NPASS Compound

Natural Product: NPC554153

Natural Product ID	NPC554153
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-7-methoxy-2-[4-[(2~{S},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxyphenyl]chromen-4-one
IUPAC Name	5-hydroxy-7-methoxy-2-[4-[(2~{S},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxyphenyl]chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 71 75 0 0 0 0 0 0 0 0999 V2000 8.8837 2.7350 -4.1419 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0733 1.6988 -3.4846 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2595 2.1283 -2.4509 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3354 3.4106 -2.0382 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5413 3.9410 -1.0886 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7094 5.3062 -0.7116 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5783 3.2274 -0.4566 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7062 3.8332 0.4455 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9355 5.0680 0.6772 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7230 3.0561 0.9625 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6316 1.7326 0.5931 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5724 0.8898 1.1393 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6681 1.2585 2.0731 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5801 0.4874 2.3709 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3898 -0.7368 1.6853 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6677 -1.4310 1.9529 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7216 -2.1410 2.2090 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6942 -1.7769 1.1814 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5493 -0.7738 1.6951 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9947 0.0834 0.5649 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5219 -0.6991 -0.5156 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8844 -0.1560 -1.6786 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5295 -0.8287 -1.5282 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6020 -2.0994 -1.9789 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8864 -2.8183 -2.0722 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4119 -3.2419 -0.8516 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9815 -2.0293 -2.7550 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1404 -1.9436 -1.9755 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3714 -0.6171 -2.9377 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2038 0.0959 -3.7506 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5672 -1.3752 2.5547 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0186 -0.5007 3.5075 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8843 -2.5503 3.3204 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5319 -2.8707 4.4717 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4250 -2.1798 3.5080 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3691 -1.0302 4.2717 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3162 -1.1264 0.7419 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3903 -0.3735 0.4424 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4764 1.2315 -0.2530 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4504 1.9084 -0.8184 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2745 1.2916 -1.7984 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1023 3.5557 -4.4151 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2486 2.3950 -5.1034 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5931 3.2223 -3.5034 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0994 4.0811 -2.4856 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6781 5.5243 -0.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0407 3.5453 1.6292 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8621 2.1922 2.5881 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0823 0.8071 3.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5645 -3.2350 1.8868 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8886 -0.1172 2.3328 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7296 0.8660 0.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1156 0.6322 0.1009 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5565 0.8450 -1.4894 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9326 -2.7346 -1.2987 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1017 -2.1860 -2.9969 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7267 -3.7973 -2.6669 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3584 -3.4356 -0.9538 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1817 -2.4825 -3.7522 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7720 -2.6394 -2.3085 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4481 -0.8975 -3.6370 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3752 -0.4056 -4.6164 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4302 -1.7845 1.9946 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7133 -0.6835 4.4358 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9294 -3.3826 2.5947 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2254 -3.5429 4.2948 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0229 -3.0366 4.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5900 -0.9203 4.8361 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2109 -2.1076 0.1797 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1318 -0.6533 -0.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2387 0.2919 -2.0599 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 5 6 1 0 5 7 2 0 7 8 1 0 8 9 2 0 8 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 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 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 19 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 15 37 1 0 37 38 2 0 11 39 1 0 39 40 1 0 40 41 2 0 41 3 1 0 40 7 1 0 38 12 1 0 35 17 1 0 29 22 1 0 1 42 1 0 1 43 1 0 1 44 1 0 4 45 1 0 6 46 1 0 10 47 1 0 13 48 1 0 14 49 1 0 17 50 1 6 19 51 1 1 20 52 1 0 20 53 1 0 22 54 1 6 24 55 1 0 24 56 1 0 25 57 1 6 26 58 1 0 27 59 1 6 28 60 1 0 29 61 1 6 30 62 1 0 31 63 1 6 32 64 1 0 33 65 1 6 34 66 1 0 35 67 1 1 36 68 1 0 37 69 1 0 38 70 1 0 41 71 1 0 M END

Standard InCHIKey	KQBGCOBMJGLTEP-MUIMGZHPSA-N
Standard InCHI	InChI=1S/C27H30O14/c1-36-13-6-14(28)20-15(29)8-17(40-18(20)7-13)11-2-4-12(5-3-11)39-27-25(35)23(33)22(32)19(41-27)10-38-26-24(34)21(31)16(30)9-37-26/h2-8,16,19,21-28,30-35H,9-10H2,1H3/t16-,19+,21-,22+,23+,24-,25+,26-,27-/m1/s1
SMILES	COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[C@@H]4O[C@@H](CO[C@H]5OC[C@@H](O)[C@@H](O)[C@H]5O)[C@H](O)[C@H](O)[C@@H]4O)C=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.16	Volume:	534.737 ? Van der Waals volume.
Dense:	1.081	LogP:	1.112 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.559 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.54 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	217.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.176	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.519	Fsp³:	0.444
MCE-18:	112.41 ? 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:	0.645	Fluc inhibitor:	0.355 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.956 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.819 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.061	Promiscuous compounds:	0.302

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.216	MDCK Permeability:	-5.278
Pgp-inhibitor:	0.0	Pgp-substrate:	0.954
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):	0.149
20% Bioavailability (F20%):	0.451	30% Bioavailability (F30%):	0.372
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.214
Plasma Protein Binding (PPB):	86.104%	Volume Distribution (VD):	-0.047
Fu:	12.712% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.963
OATP1B3 inhibitor:	0.984	BCRP inhibitor:	0.035
BSEP inhibitor:	0.77

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.018
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.022 ? 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):

1.086

Half-life (T1/2):

2.79

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.319
Human Hepatotoxicity (H-HT):	0.581	Drug-induced Liver Injury (DILI):	0.976
AMES Toxicity:	0.93	Rat Oral Acute Toxicity:	0.12
Maximum Recommended Daily Dose:	0.463	Skin Sensitization:	0.986
Carcinogencity:	0.152	Eye Corrosion:	0.0
Eye Irritation:	0.865	Respiratory Toxicity:	0.293
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.807
Hematotoxicity:	0.599	Drug-induced Nephrotoxicity:	0.776
Genotoxicity:	0.848	RPMI-8226 Immunitoxicity:	0.28
A549 Cytotoxicity:	0.474	Hek293 Cytotoxicity:	0.4
BCF:	0.436 ? 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:	3.209 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.682 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.882 ? 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
NPO53565	Salvia moorcroftiana	Species	Lamiaceae	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 NPC554153 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	19546
0.1-0.2	26132
0.2-0.3	3090
0.3-0.4	667
0.4-0.5	290
0.5-0.6	81
0.6-0.7	36
0.7-0.8	1
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8193	Intermediate Similarity	NPC22062
0.8193	Intermediate Similarity	NPC473634
0.8193	Intermediate Similarity	NPC138811
0.7614	Intermediate Similarity	NPC473623
0.7529	Intermediate Similarity	NPC295613
0.7529	Intermediate Similarity	NPC473657
0.7528	Intermediate Similarity	NPC488089
0.7442	Intermediate Similarity	NPC44931
0.7416	Intermediate Similarity	NPC209296
0.7191	Intermediate Similarity	NPC46202
0.7159	Intermediate Similarity	NPC473512
0.7159	Intermediate Similarity	NPC129827
0.7079	Intermediate Similarity	NPC204693
0.6988	Remote Similarity	NPC181712
0.6966	Remote Similarity	NPC210073
0.6867	Remote Similarity	NPC95090
0.6867	Remote Similarity	NPC27408
0.6848	Remote Similarity	NPC483707
0.6813	Remote Similarity	NPC284277
0.6813	Remote Similarity	NPC475497
0.6809	Remote Similarity	NPC101636
0.6739	Remote Similarity	NPC65711
0.6705	Remote Similarity	NPC211594
0.663	Remote Similarity	NPC64051
0.6598	Remote Similarity	NPC11468
0.6512	Remote Similarity	NPC27942
0.6484	Remote Similarity	NPC15358
0.6458	Remote Similarity	NPC298171
0.6421	Remote Similarity	NPC270675
0.6421	Remote Similarity	NPC195685
0.6316	Remote Similarity	NPC229409
0.63	Remote Similarity	NPC472993
0.6292	Remote Similarity	NPC607707
0.6275	Remote Similarity	NPC488087
0.6238	Remote Similarity	NPC473644
0.6235	Remote Similarity	NPC331652
0.6224	Remote Similarity	NPC472994
0.618	Remote Similarity	NPC22832
0.618	Remote Similarity	NPC243930
0.6176	Remote Similarity	NPC311850
0.6163	Remote Similarity	NPC39360
0.6163	Remote Similarity	NPC29763
0.6163	Remote Similarity	NPC210003
0.6154	Remote Similarity	NPC488086
0.6154	Remote Similarity	NPC172807
0.6117	Remote Similarity	NPC488083
0.6061	Remote Similarity	NPC135358
0.602	Remote Similarity	NPC475382
0.6	Remote Similarity	NPC68592
0.5977	Remote Similarity	NPC58053
0.587	Remote Similarity	NPC190003
0.5859	Remote Similarity	NPC477629
0.5843	Remote Similarity	NPC186807
0.5833	Remote Similarity	NPC186816
0.5818	Remote Similarity	NPC262222
0.5816	Remote Similarity	NPC51326
0.5795	Remote Similarity	NPC261866
0.5795	Remote Similarity	NPC19709
0.5795	Remote Similarity	NPC143851
0.5789	Remote Similarity	NPC67105
0.5789	Remote Similarity	NPC29353
0.5773	Remote Similarity	NPC475366
0.5761	Remote Similarity	NPC311830
0.5745	Remote Similarity	NPC254540
0.573	Remote Similarity	NPC189142
0.573	Remote Similarity	NPC77660
0.57	Remote Similarity	NPC231194
0.5684	Remote Similarity	NPC471079
0.5684	Remote Similarity	NPC187379
0.5684	Remote Similarity	NPC51774
0.5682	Remote Similarity	NPC473043
0.5652	Remote Similarity	NPC80188
0.5652	Remote Similarity	NPC608742
0.5648	Remote Similarity	NPC298666
0.5648	Remote Similarity	NPC198199
0.5625	Remote Similarity	NPC67326
0.5625	Remote Similarity	NPC275454
0.5625	Remote Similarity	NPC227508
0.5612	Remote Similarity	NPC488074
0.5607	Remote Similarity	NPC488088
0.56	Remote Similarity	NPC479766
0.5591	Remote Similarity	NPC293004
0.5591	Remote Similarity	NPC220169
0.5579	Remote Similarity	NPC156977
0.5545	Remote Similarity	NPC479765
0.5495	Remote Similarity	NPC120952
0.5484	Remote Similarity	NPC601144
0.5464	Remote Similarity	NPC301683
0.5408	Remote Similarity	NPC65003
0.5408	Remote Similarity	NPC479405
0.5408	Remote Similarity	NPC303913
0.5368	Remote Similarity	NPC276377
0.5361	Remote Similarity	NPC236191
0.5354	Remote Similarity	NPC479404
0.5326	Remote Similarity	NPC105025
0.5316	Remote Similarity	NPC234133
0.5312	Remote Similarity	NPC52353
0.5294	Remote Similarity	NPC142142
0.5278	Remote Similarity	NPC277532
0.5275	Remote Similarity	NPC289667
0.5258	Remote Similarity	NPC8856
0.5248	Remote Similarity	NPC479403
0.5244	Remote Similarity	NPC79908
0.5243	Remote Similarity	NPC80068
0.5238	Remote Similarity	NPC298845
0.5217	Remote Similarity	NPC93337
0.5213	Remote Similarity	NPC609451
0.5208	Remote Similarity	NPC194483
0.52	Remote Similarity	NPC122809
0.5196	Remote Similarity	NPC473327
0.519	Remote Similarity	NPC127447
0.5189	Remote Similarity	NPC121703
0.5161	Remote Similarity	NPC46420
0.5158	Remote Similarity	NPC486578
0.5158	Remote Similarity	NPC605067
0.5152	Remote Similarity	NPC142996
0.5146	Remote Similarity	NPC486577
0.5143	Remote Similarity	NPC179862
0.5122	Remote Similarity	NPC195202
0.5122	Remote Similarity	NPC223579
0.5104	Remote Similarity	NPC88023
0.5104	Remote Similarity	NPC309025
0.5096	Remote Similarity	NPC195257
0.5094	Remote Similarity	NPC244875
0.5093	Remote Similarity	NPC480796
0.5053	Remote Similarity	NPC282169
0.5053	Remote Similarity	NPC611303
0.505	Remote Similarity	NPC115674
0.5048	Remote Similarity	NPC287889
0.5046	Remote Similarity	NPC25523

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC554153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4894
0.1-0.2	4167
0.2-0.3	74
0.3-0.4	10
0.4-0.5	1
0.5-0.6	3
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
0.7416	Intermediate Similarity	NPD7054	Phase 4
0.5784	Remote Similarity	NPD7472	Pre-clinical
0.5631	Remote Similarity	NPD7808	Phase 3
0.5545	Remote Similarity	NPD7251	Phase 2

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