NPASS Compound

Natural Product: NPC326451

Natural Product ID	NPC326451
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UYNHKOIUEXICNQ-XIJSCUBXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5321912
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related 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 89 95 0 0 0 0 0 0 0 0999 V2000 6.7469 -0.4682 1.1782 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4874 -1.1334 1.0852 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5219 -2.1936 0.1651 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7234 -1.9333 -1.1084 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3115 -1.6355 -0.6561 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2566 -2.1806 -1.2780 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9780 -1.9501 -0.8045 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7929 -1.1654 0.2990 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8862 -0.6119 0.9243 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1711 -0.8217 0.4776 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3800 -0.2456 1.1201 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8052 1.0863 0.6227 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7818 2.0366 0.1734 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0705 2.7505 1.1274 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1422 3.6982 0.6979 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9347 3.9208 -0.6441 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6379 3.2136 -1.5821 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5742 2.2575 -1.1656 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9980 4.8700 -1.0658 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3294 4.3948 -0.9844 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3650 5.2551 -1.2620 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6332 4.6972 -1.1561 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8528 3.3849 -0.8013 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8310 2.5555 -0.5319 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5337 3.0912 -0.6314 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 1.1494 -0.1256 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9894 0.3032 -0.4480 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7692 -1.1026 -0.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8431 -1.9377 -0.1965 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1161 -1.4781 -0.8097 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2966 0.0206 -0.8054 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2925 0.6521 0.0046 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5465 0.7202 1.3809 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7789 -3.2873 0.1823 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6199 -3.7707 0.7545 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5616 -2.9384 0.9434 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6230 -1.5892 0.5658 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4638 -0.8951 0.8290 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3961 -3.4699 1.5317 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2259 -3.4371 2.9355 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5319 -5.1241 1.1422 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9331 -5.5470 2.4311 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8664 -4.1185 -0.0178 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1227 6.5783 -1.6174 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1167 7.5123 -1.8941 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1383 -2.4972 -1.4261 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0810 -3.3036 -2.5808 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5386 -1.1731 1.5696 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7819 0.4430 1.7779 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1614 -0.2045 0.1546 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1405 -3.1321 0.6437 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5808 -2.3960 -0.1438 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1386 -1.1270 -1.7115 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6959 -2.8574 -1.7036 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3666 -2.8099 -2.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7768 0.0269 1.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0776 -0.0884 2.2309 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3106 1.6338 1.5034 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6416 1.0231 -0.1122 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1833 2.6254 2.1878 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5702 4.2754 1.4006 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5189 3.3449 -2.6441 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1396 1.6889 -1.8875 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4695 5.3708 -1.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8592 2.9864 -0.7339 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3554 2.4796 -0.4326 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5322 1.1167 0.9391 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.7127 -0.7274 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0526 0.2213 -1.5775 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0026 -1.9141 -0.2877 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1778 -1.8835 -1.8629 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3038 0.3459 -0.5623 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1044 0.3631 -1.8681 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0918 1.6453 1.7305 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2432 -0.1020 1.6712 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6237 0.5604 1.9708 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1452 -4.4822 3.3609 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6776 -2.8473 3.2009 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1157 -2.9201 3.4021 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9820 -4.6849 3.1319 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2156 -6.3087 2.8138 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9191 -6.0550 2.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5782 -3.8646 -0.6855 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4614 7.4340 -2.9330 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9899 7.3155 -1.2471 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7886 8.5534 -1.6406 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6260 -2.7621 -3.3625 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6269 -4.2216 -2.2627 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9274 -3.6446 -2.9141 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 2 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 29 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 36 39 1 0 39 40 1 0 35 41 1 0 41 42 1 0 34 43 1 0 21 44 1 0 44 45 1 0 7 46 1 0 46 47 1 0 11 2 1 0 10 5 1 0 38 8 1 0 18 13 1 0 25 20 1 0 32 27 1 0 37 28 1 0 1 48 1 0 1 49 1 0 1 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 6 55 1 0 9 56 1 0 11 57 1 0 12 58 1 0 12 59 1 0 14 60 1 0 15 61 1 0 17 62 1 0 18 63 1 0 22 64 1 0 23 65 1 0 25 66 1 0 26 67 1 0 26 68 1 0 27 69 1 0 30 70 1 0 30 71 1 0 31 72 1 0 31 73 1 0 33 74 1 0 33 75 1 0 33 76 1 0 40 77 1 0 40 78 1 0 40 79 1 0 42 80 1 0 42 81 1 0 42 82 1 0 43 83 1 0 45 84 1 0 45 85 1 0 45 86 1 0 47 87 1 0 47 88 1 0 47 89 1 0 M END

Standard InCHIKey	UYNHKOIUEXICNQ-XIJSCUBXSA-N
Standard InCHI	InChI=1S/C38H42N2O7/c1-39-15-13-24-20-31(43-4)33-21-27(24)28(39)17-22-7-10-25(11-8-22)46-32-19-23(9-12-30(32)42-3)18-29-34-26(14-16-40(29)2)35(41)37(44-5)38(45-6)36(34)47-33/h7-12,19-21,28-29,41H,13-18H2,1-6H3/t28?,29-/m0/s1
SMILES	CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(CCN6C)C(=C(C(=C7O3)OC)OC)O)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.3	Volume:	657.796 ? Van der Waals volume.
Dense:	0.97	LogP:	3.252 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.13 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.277 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	42.0
TPSA:	82.09 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	8.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.258	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.86	Fsp³:	0.368
MCE-18:	132.308 ? 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:	0.98	Fluc inhibitor:	0.043 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.738 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.885 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.256

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.868	MDCK Permeability:	-4.736
Pgp-inhibitor:	0.61	Pgp-substrate:	0.28
PAMPA:	0.011 ? 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):	0.0
20% Bioavailability (F20%):	0.025	30% Bioavailability (F30%):	0.034
50% Bioavailability (F50%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999	MRP1:	0.995
Plasma Protein Binding (PPB):	80.543%	Volume Distribution (VD):	-0.02
Fu:	22.313% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.163
OATP1B3 inhibitor:	0.93	BCRP inhibitor:	0.671
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.984	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.093
CYP2B6-substrate:	0.987	CYP2C8-inhibitor:	0.002
HLM stability:	0.038 ? 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):

8.557

Half-life (T1/2):

2.36

ADMET: Toxicity

hERG Blockers:	0.913	hERG Blockers (10um):	0.886
Human Hepatotoxicity (H-HT):	0.361	Drug-induced Liver Injury (DILI):	0.002
AMES Toxicity:	0.579	Rat Oral Acute Toxicity:	0.585
Maximum Recommended Daily Dose:	0.91	Skin Sensitization:	0.951
Carcinogencity:	0.778	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.958
Drug-induced Neurotoxicity:	0.523	Ototoxicity:	0.865
Hematotoxicity:	0.046	Drug-induced Nephrotoxicity:	0.045
Genotoxicity:	0.065	RPMI-8226 Immunitoxicity:	0.056
A549 Cytotoxicity:	0.246	Hek293 Cytotoxicity:	0.85
BCF:	1.675 ? 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:	4.335 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.939 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.047 ? 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
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30288	Thalictrum thunbergii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30288	Thalictrum thunbergii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30288	Thalictrum thunbergii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	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 NPC326451 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	29084
0.1-0.2	19697
0.2-0.3	824
0.3-0.4	117
0.4-0.5	32
0.5-0.6	51
0.6-0.7	21
0.7-0.8	3
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC116465
0.8553	High Similarity	NPC611658
0.7778	Intermediate Similarity	NPC76682
0.7778	Intermediate Similarity	NPC10908
0.7778	Intermediate Similarity	NPC63646
0.7778	Intermediate Similarity	NPC317145
0.7778	Intermediate Similarity	NPC198498
0.7778	Intermediate Similarity	NPC115284
0.7763	Intermediate Similarity	NPC311973
0.75	Intermediate Similarity	NPC290582
0.75	Intermediate Similarity	NPC217748
0.75	Intermediate Similarity	NPC182052
0.75	Intermediate Similarity	NPC271013
0.75	Intermediate Similarity	NPC42663
0.75	Intermediate Similarity	NPC15414
0.7432	Intermediate Similarity	NPC276890
0.7403	Intermediate Similarity	NPC279228
0.7368	Intermediate Similarity	NPC603853
0.7308	Intermediate Similarity	NPC239824
0.7273	Intermediate Similarity	NPC73492
0.7273	Intermediate Similarity	NPC299990
0.7123	Intermediate Similarity	NPC30779
0.7013	Intermediate Similarity	NPC12424
0.7013	Intermediate Similarity	NPC129518
0.7013	Intermediate Similarity	NPC251580
0.7	Intermediate Similarity	NPC185639
0.7	Intermediate Similarity	NPC251735
0.7	Intermediate Similarity	NPC247639
0.7	Intermediate Similarity	NPC254441
0.7	Intermediate Similarity	NPC49075
0.7	Intermediate Similarity	NPC25084
0.7	Intermediate Similarity	NPC599951
0.6883	Remote Similarity	NPC603603
0.6875	Remote Similarity	NPC286119
0.6835	Remote Similarity	NPC480587
0.679	Remote Similarity	NPC223690
0.679	Remote Similarity	NPC9532
0.6667	Remote Similarity	NPC212237
0.6588	Remote Similarity	NPC24260
0.6456	Remote Similarity	NPC227060
0.6429	Remote Similarity	NPC181796
0.6429	Remote Similarity	NPC290005
0.6429	Remote Similarity	NPC54654
0.6429	Remote Similarity	NPC7715
0.6429	Remote Similarity	NPC328155
0.6429	Remote Similarity	NPC222661
0.6429	Remote Similarity	NPC285931
0.6364	Remote Similarity	NPC480590
0.631	Remote Similarity	NPC229373
0.6118	Remote Similarity	NPC274716
0.6118	Remote Similarity	NPC167116
0.6118	Remote Similarity	NPC609821
0.6	Remote Similarity	NPC480586
0.5977	Remote Similarity	NPC16357
0.5977	Remote Similarity	NPC302245
0.5977	Remote Similarity	NPC195538
0.5926	Remote Similarity	NPC41376
0.5909	Remote Similarity	NPC243454
0.5897	Remote Similarity	NPC317272
0.5897	Remote Similarity	NPC268503
0.589	Remote Similarity	NPC317439
0.5875	Remote Similarity	NPC256012
0.5875	Remote Similarity	NPC610965
0.5761	Remote Similarity	NPC82457
0.573	Remote Similarity	NPC475479
0.573	Remote Similarity	NPC323537
0.5667	Remote Similarity	NPC485712
0.5658	Remote Similarity	NPC104196
0.561	Remote Similarity	NPC480592
0.5595	Remote Similarity	NPC240841
0.5591	Remote Similarity	NPC11296
0.5591	Remote Similarity	NPC274661
0.5581	Remote Similarity	NPC608819
0.5579	Remote Similarity	NPC41122
0.5579	Remote Similarity	NPC318805
0.5543	Remote Similarity	NPC10871
0.5543	Remote Similarity	NPC239584
0.5529	Remote Similarity	NPC480591
0.5517	Remote Similarity	NPC475393
0.5495	Remote Similarity	NPC275680
0.5495	Remote Similarity	NPC22115
0.5426	Remote Similarity	NPC206900
0.5426	Remote Similarity	NPC281581
0.5412	Remote Similarity	NPC610959
0.5376	Remote Similarity	NPC478963
0.5368	Remote Similarity	NPC485711
0.5341	Remote Similarity	NPC600054
0.5341	Remote Similarity	NPC601504
0.5326	Remote Similarity	NPC8836
0.5278	Remote Similarity	NPC213206
0.5278	Remote Similarity	NPC188163
0.5278	Remote Similarity	NPC328750
0.5217	Remote Similarity	NPC139783
0.5217	Remote Similarity	NPC65312
0.5217	Remote Similarity	NPC601489
0.5217	Remote Similarity	NPC604804
0.5217	Remote Similarity	NPC611798
0.5169	Remote Similarity	NPC600872
0.5161	Remote Similarity	NPC249996
0.5139	Remote Similarity	NPC314682
0.5111	Remote Similarity	NPC601503
0.5067	Remote Similarity	NPC185838
0.5065	Remote Similarity	NPC135538
0.5065	Remote Similarity	NPC24233

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC326451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4786
0.1-0.2	4279
0.2-0.3	70
0.3-0.4	9
0.4-0.5	0
0.5-0.6	2
0.6-0.7	0
0.7-0.8	3
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
0.7778	Intermediate Similarity	NPD8099	Discontinued
0.7368	Intermediate Similarity	NPD8156	Discontinued
0.7273	Intermediate Similarity	NPD8095	Phase 1
0.5278	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.5051	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