NPASS Compound

Natural Product: NPC478873

Natural Product ID	NPC478873
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ASMVNRSVTWRPRB-WECZLNSMSA-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 102108 0 0 0 0 0 0 0 0999 V2000 -1.8238 3.3927 0.4444 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2959 4.6909 0.4886 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6954 5.6459 1.2691 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6029 5.2862 2.0159 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1412 3.9893 1.9634 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7486 3.0082 1.1689 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1183 1.6743 1.2153 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1157 1.5199 0.2922 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7380 2.8355 0.0430 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9315 3.1128 0.7231 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5844 4.3097 0.5442 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0958 5.2759 -0.3034 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9300 5.0298 -0.9812 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2902 3.8188 -0.7859 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7695 6.4973 -0.4807 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1934 0.9534 -0.6796 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5122 0.0845 -1.7639 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5460 -0.2293 -2.6211 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3743 -0.9930 -3.7398 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8649 -1.4861 -4.0655 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9270 -1.1992 -3.2471 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7284 -0.4082 -2.0916 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9167 -0.2317 -1.3773 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3873 -1.2000 -0.4677 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6537 -1.8835 -0.9968 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7326 -1.9292 0.1074 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0873 -2.6633 1.2582 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8717 -1.8227 1.6490 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1357 -1.3484 3.0632 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3226 -0.5958 3.1003 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7373 -0.7440 0.7775 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7054 -3.9156 0.7999 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1741 -0.6750 0.4430 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3711 -3.2236 -1.2324 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1892 -1.7054 -3.5903 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4555 -1.3011 -4.5953 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7390 0.5747 0.4350 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6524 -0.7254 1.0717 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2256 -1.0210 2.0792 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3004 -2.3019 2.6432 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5191 -3.3148 2.1937 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4005 -3.0038 1.1796 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4869 -1.7522 0.6171 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4341 -1.5869 -0.3912 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7809 -1.2612 -0.0968 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3406 -0.1359 -0.8752 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3919 -0.5639 -1.8827 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4191 -1.4758 -1.2399 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8065 -2.2367 -0.0805 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5337 -3.5408 0.1696 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4856 -4.3683 -0.9623 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4879 -2.4552 -0.3837 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4656 -0.7203 -0.7319 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8266 -1.1235 -3.0235 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9515 0.7411 0.0542 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2295 -4.0243 0.7237 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1920 -2.5939 3.6640 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2031 6.9527 1.2876 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3196 2.6551 -0.1741 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1757 4.9163 -0.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1219 6.0425 2.6385 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7303 3.7606 2.5781 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2304 1.4861 2.2496 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7964 0.8085 0.8075 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3205 2.3587 1.3902 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5008 4.5072 1.0738 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5175 5.7795 -1.6628 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3877 3.6731 -1.3411 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0195 7.0176 0.3651 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3451 1.8811 -1.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5347 0.1301 -2.4223 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0276 -2.1009 -4.9589 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5988 -1.9791 -0.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1384 -1.3467 -1.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5725 -2.5257 -0.2868 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7989 -2.7985 2.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0113 -2.4995 1.6270 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3230 -2.2596 3.6886 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3484 -0.7074 3.4652 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1122 -1.1609 3.3221 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4134 -4.5551 1.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6940 -0.3233 -0.3224 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7062 -3.5074 -2.1003 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6434 -1.3034 -4.4221 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0909 -2.0592 -4.3865 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8308 0.7440 0.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9150 -0.3256 2.5370 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4608 -4.3117 2.6305 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8711 -1.1531 1.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6115 0.4949 -1.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9312 0.3529 -2.1954 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8312 -2.1515 -2.0165 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8660 -1.6257 0.8396 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5644 -3.3208 0.4774 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0054 -4.0720 0.9780 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5289 -4.6103 -1.0792 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0254 -0.4639 -1.5309 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7212 -0.4231 -3.7401 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2943 1.0636 0.7131 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9019 -4.8990 0.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9026 -2.2684 4.5995 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4041 7.4472 2.1374 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 12 15 1 0 8 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 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 21 35 1 0 19 36 1 0 16 37 1 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 48 53 1 0 47 54 1 0 46 55 1 0 42 56 1 0 40 57 1 0 3 58 1 0 6 1 1 0 37 7 1 0 43 38 1 0 52 45 1 0 14 9 1 0 22 17 1 0 31 24 1 0 1 59 1 0 2 60 1 0 4 61 1 0 5 62 1 0 7 63 1 1 8 64 1 1 10 65 1 0 11 66 1 0 13 67 1 0 14 68 1 0 15 69 1 0 16 70 1 6 18 71 1 0 20 72 1 0 24 73 1 1 25 74 1 6 26 75 1 6 27 76 1 1 28 77 1 1 29 78 1 0 29 79 1 0 30 80 1 0 32 81 1 0 33 82 1 0 34 83 1 0 35 84 1 0 36 85 1 0 37 86 1 6 39 87 1 0 41 88 1 0 45 89 1 1 46 90 1 6 47 91 1 6 48 92 1 6 49 93 1 1 50 94 1 0 50 95 1 0 51 96 1 0 53 97 1 0 54 98 1 0 55 99 1 0 56100 1 0 57101 1 0 58102 1 0 M END

Standard InCHIKey	ASMVNRSVTWRPRB-WECZLNSMSA-N
Standard InCHI	InChI=1S/C40H44O18/c41-13-25-31(49)33(51)35(53)39(55-25)57-37-21(9-19(45)11-23(37)47)29-27(15-1-5-17(43)6-2-15)28(16-3-7-18(44)8-4-16)30(29)22-10-20(46)12-24(48)38(22)58-40-36(54)34(52)32(50)26(14-42)56-40/h1-12,25-36,39-54H,13-14H2/t25-,26-,27-,28+,29+,30-,31-,32-,33+,34+,35-,36-,39+,40+/m1/s1
SMILES	c1cc(ccc1[C@@H]1[C@H](c2ccc(cc2)O)[C@@H](c2cc(cc(c2O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O)[C@H]1c1cc(cc(c1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	812.25	Volume:	767.087 ? Van der Waals volume.
Dense:	1.059	LogP:	0.2 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.917 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.369 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	40.0
TPSA:	320.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	14.0	Rings:	7.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.098	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.32	Fsp³:	0.4
MCE-18:	164.5 ? 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:	0
Colloidal aggregators:	0.766	Fluc inhibitor:	0.378 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.02 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.331 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.585	Promiscuous compounds:	0.263

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.509	MDCK Permeability:	-4.769
Pgp-inhibitor:	0.0	Pgp-substrate:	0.108
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):	0.013
20% Bioavailability (F20%):	0.927	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02	MRP1:	0.03
Plasma Protein Binding (PPB):	79.235%	Volume Distribution (VD):	0.001
Fu:	21.897% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.005
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.013	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.05	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.331
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.539 ? 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):

1.604

Half-life (T1/2):

6.675

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.133
Human Hepatotoxicity (H-HT):	0.906	Drug-induced Liver Injury (DILI):	0.112
AMES Toxicity:	0.818	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.106	Skin Sensitization:	1.0
Carcinogencity:	0.003	Eye Corrosion:	0.0
Eye Irritation:	0.017	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.999
Hematotoxicity:	0.014	Drug-induced Nephrotoxicity:	0.874
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.134
A549 Cytotoxicity:	0.959	Hek293 Cytotoxicity:	0.922
BCF:	0.493 ? 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:	3.244 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.214 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.21 ? 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
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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
Inhibition	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
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	16.8	%	PMID[29359942]

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 NPC478873 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	22876
0.1-0.2	22661
0.2-0.3	3309
0.3-0.4	732
0.4-0.5	243
0.5-0.6	26
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	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478871
1.0	High Similarity	NPC478870
1.0	High Similarity	NPC478872
0.6667	Remote Similarity	NPC252169
0.5789	Remote Similarity	NPC484157
0.5667	Remote Similarity	NPC12308
0.5614	Remote Similarity	NPC142319
0.5606	Remote Similarity	NPC85799
0.5606	Remote Similarity	NPC303422
0.5484	Remote Similarity	NPC166168
0.5467	Remote Similarity	NPC168358
0.5441	Remote Similarity	NPC469661
0.5441	Remote Similarity	NPC65530
0.5385	Remote Similarity	NPC214910
0.5385	Remote Similarity	NPC26080
0.5385	Remote Similarity	NPC165686
0.5373	Remote Similarity	NPC59324
0.5294	Remote Similarity	NPC478888
0.5286	Remote Similarity	NPC260681
0.525	Remote Similarity	NPC100936
0.525	Remote Similarity	NPC1253
0.5181	Remote Similarity	NPC478877
0.5156	Remote Similarity	NPC40377
0.5152	Remote Similarity	NPC210015
0.5135	Remote Similarity	NPC308265
0.5132	Remote Similarity	NPC97240
0.5082	Remote Similarity	NPC9248
0.5082	Remote Similarity	NPC152722
0.5079	Remote Similarity	NPC145900
0.507	Remote Similarity	NPC121001

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478873 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5567
0.1-0.2	3466
0.2-0.3	103
0.3-0.4	12
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