NPASS Compound

Natural Product: NPC470445

Natural Product ID	NPC470445
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-(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-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-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	CHEMBL2037046
PubChem CID	57409859
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 3.4011 -0.0273 6.0656 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4702 -1.1956 5.2671 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7950 -1.0171 3.9177 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0961 -1.0337 3.4961 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1043 -1.2299 4.4133 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3917 -0.8565 2.1730 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3389 -0.6615 1.2832 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0160 -0.6439 1.7077 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7446 -0.8264 3.0559 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4420 -0.8168 3.5231 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9874 -0.4471 0.8237 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8122 -0.4362 1.2397 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2964 -0.2627 -0.5325 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6061 -0.2941 -0.8965 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5611 -0.4903 0.0312 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0683 -0.1276 -2.2497 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3982 0.1621 -2.4900 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9021 0.2703 -3.7680 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0840 0.0899 -4.8600 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7625 -0.1988 -4.6494 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2765 -0.3033 -3.3351 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9245 -0.3832 -5.7196 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6022 0.2014 -6.1661 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2064 -0.0581 -1.3720 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6489 1.2453 -1.5343 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5020 1.3313 -0.7769 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6884 1.1123 -1.3643 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1347 -0.3554 -1.2682 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2775 -0.8189 -0.0017 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2043 -0.2239 0.8085 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5761 0.3055 1.9289 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4133 0.5478 2.9845 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9498 1.8114 3.6797 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8495 0.7709 2.5703 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4213 -0.3792 1.8116 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2822 -1.2023 1.2591 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7043 -2.0180 0.1814 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5970 -3.3955 0.1510 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0971 -3.9897 1.1288 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0681 -4.1956 -1.0303 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1882 0.1311 0.7375 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5966 0.9672 3.7351 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8992 1.5169 -2.7775 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7822 2.4526 -3.1694 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4933 1.6078 -2.9485 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5236 2.3795 -3.4919 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8050 2.8125 -4.4994 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1516 2.1069 -2.9489 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3623 0.9054 5.4452 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5184 -0.0315 6.7046 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3541 0.0137 6.6484 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0869 -1.2646 4.1735 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4022 -0.8609 1.7890 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2494 -0.6231 4.5034 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0732 0.3090 -1.6409 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9324 0.4964 -3.9663 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2540 -0.5600 -3.2583 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9303 -0.5440 -5.6574 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3237 -0.4340 -6.8980 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3539 1.9485 -1.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4627 1.6728 -0.7580 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9963 -0.5400 -1.9402 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2808 -0.9283 -1.7352 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7498 0.5996 0.3099 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3647 -0.2681 3.7581 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4366 1.5793 4.6495 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8224 2.4564 3.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2032 2.3793 3.0836 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8870 1.7107 1.9814 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1316 -0.9913 2.4030 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8525 -1.7893 2.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2918 -3.5199 -1.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9970 -4.7134 -0.7111 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3279 -4.9567 -1.3257 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3499 1.0965 0.8363 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4921 1.3549 3.5603 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8114 0.6471 -3.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7501 3.3111 -2.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3413 0.7510 -3.6366 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3918 3.3208 -3.2284 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3697 2.0786 -5.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7613 1.4599 -3.3740 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 20 22 1 0 19 23 1 0 13 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 32 33 1 0 32 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 35 41 1 0 34 42 1 0 27 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 9 3 1 0 21 16 1 0 45 25 1 0 15 7 1 0 36 30 1 0 1 49 1 0 1 50 1 0 1 51 1 0 5 52 1 0 6 53 1 0 10 54 1 0 17 55 1 0 18 56 1 0 21 57 1 0 22 58 1 0 23 59 1 0 25 60 1 1 27 61 1 1 28 62 1 0 28 63 1 0 30 64 1 6 32 65 1 1 33 66 1 0 33 67 1 0 33 68 1 0 34 69 1 6 35 70 1 1 36 71 1 1 40 72 1 0 40 73 1 0 40 74 1 0 41 75 1 0 42 76 1 0 43 77 1 6 44 78 1 1 45 79 1 6 46 80 1 0 47 81 1 0 48 82 1 0 M END

Standard InCHIKey	JBDXASDPMNIEKG-YJRFCQSGSA-N
Standard InCHI	InChI=1S/C30H34O18/c1-9-18(35)23(40)28(45-10(2)31)30(44-9)43-8-16-19(36)22(39)24(41)29(47-16)48-27-21(38)17-15(7-14(34)26(42-3)20(17)37)46-25(27)11-4-5-12(32)13(33)6-11/h4-7,9,16,18-19,22-24,28-30,32-37,39-41H,8H2,1-3H3/t9-,16+,18-,19+,22-,23+,24+,28+,29-,30+/m0/s1
SMILES	COc1c(O)cc2c(c1O)c(=O)c(c(o2)c1ccc(c(c1)O)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:	682.17	Volume:	619.15 ? Van der Waals volume.
Dense:	1.102	LogP:	-0.1 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.466 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.146 ? 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:	4.977	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:	0.612	Fluc inhibitor:	0.248 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.872 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.622 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.092	Promiscuous compounds:	0.42

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.201	MDCK Permeability:	-5.426
Pgp-inhibitor:	0.0	Pgp-substrate:	0.395
PAMPA:	0.996 ? 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):	0.119
20% Bioavailability (F20%):	0.208	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.232
Plasma Protein Binding (PPB):	79.487%	Volume Distribution (VD):	-0.096
Fu:	18.989% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.475
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.287 ? 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):

2.068

Half-life (T1/2):

4.208

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.203
Human Hepatotoxicity (H-HT):	0.39	Drug-induced Liver Injury (DILI):	0.907
AMES Toxicity:	0.819	Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.032	Skin Sensitization:	0.999
Carcinogencity:	0.027	Eye Corrosion:	0.0
Eye Irritation:	0.179	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.97
Hematotoxicity:	0.052	Drug-induced Nephrotoxicity:	0.137
Genotoxicity:	0.753	RPMI-8226 Immunitoxicity:	0.064
A549 Cytotoxicity:	0.676	Hek293 Cytotoxicity:	0.262
BCF:	0.461 ? 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:	3.114 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.53 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.884 ? 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	=	1.373	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 NPC470445 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	15530
0.1-0.2	30617
0.2-0.3	2841
0.3-0.4	459
0.4-0.5	248
0.5-0.6	116
0.6-0.7	31
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	NPC470447
0.8478	Intermediate Similarity	NPC470451
0.809	Intermediate Similarity	NPC126784
0.809	Intermediate Similarity	NPC241423
0.7766	Intermediate Similarity	NPC470446
0.7529	Intermediate Similarity	NPC305811
0.75	Intermediate Similarity	NPC470455
0.75	Intermediate Similarity	NPC488073
0.75	Intermediate Similarity	NPC488074
0.7204	Intermediate Similarity	NPC473571
0.7204	Intermediate Similarity	NPC110941
0.6939	Remote Similarity	NPC470449
0.6854	Remote Similarity	NPC42773
0.6854	Remote Similarity	NPC45522
0.6701	Remote Similarity	NPC483414
0.6667	Remote Similarity	NPC116864
0.6667	Remote Similarity	NPC244776
0.6562	Remote Similarity	NPC203259
0.6562	Remote Similarity	NPC33054
0.6562	Remote Similarity	NPC176740
0.6562	Remote Similarity	NPC471725
0.6562	Remote Similarity	NPC134532
0.6562	Remote Similarity	NPC602582
0.6364	Remote Similarity	NPC470443
0.63	Remote Similarity	NPC473327
0.6275	Remote Similarity	NPC36138
0.6214	Remote Similarity	NPC470450
0.6196	Remote Similarity	NPC27640
0.6176	Remote Similarity	NPC473073
0.6176	Remote Similarity	NPC89127
0.6122	Remote Similarity	NPC67326
0.61	Remote Similarity	NPC153755
0.6061	Remote Similarity	NPC156869
0.604	Remote Similarity	NPC483415
0.6038	Remote Similarity	NPC470416
0.6022	Remote Similarity	NPC271692
0.6022	Remote Similarity	NPC488080
0.6022	Remote Similarity	NPC169977
0.6019	Remote Similarity	NPC476472
0.6019	Remote Similarity	NPC294815
0.6019	Remote Similarity	NPC16194
0.6019	Remote Similarity	NPC483412
0.598	Remote Similarity	NPC483416
0.5978	Remote Similarity	NPC127546
0.5978	Remote Similarity	NPC57625
0.5978	Remote Similarity	NPC173637
0.5978	Remote Similarity	NPC317489
0.5978	Remote Similarity	NPC223424
0.5978	Remote Similarity	NPC600591
0.596	Remote Similarity	NPC173582
0.596	Remote Similarity	NPC265885
0.596	Remote Similarity	NPC181465
0.596	Remote Similarity	NPC215710
0.596	Remote Similarity	NPC473438
0.596	Remote Similarity	NPC253788
0.59	Remote Similarity	NPC65563
0.59	Remote Similarity	NPC470949
0.5833	Remote Similarity	NPC101026
0.5833	Remote Similarity	NPC488077
0.58	Remote Similarity	NPC39834
0.5755	Remote Similarity	NPC223426
0.5729	Remote Similarity	NPC175107
0.5729	Remote Similarity	NPC219904
0.5714	Remote Similarity	NPC471669
0.5701	Remote Similarity	NPC81042
0.57	Remote Similarity	NPC609888
0.5688	Remote Similarity	NPC292019
0.5688	Remote Similarity	NPC202908
0.5688	Remote Similarity	NPC173837
0.5673	Remote Similarity	NPC122467
0.5673	Remote Similarity	NPC37668
0.5625	Remote Similarity	NPC59534
0.5619	Remote Similarity	NPC486577
0.5577	Remote Similarity	NPC480471
0.5577	Remote Similarity	NPC488076
0.5567	Remote Similarity	NPC488071
0.5545	Remote Similarity	NPC471079
0.5534	Remote Similarity	NPC470444
0.5534	Remote Similarity	NPC186816
0.55	Remote Similarity	NPC265115
0.5455	Remote Similarity	NPC223747
0.5455	Remote Similarity	NPC488075
0.5446	Remote Similarity	NPC254540
0.5431	Remote Similarity	NPC488078
0.5417	Remote Similarity	NPC145038
0.5417	Remote Similarity	NPC56077
0.5417	Remote Similarity	NPC281131
0.5417	Remote Similarity	NPC253662
0.5417	Remote Similarity	NPC265530
0.5417	Remote Similarity	NPC179950
0.5417	Remote Similarity	NPC88789
0.5417	Remote Similarity	NPC491374
0.5408	Remote Similarity	NPC611303
0.5368	Remote Similarity	NPC111929
0.5368	Remote Similarity	NPC320283
0.5368	Remote Similarity	NPC41121
0.5361	Remote Similarity	NPC46420
0.5357	Remote Similarity	NPC480441
0.5357	Remote Similarity	NPC163524
0.5347	Remote Similarity	NPC95866
0.5345	Remote Similarity	NPC162394
0.5345	Remote Similarity	NPC488736
0.5345	Remote Similarity	NPC488733
0.5321	Remote Similarity	NPC135358
0.5306	Remote Similarity	NPC216496
0.5306	Remote Similarity	NPC599850
0.53	Remote Similarity	NPC605784
0.5288	Remote Similarity	NPC233994
0.5278	Remote Similarity	NPC85751
0.5278	Remote Similarity	NPC19240
0.5278	Remote Similarity	NPC483413
0.5273	Remote Similarity	NPC244875
0.5273	Remote Similarity	NPC214621
0.5273	Remote Similarity	NPC34267
0.5268	Remote Similarity	NPC477895
0.5263	Remote Similarity	NPC139571
0.5258	Remote Similarity	NPC158674
0.5254	Remote Similarity	NPC488737
0.5254	Remote Similarity	NPC241781
0.5238	Remote Similarity	NPC129264
0.5234	Remote Similarity	NPC270448
0.5234	Remote Similarity	NPC606657
0.5229	Remote Similarity	NPC287889
0.5225	Remote Similarity	NPC89052
0.5225	Remote Similarity	NPC121703
0.5221	Remote Similarity	NPC217520
0.5221	Remote Similarity	NPC303694
0.5214	Remote Similarity	NPC488740
0.5208	Remote Similarity	NPC135599
0.5208	Remote Similarity	NPC73855
0.5208	Remote Similarity	NPC113968
0.5208	Remote Similarity	NPC328940
0.5208	Remote Similarity	NPC277174
0.5208	Remote Similarity	NPC606877
0.52	Remote Similarity	NPC120099
0.5192	Remote Similarity	NPC67105
0.5189	Remote Similarity	NPC154741
0.5185	Remote Similarity	NPC64755
0.5179	Remote Similarity	NPC189564
0.5158	Remote Similarity	NPC276222
0.5158	Remote Similarity	NPC274618
0.5158	Remote Similarity	NPC118284
0.5158	Remote Similarity	NPC608147
0.5143	Remote Similarity	NPC605592
0.514	Remote Similarity	NPC12013
0.514	Remote Similarity	NPC211532
0.514	Remote Similarity	NPC11432
0.514	Remote Similarity	NPC488364
0.514	Remote Similarity	NPC477613
0.5104	Remote Similarity	NPC67037
0.5104	Remote Similarity	NPC255615
0.5102	Remote Similarity	NPC136042
0.5096	Remote Similarity	NPC480466
0.5085	Remote Similarity	NPC156785
0.5051	Remote Similarity	NPC84362
0.5047	Remote Similarity	NPC470125
0.5046	Remote Similarity	NPC142142
0.5042	Remote Similarity	NPC480444

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470445 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4810
0.1-0.2	4290
0.2-0.3	40
0.3-0.4	4
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
0.6562	Remote Similarity	NPD6797	Phase 2
0.5865	Remote Similarity	NPD7251	Phase 2
0.5089	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