NPASS Compound

Natural Product: NPC541008

Natural Product ID	NPC541008
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6-methoxy-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6-methoxy-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{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] [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 81 85 0 0 0 0 0 0 0 0999 V2000 0.2749 -4.8836 3.0747 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7990 -4.8835 2.1613 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4304 -3.6715 1.8762 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0184 -2.5129 2.4717 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6640 -1.3172 2.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7035 -1.2019 1.3018 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3908 -0.0327 0.8773 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9626 1.2337 1.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7402 1.5087 1.6162 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5205 1.5422 0.8532 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5342 0.9306 1.4901 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5538 0.8094 0.5404 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4782 -0.3254 0.8406 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4930 -0.5160 -0.0501 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3203 -1.5989 0.2652 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5584 -1.1826 0.6405 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4203 -1.0177 -0.4052 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9400 0.0670 -1.3240 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8278 0.2729 -2.3886 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6458 -2.3258 -1.1535 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4927 -2.0716 -2.2233 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3517 -2.8690 -1.6664 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1080 -2.2644 -2.9035 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2178 -2.7168 -0.7035 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1461 -3.9371 0.0146 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2242 2.1643 0.5472 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7536 2.4848 1.7899 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2491 3.1719 0.0622 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6367 4.4301 0.5698 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1961 2.9074 0.3337 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8479 3.0515 -0.9202 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6955 2.3512 0.5847 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2710 3.5287 0.7418 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9012 2.1194 -0.0214 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6401 3.2016 -0.4627 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1321 4.4789 -0.2690 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8594 2.9742 -1.0795 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5648 4.0864 -1.5050 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3122 4.5711 -2.8113 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2759 1.6747 -1.2213 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5163 1.4471 -1.8491 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5374 0.5863 -0.7791 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3063 0.8162 -0.1569 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5859 -0.1758 0.2700 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0941 -2.4288 0.7129 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4771 -3.6121 0.9938 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8847 -4.8087 0.3962 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0394 -4.6697 4.1220 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7762 -5.8709 2.9920 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0562 -4.1228 2.8272 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1927 -2.5672 3.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3320 -0.4671 2.6845 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7602 0.9304 -0.0578 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1283 0.6533 -0.4712 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8375 -1.2388 0.9675 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9658 -0.0665 1.8303 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8472 -1.9824 1.2526 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4343 -0.7005 -0.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7524 0.9860 -0.7433 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9470 -0.2519 -1.7624 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0997 1.2384 -2.3573 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0925 -3.0686 -0.4536 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3430 -2.7941 -2.8974 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4921 -3.9587 -1.9152 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6233 -2.8781 -3.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2653 -2.7045 -1.2866 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9257 -4.0498 0.5941 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1092 2.0634 -0.1442 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0675 2.6291 2.4722 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4436 3.2743 -1.0493 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0723 4.3834 1.4367 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5751 3.7282 0.9611 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7345 2.1632 -1.3828 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2581 4.8639 0.6620 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9834 4.0693 -3.5071 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4914 5.6807 -2.7587 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2414 4.3992 -3.1096 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3539 1.9031 -1.5193 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8497 -0.4337 -0.8821 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9122 -2.4552 0.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4543 -4.7415 -0.4542 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 12 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 8 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 1 0 37 40 2 0 40 41 1 0 40 42 1 0 42 43 2 0 43 44 1 0 6 45 1 0 45 46 2 0 46 47 1 0 46 3 1 0 44 7 1 0 30 10 1 0 43 34 1 0 24 15 1 0 1 48 1 0 1 49 1 0 1 50 1 0 4 51 1 0 5 52 1 0 10 53 1 6 12 54 1 6 13 55 1 0 13 56 1 0 15 57 1 1 17 58 1 1 18 59 1 0 18 60 1 0 19 61 1 0 20 62 1 1 21 63 1 0 22 64 1 6 23 65 1 0 24 66 1 6 25 67 1 0 26 68 1 6 27 69 1 0 28 70 1 6 29 71 1 0 30 72 1 1 31 73 1 0 36 74 1 0 39 75 1 0 39 76 1 0 39 77 1 0 41 78 1 0 42 79 1 0 45 80 1 0 47 81 1 0 M END

Standard InCHIKey	SFWZUPNUMMRBQM-HDKYCGBKSA-N
Standard InCHI	InChI=1S/C29H34O18/c1-41-12-4-3-9(5-10(12)31)25-27(20(36)16-13(44-25)6-11(32)26(42-2)19(16)35)47-29-24(40)22(38)18(34)15(46-29)8-43-28-23(39)21(37)17(33)14(7-30)45-28/h3-6,14-15,17-18,21-24,28-35,37-40H,7-8H2,1-2H3/t14-,15-,17+,18+,21+,22+,23-,24-,28-,29+/m1/s1
SMILES	COC1=CC=C(C2=C(O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H](O)[C@H]3O)C(=O)C3=C(O)C(OC)=C(O)C=C3O2)C=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	670.17	Volume:	604.49 ? Van der Waals volume.
Dense:	1.109	LogP:	0.094 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.789 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.9 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	287.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.113	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.868	Fsp³:	0.483
MCE-18:	124.744 ? 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:	0
Colloidal aggregators:	0.607	Fluc inhibitor:	0.264 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.74 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.607 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.071	Promiscuous compounds:	0.452

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.38	MDCK Permeability:	-5.461
Pgp-inhibitor:	0.0	Pgp-substrate:	0.894
PAMPA:	0.994 ? 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):	0.99
20% Bioavailability (F20%):	0.909	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.535
Plasma Protein Binding (PPB):	80.454%	Volume Distribution (VD):	-0.164
Fu:	16.89% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.984
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.041
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.051	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.063
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.972 ? 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):

0.956

Half-life (T1/2):

2.941

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.052
Human Hepatotoxicity (H-HT):	0.672	Drug-induced Liver Injury (DILI):	0.943
AMES Toxicity:	0.985	Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.031	Skin Sensitization:	1.0
Carcinogencity:	0.231	Eye Corrosion:	0.0
Eye Irritation:	0.277	Respiratory Toxicity:	0.052
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.924
Hematotoxicity:	0.641	Drug-induced Nephrotoxicity:	0.713
Genotoxicity:	0.795	RPMI-8226 Immunitoxicity:	0.277
A549 Cytotoxicity:	0.985	Hek293 Cytotoxicity:	0.802
BCF:	0.252 ? 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:	2.785 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.393 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.524 ? 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
NPO46137	Brickellia microphylla	Species	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 NPC541008 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	19314
0.1-0.2	26013
0.2-0.3	3306
0.3-0.4	730
0.4-0.5	315
0.5-0.6	121
0.6-0.7	38
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.869	High Similarity	NPC488073
0.764	Intermediate Similarity	NPC126784
0.764	Intermediate Similarity	NPC241423
0.7473	Intermediate Similarity	NPC473327
0.7444	Intermediate Similarity	NPC488074
0.7333	Intermediate Similarity	NPC473571
0.7333	Intermediate Similarity	NPC110941
0.7176	Intermediate Similarity	NPC42773
0.7176	Intermediate Similarity	NPC45522
0.7158	Intermediate Similarity	NPC470446
0.7033	Intermediate Similarity	NPC156869
0.7011	Intermediate Similarity	NPC120099
0.6875	Remote Similarity	NPC470449
0.6875	Remote Similarity	NPC470445
0.686	Remote Similarity	NPC488080
0.686	Remote Similarity	NPC169977
0.6818	Remote Similarity	NPC101026
0.6818	Remote Similarity	NPC488077
0.6629	Remote Similarity	NPC21666
0.66	Remote Similarity	NPC470451
0.6598	Remote Similarity	NPC470447
0.6517	Remote Similarity	NPC60735
0.6517	Remote Similarity	NPC26230
0.6444	Remote Similarity	NPC609478
0.6292	Remote Similarity	NPC305811
0.6263	Remote Similarity	NPC476472
0.6263	Remote Similarity	NPC294815
0.6263	Remote Similarity	NPC16194
0.6238	Remote Similarity	NPC470455
0.62	Remote Similarity	NPC36138
0.6154	Remote Similarity	NPC219904
0.6146	Remote Similarity	NPC203259
0.6146	Remote Similarity	NPC33054
0.6146	Remote Similarity	NPC176740
0.6146	Remote Similarity	NPC471725
0.6146	Remote Similarity	NPC134532
0.6146	Remote Similarity	NPC602582
0.6139	Remote Similarity	NPC470450
0.6122	Remote Similarity	NPC470443
0.6117	Remote Similarity	NPC470416
0.6058	Remote Similarity	NPC292019
0.6058	Remote Similarity	NPC202908
0.6044	Remote Similarity	NPC472459
0.6042	Remote Similarity	NPC173582
0.6042	Remote Similarity	NPC265885
0.6042	Remote Similarity	NPC181465
0.6042	Remote Similarity	NPC67326
0.6042	Remote Similarity	NPC215710
0.6042	Remote Similarity	NPC473438
0.6042	Remote Similarity	NPC253788
0.5962	Remote Similarity	NPC189564
0.5938	Remote Similarity	NPC471079
0.5876	Remote Similarity	NPC39834
0.5859	Remote Similarity	NPC153755
0.5833	Remote Similarity	NPC251417
0.5824	Remote Similarity	NPC64305
0.5816	Remote Similarity	NPC65563
0.5816	Remote Similarity	NPC470949
0.5806	Remote Similarity	NPC488071
0.5806	Remote Similarity	NPC611303
0.5789	Remote Similarity	NPC203050
0.5789	Remote Similarity	NPC225434
0.5784	Remote Similarity	NPC473073
0.5773	Remote Similarity	NPC609888
0.5766	Remote Similarity	NPC488078
0.5758	Remote Similarity	NPC470444
0.575	Remote Similarity	NPC9609
0.5743	Remote Similarity	NPC209296
0.5729	Remote Similarity	NPC116864
0.5729	Remote Similarity	NPC244776
0.5699	Remote Similarity	NPC325555
0.5699	Remote Similarity	NPC226304
0.566	Remote Similarity	NPC488075
0.5652	Remote Similarity	NPC145038
0.5652	Remote Similarity	NPC56077
0.5652	Remote Similarity	NPC281131
0.5652	Remote Similarity	NPC253662
0.5652	Remote Similarity	NPC179950
0.5652	Remote Similarity	NPC88789
0.5652	Remote Similarity	NPC491374
0.5648	Remote Similarity	NPC277532
0.5644	Remote Similarity	NPC480471
0.5644	Remote Similarity	NPC488076
0.5625	Remote Similarity	NPC488072
0.56	Remote Similarity	NPC186816
0.5591	Remote Similarity	NPC24043
0.5577	Remote Similarity	NPC292929
0.5566	Remote Similarity	NPC203145
0.5556	Remote Similarity	NPC480441
0.5543	Remote Similarity	NPC289667
0.5543	Remote Similarity	NPC77672
0.5543	Remote Similarity	NPC133671
0.5543	Remote Similarity	NPC135391
0.5543	Remote Similarity	NPC78263
0.5543	Remote Similarity	NPC250069
0.5526	Remote Similarity	NPC192539
0.5524	Remote Similarity	NPC602448
0.5487	Remote Similarity	NPC488079
0.5481	Remote Similarity	NPC76831
0.5463	Remote Similarity	NPC48984
0.5417	Remote Similarity	NPC486578
0.5413	Remote Similarity	NPC25523
0.54	Remote Similarity	NPC275454
0.5376	Remote Similarity	NPC19388
0.5376	Remote Similarity	NPC240431
0.5376	Remote Similarity	NPC55786
0.5368	Remote Similarity	NPC21100
0.5368	Remote Similarity	NPC599850
0.5321	Remote Similarity	NPC219043
0.5321	Remote Similarity	NPC173837
0.5321	Remote Similarity	NPC477895
0.5319	Remote Similarity	NPC265530
0.5319	Remote Similarity	NPC136042
0.53	Remote Similarity	NPC29958
0.5288	Remote Similarity	NPC606657
0.5287	Remote Similarity	NPC37074
0.5278	Remote Similarity	NPC89052
0.5273	Remote Similarity	NPC217520
0.5263	Remote Similarity	NPC84362
0.5263	Remote Similarity	NPC603655
0.5258	Remote Similarity	NPC22832
0.5258	Remote Similarity	NPC605067
0.5248	Remote Similarity	NPC471748
0.5234	Remote Similarity	NPC223426
0.5234	Remote Similarity	NPC135358
0.5227	Remote Similarity	NPC287780
0.5227	Remote Similarity	NPC60982
0.5204	Remote Similarity	NPC206123
0.5189	Remote Similarity	NPC85751
0.5189	Remote Similarity	NPC471669
0.5189	Remote Similarity	NPC19240
0.5189	Remote Similarity	NPC89127
0.5185	Remote Similarity	NPC81042
0.5179	Remote Similarity	NPC139571
0.5179	Remote Similarity	NPC470718
0.5175	Remote Similarity	NPC198199
0.5158	Remote Similarity	NPC297987
0.5155	Remote Similarity	NPC191306
0.5155	Remote Similarity	NPC175107
0.5155	Remote Similarity	NPC285197
0.5149	Remote Similarity	NPC187379
0.5149	Remote Similarity	NPC139320
0.5146	Remote Similarity	NPC129264
0.5146	Remote Similarity	NPC204693
0.5143	Remote Similarity	NPC122467
0.5143	Remote Similarity	NPC37668
0.514	Remote Similarity	NPC287889
0.5138	Remote Similarity	NPC121703
0.5126	Remote Similarity	NPC21359
0.5126	Remote Similarity	NPC460984
0.5104	Remote Similarity	NPC27640
0.51	Remote Similarity	NPC254855
0.51	Remote Similarity	NPC94610
0.5098	Remote Similarity	NPC470405
0.5094	Remote Similarity	NPC486577
0.5085	Remote Similarity	NPC480472
0.5051	Remote Similarity	NPC223747
0.5051	Remote Similarity	NPC605784
0.505	Remote Similarity	NPC473682
0.5049	Remote Similarity	NPC22062
0.5049	Remote Similarity	NPC473634
0.5049	Remote Similarity	NPC102028
0.5049	Remote Similarity	NPC138811
0.5048	Remote Similarity	NPC12013
0.5048	Remote Similarity	NPC11432
0.5048	Remote Similarity	NPC477613
0.5046	Remote Similarity	NPC244875
0.5046	Remote Similarity	NPC214621
0.5046	Remote Similarity	NPC34267
0.5043	Remote Similarity	NPC120952
0.5042	Remote Similarity	NPC25946

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC541008 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5166
0.1-0.2	3913
0.2-0.3	59
0.3-0.4	5
0.4-0.5	2
0.5-0.6	4
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
0.6146	Remote Similarity	NPD6797	Phase 2
0.5743	Remote Similarity	NPD7054	Phase 4
0.5631	Remote Similarity	NPD7251	Phase 2
0.5566	Remote Similarity	NPD7808	Phase 3
0.5421	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