NPASS Compound

Natural Product: NPC557013

Natural Product ID	NPC557013
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-[4-hydroxy-3-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]-7-methoxy-3-[(2~{S},3~{R},4~{R},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-[4-hydroxy-3-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]-7-methoxy-3-[(2~{S},3~{R},4~{R},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-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 76 80 0 0 0 0 0 0 0 0999 V2000 -4.5994 7.3754 1.1871 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0911 6.8763 -0.0422 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5109 5.7079 -0.5667 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9432 5.1729 -1.7551 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3811 4.0281 -2.2778 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8222 3.5063 -3.4634 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3467 3.3774 -1.6034 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7640 2.2365 -2.0882 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1427 1.7295 -3.1715 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7365 1.6540 -1.3432 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1656 0.4912 -1.8500 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7254 -0.7866 -1.5802 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8599 -1.7141 -1.0767 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6043 -2.8770 -0.7741 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7457 -3.7894 0.0757 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4514 -4.9486 0.3931 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9195 -3.6274 -2.0576 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2420 -4.0446 -2.1161 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6964 -2.6868 -3.2378 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4409 -3.1960 -4.2993 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2452 -1.3074 -2.9280 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6385 -1.3068 -2.9245 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3235 2.2019 -0.1755 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2522 1.6811 0.6854 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1617 2.2057 1.9719 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8304 1.8238 2.8385 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7974 0.8894 2.4700 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7877 0.5400 3.4064 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7325 0.3578 1.2101 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6200 -0.5548 0.7536 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7095 -1.1442 1.3199 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8220 -0.8644 0.4967 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0045 -1.2613 1.1103 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2238 -0.5391 2.4269 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0466 -2.7617 1.2743 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3701 -3.3337 0.0400 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7810 -3.3250 1.8308 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7497 -4.6916 1.4866 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5355 -2.6701 1.3390 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5244 -2.9210 2.2783 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6852 0.7827 0.3402 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9533 3.3162 0.2200 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9094 3.9007 -0.4213 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4896 5.0592 0.0922 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6002 7.8448 1.0934 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2745 8.1281 1.6326 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5033 6.5674 1.9496 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7385 5.6451 -2.3053 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8019 3.6002 -3.7113 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6010 -0.7267 -0.9187 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5280 -2.6596 -0.2392 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4929 -3.2929 1.0502 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1831 -4.0879 -0.4306 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2040 -4.7444 1.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2778 -4.5086 -2.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7870 -3.6685 -1.3832 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6300 -2.6029 -3.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3709 -2.8827 -4.2067 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9245 -0.6592 -3.7654 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9638 -1.1470 -1.9866 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8786 2.9350 2.3242 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9055 2.2307 3.8455 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4229 1.2586 3.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0226 -0.8777 2.3263 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8277 -0.9772 0.4277 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6986 0.4301 2.3965 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3187 -0.3379 2.5945 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9084 -1.1771 3.2887 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8695 -2.9858 2.0052 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8897 -2.6544 -0.4704 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8409 -3.2758 2.9470 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1393 -4.8237 0.5914 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1850 -3.0559 0.3747 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7022 -3.8348 2.6640 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7063 0.3629 -0.6311 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1016 5.4151 1.0196 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 1 0 5 7 2 0 7 8 1 0 8 9 2 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 14 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 10 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 29 41 2 0 23 42 1 0 42 43 1 0 43 44 2 0 44 3 1 0 43 7 1 0 21 12 1 0 41 24 1 0 39 31 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 6 49 1 0 12 50 1 1 14 51 1 1 15 52 1 0 15 53 1 0 16 54 1 0 17 55 1 6 18 56 1 0 19 57 1 6 20 58 1 0 21 59 1 6 22 60 1 0 25 61 1 0 26 62 1 0 28 63 1 0 31 64 1 1 33 65 1 6 34 66 1 0 34 67 1 0 34 68 1 0 35 69 1 1 36 70 1 0 37 71 1 1 38 72 1 0 39 73 1 6 40 74 1 0 41 75 1 0 44 76 1 0 M END

Standard InCHIKey	PMCPOMBJNMAESR-LEFTZGBISA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(40-9)42-14-5-10(3-4-12(14)30)25-26(44-28-24(38)22(36)19(33)16(8-29)43-28)20(34)17-13(31)6-11(39-2)7-15(17)41-25/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16+,18-,19+,21-,22+,23+,24+,27-,28-/m0/s1
SMILES	COC1=CC(O)=C2C(=O)C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]3O)=C(C3=CC=C(O)C(O[C@@H]4O[C@@H](C)[C@H](O)[C@H](O)[C@H]4O)=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	0.947 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.534 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.284 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	258.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.141	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.732	Fsp³:	0.464
MCE-18:	122.073 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.64	Fluc inhibitor:	0.276 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.833 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.613 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.116	Promiscuous compounds:	0.501

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.41	MDCK Permeability:	-5.248
Pgp-inhibitor:	0.0	Pgp-substrate:	0.514
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):	0.868
20% Bioavailability (F20%):	0.14	30% Bioavailability (F30%):	0.958
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.012
Plasma Protein Binding (PPB):	82.943%	Volume Distribution (VD):	-0.057
Fu:	15.416% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.519
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.148
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.979
HLM stability:	0.825 ? 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):

2.019

Half-life (T1/2):

4.984

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.11
Human Hepatotoxicity (H-HT):	0.622	Drug-induced Liver Injury (DILI):	0.966
AMES Toxicity:	0.932	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.013	Skin Sensitization:	0.998
Carcinogencity:	0.071	Eye Corrosion:	0.0
Eye Irritation:	0.041	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.973
Hematotoxicity:	0.252	Drug-induced Nephrotoxicity:	0.41
Genotoxicity:	0.544	RPMI-8226 Immunitoxicity:	0.146
A549 Cytotoxicity:	0.381	Hek293 Cytotoxicity:	0.301
BCF:	0.426 ? 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:	3.059 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.687 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.764 ? 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
NPO49106	Coprosma spp.	Genus	Rubiaceae	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 NPC557013 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	22478
0.1-0.2	23575
0.2-0.3	2568
0.3-0.4	718
0.4-0.5	284
0.5-0.6	128
0.6-0.7	55
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
0.7927	Intermediate Similarity	NPC116458
0.7927	Intermediate Similarity	NPC246943
0.7927	Intermediate Similarity	NPC605784
0.7857	Intermediate Similarity	NPC251417
0.7654	Intermediate Similarity	NPC46420
0.7654	Intermediate Similarity	NPC271692
0.7412	Intermediate Similarity	NPC601586
0.7317	Intermediate Similarity	NPC297987
0.7317	Intermediate Similarity	NPC136042
0.7262	Intermediate Similarity	NPC611303
0.7229	Intermediate Similarity	NPC84362
0.7209	Intermediate Similarity	NPC203050
0.7209	Intermediate Similarity	NPC488072
0.7209	Intermediate Similarity	NPC225434
0.7195	Intermediate Similarity	NPC249281
0.7108	Intermediate Similarity	NPC158674
0.7093	Intermediate Similarity	NPC223747
0.6988	Remote Similarity	NPC289667
0.6977	Remote Similarity	NPC101026
0.6977	Remote Similarity	NPC488077
0.6977	Remote Similarity	NPC601144
0.6897	Remote Similarity	NPC311830
0.6702	Remote Similarity	NPC35119
0.6629	Remote Similarity	NPC276377
0.6593	Remote Similarity	NPC480466
0.6526	Remote Similarity	NPC32641
0.6526	Remote Similarity	NPC256188
0.6517	Remote Similarity	NPC206123
0.6489	Remote Similarity	NPC240306
0.6452	Remote Similarity	NPC150164
0.6404	Remote Similarity	NPC486578
0.6383	Remote Similarity	NPC186816
0.6364	Remote Similarity	NPC14187
0.6354	Remote Similarity	NPC606657
0.6316	Remote Similarity	NPC64425
0.6292	Remote Similarity	NPC488071
0.6275	Remote Similarity	NPC480441
0.6275	Remote Similarity	NPC25523
0.625	Remote Similarity	NPC24043
0.625	Remote Similarity	NPC27640
0.6224	Remote Similarity	NPC476472
0.6224	Remote Similarity	NPC294815
0.6224	Remote Similarity	NPC16194
0.6214	Remote Similarity	NPC277532
0.618	Remote Similarity	NPC42773
0.618	Remote Similarity	NPC59534
0.618	Remote Similarity	NPC45522
0.618	Remote Similarity	NPC325555
0.618	Remote Similarity	NPC226304
0.6136	Remote Similarity	NPC277205
0.6136	Remote Similarity	NPC37919
0.6129	Remote Similarity	NPC480463
0.6111	Remote Similarity	NPC285197
0.6087	Remote Similarity	NPC469931
0.6076	Remote Similarity	NPC78326
0.6067	Remote Similarity	NPC305811
0.6067	Remote Similarity	NPC488080
0.6067	Remote Similarity	NPC169977
0.6061	Remote Similarity	NPC220173
0.6055	Remote Similarity	NPC192539
0.6044	Remote Similarity	NPC22832
0.6044	Remote Similarity	NPC120099
0.6023	Remote Similarity	NPC77672
0.6023	Remote Similarity	NPC133671
0.6023	Remote Similarity	NPC135391
0.6023	Remote Similarity	NPC78263
0.6023	Remote Similarity	NPC250069
0.6023	Remote Similarity	NPC238376
0.602	Remote Similarity	NPC72016
0.6019	Remote Similarity	NPC470720
0.6	Remote Similarity	NPC472459
0.6	Remote Similarity	NPC599850
0.598	Remote Similarity	NPC121703
0.5979	Remote Similarity	NPC153755
0.5955	Remote Similarity	NPC145038
0.5955	Remote Similarity	NPC56077
0.5955	Remote Similarity	NPC281131
0.5955	Remote Similarity	NPC253662
0.5955	Remote Similarity	NPC179950
0.5955	Remote Similarity	NPC323593
0.5955	Remote Similarity	NPC88789
0.5955	Remote Similarity	NPC203500
0.5955	Remote Similarity	NPC189142
0.5955	Remote Similarity	NPC77660
0.5955	Remote Similarity	NPC491374
0.5934	Remote Similarity	NPC60735
0.5934	Remote Similarity	NPC219904
0.5934	Remote Similarity	NPC26230
0.5926	Remote Similarity	NPC470719
0.5926	Remote Similarity	NPC470717
0.5909	Remote Similarity	NPC111929
0.5909	Remote Similarity	NPC320283
0.5909	Remote Similarity	NPC41121
0.59	Remote Similarity	NPC195257
0.5889	Remote Similarity	NPC603655
0.5888	Remote Similarity	NPC295625
0.587	Remote Similarity	NPC21666
0.587	Remote Similarity	NPC197285
0.587	Remote Similarity	NPC609478
0.5865	Remote Similarity	NPC219043
0.5843	Remote Similarity	NPC127546
0.5843	Remote Similarity	NPC39360
0.5843	Remote Similarity	NPC57625
0.5843	Remote Similarity	NPC108831
0.5843	Remote Similarity	NPC19709
0.5843	Remote Similarity	NPC29763
0.5843	Remote Similarity	NPC173637
0.5843	Remote Similarity	NPC210003
0.5843	Remote Similarity	NPC317489
0.5843	Remote Similarity	NPC223424
0.5843	Remote Similarity	NPC182634
0.5843	Remote Similarity	NPC600591
0.5806	Remote Similarity	NPC602805
0.5806	Remote Similarity	NPC607707
0.58	Remote Similarity	NPC5319
0.5778	Remote Similarity	NPC64305
0.5778	Remote Similarity	NPC95090
0.5778	Remote Similarity	NPC265530
0.5778	Remote Similarity	NPC27408
0.5769	Remote Similarity	NPC473072
0.573	Remote Similarity	NPC331652
0.5727	Remote Similarity	NPC488079
0.5714	Remote Similarity	NPC349108
0.5699	Remote Similarity	NPC243930
0.5699	Remote Similarity	NPC601710
0.5684	Remote Similarity	NPC265115
0.5676	Remote Similarity	NPC138990
0.566	Remote Similarity	NPC164704
0.5644	Remote Similarity	NPC142142
0.5644	Remote Similarity	NPC486577
0.5625	Remote Similarity	NPC175429
0.5604	Remote Similarity	NPC8573
0.56	Remote Similarity	NPC470443
0.5591	Remote Similarity	NPC307938
0.5556	Remote Similarity	NPC470716
0.5514	Remote Similarity	NPC470715
0.55	Remote Similarity	NPC488073
0.5495	Remote Similarity	NPC19388
0.5495	Remote Similarity	NPC261866
0.5495	Remote Similarity	NPC240431
0.5495	Remote Similarity	NPC55786
0.5446	Remote Similarity	NPC483414
0.5446	Remote Similarity	NPC483415
0.5417	Remote Similarity	NPC267254
0.5398	Remote Similarity	NPC209550
0.5392	Remote Similarity	NPC483416
0.5385	Remote Similarity	NPC473043
0.5385	Remote Similarity	NPC135599
0.5385	Remote Similarity	NPC73855
0.5385	Remote Similarity	NPC113968
0.5385	Remote Similarity	NPC328940
0.5385	Remote Similarity	NPC277174
0.5385	Remote Similarity	NPC606877
0.5377	Remote Similarity	NPC89052
0.5376	Remote Similarity	NPC22195
0.5376	Remote Similarity	NPC245014
0.5376	Remote Similarity	NPC21190
0.5347	Remote Similarity	NPC126784
0.5347	Remote Similarity	NPC241423
0.5333	Remote Similarity	NPC288084
0.5319	Remote Similarity	NPC117260
0.531	Remote Similarity	NPC488078
0.53	Remote Similarity	NPC156869
0.5278	Remote Similarity	NPC173837
0.5275	Remote Similarity	NPC67037
0.5275	Remote Similarity	NPC255615
0.5263	Remote Similarity	NPC168584
0.5258	Remote Similarity	NPC355481
0.5253	Remote Similarity	NPC139320
0.5248	Remote Similarity	NPC473571
0.5248	Remote Similarity	NPC110941
0.5243	Remote Similarity	NPC209296
0.5243	Remote Similarity	NPC473327
0.5229	Remote Similarity	NPC217520
0.5213	Remote Similarity	NPC58716
0.5213	Remote Similarity	NPC84265
0.5213	Remote Similarity	NPC45638
0.5213	Remote Similarity	NPC73511
0.5208	Remote Similarity	NPC148710
0.5208	Remote Similarity	NPC605067
0.5208	Remote Similarity	NPC606560
0.52	Remote Similarity	NPC173582
0.52	Remote Similarity	NPC265885
0.52	Remote Similarity	NPC181465
0.52	Remote Similarity	NPC471748
0.52	Remote Similarity	NPC215710
0.52	Remote Similarity	NPC67105
0.52	Remote Similarity	NPC473438
0.52	Remote Similarity	NPC253788
0.5189	Remote Similarity	NPC135358
0.5161	Remote Similarity	NPC476405
0.5158	Remote Similarity	NPC201292
0.5149	Remote Similarity	NPC203259
0.5149	Remote Similarity	NPC33054
0.5149	Remote Similarity	NPC210073
0.5149	Remote Similarity	NPC176740
0.5149	Remote Similarity	NPC471725
0.5149	Remote Similarity	NPC134532
0.5149	Remote Similarity	NPC602582
0.5149	Remote Similarity	NPC605592

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC557013 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5620
0.1-0.2	3471
0.2-0.3	46
0.3-0.4	5
0.4-0.5	3
0.5-0.6	4
0.6-0.7	1
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
0.6061	Remote Similarity	NPD7251	Phase 2
0.5825	Remote Similarity	NPD7808	Phase 3
0.58	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5243	Remote Similarity	NPD7054	Phase 4
0.5149	Remote Similarity	NPD6797	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