NPASS Compound

Structure

CID37992 OpenBabel06191715372D 26 27 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 -4.3301 -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 2.5981 1.5000 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 -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 -2.5000 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 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 1.7321 -0.0000 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 -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 -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 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 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 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 10 2 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 17 2 0 0 0 0 13 21 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 23 2 0 0 0 0 16 8 1 6 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 24 2 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.14
Volume:	369.013
LogP:	5.218
LogD:	3.255
LogS:	-3.173
# Rotatable Bonds:	5
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.283
Synthetic Accessibility Score:	3.347
Fsp3:	0.25
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:	-5.09
MDCK Permeability:	2.194667285948526e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.344
Human Intestinal Absorption (HIA):	0.23
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	98.74103546142578%
Volume Distribution (VD):	0.452
Pgp-substrate:	2.6720032691955566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.393
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.833
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.762
CYP2D6-substrate:	0.54
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	2.977
Half-life (T1/2):	0.803

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.662
AMES Toxicity:	0.616
Rat Oral Acute Toxicity:	0.505
Maximum Recommended Daily Dose:	0.844
Skin Sensitization:	0.948
Carcinogencity:	0.298
Eye Corrosion:	0.15
Eye Irritation:	0.939
Respiratory Toxicity:	0.379

Download Data

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

Natural Product: NPC37992

Natural Product ID:	NPC37992
*Common Name:**	Isobutylalkannin
IUPAC Name:	[(1S)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 2-methylpropanoate
Synonyms:	Isobutylalkannin; Isobutyryl Alkannin
Standard InCHIKey:	BVRYLTBIGIAADD-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C20H22O6/c1-10(2)5-8-16(26-20(25)11(3)4)12-9-15(23)17-13(21)6-7-14(22)18(17)19(12)24/h5-7,9,11,16,21-22H,8H2,1-4H3/t16-/m0/s1
SMILES:	CC(=CC[C@@H](C1=CC(=O)c2c(ccc(c2C1=O)O)O)OC(=O)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453856
PubChem CID:	5318520
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502328]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17488128]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19534474]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7775984]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9209	Rhizomnium magnifolium	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11300	Eucalyptus coccifera	Species	Myrtaceae	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	2
MIC	5
Others	13

Activity Type	# Activity
Cell Line	5
Organism	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT377	Cell Line	OVCAR-3	Homo sapiens	CD50	=	2.0	ug ml-1	PMID[485821]
NPT165	Cell Line	HeLa	Homo sapiens	CD50	=	5.4	ug ml-1	PMID[485821]
NPT65	Cell Line	HepG2	Homo sapiens	CD50	=	4.0	ug ml-1	PMID[485821]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	300.0	nM	PMID[485822]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	420.0	nM	PMID[485822]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Ratio	<=	2.0	n.a.	PMID[485821]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MBC	=	6.25	ug ml-1	PMID[485821]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	3.13	ug.mL-1	PMID[485821]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MBC	=	3.13	ug ml-1	PMID[485821]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	3.13	ug.mL-1	PMID[485821]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MBC	=	3.13	ug ml-1	PMID[485821]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	3.13	ug ml-1	PMID[485821]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.56	ug.mL-1	PMID[485821]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	1.56	ug ml-1	PMID[485821]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	Ratio	<=	2.0	n.a.	PMID[485821]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	Ratio	<=	2.0	n.a.	PMID[485821]

☑ 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 NPC37992 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	302
0.1-0.2	1210
0.2-0.3	2907
0.3-0.4	6522
0.4-0.5	11409
0.5-0.6	5197
0.6-0.7	8476
0.7-0.8	6155
0.8-0.85	431
0.85-0.9	56
0.9-0.95	11
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC241349
1.0	High Similarity	NPC147542
1.0	High Similarity	NPC42262
1.0	High Similarity	NPC220496
1.0	High Similarity	NPC32749
1.0	High Similarity	NPC327916
0.9925	High Similarity	NPC216312
0.9925	High Similarity	NPC29771
0.9925	High Similarity	NPC471602
0.9925	High Similarity	NPC476477
0.9925	High Similarity	NPC111422
0.9925	High Similarity	NPC256463
0.9925	High Similarity	NPC299405
0.9925	High Similarity	NPC306835
0.9778	High Similarity	NPC257003
0.9778	High Similarity	NPC471444
0.9706	High Similarity	NPC474300
0.9635	High Similarity	NPC476473
0.9565	High Similarity	NPC274085
0.9565	High Similarity	NPC89664
0.9485	High Similarity	NPC295339
0.9412	High Similarity	NPC61590
0.9286	High Similarity	NPC103910
0.9254	High Similarity	NPC110609
0.9254	High Similarity	NPC246693
0.9254	High Similarity	NPC242358
0.9214	High Similarity	NPC21873
0.8947	High Similarity	NPC306765
0.8913	High Similarity	NPC281513
0.8913	High Similarity	NPC22222
0.8881	High Similarity	NPC477409
0.8777	High Similarity	NPC27407
0.8767	High Similarity	NPC94781
0.8722	High Similarity	NPC477153
0.8667	High Similarity	NPC3224
0.8652	High Similarity	NPC305060
0.8643	High Similarity	NPC142027
0.863	High Similarity	NPC147250
0.8623	High Similarity	NPC7012
0.8601	High Similarity	NPC315578
0.86	High Similarity	NPC470408
0.86	High Similarity	NPC182921
0.86	High Similarity	NPC218870
0.86	High Similarity	NPC474824
0.8582	High Similarity	NPC272268
0.8581	High Similarity	NPC120171
0.8581	High Similarity	NPC44378
0.8581	High Similarity	NPC280753
0.8571	High Similarity	NPC119767
0.8562	High Similarity	NPC475923
0.8562	High Similarity	NPC474630
0.8562	High Similarity	NPC474309
0.8561	High Similarity	NPC477406
0.8553	High Similarity	NPC29552
0.8542	High Similarity	NPC124365
0.8542	High Similarity	NPC130485
0.8531	High Similarity	NPC26924
0.8531	High Similarity	NPC103337
0.8531	High Similarity	NPC477408
0.8531	High Similarity	NPC114620
0.8529	High Similarity	NPC1991
0.8529	High Similarity	NPC231774
0.8523	High Similarity	NPC315520
0.8519	High Similarity	NPC234890
0.8519	High Similarity	NPC74507
0.85	High Similarity	NPC43627
0.8493	Intermediate Similarity	NPC42540
0.8493	Intermediate Similarity	NPC151607
0.8489	Intermediate Similarity	NPC470831
0.8489	Intermediate Similarity	NPC205992
0.8489	Intermediate Similarity	NPC214702
0.8487	Intermediate Similarity	NPC474861
0.8478	Intermediate Similarity	NPC278928
0.8467	Intermediate Similarity	NPC471530
0.8462	Intermediate Similarity	NPC474301
0.8462	Intermediate Similarity	NPC33144
0.8462	Intermediate Similarity	NPC478200
0.8462	Intermediate Similarity	NPC191835
0.8462	Intermediate Similarity	NPC126739
0.8462	Intermediate Similarity	NPC221104
0.8462	Intermediate Similarity	NPC197666
0.8451	Intermediate Similarity	NPC141934
0.8451	Intermediate Similarity	NPC291454
0.844	Intermediate Similarity	NPC474097
0.8429	Intermediate Similarity	NPC58685
0.8429	Intermediate Similarity	NPC309430
0.8425	Intermediate Similarity	NPC159721
0.8425	Intermediate Similarity	NPC471731
0.8425	Intermediate Similarity	NPC478202
0.8421	Intermediate Similarity	NPC66029
0.8421	Intermediate Similarity	NPC285829
0.8421	Intermediate Similarity	NPC206778
0.8417	Intermediate Similarity	NPC475741
0.8414	Intermediate Similarity	NPC478217
0.8414	Intermediate Similarity	NPC470842
0.8414	Intermediate Similarity	NPC478201
0.8414	Intermediate Similarity	NPC283292
0.8414	Intermediate Similarity	NPC149533
0.8414	Intermediate Similarity	NPC472603
0.8414	Intermediate Similarity	NPC313123
0.8414	Intermediate Similarity	NPC472035
0.8411	Intermediate Similarity	NPC474533
0.8411	Intermediate Similarity	NPC180388
0.8411	Intermediate Similarity	NPC474534
0.8411	Intermediate Similarity	NPC281272
0.8406	Intermediate Similarity	NPC165257
0.8406	Intermediate Similarity	NPC237225
0.8403	Intermediate Similarity	NPC1268
0.84	Intermediate Similarity	NPC31132
0.8394	Intermediate Similarity	NPC136342
0.8394	Intermediate Similarity	NPC49647
0.8394	Intermediate Similarity	NPC96915
0.8394	Intermediate Similarity	NPC295202
0.8394	Intermediate Similarity	NPC227741
0.8392	Intermediate Similarity	NPC71256
0.8392	Intermediate Similarity	NPC245923
0.8392	Intermediate Similarity	NPC70380
0.8389	Intermediate Similarity	NPC470479
0.8389	Intermediate Similarity	NPC228012
0.8382	Intermediate Similarity	NPC310540
0.838	Intermediate Similarity	NPC161632
0.8378	Intermediate Similarity	NPC120536
0.8378	Intermediate Similarity	NPC300540
0.837	Intermediate Similarity	NPC307174
0.8369	Intermediate Similarity	NPC115458
0.8369	Intermediate Similarity	NPC472591
0.8367	Intermediate Similarity	NPC126882
0.8367	Intermediate Similarity	NPC478203
0.8367	Intermediate Similarity	NPC210966
0.8366	Intermediate Similarity	NPC472050
0.8366	Intermediate Similarity	NPC478027
0.8356	Intermediate Similarity	NPC329493
0.8356	Intermediate Similarity	NPC471733
0.8355	Intermediate Similarity	NPC477691
0.8355	Intermediate Similarity	NPC474622
0.8355	Intermediate Similarity	NPC474621
0.8346	Intermediate Similarity	NPC232178
0.8345	Intermediate Similarity	NPC168471
0.8345	Intermediate Similarity	NPC472601
0.8345	Intermediate Similarity	NPC156872
0.8345	Intermediate Similarity	NPC472600
0.8344	Intermediate Similarity	NPC39819
0.8344	Intermediate Similarity	NPC71390
0.8333	Intermediate Similarity	NPC173980
0.8333	Intermediate Similarity	NPC177307
0.8333	Intermediate Similarity	NPC472403
0.8333	Intermediate Similarity	NPC212693
0.8333	Intermediate Similarity	NPC472602
0.8333	Intermediate Similarity	NPC9121
0.8333	Intermediate Similarity	NPC94248
0.8333	Intermediate Similarity	NPC45537
0.8322	Intermediate Similarity	NPC474813
0.8322	Intermediate Similarity	NPC472308
0.8321	Intermediate Similarity	NPC287473
0.8321	Intermediate Similarity	NPC167055
0.8321	Intermediate Similarity	NPC240744
0.8321	Intermediate Similarity	NPC131799
0.8321	Intermediate Similarity	NPC103540
0.8312	Intermediate Similarity	NPC67197
0.8311	Intermediate Similarity	NPC83272
0.8311	Intermediate Similarity	NPC257558
0.831	Intermediate Similarity	NPC288089
0.8309	Intermediate Similarity	NPC275145
0.8301	Intermediate Similarity	NPC472890
0.8301	Intermediate Similarity	NPC192219
0.8301	Intermediate Similarity	NPC174599
0.8301	Intermediate Similarity	NPC82190
0.8299	Intermediate Similarity	NPC469885
0.8299	Intermediate Similarity	NPC472006
0.8298	Intermediate Similarity	NPC477407
0.8298	Intermediate Similarity	NPC70622
0.8298	Intermediate Similarity	NPC88864
0.8289	Intermediate Similarity	NPC477690
0.8289	Intermediate Similarity	NPC76041
0.8289	Intermediate Similarity	NPC115249
0.8289	Intermediate Similarity	NPC184284
0.8288	Intermediate Similarity	NPC472604
0.8288	Intermediate Similarity	NPC53649
0.8288	Intermediate Similarity	NPC187843
0.8288	Intermediate Similarity	NPC158634
0.8288	Intermediate Similarity	NPC472605
0.8286	Intermediate Similarity	NPC123
0.8286	Intermediate Similarity	NPC31539
0.8286	Intermediate Similarity	NPC198305
0.8286	Intermediate Similarity	NPC163169
0.8278	Intermediate Similarity	NPC56204
0.8278	Intermediate Similarity	NPC205766
0.8276	Intermediate Similarity	NPC88269
0.8273	Intermediate Similarity	NPC282923
0.8267	Intermediate Similarity	NPC172329
0.8267	Intermediate Similarity	NPC2569
0.8264	Intermediate Similarity	NPC474849
0.8264	Intermediate Similarity	NPC119542
0.8264	Intermediate Similarity	NPC178467
0.8264	Intermediate Similarity	NPC301915
0.8264	Intermediate Similarity	NPC474771
0.8264	Intermediate Similarity	NPC149372
0.8264	Intermediate Similarity	NPC261292
0.8264	Intermediate Similarity	NPC65837
0.8261	Intermediate Similarity	NPC474944

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 NPC37992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	850
0.2-0.3	1526
0.3-0.4	2477
0.4-0.5	2184
0.5-0.6	1199
0.6-0.7	524
0.7-0.8	123
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8321	Intermediate Similarity	NPD1470	Approved
0.8212	Intermediate Similarity	NPD3226	Approved
0.8138	Intermediate Similarity	NPD2935	Discontinued
0.812	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD2346	Discontinued
0.8029	Intermediate Similarity	NPD1201	Approved
0.7947	Intermediate Similarity	NPD2534	Approved
0.7947	Intermediate Similarity	NPD2532	Approved
0.7947	Intermediate Similarity	NPD2533	Approved
0.7905	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2799	Discontinued
0.78	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD8150	Discontinued
0.7778	Intermediate Similarity	NPD3764	Approved
0.7771	Intermediate Similarity	NPD7819	Suspended
0.777	Intermediate Similarity	NPD5408	Approved
0.777	Intermediate Similarity	NPD5404	Approved
0.777	Intermediate Similarity	NPD5406	Approved
0.777	Intermediate Similarity	NPD5405	Approved
0.773	Intermediate Similarity	NPD7473	Discontinued
0.7721	Intermediate Similarity	NPD9493	Approved
0.7706	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD2313	Discontinued
0.7654	Intermediate Similarity	NPD6232	Discontinued
0.7619	Intermediate Similarity	NPD8312	Approved
0.7619	Intermediate Similarity	NPD8313	Approved
0.7616	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD5402	Approved
0.7609	Intermediate Similarity	NPD9545	Approved
0.7582	Intermediate Similarity	NPD3300	Phase 2
0.7566	Intermediate Similarity	NPD8166	Discontinued
0.7566	Intermediate Similarity	NPD3750	Approved
0.7566	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1551	Phase 2
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2798	Approved
0.7484	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4628	Phase 3
0.7438	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5844	Phase 1
0.7407	Intermediate Similarity	NPD7075	Discontinued
0.7388	Intermediate Similarity	NPD2182	Approved
0.7383	Intermediate Similarity	NPD447	Suspended
0.7383	Intermediate Similarity	NPD230	Phase 1
0.7378	Intermediate Similarity	NPD6959	Discontinued
0.7372	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6663	Approved
0.7358	Intermediate Similarity	NPD4380	Phase 2
0.7351	Intermediate Similarity	NPD1510	Phase 2
0.7346	Intermediate Similarity	NPD7768	Phase 2
0.7343	Intermediate Similarity	NPD9717	Approved
0.7338	Intermediate Similarity	NPD7003	Approved
0.7333	Intermediate Similarity	NPD1607	Approved
0.7333	Intermediate Similarity	NPD5710	Approved
0.7333	Intermediate Similarity	NPD5711	Approved
0.7329	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2801	Approved
0.7329	Intermediate Similarity	NPD5736	Approved
0.7325	Intermediate Similarity	NPD6273	Approved
0.732	Intermediate Similarity	NPD1549	Phase 2
0.7317	Intermediate Similarity	NPD5494	Approved
0.7315	Intermediate Similarity	NPD1240	Approved
0.7312	Intermediate Similarity	NPD7411	Suspended
0.731	Intermediate Similarity	NPD1164	Approved
0.731	Intermediate Similarity	NPD1203	Approved
0.7308	Intermediate Similarity	NPD7390	Discontinued
0.7297	Intermediate Similarity	NPD411	Approved
0.7284	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8434	Phase 2
0.7279	Intermediate Similarity	NPD6832	Phase 2
0.7279	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1934	Approved
0.726	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD9266	Approved
0.7259	Intermediate Similarity	NPD74	Approved
0.7255	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2344	Approved
0.7255	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2932	Approved
0.7254	Intermediate Similarity	NPD4626	Approved
0.725	Intermediate Similarity	NPD6599	Discontinued
0.7241	Intermediate Similarity	NPD1283	Approved
0.7237	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3748	Approved
0.7232	Intermediate Similarity	NPD6535	Approved
0.7232	Intermediate Similarity	NPD6534	Approved
0.7222	Intermediate Similarity	NPD1608	Approved
0.7203	Intermediate Similarity	NPD3496	Discontinued
0.72	Intermediate Similarity	NPD943	Approved
0.72	Intermediate Similarity	NPD2979	Phase 3
0.7198	Intermediate Similarity	NPD7435	Discontinued
0.7197	Intermediate Similarity	NPD6799	Approved
0.7195	Intermediate Similarity	NPD3749	Approved
0.7193	Intermediate Similarity	NPD6559	Discontinued
0.719	Intermediate Similarity	NPD2796	Approved
0.7185	Intermediate Similarity	NPD9263	Approved
0.7185	Intermediate Similarity	NPD9264	Approved
0.7185	Intermediate Similarity	NPD9267	Approved
0.7183	Intermediate Similarity	NPD5691	Approved
0.7179	Intermediate Similarity	NPD6190	Approved
0.7175	Intermediate Similarity	NPD6212	Phase 3
0.7175	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6213	Phase 3
0.717	Intermediate Similarity	NPD5403	Approved
0.7161	Intermediate Similarity	NPD2800	Approved
0.716	Intermediate Similarity	NPD6801	Discontinued
0.716	Intermediate Similarity	NPD6844	Discontinued
0.7153	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3882	Suspended
0.7133	Intermediate Similarity	NPD3019	Approved
0.7127	Intermediate Similarity	NPD6778	Approved
0.7127	Intermediate Similarity	NPD6780	Approved
0.7127	Intermediate Similarity	NPD6776	Approved
0.7127	Intermediate Similarity	NPD6782	Approved
0.7127	Intermediate Similarity	NPD6779	Approved
0.7127	Intermediate Similarity	NPD6781	Approved
0.7127	Intermediate Similarity	NPD6777	Approved
0.7114	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7699	Phase 2
0.7111	Intermediate Similarity	NPD7700	Phase 2
0.7091	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD164	Approved
0.7086	Intermediate Similarity	NPD4060	Phase 1
0.7081	Intermediate Similarity	NPD7458	Discontinued
0.7075	Intermediate Similarity	NPD2797	Approved
0.7073	Intermediate Similarity	NPD3817	Phase 2
0.707	Intermediate Similarity	NPD2309	Approved
0.7067	Intermediate Similarity	NPD3268	Approved
0.7065	Intermediate Similarity	NPD8320	Phase 1
0.7065	Intermediate Similarity	NPD8319	Approved
0.7063	Intermediate Similarity	NPD920	Approved
0.7059	Intermediate Similarity	NPD3818	Discontinued
0.7059	Intermediate Similarity	NPD7177	Discontinued
0.7055	Intermediate Similarity	NPD37	Approved
0.7052	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7635	Approved
0.7048	Intermediate Similarity	NPD6234	Discontinued
0.7044	Intermediate Similarity	NPD5401	Approved
0.7044	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5953	Discontinued
0.7034	Intermediate Similarity	NPD1281	Approved
0.7032	Intermediate Similarity	NPD5763	Approved
0.7032	Intermediate Similarity	NPD5762	Approved
0.7032	Intermediate Similarity	NPD1471	Phase 3
0.703	Intermediate Similarity	NPD4966	Approved
0.703	Intermediate Similarity	NPD4967	Phase 2
0.703	Intermediate Similarity	NPD4965	Approved
0.7029	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1019	Discontinued
0.7025	Intermediate Similarity	NPD7236	Approved
0.702	Intermediate Similarity	NPD520	Approved
0.7014	Intermediate Similarity	NPD17	Approved
0.7014	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1778	Approved
0.7013	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7033	Discontinued
0.7013	Intermediate Similarity	NPD4308	Phase 3
0.7011	Intermediate Similarity	NPD7697	Approved
0.7011	Intermediate Similarity	NPD7696	Phase 3
0.7011	Intermediate Similarity	NPD7698	Approved
0.7007	Intermediate Similarity	NPD1876	Approved
0.7007	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7008	Discontinued
0.6993	Remote Similarity	NPD6651	Approved
0.6981	Remote Similarity	NPD1511	Approved
0.698	Remote Similarity	NPD2861	Phase 2
0.6973	Remote Similarity	NPD7871	Phase 2
0.6973	Remote Similarity	NPD7870	Phase 2
0.6968	Remote Similarity	NPD6100	Approved
0.6968	Remote Similarity	NPD2438	Suspended
0.6968	Remote Similarity	NPD6099	Approved
0.6968	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7874	Approved
0.6959	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3751	Discontinued
0.6957	Remote Similarity	NPD6823	Phase 2
0.6954	Remote Similarity	NPD5028	Approved
0.6954	Remote Similarity	NPD5026	Approved
0.6954	Remote Similarity	NPD4954	Approved
0.6954	Remote Similarity	NPD7985	Registered
0.6954	Remote Similarity	NPD36	Approved
0.6954	Remote Similarity	NPD5034	Approved
0.6954	Remote Similarity	NPD4955	Approved
0.695	Remote Similarity	NPD9281	Approved
0.695	Remote Similarity	NPD5951	Approved
0.6944	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6167	Clinical (unspecified phase)

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