NPASS Compound

Structure

CID7178 OpenBabel06191715332D 42 44 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 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -3.4641 -0.0000 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 -0.8660 -3.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 1.7321 1.0000 0.0000 O 0 0 0 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 9 1 0 0 0 0 5 19 2 0 0 0 0 6 10 2 0 0 0 0 6 19 1 0 0 0 0 7 11 1 0 0 0 0 7 20 2 0 0 0 0 8 12 2 0 0 0 0 8 20 1 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 1 1 1 0 0 0 15 39 1 0 0 0 0 16 2 1 1 0 0 0 16 40 1 0 0 0 0 17 31 2 0 0 0 0 17 39 1 0 0 0 0 18 32 2 0 0 0 0 18 40 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 35 2 0 0 0 0 23 41 1 0 0 0 0 24 36 2 0 0 0 0 24 42 1 0 0 0 0 25 28 2 0 0 0 0 25 29 1 0 0 0 0 26 27 1 0 0 0 0 26 30 2 0 0 0 0 27 29 2 0 0 0 0 27 37 1 0 0 0 0 28 30 1 0 0 0 0 28 38 1 0 0 0 0 29 41 1 0 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.17
Volume:	572.975
LogP:	4.047
LogD:	2.478
LogS:	-3.908
# Rotatable Bonds:	14
TPSA:	186.12
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.151
Synthetic Accessibility Score:	3.743
Fsp3:	0.267
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.218
MDCK Permeability:	2.7265361495665275e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	99.54859161376953%
Volume Distribution (VD):	0.32
Pgp-substrate:	1.39404296875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.696
CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.723
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.885
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	1.257
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.351
Maximum Recommended Daily Dose:	0.053
Skin Sensitization:	0.258
Carcinogencity:	0.588
Eye Corrosion:	0.003
Eye Irritation:	0.448
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC7178

Natural Product ID:	NPC7178
*Common Name:**	Curtisian M
IUPAC Name:	[4-[(3R)-3-acetyloxybutanoyl]oxy-2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)phenyl] (3R)-3-acetyloxybutanoate
Synonyms:	Curtisian M
Standard InCHIKey:	ZSTKODOFTJPOLN-HZPDHXFCSA-N
Standard InCHI:	InChI=1S/C30H30O12/c1-15(39-17(3)31)13-23(35)41-29-25(19-5-9-21(33)10-6-19)28(38)30(42-24(36)14-16(2)40-18(4)32)26(27(29)37)20-7-11-22(34)12-8-20/h5-12,15-16,33-34,37-38H,13-14H2,1-4H3/t15-,16-/m1/s1
SMILES:	C[C@H](CC(=O)Oc1c(c2ccc(cc2)O)c(c(c(c2ccc(cc2)O)c1O)OC(=O)C[C@@H](C)OC(=O)C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558743
PubChem CID:	45267452
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002042] Terphenyls [CHEMONTID:0002126] P-terphenyls

*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
NPO16348	Paxillus curtisii	Species	Paxillaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[10805570]
NPO16348	Paxillus curtisii	Species	Paxillaceae	Eukaryota	fruiting bodies	Odae National Parks, Korea	n.a.	PMID[19450986]
NPO16348	Paxillus curtisii	Species	Paxillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16348	Paxillus curtisii	Species	Paxillaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	>	500000.0	nM	PMID[521210]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8150.0	nM	PMID[521210]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	500000.0	nM	PMID[521210]

☑ 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 NPC7178 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	358
0.1-0.2	1507
0.2-0.3	3846
0.3-0.4	10216
0.4-0.5	8471
0.5-0.6	3640
0.6-0.7	5499
0.7-0.8	7484
0.8-0.85	1432
0.85-0.9	224
0.9-0.95	13
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC62903
0.9932	High Similarity	NPC142479
0.9932	High Similarity	NPC155015
0.9796	High Similarity	NPC476154
0.9658	High Similarity	NPC113790
0.9542	High Similarity	NPC55121
0.9542	High Similarity	NPC174311
0.9521	High Similarity	NPC97937
0.9521	High Similarity	NPC275125
0.9521	High Similarity	NPC170239
0.9384	High Similarity	NPC125617
0.929	High Similarity	NPC476200
0.929	High Similarity	NPC192258
0.9276	High Similarity	NPC292385
0.9276	High Similarity	NPC125709
0.9241	High Similarity	NPC476279
0.915	High Similarity	NPC476642
0.9032	High Similarity	NPC36077
0.8974	High Similarity	NPC36354
0.8954	High Similarity	NPC163598
0.8954	High Similarity	NPC120774
0.8954	High Similarity	NPC264875
0.8904	High Similarity	NPC25111
0.8904	High Similarity	NPC90615
0.8904	High Similarity	NPC73535
0.8904	High Similarity	NPC272157
0.8904	High Similarity	NPC201145
0.8904	High Similarity	NPC6262
0.8896	High Similarity	NPC78809
0.8882	High Similarity	NPC30688
0.8882	High Similarity	NPC176903
0.8874	High Similarity	NPC208507
0.8874	High Similarity	NPC472333
0.8859	High Similarity	NPC256555
0.8859	High Similarity	NPC91492
0.8859	High Similarity	NPC7439
0.8859	High Similarity	NPC110067
0.8859	High Similarity	NPC34245
0.8844	High Similarity	NPC22517
0.8836	High Similarity	NPC300846
0.8836	High Similarity	NPC476639
0.8836	High Similarity	NPC114155
0.8827	High Similarity	NPC265214
0.8824	High Similarity	NPC294522
0.8824	High Similarity	NPC21184
0.8824	High Similarity	NPC120426
0.8824	High Similarity	NPC205727
0.8808	High Similarity	NPC268515
0.8808	High Similarity	NPC40222
0.8792	High Similarity	NPC469564
0.8784	High Similarity	NPC165026
0.8784	High Similarity	NPC73505
0.8784	High Similarity	NPC295719
0.8784	High Similarity	NPC34431
0.8776	High Similarity	NPC102904
0.8776	High Similarity	NPC326797
0.8776	High Similarity	NPC176051
0.8776	High Similarity	NPC103976
0.8776	High Similarity	NPC474282
0.8776	High Similarity	NPC107551
0.8767	High Similarity	NPC283009
0.8767	High Similarity	NPC111655
0.8767	High Similarity	NPC261873
0.8765	High Similarity	NPC67424
0.8742	High Similarity	NPC155754
0.8742	High Similarity	NPC109061
0.8742	High Similarity	NPC124747
0.8733	High Similarity	NPC477616
0.8726	High Similarity	NPC165483
0.8725	High Similarity	NPC471389
0.8718	High Similarity	NPC8712
0.8716	High Similarity	NPC245207
0.8716	High Similarity	NPC127218
0.8716	High Similarity	NPC319647
0.8716	High Similarity	NPC25966
0.8707	High Similarity	NPC472336
0.8707	High Similarity	NPC472334
0.8704	High Similarity	NPC167231
0.8704	High Similarity	NPC215802
0.8699	High Similarity	NPC103967
0.8693	High Similarity	NPC175976
0.8693	High Similarity	NPC187398
0.8693	High Similarity	NPC139839
0.8693	High Similarity	NPC476348
0.8693	High Similarity	NPC477879
0.8679	High Similarity	NPC301089
0.8675	High Similarity	NPC87883
0.8667	High Similarity	NPC472332
0.8667	High Similarity	NPC107161
0.8667	High Similarity	NPC175838
0.8667	High Similarity	NPC472335
0.8658	High Similarity	NPC291101
0.8658	High Similarity	NPC22317
0.8658	High Similarity	NPC254759
0.8658	High Similarity	NPC160283
0.8658	High Similarity	NPC266197
0.8654	High Similarity	NPC475141
0.8654	High Similarity	NPC149735
0.8654	High Similarity	NPC473236
0.8649	High Similarity	NPC276490
0.8639	High Similarity	NPC474206
0.8639	High Similarity	NPC252095
0.8639	High Similarity	NPC94750
0.8639	High Similarity	NPC470356
0.8639	High Similarity	NPC112939
0.8639	High Similarity	NPC112246
0.8639	High Similarity	NPC472337
0.8639	High Similarity	NPC121812
0.8639	High Similarity	NPC224941
0.8639	High Similarity	NPC311430
0.8627	High Similarity	NPC476347
0.8627	High Similarity	NPC15577
0.8627	High Similarity	NPC178129
0.8616	High Similarity	NPC98083
0.8616	High Similarity	NPC24339
0.8616	High Similarity	NPC94220
0.8616	High Similarity	NPC166456
0.8616	High Similarity	NPC7543
0.86	High Similarity	NPC247291
0.86	High Similarity	NPC311530
0.86	High Similarity	NPC178054
0.8599	High Similarity	NPC268484
0.8599	High Similarity	NPC473736
0.8598	High Similarity	NPC91043
0.8591	High Similarity	NPC471388
0.8591	High Similarity	NPC29868
0.8591	High Similarity	NPC212942
0.8591	High Similarity	NPC292882
0.8591	High Similarity	NPC79622
0.859	High Similarity	NPC476434
0.8581	High Similarity	NPC227503
0.8581	High Similarity	NPC265433
0.8581	High Similarity	NPC471719
0.8581	High Similarity	NPC16435
0.8581	High Similarity	NPC306441
0.8581	High Similarity	NPC162659
0.8581	High Similarity	NPC230734
0.8581	High Similarity	NPC474639
0.8581	High Similarity	NPC173660
0.8581	High Similarity	NPC270456
0.8581	High Similarity	NPC248727
0.858	High Similarity	NPC142614
0.8571	High Similarity	NPC252402
0.8571	High Similarity	NPC281549
0.8571	High Similarity	NPC48366
0.8571	High Similarity	NPC474600
0.8571	High Similarity	NPC310854
0.8571	High Similarity	NPC106215
0.8571	High Similarity	NPC102934
0.8563	High Similarity	NPC297807
0.8562	High Similarity	NPC190714
0.8562	High Similarity	NPC218884
0.8562	High Similarity	NPC474054
0.8562	High Similarity	NPC475896
0.8562	High Similarity	NPC99515
0.8562	High Similarity	NPC317053
0.8562	High Similarity	NPC260397
0.8562	High Similarity	NPC112251
0.8562	High Similarity	NPC324492
0.8562	High Similarity	NPC53889
0.8553	High Similarity	NPC45257
0.8553	High Similarity	NPC50250
0.8553	High Similarity	NPC93323
0.8553	High Similarity	NPC280092
0.8553	High Similarity	NPC12641
0.8553	High Similarity	NPC125495
0.8545	High Similarity	NPC158226
0.8543	High Similarity	NPC131971
0.8535	High Similarity	NPC150442
0.8535	High Similarity	NPC474656
0.8535	High Similarity	NPC199773
0.8535	High Similarity	NPC65591
0.8535	High Similarity	NPC178574
0.8535	High Similarity	NPC289968
0.8535	High Similarity	NPC223720
0.8533	High Similarity	NPC259519
0.8533	High Similarity	NPC308768
0.8533	High Similarity	NPC12668
0.8533	High Similarity	NPC27495
0.8533	High Similarity	NPC309124
0.8533	High Similarity	NPC184797
0.8526	High Similarity	NPC225129
0.8523	High Similarity	NPC38874
0.8523	High Similarity	NPC474886
0.8523	High Similarity	NPC476171
0.8523	High Similarity	NPC211549
0.8523	High Similarity	NPC105493
0.8523	High Similarity	NPC48956
0.8516	High Similarity	NPC475250
0.8516	High Similarity	NPC125570
0.8516	High Similarity	NPC474393
0.8516	High Similarity	NPC474347
0.8514	High Similarity	NPC47398
0.8514	High Similarity	NPC201357
0.8514	High Similarity	NPC234333
0.8514	High Similarity	NPC61946
0.8514	High Similarity	NPC151224
0.8514	High Similarity	NPC255147
0.8514	High Similarity	NPC281521
0.8514	High Similarity	NPC195022

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 NPC7178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	899
0.2-0.3	1847
0.3-0.4	2697
0.4-0.5	1686
0.5-0.6	978
0.6-0.7	579
0.7-0.8	142
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8537	High Similarity	NPD5844	Phase 1
0.8375	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6232	Discontinued
0.8311	Intermediate Similarity	NPD1613	Approved
0.8311	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD1934	Approved
0.828	Intermediate Similarity	NPD1653	Approved
0.8272	Intermediate Similarity	NPD6234	Discontinued
0.825	Intermediate Similarity	NPD2801	Approved
0.8242	Intermediate Similarity	NPD6166	Phase 2
0.8242	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD3027	Phase 3
0.8193	Intermediate Similarity	NPD7473	Discontinued
0.8163	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD3817	Phase 2
0.8075	Intermediate Similarity	NPD37	Approved
0.8061	Intermediate Similarity	NPD7199	Phase 2
0.8037	Intermediate Similarity	NPD4967	Phase 2
0.8037	Intermediate Similarity	NPD4966	Approved
0.8037	Intermediate Similarity	NPD4965	Approved
0.8012	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7074	Phase 3
0.7929	Intermediate Similarity	NPD3818	Discontinued
0.7929	Intermediate Similarity	NPD7228	Approved
0.7919	Intermediate Similarity	NPD4908	Phase 1
0.7914	Intermediate Similarity	NPD1465	Phase 2
0.7882	Intermediate Similarity	NPD7054	Approved
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7836	Intermediate Similarity	NPD7472	Approved
0.7818	Intermediate Similarity	NPD3882	Suspended
0.7815	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1511	Approved
0.7791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7763	Intermediate Similarity	NPD6233	Phase 2
0.7758	Intermediate Similarity	NPD5402	Approved
0.775	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6959	Discontinued
0.7711	Intermediate Similarity	NPD7768	Phase 2
0.7702	Intermediate Similarity	NPD1512	Approved
0.7702	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7549	Discontinued
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6798	Discontinued
0.7688	Intermediate Similarity	NPD6797	Phase 2
0.7679	Intermediate Similarity	NPD5494	Approved
0.7644	Intermediate Similarity	NPD7251	Discontinued
0.7632	Intermediate Similarity	NPD4625	Phase 3
0.7622	Intermediate Similarity	NPD6599	Discontinued
0.7616	Intermediate Similarity	NPD2861	Phase 2
0.76	Intermediate Similarity	NPD7808	Phase 3
0.7597	Intermediate Similarity	NPD4060	Phase 1
0.759	Intermediate Similarity	NPD7819	Suspended
0.759	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7411	Suspended
0.7568	Intermediate Similarity	NPD1610	Phase 2
0.7562	Intermediate Similarity	NPD6190	Approved
0.756	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD7095	Approved
0.7515	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7485	Intermediate Similarity	NPD8455	Phase 2
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6799	Approved
0.7468	Intermediate Similarity	NPD1551	Phase 2
0.7468	Intermediate Similarity	NPD2935	Discontinued
0.7467	Intermediate Similarity	NPD4749	Approved
0.745	Intermediate Similarity	NPD422	Phase 1
0.7443	Intermediate Similarity	NPD7240	Approved
0.7439	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5403	Approved
0.7438	Intermediate Similarity	NPD1652	Phase 2
0.7438	Intermediate Similarity	NPD6674	Discontinued
0.7436	Intermediate Similarity	NPD6355	Discontinued
0.7427	Intermediate Similarity	NPD8127	Discontinued
0.7423	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7266	Discontinued
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7405	Intermediate Similarity	NPD7033	Discontinued
0.7391	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3750	Approved
0.7391	Intermediate Similarity	NPD4110	Phase 3
0.7386	Intermediate Similarity	NPD3018	Phase 2
0.7384	Intermediate Similarity	NPD7229	Phase 3
0.7375	Intermediate Similarity	NPD1549	Phase 2
0.7368	Intermediate Similarity	NPD6746	Phase 2
0.7358	Intermediate Similarity	NPD6099	Approved
0.7358	Intermediate Similarity	NPD6100	Approved
0.7355	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3749	Approved
0.7351	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3226	Approved
0.7333	Intermediate Similarity	NPD1611	Approved
0.7329	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5124	Phase 1
0.7325	Intermediate Similarity	NPD447	Suspended
0.7317	Intermediate Similarity	NPD2534	Approved
0.7317	Intermediate Similarity	NPD2533	Approved
0.7317	Intermediate Similarity	NPD5401	Approved
0.7317	Intermediate Similarity	NPD2532	Approved
0.7317	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD3751	Discontinued
0.731	Intermediate Similarity	NPD919	Approved
0.7273	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7262	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2797	Approved
0.725	Intermediate Similarity	NPD2796	Approved
0.7246	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3926	Phase 2
0.7237	Intermediate Similarity	NPD2982	Phase 2
0.7237	Intermediate Similarity	NPD2983	Phase 2
0.7233	Intermediate Similarity	NPD7097	Phase 1
0.7222	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD230	Phase 1
0.7205	Intermediate Similarity	NPD5762	Approved
0.7205	Intermediate Similarity	NPD5763	Approved
0.72	Intermediate Similarity	NPD1778	Approved
0.7188	Intermediate Similarity	NPD1510	Phase 2
0.7171	Intermediate Similarity	NPD2981	Phase 2
0.717	Intermediate Similarity	NPD1607	Approved
0.7165	Intermediate Similarity	NPD7783	Phase 2
0.7165	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7680	Approved
0.7152	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3496	Discontinued
0.7152	Intermediate Similarity	NPD4140	Approved
0.7152	Intermediate Similarity	NPD3620	Phase 2
0.7151	Intermediate Similarity	NPD7038	Approved
0.7151	Intermediate Similarity	NPD7039	Approved
0.7143	Intermediate Similarity	NPD6032	Approved
0.7143	Intermediate Similarity	NPD2438	Suspended
0.7134	Intermediate Similarity	NPD3268	Approved
0.7128	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1247	Approved
0.7123	Intermediate Similarity	NPD5535	Approved
0.7108	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3686	Approved
0.7083	Intermediate Similarity	NPD3687	Approved
0.7081	Intermediate Similarity	NPD3748	Approved
0.7078	Intermediate Similarity	NPD3225	Approved
0.7075	Intermediate Similarity	NPD5283	Phase 1
0.7063	Intermediate Similarity	NPD6653	Approved
0.7059	Intermediate Similarity	NPD1608	Approved
0.7055	Intermediate Similarity	NPD228	Approved
0.7048	Intermediate Similarity	NPD7212	Phase 2
0.7048	Intermediate Similarity	NPD7213	Phase 3
0.7044	Intermediate Similarity	NPD1240	Approved
0.7041	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7985	Registered
0.7006	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7447	Phase 1
0.7006	Intermediate Similarity	NPD6832	Phase 2
0.7	Intermediate Similarity	NPD1933	Approved
0.6994	Remote Similarity	NPD2346	Discontinued
0.6994	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1535	Discovery
0.6993	Remote Similarity	NPD1091	Approved
0.6987	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4062	Phase 3
0.698	Remote Similarity	NPD6671	Approved
0.6975	Remote Similarity	NPD4308	Phase 3
0.6974	Remote Similarity	NPD4626	Approved
0.6974	Remote Similarity	NPD8151	Discontinued
0.6971	Remote Similarity	NPD4666	Phase 3
0.697	Remote Similarity	NPD8166	Discontinued
0.6968	Remote Similarity	NPD1283	Approved
0.6964	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7685	Pre-registration
0.6957	Remote Similarity	NPD8434	Phase 2
0.6954	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1481	Phase 2
0.6946	Remote Similarity	NPD4357	Discontinued
0.6946	Remote Similarity	NPD7390	Discontinued
0.694	Remote Similarity	NPD8054	Approved
0.694	Remote Similarity	NPD8053	Approved
0.6937	Remote Similarity	NPD943	Approved
0.6937	Remote Similarity	NPD1558	Phase 1
0.6937	Remote Similarity	NPD2979	Phase 3
0.6933	Remote Similarity	NPD5408	Approved
0.6933	Remote Similarity	NPD5405	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