NPASS Compound

Natural Product: NPC5194

Natural Product ID	NPC5194
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hymenistatin 1
IUPAC Name	n.a.
Synonyms	Hymenistatin 1
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2370330
PubChem CID	10102206
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

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 136140 0 0 0 0 0 0 0 0999 V2000 -5.1532 1.2930 -5.4190 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1816 0.6864 -4.3951 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8117 0.6078 -3.0473 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9598 0.0482 -1.9649 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7604 0.6211 -1.6565 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9178 1.2376 -1.1234 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6149 1.1784 -1.8142 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7882 2.0735 0.0810 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8832 2.1942 1.0468 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1801 2.7691 0.6019 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1556 2.8046 1.8019 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9930 4.2252 0.1849 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2973 3.4000 -0.2635 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4264 4.1028 0.2996 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1381 5.3782 -0.2609 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3195 3.7203 1.4906 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1186 4.7494 2.5757 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0153 5.8601 2.1282 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0988 5.1514 1.3471 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7828 3.7967 1.2444 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5071 2.6269 0.9937 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7317 1.6151 1.0616 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9243 2.3884 0.6875 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0471 0.9464 0.5592 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5712 0.0799 1.2733 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2133 0.3225 2.4560 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4754 -1.3462 0.7806 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6304 -1.3458 -0.3463 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8262 -2.1580 -0.8535 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4692 -3.4898 -0.4065 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3206 -3.6478 0.4556 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7159 -2.6293 1.2330 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3061 -1.5178 0.8875 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3148 -2.6487 2.2092 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7179 -2.5148 1.9312 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2242 -2.3111 0.6581 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2663 -2.3690 -0.1826 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6123 -2.0624 0.1699 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6880 -2.2502 -1.2117 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8267 -1.4397 -2.1768 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8503 -1.9565 -3.4514 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6918 -2.7330 0.9624 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6043 -4.2237 0.9896 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6883 -4.8544 1.8231 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0183 -2.3172 0.2633 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3215 -2.6762 3.2247 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4600 -3.6990 3.9907 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1947 -3.7481 3.2146 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9169 -4.9905 0.3134 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4784 -5.5921 -0.9522 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1553 -4.3892 -1.6013 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1767 -1.6958 -2.0417 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7703 -2.0424 0.6746 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7854 -1.4316 -0.1972 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7302 -0.5723 0.3727 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7030 -0.0159 -0.4430 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7406 -0.3047 -1.7934 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7997 -1.1566 -2.3456 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8261 -1.7131 -1.5364 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7360 0.2843 -2.5382 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4302 2.9375 -0.6088 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9203 2.5176 -0.6568 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4673 4.4221 -0.7506 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5537 1.8824 -2.6971 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9697 0.9387 -6.4420 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1938 0.9767 -5.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1105 2.3900 -5.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2484 1.3105 -4.3718 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8928 -0.2766 -4.8077 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6578 -0.1543 -3.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6935 0.0498 -1.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6168 0.9833 -2.8070 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8923 1.6232 0.6774 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1255 1.2381 1.5842 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5487 2.8665 1.9079 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6435 2.1376 -0.1299 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6468 2.9996 2.7484 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7289 1.8844 1.8949 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8740 3.6260 1.5959 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9073 4.8277 0.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5455 4.2047 -0.8334 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2082 4.6836 0.8626 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2851 5.5197 -1.2684 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0529 2.7367 1.9099 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4238 4.3523 3.5700 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9519 5.0581 2.6389 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4080 6.3746 3.0371 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4676 6.6213 1.5465 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0963 5.6734 0.3375 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0460 5.3890 1.8892 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5627 2.7911 1.4799 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2991 1.2818 2.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9487 -1.8500 1.6815 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3359 -3.9338 0.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1195 -1.6959 2.8639 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7644 -0.9482 0.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0129 -2.9319 -3.6867 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7854 -2.2330 1.9432 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7367 -4.5664 -0.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6090 -4.5084 1.3688 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5827 -5.9642 1.7472 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5198 -4.5931 2.8753 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6932 -4.6216 1.4550 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0567 -1.2044 0.3905 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8387 -2.7012 0.9297 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0824 -2.6574 -0.7620 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3182 -3.0835 3.2841 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2155 -1.7467 3.8439 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9875 -4.6933 4.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3315 -3.4198 5.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1480 -4.7499 2.7161 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6968 -3.6663 3.8714 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1718 -5.1905 0.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3658 -5.5895 1.1639 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6731 -6.0232 -1.5579 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2486 -6.3462 -0.6613 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1395 -4.7362 -1.9842 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5323 -3.9171 -2.3549 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2559 -0.7006 -2.2577 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5569 -3.0503 0.2197 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1746 -2.2733 1.6906 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6588 -0.3873 1.4154 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4245 0.6500 0.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8271 -1.3738 -3.4019 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0984 -2.3750 -2.0117 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9278 -0.0419 -3.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9684 2.4209 -1.4759 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4026 3.1595 0.0984 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9785 1.4716 -0.3117 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3447 2.6842 -1.6596 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6612 4.9530 0.1759 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2829 4.7466 -1.4656 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5360 4.7282 -1.2626 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2593 1.7998 -1.8804 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0637 2.3130 -3.5811 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7733 2.6613 -2.4366 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 2 3 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 8 13 1 0 13 14 2 3 14 15 1 0 14 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 2 0 21 23 1 0 23 24 1 0 24 25 2 3 25 26 1 0 25 27 1 0 27 28 1 0 28 29 2 3 29 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 1 0 39 40 2 3 40 41 1 0 38 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 35 46 1 0 46 47 1 0 47 48 1 0 31 49 1 0 49 50 1 0 50 51 1 0 29 52 1 0 27 53 1 0 53 54 1 0 54 55 2 0 55 56 1 0 56 57 2 0 57 58 1 0 58 59 2 0 57 60 1 0 23 61 1 0 61 62 1 0 61 63 1 0 3 64 1 0 40 4 1 0 59 54 1 0 20 16 1 0 51 30 1 0 48 34 1 0 1 65 1 0 1 66 1 0 1 67 1 0 2 68 1 0 2 69 1 0 3 70 1 6 4 71 1 1 7 72 1 0 8 73 1 1 9 74 1 0 9 75 1 0 10 76 1 0 11 77 1 0 11 78 1 0 11 79 1 0 12 80 1 0 12 81 1 0 12 82 1 0 15 83 1 0 16 84 1 1 17 85 1 0 17 86 1 0 18 87 1 0 18 88 1 0 19 89 1 0 19 90 1 0 23 91 1 1 26 92 1 0 27 93 1 1 30 94 1 1 34 95 1 1 38 96 1 6 41 97 1 0 42 98 1 1 43 99 1 0 43100 1 0 44101 1 0 44102 1 0 44103 1 0 45104 1 0 45105 1 0 45106 1 0 46107 1 0 46108 1 0 47109 1 0 47110 1 0 48111 1 0 48112 1 0 49113 1 0 49114 1 0 50115 1 0 50116 1 0 51117 1 0 51118 1 0 52119 1 0 53120 1 0 53121 1 0 55122 1 0 56123 1 0 58124 1 0 59125 1 0 60126 1 0 61127 1 0 62128 1 0 62129 1 0 62130 1 0 63131 1 0 63132 1 0 63133 1 0 64134 1 0 64135 1 0 64136 1 0 M END

Standard InCHIKey	NACGNHONDBBQGE-MXKYYYADSA-N
Standard InCHI	InChI=1S/C47H72N8O9/c1-9-28(7)38-44(61)52-39(29(8)10-2)47(64)55-23-13-16-36(55)45(62)53-21-11-14-34(53)42(59)49-33(25-30-17-19-31(56)20-18-30)41(58)50-37(27(5)6)46(63)54-22-12-15-35(54)43(60)48-32(24-26(3)4)40(57)51-38/h17-20,26-29,32-39,56H,9-16,21-25H2,1-8H3,(H,48,60)(H,49,59)(H,50,58)(H,51,57)(H,52,61)/t28-,29-,32-,33-,34-,35-,36-,37-,38-,39-/m0/s1
SMILES	CC[C@@H]([C@@H]1N=C(O)[C@H](CC(C)C)N=C(O)[C@@H]2CCCN2C(=O)[C@@H](N=C(O)[C@@H](N=C([C@H]2N(C(=O)[C@H]3N(C(=O)[C@@H](N=C1O)[C@H](CC)C)CCC3)CCC2)O)Cc1ccc(cc1)O)C(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	892.54	Volume:	916.771 ? Van der Waals volume.
Dense:	0.974	LogP:	2.314 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.714 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.266 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	45.0
TPSA:	244.11 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.162	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.456	Fsp³:	0.702
MCE-18:	137.0 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.432	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.745 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.078

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.356	MDCK Permeability:	-5.068
Pgp-inhibitor:	1.0	Pgp-substrate:	1.0
PAMPA:	0.012 ? 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):	0.987
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.664
Plasma Protein Binding (PPB):	66.193%	Volume Distribution (VD):	-0.145
Fu:	31.436% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.055
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.008	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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

1.736

Half-life (T1/2):

2.439

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.006	Rat Oral Acute Toxicity:	0.524
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	1.0
Carcinogencity:	0.949	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.717
Drug-induced Neurotoxicity:	0.028	Ototoxicity:	1.0
Hematotoxicity:	0.815	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.476 ? 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:	3.524 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.159 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.295 ? 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
NPO17477	Potentilla indica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37765360]
NPO14751	Anisodoris nobilis	Species	Discodorididae	Eukaryota	n.a.	n.a.	n.a.	PMID[7241154]
NPO9435	Acacia georginae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14751	Anisodoris nobilis	Species	Discodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28868	Pardachirus pavoninus	Species	Soleidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21698	Crinum augustum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12664	Haplanthus tentaculatus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6751	Clusia grandiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO757	Dorycnium graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11799	Ursinia saxatilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17233	Picrodendron baccatum	Species	Picrodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16836	Polyporus picipes	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16589	Clitocybe conglobata	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17477	Potentilla indica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17233	Picrodendron baccatum	Species	Picrodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16836	Polyporus picipes	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17695	Calyptranthes tricona	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15034	Intsia bijuga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9435	Acacia georginae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11480	Haematomma puniceum	Species	Haematommataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17016	Cassinia aculeata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14751	Anisodoris nobilis	Species	Discodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21698	Crinum augustum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6751	Clusia grandiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11799	Ursinia saxatilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28868	Pardachirus pavoninus	Species	Soleidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17233	Picrodendron baccatum	Species	Picrodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO757	Dorycnium graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13365	Helminthosporium euchlaenae	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17477	Potentilla indica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13830	Alcaligenes faecalis	Species	Alcaligenaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16589	Clitocybe conglobata	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17935	Pedicularis lasiophrys	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12664	Haplanthus tentaculatus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16723	Gascardia madagascariensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17160	Dimerostemma lippioides	Species	Asteraceae	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
GI50	6

Activity Type	# Activity
Cell line	6

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
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	=	40000.0	nM	DOI[10.1016/S0960-894X(01)80843-X]
NPT399	Cell line	SF-295	Homo sapiens	GI50	=	300000.0	nM	DOI[10.1016/S0960-894X(01)80843-X]
NPT376	Cell line	A498	Homo sapiens	GI50	=	700000.0	nM	DOI[10.1016/S0960-894X(01)80843-X]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	=	300000.0	nM	DOI[10.1016/S0960-894X(01)80843-X]
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	=	100000.0	nM	DOI[10.1016/S0960-894X(01)80843-X]
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	=	600000.0	nM	DOI[10.1016/S0960-894X(01)80843-X]

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 NPC5194 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	17929
0.1-0.2	30058
0.2-0.3	1371
0.3-0.4	337
0.4-0.5	108
0.5-0.6	33
0.6-0.7	14
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
0.9333	High Similarity	NPC261934
0.7949	Intermediate Similarity	NPC489556
0.7901	Intermediate Similarity	NPC489825
0.7901	Intermediate Similarity	NPC489826
0.7895	Intermediate Similarity	NPC479068
0.7349	Intermediate Similarity	NPC479070
0.7326	Intermediate Similarity	NPC302597
0.7093	Intermediate Similarity	NPC479069
0.6897	Remote Similarity	NPC489827
0.6889	Remote Similarity	NPC489828
0.6543	Remote Similarity	NPC485876
0.65	Remote Similarity	NPC242482
0.6392	Remote Similarity	NPC489823
0.631	Remote Similarity	NPC489829
0.6292	Remote Similarity	NPC101679
0.6222	Remote Similarity	NPC262166
0.6222	Remote Similarity	NPC241794
0.622	Remote Similarity	NPC224315
0.6081	Remote Similarity	NPC486124
0.6076	Remote Similarity	NPC200589
0.6071	Remote Similarity	NPC489591
0.6	Remote Similarity	NPC136797
0.5977	Remote Similarity	NPC479072
0.5977	Remote Similarity	NPC489592
0.5955	Remote Similarity	NPC488256
0.5882	Remote Similarity	NPC487230
0.587	Remote Similarity	NPC141957
0.5814	Remote Similarity	NPC202198
0.5714	Remote Similarity	NPC326349
0.5714	Remote Similarity	NPC323336
0.5714	Remote Similarity	NPC328649
0.5714	Remote Similarity	NPC479074
0.5673	Remote Similarity	NPC487229
0.5632	Remote Similarity	NPC16188
0.5607	Remote Similarity	NPC61004
0.5556	Remote Similarity	NPC489822
0.5495	Remote Similarity	NPC487674
0.5495	Remote Similarity	NPC89489
0.5455	Remote Similarity	NPC275110
0.5333	Remote Similarity	NPC489824
0.5281	Remote Similarity	NPC287401
0.5281	Remote Similarity	NPC489557
0.5269	Remote Similarity	NPC56685
0.5263	Remote Similarity	NPC242159
0.5244	Remote Similarity	NPC489594
0.5244	Remote Similarity	NPC153491
0.5222	Remote Similarity	NPC485094
0.5217	Remote Similarity	NPC6975
0.5213	Remote Similarity	NPC130309
0.5213	Remote Similarity	NPC322878
0.5205	Remote Similarity	NPC118202
0.5128	Remote Similarity	NPC479752
0.5114	Remote Similarity	NPC489593
0.5104	Remote Similarity	NPC488254
0.5049	Remote Similarity	NPC223791

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC5194 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3191
0.1-0.2	5659
0.2-0.3	266
0.3-0.4	31
0.4-0.5	3
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