NPASS Compound

Structure

NPC153417 OpenBabel07101719522D 21 22 0 0 1 0 0 0 0 0999 V2000 -4.3301 -0.5000 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 -0.5000 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 -0.8660 -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 2.5981 -1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 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 0.0000 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 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 6 1 0 0 0 0 2 10 1 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 7 1 0 0 0 0 4 11 2 0 0 0 0 5 9 2 0 0 0 0 5 21 1 0 0 0 0 6 15 2 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 17 1 6 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 13 18 2 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.06
Volume:	276.664
LogP:	0.66
LogD:	0.477
LogS:	-2.534
# Rotatable Bonds:	4
TPSA:	125.04
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	3.375
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.238
MDCK Permeability:	3.6895037283102283e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	69.1342544555664%
Volume Distribution (VD):	0.725
Pgp-substrate:	42.027626037597656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.035

ADMET: Excretion

Clearance (CL):	2.982
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.366
Carcinogencity:	0.176
Eye Corrosion:	0.019
Eye Irritation:	0.685
Respiratory Toxicity:	0.638

Download Data

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

Natural Product: NPC153417

Natural Product ID:	NPC153417
*Common Name:**	(1's)-7-Hydroxy-3-(1'-Hydroxy-3'-Butanoyl)Chromone-5-Carboxylic Acid
IUPAC Name:	7-hydroxy-3-[(1S)-1-hydroxy-3-oxobutyl]-4-oxochromene-5-carboxylic acid
Synonyms:
Standard InCHIKey:	PEKVXUBDORIMOH-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C14H12O7/c1-6(15)2-10(17)9-5-21-11-4-7(16)3-8(14(19)20)12(11)13(9)18/h3-5,10,16-17H,2H2,1H3,(H,19,20)/t10-/m0/s1
SMILES:	CC(=O)C[C@@H](c1coc2cc(cc(c2c1=O)C(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419349
PubChem CID:	73352244
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	94900.0	nM	PMID[510437]

☑ 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 NPC153417 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	362
0.1-0.2	1694
0.2-0.3	4090
0.3-0.4	8980
0.4-0.5	9528
0.5-0.6	3839
0.6-0.7	5622
0.7-0.8	5008
0.8-0.85	2887
0.85-0.9	625
0.9-0.95	56
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9379	High Similarity	NPC472036
0.9362	High Similarity	NPC92655
0.9315	High Similarity	NPC471642
0.9315	High Similarity	NPC471641
0.9315	High Similarity	NPC240622
0.9315	High Similarity	NPC240253
0.931	High Similarity	NPC472033
0.9247	High Similarity	NPC14098
0.9241	High Similarity	NPC472034
0.9236	High Similarity	NPC472006
0.9236	High Similarity	NPC51106
0.9236	High Similarity	NPC469542
0.9225	High Similarity	NPC268052
0.9184	High Similarity	NPC2569
0.9184	High Similarity	NPC172329
0.9178	High Similarity	NPC107625
0.9122	High Similarity	NPC77325
0.9122	High Similarity	NPC4423
0.911	High Similarity	NPC473692
0.911	High Similarity	NPC312789
0.9103	High Similarity	NPC478202
0.9097	High Similarity	NPC1704
0.9097	High Similarity	NPC67650
0.9097	High Similarity	NPC90411
0.9091	High Similarity	NPC32360
0.9085	High Similarity	NPC135837
0.9079	High Similarity	NPC263483
0.9078	High Similarity	NPC182496
0.9078	High Similarity	NPC180905
0.906	High Similarity	NPC295036
0.906	High Similarity	NPC470107
0.9041	High Similarity	NPC475201
0.9034	High Similarity	NPC297985
0.9034	High Similarity	NPC474385
0.9034	High Similarity	NPC469579
0.9	High Similarity	NPC70016
0.9	High Similarity	NPC215921
0.8993	High Similarity	NPC237440
0.8993	High Similarity	NPC270160
0.898	High Similarity	NPC257558
0.8966	High Similarity	NPC478201
0.8966	High Similarity	NPC158634
0.8966	High Similarity	NPC475730
0.8966	High Similarity	NPC478217
0.8966	High Similarity	NPC472035
0.8966	High Similarity	NPC313123
0.8958	High Similarity	NPC57380
0.8947	High Similarity	NPC99381
0.8933	High Similarity	NPC147735
0.8933	High Similarity	NPC469670
0.8933	High Similarity	NPC469619
0.8926	High Similarity	NPC73411
0.8926	High Similarity	NPC215711
0.8912	High Similarity	NPC210425
0.8912	High Similarity	NPC277426
0.8912	High Similarity	NPC184702
0.8912	High Similarity	NPC478203
0.8912	High Similarity	NPC210966
0.8912	High Similarity	NPC126882
0.8912	High Similarity	NPC86373
0.8912	High Similarity	NPC19896
0.8912	High Similarity	NPC280404
0.8904	High Similarity	NPC250755
0.8904	High Similarity	NPC49108
0.8904	High Similarity	NPC471640
0.8904	High Similarity	NPC471644
0.8897	High Similarity	NPC165172
0.8897	High Similarity	NPC469523
0.8889	High Similarity	NPC191835
0.8889	High Similarity	NPC472050
0.8889	High Similarity	NPC212693
0.8889	High Similarity	NPC94248
0.8889	High Similarity	NPC475974
0.8882	High Similarity	NPC155686
0.8882	High Similarity	NPC281477
0.8882	High Similarity	NPC192189
0.8881	High Similarity	NPC235115
0.8874	High Similarity	NPC470569
0.8874	High Similarity	NPC46882
0.8874	High Similarity	NPC240768
0.8874	High Similarity	NPC200773
0.8874	High Similarity	NPC132990
0.8873	High Similarity	NPC175943
0.8867	High Similarity	NPC198927
0.8859	High Similarity	NPC52106
0.8859	High Similarity	NPC210320
0.8844	High Similarity	NPC471639
0.8844	High Similarity	NPC471643
0.8836	High Similarity	NPC244923
0.8828	High Similarity	NPC247409
0.8828	High Similarity	NPC474655
0.8828	High Similarity	NPC105456
0.8828	High Similarity	NPC139634
0.8824	High Similarity	NPC82592
0.8824	High Similarity	NPC38898
0.8824	High Similarity	NPC16082
0.8819	High Similarity	NPC178467
0.8819	High Similarity	NPC149372
0.8819	High Similarity	NPC474771
0.8819	High Similarity	NPC70380
0.8819	High Similarity	NPC65837
0.8819	High Similarity	NPC193792
0.8819	High Similarity	NPC474849
0.8816	High Similarity	NPC271681
0.8816	High Similarity	NPC470340
0.8816	High Similarity	NPC167903
0.8808	High Similarity	NPC179178
0.8808	High Similarity	NPC255641
0.8808	High Similarity	NPC119929
0.8808	High Similarity	NPC290954
0.8808	High Similarity	NPC60413
0.8808	High Similarity	NPC470568
0.8803	High Similarity	NPC153783
0.8794	High Similarity	NPC219892
0.8794	High Similarity	NPC189823
0.8792	High Similarity	NPC260946
0.8776	High Similarity	NPC82913
0.8774	High Similarity	NPC470339
0.8767	High Similarity	NPC156872
0.8767	High Similarity	NPC201541
0.8759	High Similarity	NPC177307
0.8759	High Similarity	NPC9121
0.8759	High Similarity	NPC33144
0.8759	High Similarity	NPC472403
0.8759	High Similarity	NPC478200
0.8759	High Similarity	NPC472602
0.8759	High Similarity	NPC212767
0.8758	High Similarity	NPC208806
0.875	High Similarity	NPC39819
0.875	High Similarity	NPC242712
0.875	High Similarity	NPC50455
0.875	High Similarity	NPC84699
0.8742	High Similarity	NPC476684
0.8742	High Similarity	NPC6923
0.8733	High Similarity	NPC245584
0.8733	High Similarity	NPC289042
0.8733	High Similarity	NPC312929
0.8733	High Similarity	NPC56433
0.8733	High Similarity	NPC8817
0.8733	High Similarity	NPC190648
0.8733	High Similarity	NPC118027
0.8733	High Similarity	NPC126767
0.8725	High Similarity	NPC134621
0.8725	High Similarity	NPC83272
0.8725	High Similarity	NPC28632
0.8718	High Similarity	NPC243701
0.8718	High Similarity	NPC472055
0.8716	High Similarity	NPC215451
0.8716	High Similarity	NPC277369
0.871	High Similarity	NPC190020
0.871	High Similarity	NPC84935
0.871	High Similarity	NPC246466
0.871	High Similarity	NPC473395
0.871	High Similarity	NPC77679
0.8707	High Similarity	NPC53649
0.8707	High Similarity	NPC472605
0.8707	High Similarity	NPC472603
0.8707	High Similarity	NPC220106
0.8707	High Similarity	NPC472604
0.8701	High Similarity	NPC79998
0.8701	High Similarity	NPC199926
0.8699	High Similarity	NPC309154
0.8699	High Similarity	NPC278323
0.8699	High Similarity	NPC88269
0.8699	High Similarity	NPC55162
0.8699	High Similarity	NPC12175
0.8699	High Similarity	NPC275356
0.8699	High Similarity	NPC52358
0.8699	High Similarity	NPC279668
0.8699	High Similarity	NPC90665
0.8693	High Similarity	NPC470338
0.8693	High Similarity	NPC175978
0.8693	High Similarity	NPC268992
0.8693	High Similarity	NPC180944
0.8693	High Similarity	NPC113608
0.8693	High Similarity	NPC470337
0.8693	High Similarity	NPC273483
0.8693	High Similarity	NPC51824
0.8693	High Similarity	NPC474843
0.869	High Similarity	NPC235428
0.869	High Similarity	NPC87545
0.8684	High Similarity	NPC294646
0.8684	High Similarity	NPC202595
0.8684	High Similarity	NPC56204
0.8684	High Similarity	NPC96501
0.8675	High Similarity	NPC216624
0.8675	High Similarity	NPC228012
0.8667	High Similarity	NPC267509
0.8667	High Similarity	NPC163846
0.8667	High Similarity	NPC237208
0.8667	High Similarity	NPC138978
0.8667	High Similarity	NPC225173
0.8667	High Similarity	NPC470357
0.8658	High Similarity	NPC95123
0.8658	High Similarity	NPC51887
0.8658	High Similarity	NPC66404
0.8658	High Similarity	NPC470932
0.8658	High Similarity	NPC117836
0.8658	High Similarity	NPC95751
0.8658	High Similarity	NPC476178

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 NPC153417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	997
0.2-0.3	1888
0.3-0.4	2553
0.4-0.5	1825
0.5-0.6	1043
0.6-0.7	323
0.7-0.8	122
0.8-0.85	47
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD970	Clinical (unspecified phase)
0.8621	High Similarity	NPD1510	Phase 2
0.86	High Similarity	NPD2532	Approved
0.86	High Similarity	NPD2534	Approved
0.86	High Similarity	NPD2533	Approved
0.8581	High Similarity	NPD1878	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1240	Approved
0.8397	Intermediate Similarity	NPD7819	Suspended
0.8356	Intermediate Similarity	NPD1607	Approved
0.8322	Intermediate Similarity	NPD1549	Phase 2
0.8261	Intermediate Similarity	NPD6232	Discontinued
0.8255	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7473	Discontinued
0.8212	Intermediate Similarity	NPD3750	Approved
0.8205	Intermediate Similarity	NPD4380	Phase 2
0.8153	Intermediate Similarity	NPD7411	Suspended
0.8141	Intermediate Similarity	NPD3226	Approved
0.8121	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD1934	Approved
0.8067	Intermediate Similarity	NPD2796	Approved
0.8067	Intermediate Similarity	NPD2935	Discontinued
0.8052	Intermediate Similarity	NPD1511	Approved
0.805	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD230	Phase 1
0.8013	Intermediate Similarity	NPD920	Approved
0.8012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3749	Approved
0.8012	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6801	Discontinued
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7952	Intermediate Similarity	NPD3818	Discontinued
0.795	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1512	Approved
0.7947	Intermediate Similarity	NPD1551	Phase 2
0.7939	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD2801	Approved
0.7935	Intermediate Similarity	NPD6799	Approved
0.7927	Intermediate Similarity	NPD5710	Approved
0.7927	Intermediate Similarity	NPD5711	Approved
0.7908	Intermediate Similarity	NPD2800	Approved
0.7908	Intermediate Similarity	NPD1243	Approved
0.7888	Intermediate Similarity	NPD5402	Approved
0.7888	Intermediate Similarity	NPD3817	Phase 2
0.7885	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD3748	Approved
0.7862	Intermediate Similarity	NPD6599	Discontinued
0.784	Intermediate Similarity	NPD3882	Suspended
0.7826	Intermediate Similarity	NPD1465	Phase 2
0.7798	Intermediate Similarity	NPD5844	Phase 1
0.7792	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD943	Approved
0.773	Intermediate Similarity	NPD7768	Phase 2
0.7725	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6166	Phase 2
0.7719	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7054	Approved
0.7673	Intermediate Similarity	NPD5403	Approved
0.767	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7658	Intermediate Similarity	NPD5401	Approved
0.7651	Intermediate Similarity	NPD1247	Approved
0.7647	Intermediate Similarity	NPD7472	Approved
0.7647	Intermediate Similarity	NPD7074	Phase 3
0.7636	Intermediate Similarity	NPD919	Approved
0.7632	Intermediate Similarity	NPD6651	Approved
0.7628	Intermediate Similarity	NPD4628	Phase 3
0.7602	Intermediate Similarity	NPD6797	Phase 2
0.7602	Intermediate Similarity	NPD5953	Discontinued
0.7602	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5494	Approved
0.7588	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD447	Suspended
0.7558	Intermediate Similarity	NPD7251	Discontinued
0.7558	Intermediate Similarity	NPD6559	Discontinued
0.7552	Intermediate Similarity	NPD9545	Approved
0.7548	Intermediate Similarity	NPD2344	Approved
0.7546	Intermediate Similarity	NPD37	Approved
0.7535	Intermediate Similarity	NPD9493	Approved
0.7534	Intermediate Similarity	NPD9717	Approved
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD1470	Approved
0.7485	Intermediate Similarity	NPD7286	Phase 2
0.7484	Intermediate Similarity	NPD7390	Discontinued
0.7483	Intermediate Similarity	NPD2313	Discontinued
0.7466	Intermediate Similarity	NPD422	Phase 1
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7415	Intermediate Similarity	NPD9269	Phase 2
0.7413	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4967	Phase 2
0.741	Intermediate Similarity	NPD4965	Approved
0.741	Intermediate Similarity	NPD4966	Approved
0.7379	Intermediate Similarity	NPD9268	Approved
0.7372	Intermediate Similarity	NPD6100	Approved
0.7372	Intermediate Similarity	NPD6099	Approved
0.7368	Intermediate Similarity	NPD411	Approved
0.7368	Intermediate Similarity	NPD3764	Approved
0.7368	Intermediate Similarity	NPD3268	Approved
0.7358	Intermediate Similarity	NPD2309	Approved
0.7346	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD8151	Discontinued
0.7338	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2798	Approved
0.7325	Intermediate Similarity	NPD1471	Phase 3
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.7308	Intermediate Similarity	NPD7033	Discontinued
0.7297	Intermediate Similarity	NPD1608	Approved
0.7273	Intermediate Similarity	NPD8312	Approved
0.7273	Intermediate Similarity	NPD8313	Approved
0.7263	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5405	Approved
0.7261	Intermediate Similarity	NPD5406	Approved
0.7261	Intermediate Similarity	NPD5404	Approved
0.7261	Intermediate Similarity	NPD5408	Approved
0.7258	Intermediate Similarity	NPD7435	Discontinued
0.7256	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3926	Phase 2
0.7247	Intermediate Similarity	NPD8434	Phase 2
0.7246	Intermediate Similarity	NPD4288	Approved
0.7237	Intermediate Similarity	NPD6832	Phase 2
0.7233	Intermediate Similarity	NPD2654	Approved
0.723	Intermediate Similarity	NPD1201	Approved
0.7222	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1019	Discontinued
0.7216	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1283	Approved
0.7193	Intermediate Similarity	NPD7229	Phase 3
0.7189	Intermediate Similarity	NPD6777	Approved
0.7189	Intermediate Similarity	NPD6781	Approved
0.7189	Intermediate Similarity	NPD6780	Approved
0.7189	Intermediate Similarity	NPD6778	Approved
0.7189	Intermediate Similarity	NPD6782	Approved
0.7189	Intermediate Similarity	NPD6776	Approved
0.7189	Intermediate Similarity	NPD6779	Approved
0.7171	Intermediate Similarity	NPD9494	Approved
0.7152	Intermediate Similarity	NPD3266	Approved
0.7152	Intermediate Similarity	NPD1164	Approved
0.7152	Intermediate Similarity	NPD3267	Approved
0.7151	Intermediate Similarity	NPD8150	Discontinued
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7199	Phase 2
0.7126	Intermediate Similarity	NPD7228	Approved
0.7126	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5124	Phase 1
0.7115	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4626	Approved
0.7095	Intermediate Similarity	NPD17	Approved
0.7093	Intermediate Similarity	NPD6808	Phase 2
0.7093	Intermediate Similarity	NPD3787	Discontinued
0.7091	Intermediate Similarity	NPD1653	Approved
0.7089	Intermediate Similarity	NPD4308	Phase 3
0.7086	Intermediate Similarity	NPD1876	Approved
0.7081	Intermediate Similarity	NPD7003	Approved
0.7078	Intermediate Similarity	NPD3027	Phase 3
0.7074	Intermediate Similarity	NPD7697	Approved
0.7074	Intermediate Similarity	NPD7696	Phase 3
0.7074	Intermediate Similarity	NPD7698	Approved
0.7073	Intermediate Similarity	NPD6273	Approved
0.7072	Intermediate Similarity	NPD4287	Approved
0.7052	Intermediate Similarity	NPD5242	Approved
0.7051	Intermediate Similarity	NPD1613	Approved
0.7051	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7458	Discontinued
0.7039	Intermediate Similarity	NPD2797	Approved
0.7037	Intermediate Similarity	NPD7870	Phase 2
0.7037	Intermediate Similarity	NPD7871	Phase 2
0.7037	Intermediate Similarity	NPD6190	Approved
0.7031	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7874	Approved
0.7027	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1652	Phase 2
0.7018	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2403	Approved
0.7011	Intermediate Similarity	NPD4360	Phase 2
0.7011	Intermediate Similarity	NPD4363	Phase 3
0.7	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1610	Phase 2
0.7	Intermediate Similarity	NPD1281	Approved
0.6993	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3225	Approved
0.6972	Remote Similarity	NPD74	Approved
0.6972	Remote Similarity	NPD9266	Approved
0.6966	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7685	Pre-registration

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