NPASS Compound

Natural Product: NPC207928

Natural Product ID	NPC207928
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NSNUSRJUPCLYHS-HYBPNVACSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21630156
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 118124 0 0 0 0 0 0 0 0999 V2000 5.7232 1.8519 -1.8666 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2212 0.7228 -1.0081 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2869 -0.3692 -0.7092 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0514 -0.1927 0.0633 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0523 0.7481 -0.4679 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7842 0.7301 0.4541 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0508 1.5994 1.6373 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7676 1.2902 -0.5117 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2505 0.6556 -1.8178 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3660 -0.6083 -1.8518 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9208 0.0328 -1.5483 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0996 -0.8253 -1.2508 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2575 -1.8773 -2.2778 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6237 -2.1397 -2.7375 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6731 -1.5775 -2.1932 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0708 -1.8718 -2.6939 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5402 -0.5613 -3.3099 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1055 0.6082 -2.4739 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7645 0.2266 -1.0434 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5190 -0.6290 -1.0602 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4438 -1.4648 0.1905 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2720 0.1610 -1.2431 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0619 1.2580 -0.2616 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6913 1.8245 -0.1776 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6166 0.7885 -0.2516 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7059 -0.0813 0.9625 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7562 -0.4745 -0.4213 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3085 0.1381 0.6825 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7835 0.3815 0.3210 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3227 1.3549 1.3277 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1841 0.6748 2.6985 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7701 0.1797 2.8758 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7598 -0.5942 4.1954 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4643 -0.9998 4.4251 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3348 -0.6352 1.8322 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0420 -0.4036 2.7132 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6400 1.6262 1.0331 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9386 0.7901 -0.9795 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9080 -0.5870 -3.5641 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5611 0.3521 -1.6556 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4222 2.0984 -0.3646 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4326 0.1464 -1.7287 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0661 -0.8770 -1.1103 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6255 -0.4740 0.0870 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3030 -1.3812 1.2269 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5686 -1.7646 1.9501 C 0 0 2 0 0 0 0 0 0 0 0 0 10.4223 -0.5291 2.2105 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5587 0.2744 0.9249 C 0 0 1 0 0 0 0 0 0 0 0 0 11.9973 0.6130 0.6389 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7251 -0.5750 0.5102 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0373 -0.4929 -0.1358 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9059 0.2362 3.2307 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2668 -2.6698 1.1877 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4027 -0.7778 2.1163 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8512 1.6093 -2.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7118 2.8191 -1.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5199 2.0750 -2.6840 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5637 1.1788 -0.0336 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0529 -0.8549 -1.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9297 -1.2167 -0.2667 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3644 0.1560 1.0975 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5432 -1.2033 0.1938 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6297 -0.3248 0.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0641 2.0893 1.5420 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1490 0.9296 2.5310 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2910 2.3693 1.8069 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8317 2.3875 -0.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0068 1.2865 -2.6858 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7613 -1.2440 -1.0418 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4317 -1.1100 -2.8227 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1778 0.7764 -2.3268 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0520 -1.2808 -0.2402 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5529 -1.6615 -3.1154 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8909 -2.8522 -1.8286 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7622 -2.8247 -3.5585 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7253 -2.2613 -1.9181 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0047 -2.6227 -3.4901 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0406 -0.5324 -4.3242 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1410 0.9851 -2.9206 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7893 1.4810 -2.5418 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5289 1.1800 -0.5377 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4677 -1.9231 0.3173 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1248 -0.9435 1.0883 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7439 -2.3398 0.0462 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2351 0.6300 -2.2682 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7293 2.1157 -0.5815 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4497 1.0054 0.7699 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6182 2.4034 0.7783 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5588 2.5896 -0.9934 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3395 -1.0981 0.8422 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0870 0.4057 1.7718 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7253 -0.1200 1.3909 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8973 1.1198 0.9396 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2979 -0.6005 0.4843 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6778 2.2631 1.2747 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3915 1.4134 3.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1156 1.0764 2.9661 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2056 0.0240 4.9833 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3773 -1.5040 4.0456 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9349 -0.2226 4.7479 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9180 -0.2335 2.2790 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0140 0.8520 0.5432 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6146 0.2566 -1.4350 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1278 -0.5596 -4.5329 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8166 2.6910 -0.8725 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0615 -0.2138 -2.7158 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1517 0.9743 -1.9791 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4260 0.5951 0.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8133 -2.2889 0.8023 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2933 -2.1422 2.9626 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4290 -0.8805 2.4824 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9493 1.1937 0.9869 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4186 1.1955 1.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0934 1.2013 -0.2947 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5083 -1.0050 -0.3638 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4928 -0.3532 3.9174 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6582 -3.3955 0.8767 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2327 -1.4453 2.8392 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 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 19 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 32 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 17 39 1 0 9 40 1 0 5 41 1 6 2 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 48 51 1 0 47 52 1 0 46 53 1 0 45 54 1 0 40 5 1 0 51 44 1 0 25 8 1 0 35 28 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 1 3 59 1 0 3 60 1 0 4 61 1 0 4 62 1 0 6 63 1 1 7 64 1 0 7 65 1 0 7 66 1 0 8 67 1 6 9 68 1 6 10 69 1 0 10 70 1 0 11 71 1 6 12 72 1 1 13 73 1 0 13 74 1 0 14 75 1 0 16 76 1 0 16 77 1 0 17 78 1 6 18 79 1 0 18 80 1 0 19 81 1 1 21 82 1 0 21 83 1 0 21 84 1 0 22 85 1 6 23 86 1 0 23 87 1 0 24 88 1 0 24 89 1 0 26 90 1 0 26 91 1 0 26 92 1 0 28 93 1 1 29 94 1 6 30 95 1 1 31 96 1 1 32 97 1 1 33 98 1 0 33 99 1 0 34100 1 0 36101 1 0 37102 1 0 38103 1 0 39104 1 0 41105 1 0 42106 1 0 42107 1 0 44108 1 1 45109 1 6 46110 1 1 47111 1 1 48112 1 1 49113 1 0 49114 1 0 50115 1 0 52116 1 0 53117 1 0 54118 1 0 M END

Standard InCHIKey	NSNUSRJUPCLYHS-HYBPNVACSA-N
Standard InCHI	InChI=1S/C39H64O15/c1-17(16-50-35-33(47)31(45)29(43)25(14-40)51-35)7-10-39(49)18(2)28-24(54-39)13-23-21-6-5-19-11-20(42)12-27(38(19,4)22(21)8-9-37(23,28)3)53-36-34(48)32(46)30(44)26(15-41)52-36/h5,17-18,20-36,40-49H,6-16H2,1-4H3/t17-,18-,20+,21+,22-,23-,24-,25+,26+,27+,28-,29+,30-,31-,32-,33+,34+,35+,36-,37-,38-,39+/m0/s1
SMILES	C[C@@H](CC[C@@]1([C@@H](C)[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@H](C[C@H]([C@]5(C)[C@H]4CC[C@]23C)O[C@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O)O)O)O)O1)O)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	772.42	Volume:	752.422 ? Van der Waals volume.
Dense:	1.027	LogP:	1.871 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.602 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.479 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	36.0
TPSA:	248.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	10.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.123	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.999	Fsp³:	0.949
MCE-18:	135.526 ? 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:	0.632	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.208	Promiscuous compounds:	0.048

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.034	MDCK Permeability:	-5.149
Pgp-inhibitor:	0.0	Pgp-substrate:	0.961
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):	0.529
20% Bioavailability (F20%):	0.695	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.021
Plasma Protein Binding (PPB):	43.139%	Volume Distribution (VD):	-0.438
Fu:	47.171% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.094
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:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.634
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.975
HLM stability:	0.004 ? 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):

1.118

Half-life (T1/2):

2.983

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.016
Human Hepatotoxicity (H-HT):	0.759	Drug-induced Liver Injury (DILI):	0.659
AMES Toxicity:	0.804	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.128	Skin Sensitization:	1.0
Carcinogencity:	0.401	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.998
Hematotoxicity:	0.388	Drug-induced Nephrotoxicity:	0.938
Genotoxicity:	0.093	RPMI-8226 Immunitoxicity:	0.155
A549 Cytotoxicity:	0.897	Hek293 Cytotoxicity:	0.724
BCF:	1.211 ? 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:	3.286 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.497 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.697 ? 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
NPO1287	Coriaria nepalensis	Species	Coriariaceae	Eukaryota	n.a.	root	n.a.	PMID[12016873]
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	roots	n.a.	n.a.	PMID[19729316]
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9588	Atelopus chiriquiensis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22493	Xenia crassa	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25200	Takifugu niphobles	Species	Tetraodontidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22493	Xenia crassa	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9474	Clausena pentaphylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25200	Takifugu niphobles	Species	Tetraodontidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1287	Coriaria nepalensis	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16239	Rhodiola rosea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9588	Atelopus chiriquiensis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5848	Pimpinella nudicaulis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5594	Notholaena nivea	Species	Pteridaceae	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 NPC207928 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	21700
0.1-0.2	23839
0.2-0.3	3609
0.3-0.4	568
0.4-0.5	98
0.5-0.6	29
0.6-0.7	12
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9494	High Similarity	NPC476538
0.9494	High Similarity	NPC476539
0.8214	Intermediate Similarity	NPC476540
0.8214	Intermediate Similarity	NPC476541
0.6629	Remote Similarity	NPC226642
0.6598	Remote Similarity	NPC98696
0.6477	Remote Similarity	NPC485600
0.6304	Remote Similarity	NPC291203
0.6304	Remote Similarity	NPC217205
0.6275	Remote Similarity	NPC73243
0.6275	Remote Similarity	NPC244086
0.6275	Remote Similarity	NPC84956
0.6275	Remote Similarity	NPC102016
0.6275	Remote Similarity	NPC95051
0.6196	Remote Similarity	NPC485602
0.6154	Remote Similarity	NPC247037
0.5981	Remote Similarity	NPC218571
0.5981	Remote Similarity	NPC487615
0.5981	Remote Similarity	NPC249265
0.593	Remote Similarity	NPC473923
0.5926	Remote Similarity	NPC23808
0.5926	Remote Similarity	NPC87998
0.5795	Remote Similarity	NPC473476
0.5758	Remote Similarity	NPC485601
0.5556	Remote Similarity	NPC306131
0.5556	Remote Similarity	NPC200802
0.5487	Remote Similarity	NPC475357
0.5463	Remote Similarity	NPC148965
0.5437	Remote Similarity	NPC485599
0.537	Remote Similarity	NPC98018
0.537	Remote Similarity	NPC284104
0.537	Remote Similarity	NPC103616
0.5364	Remote Similarity	NPC475487
0.534	Remote Similarity	NPC70204
0.5273	Remote Similarity	NPC470863
0.5204	Remote Similarity	NPC13190
0.5182	Remote Similarity	NPC51520
0.5182	Remote Similarity	NPC303069
0.5091	Remote Similarity	NPC294129
0.5089	Remote Similarity	NPC470861
0.505	Remote Similarity	NPC486118
0.5048	Remote Similarity	NPC475670
0.5043	Remote Similarity	NPC84111
0.5043	Remote Similarity	NPC287483
0.5043	Remote Similarity	NPC470865

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC207928 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7382
0.1-0.2	1665
0.2-0.3	92
0.3-0.4	10
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