NPASS Compound

Natural Product: NPC470447

Natural Product ID	NPC470447
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-Methoxykaempferol-3-O-(2-O-Acetyl)-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name	[(2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-methyloxan-3-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2037050
PubChem CID	57409958
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 81 85 0 0 0 0 0 0 0 0999 V2000 -4.5966 5.8466 -1.7384 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8222 5.1826 -0.4997 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8444 3.8019 -0.3860 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0427 3.1111 -0.5420 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1994 3.8582 -0.8122 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1053 1.7396 -0.4362 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9734 0.9745 -0.1680 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7875 1.6582 -0.0141 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7265 3.0436 -0.1214 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5045 3.6795 0.0435 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6912 0.8900 0.2459 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5891 1.4784 0.3915 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7496 -0.5308 0.3560 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9744 -1.1133 0.1910 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0196 -0.3183 -0.0646 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2488 -2.5635 0.2663 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4198 -2.9975 -0.3773 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8508 -4.2902 -0.3618 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1213 -5.2374 0.3107 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9761 -4.8271 0.9449 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5360 -3.4912 0.9267 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5281 -6.5740 0.3497 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6388 -1.1443 0.5931 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5356 -1.7531 0.9096 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6328 -0.9348 0.9388 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6654 -1.7803 1.4042 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6892 -1.0787 2.2100 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3440 -0.0203 1.7645 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1603 0.0552 0.7023 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4573 0.3811 1.0556 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7063 1.6598 1.4056 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1907 1.9267 1.2509 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9569 2.7237 0.6759 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5350 2.3889 0.3608 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5804 1.0188 -0.3184 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5012 1.0943 -1.3901 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1852 0.7702 -2.6964 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0115 0.3874 -2.9363 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1631 0.8543 -3.8094 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0393 3.3631 -0.5104 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9927 3.9245 1.4048 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0907 -2.8044 0.4294 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0392 -2.7502 -0.7070 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2815 -2.9416 -0.0074 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2115 -4.1361 0.7136 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0646 -1.4941 -1.3040 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9309 -4.1313 0.9355 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4255 6.9232 -1.5955 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6865 5.4503 -2.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4691 5.7496 -2.4125 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3061 4.7751 -0.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0483 1.2079 -0.5598 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1050 4.2262 -0.7283 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0406 -2.2783 -0.9329 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7557 -4.5498 -0.8755 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3809 -5.5617 1.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6695 -3.2114 1.4656 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5027 -7.1217 -0.5078 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5682 -2.1025 2.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0715 -2.4003 2.2041 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3732 -1.9110 2.6018 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1702 -0.7820 3.1957 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2401 -0.9126 0.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4867 1.7822 2.4964 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4304 1.6890 0.1827 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8061 1.2623 1.8981 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4369 2.9969 1.3775 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4718 2.9501 -0.3016 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9257 2.3171 1.2874 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5915 0.6773 -0.6125 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3804 1.9242 -4.0762 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7730 0.3371 -4.7084 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1195 0.3448 -3.5604 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7480 3.9908 -0.7870 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6026 3.8463 2.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0909 -2.7901 0.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2289 -3.5556 -1.4346 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1281 -3.0227 -0.7452 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6094 -4.8443 0.1285 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1835 -1.5645 -2.2923 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6028 -4.7420 0.5758 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 4 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 8 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 19 22 1 0 13 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 34 40 1 0 33 41 1 0 26 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 9 3 1 0 21 16 1 0 44 24 1 0 15 7 1 0 35 29 1 0 1 48 1 0 1 49 1 0 1 50 1 0 5 51 1 0 6 52 1 0 10 53 1 0 17 54 1 0 18 55 1 0 20 56 1 0 21 57 1 0 22 58 1 0 24 59 1 1 26 60 1 1 27 61 1 0 27 62 1 0 29 63 1 6 31 64 1 1 32 65 1 0 32 66 1 0 32 67 1 0 33 68 1 6 34 69 1 1 35 70 1 6 39 71 1 0 39 72 1 0 39 73 1 0 40 74 1 0 41 75 1 0 42 76 1 6 43 77 1 6 44 78 1 6 45 79 1 0 46 80 1 0 47 81 1 0 M END

Standard InCHIKey	ZYGLJBBAGQITBG-ARCGLVIYSA-N
Standard InCHI	InChI=1S/C30H34O17/c1-10-18(34)23(39)28(44-11(2)31)30(43-10)42-9-16-19(35)22(38)24(40)29(46-16)47-27-21(37)17-15(8-14(33)26(41-3)20(17)36)45-25(27)12-4-6-13(32)7-5-12/h4-8,10,16,18-19,22-24,28-30,32-36,38-40H,9H2,1-3H3/t10-,16+,18-,19+,22-,23+,24+,28+,29-,30+/m0/s1
SMILES	COc1c(O)cc2c(c1O)c(=O)c(c(o2)c1ccc(cc1)O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2OC(=O)C)O)O)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.18	Volume:	610.359 ? Van der Waals volume.
Dense:	1.091	LogP:	0.09 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.603 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.288 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	31.0
TPSA:	264.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.881	Fsp³:	0.467
MCE-18:	124.364 ? 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:	0
Colloidal aggregators:	0.592	Fluc inhibitor:	0.229 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.781 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.58 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.072	Promiscuous compounds:	0.377

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.191	MDCK Permeability:	-5.378
Pgp-inhibitor:	0.002	Pgp-substrate:	0.783
PAMPA:	0.998 ? 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):	0.009
20% Bioavailability (F20%):	0.009	30% Bioavailability (F30%):	0.718
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.231
Plasma Protein Binding (PPB):	82.173%	Volume Distribution (VD):	-0.031
Fu:	15.894% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.513
BSEP inhibitor:	0.06

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.289 ? 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):

1.688

Half-life (T1/2):

3.803

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.159
Human Hepatotoxicity (H-HT):	0.451	Drug-induced Liver Injury (DILI):	0.873
AMES Toxicity:	0.795	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.039	Skin Sensitization:	0.994
Carcinogencity:	0.046	Eye Corrosion:	0.0
Eye Irritation:	0.161	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.924
Hematotoxicity:	0.074	Drug-induced Nephrotoxicity:	0.219
Genotoxicity:	0.792	RPMI-8226 Immunitoxicity:	0.107
A549 Cytotoxicity:	0.328	Hek293 Cytotoxicity:	0.482
BCF:	0.401 ? 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:	3.056 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.412 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.75 ? 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	=	1.0	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 NPC470447 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	14843
0.1-0.2	31114
0.2-0.3	3001
0.3-0.4	470
0.4-0.5	273
0.5-0.6	109
0.6-0.7	28
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8966	High Similarity	NPC470445
0.8352	Intermediate Similarity	NPC470455
0.8068	Intermediate Similarity	NPC473571
0.8068	Intermediate Similarity	NPC110941
0.7742	Intermediate Similarity	NPC470449
0.7604	Intermediate Similarity	NPC470451
0.7204	Intermediate Similarity	NPC126784
0.7204	Intermediate Similarity	NPC241423
0.701	Intermediate Similarity	NPC36138
0.6939	Remote Similarity	NPC470446
0.6939	Remote Similarity	NPC470450
0.6842	Remote Similarity	NPC488074
0.6818	Remote Similarity	NPC488080
0.6818	Remote Similarity	NPC169977
0.6733	Remote Similarity	NPC470416
0.6667	Remote Similarity	NPC488073
0.6629	Remote Similarity	NPC305811
0.6526	Remote Similarity	NPC173582
0.6526	Remote Similarity	NPC265885
0.6526	Remote Similarity	NPC181465
0.6526	Remote Similarity	NPC215710
0.6526	Remote Similarity	NPC473438
0.6526	Remote Similarity	NPC253788
0.6458	Remote Similarity	NPC65563
0.6458	Remote Similarity	NPC470949
0.6224	Remote Similarity	NPC470444
0.62	Remote Similarity	NPC473327
0.6162	Remote Similarity	NPC153755
0.6082	Remote Similarity	NPC471079
0.6078	Remote Similarity	NPC476472
0.6078	Remote Similarity	NPC294815
0.6078	Remote Similarity	NPC16194
0.6061	Remote Similarity	NPC186816
0.6042	Remote Similarity	NPC116864
0.6042	Remote Similarity	NPC244776
0.6022	Remote Similarity	NPC42773
0.6022	Remote Similarity	NPC45522
0.596	Remote Similarity	NPC203259
0.596	Remote Similarity	NPC33054
0.596	Remote Similarity	NPC176740
0.596	Remote Similarity	NPC471725
0.596	Remote Similarity	NPC134532
0.596	Remote Similarity	NPC602582
0.5941	Remote Similarity	NPC483414
0.5934	Remote Similarity	NPC111929
0.5934	Remote Similarity	NPC320283
0.5934	Remote Similarity	NPC41121
0.5914	Remote Similarity	NPC46420
0.5895	Remote Similarity	NPC101026
0.5895	Remote Similarity	NPC488077
0.5851	Remote Similarity	NPC216496
0.5769	Remote Similarity	NPC85751
0.5769	Remote Similarity	NPC19240
0.5758	Remote Similarity	NPC609888
0.5743	Remote Similarity	NPC129264
0.5741	Remote Similarity	NPC173837
0.5701	Remote Similarity	NPC121703
0.5648	Remote Similarity	NPC189564
0.5631	Remote Similarity	NPC12013
0.5631	Remote Similarity	NPC470443
0.5631	Remote Similarity	NPC11432
0.5631	Remote Similarity	NPC477613
0.5625	Remote Similarity	NPC219904
0.5619	Remote Similarity	NPC89127
0.5607	Remote Similarity	NPC214621
0.5607	Remote Similarity	NPC34267
0.5579	Remote Similarity	NPC24043
0.5577	Remote Similarity	NPC270448
0.5545	Remote Similarity	NPC67326
0.5545	Remote Similarity	NPC39834
0.5534	Remote Similarity	NPC470125
0.5532	Remote Similarity	NPC249281
0.5524	Remote Similarity	NPC142142
0.551	Remote Similarity	NPC223747
0.549	Remote Similarity	NPC156869
0.5474	Remote Similarity	NPC265530
0.5472	Remote Similarity	NPC473073
0.5464	Remote Similarity	NPC159579
0.5455	Remote Similarity	NPC276377
0.5455	Remote Similarity	NPC477895
0.5421	Remote Similarity	NPC287889
0.5421	Remote Similarity	NPC221342
0.5421	Remote Similarity	NPC476470
0.5417	Remote Similarity	NPC27640
0.5405	Remote Similarity	NPC217520
0.54	Remote Similarity	NPC172807
0.5385	Remote Similarity	NPC64425
0.537	Remote Similarity	NPC223426
0.537	Remote Similarity	NPC135358
0.537	Remote Similarity	NPC602448
0.5368	Remote Similarity	NPC127546
0.5368	Remote Similarity	NPC57625
0.5368	Remote Similarity	NPC77672
0.5368	Remote Similarity	NPC133671
0.5368	Remote Similarity	NPC135391
0.5368	Remote Similarity	NPC173637
0.5368	Remote Similarity	NPC78263
0.5368	Remote Similarity	NPC317489
0.5368	Remote Similarity	NPC250069
0.5368	Remote Similarity	NPC223424
0.5368	Remote Similarity	NPC600591
0.5351	Remote Similarity	NPC488734
0.5351	Remote Similarity	NPC488735
0.5351	Remote Similarity	NPC488732
0.5351	Remote Similarity	NPC488738
0.5333	Remote Similarity	NPC483415
0.5327	Remote Similarity	NPC483412
0.5301	Remote Similarity	NPC266960
0.53	Remote Similarity	NPC476215
0.5283	Remote Similarity	NPC483416
0.5283	Remote Similarity	NPC72016
0.5278	Remote Similarity	NPC298171
0.5273	Remote Similarity	NPC89052
0.5273	Remote Similarity	NPC203145
0.5268	Remote Similarity	NPC25523
0.5258	Remote Similarity	NPC271692
0.5253	Remote Similarity	NPC224530
0.5217	Remote Similarity	NPC488739
0.5204	Remote Similarity	NPC472459
0.52	Remote Similarity	NPC116458
0.52	Remote Similarity	NPC246943
0.5192	Remote Similarity	NPC150164
0.5185	Remote Similarity	NPC471669
0.5182	Remote Similarity	NPC244875
0.5182	Remote Similarity	NPC81042
0.5179	Remote Similarity	NPC292019
0.5179	Remote Similarity	NPC202908
0.5175	Remote Similarity	NPC139571
0.5169	Remote Similarity	NPC488737
0.5164	Remote Similarity	NPC473554
0.5152	Remote Similarity	NPC175107
0.5152	Remote Similarity	NPC129217
0.5152	Remote Similarity	NPC611303
0.514	Remote Similarity	NPC122467
0.514	Remote Similarity	NPC37668
0.5106	Remote Similarity	NPC54802
0.5106	Remote Similarity	NPC197304
0.51	Remote Similarity	NPC120099
0.5098	Remote Similarity	NPC477848
0.5094	Remote Similarity	NPC296018
0.5088	Remote Similarity	NPC277532
0.5053	Remote Similarity	NPC288084
0.505	Remote Similarity	NPC209023
0.5047	Remote Similarity	NPC75574
0.5043	Remote Similarity	NPC480445
0.5042	Remote Similarity	NPC209550

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4716
0.1-0.2	4377
0.2-0.3	46
0.3-0.4	5
0.4-0.5	3
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.596	Remote Similarity	NPD6797	Phase 2
0.5185	Remote Similarity	NPD7251	Phase 2

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