NPASS Compound

Natural Product: NPC72678

Natural Product ID	NPC72678
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FKJLKGUXRIDXTL-UKHQZXFMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	56600064
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0004361] Acylaminobenzoic acid and derivatives

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

Chemical Representations

RDKit 3D 79 80 0 0 0 0 0 0 0 0999 V2000 -6.0787 4.4369 -0.6597 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2059 4.7315 0.5531 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8145 5.1072 0.1650 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1416 3.9857 -0.6380 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1059 2.7748 0.2337 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4873 1.5530 -0.3275 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5869 0.3879 0.6446 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5542 0.4199 1.7638 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8697 1.3410 2.8939 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3169 0.5136 1.2442 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8495 -0.1774 1.1572 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9597 -1.2551 1.7301 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8848 0.4677 0.3437 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1493 0.6204 -1.0628 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6328 -0.4570 -1.9181 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1896 0.7408 -0.7867 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0303 1.7789 -0.6722 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5783 2.9193 -0.8459 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1793 0.0670 0.2151 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0897 -0.0938 1.1019 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4481 -0.5314 0.8260 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3288 -0.6637 1.8756 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6220 -1.0746 1.6415 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0735 -1.3621 0.3786 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1967 -1.2324 -0.6829 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8865 -0.8179 -0.4596 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0208 -0.6932 -1.5353 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6922 -1.5343 -1.9693 N 0 0 0 0 0 0 0 0 0 0 0 0 8.4924 -2.5237 -2.1438 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -2.8504 -3.3975 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7208 0.1788 2.4175 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3957 -0.8238 -0.1258 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4328 -1.7726 -0.2087 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4764 -1.4685 0.4234 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2963 -3.0269 -0.9822 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0111 -2.7562 -2.4435 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3793 -4.0256 -0.3582 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9432 -4.3698 1.0135 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0022 -3.4098 -0.2333 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1367 4.6515 -0.3372 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0465 3.3813 -0.9596 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8746 5.1409 -1.4888 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6543 5.6306 1.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2894 3.9179 1.2645 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8190 6.0556 -0.3957 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2175 5.1775 1.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7760 3.7941 -1.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1853 4.3511 -1.0031 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6702 3.0210 1.2315 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1871 2.4994 0.4428 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0399 1.2479 -1.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5771 0.3899 1.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6511 -0.6305 2.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2943 2.2907 2.9022 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9562 1.5217 2.9406 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5859 0.8513 3.8971 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8922 1.5742 0.7383 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5682 1.6180 -1.3873 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4736 -0.0704 -2.5660 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0934 -1.3187 -1.3603 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8802 -0.8224 -2.6493 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0391 -0.4537 2.8934 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3046 -1.1755 2.4719 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1100 -1.6842 0.2500 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6331 -1.5544 -1.9446 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7858 -3.1239 -1.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9527 -2.1964 -4.1574 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8434 0.5529 2.6909 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3222 -3.5015 -0.9767 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0428 -2.2944 -2.6336 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1868 -3.7067 -2.9900 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8391 -2.0723 -2.7866 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3018 -4.9418 -0.9454 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0216 -4.5033 0.9044 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6319 -3.5774 1.7065 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4703 -5.3396 1.2953 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7601 -2.9287 -1.1876 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0876 -2.6711 0.6093 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2811 -4.2047 -0.0120 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 8 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 2 0 13 19 1 0 19 20 2 3 20 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 25 28 1 0 28 29 2 3 29 30 1 0 20 31 1 0 7 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 37 39 1 0 17 6 1 0 26 21 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 0 2 44 1 0 3 45 1 0 3 46 1 0 4 47 1 0 4 48 1 0 5 49 1 0 5 50 1 0 6 51 1 6 7 52 1 1 8 53 1 1 9 54 1 0 9 55 1 0 9 56 1 0 13 57 1 1 14 58 1 6 15 59 1 0 15 60 1 0 15 61 1 0 22 62 1 0 23 63 1 0 24 64 1 0 27 65 1 0 29 66 1 0 30 67 1 0 31 68 1 0 35 69 1 6 36 70 1 0 36 71 1 0 36 72 1 0 37 73 1 0 38 74 1 0 38 75 1 0 38 76 1 0 39 77 1 0 39 78 1 0 39 79 1 0 M END

Standard InCHIKey	FKJLKGUXRIDXTL-UKHQZXFMSA-N
Standard InCHI	InChI=1S/C28H40N2O9/c1-7-8-9-11-20-24(39-26(34)16(4)15(2)3)18(6)38-28(36)22(17(5)37-27(20)35)30-25(33)19-12-10-13-21(23(19)32)29-14-31/h10,12-18,20,22,24,32H,7-9,11H2,1-6H3,(H,29,31)(H,30,33)/t16-,17+,18-,20+,22-,24-/m0/s1
SMILES	CCCCC[C@@H]1[C@H]([C@H](C)OC(=O)[C@H]([C@@H](C)OC1=O)N=C(c1cccc(c1O)N=CO)O)OC(=O)[C@@H](C)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	548.27	Volume:	555.745 ? Van der Waals volume.
Dense:	0.987	LogP:	4.361 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.706 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.899 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	20.0
TPSA:	164.31 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.125	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.425	Fsp³:	0.607
MCE-18:	64.444 ? 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:	0	PAINS Alert:	1
Colloidal aggregators:	0.523	Fluc inhibitor:	0.152 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.206 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.783 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.011	Promiscuous compounds:	0.263

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.276	MDCK Permeability:	-4.851
Pgp-inhibitor:	0.604	Pgp-substrate:	0.972
PAMPA:	0.456 ? 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):	0.003
20% Bioavailability (F20%):	0.19	30% Bioavailability (F30%):	0.79
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.84
Plasma Protein Binding (PPB):	92.155%	Volume Distribution (VD):	-0.353
Fu:	7.939% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.046
BSEP inhibitor:	0.969

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.884 ? 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):

1.188

Half-life (T1/2):

1.408

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.04
Human Hepatotoxicity (H-HT):	0.996	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.548	Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.018	Skin Sensitization:	1.0
Carcinogencity:	0.358	Eye Corrosion:	0.001
Eye Irritation:	0.959	Respiratory Toxicity:	0.172
Drug-induced Neurotoxicity:	0.058	Ototoxicity:	0.662
Hematotoxicity:	0.72	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.014	Hek293 Cytotoxicity:	0.018
BCF:	0.719 ? 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:	3.636 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.199 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.63 ? 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
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	DOI[10.1002/hlca.201300170.]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141877]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12735688]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14575429]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23510022]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31465225]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO23611	Conyza pallidiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6439	Lithospermum carolinense	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22028	Ligularia lankongensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23781	Lemaireocereus stellatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18919	Helenium amarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23113	Garcinia neglecta	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17801	Drimia altissima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21915	Diospyros chloroxylon	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24063	Evasterias retifera	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26544	Bolboschoenus maritimus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23431	Aconitum umbrosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23175	Streptomyces antibioticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13151.1	Pulsatilla vulgaris subsp. grandis	Subspecies	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21747	Sideritis glacialis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21175	Senecio retrorsus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23686	Selinum tenuifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16976	Phebalium rotundifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19539	Uperoleia rugosa	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23363	Nodulisporium hinnuleum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20290	Vernonia arkansana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9228.2	Narcissus pseudonarcissus subsp. radinganorum	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23981	Maytenus disticha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23268	Xanthorrhoea reflexa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23688	Lonicera nitida	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18919	Helenium amarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21175	Senecio retrorsus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21175	Senecio retrorsus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23431	Aconitum umbrosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18919	Helenium amarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17801	Drimia altissima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18919	Helenium amarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21175	Senecio retrorsus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23781	Lemaireocereus stellatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21915	Diospyros chloroxylon	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23688	Lonicera nitida	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23363	Nodulisporium hinnuleum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23686	Selinum tenuifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23611	Conyza pallidiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26544	Bolboschoenus maritimus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24063	Evasterias retifera	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23431	Aconitum umbrosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19539	Uperoleia rugosa	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9228.2	Narcissus pseudonarcissus subsp. radinganorum	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22028	Ligularia lankongensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23268	Xanthorrhoea reflexa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20290	Vernonia arkansana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23175	Streptomyces antibioticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23981	Maytenus disticha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6439	Lithospermum carolinense	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17801	Drimia altissima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13151.1	Pulsatilla vulgaris subsp. grandis	Subspecies	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18919	Helenium amarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16976	Phebalium rotundifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21747	Sideritis glacialis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23113	Garcinia neglecta	Species	Clusiaceae	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
MIC	2

Activity Type	# Activity
Organism	2

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
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	5.0	ug.mL-1	PMID[35063731]

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 NPC72678 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	11642
0.1-0.2	37285
0.2-0.3	920
0.3-0.4	7
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8986	High Similarity	NPC154662
0.8986	High Similarity	NPC254100
0.8611	High Similarity	NPC95412
0.8333	Intermediate Similarity	NPC83241

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC72678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2640
0.1-0.2	6347
0.2-0.3	163
0.3-0.4	0
0.4-0.5	0
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