NPASS Compound

Natural Product: NPC188393

Natural Product ID	NPC188393
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Luteoside C
IUPAC Name	[(2R,3R,4S,5R,6R)-5-[(2S,3S,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3-hydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms	luteoside C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL502937
PubChem CID	10723884
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 100104 0 0 0 0 0 0 0 0999 V2000 2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1700 4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 6.4004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8991 6.9134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 8.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0105 9.3548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5691 8.9037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8296 10.3809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2391 10.8939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4996 12.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9091 12.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0582 11.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7977 10.4427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3882 9.9297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9468 9.4786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6863 8.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4677 12.4330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 5.8874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1700 4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9021 4.9224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3116 4.4094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6745 5.8649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0374 7.3203 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2593 2.9103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8174 2.4969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7971 4.2007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5597 6.2706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3191 5.5525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 7.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7981 8.5069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5377 9.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1281 10.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8676 11.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0167 12.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4263 12.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6867 10.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5753 13.3897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7562 14.4158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9791 3.6241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 -2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6132 0.1849 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2149 -1.6327 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7981 -1.9284 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4603 -1.6610 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -2.7762 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7580 -0.8169 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0865 1.9801 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5302 1.9190 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0880 5.4052 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1805 7.3646 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1705 5.0639 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0235 7.8099 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7181 7.9395 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6805 11.3451 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3505 13.3353 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1696 14.3614 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1277 8.4525 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1635 7.7409 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2091 8.2618 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4258 6.5241 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6168 11.4688 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5182 3.9308 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 1.8121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5152 5.1671 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8602 6.0015 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0749 5.3273 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1634 5.6821 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4793 7.7338 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7572 2.8318 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5198 1.4331 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5243 2.8887 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9862 6.7342 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5358 7.2902 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5623 7.1344 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2753 8.7674 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3209 8.2465 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9791 9.5330 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4581 12.4874 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0963 10.4353 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3148 14.8669 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9053 15.3800 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 4.1372 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5706 2.4621 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4176 -0.9951 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6386 -3.7404 0.0000 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 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 21 26 1 0 11 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 36 37 1 0 33 38 1 6 32 39 1 0 28 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 47 49 1 0 46 50 1 0 10 51 1 0 5 52 1 0 4 53 1 0 3 54 1 0 7 2 1 0 29 9 1 0 37 31 1 0 48 43 1 0 23 18 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 6 3 59 1 1 4 60 1 6 5 61 1 6 6 62 1 1 9 63 1 6 10 64 1 1 11 65 1 6 12 66 1 0 12 67 1 0 16 68 1 0 17 69 1 0 19 70 1 0 20 71 1 0 23 72 1 0 25 73 1 0 25 74 1 0 25 75 1 0 26 76 1 0 28 77 1 6 29 78 1 1 31 79 1 6 32 80 1 6 34 81 1 0 34 82 1 0 35 83 1 0 36 84 1 0 36 85 1 0 38 86 1 0 39 87 1 0 41 88 1 0 41 89 1 0 42 90 1 0 42 91 1 0 44 92 1 0 45 93 1 0 48 94 1 0 49 95 1 0 50 96 1 0 51 97 1 0 52 98 1 0 53 99 1 0 54100 1 0 M END

Standard InCHIKey	SSINDPAYUSUNDH-DAESBZSGSA-N
Standard InCHI	InChI=1S/C35H46O19/c1-16-25(41)27(43)28(44)32(51-16)53-29-26(42)23(13-49-24(40)8-5-17-4-7-20(38)22(12-17)47-2)52-33(48-10-9-18-3-6-19(37)21(39)11-18)30(29)54-34-31(45)35(46,14-36)15-50-34/h3-8,11-12,16,23,25-34,36-39,41-46H,9-10,13-15H2,1-2H3/b8-5+/t16-,23+,25-,26+,27+,28+,29-,30+,31+,32-,33+,34-,35+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)OC)O)O[C@H]([C@@H]1O[C@H]1[C@H]([C@@](CO)(CO1)O)O)OCCc1ccc(c(c1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	770.26	Volume:	717.056 ? Van der Waals volume.
Dense:	1.074	LogP:	0.338 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.84 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.45 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	31.0
TPSA:	293.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.055	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.332	Fsp³:	0.571
MCE-18:	129.836 ? 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:	0.67	Fluc inhibitor:	0.66 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.099 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.452 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.123	Promiscuous compounds:	0.42

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.555	MDCK Permeability:	-5.301
Pgp-inhibitor:	0.0	Pgp-substrate:	0.55
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):	0.991
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.071
Plasma Protein Binding (PPB):	67.431%	Volume Distribution (VD):	-0.42
Fu:	30.907% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.123
BSEP inhibitor:	0.001

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:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.095 ? 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):

1.271

Half-life (T1/2):

3.34

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.311
Human Hepatotoxicity (H-HT):	0.306	Drug-induced Liver Injury (DILI):	0.505
AMES Toxicity:	0.967	Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.039	Skin Sensitization:	1.0
Carcinogencity:	0.027	Eye Corrosion:	0.0
Eye Irritation:	0.055	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.993
Hematotoxicity:	0.148	Drug-induced Nephrotoxicity:	0.781
Genotoxicity:	0.218	RPMI-8226 Immunitoxicity:	0.187
A549 Cytotoxicity:	0.983	Hek293 Cytotoxicity:	0.691
BCF:	0.64 ? 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:	3.267 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.021 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.223 ? 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
NPO6610	Markhamia lutea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599250]
NPO6610	Markhamia lutea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6610	Markhamia lutea	Species	Bignoniaceae	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

Activity Type	# Activity
EC50	2
Ratio IC50/EC50	2

Activity Type	# Activity
Organism	2
Others	2

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
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	EC50	=	12.0	ug.mL-1	PMID[22260257]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	EC50	=	15.5	ug.mL-1	DOI[10.1039/C4MD00325J]
NPT2	Others	Unspecified	n.a.	Ratio IC50/EC50	>	28.0	n.a.	PMID[18993063]
NPT2	Others	Unspecified	n.a.	Ratio IC50/EC50	=	12.0	n.a.	PMID[18458127]

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 NPC188393 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	15856
0.1-0.2	29502
0.2-0.3	3871
0.3-0.4	482
0.4-0.5	94
0.5-0.6	39
0.6-0.7	8
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
0.8617	High Similarity	NPC141455
0.6514	Remote Similarity	NPC470934
0.6442	Remote Similarity	NPC600370
0.6389	Remote Similarity	NPC196063
0.6389	Remote Similarity	NPC604195
0.6321	Remote Similarity	NPC610636
0.6226	Remote Similarity	NPC100998
0.6216	Remote Similarity	NPC476398
0.604	Remote Similarity	NPC321638
0.5963	Remote Similarity	NPC300894
0.5963	Remote Similarity	NPC23845
0.5882	Remote Similarity	NPC64141
0.5728	Remote Similarity	NPC328273
0.5676	Remote Similarity	NPC259347
0.5648	Remote Similarity	NPC34587
0.5636	Remote Similarity	NPC34927
0.5607	Remote Similarity	NPC47471
0.5566	Remote Similarity	NPC265648
0.5565	Remote Similarity	NPC470933
0.5417	Remote Similarity	NPC476386
0.5366	Remote Similarity	NPC257970
0.5327	Remote Similarity	NPC68092
0.5315	Remote Similarity	NPC105005
0.5294	Remote Similarity	NPC94871
0.5283	Remote Similarity	NPC40305
0.5283	Remote Similarity	NPC205195
0.5253	Remote Similarity	NPC287597
0.5238	Remote Similarity	NPC235294
0.5229	Remote Similarity	NPC611289
0.5179	Remote Similarity	NPC252292
0.5149	Remote Similarity	NPC34293
0.514	Remote Similarity	NPC171134
0.5138	Remote Similarity	NPC76406
0.5133	Remote Similarity	NPC476397
0.5133	Remote Similarity	NPC119537
0.5098	Remote Similarity	NPC470881
0.5094	Remote Similarity	NPC81515
0.5093	Remote Similarity	NPC472350
0.5093	Remote Similarity	NPC197316
0.5093	Remote Similarity	NPC89105
0.5047	Remote Similarity	NPC226005
0.5046	Remote Similarity	NPC262182
0.5044	Remote Similarity	NPC205864
0.5044	Remote Similarity	NPC298257
0.5044	Remote Similarity	NPC247032
0.5044	Remote Similarity	NPC175214
0.5043	Remote Similarity	NPC106818
0.5043	Remote Similarity	NPC232992

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC188393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4856
0.1-0.2	4193
0.2-0.3	98
0.3-0.4	2
0.4-0.5	0
0.5-0.6	1
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
0.5093	Remote Similarity	NPD7266	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