NPASS Compound

Structure

NPC476154 OpenBabel07101718282D 42 44 0 0 1 0 0 0 0 0999 V2000 4.9702 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1419 0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6567 -3.8261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.8696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1419 0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3135 1.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4851 -1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6567 -2.8696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9702 0.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1419 2.3913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3135 -1.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4851 -3.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1419 -1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4851 0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9702 -0.9565 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3135 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6567 -2.8696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3135 0.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6567 -1.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9702 1.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3135 -2.8696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3135 -0.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6567 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6567 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 -1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6567 -0.9565 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 5.7986 -1.4348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3135 -0.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4851 -2.3913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8284 1.4348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7986 2.3913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1419 -3.3478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3135 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6567 -0.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 -2.3913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 1.4348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4851 -1.4348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8284 0.4783 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 31 1 0 0 0 0 16 2 1 6 0 0 0 16 32 1 0 0 0 0 17 33 2 0 0 0 0 17 39 1 0 0 0 0 18 34 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 35 1 0 0 0 0 22 36 1 0 0 0 0 23 37 2 0 0 0 0 23 41 1 0 0 0 0 24 38 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 39 1 0 0 0 0 28 30 1 0 0 0 0 28 40 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:	2.8
LogD:	0.869
LogS:	-5.378
# 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:	0.201
Synthetic Accessibility Score:	3.677
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:	-5.379
MDCK Permeability:	2.7376439902582206e-05
Pgp-inhibitor:	0.89
Pgp-substrate:	0.954
Human Intestinal Absorption (HIA):	0.598
20% Bioavailability (F20%):	0.085
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	80.00798797607422%
Volume Distribution (VD):	0.411
Pgp-substrate:	19.29033851623535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.518
CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.86
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.911
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.361
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	1.179
Half-life (T1/2):	0.852

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.002
Drug-inuced Liver Injury (DILI):	0.442
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.801
Maximum Recommended Daily Dose:	0.738
Skin Sensitization:	0.65
Carcinogencity:	0.273
Eye Corrosion:	0.003
Eye Irritation:	0.34
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC476154

Natural Product ID:	NPC476154
*Common Name:**	Curtisian U
IUPAC Name:	[2,5-diacetyloxy-4-[(3R)-3-hydroxybutanoyl]oxy-3,6-bis(4-hydroxyphenyl)phenyl] (3R)-3-hydroxybutanoate
Synonyms:	Curtisian U
Standard InCHIKey:	ASLFGEZJFDFJAM-HZPDHXFCSA-N
Standard InCHI:	InChI=1S/C30H30O12/c1-15(31)13-23(37)41-29-25(19-5-9-21(35)10-6-19)28(40-18(4)34)30(42-24(38)14-16(2)32)26(27(29)39-17(3)33)20-7-11-22(36)12-8-20/h5-12,15-16,31-32,35-36H,13-14H2,1-4H3/t15-,16-/m1/s1
SMILES:	CC(CC(=O)OC1=C(C(=C(C(=C1OC(=O)C)C2=CC=C(C=C2)O)OC(=O)CC(C)O)OC(=O)C)C3=CC=C(C=C3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL541186
PubChem CID:	45268317
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[545960]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	500000.0	nM	PMID[545960]

☑ 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 NPC476154 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	348
0.1-0.2	1467
0.2-0.3	3744
0.3-0.4	9738
0.4-0.5	9041
0.5-0.6	3590
0.6-0.7	5535
0.7-0.8	7949
0.8-0.85	1156
0.85-0.9	114
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC155015
0.9864	High Similarity	NPC142479
0.9796	High Similarity	NPC7178
0.9796	High Similarity	NPC62903
0.9477	High Similarity	NPC476200
0.9477	High Similarity	NPC192258
0.9477	High Similarity	NPC55121
0.9456	High Similarity	NPC113790
0.9448	High Similarity	NPC125617
0.9351	High Similarity	NPC174311
0.932	High Similarity	NPC275125
0.932	High Similarity	NPC97937
0.932	High Similarity	NPC170239
0.9085	High Similarity	NPC125709
0.9085	High Similarity	NPC292385
0.9057	High Similarity	NPC476279
0.8961	High Similarity	NPC476642
0.8874	High Similarity	NPC477879
0.8846	High Similarity	NPC36077
0.8831	High Similarity	NPC78809
0.8828	High Similarity	NPC111655
0.8808	High Similarity	NPC472333
0.8808	High Similarity	NPC208507
0.879	High Similarity	NPC36354
0.8776	High Similarity	NPC22517
0.8776	High Similarity	NPC471388
0.8766	High Similarity	NPC163598
0.8766	High Similarity	NPC120774
0.8766	High Similarity	NPC264875
0.8765	High Similarity	NPC265214
0.8758	High Similarity	NPC21184
0.8758	High Similarity	NPC294522
0.8758	High Similarity	NPC205727
0.8758	High Similarity	NPC120426
0.8707	High Similarity	NPC6262
0.8707	High Similarity	NPC201145
0.8707	High Similarity	NPC73535
0.8707	High Similarity	NPC272157
0.8707	High Similarity	NPC90615
0.8707	High Similarity	NPC25111
0.8704	High Similarity	NPC67424
0.8699	High Similarity	NPC311430
0.8699	High Similarity	NPC224941
0.8693	High Similarity	NPC176903
0.8693	High Similarity	NPC30688
0.8684	High Similarity	NPC15577
0.8679	High Similarity	NPC124747
0.8679	High Similarity	NPC155754
0.8679	High Similarity	NPC109061
0.8667	High Similarity	NPC110067
0.8667	High Similarity	NPC91492
0.8667	High Similarity	NPC477616
0.8667	High Similarity	NPC7439
0.8667	High Similarity	NPC34245
0.8667	High Similarity	NPC256555
0.8662	High Similarity	NPC165483
0.8658	High Similarity	NPC471389
0.8654	High Similarity	NPC8712
0.8639	High Similarity	NPC472334
0.8639	High Similarity	NPC471719
0.8639	High Similarity	NPC476698
0.8639	High Similarity	NPC476639
0.8639	High Similarity	NPC114155
0.8639	High Similarity	NPC300846
0.8639	High Similarity	NPC173660
0.8639	High Similarity	NPC472336
0.8636	High Similarity	NPC477381
0.863	High Similarity	NPC309744
0.863	High Similarity	NPC474600
0.8627	High Similarity	NPC476348
0.8627	High Similarity	NPC187398
0.8627	High Similarity	NPC175976
0.8625	High Similarity	NPC249070
0.8618	High Similarity	NPC268515
0.8618	High Similarity	NPC40222
0.86	High Similarity	NPC469564
0.8591	High Similarity	NPC295719
0.8591	High Similarity	NPC34431
0.8591	High Similarity	NPC73505
0.8591	High Similarity	NPC165026
0.8591	High Similarity	NPC27495
0.8591	High Similarity	NPC266197
0.8591	High Similarity	NPC291101
0.859	High Similarity	NPC149735
0.859	High Similarity	NPC473236
0.8581	High Similarity	NPC326797
0.8581	High Similarity	NPC176051
0.8581	High Similarity	NPC477379
0.8581	High Similarity	NPC107551
0.8581	High Similarity	NPC103976
0.8581	High Similarity	NPC474282
0.8581	High Similarity	NPC476171
0.8581	High Similarity	NPC102904
0.858	High Similarity	NPC20216
0.8571	High Similarity	NPC61946
0.8571	High Similarity	NPC195022
0.8571	High Similarity	NPC261873
0.8571	High Similarity	NPC283009
0.8571	High Similarity	NPC472337
0.8562	High Similarity	NPC476347
0.8553	High Similarity	NPC166456
0.8553	High Similarity	NPC24339
0.8553	High Similarity	NPC98083
0.8553	High Similarity	NPC7543
0.8553	High Similarity	NPC94220
0.8535	High Similarity	NPC473425
0.8533	High Similarity	NPC178054
0.8533	High Similarity	NPC311530
0.8528	High Similarity	NPC215802
0.8528	High Similarity	NPC167231
0.8523	High Similarity	NPC164148
0.8523	High Similarity	NPC245207
0.8523	High Similarity	NPC25966
0.8523	High Similarity	NPC319647
0.8523	High Similarity	NPC127218
0.8523	High Similarity	NPC43500
0.8519	High Similarity	NPC112981
0.8514	High Similarity	NPC286843
0.8514	High Similarity	NPC16435
0.8514	High Similarity	NPC306441
0.8514	High Similarity	NPC205442
0.8506	High Similarity	NPC139839
0.8503	High Similarity	NPC310854
0.8503	High Similarity	NPC103967
0.85	High Similarity	NPC301089
0.8497	Intermediate Similarity	NPC99515
0.8497	Intermediate Similarity	NPC112251
0.8497	Intermediate Similarity	NPC324492
0.8497	Intermediate Similarity	NPC205361
0.8497	Intermediate Similarity	NPC190714
0.8497	Intermediate Similarity	NPC260397
0.8497	Intermediate Similarity	NPC474054
0.8497	Intermediate Similarity	NPC317053
0.8491	Intermediate Similarity	NPC108456
0.8487	Intermediate Similarity	NPC87883
0.8483	Intermediate Similarity	NPC476399
0.8477	Intermediate Similarity	NPC472332
0.8477	Intermediate Similarity	NPC472335
0.8477	Intermediate Similarity	NPC107161
0.8477	Intermediate Similarity	NPC175838
0.8476	Intermediate Similarity	NPC99613
0.8476	Intermediate Similarity	NPC49487
0.8471	Intermediate Similarity	NPC150442
0.8471	Intermediate Similarity	NPC475141
0.8471	Intermediate Similarity	NPC178574
0.8471	Intermediate Similarity	NPC65591
0.8467	Intermediate Similarity	NPC22317
0.8467	Intermediate Similarity	NPC160283
0.8467	Intermediate Similarity	NPC254759
0.8462	Intermediate Similarity	NPC164527
0.8462	Intermediate Similarity	NPC225129
0.8462	Intermediate Similarity	NPC213382
0.8457	Intermediate Similarity	NPC156082
0.8456	Intermediate Similarity	NPC276490
0.8456	Intermediate Similarity	NPC266006
0.8452	Intermediate Similarity	NPC475250
0.8447	Intermediate Similarity	NPC139540
0.8447	Intermediate Similarity	NPC177100
0.8446	Intermediate Similarity	NPC121812
0.8446	Intermediate Similarity	NPC252095
0.8446	Intermediate Similarity	NPC260898
0.8446	Intermediate Similarity	NPC94750
0.8446	Intermediate Similarity	NPC234333
0.8446	Intermediate Similarity	NPC112939
0.8446	Intermediate Similarity	NPC234865
0.8446	Intermediate Similarity	NPC47398
0.8446	Intermediate Similarity	NPC112246
0.8446	Intermediate Similarity	NPC470356
0.8446	Intermediate Similarity	NPC474206
0.8442	Intermediate Similarity	NPC227902
0.8442	Intermediate Similarity	NPC320671
0.8442	Intermediate Similarity	NPC320970
0.8442	Intermediate Similarity	NPC328567
0.8442	Intermediate Similarity	NPC178129
0.8442	Intermediate Similarity	NPC327412
0.8438	Intermediate Similarity	NPC287458
0.8435	Intermediate Similarity	NPC263064
0.8435	Intermediate Similarity	NPC269528
0.8435	Intermediate Similarity	NPC475840
0.8431	Intermediate Similarity	NPC181615
0.8431	Intermediate Similarity	NPC221318
0.8424	Intermediate Similarity	NPC91043
0.8424	Intermediate Similarity	NPC17219
0.8418	Intermediate Similarity	NPC473736
0.8418	Intermediate Similarity	NPC268484
0.8415	Intermediate Similarity	NPC234331
0.8411	Intermediate Similarity	NPC300611
0.8411	Intermediate Similarity	NPC247291
0.8408	Intermediate Similarity	NPC53587
0.8408	Intermediate Similarity	NPC169404
0.8408	Intermediate Similarity	NPC21902
0.8408	Intermediate Similarity	NPC476434
0.8408	Intermediate Similarity	NPC176186
0.8405	Intermediate Similarity	NPC142614
0.84	Intermediate Similarity	NPC212942
0.84	Intermediate Similarity	NPC29868
0.84	Intermediate Similarity	NPC292882
0.84	Intermediate Similarity	NPC79622
0.8397	Intermediate Similarity	NPC106334
0.8397	Intermediate Similarity	NPC158784

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 NPC476154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	895
0.2-0.3	1826
0.3-0.4	2659
0.4-0.5	1731
0.5-0.6	974
0.6-0.7	599
0.7-0.8	157
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8704	High Similarity	NPD5844	Phase 1
0.8395	Intermediate Similarity	NPD6232	Discontinued
0.8243	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1613	Approved
0.8242	Intermediate Similarity	NPD7473	Discontinued
0.8239	Intermediate Similarity	NPD37	Approved
0.8217	Intermediate Similarity	NPD1653	Approved
0.8199	Intermediate Similarity	NPD4966	Approved
0.8199	Intermediate Similarity	NPD4965	Approved
0.8199	Intermediate Similarity	NPD4967	Phase 2
0.8199	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD3027	Phase 3
0.8125	Intermediate Similarity	NPD1934	Approved
0.811	Intermediate Similarity	NPD7199	Phase 2
0.8098	Intermediate Similarity	NPD6234	Discontinued
0.8075	Intermediate Similarity	NPD2801	Approved
0.8025	Intermediate Similarity	NPD3817	Phase 2
0.7973	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD4908	Phase 1
0.7963	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6559	Discontinued
0.7882	Intermediate Similarity	NPD7074	Phase 3
0.787	Intermediate Similarity	NPD7228	Approved
0.787	Intermediate Similarity	NPD3818	Discontinued
0.7867	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7054	Approved
0.7805	Intermediate Similarity	NPD5402	Approved
0.7784	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6959	Discontinued
0.7778	Intermediate Similarity	NPD7472	Approved
0.7758	Intermediate Similarity	NPD7768	Phase 2
0.775	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7549	Discontinued
0.7744	Intermediate Similarity	NPD1465	Phase 2
0.7733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5494	Approved
0.7711	Intermediate Similarity	NPD7075	Discontinued
0.7697	Intermediate Similarity	NPD6233	Phase 2
0.7682	Intermediate Similarity	NPD4625	Phase 3
0.7667	Intermediate Similarity	NPD2861	Phase 2
0.7651	Intermediate Similarity	NPD3882	Suspended
0.7644	Intermediate Similarity	NPD7808	Phase 3
0.7636	Intermediate Similarity	NPD7819	Suspended
0.7632	Intermediate Similarity	NPD6798	Discontinued
0.763	Intermediate Similarity	NPD6797	Phase 2
0.7625	Intermediate Similarity	NPD1511	Approved
0.7622	Intermediate Similarity	NPD7411	Suspended
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7605	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7251	Discontinued
0.7576	Intermediate Similarity	NPD6801	Discontinued
0.7574	Intermediate Similarity	NPD8127	Discontinued
0.7564	Intermediate Similarity	NPD7033	Discontinued
0.7561	Intermediate Similarity	NPD6599	Discontinued
0.7561	Intermediate Similarity	NPD4380	Phase 2
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7547	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4060	Phase 1
0.7531	Intermediate Similarity	NPD1512	Approved
0.753	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8455	Phase 2
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7517	Intermediate Similarity	NPD4749	Approved
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD422	Phase 1
0.7486	Intermediate Similarity	NPD7240	Approved
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5403	Approved
0.7484	Intermediate Similarity	NPD1652	Phase 2
0.7484	Intermediate Similarity	NPD5124	Phase 1
0.7484	Intermediate Similarity	NPD6674	Discontinued
0.7484	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7451	Intermediate Similarity	NPD7095	Approved
0.7438	Intermediate Similarity	NPD4110	Phase 3
0.7438	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3750	Approved
0.7434	Intermediate Similarity	NPD3018	Phase 2
0.7427	Intermediate Similarity	NPD7229	Phase 3
0.7421	Intermediate Similarity	NPD1549	Phase 2
0.7412	Intermediate Similarity	NPD6746	Phase 2
0.7407	Intermediate Similarity	NPD6799	Approved
0.7405	Intermediate Similarity	NPD6099	Approved
0.7405	Intermediate Similarity	NPD6100	Approved
0.7403	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3749	Approved
0.7394	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3226	Approved
0.7383	Intermediate Similarity	NPD1611	Approved
0.7375	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD447	Suspended
0.7372	Intermediate Similarity	NPD6355	Discontinued
0.7362	Intermediate Similarity	NPD2533	Approved
0.7362	Intermediate Similarity	NPD5401	Approved
0.7362	Intermediate Similarity	NPD2534	Approved
0.7362	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2532	Approved
0.7358	Intermediate Similarity	NPD7266	Discontinued
0.7356	Intermediate Similarity	NPD3751	Discontinued
0.7353	Intermediate Similarity	NPD919	Approved
0.7318	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4140	Approved
0.7305	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2797	Approved
0.7303	Intermediate Similarity	NPD8313	Approved
0.7303	Intermediate Similarity	NPD8312	Approved
0.7296	Intermediate Similarity	NPD2796	Approved
0.7288	Intermediate Similarity	NPD7039	Approved
0.7288	Intermediate Similarity	NPD7038	Approved
0.7285	Intermediate Similarity	NPD2983	Phase 2
0.7285	Intermediate Similarity	NPD2982	Phase 2
0.7283	Intermediate Similarity	NPD3926	Phase 2
0.7278	Intermediate Similarity	NPD7097	Phase 1
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5763	Approved
0.725	Intermediate Similarity	NPD5762	Approved
0.7248	Intermediate Similarity	NPD1778	Approved
0.7233	Intermediate Similarity	NPD1510	Phase 2
0.7229	Intermediate Similarity	NPD3686	Approved
0.7229	Intermediate Similarity	NPD3687	Approved
0.7219	Intermediate Similarity	NPD2981	Phase 2
0.7215	Intermediate Similarity	NPD1607	Approved
0.7202	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7783	Phase 2
0.72	Intermediate Similarity	NPD3496	Discontinued
0.7188	Intermediate Similarity	NPD6032	Approved
0.7188	Intermediate Similarity	NPD2438	Suspended
0.7179	Intermediate Similarity	NPD3268	Approved
0.7172	Intermediate Similarity	NPD5535	Approved
0.7171	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1247	Approved
0.7143	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3748	Approved
0.7124	Intermediate Similarity	NPD3225	Approved
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.7107	Intermediate Similarity	NPD6653	Approved
0.7105	Intermediate Similarity	NPD1608	Approved
0.7105	Intermediate Similarity	NPD7680	Approved
0.7093	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7213	Phase 3
0.7091	Intermediate Similarity	NPD7212	Phase 2
0.7089	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3620	Phase 2
0.7089	Intermediate Similarity	NPD1240	Approved
0.7083	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7985	Registered
0.7052	Intermediate Similarity	NPD5709	Phase 3
0.7051	Intermediate Similarity	NPD6832	Phase 2
0.7048	Intermediate Similarity	NPD7447	Phase 1
0.7044	Intermediate Similarity	NPD1933	Approved
0.7044	Intermediate Similarity	NPD230	Phase 1
0.7039	Intermediate Similarity	NPD1091	Approved
0.7039	Intermediate Similarity	NPD1535	Discovery
0.7037	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6004	Phase 3
0.7037	Intermediate Similarity	NPD2346	Discontinued
0.7037	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6005	Phase 3
0.7037	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6002	Phase 3
0.703	Intermediate Similarity	NPD6667	Approved
0.703	Intermediate Similarity	NPD6666	Approved
0.7027	Intermediate Similarity	NPD6671	Approved
0.702	Intermediate Similarity	NPD4626	Approved
0.7019	Intermediate Similarity	NPD4308	Phase 3
0.7013	Intermediate Similarity	NPD1283	Approved
0.7012	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4666	Phase 3
0.701	Intermediate Similarity	NPD8151	Discontinued
0.7006	Intermediate Similarity	NPD6273	Approved
0.7006	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8434	Phase 2
0.6993	Remote Similarity	NPD1481	Phase 2
0.6988	Remote Similarity	NPD4357	Discontinued
0.6988	Remote Similarity	NPD7390	Discontinued
0.6981	Remote Similarity	NPD2979	Phase 3
0.6977	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5408	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