NPASS Compound

Natural Product: NPC283681

Natural Product ID	NPC283681
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SZKBNQQHAJTPTG-UAHSGVCYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24893062
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 11.0726 -0.5557 0.9846 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6616 -1.0553 0.8171 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9841 -1.3879 2.1006 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5495 -0.9539 2.1780 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8674 -0.8484 0.8852 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6807 0.1491 0.9233 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8770 -0.2947 2.0790 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2274 -0.0632 -0.4256 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4293 -1.5786 -0.6134 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0175 -2.1404 -0.6564 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1091 -0.9859 -0.4680 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7506 -1.1212 -1.1578 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8266 -1.8674 -0.2545 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4821 -1.3102 0.0816 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8167 0.0495 -0.4620 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3149 0.2071 -0.3869 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8678 1.3180 -1.2264 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7413 2.2042 -1.6990 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7228 1.4277 -2.4936 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2724 0.1679 -1.8286 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6617 -1.0423 -2.6748 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2664 0.1371 -1.7733 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8228 1.4171 -1.3135 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1438 1.3839 -0.5945 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9168 0.1640 -0.9638 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0478 0.1694 -2.4969 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8307 1.9504 -0.5302 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1004 2.0273 -1.0436 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0975 1.3962 -0.1090 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3520 2.2383 -0.1369 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9774 3.5426 0.5416 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9189 4.1629 -0.3879 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8603 4.7425 0.5207 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2181 3.7547 1.2495 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3807 3.3269 -1.2776 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0261 4.4175 0.6694 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4649 1.6394 0.3834 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4200 0.0938 -0.4807 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0649 -0.8656 0.4629 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2889 -1.6081 0.9903 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9569 -2.9459 1.5650 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9554 -3.7439 0.8015 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7706 -2.8000 0.5486 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2669 -1.7805 -0.2230 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5376 -4.8190 1.5763 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1719 -3.6502 1.6979 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8719 -0.8781 2.0559 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1315 -2.0036 0.5213 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6289 -0.5047 -0.1933 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8731 0.0162 0.1074 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7868 -1.3877 1.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1123 0.1451 1.8394 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3724 0.0257 0.0790 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6893 -1.9360 0.1285 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5919 -1.0169 2.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0108 -2.5126 2.2022 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0254 -1.6569 2.8646 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5542 0.0571 2.6695 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1129 1.1445 1.1486 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6369 -1.3991 2.0447 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5615 -0.2346 2.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0175 0.3246 2.3576 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0052 0.3926 -1.1136 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9941 -1.8193 -1.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8634 -2.5263 -1.7012 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8645 -2.9854 0.0117 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8408 -0.7831 0.5912 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0029 -1.8786 -1.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3714 -2.0306 0.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6747 -2.9523 -0.5571 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6661 -1.2377 1.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3252 -1.9883 -0.2568 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3865 0.8045 0.2233 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6704 0.3430 0.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7932 -0.7515 -0.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3458 0.9362 -2.1792 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1805 2.9507 -2.3919 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2783 2.6515 -0.7975 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0923 2.1419 -2.7265 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1249 1.1474 -3.5010 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6332 -0.7666 -3.7727 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0653 -1.8749 -2.5976 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6474 -1.4498 -2.3960 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4764 0.0666 -2.8922 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1383 2.0325 -0.6726 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0233 2.1104 -2.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9808 1.4201 0.5023 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7960 2.2663 -0.8202 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7077 -0.7673 -2.9440 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1386 0.2324 -2.8022 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6236 1.0937 -2.9417 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1855 1.5107 -2.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6187 1.4211 0.9054 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5593 2.4866 -1.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5109 3.2937 1.4931 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3901 5.0637 -0.8932 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3193 5.4391 1.2659 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0589 5.2615 -0.0645 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1552 3.9518 2.2135 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8654 3.9281 0.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1909 1.4700 -0.2570 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5771 -0.4368 1.3516 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0483 -1.7696 0.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6002 -2.8017 2.6149 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3877 -4.0961 -0.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4157 -2.4920 1.5380 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0454 -3.3613 -0.0420 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8831 -5.6920 1.2246 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8101 -3.3665 0.9845 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1614 -0.5901 2.6719 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8448 0.9698 0.6467 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3859 0.1802 -0.8859 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 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 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 42 45 1 0 41 46 1 0 40 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 35 28 1 0 44 39 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 1 30 94 1 6 31 95 1 1 32 96 1 6 33 97 1 0 33 98 1 0 34 99 1 0 36100 1 0 37101 1 0 39102 1 1 40103 1 6 41104 1 1 42105 1 6 43106 1 0 43107 1 0 45108 1 0 46109 1 0 47110 1 0 50111 1 0 50112 1 0 M END

Standard InCHIKey	SZKBNQQHAJTPTG-UAHSGVCYSA-N
Standard InCHI	InChI=1S/C38H62O12/c1-18-7-12-38(46-16-18)19(2)28-26(50-38)14-24-22-6-5-20-13-21(8-10-36(20,3)23(22)9-11-37(24,28)4)47-35-33(31(43)30(42)27(15-39)48-35)49-34-32(44)29(41)25(40)17-45-34/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]([C@@H](CO)O3)O)O)O[C@H]3[C@@H]([C@H]([C@@H](CO3)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:	2.68 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.393 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.453 ? 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:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.168	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:	0.756	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.016 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.138	Promiscuous compounds:	0.032

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.744	MDCK Permeability:	-5.076
Pgp-inhibitor:	0.002	Pgp-substrate:	0.002
PAMPA:	0.055 ? 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%):	0.141
50% Bioavailability (F50%):	0.856

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.895	MRP1:	0.994
Plasma Protein Binding (PPB):	70.311%	Volume Distribution (VD):	-0.404
Fu:	25.322% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.623
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.001
BSEP inhibitor:	0.769

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.98	CYP2C19-substrate:	0.022
CYP2C9-inhibitor:	0.772	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.584	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.006
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.029
HLM stability:	0.979 ? 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):

2.79

Half-life (T1/2):

3.07

ADMET: Toxicity

hERG Blockers:	0.098	hERG Blockers (10um):	0.298
Human Hepatotoxicity (H-HT):	0.694	Drug-induced Liver Injury (DILI):	0.32
AMES Toxicity:	0.43	Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.178	Skin Sensitization:	0.982
Carcinogencity:	0.085	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.033
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.998
Hematotoxicity:	0.077	Drug-induced Nephrotoxicity:	0.206
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.142
A549 Cytotoxicity:	0.438	Hek293 Cytotoxicity:	0.528
BCF:	2.358 ? 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:	4.485 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.509 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.08 ? 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 NPC283681 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	26656
0.1-0.2	19967
0.2-0.3	2534
0.3-0.4	470
0.4-0.5	93
0.5-0.6	72
0.6-0.7	37
0.7-0.8	0
0.8-0.85	2
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8765	High Similarity	NPC297348
0.8765	High Similarity	NPC249204
0.8765	High Similarity	NPC48339
0.8765	High Similarity	NPC141769
0.8765	High Similarity	NPC477547
0.8554	High Similarity	NPC477451
0.8256	Intermediate Similarity	NPC211354
0.8105	Intermediate Similarity	NPC475625
0.7912	Intermediate Similarity	NPC475351
0.7872	Intermediate Similarity	NPC128572
0.7865	Intermediate Similarity	NPC107962
0.7614	Intermediate Similarity	NPC250393
0.7579	Intermediate Similarity	NPC471464
0.7471	Intermediate Similarity	NPC177834
0.7419	Intermediate Similarity	NPC160426
0.7245	Intermediate Similarity	NPC97700
0.7245	Intermediate Similarity	NPC30856
0.7204	Intermediate Similarity	NPC6295
0.7191	Intermediate Similarity	NPC294686
0.7143	Intermediate Similarity	NPC206003
0.7143	Intermediate Similarity	NPC473610
0.7065	Intermediate Similarity	NPC19400
0.7033	Intermediate Similarity	NPC222731
0.7	Intermediate Similarity	NPC234352
0.6961	Remote Similarity	NPC232037
0.6923	Remote Similarity	NPC132080
0.6889	Remote Similarity	NPC325828
0.6882	Remote Similarity	NPC107188
0.6869	Remote Similarity	NPC51172
0.6869	Remote Similarity	NPC49032
0.6809	Remote Similarity	NPC264101
0.6701	Remote Similarity	NPC113044
0.6701	Remote Similarity	NPC283829
0.6701	Remote Similarity	NPC161676
0.6667	Remote Similarity	NPC475643
0.6667	Remote Similarity	NPC475319
0.66	Remote Similarity	NPC92890
0.6566	Remote Similarity	NPC473601
0.6538	Remote Similarity	NPC116756
0.6452	Remote Similarity	NPC291203
0.6452	Remote Similarity	NPC217205
0.6316	Remote Similarity	NPC474399
0.6273	Remote Similarity	NPC470866
0.6263	Remote Similarity	NPC141433
0.625	Remote Similarity	NPC184617
0.6226	Remote Similarity	NPC475333
0.6226	Remote Similarity	NPC224098
0.6226	Remote Similarity	NPC208383
0.6224	Remote Similarity	NPC215408
0.619	Remote Similarity	NPC115165
0.6186	Remote Similarity	NPC54619
0.6162	Remote Similarity	NPC125324
0.6162	Remote Similarity	NPC485595
0.6154	Remote Similarity	NPC481418
0.6147	Remote Similarity	NPC233433
0.6129	Remote Similarity	NPC485594
0.6117	Remote Similarity	NPC477809
0.6082	Remote Similarity	NPC128123
0.6055	Remote Similarity	NPC476112
0.6055	Remote Similarity	NPC307534
0.6018	Remote Similarity	NPC480556
0.5941	Remote Similarity	NPC195297
0.5929	Remote Similarity	NPC94086
0.5929	Remote Similarity	NPC473817
0.5922	Remote Similarity	NPC202898
0.5913	Remote Similarity	NPC220836
0.5824	Remote Similarity	NPC88962
0.5818	Remote Similarity	NPC108072
0.5818	Remote Similarity	NPC470864
0.5755	Remote Similarity	NPC274200
0.5752	Remote Similarity	NPC232054
0.5745	Remote Similarity	NPC24960
0.5729	Remote Similarity	NPC181845
0.5701	Remote Similarity	NPC480555
0.5701	Remote Similarity	NPC151134
0.5701	Remote Similarity	NPC150372
0.5636	Remote Similarity	NPC473518
0.56	Remote Similarity	NPC329807
0.5591	Remote Similarity	NPC481189
0.5586	Remote Similarity	NPC232611
0.5566	Remote Similarity	NPC470433
0.5566	Remote Similarity	NPC46190
0.5566	Remote Similarity	NPC171073
0.5545	Remote Similarity	NPC306131
0.5545	Remote Similarity	NPC200802
0.5487	Remote Similarity	NPC83137
0.5481	Remote Similarity	NPC70204
0.5463	Remote Similarity	NPC300557
0.5439	Remote Similarity	NPC480553
0.5437	Remote Similarity	NPC485601
0.5426	Remote Similarity	NPC329727
0.5426	Remote Similarity	NPC277715
0.5421	Remote Similarity	NPC602423
0.5398	Remote Similarity	NPC480554
0.5391	Remote Similarity	NPC31896
0.5364	Remote Similarity	NPC98018
0.5364	Remote Similarity	NPC284104
0.5364	Remote Similarity	NPC103616
0.5347	Remote Similarity	NPC312678
0.5347	Remote Similarity	NPC253268
0.5312	Remote Similarity	NPC473774
0.5312	Remote Similarity	NPC481419
0.5312	Remote Similarity	NPC481417
0.531	Remote Similarity	NPC194207
0.531	Remote Similarity	NPC22779
0.53	Remote Similarity	NPC485591
0.5294	Remote Similarity	NPC48463
0.5294	Remote Similarity	NPC248944
0.5294	Remote Similarity	NPC7479
0.5294	Remote Similarity	NPC257296
0.5283	Remote Similarity	NPC305423
0.5283	Remote Similarity	NPC14704
0.5268	Remote Similarity	NPC269297
0.5268	Remote Similarity	NPC222202
0.5253	Remote Similarity	NPC481423
0.5248	Remote Similarity	NPC210157
0.5238	Remote Similarity	NPC330026
0.5225	Remote Similarity	NPC294129
0.5207	Remote Similarity	NPC210569
0.5192	Remote Similarity	NPC485590
0.5172	Remote Similarity	NPC84111
0.5172	Remote Similarity	NPC287483
0.5172	Remote Similarity	NPC470865
0.5138	Remote Similarity	NPC485603
0.5094	Remote Similarity	NPC470432
0.5094	Remote Similarity	NPC230507
0.5093	Remote Similarity	NPC485605
0.5091	Remote Similarity	NPC248746
0.5088	Remote Similarity	NPC13193
0.5088	Remote Similarity	NPC309278
0.5041	Remote Similarity	NPC473505
0.5041	Remote Similarity	NPC224314
0.5038	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 NPC283681 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7652
0.1-0.2	1436
0.2-0.3	53
0.3-0.4	5
0.4-0.5	0
0.5-0.6	3
0.6-0.7	1
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
0.6889	Remote Similarity	NPD8171	Phase 2
0.5842	Remote Similarity	NPD8170	Phase 2
0.5294	Remote Similarity	NPD6928	Phase 2
0.5208	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