NPASS Compound

Natural Product: NPC475670

Natural Product ID	NPC475670
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CEUOJNPNKKLCDB-VVFBCDONSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL511017
PubChem CID	11181702
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 111118 0 0 0 0 0 0 0 0999 V2000 -9.5610 2.0630 2.9949 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4879 1.5391 2.0981 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3830 2.5958 1.9928 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4838 2.1310 1.0665 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8352 0.9567 1.4097 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3803 0.3608 2.6832 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8838 0.2366 2.5767 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1579 -0.8239 1.7226 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3172 1.1966 1.5355 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8082 -0.1293 1.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8184 -0.6942 0.2621 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9211 0.1092 0.3267 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0805 -0.6615 -1.0468 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6304 -0.8390 -0.6828 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5022 -0.4584 0.7734 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3811 0.5124 0.8852 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1693 -0.1990 0.2535 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3209 -0.0147 -1.2432 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7455 -0.0234 -1.6016 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0616 -0.4858 -3.0033 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9009 -0.4133 -3.9094 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3172 -0.6176 -3.4893 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5509 -0.9361 -2.0451 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0277 -0.6896 -1.8263 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4900 0.6279 -2.3887 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4364 0.5825 -3.9000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5215 -0.5484 -4.3880 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0377 1.7973 -4.4558 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4477 -0.9392 -0.5459 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2918 -2.0078 -0.4278 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6643 -1.6957 0.1225 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6031 -2.7386 -0.4299 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8817 -4.0747 -0.2806 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7375 -3.9506 0.7129 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7787 -3.0444 0.3463 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4084 -4.5612 -1.4826 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7875 -2.8422 0.2576 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0380 -0.4132 -0.0620 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2954 0.3182 1.0888 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4881 1.5808 1.1666 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1457 2.4798 2.1896 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4091 2.9887 1.4635 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0489 1.8469 0.7104 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6241 0.6202 1.0977 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7963 2.0401 -0.7618 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3008 3.5300 2.3553 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5627 1.7000 3.2475 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1496 1.3523 1.4579 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2926 -2.3897 -1.8592 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9971 -1.7337 1.4841 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9993 2.3549 0.7003 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9225 1.2411 3.6529 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3970 2.4297 2.3480 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2479 2.9532 3.5878 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8379 1.3771 1.0544 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8412 3.5200 1.5502 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9517 2.8498 2.9616 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9247 -0.5969 2.9263 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1727 1.0518 3.5220 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2875 0.0252 3.5996 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8816 -0.5937 1.1007 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1654 1.4593 2.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0316 -0.7417 2.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1117 -1.7304 0.5054 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4701 -1.5370 -1.6463 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2845 0.2212 -1.6637 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3805 -1.9052 -0.8889 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1789 0.7552 1.9456 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4813 1.4439 0.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7133 0.3809 0.6388 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1058 -1.2411 0.5567 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0992 1.0208 -1.4335 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1405 1.0261 -1.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4646 -1.5184 -3.0464 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8722 0.1482 -3.4685 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0375 -0.1859 -4.9607 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5262 -1.4754 -2.4744 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0093 1.5039 -1.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5801 0.7040 -2.1249 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4376 0.3578 -4.3480 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2158 -0.2664 -5.4101 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0508 -1.5027 -4.4559 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2168 1.7142 -4.9930 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4400 -2.4356 -1.4597 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6398 -1.8900 1.2360 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7274 -2.5790 -1.5265 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5602 -4.8578 0.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2509 -4.9686 0.7221 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1132 -3.8036 1.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1130 -4.9750 -2.0468 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4964 -2.3698 -0.2748 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1361 -0.3189 2.0089 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4976 2.1317 0.2061 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5409 3.3447 2.4554 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0754 3.7447 0.7452 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1695 1.9367 0.8804 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3842 3.0572 -0.9139 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7850 2.0649 -1.3121 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1766 1.2400 -1.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2323 3.4908 2.0861 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5187 1.8101 3.4584 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0487 1.3162 2.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0473 -2.7088 -0.8490 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5125 -2.7989 -2.5270 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2171 -2.9302 -2.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8450 -2.1928 2.0767 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2301 -1.5050 2.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6831 -2.5072 0.7891 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1528 2.9315 1.1804 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8608 2.1878 -0.3625 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8527 3.1009 0.7655 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 5 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 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 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 24 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 31 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 23 49 1 0 15 50 1 0 9 51 1 0 7 2 1 0 12 5 1 0 15 10 1 0 19 14 1 0 23 18 1 0 27 22 1 0 35 30 1 0 44 39 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 0 3 56 1 0 3 57 1 0 6 58 1 0 6 59 1 0 7 60 1 0 8 61 1 0 9 62 1 0 10 63 1 0 11 64 1 0 13 65 1 0 13 66 1 0 14 67 1 0 16 68 1 0 16 69 1 0 17 70 1 0 17 71 1 0 18 72 1 0 19 73 1 0 20 74 1 0 20 75 1 0 21 76 1 0 24 77 1 0 25 78 1 0 25 79 1 0 26 80 1 0 27 81 1 0 27 82 1 0 28 83 1 0 30 84 1 0 31 85 1 0 32 86 1 0 33 87 1 0 34 88 1 0 34 89 1 0 36 90 1 0 37 91 1 0 39 92 1 0 40 93 1 0 41 94 1 0 42 95 1 0 43 96 1 0 45 97 1 0 45 98 1 0 45 99 1 0 46100 1 0 47101 1 0 48102 1 0 49103 1 0 49104 1 0 49105 1 0 50106 1 0 50107 1 0 50108 1 0 51109 1 0 51110 1 0 51111 1 0 M END

Standard InCHIKey	CEUOJNPNKKLCDB-VVFBCDONSA-N
Standard InCHI	InChI=1S/C38H60O13/c1-16-14-47-38(13-24(16)40)17(2)28-26(51-38)12-23-21-7-6-19-10-20(39)11-27(37(19,5)22(21)8-9-36(23,28)4)49-35-33(30(43)25(41)15-46-35)50-34-32(45)31(44)29(42)18(3)48-34/h6,16-18,20-35,39-45H,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+/m0/s1
SMILES	CC1COC2(CC1O)C(C3C(O2)CC4C3(CCC5C4CC=C6C5(C(CC(C6)O)OC7C(C(C(CO7)O)O)OC8C(C(C(C(O8)C)O)O)O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	724.4	Volume:	708.989 ? Van der Waals volume.
Dense:	1.022	LogP:	1.82 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.676 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.769 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	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:	0.203	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.491	Fsp³:	0.947
MCE-18:	203.405 ? 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:	0.034	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.036 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.115 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.252	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.097	MDCK Permeability:	-4.94
Pgp-inhibitor:	0.0	Pgp-substrate:	0.987
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):	0.4
20% Bioavailability (F20%):	0.223	30% Bioavailability (F30%):	0.732
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03	MRP1:	1.0
Plasma Protein Binding (PPB):	42.892%	Volume Distribution (VD):	-0.478
Fu:	56.138% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.177	BCRP inhibitor:	0.004
BSEP inhibitor:	0.242

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.042	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.206	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
HLM stability:	0.0 ? 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):

1.656

Half-life (T1/2):

4.096

ADMET: Toxicity

hERG Blockers:	0.169	hERG Blockers (10um):	0.629
Human Hepatotoxicity (H-HT):	0.415	Drug-induced Liver Injury (DILI):	0.188
AMES Toxicity:	0.313	Rat Oral Acute Toxicity:	0.407
Maximum Recommended Daily Dose:	0.743	Skin Sensitization:	0.003
Carcinogencity:	0.078	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.018
Drug-induced Neurotoxicity:	0.562	Ototoxicity:	0.999
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.037
Genotoxicity:	0.004	RPMI-8226 Immunitoxicity:	0.12
A549 Cytotoxicity:	0.053	Hek293 Cytotoxicity:	0.887
BCF:	1.025 ? 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:	3.742 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.642 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.186 ? 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
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	bulbs	n.a.	n.a.	PMID[12398536]
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	n.a.	bulb	n.a.	PMID[12398536]
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	bulbs	n.a.	n.a.	PMID[15497941]
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	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

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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	5.2	ug.mL-1	PMID[9677277]
NPT924	Cell line	HSC-2	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[20702006]

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 NPC475670 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	24193
0.1-0.2	22506
0.2-0.3	2596
0.3-0.4	396
0.4-0.5	101
0.5-0.6	43
0.6-0.7	8
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8864	High Similarity	NPC70204
0.8261	Intermediate Similarity	NPC112274
0.8125	Intermediate Similarity	NPC475247
0.7802	Intermediate Similarity	NPC306131
0.7802	Intermediate Similarity	NPC200802
0.7684	Intermediate Similarity	NPC51154
0.7604	Intermediate Similarity	NPC11548
0.7228	Intermediate Similarity	NPC294129
0.6875	Remote Similarity	NPC475431
0.6822	Remote Similarity	NPC195560
0.6667	Remote Similarity	NPC229962
0.6346	Remote Similarity	NPC475403
0.6321	Remote Similarity	NPC160888
0.6239	Remote Similarity	NPC475487
0.6204	Remote Similarity	NPC148965
0.6186	Remote Similarity	NPC13190
0.5934	Remote Similarity	NPC473923
0.5926	Remote Similarity	NPC473633
0.5888	Remote Similarity	NPC476085
0.5806	Remote Similarity	NPC473476
0.5714	Remote Similarity	NPC198325
0.569	Remote Similarity	NPC479532
0.5631	Remote Similarity	NPC476540
0.5631	Remote Similarity	NPC476541
0.5607	Remote Similarity	NPC113044
0.5607	Remote Similarity	NPC283829
0.5607	Remote Similarity	NPC161676
0.5447	Remote Similarity	NPC233391
0.5429	Remote Similarity	NPC476538
0.5429	Remote Similarity	NPC476539
0.5391	Remote Similarity	NPC475333
0.5391	Remote Similarity	NPC224098
0.5391	Remote Similarity	NPC208383
0.5366	Remote Similarity	NPC207243
0.5354	Remote Similarity	NPC473774
0.5354	Remote Similarity	NPC481419
0.5354	Remote Similarity	NPC481417
0.5321	Remote Similarity	NPC305423
0.5315	Remote Similarity	NPC470433
0.5315	Remote Similarity	NPC46190
0.5315	Remote Similarity	NPC171073
0.5268	Remote Similarity	NPC248746
0.521	Remote Similarity	NPC50689
0.5182	Remote Similarity	NPC14704
0.5179	Remote Similarity	NPC602423
0.5175	Remote Similarity	NPC480555
0.5175	Remote Similarity	NPC150372
0.5152	Remote Similarity	NPC202261
0.5143	Remote Similarity	NPC477451
0.5138	Remote Similarity	NPC470432
0.5138	Remote Similarity	NPC230507
0.5122	Remote Similarity	NPC43842
0.5122	Remote Similarity	NPC480556
0.5088	Remote Similarity	NPC300557
0.505	Remote Similarity	NPC481420
0.505	Remote Similarity	NPC481421
0.5043	Remote Similarity	NPC269297
0.5043	Remote Similarity	NPC222202
0.5042	Remote Similarity	NPC480554

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7616
0.1-0.2	1486
0.2-0.3	40
0.3-0.4	7
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