NPASS Compound

Natural Product: NPC488087

Natural Product ID	NPC488087
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ILUVBMWRZKXCRT-IZHAMJLOSA-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: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

RDKit 2D 105110 0 0 0 0 0 0 0 0999 V2000 -2.2500 -13.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -13.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -14.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 -13.5249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0481 -12.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6386 -11.5347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3886 -10.2356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6386 -8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8886 -7.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2981 -7.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5586 -5.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4095 -4.6831 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 -1.5000 -5.1962 0.0000 O 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 0.7500 -3.8971 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 -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 3.0000 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 -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 -5.2500 6.4952 0.0000 C 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 -3.0000 -1.5720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 -0.0948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8886 0.8694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2981 0.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7981 0.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2981 0.3563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0481 -0.9427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2981 -2.2417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5481 -0.9427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5586 -1.1209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6386 2.1684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9895 1.2042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -1.5720 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 -5.1595 -17.0872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6595 -17.0872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4095 -18.3862 0.0000 C 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 -5.3724 -8.6251 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 -5.5312 -7.8868 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0202 -5.9847 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6676 -3.8662 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5614 -3.7617 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 -5.2500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0420 1.5191 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7500 6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 7.9952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 4.9952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9888 -2.7809 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 -5.6676 -2.9020 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 -3.0492 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2398 -0.0685 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8656 1.9664 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7367 1.7908 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9810 1.8452 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7981 -1.1437 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0481 -0.9427 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5481 -2.4427 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5481 0.5573 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0940 2.5314 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8923 2.4022 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9139 -0.1912 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8086 -4.3483 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7009 -5.9266 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 -3.6595 -19.6852 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7086 -19.1362 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1105 -17.6362 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 29 30 1 0 22 31 1 0 31 32 1 0 32 33 2 0 17 34 1 0 13 35 1 0 12 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 1 0 44 45 2 0 44 46 1 0 41 47 1 0 40 48 1 0 39 49 1 0 38 50 1 0 11 51 1 0 10 52 1 0 6 53 1 0 5 54 1 0 4 55 1 0 3 56 1 0 56 57 1 0 57 58 2 0 57 59 1 0 53 2 1 0 35 9 1 0 47 37 1 0 33 15 1 0 32 18 1 0 28 23 1 0 1 60 1 0 1 61 1 0 1 62 1 0 2 63 1 6 3 64 1 1 4 65 1 6 5 66 1 6 6 67 1 1 8 68 1 0 8 69 1 0 9 70 1 1 10 71 1 6 11 72 1 1 12 73 1 6 13 74 1 1 16 75 1 0 21 76 1 0 24 77 1 0 25 78 1 0 27 79 1 0 28 80 1 0 30 81 1 0 30 82 1 0 30 83 1 0 33 84 1 0 34 85 1 0 37 86 1 1 38 87 1 6 39 88 1 1 40 89 1 6 41 90 1 1 42 91 1 0 42 92 1 0 46 93 1 0 46 94 1 0 46 95 1 0 48 96 1 0 49 97 1 0 50 98 1 0 51 99 1 0 52100 1 0 54101 1 0 55102 1 0 59103 1 0 59104 1 0 59105 1 0 M END

Standard InCHIKey	ILUVBMWRZKXCRT-IZHAMJLOSA-N
Standard InCHI	InChI=1S/C38H46O21/c1-14-34(54-16(3)40)31(47)33(49)36(53-14)52-13-25-28(44)30(46)35(59-37-32(48)29(45)27(43)24(57-37)12-51-15(2)39)38(58-25)55-19-9-20(41)26-21(42)11-22(56-23(26)10-19)17-5-7-18(50-4)8-6-17/h5-11,14,24-25,27-38,41,43-49H,12-13H2,1-4H3/t14-,24+,25+,27+,28+,29-,30-,31-,32+,33+,34-,35+,36+,37-,38+/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)OC)oc4c3)O)O2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](COC(=O)C)O2)O)O)O)O)O)O1)O)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	838.25	Volume:	772.695 ? Van der Waals volume.
Dense:	1.085	LogP:	0.698 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.298 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.764 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	38.0
TPSA:	309.26 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.093	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.428	Fsp³:	0.553
MCE-18:	150.864 ? 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:	0.641	Fluc inhibitor:	0.546 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.84 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.495 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.08	Promiscuous compounds:	0.328

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.225	MDCK Permeability:	-5.174
Pgp-inhibitor:	0.009	Pgp-substrate:	0.667
PAMPA:	0.996 ? 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):	0.998
20% Bioavailability (F20%):	0.897	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.15
Plasma Protein Binding (PPB):	77.64%	Volume Distribution (VD):	-0.325
Fu:	20.864% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.012
BSEP inhibitor:	0.067

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.149 ? 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):

0.673

Half-life (T1/2):

4.042

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.032
Human Hepatotoxicity (H-HT):	0.352	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.982	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	0.998
Carcinogencity:	0.096	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.985
Hematotoxicity:	0.319	Drug-induced Nephrotoxicity:	0.807
Genotoxicity:	0.791	RPMI-8226 Immunitoxicity:	0.204
A549 Cytotoxicity:	0.262	Hek293 Cytotoxicity:	0.257
BCF:	0.474 ? 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:	3.202 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.92 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.139 ? 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
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	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	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
NPT804	Cell line	HT-22	Mus musculus	EC50	>	100000.0	nM	PMID[32991171]

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 NPC488087 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	16227
0.1-0.2	29593
0.2-0.3	3303
0.3-0.4	516
0.4-0.5	162
0.5-0.6	35
0.6-0.7	11
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8958	High Similarity	NPC488083
0.8866	High Similarity	NPC488088
0.8632	High Similarity	NPC11468
0.8218	Intermediate Similarity	NPC488086
0.8105	Intermediate Similarity	NPC488089
0.7692	Intermediate Similarity	NPC68592
0.7308	Intermediate Similarity	NPC473644
0.7238	Intermediate Similarity	NPC311850
0.7117	Intermediate Similarity	NPC262222
0.6972	Remote Similarity	NPC298666
0.6937	Remote Similarity	NPC120952
0.6869	Remote Similarity	NPC22062
0.6869	Remote Similarity	NPC473634
0.6869	Remote Similarity	NPC138811
0.6699	Remote Similarity	NPC479766
0.6518	Remote Similarity	NPC198199
0.6442	Remote Similarity	NPC473623
0.6162	Remote Similarity	NPC80188
0.6132	Remote Similarity	NPC209296
0.6095	Remote Similarity	NPC46202
0.5962	Remote Similarity	NPC44931
0.5825	Remote Similarity	NPC211594
0.5818	Remote Similarity	NPC101636
0.578	Remote Similarity	NPC142142
0.5755	Remote Similarity	NPC65003
0.5755	Remote Similarity	NPC210073
0.5727	Remote Similarity	NPC475382
0.5701	Remote Similarity	NPC204693
0.57	Remote Similarity	NPC181712
0.5676	Remote Similarity	NPC298171
0.5619	Remote Similarity	NPC8856
0.56	Remote Similarity	NPC95090
0.56	Remote Similarity	NPC27408
0.5586	Remote Similarity	NPC195257
0.5586	Remote Similarity	NPC479765
0.5556	Remote Similarity	NPC115674
0.5545	Remote Similarity	NPC483707
0.5481	Remote Similarity	NPC220169
0.5364	Remote Similarity	NPC64051
0.5268	Remote Similarity	NPC229409
0.5254	Remote Similarity	NPC480441
0.5254	Remote Similarity	NPC25523
0.5234	Remote Similarity	NPC172807
0.5221	Remote Similarity	NPC270675
0.5221	Remote Similarity	NPC195685
0.5217	Remote Similarity	NPC135358
0.5179	Remote Similarity	NPC65711
0.5169	Remote Similarity	NPC472993
0.5138	Remote Similarity	NPC295613
0.5138	Remote Similarity	NPC473657
0.5135	Remote Similarity	NPC122809
0.5086	Remote Similarity	NPC472994
0.5048	Remote Similarity	NPC27942
0.5046	Remote Similarity	NPC254540
0.504	Remote Similarity	NPC209550

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488087 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4997
0.1-0.2	4092
0.2-0.3	52
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
0.6132	Remote Similarity	NPD7054	Phase 4

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