NPASS Compound

Structure

CID174311 OpenBabel06191715542D 43 46 0 0 1 0 0 0 0 0999 V2000 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 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 -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 1.7321 -3.0000 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 -1.7321 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 -3.4641 4.0000 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 0.8660 -4.5000 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 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 -1.7321 4.0000 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 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 21 2 0 0 0 0 7 21 1 0 0 0 0 8 17 1 0 0 0 0 8 21 1 0 0 0 0 9 13 1 0 0 0 0 9 22 2 0 0 0 0 10 14 2 0 0 0 0 10 22 1 0 0 0 0 11 15 1 0 0 0 0 11 23 2 0 0 0 0 12 16 2 0 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 14 24 1 0 0 0 0 15 25 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 0 0 0 0 19 1 1 1 0 0 0 19 41 1 0 0 0 0 20 34 2 0 0 0 0 20 41 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 37 2 0 0 0 0 26 42 1 0 0 0 0 27 38 2 0 0 0 0 27 43 1 0 0 0 0 28 31 2 0 0 0 0 28 32 1 0 0 0 0 29 30 1 0 0 0 0 29 33 2 0 0 0 0 30 32 2 0 0 0 0 30 39 1 0 0 0 0 31 33 1 0 0 0 0 31 40 1 0 0 0 0 32 42 1 0 0 0 0 33 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.18
Volume:	593.454
LogP:	4.986
LogD:	3.04
LogS:	-3.655
# Rotatable Bonds:	13
TPSA:	159.82
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.104
Synthetic Accessibility Score:	3.337
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
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:	-5.111
MDCK Permeability:	1.5573377822875045e-05
Pgp-inhibitor:	0.783
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	100.98242950439453%
Volume Distribution (VD):	0.375
Pgp-substrate:	0.5092945694923401%

ADMET: Metabolism

CYP1A2-inhibitor:	0.896
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.964
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.91
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.218
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	1.854
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.712
Maximum Recommended Daily Dose:	0.067
Skin Sensitization:	0.571
Carcinogencity:	0.53
Eye Corrosion:	0.003
Eye Irritation:	0.413
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC174311

Natural Product ID:	NPC174311
*Common Name:**	Curtisian J
IUPAC Name:	[2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)-4-(3-phenylpropanoyloxy)phenyl] (3R)-3-acetyloxybutanoate
Synonyms:	Curtisian J
Standard InCHIKey:	ZETBADSRSFPSFF-LJQANCHMSA-N
Standard InCHI:	InChI=1S/C33H30O10/c1-19(41-20(2)34)18-27(38)43-33-29(23-11-15-25(36)16-12-23)30(39)32(28(31(33)40)22-9-13-24(35)14-10-22)42-26(37)17-8-21-6-4-3-5-7-21/h3-7,9-16,19,35-36,39-40H,8,17-18H2,1-2H3/t19-/m1/s1
SMILES:	O=C(Oc1c(c2ccc(cc2)O)c(O)c(c(c1O)c1ccc(cc1)O)OC(=O)C[C@H](OC(=O)C)C)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL541184
PubChem CID:	45268302
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[552672]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13450.0	nM	PMID[552672]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	500000.0	nM	PMID[552672]

☑ 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 NPC174311 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	378
0.1-0.2	1562
0.2-0.3	3655
0.3-0.4	9542
0.4-0.5	9226
0.5-0.6	3657
0.6-0.7	5369
0.7-0.8	7597
0.8-0.85	1568
0.85-0.9	120
0.9-0.95	13
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC55121
0.9742	High Similarity	NPC476200
0.9742	High Similarity	NPC192258
0.9608	High Similarity	NPC292385
0.9608	High Similarity	NPC125709
0.956	High Similarity	NPC476279
0.9542	High Similarity	NPC7178
0.9542	High Similarity	NPC62903
0.9484	High Similarity	NPC36077
0.9481	High Similarity	NPC155015
0.9481	High Similarity	NPC142479
0.9423	High Similarity	NPC36354
0.9351	High Similarity	NPC476154
0.9216	High Similarity	NPC113790
0.9108	High Similarity	NPC476642
0.9085	High Similarity	NPC275125
0.9085	High Similarity	NPC170239
0.9085	High Similarity	NPC97937
0.9018	High Similarity	NPC215802
0.9018	High Similarity	NPC167231
0.8954	High Similarity	NPC125617
0.8909	High Similarity	NPC91043
0.8839	High Similarity	NPC208507
0.8839	High Similarity	NPC472333
0.8827	High Similarity	NPC155754
0.8827	High Similarity	NPC124747
0.8827	High Similarity	NPC109061
0.882	High Similarity	NPC287458
0.8812	High Similarity	NPC165483
0.8795	High Similarity	NPC265214
0.8795	High Similarity	NPC476365
0.8773	High Similarity	NPC476372
0.8773	High Similarity	NPC476371
0.8765	High Similarity	NPC98892
0.8735	High Similarity	NPC67424
0.8727	High Similarity	NPC9309
0.8712	High Similarity	NPC177100
0.8712	High Similarity	NPC139540
0.8704	High Similarity	NPC94220
0.8704	High Similarity	NPC24339
0.8704	High Similarity	NPC98083
0.8704	High Similarity	NPC7543
0.8704	High Similarity	NPC166456
0.8683	High Similarity	NPC180768
0.8679	High Similarity	NPC120774
0.8679	High Similarity	NPC264875
0.8679	High Similarity	NPC163598
0.8667	High Similarity	NPC142614
0.8667	High Similarity	NPC477840
0.8663	High Similarity	NPC154527
0.8662	High Similarity	NPC139839
0.8662	High Similarity	NPC281549
0.8659	High Similarity	NPC140346
0.865	High Similarity	NPC301089
0.865	High Similarity	NPC476373
0.865	High Similarity	NPC53889
0.8647	High Similarity	NPC297807
0.8642	High Similarity	NPC125495
0.8636	High Similarity	NPC472332
0.8636	High Similarity	NPC472335
0.8631	High Similarity	NPC174700
0.8631	High Similarity	NPC476370
0.8627	High Similarity	NPC22317
0.8625	High Similarity	NPC78809
0.8625	High Similarity	NPC474656
0.8625	High Similarity	NPC473236
0.8613	High Similarity	NPC226725
0.8608	High Similarity	NPC475250
0.8608	High Similarity	NPC176903
0.8608	High Similarity	NPC30688
0.8598	High Similarity	NPC216916
0.8596	High Similarity	NPC324742
0.8589	High Similarity	NPC87317
0.8588	High Similarity	NPC216307
0.858	High Similarity	NPC476374
0.8563	High Similarity	NPC473818
0.8562	High Similarity	NPC476434
0.8553	High Similarity	NPC120426
0.8553	High Similarity	NPC294522
0.8553	High Similarity	NPC205727
0.8553	High Similarity	NPC21184
0.8547	High Similarity	NPC47883
0.8545	High Similarity	NPC477841
0.8545	High Similarity	NPC473445
0.8545	High Similarity	NPC219927
0.8538	High Similarity	NPC98546
0.8537	High Similarity	NPC24164
0.8537	High Similarity	NPC188967
0.8535	High Similarity	NPC268515
0.8535	High Similarity	NPC40222
0.8528	High Similarity	NPC156818
0.8528	High Similarity	NPC289322
0.8528	High Similarity	NPC160512
0.8528	High Similarity	NPC68324
0.8528	High Similarity	NPC38779
0.8528	High Similarity	NPC114179
0.8521	High Similarity	NPC158226
0.8514	High Similarity	NPC477083
0.8514	High Similarity	NPC477081
0.8512	High Similarity	NPC475212
0.8512	High Similarity	NPC280493
0.8509	High Similarity	NPC199773
0.8509	High Similarity	NPC65591
0.8509	High Similarity	NPC178574
0.8509	High Similarity	NPC289968
0.8506	High Similarity	NPC469650
0.8506	High Similarity	NPC111490
0.8506	High Similarity	NPC261623
0.8503	High Similarity	NPC471823
0.85	High Similarity	NPC300329
0.85	High Similarity	NPC225129
0.8497	Intermediate Similarity	NPC90615
0.8497	Intermediate Similarity	NPC73535
0.8497	Intermediate Similarity	NPC6262
0.8497	Intermediate Similarity	NPC272157
0.8497	Intermediate Similarity	NPC48956
0.8497	Intermediate Similarity	NPC201145
0.8497	Intermediate Similarity	NPC25111
0.8494	Intermediate Similarity	NPC291977
0.8494	Intermediate Similarity	NPC45943
0.8494	Intermediate Similarity	NPC272064
0.8491	Intermediate Similarity	NPC125570
0.8491	Intermediate Similarity	NPC476969
0.8491	Intermediate Similarity	NPC321657
0.8491	Intermediate Similarity	NPC318373
0.8488	Intermediate Similarity	NPC185275
0.8485	Intermediate Similarity	NPC158188
0.8476	Intermediate Similarity	NPC284127
0.8476	Intermediate Similarity	NPC190487
0.8476	Intermediate Similarity	NPC172202
0.8476	Intermediate Similarity	NPC476410
0.8476	Intermediate Similarity	NPC154304
0.8466	Intermediate Similarity	NPC55463
0.8466	Intermediate Similarity	NPC318432
0.8466	Intermediate Similarity	NPC291948
0.8466	Intermediate Similarity	NPC88803
0.8466	Intermediate Similarity	NPC300845
0.8466	Intermediate Similarity	NPC250436
0.8466	Intermediate Similarity	NPC104983
0.8466	Intermediate Similarity	NPC166116
0.8462	Intermediate Similarity	NPC34245
0.8462	Intermediate Similarity	NPC91492
0.8462	Intermediate Similarity	NPC7439
0.8462	Intermediate Similarity	NPC109827
0.8462	Intermediate Similarity	NPC17884
0.8462	Intermediate Similarity	NPC124470
0.8462	Intermediate Similarity	NPC19273
0.8462	Intermediate Similarity	NPC256555
0.8462	Intermediate Similarity	NPC110067
0.8457	Intermediate Similarity	NPC469888
0.8457	Intermediate Similarity	NPC8712
0.8457	Intermediate Similarity	NPC269625
0.8457	Intermediate Similarity	NPC469649
0.8457	Intermediate Similarity	NPC260521
0.8452	Intermediate Similarity	NPC14662
0.8452	Intermediate Similarity	NPC243877
0.8442	Intermediate Similarity	NPC22517
0.8439	Intermediate Similarity	NPC8940
0.8439	Intermediate Similarity	NPC117668
0.8438	Intermediate Similarity	NPC477612
0.8438	Intermediate Similarity	NPC221091
0.8438	Intermediate Similarity	NPC259576
0.8434	Intermediate Similarity	NPC42797
0.8434	Intermediate Similarity	NPC471745
0.8434	Intermediate Similarity	NPC249070
0.8431	Intermediate Similarity	NPC300846
0.8431	Intermediate Similarity	NPC114155
0.8431	Intermediate Similarity	NPC476639
0.843	Intermediate Similarity	NPC265380
0.8428	Intermediate Similarity	NPC187398
0.8428	Intermediate Similarity	NPC476348
0.8424	Intermediate Similarity	NPC130955
0.8421	Intermediate Similarity	NPC287243
0.8418	Intermediate Similarity	NPC95652
0.8418	Intermediate Similarity	NPC150714
0.8415	Intermediate Similarity	NPC156057
0.8415	Intermediate Similarity	NPC185526
0.8415	Intermediate Similarity	NPC162869
0.8415	Intermediate Similarity	NPC48208
0.8415	Intermediate Similarity	NPC475267
0.8415	Intermediate Similarity	NPC108456
0.8415	Intermediate Similarity	NPC474836
0.8415	Intermediate Similarity	NPC183851
0.8415	Intermediate Similarity	NPC474208
0.8415	Intermediate Similarity	NPC63454
0.8412	Intermediate Similarity	NPC271848
0.8412	Intermediate Similarity	NPC4200
0.8412	Intermediate Similarity	NPC81332
0.8412	Intermediate Similarity	NPC262580
0.8412	Intermediate Similarity	NPC475669
0.8412	Intermediate Similarity	NPC289396
0.8412	Intermediate Similarity	NPC212038
0.8409	Intermediate Similarity	NPC240200
0.8409	Intermediate Similarity	NPC473618
0.8409	Intermediate Similarity	NPC223534
0.8409	Intermediate Similarity	NPC290289
0.8409	Intermediate Similarity	NPC158214
0.8408	Intermediate Similarity	NPC171932
0.8408	Intermediate Similarity	NPC28440
0.8402	Intermediate Similarity	NPC163130

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 NPC174311 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	902
0.2-0.3	1830
0.3-0.4	2641
0.4-0.5	1753
0.5-0.6	1012
0.6-0.7	526
0.7-0.8	138
0.8-0.85	20
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8623	High Similarity	NPD5844	Phase 1
0.8466	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8282	Intermediate Similarity	NPD1934	Approved
0.8253	Intermediate Similarity	NPD6234	Discontinued
0.8232	Intermediate Similarity	NPD2801	Approved
0.8198	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7473	Discontinued
0.8133	Intermediate Similarity	NPD7768	Phase 2
0.8121	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD3817	Phase 2
0.8061	Intermediate Similarity	NPD37	Approved
0.8047	Intermediate Similarity	NPD6959	Discontinued
0.8047	Intermediate Similarity	NPD7199	Phase 2
0.8035	Intermediate Similarity	NPD7074	Phase 3
0.8024	Intermediate Similarity	NPD4966	Approved
0.8024	Intermediate Similarity	NPD4965	Approved
0.8024	Intermediate Similarity	NPD4967	Phase 2
0.8023	Intermediate Similarity	NPD7228	Approved
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.7977	Intermediate Similarity	NPD7054	Approved
0.7953	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1613	Approved
0.7931	Intermediate Similarity	NPD7472	Approved
0.7927	Intermediate Similarity	NPD1653	Approved
0.7919	Intermediate Similarity	NPD3818	Discontinued
0.7907	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD8455	Phase 2
0.7857	Intermediate Similarity	NPD3027	Phase 3
0.7857	Intermediate Similarity	NPD5402	Approved
0.7853	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6559	Discontinued
0.7811	Intermediate Similarity	NPD3882	Suspended
0.7797	Intermediate Similarity	NPD7808	Phase 3
0.7792	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1511	Approved
0.7784	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD5494	Approved
0.7765	Intermediate Similarity	NPD7075	Discontinued
0.7756	Intermediate Similarity	NPD6233	Phase 2
0.7751	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7251	Discontinued
0.7733	Intermediate Similarity	NPD8127	Discontinued
0.7727	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1512	Approved
0.7692	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7819	Suspended
0.7692	Intermediate Similarity	NPD6798	Discontinued
0.7688	Intermediate Similarity	NPD3787	Discontinued
0.7679	Intermediate Similarity	NPD7411	Suspended
0.7677	Intermediate Similarity	NPD4908	Phase 1
0.7667	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8313	Approved
0.7654	Intermediate Similarity	NPD8312	Approved
0.7619	Intermediate Similarity	NPD4380	Phase 2
0.7619	Intermediate Similarity	NPD6599	Discontinued
0.7588	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6190	Approved
0.7558	Intermediate Similarity	NPD3749	Approved
0.7554	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5403	Approved
0.7542	Intermediate Similarity	NPD7240	Approved
0.7529	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD7549	Discontinued
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7472	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6799	Approved
0.7469	Intermediate Similarity	NPD2935	Discontinued
0.7469	Intermediate Similarity	NPD1551	Phase 2
0.744	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6355	Discontinued
0.7425	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5401	Approved
0.7425	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD3751	Discontinued
0.7394	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4110	Phase 3
0.7386	Intermediate Similarity	NPD7229	Phase 3
0.7381	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1549	Phase 2
0.7371	Intermediate Similarity	NPD6746	Phase 2
0.7362	Intermediate Similarity	NPD6099	Approved
0.7362	Intermediate Similarity	NPD6100	Approved
0.7358	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3226	Approved
0.7353	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7783	Phase 2
0.7347	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7680	Approved
0.7329	Intermediate Similarity	NPD447	Suspended
0.7321	Intermediate Similarity	NPD2533	Approved
0.7321	Intermediate Similarity	NPD2532	Approved
0.7321	Intermediate Similarity	NPD2534	Approved
0.7314	Intermediate Similarity	NPD919	Approved
0.7301	Intermediate Similarity	NPD7033	Discontinued
0.7296	Intermediate Similarity	NPD4625	Phase 3
0.7289	Intermediate Similarity	NPD8166	Discontinued
0.7278	Intermediate Similarity	NPD2861	Phase 2
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4060	Phase 1
0.7267	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7390	Discontinued
0.7261	Intermediate Similarity	NPD2797	Approved
0.7256	Intermediate Similarity	NPD2796	Approved
0.7256	Intermediate Similarity	NPD5404	Approved
0.7256	Intermediate Similarity	NPD5406	Approved
0.7256	Intermediate Similarity	NPD5405	Approved
0.7256	Intermediate Similarity	NPD5408	Approved
0.7247	Intermediate Similarity	NPD3926	Phase 2
0.7245	Intermediate Similarity	NPD8151	Discontinued
0.7229	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6674	Discontinued
0.7228	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7225	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD230	Phase 1
0.7212	Intermediate Similarity	NPD7266	Discontinued
0.7195	Intermediate Similarity	NPD3748	Approved
0.7195	Intermediate Similarity	NPD1510	Phase 2
0.7188	Intermediate Similarity	NPD7095	Approved
0.7178	Intermediate Similarity	NPD1607	Approved
0.7158	Intermediate Similarity	NPD7685	Pre-registration
0.7158	Intermediate Similarity	NPD7038	Approved
0.7158	Intermediate Similarity	NPD7039	Approved
0.7152	Intermediate Similarity	NPD2438	Suspended
0.7143	Intermediate Similarity	NPD3268	Approved
0.7135	Intermediate Similarity	NPD1247	Approved
0.7134	Intermediate Similarity	NPD4749	Approved
0.7134	Intermediate Similarity	NPD7097	Phase 1
0.7126	Intermediate Similarity	NPD1652	Phase 2
0.7117	Intermediate Similarity	NPD5124	Phase 1
0.7117	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD422	Phase 1
0.7083	Intermediate Similarity	NPD7003	Approved
0.7078	Intermediate Similarity	NPD1548	Phase 1
0.7077	Intermediate Similarity	NPD7435	Discontinued
0.7076	Intermediate Similarity	NPD6273	Approved
0.707	Intermediate Similarity	NPD1608	Approved
0.7063	Intermediate Similarity	NPD3018	Phase 2
0.7059	Intermediate Similarity	NPD8434	Phase 2
0.7059	Intermediate Similarity	NPD8150	Discontinued
0.7055	Intermediate Similarity	NPD1240	Approved
0.7043	Intermediate Similarity	NPD8053	Approved
0.7043	Intermediate Similarity	NPD8054	Approved
0.7037	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7177	Discontinued
0.7031	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6832	Phase 2
0.7012	Intermediate Similarity	NPD1933	Approved
0.701	Intermediate Similarity	NPD6779	Approved
0.701	Intermediate Similarity	NPD6780	Approved
0.701	Intermediate Similarity	NPD6782	Approved
0.701	Intermediate Similarity	NPD6781	Approved
0.701	Intermediate Similarity	NPD6777	Approved
0.701	Intermediate Similarity	NPD6776	Approved
0.701	Intermediate Similarity	NPD6778	Approved
0.7006	Intermediate Similarity	NPD1535	Discovery
0.7006	Intermediate Similarity	NPD2346	Discontinued
0.7006	Intermediate Similarity	NPD1611	Approved
0.7006	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4062	Phase 3
0.6988	Remote Similarity	NPD4308	Phase 3
0.6987	Remote Similarity	NPD1778	Approved
0.6981	Remote Similarity	NPD3225	Approved
0.6981	Remote Similarity	NPD1283	Approved
0.6962	Remote Similarity	NPD1481	Phase 2
0.6954	Remote Similarity	NPD7871	Phase 2
0.6954	Remote Similarity	NPD7458	Discontinued
0.6954	Remote Similarity	NPD7870	Phase 2
0.6954	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2979	Phase 3
0.6951	Remote Similarity	NPD943	Approved
0.695	Remote Similarity	NPD7874	Approved
0.695	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6823	Phase 2
0.6937	Remote Similarity	NPD1203	Approved
0.6936	Remote Similarity	NPD920	Approved
0.6919	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2983	Phase 2
0.6918	Remote Similarity	NPD2982	Phase 2
0.6909	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5762	Approved
0.6905	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5763	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