NPASS Compound

Structure

CID277570 OpenBabel06191716082D 22 22 0 0 1 0 0 0 0 0999 V2000 -9.5263 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 -5.1962 2.0000 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 -3.4641 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 -1.7321 1.0000 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 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 4 5 3 0 0 0 0 5 6 1 0 0 0 0 6 7 3 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 21 1 0 0 0 0 11 17 1 0 0 0 0 12 11 1 1 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 6 0 0 0 14 15 1 0 0 0 0 14 19 1 1 0 0 0 15 16 1 0 0 0 0 15 20 1 6 0 0 0 16 21 1 1 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.14
Volume:	316.295
LogP:	0.815
LogD:	0.335
LogS:	-1.541
# Rotatable Bonds:	5
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.391
Synthetic Accessibility Score:	4.431
Fsp3:	0.625
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:	-4.798
MDCK Permeability:	0.00021294962789397687
Pgp-inhibitor:	0.002
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.916
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	98.07788848876953%
Volume Distribution (VD):	1.056
Pgp-substrate:	1.810239315032959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.522
CYP2C19-substrate:	0.67
CYP2C9-inhibitor:	0.837
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.512
CYP3A4-inhibitor:	0.189
CYP3A4-substrate:	0.065

ADMET: Excretion

Clearance (CL):	2.24
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.433
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.87
Rat Oral Acute Toxicity:	0.406
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.934
Carcinogencity:	0.719
Eye Corrosion:	0.071
Eye Irritation:	0.856
Respiratory Toxicity:	0.838

Download Data

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

Natural Product: NPC277570

Natural Product ID:	NPC277570
*Common Name:**	8E-Decaene-4,6-Diyn-1-O-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[(E)-dec-8-en-4,6-diynoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	QIFYDSMWESCVBZ-FAOXUISGSA-N
Standard InCHI:	InChI=1S/C16H22O6/c1-2-3-4-5-6-7-8-9-10-21-16-15(20)14(19)13(18)12(11-17)22-16/h2-3,12-20H,8-11H2,1H3/b3-2+/t12-,13-,14+,15-,16-/m1/s1
SMILES:	C/C=C/C#CC#CCCCO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011519
PubChem CID:	70695725
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17262892]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21163339]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22060189]
NPO23708	Aster koraiensis	Species	Asteraceae	Eukaryota	aerial parts	Euidang-myun, Gongju city, Chungchengnam-do, Republic of Korea	2007-Aug	PMID[22264115]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[22723874]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23371463]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Flowers	Lasa, China	n.a.	PMID[24621197]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27748595]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Bud	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5406	Veronica chamaedrys	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23708	Aster koraiensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9385	Glycosmis ovoidea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14084	Roccella fucoides	Species	Roccellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2509	Strombus gigas	Species	Strombidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14730	Bonnetia dinizii	Species	Bonnetiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2090	Baccharis thesioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO368	Dendroaspis angusticeps	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18458	Raukaua simplex	Species	Araliaceae	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

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	>	50000.0	nM	PMID[506804]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	30000.0	nM	PMID[506804]

☑ 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 NPC277570 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	295
0.1-0.2	5047
0.2-0.3	16858
0.3-0.4	13032
0.4-0.5	6191
0.5-0.6	990
0.6-0.7	210
0.7-0.8	64
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC294813
0.8571	High Similarity	NPC13143
0.8261	Intermediate Similarity	NPC472174
0.8261	Intermediate Similarity	NPC472173
0.8103	Intermediate Similarity	NPC124963
0.8103	Intermediate Similarity	NPC233726
0.8103	Intermediate Similarity	NPC23134
0.8095	Intermediate Similarity	NPC155457
0.8	Intermediate Similarity	NPC31496
0.7879	Intermediate Similarity	NPC147292
0.7826	Intermediate Similarity	NPC474078
0.7797	Intermediate Similarity	NPC326533
0.7759	Intermediate Similarity	NPC157193
0.7759	Intermediate Similarity	NPC299781
0.7759	Intermediate Similarity	NPC282143
0.7759	Intermediate Similarity	NPC42503
0.7742	Intermediate Similarity	NPC148424
0.7705	Intermediate Similarity	NPC303727
0.7619	Intermediate Similarity	NPC472025
0.7606	Intermediate Similarity	NPC55652
0.7586	Intermediate Similarity	NPC14144
0.7541	Intermediate Similarity	NPC242073
0.7541	Intermediate Similarity	NPC130683
0.7541	Intermediate Similarity	NPC145112
0.7541	Intermediate Similarity	NPC67660
0.7541	Intermediate Similarity	NPC89145
0.7541	Intermediate Similarity	NPC269166
0.7541	Intermediate Similarity	NPC157514
0.7541	Intermediate Similarity	NPC58629
0.7541	Intermediate Similarity	NPC107914
0.7541	Intermediate Similarity	NPC323361
0.7541	Intermediate Similarity	NPC165198
0.7541	Intermediate Similarity	NPC246558
0.7534	Intermediate Similarity	NPC229655
0.7432	Intermediate Similarity	NPC110813
0.7414	Intermediate Similarity	NPC277475
0.7414	Intermediate Similarity	NPC321087
0.7361	Intermediate Similarity	NPC132938
0.7344	Intermediate Similarity	NPC219040
0.7333	Intermediate Similarity	NPC133377
0.7333	Intermediate Similarity	NPC323574
0.7297	Intermediate Similarity	NPC326661
0.7273	Intermediate Similarity	NPC477763
0.7273	Intermediate Similarity	NPC477753
0.7273	Intermediate Similarity	NPC477750
0.7273	Intermediate Similarity	NPC477757
0.7273	Intermediate Similarity	NPC477762
0.7273	Intermediate Similarity	NPC472026
0.7273	Intermediate Similarity	NPC477755
0.7241	Intermediate Similarity	NPC176017
0.7241	Intermediate Similarity	NPC289758
0.7241	Intermediate Similarity	NPC69445
0.7241	Intermediate Similarity	NPC165846
0.7241	Intermediate Similarity	NPC199857
0.7241	Intermediate Similarity	NPC285364
0.7241	Intermediate Similarity	NPC92246
0.7241	Intermediate Similarity	NPC73906
0.7241	Intermediate Similarity	NPC21209
0.7241	Intermediate Similarity	NPC255377
0.7231	Intermediate Similarity	NPC34877
0.7231	Intermediate Similarity	NPC317023
0.7231	Intermediate Similarity	NPC320032
0.7231	Intermediate Similarity	NPC322855
0.7231	Intermediate Similarity	NPC290179
0.7167	Intermediate Similarity	NPC82512
0.7121	Intermediate Similarity	NPC143326
0.7051	Intermediate Similarity	NPC21693
0.7051	Intermediate Similarity	NPC280367
0.7051	Intermediate Similarity	NPC236649
0.7051	Intermediate Similarity	NPC469469
0.6962	Remote Similarity	NPC251026
0.6923	Remote Similarity	NPC100697
0.6923	Remote Similarity	NPC163362
0.6923	Remote Similarity	NPC127295
0.6897	Remote Similarity	NPC320240
0.6897	Remote Similarity	NPC70756
0.6875	Remote Similarity	NPC156089
0.6875	Remote Similarity	NPC142111
0.6875	Remote Similarity	NPC470313
0.6875	Remote Similarity	NPC473315
0.6875	Remote Similarity	NPC473500
0.6875	Remote Similarity	NPC38295
0.6857	Remote Similarity	NPC471761
0.6857	Remote Similarity	NPC12040
0.6857	Remote Similarity	NPC76881
0.6857	Remote Similarity	NPC190418
0.6857	Remote Similarity	NPC471760
0.6833	Remote Similarity	NPC230789
0.6833	Remote Similarity	NPC252918
0.6812	Remote Similarity	NPC325773
0.679	Remote Similarity	NPC266718
0.679	Remote Similarity	NPC475035
0.679	Remote Similarity	NPC473308
0.6761	Remote Similarity	NPC477764
0.6761	Remote Similarity	NPC477752
0.6761	Remote Similarity	NPC477751
0.6761	Remote Similarity	NPC477756
0.675	Remote Similarity	NPC20072
0.6724	Remote Similarity	NPC298699
0.6724	Remote Similarity	NPC134252
0.6724	Remote Similarity	NPC213159
0.6724	Remote Similarity	NPC86191
0.6724	Remote Similarity	NPC317182
0.6724	Remote Similarity	NPC291502
0.6714	Remote Similarity	NPC6848
0.6667	Remote Similarity	NPC206601
0.6667	Remote Similarity	NPC477754
0.6667	Remote Similarity	NPC477760
0.6667	Remote Similarity	NPC477761
0.6667	Remote Similarity	NPC477759
0.6667	Remote Similarity	NPC477758
0.6627	Remote Similarity	NPC208473
0.6585	Remote Similarity	NPC288471
0.6575	Remote Similarity	NPC67099
0.6575	Remote Similarity	NPC50228
0.6575	Remote Similarity	NPC97736
0.6575	Remote Similarity	NPC250619
0.6571	Remote Similarity	NPC268243
0.6567	Remote Similarity	NPC474577
0.6548	Remote Similarity	NPC118077
0.6548	Remote Similarity	NPC475186
0.6548	Remote Similarity	NPC475037
0.6548	Remote Similarity	NPC125142
0.6506	Remote Similarity	NPC73166
0.6506	Remote Similarity	NPC470658
0.6506	Remote Similarity	NPC477746
0.6506	Remote Similarity	NPC477747
0.6506	Remote Similarity	NPC470124
0.6486	Remote Similarity	NPC241265
0.6486	Remote Similarity	NPC211428
0.6486	Remote Similarity	NPC285003
0.6471	Remote Similarity	NPC470137
0.6462	Remote Similarity	NPC317501
0.6462	Remote Similarity	NPC314821
0.6462	Remote Similarity	NPC317626
0.6429	Remote Similarity	NPC470836
0.64	Remote Similarity	NPC52268
0.64	Remote Similarity	NPC53760
0.6395	Remote Similarity	NPC285588
0.6386	Remote Similarity	NPC136699
0.6386	Remote Similarity	NPC98276
0.6386	Remote Similarity	NPC259296
0.6386	Remote Similarity	NPC220167
0.6379	Remote Similarity	NPC266553
0.6333	Remote Similarity	NPC29721
0.6322	Remote Similarity	NPC74672
0.6322	Remote Similarity	NPC242503
0.6322	Remote Similarity	NPC327253
0.6322	Remote Similarity	NPC139782
0.6322	Remote Similarity	NPC473311
0.6322	Remote Similarity	NPC43074
0.6322	Remote Similarity	NPC209047
0.6316	Remote Similarity	NPC185419
0.6316	Remote Similarity	NPC184550
0.631	Remote Similarity	NPC475034
0.6279	Remote Similarity	NPC248312
0.6279	Remote Similarity	NPC471755
0.6279	Remote Similarity	NPC471756
0.6279	Remote Similarity	NPC137368
0.625	Remote Similarity	NPC309898
0.625	Remote Similarity	NPC110072
0.625	Remote Similarity	NPC111567
0.625	Remote Similarity	NPC263545
0.625	Remote Similarity	NPC473950
0.625	Remote Similarity	NPC15851
0.625	Remote Similarity	NPC282705
0.625	Remote Similarity	NPC469410
0.625	Remote Similarity	NPC475603
0.625	Remote Similarity	NPC475125
0.625	Remote Similarity	NPC61894
0.625	Remote Similarity	NPC473581
0.625	Remote Similarity	NPC182632
0.625	Remote Similarity	NPC186840
0.625	Remote Similarity	NPC473604
0.6234	Remote Similarity	NPC477311
0.6234	Remote Similarity	NPC163812
0.6234	Remote Similarity	NPC206823
0.6234	Remote Similarity	NPC291228
0.6234	Remote Similarity	NPC477303
0.6234	Remote Similarity	NPC9763
0.6234	Remote Similarity	NPC169085
0.6234	Remote Similarity	NPC308096
0.6234	Remote Similarity	NPC39266
0.6234	Remote Similarity	NPC225748
0.623	Remote Similarity	NPC62014
0.622	Remote Similarity	NPC16090
0.6216	Remote Similarity	NPC32148
0.6207	Remote Similarity	NPC50464
0.6207	Remote Similarity	NPC477748
0.6207	Remote Similarity	NPC249408
0.6207	Remote Similarity	NPC104129
0.6207	Remote Similarity	NPC22918
0.6184	Remote Similarity	NPC471879
0.618	Remote Similarity	NPC474792
0.618	Remote Similarity	NPC320552
0.618	Remote Similarity	NPC91654
0.618	Remote Similarity	NPC61201
0.618	Remote Similarity	NPC67398
0.6167	Remote Similarity	NPC320189
0.6154	Remote Similarity	NPC477305

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 NPC277570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	4827
0.2-0.3	2986
0.3-0.4	726
0.4-0.5	260
0.5-0.6	40
0.6-0.7	16
0.7-0.8	18
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
0.7797	Intermediate Similarity	NPD905	Approved
0.7797	Intermediate Similarity	NPD904	Phase 3
0.7667	Intermediate Similarity	NPD2269	Approved
0.7541	Intermediate Similarity	NPD888	Phase 3
0.7541	Intermediate Similarity	NPD891	Phase 3
0.7541	Intermediate Similarity	NPD894	Approved
0.7541	Intermediate Similarity	NPD890	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD895	Approved
0.7541	Intermediate Similarity	NPD892	Phase 3
0.7541	Intermediate Similarity	NPD893	Approved
0.7541	Intermediate Similarity	NPD889	Approved
0.7541	Intermediate Similarity	NPD887	Approved
0.7241	Intermediate Similarity	NPD9000	Phase 3
0.7241	Intermediate Similarity	NPD8998	Phase 2
0.7241	Intermediate Similarity	NPD8999	Phase 3
0.7241	Intermediate Similarity	NPD8993	Phase 1
0.7241	Intermediate Similarity	NPD8997	Approved
0.7188	Intermediate Similarity	NPD2267	Suspended
0.7015	Intermediate Similarity	NPD6123	Approved
0.7	Intermediate Similarity	NPD8966	Approved
0.7	Intermediate Similarity	NPD8965	Approved
0.6724	Remote Similarity	NPD8788	Approved
0.6615	Remote Similarity	NPD7346	Approved
0.6571	Remote Similarity	NPD847	Phase 1
0.6462	Remote Similarity	NPD9036	Phase 3
0.6462	Remote Similarity	NPD9035	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD9006	Approved
0.6324	Remote Similarity	NPD369	Approved
0.6322	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1457	Discontinued
0.6216	Remote Similarity	NPD897	Approved
0.6216	Remote Similarity	NPD896	Approved
0.6216	Remote Similarity	NPD898	Approved
0.6026	Remote Similarity	NPD3181	Approved
0.5968	Remote Similarity	NPD9218	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD9219	Approved
0.5873	Remote Similarity	NPD8994	Approved
0.5797	Remote Similarity	NPD885	Approved
0.5797	Remote Similarity	NPD884	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD7329	Approved
0.5769	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD8961	Approved
0.5645	Remote Similarity	NPD8957	Approved
0.5645	Remote Similarity	NPD8958	Phase 2
0.5641	Remote Similarity	NPD9445	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