NPASS Compound

Natural Product: NPC191662

Natural Product ID	NPC191662
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YBUMLRJVGYOZOE-PRRIITRNSA-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:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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 88 92 0 0 0 0 0 0 0 0999 V2000 4.9849 3.8025 3.0194 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0934 4.2249 1.6819 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6094 3.4080 0.6829 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0298 2.2029 0.9551 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5397 1.3751 -0.0494 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6730 1.8417 -1.3342 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2591 3.0655 -1.6422 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7348 3.8608 -0.6178 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3125 5.0691 -0.9419 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9113 0.0595 0.2171 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8664 -1.0517 0.0351 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2072 -0.7856 0.1714 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1818 -1.7533 0.0221 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7329 -3.0226 -0.2763 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4014 -3.3212 -0.4191 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4778 -2.3330 -0.2622 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0037 -2.6113 -0.4054 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4216 -1.4506 -1.1603 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9834 -1.4659 -2.5647 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4156 -0.3756 -3.2382 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5952 -0.1484 -0.4502 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4410 -0.0590 0.5621 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7657 -0.2580 -0.0920 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8048 -0.1892 0.8268 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8047 0.8858 0.3679 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7849 0.7326 -1.1540 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8751 -0.7049 -1.5050 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1175 -1.6524 -0.3956 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7040 -3.0803 -0.7593 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2686 -3.4150 -2.0065 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5559 -1.3638 0.8095 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8336 -0.8899 -2.5298 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6537 1.3371 -1.6945 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0987 0.5295 0.7422 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7688 1.4748 1.4770 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0566 1.7961 0.7455 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1551 1.7987 1.7777 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0157 0.5562 1.6010 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5898 0.6132 0.3532 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3440 1.7175 3.0603 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2253 1.0145 2.6958 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8751 2.9627 1.6785 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9790 3.0040 0.0581 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6618 -4.0437 -0.4396 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3156 -5.3638 -0.7427 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5403 -1.5030 0.1557 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5013 4.4905 3.7193 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9050 3.7877 3.3375 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4256 2.7888 3.1628 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9516 1.8884 1.9858 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3201 1.2567 -2.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3297 3.3678 -2.6672 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1227 5.8524 -0.3155 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7015 0.0695 1.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5843 0.2185 0.4086 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0283 -4.3221 -0.6563 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8870 -3.5346 -0.9979 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5103 -2.7219 0.5719 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3119 -1.6611 -1.2228 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0771 -1.2864 -2.5467 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6923 -2.3705 -3.0957 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4412 -0.5643 -3.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4007 0.6675 -1.1758 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4800 0.8997 1.1120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5941 -0.8781 1.2867 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4105 0.0026 1.8136 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5149 1.8747 0.7143 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6630 1.2734 -1.5856 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8995 -0.9961 -1.9953 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2364 -1.7060 -0.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1155 -3.8083 -0.0347 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6113 -3.2039 -0.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2124 -3.1342 -2.0210 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4047 -0.1023 -2.6267 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7238 1.3232 -2.6648 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1744 2.3963 1.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2801 1.0103 -0.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7473 0.4474 2.4130 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3146 -0.3200 1.6243 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5770 -0.2456 -0.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1523 2.7143 3.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9062 1.0841 3.8070 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5041 2.8642 0.9241 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5142 2.8048 -0.8018 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1692 -6.0170 -0.4047 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4159 -5.7328 -0.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1167 -5.5156 -1.8352 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8789 -1.4523 1.1217 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 18 21 1 0 21 22 1 0 22 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 29 30 1 0 28 31 1 0 27 32 1 0 26 33 1 0 25 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 40 41 1 0 37 42 1 1 36 43 1 0 14 44 1 0 44 45 1 0 13 46 1 0 8 3 1 0 21 10 1 0 31 24 1 0 41 35 1 0 16 11 1 0 1 47 1 0 1 48 1 0 1 49 1 0 4 50 1 0 6 51 1 0 7 52 1 0 9 53 1 0 10 54 1 1 12 55 1 0 15 56 1 0 17 57 1 0 17 58 1 0 18 59 1 6 19 60 1 0 19 61 1 0 20 62 1 0 21 63 1 6 22 64 1 0 22 65 1 0 24 66 1 1 25 67 1 6 26 68 1 6 27 69 1 6 28 70 1 1 29 71 1 0 29 72 1 0 30 73 1 0 32 74 1 0 33 75 1 0 35 76 1 1 36 77 1 6 38 78 1 0 38 79 1 0 39 80 1 0 40 81 1 0 40 82 1 0 42 83 1 0 43 84 1 0 45 85 1 0 45 86 1 0 45 87 1 0 46 88 1 0 M END

Standard InCHIKey	YBUMLRJVGYOZOE-PRRIITRNSA-N
Standard InCHI	InChI=1S/C31H42O15/c1-41-21-6-14(3-4-19(21)35)24-17-8-20(36)22(42-2)7-15(17)5-16(9-32)18(24)11-43-29-27(26(38)25(37)23(10-33)45-29)46-30-28(39)31(40,12-34)13-44-30/h3-4,6-8,16,18,23-30,32-40H,5,9-13H2,1-2H3/t16-,18-,23-,24-,25-,26+,27-,28+,29-,30+,31-/m1/s1
SMILES	COc1cc(ccc1O)[C@@H]1c2cc(c(cc2C[C@H](CO)[C@H]1CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@@](CO)(CO1)O)O)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.25	Volume:	617.984 ? Van der Waals volume.
Dense:	1.059	LogP:	-0.168 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.489 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.602 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	28.0
TPSA:	237.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.131	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.115	Fsp³:	0.613
MCE-18:	123.2 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.425	Fluc inhibitor:	0.181 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.096 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.135 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.087	Promiscuous compounds:	0.318

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.452	MDCK Permeability:	-5.364
Pgp-inhibitor:	0.0	Pgp-substrate:	0.812
PAMPA:	0.954 ? 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):	0.865
20% Bioavailability (F20%):	0.976	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.879
Plasma Protein Binding (PPB):	71.286%	Volume Distribution (VD):	-0.28
Fu:	28.482% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.02
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.022	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.985	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.504	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.288	CYP3A4-substrate:	0.821
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.051 ? 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):

1.746

Half-life (T1/2):

3.378

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.058
Human Hepatotoxicity (H-HT):	0.781	Drug-induced Liver Injury (DILI):	0.773
AMES Toxicity:	0.854	Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.076	Skin Sensitization:	1.0
Carcinogencity:	0.34	Eye Corrosion:	0.0
Eye Irritation:	0.014	Respiratory Toxicity:	0.119
Drug-induced Neurotoxicity:	0.035	Ototoxicity:	0.986
Hematotoxicity:	0.406	Drug-induced Nephrotoxicity:	0.874
Genotoxicity:	0.44	RPMI-8226 Immunitoxicity:	0.239
A549 Cytotoxicity:	0.926	Hek293 Cytotoxicity:	0.777
BCF:	0.421 ? 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:	2.822 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.483 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.468 ? 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
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10556916]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11087590]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[18181575]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19406895]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[19902967]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19917748]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20932054]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	stem	n.a.	PMID[23157017]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23157017]
NPO11601	Chandonanthus hirtellus	Species	Anastrophyllaceae	Eukaryota	n.a.	Chinese liverworts	n.a.	PMID[24491225]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25043228]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25960261]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[305622]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32603106]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37447036]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38794396]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	Antarctic	n.a.	PMID[8882433]
NPO16170	Xerula longipes	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14630	Boronia ramosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7868	Xeromphis obovata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1890	Lidbeckia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12294	Kydia calycina	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15094	Coriaria myrtifolia	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13236	Viguiera multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2756	Emerita analoga	Species	Hippidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2756	Emerita analoga	Species	Hippidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15094	Coriaria myrtifolia	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1890	Lidbeckia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14077	Chamaecyparis lawsoniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15094	Coriaria myrtifolia	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15818	Lycianthes marlipoensis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15306	Smilax japonica	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2312	Encephalosphaera lasiandra	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16170	Xerula longipes	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13360	Passiflora racemosa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9155	Kageneckia angustifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15726	Rudbeckia subtomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27787	Pseudocentrotus depressus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12517	Tylophora cordifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8611	Cornutia grandifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12294	Kydia calycina	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7056	Pedinophyllum interruptum	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11601	Chandonanthus hirtellus	Species	Anastrophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7868	Xeromphis obovata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8866	Papaver atlanticum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2756	Emerita analoga	Species	Hippidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11567	Picradeniopsis absinthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13236	Viguiera multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13626	Aconitum karakolicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14630	Boronia ramosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10624	Solidago wrightii	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 NPC191662 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	19574
0.1-0.2	27223
0.2-0.3	2826
0.3-0.4	196
0.4-0.5	25
0.5-0.6	11
0.6-0.7	3
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
0.7108	Intermediate Similarity	NPC272619
0.6437	Remote Similarity	NPC286245
0.6353	Remote Similarity	NPC471065
0.6353	Remote Similarity	NPC604724
0.5333	Remote Similarity	NPC185955
0.5333	Remote Similarity	NPC9933
0.5333	Remote Similarity	NPC145979
0.5333	Remote Similarity	NPC469706
0.5333	Remote Similarity	NPC218041
0.5333	Remote Similarity	NPC214326
0.5333	Remote Similarity	NPC260781
0.5238	Remote Similarity	NPC172230
0.5238	Remote Similarity	NPC278808
0.5125	Remote Similarity	NPC277458
0.5125	Remote Similarity	NPC307050

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC191662 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5338
0.1-0.2	3751
0.2-0.3	61
0.3-0.4	0
0.4-0.5	0
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