NPASS Compound

Natural Product: NPC576561

Natural Product ID	NPC576561
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Luteolin 7-gentiobioside
IUPAC Name	2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2~{S},4~{S},5~{S})-3,4,5-trihydroxy-6-[[(2~{R},4~{S},5~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 4.7431 -3.5827 2.8230 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9822 -2.6290 2.0410 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2647 -2.4220 1.5562 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4535 -1.3639 0.7080 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7580 -1.0260 0.1190 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8715 0.0749 -0.7318 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0866 0.3954 -1.2861 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2213 -0.3427 -1.0296 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4528 0.0112 -1.6128 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1441 -1.4348 -0.1948 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2725 -2.2117 0.0921 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8962 -1.7446 0.3599 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4448 -0.5916 0.3821 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2269 -0.7395 0.8058 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2091 0.1099 0.4243 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8928 -0.0398 0.8749 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9910 0.8730 0.4151 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3747 0.9280 0.7267 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0598 0.7468 -0.4709 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3936 1.1603 -0.4186 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9588 0.8469 -1.7823 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2700 1.1477 -1.9749 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0650 0.4044 -1.1127 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8256 -0.5024 -1.9011 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5529 -1.2801 -1.0277 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1371 -2.4750 -1.7898 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9609 -2.0300 -2.8035 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6635 -0.4117 -0.4611 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8824 -0.7403 -1.0025 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3992 1.0588 -0.8143 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4242 1.1960 -2.1945 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9614 1.3394 -0.3650 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8249 1.0813 1.0025 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4923 2.6636 -0.2345 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4353 3.0264 0.7246 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1733 3.2444 0.2370 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2809 3.4682 -0.7825 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6265 2.3121 1.3011 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4994 2.8855 1.8481 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6533 -1.0805 1.7234 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6653 -1.9437 2.1167 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4255 -3.0047 2.9805 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9589 -1.7873 1.6668 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0927 -3.0466 1.8175 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9747 0.6657 -0.9399 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1381 1.2573 -1.9420 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6236 -0.2930 -2.5678 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1025 -3.1154 0.5090 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8305 -2.6060 1.0192 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4757 0.9079 -0.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6376 0.1203 1.4266 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9476 0.6949 0.4143 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8058 -0.2688 -1.9056 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2754 1.3278 -2.5195 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4702 -0.2591 -0.4569 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9188 -1.7236 -0.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5990 -3.1945 -1.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2653 -2.9832 -2.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0541 -2.7783 -3.4567 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6196 -0.5001 0.6431 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5592 -0.8422 -0.2856 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1070 1.6939 -0.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6533 1.7360 -2.5357 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7698 2.4018 -0.5762 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3901 0.2102 1.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7597 3.1839 -1.1752 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9364 3.8498 0.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3936 4.2127 0.7274 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4126 2.8743 -1.5651 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3989 2.2081 2.0907 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2434 2.8285 1.2065 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6613 -1.2350 2.0946 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4805 -2.9170 3.9909 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 8 10 1 0 10 11 1 0 10 12 2 0 4 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 20 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 16 40 2 0 40 41 1 0 41 42 1 0 41 43 2 0 43 2 1 0 12 5 1 0 43 14 1 0 38 18 1 0 32 23 1 0 3 44 1 0 6 45 1 0 7 46 1 0 9 47 1 0 11 48 1 0 12 49 1 0 15 50 1 0 18 51 1 1 20 52 1 0 21 53 1 0 21 54 1 0 23 55 1 1 25 56 1 0 26 57 1 0 26 58 1 0 27 59 1 0 28 60 1 1 29 61 1 0 30 62 1 1 31 63 1 0 32 64 1 0 33 65 1 0 34 66 1 6 35 67 1 0 36 68 1 1 37 69 1 0 38 70 1 0 39 71 1 0 40 72 1 0 42 73 1 0 M END

Standard InCHIKey	LDTDRTSKWGQBAA-XMSKAULVSA-N
Standard InCHI	InChI=1S/C27H30O16/c28-7-17-20(33)22(35)24(37)26(42-17)39-8-18-21(34)23(36)25(38)27(43-18)40-10-4-13(31)19-14(32)6-15(41-16(19)5-10)9-1-2-11(29)12(30)3-9/h1-6,17-18,20-31,33-38H,7-8H2/t17?,18?,20-,21+,22-,23-,24?,25?,26+,27+/m0/s1
SMILES	O=C1C=C(C2=CC=C(O)C(O)=C2)OC2=CC(O[C@@H]3OC(CO[C@@H]4OC(CO)[C@H](O)[C@H](O)C4O)[C@@H](O)[C@H](O)C3O)=CC(O)=C12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	-1.259 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.229 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.106 ? 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:	0.125	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.72	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:	1
Colloidal aggregators:	0.634	Fluc inhibitor:	0.258 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.99 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.933 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.232	Promiscuous compounds:	0.376

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.493	MDCK Permeability:	-5.108
Pgp-inhibitor:	0.0	Pgp-substrate:	0.969
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):	0.993
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.819
Plasma Protein Binding (PPB):	82.417%	Volume Distribution (VD):	-0.009
Fu:	17.295% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.922
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.259
BSEP inhibitor:	0.0

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.24
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.944
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):

2.01

Half-life (T1/2):

3.744

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.221
Human Hepatotoxicity (H-HT):	0.487	Drug-induced Liver Injury (DILI):	0.967
AMES Toxicity:	0.928	Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.273	Skin Sensitization:	0.992
Carcinogencity:	0.247	Eye Corrosion:	0.0
Eye Irritation:	0.064	Respiratory Toxicity:	0.027
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.968
Hematotoxicity:	0.044	Drug-induced Nephrotoxicity:	0.094
Genotoxicity:	0.948	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.828	Hek293 Cytotoxicity:	0.679
BCF:	0.326 ? 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:	2.757 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.466 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.599 ? 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
NPO46954	Launaea cassiniana	Genus	Asteraceae	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

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

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 NPC576561 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	24815
0.1-0.2	20778
0.2-0.3	3060
0.3-0.4	700
0.4-0.5	300
0.5-0.6	123
0.6-0.7	55
0.7-0.8	1
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8765	High Similarity	NPC210073
0.8312	Intermediate Similarity	NPC189142
0.8312	Intermediate Similarity	NPC77660
0.8235	Intermediate Similarity	NPC65711
0.7765	Intermediate Similarity	NPC44931
0.7356	Intermediate Similarity	NPC275454
0.7333	Intermediate Similarity	NPC209296
0.7333	Intermediate Similarity	NPC229409
0.7326	Intermediate Similarity	NPC8856
0.7284	Intermediate Similarity	NPC39360
0.7284	Intermediate Similarity	NPC19709
0.7284	Intermediate Similarity	NPC29763
0.7284	Intermediate Similarity	NPC210003
0.7273	Intermediate Similarity	NPC22062
0.7273	Intermediate Similarity	NPC473634
0.7273	Intermediate Similarity	NPC138811
0.7159	Intermediate Similarity	NPC67105
0.7093	Intermediate Similarity	NPC190003
0.6867	Remote Similarity	NPC261866
0.686	Remote Similarity	NPC22832
0.686	Remote Similarity	NPC601144
0.6813	Remote Similarity	NPC115674
0.6786	Remote Similarity	NPC95090
0.6786	Remote Similarity	NPC277205
0.6786	Remote Similarity	NPC27408
0.6786	Remote Similarity	NPC37919
0.6782	Remote Similarity	NPC311830
0.6774	Remote Similarity	NPC473623
0.6737	Remote Similarity	NPC101636
0.6702	Remote Similarity	NPC488089
0.6667	Remote Similarity	NPC480441
0.6588	Remote Similarity	NPC136042
0.6559	Remote Similarity	NPC64051
0.6522	Remote Similarity	NPC156869
0.6512	Remote Similarity	NPC58716
0.6512	Remote Similarity	NPC84362
0.6512	Remote Similarity	NPC45638
0.6477	Remote Similarity	NPC243930
0.6452	Remote Similarity	NPC186816
0.6437	Remote Similarity	NPC201292
0.6413	Remote Similarity	NPC227508
0.6404	Remote Similarity	NPC607707
0.6395	Remote Similarity	NPC168822
0.6392	Remote Similarity	NPC298171
0.6374	Remote Similarity	NPC254540
0.6354	Remote Similarity	NPC270675
0.6354	Remote Similarity	NPC195685
0.6353	Remote Similarity	NPC473043
0.6353	Remote Similarity	NPC331652
0.6346	Remote Similarity	NPC298666
0.6346	Remote Similarity	NPC198199
0.6344	Remote Similarity	NPC479405
0.6277	Remote Similarity	NPC479404
0.6275	Remote Similarity	NPC311850
0.625	Remote Similarity	NPC27942
0.6222	Remote Similarity	NPC605784
0.6214	Remote Similarity	NPC488083
0.6211	Remote Similarity	NPC46202
0.6211	Remote Similarity	NPC488073
0.6196	Remote Similarity	NPC606546
0.6176	Remote Similarity	NPC25523
0.617	Remote Similarity	NPC218488
0.6168	Remote Similarity	NPC120952
0.6162	Remote Similarity	NPC253685
0.6162	Remote Similarity	NPC472994
0.6146	Remote Similarity	NPC479403
0.6095	Remote Similarity	NPC68592
0.6023	Remote Similarity	NPC297987
0.6023	Remote Similarity	NPC323593
0.6023	Remote Similarity	NPC203500
0.6	Remote Similarity	NPC473512
0.6	Remote Similarity	NPC65003
0.6	Remote Similarity	NPC20505
0.5955	Remote Similarity	NPC181712
0.5941	Remote Similarity	NPC14187
0.5938	Remote Similarity	NPC204693
0.5922	Remote Similarity	NPC472993
0.5909	Remote Similarity	NPC238376
0.5882	Remote Similarity	NPC11468
0.5842	Remote Similarity	NPC484301
0.5842	Remote Similarity	NPC135358
0.5833	Remote Similarity	NPC129827
0.5833	Remote Similarity	NPC3583
0.5833	Remote Similarity	NPC607513
0.58	Remote Similarity	NPC475382
0.5769	Remote Similarity	NPC108406
0.5766	Remote Similarity	NPC262222
0.573	Remote Similarity	NPC289667
0.5699	Remote Similarity	NPC116458
0.5699	Remote Similarity	NPC246943
0.567	Remote Similarity	NPC203259
0.567	Remote Similarity	NPC33054
0.567	Remote Similarity	NPC176740
0.567	Remote Similarity	NPC471725
0.567	Remote Similarity	NPC134532
0.567	Remote Similarity	NPC602582
0.5667	Remote Similarity	NPC93337
0.5667	Remote Similarity	NPC146792
0.5657	Remote Similarity	NPC470443
0.5652	Remote Similarity	NPC285197
0.5644	Remote Similarity	NPC195257
0.5619	Remote Similarity	NPC292019
0.5619	Remote Similarity	NPC202908
0.5612	Remote Similarity	NPC122809
0.5607	Remote Similarity	NPC488087
0.5604	Remote Similarity	NPC271692
0.5604	Remote Similarity	NPC105025
0.5604	Remote Similarity	NPC610763
0.56	Remote Similarity	NPC483707
0.56	Remote Similarity	NPC150767
0.5579	Remote Similarity	NPC172807
0.5567	Remote Similarity	NPC67326
0.5566	Remote Similarity	NPC473644
0.5556	Remote Similarity	NPC58053
0.5556	Remote Similarity	NPC143851
0.5545	Remote Similarity	NPC486577
0.551	Remote Similarity	NPC102028
0.551	Remote Similarity	NPC303913
0.549	Remote Similarity	NPC473073
0.5484	Remote Similarity	NPC191306
0.5484	Remote Similarity	NPC307938
0.5474	Remote Similarity	NPC601586
0.5465	Remote Similarity	NPC191154
0.5464	Remote Similarity	NPC473657
0.5446	Remote Similarity	NPC35119
0.5435	Remote Similarity	NPC245014
0.5435	Remote Similarity	NPC186807
0.5426	Remote Similarity	NPC80188
0.5426	Remote Similarity	NPC486578
0.5426	Remote Similarity	NPC601710
0.5426	Remote Similarity	NPC605067
0.5417	Remote Similarity	NPC211594
0.5408	Remote Similarity	NPC47923
0.54	Remote Similarity	NPC126784
0.54	Remote Similarity	NPC241423
0.54	Remote Similarity	NPC64425
0.54	Remote Similarity	NPC475366
0.5385	Remote Similarity	NPC45618
0.5376	Remote Similarity	NPC117260
0.5368	Remote Similarity	NPC602805
0.5364	Remote Similarity	NPC488086
0.534	Remote Similarity	NPC80068
0.5319	Remote Similarity	NPC282169
0.5306	Remote Similarity	NPC295613
0.5294	Remote Similarity	NPC32641
0.5294	Remote Similarity	NPC256188
0.5253	Remote Similarity	NPC173582
0.5253	Remote Similarity	NPC265885
0.5253	Remote Similarity	NPC181465
0.5253	Remote Similarity	NPC215710
0.5253	Remote Similarity	NPC473438
0.5253	Remote Similarity	NPC253788
0.5248	Remote Similarity	NPC475497
0.5248	Remote Similarity	NPC488074
0.5243	Remote Similarity	NPC142142
0.5234	Remote Similarity	NPC189564
0.5229	Remote Similarity	NPC277532
0.5227	Remote Similarity	NPC134819
0.5217	Remote Similarity	NPC249281
0.5217	Remote Similarity	NPC108831
0.5217	Remote Similarity	NPC83283
0.5217	Remote Similarity	NPC182634
0.5208	Remote Similarity	NPC220169
0.5204	Remote Similarity	NPC251417
0.5161	Remote Similarity	NPC145038
0.5161	Remote Similarity	NPC282987
0.5161	Remote Similarity	NPC56077
0.5161	Remote Similarity	NPC281131
0.5161	Remote Similarity	NPC253662
0.5161	Remote Similarity	NPC179950
0.5161	Remote Similarity	NPC88789
0.5161	Remote Similarity	NPC259152
0.5161	Remote Similarity	NPC491374
0.5161	Remote Similarity	NPC609879
0.5158	Remote Similarity	NPC488071
0.5158	Remote Similarity	NPC609451
0.5155	Remote Similarity	NPC276377
0.5152	Remote Similarity	NPC471079
0.514	Remote Similarity	NPC121703
0.5106	Remote Similarity	NPC46420
0.5104	Remote Similarity	NPC284960
0.5102	Remote Similarity	NPC116864
0.5102	Remote Similarity	NPC244776
0.51	Remote Similarity	NPC15358
0.51	Remote Similarity	NPC39834
0.5098	Remote Similarity	NPC284277
0.5094	Remote Similarity	NPC179862
0.506	Remote Similarity	NPC57751
0.5052	Remote Similarity	NPC88023
0.5052	Remote Similarity	NPC309025
0.505	Remote Similarity	NPC233994
0.505	Remote Similarity	NPC65563
0.505	Remote Similarity	NPC470949
0.505	Remote Similarity	NPC150164
0.5048	Remote Similarity	NPC477629
0.5047	Remote Similarity	NPC244875

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC576561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5855
0.1-0.2	3213
0.2-0.3	69
0.3-0.4	6
0.4-0.5	2
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
0.7333	Intermediate Similarity	NPD7054	Phase 4
0.6632	Remote Similarity	NPD7251	Phase 2
0.567	Remote Similarity	NPD6797	Phase 2
0.5577	Remote Similarity	NPD7472	Pre-clinical
0.5577	Remote Similarity	NPD7808	Phase 3

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