NPASS Compound

Natural Product: NPC296968

Natural Product ID	NPC296968
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QJCLMDOTVMDUCX-ACOBSCFGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21576266
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 131135 0 0 0 0 0 0 0 0999 V2000 -2.9988 4.2244 1.7495 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2031 4.4753 0.2607 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2000 5.4064 -0.2723 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3352 5.2610 -1.1709 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9623 4.2230 -2.0118 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2002 4.5568 -3.5059 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4402 5.7457 -3.9140 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2622 6.4171 -3.0475 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4464 6.1872 -5.2234 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4502 3.7673 -1.9663 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8506 2.8806 -2.7379 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4686 4.2278 -1.1169 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4562 5.1990 -0.1142 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8646 5.7731 -0.1022 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7058 4.5915 -0.4504 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8065 3.6716 -1.2092 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7546 2.3101 -0.5752 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8363 1.6526 -0.4453 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0826 0.3716 0.1057 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6591 0.1579 1.5155 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3455 1.1316 2.4272 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8339 1.0137 2.3690 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2812 -0.2976 2.7208 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2096 -0.8676 4.0149 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0394 -0.0849 5.0256 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3269 -2.2703 4.2225 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6803 -0.7654 -0.7941 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7961 -1.6104 -0.5018 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3867 -2.7431 -1.3775 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4829 -3.6812 -1.3778 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4763 -4.9154 -2.1516 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5729 -4.8725 -3.5392 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6643 -6.0101 -4.2629 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6651 -7.2533 -3.6609 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5691 -7.3291 -2.2711 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4783 -6.1597 -1.5584 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7543 -8.4212 -4.3626 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9886 -2.9858 -1.1215 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2892 -1.8857 -0.8738 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 -4.0532 -1.0380 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4109 -5.4554 -0.8439 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8231 -6.1188 -0.2648 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7096 -4.9375 0.0973 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3178 -3.9639 -0.9973 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9916 -2.6914 -0.9962 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7120 -2.1649 -0.1751 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4507 -1.8656 0.9030 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6465 -1.7180 2.1849 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4798 -1.3876 3.3634 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7202 -0.0997 3.8153 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5127 0.1576 4.9090 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1062 -0.8671 5.6074 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8831 -2.1612 5.1800 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0821 -2.3939 4.0775 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9201 -0.6172 6.7271 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3466 -0.6323 0.6986 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1957 0.0932 -0.2603 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 1.1909 -0.9926 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9562 1.2665 -1.5467 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2191 0.2372 -2.6271 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9330 1.2423 -0.5686 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3558 2.4598 -0.1803 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4095 3.2789 -0.4799 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1801 2.7600 0.8858 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2969 -0.4467 1.6775 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7682 -1.9116 -2.1989 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3543 -0.8318 -1.9971 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5720 1.7352 -0.1228 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1899 6.7135 0.3242 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9548 4.5034 2.0652 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2382 3.1861 2.0384 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6529 4.8793 2.3603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1900 5.0331 0.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6084 3.3304 -1.8594 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2827 4.6182 -3.7215 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8326 3.6950 -4.1352 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8103 7.2691 -3.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2805 6.8243 -5.5809 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6935 5.9988 -0.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3367 4.7181 0.8900 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9712 6.5423 -0.9000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1597 6.1078 0.8949 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1005 4.0615 0.4467 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5663 4.9175 -1.0768 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1794 3.5969 -2.2555 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2190 0.2614 0.1229 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5700 0.2683 1.6979 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8906 -0.8971 1.7754 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0342 0.9982 3.4878 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0376 2.1944 2.1872 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2675 1.7704 3.0954 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2013 1.3639 1.3797 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6946 -0.8924 1.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9602 0.9163 4.8914 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6870 -2.8561 3.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0556 -2.6790 5.1311 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4366 -2.1709 -2.4232 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4423 -3.1395 -1.7297 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7942 -3.8922 -0.2914 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5723 -3.9106 -3.9975 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7422 -5.9710 -5.3315 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5652 -8.2724 -1.7673 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4167 -6.2408 -0.4606 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9192 -8.9876 -4.5274 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6330 -5.9685 -1.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1999 -5.5961 -0.0626 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5539 -6.7209 0.6179 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3080 -6.7810 -1.0362 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7563 -5.2754 -0.0037 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4155 -4.6149 1.0996 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6536 -4.4791 -1.9641 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2378 -2.6730 1.0901 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0710 -2.6440 2.3138 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8973 -0.9058 2.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2412 0.7028 3.2458 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6802 1.1657 5.2358 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3604 -2.9764 5.7412 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9486 -3.4212 3.7943 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9530 -0.6379 6.6210 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8924 1.2961 -1.9277 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0307 2.2619 -2.0575 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1424 -0.3360 -2.3114 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3722 -0.4420 -2.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4880 0.6935 -3.6052 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1626 2.1711 -0.2733 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4563 3.6995 1.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9319 0.3261 1.7672 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0005 -0.9363 -2.1916 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9646 -1.0492 -2.8875 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3512 0.7516 -0.2968 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3980 7.3352 0.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 3 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 3 7 9 1 0 5 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 3 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 2 3 24 26 1 0 19 27 1 0 27 28 2 3 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 34 37 1 0 29 38 1 0 38 39 2 0 38 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 2 3 46 47 1 0 47 48 1 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 52 55 1 0 47 56 1 0 56 57 2 3 57 58 1 0 58 59 1 0 59 60 1 0 59 61 1 0 58 62 1 0 62 63 2 3 62 64 1 0 56 65 1 0 45 66 1 0 27 67 1 0 17 68 1 0 3 69 1 0 63 2 1 0 16 12 1 0 36 31 1 0 44 40 1 0 54 49 1 0 1 70 1 0 1 71 1 0 1 72 1 0 2 73 1 1 5 74 1 1 6 75 1 0 6 76 1 0 8 77 1 0 9 78 1 0 13 79 1 0 13 80 1 0 14 81 1 0 14 82 1 0 15 83 1 0 15 84 1 0 16 85 1 6 19 86 1 1 20 87 1 0 20 88 1 0 21 89 1 0 21 90 1 0 22 91 1 0 22 92 1 0 23 93 1 0 25 94 1 0 26 95 1 0 26 96 1 0 29 97 1 6 30 98 1 0 30 99 1 0 32100 1 0 33101 1 0 35102 1 0 36103 1 0 37104 1 0 41105 1 0 41106 1 0 42107 1 0 42108 1 0 43109 1 0 43110 1 0 44111 1 6 47112 1 1 48113 1 0 48114 1 0 50115 1 0 51116 1 0 53117 1 0 54118 1 0 55119 1 0 58120 1 6 59121 1 6 60122 1 0 60123 1 0 60124 1 0 61125 1 0 64126 1 0 65127 1 0 66128 1 0 67129 1 0 68130 1 0 69131 1 0 M END

Standard InCHIKey	QJCLMDOTVMDUCX-ACOBSCFGSA-N
Standard InCHI	InChI=1S/C45H62N12O12/c1-23-37(62)53-32(22-35(46)61)44(69)57-19-4-7-33(57)40(65)51-29(6-3-17-49-45(47)48)38(63)54-31(21-26-11-15-28(60)16-12-26)43(68)56-18-5-8-34(56)41(66)52-30(20-25-9-13-27(59)14-10-25)39(64)55-36(24(2)58)42(67)50-23/h9-16,23-24,29-34,36,58-60H,3-8,17-22H2,1-2H3,(H2,46,61)(H,50,67)(H,51,65)(H,52,66)(H,53,62)(H,54,63)(H,55,64)(H4,47,48,49)/t23-,24+,29-,30-,31-,32-,33-,34-,36-/m0/s1
SMILES	C[C@H]1C(=N[C@@H](CC(=N)O)C(=O)N2CCC[C@H]2C(=N[C@@H](CCCNC(=N)N)C(=N[C@@H](Cc2ccc(cc2)O)C(=O)N2CCC[C@H]2C(=N[C@@H](Cc2ccc(cc2)O)C(=N[C@@H]([C@@H](C)O)C(=N1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	962.46	Volume:	939.354 ? Van der Waals volume.
Dense:	1.025	LogP:	-2.321 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.462 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.567 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	48.0
TPSA:	402.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	15.0	Rings:	5.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.087	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.734	Fsp³:	0.511
MCE-18:	136.471 ? 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:	0.629	Fluc inhibitor:	0.308 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.905 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.005	Promiscuous compounds:	0.03

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.497	MDCK Permeability:	-5.116
Pgp-inhibitor:	0.128	Pgp-substrate:	1.0
PAMPA:	0.966 ? 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):	0.509
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.618
Plasma Protein Binding (PPB):	48.395%	Volume Distribution (VD):	-0.339
Fu:	41.422% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.987	BCRP inhibitor:	0.001
BSEP inhibitor:	0.237

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.847	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):

1.25

Half-life (T1/2):

3.18

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:	0.0	Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.574	Skin Sensitization:	1.0
Carcinogencity:	0.019	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.998
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	1.0
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.001
BCF:	0.211 ? 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:	3.004 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.07 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.832 ? 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
NPO24195	Stylissa carteri	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043426]
NPO32816	Axinella carteri	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043426]
NPO27991	Stylissa flabelliformis	Species	Axinellidae	Eukaryota	n.a.	Maldive Islands	1995	PMID[18327911]
NPO27991	Stylissa flabelliformis	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29893558]
NPO32816	Axinella carteri	Species	Axinellidae	Eukaryota	n.a.	Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[9548881]
NPO24195	Stylissa carteri	Species	Axinellidae	Eukaryota	n.a.	indopacific	n.a.	PMID[9917317]
NPO24195	Stylissa carteri	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32816	Axinella carteri	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27991	Stylissa flabelliformis	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27991	Stylissa flabelliformis	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24195	Stylissa carteri	Species	Axinellidae	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	9
MIC	10

Activity Type	# Activity
Cell line	6
Organism	10
Protein complex	1
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2890	Protein complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	>	100000.0	nM	PMID[29893558]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[29893558]
NPT111	Cell line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[29893558]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	>	50000.0	nM	PMID[29893558]
NPT81	Cell line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[29893558]
NPT1086	Cell line	SK-HEP1	Homo sapiens	IC50	>	50000.0	nM	PMID[29893558]
NPT2548	Cell line	SNU-638	Homo sapiens	IC50	>	50000.0	nM	PMID[29893558]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	128000.0	nM	PMID[29893558]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	128000.0	nM	PMID[29893558]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	128000.0	nM	PMID[29893558]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128000.0	nM	PMID[29893558]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	128000.0	nM	PMID[29893558]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	128000.0	nM	PMID[29893558]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128000.0	nM	PMID[29893558]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	128000.0	nM	PMID[29893558]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128000.0	nM	PMID[29893558]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	128000.0	nM	PMID[29893558]
NPT2	Others	Unspecified	n.a.	IC50	>	100000.0	nM	PMID[29893558]

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 NPC296968 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	17307
0.1-0.2	31192
0.2-0.3	944
0.3-0.4	279
0.4-0.5	108
0.5-0.6	24
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	Natural Product ID
0.7387	Intermediate Similarity	NPC489549
0.6061	Remote Similarity	NPC56685
0.5825	Remote Similarity	NPC485662
0.5825	Remote Similarity	NPC485663
0.5784	Remote Similarity	NPC136797
0.5714	Remote Similarity	NPC489829
0.5673	Remote Similarity	NPC241794
0.5659	Remote Similarity	NPC484875
0.5455	Remote Similarity	NPC202198
0.5455	Remote Similarity	NPC481408
0.5405	Remote Similarity	NPC328649
0.527	Remote Similarity	NPC484963
0.5268	Remote Similarity	NPC58725
0.5235	Remote Similarity	NPC486505
0.5133	Remote Similarity	NPC477632
0.5098	Remote Similarity	NPC484964
0.5096	Remote Similarity	NPC489556
0.5096	Remote Similarity	NPC489822
0.5093	Remote Similarity	NPC141957
0.5091	Remote Similarity	NPC302597
0.5082	Remote Similarity	NPC479144
0.5069	Remote Similarity	NPC329295
0.5064	Remote Similarity	NPC489536
0.5064	Remote Similarity	NPC489538
0.5064	Remote Similarity	NPC489537
0.5033	Remote Similarity	NPC485246

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC296968 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3954
0.1-0.2	4990
0.2-0.3	169
0.3-0.4	28
0.4-0.5	7
0.5-0.6	2
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
0.52	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.5167	Remote Similarity	NPD8303	Discontinued

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