NPASS Compound

Natural Product: NPC479185

Natural Product ID	NPC479185
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HFXGUURXLRDKBF-URSGQQSGSA-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]

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 133139 0 0 0 0 0 0 0 0999 V2000 6.3450 2.5427 3.0261 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8308 1.3401 2.2389 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3246 1.4700 2.0410 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0775 1.5199 3.3400 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8531 0.4815 1.2470 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5668 0.1544 3.0561 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8548 -0.8515 2.7083 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2361 -0.8795 1.4199 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2471 -1.2841 0.3960 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4079 -0.6276 -0.8029 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3469 -1.0150 -1.7413 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1639 -2.0945 -1.4922 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0151 -2.7618 -0.2969 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0670 -2.3651 0.6432 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0539 -1.8646 1.4002 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4136 -1.7046 0.0751 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0686 -2.0269 -0.9450 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1395 -1.2250 -0.1364 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5637 -1.0882 -1.4501 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3052 -1.9181 -1.5415 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8317 -1.3684 -2.3164 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1254 -1.1660 -1.6084 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2314 -0.2993 -0.4248 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7998 1.0550 -0.6511 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9947 1.1529 -1.5678 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2670 1.7813 0.6043 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4334 1.2854 1.7580 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9119 -0.1149 2.0095 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7305 -1.0177 0.8274 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1479 -1.3469 0.9337 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2855 -0.2659 1.8339 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9103 -2.0895 1.1852 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0195 -2.9110 2.2538 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9335 -2.7558 3.0649 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0398 -4.0021 2.4563 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6301 1.6265 0.8419 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3258 2.8021 0.9449 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4924 2.9575 0.0264 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7925 3.2504 0.7389 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5895 4.4801 1.5920 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2496 4.3196 2.3000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8299 2.9820 2.2554 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5144 5.5861 0.7381 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1400 2.1273 1.4698 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2711 4.0533 -0.8404 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7906 1.9861 -1.2371 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3982 3.0405 -1.5007 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3223 2.0485 -1.5958 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1116 0.7723 -2.1554 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2188 0.3598 -1.5483 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0944 1.4348 -0.9539 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3791 -0.2057 -3.2022 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7607 -0.7176 -4.0637 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3887 0.3275 -4.1211 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2454 3.1149 -2.5566 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3267 4.3356 -2.2480 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7902 4.5171 -1.0963 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4152 5.4493 -3.2321 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5189 -2.4992 -1.2242 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6080 -3.1385 -1.7914 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2668 -2.5145 -2.6640 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9333 -4.4764 -1.3604 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1832 -5.1602 -0.4314 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5012 -6.4305 -0.0171 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6003 -7.0486 -0.5397 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3876 -6.4019 -1.4786 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0380 -5.1066 -1.8813 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1475 -2.3642 -3.2947 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1408 -1.4378 2.3500 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1275 0.0802 4.3369 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2840 2.7304 2.8024 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9797 3.3992 2.7041 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4615 2.3188 4.0961 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3564 1.3796 1.2638 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5132 2.4454 1.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0546 2.0548 3.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5312 2.0400 4.1331 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3849 0.4837 3.6534 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7718 0.2125 1.5054 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8065 0.0835 1.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7820 0.2239 -1.0303 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4742 -0.4999 -2.6838 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8920 -2.3801 -2.2413 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6567 -3.6032 -0.1114 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9483 -2.8908 1.5876 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4219 -2.8991 1.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3639 -1.4230 -2.1211 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0862 -2.2195 -0.5013 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6865 -2.9020 -1.9885 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8857 -0.9029 -2.3898 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1528 -0.0862 -0.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6897 0.9007 -2.5955 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8592 0.5633 -1.3227 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2481 2.2513 -1.6393 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0856 2.8707 0.5399 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6803 1.8879 2.6725 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3778 1.3370 1.4733 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5077 -0.4664 2.9777 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4435 -2.2726 1.4718 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8194 -1.2935 0.0634 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4549 -4.9953 2.1848 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7220 -4.0519 3.5191 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1405 -3.8248 1.8317 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6149 3.6468 0.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5786 2.0729 -0.6137 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5349 3.4781 -0.0584 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4237 4.6144 2.3272 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2883 4.6834 3.3282 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4582 4.9004 1.7566 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6147 6.0046 0.7324 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7348 1.2952 1.0726 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4133 3.8230 -1.7730 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1426 2.3701 -0.6719 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2462 2.2665 -1.6370 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1136 0.9350 -0.9132 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8715 1.6603 0.0863 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5364 -0.6176 -5.1729 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9195 -1.8084 -3.9604 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 -0.1018 -3.9633 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0251 0.4151 -5.1922 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3023 -0.3034 -4.2282 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7445 1.3549 -3.8997 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5522 6.0112 -3.2527 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6471 5.0437 -4.2607 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2400 6.1467 -2.9923 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3026 -4.6340 -0.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8909 -6.9201 0.7046 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8793 -8.0606 -0.2291 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2422 -6.9346 -1.8581 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7005 -4.6691 -2.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1464 -3.2485 -2.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6485 -0.9750 3.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3543 -0.8098 4.7634 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 3 5 1 0 2 6 1 0 6 7 2 3 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 8 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 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 1 0 29 30 1 0 30 31 1 0 29 32 1 1 32 33 1 0 33 34 2 0 33 35 1 0 26 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 38 45 1 0 24 46 1 0 46 47 2 0 46 48 1 0 48 49 1 0 49 50 2 0 50 51 1 0 49 52 1 0 52 53 1 0 52 54 1 0 48 55 1 0 55 56 1 0 56 57 2 0 56 58 1 0 22 59 1 0 59 60 1 0 60 61 2 0 60 62 1 0 62 63 2 0 63 64 1 0 64 65 2 0 65 66 1 0 66 67 2 0 21 68 1 6 15 69 1 0 6 70 1 0 14 9 1 0 50 19 1 0 67 62 1 0 52 21 1 0 29 23 1 0 42 37 1 0 31 28 1 0 1 71 1 0 1 72 1 0 1 73 1 0 2 74 1 0 3 75 1 0 4 76 1 0 4 77 1 0 4 78 1 0 5 79 1 0 8 80 1 6 10 81 1 0 11 82 1 0 12 83 1 0 13 84 1 0 14 85 1 0 15 86 1 1 19 87 1 6 20 88 1 0 20 89 1 0 22 90 1 6 23 91 1 1 25 92 1 0 25 93 1 0 25 94 1 0 26 95 1 6 27 96 1 0 27 97 1 0 28 98 1 1 30 99 1 0 30100 1 0 35101 1 0 35102 1 0 35103 1 0 37104 1 6 38105 1 6 39106 1 6 40107 1 1 41108 1 0 41109 1 0 43110 1 0 44111 1 0 45112 1 0 48113 1 1 51114 1 0 51115 1 0 51116 1 0 53117 1 0 53118 1 0 53119 1 0 54120 1 0 54121 1 0 54122 1 0 58123 1 0 58124 1 0 58125 1 0 63126 1 0 64127 1 0 65128 1 0 66129 1 0 67130 1 0 68131 1 0 69132 1 0 70133 1 0 M END

Standard InCHIKey	HFXGUURXLRDKBF-URSGQQSGSA-N
Standard InCHI	InChI=1S/C50H63NO19/c1-23(25(3)52)43(60)51-35(28-15-11-9-12-16-28)37(57)45(62)67-31-20-50(63)42(69-44(61)29-17-13-10-14-18-29)40-48(8,41(59)39(66-26(4)53)34(24(31)2)47(50,6)7)32(19-33-49(40,22-65-33)70-27(5)54)68-46-38(58)36(56)30(55)21-64-46/h9-18,23,25,30-33,35-40,42,46,52,55-58,63H,19-22H2,1-8H3,(H,51,60)/t23?,25?,30-,31+,32+,33-,35+,36+,37-,38-,39-,40+,42+,46+,48-,49+,50-/m1/s1
SMILES	CC(C(C)O)C(=N[C@@H](c1ccccc1)[C@H](C(=O)O[C@H]1C[C@]2([C@H]([C@H]3[C@@](C)([C@H](C[C@@H]4[C@]3(CO4)OC(=O)C)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C)OC(=O)c1ccccc1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	981.4	Volume:	957.198 ? Van der Waals volume.
Dense:	1.025	LogP:	1.699 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.987 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.841 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	44.0
TPSA:	303.93 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.049	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.912	Fsp³:	0.6
MCE-18:	196.65 ? 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:	0.989	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.02 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.283 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.006	Promiscuous compounds:	0.044

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.773	MDCK Permeability:	-5.17
Pgp-inhibitor:	0.003	Pgp-substrate:	1.0
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%):	0.88	30% Bioavailability (F30%):	0.975
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.985
Plasma Protein Binding (PPB):	72.675%	Volume Distribution (VD):	-0.57
Fu:	23.27% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.0
BSEP inhibitor:	0.065

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:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.914 ? 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):

1.989

Half-life (T1/2):

3.852

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.027
Human Hepatotoxicity (H-HT):	0.994	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.843	Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.749	Skin Sensitization:	1.0
Carcinogencity:	0.02	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.454	Ototoxicity:	0.984
Hematotoxicity:	0.617	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.373
A549 Cytotoxicity:	0.43	Hek293 Cytotoxicity:	0.318
BCF:	0.473 ? 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:	3.321 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.134 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.159 ? 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
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23720	Taxus wallichiana	Species	Taxaceae	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

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell line	1
Others	1

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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	140.0	nM	PMID[28240909]
NPT2	Others	Unspecified	n.a.	IC50	>	250000.0	nM	PMID[28240909]

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 NPC479185 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	11415
0.1-0.2	35065
0.2-0.3	3289
0.3-0.4	31
0.4-0.5	13
0.5-0.6	15
0.6-0.7	21
0.7-0.8	1
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8972	High Similarity	NPC472391
0.8727	High Similarity	NPC479184
0.8611	High Similarity	NPC116862
0.8455	Intermediate Similarity	NPC479186
0.7807	Intermediate Similarity	NPC479173
0.7387	Intermediate Similarity	NPC479182
0.7387	Intermediate Similarity	NPC479180
0.7373	Intermediate Similarity	NPC472375
0.7241	Intermediate Similarity	NPC289383
0.6789	Remote Similarity	NPC471493
0.6783	Remote Similarity	NPC487360
0.6552	Remote Similarity	NPC33372
0.6552	Remote Similarity	NPC67246
0.6552	Remote Similarity	NPC324251
0.6552	Remote Similarity	NPC206211
0.6496	Remote Similarity	NPC471629
0.6496	Remote Similarity	NPC306001
0.641	Remote Similarity	NPC479183
0.641	Remote Similarity	NPC479181
0.6387	Remote Similarity	NPC275170
0.6379	Remote Similarity	NPC473490
0.6333	Remote Similarity	NPC486061
0.6333	Remote Similarity	NPC486060
0.6325	Remote Similarity	NPC208553
0.6325	Remote Similarity	NPC181964
0.6325	Remote Similarity	NPC307628
0.6281	Remote Similarity	NPC487361
0.621	Remote Similarity	NPC472392
0.6186	Remote Similarity	NPC471623
0.6102	Remote Similarity	NPC478328
0.582	Remote Similarity	NPC478329
0.5785	Remote Similarity	NPC453583
0.5702	Remote Similarity	NPC327699
0.561	Remote Similarity	NPC471754
0.5528	Remote Similarity	NPC191193
0.5447	Remote Similarity	NPC321072
0.5447	Remote Similarity	NPC215892
0.5447	Remote Similarity	NPC242662
0.5323	Remote Similarity	NPC102167
0.5323	Remote Similarity	NPC488127
0.528	Remote Similarity	NPC453588
0.528	Remote Similarity	NPC473400
0.521	Remote Similarity	NPC603140
0.512	Remote Similarity	NPC36607
0.5039	Remote Similarity	NPC603171

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479185 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3783
0.1-0.2	5225
0.2-0.3	129
0.3-0.4	0
0.4-0.5	5
0.5-0.6	4
0.6-0.7	2
0.7-0.8	1
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
0.7054	Intermediate Similarity	NPD8435	Phase 4
0.6325	Remote Similarity	NPD8485	Phase 4
0.6239	Remote Similarity	NPD8424	Phase 3
0.5726	Remote Similarity	NPD8486	Phase 1
0.5323	Remote Similarity	NPD8360	Approved
0.5323	Remote Similarity	NPD8361	Phase 4
0.5038	Remote Similarity	NPD8470	Clinical (unspecified phase)

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