NPASS Compound

Natural Product: NPC488075

Natural Product ID	NPC488075
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DOYPCFJFSWXZDY-MQEOUJFJSA-N
IUPAC Name	n.a.
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 91 96 0 0 0 0 0 0 0 0999 V2000 -5.7142 5.1662 -3.9399 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5569 5.0015 -3.1437 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4398 4.0388 -2.1660 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8174 4.2835 -0.8572 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7058 3.3330 0.1209 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2007 2.0679 -0.1718 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8228 1.8088 -1.4571 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9393 2.7876 -2.4575 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5410 2.4750 -3.7505 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3155 0.5675 -1.7626 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9632 0.3149 -2.9383 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1910 -0.4091 -0.7782 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5922 -0.0853 0.4717 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5329 -1.0184 1.5858 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3390 -2.3663 1.4945 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2568 -3.1676 2.6378 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3693 -2.6314 3.8934 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5650 -1.2757 3.9622 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6493 -0.4620 2.8683 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6804 -0.7356 5.2663 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2875 -3.4398 5.0427 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0823 1.1439 0.7367 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6846 -1.5967 -1.1427 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3416 -1.9449 -1.4442 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4500 -1.5962 -0.2959 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2212 -2.7115 0.3777 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1318 -4.0497 -0.1551 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3169 -4.0365 -1.6710 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8313 -5.4479 -2.0015 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0978 -5.5446 -3.3560 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2823 -3.1468 -2.0198 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2840 -4.6200 0.3729 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1575 -2.7054 1.7478 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5021 -0.6046 -0.7144 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.6304 -0.2008 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4069 1.3800 0.3646 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2051 1.7366 -0.8931 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3571 0.7434 -1.0262 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3226 0.9699 -0.0677 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3580 0.0860 -0.0390 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6949 0.6855 -0.4072 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6221 0.3708 0.7758 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0231 0.9310 2.0581 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5894 0.5042 2.1291 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4228 -0.5675 1.2178 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0328 2.3299 1.9890 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8686 0.9700 0.6125 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2247 0.0161 -1.4879 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1828 1.4508 -1.9933 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0743 1.4332 -1.3710 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5762 3.0429 -0.9694 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0091 2.5740 0.9514 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3178 5.5346 -0.5654 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6863 4.4949 -4.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7705 6.2075 -4.2889 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6346 4.9228 -3.3974 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9951 3.5157 1.1455 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7534 3.1200 -4.4925 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2700 -2.8146 0.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1033 -4.2264 2.4917 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8052 0.5965 3.0319 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4881 -1.0134 5.8235 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1442 -3.9634 5.2862 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9820 -1.1890 -2.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0851 -1.0011 0.4101 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3484 -2.5995 0.3310 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7357 -4.7705 0.0017 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6455 -3.9467 -2.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7126 -5.6983 -1.3760 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0125 -6.1554 -1.7757 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4425 -4.6795 -3.6688 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0907 -5.0921 1.2283 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6346 -2.6045 2.3359 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6426 0.7258 0.4490 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9800 0.8004 1.0913 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 -0.2580 -0.7932 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6975 0.7081 -2.0561 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1601 -0.7071 -0.7833 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6734 1.7770 -0.4785 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7813 -0.7100 0.9028 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6297 0.5417 2.8902 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4051 0.0885 3.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8811 1.3296 1.9045 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2397 2.6553 1.5008 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1685 0.9173 -0.3117 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7520 -0.7944 -1.1945 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1814 2.2859 -2.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3898 0.5013 -2.5050 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1828 3.5001 -1.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7432 3.2553 0.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8360 6.0658 0.1751 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 7 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 17 21 1 0 13 22 1 0 12 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 26 33 1 0 25 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 41 48 1 0 37 49 1 0 49 50 1 0 37 51 1 1 36 52 1 0 4 53 1 0 8 3 1 0 19 14 1 0 31 24 1 0 50 35 1 0 22 6 1 0 45 40 1 0 1 54 1 0 1 55 1 0 1 56 1 0 5 57 1 0 9 58 1 0 15 59 1 0 16 60 1 0 19 61 1 0 20 62 1 0 21 63 1 0 24 64 1 6 25 65 1 1 26 66 1 1 27 67 1 6 28 68 1 6 29 69 1 0 29 70 1 0 30 71 1 0 32 72 1 0 33 73 1 0 35 74 1 1 36 75 1 1 38 76 1 0 38 77 1 0 40 78 1 6 41 79 1 6 42 80 1 1 43 81 1 1 44 82 1 0 44 83 1 0 46 84 1 0 47 85 1 0 48 86 1 0 49 87 1 0 49 88 1 0 51 89 1 0 52 90 1 0 53 91 1 0 M END

Standard InCHIKey	DOYPCFJFSWXZDY-MQEOUJFJSA-N
Standard InCHI	InChI=1S/C32H38O21/c1-46-25-13(36)5-15-17(20(25)40)21(41)26(24(50-15)10-2-3-11(34)12(35)4-10)52-30-27(22(42)19(39)16(6-33)51-30)53-31-28(44)32(45,9-49-31)8-48-29-23(43)18(38)14(37)7-47-29/h2-5,14,16,18-19,22-23,27-31,33-40,42-45H,6-9H2,1H3/t14-,16+,18-,19-,22-,23+,27+,28-,29-,30-,31-,32+/m0/s1
SMILES	COc1c(cc2c(c1O)c(=O)c(c(c1ccc(c(c1)O)O)o2)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@@](CO[C@H]2[C@@H]([C@H]([C@H](CO2)O)O)O)(CO1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	758.19	Volume:	674.192 ? Van der Waals volume.
Dense:	1.125	LogP:	0.074 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.596 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.102 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	35.0
TPSA:	337.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	12.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.501	Fsp³:	0.531
MCE-18:	153.571 ? 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:	0.606	Fluc inhibitor:	0.265 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.741 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.603 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.134	Promiscuous compounds:	0.544

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.58	MDCK Permeability:	-5.269
Pgp-inhibitor:	0.0	Pgp-substrate:	0.724
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):	0.986
20% Bioavailability (F20%):	0.984	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.811
Plasma Protein Binding (PPB):	77.077%	Volume Distribution (VD):	-0.131
Fu:	21.187% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.011
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:	0.028
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.966
HLM stability:	0.929 ? 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):

1.097

Half-life (T1/2):

3.245

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.02
Human Hepatotoxicity (H-HT):	0.854	Drug-induced Liver Injury (DILI):	0.941
AMES Toxicity:	0.988	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.05	Skin Sensitization:	1.0
Carcinogencity:	0.119	Eye Corrosion:	0.0
Eye Irritation:	0.476	Respiratory Toxicity:	0.026
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.986
Hematotoxicity:	0.361	Drug-induced Nephrotoxicity:	0.576
Genotoxicity:	0.869	RPMI-8226 Immunitoxicity:	0.136
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.816
BCF:	0.353 ? 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:	2.803 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.492 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.592 ? 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
NPO40820	Corispermum marschallii	Species	n.a.	n.a.	Aerial Parts	n.a.	n.a.	PMID[30109803]

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
IC50	3

Activity Type	# Activity
Cell line	3

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
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	5400.0	nM	PMID[30109803]
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	24500.0	nM	PMID[30109803]
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	9700.0	nM	PMID[30109803]

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 NPC488075 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	22063
0.1-0.2	24365
0.2-0.3	2741
0.3-0.4	389
0.4-0.5	212
0.5-0.6	67
0.6-0.7	15
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8242	Intermediate Similarity	NPC480471
0.8242	Intermediate Similarity	NPC488076
0.7447	Intermediate Similarity	NPC255157
0.7447	Intermediate Similarity	NPC259896
0.6907	Remote Similarity	NPC470444
0.6804	Remote Similarity	NPC304741
0.6757	Remote Similarity	NPC480472
0.6667	Remote Similarity	NPC488074
0.6562	Remote Similarity	NPC254855
0.6562	Remote Similarity	NPC94610
0.6383	Remote Similarity	NPC42773
0.6383	Remote Similarity	NPC45522
0.6337	Remote Similarity	NPC488073
0.63	Remote Similarity	NPC155877
0.6204	Remote Similarity	NPC219043
0.6095	Remote Similarity	NPC76831
0.6055	Remote Similarity	NPC48984
0.6038	Remote Similarity	NPC292929
0.6	Remote Similarity	NPC473682
0.596	Remote Similarity	NPC170052
0.596	Remote Similarity	NPC135846
0.5856	Remote Similarity	NPC303694
0.5794	Remote Similarity	NPC473071
0.5794	Remote Similarity	NPC220173
0.5773	Remote Similarity	NPC305811
0.5773	Remote Similarity	NPC488080
0.5773	Remote Similarity	NPC169977
0.5728	Remote Similarity	NPC470405
0.5728	Remote Similarity	NPC163242
0.5728	Remote Similarity	NPC272068
0.5714	Remote Similarity	NPC126784
0.5714	Remote Similarity	NPC241423
0.5667	Remote Similarity	NPC21359
0.5667	Remote Similarity	NPC460984
0.5635	Remote Similarity	NPC487500
0.562	Remote Similarity	NPC487499
0.5591	Remote Similarity	NPC487501
0.5588	Remote Similarity	NPC95866
0.5566	Remote Similarity	NPC240306
0.5565	Remote Similarity	NPC487502
0.5537	Remote Similarity	NPC480470
0.5463	Remote Similarity	NPC122467
0.5455	Remote Similarity	NPC221342
0.5455	Remote Similarity	NPC470445
0.5455	Remote Similarity	NPC476470
0.5446	Remote Similarity	NPC101026
0.5446	Remote Similarity	NPC488077
0.5429	Remote Similarity	NPC67326
0.5417	Remote Similarity	NPC192539
0.5357	Remote Similarity	NPC14187
0.5294	Remote Similarity	NPC224530
0.5278	Remote Similarity	NPC253521
0.5278	Remote Similarity	NPC113836
0.5268	Remote Similarity	NPC470446
0.5268	Remote Similarity	NPC602448
0.5263	Remote Similarity	NPC473072
0.5258	Remote Similarity	NPC276222
0.5258	Remote Similarity	NPC274618
0.5258	Remote Similarity	NPC118284
0.5258	Remote Similarity	NPC608147
0.5234	Remote Similarity	NPC156869
0.5203	Remote Similarity	NPC25946
0.52	Remote Similarity	NPC145038
0.52	Remote Similarity	NPC56077
0.52	Remote Similarity	NPC281131
0.52	Remote Similarity	NPC253662
0.52	Remote Similarity	NPC179950
0.52	Remote Similarity	NPC88789
0.52	Remote Similarity	NPC491374
0.5196	Remote Similarity	NPC488071
0.5185	Remote Similarity	NPC473571
0.5185	Remote Similarity	NPC110941
0.5182	Remote Similarity	NPC32641
0.5182	Remote Similarity	NPC256188
0.5182	Remote Similarity	NPC35119
0.5172	Remote Similarity	NPC480441
0.513	Remote Similarity	NPC470451
0.5114	Remote Similarity	NPC163524
0.5098	Remote Similarity	NPC599850
0.5091	Remote Similarity	NPC245452
0.5089	Remote Similarity	NPC89127
0.5051	Remote Similarity	NPC67037
0.5051	Remote Similarity	NPC255615
0.5048	Remote Similarity	NPC476215
0.5047	Remote Similarity	NPC29958
0.5043	Remote Similarity	NPC89052

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5943
0.1-0.2	3173
0.2-0.3	27
0.3-0.4	5
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
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
		NPD

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