NPASS Compound

Structure

CID206579 OpenBabel06191715592D 28 32 0 0 1 0 0 0 0 0999 V2000 -5.0198 -2.0333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8456 -3.4054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5268 -0.4935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6827 -2.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5277 -1.4594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0080 -2.9218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6892 -0.0099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4877 -2.4732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3376 -2.0028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7083 0.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8584 0.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0374 -1.0621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6877 -1.9468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 0.4404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6554 -1.9724 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3552 -1.0317 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0024 -1.9501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8501 -1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5229 -0.5308 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6730 -1.0012 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8408 -0.5003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8872 -0.5918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 0.9107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8056 -2.4427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2051 -0.5613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8450 -1.4636 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 12 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 13 1 0 0 0 0 5 13 1 0 0 0 0 6 17 2 0 0 0 0 7 18 2 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 11 2 0 0 0 0 10 14 1 0 0 0 0 11 22 1 0 0 0 0 12 23 2 0 0 0 0 12 26 1 0 0 0 0 13 19 2 0 0 0 0 14 24 2 0 0 0 0 15 21 1 0 0 0 0 15 25 1 6 0 0 0 16 20 1 0 0 0 0 16 26 1 6 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 20 14 1 1 0 0 0 20 21 1 0 0 0 0 21 22 1 6 0 0 0 22 27 1 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.11
Volume:	375.299
LogP:	2.254
LogD:	1.803
LogS:	-3.802
# Rotatable Bonds:	2
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.607
Synthetic Accessibility Score:	4.848
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.794
MDCK Permeability:	4.118227298022248e-05
Pgp-inhibitor:	0.716
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.833
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.944
Plasma Protein Binding (PPB):	91.73359680175781%
Volume Distribution (VD):	1.191
Pgp-substrate:	10.024614334106445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.312
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.571
CYP2C19-substrate:	0.165
CYP2C9-inhibitor:	0.513
CYP2C9-substrate:	0.196
CYP2D6-inhibitor:	0.763
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.881
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	2.951
Half-life (T1/2):	0.47

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.695
AMES Toxicity:	0.949
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.267
Skin Sensitization:	0.143
Carcinogencity:	0.554
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC206579

Natural Product ID:	NPC206579
*Common Name:**	Decaspirone E
IUPAC Name:	n.a.
Synonyms:	Decaspirone E
Standard InCHIKey:	VCGPNYQDRSFKQN-VAKZPMALSA-N
Standard InCHI:	InChI=1S/C22H18O6/c1-12(23)26-16-9-8-15(25)21-20(16)14(24)10-11-22(21)27-17-6-2-4-13-5-3-7-18(28-22)19(13)17/h2-11,15-16,20-21,25H,1H3/t15-,16+,20-,21-/m1/s1
SMILES:	CC(=O)O[C@H]1C=C[C@H]([C@@H]2[C@@H]1C(=O)C=CC12Oc2cccc3cccc(c23)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463696
PubChem CID:	16099374
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10923847]
NPO22513	Decaisnella thyridioides	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17190439]
NPO27979	Guatteria friesiana	Species	Annonaceae	Eukaryota	Stems	n.a.	n.a.	PMID[19639965]
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23859780]
NPO27979	Guatteria friesiana	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[27300257]
NPO18233	Capparis sepiaria	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21115	Crepidiastrum keiskeanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17178	Labisia pumila	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26602	Ranunculus cantoniensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28371	Echinodontium japonicum	Species	Echinodontiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20220	Coccus citri	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22387	Guettarda speciosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21877	Aplysilla violacea	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22585	Thymus striatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22001	Delphinus longirostris	Species	Delphinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21512	Salvia cardiophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19400	Cussonia natalensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10812	Beaucarnea hookeri	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27979	Guatteria friesiana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23179	Penicillium paraherquei	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22513	Decaisnella thyridioides	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2283	Epichloe uncinata	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20542	Vellozia phalocarpa	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8904	Oreocnide frutescens	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22325	Caesalpinia sepiaria	Species	Fabaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	30.0	mm	PMID[533885]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	17.0	mm	PMID[533885]

☑ 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 NPC206579 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	320
0.1-0.2	1311
0.2-0.3	3192
0.3-0.4	7439
0.4-0.5	11676
0.5-0.6	4062
0.6-0.7	8598
0.7-0.8	6052
0.8-0.85	26
0.85-0.9	12
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC11800
0.9784	High Similarity	NPC257404
0.9433	High Similarity	NPC133585
0.9371	High Similarity	NPC97662
0.9296	High Similarity	NPC197461
0.9281	High Similarity	NPC92932
0.8921	High Similarity	NPC284232
0.8716	High Similarity	NPC47152
0.8591	High Similarity	NPC469408
0.8523	High Similarity	NPC306816
0.8467	Intermediate Similarity	NPC473951
0.8411	Intermediate Similarity	NPC301949
0.8403	Intermediate Similarity	NPC138940
0.8378	Intermediate Similarity	NPC473499
0.8323	Intermediate Similarity	NPC472150
0.8311	Intermediate Similarity	NPC193920
0.8291	Intermediate Similarity	NPC472156
0.8258	Intermediate Similarity	NPC39819
0.821	Intermediate Similarity	NPC175082
0.8187	Intermediate Similarity	NPC73148
0.816	Intermediate Similarity	NPC63470
0.8153	Intermediate Similarity	NPC185103
0.8148	Intermediate Similarity	NPC178281
0.8121	Intermediate Similarity	NPC472151
0.8101	Intermediate Similarity	NPC267242
0.8089	Intermediate Similarity	NPC281272
0.8072	Intermediate Similarity	NPC85368
0.8063	Intermediate Similarity	NPC57072
0.8063	Intermediate Similarity	NPC231475
0.8063	Intermediate Similarity	NPC193749
0.8052	Intermediate Similarity	NPC211565
0.805	Intermediate Similarity	NPC469507
0.8049	Intermediate Similarity	NPC103633
0.8041	Intermediate Similarity	NPC161856
0.8041	Intermediate Similarity	NPC281169
0.8041	Intermediate Similarity	NPC51087
0.8041	Intermediate Similarity	NPC291119
0.8038	Intermediate Similarity	NPC60084
0.8037	Intermediate Similarity	NPC99216
0.8025	Intermediate Similarity	NPC146837
0.8025	Intermediate Similarity	NPC278329
0.8025	Intermediate Similarity	NPC216752
0.8024	Intermediate Similarity	NPC470667
0.8013	Intermediate Similarity	NPC477537
0.8013	Intermediate Similarity	NPC146014
0.8012	Intermediate Similarity	NPC328093
0.8	Intermediate Similarity	NPC476026
0.8	Intermediate Similarity	NPC61284
0.8	Intermediate Similarity	NPC177742
0.8	Intermediate Similarity	NPC472152
0.8	Intermediate Similarity	NPC474441
0.8	Intermediate Similarity	NPC474398
0.8	Intermediate Similarity	NPC246274
0.8	Intermediate Similarity	NPC113428
0.8	Intermediate Similarity	NPC474401
0.7988	Intermediate Similarity	NPC178173
0.7987	Intermediate Similarity	NPC115861
0.7975	Intermediate Similarity	NPC474843
0.7975	Intermediate Similarity	NPC17432
0.7963	Intermediate Similarity	NPC472153
0.7962	Intermediate Similarity	NPC131874
0.7962	Intermediate Similarity	NPC475890
0.7962	Intermediate Similarity	NPC295036
0.7962	Intermediate Similarity	NPC470107
0.7959	Intermediate Similarity	NPC470160
0.7952	Intermediate Similarity	NPC477571
0.7952	Intermediate Similarity	NPC251144
0.7952	Intermediate Similarity	NPC477573
0.7952	Intermediate Similarity	NPC477572
0.7952	Intermediate Similarity	NPC241387
0.795	Intermediate Similarity	NPC186113
0.795	Intermediate Similarity	NPC183402
0.7949	Intermediate Similarity	NPC228012
0.7949	Intermediate Similarity	NPC146388
0.7949	Intermediate Similarity	NPC22137
0.7941	Intermediate Similarity	NPC475161
0.7941	Intermediate Similarity	NPC477860
0.7939	Intermediate Similarity	NPC472660
0.7937	Intermediate Similarity	NPC164244
0.7935	Intermediate Similarity	NPC60389
0.7935	Intermediate Similarity	NPC308799
0.7927	Intermediate Similarity	NPC297404
0.7927	Intermediate Similarity	NPC280923
0.7927	Intermediate Similarity	NPC75944
0.7927	Intermediate Similarity	NPC11608
0.7925	Intermediate Similarity	NPC279281
0.7925	Intermediate Similarity	NPC299761
0.7925	Intermediate Similarity	NPC230439
0.7925	Intermediate Similarity	NPC260604
0.7925	Intermediate Similarity	NPC299435
0.7925	Intermediate Similarity	NPC92153
0.7922	Intermediate Similarity	NPC472154
0.7917	Intermediate Similarity	NPC186800
0.7917	Intermediate Similarity	NPC68381
0.7917	Intermediate Similarity	NPC223735
0.7917	Intermediate Similarity	NPC307754
0.7914	Intermediate Similarity	NPC212099
0.7914	Intermediate Similarity	NPC473022
0.7914	Intermediate Similarity	NPC101116
0.7914	Intermediate Similarity	NPC22324
0.7904	Intermediate Similarity	NPC472620
0.7904	Intermediate Similarity	NPC315619
0.7898	Intermediate Similarity	NPC70764
0.7895	Intermediate Similarity	NPC477535
0.7892	Intermediate Similarity	NPC207574
0.7892	Intermediate Similarity	NPC297195
0.7892	Intermediate Similarity	NPC291795
0.7892	Intermediate Similarity	NPC222455
0.7888	Intermediate Similarity	NPC67197
0.7885	Intermediate Similarity	NPC71055
0.7885	Intermediate Similarity	NPC4958
0.7885	Intermediate Similarity	NPC92054
0.7885	Intermediate Similarity	NPC140722
0.7885	Intermediate Similarity	NPC142863
0.7882	Intermediate Similarity	NPC299149
0.7882	Intermediate Similarity	NPC114257
0.7882	Intermediate Similarity	NPC277710
0.7882	Intermediate Similarity	NPC153578
0.7875	Intermediate Similarity	NPC3898
0.7875	Intermediate Similarity	NPC57141
0.7871	Intermediate Similarity	NPC288531
0.787	Intermediate Similarity	NPC76112
0.787	Intermediate Similarity	NPC170018
0.787	Intermediate Similarity	NPC92403
0.787	Intermediate Similarity	NPC66820
0.787	Intermediate Similarity	NPC475246
0.7866	Intermediate Similarity	NPC74371
0.7866	Intermediate Similarity	NPC120677
0.7866	Intermediate Similarity	NPC475183
0.7862	Intermediate Similarity	NPC470841
0.7862	Intermediate Similarity	NPC215811
0.7857	Intermediate Similarity	NPC154986
0.7857	Intermediate Similarity	NPC203751
0.7853	Intermediate Similarity	NPC18380
0.7853	Intermediate Similarity	NPC71780
0.7853	Intermediate Similarity	NPC175513
0.7849	Intermediate Similarity	NPC231254
0.7848	Intermediate Similarity	NPC473966
0.7848	Intermediate Similarity	NPC93619
0.7844	Intermediate Similarity	NPC472129
0.7844	Intermediate Similarity	NPC298778
0.7844	Intermediate Similarity	NPC43434
0.7843	Intermediate Similarity	NPC20631
0.7843	Intermediate Similarity	NPC245219
0.7843	Intermediate Similarity	NPC93640
0.7843	Intermediate Similarity	NPC31081
0.7843	Intermediate Similarity	NPC145319
0.784	Intermediate Similarity	NPC43761
0.784	Intermediate Similarity	NPC226287
0.7836	Intermediate Similarity	NPC170203
0.7831	Intermediate Similarity	NPC116745
0.7831	Intermediate Similarity	NPC249977
0.7831	Intermediate Similarity	NPC298847
0.7829	Intermediate Similarity	NPC48474
0.7826	Intermediate Similarity	NPC473323
0.7824	Intermediate Similarity	NPC477682
0.7824	Intermediate Similarity	NPC477683
0.7823	Intermediate Similarity	NPC2989
0.7821	Intermediate Similarity	NPC299011
0.7821	Intermediate Similarity	NPC469758
0.7821	Intermediate Similarity	NPC474422
0.7818	Intermediate Similarity	NPC7752
0.7815	Intermediate Similarity	NPC131198
0.7812	Intermediate Similarity	NPC477691
0.7812	Intermediate Similarity	NPC135522
0.7811	Intermediate Similarity	NPC63105
0.7811	Intermediate Similarity	NPC470454
0.7811	Intermediate Similarity	NPC3718
0.7811	Intermediate Similarity	NPC294149
0.7811	Intermediate Similarity	NPC232412
0.7811	Intermediate Similarity	NPC98667
0.7811	Intermediate Similarity	NPC86809
0.7811	Intermediate Similarity	NPC199533
0.7811	Intermediate Similarity	NPC474345
0.7806	Intermediate Similarity	NPC274085
0.7806	Intermediate Similarity	NPC43716
0.7806	Intermediate Similarity	NPC89664
0.7806	Intermediate Similarity	NPC101255
0.7806	Intermediate Similarity	NPC475719
0.7806	Intermediate Similarity	NPC138915
0.7805	Intermediate Similarity	NPC56735
0.7805	Intermediate Similarity	NPC61594
0.7805	Intermediate Similarity	NPC473961
0.7801	Intermediate Similarity	NPC193193
0.7799	Intermediate Similarity	NPC215060
0.7799	Intermediate Similarity	NPC476352
0.7798	Intermediate Similarity	NPC76128
0.7798	Intermediate Similarity	NPC271385
0.7798	Intermediate Similarity	NPC111536
0.7798	Intermediate Similarity	NPC30432
0.7798	Intermediate Similarity	NPC5029
0.7791	Intermediate Similarity	NPC472618
0.7791	Intermediate Similarity	NPC292863
0.7791	Intermediate Similarity	NPC184326
0.7791	Intermediate Similarity	NPC271479
0.7785	Intermediate Similarity	NPC477381
0.7785	Intermediate Similarity	NPC100818
0.7784	Intermediate Similarity	NPC472619
0.7784	Intermediate Similarity	NPC259905
0.7784	Intermediate Similarity	NPC470206

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 NPC206579 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	850
0.2-0.3	1592
0.3-0.4	2485
0.4-0.5	2075
0.5-0.6	1212
0.6-0.7	517
0.7-0.8	140
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
0.816	Intermediate Similarity	NPD3751	Discontinued
0.8129	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2346	Discontinued
0.7914	Intermediate Similarity	NPD3787	Discontinued
0.787	Intermediate Similarity	NPD8312	Approved
0.787	Intermediate Similarity	NPD8313	Approved
0.7847	Intermediate Similarity	NPD2797	Approved
0.7823	Intermediate Similarity	NPD3268	Approved
0.7812	Intermediate Similarity	NPD7819	Suspended
0.7764	Intermediate Similarity	NPD5402	Approved
0.7756	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3750	Approved
0.7669	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2799	Discontinued
0.7613	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2313	Discontinued
0.7582	Intermediate Similarity	NPD2935	Discontinued
0.7574	Intermediate Similarity	NPD7054	Approved
0.7574	Intermediate Similarity	NPD5844	Phase 1
0.7568	Intermediate Similarity	NPD6832	Phase 2
0.7566	Intermediate Similarity	NPD7097	Phase 1
0.7562	Intermediate Similarity	NPD3226	Approved
0.7551	Intermediate Similarity	NPD2798	Approved
0.755	Intermediate Similarity	NPD1933	Approved
0.755	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5403	Approved
0.7544	Intermediate Similarity	NPD6559	Discontinued
0.7534	Intermediate Similarity	NPD3225	Approved
0.7531	Intermediate Similarity	NPD37	Approved
0.753	Intermediate Similarity	NPD6959	Discontinued
0.7529	Intermediate Similarity	NPD7074	Phase 3
0.7529	Intermediate Similarity	NPD7472	Approved
0.7516	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD6797	Phase 2
0.7484	Intermediate Similarity	NPD6273	Approved
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7483	Intermediate Similarity	NPD3266	Approved
0.7483	Intermediate Similarity	NPD5585	Approved
0.7483	Intermediate Similarity	NPD3267	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7469	Intermediate Similarity	NPD7411	Suspended
0.7458	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3749	Approved
0.7443	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7251	Discontinued
0.7434	Intermediate Similarity	NPD447	Suspended
0.7423	Intermediate Similarity	NPD6844	Discontinued
0.7421	Intermediate Similarity	NPD5401	Approved
0.7419	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7228	Approved
0.7412	Intermediate Similarity	NPD3818	Discontinued
0.7399	Intermediate Similarity	NPD7808	Phase 3
0.7397	Intermediate Similarity	NPD9717	Approved
0.7396	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7768	Phase 2
0.7394	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7003	Approved
0.7386	Intermediate Similarity	NPD6653	Approved
0.7378	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD8455	Phase 2
0.7372	Intermediate Similarity	NPD1549	Phase 2
0.7372	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1551	Phase 2
0.7351	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7075	Discontinued
0.7346	Intermediate Similarity	NPD7458	Discontinued
0.7333	Intermediate Similarity	NPD4908	Phase 1
0.7333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.732	Intermediate Similarity	NPD6355	Discontinued
0.732	Intermediate Similarity	NPD5124	Phase 1
0.732	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1934	Approved
0.7315	Intermediate Similarity	NPD5647	Approved
0.7308	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6234	Discontinued
0.7301	Intermediate Similarity	NPD4380	Phase 2
0.7294	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6166	Phase 2
0.729	Intermediate Similarity	NPD4308	Phase 3
0.7285	Intermediate Similarity	NPD4625	Phase 3
0.7284	Intermediate Similarity	NPD1653	Approved
0.7262	Intermediate Similarity	NPD5494	Approved
0.7255	Intermediate Similarity	NPD4140	Approved
0.7251	Intermediate Similarity	NPD7473	Discontinued
0.725	Intermediate Similarity	NPD6799	Approved
0.7244	Intermediate Similarity	NPD6099	Approved
0.7244	Intermediate Similarity	NPD6032	Approved
0.7244	Intermediate Similarity	NPD2796	Approved
0.7244	Intermediate Similarity	NPD6100	Approved
0.7237	Intermediate Similarity	NPD411	Approved
0.7237	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6798	Discontinued
0.7232	Intermediate Similarity	NPD8150	Discontinued
0.723	Intermediate Similarity	NPD4359	Approved
0.7229	Intermediate Similarity	NPD3817	Phase 2
0.7215	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6801	Discontinued
0.7211	Intermediate Similarity	NPD1091	Approved
0.7211	Intermediate Similarity	NPD1611	Approved
0.7205	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5762	Approved
0.7197	Intermediate Similarity	NPD7266	Discontinued
0.7197	Intermediate Similarity	NPD5763	Approved
0.7192	Intermediate Similarity	NPD4626	Approved
0.7192	Intermediate Similarity	NPD1778	Approved
0.719	Intermediate Similarity	NPD6233	Phase 2
0.7184	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1283	Approved
0.7176	Intermediate Similarity	NPD7229	Phase 3
0.7176	Intermediate Similarity	NPD6232	Discontinued
0.717	Intermediate Similarity	NPD4628	Phase 3
0.7169	Intermediate Similarity	NPD2801	Approved
0.7169	Intermediate Similarity	NPD1465	Phase 2
0.7162	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7152	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD7240	Approved
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6362	Approved
0.7124	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5691	Approved
0.7114	Intermediate Similarity	NPD4749	Approved
0.7107	Intermediate Similarity	NPD6674	Discontinued
0.7099	Intermediate Similarity	NPD2533	Approved
0.7099	Intermediate Similarity	NPD2532	Approved
0.7099	Intermediate Similarity	NPD2534	Approved
0.7097	Intermediate Similarity	NPD4622	Approved
0.7097	Intermediate Similarity	NPD4618	Approved
0.7095	Intermediate Similarity	NPD1610	Phase 2
0.7091	Intermediate Similarity	NPD6599	Discontinued
0.7089	Intermediate Similarity	NPD6002	Phase 3
0.7089	Intermediate Similarity	NPD6005	Phase 3
0.7089	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6004	Phase 3
0.7089	Intermediate Similarity	NPD2344	Approved
0.7086	Intermediate Similarity	NPD1019	Discontinued
0.7083	Intermediate Similarity	NPD3882	Suspended
0.7079	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4870	Approved
0.707	Intermediate Similarity	NPD1510	Phase 2
0.7063	Intermediate Similarity	NPD8166	Discontinued
0.7059	Intermediate Similarity	NPD7095	Approved
0.7059	Intermediate Similarity	NPD7435	Discontinued
0.7044	Intermediate Similarity	NPD2897	Discontinued
0.7037	Intermediate Similarity	NPD1511	Approved
0.7032	Intermediate Similarity	NPD1613	Approved
0.7032	Intermediate Similarity	NPD4307	Phase 2
0.7032	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4477	Approved
0.7025	Intermediate Similarity	NPD4476	Approved
0.7025	Intermediate Similarity	NPD2438	Suspended
0.7018	Intermediate Similarity	NPD8127	Discontinued
0.7013	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7985	Registered
0.7006	Intermediate Similarity	NPD5688	Approved
0.7006	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5689	Approved
0.7	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1652	Phase 2
0.6994	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6781	Approved
0.6989	Remote Similarity	NPD6777	Approved
0.6989	Remote Similarity	NPD6776	Approved
0.6989	Remote Similarity	NPD6782	Approved
0.6989	Remote Similarity	NPD6780	Approved
0.6989	Remote Similarity	NPD6779	Approved
0.6989	Remote Similarity	NPD6778	Approved
0.698	Remote Similarity	NPD422	Phase 1
0.698	Remote Similarity	NPD1281	Approved
0.6979	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7783	Phase 2
0.6968	Remote Similarity	NPD8032	Phase 2
0.6966	Remote Similarity	NPD709	Approved
0.6966	Remote Similarity	NPD6671	Approved
0.6963	Remote Similarity	NPD8151	Discontinued
0.6962	Remote Similarity	NPD4108	Discontinued
0.6959	Remote Similarity	NPD17	Approved
0.6951	Remote Similarity	NPD1512	Approved
0.6949	Remote Similarity	NPD7685	Pre-registration
0.6944	Remote Similarity	NPD1241	Discontinued
0.6944	Remote Similarity	NPD8434	Phase 2
0.6939	Remote Similarity	NPD1894	Discontinued
0.6933	Remote Similarity	NPD6143	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