NPASS Compound

Natural Product: NPC556165

Natural Product ID	NPC556165
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	7-hydroxy-5-methoxy-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-[4-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]chromen-4-one
IUPAC Name	7-hydroxy-5-methoxy-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-[4-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]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 -6.8289 4.1430 1.5565 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5950 3.4418 1.4308 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4949 4.0433 0.8285 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5230 5.3257 0.3262 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3965 5.8588 -0.2576 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4140 7.1693 -0.7751 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2566 5.1022 -0.3311 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1836 3.8021 0.1633 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3219 3.2922 0.7418 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2446 2.0107 1.2234 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2471 1.4943 1.7587 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0350 1.3056 1.1033 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0636 0.0144 1.6133 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5854 -1.0596 0.8208 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7479 -1.4465 1.5337 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5516 -2.2554 0.7922 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2261 -1.5857 -0.3845 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0307 -0.5351 -0.0161 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8741 -3.5303 0.3687 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9910 -4.4674 1.4036 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4605 -3.3357 -0.0536 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4288 -3.0637 -1.4248 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7228 -2.2534 0.7177 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3354 -2.7790 1.9433 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9455 1.8606 0.5293 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3639 1.2169 0.3618 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7587 0.0898 0.9865 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0201 -0.4501 0.7036 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8950 0.0982 -0.1776 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1461 -0.3673 -0.5111 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7084 -1.4933 0.0386 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9414 -1.3041 0.6361 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0090 -1.1365 -0.1967 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1437 0.3034 -0.6915 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2698 0.3718 -1.5374 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1275 -2.1108 -1.3244 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6683 -3.2947 -0.8398 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8439 -2.3883 -2.0292 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5582 -1.4739 -3.0343 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7510 -2.5646 -1.0367 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8366 -3.7827 -0.3985 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4710 1.2624 -0.8120 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2586 1.7951 -0.5509 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0832 3.1100 0.0771 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5107 3.6257 2.2525 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3045 4.1015 0.5521 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6899 5.1776 1.9105 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4058 5.9136 0.3830 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1104 7.9017 -0.1499 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3790 5.5242 -0.7884 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8857 -0.7210 -0.1689 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3886 -2.5840 1.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9292 -2.3746 -0.7972 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4867 -1.3935 -1.1579 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1924 -0.6205 0.9749 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4580 -3.9569 -0.4909 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7458 -4.2540 1.9844 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9017 -4.2828 0.1184 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2619 -3.3299 -1.8862 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7896 -2.0848 0.1217 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6722 -3.4910 1.7387 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1218 -0.3931 1.7230 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2675 -1.3550 1.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0540 -1.9081 0.8258 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9300 -1.2917 0.4446 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2254 0.6643 -1.1936 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3527 0.9988 0.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6991 1.2516 -1.4369 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8565 -1.6802 -2.0557 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1885 -3.6942 -1.5822 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9687 -3.3828 -2.5510 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2891 -0.8160 -3.0957 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7434 -2.5299 -1.5318 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1254 -3.8885 0.2943 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1324 1.7310 -1.5170 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9740 2.7090 -1.0740 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 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 12 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 29 42 1 0 42 43 2 0 25 44 1 0 9 3 1 0 23 14 1 0 43 26 1 0 44 8 1 0 40 31 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 6 49 1 0 7 50 1 0 14 51 1 6 16 52 1 1 17 53 1 0 17 54 1 0 18 55 1 0 19 56 1 6 20 57 1 0 21 58 1 6 22 59 1 0 23 60 1 6 24 61 1 0 27 62 1 0 28 63 1 0 31 64 1 1 33 65 1 1 34 66 1 0 34 67 1 0 35 68 1 0 36 69 1 6 37 70 1 0 38 71 1 6 39 72 1 0 40 73 1 6 41 74 1 0 42 75 1 0 43 76 1 0 M END

Standard InCHIKey	GZUKYQXUDAPZLC-YEQWUJJHSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-39-13-6-11(31)7-14-17(13)20(34)26(44-28-24(38)22(36)19(33)16(9-30)43-28)25(41-14)10-2-4-12(5-3-10)40-27-23(37)21(35)18(32)15(8-29)42-27/h2-7,15-16,18-19,21-24,27-33,35-38H,8-9H2,1H3/t15-,16+,18-,19+,21+,22-,23-,24+,27-,28+/m1/s1
SMILES	COC1=CC(O)=CC2=C1C(=O)C(O[C@@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]1O)=C(C1=CC=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C1)O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	0.359 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.126 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.521 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	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:	0.126	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.651	Fsp³:	0.464
MCE-18:	118.585 ? 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:	0.63	Fluc inhibitor:	0.286 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.704 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.587 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.109	Promiscuous compounds:	0.306

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.673	MDCK Permeability:	-5.051
Pgp-inhibitor:	0.0	Pgp-substrate:	0.354
PAMPA:	0.999 ? 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):	0.981
20% Bioavailability (F20%):	0.16	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.021
Plasma Protein Binding (PPB):	81.37%	Volume Distribution (VD):	-0.084
Fu:	16.903% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.122
BSEP inhibitor:	0.001

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:	0.954
HLM stability:	0.002 ? 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):

1.623

Half-life (T1/2):

3.632

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.032
Human Hepatotoxicity (H-HT):	0.847	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.987	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	1.0
Carcinogencity:	0.159	Eye Corrosion:	0.0
Eye Irritation:	0.061	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.971
Hematotoxicity:	0.345	Drug-induced Nephrotoxicity:	0.873
Genotoxicity:	0.87	RPMI-8226 Immunitoxicity:	0.219
A549 Cytotoxicity:	0.709	Hek293 Cytotoxicity:	0.325
BCF:	0.468 ? 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:	3.172 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.745 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.829 ? 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
NPO19803	Oxytropis ochrocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22494026]
NPO19803	Oxytropis ochrocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19803	Oxytropis ochrocephala	Species	Fabaceae	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 NPC556165 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	14266
0.1-0.2	30420
0.2-0.3	3773
0.3-0.4	861
0.4-0.5	358
0.5-0.6	120
0.6-0.7	39
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8219	Intermediate Similarity	NPC599850
0.75	Intermediate Similarity	NPC472459
0.7467	Intermediate Similarity	NPC64305
0.7105	Intermediate Similarity	NPC289667
0.675	Remote Similarity	NPC479401
0.6667	Remote Similarity	NPC120099
0.65	Remote Similarity	NPC24043
0.65	Remote Similarity	NPC488080
0.65	Remote Similarity	NPC169977
0.6456	Remote Similarity	NPC77672
0.6456	Remote Similarity	NPC133671
0.6456	Remote Similarity	NPC135391
0.6456	Remote Similarity	NPC78263
0.6456	Remote Similarity	NPC250069
0.6375	Remote Similarity	NPC297987
0.6341	Remote Similarity	NPC60735
0.6341	Remote Similarity	NPC26230
0.6265	Remote Similarity	NPC609478
0.625	Remote Similarity	NPC83283
0.622	Remote Similarity	NPC222936
0.622	Remote Similarity	NPC325555
0.622	Remote Similarity	NPC226304
0.619	Remote Similarity	NPC206123
0.619	Remote Similarity	NPC116458
0.619	Remote Similarity	NPC246943
0.6173	Remote Similarity	NPC145038
0.6173	Remote Similarity	NPC56077
0.6173	Remote Similarity	NPC281131
0.6173	Remote Similarity	NPC253662
0.6173	Remote Similarity	NPC179950
0.6173	Remote Similarity	NPC88789
0.6173	Remote Similarity	NPC491374
0.6173	Remote Similarity	NPC609879
0.6118	Remote Similarity	NPC203050
0.6118	Remote Similarity	NPC225434
0.6092	Remote Similarity	NPC476773
0.6071	Remote Similarity	NPC148710
0.6049	Remote Similarity	NPC19388
0.6049	Remote Similarity	NPC240431
0.6049	Remote Similarity	NPC55786
0.6049	Remote Similarity	NPC143851
0.6024	Remote Similarity	NPC42773
0.6024	Remote Similarity	NPC45522
0.5977	Remote Similarity	NPC251417
0.5976	Remote Similarity	NPC136042
0.5952	Remote Similarity	NPC488071
0.5914	Remote Similarity	NPC76831
0.5904	Remote Similarity	NPC84362
0.5882	Remote Similarity	NPC101026
0.5882	Remote Similarity	NPC21666
0.5882	Remote Similarity	NPC488077
0.5854	Remote Similarity	NPC58053
0.5824	Remote Similarity	NPC64425
0.5814	Remote Similarity	NPC605784
0.5806	Remote Similarity	NPC5319
0.5783	Remote Similarity	NPC95090
0.5783	Remote Similarity	NPC27408
0.5765	Remote Similarity	NPC219904
0.5758	Remote Similarity	NPC277532
0.5747	Remote Similarity	NPC488072
0.573	Remote Similarity	NPC139320
0.5714	Remote Similarity	NPC186807
0.5714	Remote Similarity	NPC46420
0.5679	Remote Similarity	NPC288084
0.5595	Remote Similarity	NPC8573
0.5595	Remote Similarity	NPC258035
0.5595	Remote Similarity	NPC156457
0.5581	Remote Similarity	NPC479402
0.5581	Remote Similarity	NPC611303
0.5542	Remote Similarity	NPC111929
0.5542	Remote Similarity	NPC320283
0.5542	Remote Similarity	NPC41121
0.5534	Remote Similarity	NPC470713
0.5529	Remote Similarity	NPC73511
0.5529	Remote Similarity	NPC603655
0.5529	Remote Similarity	NPC610763
0.5517	Remote Similarity	NPC486578
0.55	Remote Similarity	NPC470712
0.5495	Remote Similarity	NPC471748
0.5493	Remote Similarity	NPC230285
0.5476	Remote Similarity	NPC249281
0.5465	Remote Similarity	NPC138540
0.5455	Remote Similarity	NPC88023
0.5455	Remote Similarity	NPC309025
0.5422	Remote Similarity	NPC67037
0.5422	Remote Similarity	NPC255615
0.5412	Remote Similarity	NPC265530
0.5405	Remote Similarity	NPC470216
0.5402	Remote Similarity	NPC168584
0.5392	Remote Similarity	NPC470716
0.5385	Remote Similarity	NPC480466
0.5368	Remote Similarity	NPC35119
0.5349	Remote Similarity	NPC271692
0.5347	Remote Similarity	NPC470715
0.5341	Remote Similarity	NPC22832
0.5341	Remote Similarity	NPC243930
0.5301	Remote Similarity	NPC34531
0.5294	Remote Similarity	NPC127546
0.5294	Remote Similarity	NPC57625
0.5294	Remote Similarity	NPC173637
0.5294	Remote Similarity	NPC317489
0.5294	Remote Similarity	NPC223424
0.5294	Remote Similarity	NPC600591
0.5288	Remote Similarity	NPC295625
0.5287	Remote Similarity	NPC182045
0.5287	Remote Similarity	NPC100720
0.5287	Remote Similarity	NPC21100
0.5283	Remote Similarity	NPC470720
0.5281	Remote Similarity	NPC223747
0.5281	Remote Similarity	NPC607707
0.5275	Remote Similarity	NPC473682
0.5275	Remote Similarity	NPC480463
0.5269	Remote Similarity	NPC156869
0.5248	Remote Similarity	NPC48984
0.5233	Remote Similarity	NPC158674
0.5233	Remote Similarity	NPC323593
0.5233	Remote Similarity	NPC203500
0.5227	Remote Similarity	NPC191306
0.5227	Remote Similarity	NPC175107
0.5227	Remote Similarity	NPC285197
0.5227	Remote Similarity	NPC609451
0.5222	Remote Similarity	NPC170052
0.5222	Remote Similarity	NPC135846
0.5217	Remote Similarity	NPC29958
0.5213	Remote Similarity	NPC131745
0.5208	Remote Similarity	NPC32641
0.5208	Remote Similarity	NPC256188
0.5176	Remote Similarity	NPC135599
0.5176	Remote Similarity	NPC73855
0.5176	Remote Similarity	NPC113968
0.5176	Remote Similarity	NPC328940
0.5176	Remote Similarity	NPC277174
0.5176	Remote Similarity	NPC606877
0.5172	Remote Similarity	NPC305811
0.5172	Remote Similarity	NPC27640
0.5172	Remote Similarity	NPC105025
0.5169	Remote Similarity	NPC605067
0.5158	Remote Similarity	NPC488073
0.5158	Remote Similarity	NPC240306
0.5135	Remote Similarity	NPC149127
0.5116	Remote Similarity	NPC39360
0.5116	Remote Similarity	NPC29763
0.5116	Remote Similarity	NPC210003
0.5114	Remote Similarity	NPC117260
0.5111	Remote Similarity	NPC479406
0.5109	Remote Similarity	NPC278419
0.5109	Remote Similarity	NPC179198
0.51	Remote Similarity	NPC244875
0.5057	Remote Similarity	NPC93337
0.5057	Remote Similarity	NPC277205
0.5057	Remote Similarity	NPC37919
0.5057	Remote Similarity	NPC234739
0.5056	Remote Similarity	NPC159579
0.5055	Remote Similarity	NPC276377
0.5055	Remote Similarity	NPC601586
0.5054	Remote Similarity	NPC603300
0.5054	Remote Similarity	NPC609888
0.5053	Remote Similarity	NPC470444
0.5052	Remote Similarity	NPC124155
0.5052	Remote Similarity	NPC473327
0.5049	Remote Similarity	NPC25523
0.5049	Remote Similarity	NPC164704
0.5047	Remote Similarity	NPC470717

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC556165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4141
0.1-0.2	4870
0.2-0.3	123
0.3-0.4	8
0.4-0.5	7
0.5-0.6	1
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
0.5806	Remote Similarity	NPD7804	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