NPASS Compound

Natural Product: NPC110941

Natural Product ID	NPC110941
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-Alpha-L-Rhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name	5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-3-[(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]oxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2037047
PubChem CID	70694423
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 76 80 0 0 0 0 0 0 0 0999 V2000 8.1008 3.7599 1.2569 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5556 3.4827 0.0007 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7499 2.4210 -0.3080 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3503 1.2363 -0.7387 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7324 1.1179 -0.8577 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5202 0.1865 -1.0421 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1354 0.2821 -0.9306 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5953 1.4589 -0.5059 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3923 2.5314 -0.1930 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8350 3.7066 0.2319 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2502 1.5656 -0.3893 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7292 2.6552 -0.0011 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4471 0.4613 -0.7081 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0549 -0.6830 -1.1326 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3865 -0.7416 -1.2304 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3200 -1.9064 -1.5045 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9986 -1.9020 -1.8180 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3821 -3.1253 -2.0930 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0820 -4.2948 -2.0514 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4254 -4.3138 -1.7362 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0389 -3.1189 -1.4640 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4330 -5.5050 -2.3328 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0917 0.6435 -0.5454 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4022 0.2843 0.6815 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7503 -0.3722 0.3647 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4411 -0.7666 1.5120 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3831 -1.8688 1.2159 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3136 -1.6804 0.2938 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3697 -0.8518 0.3819 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5225 -1.6388 0.2400 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6426 -0.9595 -0.1502 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1110 0.0971 0.8043 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5384 -0.4299 -1.5727 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0909 -0.1633 -1.9394 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2992 0.2063 -0.7041 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7377 1.4544 -0.2656 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0886 0.9588 -2.7662 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0403 -1.3373 -2.5043 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0416 0.4366 2.1727 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8704 1.3397 2.5773 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2182 1.4513 1.5802 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4071 1.6081 2.3679 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4028 2.5827 2.9250 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6720 0.0903 3.3454 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2214 3.6436 1.2562 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6485 3.2076 2.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9170 4.8545 1.4574 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3201 0.8747 -0.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9090 -0.7659 -1.3829 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0097 4.0165 1.1933 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4416 -0.9861 -1.8922 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6773 -3.0617 -2.3364 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9711 -5.2597 -1.7077 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0890 -3.1091 -1.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9660 -6.3737 -2.3851 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0744 -0.4444 1.2442 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6493 -1.1325 2.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8055 -2.1779 2.2322 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7150 -2.7720 0.9776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4226 -0.3580 1.3637 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4600 -1.7359 -0.2114 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3507 0.2473 1.5987 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3958 1.0455 0.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0234 -0.2648 1.3158 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1409 0.4979 -1.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 -1.0416 -2.4018 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2417 0.3226 -1.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1236 1.9714 -1.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0009 1.2622 -3.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7031 -1.8983 -2.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6916 1.0409 1.5113 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4766 0.8849 3.5336 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0458 2.4093 1.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8524 0.7061 2.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0032 3.2723 2.3307 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3052 0.7651 3.6867 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 34 37 1 0 33 38 1 0 26 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 9 3 1 0 21 16 1 0 41 24 1 0 15 7 1 0 35 29 1 0 1 45 1 0 1 46 1 0 1 47 1 0 5 48 1 0 6 49 1 0 10 50 1 0 17 51 1 0 18 52 1 0 20 53 1 0 21 54 1 0 22 55 1 0 24 56 1 1 26 57 1 1 27 58 1 0 27 59 1 0 29 60 1 1 31 61 1 6 32 62 1 0 32 63 1 0 32 64 1 0 33 65 1 1 34 66 1 6 35 67 1 6 36 68 1 0 37 69 1 0 38 70 1 0 39 71 1 6 40 72 1 1 41 73 1 6 42 74 1 0 43 75 1 0 44 76 1 0 M END

Standard InCHIKey	FPVLVSUOCXHCMR-FPHOCJSOSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-16(31)20(35)22(37)27(41-9)40-8-14-17(32)21(36)23(38)28(43-14)44-26-19(34)15-13(7-12(30)25(39-2)18(15)33)42-24(26)10-3-5-11(29)6-4-10/h3-7,9,14,16-17,20-23,27-33,35-38H,8H2,1-2H3/t9-,14+,16-,17+,20+,21-,22+,23+,27+,28-/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]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	0.531 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.951 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.66 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	258.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.147	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.781	Fsp³:	0.464
MCE-18:	122.073 ? 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:	0.588	Fluc inhibitor:	0.248 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.794 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.621 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.07	Promiscuous compounds:	0.469

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.344	MDCK Permeability:	-5.283
Pgp-inhibitor:	0.0	Pgp-substrate:	0.857
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):	0.017
20% Bioavailability (F20%):	0.015	30% Bioavailability (F30%):	0.736
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.082
Plasma Protein Binding (PPB):	83.186%	Volume Distribution (VD):	-0.023
Fu:	14.276% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.518
BSEP inhibitor:	0.024

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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.991
HLM stability:	0.524 ? 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):

1.457

Half-life (T1/2):

4.038

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.216
Human Hepatotoxicity (H-HT):	0.373	Drug-induced Liver Injury (DILI):	0.707
AMES Toxicity:	0.732	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.032	Skin Sensitization:	0.983
Carcinogencity:	0.03	Eye Corrosion:	0.0
Eye Irritation:	0.163	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.944
Hematotoxicity:	0.048	Drug-induced Nephrotoxicity:	0.203
Genotoxicity:	0.436	RPMI-8226 Immunitoxicity:	0.11
A549 Cytotoxicity:	0.307	Hek293 Cytotoxicity:	0.494
BCF:	0.355 ? 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:	2.906 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.334 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.546 ? 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	=	2.059	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 NPC110941 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	17791
0.1-0.2	27961
0.2-0.3	3106
0.3-0.4	524
0.4-0.5	260
0.5-0.6	128
0.6-0.7	37
0.7-0.8	1
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473571
0.8902	High Similarity	NPC126784
0.8902	High Similarity	NPC241423
0.8182	Intermediate Similarity	NPC470449
0.8095	Intermediate Similarity	NPC173582
0.8095	Intermediate Similarity	NPC265885
0.8095	Intermediate Similarity	NPC181465
0.8095	Intermediate Similarity	NPC215710
0.8095	Intermediate Similarity	NPC473438
0.8095	Intermediate Similarity	NPC253788
0.8068	Intermediate Similarity	NPC470447
0.8	Intermediate Similarity	NPC65563
0.8	Intermediate Similarity	NPC470949
0.7816	Intermediate Similarity	NPC488073
0.7816	Intermediate Similarity	NPC488074
0.7609	Intermediate Similarity	NPC470455
0.75	Intermediate Similarity	NPC186816
0.7473	Intermediate Similarity	NPC476472
0.7473	Intermediate Similarity	NPC294815
0.7473	Intermediate Similarity	NPC16194
0.7386	Intermediate Similarity	NPC203259
0.7386	Intermediate Similarity	NPC33054
0.7386	Intermediate Similarity	NPC176740
0.7386	Intermediate Similarity	NPC471725
0.7386	Intermediate Similarity	NPC134532
0.7386	Intermediate Similarity	NPC602582
0.7312	Intermediate Similarity	NPC470446
0.7253	Intermediate Similarity	NPC473327
0.7229	Intermediate Similarity	NPC305811
0.7229	Intermediate Similarity	NPC488080
0.7229	Intermediate Similarity	NPC169977
0.7204	Intermediate Similarity	NPC36138
0.7204	Intermediate Similarity	NPC470445
0.7128	Intermediate Similarity	NPC470450
0.6966	Remote Similarity	NPC471079
0.6957	Remote Similarity	NPC470443
0.6923	Remote Similarity	NPC470444
0.6907	Remote Similarity	NPC470416
0.6889	Remote Similarity	NPC39834
0.6737	Remote Similarity	NPC473073
0.6596	Remote Similarity	NPC12013
0.6596	Remote Similarity	NPC11432
0.6596	Remote Similarity	NPC477613
0.6566	Remote Similarity	NPC470451
0.6566	Remote Similarity	NPC189564
0.6471	Remote Similarity	NPC111929
0.6471	Remote Similarity	NPC320283
0.6471	Remote Similarity	NPC41121
0.6465	Remote Similarity	NPC203145
0.6458	Remote Similarity	NPC142142
0.6452	Remote Similarity	NPC156869
0.6437	Remote Similarity	NPC46420
0.6364	Remote Similarity	NPC42773
0.6364	Remote Similarity	NPC45522
0.6344	Remote Similarity	NPC67326
0.6327	Remote Similarity	NPC221342
0.6327	Remote Similarity	NPC476470
0.6263	Remote Similarity	NPC602448
0.6222	Remote Similarity	NPC101026
0.6222	Remote Similarity	NPC488077
0.617	Remote Similarity	NPC44931
0.6146	Remote Similarity	NPC153755
0.6139	Remote Similarity	NPC89052
0.6117	Remote Similarity	NPC25523
0.6023	Remote Similarity	NPC249281
0.6022	Remote Similarity	NPC116864
0.6022	Remote Similarity	NPC244776
0.602	Remote Similarity	NPC122467
0.6019	Remote Similarity	NPC292019
0.6019	Remote Similarity	NPC202908
0.6019	Remote Similarity	NPC173837
0.5978	Remote Similarity	NPC223747
0.5955	Remote Similarity	NPC265530
0.5914	Remote Similarity	NPC276377
0.59	Remote Similarity	NPC85751
0.59	Remote Similarity	NPC19240
0.59	Remote Similarity	NPC89127
0.5895	Remote Similarity	NPC187379
0.5889	Remote Similarity	NPC24043
0.5889	Remote Similarity	NPC27640
0.5876	Remote Similarity	NPC129264
0.5843	Remote Similarity	NPC127546
0.5843	Remote Similarity	NPC57625
0.5843	Remote Similarity	NPC173637
0.5843	Remote Similarity	NPC317489
0.5843	Remote Similarity	NPC223424
0.5843	Remote Similarity	NPC600591
0.5833	Remote Similarity	NPC67105
0.5825	Remote Similarity	NPC121703
0.5816	Remote Similarity	NPC470125
0.5789	Remote Similarity	NPC473554
0.578	Remote Similarity	NPC474522
0.5761	Remote Similarity	NPC219904
0.5745	Remote Similarity	NPC476215
0.5729	Remote Similarity	NPC609888
0.5728	Remote Similarity	NPC214621
0.5728	Remote Similarity	NPC34267
0.5714	Remote Similarity	NPC204693
0.5714	Remote Similarity	NPC271692
0.57	Remote Similarity	NPC270448
0.5676	Remote Similarity	NPC241781
0.5667	Remote Similarity	NPC77672
0.5667	Remote Similarity	NPC133671
0.5667	Remote Similarity	NPC135391
0.5667	Remote Similarity	NPC78263
0.5667	Remote Similarity	NPC250069
0.5652	Remote Similarity	NPC483159
0.5652	Remote Similarity	NPC483160
0.5641	Remote Similarity	NPC266960
0.5638	Remote Similarity	NPC116458
0.5638	Remote Similarity	NPC246943
0.5625	Remote Similarity	NPC192539
0.5612	Remote Similarity	NPC22062
0.5612	Remote Similarity	NPC473634
0.5612	Remote Similarity	NPC210073
0.5612	Remote Similarity	NPC138811
0.5612	Remote Similarity	NPC150164
0.5545	Remote Similarity	NPC209296
0.5534	Remote Similarity	NPC292929
0.5514	Remote Similarity	NPC480441
0.5514	Remote Similarity	NPC217520
0.5514	Remote Similarity	NPC303694
0.551	Remote Similarity	NPC163242
0.551	Remote Similarity	NPC272068
0.55	Remote Similarity	NPC240306
0.5495	Remote Similarity	NPC156785
0.5495	Remote Similarity	NPC162394
0.5481	Remote Similarity	NPC223426
0.5474	Remote Similarity	NPC99957
0.5455	Remote Similarity	NPC303913
0.5455	Remote Similarity	NPC605592
0.5437	Remote Similarity	NPC471669
0.5421	Remote Similarity	NPC477895
0.5408	Remote Similarity	NPC139320
0.5405	Remote Similarity	NPC480445
0.5398	Remote Similarity	NPC209550
0.5393	Remote Similarity	NPC54802
0.5393	Remote Similarity	NPC197304
0.5392	Remote Similarity	NPC32641
0.5392	Remote Similarity	NPC256188
0.5392	Remote Similarity	NPC72016
0.5385	Remote Similarity	NPC135599
0.5385	Remote Similarity	NPC73855
0.5385	Remote Similarity	NPC113968
0.5385	Remote Similarity	NPC328940
0.5385	Remote Similarity	NPC277174
0.5385	Remote Similarity	NPC606877
0.5361	Remote Similarity	NPC172807
0.5354	Remote Similarity	NPC227508
0.5333	Remote Similarity	NPC288084
0.5319	Remote Similarity	NPC59534
0.53	Remote Similarity	NPC473512
0.53	Remote Similarity	NPC129827
0.5294	Remote Similarity	NPC483414
0.5294	Remote Similarity	NPC483415
0.5283	Remote Similarity	NPC81042
0.5273	Remote Similarity	NPC139571
0.5269	Remote Similarity	NPC297987
0.5269	Remote Similarity	NPC158674
0.5263	Remote Similarity	NPC159579
0.5263	Remote Similarity	NPC175107
0.5263	Remote Similarity	NPC611303
0.5258	Remote Similarity	NPC203050
0.5258	Remote Similarity	NPC225434
0.5258	Remote Similarity	NPC66087
0.5243	Remote Similarity	NPC483416
0.5243	Remote Similarity	NPC37668
0.5243	Remote Similarity	NPC35119
0.5204	Remote Similarity	NPC95866
0.5196	Remote Similarity	NPC296018
0.5185	Remote Similarity	NPC488075
0.5179	Remote Similarity	NPC488734
0.5179	Remote Similarity	NPC488735
0.5179	Remote Similarity	NPC488739
0.5179	Remote Similarity	NPC488732
0.5179	Remote Similarity	NPC488738
0.5158	Remote Similarity	NPC472459
0.5152	Remote Similarity	NPC473682
0.5143	Remote Similarity	NPC220173
0.5116	Remote Similarity	NPC469622
0.5106	Remote Similarity	NPC145038
0.5106	Remote Similarity	NPC8573
0.5106	Remote Similarity	NPC56077
0.5106	Remote Similarity	NPC281131
0.5106	Remote Similarity	NPC253662
0.5106	Remote Similarity	NPC179950
0.5106	Remote Similarity	NPC88789
0.5106	Remote Similarity	NPC491374
0.5104	Remote Similarity	NPC488071
0.5102	Remote Similarity	NPC488072
0.5094	Remote Similarity	NPC101636
0.5086	Remote Similarity	NPC480443
0.5052	Remote Similarity	NPC120099
0.5052	Remote Similarity	NPC181616
0.5051	Remote Similarity	NPC265115
0.5051	Remote Similarity	NPC477848
0.505	Remote Similarity	NPC470405
0.5049	Remote Similarity	NPC475366
0.5048	Remote Similarity	NPC486577

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC110941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5061
0.1-0.2	4033
0.2-0.3	45
0.3-0.4	5
0.4-0.5	1
0.5-0.6	3
0.6-0.7	1
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
0.7386	Intermediate Similarity	NPD6797	Phase 2
0.6392	Remote Similarity	NPD7251	Phase 2
0.5825	Remote Similarity	NPD7808	Phase 3
0.5545	Remote Similarity	NPD7054	Phase 4
0.5093	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