NPASS Compound

Natural Product: NPC136761

Natural Product ID	NPC136761
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Kaempferol 4'-O-Beta-D-Glucopyranosyl-(1->2)-Beta-D-Glucopyranoside
IUPAC Name	2-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyphenyl]-3,5,7-trihydroxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2336773
PubChem CID	71720752
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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 73 77 0 0 0 0 0 0 0 0999 V2000 -3.2982 5.9313 2.7072 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5373 4.8968 3.2481 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2777 3.8301 2.2034 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5172 2.8012 2.7538 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5197 1.6766 1.9092 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4378 0.8698 2.2131 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6649 0.5732 1.4793 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6273 -0.2638 2.0033 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7637 -0.6103 1.3299 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0181 -0.1266 0.0487 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0872 0.6989 -0.4903 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 1.0478 0.2158 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2618 -0.5605 -0.5679 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0874 -1.3663 0.0959 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2186 -1.8036 -0.3758 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0381 -2.6358 0.3509 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2428 -3.0861 -0.1834 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0625 -3.9218 0.5505 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6443 -2.7131 -1.4455 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8195 -1.8831 -2.1608 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6290 -1.4371 -1.6348 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8359 -0.6132 -2.3762 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1659 -0.2510 -3.5287 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6336 -0.1748 -1.8201 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8917 0.6542 -2.6346 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1991 -1.4939 -3.4296 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8550 0.9678 1.9477 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8517 1.9884 2.5141 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6183 3.2799 1.7607 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6601 3.0663 0.3875 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4439 2.2131 3.8393 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2157 0.6636 0.6315 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4296 -0.6870 0.4278 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5534 -1.2431 -0.4837 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1373 -2.1509 -1.3350 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0203 -2.8271 -2.1287 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5749 -3.7610 -3.0103 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0844 -1.4245 -2.2422 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0641 -0.6496 -1.3897 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8787 -0.8932 0.0757 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3850 -2.1077 0.5114 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8106 0.7181 -1.6128 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7748 -2.2974 -3.0891 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8849 6.1866 1.8380 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5834 5.2917 3.6699 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1073 4.5093 4.1175 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7394 4.3279 1.3676 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3639 2.1051 0.8845 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4957 -0.6812 3.0018 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4960 -1.2754 1.7847 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2366 1.0985 -1.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2377 1.7075 -0.2904 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7384 -2.9374 1.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1036 -3.8351 1.5585 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5744 -3.0412 -1.8984 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3083 1.3597 -3.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6759 -0.6279 -3.6493 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8030 0.0820 2.5787 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8785 1.6323 2.4483 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4306 3.9924 2.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5703 3.1689 0.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5114 1.3438 4.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2540 -1.1951 1.3989 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6842 -2.9664 -0.8374 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4122 -2.1176 -2.6916 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3633 -3.3941 -1.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3876 -4.1866 -2.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4599 -0.7480 -2.8866 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1191 -0.8299 -1.7125 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4490 -0.1058 0.6446 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0161 -2.2608 1.4288 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9801 0.8564 -2.1364 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7340 -2.3542 -2.8485 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 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 17 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 20 26 1 0 5 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 35 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 29 3 1 0 40 33 1 0 12 7 1 0 24 13 2 0 21 15 1 0 1 44 1 0 2 45 1 0 2 46 1 0 3 47 1 6 5 48 1 6 8 49 1 0 9 50 1 0 11 51 1 0 12 52 1 0 16 53 1 0 18 54 1 0 19 55 1 0 25 56 1 0 26 57 1 0 27 58 1 1 28 59 1 1 29 60 1 1 30 61 1 0 31 62 1 0 33 63 1 1 35 64 1 1 36 65 1 0 36 66 1 0 37 67 1 0 38 68 1 6 39 69 1 6 40 70 1 1 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	LKCFMVKTPNASKS-KWERPHBTSA-N
Standard InCHI	InChI=1S/C27H30O16/c28-7-14-17(32)20(35)23(38)26(41-14)43-25-21(36)18(33)15(8-29)42-27(25)39-11-3-1-9(2-4-11)24-22(37)19(34)16-12(31)5-10(30)6-13(16)40-24/h1-6,14-15,17-18,20-21,23,25-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,23-,25-,26+,27-/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2ccc(cc2)c2oc3cc(O)cc(c3c(=O)c2O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	-0.774 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.399 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.652 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.133	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.674	Fsp³:	0.444
MCE-18:	119.436 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.637	Fluc inhibitor:	0.338 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.735 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.639 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.403	Promiscuous compounds:	0.598

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.768	MDCK Permeability:	-4.934
Pgp-inhibitor:	0.0	Pgp-substrate:	0.48
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):	0.995
20% Bioavailability (F20%):	0.059	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.097
Plasma Protein Binding (PPB):	86.564%	Volume Distribution (VD):	-0.27
Fu:	11.982% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.518
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
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:	0.963
HLM stability:	0.04 ? 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):

1.442

Half-life (T1/2):

3.944

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.025
Human Hepatotoxicity (H-HT):	0.737	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.97	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.01	Skin Sensitization:	1.0
Carcinogencity:	0.237	Eye Corrosion:	0.0
Eye Irritation:	0.368	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.974
Hematotoxicity:	0.212	Drug-induced Nephrotoxicity:	0.493
Genotoxicity:	0.938	RPMI-8226 Immunitoxicity:	0.121
A549 Cytotoxicity:	0.611	Hek293 Cytotoxicity:	0.503
BCF:	0.403 ? 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:	3.004 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.508 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.675 ? 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
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17473466]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23357036]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24634069]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22311	Evolvulus alsinoides	Species	Convolvulaceae	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
Activity	4

Activity Type	# Activity
Organism	4

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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	458.2	ng/ml	PMID[9371235]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1078.0	mg/dl	PMID[9371235]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	113.1	mg/dl	PubChem BioAssay data set
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	10.91	mg kg-1	PMID[11754614]

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 NPC136761 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	20238
0.1-0.2	24843
0.2-0.3	3738
0.3-0.4	644
0.4-0.5	283
0.5-0.6	85
0.6-0.7	17
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	Natural Product ID
0.7386	Intermediate Similarity	NPC287889
0.6988	Remote Similarity	NPC170052
0.6988	Remote Similarity	NPC135846
0.6914	Remote Similarity	NPC21100
0.6905	Remote Similarity	NPC254855
0.6905	Remote Similarity	NPC94610
0.6703	Remote Similarity	NPC76831
0.6552	Remote Similarity	NPC187379
0.6477	Remote Similarity	NPC163242
0.6477	Remote Similarity	NPC272068
0.6404	Remote Similarity	NPC155877
0.6353	Remote Similarity	NPC197285
0.6341	Remote Similarity	NPC254306
0.6341	Remote Similarity	NPC143851
0.6265	Remote Similarity	NPC64305
0.6044	Remote Similarity	NPC304741
0.6042	Remote Similarity	NPC135358
0.6	Remote Similarity	NPC220173
0.5978	Remote Similarity	NPC255157
0.5978	Remote Similarity	NPC259896
0.596	Remote Similarity	NPC48984
0.5934	Remote Similarity	NPC470405
0.593	Remote Similarity	NPC472459
0.589	Remote Similarity	NPC241838
0.5882	Remote Similarity	NPC323593
0.5882	Remote Similarity	NPC203500
0.5876	Remote Similarity	NPC602448
0.5773	Remote Similarity	NPC292929
0.5714	Remote Similarity	NPC8856
0.5682	Remote Similarity	NPC285197
0.5667	Remote Similarity	NPC476215
0.5644	Remote Similarity	NPC219043
0.5618	Remote Similarity	NPC486578
0.5618	Remote Similarity	NPC224530
0.5604	Remote Similarity	NPC95866
0.5588	Remote Similarity	NPC470712
0.5556	Remote Similarity	NPC88023
0.5556	Remote Similarity	NPC309025
0.5543	Remote Similarity	NPC473682
0.5532	Remote Similarity	NPC65003
0.5521	Remote Similarity	NPC477628
0.5517	Remote Similarity	NPC156457
0.5517	Remote Similarity	NPC277205
0.5517	Remote Similarity	NPC37919
0.5506	Remote Similarity	NPC191306
0.5506	Remote Similarity	NPC60735
0.5506	Remote Similarity	NPC26230
0.5444	Remote Similarity	NPC120099
0.5444	Remote Similarity	NPC609478
0.5417	Remote Similarity	NPC240306
0.5402	Remote Similarity	NPC77672
0.5402	Remote Similarity	NPC133671
0.5402	Remote Similarity	NPC135391
0.5402	Remote Similarity	NPC78263
0.5402	Remote Similarity	NPC250069
0.5361	Remote Similarity	NPC12013
0.5361	Remote Similarity	NPC11432
0.5361	Remote Similarity	NPC477613
0.5347	Remote Similarity	NPC244875
0.5341	Remote Similarity	NPC145038
0.5341	Remote Similarity	NPC56077
0.5341	Remote Similarity	NPC281131
0.5341	Remote Similarity	NPC253662
0.5341	Remote Similarity	NPC179950
0.5341	Remote Similarity	NPC88789
0.5341	Remote Similarity	NPC491374
0.5333	Remote Similarity	NPC307938
0.5327	Remote Similarity	NPC470713
0.5319	Remote Similarity	NPC29958
0.5319	Remote Similarity	NPC139320
0.5315	Remote Similarity	NPC25946
0.5312	Remote Similarity	NPC115674
0.5312	Remote Similarity	NPC470444
0.5306	Remote Similarity	NPC122467
0.5306	Remote Similarity	NPC35119
0.5281	Remote Similarity	NPC84265
0.5268	Remote Similarity	NPC21359
0.5268	Remote Similarity	NPC460984
0.5263	Remote Similarity	NPC471748
0.5258	Remote Similarity	NPC253521
0.5258	Remote Similarity	NPC61904
0.5258	Remote Similarity	NPC113836
0.5227	Remote Similarity	NPC19388
0.5227	Remote Similarity	NPC240431
0.5227	Remote Similarity	NPC55786
0.5222	Remote Similarity	NPC138540
0.5208	Remote Similarity	NPC156869
0.5169	Remote Similarity	NPC282987
0.5161	Remote Similarity	NPC601586
0.5152	Remote Similarity	NPC32641
0.5152	Remote Similarity	NPC256188
0.5128	Remote Similarity	NPC54394
0.5128	Remote Similarity	NPC159103
0.5109	Remote Similarity	NPC601710
0.5104	Remote Similarity	NPC275454
0.5094	Remote Similarity	NPC311850
0.5056	Remote Similarity	NPC108831
0.5056	Remote Similarity	NPC182634
0.5055	Remote Similarity	NPC325555
0.5055	Remote Similarity	NPC226304
0.5055	Remote Similarity	NPC117260
0.505	Remote Similarity	NPC195257
0.5047	Remote Similarity	NPC470718

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC136761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5329
0.1-0.2	3720
0.2-0.3	89
0.3-0.4	10
0.4-0.5	2
0.5-0.6	0
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
		NPD

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