NPASS Compound

Natural Product: NPC537157

Natural Product ID	NPC537157
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7-dihydroxy-2-[3-methoxy-4-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5,7-dihydroxy-2-[3-methoxy-4-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-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 3.6683 -2.2904 1.9024 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6140 -1.3134 0.8894 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3893 -0.9232 0.4019 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2275 -1.4734 0.8909 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0253 -1.1200 0.4398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2033 -1.7981 0.9677 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4900 -1.3746 0.8319 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8736 -0.2489 0.2000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1220 0.9981 0.8220 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5120 1.0549 1.0637 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2602 1.6769 0.1317 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0330 2.8810 0.6749 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7721 3.4875 -0.3261 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6950 1.9373 -1.2228 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9327 0.8284 -2.0939 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2251 2.2257 -1.3088 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0239 3.5384 -1.7843 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6790 2.2170 0.1208 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3676 2.5765 0.2051 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4825 -2.1703 1.4057 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6908 -1.8741 1.3374 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1603 -3.3337 2.0832 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1130 -4.1454 2.6639 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4455 -3.8183 2.5847 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7692 -5.3105 3.3425 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 -5.6641 3.4370 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1102 -6.8454 4.1238 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4925 -4.8658 2.8636 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8351 -3.6898 2.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9410 -2.9342 1.6364 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0659 -0.1680 -0.5476 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1151 0.3961 -1.0481 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3481 0.0200 -0.5747 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5233 0.5570 -1.0475 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6917 1.5166 -2.0434 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3702 0.9094 -3.0985 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6479 0.5162 -2.6702 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2620 -0.3318 -3.7394 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4510 1.7893 -2.5513 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7750 1.5121 -2.2338 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8331 2.7769 -1.5980 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3129 4.0481 -1.9764 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3589 2.7719 -1.5653 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9186 3.0112 -0.2611 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3886 -3.2771 1.4554 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7090 -2.3663 2.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9953 -2.0417 2.7606 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2698 -2.2364 1.6906 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6848 0.9458 1.8354 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1255 0.9324 -0.0811 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8040 2.4797 1.4016 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4333 3.5749 1.2550 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8759 4.4489 -0.1718 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2297 2.7978 -1.7244 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6844 0.2863 -1.7406 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6875 1.5052 -1.9651 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6644 3.7367 -2.5292 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2414 3.1031 0.5917 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0410 3.0835 -0.5695 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1217 -4.2122 1.9664 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5166 -5.9528 3.8015 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2383 -6.8099 5.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4661 -5.1453 2.9397 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0177 0.1382 -0.9592 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9770 1.1432 -1.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7099 1.8080 -2.4508 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6167 -0.0298 -1.7201 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2936 0.0055 -3.9883 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3685 -1.3832 -3.3848 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6952 -0.3465 -4.6888 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4504 2.2417 -3.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9305 1.4117 -1.2819 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2859 2.5882 -0.5937 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2700 4.1531 -1.7768 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9736 3.6457 -2.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1609 2.2185 0.2785 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 6 7 2 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 11 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 7 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 2 0 26 27 1 0 26 28 1 0 28 29 2 0 29 30 1 0 5 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 33 3 1 0 43 35 1 0 30 6 1 0 18 9 1 0 29 22 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 9 49 1 1 11 50 1 6 12 51 1 0 12 52 1 0 13 53 1 0 14 54 1 6 15 55 1 0 16 56 1 6 17 57 1 0 18 58 1 1 19 59 1 0 24 60 1 0 25 61 1 0 27 62 1 0 28 63 1 0 31 64 1 0 32 65 1 0 35 66 1 6 37 67 1 1 38 68 1 0 38 69 1 0 38 70 1 0 39 71 1 6 40 72 1 0 41 73 1 1 42 74 1 0 43 75 1 6 44 76 1 0 M END

Standard InCHIKey	GVBDKXQDCPGLFU-GQDYDGNHSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(40-9)42-13-4-3-10(5-14(13)39-2)25-26(20(34)17-12(31)6-11(30)7-15(17)41-25)44-28-24(38)22(36)19(33)16(8-29)43-28/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(C2=C(O[C@@H]3O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]3O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	0.476 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.169 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.198 ? 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:	4.71	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:	0	PAINS Alert:	0
Colloidal aggregators:	0.644	Fluc inhibitor:	0.279 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.772 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.595 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.107	Promiscuous compounds:	0.518

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.541	MDCK Permeability:	-5.207
Pgp-inhibitor:	0.0	Pgp-substrate:	0.939
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):	0.991
20% Bioavailability (F20%):	0.595	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.058
Plasma Protein Binding (PPB):	84.408%	Volume Distribution (VD):	-0.047
Fu:	14.626% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.944
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.862
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.027	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.158
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.056 ? 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):

1.293

Half-life (T1/2):

3.266

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.082
Human Hepatotoxicity (H-HT):	0.718	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.983	Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.021	Skin Sensitization:	1.0
Carcinogencity:	0.089	Eye Corrosion:	0.0
Eye Irritation:	0.277	Respiratory Toxicity:	0.012
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.88
Hematotoxicity:	0.249	Drug-induced Nephrotoxicity:	0.769
Genotoxicity:	0.934	RPMI-8226 Immunitoxicity:	0.392
A549 Cytotoxicity:	0.905	Hek293 Cytotoxicity:	0.507
BCF:	0.47 ? 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:	3.196 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.693 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.868 ? 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
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO53065	Reseda gredensis	Species	Resedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Root Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13642	Pastinaca sativa	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 NPC537157 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	14981
0.1-0.2	30615
0.2-0.3	2919
0.3-0.4	804
0.4-0.5	280
0.5-0.6	99
0.6-0.7	62
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
0.7875	Intermediate Similarity	NPC472459
0.7683	Intermediate Similarity	NPC120099
0.7625	Intermediate Similarity	NPC64305
0.7561	Intermediate Similarity	NPC219904
0.75	Intermediate Similarity	NPC203050
0.75	Intermediate Similarity	NPC225434
0.7439	Intermediate Similarity	NPC325555
0.7439	Intermediate Similarity	NPC226304
0.7381	Intermediate Similarity	NPC223747
0.7381	Intermediate Similarity	NPC88023
0.7349	Intermediate Similarity	NPC60735
0.7349	Intermediate Similarity	NPC26230
0.7284	Intermediate Similarity	NPC77672
0.7284	Intermediate Similarity	NPC133671
0.7284	Intermediate Similarity	NPC135391
0.7284	Intermediate Similarity	NPC78263
0.7284	Intermediate Similarity	NPC250069
0.7262	Intermediate Similarity	NPC609478
0.7195	Intermediate Similarity	NPC145038
0.7195	Intermediate Similarity	NPC56077
0.7195	Intermediate Similarity	NPC281131
0.7195	Intermediate Similarity	NPC253662
0.7195	Intermediate Similarity	NPC265530
0.7195	Intermediate Similarity	NPC179950
0.7195	Intermediate Similarity	NPC88789
0.7195	Intermediate Similarity	NPC491374
0.716	Intermediate Similarity	NPC111929
0.716	Intermediate Similarity	NPC320283
0.716	Intermediate Similarity	NPC41121
0.7083	Intermediate Similarity	NPC48984
0.7073	Intermediate Similarity	NPC127546
0.7073	Intermediate Similarity	NPC19388
0.7073	Intermediate Similarity	NPC240431
0.7073	Intermediate Similarity	NPC57625
0.7073	Intermediate Similarity	NPC55786
0.7073	Intermediate Similarity	NPC173637
0.7073	Intermediate Similarity	NPC317489
0.7073	Intermediate Similarity	NPC223424
0.7073	Intermediate Similarity	NPC600591
0.6977	Remote Similarity	NPC309025
0.6951	Remote Similarity	NPC135599
0.6951	Remote Similarity	NPC73855
0.6951	Remote Similarity	NPC113968
0.6951	Remote Similarity	NPC328940
0.6951	Remote Similarity	NPC277174
0.6951	Remote Similarity	NPC606877
0.6506	Remote Similarity	NPC288084
0.6458	Remote Similarity	NPC220173
0.6429	Remote Similarity	NPC67037
0.6429	Remote Similarity	NPC255615
0.6421	Remote Similarity	NPC473327
0.6404	Remote Similarity	NPC116458
0.6404	Remote Similarity	NPC246943
0.6374	Remote Similarity	NPC251417
0.631	Remote Similarity	NPC34531
0.6304	Remote Similarity	NPC139320
0.6289	Remote Similarity	NPC476472
0.6289	Remote Similarity	NPC294815
0.6289	Remote Similarity	NPC16194
0.625	Remote Similarity	NPC21100
0.6238	Remote Similarity	NPC477895
0.6237	Remote Similarity	NPC471748
0.6237	Remote Similarity	NPC163242
0.6237	Remote Similarity	NPC272068
0.6222	Remote Similarity	NPC605784
0.6211	Remote Similarity	NPC153755
0.618	Remote Similarity	NPC175107
0.617	Remote Similarity	NPC155877
0.617	Remote Similarity	NPC156869
0.617	Remote Similarity	NPC605592
0.6136	Remote Similarity	NPC488080
0.6136	Remote Similarity	NPC169977
0.6129	Remote Similarity	NPC480466
0.6129	Remote Similarity	NPC29958
0.6129	Remote Similarity	NPC609888
0.6122	Remote Similarity	NPC76831
0.6111	Remote Similarity	NPC101026
0.6111	Remote Similarity	NPC488077
0.6092	Remote Similarity	NPC289667
0.6092	Remote Similarity	NPC143851
0.6067	Remote Similarity	NPC42773
0.6067	Remote Similarity	NPC45522
0.6067	Remote Similarity	NPC599850
0.6064	Remote Similarity	NPC173582
0.6064	Remote Similarity	NPC265885
0.6064	Remote Similarity	NPC181465
0.6064	Remote Similarity	NPC215710
0.6064	Remote Similarity	NPC473438
0.6064	Remote Similarity	NPC253788
0.604	Remote Similarity	NPC203145
0.6026	Remote Similarity	NPC603596
0.6022	Remote Similarity	NPC480463
0.6	Remote Similarity	NPC203259
0.6	Remote Similarity	NPC191306
0.6	Remote Similarity	NPC33054
0.6	Remote Similarity	NPC176740
0.6	Remote Similarity	NPC471725
0.6	Remote Similarity	NPC134532
0.6	Remote Similarity	NPC488071
0.6	Remote Similarity	NPC602582
0.6	Remote Similarity	NPC611303
0.598	Remote Similarity	NPC189564
0.5978	Remote Similarity	NPC170052
0.5978	Remote Similarity	NPC488072
0.5978	Remote Similarity	NPC135846
0.5963	Remote Similarity	NPC192539
0.5955	Remote Similarity	NPC305811
0.5955	Remote Similarity	NPC46420
0.5955	Remote Similarity	NPC24043
0.5934	Remote Similarity	NPC21666
0.5922	Remote Similarity	NPC219043
0.5922	Remote Similarity	NPC292019
0.5922	Remote Similarity	NPC202908
0.5914	Remote Similarity	NPC254855
0.5914	Remote Similarity	NPC116864
0.5914	Remote Similarity	NPC244776
0.5914	Remote Similarity	NPC94610
0.5895	Remote Similarity	NPC39834
0.587	Remote Similarity	NPC206123
0.587	Remote Similarity	NPC607707
0.5859	Remote Similarity	NPC5319
0.5843	Remote Similarity	NPC297987
0.5842	Remote Similarity	NPC602448
0.5824	Remote Similarity	NPC609451
0.5806	Remote Similarity	NPC476215
0.5778	Remote Similarity	NPC271692
0.5778	Remote Similarity	NPC27640
0.5761	Remote Similarity	NPC197285
0.5761	Remote Similarity	NPC224530
0.5745	Remote Similarity	NPC95866
0.5741	Remote Similarity	NPC470713
0.573	Remote Similarity	NPC249281
0.5729	Remote Similarity	NPC470405
0.5714	Remote Similarity	NPC470712
0.5699	Remote Similarity	NPC209023
0.5684	Remote Similarity	NPC278419
0.5684	Remote Similarity	NPC179198
0.5667	Remote Similarity	NPC8573
0.5667	Remote Similarity	NPC158674
0.5667	Remote Similarity	NPC136042
0.5652	Remote Similarity	NPC159579
0.5652	Remote Similarity	NPC481043
0.5619	Remote Similarity	NPC173837
0.5618	Remote Similarity	NPC476771
0.5607	Remote Similarity	NPC470718
0.5607	Remote Similarity	NPC279473
0.5604	Remote Similarity	NPC52550
0.5604	Remote Similarity	NPC84362
0.5604	Remote Similarity	NPC603655
0.56	Remote Similarity	NPC35119
0.5591	Remote Similarity	NPC243930
0.5591	Remote Similarity	NPC601710
0.5577	Remote Similarity	NPC89052
0.5556	Remote Similarity	NPC254306
0.5543	Remote Similarity	NPC216496
0.5543	Remote Similarity	NPC59534
0.5484	Remote Similarity	NPC182121
0.5484	Remote Similarity	NPC129217
0.5465	Remote Similarity	NPC78697
0.5464	Remote Similarity	NPC471079
0.5455	Remote Similarity	NPC129264
0.5455	Remote Similarity	NPC54802
0.5455	Remote Similarity	NPC197304
0.5446	Remote Similarity	NPC32641
0.5446	Remote Similarity	NPC256188
0.5437	Remote Similarity	NPC287889
0.5435	Remote Similarity	NPC349108
0.5421	Remote Similarity	NPC217520
0.5417	Remote Similarity	NPC265115
0.5408	Remote Similarity	NPC67326
0.54	Remote Similarity	NPC64425
0.5393	Remote Similarity	NPC276222
0.5393	Remote Similarity	NPC274618
0.5393	Remote Similarity	NPC118284
0.5393	Remote Similarity	NPC608147
0.5354	Remote Similarity	NPC304741
0.5349	Remote Similarity	NPC268668
0.5347	Remote Similarity	NPC12013
0.5347	Remote Similarity	NPC483414
0.5347	Remote Similarity	NPC11432
0.5347	Remote Similarity	NPC483415
0.5347	Remote Similarity	NPC477613
0.534	Remote Similarity	NPC89127
0.5326	Remote Similarity	NPC156457
0.5321	Remote Similarity	NPC139571
0.5312	Remote Similarity	NPC276377
0.5312	Remote Similarity	NPC66087
0.5312	Remote Similarity	NPC355481
0.5306	Remote Similarity	NPC187379
0.53	Remote Similarity	NPC255157
0.53	Remote Similarity	NPC470444
0.53	Remote Similarity	NPC259896
0.5294	Remote Similarity	NPC483416
0.5294	Remote Similarity	NPC122467
0.5294	Remote Similarity	NPC37668
0.5294	Remote Similarity	NPC270448
0.5294	Remote Similarity	NPC606657
0.5288	Remote Similarity	NPC292929
0.5263	Remote Similarity	NPC486578
0.5248	Remote Similarity	NPC470125

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC537157 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4826
0.1-0.2	4244
0.2-0.3	63
0.3-0.4	11
0.4-0.5	3
0.5-0.6	2
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
0.6	Remote Similarity	NPD6797	Phase 2
0.5859	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5577	Remote Similarity	NPD7808	Phase 3

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