NPASS Compound

Natural Product: NPC178919

Natural Product ID	NPC178919
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Enniatin B1
IUPAC Name	(3S,6R,9S,12R,15S,18R)-3-[(2S)-butan-2-yl]-4,10,16-trimethyl-6,9,12,15,18-penta(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Synonyms	Enniatin B1
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL446318
PubChem CID	11262300
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

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 105105 0 0 0 0 0 0 0 0999 V2000 -5.9764 -2.1609 -0.3240 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5145 -1.6625 1.0512 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8554 -0.2921 0.9372 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6648 -0.3133 0.0524 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0641 1.0567 -0.0283 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7837 2.0144 0.3430 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8118 1.3442 -0.4846 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3118 2.7156 -0.5813 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4015 2.9864 -2.0524 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5683 2.0694 -2.9156 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4759 4.3877 -2.5121 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0781 2.8314 0.1175 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3737 1.8071 0.7393 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8739 3.8434 0.3411 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6128 5.1146 -0.2148 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0718 3.6428 1.1310 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6870 3.5574 2.6316 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9991 4.8986 2.9431 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9840 3.5988 3.4022 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9287 2.5496 0.7404 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7641 2.0654 1.5375 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8828 1.9689 -0.5172 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7457 0.8407 -0.8076 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7373 -0.2417 -0.9711 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6093 0.0341 -1.4068 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8393 -1.6058 -0.6858 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6982 -2.4812 -0.8947 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9337 -2.4709 0.4128 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4972 -2.0884 1.4387 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3702 -2.8623 0.4510 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0947 -2.7654 1.6947 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1420 -1.7560 1.4411 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6348 -1.1177 2.3658 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7335 -1.3780 0.2208 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3454 -2.1794 -0.8897 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5737 -4.1218 2.0445 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4320 -5.0954 2.2148 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2604 -4.0145 3.4176 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9050 -3.7873 -1.4837 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5434 -4.4997 -1.6159 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7532 -4.7605 -0.6754 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0598 -2.0819 -0.1941 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5920 1.0304 -2.0064 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5187 2.2231 -1.9023 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8229 1.0327 -3.3068 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9149 0.7058 0.4429 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3127 -3.0156 -0.5882 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8365 -1.3943 -1.1062 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0122 -2.5565 -0.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4325 -1.6127 1.6712 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8543 -2.3868 1.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6378 0.0083 1.9816 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0701 -0.3816 -1.0495 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0844 3.4059 -0.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4804 2.5929 -2.2877 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9477 2.0382 -3.9651 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4540 2.4920 -2.9789 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6089 1.0259 -2.5679 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8990 5.1065 -1.8276 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1568 4.4563 -3.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4907 4.7046 -2.9554 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1706 5.9248 0.3542 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9612 5.2543 -1.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4464 5.3803 -0.0216 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6191 4.6335 1.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0541 2.6988 2.8446 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7434 5.6816 2.7012 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1445 4.9926 2.2776 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7079 4.9099 4.0260 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8531 4.2590 4.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7956 4.0179 2.7763 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2995 2.5809 3.7241 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3510 0.6080 0.0768 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9492 -1.8792 -1.5123 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3882 -2.3553 2.4323 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1358 -2.1384 -1.7054 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3210 -3.2905 -0.6750 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4228 -1.8265 -1.3920 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2764 -4.5668 1.3243 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5491 -4.6219 1.9849 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4499 -5.5612 3.2093 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5326 -5.9345 1.4716 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3593 -3.9200 3.2947 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8453 -3.1553 3.9836 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0690 -4.9189 4.0328 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2787 -3.7216 -2.5230 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1855 -4.8536 -0.6289 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6076 -5.3277 -2.3480 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1793 -3.7674 -2.0023 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5010 -4.7228 0.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4769 -5.8175 -0.9818 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8305 -4.6942 -0.9043 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6722 -2.4943 -1.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9164 -2.8355 0.6105 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7398 -1.3265 0.2602 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2698 0.1356 -2.0581 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7545 2.6540 -2.9076 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0282 3.0815 -1.3552 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4980 1.9709 -1.4467 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9003 1.6378 -3.2632 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5186 0.0106 -3.6153 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5180 1.3784 -4.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9138 1.5821 1.1066 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7016 1.0587 -0.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9086 0.2129 0.3864 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 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 8 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 16 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 31 36 1 0 36 37 1 0 36 38 1 0 27 39 1 0 39 40 1 0 39 41 1 0 26 42 1 0 23 43 1 0 43 44 1 0 43 45 1 0 3 46 1 0 34 4 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 2 51 1 0 3 52 1 1 4 53 1 6 8 54 1 1 9 55 1 0 10 56 1 0 10 57 1 0 10 58 1 0 11 59 1 0 11 60 1 0 11 61 1 0 15 62 1 0 15 63 1 0 15 64 1 0 16 65 1 1 17 66 1 0 18 67 1 0 18 68 1 0 18 69 1 0 19 70 1 0 19 71 1 0 19 72 1 0 23 73 1 1 27 74 1 6 31 75 1 1 35 76 1 0 35 77 1 0 35 78 1 0 36 79 1 0 37 80 1 0 37 81 1 0 37 82 1 0 38 83 1 0 38 84 1 0 38 85 1 0 39 86 1 0 40 87 1 0 40 88 1 0 40 89 1 0 41 90 1 0 41 91 1 0 41 92 1 0 42 93 1 0 42 94 1 0 42 95 1 0 43 96 1 0 44 97 1 0 44 98 1 0 44 99 1 0 45100 1 0 45101 1 0 45102 1 0 46103 1 0 46104 1 0 46105 1 0 M END

Standard InCHIKey	UQCSETXJXJTMKO-UMURLBKASA-N
Standard InCHI	InChI=1S/C34H59N3O9/c1-16-22(12)25-34(43)46-27(20(8)9)30(39)36(14)23(17(2)3)32(41)44-26(19(6)7)29(38)35(13)24(18(4)5)33(42)45-28(21(10)11)31(40)37(25)15/h17-28H,16H2,1-15H3/t22-,23-,24-,25-,26+,27+,28+/m0/s1
SMILES	CC[C@@H]([C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N1C)C(C)C)C(C)C)C)C(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	653.43	Volume:	684.347 ? Van der Waals volume.
Dense:	0.955	LogP:	4.347 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.904 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.659 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	24.0
TPSA:	139.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	0.0	Rings:	1.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.298	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.199	Fsp³:	0.824
MCE-18:	52.645 ? 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:	0
Colloidal aggregators:	0.419	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.329 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.221	Promiscuous compounds:	0.635

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.948	MDCK Permeability:	-4.401
Pgp-inhibitor:	1.0	Pgp-substrate:	0.0
PAMPA:	0.0 ? 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):	1.0
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.334
Plasma Protein Binding (PPB):	42.035%	Volume Distribution (VD):	-0.326
Fu:	46.099% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.135	CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.987 ? 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):

8.127

Half-life (T1/2):

0.497

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.018
Human Hepatotoxicity (H-HT):	0.998	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.995	Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.034	Skin Sensitization:	1.0
Carcinogencity:	0.991	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	1.0	Ototoxicity:	0.826
Hematotoxicity:	0.998	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.957
A549 Cytotoxicity:	0.889	Hek293 Cytotoxicity:	0.938
BCF:	1.639 ? 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:	3.569 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.055 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.858 ? 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
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1023/A:1025674116183]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1324982]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[13465274]
NPO40136	Fusarium sp. F31	Strain	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165149]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1536925]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180822]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562855]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17286429]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21090694]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24175613]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	seed	n.a.	PMID[24225786]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3509958]
NPO41427	Fusarium tricinctum + Streptomyces lividans/Bacillus subtilis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[35518011]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39073007]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9014349]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2993	Nototodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO40136	Fusarium sp. F31	Strain	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2993	Nototodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	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	10
Activity	1
IC50	3

Activity Type	# Activity
Organism	14

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
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	15.0	ug.mL-1	PMID[16562855]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	4.0	ug.mL-1	PMID[24175613]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	=	75.0	ug.mL-1	PMID[15165149]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	Activity	=	25.0	ug ml-1	PMID[15165149]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	2.0	ug.mL-1	PMID[16562855]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	6.25	ug.mL-1	PMID[16562855]
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	MIC	=	16.0	ug.mL-1	PMID[24175613]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	9.0	ug.mL-1	PMID[16562855]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	25.0	ug.mL-1	PMID[16562855]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	64.0	ug.mL-1	PMID[24175613]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64.0	ug.mL-1	PMID[24175613]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	8.0	ug.mL-1	PMID[24175613]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[24175613]

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 NPC178919 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	26077
0.1-0.2	22784
0.2-0.3	961
0.3-0.4	20
0.4-0.5	5
0.5-0.6	1
0.6-0.7	2
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC609395
0.8214	Intermediate Similarity	NPC212866
0.8065	Intermediate Similarity	NPC603663
0.7812	Intermediate Similarity	NPC29598
0.7568	Intermediate Similarity	NPC473741
0.7419	Intermediate Similarity	NPC606384
0.7188	Intermediate Similarity	NPC10716
0.7027	Intermediate Similarity	NPC477145
0.6857	Remote Similarity	NPC263281
0.6053	Remote Similarity	NPC604030
0.5349	Remote Similarity	NPC246005

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC178919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6885
0.1-0.2	2228
0.2-0.3	35
0.3-0.4	1
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	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8214	Intermediate Similarity	NPD7840	Approved

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