NPASS Compound

Natural Product: NPC195257

Natural Product ID	NPC195257
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Chrysoeriol-7-O-Neohesperidoside
IUPAC Name	7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
Synonyms	Chrysoeriol 7-O-Neohesperidoside; Chrysoeriol 7-O-Neohesperidosyl
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL447820
PubChem CID	44593486
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 75 79 0 0 0 0 0 0 0 0999 V2000 -1.7621 5.0518 -1.8442 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4458 4.9422 -0.6464 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5178 3.5116 -0.1777 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2223 3.0308 0.0009 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2376 1.6377 0.0677 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0246 1.2385 0.4601 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8534 0.4629 -0.3225 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5442 -0.0185 -1.5736 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4212 -0.7962 -2.3156 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1044 -1.2769 -3.5721 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6633 -1.1184 -1.8067 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0133 -0.6586 -0.5609 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1242 0.1097 0.1508 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1991 -0.9604 -0.0640 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1019 -1.6827 -0.6713 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7802 -2.1566 -1.9184 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5584 -1.8894 -2.5184 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2619 -2.3223 -3.6608 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3820 -1.9442 -0.0064 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3718 -2.7019 -0.5857 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5776 -2.9177 0.0953 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8131 -2.3913 1.3428 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8141 -1.6283 1.9243 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6319 -1.4204 1.2495 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0616 -1.1020 3.1839 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1276 -0.3126 3.8779 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0053 -2.5922 2.0411 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3216 1.2330 1.0409 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5717 2.3759 1.9878 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2801 3.4605 1.1435 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5496 2.9801 0.8638 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3378 2.8485 2.4127 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4591 0.7621 0.4137 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7317 -0.5606 0.6843 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6594 -1.3798 -0.4227 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6624 -1.2437 -1.3267 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0177 -2.6495 -1.8314 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8675 -0.5130 -0.9151 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1752 -0.4909 0.5411 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0131 -0.6767 1.4415 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1239 -1.8798 2.1352 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1643 -1.4239 0.8803 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8553 0.8039 -1.4335 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8887 4.6159 -1.7366 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0093 5.6157 0.1266 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5115 5.2916 -0.7612 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0056 2.9156 -0.9585 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5436 1.3196 -0.9715 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4086 0.1895 -2.0403 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7194 -0.6560 -4.2739 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4018 0.4780 1.1442 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4887 -2.7540 -2.4577 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2393 -3.1398 -1.5655 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3422 -3.5136 -0.3747 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8478 -0.8279 1.6947 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4001 -0.9598 4.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6910 0.3467 4.5788 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5917 0.3597 3.1771 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8993 -2.6187 1.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8941 0.3926 1.6365 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2524 2.1490 2.8137 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2473 4.4352 1.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2051 3.5900 1.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3575 2.9862 3.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9152 -0.9205 1.3798 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2274 -0.7288 -2.2337 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3473 -2.9350 -2.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0393 -2.5677 -2.2490 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9892 -3.3829 -0.9997 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7577 -0.9890 -1.4249 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6394 0.5116 0.7776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9778 0.1179 2.2452 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0112 -1.9689 2.5221 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0670 -2.2047 0.2523 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7849 1.1115 -1.5280 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 1 0 9 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 15 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 22 27 1 0 5 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 28 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 30 3 1 0 40 34 1 0 13 7 1 0 24 19 1 0 17 11 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 10 50 1 0 13 51 1 0 16 52 1 0 20 53 1 0 21 54 1 0 24 55 1 0 26 56 1 0 26 57 1 0 26 58 1 0 27 59 1 0 28 60 1 1 29 61 1 1 30 62 1 1 31 63 1 0 32 64 1 0 34 65 1 1 36 66 1 6 37 67 1 0 37 68 1 0 37 69 1 0 38 70 1 6 39 71 1 1 40 72 1 1 41 73 1 0 42 74 1 0 43 75 1 0 M END

Standard InCHIKey	LGOQXEQWOCSLEC-CYZBKYQRSA-N
Standard InCHI	InChI=1S/C28H32O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-16(41-18(20)7-12)11-3-4-13(30)17(5-11)38-2/h3-8,10,19,21-31,33-37H,9H2,1-2H3/t10-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
SMILES	OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.17	Volume:	560.823 ? Van der Waals volume.
Dense:	1.084	LogP:	-0.129 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.865 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.036 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	238.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	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:	4.672	Fsp³:	0.464
MCE-18:	118.585 ? 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:	0.633	Fluc inhibitor:	0.283 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.973 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.594 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.154	Promiscuous compounds:	0.381

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.37	MDCK Permeability:	-5.235
Pgp-inhibitor:	0.0	Pgp-substrate:	0.886
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):	0.914
20% Bioavailability (F20%):	0.47	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.445
Plasma Protein Binding (PPB):	80.097%	Volume Distribution (VD):	-0.073
Fu:	16.913% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.755
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.025
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.023
HLM stability:	0.009 ? 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):

1.751

Half-life (T1/2):

3.843

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.12
Human Hepatotoxicity (H-HT):	0.526	Drug-induced Liver Injury (DILI):	0.974
AMES Toxicity:	0.906	Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.012	Skin Sensitization:	0.998
Carcinogencity:	0.098	Eye Corrosion:	0.0
Eye Irritation:	0.31	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.947
Hematotoxicity:	0.133	Drug-induced Nephrotoxicity:	0.534
Genotoxicity:	0.652	RPMI-8226 Immunitoxicity:	0.204
A549 Cytotoxicity:	0.407	Hek293 Cytotoxicity:	0.371
BCF:	0.394 ? 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:	2.998 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.524 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.649 ? 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
NPO22304	Morinda morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542353]
NPO22304	Morinda morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20149652]
NPO22304	Morinda morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7775983]
NPO33122	microtea debilis	Species	Microteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9214739]
NPO22304	Morinda morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22304	Morinda morindoides	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
Activity	3
IC50	3

Activity Type	# Activity
Individual protein	2
Organism	1
Non-molecular	1
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1315	Individual protein	Adenosine A1 receptor	Rattus norvegicus	Activity	=	94.0	%	PMID[18177008]
NPT967	Individual protein	Xanthine dehydrogenase	Homo sapiens	IC50	>	100000.0	nM	PMID[15043407]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	>	125.0	ug.mL-1	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[9461655]
NPT2	Others	Unspecified	n.a.	Activity	=	11.2	%	PMID[7775984]
NPT2	Others	Unspecified	n.a.	Activity	=	4.6	%	PMID[16792412]

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 NPC195257 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	21740
0.1-0.2	23648
0.2-0.3	3524
0.3-0.4	574
0.4-0.5	254
0.5-0.6	67
0.6-0.7	31
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8372	Intermediate Similarity	NPC65003
0.8276	Intermediate Similarity	NPC115674
0.7614	Intermediate Similarity	NPC8856
0.7471	Intermediate Similarity	NPC311830
0.7087	Intermediate Similarity	NPC198199
0.703	Intermediate Similarity	NPC311850
0.6966	Remote Similarity	NPC601144
0.6907	Remote Similarity	NPC475382
0.6842	Remote Similarity	NPC240306
0.6735	Remote Similarity	NPC220173
0.6729	Remote Similarity	NPC120952
0.6667	Remote Similarity	NPC68592
0.6604	Remote Similarity	NPC298666
0.6593	Remote Similarity	NPC80188
0.6531	Remote Similarity	NPC32641
0.6531	Remote Similarity	NPC256188
0.6486	Remote Similarity	NPC35924
0.6471	Remote Similarity	NPC11468
0.6436	Remote Similarity	NPC253685
0.6408	Remote Similarity	NPC473072
0.6392	Remote Similarity	NPC122809
0.6364	Remote Similarity	NPC35119
0.6286	Remote Similarity	NPC473644
0.6237	Remote Similarity	NPC22832
0.6237	Remote Similarity	NPC243930
0.6168	Remote Similarity	NPC488083
0.6161	Remote Similarity	NPC262222
0.6154	Remote Similarity	NPC95090
0.6154	Remote Similarity	NPC27408
0.6111	Remote Similarity	NPC331652
0.6044	Remote Similarity	NPC39360
0.6044	Remote Similarity	NPC19709
0.6044	Remote Similarity	NPC29763
0.6044	Remote Similarity	NPC210003
0.604	Remote Similarity	NPC209296
0.6	Remote Similarity	NPC602805
0.6	Remote Similarity	NPC607707
0.5979	Remote Similarity	NPC239549
0.5978	Remote Similarity	NPC189142
0.5978	Remote Similarity	NPC77660
0.596	Remote Similarity	NPC22062
0.596	Remote Similarity	NPC473634
0.596	Remote Similarity	NPC138811
0.5904	Remote Similarity	NPC137062
0.59	Remote Similarity	NPC470444
0.5859	Remote Similarity	NPC44931
0.5826	Remote Similarity	NPC199172
0.58	Remote Similarity	NPC210073
0.5773	Remote Similarity	NPC601586
0.5766	Remote Similarity	NPC488086
0.5743	Remote Similarity	NPC257566
0.5729	Remote Similarity	NPC601710
0.57	Remote Similarity	NPC163242
0.57	Remote Similarity	NPC272068
0.5688	Remote Similarity	NPC480441
0.5688	Remote Similarity	NPC25523
0.5673	Remote Similarity	NPC142142
0.5657	Remote Similarity	NPC606546
0.5644	Remote Similarity	NPC155877
0.5607	Remote Similarity	NPC14187
0.5591	Remote Similarity	NPC473043
0.5586	Remote Similarity	NPC488087
0.5567	Remote Similarity	NPC606560
0.5556	Remote Similarity	NPC89052
0.5532	Remote Similarity	NPC261866
0.5521	Remote Similarity	NPC475942
0.5417	Remote Similarity	NPC181712
0.5385	Remote Similarity	NPC606547
0.5361	Remote Similarity	NPC27942
0.5347	Remote Similarity	NPC473682
0.5327	Remote Similarity	NPC473071
0.5299	Remote Similarity	NPC209550
0.5273	Remote Similarity	NPC25724
0.5254	Remote Similarity	NPC175429
0.5238	Remote Similarity	NPC64425
0.5229	Remote Similarity	NPC135358
0.52	Remote Similarity	NPC116458
0.52	Remote Similarity	NPC246943
0.52	Remote Similarity	NPC220169
0.52	Remote Similarity	NPC605784
0.5196	Remote Similarity	NPC251417
0.5175	Remote Similarity	NPC255799
0.5152	Remote Similarity	NPC611303
0.5149	Remote Similarity	NPC170052
0.5149	Remote Similarity	NPC190003
0.5149	Remote Similarity	NPC135846
0.5102	Remote Similarity	NPC84362
0.51	Remote Similarity	NPC486578
0.5098	Remote Similarity	NPC4390
0.5098	Remote Similarity	NPC254855
0.5098	Remote Similarity	NPC94610
0.5093	Remote Similarity	NPC479766
0.5085	Remote Similarity	NPC470720
0.5052	Remote Similarity	NPC58053
0.5052	Remote Similarity	NPC108831
0.5052	Remote Similarity	NPC238376
0.5052	Remote Similarity	NPC182634
0.505	Remote Similarity	NPC88023
0.505	Remote Similarity	NPC136761
0.505	Remote Similarity	NPC111249
0.505	Remote Similarity	NPC309025
0.5044	Remote Similarity	NPC219043
0.5044	Remote Similarity	NPC173837
0.5042	Remote Similarity	NPC138990

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC195257 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5644
0.1-0.2	3441
0.2-0.3	53
0.3-0.4	7
0.4-0.5	4
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
0.604	Remote Similarity	NPD7054	Phase 4

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