NPASS Compound

Natural Product: NPC66130

Natural Product ID	NPC66130
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	USYGRXORRSAVFG-SJJBXHEASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101316456
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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 91 0 0 0 0 0 0 0 0999 V2000 -9.1021 2.5921 -0.2592 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0355 1.7024 0.3261 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4154 1.3655 1.7381 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6964 2.4080 0.2537 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6180 1.5641 0.8206 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9426 0.4290 1.2848 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2828 1.9224 0.8814 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3470 1.0199 1.4499 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2145 0.6606 0.5410 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4293 -0.4602 1.1554 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2238 -1.7027 0.8318 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1983 -1.3203 -0.2529 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7176 0.0022 -0.7454 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5442 -0.1891 -1.6455 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8680 -0.8271 -2.8747 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7544 -1.0199 -3.7172 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4068 -0.6437 -3.3706 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8658 -1.6603 -5.0331 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7210 0.7719 -1.3265 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3012 -0.2474 2.6176 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9023 0.7034 3.3071 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7352 1.5907 2.6174 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4338 -1.2197 3.3580 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8405 -1.1430 2.8712 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4846 0.0523 2.9845 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5982 -0.0133 4.0398 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7712 -0.7862 3.4914 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0592 -0.4633 2.0661 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9161 -0.0820 1.2071 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3742 -1.1866 0.3286 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3410 -1.9500 -0.3126 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2741 -1.4440 -1.2269 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1762 -0.2307 -1.4359 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2353 -2.3280 -1.8275 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2001 -2.0194 -2.6100 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5741 -0.7204 -3.0592 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5440 0.3961 -2.2872 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8468 1.6331 -2.8696 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1747 1.7364 -4.1971 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2136 0.6146 -4.9952 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9178 -0.5787 -4.4252 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4677 2.9688 -4.7399 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9641 0.6473 1.8648 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1070 0.4833 1.9753 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6261 -2.1649 3.7303 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9038 1.2504 4.4849 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6175 3.1512 0.5406 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9002 1.9973 -0.7765 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6267 3.3128 -0.9522 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9378 0.7598 -0.2831 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6868 0.2824 1.8695 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5982 1.5826 2.4746 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3006 1.9482 2.1005 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4446 2.7729 -0.7431 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7872 3.3021 0.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8381 0.0844 1.7835 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5723 1.5394 0.2968 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3924 -0.5213 0.7064 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7345 -2.1084 1.7275 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5680 -2.5201 0.4189 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2443 -1.3270 0.0879 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1699 -2.0782 -1.0930 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7451 -0.8193 -1.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0489 0.7891 -1.8720 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5190 -0.9059 -5.8005 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8662 -2.0514 -5.2514 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0807 -2.4661 -5.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5232 0.2604 -1.5690 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7487 0.7941 4.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5151 -0.9669 4.4352 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8535 -2.2483 3.2476 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7337 0.7685 3.4534 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1805 -0.5959 4.8848 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6661 -0.4705 4.0952 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5134 -1.4071 1.6228 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3569 0.6668 0.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7497 -0.7147 -0.4910 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6732 -1.8220 0.8795 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1107 -3.4195 -1.5707 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8369 -2.8642 -2.9972 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3746 0.4144 -1.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8171 2.5333 -2.2370 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4724 0.7236 -6.0179 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9381 -1.4825 -5.0184 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3752 3.3952 -4.5839 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2565 0.8424 2.8831 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2095 -2.6882 3.1270 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3872 1.5057 5.3126 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 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 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 2 0 16 18 1 0 13 19 1 6 10 20 1 0 20 21 2 0 21 22 1 0 20 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 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 39 42 1 0 29 43 1 0 28 44 1 0 27 45 1 0 26 46 1 0 22 8 1 0 43 25 1 0 13 9 1 0 41 36 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 3 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 8 56 1 1 9 57 1 6 10 58 1 6 11 59 1 0 11 60 1 0 12 61 1 0 12 62 1 0 14 63 1 0 14 64 1 0 18 65 1 0 18 66 1 0 18 67 1 0 19 68 1 0 21 69 1 0 23 70 1 0 23 71 1 0 25 72 1 1 26 73 1 1 27 74 1 1 28 75 1 6 29 76 1 6 30 77 1 0 30 78 1 0 34 79 1 0 35 80 1 0 37 81 1 0 38 82 1 0 40 83 1 0 41 84 1 0 42 85 1 0 44 86 1 0 45 87 1 0 46 88 1 0 M END

Standard InCHIKey	USYGRXORRSAVFG-SJJBXHEASA-N
Standard InCHI	InChI=1S/C32H42O14/c1-17(2)12-25(36)46-30-26-22(10-11-32(26,40)16-44-18(3)33)20(13-42-30)14-43-31-29(39)28(38)27(37)23(45-31)15-41-24(35)9-6-19-4-7-21(34)8-5-19/h4-9,13,17,22-23,26-31,34,37-40H,10-12,14-16H2,1-3H3/b9-6-/t22-,23-,26-,27-,28+,29-,30+,31-,32+/m1/s1
SMILES	CC(C)CC(=O)O[C@H]1[C@H]2[C@H](CC[C@@]2(COC(=O)C)O)C(=CO1)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=Cc2ccc(cc2)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	650.26	Volume:	629.774 ? Van der Waals volume.
Dense:	1.033	LogP:	1.837 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.437 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.663 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	26.0
TPSA:	207.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.121	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.082	Fsp³:	0.594
MCE-18:	102.941 ? 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:	0.901	Fluc inhibitor:	0.591 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.04 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.501 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.065	Promiscuous compounds:	0.286

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.789	MDCK Permeability:	-5.079
Pgp-inhibitor:	0.001	Pgp-substrate:	0.298
PAMPA:	0.971 ? 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):	0.313
20% Bioavailability (F20%):	0.95	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042	MRP1:	0.02
Plasma Protein Binding (PPB):	79.529%	Volume Distribution (VD):	-0.371
Fu:	18.617% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.864

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.67
CYP2C19-inhibitor:	0.013	CYP2C19-substrate:	0.102
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.342	CYP3A4-substrate:	0.989
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

2.363

Half-life (T1/2):

2.157

ADMET: Toxicity

hERG Blockers:	0.1	hERG Blockers (10um):	0.233
Human Hepatotoxicity (H-HT):	0.638	Drug-induced Liver Injury (DILI):	0.232
AMES Toxicity:	0.892	Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.182	Skin Sensitization:	1.0
Carcinogencity:	0.113	Eye Corrosion:	0.0
Eye Irritation:	0.017	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.084	Ototoxicity:	0.933
Hematotoxicity:	0.062	Drug-induced Nephrotoxicity:	0.891
Genotoxicity:	0.468	RPMI-8226 Immunitoxicity:	0.19
A549 Cytotoxicity:	0.922	Hek293 Cytotoxicity:	0.776
BCF:	0.639 ? 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:	3.433 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.083 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.463 ? 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
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23540981]
NPO11313	Juniperus formosana	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24273878]
NPO11313	Juniperus formosana	Species	Cupressaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24273878]
NPO21031	Dracocephalum moldavica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36838592]
NPO11313	Juniperus formosana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37894884]
NPO8482	Piper marginatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28240	Notholaena lemmonii	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10722	Viburnum furcatum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22630	Calea cuneifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20966	Phlomis nissolii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19964	Stephania sasakii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19964	Stephania sasakii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17951	Styrax japonicus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19964	Stephania sasakii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21598	Hypselodoris porterae	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21277	Eucalyptus rubida	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20834	Artemisia pedemontana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22630	Calea cuneifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17951	Styrax japonicus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19964	Stephania sasakii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8512	Helichrysum dendroideum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22437	Eurya japonica	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11313	Juniperus formosana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28240	Notholaena lemmonii	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21781	Eucalyptus kitsoni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21031	Dracocephalum moldavica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10722	Viburnum furcatum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25742	Rhinella icterica	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10188	Verbascum spinosum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8482	Piper marginatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20966	Phlomis nissolii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21531	Pseudocyphellaria aurata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11320	Benkara malabarica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20380	Tanacetum balsamitoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20020	Murdannia triquetra	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15900	Diaphus coeruleus	Species	Myctophidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20138	Gasterosteus aculeatus	Species	Gasterosteidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20644	Mucuna urens	Species	Fabaceae	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 NPC66130 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	8933
0.1-0.2	36281
0.2-0.3	4114
0.3-0.4	443
0.4-0.5	72
0.5-0.6	12
0.6-0.7	2
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
0.7053	Intermediate Similarity	NPC487698
0.7053	Intermediate Similarity	NPC487697
0.6263	Remote Similarity	NPC184464
0.6263	Remote Similarity	NPC251062
0.5859	Remote Similarity	NPC487695
0.5859	Remote Similarity	NPC487694
0.5444	Remote Similarity	NPC479473
0.5444	Remote Similarity	NPC275721
0.5444	Remote Similarity	NPC479468
0.5444	Remote Similarity	NPC479474
0.5368	Remote Similarity	NPC154262
0.5368	Remote Similarity	NPC159387
0.5275	Remote Similarity	NPC288416
0.5263	Remote Similarity	NPC252114
0.5243	Remote Similarity	NPC487696
0.5053	Remote Similarity	NPC34293

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC66130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4282
0.1-0.2	4802
0.2-0.3	64
0.3-0.4	1
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data