NPASS Compound

Natural Product: NPC475611

Natural Product ID	NPC475611
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	24,2',3',4'-Tetra-O-Acetyl-3-O-Alpha-L-Arabinopyranosyl Hederagenin
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(acetyloxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-triacetyloxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL509280
PubChem CID	11193576
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 119124 0 0 0 0 0 0 0 0999 V2000 4.3436 2.9399 3.6936 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0611 2.4120 3.2129 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9594 2.6649 3.7979 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9941 1.5905 2.0685 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7527 1.1227 1.6711 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7493 0.2345 0.4270 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6493 -0.9433 0.8273 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3177 1.0267 -0.6800 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4962 1.1137 -1.9484 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0373 0.9202 -1.7843 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2779 -0.3871 -1.0253 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3271 -0.1977 0.3111 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0143 -1.3984 1.1350 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4712 -1.4686 1.4276 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3377 -1.2286 0.2183 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7513 -0.3426 -0.8193 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5901 -0.3922 -2.0660 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0372 -0.4973 -1.7236 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5400 -0.5768 -0.5152 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6559 -0.5679 0.6532 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4279 0.8910 1.0265 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2340 -1.2492 1.8602 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4968 -2.0008 1.6307 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5335 -1.2602 0.8299 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0280 -0.6617 -0.4233 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5506 0.7362 -0.6711 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0257 0.8862 -0.3816 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4604 0.1935 0.8876 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1937 -0.1609 1.6627 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8689 0.5321 -1.5685 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2448 2.3856 -0.1278 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6129 -2.2256 0.5333 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8996 -2.4952 -0.6444 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2903 -2.8174 1.5734 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7348 -2.5461 -0.4090 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2616 -1.4879 -1.8407 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5807 0.4684 -1.0063 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6065 1.3461 -1.0833 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8580 1.4400 -2.5113 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0324 0.1430 -3.0142 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2352 -0.5244 -2.3243 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8720 0.5620 -1.5055 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8531 0.9145 -0.3920 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4523 1.9257 0.4202 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8672 1.6441 1.7038 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7135 0.4966 2.1729 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4986 2.6910 2.5355 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1371 0.2872 -1.0106 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1683 1.1706 -1.3827 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8954 2.1644 -2.1447 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5640 1.0430 -0.9566 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6997 -1.4834 -1.4341 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0176 -2.8119 -1.4791 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8191 -3.2345 -2.3365 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4124 -3.7480 -0.5121 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1401 3.4254 4.6852 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0638 2.1054 3.9421 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7873 3.7098 3.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2355 0.5998 2.5124 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0974 2.0212 1.4772 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1936 -1.9190 0.6694 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9397 -0.9120 1.8979 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6023 -0.9414 0.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5572 2.0936 -0.4505 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9533 0.3964 -2.6811 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6283 2.1030 -2.4377 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4335 0.9336 -2.7715 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3448 1.7184 -1.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2995 0.6376 0.7792 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2607 -2.3586 0.6386 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5464 -1.3805 2.1025 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6640 -0.7387 2.2344 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6613 -2.5247 1.7625 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9182 0.7147 -0.4227 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3619 -1.2121 -2.7476 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4681 0.5503 -2.6406 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6964 -0.5034 -2.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4920 1.0540 1.5856 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2334 1.1367 1.7816 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6080 1.5944 0.2095 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5125 -1.9438 2.3370 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4577 -0.5024 2.6816 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9697 -2.1651 2.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3495 -3.0350 1.2368 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3606 -1.2788 -1.3039 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4418 0.9996 -1.7658 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9672 1.5191 -0.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9995 -0.7420 0.6433 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1567 0.8135 1.4852 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5444 -0.5998 2.6298 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5783 0.7253 1.7933 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2654 0.3613 -2.4853 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5880 1.3551 -1.8518 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5185 -0.3578 -1.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0383 2.9615 -1.0435 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3135 2.5049 0.1135 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6018 2.7066 0.7173 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0191 -3.4816 1.3436 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4846 -3.3879 0.3023 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8272 -2.6471 -0.5740 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2691 -2.7315 -1.3947 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1082 -2.5107 -1.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3855 -1.3623 -1.8445 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0341 -1.3672 -2.8867 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4005 2.4016 -0.8353 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1288 -0.4771 -2.8918 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2646 0.2296 -4.0758 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9284 -0.9706 -3.0585 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8434 1.4887 -2.1584 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7673 -0.0225 0.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4127 2.4550 3.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5887 2.6979 2.3099 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0740 3.6844 2.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2508 1.2839 -1.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7778 1.8443 -0.2112 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8193 0.0314 -0.5786 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3295 -3.4926 -0.3444 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4372 -4.7658 -0.9704 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9724 -3.7653 0.4328 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 6 5 1 1 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 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 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 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 27 31 1 0 24 32 1 6 32 33 2 0 32 34 1 0 15 35 1 6 11 36 1 6 8 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 42 48 1 0 48 49 1 0 49 50 2 0 49 51 1 0 41 52 1 0 52 53 1 0 53 54 2 0 53 55 1 0 12 6 1 0 20 15 1 0 29 24 1 0 43 38 1 0 16 11 1 0 25 19 1 0 1 56 1 0 1 57 1 0 1 58 1 0 5 59 1 0 5 60 1 0 7 61 1 0 7 62 1 0 7 63 1 0 8 64 1 1 9 65 1 0 9 66 1 0 10 67 1 0 10 68 1 0 12 69 1 1 13 70 1 0 13 71 1 0 14 72 1 0 14 73 1 0 16 74 1 1 17 75 1 0 17 76 1 0 18 77 1 0 21 78 1 0 21 79 1 0 21 80 1 0 22 81 1 0 22 82 1 0 23 83 1 0 23 84 1 0 25 85 1 6 26 86 1 0 26 87 1 0 28 88 1 0 28 89 1 0 29 90 1 0 29 91 1 0 30 92 1 0 30 93 1 0 30 94 1 0 31 95 1 0 31 96 1 0 31 97 1 0 34 98 1 0 35 99 1 0 35100 1 0 35101 1 0 36102 1 0 36103 1 0 36104 1 0 38105 1 1 40106 1 0 40107 1 0 41108 1 6 42109 1 6 43110 1 1 47111 1 0 47112 1 0 47113 1 0 51114 1 0 51115 1 0 51116 1 0 55117 1 0 55118 1 0 55119 1 0 M END

Standard InCHIKey	RNQWMEXCSFUKMK-NQSOMBOQSA-N
Standard InCHI	InChI=1S/C43H64O12/c1-24(44)51-23-40(8)31-13-16-42(10)32(12-11-28-29-21-38(5,6)17-19-43(29,37(48)49)20-18-41(28,42)9)39(31,7)15-14-33(40)55-36-35(54-27(4)47)34(53-26(3)46)30(22-50-36)52-25(2)45/h11,29-36H,12-23H2,1-10H3,(H,48,49)/t29-,30-,31+,32+,33-,34-,35+,36-,39-,40-,41+,42+,43-/m0/s1
SMILES	CC(=O)OC[C@]1(C)[C@H](CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C)O[C@@H]1OC[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	772.44	Volume:	790.609 ? Van der Waals volume.
Dense:	0.977	LogP:	2.838 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.055 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.004 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	37.0
TPSA:	160.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.117	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.545	Fsp³:	0.837
MCE-18:	131.646 ? 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:	0.989	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.034 ? 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:	0.251	Promiscuous compounds:	0.338

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.468	MDCK Permeability:	-5.215
Pgp-inhibitor:	0.849	Pgp-substrate:	0.012
PAMPA:	0.999 ? 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):	0.001
20% Bioavailability (F20%):	0.155	30% Bioavailability (F30%):	0.19
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.999
Plasma Protein Binding (PPB):	87.404%	Volume Distribution (VD):	-0.584
Fu:	7.434% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.919	BCRP inhibitor:	0.002
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.356	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.014	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.806
HLM stability:	0.682 ? 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):

1.939

Half-life (T1/2):

0.85

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.013
Human Hepatotoxicity (H-HT):	0.836	Drug-induced Liver Injury (DILI):	0.981
AMES Toxicity:	0.794	Rat Oral Acute Toxicity:	0.356
Maximum Recommended Daily Dose:	0.116	Skin Sensitization:	0.999
Carcinogencity:	0.883	Eye Corrosion:	0.002
Eye Irritation:	0.034	Respiratory Toxicity:	0.136
Drug-induced Neurotoxicity:	0.035	Ototoxicity:	0.547
Hematotoxicity:	0.847	Drug-induced Nephrotoxicity:	0.964
Genotoxicity:	0.991	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.395	Hek293 Cytotoxicity:	0.124
BCF:	0.469 ? 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:	3.993 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.797 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.168 ? 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
NPO16143.1	Phyllanthus polyphyllus	Under-species	n.a.	n.a.	leaves	n.a.	n.a.	PMID[16038539]
NPO16143.1	Phyllanthus polyphyllus	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]

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

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell line	2
Non-molecular	1

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
NPT91	Cell line	KB	Homo sapiens	IC50	=	3.7	ug.mL-1	PMID[22512738]
NPT639	Cell line	NCI-H187	Homo sapiens	IC50	=	2.2	ug.mL-1	PMID[25856683]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3.6	ug.mL-1	PMID[16038539]

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 NPC475611 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	20253
0.1-0.2	25832
0.2-0.3	2874
0.3-0.4	658
0.4-0.5	160
0.5-0.6	66
0.6-0.7	4
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
0.8554	High Similarity	NPC473538
0.6386	Remote Similarity	NPC120840
0.625	Remote Similarity	NPC23241
0.6211	Remote Similarity	NPC284807
0.6092	Remote Similarity	NPC96580
0.5851	Remote Similarity	NPC283849
0.5851	Remote Similarity	NPC28198
0.5851	Remote Similarity	NPC476123
0.5833	Remote Similarity	NPC100383
0.5667	Remote Similarity	NPC474727
0.5657	Remote Similarity	NPC191410
0.5618	Remote Similarity	NPC296164
0.5579	Remote Similarity	NPC204407
0.5567	Remote Similarity	NPC286347
0.5556	Remote Similarity	NPC294112
0.5534	Remote Similarity	NPC174679
0.5534	Remote Similarity	NPC279554
0.5534	Remote Similarity	NPC56713
0.5534	Remote Similarity	NPC59804
0.5521	Remote Similarity	NPC606107
0.5514	Remote Similarity	NPC104400
0.5514	Remote Similarity	NPC10320
0.5481	Remote Similarity	NPC127056
0.5465	Remote Similarity	NPC480946
0.5465	Remote Similarity	NPC130577
0.5465	Remote Similarity	NPC142415
0.5465	Remote Similarity	NPC102683
0.5437	Remote Similarity	NPC136877
0.5413	Remote Similarity	NPC73829
0.5402	Remote Similarity	NPC156981
0.5398	Remote Similarity	NPC280941
0.5398	Remote Similarity	NPC235772
0.5364	Remote Similarity	NPC119794
0.5341	Remote Similarity	NPC158141
0.5327	Remote Similarity	NPC469945
0.5321	Remote Similarity	NPC139044
0.5321	Remote Similarity	NPC471383
0.5283	Remote Similarity	NPC6377
0.5283	Remote Similarity	NPC488561
0.5283	Remote Similarity	NPC208381
0.5281	Remote Similarity	NPC200752
0.5281	Remote Similarity	NPC298554
0.5275	Remote Similarity	NPC488521
0.5273	Remote Similarity	NPC257468
0.5268	Remote Similarity	NPC323359
0.5263	Remote Similarity	NPC62725
0.5243	Remote Similarity	NPC164194
0.5234	Remote Similarity	NPC22956
0.5227	Remote Similarity	NPC270768
0.5227	Remote Similarity	NPC59263
0.5227	Remote Similarity	NPC210106
0.5221	Remote Similarity	NPC488564
0.5189	Remote Similarity	NPC109079
0.5176	Remote Similarity	NPC604575
0.5146	Remote Similarity	NPC475472
0.5143	Remote Similarity	NPC12288
0.514	Remote Similarity	NPC472949
0.5135	Remote Similarity	NPC481082
0.5135	Remote Similarity	NPC164419
0.5096	Remote Similarity	NPC22676
0.5096	Remote Similarity	NPC270667
0.5094	Remote Similarity	NPC25605
0.5089	Remote Similarity	NPC79718
0.5056	Remote Similarity	NPC275809
0.5056	Remote Similarity	NPC84319
0.5056	Remote Similarity	NPC52021
0.5056	Remote Similarity	NPC599947
0.5055	Remote Similarity	NPC485589
0.5053	Remote Similarity	NPC481362
0.5047	Remote Similarity	NPC114441
0.5044	Remote Similarity	NPC276093

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475611 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5826
0.1-0.2	3286
0.2-0.3	31
0.3-0.4	6
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