NPASS Compound

Natural Product: NPC489208

Natural Product ID	NPC489208
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QLIPSXKNJSLGQL-IXKPUDRESA-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: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 206216 0 0 0 0 0 0 0 0999 V2000 -7.9805 -0.2020 -1.6439 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6898 0.8785 -0.8805 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7016 0.2740 0.0935 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7989 1.2160 1.2478 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4813 0.9820 2.0519 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3711 1.1701 1.0191 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8337 1.7008 -0.1749 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4324 2.0965 1.5363 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2646 1.4166 1.7877 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2070 1.3110 3.3359 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1476 2.7470 3.8207 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0084 3.4686 3.1205 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2472 2.5751 2.3659 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0124 2.0483 1.2802 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2116 1.0608 0.6585 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6381 1.2020 -0.5775 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8215 2.2615 -1.2088 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7755 0.0774 -1.1735 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8067 -0.8834 -1.6525 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3730 -1.7186 -0.5749 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3038 -2.5680 0.0594 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0401 -3.7373 -0.8677 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9798 -3.1959 1.2909 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0628 -1.8312 0.4005 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9227 -0.4452 -0.0395 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4412 0.0491 -0.3305 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0053 0.8642 0.5155 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3704 1.4309 0.3346 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1374 0.2540 -0.2061 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6056 0.3328 0.0204 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1955 1.5459 -0.5555 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9294 0.3612 1.5116 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4040 0.4351 1.7516 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2685 -0.3681 0.8097 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4885 -1.3907 0.1117 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3768 -2.5800 1.1083 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2951 -1.9869 -1.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1616 -0.9954 -0.4084 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9228 -1.1075 -1.8739 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4213 -1.2720 -2.0397 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6364 -0.0399 -1.5674 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9285 0.9719 -2.6250 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1554 -0.3174 -1.5583 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9392 -1.7069 -2.0641 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3551 0.5078 -2.5981 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0678 0.7099 -2.2968 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7893 0.3446 -3.4809 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9703 0.3891 -0.0860 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3332 0.4628 0.1599 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0745 0.0519 -1.0791 C 0 0 1 0 0 0 0 0 0 0 0 0 11.0874 1.1353 -1.4944 C 0 0 2 0 0 0 0 0 0 0 0 0 11.8159 1.5580 -0.2701 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8287 2.1496 0.7086 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9833 3.6522 0.6715 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2949 4.0412 0.9307 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5349 1.8273 0.4488 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4570 0.4785 0.3013 O 0 0 0 0 0 0 0 0 0 0 0 0 13.8469 0.7194 0.3388 C 0 0 1 0 0 0 0 0 0 0 0 0 14.1974 0.7414 1.8307 C 0 0 1 0 0 0 0 0 0 0 0 0 13.8741 -0.6322 2.3732 C 0 0 2 0 0 0 0 0 0 0 0 0 14.8271 -1.6036 1.7035 C 0 0 1 0 0 0 0 0 0 0 0 0 15.3800 -1.0302 0.4183 C 0 0 1 0 0 0 0 0 0 0 0 0 15.8208 -2.2192 -0.4294 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7550 -3.0270 -0.7442 O 0 0 0 0 0 0 0 0 0 0 0 0 14.4636 -0.3255 -0.3208 O 0 0 0 0 0 0 0 0 0 0 0 0 15.8825 -1.7961 2.5785 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5847 -0.9606 1.9557 O 0 0 0 0 0 0 0 0 0 0 0 0 15.4874 1.1464 2.0738 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3392 2.1956 -2.0107 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7855 -1.1938 -0.9100 N 0 0 0 0 0 0 0 0 0 0 0 0 10.8970 -2.0094 -1.8733 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6511 -3.2896 -1.6239 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3703 -1.8058 -3.1516 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0953 2.8409 5.1899 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1438 0.5412 3.7365 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5281 -0.3432 2.4581 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8051 1.0018 2.1461 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3980 2.2302 2.4611 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.8648 2.2928 2.1676 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.3603 3.6955 2.4285 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.8462 4.2250 3.7210 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.3706 3.9274 3.9263 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1556 2.5383 3.8114 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9973 5.5980 3.7448 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.7569 3.7069 2.4670 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9923 1.9920 0.7871 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9014 0.1494 -0.5564 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2378 -1.2003 -0.7663 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.5709 -1.4788 -0.1734 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.4435 -1.7869 -1.4410 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.6673 -0.9805 -2.4177 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.9395 -1.2026 -3.8395 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8871 -2.4933 -4.2869 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.7731 -3.5189 -4.1345 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.8466 -3.3427 -3.5226 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.4508 -4.8734 -4.7091 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3328 -1.3699 -2.1215 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.7150 -1.3461 -1.2019 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.5006 -2.6293 0.6136 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0021 0.1437 -2.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7692 -1.0985 -1.0143 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5816 -0.4665 -2.5294 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2672 1.5013 -1.5876 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2563 -0.7195 0.3606 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7292 2.2752 0.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4148 1.6538 2.9020 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8701 0.2013 0.9295 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2985 0.3304 1.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1448 0.8151 3.6245 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0820 3.2416 3.4880 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3324 3.8448 3.9124 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3513 4.3056 2.5136 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1840 2.8732 0.5902 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4328 -1.5392 -2.4639 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6492 -0.3058 -2.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9087 -1.1992 0.2158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1108 -2.4363 -1.0401 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9832 -3.4502 -1.9357 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9128 -4.4503 -0.7638 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1692 -4.3325 -0.5223 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -4.1853 1.5278 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8668 -2.4569 2.1088 H 0 0 0 0 0 0 0 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1.8410 1.7506 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3478 4.1763 1.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7241 4.0786 -0.3221 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3864 4.9481 1.2670 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0704 1.7058 -0.1206 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4468 1.4492 2.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9372 -0.6867 3.4771 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3688 -2.5850 1.4850 H 0 0 0 0 0 0 0 0 0 0 0 0 16.3228 -0.4552 0.6089 H 0 0 0 0 0 0 0 0 0 0 0 0 16.2996 -1.8024 -1.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 16.6295 -2.8021 0.0868 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8405 -3.3900 -1.6782 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6915 -2.4353 3.2937 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3365 -1.8907 2.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 15.7447 1.8120 1.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9413 1.9921 -2.8837 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0200 -3.3348 -0.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9340 -4.1246 -1.7780 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5093 -3.3031 -2.2925 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3817 -0.8612 -3.5214 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6475 2.0673 5.5677 H 0 0 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92 1 0 92 93 1 0 93 94 1 0 94 95 2 0 94 96 1 0 91 97 1 0 90 98 1 0 89 99 1 0 7 2 1 0 14 9 1 0 25 18 1 0 43 26 1 0 56 49 1 0 65 58 1 0 83 78 1 0 97 88 1 0 46 18 1 0 41 29 1 0 38 30 1 0 1100 1 0 1101 1 0 1102 1 0 2103 1 6 3104 1 1 4105 1 6 5106 1 1 6107 1 6 9108 1 6 10109 1 1 11110 1 6 12111 1 0 12112 1 0 14113 1 6 19114 1 0 19115 1 0 20116 1 0 20117 1 0 22118 1 0 22119 1 0 22120 1 0 23121 1 0 23122 1 0 23123 1 0 24124 1 0 24125 1 0 25126 1 1 27127 1 0 28128 1 0 28129 1 0 29130 1 1 31131 1 0 31132 1 0 31133 1 0 32134 1 0 32135 1 0 33136 1 0 33137 1 0 34138 1 1 36139 1 0 36140 1 0 36141 1 0 37142 1 0 37143 1 0 37144 1 0 38145 1 1 39146 1 0 39147 1 0 40148 1 0 40149 1 0 42150 1 0 42151 1 0 42152 1 0 44153 1 0 44154 1 0 44155 1 0 45156 1 0 45157 1 0 46158 1 1 47159 1 0 49160 1 1 50161 1 6 51162 1 6 52163 1 6 53164 1 1 54165 1 0 54166 1 0 55167 1 0 58168 1 6 59169 1 1 60170 1 1 61171 1 6 62172 1 1 63173 1 0 63174 1 0 64175 1 0 66176 1 0 67177 1 0 68178 1 0 69179 1 0 72180 1 0 72181 1 0 72182 1 0 73183 1 0 74184 1 0 75185 1 0 76186 1 0 78187 1 6 79188 1 1 80189 1 6 81190 1 1 82191 1 0 82192 1 0 84193 1 0 85194 1 0 86195 1 0 88196 1 1 89197 1 1 90198 1 6 91199 1 1 92200 1 0 92201 1 0 96202 1 0 96203 1 0 96204 1 0 98205 1 0 99206 1 0 M END

Standard InCHIKey	QLIPSXKNJSLGQL-IXKPUDRESA-N
Standard InCHI	InChI=1S/C67H107NO31/c1-26-51(95-57-48(83)44(79)35(93-57)25-87-28(3)72)53(97-56-47(82)41(76)31(73)23-88-56)50(85)59(90-26)98-54-42(77)32(74)24-89-60(54)99-61(86)67-18-17-62(4,5)19-30(67)29-11-12-37-64(8)15-14-39(63(6,7)36(64)13-16-65(37,9)66(29,10)20-38(67)75)94-55-40(68-27(2)71)45(80)52(34(22-70)92-55)96-58-49(84)46(81)43(78)33(21-69)91-58/h11,26,30-60,69-70,73-85H,12-25H2,1-10H3,(H,68,71)/t26-,30-,31+,32-,33+,34+,35-,36-,37+,38+,39-,40+,41-,42-,43+,44-,45+,46-,47+,48+,49+,50+,51-,52+,53-,54+,55-,56-,57-,58-,59-,60-,64-,65+,66+,67+/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]1OC(=O)[C@]12CCC(C)(C)C[C@H]1C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)N=C(C)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O[C@H]1[C@@H]([C@H]([C@H](COC(=O)C)O1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1421.68	Volume:	1346.214 ? Van der Waals volume.
Dense:	1.056	LogP:	0.328 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.144 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.495 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	64.0
TPSA:	490.17 ? Topological Polar Surface Area.	H-Bond Acceptor:	32.0
H-Bond Donor:	16.0	Rings:	11.0
Heavy Atoms:	32.0

MedChem Properties

QED Drug-Likeness Score:	0.023	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.944	Fsp³:	0.925
MCE-18:	240.093 ? 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:	0.88	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.119	Promiscuous compounds:	0.108

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.707	MDCK Permeability:	-4.962
Pgp-inhibitor:	0.0	Pgp-substrate:	0.995
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):	0.979
20% Bioavailability (F20%):	0.854	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.009
Plasma Protein Binding (PPB):	57.44%	Volume Distribution (VD):	-0.448
Fu:	24.435% ? 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:	0.15	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.061
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):

-0.854

Half-life (T1/2):

4.089

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.994	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.014	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.892	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.84	RPMI-8226 Immunitoxicity:	0.276
A549 Cytotoxicity:	0.755	Hek293 Cytotoxicity:	0.14
BCF:	0.274 ? 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:	3.437 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.513 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.094 ? 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
NPO40002	Acacia ligulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28976773]

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	2

Activity Type	# Activity
Cell line	2

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
NPT170	Cell line	SK-MEL-28	Homo sapiens	IC50	=	25000.0	nM	PMID[28976773]
NPT859	Cell line	HFF	Homo sapiens	IC50	=	13400.0	nM	PMID[28976773]

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 NPC489208 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	24397
0.1-0.2	21849
0.2-0.3	2457
0.3-0.4	642
0.4-0.5	296
0.5-0.6	154
0.6-0.7	41
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
0.9344	High Similarity	NPC489209
0.7328	Intermediate Similarity	NPC286457
0.728	Intermediate Similarity	NPC104137
0.728	Intermediate Similarity	NPC26626
0.6917	Remote Similarity	NPC85154
0.6889	Remote Similarity	NPC470876
0.6884	Remote Similarity	NPC220160
0.6815	Remote Similarity	NPC473452
0.6767	Remote Similarity	NPC283417
0.6767	Remote Similarity	NPC200049
0.6691	Remote Similarity	NPC13998
0.6667	Remote Similarity	NPC123522
0.6667	Remote Similarity	NPC475584
0.6667	Remote Similarity	NPC475152
0.6587	Remote Similarity	NPC164389
0.6528	Remote Similarity	NPC33012
0.6474	Remote Similarity	NPC113620
0.6458	Remote Similarity	NPC8524
0.6429	Remote Similarity	NPC485563
0.6423	Remote Similarity	NPC4749
0.6408	Remote Similarity	NPC482010
0.6392	Remote Similarity	NPC100612
0.6377	Remote Similarity	NPC57484
0.6352	Remote Similarity	NPC488620
0.6328	Remote Similarity	NPC488526
0.6316	Remote Similarity	NPC815
0.6235	Remote Similarity	NPC265699
0.6225	Remote Similarity	NPC484830
0.6207	Remote Similarity	NPC102505
0.6207	Remote Similarity	NPC488514
0.6205	Remote Similarity	NPC476113
0.6203	Remote Similarity	NPC482013
0.6194	Remote Similarity	NPC210729
0.6194	Remote Similarity	NPC82931
0.6154	Remote Similarity	NPC302543
0.6145	Remote Similarity	NPC174336
0.6143	Remote Similarity	NPC21691
0.6133	Remote Similarity	NPC475177
0.6129	Remote Similarity	NPC1046
0.6118	Remote Similarity	NPC484831
0.6061	Remote Similarity	NPC64715
0.6042	Remote Similarity	NPC309223
0.604	Remote Similarity	NPC480421
0.6038	Remote Similarity	NPC23020
0.6	Remote Similarity	NPC187497
0.5971	Remote Similarity	NPC135904
0.5962	Remote Similarity	NPC233223
0.5962	Remote Similarity	NPC183816
0.5962	Remote Similarity	NPC43589
0.5959	Remote Similarity	NPC142151
0.5946	Remote Similarity	NPC51099
0.5944	Remote Similarity	NPC41061
0.5944	Remote Similarity	NPC227551
0.5938	Remote Similarity	NPC488619
0.5931	Remote Similarity	NPC261506
0.5931	Remote Similarity	NPC4328
0.5929	Remote Similarity	NPC480423
0.5924	Remote Similarity	NPC300655
0.5924	Remote Similarity	NPC13989
0.5924	Remote Similarity	NPC196874
0.5912	Remote Similarity	NPC172365
0.5909	Remote Similarity	NPC63159
0.5897	Remote Similarity	NPC484829
0.5882	Remote Similarity	NPC207738
0.5862	Remote Similarity	NPC236638
0.5862	Remote Similarity	NPC294453
0.5862	Remote Similarity	NPC305981
0.5857	Remote Similarity	NPC123199
0.585	Remote Similarity	NPC267694
0.5839	Remote Similarity	NPC11242
0.5833	Remote Similarity	NPC232237
0.5833	Remote Similarity	NPC475514
0.5813	Remote Similarity	NPC311178
0.5782	Remote Similarity	NPC70809
0.5776	Remote Similarity	NPC222951
0.5776	Remote Similarity	NPC488618
0.5764	Remote Similarity	NPC480418
0.5758	Remote Similarity	NPC322904
0.5755	Remote Similarity	NPC60557
0.5755	Remote Similarity	NPC67857
0.5714	Remote Similarity	NPC488204
0.5714	Remote Similarity	NPC79643
0.5714	Remote Similarity	NPC144644
0.5714	Remote Similarity	NPC170407
0.5705	Remote Similarity	NPC250247
0.5695	Remote Similarity	NPC480422
0.568	Remote Similarity	NPC488201
0.5667	Remote Similarity	NPC68767
0.5658	Remote Similarity	NPC485562
0.5655	Remote Similarity	NPC265841
0.5652	Remote Similarity	NPC481078
0.5646	Remote Similarity	NPC481081
0.5644	Remote Similarity	NPC475444
0.5644	Remote Similarity	NPC473679
0.5643	Remote Similarity	NPC475287
0.5639	Remote Similarity	NPC117714
0.5639	Remote Similarity	NPC30289
0.5636	Remote Similarity	NPC472270
0.5636	Remote Similarity	NPC112492
0.5634	Remote Similarity	NPC475209
0.5625	Remote Similarity	NPC481080
0.5616	Remote Similarity	NPC312650
0.5608	Remote Similarity	NPC37860
0.5563	Remote Similarity	NPC293031
0.5556	Remote Similarity	NPC105800
0.5548	Remote Similarity	NPC488308
0.5536	Remote Similarity	NPC324933
0.5533	Remote Similarity	NPC482011
0.5526	Remote Similarity	NPC153673
0.551	Remote Similarity	NPC271610
0.5507	Remote Similarity	NPC481079
0.5503	Remote Similarity	NPC298034
0.5503	Remote Similarity	NPC71065
0.5503	Remote Similarity	NPC319719
0.55	Remote Similarity	NPC329878
0.5481	Remote Similarity	NPC305267
0.5479	Remote Similarity	NPC473386
0.5461	Remote Similarity	NPC185466
0.5455	Remote Similarity	NPC480420
0.5448	Remote Similarity	NPC112352
0.5436	Remote Similarity	NPC202828
0.5436	Remote Similarity	NPC119592
0.5429	Remote Similarity	NPC187290
0.5425	Remote Similarity	NPC110385
0.5423	Remote Similarity	NPC610204
0.5419	Remote Similarity	NPC275225
0.5405	Remote Similarity	NPC258617
0.5404	Remote Similarity	NPC45606
0.5404	Remote Similarity	NPC475394
0.54	Remote Similarity	NPC482012
0.5396	Remote Similarity	NPC301449
0.5396	Remote Similarity	NPC601290
0.5375	Remote Similarity	NPC329893
0.5373	Remote Similarity	NPC263756
0.5373	Remote Similarity	NPC213674
0.5373	Remote Similarity	NPC469946
0.537	Remote Similarity	NPC220838
0.5369	Remote Similarity	NPC43550
0.5357	Remote Similarity	NPC295823
0.5357	Remote Similarity	NPC174720
0.5357	Remote Similarity	NPC475467
0.5357	Remote Similarity	NPC69811
0.5342	Remote Similarity	NPC471577
0.5338	Remote Similarity	NPC110633
0.5333	Remote Similarity	NPC478559
0.5333	Remote Similarity	NPC478560
0.5329	Remote Similarity	NPC224381
0.5329	Remote Similarity	NPC488309
0.5315	Remote Similarity	NPC76972
0.5315	Remote Similarity	NPC469782
0.5315	Remote Similarity	NPC204414
0.531	Remote Similarity	NPC603137
0.5287	Remote Similarity	NPC475527
0.528	Remote Similarity	NPC472268
0.527	Remote Similarity	NPC237191
0.5252	Remote Similarity	NPC302887
0.5245	Remote Similarity	NPC288205
0.5245	Remote Similarity	NPC51465
0.5241	Remote Similarity	NPC284449
0.5217	Remote Similarity	NPC297950
0.5208	Remote Similarity	NPC200788
0.5205	Remote Similarity	NPC219180
0.52	Remote Similarity	NPC471580
0.5189	Remote Similarity	NPC475649
0.5183	Remote Similarity	NPC475892
0.518	Remote Similarity	NPC297263
0.518	Remote Similarity	NPC488517
0.5175	Remote Similarity	NPC280941
0.5175	Remote Similarity	NPC235772
0.5172	Remote Similarity	NPC488200
0.517	Remote Similarity	NPC470218
0.517	Remote Similarity	NPC475140
0.517	Remote Similarity	NPC602995
0.5166	Remote Similarity	NPC293330
0.5166	Remote Similarity	NPC476779
0.5161	Remote Similarity	NPC480417
0.5148	Remote Similarity	NPC472269
0.5145	Remote Similarity	NPC44716
0.5141	Remote Similarity	NPC160452
0.5139	Remote Similarity	NPC475119
0.5137	Remote Similarity	NPC165204
0.5135	Remote Similarity	NPC25663
0.5135	Remote Similarity	NPC488560
0.5133	Remote Similarity	NPC22709
0.5133	Remote Similarity	NPC476780
0.5132	Remote Similarity	NPC136768
0.5132	Remote Similarity	NPC110700
0.5113	Remote Similarity	NPC48499
0.5105	Remote Similarity	NPC31838
0.5103	Remote Similarity	NPC607904
0.5103	Remote Similarity	NPC610461
0.5102	Remote Similarity	NPC480419
0.5101	Remote Similarity	NPC71391
0.5098	Remote Similarity	NPC476991
0.5068	Remote Similarity	NPC475160
0.5068	Remote Similarity	NPC473714
0.5067	Remote Similarity	NPC470518
0.5066	Remote Similarity	NPC161717
0.5059	Remote Similarity	NPC469776

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC489208 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7241
0.1-0.2	1863
0.2-0.3	43
0.3-0.4	3
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