NPASS Compound

Structure

CID155015 OpenBabel06191715522D 33 35 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 1.7321 -3.0000 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 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 0.8660 -3.5000 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 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 4.0000 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 -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 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 -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 13 1 0 0 0 0 3 7 1 0 0 0 0 3 14 2 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 9 1 0 0 0 0 5 15 2 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 1 1 1 0 0 0 12 25 1 0 0 0 0 13 26 2 0 0 0 0 13 32 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 29 2 0 0 0 0 18 33 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 24 2 0 0 0 0 21 23 2 0 0 0 0 21 30 1 0 0 0 0 22 24 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.13
Volume:	448.102
LogP:	3.18
LogD:	1.861
LogS:	-4.278
# Rotatable Bonds:	8
TPSA:	153.75
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.214
Synthetic Accessibility Score:	3.192
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.556
MDCK Permeability:	1.1564288797671907e-05
Pgp-inhibitor:	0.073
Pgp-substrate:	0.061
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	99.26834869384766%
Volume Distribution (VD):	0.422
Pgp-substrate:	1.4427461624145508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.835
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.812
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.81
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.299
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	1.408
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.013
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.422
Maximum Recommended Daily Dose:	0.145
Skin Sensitization:	0.13
Carcinogencity:	0.246
Eye Corrosion:	0.003
Eye Irritation:	0.531
Respiratory Toxicity:	0.08

Download Data

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

Natural Product: NPC155015

Natural Product ID:	NPC155015
*Common Name:**	Curtisian L
IUPAC Name:	[4-acetyloxy-2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)phenyl] (3R)-3-hydroxybutanoate
Synonyms:	Curtisian L
Standard InCHIKey:	TUDASCLVGVCARU-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C24H22O9/c1-12(25)11-18(29)33-24-20(15-5-9-17(28)10-6-15)21(30)23(32-13(2)26)19(22(24)31)14-3-7-16(27)8-4-14/h3-10,12,25,27-28,30-31H,11H2,1-2H3/t12-/m1/s1
SMILES:	C[C@H](CC(=O)Oc1c(c2ccc(cc2)O)c(c(c(c2ccc(cc2)O)c1O)OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564537
PubChem CID:	45271708
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[458308]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18640.0	nM	PMID[458308]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	500000.0	nM	PMID[458308]

☑ 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 NPC155015 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	352
0.1-0.2	1626
0.2-0.3	3910
0.3-0.4	10288
0.4-0.5	8292
0.5-0.6	3765
0.6-0.7	5572
0.7-0.8	7294
0.8-0.85	1384
0.85-0.9	195
0.9-0.95	12
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC142479
0.9932	High Similarity	NPC7178
0.9932	High Similarity	NPC62903
0.9864	High Similarity	NPC476154
0.9608	High Similarity	NPC55121
0.9592	High Similarity	NPC113790
0.9481	High Similarity	NPC174311
0.9456	High Similarity	NPC97937
0.9456	High Similarity	NPC170239
0.9456	High Similarity	NPC275125
0.9355	High Similarity	NPC192258
0.9355	High Similarity	NPC476200
0.932	High Similarity	NPC125617
0.9216	High Similarity	NPC292385
0.9216	High Similarity	NPC125709
0.9182	High Similarity	NPC476279
0.9091	High Similarity	NPC476642
0.8974	High Similarity	NPC36077
0.8961	High Similarity	NPC78809
0.894	High Similarity	NPC208507
0.894	High Similarity	NPC472333
0.8917	High Similarity	NPC36354
0.8912	High Similarity	NPC22517
0.8896	High Similarity	NPC163598
0.8896	High Similarity	NPC120774
0.8896	High Similarity	NPC264875
0.8889	High Similarity	NPC294522
0.8889	High Similarity	NPC120426
0.8889	High Similarity	NPC205727
0.8889	High Similarity	NPC265214
0.8889	High Similarity	NPC21184
0.8844	High Similarity	NPC6262
0.8844	High Similarity	NPC73535
0.8844	High Similarity	NPC90615
0.8844	High Similarity	NPC272157
0.8844	High Similarity	NPC201145
0.8844	High Similarity	NPC25111
0.8827	High Similarity	NPC67424
0.8824	High Similarity	NPC30688
0.8824	High Similarity	NPC176903
0.8805	High Similarity	NPC155754
0.8805	High Similarity	NPC124747
0.8805	High Similarity	NPC109061
0.88	High Similarity	NPC110067
0.88	High Similarity	NPC7439
0.88	High Similarity	NPC34245
0.88	High Similarity	NPC91492
0.88	High Similarity	NPC256555
0.88	High Similarity	NPC477616
0.8792	High Similarity	NPC471389
0.879	High Similarity	NPC165483
0.8782	High Similarity	NPC8712
0.8776	High Similarity	NPC476639
0.8776	High Similarity	NPC472334
0.8776	High Similarity	NPC300846
0.8776	High Similarity	NPC114155
0.8776	High Similarity	NPC472336
0.8758	High Similarity	NPC175976
0.8758	High Similarity	NPC476348
0.8758	High Similarity	NPC477879
0.8758	High Similarity	NPC187398
0.875	High Similarity	NPC268515
0.875	High Similarity	NPC40222
0.8733	High Similarity	NPC469564
0.8725	High Similarity	NPC266197
0.8725	High Similarity	NPC34431
0.8725	High Similarity	NPC73505
0.8725	High Similarity	NPC291101
0.8725	High Similarity	NPC295719
0.8725	High Similarity	NPC165026
0.8718	High Similarity	NPC149735
0.8718	High Similarity	NPC473236
0.8716	High Similarity	NPC102904
0.8716	High Similarity	NPC176051
0.8716	High Similarity	NPC103976
0.8716	High Similarity	NPC474282
0.8716	High Similarity	NPC107551
0.8716	High Similarity	NPC326797
0.8707	High Similarity	NPC261873
0.8707	High Similarity	NPC111655
0.8707	High Similarity	NPC472337
0.8707	High Similarity	NPC283009
0.8693	High Similarity	NPC15577
0.8693	High Similarity	NPC476347
0.8679	High Similarity	NPC24339
0.8679	High Similarity	NPC98083
0.8679	High Similarity	NPC166456
0.8679	High Similarity	NPC94220
0.8679	High Similarity	NPC7543
0.8667	High Similarity	NPC178054
0.8667	High Similarity	NPC311530
0.8658	High Similarity	NPC127218
0.8658	High Similarity	NPC471388
0.8658	High Similarity	NPC245207
0.8658	High Similarity	NPC319647
0.8658	High Similarity	NPC25966
0.865	High Similarity	NPC167231
0.865	High Similarity	NPC215802
0.8649	High Similarity	NPC16435
0.8649	High Similarity	NPC306441
0.8649	High Similarity	NPC471719
0.8639	High Similarity	NPC103967
0.8639	High Similarity	NPC310854
0.8636	High Similarity	NPC139839
0.8627	High Similarity	NPC112251
0.8627	High Similarity	NPC99515
0.8627	High Similarity	NPC474054
0.8627	High Similarity	NPC324492
0.8627	High Similarity	NPC317053
0.8627	High Similarity	NPC260397
0.8627	High Similarity	NPC190714
0.8625	High Similarity	NPC301089
0.8618	High Similarity	NPC87883
0.8609	High Similarity	NPC107161
0.8609	High Similarity	NPC472335
0.8609	High Similarity	NPC175838
0.8609	High Similarity	NPC472332
0.86	High Similarity	NPC254759
0.86	High Similarity	NPC160283
0.86	High Similarity	NPC22317
0.8599	High Similarity	NPC475141
0.8599	High Similarity	NPC150442
0.8599	High Similarity	NPC65591
0.8599	High Similarity	NPC178574
0.8591	High Similarity	NPC276490
0.859	High Similarity	NPC225129
0.8581	High Similarity	NPC474206
0.8581	High Similarity	NPC61946
0.8581	High Similarity	NPC470356
0.8581	High Similarity	NPC94750
0.8581	High Similarity	NPC121812
0.8581	High Similarity	NPC112246
0.8581	High Similarity	NPC112939
0.8581	High Similarity	NPC224941
0.8581	High Similarity	NPC475250
0.8581	High Similarity	NPC252095
0.8581	High Similarity	NPC260898
0.8581	High Similarity	NPC234333
0.8581	High Similarity	NPC311430
0.8581	High Similarity	NPC47398
0.8571	High Similarity	NPC177100
0.8571	High Similarity	NPC139540
0.8571	High Similarity	NPC227902
0.8571	High Similarity	NPC178129
0.8571	High Similarity	NPC328567
0.8571	High Similarity	NPC327412
0.8571	High Similarity	NPC475840
0.8571	High Similarity	NPC320671
0.8571	High Similarity	NPC320970
0.8545	High Similarity	NPC91043
0.8544	High Similarity	NPC473736
0.8544	High Similarity	NPC268484
0.8543	High Similarity	NPC247291
0.8535	High Similarity	NPC169404
0.8535	High Similarity	NPC476434
0.8535	High Similarity	NPC176186
0.8535	High Similarity	NPC53587
0.8535	High Similarity	NPC21902
0.8533	High Similarity	NPC29868
0.8533	High Similarity	NPC212942
0.8533	High Similarity	NPC292882
0.8533	High Similarity	NPC79622
0.8528	High Similarity	NPC142614
0.8526	High Similarity	NPC477381
0.8523	High Similarity	NPC474639
0.8523	High Similarity	NPC270456
0.8523	High Similarity	NPC248727
0.8523	High Similarity	NPC227503
0.8523	High Similarity	NPC265433
0.8523	High Similarity	NPC476698
0.8523	High Similarity	NPC162659
0.8523	High Similarity	NPC173660
0.8523	High Similarity	NPC230734
0.8523	High Similarity	NPC269091
0.8523	High Similarity	NPC302701
0.8519	High Similarity	NPC249070
0.8516	High Similarity	NPC281549
0.8516	High Similarity	NPC48366
0.8516	High Similarity	NPC102934
0.8516	High Similarity	NPC252402
0.8514	High Similarity	NPC170694
0.8514	High Similarity	NPC309744
0.8514	High Similarity	NPC106215
0.8514	High Similarity	NPC474600
0.8512	High Similarity	NPC297807
0.8509	High Similarity	NPC53889
0.8509	High Similarity	NPC24164
0.8506	High Similarity	NPC475896
0.8506	High Similarity	NPC205361
0.8503	High Similarity	NPC7903
0.8503	High Similarity	NPC16208
0.8503	High Similarity	NPC218884
0.8503	High Similarity	NPC184447
0.8503	High Similarity	NPC35932
0.8503	High Similarity	NPC160991
0.85	High Similarity	NPC125495
0.8497	Intermediate Similarity	NPC12641
0.8497	Intermediate Similarity	NPC470097
0.8497	Intermediate Similarity	NPC45257
0.8497	Intermediate Similarity	NPC28440

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 NPC155015 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	903
0.2-0.3	1894
0.3-0.4	2717
0.4-0.5	1655
0.5-0.6	951
0.6-0.7	561
0.7-0.8	138
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8598	High Similarity	NPD5844	Phase 1
0.8378	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1613	Approved
0.8344	Intermediate Similarity	NPD1653	Approved
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6166	Phase 2
0.8299	Intermediate Similarity	NPD3027	Phase 3
0.8293	Intermediate Similarity	NPD6232	Discontinued
0.825	Intermediate Similarity	NPD1934	Approved
0.8221	Intermediate Similarity	NPD6234	Discontinued
0.8199	Intermediate Similarity	NPD2801	Approved
0.8144	Intermediate Similarity	NPD7473	Discontinued
0.8137	Intermediate Similarity	NPD37	Approved
0.8121	Intermediate Similarity	NPD7199	Phase 2
0.8108	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD4966	Approved
0.8098	Intermediate Similarity	NPD4965	Approved
0.8098	Intermediate Similarity	NPD4967	Phase 2
0.8086	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD7074	Phase 3
0.7988	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD3818	Discontinued
0.7941	Intermediate Similarity	NPD7054	Approved
0.7917	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6559	Discontinued
0.7898	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7472	Approved
0.7867	Intermediate Similarity	NPD4908	Phase 1
0.7866	Intermediate Similarity	NPD1465	Phase 2
0.7849	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5402	Approved
0.7812	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3882	Suspended
0.7763	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1511	Approved
0.7746	Intermediate Similarity	NPD6797	Phase 2
0.7725	Intermediate Similarity	NPD7075	Discontinued
0.7712	Intermediate Similarity	NPD6233	Phase 2
0.7701	Intermediate Similarity	NPD7251	Discontinued
0.7692	Intermediate Similarity	NPD6959	Discontinued
0.7665	Intermediate Similarity	NPD7768	Phase 2
0.7657	Intermediate Similarity	NPD7549	Discontinued
0.7657	Intermediate Similarity	NPD7808	Phase 3
0.7654	Intermediate Similarity	NPD1512	Approved
0.7654	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6798	Discontinued
0.7647	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5494	Approved
0.7625	Intermediate Similarity	NPD6190	Approved
0.7619	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6801	Discontinued
0.7582	Intermediate Similarity	NPD4625	Phase 3
0.7576	Intermediate Similarity	NPD6599	Discontinued
0.7576	Intermediate Similarity	NPD4380	Phase 2
0.7566	Intermediate Similarity	NPD2861	Phase 2
0.7562	Intermediate Similarity	NPD4628	Phase 3
0.7548	Intermediate Similarity	NPD4060	Phase 1
0.7545	Intermediate Similarity	NPD7819	Suspended
0.7545	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD8455	Phase 2
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.753	Intermediate Similarity	NPD7411	Suspended
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD6674	Discontinued
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7485	Intermediate Similarity	NPD8127	Discontinued
0.7484	Intermediate Similarity	NPD7266	Discontinued
0.7468	Intermediate Similarity	NPD7095	Approved
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7457	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6799	Approved
0.7423	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1551	Phase 2
0.7421	Intermediate Similarity	NPD2935	Discontinued
0.7419	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4749	Approved
0.74	Intermediate Similarity	NPD422	Phase 1
0.7394	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5124	Phase 1
0.7389	Intermediate Similarity	NPD6355	Discontinued
0.7378	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5401	Approved
0.7375	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3751	Discontinued
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.7346	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3750	Approved
0.7346	Intermediate Similarity	NPD4110	Phase 3
0.7341	Intermediate Similarity	NPD7229	Phase 3
0.7338	Intermediate Similarity	NPD3018	Phase 2
0.733	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1549	Phase 2
0.7326	Intermediate Similarity	NPD6746	Phase 2
0.7322	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8312	Approved
0.7318	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD6100	Approved
0.7312	Intermediate Similarity	NPD6099	Approved
0.731	Intermediate Similarity	NPD3749	Approved
0.7308	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3226	Approved
0.7303	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1611	Approved
0.7278	Intermediate Similarity	NPD447	Suspended
0.7273	Intermediate Similarity	NPD2534	Approved
0.7273	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2533	Approved
0.7273	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD919	Approved
0.7267	Intermediate Similarity	NPD5763	Approved
0.7267	Intermediate Similarity	NPD5762	Approved
0.7222	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3620	Phase 2
0.7215	Intermediate Similarity	NPD4140	Approved
0.7215	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7680	Approved
0.7208	Intermediate Similarity	NPD2797	Approved
0.7207	Intermediate Similarity	NPD7039	Approved
0.7207	Intermediate Similarity	NPD7038	Approved
0.7205	Intermediate Similarity	NPD2796	Approved
0.72	Intermediate Similarity	NPD3926	Phase 2
0.719	Intermediate Similarity	NPD2983	Phase 2
0.719	Intermediate Similarity	NPD2982	Phase 2
0.7188	Intermediate Similarity	NPD7097	Phase 1
0.7182	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD230	Phase 1
0.7152	Intermediate Similarity	NPD1778	Approved
0.7143	Intermediate Similarity	NPD3686	Approved
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD3687	Approved
0.7125	Intermediate Similarity	NPD6653	Approved
0.7125	Intermediate Similarity	NPD1607	Approved
0.7124	Intermediate Similarity	NPD2981	Phase 2
0.7105	Intermediate Similarity	NPD3496	Discontinued
0.7099	Intermediate Similarity	NPD2438	Suspended
0.7099	Intermediate Similarity	NPD6032	Approved
0.7089	Intermediate Similarity	NPD3268	Approved
0.7089	Intermediate Similarity	NPD7985	Registered
0.7086	Intermediate Similarity	NPD1247	Approved
0.7075	Intermediate Similarity	NPD5535	Approved
0.7066	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1091	Approved
0.7051	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3748	Approved
0.7032	Intermediate Similarity	NPD3225	Approved
0.7029	Intermediate Similarity	NPD4666	Phase 3
0.7027	Intermediate Similarity	NPD5283	Phase 1
0.7026	Intermediate Similarity	NPD8151	Discontinued
0.7017	Intermediate Similarity	NPD7685	Pre-registration
0.7013	Intermediate Similarity	NPD1608	Approved
0.7011	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8434	Phase 2
0.7007	Intermediate Similarity	NPD228	Approved
0.7006	Intermediate Similarity	NPD7212	Phase 2
0.7006	Intermediate Similarity	NPD7213	Phase 3
0.7	Intermediate Similarity	NPD1240	Approved
0.7	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5709	Phase 3
0.6964	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7447	Phase 1
0.6962	Remote Similarity	NPD6832	Phase 2
0.6957	Remote Similarity	NPD1933	Approved
0.6951	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6002	Phase 3
0.6951	Remote Similarity	NPD6005	Phase 3
0.6951	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2346	Discontinued
0.6951	Remote Similarity	NPD6004	Phase 3
0.6948	Remote Similarity	NPD1535	Discovery
0.6946	Remote Similarity	NPD6667	Approved
0.6946	Remote Similarity	NPD6666	Approved
0.6943	Remote Similarity	NPD7435	Discontinued
0.6937	Remote Similarity	NPD4062	Phase 3
0.6933	Remote Similarity	NPD4308	Phase 3
0.6933	Remote Similarity	NPD7157	Approved
0.6933	Remote Similarity	NPD6671	Approved
0.6928	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4626	Approved
0.6928	Remote Similarity	NPD8166	Discontinued
0.6923	Remote Similarity	NPD6273	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