NPASS Compound

Natural Product: NPC6908

Natural Product ID	NPC6908
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OQWOKDQAPBSVGH-MKRZDBMGSA-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:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0000637] Glycosylglycerols [CHEMONTID:0003344] 3-O-beta-D-digalactosyl-sn-glycerols [CHEMONTID:0003343] 1-acyl-3-O-beta-D-digalactosyl-sn-glycerols

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 103104 0 0 0 0 0 0 0 0999 V2000 13.0164 1.2695 -1.7426 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0470 0.6145 -0.6936 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7527 -0.7458 -1.1718 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9698 -1.6538 -0.3329 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6057 -1.2722 0.1195 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5477 -0.1803 1.1121 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2714 0.3016 1.6378 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2952 1.0455 0.8304 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7924 0.3645 -0.3755 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6885 0.9830 -1.1494 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3387 1.0049 -0.5654 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1510 1.6843 0.7080 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7841 1.9276 1.2326 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 0.8177 1.4858 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3476 0.0154 0.3457 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4485 -1.0370 0.9845 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0275 -2.0873 1.3038 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8659 -0.7361 1.1420 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7819 -1.6029 1.6991 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0947 -2.8621 0.9786 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6468 -2.7544 -0.3954 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8003 -2.1417 -0.6311 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0574 -0.8396 -0.4586 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5906 -0.1675 -1.7153 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7817 1.2913 -1.4519 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7815 1.7032 -0.0170 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1264 0.6642 0.9509 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3361 0.8366 1.8130 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4639 0.4446 1.3145 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2212 0.7526 0.2978 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5897 1.3229 0.6786 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.5187 1.0038 -0.4697 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.7094 -0.5125 -0.5457 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3690 -1.1906 -0.3488 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2967 -2.2832 -1.3945 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0886 -2.9928 -1.3177 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3171 -0.3265 -0.5807 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3605 -0.9149 -1.6979 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9087 1.4486 -1.6463 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0907 0.6944 1.8149 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0363 -0.6592 0.5306 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5746 2.8327 0.1430 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8661 1.8112 -2.1879 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6706 -0.3995 -2.7482 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8960 -3.6109 0.8634 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4903 1.2169 -2.7091 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1420 2.3146 -1.4329 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9117 0.6492 -1.6880 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1306 1.2750 -0.8628 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4983 0.7283 0.2674 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2250 -0.6036 -2.1953 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7233 -1.2593 -1.4963 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5755 -1.8952 0.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9197 -2.6653 -0.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9562 -1.1194 -0.7541 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2154 -2.2503 0.6256 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1074 -0.5743 2.0783 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1922 0.7015 0.8945 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4814 0.9505 2.5680 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6953 -0.5674 2.1319 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5471 1.4680 1.5337 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8151 2.0510 0.4825 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6455 -0.7117 -0.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6894 0.3707 -1.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5823 0.4559 -2.1601 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9780 2.0703 -1.4094 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6266 1.3344 -1.3728 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1164 -0.1284 -0.4196 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5817 0.9767 1.5278 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7069 2.6477 0.7466 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9151 2.4929 2.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2594 2.7371 0.6001 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2935 0.0603 2.2164 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9351 1.1582 2.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0285 -0.4422 -0.3408 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6716 0.6766 -0.2888 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7164 -1.0713 1.9969 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3373 -1.8643 2.7407 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7403 -3.5098 1.6335 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5697 -3.7817 -0.8617 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8413 -2.1939 -0.9940 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1912 -0.2733 -0.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5452 -0.5950 -2.0633 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8882 1.8005 -1.9414 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7315 2.0960 0.2287 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2299 0.7003 1.7274 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2896 1.9286 2.1405 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0774 0.2218 2.7653 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7833 1.5695 -0.3253 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5043 2.4006 0.7719 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4850 1.5324 -0.3887 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3475 -0.7852 0.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3602 -1.6840 0.6385 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3025 -1.8282 -2.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1626 -2.9689 -1.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2099 -3.7735 -0.6939 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7007 -0.1577 -2.2362 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4988 2.0442 -2.1720 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4204 0.6092 2.5314 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1857 3.6326 -0.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9849 2.7604 -1.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0242 -1.0078 -3.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6444 -3.7836 -0.0646 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 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 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 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 33 38 1 0 32 39 1 0 31 40 1 0 27 41 1 0 26 42 1 0 25 43 1 0 24 44 1 0 20 45 1 0 41 23 1 0 37 30 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 7 60 1 0 8 61 1 0 8 62 1 0 9 63 1 0 9 64 1 0 10 65 1 0 10 66 1 0 11 67 1 0 11 68 1 0 12 69 1 0 12 70 1 0 13 71 1 0 13 72 1 0 14 73 1 0 14 74 1 0 15 75 1 0 15 76 1 0 19 77 1 0 19 78 1 0 20 79 1 1 21 80 1 0 21 81 1 0 23 82 1 1 24 83 1 6 25 84 1 6 26 85 1 1 27 86 1 1 28 87 1 0 28 88 1 0 30 89 1 6 31 90 1 1 32 91 1 1 33 92 1 1 34 93 1 1 35 94 1 0 35 95 1 0 36 96 1 0 38 97 1 0 39 98 1 0 40 99 1 0 42100 1 0 43101 1 0 44102 1 0 45103 1 0 M END

Standard InCHIKey	OQWOKDQAPBSVGH-MKRZDBMGSA-N
Standard InCHI	InChI=1S/C31H58O14/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-23(34)41-17-20(33)18-42-30-29(40)27(38)25(36)22(45-30)19-43-31-28(39)26(37)24(35)21(16-32)44-31/h20-22,24-33,35-40H,2-19H2,1H3/t20-,21+,22+,24-,25-,26-,27-,28+,29+,30+,31-/m0/s1
SMILES	CCCCCCCCCCCCCCCC(=O)OC[C@@H](CO[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO[C@@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O)O)O)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.38	Volume:	648.046 ? Van der Waals volume.
Dense:	1.01	LogP:	2.608 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.488 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.137 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	24.0	Rigid Bonds:	13.0
TPSA:	225.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	2.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.054	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.638	Fsp³:	0.968
MCE-18:	41.902 ? 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:	0.733	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.313	Promiscuous compounds:	0.051

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.5	MDCK Permeability:	-4.973
Pgp-inhibitor:	0.0	Pgp-substrate:	0.988
PAMPA:	0.95 ? 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):	0.725
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.956
Plasma Protein Binding (PPB):	94.853%	Volume Distribution (VD):	-0.053
Fu:	4.909% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.003
OATP1B3 inhibitor:	0.962	BCRP inhibitor:	0.011
BSEP inhibitor:	0.018

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.79
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.17 ? 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):

1.607

Half-life (T1/2):

1.426

ADMET: Toxicity

hERG Blockers:	0.05	hERG Blockers (10um):	0.189
Human Hepatotoxicity (H-HT):	0.465	Drug-induced Liver Injury (DILI):	0.492
AMES Toxicity:	0.964	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.038	Skin Sensitization:	1.0
Carcinogencity:	0.127	Eye Corrosion:	0.0
Eye Irritation:	0.479	Respiratory Toxicity:	0.411
Drug-induced Neurotoxicity:	0.03	Ototoxicity:	0.971
Hematotoxicity:	0.769	Drug-induced Nephrotoxicity:	0.959
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.219
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.58
BCF:	1.603 ? 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:	4.832 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.955 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.442 ? 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
NPO997	Peltodon longipes	Species	Lamiaceae	Eukaryota	roots	Santa Maria, South Brazil	2007-Dec	PMID[21775156]
NPO6621	Salvadora persica	Species	Salvadoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36514376]
NPO6621	Salvadora persica	Species	Salvadoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36854946]
NPO2853	Eschweilera coriacea	Species	Lecythidaceae	Eukaryota	bark	Suriname rainforest	n.a.	PMID[9677272]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23741	Aspergillus violaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2853	Eschweilera coriacea	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3809	Eucalyptus cladocalyx	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO997	Peltodon longipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1920	Podocarpus elongata	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6621	Salvadora persica	Species	Salvadoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20584	Cheilanthes fragrans	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21344	Fadogia agrestis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21534	Ostrya carpinifolia	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3809	Eucalyptus cladocalyx	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3809	Eucalyptus cladocalyx	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23741	Aspergillus violaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20584	Cheilanthes fragrans	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21600	Aconitum variegatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO997	Peltodon longipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2853	Eschweilera coriacea	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22500	Stephania dielsiana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6621	Salvadora persica	Species	Salvadoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1920	Podocarpus elongata	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21344	Fadogia agrestis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21534	Ostrya carpinifolia	Species	Betulaceae	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 NPC6908 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	19765
0.1-0.2	24550
0.2-0.3	4509
0.3-0.4	838
0.4-0.5	165
0.5-0.6	17
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC206601
0.7736	Intermediate Similarity	NPC285003
0.7547	Intermediate Similarity	NPC12040
0.6825	Remote Similarity	NPC156089
0.6667	Remote Similarity	NPC488690
0.65	Remote Similarity	NPC163812
0.6333	Remote Similarity	NPC250619
0.6324	Remote Similarity	NPC470313
0.6324	Remote Similarity	NPC473500
0.6324	Remote Similarity	NPC611497
0.6275	Remote Similarity	NPC145112
0.6032	Remote Similarity	NPC488689
0.6029	Remote Similarity	NPC38295
0.5902	Remote Similarity	NPC469469
0.5893	Remote Similarity	NPC147292
0.5758	Remote Similarity	NPC21693
0.5645	Remote Similarity	NPC143446
0.55	Remote Similarity	NPC241265
0.5467	Remote Similarity	NPC22558
0.5395	Remote Similarity	NPC476611
0.5333	Remote Similarity	NPC76881
0.5294	Remote Similarity	NPC236649
0.5273	Remote Similarity	NPC606861
0.5273	Remote Similarity	NPC607126
0.5185	Remote Similarity	NPC268243
0.5152	Remote Similarity	NPC294293
0.5143	Remote Similarity	NPC110813
0.5102	Remote Similarity	NPC323574
0.5077	Remote Similarity	NPC83839
0.5067	Remote Similarity	NPC475425

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC6908 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6680
0.1-0.2	2309
0.2-0.3	136
0.3-0.4	19
0.4-0.5	5
0.5-0.6	1
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
0.5517	Remote Similarity	NPD3181	Phase 3

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