NPASS Compound

Natural Product: NPC220169

Natural Product ID	NPC220169
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PHHUKAWWGOZQSD-XJUGCWAMSA-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 3D 59 62 0 0 0 0 0 0 0 0999 V2000 -5.7308 2.5991 0.8998 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5344 1.1523 1.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1425 0.7432 2.2929 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7313 0.3004 0.5561 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5925 -1.0400 0.9623 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1562 -2.0101 -0.0408 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2224 -2.4291 -1.1165 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3481 -1.5895 -2.3722 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6814 -1.4169 -2.7429 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9151 -2.5817 -0.7903 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3483 -1.6479 0.0475 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1787 -1.4078 1.2956 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2084 -2.6114 2.0003 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2408 -0.4446 -0.6368 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1300 0.3240 -0.8620 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2366 1.5203 -1.5850 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1144 2.2672 -1.7945 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1382 1.9022 -1.3254 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2717 2.6502 -1.5330 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2031 3.7235 -2.1767 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4889 2.1992 -1.0204 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5400 1.0205 -0.3189 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8048 0.5212 0.2318 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8220 -0.6867 0.9332 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9816 -1.2036 1.4750 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1860 -0.5442 1.3467 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1777 0.6481 0.6564 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9982 1.1752 0.1045 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3353 -1.0897 1.9030 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5988 -0.4695 1.8122 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4244 0.3446 -0.1500 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2619 0.7295 -0.6125 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1117 -0.0301 -0.4017 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1459 3.4770 -2.5103 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6256 -3.1468 0.6165 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5271 2.6000 0.1273 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0984 3.1781 1.7488 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8058 2.9984 0.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2214 -1.1695 1.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0478 -1.5559 -0.5262 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5776 -3.4588 -1.4473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9061 -0.5828 -2.2397 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8327 -2.0618 -3.2298 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6642 -0.8722 -3.5791 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3558 -1.9614 0.4097 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6891 -0.6739 1.9692 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5559 -2.6246 2.7414 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1973 1.8246 -1.9593 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3800 2.8158 -1.2003 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8747 -1.1916 1.0270 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9866 -2.1437 2.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1085 1.1801 0.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0498 2.1144 -0.4278 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4781 0.5501 2.2451 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8982 -0.4198 0.7497 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3020 -1.0923 2.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2934 -0.9531 0.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0616 4.3112 -1.9404 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8913 -3.7593 0.8606 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 7 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 11 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 6 35 1 0 12 5 1 0 33 15 1 0 32 18 1 0 28 23 1 0 1 36 1 0 1 37 1 0 1 38 1 0 5 39 1 1 6 40 1 6 7 41 1 6 8 42 1 0 8 43 1 0 9 44 1 0 11 45 1 1 12 46 1 1 13 47 1 0 16 48 1 0 21 49 1 0 24 50 1 0 25 51 1 0 27 52 1 0 28 53 1 0 30 54 1 0 30 55 1 0 30 56 1 0 33 57 1 0 34 58 1 0 35 59 1 0 M END

Standard InCHIKey	PHHUKAWWGOZQSD-XJUGCWAMSA-N
Standard InCHI	InChI=1S/C24H24O11/c1-11(26)32-23-21(29)19(10-25)35-24(22(23)30)33-14-7-15(27)20-16(28)9-17(34-18(20)8-14)12-3-5-13(31-2)6-4-12/h3-9,19,21-25,27,29-30H,10H2,1-2H3/t19-,21-,22-,23+,24-/m1/s1
SMILES	CC(=O)O[C@H]1[C@@H]([C@@H](CO)O[C@H]([C@@H]1O)Oc1cc(c2c(=O)cc(c3ccc(cc3)OC)oc2c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.13	Volume:	462.399 ? Van der Waals volume.
Dense:	1.056	LogP:	1.054 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.559 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.816 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	25.0
TPSA:	165.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.365	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.865	Fsp³:	0.333
MCE-18:	86.125 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.662	Fluc inhibitor:	0.355 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.954 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.825 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.113	Promiscuous compounds:	0.36

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.97	MDCK Permeability:	-5.079
Pgp-inhibitor:	0.054	Pgp-substrate:	0.65
PAMPA:	0.872 ? 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):	0.779
20% Bioavailability (F20%):	0.164	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.788
Plasma Protein Binding (PPB):	90.706%	Volume Distribution (VD):	-0.065
Fu:	10.428% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.525
BSEP inhibitor:	0.087

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.104	CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.486	CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.037
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.614 ? 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):

3.95

Half-life (T1/2):

2.635

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.112
Human Hepatotoxicity (H-HT):	0.579	Drug-induced Liver Injury (DILI):	0.993
AMES Toxicity:	0.926	Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.077	Skin Sensitization:	0.966
Carcinogencity:	0.545	Eye Corrosion:	0.0
Eye Irritation:	0.416	Respiratory Toxicity:	0.044
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.723
Hematotoxicity:	0.301	Drug-induced Nephrotoxicity:	0.578
Genotoxicity:	0.827	RPMI-8226 Immunitoxicity:	0.089
A549 Cytotoxicity:	0.174	Hek293 Cytotoxicity:	0.315
BCF:	0.415 ? 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:	3.199 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.574 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.779 ? 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
NPO10304	Colletotrichum gloeosporioides	Species	Glomerellaceae	Eukaryota	Artemisia mongolica	n.a.	n.a.	PMID[11087599]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908994]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[1823989]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO10304	Colletotrichum gloeosporioides	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29035525]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31444719]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31747281]
NPO5118	Zanthoxylum myriacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36627746]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38791403]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8594148]
NPO7968	Artemisia kurramensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9447	Tolypothrix tenuis	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26396	Coprinopsis atramentaria	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9265	Jasonia candicans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1252	Aglaia grandis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10304	Colletotrichum gloeosporioides	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10536	Rhabdonia verticillata	Species	Areschougiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO540	Anaphalis araneosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5118	Zanthoxylum myriacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5118	Zanthoxylum myriacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26719	Tetrapanax papyrifer	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1252	Aglaia grandis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11452	Pterocarpus officinalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26396	Coprinopsis atramentaria	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12613	Catunaregam tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8120	Episcia cupreata	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9265	Jasonia candicans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5118	Zanthoxylum myriacanthum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11544	Vernonia lanuginosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7968	Artemisia kurramensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7779	Impatiens edgeworthii	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10081	Othonna sedifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO557	Bhesa nitidissima	Species	Centroplacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10304	Colletotrichum gloeosporioides	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12153	Adenia globosa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10483	Chrysanthemum sinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7463	Ranzania japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9447	Tolypothrix tenuis	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10536	Rhabdonia verticillata	Species	Areschougiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO540	Anaphalis araneosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6802	Rothmannia wittii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26396	Coprinopsis atramentaria	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11583	Calycanthus floridus	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11452	Pterocarpus officinalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26719	Tetrapanax papyrifer	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1252	Aglaia grandis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10798	Cis punctifer	Species	Ciidae	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
IC50	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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[31747281]

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 NPC220169 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	14167
0.1-0.2	31909
0.2-0.3	2904
0.3-0.4	609
0.4-0.5	192
0.5-0.6	53
0.6-0.7	14
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	Natural Product ID
0.7375	Intermediate Similarity	NPC80188
0.7308	Intermediate Similarity	NPC95090
0.7308	Intermediate Similarity	NPC27408
0.7273	Intermediate Similarity	NPC479765
0.7045	Intermediate Similarity	NPC210961
0.6585	Remote Similarity	NPC181712
0.6353	Remote Similarity	NPC22832
0.6353	Remote Similarity	NPC243930
0.6237	Remote Similarity	NPC488089
0.6197	Remote Similarity	NPC29353
0.6145	Remote Similarity	NPC39360
0.6145	Remote Similarity	NPC29763
0.6145	Remote Similarity	NPC210003
0.6092	Remote Similarity	NPC607707
0.6044	Remote Similarity	NPC22062
0.6044	Remote Similarity	NPC473634
0.6044	Remote Similarity	NPC138811
0.604	Remote Similarity	NPC488088
0.6	Remote Similarity	NPC475382
0.598	Remote Similarity	NPC488086
0.5941	Remote Similarity	NPC488083
0.5938	Remote Similarity	NPC101636
0.5909	Remote Similarity	NPC311830
0.5895	Remote Similarity	NPC479766
0.5882	Remote Similarity	NPC189142
0.5882	Remote Similarity	NPC77660
0.5814	Remote Similarity	NPC186807
0.5795	Remote Similarity	NPC608742
0.5789	Remote Similarity	NPC473623
0.5765	Remote Similarity	NPC58053
0.5765	Remote Similarity	NPC261866
0.5747	Remote Similarity	NPC27942
0.5745	Remote Similarity	NPC46202
0.5648	Remote Similarity	NPC262222
0.5647	Remote Similarity	NPC331652
0.5625	Remote Similarity	NPC606657
0.5618	Remote Similarity	NPC601144
0.5534	Remote Similarity	NPC311850
0.5524	Remote Similarity	NPC68592
0.549	Remote Similarity	NPC473278
0.5481	Remote Similarity	NPC488087
0.5481	Remote Similarity	NPC470716
0.5446	Remote Similarity	NPC11468
0.5402	Remote Similarity	NPC19709
0.5402	Remote Similarity	NPC143851
0.5368	Remote Similarity	NPC65003
0.5333	Remote Similarity	NPC127447
0.5326	Remote Similarity	NPC190003
0.5312	Remote Similarity	NPC122809
0.5306	Remote Similarity	NPC209296
0.53	Remote Similarity	NPC298171
0.5294	Remote Similarity	NPC248739
0.5287	Remote Similarity	NPC473043
0.5278	Remote Similarity	NPC471030
0.5269	Remote Similarity	NPC211594
0.5263	Remote Similarity	NPC234133
0.5256	Remote Similarity	NPC195202
0.5256	Remote Similarity	NPC223579
0.5227	Remote Similarity	NPC289667
0.5213	Remote Similarity	NPC8856
0.52	Remote Similarity	NPC195257
0.5172	Remote Similarity	NPC158027
0.5169	Remote Similarity	NPC487213
0.5155	Remote Similarity	NPC115674
0.5152	Remote Similarity	NPC124155
0.5143	Remote Similarity	NPC473644
0.5114	Remote Similarity	NPC14606
0.5104	Remote Similarity	NPC44931
0.5065	Remote Similarity	NPC145379
0.5056	Remote Similarity	NPC121649
0.5053	Remote Similarity	NPC606546
0.5052	Remote Similarity	NPC3583

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC220169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4401
0.1-0.2	4651
0.2-0.3	86
0.3-0.4	10
0.4-0.5	1
0.5-0.6	1
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
0.5306	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