NPASS Compound

Natural Product: NPC125545

Natural Product ID	NPC125545
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NUWZVUKAGIYNSQ-VGBCUWDCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21626528
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 126131 0 0 0 0 0 0 0 0999 V2000 2.6249 -6.9236 0.4976 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2399 -7.4046 0.0132 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4392 -6.5057 -0.3453 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0877 -5.1190 -0.5623 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1034 -4.1797 -0.0878 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8354 -2.6692 -0.4372 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8212 -2.7430 -1.9592 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4344 -2.2940 0.1691 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3911 -2.4725 1.6696 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3273 -1.3976 2.2448 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1779 -1.0845 1.0646 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0655 -2.2648 0.8709 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0790 -0.9724 -0.0262 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7387 -0.7619 -1.3406 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7493 0.3596 -1.3688 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6688 0.2819 -0.1890 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7792 1.2900 -0.2529 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3923 2.6987 -0.0452 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3480 1.1817 -1.6562 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7048 1.7648 -1.8190 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6407 1.2143 -0.7861 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1393 1.3778 0.6427 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3307 2.7661 1.0757 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0861 0.4891 1.4551 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7921 0.7804 0.7591 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2182 0.7126 2.1415 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8157 0.3574 2.3106 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9145 0.2436 1.1215 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8745 1.3613 1.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9029 1.7965 -0.9450 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8539 -0.3161 -2.3588 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8939 -1.9947 0.0369 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1445 -0.6865 -0.0976 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0899 0.1421 1.1568 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4493 0.1615 1.8329 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3149 1.0490 0.9601 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8840 0.7836 -0.4926 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2034 0.9777 -1.2732 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6103 2.2795 -0.9809 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8180 2.5874 -1.6055 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5120 3.6993 -2.6040 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0767 4.9105 -1.8191 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2502 5.2810 -0.9251 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4101 4.1041 0.0289 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5148 4.4396 0.9950 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7892 2.9762 -0.6994 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0102 6.4414 -0.2400 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6952 5.9616 -2.6452 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6522 4.0175 -3.3233 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3737 -0.4435 -0.7113 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1840 2.3642 1.3261 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9798 -1.1104 1.8164 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 1.4558 0.7774 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9627 -8.8756 0.0545 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0820 -6.4462 -0.3664 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1885 -7.8406 0.8110 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4235 -6.2573 1.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5664 -7.1666 -0.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8648 -4.9363 0.0489 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2202 -4.9895 -1.6294 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0670 -4.3568 -0.6379 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3058 -4.2689 0.9731 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1896 -2.9704 -2.3229 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4531 -3.6093 -2.2838 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3204 -1.8762 -2.4190 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2638 -3.0644 -0.1377 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5584 -2.3180 2.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7364 -3.4871 1.9776 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8262 -0.6023 2.7596 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9454 -1.9385 3.0214 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2414 -2.5404 -0.1841 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6886 -3.1898 1.3565 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0349 -2.0484 1.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4587 -0.1627 0.2491 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1560 -1.7147 -1.7727 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3897 0.1188 -2.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3239 1.3373 -1.5800 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1521 -0.7215 -0.2949 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5254 3.0849 0.9700 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0550 3.3618 -0.6812 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3748 2.8944 -0.4834 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3914 0.1185 -1.9395 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6053 1.7412 -2.2997 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0885 1.4295 -2.8196 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7093 2.8762 -1.8901 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7595 0.1292 -0.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7507 3.1253 1.9233 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2576 3.5199 0.2332 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4132 2.8789 1.3882 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8232 0.4659 2.5107 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1166 0.9401 1.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0623 -0.5104 0.9828 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9253 -0.2971 0.4369 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4068 1.7436 2.5714 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8542 0.0575 2.7745 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3371 1.0579 3.0608 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7193 -0.6316 2.8572 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3534 2.2994 1.5977 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0507 1.1736 1.8683 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4377 1.6195 0.2181 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7638 2.7580 -1.2296 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9476 -0.8700 -3.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3966 -0.2742 -0.7952 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3488 -0.1569 1.8935 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3386 0.5321 2.8544 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3680 0.7612 1.1400 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2530 1.6244 -0.8506 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9763 0.9081 -2.3445 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9073 0.2257 -0.8899 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2010 1.7082 -2.1601 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7116 3.3000 -3.2713 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2662 4.5726 -1.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1783 5.3384 -1.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4331 3.9459 0.5344 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0540 5.3590 0.7092 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0840 4.6387 2.0220 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2780 3.6234 1.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8099 7.0285 -0.3549 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2335 5.9160 -3.4767 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2933 3.2577 -3.2115 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9410 2.6676 1.8920 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4703 -1.3201 2.6506 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8831 2.0282 1.5645 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0332 -9.1223 -0.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8587 -9.1042 1.1491 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8176 -9.4631 -0.2837 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 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 6 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 21 30 1 0 14 31 1 0 6 32 1 6 32 33 1 0 33 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 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 44 46 1 0 43 47 1 0 42 48 1 0 41 49 1 0 37 50 1 0 36 51 1 0 35 52 1 0 34 53 1 0 2 54 1 0 13 8 1 0 28 16 1 0 50 33 1 0 28 11 1 0 46 40 1 0 25 17 1 0 1 55 1 0 1 56 1 0 1 57 1 0 3 58 1 0 4 59 1 0 4 60 1 0 5 61 1 0 5 62 1 0 7 63 1 0 7 64 1 0 7 65 1 0 8 66 1 6 9 67 1 0 9 68 1 0 10 69 1 0 10 70 1 0 12 71 1 0 12 72 1 0 12 73 1 0 13 74 1 1 14 75 1 6 15 76 1 0 15 77 1 0 16 78 1 6 18 79 1 0 18 80 1 0 18 81 1 0 19 82 1 0 19 83 1 0 20 84 1 0 20 85 1 0 21 86 1 6 23 87 1 0 23 88 1 0 23 89 1 0 24 90 1 0 24 91 1 0 24 92 1 0 25 93 1 6 26 94 1 0 26 95 1 0 27 96 1 0 27 97 1 0 29 98 1 0 29 99 1 0 29100 1 0 30101 1 0 31102 1 0 33103 1 6 34104 1 1 35105 1 1 36106 1 6 37107 1 6 38108 1 0 38109 1 0 40110 1 6 41111 1 6 42112 1 1 43113 1 6 44114 1 1 45115 1 0 45116 1 0 45117 1 0 47118 1 0 48119 1 0 49120 1 0 51121 1 0 52122 1 0 53123 1 0 54124 1 0 54125 1 0 54126 1 0 M END

Standard InCHIKey	NUWZVUKAGIYNSQ-VGBCUWDCSA-N
Standard InCHI	InChI=1S/C42H72O12/c1-21(2)11-10-15-42(9,54-37-35(50)33(48)31(46)25(53-37)20-51-36-34(49)32(47)30(45)22(3)52-36)23-12-17-41(8)29(23)24(43)19-27-39(6)16-14-28(44)38(4,5)26(39)13-18-40(27,41)7/h11,22-37,43-50H,10,12-20H2,1-9H3/t22-,23-,24+,25+,26-,27+,28-,29-,30-,31+,32+,33-,34+,35+,36+,37-,39-,40+,41+,42-/m0/s1
SMILES	CC(=CCC[C@@](C)([C@H]1CC[C@]2(C)[C@@H]1[C@@H](C[C@@H]1[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@@]21C)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)O1)O)O)O)C

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
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	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 NPC125545 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	21249
0.1-0.2	23493
0.2-0.3	4453
0.3-0.4	565
0.4-0.5	58
0.5-0.6	24
0.6-0.7	12
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	Natural Product ID
0.7632	Intermediate Similarity	NPC66654
0.75	Intermediate Similarity	NPC213190
0.7326	Intermediate Similarity	NPC152584
0.7294	Intermediate Similarity	NPC131479
0.7176	Intermediate Similarity	NPC69737
0.6705	Remote Similarity	NPC207845
0.663	Remote Similarity	NPC208650
0.6489	Remote Similarity	NPC220427
0.6429	Remote Similarity	NPC6931
0.6429	Remote Similarity	NPC160734
0.6289	Remote Similarity	NPC159005
0.6279	Remote Similarity	NPC114874
0.6277	Remote Similarity	NPC208594
0.6122	Remote Similarity	NPC14946
0.6122	Remote Similarity	NPC63368
0.6118	Remote Similarity	NPC31907
0.61	Remote Similarity	NPC135369
0.5918	Remote Similarity	NPC160816
0.5914	Remote Similarity	NPC472719
0.59	Remote Similarity	NPC246124
0.5851	Remote Similarity	NPC127801
0.5784	Remote Similarity	NPC180183
0.5761	Remote Similarity	NPC208477
0.5755	Remote Similarity	NPC146868
0.5701	Remote Similarity	NPC488294
0.5657	Remote Similarity	NPC65167
0.5625	Remote Similarity	NPC472717
0.5618	Remote Similarity	NPC309425
0.5566	Remote Similarity	NPC241381
0.5534	Remote Similarity	NPC472718
0.5532	Remote Similarity	NPC181467
0.5398	Remote Similarity	NPC488291
0.5385	Remote Similarity	NPC157659
0.5283	Remote Similarity	NPC472716
0.5104	Remote Similarity	NPC473199
0.5102	Remote Similarity	NPC269627
0.5085	Remote Similarity	NPC488293
0.5055	Remote Similarity	NPC43912
0.5054	Remote Similarity	NPC8431
0.5049	Remote Similarity	NPC237071
0.5049	Remote Similarity	NPC238796

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC125545 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7614
0.1-0.2	1483
0.2-0.3	49
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
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
		NPD

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