NPASS Compound

Structure

NPC12040 OpenBabel07101718312D 30 31 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 2 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 3.4641 3.0000 0.0000 C 0 0 1 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 2.5981 2.5000 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 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 5.1962 3.0000 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 3.4641 4.0000 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 1.7321 3.0000 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 10 1 0 0 0 0 6 19 1 0 0 0 0 7 27 1 0 0 0 0 8 6 1 1 0 0 0 8 11 1 0 0 0 0 8 28 1 0 0 0 0 9 7 1 1 0 0 0 9 12 1 0 0 0 0 9 29 1 0 0 0 0 10 20 2 0 0 0 0 10 30 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 6 0 0 0 12 14 1 0 0 0 0 12 22 1 6 0 0 0 13 15 1 0 0 0 0 13 23 1 1 0 0 0 14 16 1 0 0 0 0 14 24 1 1 0 0 0 15 17 1 0 0 0 0 15 25 1 6 0 0 0 16 18 1 0 0 0 0 16 26 1 6 0 0 0 17 27 1 1 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.19
Volume:	405.618
LogP:	-0.848
LogD:	-0.973
LogS:	-1.216
# Rotatable Bonds:	10
TPSA:	195.6
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	2
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	4.277
Fsp3:	0.944
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.135
MDCK Permeability:	0.00013595231575891376
Pgp-inhibitor:	0.019
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.981
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	34.3701171875%
Volume Distribution (VD):	0.456
Pgp-substrate:	40.06707763671875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	1.135
Half-life (T1/2):	0.864

ADMET: Toxicity

hERG Blockers:	0.315
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.137
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.156
Carcinogencity:	0.072
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC12040

Natural Product ID:	NPC12040
*Common Name:**	6-O-(Beta-D-Glucopyranosyl)-1-O-Hexanoyl-Beta-D-Glucopyranose
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] hexanoate
Synonyms:
Standard InCHIKey:	HSEIACQHFYAWOA-NDYKIFPOSA-N
Standard InCHI:	InChI=1S/C18H32O12/c1-2-3-4-5-10(20)30-18-16(26)14(24)12(22)9(29-18)7-27-17-15(25)13(23)11(21)8(6-19)28-17/h8-9,11-19,21-26H,2-7H2,1H3/t8-,9-,11-,12-,13+,14+,15-,16-,17-,18+/m1/s1
SMILES:	CCCCCC(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387909
PubChem CID:	10741757
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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	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	6

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[566660]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	15.6	%	PMID[566660]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	59.2	%	PMID[566660]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	84.0	%	PMID[566660]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	100.0	%	PMID[566660]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.64	mg	PMID[566660]

☑ 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 NPC12040 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	811
0.1-0.2	5546
0.2-0.3	14942
0.3-0.4	11209
0.4-0.5	7468
0.5-0.6	2267
0.6-0.7	255
0.7-0.8	149
0.8-0.85	27
0.85-0.9	15
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC76881
0.9524	High Similarity	NPC50228
0.9524	High Similarity	NPC97736
0.9524	High Similarity	NPC250619
0.9375	High Similarity	NPC211428
0.9375	High Similarity	NPC285003
0.9375	High Similarity	NPC241265
0.9062	High Similarity	NPC206601
0.8955	High Similarity	NPC206823
0.8955	High Similarity	NPC163812
0.8955	High Similarity	NPC39266
0.8955	High Similarity	NPC169085
0.8955	High Similarity	NPC225748
0.8955	High Similarity	NPC9763
0.875	High Similarity	NPC471760
0.875	High Similarity	NPC471761
0.875	High Similarity	NPC190418
0.873	High Similarity	NPC325773
0.8571	High Similarity	NPC477350
0.8529	High Similarity	NPC184550
0.8529	High Similarity	NPC185419
0.8525	High Similarity	NPC472025
0.8451	Intermediate Similarity	NPC476782
0.8451	Intermediate Similarity	NPC216883
0.8451	Intermediate Similarity	NPC476781
0.8451	Intermediate Similarity	NPC476783
0.8406	Intermediate Similarity	NPC291228
0.8406	Intermediate Similarity	NPC308096
0.8387	Intermediate Similarity	NPC322855
0.8387	Intermediate Similarity	NPC320032
0.8358	Intermediate Similarity	NPC67099
0.8333	Intermediate Similarity	NPC281563
0.8333	Intermediate Similarity	NPC303727
0.8333	Intermediate Similarity	NPC477320
0.8333	Intermediate Similarity	NPC477330
0.8333	Intermediate Similarity	NPC109887
0.8333	Intermediate Similarity	NPC146380
0.8333	Intermediate Similarity	NPC477328
0.8333	Intermediate Similarity	NPC475425
0.8333	Intermediate Similarity	NPC477323
0.8333	Intermediate Similarity	NPC477329
0.8333	Intermediate Similarity	NPC477326
0.8333	Intermediate Similarity	NPC113745
0.8333	Intermediate Similarity	NPC477325
0.8219	Intermediate Similarity	NPC22742
0.8219	Intermediate Similarity	NPC477346
0.8219	Intermediate Similarity	NPC158302
0.8219	Intermediate Similarity	NPC146992
0.8219	Intermediate Similarity	NPC477344
0.8219	Intermediate Similarity	NPC294748
0.8219	Intermediate Similarity	NPC85759
0.8209	Intermediate Similarity	NPC32148
0.8167	Intermediate Similarity	NPC89145
0.8167	Intermediate Similarity	NPC246558
0.8167	Intermediate Similarity	NPC145112
0.8167	Intermediate Similarity	NPC58629
0.8167	Intermediate Similarity	NPC157514
0.8167	Intermediate Similarity	NPC269166
0.8167	Intermediate Similarity	NPC165198
0.8167	Intermediate Similarity	NPC67660
0.8167	Intermediate Similarity	NPC242073
0.8167	Intermediate Similarity	NPC107914
0.8154	Intermediate Similarity	NPC268243
0.8125	Intermediate Similarity	NPC477757
0.8125	Intermediate Similarity	NPC477763
0.8125	Intermediate Similarity	NPC477762
0.8125	Intermediate Similarity	NPC477755
0.8125	Intermediate Similarity	NPC477753
0.8125	Intermediate Similarity	NPC477750
0.8116	Intermediate Similarity	NPC53760
0.8116	Intermediate Similarity	NPC52268
0.8108	Intermediate Similarity	NPC267592
0.8095	Intermediate Similarity	NPC34877
0.8095	Intermediate Similarity	NPC290179
0.8095	Intermediate Similarity	NPC317023
0.8	Intermediate Similarity	NPC477331
0.8	Intermediate Similarity	NPC477319
0.8	Intermediate Similarity	NPC184915
0.8	Intermediate Similarity	NPC119583
0.8	Intermediate Similarity	NPC27289
0.8	Intermediate Similarity	NPC475327
0.8	Intermediate Similarity	NPC307400
0.8	Intermediate Similarity	NPC186992
0.8	Intermediate Similarity	NPC290012
0.8	Intermediate Similarity	NPC238056
0.8	Intermediate Similarity	NPC224953
0.8	Intermediate Similarity	NPC173328
0.8	Intermediate Similarity	NPC476087
0.8	Intermediate Similarity	NPC477318
0.8	Intermediate Similarity	NPC169345
0.8	Intermediate Similarity	NPC475270
0.8	Intermediate Similarity	NPC123204
0.8	Intermediate Similarity	NPC297768
0.8	Intermediate Similarity	NPC475667
0.8	Intermediate Similarity	NPC143421
0.8	Intermediate Similarity	NPC472204
0.8	Intermediate Similarity	NPC477317
0.8	Intermediate Similarity	NPC477347
0.8	Intermediate Similarity	NPC126685
0.8	Intermediate Similarity	NPC472203
0.8	Intermediate Similarity	NPC269318
0.8	Intermediate Similarity	NPC472201
0.8	Intermediate Similarity	NPC472202
0.8	Intermediate Similarity	NPC259294
0.8	Intermediate Similarity	NPC115013
0.8	Intermediate Similarity	NPC44782
0.8	Intermediate Similarity	NPC472205
0.8	Intermediate Similarity	NPC183888
0.8	Intermediate Similarity	NPC472200
0.8	Intermediate Similarity	NPC89843
0.7945	Intermediate Similarity	NPC110813
0.7838	Intermediate Similarity	NPC133377
0.7833	Intermediate Similarity	NPC233726
0.7833	Intermediate Similarity	NPC124963
0.7833	Intermediate Similarity	NPC23134
0.7833	Intermediate Similarity	NPC326533
0.7792	Intermediate Similarity	NPC477332
0.7792	Intermediate Similarity	NPC60849
0.7792	Intermediate Similarity	NPC473500
0.7792	Intermediate Similarity	NPC470313
0.7792	Intermediate Similarity	NPC38295
0.7792	Intermediate Similarity	NPC156089
0.7792	Intermediate Similarity	NPC472352
0.7778	Intermediate Similarity	NPC148424
0.7581	Intermediate Similarity	NPC130683
0.7581	Intermediate Similarity	NPC323361
0.7576	Intermediate Similarity	NPC472026
0.7536	Intermediate Similarity	NPC477751
0.7536	Intermediate Similarity	NPC477756
0.7536	Intermediate Similarity	NPC477752
0.7536	Intermediate Similarity	NPC477764
0.7532	Intermediate Similarity	NPC236649
0.7532	Intermediate Similarity	NPC21693
0.75	Intermediate Similarity	NPC157193
0.75	Intermediate Similarity	NPC299781
0.75	Intermediate Similarity	NPC282143
0.75	Intermediate Similarity	NPC42503
0.75	Intermediate Similarity	NPC6848
0.7429	Intermediate Similarity	NPC477754
0.7429	Intermediate Similarity	NPC477761
0.7429	Intermediate Similarity	NPC477760
0.7429	Intermediate Similarity	NPC477759
0.7429	Intermediate Similarity	NPC477758
0.7391	Intermediate Similarity	NPC147292
0.7385	Intermediate Similarity	NPC219040
0.7353	Intermediate Similarity	NPC317651
0.7353	Intermediate Similarity	NPC258690
0.7333	Intermediate Similarity	NPC14144
0.7284	Intermediate Similarity	NPC470657
0.725	Intermediate Similarity	NPC288471
0.7195	Intermediate Similarity	NPC31349
0.7188	Intermediate Similarity	NPC320588
0.7188	Intermediate Similarity	NPC469937
0.7188	Intermediate Similarity	NPC23155
0.7188	Intermediate Similarity	NPC53463
0.7179	Intermediate Similarity	NPC163362
0.7179	Intermediate Similarity	NPC127295
0.7167	Intermediate Similarity	NPC321087
0.7167	Intermediate Similarity	NPC277475
0.716	Intermediate Similarity	NPC83839
0.7123	Intermediate Similarity	NPC474078
0.7097	Intermediate Similarity	NPC323574
0.7059	Intermediate Similarity	NPC477349
0.7013	Intermediate Similarity	NPC474003
0.7	Intermediate Similarity	NPC255377
0.7	Intermediate Similarity	NPC69445
0.7	Intermediate Similarity	NPC165846
0.7	Intermediate Similarity	NPC289758
0.7	Intermediate Similarity	NPC73906
0.7	Intermediate Similarity	NPC199857
0.7	Intermediate Similarity	NPC92246
0.7	Intermediate Similarity	NPC285364
0.7	Intermediate Similarity	NPC21209
0.7	Intermediate Similarity	NPC176017
0.6988	Remote Similarity	NPC51662
0.6988	Remote Similarity	NPC314364
0.6941	Remote Similarity	NPC120021
0.6941	Remote Similarity	NPC216826
0.6941	Remote Similarity	NPC270908
0.6941	Remote Similarity	NPC470573
0.6941	Remote Similarity	NPC231710
0.6941	Remote Similarity	NPC65665
0.6935	Remote Similarity	NPC82512
0.6912	Remote Similarity	NPC143326
0.6905	Remote Similarity	NPC470009
0.6897	Remote Similarity	NPC44682
0.6897	Remote Similarity	NPC163409
0.6897	Remote Similarity	NPC477348
0.6897	Remote Similarity	NPC477345
0.6897	Remote Similarity	NPC238264
0.6892	Remote Similarity	NPC321873
0.6866	Remote Similarity	NPC220922
0.6857	Remote Similarity	NPC277570
0.6829	Remote Similarity	NPC125253
0.6829	Remote Similarity	NPC192025
0.6829	Remote Similarity	NPC253975
0.6812	Remote Similarity	NPC155457
0.679	Remote Similarity	NPC248415
0.6786	Remote Similarity	NPC118077
0.6786	Remote Similarity	NPC475186

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 NPC12040 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	873
0.1-0.2	4598
0.2-0.3	2435
0.3-0.4	752
0.4-0.5	298
0.5-0.6	125
0.6-0.7	44
0.7-0.8	19
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8219	Intermediate Similarity	NPD7329	Approved
0.8209	Intermediate Similarity	NPD898	Approved
0.8209	Intermediate Similarity	NPD897	Approved
0.8209	Intermediate Similarity	NPD896	Approved
0.8167	Intermediate Similarity	NPD891	Phase 3
0.8167	Intermediate Similarity	NPD890	Clinical (unspecified phase)
0.8167	Intermediate Similarity	NPD892	Phase 3
0.8167	Intermediate Similarity	NPD893	Approved
0.8167	Intermediate Similarity	NPD888	Phase 3
0.8143	Intermediate Similarity	NPD3181	Approved
0.8	Intermediate Similarity	NPD2269	Approved
0.7846	Intermediate Similarity	NPD6123	Approved
0.7833	Intermediate Similarity	NPD904	Phase 3
0.7833	Intermediate Similarity	NPD905	Approved
0.7581	Intermediate Similarity	NPD889	Approved
0.7581	Intermediate Similarity	NPD894	Approved
0.7581	Intermediate Similarity	NPD887	Approved
0.7581	Intermediate Similarity	NPD895	Approved
0.746	Intermediate Similarity	NPD7346	Approved
0.7353	Intermediate Similarity	NPD8961	Approved
0.7188	Intermediate Similarity	NPD3728	Approved
0.7188	Intermediate Similarity	NPD3730	Approved
0.7	Intermediate Similarity	NPD8997	Approved
0.7	Intermediate Similarity	NPD8998	Phase 2
0.7	Intermediate Similarity	NPD8993	Phase 1
0.7	Intermediate Similarity	NPD9000	Phase 3
0.7	Intermediate Similarity	NPD8999	Phase 3
0.697	Remote Similarity	NPD2267	Suspended
0.6866	Remote Similarity	NPD369	Approved
0.6866	Remote Similarity	NPD8959	Approved
0.6774	Remote Similarity	NPD8966	Approved
0.6774	Remote Similarity	NPD8965	Approved
0.662	Remote Similarity	NPD847	Phase 1
0.6591	Remote Similarity	NPD1447	Phase 3
0.6591	Remote Similarity	NPD1446	Phase 3
0.6556	Remote Similarity	NPD6428	Approved
0.6515	Remote Similarity	NPD9036	Phase 3
0.6515	Remote Similarity	NPD9035	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8788	Approved
0.6462	Remote Similarity	NPD1400	Approved
0.6462	Remote Similarity	NPD1399	Approved
0.6447	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD2255	Approved
0.6383	Remote Similarity	NPD8139	Approved
0.6383	Remote Similarity	NPD8082	Approved
0.6383	Remote Similarity	NPD8138	Approved
0.6383	Remote Similarity	NPD7139	Approved
0.6383	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8083	Approved
0.6383	Remote Similarity	NPD7140	Approved
0.6383	Remote Similarity	NPD8085	Approved
0.6383	Remote Similarity	NPD8086	Approved
0.6383	Remote Similarity	NPD8084	Approved
0.6316	Remote Similarity	NPD8275	Approved
0.6316	Remote Similarity	NPD8276	Approved
0.631	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3669	Approved
0.625	Remote Similarity	NPD3716	Discontinued
0.625	Remote Similarity	NPD8081	Approved
0.6186	Remote Similarity	NPD8393	Approved
0.6129	Remote Similarity	NPD9006	Approved
0.6129	Remote Similarity	NPD881	Approved
0.6125	Remote Similarity	NPD376	Approved
0.6125	Remote Similarity	NPD11	Approved
0.6122	Remote Similarity	NPD8307	Discontinued
0.6122	Remote Similarity	NPD8140	Approved
0.6119	Remote Similarity	NPD9007	Approved
0.6119	Remote Similarity	NPD9011	Approved
0.6119	Remote Similarity	NPD8960	Approved
0.6119	Remote Similarity	NPD64	Approved
0.6119	Remote Similarity	NPD9008	Approved
0.6119	Remote Similarity	NPD72	Approved
0.6119	Remote Similarity	NPD9010	Approved
0.6119	Remote Similarity	NPD65	Approved
0.6119	Remote Similarity	NPD9009	Approved
0.6119	Remote Similarity	NPD66	Approved
0.6081	Remote Similarity	NPD1457	Discontinued
0.6	Remote Similarity	NPD73	Approved
0.6	Remote Similarity	NPD6941	Approved
0.6	Remote Similarity	NPD8306	Approved
0.6	Remote Similarity	NPD8305	Approved
0.5941	Remote Similarity	NPD8087	Discontinued
0.5918	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6686	Approved
0.5882	Remote Similarity	NPD1780	Approved
0.5882	Remote Similarity	NPD1779	Approved
0.5867	Remote Similarity	NPD7909	Approved
0.5857	Remote Similarity	NPD885	Approved
0.5857	Remote Similarity	NPD884	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD46	Approved
0.5824	Remote Similarity	NPD6698	Approved
0.5816	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD9219	Approved
0.5781	Remote Similarity	NPD2699	Approved
0.5781	Remote Similarity	NPD9218	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD8133	Approved
0.5758	Remote Similarity	NPD2266	Phase 2
0.575	Remote Similarity	NPD6704	Discontinued
0.573	Remote Similarity	NPD3200	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD8994	Approved
0.5667	Remote Similarity	NPD3207	Approved
0.5667	Remote Similarity	NPD3203	Approved
0.5667	Remote Similarity	NPD3201	Approved
0.5667	Remote Similarity	NPD3208	Approved
0.5667	Remote Similarity	NPD3202	Approved
0.5667	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD3209	Approved
0.5652	Remote Similarity	NPD9050	Approved
0.5652	Remote Similarity	NPD9049	Discontinued
0.561	Remote Similarity	NPD1811	Approved
0.561	Remote Similarity	NPD1810	Approved
0.5607	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD8295	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