NPASS Compound

Natural Product: NPC134532

Natural Product ID	NPC134532
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-Dihydroxyphenyl)-5,7-Dihydroxy-3-[3,4,5-Trihydroxy-6-[(3,4,5-Trihydroxy-6-Methyloxan-2-Yl)Oxymethyl]Oxan-2-Yl]Oxychromen-4-One
IUPAC Name	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL32579
PubChem CID	5293655
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 73 77 0 0 0 0 0 0 0 0999 V2000 -5.8232 0.8824 -0.9753 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1542 -0.5834 -1.3055 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0283 -1.0981 -0.2174 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2449 -1.5599 0.9787 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1881 -2.5312 0.4968 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3465 -1.8583 -0.5384 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5404 -0.9003 0.1226 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2154 -1.2648 0.0962 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3566 -0.2018 0.7803 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5844 1.1443 0.1178 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9210 1.2049 -1.2145 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4945 0.7171 -1.1896 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8797 0.1895 0.1346 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0651 -0.6012 0.7316 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0546 -0.6650 0.0815 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2154 -0.1726 0.6521 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2323 -0.2576 2.0600 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2947 -0.7364 2.7214 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3563 0.2221 2.6890 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4401 0.1731 4.0866 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5736 0.6615 4.6836 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5871 1.1809 3.9080 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5142 1.2349 2.5362 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3616 0.7402 1.9047 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2930 0.7912 0.6105 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2314 0.3408 -0.0712 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2473 0.4303 -1.5202 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2020 1.2650 -2.1120 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3448 1.3641 -3.4822 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5510 0.6421 -4.3189 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6137 -0.1792 -3.7705 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4751 -0.2747 -2.3975 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7825 -0.9342 -4.6070 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6485 0.7014 -5.7105 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7463 1.6798 4.4876 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3795 -0.3651 4.8148 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3392 1.8167 -1.5072 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6913 0.4634 -2.1274 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1653 2.1728 0.9164 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9931 -1.2333 -1.5486 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3910 -2.9554 1.5804 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6726 -0.4795 1.6391 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0377 -0.2017 0.1295 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3094 1.3340 -1.8461 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0814 0.8489 -0.1515 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7186 1.4471 -0.6606 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7723 -0.4833 -2.2679 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5547 -2.0175 -0.6093 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9917 -2.0846 1.6369 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7311 -3.4150 0.1181 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6303 -2.6520 -0.9090 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8846 -1.5015 -0.9062 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1071 -2.1711 0.7678 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7358 -0.1137 1.8103 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6766 1.2357 -0.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9317 2.2392 -1.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6109 -0.0400 -2.0160 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1830 1.0522 0.7841 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6791 0.6442 5.7585 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3293 1.6511 1.9222 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8440 1.8500 -1.4527 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0961 2.0233 -3.8921 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7429 -0.9440 -2.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1912 -1.6568 -4.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1903 0.0486 -6.2988 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9328 2.6664 4.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5386 -0.4656 5.8276 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7991 2.4947 -1.9877 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0763 0.1598 -2.8224 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6001 2.2057 1.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4183 -3.9412 1.6627 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5062 -0.6911 2.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8507 -0.6885 0.3406 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 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 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 30 34 1 0 22 35 1 0 20 36 1 0 12 37 1 0 11 38 1 0 10 39 1 0 6 40 1 0 5 41 1 0 4 42 1 0 3 43 1 0 40 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 24 19 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 3 48 1 0 4 49 1 0 5 50 1 0 6 51 1 0 8 52 1 0 8 53 1 0 9 54 1 0 10 55 1 0 11 56 1 0 12 57 1 0 13 58 1 0 21 59 1 0 23 60 1 0 28 61 1 0 29 62 1 0 32 63 1 0 33 64 1 0 34 65 1 0 35 66 1 0 36 67 1 0 37 68 1 0 38 69 1 0 39 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	IKGXIBQEEMLURG-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3
SMILES	CC1C(C(C(C(OCC2C(C(C(C(O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)O)O)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	-0.027 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.522 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.603 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.14	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.783	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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.318	Fluc inhibitor:	0.051 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.915 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.935 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.202	Promiscuous compounds:	0.754

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.307	MDCK Permeability:	-4.996
Pgp-inhibitor:	0.0	Pgp-substrate:	0.959
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):	0.974
20% Bioavailability (F20%):	0.939	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.83
Plasma Protein Binding (PPB):	81.741%	Volume Distribution (VD):	-0.151
Fu:	19.664% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.001
OATP1B3 inhibitor:	0.941	BCRP inhibitor:	0.793
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.023	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.98
HLM stability:	0.005 ? 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):

2.05

Half-life (T1/2):

3.878

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.614
Human Hepatotoxicity (H-HT):	0.291	Drug-induced Liver Injury (DILI):	0.812
AMES Toxicity:	0.753	Rat Oral Acute Toxicity:	0.415
Maximum Recommended Daily Dose:	0.636	Skin Sensitization:	0.469
Carcinogencity:	0.111	Eye Corrosion:	0.0
Eye Irritation:	0.165	Respiratory Toxicity:	0.03
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.957
Hematotoxicity:	0.005	Drug-induced Nephrotoxicity:	0.004
Genotoxicity:	0.924	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.424	Hek293 Cytotoxicity:	0.865
BCF:	0.471 ? 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:	2.985 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.911 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.882 ? 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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1613	Cuscuta chinensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1613	Cuscuta chinensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1613	Cuscuta chinensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1613	Cuscuta chinensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1613	Cuscuta chinensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	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

Activity Type	# Activity
Potency	6

Activity Type	# Activity
Individual protein	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	3162.3	nM	PubChem BioAssay data set
NPT199	Individual protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	6309.6	nM	PubChem BioAssay data set
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	14125.4	nM	PubChem BioAssay data set

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
-	Mus musculus	LD50	=	3.484670611	mg/kg	TOXRIC

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 NPC134532 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	19329
0.1-0.2	26631
0.2-0.3	2904
0.3-0.4	486
0.4-0.5	215
0.5-0.6	39
0.6-0.7	85
0.7-0.8	1
0.8-0.85	17
0.85-0.9	3
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC203259
1.0	High Similarity	NPC33054
1.0	High Similarity	NPC176740
1.0	High Similarity	NPC471725
1.0	High Similarity	NPC602582
0.9114	High Similarity	NPC173582
0.9114	High Similarity	NPC265885
0.9114	High Similarity	NPC181465
0.9114	High Similarity	NPC215710
0.9114	High Similarity	NPC473438
0.9114	High Similarity	NPC253788
0.8875	High Similarity	NPC39834
0.8765	High Similarity	NPC156869
0.8642	High Similarity	NPC67326
0.8372	Intermediate Similarity	NPC476472
0.8372	Intermediate Similarity	NPC294815
0.8372	Intermediate Similarity	NPC16194
0.8353	Intermediate Similarity	NPC473327
0.8272	Intermediate Similarity	NPC116864
0.8272	Intermediate Similarity	NPC244776
0.8182	Intermediate Similarity	NPC127546
0.8182	Intermediate Similarity	NPC57625
0.8182	Intermediate Similarity	NPC173637
0.8182	Intermediate Similarity	NPC317489
0.8182	Intermediate Similarity	NPC223424
0.8182	Intermediate Similarity	NPC600591
0.814	Intermediate Similarity	NPC122467
0.8118	Intermediate Similarity	NPC126784
0.8118	Intermediate Similarity	NPC241423
0.8022	Intermediate Similarity	NPC292019
0.8022	Intermediate Similarity	NPC202908
0.7955	Intermediate Similarity	NPC89127
0.7857	Intermediate Similarity	NPC471079
0.7674	Intermediate Similarity	NPC65563
0.7674	Intermediate Similarity	NPC470949
0.7614	Intermediate Similarity	NPC470443
0.7471	Intermediate Similarity	NPC605592
0.7416	Intermediate Similarity	NPC12013
0.7416	Intermediate Similarity	NPC11432
0.7416	Intermediate Similarity	NPC477613
0.7386	Intermediate Similarity	NPC473571
0.7386	Intermediate Similarity	NPC110941
0.7386	Intermediate Similarity	NPC186816
0.7375	Intermediate Similarity	NPC111929
0.7375	Intermediate Similarity	NPC320283
0.7375	Intermediate Similarity	NPC41121
0.7368	Intermediate Similarity	NPC303694
0.7363	Intermediate Similarity	NPC473073
0.7363	Intermediate Similarity	NPC471669
0.734	Intermediate Similarity	NPC189564
0.7234	Intermediate Similarity	NPC203145
0.7209	Intermediate Similarity	NPC95866
0.7195	Intermediate Similarity	NPC145038
0.7195	Intermediate Similarity	NPC56077
0.7195	Intermediate Similarity	NPC281131
0.7195	Intermediate Similarity	NPC253662
0.7195	Intermediate Similarity	NPC179950
0.7195	Intermediate Similarity	NPC88789
0.7195	Intermediate Similarity	NPC491374
0.716	Intermediate Similarity	NPC135599
0.716	Intermediate Similarity	NPC73855
0.716	Intermediate Similarity	NPC113968
0.716	Intermediate Similarity	NPC328940
0.716	Intermediate Similarity	NPC277174
0.716	Intermediate Similarity	NPC606877
0.7143	Intermediate Similarity	NPC37668
0.7143	Intermediate Similarity	NPC175107
0.7129	Intermediate Similarity	NPC241781
0.7111	Intermediate Similarity	NPC488073
0.7111	Intermediate Similarity	NPC488074
0.7097	Intermediate Similarity	NPC221342
0.7097	Intermediate Similarity	NPC476470
0.7045	Intermediate Similarity	NPC187379
0.7021	Intermediate Similarity	NPC223426
0.7021	Intermediate Similarity	NPC602448
0.6947	Remote Similarity	NPC81042
0.6931	Remote Similarity	NPC156785
0.6931	Remote Similarity	NPC162394
0.6923	Remote Similarity	NPC153755
0.6914	Remote Similarity	NPC276222
0.6914	Remote Similarity	NPC274618
0.6914	Remote Similarity	NPC118284
0.6914	Remote Similarity	NPC608147
0.6889	Remote Similarity	NPC155877
0.6875	Remote Similarity	NPC89052
0.6829	Remote Similarity	NPC67037
0.6829	Remote Similarity	NPC255615
0.6782	Remote Similarity	NPC223747
0.6778	Remote Similarity	NPC471748
0.6778	Remote Similarity	NPC67105
0.6744	Remote Similarity	NPC219904
0.6735	Remote Similarity	NPC173837
0.6667	Remote Similarity	NPC470446
0.6667	Remote Similarity	NPC29958
0.6667	Remote Similarity	NPC609888
0.663	Remote Similarity	NPC129264
0.6596	Remote Similarity	NPC270448
0.6588	Remote Similarity	NPC265530
0.6571	Remote Similarity	NPC192539
0.6562	Remote Similarity	NPC470445
0.6559	Remote Similarity	NPC470125
0.6559	Remote Similarity	NPC154741
0.6538	Remote Similarity	NPC480444
0.6522	Remote Similarity	NPC210073
0.6517	Remote Similarity	NPC476215
0.6512	Remote Similarity	NPC305811
0.6512	Remote Similarity	NPC271692
0.65	Remote Similarity	NPC480441
0.6481	Remote Similarity	NPC487499
0.6471	Remote Similarity	NPC77672
0.6471	Remote Similarity	NPC133671
0.6471	Remote Similarity	NPC135391
0.6471	Remote Similarity	NPC78263
0.6471	Remote Similarity	NPC250069
0.6458	Remote Similarity	NPC85751
0.6458	Remote Similarity	NPC19240
0.6429	Remote Similarity	NPC214621
0.6429	Remote Similarity	NPC34267
0.6322	Remote Similarity	NPC52550
0.6286	Remote Similarity	NPC488740
0.6286	Remote Similarity	NPC474522
0.6286	Remote Similarity	NPC488736
0.6286	Remote Similarity	NPC488733
0.6279	Remote Similarity	NPC19388
0.6279	Remote Similarity	NPC240431
0.6279	Remote Similarity	NPC55786
0.6277	Remote Similarity	NPC255157
0.6277	Remote Similarity	NPC259896
0.6273	Remote Similarity	NPC275977
0.6264	Remote Similarity	NPC254855
0.6264	Remote Similarity	NPC94610
0.625	Remote Similarity	NPC487502
0.6237	Remote Similarity	NPC163242
0.6237	Remote Similarity	NPC272068
0.6224	Remote Similarity	NPC292929
0.619	Remote Similarity	NPC54802
0.619	Remote Similarity	NPC197304
0.6168	Remote Similarity	NPC488737
0.6161	Remote Similarity	NPC72554
0.6146	Remote Similarity	NPC245452
0.6136	Remote Similarity	NPC27640
0.6129	Remote Similarity	NPC139320
0.6118	Remote Similarity	NPC288084
0.6064	Remote Similarity	NPC44931
0.6064	Remote Similarity	NPC227508
0.6061	Remote Similarity	NPC470449
0.6058	Remote Similarity	NPC139571
0.6044	Remote Similarity	NPC605784
0.6042	Remote Similarity	NPC296018
0.6038	Remote Similarity	NPC480445
0.6034	Remote Similarity	NPC487500
0.6023	Remote Similarity	NPC64305
0.602	Remote Similarity	NPC142142
0.6019	Remote Similarity	NPC217520
0.6019	Remote Similarity	NPC25523
0.6	Remote Similarity	NPC235260
0.6	Remote Similarity	NPC159579
0.6	Remote Similarity	NPC60735
0.6	Remote Similarity	NPC155763
0.6	Remote Similarity	NPC26230
0.5983	Remote Similarity	NPC487501
0.5982	Remote Similarity	NPC473554
0.598	Remote Similarity	NPC470451
0.5978	Remote Similarity	NPC203050
0.5978	Remote Similarity	NPC225434
0.596	Remote Similarity	NPC470447
0.5955	Remote Similarity	NPC46420
0.5948	Remote Similarity	NPC97817
0.5934	Remote Similarity	NPC120099
0.593	Remote Similarity	NPC34531
0.5922	Remote Similarity	NPC477895
0.5909	Remote Similarity	NPC249281
0.5889	Remote Similarity	NPC472459
0.5889	Remote Similarity	NPC59534
0.5877	Remote Similarity	NPC30011
0.5824	Remote Similarity	NPC182121
0.5806	Remote Similarity	NPC276377
0.58	Remote Similarity	NPC135831
0.58	Remote Similarity	NPC220173
0.5794	Remote Similarity	NPC488734
0.5794	Remote Similarity	NPC488735
0.5794	Remote Similarity	NPC488739
0.5794	Remote Similarity	NPC488732
0.5794	Remote Similarity	NPC488738
0.5784	Remote Similarity	NPC14187
0.5776	Remote Similarity	NPC249560
0.5773	Remote Similarity	NPC35167
0.5745	Remote Similarity	NPC265115
0.5743	Remote Similarity	NPC287889
0.5729	Remote Similarity	NPC470405
0.5714	Remote Similarity	NPC42773
0.5714	Remote Similarity	NPC216496
0.5714	Remote Similarity	NPC45522
0.5714	Remote Similarity	NPC325555
0.5714	Remote Similarity	NPC226304
0.5714	Remote Similarity	NPC599850
0.5702	Remote Similarity	NPC482521
0.57	Remote Similarity	NPC486577
0.567	Remote Similarity	NPC304741

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC134532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5410
0.1-0.2	3686
0.2-0.3	43
0.3-0.4	3
0.4-0.5	4
0.5-0.6	1
0.6-0.7	1
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6797	Phase 2
0.7556	Intermediate Similarity	NPD7251	Phase 2
0.62	Remote Similarity	NPD7808	Phase 3
0.5446	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