NPASS Compound

Natural Product: NPC480442

Natural Product ID	NPC480442
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SSICKYJGUJQSAL-LNYDPWEUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	127039668
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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 111117 0 0 0 0 0 0 0 0999 V2000 -8.1640 -2.6627 -0.6893 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9365 -2.9338 -1.5644 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2820 -3.8933 -2.6657 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3259 -3.6781 -3.8127 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0008 -3.2690 -3.2268 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1415 -1.9256 -2.5464 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2806 -1.8346 -1.4536 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4060 -0.7461 -1.5939 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4586 -0.6609 -0.4183 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1460 -0.7872 0.8856 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0675 0.3861 1.7875 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8631 1.2786 1.5916 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9099 0.5346 0.6939 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5915 0.4097 -0.5190 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3671 1.1351 0.5893 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4862 0.3184 0.5341 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9610 -0.1230 1.7606 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4365 0.1867 2.8616 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0749 -0.9480 1.7346 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5741 -1.4071 2.9195 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6687 -2.2208 2.8911 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2365 -2.5529 1.6573 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7377 -2.0927 0.4681 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3519 -2.4329 -0.8371 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5224 -1.6788 -1.1675 N 0 0 0 0 0 0 0 0 0 0 0 0 7.8737 -2.1103 -0.8706 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6142 -0.9972 -0.1511 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9079 0.3230 -0.2152 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3664 0.6142 -1.6022 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3189 -0.4331 -1.8600 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3645 -0.2065 -2.6184 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7222 1.8483 -1.5293 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6078 -1.2544 0.5073 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1083 -0.8004 -0.6111 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0346 0.0021 -0.6542 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6202 0.4167 -1.9800 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7524 1.4261 -2.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3521 1.7630 -3.5748 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 1.0619 -4.6497 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7160 0.0406 -4.3678 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1053 -0.2874 -3.1010 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2225 -0.6838 -5.4408 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4657 1.3639 -5.9619 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3496 -3.3879 1.6818 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9724 -1.0485 4.1384 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2419 1.6176 2.7523 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1602 2.9701 3.0171 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9356 3.4303 4.1891 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9231 4.9728 4.1567 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4935 5.4440 3.9402 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4514 4.2550 3.9875 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8930 4.7250 3.9319 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1273 3.3838 3.0015 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1372 6.4245 4.8398 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8012 5.4612 3.2132 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3076 3.1064 4.0385 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2428 1.1428 1.8119 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5192 -1.0027 0.6084 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4478 -1.7561 -2.1018 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0266 -3.1579 -4.2013 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7761 -2.6124 -4.5893 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1578 -5.2227 -2.2480 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6076 -3.6434 -0.4376 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8454 -2.1826 0.2550 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9121 -2.0665 -1.2321 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1722 -3.3318 -0.8662 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3410 -3.7113 -2.9652 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1944 -4.6041 -4.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6836 -3.9798 -2.4247 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9376 -1.1253 -3.2934 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0058 0.1906 -1.6302 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8766 -0.8865 -2.5482 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7923 -1.5715 -0.5360 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8489 -1.7334 1.4290 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9665 0.0041 2.8483 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2364 2.1447 1.0021 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7963 -0.5273 1.0397 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1189 -2.6221 3.7889 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6414 -3.5132 -0.7629 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5852 -2.2958 -1.6508 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3851 -2.1536 -1.8915 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9240 -3.0710 -0.3765 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7212 -1.3130 0.9116 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6409 -0.8285 -0.5810 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6426 1.1050 0.0669 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0479 0.2889 0.4916 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1705 0.5922 -2.3349 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3601 1.9903 -0.6315 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3645 2.0199 -1.4376 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3441 2.5825 -3.7023 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7957 -1.1010 -2.9330 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8505 -1.4462 -5.3265 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0625 2.2906 -6.1537 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3149 -4.2229 1.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2391 -1.5919 4.5644 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6582 3.4548 2.1139 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5676 3.1551 5.1795 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2350 5.3382 5.1516 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4394 5.8654 2.9173 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3365 3.7763 4.9808 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1850 4.9032 2.8746 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9834 5.7353 4.4312 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5849 4.0632 4.4708 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9275 6.9447 5.1745 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9905 6.4119 3.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5934 3.5941 3.2067 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9107 0.5906 2.3104 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9856 -1.3152 1.4238 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4522 -3.3332 -5.0757 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7444 -2.4409 -4.4309 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3466 -5.6635 -2.6282 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 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 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 29 30 1 0 30 31 2 0 29 32 1 0 23 33 2 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 40 42 1 0 39 43 1 0 22 44 1 0 20 45 1 0 12 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 51 53 1 0 50 54 1 0 49 55 1 0 48 56 1 0 11 57 1 0 10 58 1 0 6 59 1 0 5 60 1 0 4 61 1 0 3 62 1 0 59 2 1 0 14 9 1 0 35 16 2 0 41 36 1 0 53 47 1 0 33 19 1 0 30 25 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 1 3 67 1 6 4 68 1 6 5 69 1 1 6 70 1 6 8 71 1 0 8 72 1 0 9 73 1 6 10 74 1 1 11 75 1 1 12 76 1 6 13 77 1 1 21 78 1 0 24 79 1 0 24 80 1 0 26 81 1 0 26 82 1 0 27 83 1 0 27 84 1 0 28 85 1 0 28 86 1 0 29 87 1 0 32 88 1 0 37 89 1 0 38 90 1 0 41 91 1 0 42 92 1 0 43 93 1 0 44 94 1 0 45 95 1 0 47 96 1 6 48 97 1 1 49 98 1 1 50 99 1 6 51100 1 1 52101 1 0 52102 1 0 52103 1 0 54104 1 0 55105 1 0 56106 1 0 57107 1 0 58108 1 0 60109 1 0 61110 1 0 62111 1 0 M END

Standard InCHIKey	SSICKYJGUJQSAL-LNYDPWEUSA-N
Standard InCHI	InChI=1S/C39H49NO22/c1-12-23(46)27(50)30(53)37(57-12)56-11-21-25(48)29(52)35(62-38-31(54)28(51)24(47)13(2)58-38)39(59-21)61-34-26(49)22-20(45)9-18(43)15(10-40-7-3-4-17(42)36(40)55)33(22)60-32(34)14-5-6-16(41)19(44)8-14/h5-6,8-9,12-13,17,21,23-25,27-31,35,37-39,41-48,50-54H,3-4,7,10-11H2,1-2H3/t12-,13-,17?,21+,23-,24-,25-,27+,28+,29-,30+,31+,35+,37+,38-,39-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(c(CN4CCCC(C4=O)O)c3oc2c2ccc(c(c2)O)O)O)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	883.27	Volume:	803.858 ? Van der Waals volume.
Dense:	1.099	LogP:	-0.005 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.677 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.988 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	43.0
TPSA:	368.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.088	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.834	Fsp³:	0.59
MCE-18:	180.645 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.598	Fluc inhibitor:	0.256 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.657 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.646 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.012	Promiscuous compounds:	0.106

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.569	MDCK Permeability:	-5.137
Pgp-inhibitor:	0.0	Pgp-substrate:	0.997
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):	0.49
20% Bioavailability (F20%):	0.822	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):	81.24%	Volume Distribution (VD):	-0.112
Fu:	18.05% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.031
BSEP inhibitor:	0.015

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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.879
HLM stability:	0.002 ? 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):

0.637

Half-life (T1/2):

6.299

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.348
Human Hepatotoxicity (H-HT):	0.256	Drug-induced Liver Injury (DILI):	0.685
AMES Toxicity:	0.756	Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.022	Skin Sensitization:	0.989
Carcinogencity:	0.005	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.994
Hematotoxicity:	0.035	Drug-induced Nephrotoxicity:	0.146
Genotoxicity:	0.749	RPMI-8226 Immunitoxicity:	0.155
A549 Cytotoxicity:	0.519	Hek293 Cytotoxicity:	0.427
BCF:	0.418 ? 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:	3.082 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.998 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.996 ? 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
NPO40038	Astragalus monspessulanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26558405]

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
Activity	1

Activity Type	# Activity
Cell line	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
NPT984	Cell line	Hepatocyte	n.a.	Activity	=	159.0	%	PMID[26558405]

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 NPC480442 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	8993
0.1-0.2	36458
0.2-0.3	3883
0.3-0.4	305
0.4-0.5	155
0.5-0.6	53
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9126	High Similarity	NPC480443
0.6887	Remote Similarity	NPC122467
0.6455	Remote Similarity	NPC89127
0.633	Remote Similarity	NPC12013
0.633	Remote Similarity	NPC11432
0.633	Remote Similarity	NPC477613
0.6207	Remote Similarity	NPC303694
0.6053	Remote Similarity	NPC602448
0.5984	Remote Similarity	NPC480444
0.5965	Remote Similarity	NPC221342
0.5965	Remote Similarity	NPC476470
0.5948	Remote Similarity	NPC89052
0.5932	Remote Similarity	NPC480441
0.5902	Remote Similarity	NPC162394
0.5833	Remote Similarity	NPC95866
0.5827	Remote Similarity	NPC487499
0.5789	Remote Similarity	NPC142142
0.5649	Remote Similarity	NPC487502
0.5645	Remote Similarity	NPC488736
0.5645	Remote Similarity	NPC488733
0.5625	Remote Similarity	NPC203259
0.5625	Remote Similarity	NPC33054
0.5625	Remote Similarity	NPC155877
0.5625	Remote Similarity	NPC176740
0.5625	Remote Similarity	NPC471725
0.5625	Remote Similarity	NPC134532
0.5625	Remote Similarity	NPC602582
0.5583	Remote Similarity	NPC173837
0.5565	Remote Similarity	NPC480445
0.5556	Remote Similarity	NPC488737
0.552	Remote Similarity	NPC488740
0.5481	Remote Similarity	NPC487500
0.5441	Remote Similarity	NPC487501
0.542	Remote Similarity	NPC473554
0.541	Remote Similarity	NPC25523
0.5391	Remote Similarity	NPC192539
0.5315	Remote Similarity	NPC476215
0.5294	Remote Similarity	NPC292929
0.5238	Remote Similarity	NPC488734
0.5238	Remote Similarity	NPC488735
0.5238	Remote Similarity	NPC488732
0.5238	Remote Similarity	NPC488738
0.5147	Remote Similarity	NPC249560
0.5133	Remote Similarity	NPC254855
0.5133	Remote Similarity	NPC94610
0.513	Remote Similarity	NPC173582
0.513	Remote Similarity	NPC265885
0.513	Remote Similarity	NPC181465
0.513	Remote Similarity	NPC215710
0.513	Remote Similarity	NPC39834
0.513	Remote Similarity	NPC163242
0.513	Remote Similarity	NPC272068
0.513	Remote Similarity	NPC473438
0.513	Remote Similarity	NPC253788
0.5128	Remote Similarity	NPC126784
0.5128	Remote Similarity	NPC241423
0.5118	Remote Similarity	NPC488739
0.5077	Remote Similarity	NPC209550
0.5043	Remote Similarity	NPC255157
0.5043	Remote Similarity	NPC259896
0.5042	Remote Similarity	NPC473327

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480442 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3585
0.1-0.2	5485
0.2-0.3	73
0.3-0.4	4
0.4-0.5	2
0.5-0.6	1
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
0.5625	Remote Similarity	NPD6797	Phase 2

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