NPASS Compound

Natural Product: NPC480444

Natural Product ID	NPC480444
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ASOAXQKETNAUHE-JCULEJJSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102294706
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 91 95 0 0 0 0 0 0 0 0999 V2000 -5.4125 -2.5267 0.3414 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0944 -3.2710 0.3654 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3986 -4.7225 0.1496 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1365 -5.4504 -0.1731 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9179 -4.6519 0.2197 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9326 -3.2459 -0.3057 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2302 -2.8474 -0.6344 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3977 -2.3596 0.6487 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3160 -1.7209 0.1158 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9962 -2.0143 0.8455 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0864 -1.5277 -0.1147 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8198 -0.0539 -0.3269 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8932 0.4380 -1.2725 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1576 0.1472 -0.7507 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6963 0.6025 0.4262 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0214 1.3701 1.1464 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0553 0.2296 0.9013 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0345 1.3312 0.6483 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4194 0.9637 1.1243 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0147 1.7522 -0.7865 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3582 0.6868 -1.7466 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3081 0.9736 -2.9689 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7324 -0.6040 -1.4187 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6430 2.4254 1.4553 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5677 0.1937 -0.8376 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4150 -0.2211 0.0414 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7323 0.1646 -0.2829 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4213 1.1938 0.3665 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0447 0.8840 1.5844 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0049 -0.2605 2.0857 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7202 1.8880 2.2372 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3674 1.6844 3.4440 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0406 2.7033 4.0870 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0797 3.9617 3.5272 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4359 4.1565 2.3304 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7454 3.1387 1.6576 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1505 3.3611 0.5288 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4722 2.4459 -0.1778 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8689 2.8650 -1.4354 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3870 2.0673 -2.4242 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7965 2.5382 -3.5710 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6573 3.8912 -3.7885 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1401 4.7290 -2.7993 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7286 4.2396 -1.6557 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0071 6.0943 -3.0063 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0630 4.4038 -4.9412 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7639 4.9990 4.1792 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3364 0.4105 4.0257 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9291 -2.2434 -1.2965 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1739 -3.3734 1.0659 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8099 -5.3680 -0.2328 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0167 -5.7630 -1.5280 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1122 -5.2815 1.2019 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3104 -1.4375 0.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0307 -2.9759 1.1659 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9710 -2.7394 -0.6077 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6237 -3.0780 1.3427 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0620 -4.7753 -0.7545 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0537 -6.4256 0.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8100 -4.5811 1.3304 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3360 -3.1942 -1.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1165 -2.0643 -0.9467 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0754 -1.4070 1.7695 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0890 -1.6676 0.3108 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9864 0.4544 0.6507 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8175 -0.0983 -2.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8032 1.5289 -1.4646 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0024 0.0736 2.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3986 -0.7085 0.4706 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5280 -0.1473 0.9840 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5232 1.1852 2.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2067 1.4772 0.5388 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0004 2.1321 -1.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7082 2.6008 -0.9947 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3653 -1.1019 -2.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6848 2.0808 2.3886 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1841 0.2340 1.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5447 2.5522 5.0234 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4493 5.1332 1.8669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4891 1.0050 -2.3308 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4166 1.8833 -4.3493 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0967 4.9128 -0.8970 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8281 6.6648 -2.7477 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6402 4.6562 -5.7579 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4345 5.4892 3.5655 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1950 0.0395 4.4041 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0319 -3.2091 -1.0307 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8423 -3.4722 1.7785 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2379 -4.7901 -0.8164 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0544 -5.8922 -1.7733 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9320 -5.7645 0.9035 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 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 2 0 15 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 18 24 1 0 12 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 43 45 1 0 42 46 1 0 34 47 1 0 32 48 1 0 11 49 1 0 10 50 1 0 5 51 1 0 4 52 1 0 3 53 1 0 7 2 1 0 26 9 1 0 38 28 2 0 44 39 1 0 36 31 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 1 3 58 1 6 4 59 1 1 5 60 1 1 6 61 1 6 9 62 1 6 10 63 1 1 11 64 1 1 12 65 1 1 13 66 1 0 13 67 1 0 17 68 1 0 17 69 1 0 19 70 1 0 19 71 1 0 19 72 1 0 20 73 1 0 20 74 1 0 23 75 1 0 24 76 1 0 26 77 1 1 33 78 1 0 35 79 1 0 40 80 1 0 41 81 1 0 44 82 1 0 45 83 1 0 46 84 1 0 47 85 1 0 48 86 1 0 49 87 1 0 50 88 1 0 51 89 1 0 52 90 1 0 53 91 1 0 M END

Standard InCHIKey	ASOAXQKETNAUHE-JCULEJJSSA-N
Standard InCHI	InChI=1S/C33H38O20/c1-11-22(41)25(44)27(46)31(49-11)53-30-26(45)23(42)18(10-48-20(40)9-33(2,47)8-19(38)39)51-32(30)52-29-24(43)21-16(37)6-13(34)7-17(21)50-28(29)12-3-4-14(35)15(36)5-12/h3-7,11,18,22-23,25-27,30-32,34-37,41-42,44-47H,8-10H2,1-2H3,(H,38,39)/t11-,18+,22-,23-,25+,26-,27+,30+,31-,32-,33?/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H]([C@@H](COC(=O)CC(C)(CC(=O)O)O)O[C@H]1Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	754.2	Volume:	685.982 ? Van der Waals volume.
Dense:	1.099	LogP:	0.86 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.317 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.536 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	32.0
TPSA:	333.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	11.0	Rings:	5.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.078	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.218	Fsp³:	0.485
MCE-18:	136.327 ? 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:	0.471	Fluc inhibitor:	0.308 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.785 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.647 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.073	Promiscuous compounds:	0.564

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.415	MDCK Permeability:	-5.278
Pgp-inhibitor:	0.0	Pgp-substrate:	0.086
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):	0.981
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.193
Plasma Protein Binding (PPB):	78.356%	Volume Distribution (VD):	-0.402
Fu:	17.345% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.789
HLM stability:	0.011 ? 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):

1.701

Half-life (T1/2):

4.117

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.021
Human Hepatotoxicity (H-HT):	0.451	Drug-induced Liver Injury (DILI):	0.973
AMES Toxicity:	0.686	Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.034	Skin Sensitization:	1.0
Carcinogencity:	0.037	Eye Corrosion:	0.0
Eye Irritation:	0.573	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.979
Hematotoxicity:	0.085	Drug-induced Nephrotoxicity:	0.812
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.238	Hek293 Cytotoxicity:	0.248
BCF:	0.325 ? 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:	2.704 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.104 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.287 ? 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
NPO40038	Astragalus monspessulanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26558405]

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

Activity Type	# Activity
Activity	1

Activity Type	# Activity
Cell line	1

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
NPT984	Cell line	Hepatocyte	n.a.	Activity	=	182.0	%	PMID[26558405]

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 NPC480444 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	10506
0.1-0.2	34828
0.2-0.3	3866
0.3-0.4	298
0.4-0.5	170
0.5-0.6	116
0.6-0.7	58
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC480445
0.8037	Intermediate Similarity	NPC209550
0.7778	Intermediate Similarity	NPC122467
0.7327	Intermediate Similarity	NPC12013
0.7327	Intermediate Similarity	NPC11432
0.7327	Intermediate Similarity	NPC477613
0.729	Intermediate Similarity	NPC303694
0.7282	Intermediate Similarity	NPC89127
0.7143	Intermediate Similarity	NPC95866
0.7143	Intermediate Similarity	NPC602448
0.703	Intermediate Similarity	NPC155877
0.7009	Intermediate Similarity	NPC89052
0.6887	Remote Similarity	NPC221342
0.6887	Remote Similarity	NPC476470
0.67	Remote Similarity	NPC476215
0.6638	Remote Similarity	NPC488737
0.6609	Remote Similarity	NPC162394
0.6609	Remote Similarity	NPC488740
0.6609	Remote Similarity	NPC488736
0.6609	Remote Similarity	NPC488733
0.6602	Remote Similarity	NPC163242
0.6602	Remote Similarity	NPC272068
0.6577	Remote Similarity	NPC173837
0.6557	Remote Similarity	NPC487502
0.6538	Remote Similarity	NPC203259
0.6538	Remote Similarity	NPC33054
0.6538	Remote Similarity	NPC176740
0.6538	Remote Similarity	NPC471725
0.6538	Remote Similarity	NPC134532
0.6538	Remote Similarity	NPC602582
0.65	Remote Similarity	NPC487499
0.6471	Remote Similarity	NPC254855
0.6471	Remote Similarity	NPC94610
0.633	Remote Similarity	NPC220173
0.6311	Remote Similarity	NPC116864
0.6311	Remote Similarity	NPC244776
0.6311	Remote Similarity	NPC473554
0.6303	Remote Similarity	NPC192539
0.6303	Remote Similarity	NPC175429
0.6299	Remote Similarity	NPC487501
0.6293	Remote Similarity	NPC488734
0.6293	Remote Similarity	NPC488735
0.6293	Remote Similarity	NPC488739
0.6293	Remote Similarity	NPC488732
0.6293	Remote Similarity	NPC488738
0.6273	Remote Similarity	NPC292929
0.625	Remote Similarity	NPC121703
0.622	Remote Similarity	NPC487500
0.6182	Remote Similarity	NPC471669
0.6168	Remote Similarity	NPC255157
0.6168	Remote Similarity	NPC259896
0.6148	Remote Similarity	NPC21359
0.6148	Remote Similarity	NPC460984
0.6132	Remote Similarity	NPC173582
0.6132	Remote Similarity	NPC265885
0.6132	Remote Similarity	NPC181465
0.6132	Remote Similarity	NPC215710
0.6132	Remote Similarity	NPC473438
0.6132	Remote Similarity	NPC253788
0.6091	Remote Similarity	NPC142142
0.6087	Remote Similarity	NPC480441
0.6075	Remote Similarity	NPC605592
0.6058	Remote Similarity	NPC170052
0.6058	Remote Similarity	NPC135846
0.6	Remote Similarity	NPC127546
0.6	Remote Similarity	NPC57625
0.6	Remote Similarity	NPC173637
0.6	Remote Similarity	NPC317489
0.6	Remote Similarity	NPC223424
0.6	Remote Similarity	NPC600591
0.5984	Remote Similarity	NPC480442
0.5984	Remote Similarity	NPC249560
0.595	Remote Similarity	NPC138990
0.5946	Remote Similarity	NPC97119
0.5926	Remote Similarity	NPC156869
0.5893	Remote Similarity	NPC476472
0.5893	Remote Similarity	NPC294815
0.5893	Remote Similarity	NPC16194
0.5862	Remote Similarity	NPC292019
0.5862	Remote Similarity	NPC202908
0.5856	Remote Similarity	NPC473327
0.5833	Remote Similarity	NPC470405
0.5833	Remote Similarity	NPC67326
0.5833	Remote Similarity	NPC39834
0.5812	Remote Similarity	NPC25523
0.5806	Remote Similarity	NPC25946
0.578	Remote Similarity	NPC304741
0.5763	Remote Similarity	NPC277532
0.5703	Remote Similarity	NPC30011
0.569	Remote Similarity	NPC203145
0.5676	Remote Similarity	NPC153755
0.5673	Remote Similarity	NPC216496
0.5664	Remote Similarity	NPC603079
0.5652	Remote Similarity	NPC223426
0.5652	Remote Similarity	NPC218161
0.5645	Remote Similarity	NPC480443
0.5619	Remote Similarity	NPC235260
0.5619	Remote Similarity	NPC155763
0.5588	Remote Similarity	NPC111929
0.5588	Remote Similarity	NPC320283
0.5588	Remote Similarity	NPC41121
0.5586	Remote Similarity	NPC35167
0.5581	Remote Similarity	NPC72554
0.5575	Remote Similarity	NPC37668
0.5565	Remote Similarity	NPC241781
0.5547	Remote Similarity	NPC275977
0.5545	Remote Similarity	NPC471748
0.5536	Remote Similarity	NPC240306
0.5528	Remote Similarity	NPC156785
0.5508	Remote Similarity	NPC189564
0.5481	Remote Similarity	NPC145038
0.5481	Remote Similarity	NPC56077
0.5481	Remote Similarity	NPC281131
0.5481	Remote Similarity	NPC253662
0.5481	Remote Similarity	NPC179950
0.5481	Remote Similarity	NPC88789
0.5481	Remote Similarity	NPC491374
0.5478	Remote Similarity	NPC473071
0.5472	Remote Similarity	NPC175107
0.547	Remote Similarity	NPC81042
0.5462	Remote Similarity	NPC219043
0.5455	Remote Similarity	NPC471079
0.5455	Remote Similarity	NPC29958
0.5446	Remote Similarity	NPC470444
0.5426	Remote Similarity	NPC231787
0.5421	Remote Similarity	NPC224530
0.5414	Remote Similarity	NPC97817
0.5398	Remote Similarity	NPC126784
0.5398	Remote Similarity	NPC241423
0.5398	Remote Similarity	NPC154741
0.537	Remote Similarity	NPC223747
0.5345	Remote Similarity	NPC85751
0.5345	Remote Similarity	NPC76831
0.5345	Remote Similarity	NPC19240
0.534	Remote Similarity	NPC67037
0.534	Remote Similarity	NPC255615
0.5339	Remote Similarity	NPC14187
0.5327	Remote Similarity	NPC219904
0.5315	Remote Similarity	NPC609888
0.531	Remote Similarity	NPC129264
0.5304	Remote Similarity	NPC32641
0.5304	Remote Similarity	NPC256188
0.5304	Remote Similarity	NPC270448
0.5288	Remote Similarity	NPC135599
0.5288	Remote Similarity	NPC73855
0.5288	Remote Similarity	NPC113968
0.5288	Remote Similarity	NPC328940
0.5288	Remote Similarity	NPC277174
0.5288	Remote Similarity	NPC606877
0.5263	Remote Similarity	NPC253521
0.5263	Remote Similarity	NPC113836
0.5243	Remote Similarity	NPC276222
0.5243	Remote Similarity	NPC274618
0.5243	Remote Similarity	NPC118284
0.5243	Remote Similarity	NPC608147
0.5221	Remote Similarity	NPC65563
0.5221	Remote Similarity	NPC470949
0.521	Remote Similarity	NPC214621
0.521	Remote Similarity	NPC34267
0.5179	Remote Similarity	NPC139320
0.5172	Remote Similarity	NPC35119
0.5164	Remote Similarity	NPC217520
0.5159	Remote Similarity	NPC474522
0.5138	Remote Similarity	NPC259957
0.513	Remote Similarity	NPC296018
0.5094	Remote Similarity	NPC77672
0.5094	Remote Similarity	NPC133671
0.5094	Remote Similarity	NPC135391
0.5094	Remote Similarity	NPC78263
0.5094	Remote Similarity	NPC250069
0.5086	Remote Similarity	NPC245452
0.5086	Remote Similarity	NPC470443
0.5085	Remote Similarity	NPC473073
0.5082	Remote Similarity	NPC48984
0.5081	Remote Similarity	NPC139571
0.5079	Remote Similarity	NPC298666
0.5071	Remote Similarity	NPC33083
0.5046	Remote Similarity	NPC60735
0.5046	Remote Similarity	NPC26230
0.5044	Remote Similarity	NPC258044
0.5044	Remote Similarity	NPC217387
0.5043	Remote Similarity	NPC144097
0.5043	Remote Similarity	NPC473571
0.5043	Remote Similarity	NPC110941
0.5043	Remote Similarity	NPC186816
0.5042	Remote Similarity	NPC470445

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480444 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3481
0.1-0.2	5580
0.2-0.3	80
0.3-0.4	6
0.4-0.5	1
0.5-0.6	1
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
0.6538	Remote Similarity	NPD6797	Phase 2
0.5214	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