NPASS Compound

Natural Product: NPC476660

Natural Product ID	NPC476660
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1,3-dihydroxypropan-2-yl (23E,25E)-tetratriaconta-23,25-dienoate
IUPAC Name	1,3-dihydroxypropan-2-yl (23E,25E)-tetratriaconta-23,25-dienoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	76320327
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0003808] Monoradylglycerols [CHEMONTID:0001133] Monoacylglycerols [CHEMONTID:0001603] 2-monoacylglycerols

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 111110 0 0 0 0 0 0 0 0999 V2000 11.9556 -0.7125 2.0960 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5038 -1.1252 2.0419 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8823 -0.8093 0.6796 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5931 -1.5250 -0.4200 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0415 -1.2603 -1.7776 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5818 -1.6906 -1.9431 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1297 -1.3893 -3.3322 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1522 0.0324 -3.7426 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2340 0.9414 -3.0647 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3279 0.6212 -2.1842 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4673 1.6513 -1.5704 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5294 1.3139 -0.6613 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7022 2.3640 -0.0773 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7521 2.6054 1.3726 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3101 1.6375 2.3685 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9283 0.2898 2.4385 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3455 -0.5044 3.5698 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9269 -0.8507 3.5585 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3509 -1.7780 2.5921 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3409 -1.5900 1.1417 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6564 -0.3856 0.5944 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8088 -0.3214 1.0221 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3687 0.9466 0.4189 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8140 1.0584 0.8455 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3556 2.3450 0.2360 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7766 2.4665 0.6686 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4717 3.7093 0.1398 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4741 3.7031 -1.3649 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1773 2.4981 -1.9381 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6112 2.4081 -1.5022 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3257 1.1974 -2.0632 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6862 -0.0907 -1.6505 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4372 -1.2594 -2.2320 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8323 -1.2118 -1.7202 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6964 -0.5127 -2.2963 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2332 -1.9272 -0.6000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5308 -1.9231 -0.0656 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5792 -1.3334 1.3229 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1087 -0.0154 1.2311 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1825 -3.2761 -0.1233 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.4617 -3.2128 0.4239 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1268 0.2475 1.5535 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2668 -0.5318 3.1619 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6443 -1.4858 1.6968 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4384 -2.2062 2.2629 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9542 -0.5724 2.8310 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9312 0.2985 0.5260 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8193 -1.1048 0.7150 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6309 -2.6305 -0.2146 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6641 -1.1922 -0.4250 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6305 -1.7712 -2.5641 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0941 -0.1580 -2.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0422 -1.2400 -1.1200 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5758 -2.8069 -1.8227 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0869 -1.8083 -3.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7564 -2.0358 -4.0123 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2092 0.4446 -3.7264 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9054 0.0639 -4.8505 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2808 2.0289 -3.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1601 -0.4034 -1.9029 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5528 2.6905 -1.8198 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4740 0.2668 -0.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8637 3.3244 -0.6463 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6168 2.1192 -0.3308 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1131 3.5590 1.5333 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7970 3.0199 1.6310 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1830 1.5887 2.4038 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5680 2.1353 3.4086 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8505 -0.2674 1.5026 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0318 0.3786 2.6785 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9769 -1.4340 3.6744 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5783 0.0723 4.5109 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3214 0.1179 3.6370 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7052 -1.2989 4.5983 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2766 -2.0445 2.9021 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8666 -2.7920 2.7696 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3291 -1.7003 0.6298 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7134 -2.4734 0.7246 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5900 -0.5527 -0.5317 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1588 0.5510 0.7263 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8828 -0.2895 2.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3555 -1.1827 0.6453 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3457 0.9374 -0.6719 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8530 1.8453 0.8188 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9231 1.0603 1.9505 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4108 0.2388 0.3805 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3437 2.2267 -0.8704 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7886 3.2237 0.5784 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8787 2.5174 1.7866 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3938 1.5814 0.3586 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4612 3.7460 0.5867 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8668 4.5690 0.5025 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4308 3.7238 -1.7345 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9529 4.6256 -1.7286 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1126 2.6018 -3.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5724 1.6069 -1.6740 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1372 3.2940 -1.9154 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7276 2.4857 -0.4002 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4228 1.2969 -3.1545 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3676 1.2539 -1.6302 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6067 -0.1327 -1.8427 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7934 -0.1854 -0.5303 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4595 -1.1445 -3.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9727 -2.2272 -1.9113 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1345 -1.2369 -0.7262 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9295 -1.9083 2.0209 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6219 -1.3037 1.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8177 0.6293 1.4203 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3037 -3.5728 -1.1988 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5881 -4.0539 0.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.1086 -2.7503 -0.1800 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 2 0 10 11 1 0 11 12 2 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 21 22 1 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 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 40 41 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 2 46 1 0 3 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 5 51 1 0 5 52 1 0 6 53 1 0 6 54 1 0 7 55 1 0 7 56 1 0 8 57 1 0 8 58 1 0 9 59 1 0 10 60 1 0 11 61 1 0 12 62 1 0 13 63 1 0 13 64 1 0 14 65 1 0 14 66 1 0 15 67 1 0 15 68 1 0 16 69 1 0 16 70 1 0 17 71 1 0 17 72 1 0 18 73 1 0 18 74 1 0 19 75 1 0 19 76 1 0 20 77 1 0 20 78 1 0 21 79 1 0 21 80 1 0 22 81 1 0 22 82 1 0 23 83 1 0 23 84 1 0 24 85 1 0 24 86 1 0 25 87 1 0 25 88 1 0 26 89 1 0 26 90 1 0 27 91 1 0 27 92 1 0 28 93 1 0 28 94 1 0 29 95 1 0 29 96 1 0 30 97 1 0 30 98 1 0 31 99 1 0 31100 1 0 32101 1 0 32102 1 0 33103 1 0 33104 1 0 37105 1 0 38106 1 0 38107 1 0 39108 1 0 40109 1 0 40110 1 0 41111 1 0 M END

Standard InCHIKey	WQBCRIDKAGGQMZ-HULFFUFUSA-N
Standard InCHI	InChI=1S/C37H70O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-32-33-37(40)41-36(34-38)35-39/h9-12,36,38-39H,2-8,13-35H2,1H3/b10-9+,12-11+
SMILES	CCCCCCCC/C=C/C=C/CCCCCCCCCCCCCCCCCCCCCC(=O)OC(CO)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.53	Volume:	675.759 ? Van der Waals volume.
Dense:	0.856	LogP:	9.45 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.964 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.801 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	34.0	Rigid Bonds:	3.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	0.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.046	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.708	Fsp³:	0.865
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.637	Fluc inhibitor:	0.191 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.801	Promiscuous compounds:	0.248

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.175	MDCK Permeability:	-4.78
Pgp-inhibitor:	0.0	Pgp-substrate:	0.186
PAMPA:	0.0 ? 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):	0.97
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.636
Plasma Protein Binding (PPB):	99.433%	Volume Distribution (VD):	1.252
Fu:	0.763% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.049
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.989
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.235
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.353
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

3.53

Half-life (T1/2):

3.21

ADMET: Toxicity

hERG Blockers:	0.543	hERG Blockers (10um):	0.745
Human Hepatotoxicity (H-HT):	0.57	Drug-induced Liver Injury (DILI):	0.031
AMES Toxicity:	0.07	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.039	Skin Sensitization:	1.0
Carcinogencity:	0.114	Eye Corrosion:	0.086
Eye Irritation:	0.878	Respiratory Toxicity:	0.376
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.628
Hematotoxicity:	0.034	Drug-induced Nephrotoxicity:	0.324
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.894	Hek293 Cytotoxicity:	0.189
BCF:	0.27 ? 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:	5.31 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.34 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.535 ? 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
NPO33615	Aspergillus sp. MF-93	Species	Aspergillaceae	Eukaryota	n.a.	Quan-Zhou Gulf, Fujian Province, China	2002	PMID[18823067]
NPO33615	Aspergillus sp. MF-93	Species	Aspergillaceae	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
Inhibition	1

Activity Type	# Activity
Organism	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
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	16.3	%	PMID[18823067]

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 NPC476660 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	16365
0.1-0.2	28991
0.2-0.3	3792
0.3-0.4	608
0.4-0.5	75
0.5-0.6	15
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC476657
0.9412	High Similarity	NPC476659
0.8824	High Similarity	NPC148192
0.8611	High Similarity	NPC476658
0.7576	Intermediate Similarity	NPC23155
0.7368	Intermediate Similarity	NPC81896
0.6389	Remote Similarity	NPC228473
0.6279	Remote Similarity	NPC48218
0.6279	Remote Similarity	NPC141481
0.6279	Remote Similarity	NPC464342
0.5952	Remote Similarity	NPC476654
0.5952	Remote Similarity	NPC476655
0.5952	Remote Similarity	NPC476656
0.587	Remote Similarity	NPC473559
0.587	Remote Similarity	NPC324981
0.5476	Remote Similarity	NPC104537
0.5405	Remote Similarity	NPC309606
0.5238	Remote Similarity	NPC277597
0.52	Remote Similarity	NPC474321
0.5143	Remote Similarity	NPC47363
0.5143	Remote Similarity	NPC287231
0.5128	Remote Similarity	NPC128061
0.5111	Remote Similarity	NPC330426
0.5111	Remote Similarity	NPC127091
0.5111	Remote Similarity	NPC22101

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476660 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6234
0.1-0.2	2741
0.2-0.3	151
0.3-0.4	19
0.4-0.5	3
0.5-0.6	2
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
0.5238	Remote Similarity	NPD3730	Pre-clinical
0.5143	Remote Similarity	NPD2699	Pre-clinical

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