NPASS Compound

Natural Product: NPC325114

Natural Product ID	NPC325114
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FWCXELAAYFYCSR-FHOGVIIHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5317637
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 75 80 0 0 0 0 0 0 0 0999 V2000 6.3847 2.0649 -0.9485 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4207 0.8878 -0.0288 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2720 -0.4346 -0.7162 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8022 -0.7931 -0.9606 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9612 -0.4269 0.2305 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9441 -1.5333 0.5641 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8146 -1.1493 -0.2507 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9368 0.3801 -0.3172 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2365 0.6940 -0.0729 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0853 0.7979 0.8293 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0796 -0.1994 0.8482 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4251 -1.4347 0.1510 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3530 -1.7274 -1.1456 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8268 -1.7354 -0.7079 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1453 -0.2712 -0.6421 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3453 0.3922 0.4434 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2573 1.8653 0.0023 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5525 2.2675 -0.7068 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6747 1.5334 -0.0926 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5773 0.0646 -0.5312 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3764 -0.6797 0.4636 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7710 -0.1948 0.5476 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0684 1.1901 0.2005 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0436 1.9744 -0.5448 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4099 1.9483 1.3473 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5711 -1.0864 -0.2087 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2164 -0.1153 -1.8968 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2730 -2.6901 0.9821 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8831 -1.6875 2.0043 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7963 -0.1571 1.2848 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3789 1.0951 1.0579 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6711 1.9727 -1.7715 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0460 2.9543 -0.3402 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4124 2.3369 -1.2846 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4077 0.9010 0.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8362 -0.4221 -1.6471 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6451 -1.2157 0.0067 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7747 -1.8549 -1.2165 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5134 -0.2129 -1.8702 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4251 -2.4609 0.1207 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0274 -1.4593 -1.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5969 0.7618 -1.3004 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7591 1.8398 0.8041 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7174 0.7204 1.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1450 -0.5086 1.9387 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0670 -2.7339 -1.4738 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1409 -0.9231 -1.8486 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3875 -2.2553 -1.4880 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9677 -2.1568 0.2887 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7813 0.1599 -1.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0611 0.4464 1.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1457 2.5472 0.8408 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4721 1.9806 -0.8001 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5008 2.0843 -1.7781 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7105 3.3689 -0.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6883 1.6207 1.0226 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8701 -0.6436 1.4705 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3422 -1.7733 0.1850 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1182 -0.3802 1.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0109 1.2240 -0.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1648 1.9559 -1.6486 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1103 3.0714 -0.2751 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6313 1.8905 1.9586 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7396 -1.9187 0.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9247 -1.1271 -2.2463 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7536 0.5978 -2.6248 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3050 -0.0644 -1.8836 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1707 -2.4963 1.9805 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2461 -3.2619 1.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4166 -3.4514 0.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2103 -2.7214 2.3397 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6271 -1.0227 2.5437 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9418 -1.5209 2.5362 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6120 1.8290 0.7253 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8103 1.4832 1.9938 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 8 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 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 22 26 1 0 20 27 1 0 12 28 1 0 6 29 1 0 5 30 1 0 30 31 1 0 31 2 1 0 9 5 1 0 12 7 1 0 16 11 1 0 20 15 1 0 24 19 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 0 3 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 6 40 1 0 7 41 1 0 8 42 1 0 10 43 1 0 10 44 1 0 11 45 1 0 13 46 1 0 13 47 1 0 14 48 1 0 14 49 1 0 15 50 1 0 16 51 1 0 17 52 1 0 17 53 1 0 18 54 1 0 18 55 1 0 19 56 1 0 21 57 1 0 21 58 1 0 22 59 1 0 23 60 1 0 24 61 1 0 24 62 1 0 25 63 1 0 26 64 1 0 27 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 29 72 1 0 29 73 1 0 31 74 1 0 31 75 1 0 M END

Standard InCHIKey	FWCXELAAYFYCSR-FHOGVIIHSA-N
Standard InCHI	InChI=1S/C27H44O4/c1-15-7-10-27(30-14-15)16(2)24-23(31-27)12-20-18-6-5-17-11-21(28)22(29)13-26(17,4)19(18)8-9-25(20,24)3/h15-24,28-29H,5-14H2,1-4H3/t15-,16?,17?,18?,19?,20?,21-,22?,23+,24?,25+,26+,27?/m1/s1
SMILES	CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CC(C(C6)O)O)C)C)C)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	432.32	Volume:	459.37 ? Van der Waals volume.
Dense:	0.941	LogP:	3.929 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.973 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.47 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	30.0
TPSA:	58.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.579	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.384	Fsp³:	1.0
MCE-18:	142.519 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.136	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.065 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.01 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.146	Promiscuous compounds:	0.012

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.129	MDCK Permeability:	-4.795
Pgp-inhibitor:	0.032	Pgp-substrate:	0.005
PAMPA:	0.061 ? 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):	0.001
20% Bioavailability (F20%):	0.012	30% Bioavailability (F30%):	0.043
50% Bioavailability (F50%):	0.842

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.955	MRP1:	0.999
Plasma Protein Binding (PPB):	92.041%	Volume Distribution (VD):	0.553
Fu:	9.889% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.026
OATP1B3 inhibitor:	0.736	BCRP inhibitor:	0.011
BSEP inhibitor:	0.975

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.826	CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	0.982	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.958	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.995	CYP2C8-inhibitor:	0.177
HLM stability:	0.778 ? 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):

20.319

Half-life (T1/2):

2.174

ADMET: Toxicity

hERG Blockers:	0.369	hERG Blockers (10um):	0.825
Human Hepatotoxicity (H-HT):	0.641	Drug-induced Liver Injury (DILI):	0.145
AMES Toxicity:	0.179	Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.827	Skin Sensitization:	0.055
Carcinogencity:	0.444	Eye Corrosion:	0.0
Eye Irritation:	0.02	Respiratory Toxicity:	0.592
Drug-induced Neurotoxicity:	0.485	Ototoxicity:	0.95
Hematotoxicity:	0.051	Drug-induced Nephrotoxicity:	0.042
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.063
A549 Cytotoxicity:	0.179	Hek293 Cytotoxicity:	0.548
BCF:	2.212 ? 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:	4.687 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.896 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.426 ? 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
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37120447]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8210	Trigonella foenum-graecum	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 NPC325114 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	25233
0.1-0.2	23075
0.2-0.3	1316
0.3-0.4	122
0.4-0.5	71
0.5-0.6	29
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC227260
0.7797	Intermediate Similarity	NPC273290
0.7797	Intermediate Similarity	NPC232044
0.7627	Intermediate Similarity	NPC248944
0.7627	Intermediate Similarity	NPC7479
0.7627	Intermediate Similarity	NPC257296
0.6406	Remote Similarity	NPC296734
0.6349	Remote Similarity	NPC24556
0.6119	Remote Similarity	NPC305808
0.6119	Remote Similarity	NPC481427
0.5857	Remote Similarity	NPC161035
0.5857	Remote Similarity	NPC170438
0.5714	Remote Similarity	NPC473774
0.5714	Remote Similarity	NPC481418
0.5714	Remote Similarity	NPC481419
0.5714	Remote Similarity	NPC481417
0.5641	Remote Similarity	NPC24960
0.5634	Remote Similarity	NPC235126
0.5634	Remote Similarity	NPC242419
0.5556	Remote Similarity	NPC177818
0.5488	Remote Similarity	NPC294686
0.5357	Remote Similarity	NPC222731
0.5325	Remote Similarity	NPC144790
0.5325	Remote Similarity	NPC149400
0.5325	Remote Similarity	NPC88962
0.5316	Remote Similarity	NPC481420
0.5316	Remote Similarity	NPC481421
0.5256	Remote Similarity	NPC277715
0.5211	Remote Similarity	NPC187159
0.5181	Remote Similarity	NPC297348
0.5181	Remote Similarity	NPC325828
0.5181	Remote Similarity	NPC249204
0.5181	Remote Similarity	NPC48339
0.5181	Remote Similarity	NPC177834
0.5181	Remote Similarity	NPC141769
0.5181	Remote Similarity	NPC477547
0.5176	Remote Similarity	NPC473616
0.5119	Remote Similarity	NPC234352
0.5059	Remote Similarity	NPC477451

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC325114 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7359
0.1-0.2	1712
0.2-0.3	65
0.3-0.4	10
0.4-0.5	1
0.5-0.6	2
0.6-0.7	0
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
0.7627	Intermediate Similarity	NPD6928	Phase 2
0.5385	Remote Similarity	NPD7991	Discontinued
0.5181	Remote Similarity	NPD8171	Phase 2

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