NPASS Compound

Natural Product: NPC11411

Natural Product ID	NPC11411
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pinoresinol-4'-O-[6'-O-(E)-Feruloyl]-Beta-D-Glucopyranoside
IUPAC Name	[(2R,3S,4S,5R,6S)-6-[4-[(3R,3aS,6R,6aS)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2251617
PubChem CID	17755816
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

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 90 95 0 0 0 0 0 0 0 0999 V2000 12.0630 -2.0384 1.6842 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5766 -3.2872 1.1928 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3901 -3.3791 0.4773 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6094 -2.2586 0.2018 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4510 -2.3881 -0.5025 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0989 -3.6544 -0.9191 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8353 -4.7684 -0.6687 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0158 -4.6373 0.0491 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8064 -5.7342 0.3354 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5993 -1.2649 -0.8156 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8279 -0.0155 -0.4767 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8911 1.0718 -0.8447 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1744 2.2378 -0.4899 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7598 0.8616 -1.5362 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7386 1.6687 -1.9748 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7905 2.2757 -1.0222 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3324 3.3735 -0.2118 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2042 4.0480 0.6028 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6195 2.8656 1.3933 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9777 1.9917 0.3096 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0263 1.1556 0.7772 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3170 0.9779 0.5536 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9809 -0.0516 1.2528 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3180 -0.2570 1.0571 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0595 0.4949 0.2057 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4394 1.5115 -0.4954 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0979 1.7195 -0.3005 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5311 2.7543 -1.0313 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2589 3.5632 -1.9268 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5011 0.2820 0.0113 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0552 -0.4624 1.2087 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2624 -1.9057 0.8981 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4325 -2.0214 0.2020 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1399 -0.8529 0.2166 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5863 -0.9749 0.3988 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3089 -0.1563 1.2473 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6647 -0.3677 1.3367 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3406 -1.3334 0.6416 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6183 -2.1513 -0.2069 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2550 -1.9627 -0.3174 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3106 -3.1354 -0.9148 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6757 -4.0191 -1.8026 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7096 -1.5175 0.7572 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4907 0.0542 1.2356 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2887 1.4579 0.7412 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2142 1.4470 -0.0982 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0904 1.3230 -0.2769 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 3.2652 2.3411 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7286 5.0247 1.3955 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9224 4.3358 -0.9950 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4951 -1.7578 2.5926 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9660 -1.2510 0.9018 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1268 -2.1133 1.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9589 -1.3229 0.5609 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1692 -3.7535 -1.4856 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5538 -5.7784 -1.0008 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2417 -5.7798 1.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6726 -1.4248 -1.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7111 0.2054 0.0746 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1993 2.5042 -2.6322 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1485 1.0930 -2.7712 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9522 2.7219 -1.6894 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0233 3.0397 0.5618 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4520 4.3806 -0.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4497 2.3104 1.8624 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6075 2.6384 -0.5058 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3863 -0.6628 1.9414 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8075 -1.0684 1.6092 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0195 2.1274 -1.1850 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5818 4.4083 -2.2393 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5488 3.0365 -2.8616 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1294 4.0533 -1.4555 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6436 -0.2967 -0.9333 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5337 -0.2435 2.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3416 -2.4560 1.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4232 -2.3102 0.2764 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9638 -0.3514 -0.7778 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8100 0.6183 1.8125 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2328 0.2731 2.0015 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7241 -2.6271 -0.9941 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2912 -3.4421 -2.6569 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8315 -4.5583 -1.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4272 -4.7877 -2.1052 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1846 -1.2609 1.6223 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9214 0.0154 2.2324 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2391 1.7532 0.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1325 2.1269 1.6153 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4886 4.2214 2.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2746 5.8922 1.1631 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2892 4.6610 -1.7093 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 8 9 1 0 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 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 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 25 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 39 41 1 0 41 42 1 0 38 43 1 0 34 44 1 0 44 45 1 0 45 46 1 0 20 47 1 0 19 48 1 0 18 49 1 0 17 50 1 0 8 3 1 0 47 16 1 0 27 22 1 0 46 30 1 0 44 31 1 0 40 35 1 0 1 51 1 0 1 52 1 0 1 53 1 0 4 54 1 0 6 55 1 0 7 56 1 0 9 57 1 0 10 58 1 0 11 59 1 0 15 60 1 0 15 61 1 0 16 62 1 6 17 63 1 1 18 64 1 6 19 65 1 1 20 66 1 6 23 67 1 0 24 68 1 0 26 69 1 0 29 70 1 0 29 71 1 0 29 72 1 0 30 73 1 6 31 74 1 1 32 75 1 0 32 76 1 0 34 77 1 6 36 78 1 0 37 79 1 0 40 80 1 0 42 81 1 0 42 82 1 0 42 83 1 0 43 84 1 0 44 85 1 1 45 86 1 0 45 87 1 0 48 88 1 0 49 89 1 0 50 90 1 0 M END

Standard InCHIKey	YJJBMEAGCOFGGM-QIWKOVHQSA-N
Standard InCHI	InChI=1S/C36H40O14/c1-43-26-12-18(4-8-23(26)37)5-11-30(39)46-17-29-31(40)32(41)33(42)36(50-29)49-25-10-7-20(14-28(25)45-3)35-22-16-47-34(21(22)15-48-35)19-6-9-24(38)27(13-19)44-2/h4-14,21-22,29,31-38,40-42H,15-17H2,1-3H3/b11-5+/t21-,22-,29-,31-,32+,33-,34+,35+,36-/m1/s1
SMILES	COc1cc(ccc1O)/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2ccc(cc2OC)[C@H]2[C@@H]3CO[C@@H](c4ccc(c(c4)OC)O)[C@@H]3CO2)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	696.24	Volume:	673.935 ? Van der Waals volume.
Dense:	1.033	LogP:	1.402 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.767 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.525 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	35.0
TPSA:	192.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.145	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.786	Fsp³:	0.417
MCE-18:	126.961 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.827	Fluc inhibitor:	0.678 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.282 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.649 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.081	Promiscuous compounds:	0.218

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.991	MDCK Permeability:	-5.326
Pgp-inhibitor:	0.022	Pgp-substrate:	0.147
PAMPA:	0.019 ? 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):	0.006
20% Bioavailability (F20%):	0.54	30% Bioavailability (F30%):	0.967
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.122
Plasma Protein Binding (PPB):	84.085%	Volume Distribution (VD):	-0.315
Fu:	15.368% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.525
BSEP inhibitor:	0.756

ADMET: Metabolism

CYP1A2-inhibitor:	0.29	CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.034	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.321	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.083 ? 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):

2.504

Half-life (T1/2):

3.709

ADMET: Toxicity

hERG Blockers:	0.052	hERG Blockers (10um):	0.342
Human Hepatotoxicity (H-HT):	0.738	Drug-induced Liver Injury (DILI):	0.985
AMES Toxicity:	0.93	Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.167	Skin Sensitization:	0.997
Carcinogencity:	0.148	Eye Corrosion:	0.0
Eye Irritation:	0.345	Respiratory Toxicity:	0.028
Drug-induced Neurotoxicity:	0.061	Ototoxicity:	0.676
Hematotoxicity:	0.122	Drug-induced Nephrotoxicity:	0.937
Genotoxicity:	0.788	RPMI-8226 Immunitoxicity:	0.433
A549 Cytotoxicity:	0.647	Hek293 Cytotoxicity:	0.538
BCF:	0.989 ? 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:	3.665 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.09 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.545 ? 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
NPO33277.1	rhus javanica	Under-species	n.a.	n.a.	root	n.a.	n.a.	PMID[17616139]

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
Inhibition	1

Activity Type	# Activity
Organism	1

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
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	34.3	%	PMID[25615796]

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 NPC11411 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	13138
0.1-0.2	31924
0.2-0.3	3683
0.3-0.4	816
0.4-0.5	232
0.5-0.6	44
0.6-0.7	9
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	Natural Product ID
0.7791	Intermediate Similarity	NPC7191
0.7791	Intermediate Similarity	NPC149873
0.7317	Intermediate Similarity	NPC471405
0.6914	Remote Similarity	NPC38041
0.6914	Remote Similarity	NPC22150
0.6628	Remote Similarity	NPC157816
0.6489	Remote Similarity	NPC59516
0.6395	Remote Similarity	NPC10205
0.6292	Remote Similarity	NPC478055
0.6207	Remote Similarity	NPC291296
0.6087	Remote Similarity	NPC479767
0.6	Remote Similarity	NPC286235
0.5978	Remote Similarity	NPC476865
0.5934	Remote Similarity	NPC476868
0.593	Remote Similarity	NPC279298
0.5926	Remote Similarity	NPC246947
0.5862	Remote Similarity	NPC137813
0.5824	Remote Similarity	NPC226005
0.5824	Remote Similarity	NPC476869
0.5814	Remote Similarity	NPC51328
0.5814	Remote Similarity	NPC55158
0.5802	Remote Similarity	NPC276753
0.5802	Remote Similarity	NPC205796
0.5761	Remote Similarity	NPC488082
0.5733	Remote Similarity	NPC27843
0.5733	Remote Similarity	NPC7171
0.5684	Remote Similarity	NPC488081
0.567	Remote Similarity	NPC125823
0.567	Remote Similarity	NPC7145
0.567	Remote Similarity	NPC143480
0.5625	Remote Similarity	NPC300262
0.5579	Remote Similarity	NPC83743
0.5567	Remote Similarity	NPC133984
0.5532	Remote Similarity	NPC112861
0.55	Remote Similarity	NPC201148
0.5474	Remote Similarity	NPC262182
0.5455	Remote Similarity	NPC157898
0.5393	Remote Similarity	NPC18979
0.5341	Remote Similarity	NPC291153
0.53	Remote Similarity	NPC3460
0.5263	Remote Similarity	NPC185307
0.5263	Remote Similarity	NPC470950
0.5248	Remote Similarity	NPC472611
0.5234	Remote Similarity	NPC480796
0.5213	Remote Similarity	NPC476864
0.514	Remote Similarity	NPC470416
0.5133	Remote Similarity	NPC488079
0.5133	Remote Similarity	NPC488078
0.5111	Remote Similarity	NPC252402
0.5111	Remote Similarity	NPC327032
0.5111	Remote Similarity	NPC102934
0.5106	Remote Similarity	NPC476867
0.5093	Remote Similarity	NPC472993
0.5053	Remote Similarity	NPC204937
0.5053	Remote Similarity	NPC134905
0.5051	Remote Similarity	NPC80732

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC11411 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4626
0.1-0.2	4415
0.2-0.3	100
0.3-0.4	8
0.4-0.5	1
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