NPASS Compound

Natural Product: NPC602423

Natural Product ID	NPC602423
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LWMZJBVLZFGRJF-OFEPKVMWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL394746
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 133141 0 0 0 0 0 0 0 0999 V2000 13.0324 0.9552 -1.5605 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9354 -0.0253 -1.1909 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1127 -0.4547 -2.3811 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0851 -1.4533 -1.8184 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1839 -0.6658 -0.9337 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6979 0.4722 -0.4146 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0282 0.5225 -0.1486 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0725 -0.2839 -1.7366 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2637 0.3119 -0.8055 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8114 0.4797 -1.2891 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 -0.1314 -0.1952 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6571 -0.6405 -0.5218 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8657 0.3293 -1.2960 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4178 0.1537 -1.1196 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8294 -0.5715 -0.2242 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6525 -0.6509 -0.1645 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0389 0.1761 1.0405 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3379 -0.0083 1.4866 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1206 1.1191 1.3500 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2839 1.6025 2.6780 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7991 2.8917 2.6597 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4290 3.1463 4.0022 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3839 2.9928 4.9439 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6629 3.2151 1.4928 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9265 3.6765 0.4355 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4381 1.9802 1.0976 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1869 1.4707 2.1190 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5423 1.3691 1.9008 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1214 2.3562 2.7573 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3110 2.7895 2.1720 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9384 3.6540 0.9730 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0500 1.5946 1.6592 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.4395 1.7480 1.7600 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6903 0.3039 2.3631 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3664 -0.7307 1.7034 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1766 0.0823 2.3010 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9672 -0.9365 1.3732 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4083 0.9035 0.6933 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3081 0.9959 -0.6873 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9103 -0.0869 -1.3518 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9475 0.3540 -2.1491 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6933 -0.6018 -2.7686 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7643 -1.1147 -1.8569 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8404 -1.7863 -3.2287 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4035 -2.2535 -4.3930 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4734 -1.2015 -3.5083 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6335 -2.1550 -4.0930 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8709 -0.7624 -2.1987 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3678 -1.9075 -1.5272 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0030 0.0997 2.1327 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8974 -1.0746 2.1061 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5913 -1.3324 0.7782 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3576 -2.8295 0.4984 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0428 -1.0051 0.7930 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8636 -2.1803 1.3266 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3067 -1.8673 1.4315 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8999 -1.3681 0.1189 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7999 -2.3480 -0.9958 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2168 -0.7133 0.3104 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4388 -1.5179 0.0873 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2055 -1.5499 1.4203 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6828 1.0961 -0.6792 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6543 1.9406 -1.8563 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6930 0.5367 -2.3604 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4602 -0.9574 -0.8377 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6877 -0.9694 -3.1599 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5636 0.4070 -2.8303 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5634 -1.8354 -2.7450 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6690 -2.2369 -1.3105 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2976 1.6155 -0.0160 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3387 0.0780 0.8295 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6857 1.2795 -0.4611 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6637 0.1168 -2.3019 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6281 1.5866 -1.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9587 0.5145 0.6749 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7029 -1.5900 -1.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1420 1.4095 -1.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0692 0.1643 -2.3982 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7231 0.6944 -1.8284 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0541 -0.2358 -1.1071 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0497 -1.6785 -0.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9847 1.2449 0.6735 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4974 1.8773 0.7943 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9054 3.5788 2.6086 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2023 2.4045 4.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7702 4.1981 4.1150 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5448 3.4169 4.6107 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3376 4.0457 1.7962 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4379 3.5541 -0.4043 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0844 2.2368 0.2475 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8685 1.6659 0.9064 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9027 3.3777 2.9018 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8415 3.7441 0.8348 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3233 4.6905 1.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3502 3.2589 0.0281 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8558 1.4190 0.5684 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6646 2.7187 1.7109 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0595 0.3858 3.3958 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2944 -0.8123 1.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8305 -0.2297 3.3150 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8006 -1.8043 1.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8702 -0.0939 0.9385 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3393 -0.7747 -0.5795 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1450 -0.1346 -3.6756 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5281 -1.6878 -2.4488 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2997 -0.3060 -1.3261 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3536 -1.8583 -1.1489 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7875 -2.5282 -2.4101 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3027 -2.6404 -4.1860 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5999 -0.3142 -4.1570 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8569 -3.0477 -3.7423 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0290 -0.0863 -2.4617 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8159 -2.4628 -2.1052 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5680 1.0584 2.2682 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6013 0.0129 3.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7318 -0.8591 2.8364 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3848 -1.9641 2.5131 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2671 -2.9900 0.6181 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7070 -3.1209 -0.4908 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7977 -3.4582 1.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2086 -0.1628 1.4970 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5018 -2.4674 2.3398 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6540 -3.0706 0.6811 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4632 -1.0799 2.1800 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8399 -2.7974 1.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5004 -1.8897 -1.9864 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9905 -3.1192 -0.8144 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6859 -2.9396 -1.2234 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1972 -0.2126 1.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3314 -2.5552 -0.1960 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1512 -0.6029 1.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2098 -1.9870 1.2932 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6455 -2.3048 2.0447 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 1 6 7 1 0 5 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 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 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 26 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 46 48 1 0 48 49 1 0 17 50 1 0 50 51 1 0 51 52 1 0 52 53 1 6 52 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 6 57 59 1 0 59 60 1 0 60 61 1 0 7 2 1 0 59 9 1 0 60 5 1 0 57 11 1 0 54 12 1 0 52 15 1 0 38 19 1 0 48 40 1 0 36 28 1 0 1 62 1 0 1 63 1 0 1 64 1 0 2 65 1 1 3 66 1 0 3 67 1 0 4 68 1 0 4 69 1 0 7 70 1 0 7 71 1 0 9 72 1 1 10 73 1 0 10 74 1 0 11 75 1 1 12 76 1 6 13 77 1 0 13 78 1 0 14 79 1 0 16 80 1 0 16 81 1 0 17 82 1 6 19 83 1 6 21 84 1 6 22 85 1 0 22 86 1 0 23 87 1 0 24 88 1 1 25 89 1 0 26 90 1 6 28 91 1 6 30 92 1 1 31 93 1 0 31 94 1 0 31 95 1 0 32 96 1 6 33 97 1 0 34 98 1 1 35 99 1 0 36100 1 1 37101 1 0 38102 1 6 40103 1 1 42104 1 6 43105 1 0 43106 1 0 43107 1 0 44108 1 1 45109 1 0 46110 1 6 47111 1 0 48112 1 6 49113 1 0 50114 1 0 50115 1 0 51116 1 0 51117 1 0 53118 1 0 53119 1 0 53120 1 0 54121 1 1 55122 1 0 55123 1 0 56124 1 0 56125 1 0 58126 1 0 58127 1 0 58128 1 0 59129 1 1 60130 1 6 61131 1 0 61132 1 0 61133 1 0 M END

Standard InCHIKey	LWMZJBVLZFGRJF-OFEPKVMWSA-N
Standard InCHI	InChI=1S/C45H72O16/c1-19-9-14-45(54-18-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-37(53)35(51)32(48)22(4)56-41)38(33(49)29(17-46)58-42)59-40-36(52)34(50)31(47)21(3)55-40/h7,19-22,24-42,46-53H,8-18H2,1-6H3/t19-,20+,21+,22-,24+,25-,26+,27+,28+,29-,30+,31+,32-,33-,34-,35+,36-,37+,38+,39-,40+,41-,42-,43+,44+,45-/m1/s1
SMILES	C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC=C5C[C@@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@H]6O[C@H]6O[C@H](C)[C@@H](O)[C@H](O)[C@@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	868.48	Volume:	847.875 ? Van der Waals volume.
Dense:	1.024	LogP:	3.626 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.899 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.687 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	48.0
TPSA:	235.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	9.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.168	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.674	Fsp³:	0.956
MCE-18:	229.091 ? 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:	0.776	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.229	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.154	MDCK Permeability:	-5.114
Pgp-inhibitor:	0.0	Pgp-substrate:	0.876
PAMPA:	0.999 ? 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):	0.003
20% Bioavailability (F20%):	0.091	30% Bioavailability (F30%):	0.965
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.006
Plasma Protein Binding (PPB):	66.067%	Volume Distribution (VD):	-0.413
Fu:	28.119% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.454
BSEP inhibitor:	0.017

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.007	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.973
HLM stability:	0.915 ? 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):

0.543

Half-life (T1/2):

3.656

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.176
Human Hepatotoxicity (H-HT):	0.326	Drug-induced Liver Injury (DILI):	0.98
AMES Toxicity:	0.803	Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.021	Skin Sensitization:	1.0
Carcinogencity:	0.046	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.998
Hematotoxicity:	0.101	Drug-induced Nephrotoxicity:	0.796
Genotoxicity:	0.006	RPMI-8226 Immunitoxicity:	0.356
A549 Cytotoxicity:	0.783	Hek293 Cytotoxicity:	0.88
BCF:	1.946 ? 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:	3.479 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.595 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.049 ? 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
NPO12084	Dioscorea bulbifera	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s00299-005-0945-9]
NPO12084	Dioscorea bulbifera	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19842682]
NPO12084	Dioscorea bulbifera	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12084	Dioscorea bulbifera	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12084	Dioscorea bulbifera	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12084	Dioscorea bulbifera	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12084	Dioscorea bulbifera	Species	Dioscoreaceae	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 NPC602423 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	23867
0.1-0.2	22481
0.2-0.3	2739
0.3-0.4	502
0.4-0.5	102
0.5-0.6	90
0.6-0.7	40
0.7-0.8	0
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC300557
0.866	High Similarity	NPC309278
0.8191	Intermediate Similarity	NPC113044
0.8191	Intermediate Similarity	NPC283829
0.8191	Intermediate Similarity	NPC161676
0.8125	Intermediate Similarity	NPC470433
0.8125	Intermediate Similarity	NPC46190
0.8125	Intermediate Similarity	NPC171073
0.8061	Intermediate Similarity	NPC480555
0.8061	Intermediate Similarity	NPC150372
0.8	Intermediate Similarity	NPC14704
0.7979	Intermediate Similarity	NPC470432
0.7979	Intermediate Similarity	NPC230507
0.7961	Intermediate Similarity	NPC477811
0.7778	Intermediate Similarity	NPC181845
0.7767	Intermediate Similarity	NPC480554
0.7647	Intermediate Similarity	NPC269297
0.7647	Intermediate Similarity	NPC222202
0.7619	Intermediate Similarity	NPC480553
0.7615	Intermediate Similarity	NPC477808
0.7573	Intermediate Similarity	NPC475333
0.7573	Intermediate Similarity	NPC224098
0.7573	Intermediate Similarity	NPC208383
0.75	Intermediate Similarity	NPC248746
0.7368	Intermediate Similarity	NPC206003
0.7368	Intermediate Similarity	NPC473610
0.7273	Intermediate Similarity	NPC480556
0.717	Intermediate Similarity	NPC194207
0.717	Intermediate Similarity	NPC22779
0.7157	Intermediate Similarity	NPC477809
0.7115	Intermediate Similarity	NPC102016
0.7115	Intermediate Similarity	NPC95051
0.7087	Intermediate Similarity	NPC42171
0.7087	Intermediate Similarity	NPC6806
0.7064	Intermediate Similarity	NPC31896
0.6903	Remote Similarity	NPC224314
0.6863	Remote Similarity	NPC475351
0.6847	Remote Similarity	NPC232054
0.6789	Remote Similarity	NPC218571
0.6789	Remote Similarity	NPC487615
0.6698	Remote Similarity	NPC150057
0.6698	Remote Similarity	NPC147753
0.6667	Remote Similarity	NPC141433
0.6638	Remote Similarity	NPC210569
0.6606	Remote Similarity	NPC32361
0.6606	Remote Similarity	NPC13193
0.6602	Remote Similarity	NPC305423
0.6569	Remote Similarity	NPC125324
0.6466	Remote Similarity	NPC477807
0.6356	Remote Similarity	NPC15918
0.6333	Remote Similarity	NPC305771
0.6333	Remote Similarity	NPC94072
0.6333	Remote Similarity	NPC169816
0.633	Remote Similarity	NPC97700
0.633	Remote Similarity	NPC184617
0.633	Remote Similarity	NPC30856
0.63	Remote Similarity	NPC477451
0.6275	Remote Similarity	NPC19400
0.625	Remote Similarity	NPC6295
0.6216	Remote Similarity	NPC475550
0.6168	Remote Similarity	NPC473601
0.6168	Remote Similarity	NPC40440
0.6147	Remote Similarity	NPC51172
0.6147	Remote Similarity	NPC49032
0.6147	Remote Similarity	NPC124677
0.614	Remote Similarity	NPC83137
0.6117	Remote Similarity	NPC306131
0.6117	Remote Similarity	NPC200802
0.6095	Remote Similarity	NPC485595
0.6066	Remote Similarity	NPC263359
0.6061	Remote Similarity	NPC485594
0.6036	Remote Similarity	NPC294129
0.6019	Remote Similarity	NPC42482
0.6	Remote Similarity	NPC48886
0.6	Remote Similarity	NPC94881
0.5982	Remote Similarity	NPC475319
0.5965	Remote Similarity	NPC232037
0.5948	Remote Similarity	NPC132080
0.5946	Remote Similarity	NPC475182
0.5941	Remote Similarity	NPC297348
0.5941	Remote Similarity	NPC249204
0.5941	Remote Similarity	NPC48339
0.5941	Remote Similarity	NPC141769
0.5941	Remote Similarity	NPC477547
0.5914	Remote Similarity	NPC100451
0.5893	Remote Similarity	NPC73243
0.5893	Remote Similarity	NPC244086
0.5893	Remote Similarity	NPC84956
0.5888	Remote Similarity	NPC70204
0.5872	Remote Similarity	NPC98696
0.5841	Remote Similarity	NPC115165
0.5818	Remote Similarity	NPC469347
0.5806	Remote Similarity	NPC244431
0.5794	Remote Similarity	NPC94272
0.5789	Remote Similarity	NPC247037
0.5784	Remote Similarity	NPC325828
0.5739	Remote Similarity	NPC116756
0.5728	Remote Similarity	NPC234352
0.5726	Remote Similarity	NPC476112
0.5726	Remote Similarity	NPC307534
0.5699	Remote Similarity	NPC235126
0.5699	Remote Similarity	NPC242419
0.5688	Remote Similarity	NPC160426
0.5641	Remote Similarity	NPC249265
0.5641	Remote Similarity	NPC470864
0.5619	Remote Similarity	NPC222731
0.5603	Remote Similarity	NPC473518
0.5596	Remote Similarity	NPC195297
0.5593	Remote Similarity	NPC23808
0.5593	Remote Similarity	NPC87998
0.5575	Remote Similarity	NPC249553
0.5575	Remote Similarity	NPC182900
0.5565	Remote Similarity	NPC79900
0.5556	Remote Similarity	NPC107962
0.5546	Remote Similarity	NPC233433
0.5526	Remote Similarity	NPC151134
0.5514	Remote Similarity	NPC211354
0.5514	Remote Similarity	NPC107188
0.5487	Remote Similarity	NPC122819
0.5455	Remote Similarity	NPC144790
0.5455	Remote Similarity	NPC149400
0.5455	Remote Similarity	NPC329807
0.541	Remote Similarity	NPC470866
0.5391	Remote Similarity	NPC128572
0.5378	Remote Similarity	NPC108072
0.5372	Remote Similarity	NPC308140
0.5364	Remote Similarity	NPC15249
0.5364	Remote Similarity	NPC25455
0.5345	Remote Similarity	NPC475247
0.5333	Remote Similarity	NPC481189
0.5328	Remote Similarity	NPC167183
0.5327	Remote Similarity	NPC250393
0.5304	Remote Similarity	NPC471464
0.5294	Remote Similarity	NPC329727
0.5294	Remote Similarity	NPC232611
0.5288	Remote Similarity	NPC165439
0.5283	Remote Similarity	NPC294686
0.5258	Remote Similarity	NPC486119
0.5248	Remote Similarity	NPC277715
0.5242	Remote Similarity	NPC94086
0.5242	Remote Similarity	NPC473817
0.5238	Remote Similarity	NPC220836
0.5207	Remote Similarity	NPC470862
0.5179	Remote Similarity	NPC475670
0.5175	Remote Similarity	NPC486388
0.5159	Remote Similarity	NPC473505
0.5147	Remote Similarity	NPC329820
0.5146	Remote Similarity	NPC481420
0.5146	Remote Similarity	NPC473774
0.5146	Remote Similarity	NPC481419
0.5146	Remote Similarity	NPC481417
0.5146	Remote Similarity	NPC481421
0.514	Remote Similarity	NPC131693
0.514	Remote Similarity	NPC475436
0.513	Remote Similarity	NPC475643
0.5126	Remote Similarity	NPC486386
0.5122	Remote Similarity	NPC287885
0.5089	Remote Similarity	NPC306991
0.5088	Remote Similarity	NPC112274
0.5083	Remote Similarity	NPC475625
0.5048	Remote Similarity	NPC486114
0.5047	Remote Similarity	NPC177834
0.5041	Remote Similarity	NPC254255
0.5039	Remote Similarity	NPC32707
0.5038	Remote Similarity	NPC481190

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC602423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7538
0.1-0.2	1519
0.2-0.3	81
0.3-0.4	6
0.4-0.5	2
0.5-0.6	3
0.6-0.7	1
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
0.6698	Remote Similarity	NPD8450	Suspended
0.5784	Remote Similarity	NPD8171	Phase 2
0.5487	Remote Similarity	NPD8449	Approved
0.5225	Remote Similarity	NPD8170	Phase 2

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