NPASS Compound

Structure

CID42776 OpenBabel06191715372D 25 29 0 0 1 0 0 0 0 0999 V2000 2.6974 -1.7888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9912 -1.2575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5845 -1.9618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7261 -2.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -2.5148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4519 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1779 -0.4192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4520 -1.6765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1030 -1.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8712 -1.7888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4520 -2.5148 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.6765 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7260 -0.4191 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4519 -1.6766 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5643 -1.2574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2776 -2.4965 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7260 -0.4191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1779 -1.2574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7260 -1.2574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7259 -1.2574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9774 -0.5418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8218 -3.1010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4303 -0.0124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4439 -2.5841 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 10 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 5 2 0 0 0 0 5 12 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 9 24 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 4 1 6 0 0 0 12 19 1 1 0 0 0 12 20 1 0 0 0 0 13 20 1 6 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 6 0 0 0 15 19 1 6 0 0 0 15 21 1 0 0 0 0 16 22 1 1 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 19 8 1 1 0 0 0 20 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	347.736
LogP:	2.223
LogD:	1.924
LogS:	-4.57
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	6.996
Fsp3:	0.75
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:	-5.539
MDCK Permeability:	2.005835085583385e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.106

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.829
Plasma Protein Binding (PPB):	59.12403106689453%
Volume Distribution (VD):	1.867
Pgp-substrate:	56.296939849853516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.487
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.652
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.449
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	7.199
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.363
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.134
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.294
Carcinogencity:	0.551
Eye Corrosion:	0.004
Eye Irritation:	0.02
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC42776

Natural Product ID:	NPC42776
*Common Name:**	SALXTEMFWBBTBS-YPDCMUIKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SALXTEMFWBBTBS-YPDCMUIKSA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-10-11-4-5-12-19(8-11,15(10)21)17(23)25-13-6-7-18(2,3)14-16(22)24-9-20(12,13)14/h4-5,11-16,21-22H,1,6-9H2,2-3H3/t11-,12-,13+,14-,15-,16-,19+,20-/m1/s1
SMILES:	O[C@@H]1OC[C@]23[C@H]1C(C)(C)CC[C@@H]2OC(=O)[C@]12[C@H]3C=C[C@H](C1)C(=C)[C@H]2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3093769
PubChem CID:	72947454
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19099464]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19697926]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2421673]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	aerial parts	Muli County, Sichuan Province, China	2011-AUG	PMID[24219809]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9599286]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19763	Meloidogyne incognita	Species	Meloidogynidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21614	Urceolaria scruposa	Species	Trichodinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17508	Danae racemosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19768	Xylosalsola arbuscula	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20336	Arctotheca calendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20470	Elaeagnus orientalis	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16409	Quercus pedunculata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1558	Ozothamnus obcordatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16021	Boletus bovinus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20543	Psydrax livida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17240	Crematogaster brevis	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20115	Melampodium argophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19889	Cereus stellatus	Species	Sagartiidae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[523172]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[523172]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[523172]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[523172]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[523172]

☑ 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 NPC42776 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	212
0.1-0.2	1253
0.2-0.3	4416
0.3-0.4	8963
0.4-0.5	12570
0.5-0.6	6424
0.6-0.7	5865
0.7-0.8	2869
0.8-0.85	107
0.85-0.9	15
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9223	High Similarity	NPC285927
0.8879	High Similarity	NPC98633
0.8879	High Similarity	NPC255655
0.8879	High Similarity	NPC130302
0.8785	High Similarity	NPC471250
0.8704	High Similarity	NPC124053
0.8654	High Similarity	NPC39683
0.8636	High Similarity	NPC285086
0.8624	High Similarity	NPC471251
0.8571	High Similarity	NPC470171
0.8496	Intermediate Similarity	NPC471249
0.8468	Intermediate Similarity	NPC9848
0.8468	Intermediate Similarity	NPC312017
0.8426	Intermediate Similarity	NPC96333
0.8426	Intermediate Similarity	NPC88833
0.8426	Intermediate Similarity	NPC61071
0.8411	Intermediate Similarity	NPC101842
0.8407	Intermediate Similarity	NPC218970
0.8349	Intermediate Similarity	NPC469845
0.8318	Intermediate Similarity	NPC140723
0.8305	Intermediate Similarity	NPC174367
0.8305	Intermediate Similarity	NPC47113
0.8304	Intermediate Similarity	NPC52634
0.8273	Intermediate Similarity	NPC143706
0.8273	Intermediate Similarity	NPC472534
0.823	Intermediate Similarity	NPC243354
0.8214	Intermediate Similarity	NPC126691
0.8198	Intermediate Similarity	NPC98069
0.8198	Intermediate Similarity	NPC49730
0.8198	Intermediate Similarity	NPC101450
0.8167	Intermediate Similarity	NPC311534
0.8165	Intermediate Similarity	NPC103172
0.8165	Intermediate Similarity	NPC164600
0.8158	Intermediate Similarity	NPC106228
0.8158	Intermediate Similarity	NPC138372
0.8148	Intermediate Similarity	NPC159442
0.8142	Intermediate Similarity	NPC194273
0.8142	Intermediate Similarity	NPC320118
0.8125	Intermediate Similarity	NPC56025
0.8091	Intermediate Similarity	NPC471246
0.8091	Intermediate Similarity	NPC293512
0.8083	Intermediate Similarity	NPC117702
0.8083	Intermediate Similarity	NPC146456
0.8083	Intermediate Similarity	NPC469757
0.8083	Intermediate Similarity	NPC471357
0.8073	Intermediate Similarity	NPC96268
0.807	Intermediate Similarity	NPC116024
0.807	Intermediate Similarity	NPC220293
0.8053	Intermediate Similarity	NPC302146
0.8053	Intermediate Similarity	NPC174836
0.8037	Intermediate Similarity	NPC218383
0.8037	Intermediate Similarity	NPC108371
0.8036	Intermediate Similarity	NPC472666
0.8036	Intermediate Similarity	NPC129340
0.8018	Intermediate Similarity	NPC232133
0.8018	Intermediate Similarity	NPC476765
0.8017	Intermediate Similarity	NPC473888
0.8017	Intermediate Similarity	NPC473620
0.8	Intermediate Similarity	NPC266728
0.8	Intermediate Similarity	NPC231530
0.8	Intermediate Similarity	NPC252296
0.8	Intermediate Similarity	NPC37600
0.8	Intermediate Similarity	NPC278628
0.8	Intermediate Similarity	NPC49492
0.8	Intermediate Similarity	NPC477236
0.7984	Intermediate Similarity	NPC478072
0.7983	Intermediate Similarity	NPC27363
0.7983	Intermediate Similarity	NPC472768
0.7982	Intermediate Similarity	NPC51978
0.7982	Intermediate Similarity	NPC139347
0.7982	Intermediate Similarity	NPC469985
0.7982	Intermediate Similarity	NPC102619
0.7966	Intermediate Similarity	NPC202051
0.7965	Intermediate Similarity	NPC285410
0.7965	Intermediate Similarity	NPC250481
0.7965	Intermediate Similarity	NPC471243
0.7965	Intermediate Similarity	NPC263827
0.7965	Intermediate Similarity	NPC470311
0.7965	Intermediate Similarity	NPC329953
0.7963	Intermediate Similarity	NPC121218
0.7963	Intermediate Similarity	NPC253886
0.7951	Intermediate Similarity	NPC251866
0.7951	Intermediate Similarity	NPC471358
0.7951	Intermediate Similarity	NPC180079
0.7951	Intermediate Similarity	NPC284406
0.7951	Intermediate Similarity	NPC471361
0.7951	Intermediate Similarity	NPC219085
0.7951	Intermediate Similarity	NPC469754
0.7951	Intermediate Similarity	NPC17896
0.7951	Intermediate Similarity	NPC89514
0.7951	Intermediate Similarity	NPC10823
0.7951	Intermediate Similarity	NPC469753
0.7951	Intermediate Similarity	NPC197707
0.7951	Intermediate Similarity	NPC6108
0.7951	Intermediate Similarity	NPC469752
0.7951	Intermediate Similarity	NPC9499
0.7951	Intermediate Similarity	NPC469755
0.7951	Intermediate Similarity	NPC471360
0.7951	Intermediate Similarity	NPC471352
0.7951	Intermediate Similarity	NPC70542
0.7951	Intermediate Similarity	NPC469751
0.7951	Intermediate Similarity	NPC471359
0.7951	Intermediate Similarity	NPC86159
0.7949	Intermediate Similarity	NPC19028
0.7949	Intermediate Similarity	NPC9674
0.7949	Intermediate Similarity	NPC122971
0.7946	Intermediate Similarity	NPC469983
0.7946	Intermediate Similarity	NPC265655
0.7946	Intermediate Similarity	NPC118225
0.7944	Intermediate Similarity	NPC477854
0.7944	Intermediate Similarity	NPC474793
0.7934	Intermediate Similarity	NPC305496
0.7934	Intermediate Similarity	NPC287423
0.7934	Intermediate Similarity	NPC42399
0.7928	Intermediate Similarity	NPC59530
0.7928	Intermediate Similarity	NPC220974
0.7928	Intermediate Similarity	NPC184512
0.7928	Intermediate Similarity	NPC469746
0.7925	Intermediate Similarity	NPC477853
0.7925	Intermediate Similarity	NPC173272
0.7913	Intermediate Similarity	NPC181145
0.7913	Intermediate Similarity	NPC470953
0.7913	Intermediate Similarity	NPC469877
0.7913	Intermediate Similarity	NPC470919
0.7913	Intermediate Similarity	NPC471398
0.7913	Intermediate Similarity	NPC117712
0.7913	Intermediate Similarity	NPC472274
0.7909	Intermediate Similarity	NPC29705
0.7909	Intermediate Similarity	NPC472227
0.7909	Intermediate Similarity	NPC244247
0.7909	Intermediate Similarity	NPC152966
0.7909	Intermediate Similarity	NPC202793
0.7909	Intermediate Similarity	NPC471293
0.7909	Intermediate Similarity	NPC472228
0.7909	Intermediate Similarity	NPC13149
0.7899	Intermediate Similarity	NPC313528
0.7899	Intermediate Similarity	NPC28532
0.7899	Intermediate Similarity	NPC470419
0.7895	Intermediate Similarity	NPC194951
0.7895	Intermediate Similarity	NPC12046
0.789	Intermediate Similarity	NPC22388
0.789	Intermediate Similarity	NPC271980
0.789	Intermediate Similarity	NPC471363
0.789	Intermediate Similarity	NPC164551
0.789	Intermediate Similarity	NPC193934
0.789	Intermediate Similarity	NPC238397
0.7886	Intermediate Similarity	NPC173347
0.7881	Intermediate Similarity	NPC112038
0.7876	Intermediate Similarity	NPC83005
0.7876	Intermediate Similarity	NPC476766
0.7876	Intermediate Similarity	NPC197428
0.7876	Intermediate Similarity	NPC163314
0.787	Intermediate Similarity	NPC267921
0.7869	Intermediate Similarity	NPC245094
0.7857	Intermediate Similarity	NPC295389
0.7857	Intermediate Similarity	NPC258323
0.7857	Intermediate Similarity	NPC94529
0.7857	Intermediate Similarity	NPC472217
0.7857	Intermediate Similarity	NPC469729
0.7857	Intermediate Similarity	NPC472219
0.7857	Intermediate Similarity	NPC469844
0.7857	Intermediate Similarity	NPC472218
0.7857	Intermediate Similarity	NPC469733
0.7857	Intermediate Similarity	NPC195708
0.7851	Intermediate Similarity	NPC250556
0.7851	Intermediate Similarity	NPC469750
0.785	Intermediate Similarity	NPC253586
0.7845	Intermediate Similarity	NPC476963
0.7845	Intermediate Similarity	NPC474046
0.7845	Intermediate Similarity	NPC470628
0.7845	Intermediate Similarity	NPC72772
0.7845	Intermediate Similarity	NPC259306
0.7845	Intermediate Similarity	NPC469794
0.784	Intermediate Similarity	NPC471234
0.784	Intermediate Similarity	NPC477234
0.7838	Intermediate Similarity	NPC12823
0.7838	Intermediate Similarity	NPC295366
0.7838	Intermediate Similarity	NPC127609
0.7838	Intermediate Similarity	NPC210178
0.7833	Intermediate Similarity	NPC204812
0.7833	Intermediate Similarity	NPC41129
0.783	Intermediate Similarity	NPC266899
0.783	Intermediate Similarity	NPC48330
0.7826	Intermediate Similarity	NPC251309
0.7826	Intermediate Similarity	NPC157441
0.7826	Intermediate Similarity	NPC293658
0.7826	Intermediate Similarity	NPC194100
0.7826	Intermediate Similarity	NPC178981
0.7826	Intermediate Similarity	NPC260665
0.7826	Intermediate Similarity	NPC471627
0.7826	Intermediate Similarity	NPC962
0.7826	Intermediate Similarity	NPC474410
0.7826	Intermediate Similarity	NPC132668
0.7826	Intermediate Similarity	NPC471173
0.7826	Intermediate Similarity	NPC75167
0.7826	Intermediate Similarity	NPC311592
0.7818	Intermediate Similarity	NPC7613
0.7818	Intermediate Similarity	NPC127933
0.7818	Intermediate Similarity	NPC134270
0.7818	Intermediate Similarity	NPC475889

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 NPC42776 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1483
0.2-0.3	3999
0.3-0.4	2328
0.4-0.5	628
0.5-0.6	250
0.6-0.7	182
0.7-0.8	92
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8205	Intermediate Similarity	NPD6370	Approved
0.8167	Intermediate Similarity	NPD7736	Approved
0.8083	Intermediate Similarity	NPD8293	Discontinued
0.8067	Intermediate Similarity	NPD7492	Approved
0.8034	Intermediate Similarity	NPD6054	Approved
0.8	Intermediate Similarity	NPD6616	Approved
0.7966	Intermediate Similarity	NPD6016	Approved
0.7966	Intermediate Similarity	NPD6015	Approved
0.7951	Intermediate Similarity	NPD7319	Approved
0.7934	Intermediate Similarity	NPD7078	Approved
0.7899	Intermediate Similarity	NPD5988	Approved
0.7881	Intermediate Similarity	NPD6059	Approved
0.7851	Intermediate Similarity	NPD7507	Approved
0.7768	Intermediate Similarity	NPD5697	Approved
0.7739	Intermediate Similarity	NPD6882	Approved
0.7731	Intermediate Similarity	NPD6319	Approved
0.7699	Intermediate Similarity	NPD6881	Approved
0.7699	Intermediate Similarity	NPD6899	Approved
0.7699	Intermediate Similarity	NPD7320	Approved
0.7679	Intermediate Similarity	NPD6675	Approved
0.7679	Intermediate Similarity	NPD6402	Approved
0.7679	Intermediate Similarity	NPD5739	Approved
0.7679	Intermediate Similarity	NPD7128	Approved
0.7679	Intermediate Similarity	NPD6008	Approved
0.7632	Intermediate Similarity	NPD6012	Approved
0.7632	Intermediate Similarity	NPD6014	Approved
0.7632	Intermediate Similarity	NPD6013	Approved
0.7627	Intermediate Similarity	NPD6009	Approved
0.7611	Intermediate Similarity	NPD6412	Phase 2
0.7611	Intermediate Similarity	NPD5701	Approved
0.7568	Intermediate Similarity	NPD5211	Phase 2
0.7565	Intermediate Similarity	NPD7102	Approved
0.7565	Intermediate Similarity	NPD7290	Approved
0.7565	Intermediate Similarity	NPD6883	Approved
0.7547	Intermediate Similarity	NPD6411	Approved
0.7544	Intermediate Similarity	NPD6011	Approved
0.7521	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.7478	Intermediate Similarity	NPD6373	Approved
0.7478	Intermediate Similarity	NPD6372	Approved
0.7477	Intermediate Similarity	NPD5779	Approved
0.7477	Intermediate Similarity	NPD5778	Approved
0.7436	Intermediate Similarity	NPD8297	Approved
0.7434	Intermediate Similarity	NPD5141	Approved
0.7414	Intermediate Similarity	NPD4634	Approved
0.7398	Intermediate Similarity	NPD8328	Phase 3
0.7391	Intermediate Similarity	NPD6686	Approved
0.7387	Intermediate Similarity	NPD5286	Approved
0.7387	Intermediate Similarity	NPD7640	Approved
0.7387	Intermediate Similarity	NPD5285	Approved
0.7387	Intermediate Similarity	NPD4696	Approved
0.7387	Intermediate Similarity	NPD7639	Approved
0.7377	Intermediate Similarity	NPD8513	Phase 3
0.7377	Intermediate Similarity	NPD8516	Approved
0.7377	Intermediate Similarity	NPD8517	Approved
0.7377	Intermediate Similarity	NPD8515	Approved
0.7364	Intermediate Similarity	NPD4755	Approved
0.7358	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6101	Approved
0.7333	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6033	Approved
0.7297	Intermediate Similarity	NPD7638	Approved
0.7273	Intermediate Similarity	NPD7328	Approved
0.7273	Intermediate Similarity	NPD7327	Approved
0.7257	Intermediate Similarity	NPD5225	Approved
0.7257	Intermediate Similarity	NPD4633	Approved
0.7257	Intermediate Similarity	NPD5226	Approved
0.7257	Intermediate Similarity	NPD5224	Approved
0.7236	Intermediate Similarity	NPD5983	Phase 2
0.7232	Intermediate Similarity	NPD4700	Approved
0.7227	Intermediate Similarity	NPD8133	Approved
0.7213	Intermediate Similarity	NPD7516	Approved
0.7203	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5175	Approved
0.7193	Intermediate Similarity	NPD5174	Approved
0.7179	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5223	Approved
0.7156	Intermediate Similarity	NPD6399	Phase 3
0.7154	Intermediate Similarity	NPD8294	Approved
0.7154	Intermediate Similarity	NPD8377	Approved
0.7143	Intermediate Similarity	NPD6053	Discontinued
0.712	Intermediate Similarity	NPD6067	Discontinued
0.712	Intermediate Similarity	NPD7604	Phase 2
0.7107	Intermediate Similarity	NPD6274	Approved
0.7097	Intermediate Similarity	NPD8033	Approved
0.7097	Intermediate Similarity	NPD8380	Approved
0.7097	Intermediate Similarity	NPD8296	Approved
0.7097	Intermediate Similarity	NPD8378	Approved
0.7097	Intermediate Similarity	NPD8379	Approved
0.7097	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8335	Approved
0.7097	Intermediate Similarity	NPD7503	Approved
0.7094	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7101	Approved
0.7073	Intermediate Similarity	NPD7100	Approved
0.7064	Intermediate Similarity	NPD6079	Approved
0.7064	Intermediate Similarity	NPD7637	Suspended
0.7054	Intermediate Similarity	NPD6083	Phase 2
0.7054	Intermediate Similarity	NPD6084	Phase 2
0.7049	Intermediate Similarity	NPD6317	Approved
0.7049	Intermediate Similarity	NPD7115	Discovery
0.7037	Intermediate Similarity	NPD5328	Approved
0.7027	Intermediate Similarity	NPD5695	Phase 3
0.7008	Intermediate Similarity	NPD6336	Discontinued
0.7	Intermediate Similarity	NPD4202	Approved
0.6992	Remote Similarity	NPD6314	Approved
0.6992	Remote Similarity	NPD6335	Approved
0.6992	Remote Similarity	NPD6313	Approved
0.6991	Remote Similarity	NPD4225	Approved
0.6964	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5222	Approved
0.6964	Remote Similarity	NPD5221	Approved
0.6949	Remote Similarity	NPD4730	Approved
0.6949	Remote Similarity	NPD4729	Approved
0.6923	Remote Similarity	NPD4768	Approved
0.6923	Remote Similarity	NPD4767	Approved
0.6916	Remote Similarity	NPD4249	Approved
0.6903	Remote Similarity	NPD5173	Approved
0.6897	Remote Similarity	NPD4754	Approved
0.6875	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6435	Approved
0.6852	Remote Similarity	NPD4251	Approved
0.6852	Remote Similarity	NPD4250	Approved
0.6842	Remote Similarity	NPD5696	Approved
0.6838	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5250	Approved
0.6833	Remote Similarity	NPD5249	Phase 3
0.6833	Remote Similarity	NPD5251	Approved
0.6833	Remote Similarity	NPD5247	Approved
0.6833	Remote Similarity	NPD5248	Approved
0.6825	Remote Similarity	NPD6909	Approved
0.6825	Remote Similarity	NPD6908	Approved
0.6822	Remote Similarity	NPD8074	Phase 3
0.6815	Remote Similarity	NPD6334	Approved
0.6815	Remote Similarity	NPD6333	Approved
0.6814	Remote Similarity	NPD7839	Suspended
0.6814	Remote Similarity	NPD4697	Phase 3
0.681	Remote Similarity	NPD7632	Discontinued
0.6807	Remote Similarity	NPD5128	Approved
0.6794	Remote Similarity	NPD5956	Approved
0.6792	Remote Similarity	NPD5362	Discontinued
0.6789	Remote Similarity	NPD6903	Approved
0.6786	Remote Similarity	NPD7748	Approved
0.6786	Remote Similarity	NPD5282	Discontinued
0.6777	Remote Similarity	NPD5215	Approved
0.6777	Remote Similarity	NPD5217	Approved
0.6777	Remote Similarity	NPD5216	Approved
0.6759	Remote Similarity	NPD7521	Approved
0.6759	Remote Similarity	NPD7146	Approved
0.6759	Remote Similarity	NPD5330	Approved
0.6759	Remote Similarity	NPD7334	Approved
0.6759	Remote Similarity	NPD6409	Approved
0.6759	Remote Similarity	NPD3618	Phase 1
0.6759	Remote Similarity	NPD5786	Approved
0.6759	Remote Similarity	NPD6684	Approved
0.6757	Remote Similarity	NPD5281	Approved
0.6757	Remote Similarity	NPD5284	Approved
0.6757	Remote Similarity	NPD7515	Phase 2
0.6757	Remote Similarity	NPD7983	Approved
0.6757	Remote Similarity	NPD8035	Phase 2
0.6757	Remote Similarity	NPD8034	Phase 2
0.6754	Remote Similarity	NPD7902	Approved
0.675	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD3665	Phase 1
0.6729	Remote Similarity	NPD3133	Approved
0.6729	Remote Similarity	NPD3666	Approved
0.6729	Remote Similarity	NPD4786	Approved
0.6727	Remote Similarity	NPD4753	Phase 2
0.6698	Remote Similarity	NPD3667	Approved
0.6697	Remote Similarity	NPD3573	Approved
0.6694	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5135	Approved
0.6694	Remote Similarity	NPD5169	Approved
0.6694	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6639	Remote Similarity	NPD5127	Approved
0.6637	Remote Similarity	NPD6001	Approved
0.6636	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5210	Approved
0.6579	Remote Similarity	NPD4629	Approved
0.6567	Remote Similarity	NPD8338	Approved
0.6557	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6371	Approved
0.6542	Remote Similarity	NPD4269	Approved
0.6542	Remote Similarity	NPD4270	Approved
0.6518	Remote Similarity	NPD5785	Approved
0.6509	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7900	Approved
0.6486	Remote Similarity	NPD6672	Approved
0.6486	Remote Similarity	NPD5737	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