NPASS Compound

Natural Product: NPC225743

Natural Product ID	NPC225743
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NGZXDRGWBULKFA-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	626931
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

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 82 88 0 0 0 0 0 0 0 0999 V2000 -6.0037 -3.2887 1.4862 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5975 -2.0345 0.9486 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.8539 -1.9850 -0.4616 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3099 -0.7909 -1.1746 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4382 0.0822 -0.3580 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1989 1.3528 -0.8184 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4050 2.2416 -0.1121 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8519 1.7944 1.0959 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1001 0.4984 1.5555 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8775 -0.3552 0.8544 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2132 -1.7442 1.2866 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3322 -2.7850 0.6569 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9068 -2.3679 0.7953 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1836 -2.7601 1.9008 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1430 -2.3501 2.0342 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7109 -1.5587 1.0611 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0124 -1.1842 -0.0173 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3134 -1.5762 -0.1663 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0127 -1.1626 1.2130 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0245 -1.2437 0.2786 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5006 -0.1977 -0.4985 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5106 -0.4841 -1.3770 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0539 0.5759 -2.2637 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2845 1.8262 -2.2627 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8221 2.2016 -0.9416 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9765 2.4479 -0.0931 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9626 1.1686 -0.3788 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6511 1.6365 1.0158 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5035 2.6068 1.0644 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6737 3.9480 0.7962 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6385 4.8484 0.8610 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6097 4.4296 1.1989 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8272 3.0755 1.4775 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2414 2.1976 1.4026 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0697 2.6578 1.8144 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6953 5.3288 1.2793 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0776 -1.7720 -1.5197 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6108 -2.7888 -0.7576 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5790 -2.4898 0.1346 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1038 -3.5695 0.9214 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1006 -4.0661 -0.8254 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1370 -4.5014 -1.6933 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1759 3.5216 -0.5945 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7590 3.9174 -1.8192 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2434 -3.8470 2.0575 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5132 -3.8971 0.7132 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8434 -3.0512 2.2187 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9805 -1.9535 -0.5633 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5434 -2.9469 -0.9496 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1407 -0.1291 -1.5512 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7729 -1.1160 -2.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6385 1.6936 -1.7663 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6416 0.2219 2.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1109 -1.7973 2.3756 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5835 -2.9581 -0.4108 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4261 -3.7239 1.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6280 -3.3714 2.6490 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7070 -2.6609 2.9043 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4323 -0.5670 -0.7760 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8958 -1.2840 -1.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0294 0.1647 -3.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1244 0.7303 -1.9825 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9963 2.6539 -2.5624 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4937 1.8326 -3.0350 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3138 1.5375 0.4329 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8857 3.3438 0.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8216 2.7148 -0.7983 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0142 1.2015 -0.9872 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4459 0.8054 1.6836 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5670 2.1271 1.4579 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6908 4.2423 0.5274 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8179 5.8919 0.6421 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0466 1.1563 1.6326 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2080 5.2811 2.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8766 -1.8812 -2.2502 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7224 -4.1042 1.5155 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9003 -3.6953 -1.8640 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6822 -5.3815 -1.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6659 -4.7789 -2.6569 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1900 3.4904 -2.6736 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8275 3.7127 -1.8123 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6305 5.0410 -1.8727 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 16 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 32 36 1 0 22 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 38 41 1 0 41 42 1 0 7 43 1 0 43 44 1 0 11 2 1 0 18 13 1 0 39 20 1 0 10 5 1 0 27 21 1 0 34 29 1 0 35 8 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 6 52 1 0 9 53 1 0 11 54 1 0 12 55 1 0 12 56 1 0 14 57 1 0 15 58 1 0 17 59 1 0 18 60 1 0 23 61 1 0 23 62 1 0 24 63 1 0 24 64 1 0 26 65 1 0 26 66 1 0 26 67 1 0 27 68 1 0 28 69 1 0 28 70 1 0 30 71 1 0 31 72 1 0 34 73 1 0 36 74 1 0 37 75 1 0 40 76 1 0 42 77 1 0 42 78 1 0 42 79 1 0 44 80 1 0 44 81 1 0 44 82 1 0 M END

Standard InCHIKey	NGZXDRGWBULKFA-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C36H38N2O6/c1-37-13-11-23-18-31(41-3)32-20-26(23)27(37)15-21-5-8-25(9-6-21)43-36-34-24(19-33(42-4)35(36)40)12-14-38(2)28(34)16-22-7-10-29(39)30(17-22)44-32/h5-10,17-20,27-28,39-40H,11-16H2,1-4H3
SMILES	CN1CCc2cc(c3cc2C1Cc1ccc(cc1)Oc1c2c(CCN(C)C2Cc2ccc(c(c2)O3)O)cc(c1O)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.27	Volume:	614.414 ? Van der Waals volume.
Dense:	0.967	LogP:	3.056 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.902 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.185 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	42.0
TPSA:	83.86 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	2.0	Rings:	8.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.27	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.764	Fsp³:	0.333
MCE-18:	130.0 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.994	Fluc inhibitor:	0.016 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.744 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.933 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.222

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.018	MDCK Permeability:	-4.799
Pgp-inhibitor:	0.101	Pgp-substrate:	0.182
PAMPA:	0.013 ? 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):	0.002
20% Bioavailability (F20%):	0.229	30% Bioavailability (F30%):	0.327
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.916	MRP1:	0.989
Plasma Protein Binding (PPB):	68.067%	Volume Distribution (VD):	-0.217
Fu:	32.552% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.578
OATP1B3 inhibitor:	0.977	BCRP inhibitor:	0.679
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.936	CYP3A4-substrate:	0.055
CYP2B6-substrate:	0.994	CYP2C8-inhibitor:	0.0
HLM stability:	0.063 ? 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):

5.972

Half-life (T1/2):

3.386

ADMET: Toxicity

hERG Blockers:	0.882	hERG Blockers (10um):	0.873
Human Hepatotoxicity (H-HT):	0.273	Drug-induced Liver Injury (DILI):	0.001
AMES Toxicity:	0.674	Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.929	Skin Sensitization:	0.95
Carcinogencity:	0.758	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.954
Drug-induced Neurotoxicity:	0.28	Ototoxicity:	0.865
Hematotoxicity:	0.022	Drug-induced Nephrotoxicity:	0.027
Genotoxicity:	0.15	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.244	Hek293 Cytotoxicity:	0.842
BCF:	1.61 ? 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:	4.223 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.535 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.902 ? 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
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13978	Cissampelos pareira	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13978	Cissampelos pareira	Species	Menispermaceae	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 NPC225743 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	29019
0.1-0.2	19265
0.2-0.3	1305
0.3-0.4	131
0.4-0.5	33
0.5-0.6	28
0.6-0.7	36
0.7-0.8	1
0.8-0.85	7
0.85-0.9	0
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC290005
0.9444	High Similarity	NPC181796
0.9444	High Similarity	NPC54654
0.9444	High Similarity	NPC7715
0.9444	High Similarity	NPC328155
0.9444	High Similarity	NPC222661
0.9444	High Similarity	NPC285931
0.8378	Intermediate Similarity	NPC279228
0.8243	Intermediate Similarity	NPC290582
0.8243	Intermediate Similarity	NPC217748
0.8243	Intermediate Similarity	NPC182052
0.8243	Intermediate Similarity	NPC271013
0.8243	Intermediate Similarity	NPC42663
0.8243	Intermediate Similarity	NPC15414
0.7922	Intermediate Similarity	NPC185639
0.7922	Intermediate Similarity	NPC251735
0.7922	Intermediate Similarity	NPC49075
0.7922	Intermediate Similarity	NPC223690
0.7922	Intermediate Similarity	NPC9532
0.7922	Intermediate Similarity	NPC599951
0.7439	Intermediate Similarity	NPC24260
0.7439	Intermediate Similarity	NPC8836
0.7432	Intermediate Similarity	NPC256012
0.7432	Intermediate Similarity	NPC610965
0.7375	Intermediate Similarity	NPC274716
0.7375	Intermediate Similarity	NPC167116
0.7375	Intermediate Similarity	NPC609821
0.7317	Intermediate Similarity	NPC212237
0.7286	Intermediate Similarity	NPC104196
0.726	Intermediate Similarity	NPC317272
0.726	Intermediate Similarity	NPC268503
0.7229	Intermediate Similarity	NPC611658
0.7079	Intermediate Similarity	NPC175890
0.7051	Intermediate Similarity	NPC240841
0.7051	Intermediate Similarity	NPC610959
0.7024	Intermediate Similarity	NPC275680
0.7024	Intermediate Similarity	NPC22115
0.6914	Remote Similarity	NPC311973
0.679	Remote Similarity	NPC608819
0.6747	Remote Similarity	NPC229373
0.6667	Remote Similarity	NPC480592
0.6667	Remote Similarity	NPC76682
0.6667	Remote Similarity	NPC10908
0.6667	Remote Similarity	NPC63646
0.6667	Remote Similarity	NPC317145
0.6667	Remote Similarity	NPC198498
0.6667	Remote Similarity	NPC115284
0.6627	Remote Similarity	NPC254441
0.6506	Remote Similarity	NPC239824
0.65	Remote Similarity	NPC603603
0.6429	Remote Similarity	NPC116465
0.6375	Remote Similarity	NPC276890
0.6333	Remote Similarity	NPC206900
0.6304	Remote Similarity	NPC41122
0.6304	Remote Similarity	NPC318805
0.6265	Remote Similarity	NPC73492
0.6265	Remote Similarity	NPC299990
0.6235	Remote Similarity	NPC601503
0.6222	Remote Similarity	NPC480586
0.622	Remote Similarity	NPC12424
0.622	Remote Similarity	NPC129518
0.622	Remote Similarity	NPC251580
0.6154	Remote Similarity	NPC11296
0.6154	Remote Similarity	NPC274661
0.6145	Remote Similarity	NPC603853
0.6136	Remote Similarity	NPC601489
0.6136	Remote Similarity	NPC604804
0.6133	Remote Similarity	NPC247639
0.6133	Remote Similarity	NPC25084
0.6118	Remote Similarity	NPC600054
0.6118	Remote Similarity	NPC601504
0.6044	Remote Similarity	NPC480590
0.6	Remote Similarity	NPC201508
0.5978	Remote Similarity	NPC82457
0.5889	Remote Similarity	NPC605743
0.5882	Remote Similarity	NPC480587
0.5843	Remote Similarity	NPC16357
0.5843	Remote Similarity	NPC302245
0.5747	Remote Similarity	NPC286119
0.5729	Remote Similarity	NPC60295
0.5625	Remote Similarity	NPC85381
0.5567	Remote Similarity	NPC191132
0.5545	Remote Similarity	NPC475654
0.5529	Remote Similarity	NPC227060
0.5435	Remote Similarity	NPC139783
0.5435	Remote Similarity	NPC65312
0.5435	Remote Similarity	NPC611798
0.5402	Remote Similarity	NPC480591
0.5393	Remote Similarity	NPC600872
0.5333	Remote Similarity	NPC185838
0.5325	Remote Similarity	NPC135538
0.5325	Remote Similarity	NPC24233
0.5325	Remote Similarity	NPC317439
0.5301	Remote Similarity	NPC30779
0.5233	Remote Similarity	NPC41376
0.5185	Remote Similarity	NPC83198
0.5161	Remote Similarity	NPC195538
0.5128	Remote Similarity	NPC321505
0.5128	Remote Similarity	NPC179825
0.5106	Remote Similarity	NPC243454
0.5048	Remote Similarity	NPC82056

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC225743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4806
0.1-0.2	4247
0.2-0.3	87
0.3-0.4	3
0.4-0.5	2
0.5-0.6	0
0.6-0.7	4
0.7-0.8	1
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
0.7273	Intermediate Similarity	NPD8054	Phase 4
0.6667	Remote Similarity	NPD8099	Discontinued
0.6341	Remote Similarity	NPD8156	Discontinued
0.6071	Remote Similarity	NPD8095	Phase 1
0.6064	Remote Similarity	NPD8053	Approved

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