NPASS Compound

Natural Product: NPC305444

Natural Product ID	NPC305444
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RDGWQQQKUDXGRS-WGSSIDGDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101188264
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 102107 0 0 0 0 0 0 0 0999 V2000 -6.7337 2.1057 -0.8717 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6646 0.9954 -0.6903 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4725 -0.2554 -0.5796 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1709 -0.1776 0.7704 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1938 -0.2077 1.9058 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9676 0.2359 3.1552 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9621 0.5745 1.7211 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7495 1.2974 0.4441 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2958 1.2323 0.0272 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5274 2.1828 0.5354 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0740 2.2911 0.2432 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6191 0.8984 -0.1190 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8854 0.8303 -0.1593 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5447 2.0781 -0.6393 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3188 0.6809 1.3095 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7438 0.3811 1.5103 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3821 -0.6386 0.6354 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7362 -0.8427 -0.6949 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7736 -2.3492 -1.0406 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5296 -0.1854 -1.8020 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9837 -0.3318 -3.0644 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3131 -0.4384 -0.7811 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6987 -0.5791 -2.1430 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8035 -0.8308 -1.8960 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3612 0.4498 -1.3133 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3781 1.4517 -2.4527 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8128 0.1680 -0.8920 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8193 -1.2165 -0.2911 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7400 0.1257 -2.0866 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8806 1.0766 -1.9816 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7370 -0.4337 0.4187 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5689 -1.4003 0.9196 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4222 -2.1000 -0.0614 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5854 -1.2198 -0.5457 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3797 -0.9158 0.6887 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4908 -0.2708 1.7199 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2992 1.1372 1.2856 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2819 1.8951 0.9960 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0334 1.6620 1.1863 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3051 -0.8619 1.9291 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8767 -2.0889 1.2513 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1500 -0.0962 -1.1980 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0353 -3.2109 0.5303 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8721 -1.6492 2.1568 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3756 -2.5892 1.4895 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9821 -2.0097 3.1624 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5982 1.7321 -1.4199 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0093 2.5228 0.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2942 2.9626 -1.4347 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3221 -0.1607 -1.3282 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9474 -1.1952 -0.7284 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8810 -1.0295 0.7886 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7677 0.7486 0.7871 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8061 -0.4610 3.3529 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3628 1.2479 3.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2414 0.1295 4.0053 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0752 -0.0801 1.9990 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9178 1.3165 2.5878 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9783 2.3939 0.6751 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9544 2.9445 1.2100 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0293 2.9798 -0.6536 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5374 2.7048 1.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9451 0.2336 0.7370 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9399 2.9486 -0.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7192 2.1743 -1.7039 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5363 2.2824 -0.1324 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7095 -0.1801 1.6908 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0298 1.5846 1.8843 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8336 0.0758 2.6007 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3234 1.3308 1.4737 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3428 -1.6063 1.1887 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9098 -2.4971 -2.1133 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8085 -2.8040 -0.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6145 -2.7670 -0.4819 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7175 0.8905 -1.6501 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5236 -0.7341 -1.8545 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3713 -1.0611 -3.5767 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7675 -1.2241 -0.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0462 -1.4953 -2.6744 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7554 0.3017 -2.7766 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7538 -1.6649 -1.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3008 -1.1342 -2.8157 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5428 2.1496 -2.4487 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3241 0.9360 -3.4584 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2967 2.0614 -2.4771 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0149 -1.4180 0.4249 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7953 -1.5151 0.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7573 -1.9104 -1.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1937 -0.8991 -2.2416 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2239 0.3375 -3.0428 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6603 2.1309 -2.1541 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6088 0.7905 -2.7956 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9287 -2.2037 1.4334 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9363 -2.4603 -0.9714 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2241 -1.8860 -1.1839 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2525 -0.2953 0.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0673 -0.1635 2.6997 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8298 2.4275 0.5327 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9976 -1.9114 2.2235 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2608 -0.1827 -2.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8244 -3.2582 1.4934 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7489 -2.9911 3.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 1 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 18 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 25 27 1 0 27 28 1 1 27 29 1 0 29 30 1 0 17 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 36 40 1 0 35 41 1 0 34 42 1 0 33 43 1 0 5 44 1 0 44 45 2 0 44 46 1 0 30 2 1 0 40 32 1 0 8 2 1 0 27 9 1 0 25 12 1 0 22 13 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 6 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 1 10 60 1 0 11 61 1 0 11 62 1 0 12 63 1 1 14 64 1 0 14 65 1 0 14 66 1 0 15 67 1 0 15 68 1 0 16 69 1 0 16 70 1 0 17 71 1 1 19 72 1 0 19 73 1 0 19 74 1 0 20 75 1 0 20 76 1 0 21 77 1 0 22 78 1 1 23 79 1 0 23 80 1 0 24 81 1 0 24 82 1 0 26 83 1 0 26 84 1 0 26 85 1 0 28 86 1 0 28 87 1 0 28 88 1 0 29 89 1 0 29 90 1 0 30 91 1 0 30 92 1 0 32 93 1 1 33 94 1 6 34 95 1 6 35 96 1 6 36 97 1 1 39 98 1 0 41 99 1 0 42100 1 0 43101 1 0 46102 1 0 M END

Standard InCHIKey	RDGWQQQKUDXGRS-WGSSIDGDSA-N
Standard InCHI	InChI=1S/C36H56O10/c1-31-13-14-32(2,30(43)44)17-20(31)19-7-8-22-33(3)11-10-23(45-29-26(40)24(38)25(39)27(46-29)28(41)42)34(4,18-37)21(33)9-12-36(22,6)35(19,5)16-15-31/h7,20-27,29,37-40H,8-18H2,1-6H3,(H,41,42)(H,43,44)/t20-,21+,22+,23-,24-,25-,26+,27-,29+,31+,32+,33-,34+,35+,36+/m0/s1
SMILES	C[C@@]12CC[C@](C)(C[C@H]2C2=CC[C@@H]3[C@@]4(C)CC[C@@H]([C@](C)(CO)[C@@H]4CC[C@@]3(C)[C@]2(C)CC1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	648.39	Volume:	659.866 ? Van der Waals volume.
Dense:	0.983	LogP:	3.186 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.775 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.332 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	34.0
TPSA:	173.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.188	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.42	Fsp³:	0.889
MCE-18:	131.294 ? 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:	0.867	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.021 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.21	Promiscuous compounds:	0.109

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.105	MDCK Permeability:	-5.207
Pgp-inhibitor:	0.0	Pgp-substrate:	0.803
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):	0.0
20% Bioavailability (F20%):	0.553	30% Bioavailability (F30%):	0.011
50% Bioavailability (F50%):	0.844

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	1.0
Plasma Protein Binding (PPB):	80.113%	Volume Distribution (VD):	-0.595
Fu:	14.243% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.029
OATP1B3 inhibitor:	0.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.01

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

0.581

Half-life (T1/2):

2.176

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.628	Drug-induced Liver Injury (DILI):	0.882
AMES Toxicity:	0.197	Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.049	Skin Sensitization:	0.998
Carcinogencity:	0.492	Eye Corrosion:	0.002
Eye Irritation:	0.264	Respiratory Toxicity:	0.26
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.905
Hematotoxicity:	0.623	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.914	RPMI-8226 Immunitoxicity:	0.032
A549 Cytotoxicity:	0.045	Hek293 Cytotoxicity:	0.042
BCF:	0.554 ? 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:	3.465 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.979 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.185 ? 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
NPO26583	Oxytropis myriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26583	Oxytropis myriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26583	Oxytropis myriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26583	Oxytropis myriophylla	Species	Fabaceae	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 NPC305444 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	20749
0.1-0.2	24791
0.2-0.3	3201
0.3-0.4	776
0.4-0.5	256
0.5-0.6	58
0.6-0.7	21
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
0.881	High Similarity	NPC482748
0.7841	Intermediate Similarity	NPC309780
0.7412	Intermediate Similarity	NPC224121
0.7283	Intermediate Similarity	NPC482751
0.6947	Remote Similarity	NPC482741
0.6947	Remote Similarity	NPC482745
0.6947	Remote Similarity	NPC482743
0.6947	Remote Similarity	NPC146753
0.6889	Remote Similarity	NPC482752
0.6629	Remote Similarity	NPC286347
0.6562	Remote Similarity	NPC473884
0.6413	Remote Similarity	NPC294112
0.6375	Remote Similarity	NPC171203
0.6375	Remote Similarity	NPC307426
0.6375	Remote Similarity	NPC98442
0.6375	Remote Similarity	NPC242468
0.6341	Remote Similarity	NPC263393
0.6327	Remote Similarity	NPC482746
0.63	Remote Similarity	NPC11551
0.6237	Remote Similarity	NPC480937
0.6162	Remote Similarity	NPC482747
0.6162	Remote Similarity	NPC202666
0.6162	Remote Similarity	NPC471961
0.6162	Remote Similarity	NPC475171
0.6162	Remote Similarity	NPC242015
0.5938	Remote Similarity	NPC480938
0.59	Remote Similarity	NPC157868
0.5865	Remote Similarity	NPC611191
0.5784	Remote Similarity	NPC242840
0.5761	Remote Similarity	NPC204407
0.5699	Remote Similarity	NPC57362
0.5699	Remote Similarity	NPC28198
0.5699	Remote Similarity	NPC476123
0.5657	Remote Similarity	NPC482726
0.5647	Remote Similarity	NPC155120
0.5647	Remote Similarity	NPC288833
0.5638	Remote Similarity	NPC177246
0.5619	Remote Similarity	NPC118440
0.56	Remote Similarity	NPC476882
0.5581	Remote Similarity	NPC474525
0.5566	Remote Similarity	NPC31193
0.5517	Remote Similarity	NPC46441
0.5514	Remote Similarity	NPC482755
0.5514	Remote Similarity	NPC95437
0.551	Remote Similarity	NPC480943
0.5481	Remote Similarity	NPC75417
0.5464	Remote Similarity	NPC471967
0.5463	Remote Similarity	NPC114692
0.5463	Remote Similarity	NPC236657
0.5429	Remote Similarity	NPC471965
0.5429	Remote Similarity	NPC482749
0.5421	Remote Similarity	NPC131469
0.5413	Remote Similarity	NPC218954
0.5412	Remote Similarity	NPC263272
0.5408	Remote Similarity	NPC476887
0.5402	Remote Similarity	NPC474964
0.5341	Remote Similarity	NPC78580
0.5341	Remote Similarity	NPC474529
0.5294	Remote Similarity	NPC603870
0.5288	Remote Similarity	NPC472949
0.5287	Remote Similarity	NPC104545
0.5248	Remote Similarity	NPC270667
0.5234	Remote Similarity	NPC14617
0.5229	Remote Similarity	NPC262199
0.5225	Remote Similarity	NPC187618
0.5225	Remote Similarity	NPC120116
0.5208	Remote Similarity	NPC606107
0.5192	Remote Similarity	NPC114441
0.5169	Remote Similarity	NPC476064
0.5158	Remote Similarity	NPC476878
0.5146	Remote Similarity	NPC136877
0.5143	Remote Similarity	NPC6377
0.5143	Remote Similarity	NPC208381
0.5116	Remote Similarity	NPC260385
0.5116	Remote Similarity	NPC110094
0.51	Remote Similarity	NPC284807
0.5057	Remote Similarity	NPC7260
0.5057	Remote Similarity	NPC210037
0.5057	Remote Similarity	NPC120968
0.5057	Remote Similarity	NPC227467
0.5057	Remote Similarity	NPC273621
0.5052	Remote Similarity	NPC283849
0.5043	Remote Similarity	NPC313110

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC305444 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6487
0.1-0.2	2605
0.2-0.3	47
0.3-0.4	5
0.4-0.5	5
0.5-0.6	0
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
0.6162	Remote Similarity	NPD8328	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