NPASS Compound

Natural Product: NPC92815

Natural Product ID	NPC92815
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Kaempferol-3-O-(3'',4""-Diacetyl-2"",6""-Di-E-P-Coumaroyl)-Glucoside
IUPAC Name	[(2R,3R,4S,5R,6S)-3,4-diacetyloxy-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3628130
PubChem CID	10328097
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl 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 96101 0 0 0 0 0 0 0 0999 V2000 7.2286 -7.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9681 -6.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1172 -5.5525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5586 -6.0037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2981 -4.5264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8886 -5.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -6.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5905 -6.9678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8509 -8.4450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2605 -8.9581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7019 -9.4092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9623 -10.8864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1867 -11.8506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5963 -11.3376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7453 -12.3018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4849 -13.7790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0753 -14.2920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0737 -13.3278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6339 -14.7432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -4.0753 0.0000 O 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 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 -3.5623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1172 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8567 -1.1209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5268 -3.1111 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 5.2981 0.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8886 0.8694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4472 1.3205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1867 2.7977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3358 3.7619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0753 5.2391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2244 6.2033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6339 5.6903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8944 4.2131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 3.2489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7830 6.6545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 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 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 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 -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 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 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 -5.1962 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 -0.7500 -3.8971 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 5.1962 0.0000 O 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 8.7058 -7.7334 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7514 -8.2544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4891 -9.4711 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7981 -4.5264 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6386 -6.3385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7753 -4.8546 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7037 -7.1527 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7077 -8.8962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3719 -11.3995 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8567 -9.8604 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1549 -11.7887 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8148 -15.7692 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4833 -13.8409 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3735 -16.2204 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -1.1209 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6595 -0.7860 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3086 -1.7502 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0398 -1.7016 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0137 -4.5206 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9363 -3.6241 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8567 0.8075 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7772 3.3108 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6658 5.7522 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9639 7.6805 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3039 3.7000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0058 1.7717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1925 6.1414 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 -3.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -1.2990 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 -0.7500 -6.4952 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 -3.0000 -7.7942 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 3.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 16 19 1 0 6 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 22 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 21 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 2 0 53 54 1 0 54 55 2 0 55 56 1 0 56 57 2 0 55 58 1 0 47 59 1 0 45 60 1 0 23 5 1 0 38 33 1 0 51 41 2 0 57 52 1 0 18 13 1 0 49 44 1 0 1 61 1 0 1 62 1 0 1 63 1 0 5 64 1 1 6 65 1 6 7 66 1 0 7 67 1 0 11 68 1 0 12 69 1 0 14 70 1 0 15 71 1 0 17 72 1 0 18 73 1 0 19 74 1 0 21 75 1 6 22 76 1 1 23 77 1 6 27 78 1 0 27 79 1 0 27 80 1 0 31 81 1 0 32 82 1 0 34 83 1 0 35 84 1 0 37 85 1 0 38 86 1 0 39 87 1 0 46 88 1 0 48 89 1 0 53 90 1 0 54 91 1 0 56 92 1 0 57 93 1 0 58 94 1 0 59 95 1 0 60 96 1 0 M END

Standard InCHIKey	IFLHDGGEJKVLAF-FEMPFSAESA-N
Standard InCHI	InChI=1S/C43H36O17/c1-22(44)55-39-33(21-54-34(51)17-7-24-3-11-27(46)12-4-24)58-43(42(41(39)56-23(2)45)59-35(52)18-8-25-5-13-28(47)14-6-25)60-40-37(53)36-31(50)19-30(49)20-32(36)57-38(40)26-9-15-29(48)16-10-26/h3-20,33,39,41-43,46-50H,21H2,1-2H3/b17-7+,18-8+/t33-,39-,41+,42-,43+/m1/s1
SMILES	CC(=O)O[C@@H]1[C@@H](COC(=O)/C=C/c2ccc(cc2)O)O[C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)/C=C/c1ccc(cc1)O)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	824.2	Volume:	797.65 ? Van der Waals volume.
Dense:	1.033	LogP:	2.715 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.402 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.487 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	42.0
TPSA:	255.02 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.064	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.702	Fsp³:	0.186
MCE-18:	127.843 ? 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:	1.0	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.879 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.643 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.406	Promiscuous compounds:	0.816

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.115	MDCK Permeability:	-5.152
Pgp-inhibitor:	0.932	Pgp-substrate:	0.024
PAMPA:	0.864 ? 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%):	0.981	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.006
Plasma Protein Binding (PPB):	92.122%	Volume Distribution (VD):	-0.049
Fu:	8.954% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.067
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.521
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.851
CYP2D6-inhibitor:	0.019	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.983 ? 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):

2.573

Half-life (T1/2):

2.277

ADMET: Toxicity

hERG Blockers:	0.106	hERG Blockers (10um):	0.405
Human Hepatotoxicity (H-HT):	0.664	Drug-induced Liver Injury (DILI):	0.985
AMES Toxicity:	0.893	Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.874	Skin Sensitization:	1.0
Carcinogencity:	0.289	Eye Corrosion:	0.0
Eye Irritation:	0.307	Respiratory Toxicity:	0.009
Drug-induced Neurotoxicity:	0.078	Ototoxicity:	0.248
Hematotoxicity:	0.013	Drug-induced Nephrotoxicity:	0.182
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.831	Hek293 Cytotoxicity:	0.995
BCF:	0.703 ? 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:	4.132 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.967 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.857 ? 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
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075766]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11112781]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[153409]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568769]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[17190463]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17870137]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[18239317]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[18239317]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18462007]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21417376]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21673922]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21848268]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	Urup Island (4557,9 N; 15044,9 E; depth 66 m)	2008-AUG	PMID[21848268]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23265519]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23317005]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23488669]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27524650]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29115831]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31182315]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31287310]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4955234]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8808	Artemisia schimperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11558	Atylosia trinervia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27848	Conoideocrella luteorostrata	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9930	Dendrodoris tuberculosa	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12893	Dermolepida albohirtum	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8777	Euryops algoensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4544	Gomortega keule	Species	Gomortegaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11949	Iris ensata	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6259	Keiferia lycopersicella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12317	Naja kaouthia	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12677	Penicillium kapuscinskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13002	Petasites georgicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1038	Phoenix loureiroi	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7050	Picea mariana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11709	Salvia parryi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12081	Streptomyces xanthochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10613	Thalictrum longistylum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8492	Viburnum urceolatum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7347	Viguiera oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4293	Allium neapolitanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2968	Anthopleura xanthogrammica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19333	Byssothecium obiones	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4816	Cycas armstrongii	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25775	Dasystenella acanthina	Species	Primnoidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1897	Ephedra aphylla	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO115	Eutreptia viridis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6302	Licaria armeniaca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6130	Mammillaria magnimamma	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3756	Munronia delavayi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2609	Neonectria candida	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18463	Plectocephalus chilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3419	Quercus suber	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO291	Suillus bovinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10870	Trichilia hirta	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10613	Thalictrum longistylum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6850	Typha domingensis	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4293	Allium neapolitanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6302	Licaria armeniaca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21679	Nuphar lutea	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO963	Litsea pungens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8492	Viburnum urceolatum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1897	Ephedra aphylla	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27848	Conoideocrella luteorostrata	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1038	Phoenix loureiroi	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9930	Dendrodoris tuberculosa	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19333	Byssothecium obiones	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12677	Penicillium kapuscinskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17226	Burkholderia pyrrocinia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3756	Munronia delavayi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2609	Neonectria candida	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6259	Keiferia lycopersicella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12081	Streptomyces xanthochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12893	Dermolepida albohirtum	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO115	Eutreptia viridis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4544	Gomortega keule	Species	Gomortegaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO658	Leucopaxillus gentianeus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6130	Mammillaria magnimamma	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4240	Elephantopus tomentosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4816	Cycas armstrongii	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11709	Salvia parryi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3124	Gloiopeltis furcata	Species	Endocladiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28092	Xyris pterygoblephara	Species	Xyridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18463	Plectocephalus chilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8777	Euryops algoensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5723	Quercus robur	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11949	Iris ensata	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO291	Suillus bovinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7050	Picea mariana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10870	Trichilia hirta	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13002	Petasites georgicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7347	Viguiera oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25775	Dasystenella acanthina	Species	Primnoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11558	Atylosia trinervia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5082	Cycas revoluta	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12317	Naja kaouthia	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10613	Thalictrum longistylum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8808	Artemisia schimperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3419	Quercus suber	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7622	Monanchora pulchra	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2968	Anthopleura xanthogrammica	Species	Actiniidae	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
Ki	5
IC50	3
Ratio IC50	1

Activity Type	# Activity
Individual protein	5
Cell line	1
Organism	2
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT233	Individual protein	Carbonic anhydrase II	Homo sapiens	Ki	=	6863.3	nM	PMID[26498393]
NPT1062	Individual protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	62.2	nM	PMID[26498393]
NPT955	Individual protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	26.6	nM	PMID[26498393]
NPT949	Individual protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	399.7	nM	PMID[26498393]
NPT947	Individual protein	Carbonic anhydrase I	Homo sapiens	Ki	>	10000.0	nM	PMID[26498393]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell line	HeLa	Homo sapiens	IC50	<	3000.0	nM	PMID[26722868]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	600.0	nM	PMID[26722868]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2100.0	nM	PMID[26722868]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	3.5	n.a.	PMID[26722868]

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 NPC92815 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	15505
0.1-0.2	30555
0.2-0.3	3105
0.3-0.4	425
0.4-0.5	193
0.5-0.6	43
0.6-0.7	24
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	NPC478277
1.0	High Similarity	NPC478276
1.0	High Similarity	NPC478275
0.7292	Intermediate Similarity	NPC101399
0.7292	Intermediate Similarity	NPC217822
0.7292	Intermediate Similarity	NPC11847
0.7292	Intermediate Similarity	NPC198938
0.7245	Intermediate Similarity	NPC218161
0.6932	Remote Similarity	NPC104677
0.6832	Remote Similarity	NPC96605
0.6832	Remote Similarity	NPC280642
0.6771	Remote Similarity	NPC473862
0.6768	Remote Similarity	NPC221288
0.6768	Remote Similarity	NPC194836
0.6768	Remote Similarity	NPC91493
0.6768	Remote Similarity	NPC605081
0.67	Remote Similarity	NPC85751
0.67	Remote Similarity	NPC19240
0.65	Remote Similarity	NPC104883
0.65	Remote Similarity	NPC488679
0.6436	Remote Similarity	NPC205824
0.633	Remote Similarity	NPC474093
0.633	Remote Similarity	NPC104910
0.625	Remote Similarity	NPC483767
0.625	Remote Similarity	NPC223426
0.625	Remote Similarity	NPC483769
0.625	Remote Similarity	NPC483768
0.625	Remote Similarity	NPC483766
0.619	Remote Similarity	NPC214621
0.619	Remote Similarity	NPC34267
0.6068	Remote Similarity	NPC231787
0.6038	Remote Similarity	NPC483765
0.5963	Remote Similarity	NPC217520
0.5938	Remote Similarity	NPC48093
0.5932	Remote Similarity	NPC275977
0.5929	Remote Similarity	NPC162394
0.5872	Remote Similarity	NPC477895
0.5818	Remote Similarity	NPC470712
0.5789	Remote Similarity	NPC156785
0.5789	Remote Similarity	NPC474522
0.5741	Remote Similarity	NPC81042
0.5702	Remote Similarity	NPC30011
0.5702	Remote Similarity	NPC72554
0.5678	Remote Similarity	NPC25946
0.567	Remote Similarity	NPC216496
0.5575	Remote Similarity	NPC470718
0.5556	Remote Similarity	NPC260504
0.5556	Remote Similarity	NPC85707
0.5556	Remote Similarity	NPC259957
0.5556	Remote Similarity	NPC36138
0.5556	Remote Similarity	NPC241781
0.5556	Remote Similarity	NPC89809
0.5556	Remote Similarity	NPC224530
0.5524	Remote Similarity	NPC470125
0.552	Remote Similarity	NPC97817
0.5439	Remote Similarity	NPC139571
0.5433	Remote Similarity	NPC475179
0.541	Remote Similarity	NPC473554
0.5403	Remote Similarity	NPC487502
0.5385	Remote Similarity	NPC33083
0.536	Remote Similarity	NPC249560
0.53	Remote Similarity	NPC159579
0.53	Remote Similarity	NPC129217
0.5246	Remote Similarity	NPC21359
0.5246	Remote Similarity	NPC460984
0.5196	Remote Similarity	NPC321478
0.5185	Remote Similarity	NPC297503
0.5182	Remote Similarity	NPC477629
0.5169	Remote Similarity	NPC470713
0.514	Remote Similarity	NPC129264
0.513	Remote Similarity	NPC164704
0.5098	Remote Similarity	NPC117478
0.5088	Remote Similarity	NPC470416
0.5046	Remote Similarity	NPC477628
0.5045	Remote Similarity	NPC188815

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC92815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4197
0.1-0.2	4897
0.2-0.3	51
0.3-0.4	4
0.4-0.5	1
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