NPASS Compound

Natural Product: NPC8198

Natural Product ID	NPC8198
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GZSOSUNBTXMUFQ-SRSKTEPCSA-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 75 79 0 0 0 0 0 0 0 0999 V2000 -7.7539 -1.6332 -0.9815 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6271 -1.1087 -0.0863 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1281 -1.3147 1.3518 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1636 -0.5457 2.2411 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8819 -0.2346 1.4994 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1201 0.5531 0.2202 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0597 1.8920 0.4834 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1150 2.6452 -0.1530 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6762 2.3270 0.1694 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8164 3.3665 -0.5120 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9582 3.2287 -1.9947 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8968 1.8001 -2.4167 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5563 0.8888 -1.2830 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2292 0.8565 -0.9345 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6676 -0.1787 -1.0105 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3952 -1.4453 -1.4807 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3513 -2.4329 -1.5251 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6345 -2.1856 -1.0940 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6211 -3.1403 -1.1194 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 -4.2751 -1.5505 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8842 -2.7850 -0.6599 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1581 -1.5262 -0.1916 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4899 -1.1406 0.2967 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7124 0.1543 0.7660 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9467 0.5510 1.2317 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9870 -0.3534 1.2340 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8089 -1.6393 0.7797 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5550 -1.9952 0.3215 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8693 -2.5636 0.7813 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2601 -0.0013 1.6964 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5098 1.3108 2.1790 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1797 -0.6614 -0.1920 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9434 -0.9315 -0.6176 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9807 0.0462 -0.5781 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0705 -3.7146 -2.0026 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3756 1.0523 -0.1785 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8753 1.6923 -3.3979 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9704 3.9654 -2.6749 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5083 3.2515 -0.0459 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3897 0.2296 -0.3193 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0707 0.4931 2.3526 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8130 -1.3586 3.3155 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1085 -2.6602 1.6990 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4777 -1.3534 -2.0177 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8889 -2.7081 -0.8738 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6724 -1.0624 -0.7326 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7696 -1.7680 -0.2246 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1525 -0.9071 1.3799 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6708 0.3398 2.6383 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4038 -1.1957 1.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3888 0.2336 -0.5436 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3186 3.7516 -0.0005 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2712 2.4866 -1.2575 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5233 2.5012 1.2798 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2142 4.4070 -0.2698 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9702 3.6828 -2.2433 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8674 1.4929 -2.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8277 -0.1518 -1.6618 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6184 -1.6743 -1.8322 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6536 -3.5474 -0.6851 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8817 0.8310 0.7499 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1372 1.5620 1.6028 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4458 -3.0080 -0.0276 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1813 -2.8405 1.7218 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3320 2.0051 1.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7922 1.4911 3.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5619 1.3539 2.5061 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2300 1.0490 -0.1965 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2576 -4.2436 -1.7749 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0095 1.4926 -2.9684 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1337 4.9447 -2.5729 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5902 2.9056 0.8940 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2969 0.3763 3.3085 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6228 -1.6762 3.8176 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0580 -2.9855 1.7231 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 27 29 1 0 26 30 1 0 30 31 1 0 22 32 1 0 32 33 1 0 33 34 2 0 17 35 1 0 13 36 1 0 12 37 1 0 11 38 1 0 10 39 1 0 6 40 1 0 5 41 1 0 4 42 1 0 3 43 1 0 40 2 1 0 36 9 1 0 34 15 1 0 33 18 1 0 28 23 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 1 3 48 1 6 4 49 1 1 5 50 1 6 6 51 1 6 8 52 1 0 8 53 1 0 9 54 1 1 10 55 1 1 11 56 1 6 12 57 1 6 13 58 1 6 16 59 1 0 21 60 1 0 24 61 1 0 25 62 1 0 28 63 1 0 29 64 1 0 31 65 1 0 31 66 1 0 31 67 1 0 34 68 1 0 35 69 1 0 37 70 1 0 38 71 1 0 39 72 1 0 41 73 1 0 42 74 1 0 43 75 1 0 M END

Standard InCHIKey	GZSOSUNBTXMUFQ-SRSKTEPCSA-N
Standard InCHI	InChI=1S/C28H32O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-8,10,19,21-30,32-37H,9H2,1-2H3/t10-,19-,21-,22-,23-,24-,25+,26-,27-,28+/m1/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(c(c5)O)OC)oc4c3)O)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.17	Volume:	560.823 ? Van der Waals volume.
Dense:	1.084	LogP:	0.921 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.27 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.937 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	238.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.686	Fsp³:	0.464
MCE-18:	118.585 ? 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:	0
Colloidal aggregators:	0.638	Fluc inhibitor:	0.303 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.892 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.801 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.074	Promiscuous compounds:	0.357

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.318	MDCK Permeability:	-5.314
Pgp-inhibitor:	0.0	Pgp-substrate:	0.959
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.825
20% Bioavailability (F20%):	0.462	30% Bioavailability (F30%):	0.972
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.355
Plasma Protein Binding (PPB):	81.674%	Volume Distribution (VD):	-0.057
Fu:	15.585% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.975
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.573
BSEP inhibitor:	0.021

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.519
HLM stability:	0.008 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.424

Half-life (T1/2):

5.41

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.307
Human Hepatotoxicity (H-HT):	0.189	Drug-induced Liver Injury (DILI):	0.639
AMES Toxicity:	0.833	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.11	Skin Sensitization:	0.693
Carcinogencity:	0.067	Eye Corrosion:	0.0
Eye Irritation:	0.193	Respiratory Toxicity:	0.016
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.96
Hematotoxicity:	0.077	Drug-induced Nephrotoxicity:	0.2
Genotoxicity:	0.078	RPMI-8226 Immunitoxicity:	0.136
A549 Cytotoxicity:	0.222	Hek293 Cytotoxicity:	0.427
BCF:	0.367 ? 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:	3.027 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.589 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.746 ? 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
NPO19220	Laurencia nidifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)81142-5]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	Eukaryota	n.a.	Antarctic	n.a.	PMID[16038562]
NPO22561	Dickeya chrysanthemi	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18803373]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24784222]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35268681]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38308284]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39410132]
NPO22561	Dickeya chrysanthemi	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17863	Artocarpus styracifolius	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18822	Dacrydium intermedium	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13651	Chondodendron toxicoferum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19412	Capsella bursa	Species	Donacidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17045	Argyreia speciosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22902	Alnus alnobetula	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18488	Streptomyces griseolus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17431	Vernonia profuga	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8673	Actinopyga echinites	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9041	Libocedrus formosana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14192	Climacoptera transoxana	Species	Tettigoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18896	Swertia chinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17562	Phyllidiella pustulosa	Species	Phyllidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16030	Lecanora coniza	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19487	Dorstenia mannii	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19064	Forsythia giraldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16705	Krameria parvifolia	Species	Krameriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19220	Laurencia nidifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18896	Swertia chinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19220	Laurencia nidifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19487	Dorstenia mannii	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2961	Lomelosia caucasica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18896	Swertia chinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17045	Argyreia speciosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19220	Laurencia nidifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8261	Gleditsia horrida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22561	Dickeya chrysanthemi	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19487	Dorstenia mannii	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19220	Laurencia nidifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19412	Capsella bursa	Species	Donacidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17431	Vernonia profuga	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14192	Climacoptera transoxana	Species	Tettigoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18822	Dacrydium intermedium	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9041	Libocedrus formosana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13651	Chondodendron toxicoferum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19064	Forsythia giraldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8261	Gleditsia horrida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8673	Actinopyga echinites	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17045	Argyreia speciosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17562	Phyllidiella pustulosa	Species	Phyllidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2961	Lomelosia caucasica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18896	Swertia chinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16705	Krameria parvifolia	Species	Krameriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO931	Malus baccata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16030	Lecanora coniza	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22902	Alnus alnobetula	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17863	Artocarpus styracifolius	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO382	Zanthoxylum scandens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18488	Streptomyces griseolus	Species	Streptomycetaceae	Bacteria	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

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

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 NPC8198 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	17977
0.1-0.2	27559
0.2-0.3	3265
0.3-0.4	620
0.4-0.5	283
0.5-0.6	96
0.6-0.7	38
0.7-0.8	1
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC209296
0.8795	High Similarity	NPC22062
0.8795	High Similarity	NPC473634
0.8795	High Similarity	NPC138811
0.8353	Intermediate Similarity	NPC210073
0.8023	Intermediate Similarity	NPC44931
0.7576	Intermediate Similarity	NPC198199
0.7391	Intermediate Similarity	NPC473623
0.7353	Intermediate Similarity	NPC120952
0.7326	Intermediate Similarity	NPC22832
0.7312	Intermediate Similarity	NPC488089
0.7253	Intermediate Similarity	NPC204693
0.7113	Intermediate Similarity	NPC11468
0.6848	Remote Similarity	NPC67105
0.6804	Remote Similarity	NPC101636
0.6744	Remote Similarity	NPC19709
0.6737	Remote Similarity	NPC65711
0.6733	Remote Similarity	NPC473644
0.6702	Remote Similarity	NPC186816
0.6667	Remote Similarity	NPC311850
0.6667	Remote Similarity	NPC227508
0.6667	Remote Similarity	NPC473327
0.6632	Remote Similarity	NPC46202
0.6629	Remote Similarity	NPC611303
0.6476	Remote Similarity	NPC68592
0.6458	Remote Similarity	NPC475366
0.6437	Remote Similarity	NPC473043
0.6437	Remote Similarity	NPC331652
0.6404	Remote Similarity	NPC181712
0.6364	Remote Similarity	NPC475382
0.6327	Remote Similarity	NPC229409
0.63	Remote Similarity	NPC298171
0.6292	Remote Similarity	NPC95090
0.6292	Remote Similarity	NPC27408
0.6237	Remote Similarity	NPC190003
0.6168	Remote Similarity	NPC488086
0.6154	Remote Similarity	NPC472993
0.6132	Remote Similarity	NPC488087
0.6126	Remote Similarity	NPC262222
0.6125	Remote Similarity	NPC223579
0.6122	Remote Similarity	NPC64051
0.6111	Remote Similarity	NPC298666
0.61	Remote Similarity	NPC270675
0.61	Remote Similarity	NPC195685
0.6082	Remote Similarity	NPC303913
0.604	Remote Similarity	NPC195257
0.6022	Remote Similarity	NPC243930
0.602	Remote Similarity	NPC115674
0.6	Remote Similarity	NPC483707
0.6	Remote Similarity	NPC211594
0.6	Remote Similarity	NPC606657
0.5981	Remote Similarity	NPC488083
0.5978	Remote Similarity	NPC27942
0.5957	Remote Similarity	NPC311830
0.5957	Remote Similarity	NPC607707
0.5941	Remote Similarity	NPC142142
0.5938	Remote Similarity	NPC254540
0.5934	Remote Similarity	NPC189142
0.5934	Remote Similarity	NPC77660
0.5922	Remote Similarity	NPC472994
0.5922	Remote Similarity	NPC135358
0.59	Remote Similarity	NPC470443
0.5876	Remote Similarity	NPC187379
0.5816	Remote Similarity	NPC275454
0.5794	Remote Similarity	NPC480441
0.5794	Remote Similarity	NPC25523
0.5773	Remote Similarity	NPC251417
0.5758	Remote Similarity	NPC65003
0.5728	Remote Similarity	NPC476472
0.5728	Remote Similarity	NPC294815
0.5728	Remote Similarity	NPC16194
0.5714	Remote Similarity	NPC295613
0.5714	Remote Similarity	NPC473657
0.5684	Remote Similarity	NPC486578
0.5684	Remote Similarity	NPC601144
0.5684	Remote Similarity	NPC605067
0.567	Remote Similarity	NPC172807
0.5652	Remote Similarity	NPC261866
0.5652	Remote Similarity	NPC39360
0.5652	Remote Similarity	NPC29763
0.5652	Remote Similarity	NPC210003
0.5644	Remote Similarity	NPC126784
0.5644	Remote Similarity	NPC241423
0.56	Remote Similarity	NPC473512
0.56	Remote Similarity	NPC129827
0.5579	Remote Similarity	NPC285197
0.5545	Remote Similarity	NPC473571
0.5545	Remote Similarity	NPC110941
0.5532	Remote Similarity	NPC46420
0.5532	Remote Similarity	NPC271692
0.55	Remote Similarity	NPC173582
0.55	Remote Similarity	NPC265885
0.55	Remote Similarity	NPC181465
0.55	Remote Similarity	NPC215710
0.55	Remote Similarity	NPC473438
0.55	Remote Similarity	NPC253788
0.5495	Remote Similarity	NPC488088
0.549	Remote Similarity	NPC284277
0.549	Remote Similarity	NPC475497
0.5484	Remote Similarity	NPC238376
0.5455	Remote Similarity	NPC8856
0.5446	Remote Similarity	NPC203259
0.5446	Remote Similarity	NPC33054
0.5446	Remote Similarity	NPC176740
0.5446	Remote Similarity	NPC471725
0.5446	Remote Similarity	NPC134532
0.5446	Remote Similarity	NPC602582
0.5426	Remote Similarity	NPC158674
0.5417	Remote Similarity	NPC191306
0.5385	Remote Similarity	NPC51326
0.5361	Remote Similarity	NPC80188
0.5347	Remote Similarity	NPC39834
0.5333	Remote Similarity	NPC479766
0.5319	Remote Similarity	NPC249281
0.5319	Remote Similarity	NPC108831
0.5319	Remote Similarity	NPC182634
0.5306	Remote Similarity	NPC99957
0.5306	Remote Similarity	NPC220169
0.5294	Remote Similarity	NPC479405
0.5283	Remote Similarity	NPC479765
0.5283	Remote Similarity	NPC473073
0.5258	Remote Similarity	NPC219904
0.5253	Remote Similarity	NPC276377
0.5243	Remote Similarity	NPC479404
0.5204	Remote Similarity	NPC181616
0.5204	Remote Similarity	NPC608742
0.5196	Remote Similarity	NPC15358
0.5158	Remote Similarity	NPC58053
0.5146	Remote Similarity	NPC65563
0.5146	Remote Similarity	NPC475155
0.5146	Remote Similarity	NPC470949
0.5143	Remote Similarity	NPC479403
0.514	Remote Similarity	NPC80068
0.514	Remote Similarity	NPC477629
0.5138	Remote Similarity	NPC14187
0.5135	Remote Similarity	NPC480796
0.5114	Remote Similarity	NPC469622
0.5096	Remote Similarity	NPC257566
0.5094	Remote Similarity	NPC32641
0.5094	Remote Similarity	NPC256188
0.5093	Remote Similarity	NPC235575
0.5091	Remote Similarity	NPC121703
0.506	Remote Similarity	NPC29353
0.5052	Remote Similarity	NPC186807
0.5048	Remote Similarity	NPC240306
0.5047	Remote Similarity	NPC486577
0.5044	Remote Similarity	NPC277532

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC8198 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4785
0.1-0.2	4282
0.2-0.3	71
0.3-0.4	5
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7054	Phase 4
0.7474	Intermediate Similarity	NPD7472	Pre-clinical
0.6275	Remote Similarity	NPD7808	Phase 3
0.62	Remote Similarity	NPD7251	Phase 2
0.5446	Remote Similarity	NPD6797	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data