NPASS Compound

Natural Product: NPC87781

Natural Product ID	NPC87781
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DHHFDKNIEVKVKS-RYGANQNKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6325438
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001435] Betalains [CHEMONTID:0001434] Betacyanins 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 65 68 0 0 0 0 0 0 0 0999 V2000 -3.1427 -0.3011 -0.0475 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3329 -0.8436 0.1426 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5648 -0.3070 -0.3885 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7427 -0.6553 0.1630 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9556 -0.1093 -0.3817 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9021 0.6802 -1.3574 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2031 -0.4238 0.1344 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7383 -1.5621 1.2723 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5233 -1.7900 1.9910 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4253 -2.0820 0.9576 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6336 -2.8284 3.0160 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7274 -3.4293 3.2088 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5308 -3.1605 3.7853 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9112 0.8982 -0.8081 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8382 1.5218 -1.0460 N 0 0 0 0 0 4 0 0 0 0 0 0 -0.5242 1.1309 -0.5548 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0816 0.5871 0.6273 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2476 0.2867 0.8603 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1690 0.5402 -0.1232 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7118 1.1024 -1.3396 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4020 1.3930 -1.5555 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3715 2.0089 -2.6839 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5122 2.6807 -1.8529 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5221 3.2202 -2.7302 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6138 2.6470 -2.9324 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3588 4.4313 -3.4257 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5041 0.3167 -0.0861 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3804 -0.1886 0.8500 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9645 -1.4607 0.3454 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4379 -1.5867 0.3252 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2245 -0.3618 0.6208 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4161 0.9105 0.4984 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3160 1.4186 -0.9074 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5482 0.6615 -1.7498 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2654 0.7977 1.1898 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6989 -0.4112 1.9402 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8907 -2.0724 -0.9289 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4521 -2.5557 1.0862 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6553 -0.2588 2.0559 O 0 0 0 0 0 1 0 0 0 0 0 0 -2.2585 -0.8062 0.3734 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5348 0.3694 -1.2303 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0647 -0.2765 -0.4104 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6466 -2.0333 1.5177 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2415 -0.8182 2.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8418 -2.9231 0.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4765 -2.3629 1.4365 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5939 -3.8159 4.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8243 1.3485 -1.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7977 0.4030 1.4415 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4290 1.3105 -2.1301 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1939 2.7529 -3.2375 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8409 1.2111 -3.2549 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9863 3.4424 -1.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8105 4.5360 -4.3233 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8315 -0.4226 1.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5812 -1.6802 -0.6966 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8026 -2.3901 1.0361 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1241 -0.2837 -0.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0341 1.6883 1.0488 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3494 1.5297 -1.2993 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9072 2.4542 -0.8535 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9638 0.6609 -2.6665 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8763 0.5164 2.2829 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5202 -3.0073 -0.9911 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1768 -2.2483 1.9864 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 3 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 5 7 1 0 4 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 11 12 2 0 11 13 1 0 1 14 1 0 14 15 2 3 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 19 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 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 18 39 1 0 10 2 1 0 23 15 1 0 35 28 1 0 21 16 1 0 1 40 1 0 3 41 1 0 7 42 1 0 8 43 1 0 9 44 1 1 10 45 1 0 10 46 1 0 13 47 1 0 14 48 1 0 17 49 1 0 20 50 1 0 22 51 1 0 22 52 1 0 23 53 1 1 26 54 1 0 28 55 1 1 29 56 1 6 30 57 1 1 31 58 1 6 32 59 1 1 33 60 1 0 33 61 1 0 34 62 1 0 36 63 1 0 37 64 1 0 38 65 1 0 M CHG 2 15 1 39 -1 M END

Standard InCHIKey	DHHFDKNIEVKVKS-RYGANQNKSA-N
Standard InCHI	InChI=1S/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27,29-31H,4-5,8H2,(H4,28,32,33,34,35,36,37)/t12-,14+,17-,18-,19+,20-,24-/m1/s1
SMILES	C(=C1C=C(C(=O)O)N[C@H](C1)C(=O)O)C=[N+]1c2cc(c(cc2C[C@H]1C(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[O-]

Calculated Properties

Physi-Chem Properties

Molecular Weight:	550.14	Volume:	501.973 ? Van der Waals volume.
Dense:	1.096	LogP:	-1.845 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.749 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.149 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	27.0
TPSA:	249.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.152	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.378	Fsp³:	0.417
MCE-18:	102.353 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.663	Fluc inhibitor:	0.324 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.044 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.642 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.069	Promiscuous compounds:	0.146

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.253	MDCK Permeability:	-5.172
Pgp-inhibitor:	0.0	Pgp-substrate:	0.029
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):	0.487
20% Bioavailability (F20%):	0.448	30% Bioavailability (F30%):	0.863
50% Bioavailability (F50%):	0.89

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.975
Plasma Protein Binding (PPB):	51.396%	Volume Distribution (VD):	-0.528
Fu:	47.88% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

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:	0.0
HLM stability:	0.0 ? 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):

1.367

Half-life (T1/2):

4.009

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.853	Drug-induced Liver Injury (DILI):	0.985
AMES Toxicity:	0.737	Rat Oral Acute Toxicity:	0.145
Maximum Recommended Daily Dose:	0.104	Skin Sensitization:	1.0
Carcinogencity:	0.028	Eye Corrosion:	0.0
Eye Irritation:	0.16	Respiratory Toxicity:	0.131
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.989
Hematotoxicity:	0.115	Drug-induced Nephrotoxicity:	0.955
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.015
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.008
BCF:	0.181 ? 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:	2.907 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.511 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.611 ? 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
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.carres.2012.01.012]
NPO4302	Stylocheilus longicauda	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924193]
NPO4302	Stylocheilus longicauda	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076568]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880321]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22708987]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	bark	n.a.	PMID[22708987]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614422]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562741]
NPO6545	Artemisia sieversiana	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29122483]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29517238]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31625751]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	Along the Valencian coast, Spain	2020-Jun&Jul	PMID[35161358]
NPO4302	Stylocheilus longicauda	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[4833645]
NPO1653	Streptomyces longissimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[903851]
NPO118	Ustilago maydis	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1653	Streptomyces longissimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10583	Streptomyces echinatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5427	Sabal peregrina	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6048	Sarcodictyon roseum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4302	Stylocheilus longicauda	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6545	Artemisia sieversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4080	Salix purpurea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8775	Streptomyces rubellomurinus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5525	Mesembryanthemum edule	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7507	Portulaca grandiflora	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15839	Nicotiana repanda	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1034	Ophiorrhiza liukiuensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8240	Opuntia vulgaris	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Herb	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO118	Ustilago maydis	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6545	Artemisia sieversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7507	Portulaca grandiflora	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5525	Mesembryanthemum edule	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8240	Opuntia vulgaris	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1034	Ophiorrhiza liukiuensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4080	Salix purpurea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1034	Ophiorrhiza liukiuensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6545	Artemisia sieversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5525	Mesembryanthemum edule	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8240	Opuntia vulgaris	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7507	Portulaca grandiflora	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4080	Salix purpurea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO118	Ustilago maydis	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6545	Artemisia sieversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4080	Salix purpurea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO118	Ustilago maydis	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15839	Nicotiana repanda	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7507	Portulaca grandiflora	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7271	Stachys affinis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10583	Streptomyces echinatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4302	Stylocheilus longicauda	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4080	Salix purpurea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1034	Ophiorrhiza liukiuensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6545	Artemisia sieversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5427	Sabal peregrina	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1653	Streptomyces longissimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8240	Opuntia vulgaris	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9978	Indigofera microcarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9332	Corydalis longipes	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6048	Sarcodictyon roseum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4506	Corydalis paniculigera	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8775	Streptomyces rubellomurinus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2178	Cachrys trifida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12980	Acronychia pedunculata	Species	Rutaceae	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 NPC87781 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	19357
0.1-0.2	28747
0.2-0.3	1667
0.3-0.4	88
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC87781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4534
0.1-0.2	4589
0.2-0.3	22
0.3-0.4	5
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