NPASS Compound

Natural Product: NPC533709

Natural Product ID	NPC533709
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~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-[3-hydroxy-4-[(2~{S},3~{R},4~{R},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-[3-hydroxy-4-[(2~{S},3~{R},4~{R},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-carboxylic acid
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 72 76 0 0 0 0 0 0 0 0999 V2000 8.4363 2.3678 2.1493 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1989 2.0209 1.2129 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5752 2.0626 1.4698 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6725 1.5792 -0.1261 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3009 1.6463 -0.0632 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6849 0.5389 -0.6561 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3184 0.7147 -0.7042 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3774 -0.1269 -0.1693 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6536 -1.2858 0.5023 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6538 -2.1002 1.0238 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9778 -3.2855 1.7089 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3370 -1.7320 0.8614 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2958 -2.4827 1.3472 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5769 -3.5435 1.9608 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0019 -2.0498 1.1459 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2845 -0.8844 0.4709 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6370 -0.3897 0.2358 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7370 -1.0599 0.6794 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0328 -0.5587 0.4382 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2293 0.6064 -0.2430 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4746 1.1217 -0.4945 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6650 0.5597 -0.1085 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5336 0.3750 -1.2204 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5348 -0.5114 -0.8744 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4745 -0.5965 -2.0800 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9694 0.7056 -2.3024 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3536 -0.0976 0.2981 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.8465 -1.2771 0.9009 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6163 0.6574 1.3485 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1157 -0.1603 2.3632 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4812 1.4976 0.8046 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7141 1.9770 1.8366 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0741 1.2641 -0.6817 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2886 2.4567 -1.3784 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8044 0.7906 -0.4557 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7569 -0.2038 0.0264 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9997 -0.5752 0.1936 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0448 0.2067 -0.3106 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3126 0.4355 -2.0483 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5110 -0.4564 -2.7735 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6948 -0.1477 -1.8507 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5194 0.3436 -2.8650 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2141 0.2306 -0.5024 C 0 0 1 0 0 0 0 0 0 0 0 0 10.6121 0.3316 -0.5297 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9052 1.7323 2.3814 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0692 2.3081 -0.8666 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0114 -0.3741 -0.1300 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6671 -1.5908 0.6401 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2061 -3.2858 2.6940 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8175 -2.6659 1.5430 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6321 -1.9828 1.2210 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8426 -1.1534 0.8247 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5975 -0.3886 0.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0681 -1.5147 -0.7790 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3371 -1.1967 -1.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9588 -0.9822 -2.9686 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3822 1.3743 -1.8661 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2543 0.4577 -0.0340 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2272 -2.0395 0.6787 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3625 1.3402 1.8504 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4245 -1.0880 2.2971 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8887 2.2764 0.1446 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1470 2.8022 2.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1045 2.5566 -2.3625 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9443 1.3542 -0.8260 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7842 1.1156 -0.8354 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3407 1.4359 -2.5278 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5695 -0.2263 -2.7342 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5880 -1.2537 -1.9233 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9688 1.1501 -2.4678 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9989 -0.5420 0.2885 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0198 -0.5841 -0.5838 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 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 10 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 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 24 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 20 33 1 0 33 34 1 0 33 35 2 0 16 36 1 0 36 37 1 0 37 38 2 0 6 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 43 4 1 0 38 8 1 0 37 12 1 0 35 17 1 0 31 22 1 0 3 45 1 0 4 46 1 6 6 47 1 1 9 48 1 0 11 49 1 0 15 50 1 0 18 51 1 0 19 52 1 0 22 53 1 1 24 54 1 1 25 55 1 0 25 56 1 0 26 57 1 0 27 58 1 6 28 59 1 0 29 60 1 1 30 61 1 0 31 62 1 6 32 63 1 0 34 64 1 0 35 65 1 0 38 66 1 0 39 67 1 6 40 68 1 0 41 69 1 1 42 70 1 0 43 71 1 1 44 72 1 0 M END

Standard InCHIKey	DUNZXXOAZWJFBE-OTMXKAEZSA-N
Standard InCHI	InChI=1S/C27H28O17/c28-7-16-18(32)19(33)22(36)27(43-16)42-13-2-1-8(3-10(13)29)14-6-12(31)17-11(30)4-9(5-15(17)41-14)40-26-23(37)20(34)21(35)24(44-26)25(38)39/h1-6,16,18-24,26-30,32-37H,7H2,(H,38,39)/t16-,18-,19-,20+,21-,22-,23-,24-,26-,27-/m1/s1
SMILES	O=C(O)[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(C4=CC=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]5O)C(O)=C4)OC3=C2)[C@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.13	Volume:	558.471 ? Van der Waals volume.
Dense:	1.118	LogP:	-0.208 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.692 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.725 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	31.0
TPSA:	286.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.128	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.763	Fsp³:	0.407
MCE-18:	123.421 ? 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:	0.506	Fluc inhibitor:	0.33 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.882 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.664 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.331	Promiscuous compounds:	0.502

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.51	MDCK Permeability:	-5.049
Pgp-inhibitor:	0.0	Pgp-substrate:	0.83
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):	0.905
20% Bioavailability (F20%):	0.377	30% Bioavailability (F30%):	0.98
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.761
Plasma Protein Binding (PPB):	73.814%	Volume Distribution (VD):	-0.177
Fu:	23.095% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.829
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.03
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.241	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:	0.158
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):

1.211

Half-life (T1/2):

6.466

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.018
Human Hepatotoxicity (H-HT):	0.478	Drug-induced Liver Injury (DILI):	0.953
AMES Toxicity:	0.704	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.01	Skin Sensitization:	0.956
Carcinogencity:	0.016	Eye Corrosion:	0.0
Eye Irritation:	0.054	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.981
Hematotoxicity:	0.055	Drug-induced Nephrotoxicity:	0.555
Genotoxicity:	0.293	RPMI-8226 Immunitoxicity:	0.09
A549 Cytotoxicity:	0.061	Hek293 Cytotoxicity:	0.067
BCF:	0.23 ? 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:	2.737 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.377 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.417 ? 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
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[23507295]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34889124]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO14621	Cuminum cyminum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14621	Cuminum cyminum	Species	Apiaceae	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 NPC533709 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	23196
0.1-0.2	23629
0.2-0.3	2127
0.3-0.4	609
0.4-0.5	192
0.5-0.6	79
0.6-0.7	18
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
0.7674	Intermediate Similarity	NPC22832
0.7356	Intermediate Similarity	NPC20505
0.7273	Intermediate Similarity	NPC608742
0.7033	Intermediate Similarity	NPC600989
0.7011	Intermediate Similarity	NPC189142
0.7011	Intermediate Similarity	NPC77660
0.6966	Remote Similarity	NPC282169
0.6889	Remote Similarity	NPC601144
0.6869	Remote Similarity	NPC253685
0.6818	Remote Similarity	NPC95090
0.6818	Remote Similarity	NPC27408
0.6593	Remote Similarity	NPC191306
0.6593	Remote Similarity	NPC285197
0.6522	Remote Similarity	NPC243930
0.6522	Remote Similarity	NPC605067
0.6517	Remote Similarity	NPC261866
0.6517	Remote Similarity	NPC39360
0.6517	Remote Similarity	NPC29763
0.6517	Remote Similarity	NPC210003
0.6452	Remote Similarity	NPC311830
0.6344	Remote Similarity	NPC486578
0.6277	Remote Similarity	NPC607707
0.625	Remote Similarity	NPC251417
0.6139	Remote Similarity	NPC229409
0.5978	Remote Similarity	NPC19709
0.5941	Remote Similarity	NPC46202
0.5918	Remote Similarity	NPC8856
0.5895	Remote Similarity	NPC237435
0.5851	Remote Similarity	NPC58716
0.5833	Remote Similarity	NPC43211
0.5825	Remote Similarity	NPC209296
0.5806	Remote Similarity	NPC289667
0.5784	Remote Similarity	NPC64051
0.5758	Remote Similarity	NPC606546
0.5714	Remote Similarity	NPC190003
0.5699	Remote Similarity	NPC473043
0.5684	Remote Similarity	NPC181712
0.5638	Remote Similarity	NPC58053
0.5638	Remote Similarity	NPC143851
0.5579	Remote Similarity	NPC168822
0.5579	Remote Similarity	NPC277205
0.5579	Remote Similarity	NPC37919
0.5579	Remote Similarity	NPC136042
0.5567	Remote Similarity	NPC135277
0.5534	Remote Similarity	NPC115674
0.5532	Remote Similarity	NPC331652
0.5526	Remote Similarity	NPC198199
0.5521	Remote Similarity	NPC186807
0.5521	Remote Similarity	NPC84362
0.5521	Remote Similarity	NPC45638
0.5517	Remote Similarity	NPC120952
0.551	Remote Similarity	NPC115760
0.551	Remote Similarity	NPC601710
0.5474	Remote Similarity	NPC45618
0.5464	Remote Similarity	NPC27942
0.5464	Remote Similarity	NPC201292
0.5421	Remote Similarity	NPC256760
0.5417	Remote Similarity	NPC297987
0.5417	Remote Similarity	NPC146792
0.54	Remote Similarity	NPC601586
0.5306	Remote Similarity	NPC21100
0.5306	Remote Similarity	NPC101191
0.53	Remote Similarity	NPC605784
0.5288	Remote Similarity	NPC210073
0.5283	Remote Similarity	NPC65711
0.5278	Remote Similarity	NPC475382
0.5258	Remote Similarity	NPC323593
0.5258	Remote Similarity	NPC203500
0.5253	Remote Similarity	NPC60735
0.5253	Remote Similarity	NPC26230
0.5253	Remote Similarity	NPC210094
0.5253	Remote Similarity	NPC609451
0.5253	Remote Similarity	NPC611303
0.5214	Remote Similarity	NPC470719
0.52	Remote Similarity	NPC284960
0.52	Remote Similarity	NPC80188
0.52	Remote Similarity	NPC609478
0.52	Remote Similarity	NPC610187
0.5189	Remote Similarity	NPC64425
0.5175	Remote Similarity	NPC277532
0.5172	Remote Similarity	NPC223579
0.5149	Remote Similarity	NPC88023
0.5149	Remote Similarity	NPC116458
0.5149	Remote Similarity	NPC246943
0.5149	Remote Similarity	NPC220169
0.5149	Remote Similarity	NPC309025
0.5149	Remote Similarity	NPC602805
0.5143	Remote Similarity	NPC22062
0.5143	Remote Similarity	NPC65003
0.5143	Remote Similarity	NPC473634
0.5143	Remote Similarity	NPC138811
0.5138	Remote Similarity	NPC195257
0.5135	Remote Similarity	NPC14187
0.5102	Remote Similarity	NPC93337
0.51	Remote Similarity	NPC307938
0.5054	Remote Similarity	NPC191154
0.5051	Remote Similarity	NPC105025
0.5051	Remote Similarity	NPC610763
0.505	Remote Similarity	NPC21666
0.5046	Remote Similarity	NPC479766
0.5046	Remote Similarity	NPC270675
0.5046	Remote Similarity	NPC195685
0.5045	Remote Similarity	NPC484301

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC533709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4576
0.1-0.2	4495
0.2-0.3	62
0.3-0.4	12
0.4-0.5	3
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
0.5895	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5825	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