NPASS Compound

Natural Product: NPC100998

Natural Product ID	NPC100998
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Leucosceptoside A
IUPAC Name	[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL450121
PubChem CID	10394343
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 83 86 0 0 0 0 0 0 0 0999 V2000 1.4760 0.5560 -4.0418 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3454 0.8468 -3.3245 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5010 0.3910 -1.8860 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5720 1.0045 -1.2649 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7887 0.2964 -0.0776 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0372 0.6241 0.4173 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9013 -0.4684 0.4289 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2254 0.0101 1.0173 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1545 -1.1350 1.0289 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9670 -1.3457 -0.0532 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8412 -2.4200 -0.0694 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8780 -3.2691 1.0206 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0545 -3.0448 2.1029 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1758 -1.9679 2.1228 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0894 -3.8930 3.1952 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7587 -4.3535 1.0069 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6644 0.5674 0.8985 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4535 1.3252 0.2019 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7595 0.7377 -1.1458 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5931 -0.4035 -1.0413 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8094 -0.5378 -1.6308 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2547 0.4134 -2.3392 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5934 -1.7735 -1.4462 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7684 -1.9518 -2.0085 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4937 -3.1917 -1.7868 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7182 -3.3620 -2.4419 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4680 -4.5017 -2.2784 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0332 -5.5409 -1.4471 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8397 -5.3804 -0.8050 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0903 -4.2183 -0.9803 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3545 -6.3918 0.0434 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1102 -6.2101 0.7127 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8301 -6.6681 -1.3193 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0935 2.6621 0.1302 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9409 3.4973 0.8789 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5838 4.3265 0.0241 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9623 5.4854 -0.3300 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8156 6.2107 -1.3449 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 6.3105 0.9307 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2466 5.5459 1.7450 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1688 4.1255 1.9853 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8558 4.0895 3.1984 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5525 6.2012 2.9370 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2985 7.5837 0.6637 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1666 -0.5996 1.4462 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6520 -0.4012 -3.9957 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5410 0.3218 -3.7701 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1005 1.9303 -3.3477 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6345 -0.7197 -1.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7888 -0.7756 -0.3386 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5205 -1.2855 1.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0864 -0.7846 -0.6162 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6478 0.8654 0.4866 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0777 0.3298 2.0818 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9550 -0.6897 -0.9278 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4682 -2.5580 -0.9366 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5577 -1.8396 2.9876 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3817 -4.6383 3.2439 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8934 -4.9290 0.1846 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0672 1.1907 1.7066 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3556 1.2528 0.8246 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2921 1.4997 -1.7490 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1173 -2.5187 -0.8117 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1682 -1.1591 -2.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0397 -2.5450 -3.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4115 -4.6352 -2.7833 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1446 -4.1291 -0.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7909 -7.1704 1.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1377 -5.3631 1.4001 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3779 -6.0022 -0.1172 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3812 -6.9403 -2.1254 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6916 2.8136 1.3324 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0249 5.2501 -0.7858 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8787 6.2226 -1.0794 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6078 5.8090 -2.3585 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4704 7.2810 -1.3695 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7218 6.3114 1.5191 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1925 5.5783 1.1300 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7684 3.5388 2.1438 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2988 4.3377 3.9550 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3402 6.8134 2.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0943 7.9853 1.5623 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3618 -0.4293 2.2572 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 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 12 16 1 0 5 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 28 33 1 0 18 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 17 45 1 0 19 3 1 0 30 25 1 0 41 35 1 0 14 9 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 6 5 50 1 6 7 51 1 0 7 52 1 0 8 53 1 0 8 54 1 0 10 55 1 0 11 56 1 0 14 57 1 0 15 58 1 0 16 59 1 0 17 60 1 1 18 61 1 1 19 62 1 6 23 63 1 0 24 64 1 0 26 65 1 0 27 66 1 0 30 67 1 0 32 68 1 0 32 69 1 0 32 70 1 0 33 71 1 0 35 72 1 1 37 73 1 6 38 74 1 0 38 75 1 0 38 76 1 0 39 77 1 1 40 78 1 6 41 79 1 1 42 80 1 0 43 81 1 0 44 82 1 0 45 83 1 0 M END

Standard InCHIKey	ZMYQRHSOVRDQDL-CPPDSBOHSA-N
Standard InCHI	InChI=1S/C30H38O15/c1-14-23(36)24(37)25(38)30(42-14)45-28-26(39)29(41-10-9-16-3-6-17(32)19(34)11-16)43-21(13-31)27(28)44-22(35)8-5-15-4-7-18(33)20(12-15)40-2/h3-8,11-12,14,21,23-34,36-39H,9-10,13H2,1-2H3/b8-5+/t14-,21+,23-,24+,25+,26+,27+,28+,29+,30-/m0/s1
SMILES	OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)OC)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.22	Volume:	603.972 ? Van der Waals volume.
Dense:	1.057	LogP:	-0.093 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.799 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.347 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	26.0
TPSA:	234.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.086	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.694	Fsp³:	0.5
MCE-18:	99.889 ? 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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.727	Fluc inhibitor:	0.663 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.166 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.55 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.133	Promiscuous compounds:	0.313

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.326	MDCK Permeability:	-5.369
Pgp-inhibitor:	0.0	Pgp-substrate:	0.462
PAMPA:	0.998 ? 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):	0.715
20% Bioavailability (F20%):	0.98	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.043
Plasma Protein Binding (PPB):	69.75%	Volume Distribution (VD):	-0.327
Fu:	27.659% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.043
BSEP inhibitor:	0.018

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.983
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.67 ? 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):

2.847

Half-life (T1/2):

3.385

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.325
Human Hepatotoxicity (H-HT):	0.348	Drug-induced Liver Injury (DILI):	0.62
AMES Toxicity:	0.951	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.021	Skin Sensitization:	1.0
Carcinogencity:	0.034	Eye Corrosion:	0.0
Eye Irritation:	0.036	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.992
Hematotoxicity:	0.15	Drug-induced Nephrotoxicity:	0.489
Genotoxicity:	0.169	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.944	Hek293 Cytotoxicity:	0.626
BCF:	0.696 ? 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:	3.313 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.03 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.247 ? 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
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s00253-012-4489-y]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/ncomms4886]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1093/oxfordjournals.pcp.a076462]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[10395493]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858748]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1367520]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17287127]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19093848]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[19093848]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21381678]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22118684]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO16360	Gardenia carinata	Species	Rubiaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[23550966]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	PMID[24669201]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24840014]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2488968]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[2610694]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562611]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26692349]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[31180680]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33089690]
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39419301]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8626236]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834166]
NPO16764	Penstemon linarioides	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834166]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22203	Tapinella panuoides	Species	Tapinellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15404	Streptomyces erythrochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2028	Campsis grandiflora	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15898	Streptomyces noursei	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15108	Angiopteris evecta	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14454	Plectranthus lanuginosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12472	Buddleja davidii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14965	Lepidophorum repandum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15621	Lethasterias fusca	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11584	Artemisia argentea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12480	Brodiaea californica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28240	Notholaena lemmonii	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4436	Trillium erectum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16598	Helenium elegans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13743	Populus yunnanensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15087	Alstonia pittieri	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16161	Stephania aculeata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12777	Laurencia pacifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1124	Scapania aequiloba	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10061	Sideritis ozturkii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12472	Buddleja davidii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4436	Trillium erectum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2656	Phtheirospermum japonicum	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16598	Helenium elegans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2028	Campsis grandiflora	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10061	Sideritis ozturkii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4436	Trillium erectum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12472	Buddleja davidii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2656	Phtheirospermum japonicum	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16598	Helenium elegans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2028	Campsis grandiflora	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16598	Helenium elegans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2028	Campsis grandiflora	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13477	Cyberlindnera jadinii	Species	Phaffomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22203	Tapinella panuoides	Species	Tapinellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11903	Alysicarpus bupleurifolius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13225	Spergula japonica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO255	Solanum pseudopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16161	Stephania aculeata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15087	Alstonia pittieri	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28240	Notholaena lemmonii	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14454	Plectranthus lanuginosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11584	Artemisia argentea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2667	Acacia lasiopetala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27134	Euphrasia rubra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8556	Eucalyptus kitsoniana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10527	Cyathula tomentosa	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26381	Bombus pascuorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15513	Pseudocyphellaria rubella	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15806	Rhododendron campylocarpum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1777	Toddalia aculeata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9299.3	Hordeum vulgare var. distichon	Varieties	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15718	Lindera sericea	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1124	Scapania aequiloba	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15108	Angiopteris evecta	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13460	Asphodeline damascena	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO15898	Streptomyces noursei	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22101	Himantoglossum hircinum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15404	Streptomyces erythrochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26951	Gymnopus androsaceus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13743	Populus yunnanensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11243	Exochorda giraldii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2028	Campsis grandiflora	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12777	Laurencia pacifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16598	Helenium elegans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12480	Brodiaea californica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21851	Chaetomella raphigera	Species	Chaetomellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14965	Lepidophorum repandum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29322	Rhodanthe maryonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15621	Lethasterias fusca	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15523	Euphorbia calycina	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16764	Penstemon linarioides	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12472	Buddleja davidii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4436	Trillium erectum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16360	Gardenia carinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10061	Sideritis ozturkii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14042	Rollinia dolabripetala	Species	Annonaceae	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
NPO18048	Phlomis crinita	Methanolic extract	Flowers	0.20 Â± 0.01	n.a.	n.a.	%	PMID[39419301]

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Inhibition	1
IC50	1

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT182	Individual protein	Protein kinase C alpha	Homo sapiens	IC50	=	19000.0	nM	PMID[9834166]
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	Inhibition	=	21.65	%	PMID[17287127]

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 NPC100998 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	12951
0.1-0.2	30690
0.2-0.3	5300
0.3-0.4	744
0.4-0.5	105
0.5-0.6	25
0.6-0.7	23
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC34587
0.9048	High Similarity	NPC34927
0.8415	Intermediate Similarity	NPC472350
0.8415	Intermediate Similarity	NPC197316
0.8415	Intermediate Similarity	NPC89105
0.8372	Intermediate Similarity	NPC252292
0.7895	Intermediate Similarity	NPC94871
0.7841	Intermediate Similarity	NPC269141
0.7609	Intermediate Similarity	NPC259347
0.7604	Intermediate Similarity	NPC306890
0.7579	Intermediate Similarity	NPC470933
0.7529	Intermediate Similarity	NPC46137
0.7283	Intermediate Similarity	NPC112
0.7216	Intermediate Similarity	NPC471062
0.7172	Intermediate Similarity	NPC473427
0.7143	Intermediate Similarity	NPC470934
0.7033	Intermediate Similarity	NPC263829
0.7	Intermediate Similarity	NPC76406
0.6989	Remote Similarity	NPC298257
0.6989	Remote Similarity	NPC175214
0.6979	Remote Similarity	NPC476382
0.6966	Remote Similarity	NPC483705
0.6961	Remote Similarity	NPC476386
0.6923	Remote Similarity	NPC611289
0.6857	Remote Similarity	NPC257970
0.6854	Remote Similarity	NPC483706
0.6632	Remote Similarity	NPC205864
0.6632	Remote Similarity	NPC247032
0.6598	Remote Similarity	NPC96795
0.6598	Remote Similarity	NPC264632
0.6566	Remote Similarity	NPC106818
0.6531	Remote Similarity	NPC300894
0.6531	Remote Similarity	NPC23845
0.6522	Remote Similarity	NPC134405
0.6471	Remote Similarity	NPC87403
0.6392	Remote Similarity	NPC296954
0.6392	Remote Similarity	NPC600370
0.6263	Remote Similarity	NPC232992
0.6239	Remote Similarity	NPC470927
0.6226	Remote Similarity	NPC188393
0.617	Remote Similarity	NPC68092
0.5979	Remote Similarity	NPC106677
0.5941	Remote Similarity	NPC610636
0.5914	Remote Similarity	NPC81515
0.59	Remote Similarity	NPC119537
0.5849	Remote Similarity	NPC476398
0.5795	Remote Similarity	NPC886
0.5789	Remote Similarity	NPC64141
0.5778	Remote Similarity	NPC473285
0.5769	Remote Similarity	NPC476384
0.5701	Remote Similarity	NPC64195
0.566	Remote Similarity	NPC476380
0.5421	Remote Similarity	NPC196063
0.5421	Remote Similarity	NPC604195
0.537	Remote Similarity	NPC476381
0.5349	Remote Similarity	NPC157554
0.5326	Remote Similarity	NPC35731
0.5306	Remote Similarity	NPC205195
0.5268	Remote Similarity	NPC229505
0.5248	Remote Similarity	NPC476377
0.5185	Remote Similarity	NPC476375
0.5109	Remote Similarity	NPC287597
0.5102	Remote Similarity	NPC235294
0.5093	Remote Similarity	NPC141455
0.5091	Remote Similarity	NPC476378
0.505	Remote Similarity	NPC222433

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC100998 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4200
0.1-0.2	4774
0.2-0.3	172
0.3-0.4	3
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8415	Intermediate Similarity	NPD7266	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