NPASS Compound

Natural Product: NPC514662

Natural Product ID	NPC514662
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,6-dihydroxy-2-[3-hydroxy-4-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5,6-dihydroxy-2-[3-hydroxy-4-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-7-[(2~{S},3~{R},4~{S},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 74 78 0 0 0 0 0 0 0 0999 V2000 1.0272 -2.3862 4.2817 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8219 -1.8370 3.1696 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4867 -1.5544 2.7466 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6822 -0.9616 1.5411 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0270 -0.6596 1.0727 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2075 -0.1318 -0.2037 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4644 0.1846 -0.7110 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5814 -0.0162 0.0414 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8378 0.2702 -0.3938 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2873 0.7534 -1.6068 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8783 1.9706 -1.5909 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1529 2.1114 -1.1691 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2524 2.9708 0.1078 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7412 4.2513 -0.1244 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0179 0.9090 -1.0852 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1811 1.0063 -1.8886 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3635 -0.4099 -1.2965 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9130 -1.0059 -0.1193 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1781 -0.3137 -2.2538 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6382 0.0805 -3.4872 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4151 -0.5449 1.3226 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5658 -0.7437 2.0731 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1517 -0.8548 1.8133 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3604 -0.6515 0.7703 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -0.8888 1.1096 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6558 -0.5527 0.2881 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9944 -0.7853 0.6077 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9290 -0.3984 -0.3016 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3032 -0.5325 -0.3321 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8835 0.6732 0.0960 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2770 0.5735 0.0149 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8969 1.6362 0.9014 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2736 1.5197 0.8063 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6244 0.7939 -1.4340 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0058 0.7009 -1.6362 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9021 -0.1874 -2.2763 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4889 0.4614 -3.4762 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7570 -0.9136 -1.7092 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0779 -2.2897 -1.6422 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2165 -1.3859 1.8213 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4824 -1.6708 2.2579 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1626 -1.7303 2.6605 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3916 -2.3454 3.9056 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8517 -1.4925 2.3281 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3148 -1.8149 3.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3153 0.0316 -0.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5352 0.5995 -1.7264 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4111 0.8390 -2.3114 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6549 2.7840 -1.9439 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3257 3.1295 0.3627 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7049 2.5405 0.9466 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3435 4.3461 -1.0281 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4438 0.8772 -0.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8015 0.2848 -1.5815 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0859 -1.1094 -1.7642 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9720 -0.4072 0.6662 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6378 -1.2630 -2.2268 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9252 -0.6979 -4.0378 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7151 -1.6769 2.4206 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0935 -1.2632 2.8241 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4546 -0.0767 -0.6628 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6339 -1.2715 0.4182 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6529 -0.4148 0.3229 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6111 1.3844 1.9461 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5258 2.6448 0.6664 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5745 0.5989 0.7168 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2554 1.8154 -1.6883 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4428 1.5784 -1.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6771 -0.9254 -2.6604 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4735 1.4547 -3.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8860 -0.8811 -2.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0510 -2.7386 -2.4943 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7621 -1.3588 3.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3164 -2.6319 4.2126 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 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 8 21 1 0 21 22 1 0 21 23 2 0 4 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 27 40 2 0 40 41 1 0 40 42 1 0 42 43 1 0 42 44 2 0 44 2 1 0 23 5 1 0 44 25 1 0 19 10 1 0 38 29 1 0 3 45 1 0 6 46 1 0 7 47 1 0 10 48 1 6 12 49 1 6 13 50 1 0 13 51 1 0 14 52 1 0 15 53 1 1 16 54 1 0 17 55 1 6 18 56 1 0 19 57 1 6 20 58 1 0 22 59 1 0 23 60 1 0 26 61 1 0 29 62 1 1 31 63 1 1 32 64 1 0 32 65 1 0 33 66 1 0 34 67 1 6 35 68 1 0 36 69 1 6 37 70 1 0 38 71 1 6 39 72 1 0 41 73 1 0 43 74 1 0 M END

Standard InCHIKey	MEDQUZYOAMPIAV-IJTBWITGSA-N
Standard InCHI	InChI=1S/C27H30O17/c28-6-15-19(33)22(36)24(38)26(43-15)41-11-2-1-8(3-9(11)30)12-4-10(31)17-13(40-12)5-14(18(32)21(17)35)42-27-25(39)23(37)20(34)16(7-29)44-27/h1-5,15-16,19-20,22-30,32-39H,6-7H2/t15-,16-,19-,20-,22+,23+,24-,25-,26-,27-/m1/s1
SMILES	O=C1C=C(C2=CC=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(O)=C2)OC2=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C(O)C(O)=C12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	626.15	Volume:	561.108 ? Van der Waals volume.
Dense:	1.116	LogP:	-0.039 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.846 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.501 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	289.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	11.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.116	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.803	Fsp³:	0.444
MCE-18:	122.949 ? 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:	1
Colloidal aggregators:	0.64	Fluc inhibitor:	0.311 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.921 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.602 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.328	Promiscuous compounds:	0.605

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.677	MDCK Permeability:	-4.978
Pgp-inhibitor:	0.0	Pgp-substrate:	0.282
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):	0.988
20% Bioavailability (F20%):	0.506	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.133
Plasma Protein Binding (PPB):	80.262%	Volume Distribution (VD):	-0.086
Fu:	18.892% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.65
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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.003
HLM stability:	0.0 ? 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):

1.579

Half-life (T1/2):

5.997

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.016
Human Hepatotoxicity (H-HT):	0.753	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.971	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	1.0
Carcinogencity:	0.099	Eye Corrosion:	0.0
Eye Irritation:	0.016	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.993
Hematotoxicity:	0.269	Drug-induced Nephrotoxicity:	0.757
Genotoxicity:	0.898	RPMI-8226 Immunitoxicity:	0.13
A549 Cytotoxicity:	0.438	Hek293 Cytotoxicity:	0.212
BCF:	0.245 ? 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:	2.582 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.34 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.314 ? 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
NPO13512	Opuntia ficus-indica	Species	Cactaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.indcrop.2014.08.046]
NPO13512	Opuntia ficus-indica	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39339457]
NPO13512	Opuntia ficus-indica	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13512	Opuntia ficus-indica	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13512	Opuntia ficus-indica	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13512	Opuntia ficus-indica	Species	Cactaceae	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 NPC514662 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	22505
0.1-0.2	23622
0.2-0.3	2506
0.3-0.4	868
0.4-0.5	262
0.5-0.6	47
0.6-0.7	36
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8472	Intermediate Similarity	NPC58716
0.8194	Intermediate Similarity	NPC45618
0.8082	Intermediate Similarity	NPC146792
0.7895	Intermediate Similarity	NPC605067
0.7532	Intermediate Similarity	NPC191306
0.7436	Intermediate Similarity	NPC22832
0.7024	Intermediate Similarity	NPC3583
0.6625	Remote Similarity	NPC245014
0.6582	Remote Similarity	NPC58053
0.65	Remote Similarity	NPC95090
0.65	Remote Similarity	NPC27408
0.65	Remote Similarity	NPC189142
0.65	Remote Similarity	NPC77660
0.6463	Remote Similarity	NPC285197
0.642	Remote Similarity	NPC186807
0.642	Remote Similarity	NPC84265
0.642	Remote Similarity	NPC45638
0.6386	Remote Similarity	NPC486578
0.6386	Remote Similarity	NPC601144
0.6375	Remote Similarity	NPC261866
0.6374	Remote Similarity	NPC256760
0.6341	Remote Similarity	NPC201292
0.6265	Remote Similarity	NPC609451
0.6197	Remote Similarity	NPC212678
0.619	Remote Similarity	NPC243930
0.6173	Remote Similarity	NPC39360
0.6173	Remote Similarity	NPC29763
0.6173	Remote Similarity	NPC210003
0.6173	Remote Similarity	NPC143851
0.6145	Remote Similarity	NPC21100
0.6118	Remote Similarity	NPC311830
0.6118	Remote Similarity	NPC602805
0.6118	Remote Similarity	NPC607707
0.6098	Remote Similarity	NPC93337
0.6098	Remote Similarity	NPC168822
0.6092	Remote Similarity	NPC251417
0.6071	Remote Similarity	NPC60735
0.6071	Remote Similarity	NPC26230
0.6047	Remote Similarity	NPC469931
0.6024	Remote Similarity	NPC105025
0.6	Remote Similarity	NPC21666
0.6	Remote Similarity	NPC601710
0.6	Remote Similarity	NPC609478
0.5747	Remote Similarity	NPC88023
0.5747	Remote Similarity	NPC309025
0.5714	Remote Similarity	NPC607513
0.5632	Remote Similarity	NPC284960
0.5632	Remote Similarity	NPC120099
0.5595	Remote Similarity	NPC289667
0.5517	Remote Similarity	NPC237435
0.5495	Remote Similarity	NPC603300
0.5474	Remote Similarity	NPC209296
0.5474	Remote Similarity	NPC150767
0.5465	Remote Similarity	NPC610763
0.5455	Remote Similarity	NPC43211
0.5412	Remote Similarity	NPC254306
0.5412	Remote Similarity	NPC19709
0.5412	Remote Similarity	NPC83283
0.5402	Remote Similarity	NPC182045
0.5385	Remote Similarity	NPC8856
0.5349	Remote Similarity	NPC259152
0.5333	Remote Similarity	NPC198199
0.5287	Remote Similarity	NPC181712
0.527	Remote Similarity	NPC57030
0.5227	Remote Similarity	NPC222936
0.5222	Remote Similarity	NPC307518
0.52	Remote Similarity	NPC162313
0.5185	Remote Similarity	NPC120952
0.5172	Remote Similarity	NPC297987
0.5172	Remote Similarity	NPC64305
0.5172	Remote Similarity	NPC277205
0.5172	Remote Similarity	NPC37919
0.5172	Remote Similarity	NPC136042
0.5165	Remote Similarity	NPC190003
0.5165	Remote Similarity	NPC601586
0.5116	Remote Similarity	NPC473043
0.5116	Remote Similarity	NPC331652
0.5114	Remote Similarity	NPC84362
0.5111	Remote Similarity	NPC115760
0.5111	Remote Similarity	NPC229729
0.5109	Remote Similarity	NPC477848
0.5109	Remote Similarity	NPC600989
0.5065	Remote Similarity	NPC160951
0.5065	Remote Similarity	NPC283600
0.5063	Remote Similarity	NPC485299
0.5057	Remote Similarity	NPC110349
0.5056	Remote Similarity	NPC472459
0.5056	Remote Similarity	NPC27942
0.5056	Remote Similarity	NPC117260
0.5054	Remote Similarity	NPC254540

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC514662 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5451
0.1-0.2	3608
0.2-0.3	74
0.3-0.4	11
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
0.5517	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5474	Remote Similarity	NPD7054	Phase 4

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