NPASS Compound

Natural Product: NPC244726

Natural Product ID	NPC244726
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DITLNCLWUCYKIJ-UFBWWRLXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24893536
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal 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 118125 0 0 0 0 0 0 0 0999 V2000 11.1629 0.4241 0.6111 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9600 0.9524 -0.1614 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7442 0.3510 0.4685 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4919 1.2819 1.6386 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9763 1.2571 1.7088 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6140 1.3790 0.2479 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1574 1.2276 -0.0315 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4036 1.7785 1.1881 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9599 1.6180 0.8847 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4471 0.7705 0.0018 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9526 0.7819 -0.1386 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4065 -0.6050 -0.2889 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2585 -1.4357 -1.2377 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6753 -1.5219 -0.7788 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2906 -0.1379 -0.8069 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3194 0.3130 -2.2591 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6820 -0.1583 -0.2128 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5865 -1.0317 -1.0392 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9885 -1.0037 -0.4990 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5132 0.3994 -0.4083 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8225 0.8757 -1.8134 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8704 -0.5478 -0.8001 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8205 -1.1025 0.0104 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9388 -0.1247 0.2324 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9913 -0.7218 1.1650 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4631 -2.0073 0.4403 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2659 -2.8684 0.2735 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5157 -4.2556 -0.2157 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3712 -4.9880 0.5880 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3762 -2.2264 -0.6079 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5088 -2.5782 1.1633 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6912 -2.4669 0.4403 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4170 -3.7470 0.2115 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8567 -3.5516 0.6561 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7864 -3.3194 2.1666 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9289 -2.0637 2.3558 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7920 -1.0084 3.0155 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5219 -1.5430 1.1332 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1027 -4.3811 2.7759 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3621 -2.3926 0.0973 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4707 -4.1283 -1.1322 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0075 0.1920 1.2847 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5584 1.1456 0.5622 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8992 2.0953 -0.3789 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7518 3.1463 0.3196 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3107 4.5313 -0.1261 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9541 4.5639 -1.5747 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0323 3.4653 -1.9446 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6046 2.5816 -3.0396 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7239 2.6835 -0.8497 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5044 5.8219 -1.9815 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2622 5.4920 0.2119 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0621 2.9677 -0.0961 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0053 2.5226 1.2313 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8293 2.3853 0.1256 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3821 3.3312 -0.5341 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9229 0.4989 1.6933 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0777 0.9978 0.4270 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2939 -0.6777 0.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0464 0.7274 -1.2439 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9277 -0.6535 0.9012 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9526 0.9137 2.5814 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7058 0.2549 2.1209 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6188 2.0841 2.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9141 2.4047 -0.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8659 1.8690 -0.8848 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6318 1.0369 2.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6872 2.8010 1.4339 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2844 2.2811 1.4673 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6976 1.4043 -1.0209 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4690 1.2399 0.7417 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4650 -1.0977 0.7042 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7948 -2.4338 -1.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1716 -0.9548 -2.2279 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6938 -1.8793 0.2693 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2393 -2.1496 -1.4821 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3174 0.7504 -2.5255 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1575 -0.5297 -2.9611 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5876 1.1423 -2.4386 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5764 -0.6348 0.7914 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5241 -0.8358 -2.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2162 -2.0879 -0.9011 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9398 -1.4215 0.5444 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6652 -1.5826 -1.1376 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3569 1.8592 -1.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3570 0.1193 -2.4181 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8435 1.0608 -2.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3370 -1.4720 0.9269 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4613 -0.0431 -0.7676 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5439 -1.0299 2.1282 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7997 -1.6354 -0.5444 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7810 -2.9774 1.2876 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5444 -4.8274 -0.2126 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8869 -4.3199 -1.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9091 -5.3389 1.4083 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5435 -1.9674 -0.5560 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0444 -4.6175 0.7808 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4644 -4.4346 0.4448 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7966 -3.1800 2.5484 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0177 -2.2646 2.9384 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8112 -1.0549 2.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3424 -0.0190 2.7705 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7455 -1.1911 4.1103 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0277 -4.2018 3.7295 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8704 -2.5929 -0.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4677 -5.1172 -1.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5288 0.2128 0.4484 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4243 1.6636 -1.2507 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7189 3.0580 1.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3970 4.7735 0.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9177 4.3855 -2.1424 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1018 3.9360 -2.3545 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7075 2.6691 -2.9910 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2485 2.9587 -4.0277 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2306 1.5572 -2.8923 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1646 6.2827 -2.5541 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4399 6.1263 -0.5293 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6347 3.7363 0.2094 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 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 12 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 26 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 35 39 1 0 34 40 1 0 33 41 1 0 25 42 1 0 24 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 48 50 1 0 47 51 1 0 46 52 1 0 45 53 1 0 4 54 1 0 54 55 1 0 55 56 2 0 55 2 1 0 20 3 1 0 30 23 1 0 38 32 1 0 50 44 1 0 20 6 1 0 17 7 1 0 15 10 1 0 1 57 1 0 1 58 1 0 1 59 1 0 2 60 1 0 3 61 1 0 4 62 1 0 5 63 1 0 5 64 1 0 6 65 1 0 7 66 1 0 8 67 1 0 8 68 1 0 9 69 1 0 11 70 1 0 11 71 1 0 12 72 1 0 13 73 1 0 13 74 1 0 14 75 1 0 14 76 1 0 16 77 1 0 16 78 1 0 16 79 1 0 17 80 1 0 18 81 1 0 18 82 1 0 19 83 1 0 19 84 1 0 21 85 1 0 21 86 1 0 21 87 1 0 23 88 1 1 24 89 1 6 25 90 1 1 26 91 1 6 27 92 1 1 28 93 1 0 28 94 1 0 29 95 1 0 32 96 1 6 33 97 1 1 34 98 1 1 35 99 1 1 36100 1 1 37101 1 0 37102 1 0 37103 1 0 39104 1 0 40105 1 0 41106 1 0 42107 1 0 44108 1 6 45109 1 1 46110 1 1 47111 1 6 48112 1 6 49113 1 0 49114 1 0 49115 1 0 51116 1 0 52117 1 0 53118 1 0 M END

Standard InCHIKey	DITLNCLWUCYKIJ-UFBWWRLXSA-N
Standard InCHI	InChI=1S/C40H62O16/c1-15-25-23(53-35(15)49)13-22-20-7-6-18-12-19(8-10-39(18,4)21(20)9-11-40(22,25)5)52-38-34(56-37-31(47)29(45)27(43)17(3)51-37)32(48)33(24(14-41)54-38)55-36-30(46)28(44)26(42)16(2)50-36/h6,15-17,19-34,36-38,41-48H,7-14H2,1-5H3/t15?,16-,17-,19?,20?,21?,22?,23?,24+,25?,26-,27-,28+,29+,30+,31+,32-,33+,34+,36-,37-,38+,39-,40-/m0/s1
SMILES	CC1C2C(CC3C4CC=C5CC(CC[C@]5(C)C4CC[C@]23C)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)OC1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	798.4	Volume:	767.315 ? Van der Waals volume.
Dense:	1.041	LogP:	0.759 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.412 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.173 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	43.0
TPSA:	243.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	8.0
Heavy Atoms:	16.0

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:	6.011	Fsp³:	0.925
MCE-18:	151.481 ? 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:	0.596	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:	0.025 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.195	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.233	MDCK Permeability:	-5.1
Pgp-inhibitor:	0.0	Pgp-substrate:	0.725
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):	0.042
20% Bioavailability (F20%):	0.147	30% Bioavailability (F30%):	0.472
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034	MRP1:	0.942
Plasma Protein Binding (PPB):	67.401%	Volume Distribution (VD):	-0.41
Fu:	27.037% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.964
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.0
BSEP inhibitor:	0.01

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:	0.685	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.632
HLM stability:	0.098 ? 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):

0.309

Half-life (T1/2):

3.162

ADMET: Toxicity

hERG Blockers:	0.038	hERG Blockers (10um):	0.281
Human Hepatotoxicity (H-HT):	0.433	Drug-induced Liver Injury (DILI):	0.749
AMES Toxicity:	0.531	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.023	Skin Sensitization:	0.993
Carcinogencity:	0.017	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.048	Drug-induced Nephrotoxicity:	0.305
Genotoxicity:	0.007	RPMI-8226 Immunitoxicity:	0.16
A549 Cytotoxicity:	0.464	Hek293 Cytotoxicity:	0.455
BCF:	0.887 ? 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:	3.511 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.158 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.118 ? 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
NPO10541	Dioscorea spongiosa	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12762799]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	Whole plant	n.a.	steroidal saponins	PMID[16933867]
NPO10541	Dioscorea spongiosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10541	Dioscorea spongiosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10541	Dioscorea spongiosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17650	Dioscorea septemloba	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10541	Dioscorea spongiosa	Species	Dioscoreaceae	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 NPC244726 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	20514
0.1-0.2	24184
0.2-0.3	4048
0.3-0.4	945
0.4-0.5	93
0.5-0.6	36
0.6-0.7	25
0.7-0.8	1
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
0.7609	Intermediate Similarity	NPC94272
0.7347	Intermediate Similarity	NPC475182
0.7273	Intermediate Similarity	NPC165439
0.7216	Intermediate Similarity	NPC470433
0.7216	Intermediate Similarity	NPC46190
0.7216	Intermediate Similarity	NPC171073
0.7143	Intermediate Similarity	NPC248746
0.7143	Intermediate Similarity	NPC122819
0.71	Intermediate Similarity	NPC73243
0.71	Intermediate Similarity	NPC244086
0.71	Intermediate Similarity	NPC84956
0.7071	Intermediate Similarity	NPC42171
0.7	Intermediate Similarity	NPC480555
0.7	Intermediate Similarity	NPC150372
0.6961	Remote Similarity	NPC247037
0.6961	Remote Similarity	NPC269297
0.6961	Remote Similarity	NPC222202
0.6893	Remote Similarity	NPC475333
0.6893	Remote Similarity	NPC224098
0.6893	Remote Similarity	NPC208383
0.6857	Remote Similarity	NPC23808
0.6857	Remote Similarity	NPC87998
0.6827	Remote Similarity	NPC194207
0.6827	Remote Similarity	NPC22779
0.6762	Remote Similarity	NPC249265
0.6729	Remote Similarity	NPC287885
0.67	Remote Similarity	NPC265275
0.6604	Remote Similarity	NPC480554
0.6574	Remote Similarity	NPC308140
0.6514	Remote Similarity	NPC232054
0.6481	Remote Similarity	NPC480553
0.6429	Remote Similarity	NPC224314
0.6339	Remote Similarity	NPC480556
0.6095	Remote Similarity	NPC124677
0.604	Remote Similarity	NPC470432
0.604	Remote Similarity	NPC230507
0.604	Remote Similarity	NPC15249
0.604	Remote Similarity	NPC25455
0.6019	Remote Similarity	NPC486386
0.5963	Remote Similarity	NPC32361
0.5962	Remote Similarity	NPC98696
0.5922	Remote Similarity	NPC305423
0.5922	Remote Similarity	NPC113044
0.5922	Remote Similarity	NPC283829
0.5922	Remote Similarity	NPC161676
0.5909	Remote Similarity	NPC254255
0.5895	Remote Similarity	NPC486114
0.5833	Remote Similarity	NPC102016
0.5833	Remote Similarity	NPC95051
0.5818	Remote Similarity	NPC13193
0.5794	Remote Similarity	NPC6806
0.5769	Remote Similarity	NPC470748
0.5755	Remote Similarity	NPC602423
0.5678	Remote Similarity	NPC477808
0.5648	Remote Similarity	NPC300557
0.5631	Remote Similarity	NPC295980
0.5596	Remote Similarity	NPC150057
0.5596	Remote Similarity	NPC147753
0.5575	Remote Similarity	NPC218571
0.5575	Remote Similarity	NPC487615
0.5556	Remote Similarity	NPC477809
0.5536	Remote Similarity	NPC309278
0.5478	Remote Similarity	NPC256983
0.5472	Remote Similarity	NPC600116
0.5437	Remote Similarity	NPC19400
0.537	Remote Similarity	NPC486388
0.5327	Remote Similarity	NPC14704
0.531	Remote Similarity	NPC475550
0.5283	Remote Similarity	NPC306991
0.5283	Remote Similarity	NPC485595
0.5283	Remote Similarity	NPC6295
0.5225	Remote Similarity	NPC48886
0.5225	Remote Similarity	NPC94881
0.5149	Remote Similarity	NPC181845
0.5098	Remote Similarity	NPC272015

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC244726 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7191
0.1-0.2	1833
0.2-0.3	110
0.3-0.4	13
0.4-0.5	1
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
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
0.7143	Intermediate Similarity	NPD8449	Approved
0.5596	Remote Similarity	NPD8450	Suspended

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