NPASS Compound

Natural Product: NPC271825

Natural Product ID	NPC271825
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YWCRAJAMRXTUHR-LCFFHKHSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5320663
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 112119 0 0 0 0 0 0 0 0999 V2000 -10.7063 -0.5450 3.0744 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6173 -0.6035 2.0265 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6136 0.6446 1.1755 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3822 0.5434 0.2673 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0317 -0.9000 0.0362 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1435 -0.9842 -1.2181 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8039 -0.3961 -2.4147 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9572 -0.2209 -0.7187 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9669 -0.6155 0.7690 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6647 -1.4204 0.9292 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8085 -0.6406 0.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4494 -1.1567 -0.2721 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7218 -1.6543 0.9309 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8565 -0.6623 1.6107 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1304 -0.1420 0.5908 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0164 -1.2409 0.0465 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0420 -0.5166 -0.8400 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2208 -0.0249 -2.0405 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3430 1.0739 -1.5426 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6272 0.5993 -0.4498 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0837 1.9166 0.1953 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7441 -0.1356 -1.0992 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7072 0.9315 -1.6384 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9790 0.3788 -2.1667 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6449 -0.6308 -1.2719 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6245 -1.9480 -1.9719 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4033 0.6209 -0.1332 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7743 0.7164 0.0923 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2375 2.0299 -0.5076 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5834 2.4590 0.0382 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1869 1.2424 0.7270 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2643 0.8808 1.8717 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9570 0.8011 1.4697 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4383 1.4943 1.2306 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3622 0.6709 0.6429 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5227 1.4295 0.0404 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3701 0.4692 -0.7262 C 0 0 2 0 0 0 0 0 0 0 0 0 10.0713 -0.9448 -0.3478 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7011 -1.1497 1.0807 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9569 -1.3886 1.8834 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6824 -2.3989 1.2373 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8974 -0.1761 1.6109 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1497 -1.5428 -1.2387 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7111 0.7768 -0.4942 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1146 2.5204 -0.7011 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4238 3.4525 0.9781 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2440 1.9373 -1.8991 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0839 -1.3650 0.9812 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1212 -1.7305 -0.0511 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7259 -1.8298 1.1749 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5938 0.0406 2.6964 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3724 0.0151 3.9805 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9975 -1.5572 3.4186 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6525 -0.6278 2.5751 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5231 1.5345 1.8574 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5056 0.7596 0.5619 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5885 1.1069 0.7808 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6317 1.0861 -0.6564 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9393 -2.0910 -1.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2343 0.4578 -2.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8773 -0.1540 -2.2618 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8000 -1.1877 -3.2193 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1692 0.8509 -0.8380 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8468 0.2620 1.4203 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3812 -1.3566 2.0025 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8017 -2.4735 0.6920 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8319 0.4237 0.3697 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5936 -2.0741 -0.9242 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0892 -2.5501 0.6878 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4768 -2.0268 1.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3833 0.1915 2.0510 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2637 -1.1853 2.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7844 0.5826 1.1222 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5209 -1.7243 0.8849 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4070 -1.9228 -0.5759 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8647 -1.1662 -1.1193 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9394 0.3987 -2.7441 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6764 -0.8516 -2.5135 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1585 1.6383 -2.3274 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0138 1.8092 -1.0085 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1855 2.7208 -0.5592 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2078 2.2361 0.8323 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9259 1.7913 0.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3182 -0.6002 -2.0403 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1805 1.4331 -2.5019 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9194 1.7133 -0.9160 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7611 -0.0444 -3.1916 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6794 1.1986 -2.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4659 -1.9365 -2.7130 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5977 -2.8261 -1.3383 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7040 -1.9801 -2.6274 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2504 -0.1567 -0.3561 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4474 2.7978 -0.2613 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2050 2.7766 -0.8267 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2316 0.4480 -0.0210 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3632 1.7268 2.6131 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5417 -0.0321 2.3953 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8502 0.0165 -0.0890 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1205 1.8218 0.9097 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1654 0.6087 -1.8071 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0241 -1.5265 -0.5277 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1194 -2.1163 1.1324 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6078 -0.4898 1.8950 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7416 -1.7242 2.9186 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6349 -2.1592 1.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0775 -1.0271 -2.0710 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1556 1.0721 -1.3100 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1642 3.3369 -0.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6643 4.0353 0.7519 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5280 2.7862 -2.2947 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3606 -2.7070 1.7432 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8216 -2.0276 1.0011 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 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 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 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 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 31 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 30 46 1 0 29 47 1 0 9 48 1 0 5 49 1 0 49 50 1 0 50 2 1 0 48 5 1 0 25 8 1 0 33 28 1 0 42 35 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 51 1 0 1 52 1 0 1 53 1 0 2 54 1 0 3 55 1 0 3 56 1 0 4 57 1 0 4 58 1 0 6 59 1 0 7 60 1 0 7 61 1 0 7 62 1 0 8 63 1 0 9 64 1 0 10 65 1 0 10 66 1 0 11 67 1 0 12 68 1 0 13 69 1 0 13 70 1 0 14 71 1 0 14 72 1 0 15 73 1 0 16 74 1 0 16 75 1 0 17 76 1 0 18 77 1 0 18 78 1 0 19 79 1 0 19 80 1 0 21 81 1 0 21 82 1 0 21 83 1 0 22 84 1 0 23 85 1 0 23 86 1 0 24 87 1 0 24 88 1 0 26 89 1 0 26 90 1 0 26 91 1 0 28 92 1 6 29 93 1 6 30 94 1 6 31 95 1 6 32 96 1 0 32 97 1 0 35 98 1 6 36 99 1 1 37100 1 6 38101 1 1 39102 1 6 40103 1 0 40104 1 0 41105 1 0 43106 1 0 44107 1 0 45108 1 0 46109 1 0 47110 1 0 50111 1 0 50112 1 0 M END

Standard InCHIKey	YWCRAJAMRXTUHR-LCFFHKHSSA-N
Standard InCHI	InChI=1S/C38H62O12/c1-18-7-12-38(46-16-18)19(2)28-25(50-38)14-24-22-6-5-20-13-21(8-10-36(20,3)23(22)9-11-37(24,28)4)47-34-32(43)30(41)27(17-45-34)49-35-33(44)31(42)29(40)26(15-39)48-35/h18-35,39-44H,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?/m1/s1
SMILES	CC1CCC2(C(C)C3C(CC4C5CCC6CC(CCC6(C)C5CCC34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	710.42	Volume:	702.835 ? Van der Waals volume.
Dense:	1.011	LogP:	2.97 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.529 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.125 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	42.0
TPSA:	176.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	8.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.23	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.178	Fsp³:	1.0
MCE-18:	197.289 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.736	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.031 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.018 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.134	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.804	MDCK Permeability:	-5.054
Pgp-inhibitor:	0.004	Pgp-substrate:	0.005
PAMPA:	0.033 ? 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):	0.002
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.267
50% Bioavailability (F50%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.748	MRP1:	0.998
Plasma Protein Binding (PPB):	72.549%	Volume Distribution (VD):	-0.34
Fu:	23.789% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.333
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.001
BSEP inhibitor:	0.552

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.949	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.215	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.005	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.004	CYP2C8-inhibitor:	0.033
HLM stability:	0.953 ? 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):

2.957

Half-life (T1/2):

2.988

ADMET: Toxicity

hERG Blockers:	0.092	hERG Blockers (10um):	0.182
Human Hepatotoxicity (H-HT):	0.79	Drug-induced Liver Injury (DILI):	0.688
AMES Toxicity:	0.873	Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.232	Skin Sensitization:	0.993
Carcinogencity:	0.205	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.036
Drug-induced Neurotoxicity:	0.029	Ototoxicity:	0.998
Hematotoxicity:	0.155	Drug-induced Nephrotoxicity:	0.181
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.176
A549 Cytotoxicity:	0.886	Hek293 Cytotoxicity:	0.82
BCF:	2.414 ? 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:	4.504 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.42 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.079 ? 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
NPO6867	Asparagus curillus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6867	Asparagus curillus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6867	Asparagus curillus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6867	Asparagus curillus	Species	Asparagaceae	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 NPC271825 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	25245
0.1-0.2	20916
0.2-0.3	2866
0.3-0.4	558
0.4-0.5	140
0.5-0.6	86
0.6-0.7	26
0.7-0.8	0
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8554	High Similarity	NPC211354
0.8554	High Similarity	NPC107188
0.8171	Intermediate Similarity	NPC325828
0.8171	Intermediate Similarity	NPC177834
0.8072	Intermediate Similarity	NPC234352
0.7952	Intermediate Similarity	NPC297348
0.7952	Intermediate Similarity	NPC249204
0.7952	Intermediate Similarity	NPC48339
0.7952	Intermediate Similarity	NPC141769
0.7952	Intermediate Similarity	NPC477547
0.7727	Intermediate Similarity	NPC107962
0.7667	Intermediate Similarity	NPC160426
0.7558	Intermediate Similarity	NPC477451
0.7471	Intermediate Similarity	NPC250393
0.7386	Intermediate Similarity	NPC206003
0.7386	Intermediate Similarity	NPC473610
0.7204	Intermediate Similarity	NPC475351
0.7188	Intermediate Similarity	NPC128572
0.7113	Intermediate Similarity	NPC97700
0.7113	Intermediate Similarity	NPC30856
0.7093	Intermediate Similarity	NPC485594
0.7065	Intermediate Similarity	NPC6295
0.6939	Remote Similarity	NPC184617
0.6875	Remote Similarity	NPC475643
0.6796	Remote Similarity	NPC132080
0.6774	Remote Similarity	NPC215408
0.6739	Remote Similarity	NPC19400
0.6733	Remote Similarity	NPC475625
0.6699	Remote Similarity	NPC83137
0.6667	Remote Similarity	NPC294686
0.6629	Remote Similarity	NPC181845
0.6526	Remote Similarity	NPC125324
0.6505	Remote Similarity	NPC232037
0.6489	Remote Similarity	NPC264101
0.6477	Remote Similarity	NPC24960
0.6465	Remote Similarity	NPC92890
0.6442	Remote Similarity	NPC470864
0.6408	Remote Similarity	NPC116756
0.64	Remote Similarity	NPC51172
0.64	Remote Similarity	NPC49032
0.6344	Remote Similarity	NPC222731
0.6238	Remote Similarity	NPC471464
0.6147	Remote Similarity	NPC470866
0.6136	Remote Similarity	NPC277715
0.61	Remote Similarity	NPC473601
0.61	Remote Similarity	NPC202898
0.6058	Remote Similarity	NPC475319
0.6019	Remote Similarity	NPC233433
0.598	Remote Similarity	NPC477809
0.596	Remote Similarity	NPC195297
0.5905	Remote Similarity	NPC115165
0.59	Remote Similarity	NPC113044
0.59	Remote Similarity	NPC283829
0.59	Remote Similarity	NPC14704
0.59	Remote Similarity	NPC161676
0.5876	Remote Similarity	NPC54619
0.5859	Remote Similarity	NPC470432
0.5859	Remote Similarity	NPC230507
0.5859	Remote Similarity	NPC485595
0.5824	Remote Similarity	NPC473774
0.5824	Remote Similarity	NPC481419
0.5824	Remote Similarity	NPC481417
0.5789	Remote Similarity	NPC291203
0.5789	Remote Similarity	NPC220836
0.5789	Remote Similarity	NPC217205
0.5769	Remote Similarity	NPC6806
0.5726	Remote Similarity	NPC481189
0.567	Remote Similarity	NPC474399
0.5667	Remote Similarity	NPC481190
0.5636	Remote Similarity	NPC476112
0.5636	Remote Similarity	NPC307534
0.5619	Remote Similarity	NPC300557
0.561	Remote Similarity	NPC329807
0.5591	Remote Similarity	NPC172838
0.5566	Remote Similarity	NPC480555
0.5566	Remote Similarity	NPC150372
0.5556	Remote Similarity	NPC329727
0.5526	Remote Similarity	NPC94086
0.5526	Remote Similarity	NPC473817
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	NPC481418
0.5484	Remote Similarity	NPC481421
0.5455	Remote Similarity	NPC128123
0.5455	Remote Similarity	NPC121453
0.5429	Remote Similarity	NPC602423
0.5421	Remote Similarity	NPC151134
0.5405	Remote Similarity	NPC108072
0.5366	Remote Similarity	NPC330026
0.5364	Remote Similarity	NPC473518
0.5357	Remote Similarity	NPC470862
0.5315	Remote Similarity	NPC232611
0.531	Remote Similarity	NPC480553
0.531	Remote Similarity	NPC477811
0.5283	Remote Similarity	NPC470433
0.5283	Remote Similarity	NPC46190
0.5283	Remote Similarity	NPC171073
0.5263	Remote Similarity	NPC485600
0.5253	Remote Similarity	NPC30483
0.5253	Remote Similarity	NPC470897
0.5248	Remote Similarity	NPC306131
0.5248	Remote Similarity	NPC200802
0.5225	Remote Similarity	NPC475333
0.5225	Remote Similarity	NPC224098
0.5225	Remote Similarity	NPC309278
0.5225	Remote Similarity	NPC208383
0.5192	Remote Similarity	NPC70204
0.5179	Remote Similarity	NPC194207
0.5179	Remote Similarity	NPC22779
0.5161	Remote Similarity	NPC88962
0.5152	Remote Similarity	NPC131693
0.5152	Remote Similarity	NPC475436
0.5152	Remote Similarity	NPC80191
0.5143	Remote Similarity	NPC479357
0.5135	Remote Similarity	NPC470863
0.5135	Remote Similarity	NPC269297
0.5135	Remote Similarity	NPC222202
0.5135	Remote Similarity	NPC475550
0.5133	Remote Similarity	NPC480554
0.513	Remote Similarity	NPC31896
0.5119	Remote Similarity	NPC227260
0.5102	Remote Similarity	NPC481424
0.5102	Remote Similarity	NPC481422
0.5091	Remote Similarity	NPC98018
0.5091	Remote Similarity	NPC284104
0.5091	Remote Similarity	NPC103616
0.5085	Remote Similarity	NPC480556
0.5051	Remote Similarity	NPC485602
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 NPC271825 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7526
0.1-0.2	1534
0.2-0.3	74
0.3-0.4	10
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8171	Intermediate Similarity	NPD8171	Phase 2
0.6882	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