NPASS Compound

Natural Product: NPC536305

Natural Product ID	NPC536305
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{R},3~{S},4~{S},5~{R},6~{S})-6-[2-[4-[(2~{S},3~{R},4~{R},5~{S},6~{R})-6-[(2-carboxyacetyl)oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxyphenyl]-5-hydroxy-4-oxo-chromen-7-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{R},3~{S},4~{S},5~{R},6~{S})-6-[2-[4-[(2~{S},3~{R},4~{R},5~{S},6~{R})-6-[(2-carboxyacetyl)oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxyphenyl]-5-hydroxy-4-oxo-chromen-7-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0002934] Flavonoid O-glucuronides [CHEMONTID:0003534] Flavonoid-7-O-glucuronides

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 79 83 0 0 0 0 0 0 0 0999 V2000 11.8421 2.7867 -0.8742 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7052 2.3069 0.2820 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1234 3.0541 1.3684 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1133 0.9858 0.4677 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7435 0.8927 -0.1499 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7815 1.3635 0.5135 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4820 0.3379 -1.3685 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2249 0.2197 -1.9951 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3333 -0.6266 -1.1619 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0542 -0.7921 -1.6891 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2458 -1.3569 -0.7082 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9883 -1.5714 -1.2190 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8316 -1.0645 -0.6774 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7946 -0.2837 0.4339 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5756 0.1992 0.9327 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3910 -0.0962 0.3250 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9067 0.3935 0.8437 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9958 1.1877 1.9634 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2125 1.6334 2.4312 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3255 2.3645 3.4577 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3538 1.2699 1.7567 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6042 1.6770 2.1684 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7067 2.4791 3.2984 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7120 1.2693 1.4362 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6298 0.4771 0.3172 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7212 0.0701 -0.4106 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0628 0.3432 -0.1934 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8010 -0.8055 0.1071 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9525 -0.9495 -0.6204 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.7787 -2.0153 0.0231 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3767 -2.6154 1.0557 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0216 -2.3920 -0.4835 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8188 0.3092 -0.5762 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.1932 0.4755 0.7561 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0538 1.5222 -0.9979 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.6494 2.1391 -2.1008 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6583 1.0950 -1.3659 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9049 2.2486 -1.5512 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3425 0.0868 -0.0641 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2269 0.4701 0.6336 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0220 0.0831 0.2470 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4343 -0.8898 -0.8048 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6153 -1.3719 -1.3094 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7939 -2.6920 -0.2258 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9708 -3.2401 0.7628 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2225 -2.5956 0.2194 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3765 -1.7092 1.2896 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0010 -1.9843 -0.9432 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3249 -1.7655 -0.6601 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6671 3.9046 1.2870 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9896 0.7043 1.5277 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7562 0.1746 0.0094 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4217 -0.3389 -2.9544 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7915 1.2053 -2.2600 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1889 -0.1366 -0.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3205 -0.6874 0.1690 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6850 0.0049 0.9882 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6201 0.8165 1.8223 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1157 1.4853 2.5112 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0284 2.0383 4.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6721 1.6123 1.7975 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1722 0.9988 0.6865 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7658 -1.2827 -1.6695 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3590 -3.3396 -0.4036 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7120 0.1266 -1.2084 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4341 1.4260 0.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9609 2.2808 -0.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0923 2.8998 -2.4294 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6433 0.5044 -2.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9382 2.1049 -1.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2348 -0.5416 -0.9439 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5073 -1.1272 -1.2951 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6630 -1.9958 -2.1952 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7463 -3.3759 -1.0956 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7718 -2.5816 1.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6489 -3.5463 0.5436 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5398 -1.3649 1.6566 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9375 -2.6139 -1.8510 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9504 -2.2785 -1.2652 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 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 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 29 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 25 39 1 0 39 40 2 0 40 41 1 0 16 42 1 0 42 43 2 0 11 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 46 48 1 0 48 49 1 0 48 9 1 0 43 13 1 0 41 17 1 0 40 21 1 0 37 27 1 0 3 50 1 0 4 51 1 0 4 52 1 0 8 53 1 0 8 54 1 0 9 55 1 1 11 56 1 1 14 57 1 0 15 58 1 0 18 59 1 0 23 60 1 0 24 61 1 0 27 62 1 1 29 63 1 6 32 64 1 0 33 65 1 6 34 66 1 0 35 67 1 1 36 68 1 0 37 69 1 6 38 70 1 0 39 71 1 0 42 72 1 0 43 73 1 0 44 74 1 6 45 75 1 0 46 76 1 1 47 77 1 0 48 78 1 6 49 79 1 0 M END

Standard InCHIKey	KWPZKEPPMDOLFK-PFQJCDAJSA-N
Standard InCHI	InChI=1S/C30H30O19/c31-13-5-12(46-30-26(41)23(38)24(39)27(49-30)28(42)43)6-16-20(13)14(32)7-15(47-16)10-1-3-11(4-2-10)45-29-25(40)22(37)21(36)17(48-29)9-44-19(35)8-18(33)34/h1-7,17,21-27,29-31,36-41H,8-9H2,(H,33,34)(H,42,43)/t17-,21-,22-,23+,24+,25-,26-,27-,29-,30-/m1/s1
SMILES	O=C(O)CC(=O)OC[C@H]1O[C@@H](OC2=CC=C(C3=CC(=O)C4=C(O)C=C(O[C@@H]5O[C@@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O)C=C4O3)C=C2)[C@H](O)[C@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	694.14	Volume:	622.667 ? Van der Waals volume.
Dense:	1.115	LogP:	-0.602 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.356 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.758 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	33.0
TPSA:	309.64 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.079	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.854	Fsp³:	0.4
MCE-18:	125.143 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.449	Fluc inhibitor:	0.42 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.929 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.642 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.098	Promiscuous compounds:	0.445

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.366	MDCK Permeability:	-5.08
Pgp-inhibitor:	0.0	Pgp-substrate:	0.292
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):	0.301
20% Bioavailability (F20%):	0.045	30% Bioavailability (F30%):	0.089
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.966
Plasma Protein Binding (PPB):	75.853%	Volume Distribution (VD):	-0.247
Fu:	21.178% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.17
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.0
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:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.228
HLM stability:	0.001 ? 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):

0.667

Half-life (T1/2):

4.754

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.005
Human Hepatotoxicity (H-HT):	0.424	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.93	Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.008	Skin Sensitization:	0.998
Carcinogencity:	0.024	Eye Corrosion:	0.0
Eye Irritation:	0.05	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.933
Hematotoxicity:	0.487	Drug-induced Nephrotoxicity:	0.984
Genotoxicity:	0.996	RPMI-8226 Immunitoxicity:	0.138
A549 Cytotoxicity:	0.018	Hek293 Cytotoxicity:	0.03
BCF:	0.115 ? 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:	2.704 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.197 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.354 ? 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
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(91)83628-X]
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11352	Centaurea cyanus	Species	Asteraceae	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 NPC536305 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	20973
0.1-0.2	26198
0.2-0.3	1966
0.3-0.4	491
0.4-0.5	161
0.5-0.6	49
0.6-0.7	13
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8523	High Similarity	NPC46202
0.8132	Intermediate Similarity	NPC229409
0.8111	Intermediate Similarity	NPC64051
0.75	Intermediate Similarity	NPC608742
0.7	Intermediate Similarity	NPC282169
0.6813	Remote Similarity	NPC20505
0.6768	Remote Similarity	NPC479766
0.67	Remote Similarity	NPC479765
0.6429	Remote Similarity	NPC22062
0.6429	Remote Similarity	NPC473634
0.6429	Remote Similarity	NPC138811
0.6176	Remote Similarity	NPC473623
0.6117	Remote Similarity	NPC270675
0.6117	Remote Similarity	NPC488089
0.6117	Remote Similarity	NPC195685
0.6064	Remote Similarity	NPC181712
0.602	Remote Similarity	NPC211594
0.6	Remote Similarity	NPC44931
0.5957	Remote Similarity	NPC95090
0.5957	Remote Similarity	NPC27408
0.5943	Remote Similarity	NPC472994
0.5941	Remote Similarity	NPC210073
0.5865	Remote Similarity	NPC209296
0.5794	Remote Similarity	NPC253685
0.5769	Remote Similarity	NPC65711
0.5766	Remote Similarity	NPC277532
0.5758	Remote Similarity	NPC190003
0.5727	Remote Similarity	NPC472993
0.5701	Remote Similarity	NPC101636
0.5701	Remote Similarity	NPC298171
0.567	Remote Similarity	NPC27942
0.5612	Remote Similarity	NPC237435
0.5579	Remote Similarity	NPC331652
0.5556	Remote Similarity	NPC43211
0.5545	Remote Similarity	NPC121703
0.5545	Remote Similarity	NPC11468
0.5545	Remote Similarity	NPC600989
0.5521	Remote Similarity	NPC39360
0.5521	Remote Similarity	NPC19709
0.5521	Remote Similarity	NPC29763
0.5521	Remote Similarity	NPC210003
0.5464	Remote Similarity	NPC189142
0.5464	Remote Similarity	NPC77660
0.5463	Remote Similarity	NPC477629
0.5429	Remote Similarity	NPC204693
0.5417	Remote Similarity	NPC473043
0.54	Remote Similarity	NPC22832
0.54	Remote Similarity	NPC243930
0.54	Remote Similarity	NPC601144
0.5392	Remote Similarity	NPC172807
0.5347	Remote Similarity	NPC607707
0.534	Remote Similarity	NPC254540
0.5304	Remote Similarity	NPC488087
0.5278	Remote Similarity	NPC483707
0.5214	Remote Similarity	NPC488086
0.5204	Remote Similarity	NPC261866
0.52	Remote Similarity	NPC101191
0.5196	Remote Similarity	NPC311830
0.5149	Remote Similarity	NPC210094
0.5098	Remote Similarity	NPC115760
0.5098	Remote Similarity	NPC610187
0.5085	Remote Similarity	NPC68592
0.5051	Remote Similarity	NPC289667
0.5051	Remote Similarity	NPC58053
0.5051	Remote Similarity	NPC143851
0.5045	Remote Similarity	NPC80068
0.5045	Remote Similarity	NPC475382

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC536305 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4140
0.1-0.2	4919
0.2-0.3	82
0.3-0.4	3
0.4-0.5	4
0.5-0.6	2
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
0.5865	Remote Similarity	NPD7054	Phase 4
0.5612	Remote Similarity	NPD4338	Clinical (unspecified phase)

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