.6757	Remote Similarity	NPC272050
0.6757	Remote Similarity	NPC273197
0.6757	Remote Similarity	NPC234339
0.6754	Remote Similarity	NPC47880
0.6754	Remote Similarity	NPC471412
0.6754	Remote Similarity	NPC244456
0.6754	Remote Similarity	NPC469657
0.6754	Remote Similarity	NPC201718
0.6754	Remote Similarity	NPC472643
0.6754	Remote Similarity	NPC471699
0.675	Remote Similarity	NPC317687
0.6748	Remote Similarity	NPC284707
0.6748	Remote Similarity	NPC315974
0.6746	Remote Similarity	NPC120724
0.6729	Remote Similarity	NPC160138
0.6729	Remote Similarity	NPC86005
0.6729	Remote Similarity	NPC471738
0.6729	Remote Similarity	NPC477959
0.6726	Remote Similarity	NPC264378
0.6724	Remote Similarity	NPC474741
0.6724	Remote Similarity	NPC472756
0.6724	Remote Similarity	NPC472748
0.6723	Remote Similarity	NPC472508
0.6723	Remote Similarity	NPC5103
0.6721	Remote Similarity	NPC478216
0.672	Remote Similarity	NPC472000
0.672	Remote Similarity	NPC471999
0.6698	Remote Similarity	NPC242233
0.6697	Remote Similarity	NPC265856
0.6697	Remote Similarity	NPC71533
0.6697	Remote Similarity	NPC106510
0.6697	Remote Similarity	NPC166554
0.6696	Remote Similarity	NPC135576
0.6696	Remote Similarity	NPC93271

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 NPC199107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1527
0.2-0.3	3935
0.3-0.4	2410
0.4-0.5	840
0.5-0.6	238
0.6-0.7	20
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
0.6727	Remote Similarity	NPD5778	Approved
0.6727	Remote Similarity	NPD5779	Approved
0.6612	Remote Similarity	NPD6053	Discontinued
0.6509	Remote Similarity	NPD6110	Phase 1
0.6486	Remote Similarity	NPD7983	Approved
0.648	Remote Similarity	NPD6335	Approved
0.648	Remote Similarity	NPD6313	Approved
0.648	Remote Similarity	NPD6314	Approved
0.6457	Remote Similarity	NPD8513	Phase 3
0.6457	Remote Similarity	NPD5983	Phase 2
0.6408	Remote Similarity	NPD4756	Discovery
0.6385	Remote Similarity	NPD6336	Discontinued
0.6372	Remote Similarity	NPD5282	Discontinued
0.6328	Remote Similarity	NPD8516	Approved
0.6328	Remote Similarity	NPD8517	Approved
0.6328	Remote Similarity	NPD8515	Approved
0.632	Remote Similarity	NPD6868	Approved
0.6306	Remote Similarity	NPD6101	Approved
0.6306	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD7100	Approved
0.6299	Remote Similarity	NPD7101	Approved
0.6293	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4632	Approved
0.6288	Remote Similarity	NPD6033	Approved
0.627	Remote Similarity	NPD6009	Approved
0.6262	Remote Similarity	NPD5209	Approved
0.6261	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD6698	Approved
0.625	Remote Similarity	NPD46	Approved
0.6198	Remote Similarity	NPD5697	Approved
0.6195	Remote Similarity	NPD7637	Suspended
0.6195	Remote Similarity	NPD6411	Approved
0.6174	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7638	Approved
0.6148	Remote Similarity	NPD6899	Approved
0.6148	Remote Similarity	NPD6881	Approved
0.6148	Remote Similarity	NPD6011	Approved
0.6142	Remote Similarity	NPD7115	Discovery
0.6116	Remote Similarity	NPD7128	Approved
0.6116	Remote Similarity	NPD6675	Approved
0.6116	Remote Similarity	NPD6402	Approved
0.6116	Remote Similarity	NPD5739	Approved
0.6106	Remote Similarity	NPD7838	Discovery
0.6106	Remote Similarity	NPD5785	Approved
0.6102	Remote Similarity	NPD7639	Approved
0.6102	Remote Similarity	NPD7640	Approved
0.6098	Remote Similarity	NPD6012	Approved
0.6098	Remote Similarity	NPD6013	Approved
0.6098	Remote Similarity	NPD6014	Approved
0.609	Remote Similarity	NPD8074	Phase 3
0.6075	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5701	Approved
0.6066	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7492	Approved
0.6055	Remote Similarity	NPD7154	Phase 3
0.6048	Remote Similarity	NPD7290	Approved
0.6048	Remote Similarity	NPD6883	Approved
0.6048	Remote Similarity	NPD5169	Approved
0.6048	Remote Similarity	NPD7102	Approved
0.6036	Remote Similarity	NPD4249	Approved
0.6036	Remote Similarity	NPD5786	Approved
0.6034	Remote Similarity	NPD5654	Approved
0.6029	Remote Similarity	NPD7260	Phase 2
0.6016	Remote Similarity	NPD7320	Approved
0.6015	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD5127	Approved
0.6	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD6847	Approved
0.5983	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4251	Approved
0.5982	Remote Similarity	NPD4250	Approved
0.597	Remote Similarity	NPD7078	Approved
0.5968	Remote Similarity	NPD6373	Approved
0.5968	Remote Similarity	NPD6372	Approved
0.5954	Remote Similarity	NPD6016	Approved
0.5954	Remote Similarity	NPD6015	Approved
0.5952	Remote Similarity	NPD8297	Approved
0.5952	Remote Similarity	NPD6882	Approved
0.5946	Remote Similarity	NPD5363	Approved
0.5932	Remote Similarity	NPD6083	Phase 2
0.5932	Remote Similarity	NPD6084	Phase 2
0.5932	Remote Similarity	NPD5959	Approved
0.5926	Remote Similarity	NPD4252	Approved
0.5926	Remote Similarity	NPD7736	Approved
0.592	Remote Similarity	NPD6371	Approved
0.5909	Remote Similarity	NPD6370	Approved
0.5909	Remote Similarity	NPD5988	Approved
0.5897	Remote Similarity	NPD5695	Phase 3
0.5887	Remote Similarity	NPD5168	Approved
0.5887	Remote Similarity	NPD5128	Approved
0.5887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4225	Approved
0.5878	Remote Similarity	NPD6059	Approved
0.5873	Remote Similarity	NPD1719	Phase 1
0.5873	Remote Similarity	NPD5216	Approved
0.5873	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD5215	Approved
0.5873	Remote Similarity	NPD5217	Approved
0.5872	Remote Similarity	NPD5369	Approved
0.5865	Remote Similarity	NPD7604	Phase 2
0.5859	Remote Similarity	NPD5167	Approved
0.5852	Remote Similarity	NPD8293	Discontinued
0.584	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD5956	Approved
0.5818	Remote Similarity	NPD4269	Approved
0.5818	Remote Similarity	NPD4270	Approved
0.5816	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD1696	Phase 3
0.5804	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD1694	Approved
0.5794	Remote Similarity	NPD4634	Approved
0.5789	Remote Similarity	NPD8080	Discontinued
0.5776	Remote Similarity	NPD5693	Phase 1
0.5776	Remote Similarity	NPD5694	Approved
0.5769	Remote Similarity	NPD6317	Approved
0.5766	Remote Similarity	NPD7319	Approved
0.576	Remote Similarity	NPD6686	Approved
0.575	Remote Similarity	NPD5696	Approved
0.5746	Remote Similarity	NPD7829	Approved
0.5746	Remote Similarity	NPD8328	Phase 3
0.5746	Remote Similarity	NPD7830	Approved
0.5743	Remote Similarity	NPD3704	Approved
0.5738	Remote Similarity	NPD5211	Phase 2
0.5726	Remote Similarity	NPD5048	Discontinued
0.5726	Remote Similarity	NPD6008	Approved
0.5714	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8444	Approved
0.5714	Remote Similarity	NPD5222	Approved
0.5714	Remote Similarity	NPD5221	Approved
0.5714	Remote Similarity	NPD7503	Approved
0.5702	Remote Similarity	NPD5285	Approved
0.5702	Remote Similarity	NPD5286	Approved
0.5702	Remote Similarity	NPD4696	Approved
0.5702	Remote Similarity	NPD6648	Approved
0.5692	Remote Similarity	NPD6274	Approved
0.569	Remote Similarity	NPD5692	Phase 3
0.5682	Remote Similarity	NPD4522	Approved
0.568	Remote Similarity	NPD6614	Approved
0.5676	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6435	Approved
0.5669	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD2067	Discontinued
0.5667	Remote Similarity	NPD4755	Approved
0.5667	Remote Similarity	NPD5173	Approved
0.5662	Remote Similarity	NPD7507	Approved
0.5656	Remote Similarity	NPD5223	Approved
0.5656	Remote Similarity	NPD5344	Discontinued
0.5652	Remote Similarity	NPD6672	Approved
0.5652	Remote Similarity	NPD5737	Approved
0.5645	Remote Similarity	NPD5141	Approved
0.5643	Remote Similarity	NPD6845	Suspended
0.5641	Remote Similarity	NPD6050	Approved
0.5641	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5362	Discontinued
0.5614	Remote Similarity	NPD5279	Phase 3
0.561	Remote Similarity	NPD5225	Approved
0.561	Remote Similarity	NPD5224	Approved
0.561	Remote Similarity	NPD5226	Approved
0.561	Remote Similarity	NPD7632	Discontinued
0.561	Remote Similarity	NPD4633	Approved
0.5607	Remote Similarity	NPD8039	Approved
0.5603	Remote Similarity	NPD5370	Suspended
0.5603	Remote Similarity	NPD7285	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