NPASS Compound

Natural Product: NPC125578

Natural Product ID	NPC125578
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-Hydroxy-5-Methoxy-3-Hexadecyl-1,4-Benzoquinone
IUPAC Name	3-hexadecyl-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3416175
PubChem CID	5318477
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0002495] Quinones [CHEMONTID:0002384] Benzoquinones [CHEMONTID:0002494] P-benzoquinones

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 65 65 0 0 0 0 0 0 0 0999 V2000 8.6016 1.5914 1.6107 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6297 1.8834 0.4947 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5186 0.6908 -0.4158 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0343 -0.5386 0.2951 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6876 -0.3840 0.9121 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6126 -0.0548 -0.0857 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4587 -1.1205 -1.1467 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3955 -0.7930 -2.1333 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0210 -0.6305 -1.5299 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5348 -1.8500 -0.8323 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1655 -1.6228 -0.2459 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8276 -1.2801 -1.3047 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1990 -1.0687 -0.6567 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1374 -0.7284 -1.7900 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5304 -0.5068 -1.2559 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5321 0.6297 -0.2652 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9052 0.8311 0.2292 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5307 1.9759 0.0030 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8783 2.9842 -0.7060 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8960 2.2123 0.4809 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5254 3.2783 0.2895 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5595 1.1488 1.2201 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9541 0.0014 1.4569 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5760 -0.2198 0.9668 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0515 -1.3313 1.2236 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5907 -0.9897 2.1538 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6042 -1.0597 3.5679 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4758 1.0713 1.1553 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1303 0.9286 2.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9610 2.5356 2.0684 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6616 2.2632 0.8481 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0822 2.7114 -0.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9344 0.9387 -1.3255 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5574 0.4664 -0.7749 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0105 -1.3710 -0.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8089 -0.8143 1.0394 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6435 0.3183 1.7475 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4131 -1.3904 1.3439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7966 0.9368 -0.5353 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6319 -0.0004 0.4649 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3252 -2.1013 -0.6494 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4296 -1.1874 -1.6893 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6972 0.1299 -2.6686 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3069 -1.5776 -2.9116 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3079 -0.3988 -2.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0709 0.2095 -0.8108 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2125 -2.1396 0.0005 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4204 -2.7082 -1.5563 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1569 -0.8058 0.5033 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1887 -2.5529 0.2483 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9068 -2.0426 -2.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6254 -0.3067 -1.8204 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5157 -1.9222 -0.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0763 -0.1226 -0.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1186 -1.4656 -2.6008 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8039 0.2530 -2.2121 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2411 -0.2400 -2.0860 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8616 -1.4235 -0.7339 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0957 1.5496 -0.7048 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9135 0.3691 0.6213 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5192 3.8240 -0.2378 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5795 1.2608 1.6048 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1716 -1.9341 3.9286 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6131 -1.0366 4.0223 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1653 -0.1523 3.9325 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 18 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 26 27 1 0 24 17 1 0 1 28 1 0 1 29 1 0 1 30 1 0 2 31 1 0 2 32 1 0 3 33 1 0 3 34 1 0 4 35 1 0 4 36 1 0 5 37 1 0 5 38 1 0 6 39 1 0 6 40 1 0 7 41 1 0 7 42 1 0 8 43 1 0 8 44 1 0 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 14 55 1 0 14 56 1 0 15 57 1 0 15 58 1 0 16 59 1 0 16 60 1 0 19 61 1 0 22 62 1 0 27 63 1 0 27 64 1 0 27 65 1 0 M END

Standard InCHIKey	WQIANGZKDMBPFV-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C23H38O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-22(25)20(24)18-21(27-2)23(19)26/h18,25H,3-17H2,1-2H3
SMILES	CCCCCCCCCCCCCCCCC1=C(O)C(=O)C=C(C1=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	378.28	Volume:	422.423 ? Van der Waals volume.
Dense:	0.896	LogP:	6.745 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.2 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.33 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	8.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	1.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.251	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.509	Fsp³:	0.739
MCE-18:	8.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	1
Colloidal aggregators:	0.66	Fluc inhibitor:	0.949 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.159 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.897	Promiscuous compounds:	0.178

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.024	MDCK Permeability:	-4.834
Pgp-inhibitor:	0.012	Pgp-substrate:	0.028
PAMPA:	0.003 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.994
20% Bioavailability (F20%):	0.958	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.97
Plasma Protein Binding (PPB):	99.54%	Volume Distribution (VD):	1.245
Fu:	0.892% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.897
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.851
BSEP inhibitor:	0.707

ADMET: Metabolism

CYP1A2-inhibitor:	0.237	CYP1A2-substrate:	0.989
CYP2C19-inhibitor:	0.016	CYP2C19-substrate:	0.453
CYP2C9-inhibitor:	0.998	CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.977	CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.419	CYP2C8-inhibitor:	0.967
HLM stability:	0.165 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

3.243

Half-life (T1/2):

1.609

ADMET: Toxicity

hERG Blockers:	0.257	hERG Blockers (10um):	0.647
Human Hepatotoxicity (H-HT):	0.641	Drug-induced Liver Injury (DILI):	0.345
AMES Toxicity:	0.148	Rat Oral Acute Toxicity:	0.287
Maximum Recommended Daily Dose:	0.498	Skin Sensitization:	0.982
Carcinogencity:	0.427	Eye Corrosion:	0.892
Eye Irritation:	0.995	Respiratory Toxicity:	0.93
Drug-induced Neurotoxicity:	0.049	Ototoxicity:	0.15
Hematotoxicity:	0.407	Drug-induced Nephrotoxicity:	0.206
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.623	Hek293 Cytotoxicity:	0.218
BCF:	0.71 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.964 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.568 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.005 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10869197]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812212]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33780581]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36270431]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38257257]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38893531]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39104562]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9834145]
NPO942	Perophora namei	Species	Perophoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3733	Senecio triangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2781	Iris kumaonensis	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2566	Nocardiopsaceae	Species	Nocardiopsaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6516	Aspidosperma megalocarpon	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3733	Senecio triangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5561	Thenea muricata	Species	Theneidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO942	Perophora namei	Species	Perophoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2781	Iris kumaonensis	Species	Tarachodidae	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	Organism Name	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
Activity	4
IC50	4

Activity Type	# Activity
Individual protein	8

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1119	Individual protein	Arachidonate 12-lipoxygenase	Homo sapiens	Activity	=	137.5	%	PMID[25765759]
NPT3167	Individual protein	Macrophage-expressed gene 1 protein	Homo sapiens	IC50	>	10000.0	nM	PMID[25765759]
NPT3167	Individual protein	Macrophage-expressed gene 1 protein	Homo sapiens	Activity	=	68.4	%	PMID[25765759]
NPT792	Individual protein	Arachidonate 15-lipoxygenase	Homo sapiens	Activity	=	118.9	%	PMID[25765759]
NPT570	Individual protein	Arachidonate 5-lipoxygenase	Homo sapiens	Activity	=	60.1	%	PMID[25765759]
NPT570	Individual protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	>	10000.0	nM	PMID[25765759]
NPT570	Individual protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	1000.0	nM	PMID[25765759]
NPT570	Individual protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	1100.0	nM	PMID[25765759]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC125578 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	17882
0.1-0.2	30015
0.2-0.3	1860
0.3-0.4	56
0.4-0.5	24
0.5-0.6	10
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC243272
1.0	High Similarity	NPC146376
0.8718	High Similarity	NPC94743
0.7949	Intermediate Similarity	NPC264178
0.7674	Intermediate Similarity	NPC291062
0.6923	Remote Similarity	NPC53109
0.6889	Remote Similarity	NPC262673
0.5745	Remote Similarity	NPC487227
0.5476	Remote Similarity	NPC606251
0.537	Remote Similarity	NPC603676
0.5238	Remote Similarity	NPC7029
0.5238	Remote Similarity	NPC143168
0.5116	Remote Similarity	NPC474400
0.5116	Remote Similarity	NPC98897
0.5116	Remote Similarity	NPC151728
0.5116	Remote Similarity	NPC34622
0.5111	Remote Similarity	NPC134385

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC125578 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6333
0.1-0.2	2767
0.2-0.3	46
0.3-0.4	2
0.4-0.5	1
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
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
0.5238	Remote Similarity	NPD2664	Clinical (unspecified phase)

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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