NPASS Compound

Natural Product: NPC488277

Natural Product ID	NPC488277
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KTADSKAWOWWNDC-OBQKRMBVSA-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 97102 0 0 0 0 0 0 0 0999 V2000 8.9303 -0.4755 -2.2485 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0168 -1.2369 -1.3040 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8304 -2.3072 -0.6228 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3780 -2.4432 0.8073 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8818 -2.2594 0.8688 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4640 -0.9355 0.3707 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3706 -1.0345 -0.4665 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3593 -0.1631 -0.2602 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6265 -0.1906 1.0475 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3274 -1.5779 1.4830 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8941 -2.0089 1.2910 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1927 -1.0614 0.3396 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3093 0.3343 0.8374 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6385 0.7296 1.1192 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8695 1.2141 -0.1633 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3187 2.4689 -0.0774 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3134 3.5087 -0.0503 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5324 3.2178 -0.0857 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9346 4.8258 0.0130 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8405 5.8624 0.0449 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4219 7.1872 0.1136 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0767 7.4386 0.1478 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8213 6.4081 0.1152 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4241 5.0596 0.0470 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2739 4.1014 0.0223 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9701 2.7734 -0.0365 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1471 1.9180 -0.0467 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2658 0.8002 0.6907 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4171 -0.0161 0.6170 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4342 0.3318 -0.2199 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3539 1.4639 -0.9927 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2077 2.2478 -0.8966 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4262 1.7562 -1.8202 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3721 2.9112 -2.6226 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5795 -0.4919 -0.2696 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6921 -1.5605 0.5885 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8666 -2.4589 0.4822 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9356 -3.2015 -0.7984 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2863 -3.8142 -1.0684 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4234 -3.2154 -0.3252 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0770 -2.4424 0.9049 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1595 -1.6178 1.2316 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0013 -1.6106 0.6355 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3115 -4.2325 0.0851 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5157 -3.6891 -2.4403 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9656 -4.2371 -0.7166 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3305 8.7865 0.2181 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1933 5.5690 0.0069 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1421 -1.4173 0.1871 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7844 -3.2874 0.7966 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6410 -1.7825 2.8511 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5163 -0.3215 -0.3756 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4172 -2.5705 2.1539 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0334 -1.5713 1.6696 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6931 -3.5474 -1.2920 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6671 -1.1770 -2.7226 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5207 0.2705 -1.6833 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3734 0.0057 -3.0790 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2249 -1.7161 -1.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9326 -2.0612 -0.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5595 -3.5062 1.1411 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4182 -3.0359 0.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2589 -0.1597 1.1672 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8041 0.9071 -0.3054 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6517 -0.2481 -1.1189 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3967 0.1812 1.8505 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9701 -2.2835 0.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3762 -1.9439 2.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6242 -1.1245 -0.6885 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7134 0.5061 1.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1561 8.0026 0.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8778 6.6150 0.1419 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5258 0.4728 1.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5034 -0.9067 1.2159 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1101 3.1310 -1.4779 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1445 2.8925 -3.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3575 3.0757 -3.0586 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5764 3.7918 -1.9450 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7850 -2.2242 0.3696 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4847 -1.2712 1.6652 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8461 -3.1513 1.3731 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5871 -2.5561 -1.6241 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2364 -4.9191 -0.8668 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9685 -2.5067 -1.0031 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7727 -3.0727 1.7769 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7984 -0.7270 1.4785 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9615 -3.7921 0.7038 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4481 -3.4093 -2.5947 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6436 -4.4974 -1.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8585 9.1262 1.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9303 6.2558 0.0936 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4861 -1.0400 -0.6515 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9051 -3.3506 -0.1936 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7113 -2.7586 3.0019 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6107 -1.8117 2.7639 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6399 -0.6848 1.6058 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1207 -3.4326 -2.2096 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 7 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 30 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 41 43 1 0 40 44 1 0 39 45 1 0 38 46 1 0 22 47 1 0 20 48 1 0 12 49 1 0 11 50 1 0 10 51 1 0 6 52 1 0 5 53 1 0 4 54 1 0 3 55 1 0 52 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 43 37 1 0 24 19 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 6 3 60 1 1 4 61 1 1 5 62 1 6 6 63 1 1 8 64 1 0 8 65 1 0 9 66 1 1 10 67 1 6 11 68 1 1 12 69 1 6 13 70 1 1 21 71 1 0 23 72 1 0 28 73 1 0 29 74 1 0 32 75 1 0 34 76 1 0 34 77 1 0 34 78 1 0 36 79 1 0 36 80 1 0 37 81 1 1 38 82 1 6 39 83 1 6 40 84 1 6 41 85 1 1 42 86 1 0 44 87 1 0 45 88 1 0 46 89 1 0 47 90 1 0 48 91 1 0 49 92 1 0 50 93 1 0 51 94 1 0 53 95 1 0 54 96 1 0 55 97 1 0 M END

Standard InCHIKey	KTADSKAWOWWNDC-OBQKRMBVSA-N
Standard InCHI	InChI=1S/C34H42O21/c1-10-20(37)24(41)28(45)33(51-10)50-9-18-22(39)26(43)29(46)34(54-18)55-31-23(40)19-13(36)6-12(35)7-16(19)52-30(31)11-3-4-14(15(5-11)48-2)49-8-17-21(38)25(42)27(44)32(47)53-17/h3-7,10,17-18,20-22,24-29,32-39,41-47H,8-9H2,1-2H3/t10-,17+,18+,20-,21+,22+,24+,25-,26-,27+,28+,29+,32+,33+,34-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)OC)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O)O2)O)O)O)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	786.22	Volume:	708.784 ? Van der Waals volume.
Dense:	1.109	LogP:	-0.297 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.555 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.753 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	36.0
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:	0.093	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.39	Fsp³:	0.559
MCE-18:	153.34 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.632	Fluc inhibitor:	0.303 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.665 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.51 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.043	Promiscuous compounds:	0.471

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.533	MDCK Permeability:	-5.116
Pgp-inhibitor:	0.0	Pgp-substrate:	0.989
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):	0.699
20% Bioavailability (F20%):	0.026	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	82.057%	Volume Distribution (VD):	-0.148
Fu:	16.094% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.74
BSEP inhibitor:	0.008

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.009
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.979
HLM stability:	0.025 ? 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):

0.684

Half-life (T1/2):

4.984

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.098
Human Hepatotoxicity (H-HT):	0.322	Drug-induced Liver Injury (DILI):	0.933
AMES Toxicity:	0.912	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	0.988
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.044	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.992
Hematotoxicity:	0.029	Drug-induced Nephrotoxicity:	0.726
Genotoxicity:	0.676	RPMI-8226 Immunitoxicity:	0.251
A549 Cytotoxicity:	0.118	Hek293 Cytotoxicity:	0.198
BCF:	0.362 ? 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:	3.062 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.704 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.764 ? 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
NPO40254	Opuntia humifusa	Species	Cactaceae	Eukaryota	Cladodes	n.a.	n.a.	PMID[32118424]
NPO40254	Opuntia humifusa	Species	Cactaceae	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 NPC488277 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	19173
0.1-0.2	27361
0.2-0.3	2524
0.3-0.4	418
0.4-0.5	228
0.5-0.6	108
0.6-0.7	26
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	Natural Product ID
0.7475	Intermediate Similarity	NPC473327
0.7327	Intermediate Similarity	NPC476472
0.7327	Intermediate Similarity	NPC294815
0.7327	Intermediate Similarity	NPC16194
0.7143	Intermediate Similarity	NPC173582
0.7143	Intermediate Similarity	NPC265885
0.7143	Intermediate Similarity	NPC181465
0.7143	Intermediate Similarity	NPC215710
0.7143	Intermediate Similarity	NPC473438
0.7143	Intermediate Similarity	NPC253788
0.7071	Intermediate Similarity	NPC203259
0.7071	Intermediate Similarity	NPC33054
0.7071	Intermediate Similarity	NPC176740
0.7071	Intermediate Similarity	NPC471725
0.7071	Intermediate Similarity	NPC134532
0.7071	Intermediate Similarity	NPC602582
0.697	Remote Similarity	NPC39834
0.6535	Remote Similarity	NPC187379
0.6306	Remote Similarity	NPC173837
0.6306	Remote Similarity	NPC477895
0.6286	Remote Similarity	NPC153755
0.6273	Remote Similarity	NPC89052
0.625	Remote Similarity	NPC156869
0.6216	Remote Similarity	NPC189564
0.6214	Remote Similarity	NPC471079
0.6214	Remote Similarity	NPC609888
0.619	Remote Similarity	NPC473571
0.619	Remote Similarity	NPC110941
0.6161	Remote Similarity	NPC292019
0.6161	Remote Similarity	NPC202908
0.6154	Remote Similarity	NPC67326
0.6132	Remote Similarity	NPC126784
0.6132	Remote Similarity	NPC241423
0.6126	Remote Similarity	NPC203145
0.61	Remote Similarity	NPC219904
0.6075	Remote Similarity	NPC12013
0.6075	Remote Similarity	NPC11432
0.6075	Remote Similarity	NPC477613
0.6055	Remote Similarity	NPC89127
0.6019	Remote Similarity	NPC116864
0.6019	Remote Similarity	NPC122467
0.6019	Remote Similarity	NPC244776
0.598	Remote Similarity	NPC223747
0.5943	Remote Similarity	NPC65563
0.5943	Remote Similarity	NPC470949
0.5888	Remote Similarity	NPC186816
0.5856	Remote Similarity	NPC221342
0.5856	Remote Similarity	NPC476470
0.5804	Remote Similarity	NPC602448
0.58	Remote Similarity	NPC265530
0.5785	Remote Similarity	NPC192539
0.578	Remote Similarity	NPC470443
0.5758	Remote Similarity	NPC111929
0.5758	Remote Similarity	NPC320283
0.5758	Remote Similarity	NPC41121
0.5739	Remote Similarity	NPC48984
0.5702	Remote Similarity	NPC241781
0.57	Remote Similarity	NPC127546
0.57	Remote Similarity	NPC57625
0.57	Remote Similarity	NPC173637
0.57	Remote Similarity	NPC317489
0.57	Remote Similarity	NPC223424
0.57	Remote Similarity	NPC600591
0.5625	Remote Similarity	NPC471669
0.56	Remote Similarity	NPC135599
0.56	Remote Similarity	NPC73855
0.56	Remote Similarity	NPC113968
0.56	Remote Similarity	NPC328940
0.56	Remote Similarity	NPC277174
0.56	Remote Similarity	NPC606877
0.5556	Remote Similarity	NPC217520
0.5556	Remote Similarity	NPC303694
0.5534	Remote Similarity	NPC472459
0.5487	Remote Similarity	NPC473073
0.5462	Remote Similarity	NPC139571
0.5455	Remote Similarity	NPC129264
0.5439	Remote Similarity	NPC287889
0.5439	Remote Similarity	NPC470449
0.5433	Remote Similarity	NPC473554
0.5429	Remote Similarity	NPC120099
0.541	Remote Similarity	NPC162394
0.5405	Remote Similarity	NPC488073
0.5405	Remote Similarity	NPC488074
0.5391	Remote Similarity	NPC470446
0.5364	Remote Similarity	NPC605592
0.5351	Remote Similarity	NPC470447
0.5351	Remote Similarity	NPC85751
0.5351	Remote Similarity	NPC19240
0.5351	Remote Similarity	NPC220173
0.534	Remote Similarity	NPC64305
0.5333	Remote Similarity	NPC175107
0.5327	Remote Similarity	NPC203050
0.5327	Remote Similarity	NPC225434
0.5327	Remote Similarity	NPC476215
0.531	Remote Similarity	NPC37668
0.531	Remote Similarity	NPC270448
0.5304	Remote Similarity	NPC470445
0.5285	Remote Similarity	NPC156785
0.5285	Remote Similarity	NPC474522
0.5278	Remote Similarity	NPC95866
0.5273	Remote Similarity	NPC67105
0.5268	Remote Similarity	NPC470125
0.5268	Remote Similarity	NPC475366
0.5263	Remote Similarity	NPC142142
0.5259	Remote Similarity	NPC223426
0.5238	Remote Similarity	NPC325555
0.5238	Remote Similarity	NPC226304
0.5225	Remote Similarity	NPC22062
0.5225	Remote Similarity	NPC473634
0.5225	Remote Similarity	NPC138811
0.5214	Remote Similarity	NPC214621
0.5214	Remote Similarity	NPC34267
0.5214	Remote Similarity	NPC81042
0.5203	Remote Similarity	NPC480445
0.5189	Remote Similarity	NPC60735
0.5189	Remote Similarity	NPC26230
0.5179	Remote Similarity	NPC204693
0.5175	Remote Similarity	NPC209296
0.5172	Remote Similarity	NPC292929
0.514	Remote Similarity	NPC609478
0.5135	Remote Similarity	NPC163242
0.5135	Remote Similarity	NPC272068
0.5135	Remote Similarity	NPC227508
0.5122	Remote Similarity	NPC488734
0.5122	Remote Similarity	NPC488735
0.5122	Remote Similarity	NPC488732
0.5122	Remote Similarity	NPC488738
0.512	Remote Similarity	NPC480444
0.5116	Remote Similarity	NPC487499
0.5096	Remote Similarity	NPC77672
0.5096	Remote Similarity	NPC133671
0.5096	Remote Similarity	NPC135391
0.5096	Remote Similarity	NPC78263
0.5096	Remote Similarity	NPC250069
0.5093	Remote Similarity	NPC209023
0.5089	Remote Similarity	NPC155877
0.5086	Remote Similarity	NPC76831
0.5048	Remote Similarity	NPC145038
0.5048	Remote Similarity	NPC56077
0.5048	Remote Similarity	NPC281131
0.5048	Remote Similarity	NPC253662
0.5048	Remote Similarity	NPC179950
0.5048	Remote Similarity	NPC88789
0.5048	Remote Similarity	NPC491374
0.5047	Remote Similarity	NPC159579
0.5045	Remote Similarity	NPC139320
0.5041	Remote Similarity	NPC25523
0.504	Remote Similarity	NPC488736
0.504	Remote Similarity	NPC488733
0.5037	Remote Similarity	NPC487500

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488277 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5379
0.1-0.2	3722
0.2-0.3	40
0.3-0.4	3
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
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
0.7071	Intermediate Similarity	NPD6797	Phase 2
0.6574	Remote Similarity	NPD7808	Phase 3
0.5625	Remote Similarity	NPD7251	Phase 2
0.5175	Remote Similarity	NPD7054	Phase 4

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