NPASS Compound

Natural Product: NPC138261

Natural Product ID	NPC138261
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TZVDWGXUGGUMCE-JVHXOXOBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	111220
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 -5.2567 -2.5822 1.5497 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9119 -1.3441 0.7033 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9134 -1.7629 -0.7114 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9829 -1.0426 -1.6180 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4450 0.2628 -1.0152 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7283 1.1153 -0.8867 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5086 0.8236 -2.0387 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0692 0.8276 -1.7675 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7229 0.9923 -0.3003 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2638 2.3429 0.0448 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7430 1.0015 -0.0701 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5237 1.9884 -0.4424 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0045 2.0682 -0.2435 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4660 0.6314 -0.3026 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9198 0.5513 -0.5061 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7727 1.4662 0.3251 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1343 1.0153 -1.9661 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4504 -0.8655 -0.4770 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2691 -1.7876 -0.3387 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4419 -1.4858 0.8832 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8427 -0.0879 0.8308 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1470 0.5514 2.1699 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3379 -0.1724 0.5793 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5759 -0.5018 1.8050 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8712 -0.0841 1.8155 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4040 -0.1428 0.4050 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1792 -1.4994 -0.0913 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8902 0.1400 0.3489 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6540 -0.7801 1.2589 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0529 -0.0577 2.5619 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3732 -1.0399 0.5694 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2694 -3.1151 1.6648 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9744 -3.2244 1.0406 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5427 -2.2620 2.5641 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7522 -0.6287 0.9564 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9902 -1.7575 -1.0633 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6378 -2.8584 -0.7669 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6238 -0.6815 -2.4878 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2190 -1.6368 -2.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6278 1.9211 -1.6733 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7555 1.6517 0.0711 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6439 0.5925 -1.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8675 1.8817 -2.2283 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6377 0.3490 -3.0605 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6182 1.7517 -2.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4757 0.0068 -2.2228 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1945 2.6391 1.0917 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6984 3.0790 -0.5939 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2974 2.5429 -0.3782 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1520 2.8804 -0.9646 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2054 2.5503 0.7320 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5076 2.6461 -1.0218 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9753 0.2153 -1.2371 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2237 2.3336 0.7012 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6021 1.8980 -0.3097 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3487 0.9079 1.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2531 0.7682 -2.5843 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0665 0.5542 -2.3352 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3003 2.1125 -1.9665 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9888 -1.1604 -1.4006 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6902 -1.7619 -1.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6644 -2.8172 -0.2170 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0274 -1.6716 1.7911 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6010 -2.2107 0.8886 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2510 0.7807 2.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0028 -0.1700 3.0186 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5397 1.4309 2.3992 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2854 -0.9643 -0.2188 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0350 0.1016 2.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6810 -1.5505 2.1530 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4002 -0.7746 2.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0032 0.9522 2.1831 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8133 -1.6475 -1.1107 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1381 -2.1062 -0.0637 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5707 -2.1625 0.6028 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9986 1.1584 0.8328 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0402 -1.6299 1.6590 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9704 0.5563 2.3570 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3092 -0.7688 3.3477 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2809 0.6722 2.8705 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8022 -1.9152 0.3928 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 1 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 26 28 1 0 28 29 1 0 29 30 1 0 18 31 1 0 29 2 1 0 28 5 1 0 26 9 1 0 23 11 1 0 21 14 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 6 3 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 6 40 1 0 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 10 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 6 16 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 17 59 1 0 18 60 1 6 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 6 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 27 73 1 0 27 74 1 0 27 75 1 0 28 76 1 1 29 77 1 1 30 78 1 0 30 79 1 0 30 80 1 0 31 81 1 0 M END

Standard InCHIKey	TZVDWGXUGGUMCE-JVHXOXOBSA-N
Standard InCHI	InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)22-9-10-23-26(3,4)24(31)13-15-28(23,6)21(22)12-16-30(29,8)25(27)20(19)2/h9,19-21,23-25,31H,10-18H2,1-8H3/t19-,20+,21+,23+,24+,25-,27-,28-,29-,30+/m1/s1
SMILES	C[C@@H]1CC[C@]2(C)CC[C@]3(C)C4=CC[C@H]5C(C)(C)[C@H](CC[C@]5(C)[C@H]4CC[C@@]3(C)[C@@H]2[C@H]1C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	426.39	Volume:	490.807 ? Van der Waals volume.
Dense:	0.869	LogP:	6.262 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.545 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.741 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	26.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.389	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.861	Fsp³:	0.933
MCE-18:	99.517 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.801	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.564	Promiscuous compounds:	0.059

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.146	MDCK Permeability:	-4.754
Pgp-inhibitor:	0.935	Pgp-substrate:	0.07
PAMPA:	0.364 ? 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):	0.0
20% Bioavailability (F20%):	0.481	30% Bioavailability (F30%):	0.082
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973	MRP1:	0.837
Plasma Protein Binding (PPB):	92.96%	Volume Distribution (VD):	-0.136
Fu:	7.026% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.964
BSEP inhibitor:	0.987

ADMET: Metabolism

CYP1A2-inhibitor:	0.024	CYP1A2-substrate:	0.571
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.945
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.074	CYP2D6-substrate:	0.95
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.983 ? 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):

14.903

Half-life (T1/2):

0.632

ADMET: Toxicity

hERG Blockers:	0.124	hERG Blockers (10um):	0.379
Human Hepatotoxicity (H-HT):	0.583	Drug-induced Liver Injury (DILI):	0.086
AMES Toxicity:	0.183	Rat Oral Acute Toxicity:	0.358
Maximum Recommended Daily Dose:	0.815	Skin Sensitization:	0.801
Carcinogencity:	0.9	Eye Corrosion:	0.033
Eye Irritation:	0.71	Respiratory Toxicity:	0.822
Drug-induced Neurotoxicity:	0.055	Ototoxicity:	0.51
Hematotoxicity:	0.327	Drug-induced Nephrotoxicity:	0.382
Genotoxicity:	0.481	RPMI-8226 Immunitoxicity:	0.072
A549 Cytotoxicity:	0.239	Hek293 Cytotoxicity:	0.679
BCF:	2.959 ? 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:	4.636 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.154 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.257 ? 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
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/j.tet.2012.03.006]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[10.1016/j.tet.2012.03.006]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543912]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880321]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[16317898]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	whole plants	Sendai, Miyagi Prefecture, Japan	2000-Sep	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17397219]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[17449162]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[19235686]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19666019]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[22707864]
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[22708987]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22940450]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23088673]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[2393954]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[25594733]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614422]
NPO6429	Phlomis regelii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29468889]
NPO1429	Callicarpa arborea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32628479]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32881525]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[7912074]
NPO17794	Streptomyces violaceusniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8557611]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6815	Streptomyces sclerotialus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28142	Anthoceros agrestis	Species	Anthocerotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1429	Callicarpa arborea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28299	Leucaena diversifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17794	Streptomyces violaceusniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3659	Limonium bicolor	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28157	Vriesea regina	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4095	Hedysarum multijugum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28007	Cakile maritima	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1429	Callicarpa arborea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4095	Hedysarum multijugum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1429	Callicarpa arborea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24480	Diospyros ebenum	Species	Ebenaceae	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]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6429	Phlomis regelii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6988	Diploschistes cretaceus	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6815	Streptomyces sclerotialus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28157	Vriesea regina	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28299	Leucaena diversifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17794	Streptomyces violaceusniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27863	Diospyros nigra	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4789	Adiantum caudatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4095	Hedysarum multijugum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8037	Bryum rutilans	Species	Bryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6223	Ceiba insignis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1429	Callicarpa arborea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3659	Limonium bicolor	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28332	Lecidea tumida	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27972	Clitocybe phosphorea	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28007	Cakile maritima	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28142	Anthoceros agrestis	Species	Anthocerotaceae	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 NPC138261 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	26828
0.1-0.2	19352
0.2-0.3	2946
0.3-0.4	567
0.4-0.5	108
0.5-0.6	49
0.6-0.7	5
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
0.6491	Remote Similarity	NPC27765
0.6491	Remote Similarity	NPC122418
0.6491	Remote Similarity	NPC491014
0.6066	Remote Similarity	NPC30166
0.6032	Remote Similarity	NPC470077
0.5932	Remote Similarity	NPC290598
0.5932	Remote Similarity	NPC30590
0.5902	Remote Similarity	NPC1319
0.5781	Remote Similarity	NPC125399
0.5781	Remote Similarity	NPC486522
0.5781	Remote Similarity	NPC470049
0.5714	Remote Similarity	NPC328052
0.5692	Remote Similarity	NPC477579
0.5672	Remote Similarity	NPC472240
0.5672	Remote Similarity	NPC262858
0.5625	Remote Similarity	NPC470224
0.5574	Remote Similarity	NPC100334
0.5556	Remote Similarity	NPC40394
0.5538	Remote Similarity	NPC40552
0.5522	Remote Similarity	NPC142361
0.5522	Remote Similarity	NPC474684
0.5469	Remote Similarity	NPC95594
0.5455	Remote Similarity	NPC486523
0.541	Remote Similarity	NPC120098
0.5397	Remote Similarity	NPC101475
0.5373	Remote Similarity	NPC318390
0.5312	Remote Similarity	NPC235341
0.5294	Remote Similarity	NPC210268
0.5294	Remote Similarity	NPC190604
0.5217	Remote Similarity	NPC484789
0.5217	Remote Similarity	NPC484801
0.5217	Remote Similarity	NPC470375
0.5217	Remote Similarity	NPC484786
0.5217	Remote Similarity	NPC470376
0.5217	Remote Similarity	NPC484787
0.5217	Remote Similarity	NPC484788
0.5217	Remote Similarity	NPC480720
0.5156	Remote Similarity	NPC132478
0.5156	Remote Similarity	NPC196753
0.5143	Remote Similarity	NPC471293
0.5143	Remote Similarity	NPC49776
0.5143	Remote Similarity	NPC63118
0.5143	Remote Similarity	NPC324598
0.5143	Remote Similarity	NPC474436
0.5077	Remote Similarity	NPC291379
0.5075	Remote Similarity	NPC246708
0.5072	Remote Similarity	NPC171203
0.5072	Remote Similarity	NPC307426
0.5072	Remote Similarity	NPC98442
0.5072	Remote Similarity	NPC242468
0.507	Remote Similarity	NPC484791
0.507	Remote Similarity	NPC5358
0.507	Remote Similarity	NPC484790
0.507	Remote Similarity	NPC216260

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC138261 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8072
0.1-0.2	1026
0.2-0.3	47
0.3-0.4	4
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