NPASS Compound

Natural Product: NPC193907

Natural Product ID	NPC193907
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FIADIPXEFYWJQV-ZZZYEPHESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11547321
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 79 83 0 0 0 0 0 0 0 0999 V2000 -3.2123 -3.0785 1.7158 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0012 -2.0694 1.9148 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9879 -2.1404 3.0498 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0275 -0.8094 1.1253 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3795 -0.7097 0.4051 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0582 -0.4844 -1.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7531 0.2164 -0.9524 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9962 0.2702 -2.2598 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5918 0.7668 -2.0293 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9226 0.1340 -0.8393 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6772 -1.3182 -1.2359 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7746 0.0825 0.3929 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0454 -0.4602 1.5586 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2977 0.2664 1.7654 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0913 0.1136 0.4847 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5561 0.2614 0.6655 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9829 1.2321 1.7088 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0577 -1.1067 1.1881 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5159 -1.2655 1.1788 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1879 -0.0490 0.6909 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0547 0.4746 1.3541 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 0.4466 -0.6326 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3423 -0.5478 -1.6376 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3363 1.7584 -1.0034 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2329 0.4025 -0.6777 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6066 1.4141 -1.5882 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1881 0.9537 -1.8687 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4018 0.8759 -0.5931 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0217 2.2907 -0.2507 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7402 2.7175 -1.2658 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0294 -0.6945 0.0449 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9361 1.5764 -0.4681 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5937 2.5530 -1.2199 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4557 1.9537 0.7541 O 0 0 0 0 0 1 0 0 0 0 0 0 -2.4930 -3.0740 0.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2605 -3.9500 2.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4882 -1.8258 3.9970 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8444 -1.4556 2.8911 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4136 -3.1666 3.1240 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9011 0.0281 1.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9116 0.1753 0.7864 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9605 -1.6503 0.5611 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8368 0.0492 -1.5923 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9254 -1.5093 -1.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0478 -0.6802 -2.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5098 1.0324 -2.8831 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0009 0.4118 -2.9281 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5372 1.8522 -2.0613 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8055 -2.0278 -0.4080 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2810 -1.5156 -1.6972 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4520 -1.6374 -1.9968 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1862 1.0689 0.7037 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8226 -1.5422 1.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6200 -0.2633 2.4879 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1723 1.2827 2.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8290 -0.3164 2.5443 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9192 -0.9752 0.2048 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7491 1.9541 1.4284 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3959 0.7509 2.6498 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1320 1.8426 2.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5300 -1.8968 0.6000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6872 -1.1998 2.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7744 -2.0826 0.4412 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9246 -1.6301 2.1442 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4555 -0.0634 -2.6339 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3658 -0.8172 -1.3037 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6877 -1.4337 -1.7559 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4285 1.6809 -0.7421 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9545 2.6412 -0.5209 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3227 1.8858 -2.1204 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9795 -0.5909 -1.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1403 1.2737 -2.5795 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2477 0.0622 -2.4716 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6650 1.7249 -2.5098 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3125 3.0327 -1.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0705 2.4762 -0.1772 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4538 2.6843 0.6673 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5932 3.0153 -0.3618 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8036 -1.6476 -0.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 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 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 26 30 1 0 12 31 1 0 7 32 1 1 32 33 2 0 32 34 1 0 31 4 1 0 31 7 1 0 28 10 1 0 28 15 1 0 25 16 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 1 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 8 45 1 0 8 46 1 0 9 47 1 0 9 48 1 0 11 49 1 0 11 50 1 0 11 51 1 0 12 52 1 1 13 53 1 0 13 54 1 0 14 55 1 0 14 56 1 0 15 57 1 6 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 0 19 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 24 68 1 0 24 69 1 0 24 70 1 0 25 71 1 6 26 72 1 6 27 73 1 0 27 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 31 79 1 6 M CHG 1 34 -1 M END

Standard InCHIKey	FIADIPXEFYWJQV-ZZZYEPHESA-N
Standard InCHI	InChI=1S/C30H46O4/c1-17(2)18-10-13-30(25(33)34)15-14-28(6)19(23(18)30)8-9-21-27(5)12-11-22(32)26(3,4)24(27)20(31)16-29(21,28)7/h18-21,23-24,31H,1,8-16H2,2-7H3,(H,33,34)/p-1/t18-,19+,20+,21+,23+,24-,27+,28+,29+,30-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5[C@@H](C[C@@]34C)O)[C@@H]12)C(=O)[O-]

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	3.022 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.8 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.284 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.467	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.887	Fsp³:	0.867
MCE-18:	105.857 ? 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:	0.964	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.353	Promiscuous compounds:	0.222

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.438	MDCK Permeability:	-5.065
Pgp-inhibitor:	0.002	Pgp-substrate:	0.002
PAMPA:	0.849 ? 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%):	0.002	30% Bioavailability (F30%):	0.04
50% Bioavailability (F50%):	0.426

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.241	MRP1:	0.995
Plasma Protein Binding (PPB):	97.115%	Volume Distribution (VD):	-0.174
Fu:	2.881% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.018
BSEP inhibitor:	0.761

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.049	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.111	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.956	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.003
HLM stability:	0.001 ? 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):

6.096

Half-life (T1/2):

0.819

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.067
Human Hepatotoxicity (H-HT):	0.718	Drug-induced Liver Injury (DILI):	0.61
AMES Toxicity:	0.221	Rat Oral Acute Toxicity:	0.339
Maximum Recommended Daily Dose:	0.513	Skin Sensitization:	0.97
Carcinogencity:	0.892	Eye Corrosion:	0.074
Eye Irritation:	0.556	Respiratory Toxicity:	0.885
Drug-induced Neurotoxicity:	0.101	Ototoxicity:	0.63
Hematotoxicity:	0.728	Drug-induced Nephrotoxicity:	0.773
Genotoxicity:	0.863	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.088	Hek293 Cytotoxicity:	0.159
BCF:	0.503 ? 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:	3.259 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.744 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.16 ? 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
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)83457-3]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075772]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843567]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043405]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16155971]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125219]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17665952]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18345641]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19824618]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21667999]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27592135]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[324959]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33325237]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO2304	Byssovorax cruenta	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10806	Achillea roseoalba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1355	Urechis caupo	Species	Urechidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5319	Ulmus thomasii	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6310	Ruta bracteosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7766	Pericopsis schliebenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO276	Miscanthus sacchariflorus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25481	Lonchocarpus oaxacensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8103	Lecanora melanophthalma	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7060	Ficus ruficaulis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4516	Fasciospongia rimosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3830	Euplotes rariseta	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9903	Engelhardia spicata	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24370	Crassocephalum crepidioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15610	Citrus trifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2304	Byssovorax cruenta	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4516	Fasciospongia rimosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5319	Ulmus thomasii	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10806	Achillea roseoalba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO276	Miscanthus sacchariflorus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7060	Ficus ruficaulis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1355	Urechis caupo	Species	Urechidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7766	Pericopsis schliebenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8103	Lecanora melanophthalma	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9903	Engelhardia spicata	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25481	Lonchocarpus oaxacensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15610	Citrus trifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24370	Crassocephalum crepidioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3830	Euplotes rariseta	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6310	Ruta bracteosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	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
FIC	5
MIC	21
FICI	5

Activity Type	# Activity
Organism	31

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
NPT1207	Organism	Acinetobacter	Acinetobacter	MIC	>	1024.0	ug.mL-1	PMID[33892286]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	1024.0	ug.mL-1	PMID[33892286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FIC	=	0.25	n.a.	PMID[33892286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[33892286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FIC	=	0.5	n.a.	PMID[33892286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FICI	=	1.0	n.a.	PMID[33892286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[33892286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FIC	=	1.0	n.a.	PMID[33892286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FICI	=	0.75	n.a.	PMID[33892286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FICI	=	2.0	n.a.	PMID[33892286]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	1024.0	ug.mL-1	PMID[33892286]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	1024.0	ug.mL-1	PMID[33892286]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	32.0	ug.mL-1	PMID[33892286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[33892286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FICI	=	0.49	n.a.	PMID[33892286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FICI	=	0.53	n.a.	PMID[33892286]

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 NPC193907 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	21770
0.1-0.2	25212
0.2-0.3	2667
0.3-0.4	165
0.4-0.5	29
0.5-0.6	9
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.746	Intermediate Similarity	NPC474719
0.6	Remote Similarity	NPC475745
0.5909	Remote Similarity	NPC116146
0.5909	Remote Similarity	NPC474482
0.5588	Remote Similarity	NPC472738
0.5588	Remote Similarity	NPC472739
0.5455	Remote Similarity	NPC23884
0.5417	Remote Similarity	NPC244356
0.5417	Remote Similarity	NPC224060
0.5217	Remote Similarity	NPC192744
0.507	Remote Similarity	NPC291373

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC193907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6027
0.1-0.2	3013
0.2-0.3	107
0.3-0.4	2
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