NPASS Compound

Natural Product: NPC487502

Natural Product ID	NPC487502
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PMQYHSJQIYKYMR-ZUMRTIEQSA-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] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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

RDKit 3D 107113 0 0 0 0 0 0 0 0999 V2000 -4.0531 3.5828 3.8050 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3241 3.8934 2.3272 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2617 5.0497 2.2927 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2762 5.8441 1.0329 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9625 5.7639 0.2674 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4519 4.3148 0.3084 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4707 3.4282 -0.0014 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2654 2.6742 -1.1284 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0093 1.8033 -1.0597 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1035 0.9124 -2.3108 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7874 0.1582 -2.3365 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4158 -0.3938 -1.0279 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3975 -0.1516 0.0744 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1457 0.9748 0.0125 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2757 -1.2266 0.3326 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8875 -2.2903 1.1359 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8378 -2.0051 2.5114 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1270 -0.8805 2.9721 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4586 -2.9911 3.3910 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3915 -2.7552 4.7642 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0075 -3.7504 5.6338 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6972 -4.9755 5.0794 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7592 -5.2210 3.7310 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1491 -4.2136 2.8381 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2112 -4.4347 1.5640 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -3.5235 0.6561 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6179 -3.9131 -0.7466 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1645 -3.1925 -1.7671 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1726 -3.6572 -3.0762 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6214 -4.8773 -3.3930 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0669 -5.6143 -2.3790 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0701 -5.1344 -1.0897 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5081 -6.8436 -2.6767 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6476 -5.3173 -4.7291 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3072 -5.9842 5.9700 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7128 -1.5050 5.2847 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2277 0.2790 -0.5981 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7490 -0.6340 -0.2874 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0788 -0.3736 -0.9870 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0955 -0.9234 -0.0582 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1650 0.0011 0.4298 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2513 0.2741 -0.3310 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5149 0.8358 -1.5185 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5594 1.2645 -2.2028 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8860 0.9708 -2.0514 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8950 0.5346 -1.3514 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2975 0.5919 -1.7290 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2713 0.0981 -0.8608 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6082 0.1441 -1.1860 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0631 0.6732 -2.3731 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0953 1.1637 -3.2367 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7385 1.1201 -2.9131 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4079 0.7211 -2.7029 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2126 -1.3075 1.1729 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1197 -0.4990 1.0659 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7053 -2.1206 -0.4651 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1161 -1.0773 -2.1998 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8428 -0.7550 -3.3689 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2626 1.6543 -3.4505 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1221 4.0981 1.6443 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0505 6.5440 0.9743 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4212 7.2040 1.3850 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5678 4.5289 2.4612 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0204 3.1570 4.1847 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8030 4.5144 4.3515 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2750 2.8177 3.8377 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8543 2.9907 1.9345 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0428 5.6992 3.1915 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1248 5.6213 0.3453 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1189 6.1076 -0.7691 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6158 4.2862 -0.3880 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1629 2.0606 -1.2974 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1829 3.3672 -2.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1167 2.4218 -1.0790 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9062 0.1811 -2.0964 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0322 0.9336 -2.6775 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1454 -1.4437 -1.0531 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7756 -0.0979 1.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9497 -3.5856 6.7005 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5176 -6.1828 3.2925 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6134 -2.2395 -1.5899 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6223 -3.0434 -3.8497 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6190 -5.7563 -0.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6480 -7.2628 -3.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5054 -5.2413 -5.2856 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3192 -6.2505 5.9346 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9463 -1.0255 5.7834 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4925 -1.6818 -0.4349 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2171 0.7279 -1.1228 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6865 0.9815 0.7708 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5234 -0.4209 1.4247 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0556 1.4225 -3.0032 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6472 0.0832 -0.3870 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9233 -0.3276 0.0898 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3453 -0.2460 -0.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4233 1.5833 -4.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9937 1.5089 -3.6057 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9573 1.5740 -2.5512 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8036 -1.1967 2.1019 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9451 -2.3638 1.0335 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6700 -2.0499 -0.3299 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7888 -0.6770 -2.7789 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1188 -0.7008 -4.0290 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6106 1.1235 -4.2083 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5842 7.1645 0.3490 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2103 7.6180 0.9803 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1768 5.2891 2.2589 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 30 34 1 0 22 35 1 0 20 36 1 0 12 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 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 50 53 1 0 40 54 1 0 54 55 1 0 40 56 1 6 39 57 1 0 11 58 1 0 10 59 1 0 6 60 1 0 5 61 1 0 4 62 1 0 3 63 1 0 60 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 55 38 1 0 24 19 1 0 52 47 1 0 1 64 1 0 1 65 1 0 1 66 1 0 2 67 1 6 3 68 1 1 4 69 1 6 5 70 1 6 6 71 1 6 8 72 1 0 8 73 1 0 9 74 1 1 10 75 1 1 11 76 1 6 12 77 1 6 13 78 1 1 21 79 1 0 23 80 1 0 28 81 1 0 29 82 1 0 32 83 1 0 33 84 1 0 34 85 1 0 35 86 1 0 36 87 1 0 38 88 1 1 39 89 1 6 41 90 1 0 41 91 1 0 45 92 1 0 46 93 1 0 48 94 1 0 49 95 1 0 51 96 1 0 52 97 1 0 53 98 1 0 54 99 1 0 54100 1 0 56101 1 0 57102 1 0 58103 1 0 59104 1 0 61105 1 0 62106 1 0 63107 1 0 M END

Standard InCHIKey	PMQYHSJQIYKYMR-ZUMRTIEQSA-N
Standard InCHI	InChI=1S/C41H44O22/c1-16-28(48)31(51)33(53)38(59-16)56-13-25-29(49)32(52)36(63-40-37(54)41(55,15-58-40)14-57-26(47)9-4-17-2-6-19(42)7-3-17)39(61-25)62-35-30(50)27-23(46)11-20(43)12-24(27)60-34(35)18-5-8-21(44)22(45)10-18/h2-12,16,25,28-29,31-33,36-40,42-46,48-49,51-55H,13-15H2,1H3/b9-4+/t16-,25+,28-,29+,31+,32-,33+,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](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)O)O)O)O)O[C@H]2[C@@H]([C@@](COC(=O)/C=C/c3ccc(cc3)O)(CO2)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	888.23	Volume:	816.908 ? Van der Waals volume.
Dense:	1.087	LogP:	1.294 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.487 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.234 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	43.0
TPSA:	354.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	12.0	Rings:	7.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.045	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.701	Fsp³:	0.415
MCE-18:	170.655 ? 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:	0.683	Fluc inhibitor:	0.477 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.769 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.268	Promiscuous compounds:	0.515

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.594	MDCK Permeability:	-5.185
Pgp-inhibitor:	0.0	Pgp-substrate:	0.574
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):	0.313
20% Bioavailability (F20%):	0.988	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	84.874%	Volume Distribution (VD):	-0.056
Fu:	12.214% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.317
BSEP inhibitor:	0.012

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:	0.847
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.227
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.74 ? 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):

1.068

Half-life (T1/2):

5.266

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.205
Human Hepatotoxicity (H-HT):	0.534	Drug-induced Liver Injury (DILI):	0.959
AMES Toxicity:	0.934	Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.615	Skin Sensitization:	1.0
Carcinogencity:	0.067	Eye Corrosion:	0.0
Eye Irritation:	0.181	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.96
Hematotoxicity:	0.021	Drug-induced Nephrotoxicity:	0.321
Genotoxicity:	0.989	RPMI-8226 Immunitoxicity:	0.155
A549 Cytotoxicity:	0.959	Hek293 Cytotoxicity:	0.95
BCF:	0.658 ? 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:	3.44 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.821 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.332 ? 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
NPO41013	Polygala flavescens ssp. flavescens	Strain	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28692289]

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
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT644	Individual protein	L-lactate dehydrogenase A chain	Homo sapiens	IC50	>	500000.0	nM	PMID[28692289]

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 NPC487502 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	15408
0.1-0.2	30394
0.2-0.3	3291
0.3-0.4	428
0.4-0.5	180
0.5-0.6	105
0.6-0.7	38
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9035	High Similarity	NPC487501
0.8783	High Similarity	NPC487500
0.8273	Intermediate Similarity	NPC162394
0.7778	Intermediate Similarity	NPC487499
0.7568	Intermediate Similarity	NPC303694
0.7383	Intermediate Similarity	NPC122467
0.7131	Intermediate Similarity	NPC275977
0.7131	Intermediate Similarity	NPC473554
0.7091	Intermediate Similarity	NPC89127
0.7059	Intermediate Similarity	NPC241781
0.704	Intermediate Similarity	NPC249560
0.6972	Remote Similarity	NPC12013
0.6972	Remote Similarity	NPC11432
0.6972	Remote Similarity	NPC477613
0.688	Remote Similarity	NPC30011
0.688	Remote Similarity	NPC72554
0.6875	Remote Similarity	NPC221342
0.6875	Remote Similarity	NPC476470
0.675	Remote Similarity	NPC156785
0.6667	Remote Similarity	NPC97817
0.6667	Remote Similarity	NPC223426
0.6667	Remote Similarity	NPC218161
0.6667	Remote Similarity	NPC602448
0.656	Remote Similarity	NPC21359
0.656	Remote Similarity	NPC460984
0.6557	Remote Similarity	NPC480444
0.6552	Remote Similarity	NPC89052
0.6457	Remote Similarity	NPC231787
0.6341	Remote Similarity	NPC488740
0.6341	Remote Similarity	NPC488736
0.6341	Remote Similarity	NPC488733
0.633	Remote Similarity	NPC95866
0.6303	Remote Similarity	NPC173837
0.626	Remote Similarity	NPC480445
0.625	Remote Similarity	NPC203259
0.625	Remote Similarity	NPC33054
0.625	Remote Similarity	NPC33083
0.625	Remote Similarity	NPC176740
0.625	Remote Similarity	NPC471725
0.625	Remote Similarity	NPC134532
0.625	Remote Similarity	NPC602582
0.624	Remote Similarity	NPC488737
0.622	Remote Similarity	NPC25946
0.6207	Remote Similarity	NPC85751
0.6207	Remote Similarity	NPC19240
0.6186	Remote Similarity	NPC81042
0.6154	Remote Similarity	NPC292929
0.6106	Remote Similarity	NPC155877
0.6063	Remote Similarity	NPC192539
0.5952	Remote Similarity	NPC474522
0.5946	Remote Similarity	NPC476215
0.592	Remote Similarity	NPC488734
0.592	Remote Similarity	NPC488735
0.592	Remote Similarity	NPC488739
0.592	Remote Similarity	NPC488732
0.592	Remote Similarity	NPC488738
0.5917	Remote Similarity	NPC214621
0.5917	Remote Similarity	NPC34267
0.5902	Remote Similarity	NPC477895
0.5877	Remote Similarity	NPC173582
0.5877	Remote Similarity	NPC265885
0.5877	Remote Similarity	NPC181465
0.5877	Remote Similarity	NPC215710
0.5877	Remote Similarity	NPC473438
0.5877	Remote Similarity	NPC253788
0.5854	Remote Similarity	NPC217520
0.5847	Remote Similarity	NPC142142
0.5776	Remote Similarity	NPC255157
0.5776	Remote Similarity	NPC259896
0.5763	Remote Similarity	NPC473327
0.576	Remote Similarity	NPC470718
0.5739	Remote Similarity	NPC163242
0.5739	Remote Similarity	NPC272068
0.5726	Remote Similarity	NPC480441
0.5714	Remote Similarity	NPC221288
0.5714	Remote Similarity	NPC194836
0.5714	Remote Similarity	NPC91493
0.5714	Remote Similarity	NPC605081
0.5649	Remote Similarity	NPC480442
0.5614	Remote Similarity	NPC254855
0.5614	Remote Similarity	NPC94610
0.5603	Remote Similarity	NPC67326
0.5603	Remote Similarity	NPC39834
0.56	Remote Similarity	NPC470712
0.5583	Remote Similarity	NPC101399
0.5583	Remote Similarity	NPC97119
0.5583	Remote Similarity	NPC217822
0.5583	Remote Similarity	NPC11847
0.5583	Remote Similarity	NPC198938
0.5565	Remote Similarity	NPC488075
0.5556	Remote Similarity	NPC156869
0.5537	Remote Similarity	NPC476472
0.5537	Remote Similarity	NPC294815
0.5537	Remote Similarity	NPC16194
0.5528	Remote Similarity	NPC96605
0.5528	Remote Similarity	NPC280642
0.5528	Remote Similarity	NPC483765
0.5512	Remote Similarity	NPC139571
0.5492	Remote Similarity	NPC260504
0.5492	Remote Similarity	NPC89809
0.5478	Remote Similarity	NPC116864
0.5478	Remote Similarity	NPC244776
0.5476	Remote Similarity	NPC25523
0.5447	Remote Similarity	NPC483767
0.5447	Remote Similarity	NPC483769
0.5447	Remote Similarity	NPC483768
0.5447	Remote Similarity	NPC483766
0.5424	Remote Similarity	NPC304741
0.541	Remote Similarity	NPC220173
0.5403	Remote Similarity	NPC478277
0.5403	Remote Similarity	NPC478276
0.5403	Remote Similarity	NPC478275
0.5403	Remote Similarity	NPC92815
0.5379	Remote Similarity	NPC209550
0.5378	Remote Similarity	NPC35167
0.5372	Remote Similarity	NPC104883
0.5372	Remote Similarity	NPC488679
0.5338	Remote Similarity	NPC480443
0.5333	Remote Similarity	NPC470125
0.5333	Remote Similarity	NPC126784
0.5333	Remote Similarity	NPC241423
0.5328	Remote Similarity	NPC603079
0.5315	Remote Similarity	NPC127546
0.5315	Remote Similarity	NPC57625
0.5315	Remote Similarity	NPC173637
0.5315	Remote Similarity	NPC317489
0.5315	Remote Similarity	NPC223424
0.5315	Remote Similarity	NPC600591
0.5299	Remote Similarity	NPC480472
0.5289	Remote Similarity	NPC245452
0.5285	Remote Similarity	NPC471669
0.5285	Remote Similarity	NPC477629
0.5276	Remote Similarity	NPC292019
0.5276	Remote Similarity	NPC202908
0.5259	Remote Similarity	NPC170052
0.5259	Remote Similarity	NPC135846
0.5254	Remote Similarity	NPC471079
0.5242	Remote Similarity	NPC36138
0.5238	Remote Similarity	NPC203145
0.5191	Remote Similarity	NPC474093
0.5191	Remote Similarity	NPC104910
0.5175	Remote Similarity	NPC216496
0.5167	Remote Similarity	NPC605592
0.5147	Remote Similarity	NPC199172
0.5124	Remote Similarity	NPC129264
0.5122	Remote Similarity	NPC37668
0.5083	Remote Similarity	NPC470405
0.5081	Remote Similarity	NPC205824
0.5068	Remote Similarity	NPC482521
0.5041	Remote Similarity	NPC65563
0.5041	Remote Similarity	NPC470949
0.504	Remote Similarity	NPC76831
0.5039	Remote Similarity	NPC219043
0.5038	Remote Similarity	NPC470713

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC487502 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4781
0.1-0.2	4324
0.2-0.3	36
0.3-0.4	5
0.4-0.5	3
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
0.625	Remote Similarity	NPD6797	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