NPASS Compound

Natural Product: NPC282435

Natural Product ID	NPC282435
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YSNOWCXOGYYBJB-DYUFTDJRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24862642
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 105109 0 0 0 0 0 0 0 0999 V2000 -8.6863 0.2730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2768 0.7860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0163 2.2632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1277 -0.1782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7181 0.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3086 0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0481 -0.6293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 -1.1424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -0.1782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2829 1.8338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6458 0.3784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0877 -0.0351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1667 1.0069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4506 -1.4905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8924 -1.9040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2553 -3.3594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6972 -3.7729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0601 -5.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9811 -6.2703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5392 -5.8568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1763 -4.4014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3440 -7.7257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4054 3.4980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6659 4.9753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3415 5.6795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1924 6.6436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9567 7.6078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3662 7.0948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6267 5.6176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5153 8.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2548 9.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4039 10.5004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1434 11.9776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2925 12.9418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7020 12.4287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9625 10.9515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8134 9.9873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3720 10.4385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6325 8.9613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8511 13.3929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2625 4.6375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2278 6.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9018 3.3934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 4.6370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2522 6.0553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2369 4.5323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0757 5.7759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5720 5.6712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2296 4.3231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7259 4.2184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5647 5.4620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9072 6.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4108 6.9148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0611 5.3573 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 0.3349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -2.1065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3086 -2.1065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1993 1.6825 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1733 -1.1366 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0958 -0.2401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3808 -1.1267 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2312 1.7444 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 2.1469 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5369 -0.8122 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 -2.4414 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4132 -1.3761 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7388 1.1162 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0415 1.1296 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7717 2.0166 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3715 -2.5325 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9715 -0.8620 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7762 -2.7309 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5020 -5.6418 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4602 -6.8988 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7344 -3.9879 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2650 -8.7677 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6401 2.0165 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1650 4.9230 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1803 6.9230 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7718 5.4946 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1566 7.7927 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9248 7.5459 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8453 10.0492 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7339 12.4906 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0320 14.4190 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0739 8.5101 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1097 9.2217 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1553 8.7008 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8930 7.4841 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2606 12.8799 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6767 6.7543 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8945 3.1841 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4181 7.1241 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3908 3.0795 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3835 2.8702 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7460 8.0537 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7533 8.2630 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8999 6.6009 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 1.6205 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9720 -1.7691 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7181 -2.6196 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 13 12 1 6 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 13 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 1 0 39 44 1 0 29 45 1 0 28 46 1 0 27 47 1 0 47 48 1 0 48 49 2 0 48 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 53 54 1 0 54 55 2 0 55 56 1 0 56 57 2 0 55 58 1 0 9 59 1 0 8 60 1 0 7 61 1 0 11 6 1 0 45 13 1 0 57 52 1 0 25 20 1 0 41 36 1 0 1 62 1 0 1 63 1 0 1 64 1 0 5 65 1 0 5 66 1 0 6 67 1 6 7 68 1 1 8 69 1 6 9 70 1 1 10 71 1 1 14 72 1 0 14 73 1 0 18 74 1 0 19 75 1 0 21 76 1 0 22 77 1 0 24 78 1 0 25 79 1 0 26 80 1 0 27 81 1 1 28 82 1 6 29 83 1 1 30 84 1 0 30 85 1 0 34 86 1 0 35 87 1 0 37 88 1 0 38 89 1 0 41 90 1 0 43 91 1 0 43 92 1 0 43 93 1 0 44 94 1 0 46 95 1 0 50 96 1 0 51 97 1 0 53 98 1 0 54 99 1 0 56100 1 0 57101 1 0 58102 1 0 59103 1 0 60104 1 0 61105 1 0 M END

Standard InCHIKey	YSNOWCXOGYYBJB-DYUFTDJRSA-N
Standard InCHI	InChI=1S/C42H44O19/c1-23(43)55-20-31-36(50)38(52)39(53)41(58-31)61-42(22-57-34(48)16-8-24-3-11-27(44)12-4-24)40(59-35(49)18-9-25-5-13-28(45)14-6-25)37(51)32(60-42)21-56-33(47)17-10-26-7-15-29(46)30(19-26)54-2/h3-19,31-32,36-41,44-46,50-53H,20-22H2,1-2H3/b16-8+,17-10+,18-9+/t31-,32-,36-,37-,38+,39-,40+,41-,42+/m1/s1
SMILES	CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@]1(COC(=O)/C=C/c2ccc(cc2)O)[C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)OC)O)O1)O)OC(=O)/C=C/c1ccc(cc1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	852.25	Volume:	817.037 ? Van der Waals volume.
Dense:	1.043	LogP:	1.596 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.879 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.649 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	20.0	Rigid Bonds:	36.0
TPSA:	283.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.06	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.206	Fsp³:	0.333
MCE-18:	122.893 ? 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:	0.963	Fluc inhibitor:	0.999 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.16 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.151	Promiscuous compounds:	0.135

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.152	MDCK Permeability:	-5.373
Pgp-inhibitor:	0.742	Pgp-substrate:	0.008
PAMPA:	0.945 ? 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):	0.039
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	84.855%	Volume Distribution (VD):	-0.316
Fu:	13.373% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.655
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.976
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.655 ? 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):

1.193

Half-life (T1/2):

3.414

ADMET: Toxicity

hERG Blockers:	0.079	hERG Blockers (10um):	0.625
Human Hepatotoxicity (H-HT):	0.461	Drug-induced Liver Injury (DILI):	0.905
AMES Toxicity:	0.911	Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.686	Skin Sensitization:	1.0
Carcinogencity:	0.019	Eye Corrosion:	0.0
Eye Irritation:	0.023	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.119	Ototoxicity:	0.853
Hematotoxicity:	0.05	Drug-induced Nephrotoxicity:	0.804
Genotoxicity:	0.858	RPMI-8226 Immunitoxicity:	0.219
A549 Cytotoxicity:	0.393	Hek293 Cytotoxicity:	0.912
BCF:	0.358 ? 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:	3.481 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.989 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.58 ? 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
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO5577	Methylobacterium rhodinum	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15933032]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[18620454]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	red sea	n.a.	PMID[18656986]
NPO25024	Lycoris traubii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19013823]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[21542602]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21542602]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO5577	Methylobacterium rhodinum	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28862	Crotalaria anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29311	Securinega melanthesoides	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26970	Lygodium flexuosum	Species	Lygodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29003	Croton poilanei	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29362	Euonymus sachalinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28984	Dasymaschalon sootepense	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14557	Dictyopteris undulata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26970	Lygodium flexuosum	Species	Lygodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28862	Crotalaria anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO26970	Lygodium flexuosum	Species	Lygodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28862	Crotalaria anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29449	Boehmeria nivea	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29449	Boehmeria nivea	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26970	Lygodium flexuosum	Species	Lygodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21700	Capsicum tetragonum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14557	Dictyopteris undulata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28820	Saccharum spontaneum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25024	Lycoris traubii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28984	Dasymaschalon sootepense	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11769	Eupatorium adenophorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29199	Lobophytum chevalieri	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28862	Crotalaria anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29379	Felicia erigeroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29188	Guatteria melosma	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29046	Tsuga mertensiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29362	Euonymus sachalinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29413	Lupinus paniculatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29311	Securinega melanthesoides	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28754	Thelephora palmata	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28666	Strychnos staudtii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29449	Boehmeria nivea	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29003	Croton poilanei	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5577	Methylobacterium rhodinum	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28783	Dictyoloma incanescens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29034	Suberea mollis	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	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 NPC282435 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	11284
0.1-0.2	33052
0.2-0.3	4533
0.3-0.4	781
0.4-0.5	148
0.5-0.6	33
0.6-0.7	13
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC201148
0.9625	High Similarity	NPC125823
0.9625	High Similarity	NPC7145
0.9625	High Similarity	NPC143480
0.881	High Similarity	NPC3460
0.8068	Intermediate Similarity	NPC215095
0.8023	Intermediate Similarity	NPC300262
0.7955	Intermediate Similarity	NPC85192
0.75	Intermediate Similarity	NPC28637
0.7053	Intermediate Similarity	NPC28651
0.7	Intermediate Similarity	NPC83743
0.6947	Remote Similarity	NPC261122
0.6889	Remote Similarity	NPC262182
0.6556	Remote Similarity	NPC226005
0.6526	Remote Similarity	NPC287615
0.6526	Remote Similarity	NPC199311
0.6484	Remote Similarity	NPC471881
0.6444	Remote Similarity	NPC472612
0.6224	Remote Similarity	NPC472611
0.6224	Remote Similarity	NPC210611
0.6211	Remote Similarity	NPC80732
0.6111	Remote Similarity	NPC225307
0.6042	Remote Similarity	NPC216819
0.6022	Remote Similarity	NPC476869
0.5978	Remote Similarity	NPC35288
0.5957	Remote Similarity	NPC90896
0.5851	Remote Similarity	NPC471882
0.5816	Remote Similarity	NPC192763
0.5806	Remote Similarity	NPC45224
0.567	Remote Similarity	NPC476865
0.5657	Remote Similarity	NPC283839
0.5532	Remote Similarity	NPC291296
0.551	Remote Similarity	NPC289967
0.55	Remote Similarity	NPC11411
0.5495	Remote Similarity	NPC484988
0.5474	Remote Similarity	NPC471405
0.5464	Remote Similarity	NPC476868
0.5424	Remote Similarity	NPC246024
0.5368	Remote Similarity	NPC10205
0.5361	Remote Similarity	NPC476866
0.5288	Remote Similarity	NPC600370
0.5222	Remote Similarity	NPC479473
0.5222	Remote Similarity	NPC275721
0.5222	Remote Similarity	NPC288416
0.5222	Remote Similarity	NPC479468
0.5222	Remote Similarity	NPC479474
0.5217	Remote Similarity	NPC291153
0.5213	Remote Similarity	NPC219677
0.5172	Remote Similarity	NPC157554
0.5164	Remote Similarity	NPC601579
0.5161	Remote Similarity	NPC34293
0.5155	Remote Similarity	NPC471883
0.5155	Remote Similarity	NPC484687
0.5098	Remote Similarity	NPC488081
0.5096	Remote Similarity	NPC173343
0.5091	Remote Similarity	NPC479771
0.5052	Remote Similarity	NPC281798

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC282435 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4110
0.1-0.2	4939
0.2-0.3	97
0.3-0.4	3
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data