NPASS Compound

Natural Product: NPC211965

Natural Product ID	NPC211965
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XJFLVHACNKUYQE-RTTGRMBWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24775610
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

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 139146 0 0 0 0 0 0 0 0999 V2000 -13.8234 2.7738 0.4135 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9344 1.3982 0.9711 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0663 0.3248 0.7057 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5696 -0.7070 1.4337 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.6940 -0.2686 2.1064 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.8573 0.9696 1.7972 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8688 0.4401 -0.1940 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.3391 0.7648 -1.6179 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0322 1.5578 0.3556 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5666 1.4384 0.2250 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0236 0.0478 0.3665 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7273 -0.9097 -0.5732 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1906 -2.2876 -0.4228 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8307 -2.3635 0.1900 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0684 -1.3298 0.3876 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7243 -1.4604 1.0010 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8157 -0.4378 0.4221 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3000 0.9645 0.4248 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7579 1.0655 0.7445 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5692 0.0342 -0.0119 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4219 0.1365 -1.5069 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5501 1.7785 1.2963 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2603 -0.8240 -0.7962 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9029 -1.0111 -0.8015 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6083 -2.4500 -1.1443 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1728 -2.7383 -0.7480 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3532 -1.5269 -1.0411 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0245 -0.6440 -2.0863 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0156 -1.3626 -3.4065 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2354 -0.1714 -1.6787 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0550 -0.7487 0.0662 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -0.5003 0.2499 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5712 0.9804 0.3805 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0052 1.2257 0.6667 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7805 0.0833 1.2500 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0141 -1.1176 1.6411 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3641 -2.3663 0.8153 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6291 -0.9987 1.5331 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9182 -0.1903 0.4548 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1091 0.1371 1.0411 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0791 -1.0032 1.2250 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3264 -0.8931 0.3945 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9399 0.4785 0.3530 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9843 1.4498 0.9580 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3121 2.9042 0.6188 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2971 3.0197 -0.7721 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7288 1.2252 0.4040 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2129 0.5485 0.8935 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2024 0.8691 -0.0527 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8551 2.2029 0.2153 C 0 0 1 0 0 0 0 0 0 0 0 0 13.3443 2.1623 -0.0646 C 0 0 2 0 0 0 0 0 0 0 0 0 13.6584 1.2560 -1.2316 C 0 0 1 0 0 0 0 0 0 0 0 0 13.0265 -0.0924 -1.1403 C 0 0 1 0 0 0 0 0 0 0 0 0 14.0633 -1.2012 -1.0405 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4853 -2.4419 -1.1310 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0876 -0.1666 -0.1513 O 0 0 0 0 0 0 0 0 0 0 0 0 13.1960 1.9126 -2.3703 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9954 1.6713 1.0611 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3555 3.1922 -0.6322 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1180 -1.4231 -0.9013 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4880 -1.1391 2.5703 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7151 1.6764 -0.4486 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1459 2.9853 -0.3652 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0794 -3.1053 0.5932 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6493 -4.3960 0.7866 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1799 -0.8454 -0.2739 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7648 -1.8920 -0.1031 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.6565 2.8189 -0.6609 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.8259 3.2774 0.5727 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1280 3.4173 1.0195 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2070 -1.7161 1.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.3082 -0.8730 2.7662 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4405 0.6796 -1.7087 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9339 1.7494 -1.9344 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9265 0.0357 -2.3627 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3683 1.8238 1.3944 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3359 2.4731 -0.2417 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2030 1.9672 -0.6785 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1145 2.0243 1.0822 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2110 -0.2908 1.3951 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6283 -0.5761 -1.6333 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0889 -2.7421 -1.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9041 -2.9783 0.1084 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5233 -3.3903 0.4650 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8539 -1.2111 2.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3653 -2.4834 0.9558 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9048 -0.4280 1.1104 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1904 1.4585 -0.5822 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9213 0.8420 1.8292 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1531 2.0712 0.5229 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4368 0.4748 -1.8497 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1636 0.8116 -1.9827 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5704 -0.8915 -1.9567 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5848 1.6797 1.0780 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5170 -0.8053 0.2172 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8164 -2.6981 -2.1875 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3200 -3.0589 -0.5196 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8597 -3.6285 -1.3424 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6025 -1.8306 -1.5095 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3279 0.2383 -2.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2522 -0.9495 -4.1211 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7176 -2.4465 -3.3074 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9976 -1.2779 -3.9376 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9554 -0.9324 -0.5161 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1760 1.5390 -0.4919 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 1.3259 1.2424 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0170 2.1304 1.3554 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2354 0.4983 2.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2102 -1.4333 2.6946 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2468 -2.8866 1.2346 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5336 -3.0884 0.7884 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6161 -2.1069 -0.2320 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8910 0.5310 2.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6166 -1.9855 0.9713 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0878 -1.5762 0.8484 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0551 0.7262 -0.7316 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9704 1.4120 2.0646 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4255 3.4966 0.9788 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2284 3.2606 1.0931 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0136 3.9486 -1.0098 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6748 0.9762 -1.0224 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6183 2.5213 1.2502 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6864 3.1941 -0.2323 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7678 1.1766 -1.3671 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4970 -0.2889 -2.1106 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7688 -1.0812 -1.8896 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6937 -1.0661 -0.1149 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7776 -2.9200 -1.9625 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6475 2.8090 -2.3901 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3560 1.2587 1.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2563 4.0678 -0.2162 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0094 -1.4792 -1.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7374 -2.0850 2.7628 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8223 3.2056 0.4745 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2835 3.7147 -0.4032 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7161 3.1827 -1.2981 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3267 -5.1304 0.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7133 -4.5801 1.8955 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 -4.5623 0.5150 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 3 7 1 0 7 8 1 6 7 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 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 18 22 1 0 17 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 27 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 36 38 1 0 35 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 45 46 1 0 44 47 1 0 43 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 53 56 1 0 52 57 1 0 51 58 1 0 50 59 1 0 42 60 1 0 41 61 1 0 34 62 1 0 62 63 1 0 26 64 1 0 64 65 1 0 12 66 1 0 66 67 2 0 6 2 1 0 66 7 1 0 20 11 1 0 30 24 1 0 38 32 1 0 47 40 1 0 56 49 1 0 20 15 1 0 1 68 1 0 1 69 1 0 1 70 1 0 4 71 1 0 5 72 1 0 8 73 1 0 8 74 1 0 8 75 1 0 9 76 1 0 9 77 1 0 10 78 1 0 10 79 1 0 11 80 1 1 12 81 1 6 13 82 1 0 13 83 1 0 14 84 1 0 16 85 1 0 16 86 1 0 17 87 1 1 18 88 1 6 19 89 1 0 19 90 1 0 21 91 1 0 21 92 1 0 21 93 1 0 22 94 1 0 24 95 1 1 25 96 1 0 25 97 1 0 26 98 1 6 27 99 1 6 28100 1 6 29101 1 0 29102 1 0 29103 1 0 32104 1 6 33105 1 0 33106 1 0 34107 1 1 35108 1 1 36109 1 1 37110 1 0 37111 1 0 37112 1 0 40113 1 1 41114 1 6 42115 1 1 43116 1 6 44117 1 1 45118 1 0 45119 1 0 46120 1 0 49121 1 6 50122 1 1 51123 1 6 52124 1 6 53125 1 6 54126 1 0 54127 1 0 55128 1 0 57129 1 0 58130 1 0 59131 1 0 60132 1 0 61133 1 0 63134 1 0 63135 1 0 63136 1 0 65137 1 0 65138 1 0 65139 1 0 M END

Standard InCHIKey	XJFLVHACNKUYQE-RTTGRMBWSA-N
Standard InCHI	InChI=1S/C47H72O20/c1-20-25(11-13-59-20)46(4)12-10-26-24(43(46)56)9-8-23-14-28(27(50)17-47(23,26)5)62-33-15-29(57-6)40(21(2)60-33)65-34-16-30(58-7)41(22(3)61-34)66-45-39(55)37(53)42(32(19-49)64-45)67-44-38(54)36(52)35(51)31(18-48)63-44/h8,11,13,21-22,24,26-42,44-45,48-55H,9-10,12,14-19H2,1-7H3/t21-,22+,24-,26+,27-,28-,29+,30+,31-,32-,33+,34+,35-,36+,37-,38-,39-,40-,41-,42-,44+,45+,46-,47+/m1/s1
SMILES	Cc1c(cco1)[C@@]1(C)CC[C@H]2[C@@H](CC=C3C[C@H]([C@@H](C[C@]23C)O)O[C@H]2C[C@@H]([C@@H]([C@@H](C)O2)O[C@H]2C[C@@H]([C@@H]([C@H](C)O2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O)OC)OC)C1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	956.46	Volume:	918.275 ? Van der Waals volume.
Dense:	1.042	LogP:	0.6 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.301 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.717 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	46.0
TPSA:	284.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	8.0	Rings:	8.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.121	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.551	Fsp³:	0.851
MCE-18:	207.908 ? 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:	0.625	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.262	Promiscuous compounds:	0.048

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.932	MDCK Permeability:	-5.346
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
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):	0.0
20% Bioavailability (F20%):	0.009	30% Bioavailability (F30%):	0.263
50% Bioavailability (F50%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.707
Plasma Protein Binding (PPB):	73.479%	Volume Distribution (VD):	-0.358
Fu:	22.717% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.896	BCRP inhibitor:	0.009
BSEP inhibitor:	0.634

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	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:	0.02
CYP3A4-inhibitor:	0.76	CYP3A4-substrate:	0.725
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.021
HLM stability:	0.006 ? 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):

0.719

Half-life (T1/2):

4.205

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.009
Human Hepatotoxicity (H-HT):	0.822	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.99	Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.148	Skin Sensitization:	1.0
Carcinogencity:	0.611	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.778	Drug-induced Nephrotoxicity:	0.949
Genotoxicity:	0.899	RPMI-8226 Immunitoxicity:	0.32
A549 Cytotoxicity:	0.957	Hek293 Cytotoxicity:	0.733
BCF:	0.623 ? 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:	3.202 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.714 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.808 ? 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
NPO27831	Phakellia flabellata	Species	Bubaridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00445a028]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11374953]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15056914]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270557]
NPO27850	Trichilia catigua	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[18020420]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19948405]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20415462]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23672042]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24024763]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36483735]
NPO28333	Syzygium levinei	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38005226]
NPO28214	Phyllosticta cirsii	Species	Phyllostictaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28176	Russula lepida	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28158	Polygala fruticosa	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28494	Hydroclathrus tenuis	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28525	Urginea riparia	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28425	Senecio miser	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28543	Alcyonium coralloides	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28507	Hymenoxys grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28228	Kielmeyera rubriflora	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27850	Trichilia catigua	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29373	Trichoplusia ni	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27918	Pterocarpus macrocarpus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27973	Simaba cuneata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28158	Polygala fruticosa	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28300	Sorbaria arborea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28176	Russula lepida	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28507	Hymenoxys grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28158	Polygala fruticosa	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28300	Sorbaria arborea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28300	Sorbaria arborea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27938	Meliosma wightii	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11786	Cylindropuntia leptocaulis	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28228	Kielmeyera rubriflora	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28443	Larix lyallii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28300	Sorbaria arborea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28651	Othonna tagetes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28333	Syzygium levinei	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27850	Trichilia catigua	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28009	Pellina semitubulosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27891	Lethariella sinensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28593	Pteris pedata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27956	Eupatoriastrum nelsonii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27973	Simaba cuneata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28176	Russula lepida	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28404	Chasmanthera dependens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28461	Crepis czerepanovii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29373	Trichoplusia ni	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28479	Campanula hypopolia	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28158	Polygala fruticosa	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28494	Hydroclathrus tenuis	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28425	Senecio miser	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28214	Phyllosticta cirsii	Species	Phyllostictaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27906	Philadelphus coronarius	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25330	Maackia floribunda	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28668	Agave cocui	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28611	Phragmatobia fuliginosa	Species	Erebidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28525	Urginea riparia	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27918	Pterocarpus macrocarpus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28316	Scandix pecten-veneris	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9245	Ventilago madraspatana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27831	Phakellia flabellata	Species	Bubaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28071	Dendrobates auratus	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28282	Turbina corymbosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28507	Hymenoxys grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10135	Tripteris microcarpa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28543	Alcyonium coralloides	Species	Alcyoniidae	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 NPC211965 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	11907
0.1-0.2	33878
0.2-0.3	3856
0.3-0.4	211
0.4-0.5	7
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC211965 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4299
0.1-0.2	4760
0.2-0.3	89
0.3-0.4	2
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