NPASS Compound

Natural Product: NPC129560

Natural Product ID	NPC129560
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DZVIFFMYEULLBY-CABPEOBRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102005082
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene 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 105110 0 0 0 0 0 0 0 0999 V2000 2.0890 -3.4296 -3.9284 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9057 -3.0791 -2.4386 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6437 -4.4058 -1.7653 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2361 -2.4926 -2.0210 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1073 -2.2635 -0.5287 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2254 -1.0120 -0.3410 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7901 -1.0639 1.0746 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5963 -0.2459 1.4415 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5642 -0.5452 0.4709 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7958 -2.0159 0.6717 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0076 -0.1934 -0.8388 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5828 0.7184 -1.5661 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7976 1.4734 -1.1930 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6015 0.5284 -0.3268 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0257 0.9480 -0.1696 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2681 2.3773 0.1410 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6676 0.7106 -1.5504 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1580 0.6806 -1.4939 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7159 -0.3198 -0.5456 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1558 -0.0267 0.8400 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5246 -1.2950 1.6443 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8363 1.0924 1.5331 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2002 0.7250 1.6601 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6866 -0.0231 0.7666 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9896 -0.0630 2.1130 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6106 -0.6315 1.8117 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7988 0.2283 0.8745 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3251 1.4469 1.6282 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0209 1.0539 2.8524 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0994 -0.2679 -0.5742 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5866 0.3114 -2.7876 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2086 -0.8621 -1.3844 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8458 -2.0709 -2.2110 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2224 0.0985 -0.4528 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0924 0.9289 -1.3791 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2827 0.2459 0.4245 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2124 1.3200 0.2745 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1552 2.1323 1.5506 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4978 2.6564 1.9761 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4203 2.8856 0.8127 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3881 1.7848 -0.2042 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7584 1.1266 -0.2782 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0885 0.5189 0.9326 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4784 0.7981 0.0841 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0536 4.0674 0.1719 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0607 1.8265 2.9326 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2296 3.1592 1.3573 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3254 -4.1301 -4.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1225 -3.6973 -4.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8953 -2.4617 -4.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6132 -4.9376 -1.6843 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0178 -5.0179 -2.4695 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0961 -4.3432 -0.8273 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3357 -1.5138 -2.5549 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0920 -3.1403 -2.2330 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5799 -3.1439 -0.1111 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0704 -2.1747 -0.0298 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7773 -2.1105 1.5072 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6222 -0.6222 1.7183 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9173 0.8126 1.3845 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3135 -0.5509 2.4712 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0261 -2.1537 1.7427 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1196 -2.6209 0.5105 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5633 -2.4872 0.0794 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1580 0.9816 -2.5558 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3761 1.8130 -2.0803 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5596 2.4073 -0.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6424 -0.4350 -0.9242 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4126 2.9830 -0.2182 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5201 2.6040 1.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1333 2.8111 -0.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2045 -0.1517 -2.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3980 1.6248 -2.1577 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5723 1.6812 -1.3248 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3233 -1.3346 -0.8255 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5358 -1.0623 2.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7905 -2.0828 1.3773 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5126 -1.6872 1.2882 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8470 2.0586 1.0265 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4620 1.1361 2.5740 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7936 1.2979 1.1470 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4238 -1.0382 0.3172 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5076 -0.8876 2.6865 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8778 -1.5515 1.2464 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1191 -0.8190 2.7837 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6167 2.0747 1.0979 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1544 2.1116 1.9381 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8687 1.0896 2.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2736 0.8827 3.7985 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3495 0.0262 -1.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9193 -0.2224 -3.2648 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6533 -0.1665 -2.1747 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5251 -1.7518 -3.2562 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1267 -2.5331 -1.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9374 1.9329 -0.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7826 1.4760 2.3604 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3062 3.6691 2.4308 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4477 3.0130 1.2162 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1718 2.1710 -1.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5544 1.8177 -0.5715 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7389 0.3088 -1.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8646 -0.0716 0.7845 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8718 4.3652 -0.3369 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9815 0.8845 2.6974 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7646 3.3301 2.2133 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 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 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 25 29 1 0 19 30 1 0 18 31 1 0 11 32 1 0 32 33 1 0 6 34 1 1 34 35 2 0 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 39 46 1 0 38 47 1 0 33 2 1 0 44 37 1 0 32 6 1 0 27 9 1 0 27 14 1 0 24 15 1 0 1 48 1 0 1 49 1 0 1 50 1 0 3 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 10 62 1 0 10 63 1 0 10 64 1 0 12 65 1 0 13 66 1 0 13 67 1 0 14 68 1 6 16 69 1 0 16 70 1 0 16 71 1 0 17 72 1 0 17 73 1 0 18 74 1 1 19 75 1 6 21 76 1 0 21 77 1 0 21 78 1 0 22 79 1 0 22 80 1 0 23 81 1 0 24 82 1 6 25 83 1 1 26 84 1 0 26 85 1 0 28 86 1 0 28 87 1 0 28 88 1 0 29 89 1 0 30 90 1 0 31 91 1 0 32 92 1 6 33 93 1 0 33 94 1 0 37 95 1 6 38 96 1 1 39 97 1 1 40 98 1 1 41 99 1 6 42100 1 0 42101 1 0 43102 1 0 45103 1 0 46104 1 0 47105 1 0 M END

Standard InCHIKey	DZVIFFMYEULLBY-CABPEOBRSA-N
Standard InCHI	InChI=1S/C36H58O11/c1-31(2)9-11-36(30(45)47-29-26(43)25(42)24(41)22(16-37)46-29)12-10-34(5)18(19(36)13-31)7-8-23-32(3)14-21(40)28(44)33(4,17-38)27(32)20(39)15-35(23,34)6/h7,19-29,37-44H,8-17H2,1-6H3/t19-,20+,21+,22+,23+,24+,25-,26+,27+,28-,29-,32+,33+,34+,35+,36-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@](C)(CO)[C@@H]5[C@@H](C[C@@]34C)O)O)O)[C@@H]2C1)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.4	Volume:	671.293 ? Van der Waals volume.
Dense:	0.993	LogP:	1.311 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.915 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.1 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	197.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.16	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.625	Fsp³:	0.917
MCE-18:	133.507 ? 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:	0.748	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.043 ? 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:	0.167	Promiscuous compounds:	0.115

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.115	MDCK Permeability:	-5.191
Pgp-inhibitor:	0.0	Pgp-substrate:	0.348
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):	0.329
20% Bioavailability (F20%):	0.957	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95	MRP1:	0.281
Plasma Protein Binding (PPB):	72.901%	Volume Distribution (VD):	-0.4
Fu:	20.567% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.005
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.011	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.545
HLM stability:	0.036 ? 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):

1.345

Half-life (T1/2):

3.143

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.024
Human Hepatotoxicity (H-HT):	0.669	Drug-induced Liver Injury (DILI):	0.397
AMES Toxicity:	0.795	Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.048	Skin Sensitization:	0.999
Carcinogencity:	0.424	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.037
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.993
Hematotoxicity:	0.672	Drug-induced Nephrotoxicity:	0.967
Genotoxicity:	0.813	RPMI-8226 Immunitoxicity:	0.135
A549 Cytotoxicity:	0.479	Hek293 Cytotoxicity:	0.227
BCF:	1.033 ? 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:	3.409 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.874 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.06 ? 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
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26650	Terminalia chebula	Species	Combretaceae	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 NPC129560 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	20721
0.1-0.2	24341
0.2-0.3	3816
0.3-0.4	731
0.4-0.5	137
0.5-0.6	82
0.6-0.7	19
0.7-0.8	0
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	NPC199457
0.8442	Intermediate Similarity	NPC306746
0.7439	Intermediate Similarity	NPC68419
0.7195	Intermediate Similarity	NPC237503
0.7024	Intermediate Similarity	NPC48249
0.7024	Intermediate Similarity	NPC604133
0.6951	Remote Similarity	NPC167383
0.6588	Remote Similarity	NPC116794
0.6552	Remote Similarity	NPC271138
0.6484	Remote Similarity	NPC29069
0.6437	Remote Similarity	NPC64106
0.6374	Remote Similarity	NPC214484
0.6364	Remote Similarity	NPC102914
0.6364	Remote Similarity	NPC110139
0.6364	Remote Similarity	NPC108709
0.6333	Remote Similarity	NPC209894
0.6292	Remote Similarity	NPC220984
0.6211	Remote Similarity	NPC150400
0.6105	Remote Similarity	NPC235405
0.6092	Remote Similarity	NPC605954
0.6067	Remote Similarity	NPC310014
0.6067	Remote Similarity	NPC269315
0.6064	Remote Similarity	NPC48499
0.6042	Remote Similarity	NPC249848
0.6042	Remote Similarity	NPC107966
0.5979	Remote Similarity	NPC295371
0.5979	Remote Similarity	NPC473884
0.5979	Remote Similarity	NPC39211
0.5938	Remote Similarity	NPC475516
0.5918	Remote Similarity	NPC469946
0.59	Remote Similarity	NPC40775
0.59	Remote Similarity	NPC10607
0.5889	Remote Similarity	NPC7870
0.5889	Remote Similarity	NPC75747
0.5862	Remote Similarity	NPC240125
0.5859	Remote Similarity	NPC223301
0.5859	Remote Similarity	NPC171544
0.5851	Remote Similarity	NPC238935
0.5842	Remote Similarity	NPC235438
0.5816	Remote Similarity	NPC157868
0.58	Remote Similarity	NPC30735
0.5784	Remote Similarity	NPC222580
0.5784	Remote Similarity	NPC297263
0.5743	Remote Similarity	NPC46665
0.5728	Remote Similarity	NPC601659
0.5714	Remote Similarity	NPC96641
0.5714	Remote Similarity	NPC481030
0.5714	Remote Similarity	NPC163183
0.57	Remote Similarity	NPC192791
0.57	Remote Similarity	NPC242840
0.57	Remote Similarity	NPC112352
0.5686	Remote Similarity	NPC475591
0.5686	Remote Similarity	NPC236870
0.5684	Remote Similarity	NPC90856
0.5612	Remote Similarity	NPC139894
0.5604	Remote Similarity	NPC37739
0.56	Remote Similarity	NPC473343
0.5588	Remote Similarity	NPC251768
0.5588	Remote Similarity	NPC159309
0.5588	Remote Similarity	NPC86222
0.5566	Remote Similarity	NPC80986
0.5556	Remote Similarity	NPC473373
0.5543	Remote Similarity	NPC187056
0.5543	Remote Similarity	NPC606216
0.5543	Remote Similarity	NPC607023
0.5534	Remote Similarity	NPC63159
0.5524	Remote Similarity	NPC281148
0.5524	Remote Similarity	NPC104372
0.5517	Remote Similarity	NPC477463
0.5514	Remote Similarity	NPC31838
0.5437	Remote Similarity	NPC102439
0.5437	Remote Similarity	NPC473459
0.5393	Remote Similarity	NPC191763
0.5385	Remote Similarity	NPC46388
0.5377	Remote Similarity	NPC114484
0.5376	Remote Similarity	NPC137917
0.5376	Remote Similarity	NPC212968
0.537	Remote Similarity	NPC187290
0.5366	Remote Similarity	NPC136313
0.534	Remote Similarity	NPC109588
0.534	Remote Similarity	NPC104071
0.5333	Remote Similarity	NPC609763
0.5327	Remote Similarity	NPC301449
0.5327	Remote Similarity	NPC601290
0.531	Remote Similarity	NPC100639
0.5253	Remote Similarity	NPC475208
0.5229	Remote Similarity	NPC481078
0.5225	Remote Similarity	NPC300419
0.5192	Remote Similarity	NPC309714
0.5185	Remote Similarity	NPC481079
0.5182	Remote Similarity	NPC75287
0.5175	Remote Similarity	NPC470218
0.5165	Remote Similarity	NPC91583
0.5161	Remote Similarity	NPC477464
0.5143	Remote Similarity	NPC480475
0.5138	Remote Similarity	NPC241909
0.5133	Remote Similarity	NPC475899
0.5133	Remote Similarity	NPC481031
0.5119	Remote Similarity	NPC481361
0.5088	Remote Similarity	NPC135904
0.5052	Remote Similarity	NPC256798
0.5051	Remote Similarity	NPC189884
0.5051	Remote Similarity	NPC138334
0.5047	Remote Similarity	NPC475504
0.5044	Remote Similarity	NPC79643
0.5043	Remote Similarity	NPC475160
0.5043	Remote Similarity	NPC473714

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC129560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7224
0.1-0.2	1870
0.2-0.3	53
0.3-0.4	3
0.4-0.5	0
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