NPASS Compound

Natural Product: NPC470443

Natural Product ID	NPC470443
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-Hydroxy-7-Methoxyquercetin-3-O-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name	2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2037042
PubChem CID	57409858
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 77 81 0 0 0 0 0 0 0 0999 V2000 -2.9687 0.2628 -3.7768 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5196 -0.6206 -2.6284 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6672 -1.4481 -2.1072 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0809 -0.9912 -0.7290 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9724 0.4958 -0.6847 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5350 0.9303 -0.9283 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8009 0.0384 -1.6659 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8893 1.1739 0.2800 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5661 2.4928 0.5099 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8647 2.5877 1.8427 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8397 2.2736 2.9622 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1911 1.4886 4.0668 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5377 0.2508 3.4703 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2067 0.5455 2.2494 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3094 1.9148 1.9516 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5859 0.0892 2.2395 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2586 0.0311 1.0238 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2535 -1.0867 0.2717 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9321 -1.0101 -0.8827 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5664 0.0547 -1.2825 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2600 0.0914 -2.4847 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9311 1.2352 -2.8919 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9405 2.3928 -2.1175 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2554 2.3655 -0.9234 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5892 1.2061 -0.5346 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9265 1.2190 0.6506 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8828 2.2299 1.4177 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2164 3.4821 -0.0903 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6178 3.5345 -2.5371 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6223 1.2731 -4.0890 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7226 0.2018 -5.0003 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5984 -2.3485 0.5725 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0382 -2.7281 1.7450 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3843 -3.9460 1.9312 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2851 -4.8340 0.8935 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -4.4892 -0.3269 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4773 -3.2880 -0.4702 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3572 -6.0691 1.0201 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1504 -4.2244 3.1685 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2059 -0.4148 4.4571 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1294 1.1683 5.0214 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3536 3.4673 3.5223 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4008 1.0295 0.5485 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3898 -1.3874 -0.4652 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2465 -2.7892 -1.9763 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3244 1.1572 -3.9037 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8846 -0.2905 -4.7512 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0323 0.5239 -3.6828 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7808 -1.3440 -3.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5208 -1.4295 -2.8337 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4182 -1.5035 -0.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6809 0.9161 -1.4319 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6135 1.9051 -1.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9710 2.9434 -0.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5181 3.0824 0.5269 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6117 3.6838 1.9537 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7295 1.7210 2.6046 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4512 2.1601 4.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3915 -0.4427 3.2316 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2121 0.1043 1.3289 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2453 -0.8174 -3.0862 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0413 4.0246 0.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9402 4.1498 -1.7746 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5529 0.4133 -5.7213 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8713 -0.7420 -4.4611 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7607 0.1729 -5.5737 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1215 -2.0733 2.5862 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7627 -5.2043 -1.1523 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9085 -3.0450 -1.4382 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0331 -6.3909 0.3237 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1570 -4.4124 3.2905 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3289 -1.1105 4.9277 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6336 1.9816 5.2397 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2048 4.1523 2.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6526 1.9954 0.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7693 -0.9533 0.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7360 -3.1790 -1.2287 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 6 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 14 15 1 0 14 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 24 28 1 0 23 29 1 0 22 30 1 0 30 31 1 0 18 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 35 38 1 0 34 39 1 0 13 40 1 0 12 41 1 0 11 42 1 0 5 43 1 0 4 44 1 0 3 45 1 0 7 2 1 0 15 10 1 0 26 17 1 0 25 20 1 0 37 32 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 3 50 1 0 4 51 1 0 5 52 1 0 6 53 1 0 9 54 1 0 9 55 1 0 10 56 1 0 11 57 1 0 12 58 1 0 13 59 1 0 14 60 1 0 21 61 1 0 28 62 1 0 29 63 1 0 31 64 1 0 31 65 1 0 31 66 1 0 33 67 1 0 36 68 1 0 37 69 1 0 38 70 1 0 39 71 1 0 40 72 1 0 41 73 1 0 42 74 1 0 43 75 1 0 44 76 1 0 45 77 1 0 M END

Standard InCHIKey	XAONDIJHQOKTPT-FEKXXYJASA-N
Standard InCHI	InChI=1S/C28H32O17/c1-8-16(31)21(36)23(38)27(42-8)41-7-14-18(33)22(37)24(39)28(44-14)45-26-20(35)15-12(6-13(40-2)17(32)19(15)34)43-25(26)9-3-4-10(29)11(30)5-9/h3-6,8,14,16,18,21-24,27-34,36-39H,7H2,1-2H3/t8-,14+,16-,18+,21+,22-,23+,24+,27+,28-/m0/s1
SMILES	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=C(C(=C4C3=O)O)O)OC)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	640.16	Volume:	578.404 ? Van der Waals volume.
Dense:	1.107	LogP:	-0.789 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.15 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.103 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	278.66 ? 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:	0.129	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.848	Fsp³:	0.464
MCE-18:	125.561 ? 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:	0.294	Fluc inhibitor:	0.049 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.879 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.93 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.11	Promiscuous compounds:	0.53

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.163	MDCK Permeability:	-5.168
Pgp-inhibitor:	0.0	Pgp-substrate:	0.768
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):	0.998
20% Bioavailability (F20%):	0.962	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.944
Plasma Protein Binding (PPB):	78.522%	Volume Distribution (VD):	-0.172
Fu:	22.952% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.008
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.769
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	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:	0.274
HLM stability:	0.001 ? 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):

2.016

Half-life (T1/2):

4.266

ADMET: Toxicity

hERG Blockers:	0.035	hERG Blockers (10um):	0.615
Human Hepatotoxicity (H-HT):	0.296	Drug-induced Liver Injury (DILI):	0.875
AMES Toxicity:	0.658	Rat Oral Acute Toxicity:	0.327
Maximum Recommended Daily Dose:	0.345	Skin Sensitization:	0.562
Carcinogencity:	0.081	Eye Corrosion:	0.0
Eye Irritation:	0.034	Respiratory Toxicity:	0.019
Drug-induced Neurotoxicity:	0.051	Ototoxicity:	0.983
Hematotoxicity:	0.011	Drug-induced Nephrotoxicity:	0.012
Genotoxicity:	0.514	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.445	Hek293 Cytotoxicity:	0.641
BCF:	0.49 ? 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:	3.041 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.062 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.956 ? 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
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	Flowers	Santana do Riacho, State Minas Gerais, Brazil	n.a.	PMID[22506638]
NPO33486	paepalanthus geniculatus	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Activity	1

Activity Type	# Activity
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	1.545	mM	PMID[22506638]

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 NPC470443 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	20652
0.1-0.2	25551
0.2-0.3	2743
0.3-0.4	481
0.4-0.5	242
0.5-0.6	122
0.6-0.7	44
0.7-0.8	2
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
0.7841	Intermediate Similarity	NPC126784
0.7841	Intermediate Similarity	NPC241423
0.7614	Intermediate Similarity	NPC203259
0.7614	Intermediate Similarity	NPC33054
0.7614	Intermediate Similarity	NPC176740
0.7614	Intermediate Similarity	NPC471725
0.7614	Intermediate Similarity	NPC134532
0.7614	Intermediate Similarity	NPC602582
0.75	Intermediate Similarity	NPC473073
0.7222	Intermediate Similarity	NPC65563
0.7222	Intermediate Similarity	NPC470949
0.7143	Intermediate Similarity	NPC186816
0.6957	Remote Similarity	NPC473571
0.6957	Remote Similarity	NPC110941
0.6947	Remote Similarity	NPC476472
0.6947	Remote Similarity	NPC294815
0.6947	Remote Similarity	NPC16194
0.6923	Remote Similarity	NPC173582
0.6923	Remote Similarity	NPC265885
0.6923	Remote Similarity	NPC181465
0.6923	Remote Similarity	NPC215710
0.6923	Remote Similarity	NPC473438
0.6923	Remote Similarity	NPC253788
0.6915	Remote Similarity	NPC473327
0.6882	Remote Similarity	NPC488073
0.686	Remote Similarity	NPC271692
0.6739	Remote Similarity	NPC39834
0.6702	Remote Similarity	NPC488074
0.6667	Remote Similarity	NPC27640
0.6667	Remote Similarity	NPC156869
0.6559	Remote Similarity	NPC67326
0.6559	Remote Similarity	NPC67105
0.6489	Remote Similarity	NPC210073
0.6471	Remote Similarity	NPC480441
0.6465	Remote Similarity	NPC470446
0.6364	Remote Similarity	NPC470445
0.6292	Remote Similarity	NPC305811
0.6237	Remote Similarity	NPC116864
0.6237	Remote Similarity	NPC244776
0.6224	Remote Similarity	NPC122467
0.6214	Remote Similarity	NPC292019
0.6214	Remote Similarity	NPC202908
0.6162	Remote Similarity	NPC142142
0.6111	Remote Similarity	NPC46420
0.61	Remote Similarity	NPC89127
0.6087	Remote Similarity	NPC181616
0.6067	Remote Similarity	NPC127546
0.6067	Remote Similarity	NPC57625
0.6067	Remote Similarity	NPC173637
0.6067	Remote Similarity	NPC317489
0.6067	Remote Similarity	NPC223424
0.6067	Remote Similarity	NPC600591
0.6044	Remote Similarity	NPC59534
0.6022	Remote Similarity	NPC605784
0.6	Remote Similarity	NPC158674
0.6	Remote Similarity	NPC486577
0.596	Remote Similarity	NPC483414
0.596	Remote Similarity	NPC483415
0.5938	Remote Similarity	NPC471079
0.59	Remote Similarity	NPC483416
0.59	Remote Similarity	NPC209296
0.5876	Remote Similarity	NPC44931
0.5876	Remote Similarity	NPC227508
0.5849	Remote Similarity	NPC25523
0.5816	Remote Similarity	NPC22062
0.5816	Remote Similarity	NPC473634
0.5816	Remote Similarity	NPC138811
0.581	Remote Similarity	NPC470451
0.5806	Remote Similarity	NPC488071
0.5806	Remote Similarity	NPC611303
0.5769	Remote Similarity	NPC14187
0.5758	Remote Similarity	NPC204693
0.575	Remote Similarity	NPC305663
0.5729	Remote Similarity	NPC265115
0.5728	Remote Similarity	NPC470449
0.5714	Remote Similarity	NPC89052
0.5714	Remote Similarity	NPC249281
0.5701	Remote Similarity	NPC303694
0.57	Remote Similarity	NPC153755
0.566	Remote Similarity	NPC189564
0.5657	Remote Similarity	NPC605592
0.5652	Remote Similarity	NPC136042
0.5644	Remote Similarity	NPC12013
0.5644	Remote Similarity	NPC11432
0.5644	Remote Similarity	NPC477613
0.5631	Remote Similarity	NPC470447
0.5631	Remote Similarity	NPC471669
0.5625	Remote Similarity	NPC276377
0.5607	Remote Similarity	NPC173837
0.5591	Remote Similarity	NPC84362
0.5575	Remote Similarity	NPC241781
0.5567	Remote Similarity	NPC477848
0.5566	Remote Similarity	NPC203145
0.5532	Remote Similarity	NPC42773
0.5532	Remote Similarity	NPC45522
0.5521	Remote Similarity	NPC223747
0.551	Remote Similarity	NPC254540
0.5487	Remote Similarity	NPC488078
0.5474	Remote Similarity	NPC175107
0.5474	Remote Similarity	NPC219904
0.5455	Remote Similarity	NPC480466
0.5455	Remote Similarity	NPC609888
0.5437	Remote Similarity	NPC37668
0.5435	Remote Similarity	NPC111929
0.5435	Remote Similarity	NPC320283
0.5435	Remote Similarity	NPC41121
0.5429	Remote Similarity	NPC221342
0.5429	Remote Similarity	NPC476470
0.5426	Remote Similarity	NPC245014
0.5421	Remote Similarity	NPC121703
0.5408	Remote Similarity	NPC95866
0.5398	Remote Similarity	NPC156785
0.5398	Remote Similarity	NPC162394
0.5377	Remote Similarity	NPC223426
0.5377	Remote Similarity	NPC602448
0.5368	Remote Similarity	NPC599850
0.5361	Remote Similarity	NPC99957
0.5361	Remote Similarity	NPC116458
0.5361	Remote Similarity	NPC246943
0.5347	Remote Similarity	NPC233994
0.5347	Remote Similarity	NPC150164
0.5327	Remote Similarity	NPC470455
0.5327	Remote Similarity	NPC81042
0.5327	Remote Similarity	NPC603856
0.5319	Remote Similarity	NPC145038
0.5319	Remote Similarity	NPC56077
0.5319	Remote Similarity	NPC281131
0.5319	Remote Similarity	NPC253662
0.5319	Remote Similarity	NPC179950
0.5319	Remote Similarity	NPC88789
0.5319	Remote Similarity	NPC491374
0.53	Remote Similarity	NPC187379
0.5288	Remote Similarity	NPC606657
0.5269	Remote Similarity	NPC135599
0.5269	Remote Similarity	NPC73855
0.5269	Remote Similarity	NPC113968
0.5269	Remote Similarity	NPC328940
0.5269	Remote Similarity	NPC277174
0.5269	Remote Similarity	NPC606877
0.5263	Remote Similarity	NPC58716
0.5263	Remote Similarity	NPC349108
0.5259	Remote Similarity	NPC192539
0.5243	Remote Similarity	NPC240306
0.5243	Remote Similarity	NPC475366
0.5238	Remote Similarity	NPC64755
0.5213	Remote Similarity	NPC238376
0.52	Remote Similarity	NPC251417
0.5196	Remote Similarity	NPC155877
0.5196	Remote Similarity	NPC303913
0.5192	Remote Similarity	NPC211532
0.5192	Remote Similarity	NPC65711
0.5192	Remote Similarity	NPC488364
0.5189	Remote Similarity	NPC473071
0.5189	Remote Similarity	NPC483412
0.5158	Remote Similarity	NPC265530
0.5143	Remote Similarity	NPC32641
0.5143	Remote Similarity	NPC256188
0.5143	Remote Similarity	NPC72016
0.512	Remote Similarity	NPC487500
0.5104	Remote Similarity	NPC24043
0.5098	Remote Similarity	NPC471748
0.5098	Remote Similarity	NPC275454
0.5086	Remote Similarity	NPC480444
0.5083	Remote Similarity	NPC487499
0.5079	Remote Similarity	NPC487501
0.5078	Remote Similarity	NPC482520
0.5078	Remote Similarity	NPC482521
0.5078	Remote Similarity	NPC482519
0.5054	Remote Similarity	NPC276222
0.5054	Remote Similarity	NPC274618
0.5054	Remote Similarity	NPC118284
0.5054	Remote Similarity	NPC608147
0.5053	Remote Similarity	NPC19709
0.5049	Remote Similarity	NPC473512
0.5047	Remote Similarity	NPC483413
0.5044	Remote Similarity	NPC139571
0.5043	Remote Similarity	NPC209550
0.5041	Remote Similarity	NPC473554

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470443 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5427
0.1-0.2	3677
0.2-0.3	36
0.3-0.4	4
0.4-0.5	1
0.5-0.6	2
0.6-0.7	1
0.7-0.8	2
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
0.7614	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD7251	Phase 2
0.6176	Remote Similarity	NPD7808	Phase 3
0.59	Remote Similarity	NPD7054	Phase 4
0.5278	Remote Similarity	NPD7472	Pre-clinical

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