NPASS Compound

Natural Product: NPC545768

Natural Product ID	NPC545768
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2~{R},3~{S},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-3-yl]oxy-tetrahydropyran-2-yl]methyl acetate
IUPAC Name	[(2~{R},3~{S},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-3-yl]oxy-tetrahydropyran-2-yl]methyl acetate
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 77 81 0 0 0 0 0 0 0 0999 V2000 -7.9983 4.0083 -1.3824 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6500 3.5685 -0.9483 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0306 4.2496 -0.1131 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0687 2.4171 -1.4536 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7857 1.9674 -1.0629 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5292 0.6782 -1.8483 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3333 0.1106 -1.5849 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2541 -0.7961 -0.5365 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5707 -0.2164 0.5821 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2090 -0.4430 0.7673 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7060 -1.4185 1.5401 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 -2.3809 2.3188 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8962 -3.5275 2.7926 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5405 -4.4431 3.5616 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8770 -4.2539 3.9058 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5306 -5.1937 4.6914 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4859 -3.1137 3.4324 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8292 -2.1811 2.6500 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6226 -1.5233 1.6055 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4461 -0.7348 0.9681 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8247 -0.8984 1.0799 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7443 -0.1038 0.4368 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0628 -0.3518 0.6165 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0918 0.3587 0.0354 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9690 -0.4448 -0.7033 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6585 0.3491 -1.5838 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9286 0.2826 -2.9303 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8525 1.7623 -1.1465 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0965 2.1824 -1.6713 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9287 1.9267 0.3444 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2570 1.7588 0.7314 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9952 1.0245 1.0938 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1964 1.7223 1.9990 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2677 0.9013 -0.3553 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8874 1.1126 -0.5050 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3648 2.1195 -1.2979 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0019 0.2892 0.1606 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3592 0.4366 0.0594 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8248 1.3399 -0.6521 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5206 -1.4488 -0.1838 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3696 -0.6883 0.6405 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3198 -1.6116 -1.4932 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3800 -2.4709 -1.3411 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7363 -0.1936 -1.8281 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4543 -0.2152 -3.0004 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6597 3.1645 -1.6562 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5114 4.5541 -0.5391 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9459 4.7376 -2.2266 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6391 1.8663 0.0079 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0774 2.7638 -1.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4620 1.0565 -2.9215 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5396 -1.5826 -0.9265 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1622 -3.6624 2.5099 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0271 -5.3487 3.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3665 -6.1747 4.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5332 -2.9641 3.7011 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3493 -1.2930 2.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1847 -1.6911 1.7047 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8179 1.1900 -0.6371 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6467 -0.1408 -1.7740 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8923 -0.7902 -3.1992 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8951 0.6771 -2.8454 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5196 0.8290 -3.7019 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1040 2.4405 -1.6156 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4433 2.9687 -1.1668 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5893 2.9818 0.5624 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6415 2.6628 0.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5494 0.2426 1.6519 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2631 1.3797 2.9061 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9186 1.5742 -0.8982 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0607 1.8895 -2.2430 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4243 -2.4841 0.2093 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8445 -1.2747 1.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6326 -1.9423 -2.2945 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4026 -2.9455 -0.4852 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4361 0.1540 -1.0160 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2562 -0.7515 -2.8763 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 15 17 1 0 17 18 2 0 11 19 1 0 19 20 1 0 20 21 2 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 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 22 34 2 0 34 35 1 0 35 36 1 0 35 37 2 0 37 38 1 0 38 39 2 0 8 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 44 6 1 0 38 10 1 0 18 12 1 0 37 20 1 0 32 24 1 0 1 46 1 0 1 47 1 0 1 48 1 0 5 49 1 0 5 50 1 0 6 51 1 6 8 52 1 6 13 53 1 0 14 54 1 0 16 55 1 0 17 56 1 0 18 57 1 0 21 58 1 0 24 59 1 6 26 60 1 6 27 61 1 0 27 62 1 0 27 63 1 0 28 64 1 6 29 65 1 0 30 66 1 6 31 67 1 0 32 68 1 1 33 69 1 0 34 70 1 0 36 71 1 0 40 72 1 1 41 73 1 0 42 74 1 6 43 75 1 0 44 76 1 1 45 77 1 0 M END

Standard InCHIKey	GMYLPJSOUAYAGD-VVAUDJEDSA-N
Standard InCHI	InChI=1S/C29H32O16/c1-10-19(33)22(36)24(38)28(41-10)42-14-7-15(32)18-16(8-14)43-26(12-3-5-13(31)6-4-12)27(21(18)35)45-29-25(39)23(37)20(34)17(44-29)9-40-11(2)30/h3-8,10,17,19-20,22-25,28-29,31-34,36-39H,9H2,1-2H3/t10-,17+,19-,20+,22-,23-,24+,25-,28-,29-/m0/s1
SMILES	CC(=O)OC[C@H]1O[C@@H](OC2=C(C3=CC=C(O)C=C3)OC3=CC(O[C@@H]4O[C@@H](C)[C@H](O)[C@H](O)[C@H]4O)=CC(O)=C3C2=O)[C@@H](O)[C@@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	636.17	Volume:	584.273 ? Van der Waals volume.
Dense:	1.089	LogP:	0.912 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.266 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.775 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	31.0
TPSA:	255.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.142	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.735	Fsp³:	0.448
MCE-18:	121.667 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.626	Fluc inhibitor:	0.323 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.855 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.679 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.06	Promiscuous compounds:	0.468

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.301	MDCK Permeability:	-5.169
Pgp-inhibitor:	0.0	Pgp-substrate:	0.911
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):	0.009
20% Bioavailability (F20%):	0.013	30% Bioavailability (F30%):	0.666
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.022
Plasma Protein Binding (PPB):	85.052%	Volume Distribution (VD):	-0.069
Fu:	15.982% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.239
BSEP inhibitor:	0.656

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:	0.48
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.972
HLM stability:	0.699 ? 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):

1.62

Half-life (T1/2):

4.042

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.221
Human Hepatotoxicity (H-HT):	0.464	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.934	Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.015	Skin Sensitization:	0.997
Carcinogencity:	0.054	Eye Corrosion:	0.0
Eye Irritation:	0.06	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.936
Hematotoxicity:	0.124	Drug-induced Nephrotoxicity:	0.462
Genotoxicity:	0.887	RPMI-8226 Immunitoxicity:	0.135
A549 Cytotoxicity:	0.321	Hek293 Cytotoxicity:	0.271
BCF:	0.489 ? 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:	3.125 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.662 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.846 ? 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
NPO49941	Equisetum telmateja	Genus	Equisetaceae	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 NPC545768 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	16539
0.1-0.2	29624
0.2-0.3	2735
0.3-0.4	442
0.4-0.5	265
0.5-0.6	112
0.6-0.7	75
0.7-0.8	0
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
0.8659	High Similarity	NPC186816
0.8421	Intermediate Similarity	NPC249281
0.8205	Intermediate Similarity	NPC46420
0.8148	Intermediate Similarity	NPC276377
0.7931	Intermediate Similarity	NPC72016
0.7805	Intermediate Similarity	NPC116458
0.7805	Intermediate Similarity	NPC246943
0.7674	Intermediate Similarity	NPC150164
0.7419	Intermediate Similarity	NPC121703
0.7317	Intermediate Similarity	NPC271692
0.7195	Intermediate Similarity	NPC297987
0.7011	Intermediate Similarity	NPC116864
0.7011	Intermediate Similarity	NPC244776
0.6977	Remote Similarity	NPC605784
0.6966	Remote Similarity	NPC173582
0.6966	Remote Similarity	NPC265885
0.6966	Remote Similarity	NPC181465
0.6966	Remote Similarity	NPC215710
0.6966	Remote Similarity	NPC473438
0.6966	Remote Similarity	NPC253788
0.6941	Remote Similarity	NPC611303
0.6837	Remote Similarity	NPC25523
0.6786	Remote Similarity	NPC158674
0.6778	Remote Similarity	NPC44931
0.6774	Remote Similarity	NPC32641
0.6774	Remote Similarity	NPC256188
0.6774	Remote Similarity	NPC35119
0.6747	Remote Similarity	NPC111929
0.6747	Remote Similarity	NPC320283
0.6747	Remote Similarity	NPC41121
0.6739	Remote Similarity	NPC64425
0.6702	Remote Similarity	NPC142142
0.6667	Remote Similarity	NPC108831
0.6667	Remote Similarity	NPC182634
0.6559	Remote Similarity	NPC153755
0.6559	Remote Similarity	NPC64051
0.6556	Remote Similarity	NPC251417
0.6548	Remote Similarity	NPC331652
0.6522	Remote Similarity	NPC65563
0.6522	Remote Similarity	NPC470949
0.6471	Remote Similarity	NPC289667
0.6452	Remote Similarity	NPC473571
0.6452	Remote Similarity	NPC110941
0.6436	Remote Similarity	NPC277532
0.6421	Remote Similarity	NPC606657
0.6413	Remote Similarity	NPC67105
0.6395	Remote Similarity	NPC136042
0.6354	Remote Similarity	NPC486577
0.6344	Remote Similarity	NPC203259
0.6344	Remote Similarity	NPC33054
0.6344	Remote Similarity	NPC210073
0.6344	Remote Similarity	NPC176740
0.6344	Remote Similarity	NPC471725
0.6344	Remote Similarity	NPC134532
0.6344	Remote Similarity	NPC602582
0.6321	Remote Similarity	NPC209550
0.6304	Remote Similarity	NPC471079
0.6304	Remote Similarity	NPC609888
0.6289	Remote Similarity	NPC470447
0.6289	Remote Similarity	NPC85751
0.6289	Remote Similarity	NPC19240
0.6279	Remote Similarity	NPC238376
0.6224	Remote Similarity	NPC101636
0.6224	Remote Similarity	NPC298171
0.6211	Remote Similarity	NPC240306
0.6186	Remote Similarity	NPC270675
0.6186	Remote Similarity	NPC195685
0.6176	Remote Similarity	NPC480441
0.6146	Remote Similarity	NPC470443
0.6122	Remote Similarity	NPC80068
0.6105	Remote Similarity	NPC129264
0.61	Remote Similarity	NPC214621
0.61	Remote Similarity	NPC34267
0.6092	Remote Similarity	NPC127546
0.6092	Remote Similarity	NPC57625
0.6092	Remote Similarity	NPC19709
0.6092	Remote Similarity	NPC173637
0.6092	Remote Similarity	NPC317489
0.6092	Remote Similarity	NPC223424
0.6092	Remote Similarity	NPC600591
0.6087	Remote Similarity	NPC172807
0.6087	Remote Similarity	NPC477848
0.6082	Remote Similarity	NPC229409
0.6	Remote Similarity	NPC22062
0.6	Remote Similarity	NPC473634
0.6	Remote Similarity	NPC470450
0.6	Remote Similarity	NPC472994
0.6	Remote Similarity	NPC138811
0.596	Remote Similarity	NPC476472
0.596	Remote Similarity	NPC294815
0.596	Remote Similarity	NPC473073
0.596	Remote Similarity	NPC16194
0.596	Remote Similarity	NPC471669
0.5955	Remote Similarity	NPC84362
0.5955	Remote Similarity	NPC27640
0.5941	Remote Similarity	NPC470455
0.5941	Remote Similarity	NPC14187
0.5918	Remote Similarity	NPC270448
0.5918	Remote Similarity	NPC209296
0.5918	Remote Similarity	NPC473327
0.59	Remote Similarity	NPC36138
0.59	Remote Similarity	NPC470449
0.5895	Remote Similarity	NPC39834
0.5895	Remote Similarity	NPC227508
0.5876	Remote Similarity	NPC470125
0.5876	Remote Similarity	NPC126784
0.5876	Remote Similarity	NPC241423
0.5842	Remote Similarity	NPC223426
0.5833	Remote Similarity	NPC303913
0.5825	Remote Similarity	NPC189564
0.5769	Remote Similarity	NPC480796
0.5769	Remote Similarity	NPC472993
0.5745	Remote Similarity	NPC265115
0.5743	Remote Similarity	NPC470445
0.573	Remote Similarity	NPC77672
0.573	Remote Similarity	NPC133671
0.573	Remote Similarity	NPC135391
0.573	Remote Similarity	NPC78263
0.573	Remote Similarity	NPC250069
0.5729	Remote Similarity	NPC67326
0.5714	Remote Similarity	NPC59534
0.5714	Remote Similarity	NPC46202
0.5714	Remote Similarity	NPC27942
0.5714	Remote Similarity	NPC164704
0.5699	Remote Similarity	NPC223747
0.5684	Remote Similarity	NPC254540
0.5673	Remote Similarity	NPC470416
0.567	Remote Similarity	NPC156869
0.5667	Remote Similarity	NPC323593
0.5667	Remote Similarity	NPC203500
0.5657	Remote Similarity	NPC12013
0.5657	Remote Similarity	NPC483414
0.5657	Remote Similarity	NPC11432
0.5657	Remote Similarity	NPC483415
0.5657	Remote Similarity	NPC477613
0.5652	Remote Similarity	NPC159579
0.5652	Remote Similarity	NPC219904
0.5638	Remote Similarity	NPC66087
0.5638	Remote Similarity	NPC190003
0.5631	Remote Similarity	NPC81042
0.5618	Remote Similarity	NPC473043
0.5618	Remote Similarity	NPC135599
0.5618	Remote Similarity	NPC73855
0.5618	Remote Similarity	NPC113968
0.5618	Remote Similarity	NPC328940
0.5618	Remote Similarity	NPC277174
0.5618	Remote Similarity	NPC606877
0.5604	Remote Similarity	NPC305811
0.5604	Remote Similarity	NPC24043
0.56	Remote Similarity	NPC483416
0.5596	Remote Similarity	NPC298666
0.5586	Remote Similarity	NPC138990
0.5577	Remote Similarity	NPC203145
0.5566	Remote Similarity	NPC217520
0.5556	Remote Similarity	NPC39360
0.5556	Remote Similarity	NPC29763
0.5556	Remote Similarity	NPC210003
0.5556	Remote Similarity	NPC348541
0.5536	Remote Similarity	NPC175429
0.5505	Remote Similarity	NPC488739
0.55	Remote Similarity	NPC65711
0.5495	Remote Similarity	NPC265530
0.5495	Remote Similarity	NPC470720
0.5484	Remote Similarity	NPC129217
0.5472	Remote Similarity	NPC477895
0.5463	Remote Similarity	NPC470716
0.5455	Remote Similarity	NPC54802
0.5455	Remote Similarity	NPC197304
0.5455	Remote Similarity	NPC480445
0.5446	Remote Similarity	NPC37668
0.5443	Remote Similarity	NPC146679
0.5437	Remote Similarity	NPC221342
0.5437	Remote Similarity	NPC476470
0.5429	Remote Similarity	NPC11468
0.5421	Remote Similarity	NPC470715
0.5417	Remote Similarity	NPC211594
0.5405	Remote Similarity	NPC470717
0.54	Remote Similarity	NPC296018
0.54	Remote Similarity	NPC488074
0.5393	Remote Similarity	NPC288084
0.5392	Remote Similarity	NPC488089
0.5385	Remote Similarity	NPC470446
0.5385	Remote Similarity	NPC476405
0.5385	Remote Similarity	NPC602448
0.5376	Remote Similarity	NPC216496
0.5364	Remote Similarity	NPC488734
0.5364	Remote Similarity	NPC488735
0.5364	Remote Similarity	NPC488732
0.5364	Remote Similarity	NPC488738
0.534	Remote Similarity	NPC89127
0.5327	Remote Similarity	NPC292019
0.5327	Remote Similarity	NPC202908
0.5326	Remote Similarity	NPC64305
0.5326	Remote Similarity	NPC277205
0.5326	Remote Similarity	NPC37919
0.5321	Remote Similarity	NPC139571
0.5319	Remote Similarity	NPC175107
0.5312	Remote Similarity	NPC476215
0.5312	Remote Similarity	NPC355481
0.5306	Remote Similarity	NPC480466

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC545768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4671
0.1-0.2	4406
0.2-0.3	61
0.3-0.4	5
0.4-0.5	3
0.5-0.6	1
0.6-0.7	3
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
0.6989	Remote Similarity	NPD7251	Phase 2
0.6531	Remote Similarity	NPD7808	Phase 3
0.6344	Remote Similarity	NPD6797	Phase 2
0.5918	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