NPASS Compound

Natural Product: NPC263545

Natural Product ID	NPC263545
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-O-Beta-Dglucopyranosyl-(2S,3R,4E,8E)-2-[(2'r)-Hydroxyicosanoyl-Amino]-4, 8-Octadecadiene-1,3-Diol
IUPAC Name	(2R)-2-hydroxy-N-[(2S,3R,4E,8E)-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]icosanamide
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3121696
PubChem CID	10771481
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000257] Sphingolipids [CHEMONTID:0003258] Glycosphingolipids [CHEMONTID:0001419] Neutral glycosphingolipids [CHEMONTID:0001428] Simple glycosylceramides [CHEMONTID:0004305] Glycosyl-N-acylsphingosines

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 137137 0 0 0 0 0 0 0 0999 V2000 13.4660 1.5316 3.0487 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3707 0.5277 2.6601 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2837 0.4919 1.1697 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2280 -0.4937 0.7137 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8611 -0.1543 1.2221 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8695 -1.1819 0.7593 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8419 -1.1688 -0.7802 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8548 -2.1697 -1.2904 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6561 -2.3345 -2.7150 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0598 -1.4645 -3.6856 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3797 -0.0954 -4.0426 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0932 1.0264 -3.0966 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6256 1.1145 -2.7725 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2565 2.2028 -1.8280 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8805 2.1000 -0.4681 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4532 0.8122 0.2208 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9714 0.7153 0.4381 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4151 1.7847 1.3077 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8937 1.6612 1.5100 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5839 0.3664 2.1259 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5099 -0.3091 2.0398 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6960 -0.0438 1.3493 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8295 -0.0330 2.3841 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0869 0.4481 1.7552 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3350 1.7222 1.5859 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5543 2.2845 0.9702 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5350 1.2500 0.5309 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7260 1.8948 -0.1016 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8362 3.1918 -0.2259 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0047 3.8574 -0.8506 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0305 2.8651 -1.3142 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1948 3.5598 -1.9733 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8745 4.4926 -1.0286 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4050 3.7683 0.1643 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4208 2.7362 -0.2860 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9980 1.9872 0.9085 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0006 0.9935 0.3425 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.0482 1.8253 -0.3853 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9553 -1.2286 3.0487 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9818 -1.0814 0.2863 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1099 -2.3589 0.8245 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3955 -3.3172 -0.1073 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6739 -3.8204 0.1457 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8793 -5.0507 -0.4386 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3421 -5.4072 -0.3026 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7158 -5.4754 1.0346 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0796 -6.1470 0.2416 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7623 -5.5721 0.7537 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3514 -4.3857 -0.1014 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1092 -4.8425 -1.4175 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8633 -5.1737 2.0846 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8782 -7.1602 -0.6611 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6094 -0.1929 2.9179 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2555 1.7333 0.2698 O 0 0 0 0 0 0 0 0 0 0 0 0 13.1073 2.5606 3.0714 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8075 1.2736 4.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2909 1.4793 2.2978 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4335 0.8097 3.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6476 -0.4836 3.0182 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2420 0.1366 0.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9971 1.4869 0.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2384 -0.4137 -0.4139 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4764 -1.5371 0.9451 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8270 -0.0519 2.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5284 0.8248 0.7602 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8701 -0.9092 1.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1074 -2.1996 1.1352 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8528 -1.5786 -1.1446 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7916 -0.1588 -1.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2651 -3.1774 -0.8973 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8860 -2.1117 -0.7073 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6739 -2.6850 -3.1817 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0758 -3.3579 -2.8362 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0788 -2.0850 -4.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8920 -1.4670 -3.5690 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7844 0.1594 -4.9961 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4400 -0.0108 -4.4484 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2923 1.9762 -3.7518 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7997 1.1177 -2.3270 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3196 0.1356 -2.3563 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 1.2572 -3.7039 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1577 2.2340 -1.6879 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5343 3.2071 -2.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4789 2.9241 0.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9717 2.2259 -0.4658 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7286 -0.0776 -0.3804 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9713 0.7033 1.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7955 -0.3052 0.8581 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4180 0.7358 -0.5243 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8303 1.6223 2.3476 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6727 2.8015 1.0225 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5845 2.5317 2.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7686 0.9388 0.8548 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5274 0.7356 3.1384 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8184 -0.2869 1.4312 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5886 2.4399 1.9218 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0607 2.9758 1.6849 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2499 2.8965 0.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8916 0.5972 1.3313 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0827 0.5801 -0.2455 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5254 1.2557 -0.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0416 3.8352 0.1427 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4918 4.5175 -0.0931 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6075 4.4614 -1.7016 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5650 2.1962 -2.0799 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3643 2.2041 -0.4773 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9024 2.8152 -2.3790 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7571 4.1050 -2.8511 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7618 4.9181 -1.5664 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2120 5.3226 -0.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9515 4.4828 0.8118 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6147 3.2940 0.7837 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9535 1.9328 -0.9160 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2073 3.2552 -0.8501 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1819 1.3887 1.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4922 2.6420 1.6244 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4708 0.3505 -0.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5041 0.4030 1.1395 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.8599 1.7633 -1.4861 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.0435 2.8837 -0.0793 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.0527 1.4087 -0.1596 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9195 -1.4918 3.0556 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8822 -0.7509 -0.2619 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1478 -1.1111 -0.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4481 -2.8168 -1.1090 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6269 -4.9882 -1.5242 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0025 -4.6214 -0.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5614 -6.4044 -0.7442 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5337 -6.0245 1.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6127 -6.5379 1.1350 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0019 -6.3630 0.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6362 -4.0562 0.2880 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7329 -5.3630 -1.4402 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2438 -5.8744 2.6563 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6453 -7.2357 -1.2890 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3931 -0.8577 3.6565 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7512 2.3091 -0.3790 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 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 2 3 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 23 39 1 0 22 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 48 51 1 0 47 52 1 0 20 53 1 0 19 54 1 0 49 42 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 0 2 59 1 0 3 60 1 0 3 61 1 0 4 62 1 0 4 63 1 0 5 64 1 0 5 65 1 0 6 66 1 0 6 67 1 0 7 68 1 0 7 69 1 0 8 70 1 0 8 71 1 0 9 72 1 0 9 73 1 0 10 74 1 0 10 75 1 0 11 76 1 0 11 77 1 0 12 78 1 0 12 79 1 0 13 80 1 0 13 81 1 0 14 82 1 0 14 83 1 0 15 84 1 0 15 85 1 0 16 86 1 0 16 87 1 0 17 88 1 0 17 89 1 0 18 90 1 0 18 91 1 0 19 92 1 1 22 93 1 6 23 94 1 1 24 95 1 0 25 96 1 0 26 97 1 0 26 98 1 0 27 99 1 0 27100 1 0 28101 1 0 29102 1 0 30103 1 0 30104 1 0 31105 1 0 31106 1 0 32107 1 0 32108 1 0 33109 1 0 33110 1 0 34111 1 0 34112 1 0 35113 1 0 35114 1 0 36115 1 0 36116 1 0 37117 1 0 37118 1 0 38119 1 0 38120 1 0 38121 1 0 39122 1 0 40123 1 0 40124 1 0 42125 1 6 44126 1 6 45127 1 0 45128 1 0 46129 1 0 47130 1 1 48131 1 1 49132 1 1 50133 1 0 51134 1 0 52135 1 0 53136 1 0 54137 1 0 M END

Standard InCHIKey	DCBUKXJYPRDHOR-FCZHZXJDSA-N
Standard InCHI	InChI=1S/C44H83NO9/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-33-38(48)43(52)45-36(35-53-44-42(51)41(50)40(49)39(34-46)54-44)37(47)32-30-28-26-24-22-20-16-14-12-10-8-6-4-2/h22,24,30,32,36-42,44,46-51H,3-21,23,25-29,31,33-35H2,1-2H3,(H,45,52)/b24-22+,32-30+/t36-,37+,38+,39+,40+,41-,42+,44+/m0/s1
SMILES	CCCCCCCCCCCCCCCCCC[C@H](C(=N[C@H]([C@@H](/C=C/CC/C=C/CCCCCCCCC)O)CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12583	Sauromatum giganteum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28394604]
NPO28204	Arisaema amurense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882436]
NPO28204	Arisaema amurense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12583	Sauromatum giganteum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28204	Arisaema amurense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12583	Sauromatum giganteum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28204	Arisaema amurense	Species	Araceae	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
FC	1
EC50	1

Activity Type	# Activity
Cell line	1
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
NPT681	Cell line	PC-12	Rattus norvegicus	EC50	=	12400.0	nM	PMID[28394604]
NPT2	Others	Unspecified	n.a.	FC	=	3.12	n.a.	PMID[24556145]

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 NPC263545 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	21958
0.1-0.2	23279
0.2-0.3	4252
0.3-0.4	277
0.4-0.5	36
0.5-0.6	9
0.6-0.7	1
0.7-0.8	1
0.8-0.85	7
0.85-0.9	5
0.9-0.95	2
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473950
1.0	High Similarity	NPC111567
1.0	High Similarity	NPC186840
1.0	High Similarity	NPC144916
1.0	High Similarity	NPC486421
1.0	High Similarity	NPC309898
1.0	High Similarity	NPC273493
1.0	High Similarity	NPC475125
1.0	High Similarity	NPC486419
1.0	High Similarity	NPC15851
1.0	High Similarity	NPC115448
1.0	High Similarity	NPC20819
1.0	High Similarity	NPC486418
1.0	High Similarity	NPC473604
1.0	High Similarity	NPC486420
1.0	High Similarity	NPC479188
1.0	High Similarity	NPC81468
0.95	High Similarity	NPC158445
0.95	High Similarity	NPC157353
0.95	High Similarity	NPC282088
0.9333	High Similarity	NPC156782
0.9333	High Similarity	NPC54961
0.8689	High Similarity	NPC282705
0.8689	High Similarity	NPC182632
0.8636	High Similarity	NPC8098
0.8636	High Similarity	NPC183449
0.8636	High Similarity	NPC197294
0.8308	Intermediate Similarity	NPC3568
0.8308	Intermediate Similarity	NPC17290
0.8308	Intermediate Similarity	NPC192066
0.8308	Intermediate Similarity	NPC256570
0.8095	Intermediate Similarity	NPC242503
0.8065	Intermediate Similarity	NPC61894
0.8065	Intermediate Similarity	NPC297079
0.7778	Intermediate Similarity	NPC43074
0.7778	Intermediate Similarity	NPC139782
0.7778	Intermediate Similarity	NPC74672
0.7778	Intermediate Similarity	NPC209047
0.7536	Intermediate Similarity	NPC23454
0.7536	Intermediate Similarity	NPC70323
0.7536	Intermediate Similarity	NPC262312
0.7536	Intermediate Similarity	NPC35269
0.7429	Intermediate Similarity	NPC45313
0.6892	Remote Similarity	NPC201128
0.589	Remote Similarity	NPC473581
0.5753	Remote Similarity	NPC602861
0.5574	Remote Similarity	NPC288086
0.5541	Remote Similarity	NPC475603
0.5541	Remote Similarity	NPC600808
0.5352	Remote Similarity	NPC488689
0.5217	Remote Similarity	NPC469469
0.5135	Remote Similarity	NPC21693
0.5062	Remote Similarity	NPC604736

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC263545 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6263
0.1-0.2	2725
0.2-0.3	154
0.3-0.4	7
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
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
0.7778	Intermediate Similarity	NPD8522	Clinical (unspecified phase)

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