NPASS Compound

Natural Product: NPC167667

Natural Product ID	NPC167667
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OWHOEKLNSDNYTQ-IDAMAFBJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10720804
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0003109] Flavaglines

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 68 72 0 0 0 0 0 0 0 0999 V2000 -4.7087 2.7579 3.2491 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0757 2.1641 2.0282 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0979 1.6923 1.1808 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4763 1.1161 -0.0023 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4936 0.6314 -0.8749 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1720 0.7140 -0.5848 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7873 1.2998 0.6164 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7592 1.7829 1.4872 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4240 1.2903 0.7244 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1465 0.3880 -0.2170 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3895 0.8181 -0.7681 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8979 0.6580 -2.0327 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1378 1.1289 -2.4498 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9039 1.8004 -1.5257 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4638 2.0020 -0.2354 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2376 1.5164 0.1137 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2875 2.6934 0.6649 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7827 2.8673 1.9729 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1510 2.2890 -1.8991 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6187 2.1028 -3.2387 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0666 -0.9904 0.3591 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9799 -1.2965 1.4282 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4759 -1.4761 2.7162 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2765 -1.7747 3.7967 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6224 -1.9070 3.6338 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1590 -1.7347 2.3650 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3402 -1.4368 1.3003 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0918 -1.8352 -0.8594 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9368 -1.1334 -1.7354 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9362 0.3073 -1.2735 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6792 1.1078 -2.3862 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1622 -1.7064 -1.4435 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3549 -3.2231 -0.6430 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7206 -3.5159 0.5494 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4095 -4.1981 -1.5865 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8604 -5.4968 -1.2473 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9229 0.0627 -2.0509 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2923 -0.0359 -2.3769 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9602 2.1946 3.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3050 3.7871 3.0555 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5946 2.8692 3.9316 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5143 1.0414 -0.2461 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4958 2.2461 2.4295 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2808 0.1166 -2.7322 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4191 0.9357 -3.4735 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9215 1.6958 1.1423 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5328 3.3974 2.5857 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8049 3.3875 1.9740 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6883 1.8314 2.4114 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4953 2.7621 -3.4382 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9010 1.0449 -3.3908 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7874 2.3561 -3.9159 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9875 -1.0472 0.7715 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5905 -1.3834 2.9165 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8692 -1.9140 4.7968 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2597 -2.1399 4.4722 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2326 -1.8506 2.2813 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7774 -1.3121 0.3319 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0421 -1.8391 -1.4097 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6679 -1.2433 -2.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4814 1.0546 -2.9473 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4137 -1.6825 -0.5109 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0651 -6.1401 -1.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4975 -5.9221 -2.0298 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3062 -5.5256 -0.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7330 0.9799 -2.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8508 -0.4967 -1.5246 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4381 -0.6335 -3.3011 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 6 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 14 19 1 0 19 20 1 0 10 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 21 28 1 0 28 29 1 0 29 30 1 0 30 31 1 6 29 32 1 0 28 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 5 37 1 0 37 38 1 0 8 3 1 0 30 10 1 0 30 6 1 0 16 11 1 0 27 22 1 0 1 39 1 0 1 40 1 0 1 41 1 0 4 42 1 0 8 43 1 0 12 44 1 0 13 45 1 0 16 46 1 0 18 47 1 0 18 48 1 0 18 49 1 0 20 50 1 0 20 51 1 0 20 52 1 0 21 53 1 1 23 54 1 0 24 55 1 0 25 56 1 0 26 57 1 0 27 58 1 0 28 59 1 6 29 60 1 6 31 61 1 0 32 62 1 0 36 63 1 0 36 64 1 0 36 65 1 0 38 66 1 0 38 67 1 0 38 68 1 0 M END

Standard InCHIKey	OWHOEKLNSDNYTQ-IDAMAFBJSA-N
Standard InCHI	InChI=1S/C29H30O9/c1-33-18-14-21(36-4)25-22(15-18)38-29(17-11-12-19(34-2)20(13-17)35-3)24(16-9-7-6-8-10-16)23(27(31)37-5)26(30)28(25,29)32/h6-15,23-24,26,30,32H,1-5H3/t23-,24-,26-,28+,29+/m1/s1
SMILES	COc1cc(c2c(c1)O[C@@]1(c3ccc(c(c3)OC)OC)[C@H](c3ccccc3)[C@H]([C@H]([C@@]21O)O)C(=O)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	522.19	Volume:	520.105 ? Van der Waals volume.
Dense:	1.004	LogP:	2.94 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.219 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.337 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	27.0
TPSA:	112.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.452	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.993	Fsp³:	0.345
MCE-18:	107.462 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.086	Fluc inhibitor:	0.335 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.145 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.383 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.138	Promiscuous compounds:	0.052

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.646	MDCK Permeability:	-4.658
Pgp-inhibitor:	0.825	Pgp-substrate:	0.048
PAMPA:	0.007 ? 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):	0.008
20% Bioavailability (F20%):	0.014	30% Bioavailability (F30%):	0.059
50% Bioavailability (F50%):	0.815

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042	MRP1:	0.797
Plasma Protein Binding (PPB):	89.524%	Volume Distribution (VD):	0.103
Fu:	10.655% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.623
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.585	CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.725	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.053	CYP2C9-substrate:	0.242
CYP2D6-inhibitor:	0.981	CYP2D6-substrate:	0.714
CYP3A4-inhibitor:	0.979	CYP3A4-substrate:	0.076
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.279
HLM stability:	0.509 ? 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):

6.985

Half-life (T1/2):

2.002

ADMET: Toxicity

hERG Blockers:	0.192	hERG Blockers (10um):	0.502
Human Hepatotoxicity (H-HT):	0.948	Drug-induced Liver Injury (DILI):	0.586
AMES Toxicity:	0.228	Rat Oral Acute Toxicity:	0.467
Maximum Recommended Daily Dose:	0.884	Skin Sensitization:	0.777
Carcinogencity:	0.073	Eye Corrosion:	0.0
Eye Irritation:	0.504	Respiratory Toxicity:	0.913
Drug-induced Neurotoxicity:	0.623	Ototoxicity:	0.833
Hematotoxicity:	0.294	Drug-induced Nephrotoxicity:	0.938
Genotoxicity:	0.47	RPMI-8226 Immunitoxicity:	0.194
A549 Cytotoxicity:	0.033	Hek293 Cytotoxicity:	0.349
BCF:	1.002 ? 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:	3.672 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.073 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.25 ? 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
NPO13294	Pinus yunnanensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28052	Miriquidica leucophaea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18179	Leucopaxillus amarus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23171	Hygrophorus olivaceoalbus	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20222	Franseria ambrosioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19682	Duguetia chrysocarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20667	Cereus queretaroensis	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23092	Ammodendron karelinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27623	Citrus japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21632	Chlorobium phaeovibrioides	Species	Chlorobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	Leaf Diffusate	n.a.	n.a.	Database[FooDB]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27623	Citrus japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23171	Hygrophorus olivaceoalbus	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20222	Franseria ambrosioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21632	Chlorobium phaeovibrioides	Species	Chlorobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18179	Leucopaxillus amarus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13294	Pinus yunnanensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22318	Sechium edule	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20667	Cereus queretaroensis	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19682	Duguetia chrysocarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27623	Citrus japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28052	Miriquidica leucophaea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23092	Ammodendron karelinii	Species	Fabaceae	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

Molecular-level activity

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

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 NPC167667 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	19424
0.1-0.2	28088
0.2-0.3	2297
0.3-0.4	16
0.4-0.5	13
0.5-0.6	9
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8772	High Similarity	NPC73422
0.8548	High Similarity	NPC23593
0.7273	Intermediate Similarity	NPC236089
0.6462	Remote Similarity	NPC51543
0.641	Remote Similarity	NPC271755
0.641	Remote Similarity	NPC254071
0.641	Remote Similarity	NPC149502
0.641	Remote Similarity	NPC222665
0.6406	Remote Similarity	NPC206061
0.6364	Remote Similarity	NPC87363
0.5789	Remote Similarity	NPC263955
0.5735	Remote Similarity	NPC209473
0.5714	Remote Similarity	NPC189730
0.5634	Remote Similarity	NPC90336
0.5616	Remote Similarity	NPC107739
0.5616	Remote Similarity	NPC235698
0.5606	Remote Similarity	NPC184607
0.5185	Remote Similarity	NPC258128
0.5181	Remote Similarity	NPC475621

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC167667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3388
0.1-0.2	5474
0.2-0.3	288
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
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
		NPD

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