NPASS Compound

Natural Product: NPC486130

Natural Product ID	NPC486130
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UXYWJXUPABRMMS-DMTJNRQSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0002125] Alkyl glycosides [CHEMONTID:0001754] Simplexides

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 103109 0 0 0 0 0 0 0 0999 V2000 -4.7300 -1.7311 2.6802 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4948 -1.2908 1.2737 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1375 0.0593 0.9512 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9838 0.9828 0.6251 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0358 0.8478 1.8376 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3494 -0.4862 1.6458 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1560 -1.3371 0.8920 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1571 -0.2557 0.9850 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0326 -0.6839 1.7296 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5709 -1.8084 0.9377 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2410 -1.2373 -0.2640 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2117 -0.1319 0.0113 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3100 0.2210 1.4747 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1501 -0.6879 2.2998 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1088 -1.5273 1.4401 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6337 -0.6008 0.4025 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5674 -0.3535 -0.6263 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9958 0.7099 -1.5614 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4079 1.0376 -1.7006 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4383 0.2594 -0.9413 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0801 1.1079 0.1251 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4972 -0.3240 -1.8217 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2048 -1.7963 -1.9918 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7652 -1.8855 -1.4638 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8816 -0.9716 -0.2716 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8030 -1.5083 0.5860 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8945 -0.1145 -1.4025 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7510 0.6328 -2.1171 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0441 0.6597 -1.4677 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1029 1.2459 -1.8209 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9253 -0.0992 -0.3408 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6380 -0.6323 -0.2605 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9155 0.4223 2.0153 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7003 1.0284 -0.6222 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1933 1.9309 1.7787 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3580 2.3075 0.4628 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9113 2.7359 -0.7959 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9780 0.0257 -0.1219 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2419 0.5451 0.1010 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3371 -0.4500 0.0961 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6537 0.2641 -0.1824 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6220 0.9134 -1.5522 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2255 1.4655 -1.7677 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4831 0.7171 -2.8203 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3364 1.4208 -3.1914 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5315 1.6903 -0.5975 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6190 1.8513 -1.6748 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7046 -0.6508 -0.1856 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4949 -1.0403 1.3612 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7192 -1.3327 3.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9898 -1.4056 3.4099 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8027 -2.8402 2.7731 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0199 -2.0285 0.6093 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5907 0.4971 1.8678 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4576 0.5924 -0.2665 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6966 0.8735 2.7276 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0794 -0.9578 2.6304 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3811 -1.1261 2.7064 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3048 -2.4201 0.5638 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1763 -2.5131 1.5093 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8181 -2.0349 -0.8192 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4411 -0.9312 -0.9785 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7884 1.2462 1.5017 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8532 -0.0920 2.9577 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5928 -1.3228 3.0218 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -1.8717 2.1028 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6258 -2.4298 1.0538 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8020 0.3967 0.9101 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4671 -1.3285 -1.1901 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5627 0.4428 -2.5747 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3955 1.6341 -1.2945 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7294 0.9917 -2.7856 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5777 2.1255 -1.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0725 1.4954 -0.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3826 1.9898 0.2908 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1204 0.6184 1.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3229 0.1215 -2.8456 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2734 -2.0993 -3.0511 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8589 -2.4397 -1.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1668 -1.4246 -2.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4628 -2.9050 -1.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6341 -2.4823 0.6484 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5122 1.1462 -3.0500 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7518 -1.7490 -0.2903 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2438 -0.3375 0.7382 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4778 1.3772 1.6467 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0315 0.5699 3.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7185 1.8108 -0.0486 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6859 2.7072 2.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1829 3.7895 -0.9936 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7804 2.6832 -0.7880 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2144 2.0914 -1.6219 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1792 0.8927 1.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2727 -1.2641 -0.6409 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8769 1.0286 0.5643 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7891 0.1161 -2.2923 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4225 2.4960 -2.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2853 -0.3200 -2.5674 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1714 0.6793 -3.7173 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1078 1.1381 -4.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2141 1.7748 -0.8883 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0539 -0.7897 0.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6076 -0.3577 2.0748 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 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 22 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 13 33 1 0 12 34 1 6 5 35 1 0 4 36 1 0 36 37 1 0 3 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 44 45 1 0 43 46 1 0 42 47 1 0 41 48 1 0 40 49 1 0 7 2 1 0 33 9 1 0 46 39 1 0 17 12 1 0 25 20 1 0 32 27 1 0 25 16 1 0 1 50 1 0 1 51 1 0 1 52 1 0 2 53 1 6 3 54 1 1 4 55 1 6 5 56 1 1 6 57 1 1 9 58 1 1 10 59 1 0 10 60 1 0 11 61 1 0 11 62 1 0 13 63 1 6 14 64 1 0 14 65 1 0 15 66 1 0 15 67 1 0 16 68 1 1 17 69 1 6 18 70 1 0 18 71 1 0 19 72 1 0 19 73 1 0 21 74 1 0 21 75 1 0 21 76 1 0 22 77 1 6 23 78 1 0 23 79 1 0 24 80 1 0 24 81 1 0 26 82 1 0 28 83 1 0 32 84 1 0 32 85 1 0 33 86 1 0 33 87 1 0 34 88 1 0 35 89 1 0 37 90 1 0 37 91 1 0 37 92 1 0 39 93 1 1 40 94 1 6 41 95 1 1 42 96 1 6 43 97 1 6 44 98 1 0 44 99 1 0 45100 1 0 47101 1 0 48102 1 0 49103 1 0 M END

Standard InCHIKey	UXYWJXUPABRMMS-DMTJNRQSSA-N
Standard InCHI	InChI=1S/C35H54O14/c1-16-29(49-31-27(40)26(39)25(38)23(14-36)48-31)30(44-3)28(41)32(46-16)47-19-6-10-34(42)18(13-19)4-5-22-21(34)7-9-33(2)20(8-11-35(22,33)43)17-12-24(37)45-15-17/h12,16,18-23,25-32,36,38-43H,4-11,13-15H2,1-3H3/t16-,18+,19-,20+,21-,22+,23-,25-,26+,27-,28-,29-,30-,31+,32-,33+,34+,35-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)O[C@H]1CC[C@]2([C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1)O)O)OC)O[C@@H]1[C@H]([C@@H]([C@H]([C@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	698.35	Volume:	671.811 ? Van der Waals volume.
Dense:	1.04	LogP:	-0.822 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.042 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.413 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	38.0
TPSA:	214.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.134	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.726	Fsp³:	0.914
MCE-18:	133.284 ? 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:	0.677	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.166	Promiscuous compounds:	0.303

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.463	MDCK Permeability:	-5.225
Pgp-inhibitor:	0.002	Pgp-substrate:	0.982
PAMPA:	0.995 ? 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):	0.389
20% Bioavailability (F20%):	0.195	30% Bioavailability (F30%):	0.767
50% Bioavailability (F50%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072	MRP1:	0.11
Plasma Protein Binding (PPB):	48.673%	Volume Distribution (VD):	-0.465
Fu:	56.614% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.203
BSEP inhibitor:	0.097

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.422
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.154
HLM stability:	0.001 ? 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):

1.057

Half-life (T1/2):

4.011

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.32
Human Hepatotoxicity (H-HT):	0.642	Drug-induced Liver Injury (DILI):	0.91
AMES Toxicity:	0.908	Rat Oral Acute Toxicity:	0.85
Maximum Recommended Daily Dose:	0.992	Skin Sensitization:	1.0
Carcinogencity:	0.557	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.835
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.942
Hematotoxicity:	0.761	Drug-induced Nephrotoxicity:	0.99
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.894
A549 Cytotoxicity:	0.718	Hek293 Cytotoxicity:	0.956
BCF:	0.565 ? 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:	3.146 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.511 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.702 ? 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
NPO8402	Thevetia peruviana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26714048]
NPO8402	Thevetia peruviana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39027575]
NPO8402	Thevetia peruviana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8402	Thevetia peruviana	Species	Apocynaceae	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

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell line	1
Non-molecular	2
Others	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
NPT1312	Cell line	SW1990	Homo sapiens	IC50	>	10000.0	nM	PMID[26714048]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[26714048]
NPT27	Others	Unspecified	n.a.	IC50	>	10000.0	nM	PMID[26714048]

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 NPC486130 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	13650
0.1-0.2	31028
0.2-0.3	4337
0.3-0.4	651
0.4-0.5	74
0.5-0.6	56
0.6-0.7	40
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC486131
0.7841	Intermediate Similarity	NPC486127
0.7753	Intermediate Similarity	NPC486143
0.7753	Intermediate Similarity	NPC486135
0.7753	Intermediate Similarity	NPC486142
0.7753	Intermediate Similarity	NPC486137
0.7753	Intermediate Similarity	NPC486149
0.7667	Intermediate Similarity	NPC232785
0.7667	Intermediate Similarity	NPC486139
0.7444	Intermediate Similarity	NPC475629
0.7419	Intermediate Similarity	NPC486132
0.734	Intermediate Similarity	NPC486128
0.7263	Intermediate Similarity	NPC486144
0.7263	Intermediate Similarity	NPC486145
0.7263	Intermediate Similarity	NPC486147
0.7263	Intermediate Similarity	NPC486136
0.7263	Intermediate Similarity	NPC486148
0.7041	Intermediate Similarity	NPC486140
0.6977	Remote Similarity	NPC486129
0.697	Remote Similarity	NPC486133
0.6939	Remote Similarity	NPC120390
0.6667	Remote Similarity	NPC474423
0.6635	Remote Similarity	NPC486152
0.6526	Remote Similarity	NPC231518
0.6526	Remote Similarity	NPC488944
0.6517	Remote Similarity	NPC5311
0.6517	Remote Similarity	NPC77299
0.6517	Remote Similarity	NPC480906
0.6495	Remote Similarity	NPC329986
0.6495	Remote Similarity	NPC140092
0.6489	Remote Similarity	NPC236973
0.6489	Remote Similarity	NPC32177
0.6489	Remote Similarity	NPC469756
0.6489	Remote Similarity	NPC275901
0.6444	Remote Similarity	NPC480914
0.6421	Remote Similarity	NPC188234
0.6327	Remote Similarity	NPC486146
0.6275	Remote Similarity	NPC475419
0.6263	Remote Similarity	NPC486138
0.6263	Remote Similarity	NPC276838
0.625	Remote Similarity	NPC480910
0.625	Remote Similarity	NPC480909
0.6222	Remote Similarity	NPC84987
0.6211	Remote Similarity	NPC30483
0.6211	Remote Similarity	NPC470897
0.617	Remote Similarity	NPC480907
0.6162	Remote Similarity	NPC146857
0.6139	Remote Similarity	NPC479360
0.6139	Remote Similarity	NPC479359
0.6139	Remote Similarity	NPC488943
0.6139	Remote Similarity	NPC488942
0.6082	Remote Similarity	NPC32793
0.6082	Remote Similarity	NPC116075
0.6082	Remote Similarity	NPC240070
0.6058	Remote Similarity	NPC486134
0.6058	Remote Similarity	NPC486141
0.6	Remote Similarity	NPC329784
0.6	Remote Similarity	NPC486150
0.5979	Remote Similarity	NPC292467
0.5962	Remote Similarity	NPC74259
0.596	Remote Similarity	NPC125077
0.5918	Remote Similarity	NPC479353
0.5918	Remote Similarity	NPC479354
0.5914	Remote Similarity	NPC76572
0.5914	Remote Similarity	NPC193382
0.5905	Remote Similarity	NPC474908
0.5905	Remote Similarity	NPC329675
0.5905	Remote Similarity	NPC194716
0.5859	Remote Similarity	NPC264336
0.5859	Remote Similarity	NPC488941
0.5859	Remote Similarity	NPC488940
0.5794	Remote Similarity	NPC488945
0.5794	Remote Similarity	NPC488946
0.5769	Remote Similarity	NPC475590
0.5761	Remote Similarity	NPC99620
0.5758	Remote Similarity	NPC475556
0.5758	Remote Similarity	NPC311706
0.5743	Remote Similarity	NPC469749
0.5644	Remote Similarity	NPC59288
0.5638	Remote Similarity	NPC469750
0.5577	Remote Similarity	NPC479357
0.5534	Remote Similarity	NPC247190
0.5474	Remote Similarity	NPC157376
0.5474	Remote Similarity	NPC142066
0.5474	Remote Similarity	NPC603972
0.5464	Remote Similarity	NPC305574
0.5426	Remote Similarity	NPC99728
0.5426	Remote Similarity	NPC87250
0.5426	Remote Similarity	NPC244402
0.5426	Remote Similarity	NPC50305
0.5392	Remote Similarity	NPC610296
0.5368	Remote Similarity	NPC196429
0.5312	Remote Similarity	NPC486126
0.5312	Remote Similarity	NPC17896
0.5312	Remote Similarity	NPC469755
0.5312	Remote Similarity	NPC284406
0.5312	Remote Similarity	NPC197707
0.5312	Remote Similarity	NPC251866
0.5258	Remote Similarity	NPC199428
0.5258	Remote Similarity	NPC243196
0.5258	Remote Similarity	NPC109448
0.5258	Remote Similarity	NPC310341
0.5208	Remote Similarity	NPC309034
0.5204	Remote Similarity	NPC146456
0.5204	Remote Similarity	NPC250556
0.5196	Remote Similarity	NPC27363
0.5192	Remote Similarity	NPC208193
0.5182	Remote Similarity	NPC117445
0.5182	Remote Similarity	NPC308262
0.5155	Remote Similarity	NPC480915
0.5152	Remote Similarity	NPC483822
0.5093	Remote Similarity	NPC488938
0.5093	Remote Similarity	NPC488937
0.505	Remote Similarity	NPC72260

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5777
0.1-0.2	3275
0.2-0.3	78
0.3-0.4	9
0.4-0.5	7
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
0.6526	Remote Similarity	NPD8033	Approved
0.5312	Remote Similarity	NPD7319	Approved
0.5204	Remote Similarity	NPD7507	Pre-clinical
0.505	Remote Similarity	NPD8294	Phase 4

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