NPASS Compound

Natural Product: NPC187379

Natural Product ID	NPC187379
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-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name	3,5,7-trihydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2336772
PubChem CID	71600048
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 72 76 0 0 0 0 0 0 0 0999 V2000 -4.8944 -3.5465 0.3905 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5577 -2.4297 -0.3841 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0163 -2.3845 0.0575 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5459 -1.0384 -0.3852 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6447 -0.4934 -1.4722 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2695 -0.1932 -0.9055 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3295 0.0097 -1.8777 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7257 1.2556 -1.8845 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9772 1.5816 -0.6228 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3228 2.9618 -0.7177 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0997 3.3924 0.7245 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6020 2.1897 1.4543 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0170 1.1248 0.5361 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1495 1.5469 -0.0714 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4004 0.9945 0.1458 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6658 -0.0390 1.0035 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9660 -0.5151 1.1415 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0293 -0.0196 0.4705 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7527 1.0343 -0.4030 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4920 1.5243 -0.5618 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3972 -0.4928 0.5968 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8329 -1.4906 1.4253 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1773 -1.8817 1.4806 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5717 -2.7965 2.2417 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0808 -1.2437 0.6797 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4318 -1.5701 0.6730 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3405 -0.9267 -0.1350 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8628 0.0854 -0.9676 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5259 0.4009 -0.9538 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5963 -0.2515 -0.1325 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3424 0.0798 -0.1529 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7817 0.7337 -1.7829 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9010 -2.5850 1.5100 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9443 -2.1616 2.2540 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9770 0.6742 -0.3766 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5258 1.5971 2.2798 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2932 4.5050 0.8280 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1288 3.8611 -1.4017 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9211 -1.2408 -0.0336 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2571 0.7006 -1.9179 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5799 -0.1654 0.7003 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6996 -3.4482 -0.5061 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3761 -4.5141 0.1255 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1255 -3.3808 1.4714 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7967 -3.5707 0.2488 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5208 -2.6505 -1.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0909 -2.4626 1.1683 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5548 -1.2184 -0.8118 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6249 -1.1729 -2.3249 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3979 0.7018 -0.2707 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0074 1.2902 -2.7301 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4911 2.0502 -2.0892 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6659 1.5856 0.2393 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3618 2.8760 -1.2638 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1332 3.6033 1.1318 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7440 2.5206 2.0994 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8197 0.2637 1.1938 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8598 -0.5042 1.5924 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0657 -1.3279 1.8376 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5456 1.5020 -0.9912 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2785 2.3520 -1.2482 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3972 -1.1589 -0.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1698 1.1812 -1.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0740 0.1937 -2.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8523 -2.5335 1.8801 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1341 -2.2201 3.2473 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1504 0.7436 2.6112 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7009 4.3692 1.6290 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9499 3.7444 -2.3769 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2104 1.3934 -1.1865 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4935 0.1895 0.7520 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0189 -3.1852 -1.4031 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 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 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 18 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 28 32 1 0 26 33 1 0 22 34 1 0 13 35 1 0 12 36 1 0 11 37 1 0 10 38 1 0 6 39 1 0 5 40 1 0 4 41 1 0 3 42 1 0 39 2 1 0 35 9 1 0 20 15 1 0 31 21 1 0 30 25 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 6 3 47 1 1 4 48 1 6 5 49 1 6 6 50 1 1 8 51 1 0 8 52 1 0 9 53 1 1 10 54 1 6 11 55 1 1 12 56 1 1 13 57 1 1 16 58 1 0 17 59 1 0 19 60 1 0 20 61 1 0 27 62 1 0 29 63 1 0 32 64 1 0 33 65 1 0 34 66 1 0 36 67 1 0 37 68 1 0 38 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	NTBNRFPZTCXMTF-QETNVOEASA-N
Standard InCHI	InChI=1S/C27H30O15/c1-9-17(30)20(33)23(36)26(39-9)38-8-15-18(31)21(34)24(37)27(42-15)40-12-4-2-10(3-5-12)25-22(35)19(32)16-13(29)6-11(28)7-14(16)41-25/h2-7,9,15,17-18,20-21,23-24,26-31,33-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,23+,24+,26+,27+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3ccc(cc3)c3c(c(=O)c4c(cc(cc4o3)O)O)O)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	0.822 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.277 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.666 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.671	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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.615	Fluc inhibitor:	0.357 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.769 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.659 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.157	Promiscuous compounds:	0.567

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.554	MDCK Permeability:	-5.108
Pgp-inhibitor:	0.0	Pgp-substrate:	0.887
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):	0.985
20% Bioavailability (F20%):	0.242	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.14
Plasma Protein Binding (PPB):	87.639%	Volume Distribution (VD):	-0.173
Fu:	10.708% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.835
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.843 ? 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):

1.204

Half-life (T1/2):

4.179

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.219
Human Hepatotoxicity (H-HT):	0.426	Drug-induced Liver Injury (DILI):	0.984
AMES Toxicity:	0.879	Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.1	Skin Sensitization:	0.83
Carcinogencity:	0.098	Eye Corrosion:	0.0
Eye Irritation:	0.724	Respiratory Toxicity:	0.024
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.806
Hematotoxicity:	0.055	Drug-induced Nephrotoxicity:	0.623
Genotoxicity:	0.89	RPMI-8226 Immunitoxicity:	0.224
A549 Cytotoxicity:	0.434	Hek293 Cytotoxicity:	0.488
BCF:	0.667 ? 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:	3.383 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.721 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.054 ? 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	=	239.2	ng/ml	PMID[10514320]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	521.4	mg/dl	PMID[12608855]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	105.13	mg/dl	DOI[10.6019/CHEMBL1201861]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	8.47	mg kg-1	PMID[26254943]

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 NPC187379 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	15399
0.1-0.2	30031
0.2-0.3	3387
0.3-0.4	578
0.4-0.5	317
0.5-0.6	99
0.6-0.7	24
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8046	Intermediate Similarity	NPC287889
0.7126	Intermediate Similarity	NPC173582
0.7126	Intermediate Similarity	NPC265885
0.7126	Intermediate Similarity	NPC181465
0.7126	Intermediate Similarity	NPC215710
0.7126	Intermediate Similarity	NPC67105
0.7126	Intermediate Similarity	NPC473438
0.7126	Intermediate Similarity	NPC253788
0.7111	Intermediate Similarity	NPC473327
0.7045	Intermediate Similarity	NPC203259
0.7045	Intermediate Similarity	NPC33054
0.7045	Intermediate Similarity	NPC176740
0.7045	Intermediate Similarity	NPC471725
0.7045	Intermediate Similarity	NPC134532
0.7045	Intermediate Similarity	NPC602582
0.6932	Remote Similarity	NPC39834
0.6932	Remote Similarity	NPC227508
0.6632	Remote Similarity	NPC135358
0.6596	Remote Similarity	NPC476472
0.6596	Remote Similarity	NPC294815
0.6596	Remote Similarity	NPC16194
0.6552	Remote Similarity	NPC136761
0.6304	Remote Similarity	NPC22062
0.6304	Remote Similarity	NPC473634
0.6304	Remote Similarity	NPC138811
0.6237	Remote Similarity	NPC204693
0.6207	Remote Similarity	NPC21100
0.6129	Remote Similarity	NPC156869
0.6105	Remote Similarity	NPC12013
0.6105	Remote Similarity	NPC11432
0.6105	Remote Similarity	NPC477613
0.6087	Remote Similarity	NPC471079
0.6082	Remote Similarity	NPC89127
0.6047	Remote Similarity	NPC108831
0.6047	Remote Similarity	NPC182634
0.6042	Remote Similarity	NPC122467
0.6022	Remote Similarity	NPC44931
0.6022	Remote Similarity	NPC67326
0.6022	Remote Similarity	NPC275454
0.5957	Remote Similarity	NPC65563
0.5957	Remote Similarity	NPC470949
0.59	Remote Similarity	NPC244875
0.5895	Remote Similarity	NPC473571
0.5895	Remote Similarity	NPC110941
0.5895	Remote Similarity	NPC186816
0.5876	Remote Similarity	NPC209296
0.587	Remote Similarity	NPC116864
0.587	Remote Similarity	NPC244776
0.5862	Remote Similarity	NPC254306
0.5859	Remote Similarity	NPC221342
0.5859	Remote Similarity	NPC476470
0.58	Remote Similarity	NPC602448
0.5789	Remote Similarity	NPC210073
0.5784	Remote Similarity	NPC189564
0.5758	Remote Similarity	NPC477629
0.5728	Remote Similarity	NPC292019
0.5728	Remote Similarity	NPC202908
0.5728	Remote Similarity	NPC173837
0.5714	Remote Similarity	NPC197285
0.5699	Remote Similarity	NPC477848
0.5686	Remote Similarity	NPC89052
0.5686	Remote Similarity	NPC203145
0.5682	Remote Similarity	NPC238376
0.5682	Remote Similarity	NPC143851
0.567	Remote Similarity	NPC126784
0.567	Remote Similarity	NPC241423
0.5625	Remote Similarity	NPC303913
0.5618	Remote Similarity	NPC64305
0.5604	Remote Similarity	NPC219904
0.5584	Remote Similarity	NPC241838
0.5579	Remote Similarity	NPC609888
0.5568	Remote Similarity	NPC111929
0.5568	Remote Similarity	NPC320283
0.5568	Remote Similarity	NPC41121
0.5524	Remote Similarity	NPC303694
0.551	Remote Similarity	NPC475366
0.551	Remote Similarity	NPC153755
0.5506	Remote Similarity	NPC127546
0.5506	Remote Similarity	NPC57625
0.5506	Remote Similarity	NPC173637
0.5506	Remote Similarity	NPC317489
0.5506	Remote Similarity	NPC223424
0.5506	Remote Similarity	NPC600591
0.5495	Remote Similarity	NPC192539
0.5446	Remote Similarity	NPC80068
0.5446	Remote Similarity	NPC76831
0.54	Remote Similarity	NPC483707
0.5393	Remote Similarity	NPC135599
0.5393	Remote Similarity	NPC73855
0.5393	Remote Similarity	NPC113968
0.5393	Remote Similarity	NPC328940
0.5393	Remote Similarity	NPC277174
0.5393	Remote Similarity	NPC606877
0.5364	Remote Similarity	NPC162394
0.5333	Remote Similarity	NPC476405
0.5326	Remote Similarity	NPC472459
0.5306	Remote Similarity	NPC233994
0.53	Remote Similarity	NPC470443
0.5294	Remote Similarity	NPC471669
0.5275	Remote Similarity	NPC265530
0.5275	Remote Similarity	NPC323593
0.5275	Remote Similarity	NPC203500
0.5268	Remote Similarity	NPC241781
0.5263	Remote Similarity	NPC476215
0.5253	Remote Similarity	NPC129264
0.5248	Remote Similarity	NPC473623
0.5238	Remote Similarity	NPC11468
0.5208	Remote Similarity	NPC95866
0.5196	Remote Similarity	NPC488089
0.5158	Remote Similarity	NPC223747
0.5158	Remote Similarity	NPC99957
0.5152	Remote Similarity	NPC475155
0.5152	Remote Similarity	NPC605592
0.5149	Remote Similarity	NPC211532
0.5149	Remote Similarity	NPC488364
0.5146	Remote Similarity	NPC85751
0.5146	Remote Similarity	NPC473073
0.5146	Remote Similarity	NPC19240
0.514	Remote Similarity	NPC480796
0.514	Remote Similarity	NPC477895
0.5128	Remote Similarity	NPC473554
0.5106	Remote Similarity	NPC285197
0.5098	Remote Similarity	NPC37668
0.5098	Remote Similarity	NPC270448
0.5096	Remote Similarity	NPC292929
0.5096	Remote Similarity	NPC101636
0.5093	Remote Similarity	NPC25523
0.5089	Remote Similarity	NPC156785
0.5089	Remote Similarity	NPC474522
0.5053	Remote Similarity	NPC181616
0.5053	Remote Similarity	NPC486578
0.5052	Remote Similarity	NPC211594
0.5051	Remote Similarity	NPC163242
0.5051	Remote Similarity	NPC272068
0.505	Remote Similarity	NPC470125
0.5049	Remote Similarity	NPC142142
0.5048	Remote Similarity	NPC223426
0.5043	Remote Similarity	NPC487499

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC187379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4454
0.1-0.2	4615
0.2-0.3	68
0.3-0.4	6
0.4-0.5	2
0.5-0.6	4
0.6-0.7	0
0.7-0.8	1
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
0.7045	Intermediate Similarity	NPD6797	Phase 2
0.5876	Remote Similarity	NPD7054	Phase 4
0.5686	Remote Similarity	NPD7808	Phase 3
0.5446	Remote Similarity	NPD7251	Phase 2
0.5238	Remote Similarity	NPD7472	Pre-clinical

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