NPASS Compound

Natural Product: NPC308472

Natural Product ID	NPC308472
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BMLXJHRQBRRIJE-IWZLKQDZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10865825
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 109115 0 0 0 0 0 0 0 0999 V2000 -5.2503 -3.6952 -1.2538 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3760 -3.0393 -0.5065 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9026 -4.0609 0.4848 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8371 -3.4200 1.8774 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3834 -3.0345 2.0839 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9044 -2.1716 0.9387 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9745 -1.8536 0.1470 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.1050 1.3711 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8447 -1.1218 0.9670 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8936 -1.1069 2.1513 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4850 -0.8078 1.7322 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3003 -0.0284 0.4988 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0322 -0.4941 -0.1235 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0335 -0.5126 0.8141 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2492 -0.9577 0.2838 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3407 0.0114 0.4519 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7307 -0.5658 0.5247 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7238 -2.0237 0.9324 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4489 -2.3228 1.7413 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5582 -3.7600 2.1902 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4367 -2.2261 0.8178 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7885 -2.3700 1.7570 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4950 -0.3123 -0.6107 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6040 0.4494 -0.3753 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8360 -0.3032 -0.8193 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0968 0.4976 -0.5764 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9282 1.9628 -0.9504 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5706 2.4736 -0.5520 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6188 1.6437 -1.1446 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8807 2.7437 -0.3304 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1476 -0.0990 -1.2265 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9970 -1.5328 -0.2261 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3430 0.8521 -0.6893 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3018 -0.0414 -0.4387 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5246 0.1198 0.1674 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5759 0.5533 -0.6709 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0044 1.8833 -0.7201 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9251 2.3125 0.2360 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4002 1.5799 1.1351 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3741 3.6255 0.2325 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2845 4.0852 1.1647 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7348 5.3853 1.1707 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2558 6.2412 0.2145 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3488 5.8246 -0.7323 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9038 4.4971 -0.7203 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0608 4.0516 -1.5770 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5756 2.8026 -1.6492 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6278 2.4984 -2.7076 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2396 1.2725 -3.1190 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2837 1.0772 -4.1257 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7006 2.1452 -4.7393 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0781 3.4067 -4.3410 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0182 3.5826 -3.3502 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2419 1.9345 -5.7320 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7277 7.5685 0.2360 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7545 3.2013 2.1218 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2939 -1.9837 1.6790 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8768 -2.3277 2.8228 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6604 -4.2201 2.1959 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1894 -4.4036 2.8030 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2163 -4.3581 0.1159 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7267 -4.2481 -2.1155 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5260 -3.0012 -1.6959 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7576 -4.5192 -0.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1604 -2.7209 -1.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3482 -5.0094 0.4706 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5161 -2.5647 1.8627 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3349 -2.4900 3.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2222 -2.8183 0.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6738 -2.0224 0.3324 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2728 -0.3455 2.8603 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0317 -0.2369 2.5969 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0903 1.0448 0.7738 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9454 -1.5070 -0.5642 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2395 0.1993 -0.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0371 -1.1560 -0.8119 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1230 0.6940 1.3008 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2511 -0.0429 1.3571 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7070 -2.7201 0.0879 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3515 -1.6071 2.5817 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5561 -4.1895 2.4022 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9422 -4.3393 1.3055 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2786 -3.8998 2.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6043 -2.0161 2.6575 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7430 0.7315 0.6864 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8173 -0.4902 -1.9315 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2616 0.4869 0.5412 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0457 2.0887 -2.0491 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4260 3.4867 -0.9282 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4051 2.4390 0.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4842 3.5534 0.0487 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9240 -0.2619 -2.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4621 -2.2194 -0.6978 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9614 1.7284 -0.5155 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3650 0.9567 0.9147 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4451 5.7121 1.9124 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9783 6.5056 -1.4813 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6809 0.4060 -2.6937 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0030 0.0818 -4.4224 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6154 4.2498 -4.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2793 4.5875 -3.0740 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3994 2.5777 -6.4965 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7442 7.6593 0.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6028 3.3085 3.1064 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0638 -2.6002 1.0117 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9949 -2.7217 2.9359 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1874 -4.9461 2.6105 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9256 -4.0430 3.3505 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8831 -3.7842 0.5679 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 18 22 1 0 17 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 26 31 1 0 25 32 1 0 16 33 1 0 12 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 51 54 1 0 43 55 1 0 41 56 1 0 11 57 1 0 10 58 1 0 5 59 1 0 4 60 1 0 3 61 1 0 7 2 1 0 35 9 1 0 47 37 2 0 53 48 1 0 21 15 1 0 29 24 1 0 45 40 1 0 1 62 1 0 1 63 1 0 1 64 1 0 2 65 1 6 3 66 1 1 4 67 1 6 5 68 1 1 6 69 1 6 9 70 1 6 10 71 1 1 11 72 1 1 12 73 1 1 13 74 1 0 13 75 1 0 15 76 1 6 16 77 1 1 17 78 1 1 18 79 1 6 19 80 1 1 20 81 1 0 20 82 1 0 20 83 1 0 22 84 1 0 24 85 1 1 25 86 1 6 26 87 1 1 27 88 1 6 28 89 1 0 28 90 1 0 30 91 1 0 31 92 1 0 32 93 1 0 33 94 1 0 35 95 1 1 42 96 1 0 44 97 1 0 49 98 1 0 50 99 1 0 52100 1 0 53101 1 0 54102 1 0 55103 1 0 56104 1 0 57105 1 0 58106 1 0 59107 1 0 60108 1 0 61109 1 0 M END

Standard InCHIKey	BMLXJHRQBRRIJE-IWZLKQDZSA-N
Standard InCHI	InChI=1S/C38H48O23/c1-11-21(43)26(48)29(51)37(56-11)61-34-27(49)24(46)19(10-54-36-30(52)32(22(44)12(2)55-36)59-35-28(50)23(45)17(42)9-53-35)58-38(34)60-33-25(47)20-16(41)7-15(40)8-18(20)57-31(33)13-3-5-14(39)6-4-13/h3-8,11-12,17,19,21-24,26-30,32,34-46,48-52H,9-10H2,1-2H3/t11-,12-,17+,19+,21-,22-,23-,24-,26+,27-,28+,29+,30+,32+,34+,35-,36+,37-,38-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H]([C@@H](CO[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O)O[C@H]1Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	872.26	Volume:	786.992 ? Van der Waals volume.
Dense:	1.108	LogP:	0.585 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.13 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.126 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	42.0
TPSA:	367.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.092	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.839	Fsp³:	0.605
MCE-18:	179.131 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.631	Fluc inhibitor:	0.288 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.605 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.403 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.308	Promiscuous compounds:	0.562

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.927	MDCK Permeability:	-4.876
Pgp-inhibitor:	0.0	Pgp-substrate:	0.998
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):	0.657
20% Bioavailability (F20%):	0.527	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.049
Plasma Protein Binding (PPB):	77.078%	Volume Distribution (VD):	-0.179
Fu:	21.728% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.054
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:	0.063
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.024
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.989 ? 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):

0.464

Half-life (T1/2):

5.312

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.065
Human Hepatotoxicity (H-HT):	0.392	Drug-induced Liver Injury (DILI):	0.958
AMES Toxicity:	0.95	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.015	Skin Sensitization:	1.0
Carcinogencity:	0.01	Eye Corrosion:	0.0
Eye Irritation:	0.204	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.984
Hematotoxicity:	0.087	Drug-induced Nephrotoxicity:	0.718
Genotoxicity:	0.933	RPMI-8226 Immunitoxicity:	0.323
A549 Cytotoxicity:	0.806	Hek293 Cytotoxicity:	0.867
BCF:	0.383 ? 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:	2.771 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.44 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.478 ? 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
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1007/s11418-005-0009-z]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257536]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19177635]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19433363]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	Sunan County, Gansu Province, China	2006-JUN	PMID[20684529]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[22032651]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22032651]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	whole plant	Guide County, Qinghai Province, China	2008-AUG	PMID[22775441]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30219526]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36599374]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2439	Diplopterygium glaucum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2670	Maytenus chuchuhuasha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3838	Chrysosporum ovalisporum	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO593	Wikstroemia viridiflora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13474	Euphrasia genargentea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9594	Lysimachia fordiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9737	Ampelocera edentula	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5086	Alternaria macrospora	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21472	Pterolobium hexapetalum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9998	Abies excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10038.1	Abies pinsapo var. marocana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9091	Orthosiphon spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1293	Streptomyces matensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10132	Schizophyllum lobatum	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9867	Ixeris debilis	Species	Asteraceae	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 NPC308472 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	23904
0.1-0.2	22501
0.2-0.3	2788
0.3-0.4	327
0.4-0.5	175
0.5-0.6	84
0.6-0.7	53
0.7-0.8	0
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8925	High Similarity	NPC221342
0.8925	High Similarity	NPC476470
0.8495	Intermediate Similarity	NPC12013
0.8495	Intermediate Similarity	NPC11432
0.8495	Intermediate Similarity	NPC477613
0.8061	Intermediate Similarity	NPC602448
0.7959	Intermediate Similarity	NPC292929
0.7835	Intermediate Similarity	NPC122467
0.7379	Intermediate Similarity	NPC89052
0.7308	Intermediate Similarity	NPC189564
0.7263	Intermediate Similarity	NPC476215
0.7212	Intermediate Similarity	NPC203145
0.7207	Intermediate Similarity	NPC192539
0.717	Intermediate Similarity	NPC303694
0.7157	Intermediate Similarity	NPC89127
0.7071	Intermediate Similarity	NPC304741
0.7059	Intermediate Similarity	NPC142142
0.697	Remote Similarity	NPC173582
0.697	Remote Similarity	NPC265885
0.697	Remote Similarity	NPC181465
0.697	Remote Similarity	NPC215710
0.697	Remote Similarity	NPC163242
0.697	Remote Similarity	NPC272068
0.697	Remote Similarity	NPC473438
0.697	Remote Similarity	NPC253788
0.6869	Remote Similarity	NPC471079
0.6847	Remote Similarity	NPC480445
0.6807	Remote Similarity	NPC249560
0.6759	Remote Similarity	NPC292019
0.6759	Remote Similarity	NPC202908
0.6759	Remote Similarity	NPC173837
0.6752	Remote Similarity	NPC473554
0.6667	Remote Similarity	NPC95866
0.6545	Remote Similarity	NPC25523
0.6508	Remote Similarity	NPC33083
0.6505	Remote Similarity	NPC255157
0.6505	Remote Similarity	NPC259896
0.6491	Remote Similarity	NPC162394
0.6471	Remote Similarity	NPC470405
0.6435	Remote Similarity	NPC480444
0.6408	Remote Similarity	NPC203259
0.6408	Remote Similarity	NPC33054
0.6408	Remote Similarity	NPC155877
0.6408	Remote Similarity	NPC176740
0.6408	Remote Similarity	NPC471725
0.6408	Remote Similarity	NPC134532
0.6408	Remote Similarity	NPC602582
0.64	Remote Similarity	NPC170052
0.64	Remote Similarity	NPC135846
0.6387	Remote Similarity	NPC487499
0.6316	Remote Similarity	NPC488734
0.6316	Remote Similarity	NPC488735
0.6316	Remote Similarity	NPC488739
0.6316	Remote Similarity	NPC488732
0.6316	Remote Similarity	NPC488738
0.6311	Remote Similarity	NPC67326
0.6311	Remote Similarity	NPC487502
0.6204	Remote Similarity	NPC76831
0.6198	Remote Similarity	NPC275977
0.6102	Remote Similarity	NPC488737
0.6066	Remote Similarity	NPC231787
0.6055	Remote Similarity	NPC476472
0.6055	Remote Similarity	NPC294815
0.6055	Remote Similarity	NPC16194
0.6055	Remote Similarity	NPC220173
0.605	Remote Similarity	NPC480443
0.6019	Remote Similarity	NPC473327
0.6018	Remote Similarity	NPC219043
0.6	Remote Similarity	NPC216496
0.6	Remote Similarity	NPC39834
0.5984	Remote Similarity	NPC487500
0.5965	Remote Similarity	NPC480441
0.5938	Remote Similarity	NPC487501
0.5932	Remote Similarity	NPC488740
0.5932	Remote Similarity	NPC488736
0.5932	Remote Similarity	NPC488733
0.5918	Remote Similarity	NPC111929
0.5918	Remote Similarity	NPC320283
0.5918	Remote Similarity	NPC41121
0.5877	Remote Similarity	NPC48984
0.5865	Remote Similarity	NPC254855
0.5865	Remote Similarity	NPC94610
0.5833	Remote Similarity	NPC209550
0.5833	Remote Similarity	NPC240306
0.5833	Remote Similarity	NPC241781
0.5794	Remote Similarity	NPC65563
0.5794	Remote Similarity	NPC470949
0.5773	Remote Similarity	NPC54802
0.5773	Remote Similarity	NPC197304
0.5741	Remote Similarity	NPC470444
0.5741	Remote Similarity	NPC473571
0.5741	Remote Similarity	NPC110941
0.5741	Remote Similarity	NPC186816
0.5714	Remote Similarity	NPC30011
0.5714	Remote Similarity	NPC72554
0.5648	Remote Similarity	NPC156869
0.5631	Remote Similarity	NPC129217
0.5631	Remote Similarity	NPC48093
0.561	Remote Similarity	NPC480442
0.5586	Remote Similarity	NPC32641
0.5586	Remote Similarity	NPC256188
0.5577	Remote Similarity	NPC259957
0.5577	Remote Similarity	NPC224530
0.5565	Remote Similarity	NPC25946
0.5538	Remote Similarity	NPC97817
0.5536	Remote Similarity	NPC603079
0.5526	Remote Similarity	NPC218161
0.5495	Remote Similarity	NPC245452
0.5446	Remote Similarity	NPC35119
0.541	Remote Similarity	NPC474522
0.5392	Remote Similarity	NPC127546
0.5392	Remote Similarity	NPC57625
0.5392	Remote Similarity	NPC173637
0.5392	Remote Similarity	NPC317489
0.5392	Remote Similarity	NPC223424
0.5392	Remote Similarity	NPC600591
0.5364	Remote Similarity	NPC605592
0.5333	Remote Similarity	NPC159579
0.5327	Remote Similarity	NPC276377
0.5321	Remote Similarity	NPC187379
0.5321	Remote Similarity	NPC139320
0.5278	Remote Similarity	NPC116864
0.5278	Remote Similarity	NPC244776
0.5268	Remote Similarity	NPC126784
0.5268	Remote Similarity	NPC241423
0.5268	Remote Similarity	NPC488074
0.5248	Remote Similarity	NPC276222
0.5248	Remote Similarity	NPC274618
0.5248	Remote Similarity	NPC118284
0.5248	Remote Similarity	NPC608147
0.5243	Remote Similarity	NPC77672
0.5243	Remote Similarity	NPC133671
0.5243	Remote Similarity	NPC135391
0.5243	Remote Similarity	NPC78263
0.5243	Remote Similarity	NPC250069
0.5217	Remote Similarity	NPC471669
0.5203	Remote Similarity	NPC298666
0.5179	Remote Similarity	NPC129264
0.5161	Remote Similarity	NPC156785
0.5156	Remote Similarity	NPC21359
0.5156	Remote Similarity	NPC460984
0.5143	Remote Similarity	NPC52550
0.5133	Remote Similarity	NPC470125
0.513	Remote Similarity	NPC97119
0.5122	Remote Similarity	NPC488086
0.5098	Remote Similarity	NPC288084
0.5093	Remote Similarity	NPC223747
0.5086	Remote Similarity	NPC85751
0.5086	Remote Similarity	NPC19240
0.5085	Remote Similarity	NPC14187
0.5047	Remote Similarity	NPC219904
0.5044	Remote Similarity	NPC35167
0.5043	Remote Similarity	NPC270448
0.5043	Remote Similarity	NPC470449

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC308472 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6237
0.1-0.2	2869
0.2-0.3	36
0.3-0.4	4
0.4-0.5	2
0.5-0.6	1
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	Drug ID	Developmental Stage
0.6408	Remote Similarity	NPD6797	Phase 2
0.5086	Remote Similarity	NPD7251	Phase 2

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