NPASS Compound

Natural Product: NPC470446

Natural Product ID	NPC470446
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-Methoxyquercetin-3-O-(4-O-Acetyl)-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name	[(2S,3R,4S,5R,6R)-6-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-2-methyloxan-3-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2037048
PubChem CID	57409957
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 82 86 0 0 0 0 0 0 0 0999 V2000 -5.3734 -1.8406 2.8849 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5032 -1.1085 1.9073 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3009 0.0189 1.2719 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7889 -0.5247 -0.0747 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5288 -0.7204 -0.9068 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4051 -1.2297 -0.0422 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0149 -2.0137 0.9574 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5064 -1.9091 -0.8188 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2051 -1.4158 -0.6986 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3295 -2.1916 -1.6576 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8637 -2.1282 -3.0702 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0051 -1.2599 -3.9455 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4299 -0.0483 -3.1504 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1612 -0.4630 -1.9267 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0069 -1.7897 -1.6039 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 -0.0741 -2.0184 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1470 0.5556 -0.9291 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8973 -0.1763 -0.0692 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4252 0.5227 0.9526 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2702 1.7839 1.1487 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5218 2.5660 0.2987 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9399 1.9230 -0.7800 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2494 2.5848 -1.5847 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3666 3.9205 0.5277 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9578 4.5392 1.6201 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7208 3.7693 2.4965 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8550 2.4374 2.2435 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3098 4.4038 3.5919 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8226 5.8776 1.8726 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6461 6.9120 1.4237 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6009 4.6789 -0.3579 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1811 -1.5984 -0.1416 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7204 -2.2142 0.9899 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0780 -3.5326 1.0331 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9184 -4.3479 -0.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3843 -3.7519 -1.2133 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0331 -2.4186 -1.2241 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2608 -5.6827 -0.0943 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6135 -4.1308 2.1732 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2064 0.8263 -3.9346 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1272 -1.9165 -4.4253 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0128 -3.4106 -3.6173 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1679 0.4341 -1.5681 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5852 0.4180 -0.6729 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4404 0.2568 2.0669 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7371 1.4997 2.6218 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9439 2.4372 2.3883 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9636 1.6092 3.4421 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0217 -2.5592 2.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8006 -2.4630 3.5958 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0530 -1.1301 3.4060 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6767 -0.6187 2.4640 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7085 0.9410 1.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2746 -1.4810 0.1485 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7699 -1.5530 -1.6229 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9460 -0.3572 0.4993 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8989 -1.6561 0.3698 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1492 -0.3331 -0.7783 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3561 -3.2532 -1.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8827 -1.6637 -3.0568 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5978 -0.8721 -4.8240 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5205 0.5136 -2.9007 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7724 0.1257 -1.0332 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4437 1.8117 2.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8271 5.2606 3.3810 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0719 7.5244 2.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4042 6.5680 0.6918 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0070 7.6415 0.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0860 5.4728 -0.0060 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8750 -1.6227 1.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2328 -4.3398 -2.1264 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6409 -2.0052 -2.1329 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2336 -6.0268 -0.1270 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7147 -5.1166 2.2784 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9389 0.6791 -4.8815 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0044 -2.8779 -4.5615 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4248 -4.0760 -3.1952 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7463 0.5207 -2.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3026 -0.0600 -1.1558 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1004 2.6483 3.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8484 0.9445 4.3446 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8861 1.3362 2.9238 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 21 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 25 29 1 0 29 30 1 0 24 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 45 46 1 0 46 47 2 0 46 48 1 0 7 2 1 0 15 10 1 0 22 17 1 0 27 20 1 0 37 32 1 0 1 49 1 0 1 50 1 0 1 51 1 0 2 52 1 0 3 53 1 0 4 54 1 0 5 55 1 0 6 56 1 0 9 57 1 0 9 58 1 0 10 59 1 0 11 60 1 0 12 61 1 0 13 62 1 0 14 63 1 0 27 64 1 0 28 65 1 0 30 66 1 0 30 67 1 0 30 68 1 0 31 69 1 0 33 70 1 0 36 71 1 0 37 72 1 0 38 73 1 0 39 74 1 0 40 75 1 0 41 76 1 0 42 77 1 0 43 78 1 0 44 79 1 0 48 80 1 0 48 81 1 0 48 82 1 0 M END

Standard InCHIKey	NMYATQQEONGBHA-ASCKONKUSA-N
Standard InCHI	InChI=1S/C30H34O18/c1-9-25(45-10(2)31)22(39)24(41)29(44-9)43-8-16-18(35)21(38)23(40)30(47-16)48-28-20(37)17-15(7-14(34)27(42-3)19(17)36)46-26(28)11-4-5-12(32)13(33)6-11/h4-7,9,16,18,21-25,29-30,32-36,38-41H,8H2,1-3H3/t9-,16+,18+,21-,22-,23+,24+,25-,29+,30-/m0/s1
SMILES	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=C(C3=O)C(=C(C(=C4)O)OC)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	682.17	Volume:	619.15 ? Van der Waals volume.
Dense:	1.102	LogP:	0.263 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.898 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.047 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	31.0
TPSA:	284.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.101	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.974	Fsp³:	0.467
MCE-18:	127.818 ? 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:	0.282	Fluc inhibitor:	0.031 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.91 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.904 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.091	Promiscuous compounds:	0.24

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.149	MDCK Permeability:	-5.289
Pgp-inhibitor:	0.0	Pgp-substrate:	0.864
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):	0.944
20% Bioavailability (F20%):	0.786	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.935
Plasma Protein Binding (PPB):	77.42%	Volume Distribution (VD):	-0.166
Fu:	23.189% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.005
OATP1B3 inhibitor:	0.944	BCRP inhibitor:	0.351
BSEP inhibitor:	0.013

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.018	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.426 ? 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):

2.129

Half-life (T1/2):

3.338

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.501
Human Hepatotoxicity (H-HT):	0.335	Drug-induced Liver Injury (DILI):	0.849
AMES Toxicity:	0.715	Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.476	Skin Sensitization:	0.642
Carcinogencity:	0.077	Eye Corrosion:	0.0
Eye Irritation:	0.028	Respiratory Toxicity:	0.024
Drug-induced Neurotoxicity:	0.037	Ototoxicity:	0.974
Hematotoxicity:	0.013	Drug-induced Nephrotoxicity:	0.011
Genotoxicity:	0.795	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.428	Hek293 Cytotoxicity:	0.676
BCF:	0.443 ? 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:	3.053 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.938 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.939 ? 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	=	2.16	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 NPC470446 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	14654
0.1-0.2	31359
0.2-0.3	2972
0.3-0.4	473
0.4-0.5	248
0.5-0.6	96
0.6-0.7	34
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8977	High Similarity	NPC470449
0.8202	Intermediate Similarity	NPC126784
0.8202	Intermediate Similarity	NPC241423
0.8191	Intermediate Similarity	NPC470451
0.8	Intermediate Similarity	NPC488073
0.7802	Intermediate Similarity	NPC488074
0.7766	Intermediate Similarity	NPC470445
0.7312	Intermediate Similarity	NPC473571
0.7312	Intermediate Similarity	NPC110941
0.7071	Intermediate Similarity	NPC470455
0.7045	Intermediate Similarity	NPC305811
0.6939	Remote Similarity	NPC470447
0.6778	Remote Similarity	NPC42773
0.6778	Remote Similarity	NPC45522
0.6667	Remote Similarity	NPC203259
0.6667	Remote Similarity	NPC33054
0.6667	Remote Similarity	NPC176740
0.6667	Remote Similarity	NPC471725
0.6667	Remote Similarity	NPC134532
0.6667	Remote Similarity	NPC602582
0.6633	Remote Similarity	NPC483415
0.6596	Remote Similarity	NPC116864
0.6596	Remote Similarity	NPC244776
0.6495	Remote Similarity	NPC156869
0.6465	Remote Similarity	NPC470443
0.6436	Remote Similarity	NPC471669
0.6392	Remote Similarity	NPC67326
0.6275	Remote Similarity	NPC473073
0.6238	Remote Similarity	NPC473327
0.6214	Remote Similarity	NPC36138
0.6154	Remote Similarity	NPC470450
0.6117	Remote Similarity	NPC476472
0.6117	Remote Similarity	NPC294815
0.6117	Remote Similarity	NPC16194
0.6075	Remote Similarity	NPC292019
0.6075	Remote Similarity	NPC202908
0.6061	Remote Similarity	NPC173582
0.6061	Remote Similarity	NPC265885
0.6061	Remote Similarity	NPC181465
0.6061	Remote Similarity	NPC215710
0.6061	Remote Similarity	NPC473438
0.6061	Remote Similarity	NPC253788
0.604	Remote Similarity	NPC153755
0.6	Remote Similarity	NPC65563
0.6	Remote Similarity	NPC470949
0.5981	Remote Similarity	NPC470416
0.5962	Remote Similarity	NPC483413
0.5962	Remote Similarity	NPC483412
0.5957	Remote Similarity	NPC488080
0.5957	Remote Similarity	NPC169977
0.59	Remote Similarity	NPC39834
0.5876	Remote Similarity	NPC209023
0.5865	Remote Similarity	NPC488089
0.5833	Remote Similarity	NPC159579
0.581	Remote Similarity	NPC89127
0.58	Remote Similarity	NPC471079
0.5789	Remote Similarity	NPC27640
0.5773	Remote Similarity	NPC101026
0.5773	Remote Similarity	NPC488077
0.5769	Remote Similarity	NPC483416
0.5701	Remote Similarity	NPC223426
0.5673	Remote Similarity	NPC483414
0.567	Remote Similarity	NPC182121
0.567	Remote Similarity	NPC175107
0.5648	Remote Similarity	NPC81042
0.5644	Remote Similarity	NPC609888
0.5631	Remote Similarity	NPC186816
0.5625	Remote Similarity	NPC271692
0.5619	Remote Similarity	NPC37668
0.5588	Remote Similarity	NPC471748
0.5579	Remote Similarity	NPC127546
0.5579	Remote Similarity	NPC57625
0.5579	Remote Similarity	NPC173637
0.5579	Remote Similarity	NPC317489
0.5579	Remote Similarity	NPC223424
0.5579	Remote Similarity	NPC600591
0.5566	Remote Similarity	NPC486577
0.5545	Remote Similarity	NPC189564
0.551	Remote Similarity	NPC488071
0.5492	Remote Similarity	NPC72554
0.5472	Remote Similarity	NPC122467
0.547	Remote Similarity	NPC241781
0.5431	Remote Similarity	NPC156785
0.5408	Remote Similarity	NPC599850
0.5392	Remote Similarity	NPC254540
0.5385	Remote Similarity	NPC488078
0.5377	Remote Similarity	NPC480471
0.5377	Remote Similarity	NPC488076
0.5361	Remote Similarity	NPC145038
0.5361	Remote Similarity	NPC56077
0.5361	Remote Similarity	NPC281131
0.5361	Remote Similarity	NPC253662
0.5361	Remote Similarity	NPC179950
0.5361	Remote Similarity	NPC88789
0.5361	Remote Similarity	NPC491374
0.5357	Remote Similarity	NPC173837
0.5317	Remote Similarity	NPC97817
0.5294	Remote Similarity	NPC163524
0.5288	Remote Similarity	NPC67105
0.5268	Remote Similarity	NPC488075
0.5253	Remote Similarity	NPC59534
0.5242	Remote Similarity	NPC30011
0.5238	Remote Similarity	NPC233994
0.5238	Remote Similarity	NPC605592
0.5229	Remote Similarity	NPC85751
0.5229	Remote Similarity	NPC19240
0.5225	Remote Similarity	NPC214621
0.5225	Remote Similarity	NPC34267
0.5217	Remote Similarity	NPC139571
0.52	Remote Similarity	NPC219904
0.5192	Remote Similarity	NPC29958
0.5189	Remote Similarity	NPC129264
0.5185	Remote Similarity	NPC270448
0.5179	Remote Similarity	NPC121703
0.5179	Remote Similarity	NPC203145
0.5175	Remote Similarity	NPC480441
0.5175	Remote Similarity	NPC217520
0.5169	Remote Similarity	NPC162394
0.5146	Remote Similarity	NPC265115
0.514	Remote Similarity	NPC154741
0.5115	Remote Similarity	NPC482521
0.5104	Remote Similarity	NPC276222
0.5104	Remote Similarity	NPC274618
0.5104	Remote Similarity	NPC118284
0.5104	Remote Similarity	NPC608147
0.5098	Remote Similarity	NPC223747
0.5094	Remote Similarity	NPC210073
0.5093	Remote Similarity	NPC75574
0.5093	Remote Similarity	NPC211532
0.5093	Remote Similarity	NPC488364
0.5088	Remote Similarity	NPC477895
0.5052	Remote Similarity	NPC67037
0.5052	Remote Similarity	NPC255615
0.5051	Remote Similarity	NPC265530
0.5051	Remote Similarity	NPC136042
0.5048	Remote Similarity	NPC139320
0.5047	Remote Similarity	NPC470444
0.5046	Remote Similarity	NPC104883
0.5046	Remote Similarity	NPC488679
0.5044	Remote Similarity	NPC89052
0.5043	Remote Similarity	NPC303694

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470446 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4707
0.1-0.2	4390
0.2-0.3	42
0.3-0.4	6
0.4-0.5	2
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
0.6667	Remote Similarity	NPD6797	Phase 2
0.5962	Remote Similarity	NPD7251	Phase 2
0.5044	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