NPASS Compound

Natural Product: NPC195807

Natural Product ID	NPC195807
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DTHALOCPATWECM-PVHPJOTLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 100105 0 0 0 0 0 0 0 0999 V2000 11.7465 0.5980 0.8738 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9842 1.4919 -0.1214 C 0 0 1 0 0 0 0 0 0 0 0 0 11.6427 1.2499 -1.4605 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5431 1.2842 -2.5138 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5649 2.3308 -2.0711 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7977 1.8069 -0.8744 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8113 0.9242 -1.2199 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5451 1.1984 -0.7523 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6316 0.0857 -1.2618 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3385 -1.2044 -1.0125 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1303 -1.5333 0.4690 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6334 -1.6982 0.6071 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9607 -0.3613 0.3286 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5869 -0.5513 0.2844 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6315 -0.0190 1.0828 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9156 0.8358 2.1187 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9262 1.3824 2.9383 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3834 1.0356 2.6777 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4319 1.5288 3.4378 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1439 2.3083 4.3792 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7088 1.1450 3.1247 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0099 0.2889 2.0884 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3652 -0.1357 1.7321 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5565 -0.9788 0.6346 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7940 -1.4255 0.2381 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9374 -1.0329 0.9501 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7517 -0.2107 2.0206 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4821 0.2413 2.4190 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8861 0.1839 2.7290 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8336 1.0455 3.8546 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1718 -1.5159 0.4995 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0231 -0.7577 -0.3223 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.4077 -0.8042 0.2547 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.4419 -0.0628 -0.5240 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.1965 -0.2753 -2.0005 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7325 -0.1452 -2.3269 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5073 -0.1206 -3.7996 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8536 -1.2895 -4.4453 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9959 -1.1516 -1.6638 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6698 -1.5548 -2.3210 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.6842 -0.6639 -0.2473 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8496 -2.1156 0.4504 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9979 -2.2499 -0.8316 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0057 -2.7540 -1.6712 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9798 -0.1442 1.4065 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7337 0.1854 1.6555 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2752 -0.3321 0.8706 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2234 2.2315 3.9664 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3412 0.1846 -0.8940 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2521 -2.6509 -0.3312 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6979 -2.7955 0.7480 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8654 -2.2648 -1.7442 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6764 1.1022 -0.0435 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2597 3.4660 -1.6730 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8728 0.0573 -2.5677 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4893 2.3215 -1.7379 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5752 0.9167 1.9138 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8041 0.4720 0.5955 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2878 -0.4266 0.7612 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1671 2.5241 0.2602 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1954 0.2809 -1.4943 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9146 1.5588 -3.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9181 2.6176 -2.9245 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4011 2.6402 -0.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1716 2.1972 -0.9732 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5665 1.0792 0.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6511 0.2187 -2.3952 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4276 -1.0211 -1.1301 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5481 -0.7917 1.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4089 -1.9771 1.6324 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2215 0.2893 1.1772 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9048 1.1235 2.3466 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5237 1.5412 3.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6588 -1.2595 0.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3899 0.8996 3.2840 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7892 0.8878 4.4172 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0036 0.8481 4.5289 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8626 2.1132 3.4906 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6582 0.2866 -0.3032 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3140 -0.3849 1.2997 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5419 0.9991 -0.2499 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7583 0.4600 -2.5745 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3915 0.8428 -1.9213 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4835 0.2281 -4.0777 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2015 0.6698 -4.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4327 -1.3069 -5.3618 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9433 -2.1789 -2.5339 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6733 -1.6464 -0.3756 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2757 -2.7528 -0.0775 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1664 -2.3233 -2.7023 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 -3.8809 -1.7449 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9680 -2.4868 -1.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0632 -1.0035 0.0559 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0497 2.8375 3.8581 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4430 -2.3575 -0.8188 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9130 -2.8472 1.7249 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3360 -3.0784 -1.4338 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6896 3.9366 -0.9836 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1710 -0.4921 -1.7891 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4460 2.0328 -1.7641 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 7 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 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 26 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 25 43 1 0 43 44 1 0 22 45 1 0 45 46 1 0 46 47 2 0 17 48 1 0 13 49 1 0 12 50 1 0 11 51 1 0 10 52 1 0 6 53 1 0 5 54 1 0 4 55 1 0 3 56 1 0 53 2 1 0 49 9 1 0 47 15 1 0 46 18 1 0 28 23 1 0 39 32 1 0 1 57 1 0 1 58 1 0 1 59 1 0 2 60 1 1 3 61 1 1 4 62 1 6 5 63 1 6 6 64 1 1 8 65 1 0 8 66 1 0 9 67 1 6 10 68 1 1 11 69 1 1 12 70 1 1 13 71 1 1 16 72 1 0 21 73 1 0 24 74 1 0 28 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 32 79 1 6 33 80 1 1 34 81 1 6 35 82 1 6 36 83 1 1 37 84 1 0 37 85 1 0 38 86 1 0 40 87 1 0 41 88 1 0 42 89 1 0 44 90 1 0 44 91 1 0 44 92 1 0 47 93 1 0 48 94 1 0 50 95 1 0 51 96 1 0 52 97 1 0 54 98 1 0 55 99 1 0 56100 1 0 M END

Standard InCHIKey	DTHALOCPATWECM-PVHPJOTLSA-N
Standard InCHI	InChI=1S/C35H44O21/c1-11-23(39)26(42)29(45)33(51-11)50-10-21-25(41)28(44)30(46)34(55-21)52-13-6-14(37)22-15(38)8-16(53-17(22)7-13)12-4-18(48-2)32(19(5-12)49-3)56-35-31(47)27(43)24(40)20(9-36)54-35/h4-8,11,20-21,23-31,33-37,39-47H,9-10H2,1-3H3/t11-,20-,21-,23-,24+,25-,26+,27+,28-,29-,30-,31+,33-,34+,35+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](OC[C@H]2[C@@H]([C@@H]([C@@H]([C@H](Oc3cc(c4c(=O)cc(c5cc(c(c(c5)OC)O[C@@H]5[C@@H]([C@@H]([C@@H]([C@H](CO)O5)O)O)O)OC)oc4c3)O)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	800.24	Volume:	726.08 ? Van der Waals volume.
Dense:	1.102	LogP:	-0.88 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.163 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.44 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	36.0
TPSA:	326.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.394	Fsp³:	0.571
MCE-18:	152.455 ? 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:	0.644	Fluc inhibitor:	0.101 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.919 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.508 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.065	Promiscuous compounds:	0.392

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.587	MDCK Permeability:	-5.229
Pgp-inhibitor:	0.0	Pgp-substrate:	0.969
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):	0.907
20% Bioavailability (F20%):	0.725	30% Bioavailability (F30%):	0.988
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.105
Plasma Protein Binding (PPB):	81.422%	Volume Distribution (VD):	-0.098
Fu:	16.609% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.093
BSEP inhibitor:	0.048

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.717
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.988
HLM stability:	0.032 ? 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):

0.49

Half-life (T1/2):

4.662

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.121
Human Hepatotoxicity (H-HT):	0.388	Drug-induced Liver Injury (DILI):	0.965
AMES Toxicity:	0.918	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	0.994
Carcinogencity:	0.019	Eye Corrosion:	0.0
Eye Irritation:	0.021	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.995
Hematotoxicity:	0.357	Drug-induced Nephrotoxicity:	0.941
Genotoxicity:	0.1	RPMI-8226 Immunitoxicity:	0.426
A549 Cytotoxicity:	0.495	Hek293 Cytotoxicity:	0.203
BCF:	0.217 ? 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:	3.012 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.677 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.748 ? 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
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO9130	Phyllospongia papyracea	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17455979]
NPO9130	Phyllospongia papyracea	Species	Thorectidae	Eukaryota	n.a.	Papua New Guinea, at depths of 60 ft (914948? S, 15046808? E)	n.a.	PMID[17455979]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34332066]
NPO18491	Hyacinthus orientalis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599261]
NPO27293	Sus scrofa	Species	Suidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18491	Hyacinthus orientalis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13822	Aconitum fischeri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18743	Lagascea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9130	Phyllospongia papyracea	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6288	Talaromyces islandicus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19066	Pisolithus arhizus	Species	Pisolithaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27293	Sus scrofa	Species	Suidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4156	Apocynum androsaemifolium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18491	Hyacinthus orientalis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13822	Aconitum fischeri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18491	Hyacinthus orientalis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13822	Aconitum fischeri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4156	Apocynum androsaemifolium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27293	Sus scrofa	Species	Suidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13822	Aconitum fischeri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4156	Apocynum androsaemifolium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18743	Lagascea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6288	Talaromyces islandicus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11751	Tetracera alnifolia	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19066	Pisolithus arhizus	Species	Pisolithaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18491	Hyacinthus orientalis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17182	Pulmonaria mollis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4156	Apocynum androsaemifolium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27293	Sus scrofa	Species	Suidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18982	Espeletia grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9130	Phyllospongia papyracea	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13822	Aconitum fischeri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19349	Phlegmariurus yunnanensis	Species	Lycopodiaceae	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 NPC195807 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	20959
0.1-0.2	24084
0.2-0.3	3655
0.3-0.4	780
0.4-0.5	228
0.5-0.6	95
0.6-0.7	37
0.7-0.8	1
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
0.7778	Intermediate Similarity	NPC22062
0.7778	Intermediate Similarity	NPC473634
0.7778	Intermediate Similarity	NPC138811
0.7473	Intermediate Similarity	NPC44931
0.7447	Intermediate Similarity	NPC209296
0.7391	Intermediate Similarity	NPC210073
0.6813	Remote Similarity	NPC243930
0.6739	Remote Similarity	NPC607707
0.6731	Remote Similarity	NPC311850
0.6598	Remote Similarity	NPC204693
0.6566	Remote Similarity	NPC473623
0.6556	Remote Similarity	NPC95090
0.6556	Remote Similarity	NPC27408
0.6542	Remote Similarity	NPC68592
0.65	Remote Similarity	NPC488089
0.6481	Remote Similarity	NPC198199
0.6392	Remote Similarity	NPC275454
0.6392	Remote Similarity	NPC67105
0.6392	Remote Similarity	NPC227508
0.6383	Remote Similarity	NPC311830
0.6346	Remote Similarity	NPC11468
0.6306	Remote Similarity	NPC120952
0.6277	Remote Similarity	NPC22832
0.6275	Remote Similarity	NPC475382
0.6264	Remote Similarity	NPC261866
0.6264	Remote Similarity	NPC39360
0.6264	Remote Similarity	NPC29763
0.6264	Remote Similarity	NPC210003
0.6214	Remote Similarity	NPC101636
0.62	Remote Similarity	NPC475366
0.6196	Remote Similarity	NPC189142
0.6196	Remote Similarity	NPC77660
0.6195	Remote Similarity	NPC262222
0.6182	Remote Similarity	NPC298666
0.6154	Remote Similarity	NPC135358
0.6139	Remote Similarity	NPC65711
0.6105	Remote Similarity	NPC601144
0.61	Remote Similarity	NPC186816
0.6055	Remote Similarity	NPC488083
0.604	Remote Similarity	NPC46202
0.6019	Remote Similarity	NPC480441
0.6019	Remote Similarity	NPC473644
0.6019	Remote Similarity	NPC25523
0.5978	Remote Similarity	NPC473043
0.5978	Remote Similarity	NPC331652
0.5962	Remote Similarity	NPC195257
0.5914	Remote Similarity	NPC19709
0.59	Remote Similarity	NPC15358
0.5842	Remote Similarity	NPC65003
0.5784	Remote Similarity	NPC115674
0.5755	Remote Similarity	NPC298171
0.5745	Remote Similarity	NPC110349
0.5728	Remote Similarity	NPC64051
0.5625	Remote Similarity	NPC181712
0.5619	Remote Similarity	NPC229409
0.5579	Remote Similarity	NPC58053
0.5534	Remote Similarity	NPC479405
0.5534	Remote Similarity	NPC303913
0.5526	Remote Similarity	NPC488086
0.551	Remote Similarity	NPC609451
0.5487	Remote Similarity	NPC488087
0.5481	Remote Similarity	NPC479404
0.5472	Remote Similarity	NPC483707
0.5464	Remote Similarity	NPC186807
0.5455	Remote Similarity	NPC284960
0.5446	Remote Similarity	NPC211594
0.5421	Remote Similarity	NPC270675
0.5421	Remote Similarity	NPC195685
0.5408	Remote Similarity	NPC27942
0.54	Remote Similarity	NPC88023
0.54	Remote Similarity	NPC116458
0.54	Remote Similarity	NPC246943
0.54	Remote Similarity	NPC309025
0.54	Remote Similarity	NPC605784
0.5392	Remote Similarity	NPC8856
0.5377	Remote Similarity	NPC479403
0.5364	Remote Similarity	NPC14187
0.5361	Remote Similarity	NPC93337
0.5361	Remote Similarity	NPC277205
0.5361	Remote Similarity	NPC37919
0.5361	Remote Similarity	NPC323593
0.5361	Remote Similarity	NPC203500
0.5357	Remote Similarity	NPC472993
0.5347	Remote Similarity	NPC190003
0.5347	Remote Similarity	NPC601586
0.534	Remote Similarity	NPC187379
0.5306	Remote Similarity	NPC84362
0.5306	Remote Similarity	NPC105025
0.5306	Remote Similarity	NPC45638
0.53	Remote Similarity	NPC80188
0.53	Remote Similarity	NPC486578
0.5294	Remote Similarity	NPC33265
0.5294	Remote Similarity	NPC172807
0.5283	Remote Similarity	NPC284277
0.5283	Remote Similarity	NPC475497
0.5278	Remote Similarity	NPC142142
0.5273	Remote Similarity	NPC472994
0.5263	Remote Similarity	NPC277532
0.5253	Remote Similarity	NPC201292
0.5248	Remote Similarity	NPC99957
0.5248	Remote Similarity	NPC220169
0.5248	Remote Similarity	NPC602805
0.5243	Remote Similarity	NPC254540
0.5243	Remote Similarity	NPC251417
0.5238	Remote Similarity	NPC473512
0.5238	Remote Similarity	NPC129827
0.5238	Remote Similarity	NPC102028
0.5234	Remote Similarity	NPC470443
0.5225	Remote Similarity	NPC244875
0.52	Remote Similarity	NPC285197
0.5149	Remote Similarity	NPC605067
0.5106	Remote Similarity	NPC134819
0.5102	Remote Similarity	NPC289667
0.5102	Remote Similarity	NPC108831
0.5102	Remote Similarity	NPC238376
0.5102	Remote Similarity	NPC143851
0.5102	Remote Similarity	NPC182634
0.51	Remote Similarity	NPC222936
0.51	Remote Similarity	NPC182045
0.5091	Remote Similarity	NPC476472
0.5091	Remote Similarity	NPC294815
0.5091	Remote Similarity	NPC473073
0.5091	Remote Similarity	NPC16194
0.5051	Remote Similarity	NPC297987
0.5051	Remote Similarity	NPC158674
0.5051	Remote Similarity	NPC136042
0.505	Remote Similarity	NPC307938
0.5049	Remote Similarity	NPC267254
0.5048	Remote Similarity	NPC295613
0.5048	Remote Similarity	NPC473657
0.5047	Remote Similarity	NPC257566
0.5047	Remote Similarity	NPC473571
0.5047	Remote Similarity	NPC110941
0.5046	Remote Similarity	NPC32641
0.5046	Remote Similarity	NPC256188
0.5046	Remote Similarity	NPC35119
0.5046	Remote Similarity	NPC473327
0.5045	Remote Similarity	NPC287889

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC195807 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5347
0.1-0.2	3729
0.2-0.3	62
0.3-0.4	6
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
0.7-0.8	1
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
0.7447	Intermediate Similarity	NPD7054	Phase 4
0.6038	Remote Similarity	NPD7808	Phase 3
0.581	Remote Similarity	NPD7251	Phase 2
0.5741	Remote Similarity	NPD7472	Pre-clinical

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