NPASS Compound

Natural Product: NPC305423

Natural Product ID	NPC305423
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DABWSYUOALRPOQ-IPBGRLBVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL442835
PubChem CID	11331681
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 115122 0 0 0 0 0 0 0 0999 V2000 10.1493 3.1594 1.6490 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5531 2.5947 0.3834 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1616 1.1232 0.5753 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9149 0.9850 1.1370 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8693 1.3263 0.3068 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2655 0.0888 -0.3206 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1987 -1.0821 -0.2967 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1256 -0.2087 0.6136 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8025 1.1662 1.1475 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5304 1.5104 0.3520 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8390 0.2058 0.4570 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6191 0.0065 -0.3922 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5590 1.0034 0.1028 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7133 0.6407 -0.5640 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 -0.5345 -1.0763 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3130 -0.7491 -1.7161 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8974 -1.9811 -1.0418 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9887 -3.1351 -1.3890 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7112 -2.9755 -0.6053 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0309 -1.6804 -1.0551 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4195 -1.8960 -2.4821 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1172 -1.3605 -0.1256 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1303 -2.4564 -0.1343 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4668 -2.1049 0.4214 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8949 -0.7436 -0.0584 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0216 -0.7878 -1.5413 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1816 -2.1463 -1.4841 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0535 -2.1278 -0.4014 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0174 -1.0058 -0.5174 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4190 -1.3321 -0.8628 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7938 -2.7860 -0.7538 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8647 -3.3938 0.2763 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2577 -4.8234 0.5181 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5135 -4.9383 1.1154 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6083 -3.3913 -0.3168 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1216 -2.9173 -0.4217 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7614 -0.8642 -2.1549 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0403 -0.1998 0.6410 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6171 1.0895 0.4246 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7884 2.0182 0.7107 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2417 3.4399 0.6419 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0619 3.6152 1.5704 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7936 2.2889 2.2364 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5321 2.3628 3.1001 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5453 1.3463 1.2695 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2897 4.6314 2.4976 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8572 3.7365 -0.6620 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6525 1.9094 -0.4034 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8383 2.0031 0.9272 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4269 2.2763 -0.7555 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2746 3.3110 -0.0135 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4896 4.3975 -0.8239 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3864 2.9988 -1.3626 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6307 4.0826 1.9220 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1462 2.3818 2.4443 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2147 3.3845 1.4428 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2485 2.7061 -0.4771 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9051 0.6377 1.2356 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2756 0.6629 -0.4224 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9833 0.3628 -1.3347 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5858 -2.0119 -0.1054 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9146 -1.0500 0.5565 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7083 -1.2638 -1.2619 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4474 -0.8453 1.4406 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4773 1.0699 2.2098 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9912 2.3452 0.8180 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7773 1.7159 -0.7042 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5552 -0.0512 1.4981 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7909 0.2757 -1.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9210 2.0160 -0.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4044 0.9369 1.1831 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4710 1.4277 -0.6233 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9946 0.1221 -1.5366 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2301 -0.9439 -2.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8264 -1.8679 0.0741 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4300 -4.1115 -1.0739 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7395 -3.2225 -2.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0130 -3.7767 -0.7511 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9522 -2.8777 0.4927 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0489 -1.0206 -2.7855 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4605 -1.8571 -3.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9472 -2.8456 -2.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6421 -1.3293 0.9057 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2664 -2.9606 -1.1127 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7150 -3.2742 0.5315 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1772 -2.8987 0.1938 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3630 -2.0995 1.5463 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2467 -1.4110 -1.9866 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9833 -1.3441 -1.7576 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0093 0.1940 -2.0411 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4400 -1.9769 0.5207 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6339 -0.3048 -1.3180 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1228 -0.7878 -0.1840 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5401 -3.2624 -1.7376 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8278 -2.8025 1.2161 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4864 -5.3808 1.0657 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3474 -5.3073 -0.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4305 -5.5897 1.8691 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4311 -3.8082 -0.7331 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5961 -1.2977 -2.4693 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3274 1.2893 -0.6276 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2947 1.8097 1.6505 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0178 4.1802 0.9389 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1427 3.8931 1.0046 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6119 2.0139 2.9292 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6261 2.3968 2.4350 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5825 3.2370 3.7554 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5458 1.4559 3.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0002 5.2669 2.1969 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6633 4.0189 -1.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5956 1.8654 -0.1065 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9738 1.7600 -1.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6979 3.6113 0.8893 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8345 5.1588 -0.2688 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0698 3.6887 -0.6961 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 5 4 1 1 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 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 17 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 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 43 45 1 0 42 46 1 0 41 47 1 0 40 48 1 0 9 49 1 0 5 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 51 2 1 0 49 5 1 0 25 8 1 0 35 28 1 0 45 39 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 6 3 58 1 0 3 59 1 0 6 60 1 6 7 61 1 0 7 62 1 0 7 63 1 0 8 64 1 1 9 65 1 1 10 66 1 0 10 67 1 0 11 68 1 1 12 69 1 6 13 70 1 0 13 71 1 0 14 72 1 0 16 73 1 0 16 74 1 0 17 75 1 1 18 76 1 0 18 77 1 0 19 78 1 0 19 79 1 0 21 80 1 0 21 81 1 0 21 82 1 0 22 83 1 1 23 84 1 0 23 85 1 0 24 86 1 0 24 87 1 0 26 88 1 0 26 89 1 0 26 90 1 0 28 91 1 1 29 92 1 6 30 93 1 1 31 94 1 6 32 95 1 1 33 96 1 0 33 97 1 0 34 98 1 0 36 99 1 0 37100 1 0 39101 1 6 40102 1 1 41103 1 1 42104 1 6 43105 1 1 44106 1 0 44107 1 0 44108 1 0 46109 1 0 47110 1 0 48111 1 0 50112 1 6 51113 1 1 52114 1 0 53115 1 0 M END

Standard InCHIKey	DABWSYUOALRPOQ-IPBGRLBVSA-N
Standard InCHI	InChI=1S/C39H62O14/c1-16-15-48-39(34(47)27(16)41)17(2)26-24(53-39)13-23-21-7-6-19-12-20(8-10-37(19,4)22(21)9-11-38(23,26)5)50-36-33(31(45)29(43)25(14-40)51-36)52-35-32(46)30(44)28(42)18(3)49-35/h6,16-18,20-36,40-47H,7-15H2,1-5H3/t16-,17-,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]1CO[C@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)O2)[C@H]([C@@H]1O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	754.41	Volume:	735.075 ? Van der Waals volume.
Dense:	1.026	LogP:	2.252 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.699 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.635 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	42.0
TPSA:	217.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	8.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.178	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.439	Fsp³:	0.949
MCE-18:	206.053 ? 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:	0.703	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.203	Promiscuous compounds:	0.012

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.059	MDCK Permeability:	-5.089
Pgp-inhibitor:	0.0	Pgp-substrate:	0.561
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):	0.005
20% Bioavailability (F20%):	0.235	30% Bioavailability (F30%):	0.973
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	0.045
Plasma Protein Binding (PPB):	78.454%	Volume Distribution (VD):	-0.396
Fu:	15.434% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.031
BSEP inhibitor:	0.011

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:	0.0	CYP3A4-substrate:	0.016
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.018
HLM stability:	0.041 ? 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):

0.767

Half-life (T1/2):

3.249

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.037
Human Hepatotoxicity (H-HT):	0.422	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.82	Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.015	Skin Sensitization:	1.0
Carcinogencity:	0.087	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.171
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.652	Drug-induced Nephrotoxicity:	0.989
Genotoxicity:	0.209	RPMI-8226 Immunitoxicity:	0.566
A549 Cytotoxicity:	0.768	Hek293 Cytotoxicity:	0.588
BCF:	1.795 ? 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:	3.436 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.498 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.925 ? 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
NPO27960	Dioscorea polygonoides	Species	Dioscoreaceae	Eukaryota	tubers	n.a.	n.a.	PMID[16038563]
NPO27960	Dioscorea polygonoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27960	Dioscorea polygonoides	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

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell line	2

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
NPT924	Cell line	HSC-2	Homo sapiens	IC50	>	200000.0	nM	DOI[10.1016/j.indcrop.2012.05.026]
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	200000.0	nM	DOI[10.1016/j.indcrop.2012.05.026]

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 NPC305423 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	23649
0.1-0.2	22329
0.2-0.3	2867
0.3-0.4	792
0.4-0.5	121
0.5-0.6	56
0.6-0.7	38
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8065	Intermediate Similarity	NPC113044
0.8065	Intermediate Similarity	NPC283829
0.8065	Intermediate Similarity	NPC161676
0.6893	Remote Similarity	NPC480555
0.6893	Remote Similarity	NPC150372
0.6887	Remote Similarity	NPC63609
0.6863	Remote Similarity	NPC477809
0.6832	Remote Similarity	NPC98696
0.6765	Remote Similarity	NPC470433
0.6765	Remote Similarity	NPC46190
0.6765	Remote Similarity	NPC171073
0.6699	Remote Similarity	NPC248746
0.6635	Remote Similarity	NPC42171
0.6635	Remote Similarity	NPC300557
0.6602	Remote Similarity	NPC602423
0.6545	Remote Similarity	NPC480553
0.6535	Remote Similarity	NPC141433
0.6526	Remote Similarity	NPC181845
0.6514	Remote Similarity	NPC480554
0.6471	Remote Similarity	NPC14704
0.6422	Remote Similarity	NPC194207
0.6422	Remote Similarity	NPC22779
0.6389	Remote Similarity	NPC269297
0.6389	Remote Similarity	NPC222202
0.6346	Remote Similarity	NPC40440
0.633	Remote Similarity	NPC475333
0.633	Remote Similarity	NPC224098
0.633	Remote Similarity	NPC208383
0.6275	Remote Similarity	NPC470432
0.6275	Remote Similarity	NPC230507
0.6182	Remote Similarity	NPC13193
0.6182	Remote Similarity	NPC309278
0.6168	Remote Similarity	NPC6806
0.6162	Remote Similarity	NPC477451
0.614	Remote Similarity	NPC232054
0.6121	Remote Similarity	NPC480556
0.6117	Remote Similarity	NPC94272
0.6038	Remote Similarity	NPC197231
0.6038	Remote Similarity	NPC486388
0.6	Remote Similarity	NPC470748
0.6	Remote Similarity	NPC600116
0.5963	Remote Similarity	NPC475182
0.5962	Remote Similarity	NPC306991
0.5946	Remote Similarity	NPC475550
0.5909	Remote Similarity	NPC73243
0.5909	Remote Similarity	NPC244086
0.5909	Remote Similarity	NPC84956
0.5804	Remote Similarity	NPC247037
0.58	Remote Similarity	NPC297348
0.58	Remote Similarity	NPC249204
0.58	Remote Similarity	NPC48339
0.58	Remote Similarity	NPC141769
0.58	Remote Similarity	NPC477547
0.5798	Remote Similarity	NPC224314
0.5766	Remote Similarity	NPC102016
0.5766	Remote Similarity	NPC95051
0.5673	Remote Similarity	NPC306131
0.5673	Remote Similarity	NPC200802
0.5652	Remote Similarity	NPC249265
0.5648	Remote Similarity	NPC19888
0.5636	Remote Similarity	NPC122819
0.5603	Remote Similarity	NPC23808
0.5603	Remote Similarity	NPC87998
0.5536	Remote Similarity	NPC150057
0.5536	Remote Similarity	NPC147753
0.5517	Remote Similarity	NPC218571
0.5517	Remote Similarity	NPC487615
0.5492	Remote Similarity	NPC477808
0.5481	Remote Similarity	NPC222731
0.5478	Remote Similarity	NPC32361
0.5472	Remote Similarity	NPC600456
0.5424	Remote Similarity	NPC477811
0.5378	Remote Similarity	NPC308140
0.5364	Remote Similarity	NPC51154
0.534	Remote Similarity	NPC272015
0.5321	Remote Similarity	NPC475670
0.531	Remote Similarity	NPC124677
0.5294	Remote Similarity	NPC165439
0.5278	Remote Similarity	NPC107962
0.5278	Remote Similarity	NPC295980
0.525	Remote Similarity	NPC287885
0.5234	Remote Similarity	NPC211354
0.5229	Remote Similarity	NPC15249
0.5229	Remote Similarity	NPC25455
0.5229	Remote Similarity	NPC6295
0.5179	Remote Similarity	NPC161738
0.5143	Remote Similarity	NPC294686
0.5138	Remote Similarity	NPC485601
0.5093	Remote Similarity	NPC54619
0.5093	Remote Similarity	NPC19400
0.5091	Remote Similarity	NPC485595
0.5052	Remote Similarity	NPC22140
0.5052	Remote Similarity	NPC243728
0.5052	Remote Similarity	NPC158088
0.5045	Remote Similarity	NPC70204
0.5044	Remote Similarity	NPC42482
0.5044	Remote Similarity	NPC11548

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC305423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7521
0.1-0.2	1544
0.2-0.3	71
0.3-0.4	10
0.4-0.5	2
0.5-0.6	2
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
0.5636	Remote Similarity	NPD8449	Approved
0.5536	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