NPASS Compound

Natural Product: NPC523567

Natural Product ID	NPC523567
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-6-[[(2~{R},3~{S},4~{R},5~{R})-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-chromen-4-one
IUPAC Name	7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-6-[[(2~{R},3~{S},4~{R},5~{R})-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-chromen-4-one
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 69 73 0 0 0 0 0 0 0 0999 V2000 -6.2387 3.6690 0.5117 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7218 2.5345 0.3970 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4490 1.3640 0.5562 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9008 0.1113 0.4344 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6508 -1.1356 0.5987 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0135 -2.3554 0.4486 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7037 -3.5454 0.6014 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0547 -3.5605 0.9097 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7651 -4.7570 1.0670 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6904 -2.3498 1.0594 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0427 -2.3600 1.3681 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9815 -1.1506 0.9022 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6166 0.0543 0.1514 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8715 1.1305 -0.0117 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5140 0.9761 -0.3106 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6528 2.0291 -0.4990 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3312 1.9565 -0.7896 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4105 0.8051 -0.9588 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4008 0.6675 0.0226 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2503 1.7678 0.0493 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4525 1.4103 0.8982 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0680 0.3295 0.3208 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1894 -0.1253 0.9787 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3263 -0.0171 0.1829 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2908 -0.8148 0.7890 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2732 -1.2646 -0.2650 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2660 -2.0756 0.3100 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5555 -2.0061 1.3619 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7698 -3.1242 0.5546 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1280 -1.5678 1.3615 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4109 -2.3420 0.4363 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7673 2.0600 -1.3537 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1139 2.4087 -1.3347 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5198 0.8207 -2.1874 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1835 0.8788 -3.4091 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0196 0.6934 -2.3513 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6463 -0.4577 -3.0083 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2297 3.3058 -0.3710 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5562 3.4923 -0.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1334 4.7467 0.0490 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3804 2.4026 0.1013 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5051 1.4533 0.7886 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9629 -2.3520 0.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2016 -4.4828 0.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5626 -4.7204 1.6990 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5670 -1.4965 1.2271 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5437 -0.2507 1.0339 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1480 -0.0395 -0.3916 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2315 -0.0856 -0.8478 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7086 2.6061 0.4858 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1034 1.2230 1.9338 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1348 2.3056 0.9446 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3575 0.5091 1.8725 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8220 -0.3268 1.6107 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7441 -0.3577 -0.6916 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7296 -1.8647 -1.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8137 -1.5487 0.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8810 -2.2398 2.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4946 -3.6845 0.9339 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6390 -1.6616 2.3531 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7959 -3.2651 0.5101 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1226 2.8713 -1.7496 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1714 3.3196 -1.7235 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8421 -0.0979 -1.6195 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.6029 -4.1761 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6982 1.6208 -2.8995 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2721 -0.3239 -3.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5969 4.1677 -0.5091 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6110 5.5962 0.0299 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 8 10 1 0 10 11 1 0 10 12 2 0 4 13 1 0 13 14 1 0 14 15 2 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 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 20 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 16 38 2 0 38 39 1 0 39 40 1 0 39 41 2 0 41 2 1 0 12 5 1 0 41 14 1 0 36 18 1 0 30 23 1 0 3 42 1 0 6 43 1 0 7 44 1 0 9 45 1 0 11 46 1 0 12 47 1 0 15 48 1 0 18 49 1 1 20 50 1 1 21 51 1 0 21 52 1 0 23 53 1 1 25 54 1 1 26 55 1 0 26 56 1 0 27 57 1 0 28 58 1 1 29 59 1 0 30 60 1 1 31 61 1 0 32 62 1 6 33 63 1 0 34 64 1 1 35 65 1 0 36 66 1 6 37 67 1 0 38 68 1 0 40 69 1 0 M END

Standard InCHIKey	DUJKQJGBZKOHJV-DEEXAQIXSA-N
Standard InCHI	InChI=1S/C26H28O15/c27-7-17-20(32)23(35)25(40-17)37-8-18-21(33)22(34)24(36)26(41-18)38-10-4-13(30)19-14(31)6-15(39-16(19)5-10)9-1-2-11(28)12(29)3-9/h1-6,17-18,20-30,32-36H,7-8H2/t17-,18+,20+,21-,22+,23+,24-,25-,26-/m1/s1
SMILES	O=C1C=C(C2=CC=C(O)C(O)=C2)OC2=CC(O[C@@H]3O[C@@H](CO[C@@H]4O[C@H](CO)[C@H](O)[C@@H]4O)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	580.14	Volume:	526.232 ? Van der Waals volume.
Dense:	1.102	LogP:	0.556 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.976 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.92 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	29.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.14	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.597	Fsp³:	0.423
MCE-18:	115.054 ? 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:	1
Colloidal aggregators:	0.66	Fluc inhibitor:	0.303 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.984 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.61 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.189	Promiscuous compounds:	0.488

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.525	MDCK Permeability:	-5.059
Pgp-inhibitor:	0.0	Pgp-substrate:	0.56
PAMPA:	1.0 ? 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):	0.994
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.861
Plasma Protein Binding (PPB):	82.27%	Volume Distribution (VD):	-0.014
Fu:	15.901% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.966
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.02
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.101
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.576
HLM stability:	0.013 ? 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):

2.536

Half-life (T1/2):

3.623

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.082
Human Hepatotoxicity (H-HT):	0.602	Drug-induced Liver Injury (DILI):	0.987
AMES Toxicity:	0.988	Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.056	Skin Sensitization:	1.0
Carcinogencity:	0.28	Eye Corrosion:	0.0
Eye Irritation:	0.498	Respiratory Toxicity:	0.024
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.954
Hematotoxicity:	0.332	Drug-induced Nephrotoxicity:	0.371
Genotoxicity:	0.976	RPMI-8226 Immunitoxicity:	0.092
A549 Cytotoxicity:	0.988	Hek293 Cytotoxicity:	0.713
BCF:	0.398 ? 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:	2.992 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.582 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.677 ? 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
NPO46381	Dacrydium spp.	Genus	Podocarpaceae	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 NPC523567 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	24280
0.1-0.2	21833
0.2-0.3	2661
0.3-0.4	619
0.4-0.5	288
0.5-0.6	117
0.6-0.7	42
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8642	High Similarity	NPC210073
0.8333	Intermediate Similarity	NPC65711
0.7949	Intermediate Similarity	NPC189142
0.7949	Intermediate Similarity	NPC77660
0.7647	Intermediate Similarity	NPC44931
0.7416	Intermediate Similarity	NPC229409
0.7375	Intermediate Similarity	NPC19709
0.7222	Intermediate Similarity	NPC209296
0.7176	Intermediate Similarity	NPC190003
0.7159	Intermediate Similarity	NPC22062
0.7159	Intermediate Similarity	NPC473634
0.7159	Intermediate Similarity	NPC138811
0.7045	Intermediate Similarity	NPC67105
0.6957	Remote Similarity	NPC488089
0.6951	Remote Similarity	NPC39360
0.6951	Remote Similarity	NPC29763
0.6951	Remote Similarity	NPC210003
0.6854	Remote Similarity	NPC275454
0.6848	Remote Similarity	NPC473623
0.6818	Remote Similarity	NPC8856
0.6809	Remote Similarity	NPC101636
0.663	Remote Similarity	NPC64051
0.6552	Remote Similarity	NPC22832
0.6552	Remote Similarity	NPC601144
0.6548	Remote Similarity	NPC261866
0.6522	Remote Similarity	NPC115674
0.6477	Remote Similarity	NPC311830
0.6471	Remote Similarity	NPC95090
0.6471	Remote Similarity	NPC277205
0.6471	Remote Similarity	NPC27408
0.6471	Remote Similarity	NPC37919
0.6458	Remote Similarity	NPC298171
0.6444	Remote Similarity	NPC254540
0.6429	Remote Similarity	NPC473043
0.6429	Remote Similarity	NPC331652
0.6421	Remote Similarity	NPC270675
0.6421	Remote Similarity	NPC195685
0.6344	Remote Similarity	NPC186816
0.6322	Remote Similarity	NPC27942
0.6304	Remote Similarity	NPC227508
0.6279	Remote Similarity	NPC136042
0.6277	Remote Similarity	NPC46202
0.6238	Remote Similarity	NPC480441
0.6224	Remote Similarity	NPC472994
0.6207	Remote Similarity	NPC58716
0.6207	Remote Similarity	NPC84362
0.6207	Remote Similarity	NPC45638
0.618	Remote Similarity	NPC243930
0.6136	Remote Similarity	NPC201292
0.6111	Remote Similarity	NPC607707
0.6092	Remote Similarity	NPC168822
0.6087	Remote Similarity	NPC606546
0.6067	Remote Similarity	NPC20505
0.6064	Remote Similarity	NPC156869
0.6023	Remote Similarity	NPC181712
0.598	Remote Similarity	NPC472993
0.5977	Remote Similarity	NPC238376
0.5962	Remote Similarity	NPC488083
0.5943	Remote Similarity	NPC298666
0.5943	Remote Similarity	NPC198199
0.5934	Remote Similarity	NPC605784
0.59	Remote Similarity	NPC484301
0.59	Remote Similarity	NPC253685
0.5895	Remote Similarity	NPC473512
0.5895	Remote Similarity	NPC479405
0.5865	Remote Similarity	NPC311850
0.5844	Remote Similarity	NPC108406
0.5833	Remote Similarity	NPC204693
0.5833	Remote Similarity	NPC479404
0.5784	Remote Similarity	NPC11468
0.578	Remote Similarity	NPC120952
0.5773	Remote Similarity	NPC488073
0.5769	Remote Similarity	NPC25523
0.573	Remote Similarity	NPC297987
0.573	Remote Similarity	NPC323593
0.573	Remote Similarity	NPC203500
0.5729	Remote Similarity	NPC65003
0.5729	Remote Similarity	NPC129827
0.5729	Remote Similarity	NPC218488
0.5714	Remote Similarity	NPC479403
0.5701	Remote Similarity	NPC68592
0.5667	Remote Similarity	NPC271692
0.566	Remote Similarity	NPC488087
0.5638	Remote Similarity	NPC172807
0.56	Remote Similarity	NPC486577
0.5567	Remote Similarity	NPC203259
0.5567	Remote Similarity	NPC33054
0.5567	Remote Similarity	NPC176740
0.5567	Remote Similarity	NPC471725
0.5567	Remote Similarity	NPC134532
0.5567	Remote Similarity	NPC602582
0.5567	Remote Similarity	NPC607513
0.5556	Remote Similarity	NPC470443
0.5545	Remote Similarity	NPC475382
0.5534	Remote Similarity	NPC14187
0.551	Remote Similarity	NPC122809
0.55	Remote Similarity	NPC483707
0.5474	Remote Similarity	NPC211594
0.5472	Remote Similarity	NPC473644
0.5464	Remote Similarity	NPC67326
0.5444	Remote Similarity	NPC289667
0.5437	Remote Similarity	NPC135358
0.5426	Remote Similarity	NPC116458
0.5426	Remote Similarity	NPC246943
0.5408	Remote Similarity	NPC303913
0.5408	Remote Similarity	NPC3583
0.5398	Remote Similarity	NPC262222
0.5392	Remote Similarity	NPC80068
0.5392	Remote Similarity	NPC195257
0.5392	Remote Similarity	NPC473073
0.5385	Remote Similarity	NPC93337
0.5385	Remote Similarity	NPC146792
0.5376	Remote Similarity	NPC282169
0.5376	Remote Similarity	NPC285197
0.5361	Remote Similarity	NPC473657
0.5347	Remote Similarity	NPC150767
0.5326	Remote Similarity	NPC105025
0.5326	Remote Similarity	NPC610763
0.5319	Remote Similarity	NPC80188
0.53	Remote Similarity	NPC126784
0.53	Remote Similarity	NPC241423
0.53	Remote Similarity	NPC475366
0.5275	Remote Similarity	NPC58053
0.5275	Remote Similarity	NPC249281
0.5275	Remote Similarity	NPC108831
0.5275	Remote Similarity	NPC143851
0.5275	Remote Similarity	NPC182634
0.5273	Remote Similarity	NPC488086
0.5263	Remote Similarity	NPC220169
0.5234	Remote Similarity	NPC292019
0.5234	Remote Similarity	NPC202908
0.5213	Remote Similarity	NPC191306
0.5213	Remote Similarity	NPC307938
0.5208	Remote Similarity	NPC276377
0.5208	Remote Similarity	NPC601586
0.5204	Remote Similarity	NPC295613
0.5189	Remote Similarity	NPC121703
0.5182	Remote Similarity	NPC488088
0.5172	Remote Similarity	NPC191154
0.5161	Remote Similarity	NPC245014
0.5161	Remote Similarity	NPC186807
0.5161	Remote Similarity	NPC46420
0.5158	Remote Similarity	NPC486578
0.5158	Remote Similarity	NPC601710
0.5158	Remote Similarity	NPC605067
0.5155	Remote Similarity	NPC116864
0.5155	Remote Similarity	NPC244776
0.5152	Remote Similarity	NPC173582
0.5152	Remote Similarity	NPC265885
0.5152	Remote Similarity	NPC181465
0.5152	Remote Similarity	NPC215710
0.5152	Remote Similarity	NPC473438
0.5152	Remote Similarity	NPC253788
0.5149	Remote Similarity	NPC64425
0.5149	Remote Similarity	NPC475497
0.5149	Remote Similarity	NPC488074
0.5146	Remote Similarity	NPC142142
0.5143	Remote Similarity	NPC470446
0.5143	Remote Similarity	NPC179862
0.5109	Remote Similarity	NPC45618
0.5106	Remote Similarity	NPC117260
0.5104	Remote Similarity	NPC602805
0.51	Remote Similarity	NPC233994
0.51	Remote Similarity	NPC102028
0.51	Remote Similarity	NPC150164
0.5096	Remote Similarity	NPC477629
0.5054	Remote Similarity	NPC158674
0.5051	Remote Similarity	NPC471079
0.5049	Remote Similarity	NPC210961
0.5049	Remote Similarity	NPC32641
0.5049	Remote Similarity	NPC256188
0.5049	Remote Similarity	NPC35119

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC523567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5771
0.1-0.2	3314
0.2-0.3	51
0.3-0.4	7
0.4-0.5	2
0.5-0.6	3
0.6-0.7	1
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
0.7222	Intermediate Similarity	NPD7054	Phase 4
0.6526	Remote Similarity	NPD7251	Phase 2
0.5567	Remote Similarity	NPD6797	Phase 2
0.5481	Remote Similarity	NPD7472	Pre-clinical
0.5481	Remote Similarity	NPD7808	Phase 3

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