NPASS Compound

Structure

CID162939 OpenBabel06191715532D 23 23 0 0 1 0 0 0 0 0999 V2000 -3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 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 -2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 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 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 -1.7321 -7.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 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 0.8660 -1.5000 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 0.0000 -1.0000 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 -0.0000 0.0000 C 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 -0.8660 -2.5000 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 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 13 2 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 11 20 2 0 0 0 0 12 2 1 1 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 16 21 2 0 0 0 0 17 19 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.17
Volume:	345.329
LogP:	3.28
LogD:	1.944
LogS:	-2.438
# Rotatable Bonds:	7
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	3.398
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.97
MDCK Permeability:	1.66006175277289e-05
Pgp-inhibitor:	0.294
Pgp-substrate:	0.324
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.784
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.446
Plasma Protein Binding (PPB):	95.14250946044922%
Volume Distribution (VD):	0.924
Pgp-substrate:	2.3758678436279297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.777
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.553
CYP2C19-substrate:	0.365
CYP2C9-inhibitor:	0.772
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.644
CYP2D6-substrate:	0.711
CYP3A4-inhibitor:	0.445
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	5.712
Half-life (T1/2):	0.938

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.201
Drug-inuced Liver Injury (DILI):	0.209
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.886
Carcinogencity:	0.13
Eye Corrosion:	0.224
Eye Irritation:	0.854
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC162939

Natural Product ID:	NPC162939
*Common Name:**	6-[(3E,5E,7S)-5,7-Dimethyl-2-Oxonona-3,5-Dienyl]-2,4-Dihydroxy-3-Methylbenzaldehyde
IUPAC Name:	6-[(3E,5E,7S)-5,7-dimethyl-2-oxonona-3,5-dienyl]-2,4-dihydroxy-3-methylbenzaldehyde
Synonyms:
Standard InCHIKey:	SRUILBLGVMJFPG-YDROHTJRSA-N
Standard InCHI:	InChI=1S/C19H24O4/c1-5-12(2)8-13(3)6-7-16(21)9-15-10-18(22)14(4)19(23)17(15)11-20/h6-8,10-12,22-23H,5,9H2,1-4H3/b7-6+,13-8+/t12-/m0/s1
SMILES:	CC[C@H](C)/C=C(C)/C=C/C(=O)Cc1cc(c(C)c(c1C=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1456313
PubChem CID:	16745396
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000124] Aldehydes [CHEMONTID:0003213] Aryl-aldehydes [CHEMONTID:0001345] Benzaldehydes [CHEMONTID:0003978] Hydroxybenzaldehydes

*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
NPO13628	Rabdosia longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13628	Rabdosia longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14633	Tridacna maxima	Species	Tridacnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13628	Rabdosia longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10933	Stenanthera gabonensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15729	Streptomyces karnatakensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7875	Pseudocyphellaria berberina	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16003	Machaerium incorruptibile	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3508	Aglaia tenuicaulis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20456	Chrysanthemum tatsienense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5308	Stilpnopappus trichospiroides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9160	Plantago nivalis	Species	Plantaginaceae	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
EC50	1
Potency	26

Activity Type	# Activity
Individual Protein	21
Organism	2
Others	1
PROTEIN COMPLEX	3
Protein-Protein Interaction	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	31622.8	nM	PMID[567768]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	35481.3	nM	PMID[567768]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	39810.7	nM	PMID[567768]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	28183.8	nM	PMID[567768]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	89125.1	nM	PMID[567768]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	35481.3	nM	PMID[567768]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[567768]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	794.3	nM	PMID[567768]
NPT1415	Individual Protein	Heat shock factor protein 1	Mus musculus	EC50	=	27470.0	nM	PMID[567768]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[567768]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[567768]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[567768]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[567768]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[567768]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[567768]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[567768]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[567768]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	28183.8	nM	PMID[567768]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[567768]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	8275.3	nM	PMID[567768]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[567768]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	70794.6	nM	PMID[567768]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[567768]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[567768]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	13115.4	nM	PMID[567768]
NPT2	Others	Unspecified		Potency	n.a.	31622.8	nM	PMID[567768]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[567768]

☑ 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 NPC162939 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	351
0.1-0.2	1521
0.2-0.3	3634
0.3-0.4	10195
0.4-0.5	9300
0.5-0.6	4822
0.6-0.7	7187
0.7-0.8	4881
0.8-0.85	601
0.85-0.9	187
0.9-0.95	15
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9621	High Similarity	NPC474519
0.9318	High Similarity	NPC62219
0.9259	High Similarity	NPC278375
0.9209	High Similarity	NPC193555
0.9209	High Similarity	NPC73061
0.9111	High Similarity	NPC48036
0.9065	High Similarity	NPC181560
0.9065	High Similarity	NPC169452
0.9044	High Similarity	NPC282780
0.9044	High Similarity	NPC166480
0.9	High Similarity	NPC187843
0.8993	High Similarity	NPC138099
0.8993	High Similarity	NPC242994
0.8978	High Similarity	NPC290803
0.8971	High Similarity	NPC37299
0.8971	High Similarity	NPC180261
0.8963	High Similarity	NPC275504
0.8939	High Similarity	NPC477454
0.8936	High Similarity	NPC135524
0.8929	High Similarity	NPC99441
0.8921	High Similarity	NPC472403
0.8921	High Similarity	NPC177307
0.8921	High Similarity	NPC9121
0.8913	High Similarity	NPC191976
0.8913	High Similarity	NPC118919
0.8913	High Similarity	NPC86524
0.8905	High Similarity	NPC474394
0.8872	High Similarity	NPC473691
0.8865	High Similarity	NPC204045
0.8865	High Similarity	NPC305845
0.8865	High Similarity	NPC37530
0.8849	High Similarity	NPC65837
0.8849	High Similarity	NPC474771
0.8849	High Similarity	NPC53414
0.8849	High Similarity	NPC474849
0.8849	High Similarity	NPC471905
0.8849	High Similarity	NPC149372
0.8849	High Similarity	NPC178467
0.8849	High Similarity	NPC53206
0.8832	High Similarity	NPC267205
0.8824	High Similarity	NPC41847
0.8815	High Similarity	NPC92624
0.8815	High Similarity	NPC109123
0.8815	High Similarity	NPC476119
0.8811	High Similarity	NPC193703
0.8811	High Similarity	NPC21599
0.8803	High Similarity	NPC474961
0.8797	High Similarity	NPC475733
0.8794	High Similarity	NPC183345
0.8788	High Similarity	NPC65761
0.8788	High Similarity	NPC472029
0.8788	High Similarity	NPC306288
0.8786	High Similarity	NPC475974
0.8784	High Similarity	NPC208806
0.8777	High Similarity	NPC254847
0.8759	High Similarity	NPC175738
0.875	High Similarity	NPC247477
0.875	High Similarity	NPC259942
0.875	High Similarity	NPC34482
0.875	High Similarity	NPC17840
0.8741	High Similarity	NPC474203
0.8741	High Similarity	NPC313047
0.8741	High Similarity	NPC295712
0.8741	High Similarity	NPC473017
0.8741	High Similarity	NPC41263
0.8741	High Similarity	NPC451542
0.8732	High Similarity	NPC313123
0.8732	High Similarity	NPC478217
0.8732	High Similarity	NPC478201
0.8732	High Similarity	NPC472035
0.8723	High Similarity	NPC190457
0.8712	High Similarity	NPC218333
0.8712	High Similarity	NPC309765
0.8712	High Similarity	NPC91105
0.8696	High Similarity	NPC213485
0.8696	High Similarity	NPC40524
0.8696	High Similarity	NPC139074
0.8696	High Similarity	NPC477139
0.869	High Similarity	NPC470570
0.8686	High Similarity	NPC475042
0.8681	High Similarity	NPC151607
0.8681	High Similarity	NPC42540
0.8681	High Similarity	NPC471906
0.8681	High Similarity	NPC48762
0.8681	High Similarity	NPC244691
0.8676	High Similarity	NPC474998
0.8667	High Similarity	NPC105157
0.8667	High Similarity	NPC190043
0.8667	High Similarity	NPC266689
0.8667	High Similarity	NPC100067
0.8667	High Similarity	NPC98254
0.8667	High Similarity	NPC30501
0.8667	High Similarity	NPC103356
0.8667	High Similarity	NPC72158
0.8667	High Similarity	NPC23126
0.8667	High Similarity	NPC169250
0.8667	High Similarity	NPC162612
0.8643	High Similarity	NPC158481
0.8636	High Similarity	NPC303737
0.8636	High Similarity	NPC215392
0.8636	High Similarity	NPC226275
0.8633	High Similarity	NPC44437
0.8621	High Similarity	NPC12402
0.8611	High Similarity	NPC174905
0.8611	High Similarity	NPC159721
0.8611	High Similarity	NPC478202
0.8611	High Similarity	NPC293545
0.8603	High Similarity	NPC21305
0.8603	High Similarity	NPC3009
0.8603	High Similarity	NPC221777
0.8601	High Similarity	NPC246638
0.8601	High Similarity	NPC290550
0.8593	High Similarity	NPC267846
0.8593	High Similarity	NPC62952
0.8592	High Similarity	NPC143438
0.8592	High Similarity	NPC474655
0.8582	High Similarity	NPC222633
0.8582	High Similarity	NPC290030
0.8582	High Similarity	NPC194579
0.8582	High Similarity	NPC471452
0.8582	High Similarity	NPC53001
0.8582	High Similarity	NPC71256
0.8571	High Similarity	NPC475917
0.8571	High Similarity	NPC283590
0.8571	High Similarity	NPC61153
0.8571	High Similarity	NPC70859
0.8571	High Similarity	NPC130899
0.8561	High Similarity	NPC115458
0.8561	High Similarity	NPC146642
0.8561	High Similarity	NPC149246
0.8552	High Similarity	NPC126882
0.8552	High Similarity	NPC210966
0.8552	High Similarity	NPC478203
0.8551	High Similarity	NPC85342
0.8542	High Similarity	NPC291078
0.8542	High Similarity	NPC137649
0.8531	High Similarity	NPC109232
0.8529	High Similarity	NPC116513
0.8521	High Similarity	NPC4214
0.8521	High Similarity	NPC191835
0.8521	High Similarity	NPC33144
0.8521	High Similarity	NPC478200
0.8521	High Similarity	NPC87723
0.8521	High Similarity	NPC13715
0.8521	High Similarity	NPC123714
0.8519	High Similarity	NPC262671
0.8519	High Similarity	NPC201728
0.8514	High Similarity	NPC477221
0.8514	High Similarity	NPC329933
0.8511	High Similarity	NPC65005
0.8511	High Similarity	NPC264112
0.8511	High Similarity	NPC194764
0.8503	High Similarity	NPC290194
0.85	High Similarity	NPC12070
0.85	High Similarity	NPC474117
0.85	High Similarity	NPC474224
0.8493	Intermediate Similarity	NPC257558
0.8493	Intermediate Similarity	NPC472034
0.8485	Intermediate Similarity	NPC294964
0.8485	Intermediate Similarity	NPC294037
0.8483	Intermediate Similarity	NPC354984
0.8483	Intermediate Similarity	NPC471731
0.8483	Intermediate Similarity	NPC84266
0.8478	Intermediate Similarity	NPC147757
0.8472	Intermediate Similarity	NPC110810
0.8472	Intermediate Similarity	NPC470842
0.8472	Intermediate Similarity	NPC472603
0.8472	Intermediate Similarity	NPC472904
0.8462	Intermediate Similarity	NPC92655
0.8462	Intermediate Similarity	NPC472903
0.8456	Intermediate Similarity	NPC227741
0.8456	Intermediate Similarity	NPC295202
0.8456	Intermediate Similarity	NPC255641
0.8456	Intermediate Similarity	NPC470568
0.8456	Intermediate Similarity	NPC290954
0.8456	Intermediate Similarity	NPC473751
0.8456	Intermediate Similarity	NPC160499
0.8456	Intermediate Similarity	NPC136342
0.8456	Intermediate Similarity	NPC49647
0.8456	Intermediate Similarity	NPC8745
0.8451	Intermediate Similarity	NPC70380
0.8444	Intermediate Similarity	NPC13238
0.844	Intermediate Similarity	NPC161632
0.844	Intermediate Similarity	NPC249272
0.844	Intermediate Similarity	NPC470210
0.844	Intermediate Similarity	NPC474076
0.8435	Intermediate Similarity	NPC225173
0.8435	Intermediate Similarity	NPC110882
0.8435	Intermediate Similarity	NPC143685
0.8435	Intermediate Similarity	NPC163846
0.8435	Intermediate Similarity	NPC271944
0.8435	Intermediate Similarity	NPC472033
0.8435	Intermediate Similarity	NPC85393
0.8433	Intermediate Similarity	NPC282577
0.8429	Intermediate Similarity	NPC114183
0.8425	Intermediate Similarity	NPC227841
0.8414	Intermediate Similarity	NPC182255
0.8414	Intermediate Similarity	NPC49108
0.8414	Intermediate Similarity	NPC471733
0.8414	Intermediate Similarity	NPC94076

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 NPC162939 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	1002
0.2-0.3	1653
0.3-0.4	2846
0.4-0.5	1920
0.5-0.6	1006
0.6-0.7	315
0.7-0.8	86
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8777	High Similarity	NPD1509	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD7390	Discontinued
0.8125	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2533	Approved
0.8121	Intermediate Similarity	NPD2532	Approved
0.8121	Intermediate Similarity	NPD2534	Approved
0.8099	Intermediate Similarity	NPD943	Approved
0.8069	Intermediate Similarity	NPD5408	Approved
0.8069	Intermediate Similarity	NPD5405	Approved
0.8069	Intermediate Similarity	NPD5406	Approved
0.8069	Intermediate Similarity	NPD5404	Approved
0.7986	Intermediate Similarity	NPD1607	Approved
0.7986	Intermediate Similarity	NPD1470	Approved
0.7959	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD1201	Approved
0.7935	Intermediate Similarity	NPD7819	Suspended
0.7885	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1510	Phase 2
0.7847	Intermediate Similarity	NPD1240	Approved
0.7778	Intermediate Similarity	NPD7473	Discontinued
0.7763	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6959	Discontinued
0.7707	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6232	Discontinued
0.7692	Intermediate Similarity	NPD7411	Suspended
0.7647	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4380	Phase 2
0.7609	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1549	Phase 2
0.7584	Intermediate Similarity	NPD2935	Discontinued
0.7533	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6651	Approved
0.7483	Intermediate Similarity	NPD1164	Approved
0.7467	Intermediate Similarity	NPD2796	Approved
0.7467	Intermediate Similarity	NPD1551	Phase 2
0.7453	Intermediate Similarity	NPD7075	Discontinued
0.7452	Intermediate Similarity	NPD3226	Approved
0.7421	Intermediate Similarity	NPD1934	Approved
0.7405	Intermediate Similarity	NPD6599	Discontinued
0.7391	Intermediate Similarity	NPD3882	Suspended
0.7388	Intermediate Similarity	NPD4750	Phase 3
0.7378	Intermediate Similarity	NPD5710	Approved
0.7378	Intermediate Similarity	NPD5711	Approved
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6559	Discontinued
0.732	Intermediate Similarity	NPD2800	Approved
0.732	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD230	Phase 1
0.7305	Intermediate Similarity	NPD3019	Approved
0.7305	Intermediate Similarity	NPD2932	Approved
0.729	Intermediate Similarity	NPD3300	Phase 2
0.7285	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD9269	Phase 2
0.7273	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3750	Approved
0.7267	Intermediate Similarity	NPD2801	Approved
0.7266	Intermediate Similarity	NPD9493	Approved
0.7262	Intermediate Similarity	NPD6020	Phase 2
0.7262	Intermediate Similarity	NPD5844	Phase 1
0.7256	Intermediate Similarity	NPD5494	Approved
0.7244	Intermediate Similarity	NPD6799	Approved
0.7244	Intermediate Similarity	NPD1511	Approved
0.7237	Intermediate Similarity	NPD6100	Approved
0.7237	Intermediate Similarity	NPD6099	Approved
0.7234	Intermediate Similarity	NPD9268	Approved
0.7215	Intermediate Similarity	NPD920	Approved
0.7212	Intermediate Similarity	NPD1247	Approved
0.7205	Intermediate Similarity	NPD6801	Discontinued
0.719	Intermediate Similarity	NPD2346	Discontinued
0.7185	Intermediate Similarity	NPD9266	Approved
0.7185	Intermediate Similarity	NPD74	Approved
0.7179	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2799	Discontinued
0.7163	Intermediate Similarity	NPD9545	Approved
0.7161	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1512	Approved
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3749	Approved
0.7121	Intermediate Similarity	NPD940	Approved
0.7121	Intermediate Similarity	NPD846	Approved
0.7111	Intermediate Similarity	NPD9267	Approved
0.7111	Intermediate Similarity	NPD9264	Approved
0.7111	Intermediate Similarity	NPD9263	Approved
0.7111	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD919	Approved
0.7089	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6166	Phase 2
0.7063	Intermediate Similarity	NPD4626	Approved
0.7051	Intermediate Similarity	NPD7003	Approved
0.7029	Intermediate Similarity	NPD8150	Discontinued
0.7019	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7458	Discontinued
0.7012	Intermediate Similarity	NPD3817	Phase 2
0.7	Intermediate Similarity	NPD3818	Discontinued
0.6994	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1243	Approved
0.6978	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5953	Discontinued
0.6968	Remote Similarity	NPD2344	Approved
0.6966	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2798	Approved
0.6948	Remote Similarity	NPD3748	Approved
0.6943	Remote Similarity	NPD4628	Phase 3
0.6939	Remote Similarity	NPD1283	Approved
0.6919	Remote Similarity	NPD7074	Phase 3
0.6918	Remote Similarity	NPD3972	Approved
0.6913	Remote Similarity	NPD9494	Approved
0.6897	Remote Similarity	NPD3026	Approved
0.6897	Remote Similarity	NPD3023	Approved
0.6887	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD411	Approved
0.6887	Remote Similarity	NPD3764	Approved
0.6879	Remote Similarity	NPD9281	Approved
0.6879	Remote Similarity	NPD2654	Approved
0.6875	Remote Similarity	NPD1651	Approved
0.6875	Remote Similarity	NPD3024	Approved
0.6875	Remote Similarity	NPD3025	Approved
0.6875	Remote Similarity	NPD5691	Approved
0.6867	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7054	Approved
0.686	Remote Similarity	NPD7286	Phase 2
0.6859	Remote Similarity	NPD1471	Phase 3
0.6857	Remote Similarity	NPD7635	Approved
0.6846	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6663	Approved
0.6835	Remote Similarity	NPD8166	Discontinued
0.6835	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7472	Approved
0.6821	Remote Similarity	NPD4625	Phase 3
0.6818	Remote Similarity	NPD288	Approved
0.6815	Remote Similarity	NPD9261	Approved
0.6803	Remote Similarity	NPD9717	Approved
0.68	Remote Similarity	NPD5736	Approved
0.6796	Remote Similarity	NPD6535	Approved
0.6796	Remote Similarity	NPD6534	Approved
0.6792	Remote Similarity	NPD2309	Approved
0.6782	Remote Similarity	NPD6797	Phase 2
0.6776	Remote Similarity	NPD3268	Approved
0.6776	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5951	Approved
0.6761	Remote Similarity	NPD8313	Approved
0.6761	Remote Similarity	NPD8312	Approved
0.6761	Remote Similarity	NPD5035	Approved
0.676	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7251	Discontinued
0.6742	Remote Similarity	NPD844	Approved
0.6735	Remote Similarity	NPD1281	Approved
0.6725	Remote Similarity	NPD3926	Phase 2
0.6711	Remote Similarity	NPD1876	Approved
0.6707	Remote Similarity	NPD5402	Approved
0.6705	Remote Similarity	NPD7808	Phase 3
0.6703	Remote Similarity	NPD6777	Approved
0.6703	Remote Similarity	NPD6781	Approved
0.6703	Remote Similarity	NPD6779	Approved
0.6703	Remote Similarity	NPD6780	Approved
0.6703	Remote Similarity	NPD6778	Approved
0.6703	Remote Similarity	NPD6782	Approved
0.6703	Remote Similarity	NPD6776	Approved
0.669	Remote Similarity	NPD3091	Approved
0.6688	Remote Similarity	NPD2979	Phase 3
0.6687	Remote Similarity	NPD37	Approved
0.6687	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5403	Approved
0.6685	Remote Similarity	NPD7700	Phase 2
0.6685	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD1242	Phase 1
0.6667	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8319	Approved
0.6649	Remote Similarity	NPD8320	Phase 1
0.6648	Remote Similarity	NPD8434	Phase 2
0.6647	Remote Similarity	NPD5760	Phase 2
0.6647	Remote Similarity	NPD5761	Phase 2
0.6647	Remote Similarity	NPD1465	Phase 2
0.6646	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4908	Phase 1
0.6645	Remote Similarity	NPD6832	Phase 2
0.6645	Remote Similarity	NPD447	Suspended
0.6644	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4749	Approved
0.6629	Remote Similarity	NPD4956	Approved
0.6629	Remote Similarity	NPD1729	Discontinued
0.6626	Remote Similarity	NPD6273	Approved
0.6625	Remote Similarity	NPD3400	Discontinued
0.6623	Remote Similarity	NPD520	Approved
0.6622	Remote Similarity	NPD3092	Approved
0.6619	Remote Similarity	NPD2342	Discontinued
0.6612	Remote Similarity	NPD4363	Phase 3

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