NPASS Compound

Natural Product: NPC526263

Natural Product ID	NPC526263
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(6~{R})-6-[[4-[5-[[(1~{S})-6,7-dimethoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-1-yl]methyl]-2,3-dimethoxy-phenoxy]phenyl]methyl]-4-methoxy-7-methyl-8,9-dihydro-6~{H}-[1,3]dioxolo[4,5-f]isoquinoline
IUPAC Name	(6~{R})-6-[[4-[5-[[(1~{S})-6,7-dimethoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-1-yl]methyl]-2,3-dimethoxy-phenoxy]phenyl]methyl]-4-methoxy-7-methyl-8,9-dihydro-6~{H}-[1,3]dioxolo[4,5-f]isoquinoline
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 96102 0 0 0 0 0 0 0 0999 V2000 -9.2280 3.6144 -2.3874 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3131 2.3802 -1.7050 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1625 1.7437 -1.2661 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9360 2.3103 -1.4913 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7590 1.7084 -1.0695 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8384 0.5232 -0.4157 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1089 -0.0481 -0.1912 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2751 0.5346 -0.6012 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5331 -0.0098 -0.3903 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6385 -1.2443 0.2900 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6451 -0.1830 0.0687 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6094 -0.2603 1.5894 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3821 -0.9716 2.0363 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3089 -2.3434 2.1783 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1531 -2.9645 2.5965 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0585 -4.3454 2.7454 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1235 -5.2201 2.4833 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0272 -2.2248 2.8874 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1325 -2.8683 3.3098 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2673 -3.0483 4.7192 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0575 -0.8457 2.7585 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0638 -0.0783 3.0477 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2363 -0.2329 2.3287 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3667 -1.0677 1.2393 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 -1.1563 0.5772 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6750 -0.4217 0.9940 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9872 -0.5105 0.2819 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9832 0.5693 -0.7893 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2428 0.5717 -1.5578 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5755 -0.5914 -2.2391 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7317 -0.6948 -2.9838 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0792 -1.8474 -3.6701 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1782 -2.9485 -3.5782 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5875 0.3811 -3.0598 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8126 0.6173 -3.7058 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4419 1.7375 -3.1029 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3179 2.4770 -2.6400 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2960 1.5567 -2.3985 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1137 1.6258 -1.6525 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7787 2.8790 -0.9388 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8878 2.5596 0.2105 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7053 1.8262 -0.1538 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7513 2.6292 -0.8856 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5120 0.4047 2.0884 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3187 0.5150 2.7637 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2458 -0.2539 2.3326 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4564 0.3389 -0.4757 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9753 -0.4088 -1.6088 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3298 1.7500 -0.5718 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4549 2.3890 -1.3460 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5468 4.3409 -1.8968 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2311 4.0922 -2.4795 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8849 3.4481 -3.4433 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8205 3.2697 -2.0174 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1615 -0.9984 0.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6774 -1.4017 0.6826 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3765 -2.1082 -0.3413 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9805 -1.3013 1.1954 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7332 -1.2497 -0.2968 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5495 0.7735 1.9695 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5050 -0.7570 1.9885 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1804 -2.9615 1.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3031 -5.1924 1.3756 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7915 -6.2353 2.8026 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0100 -4.8613 3.0411 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2564 -3.4667 4.9809 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1398 -2.0685 5.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5695 -3.7127 5.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5386 -1.6443 0.8975 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7353 -1.7974 -0.2794 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8035 -0.3390 1.0169 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1422 -1.4932 -0.1737 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1518 0.3348 -1.4810 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9050 -1.4466 -2.1850 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4300 -3.7412 -4.3082 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0372 -3.3038 -2.5491 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1755 -2.5434 -3.8953 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0285 1.3779 -2.2375 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0237 2.2862 -3.8495 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2772 3.5492 -1.6691 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7028 3.3534 -0.5225 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5292 3.5439 0.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4651 2.0815 1.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4171 2.0169 -1.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8655 2.7624 -0.2307 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1688 3.6075 -1.1999 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3726 0.9903 2.4239 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2215 1.1799 3.6294 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2435 0.8197 2.2400 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7135 -0.4682 -2.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9821 -0.0372 -1.9285 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8089 -1.4643 -1.2519 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2617 2.2131 0.4202 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3559 1.9563 -1.0993 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1926 2.2614 -2.4252 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5206 3.4816 -1.1712 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 9 10 1 0 6 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 2 0 18 19 1 0 19 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 2 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 26 44 1 0 44 45 2 0 21 46 2 0 11 47 1 0 47 48 1 0 47 49 1 0 49 50 1 0 8 3 1 0 46 13 1 0 50 5 1 0 45 23 1 0 42 28 1 0 39 29 1 0 38 34 1 0 1 51 1 0 1 52 1 0 1 53 1 0 4 54 1 0 7 55 1 0 10 56 1 0 10 57 1 0 10 58 1 0 11 59 1 6 12 60 1 0 12 61 1 0 14 62 1 0 17 63 1 0 17 64 1 0 17 65 1 0 20 66 1 0 20 67 1 0 20 68 1 0 24 69 1 0 25 70 1 0 27 71 1 0 27 72 1 0 28 73 1 6 30 74 1 0 33 75 1 0 33 76 1 0 33 77 1 0 36 78 1 0 36 79 1 0 40 80 1 0 40 81 1 0 41 82 1 0 41 83 1 0 43 84 1 0 43 85 1 0 43 86 1 0 44 87 1 0 45 88 1 0 46 89 1 0 48 90 1 0 48 91 1 0 48 92 1 0 49 93 1 0 49 94 1 0 50 95 1 0 50 96 1 0 M END

Standard InCHIKey	YJLUBKAIDVYKEO-AJQTZOPKSA-N
Standard InCHI	InChI=1S/C40H46N2O8/c1-41-14-12-26-20-33(43-3)34(44-4)21-29(26)31(41)17-25-18-35(45-5)39(47-7)37(19-25)50-27-10-8-24(9-11-27)16-32-30-22-36(46-6)40-38(48-23-49-40)28(30)13-15-42(32)2/h8-11,18-22,31-32H,12-17,23H2,1-7H3/t31-,32+/m0/s1
SMILES	COC1=CC2=C(C=C1OC)[C@H](CC1=CC(OC)=C(OC)C(OC3=CC=C(C[C@@H]4C5=CC(OC)=C6OCOC6=C5CCN4C)C=C3)=C1)N(C)CC2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	682.33	Volume:	701.178 ? Van der Waals volume.
Dense:	0.973	LogP:	2.821 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.823 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.243 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	38.0
TPSA:	80.32 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	0.0	Rings:	7.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.169	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.94	Fsp³:	0.4
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:	0	PAINS Alert:	0
Colloidal aggregators:	0.978	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.629 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.594 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.504

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.826	MDCK Permeability:	-4.714
Pgp-inhibitor:	0.999	Pgp-substrate:	0.486
PAMPA:	0.0 ? 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%):	0.477	30% Bioavailability (F30%):	0.005
50% Bioavailability (F50%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995	MRP1:	0.989
Plasma Protein Binding (PPB):	74.417%	Volume Distribution (VD):	0.134
Fu:	23.972% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.899
OATP1B3 inhibitor:	0.45	BCRP inhibitor:	0.622
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.231
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.994	CYP2C8-inhibitor:	0.201
HLM stability:	0.282 ? 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):

7.449

Half-life (T1/2):

2.321

ADMET: Toxicity

hERG Blockers:	0.931	hERG Blockers (10um):	0.796
Human Hepatotoxicity (H-HT):	0.897	Drug-induced Liver Injury (DILI):	0.043
AMES Toxicity:	0.578	Rat Oral Acute Toxicity:	0.874
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	0.061
Carcinogencity:	0.563	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.956
Drug-induced Neurotoxicity:	0.994	Ototoxicity:	0.643
Hematotoxicity:	0.021	Drug-induced Nephrotoxicity:	0.505
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.12
A549 Cytotoxicity:	0.255	Hek293 Cytotoxicity:	0.708
BCF:	2.33 ? 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:	4.96 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.737 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.072 ? 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
NPO47479	Isopyrum thalicroides	Genus	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC526263 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	33184
0.1-0.2	15482
0.2-0.3	910
0.3-0.4	131
0.4-0.5	89
0.5-0.6	51
0.6-0.7	8
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
0.6957	Remote Similarity	NPC247639
0.6957	Remote Similarity	NPC25084
0.6375	Remote Similarity	NPC73492
0.6375	Remote Similarity	NPC299990
0.6203	Remote Similarity	NPC227060
0.6076	Remote Similarity	NPC276890
0.6049	Remote Similarity	NPC603853
0.6	Remote Similarity	NPC603603
0.5955	Remote Similarity	NPC478965
0.5949	Remote Similarity	NPC76682
0.5949	Remote Similarity	NPC10908
0.5949	Remote Similarity	NPC63646
0.5949	Remote Similarity	NPC317145
0.5949	Remote Similarity	NPC198498
0.5949	Remote Similarity	NPC115284
0.5735	Remote Similarity	NPC314682
0.5652	Remote Similarity	NPC213206
0.5652	Remote Similarity	NPC188163
0.5652	Remote Similarity	NPC328750
0.5641	Remote Similarity	NPC317272
0.5641	Remote Similarity	NPC268503
0.5542	Remote Similarity	NPC12424
0.5542	Remote Similarity	NPC129518
0.5542	Remote Similarity	NPC251580
0.5517	Remote Similarity	NPC229373
0.5465	Remote Similarity	NPC475393
0.5444	Remote Similarity	NPC24260
0.5412	Remote Similarity	NPC290582
0.5412	Remote Similarity	NPC217748
0.5412	Remote Similarity	NPC182052
0.5412	Remote Similarity	NPC271013
0.5412	Remote Similarity	NPC42663
0.5412	Remote Similarity	NPC15414
0.5412	Remote Similarity	NPC480587
0.5408	Remote Similarity	NPC478969
0.5405	Remote Similarity	NPC317439
0.5393	Remote Similarity	NPC302275
0.5375	Remote Similarity	NPC30779
0.5349	Remote Similarity	NPC279228
0.5287	Remote Similarity	NPC311973
0.5287	Remote Similarity	NPC286119
0.5244	Remote Similarity	NPC256012
0.5244	Remote Similarity	NPC610965
0.5227	Remote Similarity	NPC254441
0.5227	Remote Similarity	NPC116465
0.5227	Remote Similarity	NPC223690
0.5227	Remote Similarity	NPC9532
0.5195	Remote Similarity	NPC27887
0.5176	Remote Similarity	NPC240841
0.5165	Remote Similarity	NPC212237
0.5165	Remote Similarity	NPC243454
0.5114	Remote Similarity	NPC239824
0.5114	Remote Similarity	NPC112248
0.5056	Remote Similarity	NPC185639
0.5056	Remote Similarity	NPC251735
0.5056	Remote Similarity	NPC49075
0.5056	Remote Similarity	NPC599951
0.5055	Remote Similarity	NPC195538
0.5053	Remote Similarity	NPC281581

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC526263 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4927
0.1-0.2	4099
0.2-0.3	109
0.3-0.4	7
0.4-0.5	4
0.5-0.6	4
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
0.5949	Remote Similarity	NPD8099	Discontinued
0.5663	Remote Similarity	NPD8156	Discontinued
0.5652	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.5412	Remote Similarity	NPD8095	Phase 1

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