NPASS Compound

Structure

CID224270 OpenBabel06191716022D 27 28 0 0 1 0 0 0 0 0999 V2000 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 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 -2.0000 0.0000 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 8.6603 1.0000 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 6.9282 1.0000 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 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 -2.0000 -1.7321 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 -0.8660 1.5000 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 -0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 9 13 2 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 26 1 0 0 0 0 12 2 1 1 0 0 0 14 23 2 0 0 0 0 14 27 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 24 2 0 0 0 0 20 21 1 0 0 0 0 20 25 2 0 0 0 0 21 5 1 6 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.12
Volume:	392.73
LogP:	4.128
LogD:	2.422
LogS:	-4.589
# Rotatable Bonds:	6
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	4.461
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.685
MDCK Permeability:	2.0266730643925257e-05
Pgp-inhibitor:	0.106
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.83
Plasma Protein Binding (PPB):	81.94905853271484%
Volume Distribution (VD):	2.203
Pgp-substrate:	14.768570899963379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.558
CYP2C19-inhibitor:	0.949
CYP2C19-substrate:	0.475
CYP2C9-inhibitor:	0.898
CYP2C9-substrate:	0.103
CYP2D6-inhibitor:	0.865
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.619

ADMET: Excretion

Clearance (CL):	1.383
Half-life (T1/2):	0.667

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.905
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.247
Rat Oral Acute Toxicity:	0.65
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.935
Carcinogencity:	0.944
Eye Corrosion:	0.004
Eye Irritation:	0.04
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC224270

Natural Product ID:	NPC224270
*Common Name:**	Sclerotiorin
IUPAC Name:	[(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-7-methyl-6,8-dioxoisochromen-7-yl] acetate
Synonyms:	Sclerotiorin
Standard InCHIKey:	SWJLTKXURNHVHE-UPWXJBBJSA-N
Standard InCHI:	InChI=1S/C21H23ClO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-26-15)19(24)21(5,27-14(4)23)20(25)18(16)22/h7-12H,6H2,1-5H3/b8-7+,13-9+/t12-,21+/m0/s1
SMILES:	CC[C@H](C)/C=C(C)/C=C/C1=CC2=C(C(=O)[C@@](C)(C(=O)C2=CO1)OC(=O)C)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095515
PubChem CID:	6436015
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003477] Azaphilones

*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
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	atlantic-forest-soil	n.a.	PMID[20450206]
NPO13628	Rabdosia longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13628	Rabdosia longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10933	Stenanthera gabonensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15729	Streptomyces karnatakensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7875	Pseudocyphellaria berberina	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16003	Machaerium incorruptibile	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3508	Aglaia tenuicaulis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20456	Chrysanthemum tatsienense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5308	Stilpnopappus trichospiroides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9160	Plantago nivalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14633	Tridacna maxima	Species	Tridacnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13628	Rabdosia longituba	Species	Lamiaceae	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
AC50	2
IC50	1
Others	3
Potency	33

Activity Type	# Activity
Cell Line	1
Individual Protein	29
Organism	1
Others	6
PROTEIN COMPLEX	3
PROTEIN-PROTEIN INTERACTION	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[524247]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[524247]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[524247]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[524247]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[524247]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[524247]
NPT534	Individual Protein	Phosphoglycerate kinase, glycosomal	Trypanosoma brucei brucei	Potency	n.a.	22387.2	nM	PMID[524247]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4.6	nM	PMID[524247]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[524247]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[524247]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	5623.4	nM	PMID[524247]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	3.54	%	PMID[524248]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[524247]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[524247]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[524247]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[524247]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[524247]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[524247]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	=	8.0	mm	PMID[524246]
NPT2	Others	Unspecified		Potency	n.a.	20596.2	nM	PMID[524247]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[524247]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[524247]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	50118.7	nM	PMID[524247]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[524247]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[524247]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[524247]
NPT698	Individual Protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[524247]
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	AC50	=	800.0	nM	PMID[524247]
NPT919	Individual Protein	HSP90	Plasmodium falciparum 3D7	AC50	=	2109.0	nM	PMID[524247]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[524247]
NPT821	Individual Protein	Werner syndrome ATP-dependent helicase	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[524247]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[524247]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	6.21	%	PMID[524248]
NPT920	Individual Protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[524247]
NPT2	Others	Unspecified		Potency	n.a.	28183.8	nM	PMID[524247]
NPT2	Others	Unspecified		Potency	n.a.	19952.6	nM	PMID[524247]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	1062.1	nM	PMID[524247]
NPT2	Others	Unspecified		Potency	n.a.	15848.9	nM	PMID[524247]
NPT2	Others	Unspecified		IC50	=	76500.0	nM	PMID[524250]

☑ 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 NPC224270 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	1596
0.2-0.3	6979
0.3-0.4	17377
0.4-0.5	11525
0.5-0.6	4271
0.6-0.7	666
0.7-0.8	52
0.8-0.85	15
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC12727
0.9432	High Similarity	NPC143210
0.8636	High Similarity	NPC291712
0.8523	High Similarity	NPC281172
0.8384	Intermediate Similarity	NPC232969
0.8384	Intermediate Similarity	NPC199107
0.837	Intermediate Similarity	NPC32552
0.837	Intermediate Similarity	NPC193396
0.837	Intermediate Similarity	NPC32944
0.8367	Intermediate Similarity	NPC272528
0.8172	Intermediate Similarity	NPC166110
0.8152	Intermediate Similarity	NPC95364
0.8152	Intermediate Similarity	NPC142159
0.8125	Intermediate Similarity	NPC134083
0.8085	Intermediate Similarity	NPC248193
0.7959	Intermediate Similarity	NPC215253
0.7959	Intermediate Similarity	NPC185253
0.7879	Intermediate Similarity	NPC224172
0.7857	Intermediate Similarity	NPC166770
0.77	Intermediate Similarity	NPC469851
0.7551	Intermediate Similarity	NPC471698
0.7549	Intermediate Similarity	NPC297281
0.7549	Intermediate Similarity	NPC25666
0.7549	Intermediate Similarity	NPC271059
0.7549	Intermediate Similarity	NPC473144
0.7523	Intermediate Similarity	NPC243298
0.7475	Intermediate Similarity	NPC318082
0.7404	Intermediate Similarity	NPC469852
0.7387	Intermediate Similarity	NPC245320
0.7347	Intermediate Similarity	NPC282644
0.7347	Intermediate Similarity	NPC29798
0.7321	Intermediate Similarity	NPC476815
0.7321	Intermediate Similarity	NPC31641
0.7321	Intermediate Similarity	NPC473145
0.7312	Intermediate Similarity	NPC288281
0.7308	Intermediate Similarity	NPC9436
0.7222	Intermediate Similarity	NPC471225
0.7209	Intermediate Similarity	NPC470693
0.72	Intermediate Similarity	NPC31021
0.717	Intermediate Similarity	NPC469853
0.7128	Intermediate Similarity	NPC16488
0.7103	Intermediate Similarity	NPC327106
0.7091	Intermediate Similarity	NPC321496
0.7033	Intermediate Similarity	NPC180290
0.703	Intermediate Similarity	NPC295347
0.7021	Intermediate Similarity	NPC221231
0.7021	Intermediate Similarity	NPC471326
0.7019	Intermediate Similarity	NPC471699
0.6966	Remote Similarity	NPC287878
0.6947	Remote Similarity	NPC118423
0.6931	Remote Similarity	NPC38830
0.6907	Remote Similarity	NPC234038
0.6907	Remote Similarity	NPC472863
0.6907	Remote Similarity	NPC316426
0.6907	Remote Similarity	NPC168248
0.6907	Remote Similarity	NPC315395
0.69	Remote Similarity	NPC45579
0.6893	Remote Similarity	NPC208094
0.6869	Remote Similarity	NPC280833
0.6869	Remote Similarity	NPC284561
0.686	Remote Similarity	NPC191233
0.6848	Remote Similarity	NPC473825
0.6848	Remote Similarity	NPC316324
0.6842	Remote Similarity	NPC268122
0.6837	Remote Similarity	NPC103743
0.6837	Remote Similarity	NPC476079
0.6837	Remote Similarity	NPC113370
0.6804	Remote Similarity	NPC470177
0.6804	Remote Similarity	NPC307112
0.68	Remote Similarity	NPC469372
0.6796	Remote Similarity	NPC299396
0.6796	Remote Similarity	NPC301596
0.6796	Remote Similarity	NPC172998
0.6778	Remote Similarity	NPC276336
0.6774	Remote Similarity	NPC99182
0.6771	Remote Similarity	NPC475083
0.6768	Remote Similarity	NPC26078
0.6768	Remote Similarity	NPC473658
0.6744	Remote Similarity	NPC470688
0.6744	Remote Similarity	NPC220766
0.6739	Remote Similarity	NPC40353
0.6737	Remote Similarity	NPC475833
0.6737	Remote Similarity	NPC42470
0.6735	Remote Similarity	NPC203795
0.6705	Remote Similarity	NPC470256
0.6705	Remote Similarity	NPC134385
0.6703	Remote Similarity	NPC122244
0.6703	Remote Similarity	NPC476355
0.6703	Remote Similarity	NPC470686
0.6701	Remote Similarity	NPC196487
0.6701	Remote Similarity	NPC474359
0.6701	Remote Similarity	NPC14575
0.67	Remote Similarity	NPC51358
0.67	Remote Similarity	NPC307092
0.67	Remote Similarity	NPC474844
0.6699	Remote Similarity	NPC234339
0.6699	Remote Similarity	NPC273197
0.6698	Remote Similarity	NPC194028
0.6698	Remote Similarity	NPC168319
0.6667	Remote Similarity	NPC68156
0.6667	Remote Similarity	NPC10080
0.6667	Remote Similarity	NPC181327
0.6667	Remote Similarity	NPC75315
0.6667	Remote Similarity	NPC163016
0.6667	Remote Similarity	NPC125925
0.6667	Remote Similarity	NPC94200
0.6667	Remote Similarity	NPC123908
0.6667	Remote Similarity	NPC1108
0.6667	Remote Similarity	NPC97173
0.6634	Remote Similarity	NPC213636
0.6634	Remote Similarity	NPC253177
0.6634	Remote Similarity	NPC469595
0.6634	Remote Similarity	NPC280592
0.6634	Remote Similarity	NPC212679
0.6634	Remote Similarity	NPC220454
0.6633	Remote Similarity	NPC67081
0.6633	Remote Similarity	NPC189311
0.6633	Remote Similarity	NPC471223
0.6633	Remote Similarity	NPC130030
0.6633	Remote Similarity	NPC471060
0.6632	Remote Similarity	NPC160582
0.6629	Remote Similarity	NPC151481
0.6602	Remote Similarity	NPC476596
0.6602	Remote Similarity	NPC477129
0.6602	Remote Similarity	NPC477130
0.66	Remote Similarity	NPC475902
0.66	Remote Similarity	NPC472302
0.66	Remote Similarity	NPC196407
0.66	Remote Similarity	NPC471057
0.66	Remote Similarity	NPC471058
0.6598	Remote Similarity	NPC474703
0.6598	Remote Similarity	NPC222358
0.6591	Remote Similarity	NPC21998
0.6591	Remote Similarity	NPC194871
0.6591	Remote Similarity	NPC203335
0.6577	Remote Similarity	NPC228477
0.6577	Remote Similarity	NPC137911
0.6571	Remote Similarity	NPC202705
0.6571	Remote Similarity	NPC245521
0.6569	Remote Similarity	NPC471329
0.6569	Remote Similarity	NPC296114
0.6569	Remote Similarity	NPC469538
0.6566	Remote Similarity	NPC220478
0.6566	Remote Similarity	NPC279859
0.6566	Remote Similarity	NPC38576
0.6559	Remote Similarity	NPC27205
0.6559	Remote Similarity	NPC123360
0.6556	Remote Similarity	NPC59558
0.6556	Remote Similarity	NPC315285
0.6545	Remote Similarity	NPC266514
0.6535	Remote Similarity	NPC115179
0.6535	Remote Similarity	NPC106040
0.6535	Remote Similarity	NPC36668
0.6535	Remote Similarity	NPC471054
0.6535	Remote Similarity	NPC118011
0.6535	Remote Similarity	NPC212598
0.6531	Remote Similarity	NPC30486
0.6526	Remote Similarity	NPC473980
0.6526	Remote Similarity	NPC178277
0.6526	Remote Similarity	NPC471299
0.6526	Remote Similarity	NPC63649
0.6526	Remote Similarity	NPC270126
0.6526	Remote Similarity	NPC473981
0.6526	Remote Similarity	NPC264227
0.6526	Remote Similarity	NPC472965
0.6526	Remote Similarity	NPC271632
0.6522	Remote Similarity	NPC15499
0.6522	Remote Similarity	NPC474758
0.6522	Remote Similarity	NPC259599
0.6522	Remote Similarity	NPC117746
0.6522	Remote Similarity	NPC294434
0.6522	Remote Similarity	NPC140287
0.6518	Remote Similarity	NPC89408
0.6512	Remote Similarity	NPC155849
0.6512	Remote Similarity	NPC474774
0.6509	Remote Similarity	NPC264378
0.6505	Remote Similarity	NPC469939
0.6505	Remote Similarity	NPC476598
0.6505	Remote Similarity	NPC476597
0.6505	Remote Similarity	NPC242637
0.65	Remote Similarity	NPC478145
0.6495	Remote Similarity	NPC85772
0.6495	Remote Similarity	NPC475690
0.6491	Remote Similarity	NPC326264
0.6489	Remote Similarity	NPC41780
0.6489	Remote Similarity	NPC57744
0.6489	Remote Similarity	NPC187568
0.6489	Remote Similarity	NPC82666
0.6489	Remote Similarity	NPC315394
0.6486	Remote Similarity	NPC264819
0.6484	Remote Similarity	NPC163003
0.6484	Remote Similarity	NPC181587
0.6484	Remote Similarity	NPC474539
0.6484	Remote Similarity	NPC133098
0.6481	Remote Similarity	NPC197835
0.6481	Remote Similarity	NPC189609
0.6481	Remote Similarity	NPC140591
0.6481	Remote Similarity	NPC291500
0.6481	Remote Similarity	NPC303653
0.6471	Remote Similarity	NPC265856

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 NPC224270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1635
0.2-0.3	4137
0.3-0.4	2378
0.4-0.5	639
0.5-0.6	159
0.6-0.7	8
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
0.6848	Remote Similarity	NPD4756	Discovery
0.6538	Remote Similarity	NPD5654	Approved
0.6495	Remote Similarity	NPD5209	Approved
0.6415	Remote Similarity	NPD5959	Approved
0.63	Remote Similarity	NPD1694	Approved
0.6292	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD6614	Approved
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD5694	Approved
0.6162	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5692	Phase 3
0.6134	Remote Similarity	NPD6314	Approved
0.6134	Remote Similarity	NPD6313	Approved
0.6134	Remote Similarity	NPD6335	Approved
0.6122	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6672	Approved
0.6117	Remote Similarity	NPD5737	Approved
0.6095	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6868	Approved
0.595	Remote Similarity	NPD7100	Approved
0.595	Remote Similarity	NPD7101	Approved
0.593	Remote Similarity	NPD8779	Phase 3
0.5926	Remote Similarity	NPD5695	Phase 3
0.5909	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6080	Approved
0.5905	Remote Similarity	NPD6904	Approved
0.5905	Remote Similarity	NPD6673	Approved
0.5889	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD3573	Approved
0.5826	Remote Similarity	NPD5697	Approved
0.5818	Remote Similarity	NPD6084	Phase 2
0.5818	Remote Similarity	NPD6083	Phase 2
0.5812	Remote Similarity	NPD2067	Discontinued
0.5785	Remote Similarity	NPD7115	Discovery
0.5784	Remote Similarity	NPD6110	Phase 1
0.5784	Remote Similarity	NPD7154	Phase 3
0.5776	Remote Similarity	NPD6881	Approved
0.5776	Remote Similarity	NPD6899	Approved
0.5776	Remote Similarity	NPD6011	Approved
0.5766	Remote Similarity	NPD5696	Approved
0.5761	Remote Similarity	NPD3704	Approved
0.5755	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5779	Approved
0.5741	Remote Similarity	NPD5778	Approved
0.5728	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5983	Phase 2
0.5726	Remote Similarity	NPD6014	Approved
0.5726	Remote Similarity	NPD6013	Approved
0.5726	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD6053	Discontinued
0.5701	Remote Similarity	NPD6698	Approved
0.5701	Remote Similarity	NPD5785	Approved
0.5701	Remote Similarity	NPD46	Approved
0.5701	Remote Similarity	NPD5207	Approved
0.5701	Remote Similarity	NPD7838	Discovery
0.5678	Remote Similarity	NPD5169	Approved
0.5678	Remote Similarity	NPD6883	Approved
0.5678	Remote Similarity	NPD7102	Approved
0.5678	Remote Similarity	NPD7290	Approved
0.5673	Remote Similarity	NPD1696	Phase 3
0.5669	Remote Similarity	NPD6336	Discontinued
0.5644	Remote Similarity	NPD4695	Discontinued
0.563	Remote Similarity	NPD8130	Phase 1
0.563	Remote Similarity	NPD6650	Approved
0.563	Remote Similarity	NPD6869	Approved
0.563	Remote Similarity	NPD6649	Approved
0.563	Remote Similarity	NPD6847	Approved
0.563	Remote Similarity	NPD6617	Approved
0.563	Remote Similarity	NPD5127	Approved
0.5619	Remote Similarity	NPD5330	Approved
0.5619	Remote Similarity	NPD6684	Approved
0.5619	Remote Similarity	NPD6098	Approved
0.5619	Remote Similarity	NPD7521	Approved
0.5619	Remote Similarity	NPD7334	Approved
0.5619	Remote Similarity	NPD7146	Approved
0.5619	Remote Similarity	NPD6409	Approved
0.5614	Remote Similarity	NPD5091	Approved
0.5607	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6101	Approved
0.5604	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD5739	Approved
0.5603	Remote Similarity	NPD6402	Approved
0.5603	Remote Similarity	NPD7128	Approved
0.5603	Remote Similarity	NPD6675	Approved

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