NPASS Compound

Structure

CID290927 OpenBabel06191716102D 22 23 0 0 0 0 0 0 0 0999 V2000 4.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 13 1 0 0 0 0 3 13 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 20 2 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 19 2 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.16
Volume:	327.983
LogP:	5.862
LogD:	4.381
LogS:	-4.882
# Rotatable Bonds:	6
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	3.149
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.832
MDCK Permeability:	2.1042795196990483e-05
Pgp-inhibitor:	0.185
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.76
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	97.61363220214844%
Volume Distribution (VD):	3.882
Pgp-substrate:	5.287134170532227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.421
CYP2C19-inhibitor:	0.942
CYP2C19-substrate:	0.2
CYP2C9-inhibitor:	0.813
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.607
CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.496
CYP3A4-substrate:	0.118

ADMET: Excretion

Clearance (CL):	5.629
Half-life (T1/2):	0.136

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.792
Drug-inuced Liver Injury (DILI):	0.733
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.884
Carcinogencity:	0.638
Eye Corrosion:	0.082
Eye Irritation:	0.939
Respiratory Toxicity:	0.774

Download Data

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

Natural Product: NPC290927

Natural Product ID:	NPC290927
*Common Name:**	2-(2',3-Epoxy-1',3'-Heptadienyl)-6-Hydroxy-5-(3-Methyl-2-Butenyl)Benzaldehyde
IUPAC Name:	5-hydroxy-6-(3-methylbut-2-enyl)-2-[(E)-pent-1-enyl]-1-benzofuran-4-carbaldehyde
Synonyms:
Standard InCHIKey:	SBYYFNVKZGJIPR-VOTSOKGWSA-N
Standard InCHI:	InChI=1S/C19H22O3/c1-4-5-6-7-15-11-16-17(12-20)19(21)14(9-8-13(2)3)10-18(16)22-15/h6-8,10-12,21H,4-5,9H2,1-3H3/b7-6+
SMILES:	CCC/C=C/c1oc2c(c1)c(C=O)c(c(c2)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462797
PubChem CID:	44559107
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO30824	Eurotium repens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667972]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	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	8
Others	5

Activity Type	# Activity
Individual Protein	5
Organism	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[574308]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[574308]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[574308]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	<	40.0	%	PMID[574308]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Activity	<	40.0	%	PMID[574308]
NPT1	Others	Radical scavenging activity		IC50	=	88.0	ug.mL-1	PMID[574307]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.8	ug.mL-1	PMID[574309]
NPT1666	Organism	Plasmodium falciparum D6	Plasmodium falciparum D6	IC50	=	3.0	ug.mL-1	PMID[574309]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	6.2	ug.mL-1	PMID[574309]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	5.4	ug.mL-1	PMID[574309]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	7.75	ug.mL-1	PMID[574309]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	5.31	ug.mL-1	PMID[574309]
NPT554	Organism	Candida glabrata	Candida glabrata	IC50	=	1.13	ug.mL-1	PMID[574309]

☑ 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 NPC290927 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	392
0.1-0.2	1686
0.2-0.3	3929
0.3-0.4	10694
0.4-0.5	8222
0.5-0.6	4425
0.6-0.7	6581
0.7-0.8	6145
0.8-0.85	565
0.85-0.9	56
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9226	High Similarity	NPC24761
0.8861	High Similarity	NPC269117
0.8839	High Similarity	NPC84721
0.879	High Similarity	NPC212967
0.879	High Similarity	NPC246647
0.879	High Similarity	NPC164110
0.879	High Similarity	NPC96342
0.8726	High Similarity	NPC180924
0.8726	High Similarity	NPC221992
0.871	High Similarity	NPC145830
0.8701	High Similarity	NPC226578
0.8699	High Similarity	NPC265793
0.8675	High Similarity	NPC117674
0.8662	High Similarity	NPC148938
0.8627	High Similarity	NPC281398
0.8618	High Similarity	NPC93241
0.8618	High Similarity	NPC27798
0.8609	High Similarity	NPC329493
0.8608	High Similarity	NPC247677
0.8608	High Similarity	NPC160015
0.8599	High Similarity	NPC179170
0.8599	High Similarity	NPC235333
0.859	High Similarity	NPC116604
0.8581	High Similarity	NPC278832
0.8581	High Similarity	NPC64157
0.8571	High Similarity	NPC252208
0.8553	High Similarity	NPC473282
0.8553	High Similarity	NPC260902
0.8553	High Similarity	NPC104380
0.8553	High Similarity	NPC217602
0.8553	High Similarity	NPC317900
0.8553	High Similarity	NPC299094
0.8553	High Similarity	NPC10051
0.8553	High Similarity	NPC476404
0.8553	High Similarity	NPC296957
0.8553	High Similarity	NPC294300
0.8553	High Similarity	NPC44199
0.8544	High Similarity	NPC297531
0.8544	High Similarity	NPC213936
0.8543	High Similarity	NPC124365
0.8535	High Similarity	NPC253872
0.8535	High Similarity	NPC263676
0.8535	High Similarity	NPC207624
0.8526	High Similarity	NPC13282
0.8523	High Similarity	NPC130976
0.8506	High Similarity	NPC300540
0.8506	High Similarity	NPC308799
0.85	High Similarity	NPC472877
0.85	High Similarity	NPC476349
0.85	High Similarity	NPC477692
0.85	High Similarity	NPC476350
0.8497	Intermediate Similarity	NPC89664
0.8497	Intermediate Similarity	NPC274085
0.8497	Intermediate Similarity	NPC469642
0.8481	Intermediate Similarity	NPC158261
0.8481	Intermediate Similarity	NPC42458
0.8481	Intermediate Similarity	NPC208806
0.8471	Intermediate Similarity	NPC115324
0.8471	Intermediate Similarity	NPC58668
0.8471	Intermediate Similarity	NPC106372
0.8471	Intermediate Similarity	NPC170169
0.8471	Intermediate Similarity	NPC193976
0.8471	Intermediate Similarity	NPC23668
0.8467	Intermediate Similarity	NPC98395
0.8466	Intermediate Similarity	NPC136641
0.8457	Intermediate Similarity	NPC193998
0.8452	Intermediate Similarity	NPC113428
0.8452	Intermediate Similarity	NPC61284
0.8447	Intermediate Similarity	NPC472781
0.8447	Intermediate Similarity	NPC472782
0.8447	Intermediate Similarity	NPC143050
0.8438	Intermediate Similarity	NPC268360
0.8431	Intermediate Similarity	NPC158871
0.8428	Intermediate Similarity	NPC233776
0.8428	Intermediate Similarity	NPC198490
0.8418	Intermediate Similarity	NPC40356
0.8418	Intermediate Similarity	NPC67654
0.8418	Intermediate Similarity	NPC154683
0.8418	Intermediate Similarity	NPC142308
0.8415	Intermediate Similarity	NPC191012
0.8411	Intermediate Similarity	NPC1268
0.8408	Intermediate Similarity	NPC230713
0.8408	Intermediate Similarity	NPC167576
0.8408	Intermediate Similarity	NPC144010
0.8408	Intermediate Similarity	NPC472406
0.8408	Intermediate Similarity	NPC78335
0.8397	Intermediate Similarity	NPC5537
0.8395	Intermediate Similarity	NPC304387
0.8395	Intermediate Similarity	NPC472780
0.8395	Intermediate Similarity	NPC472783
0.8393	Intermediate Similarity	NPC295914
0.8389	Intermediate Similarity	NPC281513
0.8389	Intermediate Similarity	NPC22222
0.8385	Intermediate Similarity	NPC472299
0.8377	Intermediate Similarity	NPC477409
0.8377	Intermediate Similarity	NPC469385
0.8365	Intermediate Similarity	NPC1477
0.8365	Intermediate Similarity	NPC477691
0.8365	Intermediate Similarity	NPC213608
0.8365	Intermediate Similarity	NPC135522
0.8365	Intermediate Similarity	NPC183874
0.8365	Intermediate Similarity	NPC88958
0.8364	Intermediate Similarity	NPC186392
0.8354	Intermediate Similarity	NPC156244
0.8354	Intermediate Similarity	NPC291110
0.8353	Intermediate Similarity	NPC475996
0.8344	Intermediate Similarity	NPC62735
0.8344	Intermediate Similarity	NPC37226
0.8344	Intermediate Similarity	NPC226644
0.8344	Intermediate Similarity	NPC178202
0.8344	Intermediate Similarity	NPC233707
0.8333	Intermediate Similarity	NPC198427
0.8333	Intermediate Similarity	NPC313368
0.8323	Intermediate Similarity	NPC98926
0.8322	Intermediate Similarity	NPC209858
0.8313	Intermediate Similarity	NPC99199
0.8304	Intermediate Similarity	NPC8927
0.8304	Intermediate Similarity	NPC228209
0.8303	Intermediate Similarity	NPC277480
0.8303	Intermediate Similarity	NPC53640
0.8302	Intermediate Similarity	NPC24232
0.8302	Intermediate Similarity	NPC477690
0.8302	Intermediate Similarity	NPC38361
0.8302	Intermediate Similarity	NPC130015
0.8302	Intermediate Similarity	NPC10429
0.8302	Intermediate Similarity	NPC5871
0.8301	Intermediate Similarity	NPC28337
0.8293	Intermediate Similarity	NPC101769
0.8293	Intermediate Similarity	NPC100849
0.8291	Intermediate Similarity	NPC294646
0.8291	Intermediate Similarity	NPC227122
0.828	Intermediate Similarity	NPC135325
0.8274	Intermediate Similarity	NPC277510
0.8272	Intermediate Similarity	NPC228501
0.8269	Intermediate Similarity	NPC190572
0.8269	Intermediate Similarity	NPC300267
0.8269	Intermediate Similarity	NPC51641
0.8253	Intermediate Similarity	NPC472660
0.8253	Intermediate Similarity	NPC473945
0.8253	Intermediate Similarity	NPC247973
0.8253	Intermediate Similarity	NPC95715
0.825	Intermediate Similarity	NPC472462
0.825	Intermediate Similarity	NPC169990
0.825	Intermediate Similarity	NPC122365
0.825	Intermediate Similarity	NPC72370
0.825	Intermediate Similarity	NPC214632
0.825	Intermediate Similarity	NPC210942
0.8247	Intermediate Similarity	NPC69755
0.8242	Intermediate Similarity	NPC37183
0.8242	Intermediate Similarity	NPC38914
0.8242	Intermediate Similarity	NPC472784
0.8239	Intermediate Similarity	NPC72958
0.8239	Intermediate Similarity	NPC258249
0.8239	Intermediate Similarity	NPC471613
0.8239	Intermediate Similarity	NPC474417
0.8239	Intermediate Similarity	NPC149526
0.8239	Intermediate Similarity	NPC232645
0.8235	Intermediate Similarity	NPC23553
0.8235	Intermediate Similarity	NPC221820
0.8235	Intermediate Similarity	NPC77179
0.8229	Intermediate Similarity	NPC60848
0.8228	Intermediate Similarity	NPC296030
0.8228	Intermediate Similarity	NPC65589
0.8228	Intermediate Similarity	NPC288036
0.8228	Intermediate Similarity	NPC39929
0.8228	Intermediate Similarity	NPC97029
0.8228	Intermediate Similarity	NPC266499
0.8228	Intermediate Similarity	NPC97028
0.8228	Intermediate Similarity	NPC100985
0.8228	Intermediate Similarity	NPC158338
0.8221	Intermediate Similarity	NPC476506
0.8221	Intermediate Similarity	NPC470810
0.8221	Intermediate Similarity	NPC284495
0.8217	Intermediate Similarity	NPC17816
0.8217	Intermediate Similarity	NPC12148
0.8217	Intermediate Similarity	NPC478018
0.8217	Intermediate Similarity	NPC71055
0.8217	Intermediate Similarity	NPC150215
0.8217	Intermediate Similarity	NPC137296
0.8217	Intermediate Similarity	NPC130581
0.8214	Intermediate Similarity	NPC307286
0.8212	Intermediate Similarity	NPC141934
0.8212	Intermediate Similarity	NPC163029
0.821	Intermediate Similarity	NPC269495
0.821	Intermediate Similarity	NPC270044
0.821	Intermediate Similarity	NPC201127
0.821	Intermediate Similarity	NPC263483
0.821	Intermediate Similarity	NPC196448
0.821	Intermediate Similarity	NPC65504
0.821	Intermediate Similarity	NPC123153
0.8199	Intermediate Similarity	NPC89625
0.8199	Intermediate Similarity	NPC149618
0.8194	Intermediate Similarity	NPC476473
0.8194	Intermediate Similarity	NPC53016
0.8188	Intermediate Similarity	NPC118253
0.8187	Intermediate Similarity	NPC271681
0.8187	Intermediate Similarity	NPC474843
0.8187	Intermediate Similarity	NPC87708
0.8187	Intermediate Similarity	NPC281272
0.8182	Intermediate Similarity	NPC308156

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 NPC290927 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	1007
0.2-0.3	1616
0.3-0.4	2706
0.4-0.5	1926
0.5-0.6	1054
0.6-0.7	336
0.7-0.8	141
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD3226	Approved
0.8224	Intermediate Similarity	NPD2344	Approved
0.8105	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD2532	Approved
0.8089	Intermediate Similarity	NPD2533	Approved
0.8089	Intermediate Similarity	NPD2534	Approved
0.8061	Intermediate Similarity	NPD1247	Approved
0.8013	Intermediate Similarity	NPD2309	Approved
0.7987	Intermediate Similarity	NPD1471	Phase 3
0.7987	Intermediate Similarity	NPD2346	Discontinued
0.7875	Intermediate Similarity	NPD920	Approved
0.7862	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7844	Intermediate Similarity	NPD6959	Discontinued
0.7805	Intermediate Similarity	NPD7819	Suspended
0.7771	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6232	Discontinued
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7679	Intermediate Similarity	NPD5494	Approved
0.7665	Intermediate Similarity	NPD3749	Approved
0.7661	Intermediate Similarity	NPD7473	Discontinued
0.7651	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8434	Phase 2
0.7613	Intermediate Similarity	NPD1607	Approved
0.7605	Intermediate Similarity	NPD3882	Suspended
0.759	Intermediate Similarity	NPD2801	Approved
0.7582	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1551	Phase 2
0.7576	Intermediate Similarity	NPD7411	Suspended
0.7572	Intermediate Similarity	NPD5844	Phase 1
0.7547	Intermediate Similarity	NPD1243	Approved
0.7547	Intermediate Similarity	NPD2800	Approved
0.7533	Intermediate Similarity	NPD6696	Suspended
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1240	Approved
0.7484	Intermediate Similarity	NPD1549	Phase 2
0.7483	Intermediate Similarity	NPD1470	Approved
0.7468	Intermediate Similarity	NPD2796	Approved
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2296	Approved
0.7425	Intermediate Similarity	NPD1934	Approved
0.7423	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4380	Phase 2
0.7405	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1510	Phase 2
0.7391	Intermediate Similarity	NPD4628	Phase 3
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.7381	Intermediate Similarity	NPD5760	Phase 2
0.7381	Intermediate Similarity	NPD5761	Phase 2
0.7375	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8313	Approved
0.736	Intermediate Similarity	NPD8312	Approved
0.7353	Intermediate Similarity	NPD7075	Discontinued
0.7349	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD1201	Approved
0.7321	Intermediate Similarity	NPD6279	Approved
0.7321	Intermediate Similarity	NPD6280	Approved
0.7314	Intermediate Similarity	NPD7177	Discontinued
0.7314	Intermediate Similarity	NPD3818	Discontinued
0.7305	Intermediate Similarity	NPD6599	Discontinued
0.7294	Intermediate Similarity	NPD7768	Phase 2
0.7278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1511	Approved
0.725	Intermediate Similarity	NPD6100	Approved
0.725	Intermediate Similarity	NPD6099	Approved
0.7235	Intermediate Similarity	NPD5402	Approved
0.7219	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2798	Approved
0.7184	Intermediate Similarity	NPD6808	Phase 2
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7179	Intermediate Similarity	NPD4625	Phase 3
0.7178	Intermediate Similarity	NPD3750	Approved
0.7178	Intermediate Similarity	NPD7003	Approved
0.7178	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1608	Approved
0.7169	Intermediate Similarity	NPD1512	Approved
0.7162	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD7390	Discontinued
0.7151	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD411	Approved
0.7133	Intermediate Similarity	NPD1651	Approved
0.7118	Intermediate Similarity	NPD6844	Discontinued
0.7118	Intermediate Similarity	NPD6801	Discontinued
0.7107	Intermediate Similarity	NPD447	Suspended
0.7102	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6166	Phase 2
0.7095	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5953	Discontinued
0.7086	Intermediate Similarity	NPD1778	Approved
0.7086	Intermediate Similarity	NPD4626	Approved
0.7078	Intermediate Similarity	NPD1283	Approved
0.7073	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7697	Approved
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7068	Intermediate Similarity	NPD7696	Phase 3
0.7068	Intermediate Similarity	NPD7698	Approved
0.7066	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD9717	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.7051	Intermediate Similarity	NPD2861	Phase 2
0.7051	Intermediate Similarity	NPD9494	Approved
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7037	Intermediate Similarity	NPD5408	Approved
0.7037	Intermediate Similarity	NPD5405	Approved
0.7037	Intermediate Similarity	NPD5404	Approved
0.7037	Intermediate Similarity	NPD5406	Approved
0.7035	Intermediate Similarity	NPD3817	Phase 2
0.7032	Intermediate Similarity	NPD1203	Approved
0.7031	Intermediate Similarity	NPD7870	Phase 2
0.7031	Intermediate Similarity	NPD7871	Phase 2
0.7025	Intermediate Similarity	NPD3268	Approved
0.7025	Intermediate Similarity	NPD3764	Approved
0.7022	Intermediate Similarity	NPD2163	Approved
0.7022	Intermediate Similarity	NPD3751	Discontinued
0.702	Intermediate Similarity	NPD5691	Approved
0.7017	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6832	Phase 2
0.7	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6002	Phase 3
0.6994	Remote Similarity	NPD6005	Phase 3
0.6994	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6004	Phase 3
0.6993	Remote Similarity	NPD1611	Approved
0.6989	Remote Similarity	NPD7229	Phase 3
0.6983	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7286	Phase 2
0.6975	Remote Similarity	NPD7033	Discontinued
0.6974	Remote Similarity	NPD17	Approved
0.6968	Remote Similarity	NPD1876	Approved
0.6961	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD9545	Approved
0.6944	Remote Similarity	NPD7074	Phase 3
0.6944	Remote Similarity	NPD1729	Discontinued
0.6941	Remote Similarity	NPD7458	Discontinued
0.6937	Remote Similarity	NPD2979	Phase 3
0.6928	Remote Similarity	NPD3496	Discontinued
0.6923	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7701	Phase 2
0.6915	Remote Similarity	NPD6534	Approved
0.6915	Remote Similarity	NPD6535	Approved
0.6911	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7054	Approved
0.6883	Remote Similarity	NPD1281	Approved
0.6879	Remote Similarity	NPD1465	Phase 2
0.6871	Remote Similarity	NPD3748	Approved
0.6871	Remote Similarity	NPD4308	Phase 3
0.6868	Remote Similarity	NPD6764	Approved
0.6868	Remote Similarity	NPD6765	Approved
0.6867	Remote Similarity	NPD6671	Approved
0.6862	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6212	Phase 3
0.6862	Remote Similarity	NPD6213	Phase 3
0.6859	Remote Similarity	NPD8285	Discontinued
0.6853	Remote Similarity	NPD7874	Approved
0.6853	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6651	Approved
0.6851	Remote Similarity	NPD7472	Approved
0.6846	Remote Similarity	NPD1398	Phase 1
0.6839	Remote Similarity	NPD6823	Phase 2
0.6832	Remote Similarity	NPD4060	Phase 1
0.6829	Remote Similarity	NPD4476	Approved
0.6829	Remote Similarity	NPD4477	Approved
0.6824	Remote Similarity	NPD5403	Approved
0.6821	Remote Similarity	NPD9493	Approved
0.6821	Remote Similarity	NPD7340	Approved
0.6818	Remote Similarity	NPD7801	Approved
0.6818	Remote Similarity	NPD7783	Phase 2
0.6818	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2797	Approved
0.6813	Remote Similarity	NPD6797	Phase 2
0.6813	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7699	Phase 2

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