NPASS Compound

Natural Product: NPC571123

Natural Product ID	NPC571123
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Asparogoside C
IUPAC Name	(2~{S},3~{R},4~{S},5~{S},6~{R})-2-[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,5-dihydroxy-2-(hydroxymethyl)-6-[(4~{S},5'~{S},7~{S},8~{R},9~{S},13~{S})-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-tetrahydropyran]-16-yl]oxy-tetrahydropyran-4-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
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: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 116123 0 0 0 0 0 0 0 0999 V2000 10.1478 0.0812 3.7505 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4788 -0.9231 2.8236 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4720 -1.7729 3.5672 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4647 -2.2774 2.5377 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7641 -1.1601 1.8478 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3947 0.0255 2.2372 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7292 -0.1206 1.7842 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8918 -1.1979 0.4356 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0615 -0.1323 0.0662 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5724 -0.2611 -1.3788 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0961 -0.0075 -1.2195 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2442 -0.3072 -2.3835 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1838 0.9953 -3.2044 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0133 1.8284 -2.7473 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7647 1.1241 -3.2331 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4108 1.7758 -2.6174 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7318 1.1003 -2.8930 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3763 0.9624 -1.6766 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5556 1.6781 -1.5545 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4790 2.6558 -0.5758 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3096 2.1187 0.6953 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8680 1.9215 1.0724 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1347 3.1018 1.0626 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0985 0.8206 0.8326 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4570 0.6962 2.1655 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2957 0.8294 -0.0846 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2715 -0.0492 0.2271 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4613 0.4531 0.6646 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6750 0.0077 1.9528 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9343 0.0004 2.4411 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3417 -1.3648 2.9971 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5019 -1.7427 4.0435 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0471 0.5395 1.6374 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.5969 1.7211 2.2067 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8020 0.7220 0.1737 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.8580 0.2841 -0.6118 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5817 -0.1040 -0.1896 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3306 -0.1131 -1.5348 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8021 0.8347 -1.5066 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7708 1.3772 -2.3570 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5245 -0.2092 -3.5716 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4974 -0.9742 -2.7174 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8411 -0.3587 -3.0885 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2208 -0.9950 -4.4315 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8752 -0.8563 -2.0913 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4175 -0.7740 -0.6945 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4112 -0.5759 0.3787 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8250 -0.8730 0.0068 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0841 -2.3212 -0.2666 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8228 -0.2329 0.9429 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2687 -1.1166 2.0737 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0170 -0.4285 3.3977 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4161 0.9018 3.9094 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9817 0.5490 3.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5099 -0.3652 4.6753 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2308 -1.6116 2.3784 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9055 -1.1532 4.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9198 -2.6419 4.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8782 -3.0278 1.8622 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6805 -2.8206 3.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1869 0.8742 1.6012 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7135 -0.6456 0.7995 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5684 0.8475 0.2204 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0721 0.5497 -1.9708 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8249 -1.2268 -1.8251 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9878 1.0416 -0.8542 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8120 -1.0070 -3.0524 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1026 0.8170 -4.2717 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0944 1.5999 -3.0207 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0926 2.8135 -3.2148 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0065 1.9864 -1.6509 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7147 1.3543 -4.3396 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2285 1.9833 -1.5455 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4875 2.8138 -3.0637 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3696 1.7426 -3.5500 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6269 2.2353 -2.5362 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7592 2.8330 1.4028 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3380 1.2018 0.4054 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8018 1.5679 2.1471 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2226 2.9475 0.6955 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3641 0.0228 0.6193 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9996 1.5125 2.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7469 1.8607 0.0697 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4953 1.5618 0.7141 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8945 0.6443 3.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3529 -1.2337 3.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4107 -2.1408 2.2159 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6892 -2.6591 4.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9188 -0.1808 1.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9061 1.4903 3.1190 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6114 1.7859 -0.0855 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2699 1.0345 -1.1234 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7905 -1.1501 0.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5139 0.7531 -1.9836 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6258 -0.1949 -1.8907 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3363 1.4728 -3.2613 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0968 -0.0630 -4.5616 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4586 -0.7931 -3.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8076 -0.7926 -1.6870 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4398 -2.0416 -3.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5253 -1.7985 -4.7344 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1760 -0.2199 -5.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2230 -1.4110 -4.4218 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9425 -1.9641 -2.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6152 0.0088 -0.5295 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8534 -1.7224 -0.4255 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1471 -1.1451 1.3163 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3951 0.5007 0.7302 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3528 -2.9900 0.2523 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0893 -2.6572 0.1097 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1247 -2.5473 -1.3742 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4399 0.7423 1.2416 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8054 -2.0968 2.1093 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6811 0.4405 3.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1698 -1.1233 4.2566 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9750 0.0075 3.4231 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 5 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 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 24 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 30 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 26 39 1 0 39 40 1 0 17 41 1 0 41 42 1 0 42 43 1 0 43 44 1 6 43 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 6 48 50 1 0 50 51 1 0 51 52 1 0 7 2 1 0 50 9 1 0 51 5 1 0 48 11 1 0 45 12 1 0 43 15 1 0 39 19 1 0 37 28 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 6 3 57 1 0 3 58 1 0 4 59 1 0 4 60 1 0 7 61 1 0 7 62 1 0 9 63 1 6 10 64 1 0 10 65 1 0 11 66 1 0 12 67 1 0 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 0 16 73 1 0 16 74 1 0 17 75 1 0 19 76 1 6 21 77 1 1 22 78 1 0 22 79 1 0 23 80 1 0 24 81 1 6 25 82 1 0 26 83 1 1 28 84 1 1 30 85 1 1 31 86 1 0 31 87 1 0 32 88 1 0 33 89 1 6 34 90 1 0 35 91 1 1 36 92 1 0 37 93 1 1 38 94 1 0 39 95 1 6 40 96 1 0 41 97 1 0 41 98 1 0 42 99 1 0 42100 1 0 44101 1 0 44102 1 0 44103 1 0 45104 1 0 46105 1 0 46106 1 0 47107 1 0 47108 1 0 49109 1 0 49110 1 0 49111 1 0 50112 1 1 51113 1 1 52114 1 0 52115 1 0 52116 1 0 M END

Standard InCHIKey	ZJCKMLSMXPLTKX-GMUIGVSZSA-N
Standard InCHI	InChI=1S/C39H64O13/c1-18-7-12-39(47-17-18)19(2)28-25(52-39)14-24-22-6-5-20-13-21(8-10-37(20,3)23(22)9-11-38(24,28)4)48-36-33(46)34(30(43)27(16-41)50-36)51-35-32(45)31(44)29(42)26(15-40)49-35/h18-36,40-46H,5-17H2,1-4H3/t18-,19-,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]1CCC2(OC1)O[C@H]1CC3C4CCC5CC(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)CC[C@]5(C)C4CC[C@]3(C)[C@H]1[C@@H]2C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	740.43	Volume:	728.921 ? Van der Waals volume.
Dense:	1.016	LogP:	2.247 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.915 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.497 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	42.0
TPSA:	196.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	8.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.194	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.206	Fsp³:	1.0
MCE-18:	200.0 ? 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:	0.63	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? 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:	0.128	Promiscuous compounds:	0.006

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.139	MDCK Permeability:	-5.053
Pgp-inhibitor:	0.011	Pgp-substrate:	0.079
PAMPA:	0.5 ? 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):	0.0
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.72
50% Bioavailability (F50%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028	MRP1:	0.522
Plasma Protein Binding (PPB):	76.489%	Volume Distribution (VD):	-0.445
Fu:	22.031% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.052
BSEP inhibitor:	0.355

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.951	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.037	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.462	CYP3A4-substrate:	0.038
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.345
HLM stability:	0.954 ? 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):

1.945

Half-life (T1/2):

3.407

ADMET: Toxicity

hERG Blockers:	0.04	hERG Blockers (10um):	0.078
Human Hepatotoxicity (H-HT):	0.884	Drug-induced Liver Injury (DILI):	0.83
AMES Toxicity:	0.872	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.092	Skin Sensitization:	1.0
Carcinogencity:	0.535	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.014
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.998
Hematotoxicity:	0.093	Drug-induced Nephrotoxicity:	0.707
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.151
A549 Cytotoxicity:	0.812	Hek293 Cytotoxicity:	0.704
BCF:	1.846 ? 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:	3.755 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.045 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.389 ? 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
NPO47249	Asparagus officinalis L.	Genus	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO54874	Asparagus tenuifolius Lam.	Genus	Asparagaceae	Eukaryota	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

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 NPC571123 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	27699
0.1-0.2	18946
0.2-0.3	2576
0.3-0.4	378
0.4-0.5	118
0.5-0.6	83
0.6-0.7	32
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC234352
0.8242	Intermediate Similarity	NPC184617
0.7952	Intermediate Similarity	NPC297348
0.7952	Intermediate Similarity	NPC325828
0.7952	Intermediate Similarity	NPC249204
0.7952	Intermediate Similarity	NPC48339
0.7952	Intermediate Similarity	NPC141769
0.7952	Intermediate Similarity	NPC477547
0.7791	Intermediate Similarity	NPC206003
0.7791	Intermediate Similarity	NPC473610
0.7653	Intermediate Similarity	NPC132080
0.7604	Intermediate Similarity	NPC475625
0.7558	Intermediate Similarity	NPC477451
0.7528	Intermediate Similarity	NPC107962
0.75	Intermediate Similarity	NPC211354
0.75	Intermediate Similarity	NPC107188
0.7347	Intermediate Similarity	NPC232037
0.7283	Intermediate Similarity	NPC14704
0.7273	Intermediate Similarity	NPC470864
0.7253	Intermediate Similarity	NPC6295
0.7204	Intermediate Similarity	NPC475351
0.7126	Intermediate Similarity	NPC177834
0.7097	Intermediate Similarity	NPC160426
0.7093	Intermediate Similarity	NPC485594
0.6939	Remote Similarity	NPC97700
0.6939	Remote Similarity	NPC30856
0.6923	Remote Similarity	NPC470866
0.6923	Remote Similarity	NPC19400
0.6889	Remote Similarity	NPC250393
0.6702	Remote Similarity	NPC125324
0.6667	Remote Similarity	NPC128572
0.6667	Remote Similarity	NPC294686
0.6629	Remote Similarity	NPC181845
0.6514	Remote Similarity	NPC220836
0.6477	Remote Similarity	NPC24960
0.6476	Remote Similarity	NPC480553
0.6381	Remote Similarity	NPC476112
0.6381	Remote Similarity	NPC307534
0.6364	Remote Similarity	NPC475643
0.6344	Remote Similarity	NPC222731
0.63	Remote Similarity	NPC92890
0.6286	Remote Similarity	NPC480554
0.625	Remote Similarity	NPC116756
0.6239	Remote Similarity	NPC94086
0.6239	Remote Similarity	NPC473817
0.6238	Remote Similarity	NPC51172
0.6238	Remote Similarity	NPC49032
0.6136	Remote Similarity	NPC277715
0.6129	Remote Similarity	NPC131693
0.6129	Remote Similarity	NPC475436
0.6122	Remote Similarity	NPC195297
0.61	Remote Similarity	NPC473601
0.6078	Remote Similarity	NPC471464
0.6075	Remote Similarity	NPC470862
0.6058	Remote Similarity	NPC475319
0.602	Remote Similarity	NPC485595
0.5979	Remote Similarity	NPC264101
0.5922	Remote Similarity	NPC300557
0.5918	Remote Similarity	NPC215408
0.59	Remote Similarity	NPC113044
0.59	Remote Similarity	NPC283829
0.59	Remote Similarity	NPC161676
0.5893	Remote Similarity	NPC480556
0.5872	Remote Similarity	NPC233433
0.5854	Remote Similarity	NPC481189
0.5849	Remote Similarity	NPC470863
0.5825	Remote Similarity	NPC477809
0.5824	Remote Similarity	NPC473774
0.5824	Remote Similarity	NPC481419
0.5824	Remote Similarity	NPC481417
0.5798	Remote Similarity	NPC481190
0.578	Remote Similarity	NPC83137
0.5755	Remote Similarity	NPC115165
0.5728	Remote Similarity	NPC602423
0.5714	Remote Similarity	NPC480555
0.5714	Remote Similarity	NPC54619
0.5714	Remote Similarity	NPC150372
0.57	Remote Similarity	NPC470432
0.57	Remote Similarity	NPC230507
0.567	Remote Similarity	NPC474399
0.562	Remote Similarity	NPC330026
0.561	Remote Similarity	NPC329807
0.5603	Remote Similarity	NPC210569
0.5586	Remote Similarity	NPC84111
0.5586	Remote Similarity	NPC287483
0.5586	Remote Similarity	NPC470865
0.5586	Remote Similarity	NPC477811
0.5556	Remote Similarity	NPC329727
0.5495	Remote Similarity	NPC144790
0.5495	Remote Similarity	NPC149400
0.549	Remote Similarity	NPC141433
0.5488	Remote Similarity	NPC248944
0.5488	Remote Similarity	NPC7479
0.5488	Remote Similarity	NPC257296
0.5484	Remote Similarity	NPC481420
0.5484	Remote Similarity	NPC481421
0.5464	Remote Similarity	NPC291203
0.5464	Remote Similarity	NPC217205
0.5439	Remote Similarity	NPC470867
0.5429	Remote Similarity	NPC470433
0.5429	Remote Similarity	NPC46190
0.5429	Remote Similarity	NPC171073
0.5429	Remote Similarity	NPC485603
0.5354	Remote Similarity	NPC312678
0.5354	Remote Similarity	NPC253268
0.5333	Remote Similarity	NPC202898
0.5327	Remote Similarity	NPC6806
0.53	Remote Similarity	NPC121453
0.5299	Remote Similarity	NPC473505
0.5278	Remote Similarity	NPC151134
0.5278	Remote Similarity	NPC485604
0.5268	Remote Similarity	NPC108072
0.5248	Remote Similarity	NPC306131
0.5248	Remote Similarity	NPC200802
0.5225	Remote Similarity	NPC473518
0.5225	Remote Similarity	NPC309278
0.5207	Remote Similarity	NPC305771
0.5207	Remote Similarity	NPC94072
0.5207	Remote Similarity	NPC169816
0.5196	Remote Similarity	NPC485590
0.5189	Remote Similarity	NPC42482
0.5179	Remote Similarity	NPC232611
0.5169	Remote Similarity	NPC224314
0.5158	Remote Similarity	NPC481418
0.5149	Remote Similarity	NPC128123
0.5135	Remote Similarity	NPC269297
0.5135	Remote Similarity	NPC222202
0.5126	Remote Similarity	NPC477808
0.5119	Remote Similarity	NPC227260
0.5094	Remote Similarity	NPC485605
0.5089	Remote Similarity	NPC475333
0.5089	Remote Similarity	NPC224098
0.5089	Remote Similarity	NPC208383
0.5082	Remote Similarity	NPC263359
0.5048	Remote Similarity	NPC70204
0.5044	Remote Similarity	NPC194207
0.5044	Remote Similarity	NPC22779
0.5042	Remote Similarity	NPC477807
0.5039	Remote Similarity	NPC329820

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC571123 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7688
0.1-0.2	1380
0.2-0.3	67
0.3-0.4	10
0.4-0.5	1
0.5-0.6	2
0.6-0.7	1
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
0.7952	Intermediate Similarity	NPD8171	Phase 2
0.6702	Remote Similarity	NPD8170	Phase 2
0.5488	Remote Similarity	NPD6928	Phase 2
0.5376	Remote Similarity	NPD7991	Discontinued

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