NPASS Compound

Natural Product: NPC571058

Natural Product ID	NPC571058
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-7-[(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-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-7-[(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-methyl-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 75 79 0 0 0 0 0 0 0 0999 V2000 -8.6366 -2.0882 0.4567 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7472 -1.3870 1.3289 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5046 -0.9767 0.8541 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3172 0.2580 0.3194 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3367 1.2929 0.1790 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0218 2.4025 -0.6031 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9048 3.4479 -0.7623 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1420 3.4487 -0.1568 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0450 4.4847 -0.3016 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4743 2.3621 0.6216 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5615 1.3123 0.7694 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0834 0.5175 -0.1063 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0756 -0.2918 -0.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8286 0.0657 -0.5175 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7107 -0.7669 -0.4803 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5022 -0.3185 -0.9736 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6521 -1.0468 -0.9870 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7050 -0.4259 -0.2599 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5870 -1.4487 0.0760 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8024 -0.9460 0.8019 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5325 -0.0365 0.0507 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6478 0.4410 0.6850 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6382 1.8300 0.8628 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7592 2.1110 1.6743 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6262 3.4021 2.4071 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9608 2.0583 0.7659 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7618 2.9698 -0.2709 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1156 0.6617 0.2623 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9239 0.7231 -0.8935 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8504 -0.0172 -0.1142 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0010 -1.3881 0.1571 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9281 -2.1618 -1.2077 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2427 -2.5324 -1.3090 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6026 -1.2824 -2.4216 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2422 -0.0657 -2.3667 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0949 -1.1641 -2.4621 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6031 -2.3529 -3.0071 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9025 -2.0116 0.0621 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1353 -2.4145 0.5436 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2957 -3.6805 1.0862 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2207 -1.5523 0.4862 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4595 -1.9072 0.9496 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6561 -3.0431 1.4501 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5732 -1.5138 0.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1778 -2.2519 -0.5360 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8558 -3.0762 0.9362 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0577 2.4229 -1.0881 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6429 4.3000 -1.3729 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9655 5.1994 -1.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4345 2.3430 1.1028 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8609 0.5072 1.4062 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7262 1.0603 -0.9376 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5490 -2.0384 -0.5656 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0451 -2.1346 0.7592 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4226 -1.7827 1.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4434 -0.4009 1.7011 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7858 0.0139 1.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8807 1.2762 2.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8534 4.2901 1.8038 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3597 3.3856 3.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6245 3.4330 2.8804 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8924 2.3150 1.3283 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2193 2.5733 -1.0040 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7023 0.0565 0.9907 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5981 0.0921 -1.5818 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6109 0.0662 -1.1886 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8157 -1.5618 0.6987 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2923 -3.0582 -1.2886 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3344 -3.2644 -1.9693 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9720 -1.8570 -3.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5817 0.6505 -2.4630 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7636 -0.2784 -3.0368 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2136 -2.6652 -2.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1000 -2.7191 0.1322 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8541 -3.8649 1.9805 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 8 10 1 0 10 11 2 0 4 12 1 0 12 13 1 0 13 14 2 0 14 15 1 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 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 19 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 15 38 2 0 38 39 1 0 39 40 1 0 39 41 2 0 41 42 1 0 42 43 2 0 42 3 1 0 11 5 1 0 41 13 1 0 36 17 1 0 30 22 1 0 1 44 1 0 1 45 1 0 1 46 1 0 6 47 1 0 7 48 1 0 9 49 1 0 10 50 1 0 11 51 1 0 14 52 1 0 17 53 1 1 19 54 1 1 20 55 1 0 20 56 1 0 22 57 1 1 24 58 1 1 25 59 1 0 25 60 1 0 25 61 1 0 26 62 1 1 27 63 1 0 28 64 1 1 29 65 1 0 30 66 1 6 31 67 1 0 32 68 1 6 33 69 1 0 34 70 1 6 35 71 1 0 36 72 1 6 37 73 1 0 38 74 1 0 40 75 1 0 M END

Standard InCHIKey	DDCXRGLXWQTCFL-MPDZKVBKSA-N
Standard InCHI	InChI=1S/C28H32O15/c1-10-18(31)21(34)23(36)27(40-10)39-9-16-19(32)22(35)24(37)28(43-16)41-13-7-14(30)17-15(8-13)42-25(26(38-2)20(17)33)11-3-5-12(29)6-4-11/h3-8,10,16,18-19,21-24,27-32,34-37H,9H2,1-2H3/t10-,16-,18+,19+,21+,22+,23-,24-,27-,28-/m1/s1
SMILES	COC1=C(C2=CC=C(O)C=C2)OC2=CC(O[C@@H]3O[C@H](CO[C@@H]4O[C@H](C)[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H](O)[C@H]3O)=CC(O)=C2C1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.17	Volume:	560.823 ? Van der Waals volume.
Dense:	1.084	LogP:	1.278 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.644 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.485 ? 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:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.677	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:	0	PAINS Alert:	0
Colloidal aggregators:	0.582	Fluc inhibitor:	0.261 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.775 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.768 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.061	Promiscuous compounds:	0.451

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.393	MDCK Permeability:	-5.279
Pgp-inhibitor:	0.0	Pgp-substrate:	0.961
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):	0.953
20% Bioavailability (F20%):	0.577	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.755
Plasma Protein Binding (PPB):	85.679%	Volume Distribution (VD):	-0.073
Fu:	12.642% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.81
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.26
BSEP inhibitor:	0.005

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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.052
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.889
HLM stability:	0.602 ? 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):

1.354

Half-life (T1/2):

2.928

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.107
Human Hepatotoxicity (H-HT):	0.544	Drug-induced Liver Injury (DILI):	0.979
AMES Toxicity:	0.98	Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.043	Skin Sensitization:	1.0
Carcinogencity:	0.234	Eye Corrosion:	0.0
Eye Irritation:	0.356	Respiratory Toxicity:	0.052
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.856
Hematotoxicity:	0.458	Drug-induced Nephrotoxicity:	0.522
Genotoxicity:	0.981	RPMI-8226 Immunitoxicity:	0.216
A549 Cytotoxicity:	0.953	Hek293 Cytotoxicity:	0.874
BCF:	0.444 ? 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:	3.043 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.511 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.611 ? 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
NPO25149	Centaurea arguta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18976	Centaurea arbutifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25149	Centaurea arguta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18976	Centaurea arbutifolia	Species	Asteraceae	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

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 NPC571058 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	19426
0.1-0.2	26205
0.2-0.3	3158
0.3-0.4	532
0.4-0.5	285
0.5-0.6	115
0.6-0.7	51
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC186816
0.7955	Intermediate Similarity	NPC142142
0.7882	Intermediate Similarity	NPC44931
0.7875	Intermediate Similarity	NPC46420
0.7674	Intermediate Similarity	NPC173582
0.7674	Intermediate Similarity	NPC265885
0.7674	Intermediate Similarity	NPC181465
0.7674	Intermediate Similarity	NPC215710
0.7674	Intermediate Similarity	NPC473438
0.7674	Intermediate Similarity	NPC253788
0.766	Intermediate Similarity	NPC25523
0.7625	Intermediate Similarity	NPC249281
0.75	Intermediate Similarity	NPC473571
0.75	Intermediate Similarity	NPC110941
0.7471	Intermediate Similarity	NPC67105
0.7412	Intermediate Similarity	NPC276377
0.7386	Intermediate Similarity	NPC210073
0.7191	Intermediate Similarity	NPC22062
0.7191	Intermediate Similarity	NPC65563
0.7191	Intermediate Similarity	NPC473634
0.7191	Intermediate Similarity	NPC470949
0.7191	Intermediate Similarity	NPC138811
0.7143	Intermediate Similarity	NPC470443
0.7093	Intermediate Similarity	NPC116458
0.7093	Intermediate Similarity	NPC246943
0.7065	Intermediate Similarity	NPC209296
0.7024	Intermediate Similarity	NPC271692
0.7	Intermediate Similarity	NPC203259
0.7	Intermediate Similarity	NPC33054
0.7	Intermediate Similarity	NPC176740
0.7	Intermediate Similarity	NPC471725
0.7	Intermediate Similarity	NPC134532
0.7	Intermediate Similarity	NPC150164
0.7	Intermediate Similarity	NPC602582
0.6939	Remote Similarity	NPC480441
0.6915	Remote Similarity	NPC476472
0.6915	Remote Similarity	NPC294815
0.6915	Remote Similarity	NPC16194
0.6889	Remote Similarity	NPC227508
0.6882	Remote Similarity	NPC32641
0.6882	Remote Similarity	NPC256188
0.6848	Remote Similarity	NPC126784
0.6848	Remote Similarity	NPC240306
0.6848	Remote Similarity	NPC241423
0.6813	Remote Similarity	NPC303913
0.6804	Remote Similarity	NPC121703
0.6706	Remote Similarity	NPC297987
0.6702	Remote Similarity	NPC72016
0.6702	Remote Similarity	NPC35119
0.6702	Remote Similarity	NPC473327
0.6593	Remote Similarity	NPC471079
0.6562	Remote Similarity	NPC473073
0.6522	Remote Similarity	NPC39834
0.6512	Remote Similarity	NPC158674
0.6495	Remote Similarity	NPC101636
0.6477	Remote Similarity	NPC611303
0.6437	Remote Similarity	NPC84362
0.6421	Remote Similarity	NPC12013
0.6421	Remote Similarity	NPC11432
0.6421	Remote Similarity	NPC477613
0.6395	Remote Similarity	NPC108831
0.6395	Remote Similarity	NPC182634
0.6333	Remote Similarity	NPC605784
0.6279	Remote Similarity	NPC331652
0.6262	Remote Similarity	NPC209550
0.6238	Remote Similarity	NPC189564
0.62	Remote Similarity	NPC14187
0.6162	Remote Similarity	NPC470449
0.6162	Remote Similarity	NPC221342
0.6162	Remote Similarity	NPC476470
0.6146	Remote Similarity	NPC64425
0.6139	Remote Similarity	NPC203145
0.6122	Remote Similarity	NPC486577
0.6105	Remote Similarity	NPC156869
0.61	Remote Similarity	NPC602448
0.6092	Remote Similarity	NPC111929
0.6092	Remote Similarity	NPC320283
0.6092	Remote Similarity	NPC41121
0.6061	Remote Similarity	NPC470447
0.6042	Remote Similarity	NPC204693
0.6023	Remote Similarity	NPC238376
0.602	Remote Similarity	NPC473623
0.6	Remote Similarity	NPC298171
0.6	Remote Similarity	NPC67326
0.6	Remote Similarity	NPC275454
0.5979	Remote Similarity	NPC488073
0.5979	Remote Similarity	NPC488074
0.5974	Remote Similarity	NPC146679
0.596	Remote Similarity	NPC488089
0.5955	Remote Similarity	NPC136042
0.5938	Remote Similarity	NPC479405
0.5918	Remote Similarity	NPC65711
0.5905	Remote Similarity	NPC277532
0.5895	Remote Similarity	NPC187379
0.5876	Remote Similarity	NPC479404
0.5859	Remote Similarity	NPC122467
0.5859	Remote Similarity	NPC606657
0.5843	Remote Similarity	NPC289667
0.5843	Remote Similarity	NPC19709
0.5825	Remote Similarity	NPC89052
0.5825	Remote Similarity	NPC11468
0.5818	Remote Similarity	NPC138990
0.5816	Remote Similarity	NPC64051
0.5789	Remote Similarity	NPC251417
0.5784	Remote Similarity	NPC135358
0.5773	Remote Similarity	NPC473512
0.5773	Remote Similarity	NPC129827
0.5766	Remote Similarity	NPC175429
0.5743	Remote Similarity	NPC89127
0.5728	Remote Similarity	NPC470455
0.5714	Remote Similarity	NPC292019
0.5714	Remote Similarity	NPC202908
0.5714	Remote Similarity	NPC27640
0.5714	Remote Similarity	NPC173837
0.5688	Remote Similarity	NPC298666
0.5684	Remote Similarity	NPC116864
0.5684	Remote Similarity	NPC244776
0.5657	Remote Similarity	NPC153755
0.5652	Remote Similarity	NPC27942
0.5644	Remote Similarity	NPC270675
0.5644	Remote Similarity	NPC195685
0.5631	Remote Similarity	NPC470446
0.5604	Remote Similarity	NPC323593
0.5604	Remote Similarity	NPC203500
0.56	Remote Similarity	NPC479403
0.5588	Remote Similarity	NPC80068
0.5579	Remote Similarity	NPC476215
0.5566	Remote Similarity	NPC480796
0.5566	Remote Similarity	NPC472993
0.5556	Remote Similarity	NPC129264
0.5543	Remote Similarity	NPC24043
0.5534	Remote Similarity	NPC470445
0.5521	Remote Similarity	NPC172807
0.5517	Remote Similarity	NPC473554
0.5517	Remote Similarity	NPC483159
0.5517	Remote Similarity	NPC483160
0.5514	Remote Similarity	NPC473644
0.55	Remote Similarity	NPC470125
0.55	Remote Similarity	NPC475366
0.5495	Remote Similarity	NPC127546
0.5495	Remote Similarity	NPC39360
0.5495	Remote Similarity	NPC57625
0.5495	Remote Similarity	NPC29763
0.5495	Remote Similarity	NPC173637
0.5495	Remote Similarity	NPC210003
0.5495	Remote Similarity	NPC317489
0.5495	Remote Similarity	NPC223424
0.5495	Remote Similarity	NPC600591
0.5484	Remote Similarity	NPC59534
0.5481	Remote Similarity	NPC470450
0.5481	Remote Similarity	NPC472994
0.5474	Remote Similarity	NPC223747
0.5474	Remote Similarity	NPC99957
0.5463	Remote Similarity	NPC311850
0.5455	Remote Similarity	NPC65003
0.5437	Remote Similarity	NPC85751
0.5437	Remote Similarity	NPC19240
0.5408	Remote Similarity	NPC609888
0.5405	Remote Similarity	NPC198199
0.5392	Remote Similarity	NPC270448
0.5392	Remote Similarity	NPC229409
0.5385	Remote Similarity	NPC292929
0.5385	Remote Similarity	NPC473043
0.5385	Remote Similarity	NPC36138
0.5376	Remote Similarity	NPC305811
0.537	Remote Similarity	NPC303694
0.537	Remote Similarity	NPC164704
0.5361	Remote Similarity	NPC265115
0.5357	Remote Similarity	NPC474522
0.5357	Remote Similarity	NPC470717
0.5354	Remote Similarity	NPC163242
0.5354	Remote Similarity	NPC272068
0.5351	Remote Similarity	NPC192539
0.5347	Remote Similarity	NPC46202
0.5326	Remote Similarity	NPC77672
0.5326	Remote Similarity	NPC133671
0.5326	Remote Similarity	NPC135391
0.5326	Remote Similarity	NPC78263
0.5326	Remote Similarity	NPC250069
0.5326	Remote Similarity	NPC348541
0.5315	Remote Similarity	NPC68592
0.531	Remote Similarity	NPC470720
0.5294	Remote Similarity	NPC469622
0.5283	Remote Similarity	NPC214621
0.5283	Remote Similarity	NPC34267
0.5269	Remote Similarity	NPC265530
0.5269	Remote Similarity	NPC277205
0.5269	Remote Similarity	NPC37919
0.5263	Remote Similarity	NPC120952
0.5263	Remote Similarity	NPC219904
0.5263	Remote Similarity	NPC241781
0.5258	Remote Similarity	NPC190003
0.5248	Remote Similarity	NPC470444
0.5221	Remote Similarity	NPC162394
0.5213	Remote Similarity	NPC488080
0.5213	Remote Similarity	NPC169977
0.5208	Remote Similarity	NPC181616
0.5204	Remote Similarity	NPC477848
0.5185	Remote Similarity	NPC188871
0.5185	Remote Similarity	NPC470416

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC571058 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5209
0.1-0.2	3879
0.2-0.3	54
0.3-0.4	1
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
0.7-0.8	3
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
0.7667	Intermediate Similarity	NPD7251	Phase 2
0.7065	Intermediate Similarity	NPD7054	Phase 4
0.7	Intermediate Similarity	NPD6797	Phase 2
0.6979	Remote Similarity	NPD7808	Phase 3
0.5524	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