NPASS Compound

Natural Product: NPC474522

Natural Product ID	NPC474522
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Kaempferol 3-O-Alpha-L-Rhamnopyranosyl(1->6)-(4-O-Trans-P-Coumaroyl)-Beta-D-Galactopyranoside
IUPAC Name	[(2R,3R,4R,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4,5-dihydroxy-2-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-phenylprop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL470714
PubChem CID	44566735
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 88 93 0 0 0 0 0 0 0 0999 V2000 -2.5618 -4.2883 0.6408 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6342 -3.5844 -0.7207 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2862 -4.4561 -1.7410 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6467 -4.0141 -2.1619 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8948 -2.5461 -2.1593 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7028 -1.7723 -1.7134 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2708 -2.3925 -0.5044 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6239 -1.7676 -2.5399 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0114 -0.5366 -2.7576 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4619 0.0443 -1.4791 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9128 1.3965 -1.7370 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6445 1.2236 -1.7588 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0222 0.8249 -0.3695 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3207 -0.4599 -0.0452 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5439 -0.8884 -0.9962 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2389 -1.4901 0.2352 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3707 -1.4457 0.9875 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6010 -1.4989 0.4349 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6628 -1.4171 1.2549 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5314 -1.2938 2.5491 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6705 -1.2138 3.3271 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5794 -1.0877 4.6747 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3295 -1.0349 5.3079 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1886 -1.1121 4.5513 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2838 -1.2410 3.1675 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1859 -1.3201 2.3609 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0153 -1.2759 2.8858 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9034 -1.0730 5.0694 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6715 -1.0031 5.5058 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9159 -1.6553 -0.9974 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2578 -1.5317 -1.4056 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5923 -1.7449 -2.7239 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6634 -2.0781 -3.6768 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3431 -2.2062 -3.3109 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0377 -1.9802 -1.9494 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0738 -2.2810 -5.0119 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3641 0.8721 -0.1168 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.2662 -2.6844 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1748 2.2968 -0.6988 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3450 3.6530 -0.8978 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2103 4.1202 -2.0381 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6836 4.5155 0.2585 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7266 5.8192 0.0696 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0889 6.6818 1.2376 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4603 6.1507 2.4396 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7854 6.9757 3.5066 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7277 8.3250 3.3386 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3513 8.9017 2.1217 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0399 8.0520 1.0979 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8877 -2.3247 -1.1670 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5664 -4.7148 -1.3441 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3345 -5.7592 -1.1957 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1028 -3.5742 1.3447 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9443 -5.2046 0.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6051 -4.4871 0.9450 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5620 -3.4413 -1.0304 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6646 -4.5759 -2.6666 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8570 -4.4037 -3.1977 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3483 -2.1775 -3.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9401 -0.7321 -1.4020 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7016 0.1811 -3.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2048 -0.7324 -3.4948 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3030 0.0774 -0.7101 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1463 1.8698 -2.7161 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0716 2.2000 -2.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5484 1.6547 0.2836 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1537 -0.2573 0.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6520 -1.2533 2.8315 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2565 -0.9357 6.3780 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5154 -1.9803 5.3323 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9751 -0.2239 6.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9800 -1.2829 -0.6730 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6264 -1.6554 -3.0592 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6059 -2.4635 -4.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9731 -2.1086 -1.7229 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0871 -2.3494 -5.1872 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8292 1.0408 -0.9809 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8009 0.5600 -3.6167 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8693 4.0729 1.1925 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5192 6.3112 -0.8462 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5204 5.0827 2.6285 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0898 6.5610 4.4858 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9663 9.0042 4.1562 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3246 9.9902 2.0659 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7384 8.5081 0.1416 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4951 -1.9991 -0.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3030 -5.0828 -1.8669 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0474 -5.8229 -0.5105 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 22 29 1 0 18 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 13 37 1 0 12 38 1 0 11 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 2 3 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 5 50 1 0 4 51 1 0 3 52 1 0 7 2 1 0 15 10 1 0 26 17 1 0 25 20 1 0 35 30 1 0 49 44 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 0 3 57 1 0 4 58 1 0 5 59 1 0 6 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 11 64 1 0 12 65 1 0 13 66 1 0 14 67 1 0 21 68 1 0 23 69 1 0 28 70 1 0 29 71 1 0 31 72 1 0 32 73 1 0 34 74 1 0 35 75 1 0 36 76 1 0 37 77 1 0 38 78 1 0 42 79 1 0 43 80 1 0 45 81 1 0 46 82 1 0 47 83 1 0 48 84 1 0 49 85 1 0 50 86 1 0 51 87 1 0 52 88 1 0 M END

Standard InCHIKey	NVACRDDCQWUEKZ-PBCNUSJZSA-N
Standard InCHI	InChI=1S/C36H36O16/c1-16-26(41)28(43)30(45)35(48-16)47-15-23-33(51-24(40)12-7-17-5-3-2-4-6-17)29(44)31(46)36(50-23)52-34-27(42)25-21(39)13-20(38)14-22(25)49-32(34)18-8-10-19(37)11-9-18/h2-14,16,23,26,28-31,33,35-39,41,43-46H,15H2,1H3/b12-7+/t16-,23+,26-,28+,29+,30+,31+,33-,35+,36-/m0/s1
SMILES	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)OC(=O)C=CC6=CC=CC=C6)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	724.2	Volume:	686.243 ? Van der Waals volume.
Dense:	1.055	LogP:	1.17 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.555 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.702 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	38.0
TPSA:	255.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.088	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.912	Fsp³:	0.333
MCE-18:	133.25 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.692	Fluc inhibitor:	0.397 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.814 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.984 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.325	Promiscuous compounds:	0.418

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.177	MDCK Permeability:	-5.217
Pgp-inhibitor:	0.0	Pgp-substrate:	0.948
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):	0.265
20% Bioavailability (F20%):	0.383	30% Bioavailability (F30%):	0.988
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.909
Plasma Protein Binding (PPB):	87.886%	Volume Distribution (VD):	-0.147
Fu:	12.181% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.006
OATP1B3 inhibitor:	0.959	BCRP inhibitor:	0.528
BSEP inhibitor:	0.55

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.005	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:	1.0
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):

1.309

Half-life (T1/2):

3.207

ADMET: Toxicity

hERG Blockers:	0.063	hERG Blockers (10um):	0.66
Human Hepatotoxicity (H-HT):	0.381	Drug-induced Liver Injury (DILI):	0.828
AMES Toxicity:	0.769	Rat Oral Acute Toxicity:	0.445
Maximum Recommended Daily Dose:	0.882	Skin Sensitization:	0.824
Carcinogencity:	0.102	Eye Corrosion:	0.0
Eye Irritation:	0.045	Respiratory Toxicity:	0.031
Drug-induced Neurotoxicity:	0.3	Ototoxicity:	0.836
Hematotoxicity:	0.004	Drug-induced Nephrotoxicity:	0.053
Genotoxicity:	0.908	RPMI-8226 Immunitoxicity:	0.076
A549 Cytotoxicity:	0.35	Hek293 Cytotoxicity:	0.983
BCF:	0.76 ? 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:	3.62 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.266 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.55 ? 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
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043423]
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10828	Adina racemosa	Species	Rubiaceae	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
FC	2

Activity Type	# Activity
Others	2

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
NPT2	Others	Unspecified	n.a.	FC	=	2.0	n.a.	PMID[25899338]

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 NPC474522 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	12776
0.1-0.2	32377
0.2-0.3	3855
0.3-0.4	480
0.4-0.5	174
0.5-0.6	138
0.6-0.7	49
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8812	High Similarity	NPC156785
0.7522	Intermediate Similarity	NPC231787
0.7327	Intermediate Similarity	NPC104883
0.7327	Intermediate Similarity	NPC488679
0.7094	Intermediate Similarity	NPC30011
0.6991	Remote Similarity	NPC241781
0.6832	Remote Similarity	NPC173582
0.6832	Remote Similarity	NPC265885
0.6832	Remote Similarity	NPC181465
0.6832	Remote Similarity	NPC215710
0.6832	Remote Similarity	NPC473438
0.6832	Remote Similarity	NPC253788
0.6814	Remote Similarity	NPC162394
0.6698	Remote Similarity	NPC85751
0.6698	Remote Similarity	NPC19240
0.6667	Remote Similarity	NPC72554
0.65	Remote Similarity	NPC275977
0.6452	Remote Similarity	NPC97817
0.6364	Remote Similarity	NPC214621
0.6364	Remote Similarity	NPC34267
0.6296	Remote Similarity	NPC101399
0.6296	Remote Similarity	NPC217822
0.6296	Remote Similarity	NPC11847
0.6296	Remote Similarity	NPC198938
0.6289	Remote Similarity	NPC111929
0.6289	Remote Similarity	NPC320283
0.6289	Remote Similarity	NPC41121
0.6286	Remote Similarity	NPC203259
0.6286	Remote Similarity	NPC33054
0.6286	Remote Similarity	NPC176740
0.6286	Remote Similarity	NPC471725
0.6286	Remote Similarity	NPC134532
0.6286	Remote Similarity	NPC602582
0.6273	Remote Similarity	NPC223426
0.6147	Remote Similarity	NPC221288
0.6147	Remote Similarity	NPC194836
0.6147	Remote Similarity	NPC91493
0.6147	Remote Similarity	NPC605081
0.6139	Remote Similarity	NPC159579
0.6111	Remote Similarity	NPC12013
0.6111	Remote Similarity	NPC11432
0.6111	Remote Similarity	NPC477613
0.6098	Remote Similarity	NPC473554
0.6091	Remote Similarity	NPC476472
0.6091	Remote Similarity	NPC294815
0.6091	Remote Similarity	NPC16194
0.6071	Remote Similarity	NPC96605
0.6071	Remote Similarity	NPC280642
0.6055	Remote Similarity	NPC473327
0.6038	Remote Similarity	NPC39834
0.6019	Remote Similarity	NPC470125
0.6018	Remote Similarity	NPC203145
0.6	Remote Similarity	NPC205824
0.6	Remote Similarity	NPC217520
0.5982	Remote Similarity	NPC218161
0.5981	Remote Similarity	NPC605592
0.5954	Remote Similarity	NPC482521
0.5952	Remote Similarity	NPC487502
0.5943	Remote Similarity	NPC471079
0.5943	Remote Similarity	NPC139320
0.5929	Remote Similarity	NPC81042
0.5913	Remote Similarity	NPC477895
0.5893	Remote Similarity	NPC221342
0.5893	Remote Similarity	NPC476470
0.5862	Remote Similarity	NPC470712
0.5841	Remote Similarity	NPC602448
0.581	Remote Similarity	NPC476215
0.5804	Remote Similarity	NPC89127
0.5789	Remote Similarity	NPC478277
0.5789	Remote Similarity	NPC478276
0.5789	Remote Similarity	NPC478275
0.5789	Remote Similarity	NPC92815
0.5781	Remote Similarity	NPC249560
0.578	Remote Similarity	NPC129264
0.578	Remote Similarity	NPC473571
0.578	Remote Similarity	NPC110941
0.5743	Remote Similarity	NPC127546
0.5743	Remote Similarity	NPC57625
0.5743	Remote Similarity	NPC173637
0.5743	Remote Similarity	NPC317489
0.5743	Remote Similarity	NPC223424
0.5743	Remote Similarity	NPC600591
0.5702	Remote Similarity	NPC483767
0.5702	Remote Similarity	NPC483769
0.5702	Remote Similarity	NPC483768
0.5702	Remote Similarity	NPC483766
0.569	Remote Similarity	NPC189564
0.5688	Remote Similarity	NPC65563
0.5688	Remote Similarity	NPC470949
0.5672	Remote Similarity	NPC33083
0.5667	Remote Similarity	NPC474093
0.5667	Remote Similarity	NPC104910
0.5664	Remote Similarity	NPC471669
0.5641	Remote Similarity	NPC173837
0.5636	Remote Similarity	NPC186816
0.563	Remote Similarity	NPC139571
0.563	Remote Similarity	NPC470718
0.5625	Remote Similarity	NPC122467
0.5614	Remote Similarity	NPC36138
0.56	Remote Similarity	NPC288084
0.5597	Remote Similarity	NPC482520
0.5597	Remote Similarity	NPC482519
0.5596	Remote Similarity	NPC163242
0.5596	Remote Similarity	NPC272068
0.5588	Remote Similarity	NPC77672
0.5588	Remote Similarity	NPC133671
0.5588	Remote Similarity	NPC135391
0.5588	Remote Similarity	NPC78263
0.5588	Remote Similarity	NPC250069
0.5566	Remote Similarity	NPC223747
0.5545	Remote Similarity	NPC156869
0.5534	Remote Similarity	NPC265530
0.5526	Remote Similarity	NPC135831
0.5524	Remote Similarity	NPC219904
0.5517	Remote Similarity	NPC483765
0.5512	Remote Similarity	NPC487499
0.5492	Remote Similarity	NPC480445
0.549	Remote Similarity	NPC135599
0.549	Remote Similarity	NPC73855
0.549	Remote Similarity	NPC113968
0.549	Remote Similarity	NPC328940
0.549	Remote Similarity	NPC277174
0.549	Remote Similarity	NPC606877
0.5489	Remote Similarity	NPC487501
0.5487	Remote Similarity	NPC270448
0.5476	Remote Similarity	NPC25946
0.547	Remote Similarity	NPC89052
0.5463	Remote Similarity	NPC116864
0.5463	Remote Similarity	NPC244776
0.5455	Remote Similarity	NPC471748
0.5455	Remote Similarity	NPC67326
0.5446	Remote Similarity	NPC296018
0.5429	Remote Similarity	NPC216496
0.5421	Remote Similarity	NPC209023
0.5414	Remote Similarity	NPC487500
0.5377	Remote Similarity	NPC182121
0.5377	Remote Similarity	NPC175107
0.5377	Remote Similarity	NPC129217
0.5366	Remote Similarity	NPC470713
0.5364	Remote Similarity	NPC29958
0.5347	Remote Similarity	NPC54802
0.5347	Remote Similarity	NPC197304
0.5345	Remote Similarity	NPC470449
0.5327	Remote Similarity	NPC85707
0.5321	Remote Similarity	NPC95866
0.531	Remote Similarity	NPC126784
0.531	Remote Similarity	NPC241423
0.531	Remote Similarity	NPC153755
0.5294	Remote Similarity	NPC470416
0.5285	Remote Similarity	NPC488734
0.5285	Remote Similarity	NPC488735
0.5285	Remote Similarity	NPC488739
0.5285	Remote Similarity	NPC488732
0.5285	Remote Similarity	NPC488738
0.5263	Remote Similarity	NPC75574
0.525	Remote Similarity	NPC292019
0.525	Remote Similarity	NPC202908
0.5234	Remote Similarity	NPC48093
0.5214	Remote Similarity	NPC292929
0.5207	Remote Similarity	NPC303694
0.5207	Remote Similarity	NPC164704
0.5197	Remote Similarity	NPC192539
0.5189	Remote Similarity	NPC46420
0.5179	Remote Similarity	NPC470405
0.5159	Remote Similarity	NPC480444
0.5143	Remote Similarity	NPC249281
0.5133	Remote Similarity	NPC155877
0.5133	Remote Similarity	NPC304741
0.5128	Remote Similarity	NPC477629
0.5118	Remote Similarity	NPC488737
0.5096	Remote Similarity	NPC67037
0.5096	Remote Similarity	NPC255615
0.5094	Remote Similarity	NPC145038
0.5094	Remote Similarity	NPC56077
0.5094	Remote Similarity	NPC281131
0.5094	Remote Similarity	NPC64305
0.5094	Remote Similarity	NPC253662
0.5094	Remote Similarity	NPC179950
0.5094	Remote Similarity	NPC88789
0.5094	Remote Similarity	NPC491374
0.5091	Remote Similarity	NPC170052
0.5091	Remote Similarity	NPC276377
0.5091	Remote Similarity	NPC135846
0.5089	Remote Similarity	NPC187379
0.5086	Remote Similarity	NPC37668
0.5077	Remote Similarity	NPC21359
0.5077	Remote Similarity	NPC460984
0.5046	Remote Similarity	NPC259957
0.5046	Remote Similarity	NPC224530
0.5043	Remote Similarity	NPC142142
0.5043	Remote Similarity	NPC154741
0.5039	Remote Similarity	NPC470720

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474522 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3543
0.1-0.2	5523
0.2-0.3	73
0.3-0.4	7
0.4-0.5	3
0.5-0.6	0
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
0.6286	Remote Similarity	NPD6797	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