NPASS Compound

Natural Product: NPC269904

Natural Product ID	NPC269904
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XEOMCDDFSGTWFB-RXFKRDKPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11377340
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 81 85 0 0 0 0 0 0 0 0999 V2000 -7.5016 1.6668 4.4691 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2152 1.0654 4.0585 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5284 0.4648 4.9172 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7406 1.1381 2.7680 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5087 0.5643 2.3661 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3471 0.8487 0.8858 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5896 0.5569 0.1119 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7591 -0.8795 -0.2722 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3950 -1.5391 -0.2978 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4245 -0.4851 -0.7646 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1820 0.3205 0.3577 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2725 -1.0860 -1.1897 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9043 -0.7785 -2.4842 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7522 -1.9449 -3.4032 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9397 -1.6966 -4.6380 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0400 -0.5854 -4.5743 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3017 0.0190 -5.9479 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8348 0.7089 -6.4044 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2770 0.4355 -3.6823 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5388 -0.1117 -2.4034 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5291 0.9666 -1.5217 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4997 1.2738 -0.6561 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3703 2.3711 0.2104 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3843 2.7044 1.0831 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5623 1.9934 1.1577 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5796 2.3270 2.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4637 3.3009 2.8001 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7284 1.5230 2.0104 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8206 0.4541 1.1499 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0214 -0.3620 1.1476 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0393 -1.4431 0.2585 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1473 -2.2788 0.1819 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2441 -2.0420 0.9910 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2443 -0.9842 1.8716 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1220 -0.1751 1.9174 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3639 -0.7931 2.6563 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3967 0.2868 3.5675 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3175 -2.9135 0.8660 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8085 0.2105 0.3551 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7056 0.9137 0.3169 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 0.5720 -0.5726 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2687 3.7993 1.9511 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2983 -2.8604 -5.0810 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0160 -2.4107 -3.8514 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3612 -2.6347 -1.1397 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6642 -1.5577 0.5408 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7292 1.4453 -0.9439 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3252 1.4185 3.7577 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8133 1.2605 5.4571 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4564 2.7876 4.4999 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6966 1.1099 2.9326 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4212 -0.4817 2.6436 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2113 1.9723 0.8279 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4509 0.7971 0.8048 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1582 -0.9121 -1.3042 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0823 -1.8681 0.7200 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9198 0.1286 -1.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6401 -0.0586 -2.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2926 -2.8071 -2.8765 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6512 -1.4400 -5.4836 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0215 -1.0107 -4.2324 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1542 0.7122 -5.9345 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5432 -0.7829 -6.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1229 1.3632 -5.7153 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2411 -0.8417 -2.1427 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5399 2.9428 0.1762 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5202 1.7627 2.6754 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1845 -1.6313 -0.3724 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1419 -3.1171 -0.5244 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1485 0.6316 2.6061 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4201 0.4928 3.9412 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0173 1.2364 3.1327 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7444 0.0803 4.4630 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2548 -2.7096 1.1750 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8460 -0.2789 -1.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7647 3.6797 2.8255 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4648 -3.6031 -4.4519 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6118 -1.6150 -3.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2611 -2.9941 -1.3305 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3422 -0.9067 0.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3376 2.3138 -0.6473 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 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 33 38 1 0 29 39 1 0 39 40 1 0 40 41 2 0 24 42 1 0 15 43 1 0 14 44 1 0 9 45 1 0 8 46 1 0 7 47 1 0 11 6 1 0 20 13 1 0 41 22 1 0 40 25 1 0 35 30 1 0 1 48 1 0 1 49 1 0 1 50 1 0 5 51 1 0 5 52 1 0 6 53 1 1 7 54 1 1 8 55 1 6 9 56 1 1 10 57 1 6 13 58 1 6 14 59 1 1 15 60 1 6 16 61 1 1 17 62 1 0 17 63 1 0 18 64 1 0 20 65 1 1 23 66 1 0 28 67 1 0 31 68 1 0 32 69 1 0 35 70 1 0 37 71 1 0 37 72 1 0 37 73 1 0 38 74 1 0 41 75 1 0 42 76 1 0 43 77 1 0 44 78 1 0 45 79 1 0 46 80 1 0 47 81 1 0 M END

Standard InCHIKey	XEOMCDDFSGTWFB-RXFKRDKPSA-N
Standard InCHI	InChI=1S/C30H34O17/c1-11(32)42-10-21-24(37)25(38)27(40)29(46-21)47-28-26(39)23(36)20(9-31)45-30(28)43-13-6-15(34)22-16(35)8-17(44-19(22)7-13)12-3-4-14(33)18(5-12)41-2/h3-8,20-21,23-31,33-34,36-40H,9-10H2,1-2H3/t20-,21-,23-,24-,25+,26+,27-,28-,29+,30-/m1/s1
SMILES	CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1cc(c2c(=O)cc(c3ccc(c(c3)OC)O)oc2c1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.18	Volume:	610.359 ? Van der Waals volume.
Dense:	1.091	LogP:	-0.125 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.868 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.251 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	31.0
TPSA:	264.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.12	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.768	Fsp³:	0.467
MCE-18:	120.909 ? 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:	0.658	Fluc inhibitor:	0.303 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.97 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.646 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.063	Promiscuous compounds:	0.438

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.321	MDCK Permeability:	-5.204
Pgp-inhibitor:	0.0	Pgp-substrate:	0.317
PAMPA:	0.968 ? 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):	0.988
20% Bioavailability (F20%):	0.828	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.087
Plasma Protein Binding (PPB):	78.009%	Volume Distribution (VD):	-0.166
Fu:	19.215% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.271
BSEP inhibitor:	0.012

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.142
HLM stability:	0.007 ? 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):

1.231

Half-life (T1/2):

3.799

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.041
Human Hepatotoxicity (H-HT):	0.589	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.98	Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.008	Skin Sensitization:	1.0
Carcinogencity:	0.294	Eye Corrosion:	0.0
Eye Irritation:	0.109	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.95
Hematotoxicity:	0.293	Drug-induced Nephrotoxicity:	0.715
Genotoxicity:	0.936	RPMI-8226 Immunitoxicity:	0.167
A549 Cytotoxicity:	0.556	Hek293 Cytotoxicity:	0.426
BCF:	0.395 ? 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:	2.931 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.518 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.661 ? 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
NPO874	Narthecium asiaticum	Species	Nartheciaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14980692]
NPO244	Stachyurus himalaicus	Species	Stachyuraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17851408]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[20167482]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21608987]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[27113553]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2801129]
NPO23104	Wedelia scaberrima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2277	Angylocalyx braunii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4000	Archidendron lucidum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7235	Brachychiton populneum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2213	Chavica betle	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5599	Chrysocoma peduncularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4786	Chrysotila lamellosa	Species	Isochrysidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7379	Clostridium butyricum	Species	Clostridiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1384	Cucumis myriocarpus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO962	Vernonanthura pinguis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO874	Narthecium asiaticum	Species	Nartheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7897	Passiflora foetida	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7026	Vismia orientalis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO591	Penicillium meleagrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5154	Tsuga diversifolia	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7098	Phebalium ambiens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1249	Euphorbia sieboldiana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO244	Stachyurus himalaicus	Species	Stachyuraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7026	Vismia orientalis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1384	Cucumis myriocarpus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7026	Vismia orientalis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1384	Cucumis myriocarpus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO244	Stachyurus himalaicus	Species	Stachyuraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO874	Narthecium asiaticum	Species	Nartheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5599	Chrysocoma peduncularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO591	Penicillium meleagrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO244	Stachyurus himalaicus	Species	Stachyuraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO962	Vernonanthura pinguis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4000	Archidendron lucidum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4786	Chrysotila lamellosa	Species	Isochrysidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10856	Passiflora edulis	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7098	Phebalium ambiens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2213	Chavica betle	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7026	Vismia orientalis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1249	Euphorbia sieboldiana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7379	Clostridium butyricum	Species	Clostridiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2277	Angylocalyx braunii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7235	Brachychiton populneum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5154	Tsuga diversifolia	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7897	Passiflora foetida	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23104	Wedelia scaberrima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1384	Cucumis myriocarpus	Species	Cucurbitaceae	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

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 NPC269904 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	16083
0.1-0.2	28680
0.2-0.3	4093
0.3-0.4	657
0.4-0.5	253
0.5-0.6	66
0.6-0.7	18
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	Natural Product ID
0.8298	Intermediate Similarity	NPC195257
0.7255	Intermediate Similarity	NPC11468
0.7156	Intermediate Similarity	NPC120952
0.7103	Intermediate Similarity	NPC68592
0.7037	Intermediate Similarity	NPC298666
0.6979	Remote Similarity	NPC8856
0.6939	Remote Similarity	NPC65003
0.6916	Remote Similarity	NPC488087
0.6881	Remote Similarity	NPC198199
0.6869	Remote Similarity	NPC115674
0.6842	Remote Similarity	NPC311830
0.6822	Remote Similarity	NPC311850
0.6789	Remote Similarity	NPC488086
0.6759	Remote Similarity	NPC488083
0.6609	Remote Similarity	NPC35924
0.6562	Remote Similarity	NPC80188
0.6392	Remote Similarity	NPC601144
0.6214	Remote Similarity	NPC122809
0.6154	Remote Similarity	NPC262222
0.6126	Remote Similarity	NPC473644
0.6111	Remote Similarity	NPC253685
0.6106	Remote Similarity	NPC488088
0.6038	Remote Similarity	NPC209296
0.5981	Remote Similarity	NPC479766
0.5966	Remote Similarity	NPC199172
0.5962	Remote Similarity	NPC22062
0.5962	Remote Similarity	NPC473634
0.5962	Remote Similarity	NPC138811
0.5926	Remote Similarity	NPC475382
0.59	Remote Similarity	NPC22832
0.59	Remote Similarity	NPC243930
0.5849	Remote Similarity	NPC46202
0.5849	Remote Similarity	NPC240306
0.5842	Remote Similarity	NPC607707
0.5816	Remote Similarity	NPC95090
0.5816	Remote Similarity	NPC27408
0.5752	Remote Similarity	NPC472993
0.5714	Remote Similarity	NPC44931
0.5701	Remote Similarity	NPC64051
0.5688	Remote Similarity	NPC488089
0.566	Remote Similarity	NPC210073
0.5636	Remote Similarity	NPC220173
0.5596	Remote Similarity	NPC473623
0.5596	Remote Similarity	NPC229409
0.5556	Remote Similarity	NPC39360
0.5556	Remote Similarity	NPC29763
0.5556	Remote Similarity	NPC137062
0.5556	Remote Similarity	NPC210003
0.5545	Remote Similarity	NPC270675
0.5545	Remote Similarity	NPC195685
0.5536	Remote Similarity	NPC135358
0.5534	Remote Similarity	NPC602805
0.55	Remote Similarity	NPC189142
0.55	Remote Similarity	NPC77660
0.5481	Remote Similarity	NPC601586
0.5455	Remote Similarity	NPC209550
0.5455	Remote Similarity	NPC32641
0.5455	Remote Similarity	NPC256188
0.5455	Remote Similarity	NPC35119
0.5447	Remote Similarity	NPC25946
0.5446	Remote Similarity	NPC101636
0.5431	Remote Similarity	NPC480441
0.5431	Remote Similarity	NPC25523
0.5429	Remote Similarity	NPC172807
0.5429	Remote Similarity	NPC211594
0.5405	Remote Similarity	NPC142142
0.5403	Remote Similarity	NPC21359
0.5403	Remote Similarity	NPC460984
0.5398	Remote Similarity	NPC472994
0.5391	Remote Similarity	NPC473072
0.5377	Remote Similarity	NPC254540
0.5364	Remote Similarity	NPC65711
0.5333	Remote Similarity	NPC190003
0.531	Remote Similarity	NPC298171
0.5304	Remote Similarity	NPC89052
0.5294	Remote Similarity	NPC181712
0.5289	Remote Similarity	NPC471030
0.5288	Remote Similarity	NPC601710
0.5273	Remote Similarity	NPC64425
0.5273	Remote Similarity	NPC153755
0.5243	Remote Similarity	NPC27942
0.5238	Remote Similarity	NPC220169
0.5234	Remote Similarity	NPC239549
0.5234	Remote Similarity	NPC606546
0.5149	Remote Similarity	NPC331652
0.5098	Remote Similarity	NPC261866
0.5098	Remote Similarity	NPC19709
0.5088	Remote Similarity	NPC479765
0.5085	Remote Similarity	NPC173837

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC269904 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4847
0.1-0.2	4227
0.2-0.3	65
0.3-0.4	7
0.4-0.5	3
0.5-0.6	0
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6038	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