NPASS Compound

Natural Product: NPC87425

Natural Product ID	NPC87425
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VUEGHZSQVJADCO-LDNGJIBLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	3086656
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 182191 0 0 0 0 0 0 0 0999 V2000 -9.2555 -4.6623 -0.0108 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0961 -3.1385 -0.0553 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3650 -2.5047 -0.4926 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6028 -1.1226 0.0152 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7008 -0.6645 1.1100 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3744 -1.3647 1.0907 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6584 -2.7501 1.1868 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8046 -1.2001 -0.1690 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5020 -0.6740 -0.0606 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5216 0.6631 -0.7494 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9589 0.4017 -2.2017 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9950 -0.6294 -2.7650 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0180 -1.8020 -2.0595 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5291 -1.5844 -0.7427 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2858 -1.0305 -0.8562 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2602 -1.8454 -0.3593 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3697 -2.3534 -1.4743 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0187 -1.7248 -1.5453 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0307 -0.2801 -1.1172 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8974 0.3819 -2.1267 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4755 -0.2064 0.3001 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7206 1.2221 0.6464 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3701 1.9064 0.6464 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4281 1.7247 -0.6244 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1534 2.7707 -1.5887 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3555 0.3401 -1.1760 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3453 -0.6238 -0.6307 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5332 -0.0236 -0.0019 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7677 1.2244 0.1603 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9689 1.7663 0.7902 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9402 0.8172 1.3750 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7978 1.6478 2.3151 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9866 0.8002 2.6900 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9851 1.8171 3.6099 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2300 2.9430 1.7752 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5743 3.5264 0.5957 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7132 2.5979 -0.2450 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8401 3.3933 -1.1425 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 2.7879 -1.5599 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8083 2.2290 -0.3324 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7352 3.3199 0.7324 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6751 1.7973 -1.0485 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3339 1.3347 -2.1926 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9672 1.5008 -0.6546 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8591 0.7373 -1.4423 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9678 1.5716 -2.0526 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9571 2.0642 -1.0456 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8806 1.2138 0.1924 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6678 -0.2171 -0.3294 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9811 -1.1188 0.8113 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3020 -1.1448 1.2100 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1817 -1.6664 0.2715 C 0 0 1 0 0 0 0 0 0 0 0 0 13.3126 -0.8039 -0.1400 C 0 0 1 0 0 0 0 0 0 0 0 0 14.5209 -1.2305 0.7151 C 0 0 2 0 0 0 0 0 0 0 0 0 14.9536 -2.5625 0.1117 C 0 0 1 0 0 0 0 0 0 0 0 0 13.6634 -3.3506 -0.1188 C 0 0 1 0 0 0 0 0 0 0 0 0 13.9600 -4.8057 0.2812 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9638 -5.3574 -0.4869 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6493 -2.9348 0.7316 O 0 0 0 0 0 0 0 0 0 0 0 0 15.7063 -2.4149 -1.0333 O 0 0 0 0 0 0 0 0 0 0 0 0 14.1031 -1.5140 2.0186 O 0 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0 0 0 -13.1384 0.7154 0.9618 O 0 0 0 0 0 0 0 0 0 0 0 0 -16.3268 1.2660 -0.4583 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.9065 -1.2721 1.5706 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.2933 -0.2623 -1.7660 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3553 -2.4421 -1.9029 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2431 -4.9999 -1.0520 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4456 -5.0866 0.6031 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2545 -4.8684 0.4156 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2716 -2.9627 -0.7875 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1930 -3.2209 -0.2474 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6125 -0.3395 -0.7728 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4865 0.4308 1.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7137 -1.0456 1.9138 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2488 -0.5117 1.0137 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2851 1.3463 -0.3072 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9825 0.0120 -2.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9655 -0.1962 -2.6993 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2664 -0.7780 -3.8139 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5034 -2.5825 -0.2201 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7926 -2.7416 0.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 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0 0 0 0 0 0 0 0 9.0319 1.5091 0.8471 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3079 -0.3299 -1.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4124 -0.7427 1.7121 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5642 -2.1321 0.6320 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5780 -1.9336 -0.6234 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1827 0.2679 -0.1229 H 0 0 0 0 0 0 0 0 0 0 0 0 15.3078 -0.4778 0.7358 H 0 0 0 0 0 0 0 0 0 0 0 0 15.5454 -3.0790 0.9228 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4035 -3.3788 -1.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3303 -4.7303 1.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0307 -5.3797 0.3015 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5885 -5.6896 -1.3392 H 0 0 0 0 0 0 0 0 0 0 0 0 16.6371 -2.2031 -0.7794 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6157 -1.0611 2.7066 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5144 -0.5215 -1.6975 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6513 1.9666 0.7468 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2936 3.8425 -1.4703 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0539 0.0022 -3.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9013 0.4191 1.3617 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9068 -0.3974 2.6747 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2226 -1.3162 1.9604 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3565 -2.9899 0.9168 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3761 -1.9251 2.4406 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1472 -3.0220 2.9892 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6401 2.1317 -2.7395 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3398 2.0511 -1.3960 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1046 -1.6890 2.7752 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2268 0.4071 -0.8163 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 -1.9582 -0.6494 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.0215 -1.1688 -0.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.9248 0.9757 1.5309 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9063 1.9126 -0.5538 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5207 2.3591 2.4326 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2952 3.2434 1.4964 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9042 4.0121 0.1140 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.9504 1.9798 -1.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.7087 -2.2286 1.3679 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.0167 -0.8011 -2.5418 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7366 -1.7052 -2.1470 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 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 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 32 34 1 0 32 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 1 37 42 1 6 42 43 2 0 42 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 56 59 1 0 55 60 1 0 54 61 1 0 53 62 1 0 49 63 1 0 48 64 1 0 47 65 1 0 46 66 1 0 21 67 1 0 67 68 1 1 67 69 1 0 69 70 1 0 11 71 1 0 10 72 1 0 5 73 1 0 4 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 80 81 1 0 79 82 1 0 78 83 1 0 77 84 1 0 76 85 1 0 3 86 1 0 7 2 1 0 14 9 1 0 67 16 1 0 82 75 1 0 26 19 1 0 40 29 1 0 63 45 1 0 40 24 1 0 59 52 1 0 37 30 1 0 1 87 1 0 1 88 1 0 1 89 1 0 2 90 1 6 3 91 1 6 4 92 1 6 5 93 1 6 6 94 1 1 9 95 1 1 10 96 1 1 11 97 1 1 12 98 1 0 12 99 1 0 14100 1 1 16101 1 1 17102 1 0 17103 1 0 18104 1 0 18105 1 0 20106 1 0 20107 1 0 20108 1 0 21109 1 0 22110 1 0 22111 1 0 23112 1 0 23113 1 0 25114 1 0 25115 1 0 25116 1 0 26117 1 0 27118 1 0 27119 1 0 28120 1 0 30121 1 0 31122 1 0 31123 1 0 33124 1 0 33125 1 0 33126 1 0 34127 1 0 34128 1 0 34129 1 0 35130 1 0 35131 1 0 36132 1 0 36133 1 0 38134 1 0 38135 1 0 39136 1 0 39137 1 0 41138 1 0 41139 1 0 41140 1 0 45141 1 6 46142 1 6 47143 1 6 48144 1 1 49145 1 6 50146 1 0 50147 1 0 52148 1 6 53149 1 6 54150 1 1 55151 1 1 56152 1 6 57153 1 0 57154 1 0 58155 1 0 60156 1 0 61157 1 0 62158 1 0 64159 1 0 65160 1 0 66161 1 0 68162 1 0 68163 1 0 68164 1 0 69165 1 0 69166 1 0 70167 1 0 71168 1 0 72169 1 0 73170 1 0 75171 1 6 76172 1 6 77173 1 6 78174 1 1 79175 1 6 80176 1 0 80177 1 0 81178 1 0 83179 1 0 84180 1 0 85181 1 0 86182 1 0 M END

Standard InCHIKey	VUEGHZSQVJADCO-LDNGJIBLSA-N
Standard InCHI	InChI=1S/C59H96O27/c1-24-34(64)46(84-49-43(73)40(70)37(67)29(20-61)81-49)45(75)51(79-24)85-47-35(65)27(63)21-77-52(47)83-33-11-12-55(4)31(56(33,5)23-62)10-13-58(7)32(55)9-8-25-26-18-54(2,3)14-16-59(26,17-15-57(25,58)6)53(76)86-50-44(74)41(71)38(68)30(82-50)22-78-48-42(72)39(69)36(66)28(19-60)80-48/h8,24,26-52,60-75H,9-23H2,1-7H3/t24-,26?,27-,28+,29+,30+,31?,32?,33-,34-,35-,36+,37+,38+,39-,40-,41-,42+,43+,44+,45+,46+,47+,48+,49-,50-,51-,52-,55-,56-,57+,58+,59-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](CO[C@H]1O[C@H]1CC[C@@]2(C)C(CC[C@]3(C)C2CC=C2C4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O2)O)O)O)[C@]1(C)CO)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1236.61	Volume:	1175.518 ? Van der Waals volume.
Dense:	1.052	LogP:	0.602 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.648 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.211 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	57.0
TPSA:	433.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	27.0
H-Bond Donor:	16.0	Rings:	10.0
Heavy Atoms:	27.0

MedChem Properties

QED Drug-Likeness Score:	0.045	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.28	Fsp³:	0.949
MCE-18:	217.043 ? 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:	0.691	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.065 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.264	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.268	MDCK Permeability:	-4.955
Pgp-inhibitor:	0.0	Pgp-substrate:	0.071
PAMPA:	1.0 ? 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):	0.508
20% Bioavailability (F20%):	0.047	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.573	MRP1:	0.007
Plasma Protein Binding (PPB):	61.724%	Volume Distribution (VD):	-0.277
Fu:	19.614% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.328
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):

-1.086

Half-life (T1/2):

5.51

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.004
Human Hepatotoxicity (H-HT):	0.808	Drug-induced Liver Injury (DILI):	0.868
AMES Toxicity:	0.941	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.008	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.113	Drug-induced Nephrotoxicity:	0.971
Genotoxicity:	0.063	RPMI-8226 Immunitoxicity:	0.327
A549 Cytotoxicity:	0.968	Hek293 Cytotoxicity:	0.788
BCF:	1.398 ? 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:	3.724 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.243 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.3 ? 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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[22822669]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	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 NPC87425 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	23891
0.1-0.2	21761
0.2-0.3	2893
0.3-0.4	730
0.4-0.5	310
0.5-0.6	92
0.6-0.7	69
0.7-0.8	0
0.8-0.85	9
0.85-0.9	7
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9223	High Similarity	NPC79643
0.9	High Similarity	NPC298034
0.9	High Similarity	NPC71065
0.8868	High Similarity	NPC123199
0.8818	High Similarity	NPC293330
0.8713	High Similarity	NPC475504
0.8571	High Similarity	NPC202828
0.8571	High Similarity	NPC119592
0.8559	High Similarity	NPC41061
0.8559	High Similarity	NPC227551
0.8407	Intermediate Similarity	NPC305981
0.8333	Intermediate Similarity	NPC261506
0.8333	Intermediate Similarity	NPC4328
0.8319	Intermediate Similarity	NPC65105
0.8302	Intermediate Similarity	NPC481078
0.8252	Intermediate Similarity	NPC63159
0.8073	Intermediate Similarity	NPC76972
0.8073	Intermediate Similarity	NPC469782
0.8073	Intermediate Similarity	NPC204414
0.7931	Intermediate Similarity	NPC236638
0.7931	Intermediate Similarity	NPC294453
0.7778	Intermediate Similarity	NPC481081
0.7767	Intermediate Similarity	NPC295371
0.7699	Intermediate Similarity	NPC135904
0.7692	Intermediate Similarity	NPC43550
0.7667	Intermediate Similarity	NPC250247
0.7619	Intermediate Similarity	NPC112352
0.75	Intermediate Similarity	NPC481080
0.7434	Intermediate Similarity	NPC60557
0.7434	Intermediate Similarity	NPC475287
0.7434	Intermediate Similarity	NPC67857
0.7328	Intermediate Similarity	NPC100639
0.7212	Intermediate Similarity	NPC48499
0.7154	Intermediate Similarity	NPC220160
0.7094	Intermediate Similarity	NPC155410
0.708	Intermediate Similarity	NPC241909
0.7064	Intermediate Similarity	NPC309714
0.7009	Intermediate Similarity	NPC150400
0.7	Intermediate Similarity	NPC473459
0.6957	Remote Similarity	NPC469775
0.6942	Remote Similarity	NPC110633
0.6929	Remote Similarity	NPC469774
0.6923	Remote Similarity	NPC469777
0.6891	Remote Similarity	NPC471550
0.6852	Remote Similarity	NPC473373
0.6842	Remote Similarity	NPC481079
0.6792	Remote Similarity	NPC29069
0.6783	Remote Similarity	NPC100925
0.6781	Remote Similarity	NPC469772
0.678	Remote Similarity	NPC192600
0.6754	Remote Similarity	NPC276093
0.675	Remote Similarity	NPC475160
0.675	Remote Similarity	NPC473714
0.6727	Remote Similarity	NPC469946
0.6721	Remote Similarity	NPC476068
0.6689	Remote Similarity	NPC469773
0.6667	Remote Similarity	NPC219180
0.664	Remote Similarity	NPC136768
0.6612	Remote Similarity	NPC470218
0.6612	Remote Similarity	NPC191827
0.6557	Remote Similarity	NPC488560
0.6549	Remote Similarity	NPC480475
0.6535	Remote Similarity	NPC70809
0.6528	Remote Similarity	NPC469778
0.6518	Remote Similarity	NPC223301
0.6518	Remote Similarity	NPC171544
0.6496	Remote Similarity	NPC295823
0.6496	Remote Similarity	NPC174720
0.6496	Remote Similarity	NPC475467
0.648	Remote Similarity	NPC258617
0.6479	Remote Similarity	NPC469776
0.6466	Remote Similarity	NPC104372
0.6458	Remote Similarity	NPC32723
0.6455	Remote Similarity	NPC475516
0.6446	Remote Similarity	NPC323341
0.6446	Remote Similarity	NPC165204
0.6435	Remote Similarity	NPC297263
0.6414	Remote Similarity	NPC481323
0.6404	Remote Similarity	NPC46665
0.6357	Remote Similarity	NPC224381
0.6333	Remote Similarity	NPC295941
0.6327	Remote Similarity	NPC135334
0.632	Remote Similarity	NPC57484
0.6316	Remote Similarity	NPC160415
0.6311	Remote Similarity	NPC133818
0.6303	Remote Similarity	NPC31838
0.6293	Remote Similarity	NPC222580
0.6293	Remote Similarity	NPC609763
0.6284	Remote Similarity	NPC481324
0.6283	Remote Similarity	NPC473343
0.6271	Remote Similarity	NPC301449
0.6271	Remote Similarity	NPC324875
0.6271	Remote Similarity	NPC292677
0.6271	Remote Similarity	NPC601290
0.6261	Remote Similarity	NPC251768
0.6261	Remote Similarity	NPC102439
0.625	Remote Similarity	NPC75287
0.6174	Remote Similarity	NPC104071
0.6165	Remote Similarity	NPC480422
0.6087	Remote Similarity	NPC192791
0.6083	Remote Similarity	NPC187618
0.6083	Remote Similarity	NPC480474
0.6053	Remote Similarity	NPC473884
0.605	Remote Similarity	NPC114484
0.6047	Remote Similarity	NPC471385
0.6047	Remote Similarity	NPC161717
0.6033	Remote Similarity	NPC187290
0.6	Remote Similarity	NPC166422
0.5983	Remote Similarity	NPC10607
0.5983	Remote Similarity	NPC159309
0.5983	Remote Similarity	NPC86222
0.5963	Remote Similarity	NPC256798
0.595	Remote Similarity	NPC480473
0.595	Remote Similarity	NPC80986
0.5946	Remote Similarity	NPC90856
0.5946	Remote Similarity	NPC214484
0.5943	Remote Similarity	NPC237503
0.5932	Remote Similarity	NPC475591
0.5932	Remote Similarity	NPC236870
0.592	Remote Similarity	NPC475899
0.5913	Remote Similarity	NPC39211
0.5905	Remote Similarity	NPC167383
0.5902	Remote Similarity	NPC475486
0.5897	Remote Similarity	NPC109588
0.5891	Remote Similarity	NPC480418
0.5877	Remote Similarity	NPC139894
0.5877	Remote Similarity	NPC59804
0.5873	Remote Similarity	NPC251263
0.5847	Remote Similarity	NPC164389
0.582	Remote Similarity	NPC69811
0.5814	Remote Similarity	NPC21691
0.5804	Remote Similarity	NPC189884
0.5804	Remote Similarity	NPC138334
0.5794	Remote Similarity	NPC471384
0.5769	Remote Similarity	NPC473452
0.5763	Remote Similarity	NPC30735
0.576	Remote Similarity	NPC313110
0.5758	Remote Similarity	NPC135849
0.5748	Remote Similarity	NPC480419
0.5739	Remote Similarity	NPC235405
0.5736	Remote Similarity	NPC4749
0.5725	Remote Similarity	NPC475514
0.5702	Remote Similarity	NPC486563
0.569	Remote Similarity	NPC249848
0.569	Remote Similarity	NPC107966
0.5667	Remote Similarity	NPC148417
0.5667	Remote Similarity	NPC139044
0.5667	Remote Similarity	NPC235438
0.5652	Remote Similarity	NPC33012
0.5625	Remote Similarity	NPC209894
0.562	Remote Similarity	NPC481082
0.562	Remote Similarity	NPC164419
0.561	Remote Similarity	NPC486564
0.561	Remote Similarity	NPC218954
0.5603	Remote Similarity	NPC174679
0.5603	Remote Similarity	NPC279554
0.5597	Remote Similarity	NPC302543
0.5593	Remote Similarity	NPC263756
0.5593	Remote Similarity	NPC213674
0.5583	Remote Similarity	NPC488526
0.5583	Remote Similarity	NPC173859
0.5583	Remote Similarity	NPC305267
0.5583	Remote Similarity	NPC148603
0.5581	Remote Similarity	NPC283417
0.5581	Remote Similarity	NPC200049
0.558	Remote Similarity	NPC8524
0.5556	Remote Similarity	NPC173583
0.5556	Remote Similarity	NPC472268
0.5547	Remote Similarity	NPC480417
0.5547	Remote Similarity	NPC470911
0.5538	Remote Similarity	NPC54636
0.5532	Remote Similarity	NPC475368
0.553	Remote Similarity	NPC13998
0.5508	Remote Similarity	NPC470512
0.5508	Remote Similarity	NPC157868
0.5496	Remote Similarity	NPC85154
0.5486	Remote Similarity	NPC297950
0.5462	Remote Similarity	NPC471547
0.5462	Remote Similarity	NPC161674
0.5455	Remote Similarity	NPC40775
0.544	Remote Similarity	NPC96641
0.544	Remote Similarity	NPC163183
0.5435	Remote Similarity	NPC102505
0.5435	Remote Similarity	NPC488514
0.5431	Remote Similarity	NPC475208
0.5429	Remote Similarity	NPC477464
0.5424	Remote Similarity	NPC127056
0.5417	Remote Similarity	NPC242840
0.5403	Remote Similarity	NPC281148
0.5398	Remote Similarity	NPC128925
0.5397	Remote Similarity	NPC104137
0.5397	Remote Similarity	NPC26626
0.5385	Remote Similarity	NPC136877
0.5372	Remote Similarity	NPC471548
0.5328	Remote Similarity	NPC473401
0.5328	Remote Similarity	NPC11551
0.5324	Remote Similarity	NPC68767
0.5312	Remote Similarity	NPC476992
0.5299	Remote Similarity	NPC179434
0.5299	Remote Similarity	NPC286457

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC87425 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7617
0.1-0.2	1476
0.2-0.3	50
0.3-0.4	7
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