NPASS Compound

Structure

CID33717 OpenBabel06191715362D 27 28 0 0 0 0 0 0 0 0999 V2000 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 -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 2.5981 1.5000 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 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 17 2 0 0 0 0 10 18 1 0 0 0 0 11 18 2 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 14 22 2 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 21 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 22 27 1 0 0 0 0 23 25 1 0 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.22
Volume:	411.826
LogP:	6.362
LogD:	4.802
LogS:	-4.712
# Rotatable Bonds:	8
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.431
Synthetic Accessibility Score:	2.812
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.794
MDCK Permeability:	2.6489762603887357e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.066
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.078
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	98.49502563476562%
Volume Distribution (VD):	0.536
Pgp-substrate:	1.3200900554656982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.932
CYP1A2-substrate:	0.226
CYP2C19-inhibitor:	0.844
CYP2C19-substrate:	0.121
CYP2C9-inhibitor:	0.919
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.378
CYP2D6-substrate:	0.804
CYP3A4-inhibitor:	0.447
CYP3A4-substrate:	0.117

ADMET: Excretion

Clearance (CL):	2.788
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.921
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.18
Skin Sensitization:	0.953
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.124
Respiratory Toxicity:	0.05

Download Data

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

Natural Product: NPC33717

Natural Product ID:	NPC33717
*Common Name:**	4-Hydroxy-3-[(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-Trienyl]Chromen-2-One
IUPAC Name:	4-hydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]chromen-2-one
Synonyms:
Standard InCHIKey:	NJJDBBUWWOAOLD-CFBAGHHKSA-N
Standard InCHI:	InChI=1S/C24H30O3/c1-17(2)9-7-10-18(3)11-8-12-19(4)15-16-21-23(25)20-13-5-6-14-22(20)27-24(21)26/h5-6,9,11,13-15,25H,7-8,10,12,16H2,1-4H3/b18-11+,19-15+
SMILES:	C/C(=CCc1c(=O)oc2c(c1O)cccc2)/CC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL268393
PubChem CID:	54679300
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	DOI[10.1016/0045-6535(91)90110-Y]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO163	Daucus carota	Species	Apiaceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1176	Organism	Mycobacterium fortuitum	Mycobacterium fortuitum	MIC	=	2.0	ug.mL-1	PMID[500870]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	0.5	ug.mL-1	PMID[500870]

☑ 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 NPC33717 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	322
0.1-0.2	1714
0.2-0.3	4647
0.3-0.4	10686
0.4-0.5	7464
0.5-0.6	4903
0.6-0.7	6322
0.7-0.8	5184
0.8-0.85	1120
0.85-0.9	284
0.9-0.95	46
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC31314
0.9643	High Similarity	NPC193193
0.9643	High Similarity	NPC474874
0.9444	High Similarity	NPC141068
0.9	High Similarity	NPC149545
0.8908	High Similarity	NPC229113
0.8852	High Similarity	NPC238309
0.8852	High Similarity	NPC474289
0.8814	High Similarity	NPC52247
0.8807	High Similarity	NPC139891
0.878	High Similarity	NPC2989
0.8739	High Similarity	NPC311219
0.8707	High Similarity	NPC263754
0.8707	High Similarity	NPC183154
0.8689	High Similarity	NPC121740
0.8689	High Similarity	NPC243688
0.8689	High Similarity	NPC224774
0.8689	High Similarity	NPC258567
0.8655	High Similarity	NPC187868
0.8644	High Similarity	NPC247553
0.8644	High Similarity	NPC14177
0.8636	High Similarity	NPC227255
0.8621	High Similarity	NPC128633
0.8621	High Similarity	NPC163398
0.8618	High Similarity	NPC469453
0.8596	High Similarity	NPC266116
0.8595	High Similarity	NPC89630
0.8571	High Similarity	NPC302107
0.8571	High Similarity	NPC235190
0.8571	High Similarity	NPC180006
0.8559	High Similarity	NPC264976
0.8537	High Similarity	NPC95034
0.8537	High Similarity	NPC142087
0.8525	High Similarity	NPC244495
0.8525	High Similarity	NPC93219
0.8512	High Similarity	NPC248786
0.848	Intermediate Similarity	NPC32463
0.8475	Intermediate Similarity	NPC265547
0.8475	Intermediate Similarity	NPC152306
0.8475	Intermediate Similarity	NPC96705
0.8448	Intermediate Similarity	NPC114144
0.8448	Intermediate Similarity	NPC87563
0.843	Intermediate Similarity	NPC302211
0.8417	Intermediate Similarity	NPC163200
0.8403	Intermediate Similarity	NPC281356
0.8403	Intermediate Similarity	NPC298796
0.8376	Intermediate Similarity	NPC51345
0.8374	Intermediate Similarity	NPC168259
0.8372	Intermediate Similarity	NPC246177
0.8372	Intermediate Similarity	NPC317045
0.8361	Intermediate Similarity	NPC109675
0.8361	Intermediate Similarity	NPC273772
0.8348	Intermediate Similarity	NPC233238
0.8347	Intermediate Similarity	NPC476165
0.8333	Intermediate Similarity	NPC230951
0.8333	Intermediate Similarity	NPC113098
0.832	Intermediate Similarity	NPC157212
0.832	Intermediate Similarity	NPC185066
0.8319	Intermediate Similarity	NPC157473
0.8319	Intermediate Similarity	NPC151530
0.8304	Intermediate Similarity	NPC473393
0.8295	Intermediate Similarity	NPC281169
0.8295	Intermediate Similarity	NPC291119
0.8293	Intermediate Similarity	NPC27671
0.8293	Intermediate Similarity	NPC201667
0.8293	Intermediate Similarity	NPC73413
0.8281	Intermediate Similarity	NPC31849
0.8279	Intermediate Similarity	NPC248429
0.8279	Intermediate Similarity	NPC96286
0.8276	Intermediate Similarity	NPC199462
0.8276	Intermediate Similarity	NPC474920
0.8273	Intermediate Similarity	NPC107101
0.8268	Intermediate Similarity	NPC272650
0.8268	Intermediate Similarity	NPC29734
0.8268	Intermediate Similarity	NPC267336
0.8264	Intermediate Similarity	NPC307253
0.8254	Intermediate Similarity	NPC187907
0.825	Intermediate Similarity	NPC98748
0.8244	Intermediate Similarity	NPC327612
0.8244	Intermediate Similarity	NPC73078
0.8244	Intermediate Similarity	NPC148738
0.8244	Intermediate Similarity	NPC319870
0.8235	Intermediate Similarity	NPC45104
0.823	Intermediate Similarity	NPC176971
0.8226	Intermediate Similarity	NPC4164
0.8226	Intermediate Similarity	NPC88403
0.822	Intermediate Similarity	NPC296526
0.8217	Intermediate Similarity	NPC131950
0.8214	Intermediate Similarity	NPC2518
0.8214	Intermediate Similarity	NPC109637
0.8211	Intermediate Similarity	NPC472518
0.8211	Intermediate Similarity	NPC315807
0.8203	Intermediate Similarity	NPC317601
0.8203	Intermediate Similarity	NPC307289
0.8203	Intermediate Similarity	NPC329427
0.8198	Intermediate Similarity	NPC307425
0.8189	Intermediate Similarity	NPC86774
0.8189	Intermediate Similarity	NPC327457
0.8182	Intermediate Similarity	NPC71903
0.8175	Intermediate Similarity	NPC472519
0.8175	Intermediate Similarity	NPC2401
0.8175	Intermediate Similarity	NPC81261
0.8174	Intermediate Similarity	NPC259554
0.8168	Intermediate Similarity	NPC471069
0.8168	Intermediate Similarity	NPC471068
0.8154	Intermediate Similarity	NPC161856
0.8154	Intermediate Similarity	NPC51087
0.8154	Intermediate Similarity	NPC61499
0.8145	Intermediate Similarity	NPC474237
0.8145	Intermediate Similarity	NPC193805
0.8145	Intermediate Similarity	NPC291899
0.8145	Intermediate Similarity	NPC140521
0.8145	Intermediate Similarity	NPC98509
0.8145	Intermediate Similarity	NPC221798
0.8142	Intermediate Similarity	NPC128730
0.8142	Intermediate Similarity	NPC127676
0.8142	Intermediate Similarity	NPC288760
0.8142	Intermediate Similarity	NPC473855
0.814	Intermediate Similarity	NPC469449
0.814	Intermediate Similarity	NPC2363
0.8136	Intermediate Similarity	NPC235250
0.813	Intermediate Similarity	NPC13007
0.813	Intermediate Similarity	NPC257188
0.812	Intermediate Similarity	NPC310370
0.812	Intermediate Similarity	NPC170812
0.812	Intermediate Similarity	NPC183642
0.812	Intermediate Similarity	NPC280760
0.8115	Intermediate Similarity	NPC322569
0.8115	Intermediate Similarity	NPC319378
0.8106	Intermediate Similarity	NPC471070
0.8106	Intermediate Similarity	NPC151946
0.8106	Intermediate Similarity	NPC471071
0.8106	Intermediate Similarity	NPC471072
0.8103	Intermediate Similarity	NPC473809
0.8099	Intermediate Similarity	NPC137294
0.8099	Intermediate Similarity	NPC90522
0.8099	Intermediate Similarity	NPC328459
0.8099	Intermediate Similarity	NPC85895
0.8099	Intermediate Similarity	NPC43435
0.8092	Intermediate Similarity	NPC223616
0.8092	Intermediate Similarity	NPC26954
0.8092	Intermediate Similarity	NPC38099
0.8083	Intermediate Similarity	NPC217423
0.808	Intermediate Similarity	NPC232692
0.808	Intermediate Similarity	NPC202594
0.808	Intermediate Similarity	NPC249836
0.808	Intermediate Similarity	NPC471827
0.808	Intermediate Similarity	NPC471828
0.8077	Intermediate Similarity	NPC326600
0.8077	Intermediate Similarity	NPC204353
0.8077	Intermediate Similarity	NPC50896
0.807	Intermediate Similarity	NPC326447
0.8067	Intermediate Similarity	NPC188907
0.8067	Intermediate Similarity	NPC473718
0.8062	Intermediate Similarity	NPC194277
0.8062	Intermediate Similarity	NPC281558
0.8053	Intermediate Similarity	NPC283546
0.8049	Intermediate Similarity	NPC144418
0.8033	Intermediate Similarity	NPC72977
0.8033	Intermediate Similarity	NPC470092
0.8033	Intermediate Similarity	NPC168050
0.8031	Intermediate Similarity	NPC219923
0.803	Intermediate Similarity	NPC155963
0.8017	Intermediate Similarity	NPC234639
0.8017	Intermediate Similarity	NPC293424
0.8017	Intermediate Similarity	NPC94637
0.8016	Intermediate Similarity	NPC101894
0.8016	Intermediate Similarity	NPC474476
0.8016	Intermediate Similarity	NPC329272
0.8	Intermediate Similarity	NPC128825
0.8	Intermediate Similarity	NPC111347
0.8	Intermediate Similarity	NPC19290
0.8	Intermediate Similarity	NPC265910
0.8	Intermediate Similarity	NPC6888
0.8	Intermediate Similarity	NPC78446
0.8	Intermediate Similarity	NPC83535
0.8	Intermediate Similarity	NPC91475
0.8	Intermediate Similarity	NPC163557
0.8	Intermediate Similarity	NPC194034
0.7985	Intermediate Similarity	NPC195357
0.7985	Intermediate Similarity	NPC155552
0.7985	Intermediate Similarity	NPC152771
0.7984	Intermediate Similarity	NPC477151
0.7984	Intermediate Similarity	NPC69403
0.7984	Intermediate Similarity	NPC132518
0.7984	Intermediate Similarity	NPC250727
0.7984	Intermediate Similarity	NPC291189
0.7982	Intermediate Similarity	NPC470393
0.797	Intermediate Similarity	NPC164148
0.797	Intermediate Similarity	NPC332594
0.797	Intermediate Similarity	NPC211110
0.797	Intermediate Similarity	NPC279573
0.797	Intermediate Similarity	NPC221046
0.797	Intermediate Similarity	NPC43500
0.7969	Intermediate Similarity	NPC168710
0.7967	Intermediate Similarity	NPC218753
0.7965	Intermediate Similarity	NPC179686
0.7965	Intermediate Similarity	NPC192596
0.7955	Intermediate Similarity	NPC115861
0.7953	Intermediate Similarity	NPC473993

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 NPC33717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	977
0.2-0.3	1453
0.3-0.4	2573
0.4-0.5	2047
0.5-0.6	1221
0.6-0.7	403
0.7-0.8	127
0.8-0.85	31
0.85-0.9	9
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9153	High Similarity	NPD2797	Approved
0.8908	High Similarity	NPD3225	Approved
0.8814	High Similarity	NPD422	Phase 1
0.8807	High Similarity	NPD9697	Approved
0.878	High Similarity	NPD3268	Approved
0.8739	High Similarity	NPD9717	Approved
0.8525	High Similarity	NPD1203	Approved
0.8374	Intermediate Similarity	NPD3267	Approved
0.8374	Intermediate Similarity	NPD3266	Approved
0.8264	Intermediate Similarity	NPD3496	Discontinued
0.8231	Intermediate Similarity	NPD4308	Phase 3
0.8182	Intermediate Similarity	NPD1778	Approved
0.8175	Intermediate Similarity	NPD6832	Phase 2
0.812	Intermediate Similarity	NPD5535	Approved
0.807	Intermediate Similarity	NPD3134	Approved
0.8047	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD411	Approved
0.8	Intermediate Similarity	NPD9493	Approved
0.8	Intermediate Similarity	NPD447	Suspended
0.8	Intermediate Similarity	NPD290	Approved
0.7923	Intermediate Similarity	NPD4307	Phase 2
0.7917	Intermediate Similarity	NPD6671	Approved
0.7891	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD4626	Approved
0.7874	Intermediate Similarity	NPD1019	Discontinued
0.7869	Intermediate Similarity	NPD1894	Discontinued
0.7863	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD5124	Phase 1
0.7845	Intermediate Similarity	NPD1358	Approved
0.782	Intermediate Similarity	NPD7033	Discontinued
0.7805	Intermediate Similarity	NPD5585	Approved
0.7769	Intermediate Similarity	NPD1296	Phase 2
0.7769	Intermediate Similarity	NPD6798	Discontinued
0.7769	Intermediate Similarity	NPD2313	Discontinued
0.776	Intermediate Similarity	NPD1535	Discovery
0.7759	Intermediate Similarity	NPD968	Approved
0.775	Intermediate Similarity	NPD1241	Discontinued
0.7727	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1548	Phase 1
0.7698	Intermediate Similarity	NPD1481	Phase 2
0.7698	Intermediate Similarity	NPD1608	Approved
0.7687	Intermediate Similarity	NPD2799	Discontinued
0.768	Intermediate Similarity	NPD3847	Discontinued
0.7664	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD3750	Approved
0.7661	Intermediate Similarity	NPD5691	Approved
0.7634	Intermediate Similarity	NPD1048	Approved
0.763	Intermediate Similarity	NPD1551	Phase 2
0.763	Intermediate Similarity	NPD2935	Discontinued
0.7627	Intermediate Similarity	NPD2684	Approved
0.7619	Intermediate Similarity	NPD1091	Approved
0.7615	Intermediate Similarity	NPD2614	Approved
0.7597	Intermediate Similarity	NPD2798	Approved
0.7594	Intermediate Similarity	NPD6355	Discontinued
0.7594	Intermediate Similarity	NPD1933	Approved
0.7591	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1652	Phase 2
0.7576	Intermediate Similarity	NPD6233	Phase 2
0.7557	Intermediate Similarity	NPD7095	Approved
0.7542	Intermediate Similarity	NPD9267	Approved
0.7542	Intermediate Similarity	NPD9263	Approved
0.7542	Intermediate Similarity	NPD9264	Approved
0.7519	Intermediate Similarity	NPD4060	Phase 1
0.7519	Intermediate Similarity	NPD6362	Approved
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD4359	Approved
0.748	Intermediate Similarity	NPD1611	Approved
0.7479	Intermediate Similarity	NPD74	Approved
0.7479	Intermediate Similarity	NPD9266	Approved
0.746	Intermediate Similarity	NPD17	Approved
0.7444	Intermediate Similarity	NPD4062	Phase 3
0.744	Intermediate Similarity	NPD9545	Approved
0.7426	Intermediate Similarity	NPD3748	Approved
0.7424	Intermediate Similarity	NPD5163	Phase 2
0.741	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6653	Approved
0.7391	Intermediate Similarity	NPD2424	Discontinued
0.7391	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7843	Approved
0.7377	Intermediate Similarity	NPD821	Approved
0.7376	Intermediate Similarity	NPD6799	Approved
0.7372	Intermediate Similarity	NPD4476	Approved
0.7372	Intermediate Similarity	NPD6032	Approved
0.7372	Intermediate Similarity	NPD4477	Approved
0.7364	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7097	Phase 1
0.7348	Intermediate Similarity	NPD4908	Phase 1
0.7344	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1610	Phase 2
0.7343	Intermediate Similarity	NPD5403	Approved
0.7333	Intermediate Similarity	NPD4340	Discontinued
0.7328	Intermediate Similarity	NPD5647	Approved
0.7324	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6004	Phase 3
0.7319	Intermediate Similarity	NPD6002	Phase 3
0.7319	Intermediate Similarity	NPD2346	Discontinued
0.7319	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6005	Phase 3
0.7319	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4625	Phase 3
0.7288	Intermediate Similarity	NPD5909	Discontinued
0.7286	Intermediate Similarity	NPD4628	Phase 3
0.726	Intermediate Similarity	NPD7411	Suspended
0.7259	Intermediate Similarity	NPD4140	Approved
0.7259	Intermediate Similarity	NPD1240	Approved
0.7252	Intermediate Similarity	NPD987	Approved
0.7246	Intermediate Similarity	NPD2796	Approved
0.7246	Intermediate Similarity	NPD2862	Discontinued
0.7246	Intermediate Similarity	NPD6099	Approved
0.7246	Intermediate Similarity	NPD6100	Approved
0.7241	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5536	Phase 2
0.7214	Intermediate Similarity	NPD1243	Approved
0.7206	Intermediate Similarity	NPD4622	Approved
0.7206	Intermediate Similarity	NPD4618	Approved
0.7206	Intermediate Similarity	NPD1184	Approved
0.7203	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5401	Approved
0.7203	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9261	Approved
0.7203	Intermediate Similarity	NPD1578	Phase 2
0.72	Intermediate Similarity	NPD2557	Approved
0.72	Intermediate Similarity	NPD7157	Approved
0.7194	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2344	Approved
0.7193	Intermediate Similarity	NPD2934	Approved
0.7193	Intermediate Similarity	NPD2933	Approved
0.7185	Intermediate Similarity	NPD8032	Phase 2
0.7183	Intermediate Similarity	NPD6666	Approved
0.7183	Intermediate Similarity	NPD6667	Approved
0.7176	Intermediate Similarity	NPD1283	Approved
0.7172	Intermediate Similarity	NPD1653	Approved
0.7163	Intermediate Similarity	NPD7003	Approved
0.7153	Intermediate Similarity	NPD1607	Approved
0.7143	Intermediate Similarity	NPD454	Approved
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD2237	Approved
0.7132	Intermediate Similarity	NPD2203	Discontinued
0.713	Intermediate Similarity	NPD2859	Approved
0.713	Intermediate Similarity	NPD2860	Approved
0.7123	Intermediate Similarity	NPD3226	Approved
0.712	Intermediate Similarity	NPD9281	Approved
0.7119	Intermediate Similarity	NPD940	Approved
0.7119	Intermediate Similarity	NPD846	Approved
0.7111	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5689	Approved
0.7101	Intermediate Similarity	NPD5688	Approved
0.7099	Intermediate Similarity	NPD6583	Phase 3
0.7099	Intermediate Similarity	NPD6582	Phase 2
0.7095	Intermediate Similarity	NPD6801	Discontinued
0.7087	Intermediate Similarity	NPD1758	Phase 1
0.7087	Intermediate Similarity	NPD7644	Approved
0.7075	Intermediate Similarity	NPD6502	Phase 2
0.7075	Intermediate Similarity	NPD6599	Discontinued
0.7071	Intermediate Similarity	NPD5763	Approved
0.7071	Intermediate Similarity	NPD5762	Approved
0.7071	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3690	Phase 2
0.7068	Intermediate Similarity	NPD3691	Phase 2
0.7067	Intermediate Similarity	NPD7768	Phase 2
0.7063	Intermediate Similarity	NPD709	Approved
0.7063	Intermediate Similarity	NPD7440	Discontinued
0.7059	Intermediate Similarity	NPD4870	Approved
0.7054	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1510	Phase 2
0.7047	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7819	Suspended
0.7042	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3251	Approved
0.7034	Intermediate Similarity	NPD6273	Approved
0.7034	Intermediate Similarity	NPD5049	Phase 3
0.7031	Intermediate Similarity	NPD2486	Discontinued
0.7031	Intermediate Similarity	NPD1759	Phase 1
0.7027	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2366	Approved
0.7027	Intermediate Similarity	NPD1282	Approved
0.7023	Intermediate Similarity	NPD3972	Approved
0.7023	Intermediate Similarity	NPD2235	Phase 2
0.7023	Intermediate Similarity	NPD2231	Phase 2
0.7021	Intermediate Similarity	NPD4534	Discontinued
0.7021	Intermediate Similarity	NPD7974	Phase 3
0.702	Intermediate Similarity	NPD7075	Discontinued
0.7016	Intermediate Similarity	NPD228	Approved
0.7015	Intermediate Similarity	NPD2861	Phase 2
0.7014	Intermediate Similarity	NPD1511	Approved
0.7014	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5402	Approved
0.7	Intermediate Similarity	NPD3817	Phase 2
0.6993	Remote Similarity	NPD2354	Approved
0.6993	Remote Similarity	NPD2309	Approved
0.6992	Remote Similarity	NPD5451	Approved
0.6983	Remote Similarity	NPD844	Approved
0.6978	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3444	Approved
0.6977	Remote Similarity	NPD3443	Approved
0.6977	Remote Similarity	NPD3049	Approved
0.6977	Remote Similarity	NPD3445	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data