NPASS Compound

Natural Product: NPC298666

Natural Product ID	NPC298666
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Apigenin-7-O-Beta-D-Glucopyranosyl-(1->2)-Beta-D-Glucopyranosyl-(1->2)-[Alpha-L-Rhamnopyranosyl-(1->6)]-Beta-D-Glucopyranoside
IUPAC Name	[(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2336744
PubChem CID	71720749
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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

Chemical Representations

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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 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 O 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 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 -6.6734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6595 -3.3841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4095 -2.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5586 -3.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9681 -2.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2286 -1.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0796 -0.0948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3296 1.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5796 2.5033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3296 3.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8296 3.8023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5796 5.1013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6700 -0.6078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9786 0.2401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4681 -2.5362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 -4.3483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8086 -4.3483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5481 -5.8255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6972 -6.7897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1067 -6.2766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3672 -4.7994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1172 -3.5004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8672 -2.2013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2181 -3.8352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6067 -6.2766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4472 -8.0887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7981 -7.1245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 -4.3483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7981 -7.1245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4895 -12.4988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5481 -12.0477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0586 -14.8239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4095 -15.7881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -13.9761 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2500 -15.4761 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2500 -12.4761 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4895 -15.4533 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 -15.4533 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7181 -13.0119 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 -10.5705 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3806 -10.7177 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2578 -9.5226 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0194 -8.3505 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 -8.6017 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7367 -8.5590 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8951 -6.3283 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7578 -4.0256 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 -3.7189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2054 4.2601 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5861 1.2173 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2388 6.6780 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.5720 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6770 -4.2628 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7408 -3.8219 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6902 -1.3964 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1025 1.0023 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5275 2.1070 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1316 0.3015 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1662 6.5433 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9603 5.6874 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1376 4.6880 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5652 1.6820 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3709 -1.3383 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9133 -2.8519 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0563 -5.6688 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6742 -7.8867 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5453 -7.7111 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8288 -5.1368 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4980 -4.0864 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8182 -2.7504 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1172 -0.9023 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6488 -5.1977 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9360 -8.2715 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3842 -8.5053 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7974 -4.1654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9639 -6.1806 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2981 -10.7487 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5586 -14.8239 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -17.0872 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 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 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 26 29 1 0 22 30 1 0 30 31 1 0 31 32 2 0 17 33 1 0 13 34 1 0 12 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 2 0 43 45 1 0 40 46 1 0 39 47 1 0 38 48 1 0 37 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 53 58 1 0 52 59 1 0 51 60 1 0 11 61 1 0 10 62 1 0 6 63 1 0 5 64 1 0 4 65 1 0 3 66 1 0 63 2 1 0 34 9 1 0 46 36 1 0 57 50 1 0 32 15 1 0 31 18 1 0 28 23 1 0 1 67 1 0 1 68 1 0 1 69 1 0 2 70 1 6 3 71 1 1 4 72 1 6 5 73 1 6 6 74 1 1 8 75 1 0 8 76 1 0 9 77 1 1 10 78 1 6 11 79 1 1 12 80 1 6 13 81 1 1 16 82 1 0 21 83 1 0 24 84 1 0 25 85 1 0 27 86 1 0 28 87 1 0 29 88 1 0 32 89 1 0 33 90 1 0 36 91 1 6 37 92 1 1 38 93 1 6 39 94 1 1 40 95 1 6 41 96 1 0 41 97 1 0 45 98 1 0 45 99 1 0 45100 1 0 47101 1 0 48102 1 0 50103 1 6 51104 1 1 52105 1 6 53106 1 1 54107 1 6 55108 1 0 55109 1 0 56110 1 0 58111 1 0 59112 1 0 60113 1 0 61114 1 0 62115 1 0 64116 1 0 65117 1 0 66118 1 0 M END

Standard InCHIKey	IGEMAARQFGMGBZ-OTGHDJAGSA-N
Standard InCHI	InChI=1S/C41H52O25/c1-13-26(47)30(51)34(55)38(59-13)58-12-24-29(50)32(53)36(40(63-24)60-17-7-18(45)25-19(46)9-20(61-21(25)8-17)15-3-5-16(44)6-4-15)66-41-37(33(54)28(49)23(64-41)11-57-14(2)43)65-39-35(56)31(52)27(48)22(10-42)62-39/h3-9,13,22-24,26-42,44-45,47-56H,10-12H2,1-2H3/t13-,22+,23+,24+,26-,27+,28+,29+,30+,31-,32-,33-,34+,35+,36+,37+,38+,39-,40+,41-/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](Oc3cc(c4c(=O)cc(c5ccc(cc5)O)oc4c3)O)O2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](COC(=O)C)O2)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	944.28	Volume:	853.824 ? Van der Waals volume.
Dense:	1.106	LogP:	-1.29 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.088 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.717 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	43.0
TPSA:	393.34 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.071	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.938	Fsp³:	0.61
MCE-18:	180.303 ? 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:	0.616	Fluc inhibitor:	0.457 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.73 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.46 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.285	Promiscuous compounds:	0.405

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.885	MDCK Permeability:	-4.831
Pgp-inhibitor:	0.0	Pgp-substrate:	0.945
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):	0.952
20% Bioavailability (F20%):	0.162	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.02
Plasma Protein Binding (PPB):	77.11%	Volume Distribution (VD):	-0.111
Fu:	20.958% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.008
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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.524
HLM stability:	0.001 ? 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):

0.282

Half-life (T1/2):

5.281

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.017
Human Hepatotoxicity (H-HT):	0.424	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.972	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.014	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.078	Drug-induced Nephrotoxicity:	0.766
Genotoxicity:	0.873	RPMI-8226 Immunitoxicity:	0.228
A549 Cytotoxicity:	0.51	Hek293 Cytotoxicity:	0.35
BCF:	0.349 ? 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:	2.792 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.499 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.663 ? 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
NPO32535	dracocephalum ruyschiana	Species	Lamiaceae	Eukaryota	aerial parts	Mongolian	n.a.	PMID[23356964]

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	1

Activity Type	# Activity
Others	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
NPT1	Others	Radical scavenging activity	n.a.	IC50	>	200.0	ug.mL-1	PMID[12798338]

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 NPC298666 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	18515
0.1-0.2	26364
0.2-0.3	4053
0.3-0.4	587
0.4-0.5	233
0.5-0.6	68
0.6-0.7	21
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9082	High Similarity	NPC68592
0.8544	High Similarity	NPC120952
0.84	Intermediate Similarity	NPC311850
0.8	Intermediate Similarity	NPC11468
0.7905	Intermediate Similarity	NPC198199
0.7708	Intermediate Similarity	NPC65003
0.7545	Intermediate Similarity	NPC262222
0.729	Intermediate Similarity	NPC488083
0.7103	Intermediate Similarity	NPC473644
0.7103	Intermediate Similarity	NPC25523
0.7071	Intermediate Similarity	NPC44931
0.7	Intermediate Similarity	NPC488086
0.6972	Remote Similarity	NPC488087
0.6931	Remote Similarity	NPC115674
0.6667	Remote Similarity	NPC142142
0.6636	Remote Similarity	NPC480441
0.6604	Remote Similarity	NPC195257
0.6535	Remote Similarity	NPC8856
0.6505	Remote Similarity	NPC22062
0.6505	Remote Similarity	NPC473634
0.6505	Remote Similarity	NPC138811
0.6346	Remote Similarity	NPC210073
0.633	Remote Similarity	NPC602448
0.6316	Remote Similarity	NPC488088
0.6296	Remote Similarity	NPC475382
0.6286	Remote Similarity	NPC122809
0.6239	Remote Similarity	NPC101636
0.6122	Remote Similarity	NPC39360
0.6122	Remote Similarity	NPC29763
0.6122	Remote Similarity	NPC210003
0.6111	Remote Similarity	NPC209296
0.6075	Remote Similarity	NPC240306
0.602	Remote Similarity	NPC331652
0.5963	Remote Similarity	NPC32641
0.5963	Remote Similarity	NPC256188
0.5963	Remote Similarity	NPC35119
0.5946	Remote Similarity	NPC298171
0.5917	Remote Similarity	NPC209550
0.5872	Remote Similarity	NPC12013
0.5872	Remote Similarity	NPC11432
0.5872	Remote Similarity	NPC477613
0.5825	Remote Similarity	NPC80188
0.578	Remote Similarity	NPC64051
0.5766	Remote Similarity	NPC479766
0.5688	Remote Similarity	NPC186816
0.5625	Remote Similarity	NPC270675
0.5625	Remote Similarity	NPC488089
0.5625	Remote Similarity	NPC195685
0.5614	Remote Similarity	NPC253685
0.5614	Remote Similarity	NPC135358
0.5588	Remote Similarity	NPC95090
0.5588	Remote Similarity	NPC27408
0.5536	Remote Similarity	NPC122467
0.5536	Remote Similarity	NPC473623
0.5526	Remote Similarity	NPC292929
0.5526	Remote Similarity	NPC221342
0.5526	Remote Similarity	NPC476470
0.5505	Remote Similarity	NPC67105
0.5481	Remote Similarity	NPC27942
0.5478	Remote Similarity	NPC472994
0.5437	Remote Similarity	NPC189142
0.5437	Remote Similarity	NPC77660
0.5431	Remote Similarity	NPC14187
0.5405	Remote Similarity	NPC204693
0.5397	Remote Similarity	NPC199172
0.537	Remote Similarity	NPC172807
0.5357	Remote Similarity	NPC64425
0.534	Remote Similarity	NPC19709
0.531	Remote Similarity	NPC65711
0.5304	Remote Similarity	NPC89127
0.5294	Remote Similarity	NPC472993
0.5285	Remote Similarity	NPC480445
0.5263	Remote Similarity	NPC229409
0.5254	Remote Similarity	NPC89052
0.5238	Remote Similarity	NPC192539
0.5234	Remote Similarity	NPC22832
0.5234	Remote Similarity	NPC243930
0.5234	Remote Similarity	NPC601144
0.5225	Remote Similarity	NPC163242
0.5225	Remote Similarity	NPC272068
0.5225	Remote Similarity	NPC47923
0.5221	Remote Similarity	NPC46202
0.5192	Remote Similarity	NPC261866
0.5185	Remote Similarity	NPC116458
0.5185	Remote Similarity	NPC246943
0.5185	Remote Similarity	NPC311830
0.5185	Remote Similarity	NPC607707
0.5179	Remote Similarity	NPC479405
0.5179	Remote Similarity	NPC303913
0.5154	Remote Similarity	NPC473554
0.5143	Remote Similarity	NPC323593
0.5143	Remote Similarity	NPC203500
0.5138	Remote Similarity	NPC190003
0.5133	Remote Similarity	NPC479404
0.5124	Remote Similarity	NPC303694
0.5089	Remote Similarity	NPC275454
0.5089	Remote Similarity	NPC227508
0.5079	Remote Similarity	NPC480444
0.5048	Remote Similarity	NPC108831
0.5048	Remote Similarity	NPC182634
0.5041	Remote Similarity	NPC173837

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC298666 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5292
0.1-0.2	3783
0.2-0.3	67
0.3-0.4	3
0.4-0.5	3
0.5-0.6	1
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
0.6111	Remote Similarity	NPD7054	Phase 4
0.5043	Remote Similarity	NPD7251	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