NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	258.152
LogP:	3.042
LogD:	3.445
LogS:	-4.486
# Rotatable Bonds:	0
TPSA:	42.74
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.522
Synthetic Accessibility Score:	4.813
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.597
MDCK Permeability:	2.7077561753685586e-05
Pgp-inhibitor:	0.096
Pgp-substrate:	0.042
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.854
Plasma Protein Binding (PPB):	80.65116882324219%
Volume Distribution (VD):	1.583
Pgp-substrate:	22.21248435974121%

ADMET: Metabolism

CYP1A2-inhibitor:	0.37
CYP1A2-substrate:	0.436
CYP2C19-inhibitor:	0.56
CYP2C19-substrate:	0.572
CYP2C9-inhibitor:	0.43
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.528
CYP3A4-inhibitor:	0.155
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	14.698
Half-life (T1/2):	0.204

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.837
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.13
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.225
Carcinogencity:	0.824
Eye Corrosion:	0.004
Eye Irritation:	0.053
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC45947

Natural Product ID:	NPC45947
*Common Name:**	DHQZOOQNUWHCML-IIRLODAESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DHQZOOQNUWHCML-IIRLODAESA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-8-4-11(16)14-10(3)7-17-12(14)6-9(2)15-13(5-8)18-15/h7-8,13,15H,2,4-6H2,1,3H3/t8-,13-,15-/m0/s1
SMILES:	C[C@H]1CC(=O)c2c(C)coc2CC(=C)[C@H]2[C@H](C1)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484254
PubChem CID:	10444597
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0003671] Aryl alkyl ketones

*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
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	roots	northern Saudi desert	n.a.	PMID[10924184]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18177010]
NPO8286	Porophyllum ruderale	Species	Asteraceae	Eukaryota	n.a.	Along the Valencian coast, Spain	2020-Jun&Jul	PMID[35161358]
NPO11719	Lamellomorpha strongylata	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644054]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7730	Commiphora myrrha	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13613	Lophophora williamsii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7730	Commiphora myrrha	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13613	Lophophora williamsii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7730	Commiphora myrrha	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3693	Calpurnia aurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5284	Ramalina hierrensis	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9883	Allium giganteum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11719	Lamellomorpha strongylata	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14610	Ophiopogon intermedius	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1586	Gorgonocephalus chilensis	Species	Gorgonocephalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8810	Pinus austriaca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8286	Porophyllum ruderale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29336	Corynandra chelidonii	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9036	Dipteryx lacunifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2328	Lagochilus setulosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4463	Cytisus canariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5886	Fossombronia alaskana	Species	Fossombroniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9639	Prunus puddum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4236	Microscleroderma spirophora	Species	Scleritodermidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6022	Cytisus supinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25831	Siphonoglossa sessilis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13613	Lophophora williamsii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8985	Gazania rigens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10085	Aspergillus varians	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4964	Traversia baccharoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24891	Elmerina caryae	Species	Aporpiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	40000.0	nM	PMID[487504]

☑ 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 NPC45947 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	391
0.1-0.2	1627
0.2-0.3	4763
0.3-0.4	11355
0.4-0.5	9255
0.5-0.6	7359
0.6-0.7	7264
0.7-0.8	645
0.8-0.85	27
0.85-0.9	7
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC200718
0.8741	High Similarity	NPC474615
0.8731	High Similarity	NPC286130
0.8538	High Similarity	NPC184391
0.8507	High Similarity	NPC106247
0.85	High Similarity	NPC195920
0.8478	Intermediate Similarity	NPC248795
0.844	Intermediate Similarity	NPC475864
0.8392	Intermediate Similarity	NPC475904
0.8392	Intermediate Similarity	NPC474270
0.8322	Intermediate Similarity	NPC474220
0.8322	Intermediate Similarity	NPC474255
0.8322	Intermediate Similarity	NPC471618
0.8273	Intermediate Similarity	NPC282973
0.8239	Intermediate Similarity	NPC37488
0.8226	Intermediate Similarity	NPC22678
0.8182	Intermediate Similarity	NPC97904
0.8182	Intermediate Similarity	NPC216810
0.8148	Intermediate Similarity	NPC136340
0.8143	Intermediate Similarity	NPC18904
0.8129	Intermediate Similarity	NPC177262
0.8125	Intermediate Similarity	NPC474317
0.811	Intermediate Similarity	NPC79202
0.811	Intermediate Similarity	NPC59035
0.811	Intermediate Similarity	NPC45536
0.8099	Intermediate Similarity	NPC254198
0.8099	Intermediate Similarity	NPC205071
0.8099	Intermediate Similarity	NPC64568
0.8095	Intermediate Similarity	NPC474219
0.8095	Intermediate Similarity	NPC474378
0.8069	Intermediate Similarity	NPC19747
0.8058	Intermediate Similarity	NPC473268
0.8056	Intermediate Similarity	NPC62799
0.8047	Intermediate Similarity	NPC227660
0.8042	Intermediate Similarity	NPC84479
0.7972	Intermediate Similarity	NPC110305
0.7939	Intermediate Similarity	NPC79557
0.7939	Intermediate Similarity	NPC97566
0.7931	Intermediate Similarity	NPC104924
0.7914	Intermediate Similarity	NPC159786
0.7902	Intermediate Similarity	NPC473152
0.7899	Intermediate Similarity	NPC293253
0.7899	Intermediate Similarity	NPC214097
0.7895	Intermediate Similarity	NPC118853
0.7879	Intermediate Similarity	NPC323118
0.78	Intermediate Similarity	NPC114880
0.7794	Intermediate Similarity	NPC329707
0.777	Intermediate Similarity	NPC211625
0.7761	Intermediate Similarity	NPC178382
0.7752	Intermediate Similarity	NPC205523
0.7746	Intermediate Similarity	NPC472376
0.7724	Intermediate Similarity	NPC103134
0.7704	Intermediate Similarity	NPC471074
0.7704	Intermediate Similarity	NPC473885
0.7667	Intermediate Similarity	NPC472406
0.766	Intermediate Similarity	NPC247743
0.7643	Intermediate Similarity	NPC470740
0.7639	Intermediate Similarity	NPC61157
0.7639	Intermediate Similarity	NPC218204
0.7639	Intermediate Similarity	NPC473681
0.7635	Intermediate Similarity	NPC224418
0.7634	Intermediate Similarity	NPC217180
0.7634	Intermediate Similarity	NPC312525
0.7632	Intermediate Similarity	NPC42458
0.7632	Intermediate Similarity	NPC158261
0.7632	Intermediate Similarity	NPC472786
0.7616	Intermediate Similarity	NPC475777
0.7571	Intermediate Similarity	NPC471544
0.7571	Intermediate Similarity	NPC473344
0.7571	Intermediate Similarity	NPC471545
0.7569	Intermediate Similarity	NPC107571
0.7568	Intermediate Similarity	NPC233763
0.7566	Intermediate Similarity	NPC67654
0.7551	Intermediate Similarity	NPC261733
0.7551	Intermediate Similarity	NPC117674
0.7551	Intermediate Similarity	NPC218712
0.7551	Intermediate Similarity	NPC307346
0.7551	Intermediate Similarity	NPC267004
0.7548	Intermediate Similarity	NPC333139
0.7548	Intermediate Similarity	NPC476349
0.7548	Intermediate Similarity	NPC476350
0.7535	Intermediate Similarity	NPC158525
0.7534	Intermediate Similarity	NPC263337
0.7532	Intermediate Similarity	NPC279768
0.7532	Intermediate Similarity	NPC160015
0.7532	Intermediate Similarity	NPC81405
0.7532	Intermediate Similarity	NPC247677
0.7519	Intermediate Similarity	NPC244862
0.7519	Intermediate Similarity	NPC67345
0.7518	Intermediate Similarity	NPC470858
0.7518	Intermediate Similarity	NPC470859
0.7517	Intermediate Similarity	NPC148374
0.7517	Intermediate Similarity	NPC190572
0.7517	Intermediate Similarity	NPC281398
0.7516	Intermediate Similarity	NPC75310
0.7516	Intermediate Similarity	NPC290927
0.7516	Intermediate Similarity	NPC472785
0.75	Intermediate Similarity	NPC65735
0.75	Intermediate Similarity	NPC156244
0.75	Intermediate Similarity	NPC93241
0.75	Intermediate Similarity	NPC27798
0.75	Intermediate Similarity	NPC188377
0.7484	Intermediate Similarity	NPC260902
0.7484	Intermediate Similarity	NPC296957
0.7484	Intermediate Similarity	NPC140952
0.7483	Intermediate Similarity	NPC22248
0.7483	Intermediate Similarity	NPC303217
0.7483	Intermediate Similarity	NPC46896
0.7483	Intermediate Similarity	NPC214572
0.7483	Intermediate Similarity	NPC146872
0.7482	Intermediate Similarity	NPC59502
0.7468	Intermediate Similarity	NPC474542
0.7467	Intermediate Similarity	NPC198427
0.7464	Intermediate Similarity	NPC141059
0.7464	Intermediate Similarity	NPC137570
0.7447	Intermediate Similarity	NPC473982
0.7447	Intermediate Similarity	NPC471995
0.7436	Intermediate Similarity	NPC287559
0.7434	Intermediate Similarity	NPC191104
0.7432	Intermediate Similarity	NPC86935
0.7431	Intermediate Similarity	NPC310043
0.7431	Intermediate Similarity	NPC42400
0.7431	Intermediate Similarity	NPC4764
0.7429	Intermediate Similarity	NPC21460
0.7421	Intermediate Similarity	NPC136641
0.7415	Intermediate Similarity	NPC62103
0.7415	Intermediate Similarity	NPC20578
0.7415	Intermediate Similarity	NPC470856
0.7407	Intermediate Similarity	NPC115859
0.7407	Intermediate Similarity	NPC1848
0.7405	Intermediate Similarity	NPC472664
0.7405	Intermediate Similarity	NPC56358
0.7402	Intermediate Similarity	NPC140688
0.74	Intermediate Similarity	NPC221809
0.74	Intermediate Similarity	NPC71821
0.74	Intermediate Similarity	NPC10088
0.7397	Intermediate Similarity	NPC470399
0.7391	Intermediate Similarity	NPC83301
0.7388	Intermediate Similarity	NPC137710
0.7386	Intermediate Similarity	NPC470380
0.7379	Intermediate Similarity	NPC29638
0.7379	Intermediate Similarity	NPC220094
0.7379	Intermediate Similarity	NPC236532
0.7379	Intermediate Similarity	NPC476943
0.7376	Intermediate Similarity	NPC477645
0.7372	Intermediate Similarity	NPC141252
0.7372	Intermediate Similarity	NPC11799
0.7372	Intermediate Similarity	NPC474611
0.7372	Intermediate Similarity	NPC116639
0.7372	Intermediate Similarity	NPC473368
0.7368	Intermediate Similarity	NPC88445
0.7365	Intermediate Similarity	NPC223415
0.7365	Intermediate Similarity	NPC470741
0.7355	Intermediate Similarity	NPC250769
0.7355	Intermediate Similarity	NPC104736
0.7355	Intermediate Similarity	NPC295608
0.7355	Intermediate Similarity	NPC41880
0.7355	Intermediate Similarity	NPC278010
0.7353	Intermediate Similarity	NPC174915
0.7353	Intermediate Similarity	NPC263870
0.7353	Intermediate Similarity	NPC270807
0.7351	Intermediate Similarity	NPC74539
0.7351	Intermediate Similarity	NPC304443
0.7348	Intermediate Similarity	NPC150895
0.7348	Intermediate Similarity	NPC28054
0.7347	Intermediate Similarity	NPC137009
0.7343	Intermediate Similarity	NPC471998
0.7338	Intermediate Similarity	NPC319140
0.7338	Intermediate Similarity	NPC95567
0.7333	Intermediate Similarity	NPC246903
0.7333	Intermediate Similarity	NPC276676
0.7329	Intermediate Similarity	NPC265181
0.7329	Intermediate Similarity	NPC233707
0.7329	Intermediate Similarity	NPC98395
0.7324	Intermediate Similarity	NPC477412
0.7323	Intermediate Similarity	NPC42471
0.732	Intermediate Similarity	NPC472787
0.732	Intermediate Similarity	NPC144010
0.732	Intermediate Similarity	NPC135303
0.732	Intermediate Similarity	NPC148423
0.7315	Intermediate Similarity	NPC470636
0.7315	Intermediate Similarity	NPC96791
0.7315	Intermediate Similarity	NPC226942
0.7315	Intermediate Similarity	NPC472344
0.7312	Intermediate Similarity	NPC473766
0.7312	Intermediate Similarity	NPC473753
0.7312	Intermediate Similarity	NPC270312
0.731	Intermediate Similarity	NPC310830
0.7308	Intermediate Similarity	NPC474386
0.7308	Intermediate Similarity	NPC304692
0.7305	Intermediate Similarity	NPC473894
0.7303	Intermediate Similarity	NPC329180
0.7303	Intermediate Similarity	NPC306788
0.7292	Intermediate Similarity	NPC209858
0.729	Intermediate Similarity	NPC179170
0.729	Intermediate Similarity	NPC131725
0.7273	Intermediate Similarity	NPC145830
0.7273	Intermediate Similarity	NPC75906
0.7273	Intermediate Similarity	NPC474425
0.7273	Intermediate Similarity	NPC471613

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 NPC45947 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	1096
0.2-0.3	2118
0.3-0.4	2951
0.4-0.5	1723
0.5-0.6	727
0.6-0.7	173
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7548	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD920	Approved
0.7333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1471	Phase 3
0.7329	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2344	Approved
0.726	Intermediate Similarity	NPD2796	Approved
0.72	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2309	Approved
0.7114	Intermediate Similarity	NPD2800	Approved
0.7114	Intermediate Similarity	NPD1243	Approved
0.7101	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6279	Approved
0.7006	Intermediate Similarity	NPD6280	Approved
0.6957	Remote Similarity	NPD17	Approved
0.6957	Remote Similarity	NPD5494	Approved
0.6914	Remote Similarity	NPD1247	Approved
0.6909	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD2532	Approved
0.6883	Remote Similarity	NPD2534	Approved
0.6883	Remote Similarity	NPD2533	Approved
0.6867	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5761	Phase 2
0.6855	Remote Similarity	NPD5760	Phase 2
0.6831	Remote Similarity	NPD1876	Approved
0.6829	Remote Similarity	NPD3926	Phase 2
0.6821	Remote Similarity	NPD1549	Phase 2
0.6815	Remote Similarity	NPD1241	Discontinued
0.6809	Remote Similarity	NPD3972	Approved
0.6809	Remote Similarity	NPD1608	Approved
0.679	Remote Similarity	NPD919	Approved
0.6774	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6808	Phase 2
0.6744	Remote Similarity	NPD8434	Phase 2
0.6736	Remote Similarity	NPD2798	Approved
0.6733	Remote Similarity	NPD2799	Discontinued
0.6732	Remote Similarity	NPD4628	Phase 3
0.6708	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2313	Discontinued
0.6646	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6832	Phase 2
0.6623	Remote Similarity	NPD1510	Phase 2
0.6621	Remote Similarity	NPD1019	Discontinued
0.6605	Remote Similarity	NPD2296	Approved
0.6604	Remote Similarity	NPD3226	Approved
0.6603	Remote Similarity	NPD6799	Approved
0.6601	Remote Similarity	NPD970	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6651	Approved
0.66	Remote Similarity	NPD1607	Approved
0.6593	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1934	Approved
0.6579	Remote Similarity	NPD1551	Phase 2
0.6564	Remote Similarity	NPD3882	Suspended
0.6562	Remote Similarity	NPD6599	Discontinued
0.6558	Remote Similarity	NPD2654	Approved
0.6558	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7819	Suspended
0.6536	Remote Similarity	NPD6002	Phase 3
0.6536	Remote Similarity	NPD2346	Discontinued
0.6536	Remote Similarity	NPD6005	Phase 3
0.6536	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD6004	Phase 3
0.6524	Remote Similarity	NPD3749	Approved
0.65	Remote Similarity	NPD9092	Discovery
0.6488	Remote Similarity	NPD2403	Approved
0.6479	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3140	Approved
0.6467	Remote Similarity	NPD3142	Approved
0.646	Remote Similarity	NPD4380	Phase 2
0.6458	Remote Similarity	NPD9717	Approved
0.6456	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD9545	Approved
0.6453	Remote Similarity	NPD6559	Discontinued
0.6442	Remote Similarity	NPD2801	Approved
0.6424	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7075	Discontinued
0.6423	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7411	Suspended
0.6412	Remote Similarity	NPD3818	Discontinued
0.641	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5585	Approved
0.6407	Remote Similarity	NPD6959	Discontinued
0.6405	Remote Similarity	NPD7033	Discontinued
0.6402	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD3817	Phase 2
0.6395	Remote Similarity	NPD5647	Approved
0.6392	Remote Similarity	NPD1511	Approved
0.638	Remote Similarity	NPD6801	Discontinued
0.6358	Remote Similarity	NPD6764	Approved
0.6358	Remote Similarity	NPD6765	Approved
0.6351	Remote Similarity	NPD9494	Approved
0.6327	Remote Similarity	NPD3266	Approved
0.6327	Remote Similarity	NPD3267	Approved
0.6324	Remote Similarity	NPD2182	Approved
0.6316	Remote Similarity	NPD447	Suspended
0.6312	Remote Similarity	NPD1512	Approved
0.6303	Remote Similarity	NPD5402	Approved
0.6299	Remote Similarity	NPD3748	Approved
0.6294	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6166	Phase 2
0.6273	Remote Similarity	NPD5403	Approved
0.6272	Remote Similarity	NPD5711	Approved
0.6272	Remote Similarity	NPD5710	Approved
0.6266	Remote Similarity	NPD3887	Approved
0.6258	Remote Similarity	NPD6099	Approved
0.6258	Remote Similarity	NPD6100	Approved
0.625	Remote Similarity	NPD1778	Approved
0.625	Remote Similarity	NPD4662	Approved
0.625	Remote Similarity	NPD5401	Approved
0.625	Remote Similarity	NPD4661	Approved
0.625	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD3268	Approved
0.6225	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD2797	Approved
0.6216	Remote Similarity	NPD1203	Approved
0.6215	Remote Similarity	NPD6785	Approved
0.6215	Remote Similarity	NPD6784	Approved
0.6211	Remote Similarity	NPD6273	Approved
0.6209	Remote Similarity	NPD6355	Discontinued
0.6209	Remote Similarity	NPD4618	Approved
0.6209	Remote Similarity	NPD4622	Approved
0.6199	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4359	Approved
0.6185	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6844	Discontinued
0.6181	Remote Similarity	NPD1651	Approved
0.6173	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD3869	Phase 3
0.6173	Remote Similarity	NPD3873	Phase 3
0.6171	Remote Similarity	NPD1298	Discontinued
0.6168	Remote Similarity	NPD7768	Phase 2
0.6168	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD7473	Discontinued
0.6154	Remote Similarity	NPD2935	Discontinued
0.6149	Remote Similarity	NPD7074	Phase 3
0.6148	Remote Similarity	NPD164	Approved
0.6129	Remote Similarity	NPD5688	Approved
0.6129	Remote Similarity	NPD5689	Approved
0.6127	Remote Similarity	NPD2163	Approved
0.6118	Remote Similarity	NPD411	Approved
0.6118	Remote Similarity	NPD3764	Approved
0.6114	Remote Similarity	NPD5953	Discontinued
0.6104	Remote Similarity	NPD230	Phase 1
0.6104	Remote Similarity	NPD1933	Approved
0.6101	Remote Similarity	NPD3750	Approved
0.6092	Remote Similarity	NPD7054	Approved
0.6087	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD9493	Approved
0.6082	Remote Similarity	NPD6232	Discontinued
0.6078	Remote Similarity	NPD8032	Phase 2
0.6078	Remote Similarity	NPD4870	Approved
0.6067	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3134	Approved
0.6057	Remote Similarity	NPD7472	Approved
0.6057	Remote Similarity	NPD1729	Discontinued
0.6054	Remote Similarity	NPD1281	Approved
0.6043	Remote Similarity	NPD2067	Discontinued
0.6039	Remote Similarity	NPD2979	Phase 3
0.6039	Remote Similarity	NPD4307	Phase 2
0.6034	Remote Similarity	NPD3751	Discontinued
0.6026	Remote Similarity	NPD2861	Phase 2
0.6025	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD6386	Approved
0.6024	Remote Similarity	NPD5890	Approved
0.6024	Remote Similarity	NPD5889	Approved
0.6024	Remote Similarity	NPD6385	Approved
0.6023	Remote Similarity	NPD6797	Phase 2
0.6022	Remote Similarity	NPD8285	Discontinued
0.6013	Remote Similarity	NPD2353	Approved
0.6013	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD5353	Approved
0.6012	Remote Similarity	NPD2186	Approved
0.6011	Remote Similarity	NPD8313	Approved
0.6011	Remote Similarity	NPD8312	Approved
0.6	Remote Similarity	NPD1470	Approved
0.6	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2649	Approved
0.6	Remote Similarity	NPD2651	Approved
0.6	Remote Similarity	NPD7286	Phase 2
0.6	Remote Similarity	NPD1894	Discontinued
0.6	Remote Similarity	NPD6362	Approved
0.5989	Remote Similarity	NPD7251	Discontinued
0.5988	Remote Similarity	NPD3787	Discontinued
0.5988	Remote Similarity	NPD7577	Discontinued
0.5986	Remote Similarity	NPD3496	Discontinued
0.5976	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5975	Remote Similarity	NPD2424	Discontinued
0.5972	Remote Similarity	NPD405	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