NPASS Compound

Natural Product: NPC604133

Natural Product ID	NPC604133
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YDQIRODFTJGGMP-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1970059
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 125131 0 0 0 0 0 0 0 0999 V2000 -4.7323 -3.9886 -3.0679 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8204 -2.6820 -2.2632 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2461 -2.6915 -1.6832 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7638 -1.5568 -3.2211 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3261 -0.2596 -2.6741 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 -0.2463 -1.6389 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7154 0.9001 -0.7296 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0128 1.9119 -0.5253 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9473 0.8418 -0.0978 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4075 1.8799 0.7498 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8536 1.3886 1.9720 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0329 2.4640 2.8350 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8804 2.0634 4.0319 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0682 3.1280 4.8997 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7521 3.6233 2.1719 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6472 4.2333 3.0526 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5778 3.1304 0.9852 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5483 2.2521 1.4335 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6378 2.4616 0.0391 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3259 1.3908 -0.5683 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9536 0.2543 -2.1898 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.0916 -1.5001 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5817 -1.5914 -1.2046 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9092 -2.1971 -2.5418 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1094 -1.8879 -3.5886 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7493 -1.6472 -0.2414 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5102 -1.7450 1.0319 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1918 -1.8046 1.7351 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8739 -2.2381 0.8272 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2153 -1.6642 1.3413 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3713 -2.5147 0.9339 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1817 -1.7309 2.8532 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3425 -0.9178 3.4533 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2007 -1.0186 4.8376 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0445 0.5122 3.0697 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9370 1.3836 3.6777 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1455 0.6951 1.5546 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5479 2.1009 1.3268 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5790 0.7252 1.2183 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4576 0.4853 2.1187 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1269 0.9996 -0.0213 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5183 1.0182 -0.2828 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8105 2.3691 -0.5829 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1658 2.6001 -0.3647 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5135 3.9858 -0.8713 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7663 4.9494 -0.1977 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9229 1.5559 -1.1604 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0488 2.1047 -1.7393 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0235 0.9258 -2.2105 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3936 1.8929 -2.9905 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9179 0.1828 -1.4567 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4532 -1.0118 -0.9751 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2889 -0.2635 0.8308 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5245 -0.3723 -0.6267 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8498 -1.5108 -1.3204 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6605 -2.1223 -0.6423 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6390 -3.6173 -1.1191 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1510 -1.4651 -0.7637 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8224 -2.7035 -1.1882 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6633 -4.2079 -3.1991 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2663 -4.7833 -2.5037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1740 -3.7901 -4.0512 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9934 -2.5973 -2.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3185 -3.5954 -1.0638 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2866 -1.8216 -0.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7319 -1.4298 -3.7384 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0447 -1.8456 -4.0455 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2678 0.3052 -2.4020 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9391 0.3497 -3.5491 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6867 2.7114 0.8421 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0639 2.8385 3.2008 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8872 1.7604 3.6288 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4911 1.1752 4.5484 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2898 3.7063 4.9991 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0279 4.3777 1.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4078 4.5968 2.5284 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0447 4.0405 0.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1691 2.0511 0.6801 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2938 3.1199 -0.7938 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4635 0.6434 0.0680 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9590 0.0513 -3.2850 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9217 1.3967 -2.2028 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4830 0.5358 -0.6247 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1138 0.1223 -2.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9431 -1.9047 -2.8937 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9395 -3.2906 -2.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5425 -2.0944 -4.4332 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4423 -1.7916 1.6616 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0056 -0.7882 2.2035 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3523 -2.4602 2.6272 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0625 -3.3256 1.1394 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1198 -2.0192 0.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1540 -3.4942 0.5034 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0201 -2.7922 1.8416 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4212 -2.8046 3.1204 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3083 -1.3649 3.3545 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3209 -1.2731 3.1540 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7568 -1.7435 5.1988 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0297 0.7577 3.4234 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5926 0.9137 4.2507 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4089 2.2936 0.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5689 2.1314 1.8132 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2383 2.8822 1.7104 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1155 0.7852 0.6338 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4336 2.5814 0.7140 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5857 4.1625 -0.5854 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4570 4.0782 -1.9551 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8453 4.8958 -0.5789 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2047 0.7400 -0.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7715 2.1156 -1.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6483 0.2400 -2.7974 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0660 2.2494 -3.6490 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0273 0.0202 -2.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2988 -1.2521 -1.4549 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2288 0.1384 0.9379 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2357 0.6298 -1.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6155 -0.4171 -0.8155 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6268 -2.3087 -1.5022 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6601 -1.1333 -2.3510 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3277 -4.0792 -0.8231 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3458 -4.2385 -0.5330 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9597 -3.7253 -2.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7769 -1.1844 0.1554 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3360 -3.2463 -0.3165 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0218 -3.4645 -1.4422 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 6 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 26 27 2 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 33 34 1 0 33 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 37 39 1 0 39 40 2 0 39 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 47 48 1 0 47 49 1 0 49 50 1 0 49 51 1 0 51 52 1 0 37 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 26 58 1 0 58 59 1 0 59 2 1 0 58 6 1 0 19 10 1 0 56 23 1 0 56 29 1 0 53 30 1 0 51 42 1 0 1 60 1 0 1 61 1 0 1 62 1 0 3 63 1 0 3 64 1 0 3 65 1 0 4 66 1 0 4 67 1 0 5 68 1 0 5 69 1 0 10 70 1 0 12 71 1 0 13 72 1 0 13 73 1 0 14 74 1 0 15 75 1 0 16 76 1 0 17 77 1 0 18 78 1 0 19 79 1 0 20 80 1 0 21 81 1 0 21 82 1 0 22 83 1 0 22 84 1 0 24 85 1 0 24 86 1 0 25 87 1 0 27 88 1 0 28 89 1 0 28 90 1 0 29 91 1 0 31 92 1 0 31 93 1 0 31 94 1 0 32 95 1 0 32 96 1 0 33 97 1 0 34 98 1 0 35 99 1 0 36100 1 0 38101 1 0 38102 1 0 38103 1 0 42104 1 0 44105 1 0 45106 1 0 45107 1 0 46108 1 0 47109 1 0 48110 1 0 49111 1 0 50112 1 0 51113 1 0 52114 1 0 53115 1 0 54116 1 0 54117 1 0 55118 1 0 55119 1 0 57120 1 0 57121 1 0 57122 1 0 58123 1 0 59124 1 0 59125 1 0 M END

Standard InCHIKey	YDQIRODFTJGGMP-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C42H66O17/c1-37(2)10-11-41(36(55)59-34-31(52)29(50)27(48)23(17-44)57-34)12-13-42(18-45)19(20(41)14-37)6-7-24-38(3)15-21(46)32(53)40(5,25(38)8-9-39(24,42)4)35(54)58-33-30(51)28(49)26(47)22(16-43)56-33/h6,20-34,43-53H,7-18H2,1-5H3
SMILES	CC1(C)CCC2(C(=O)OC3OC(CO)C(O)C(O)C3O)CCC3(CO)C(=CCC4C5(C)CC(O)C(O)C(C)(C(=O)OC6OC(CO)C(O)C(O)C6O)C5CCC43C)C2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	842.43	Volume:	816.617 ? Van der Waals volume.
Dense:	1.032	LogP:	0.359 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.382 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.838 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	40.0
TPSA:	293.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	11.0	Rings:	7.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.106	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.132	Fsp³:	0.905
MCE-18:	156.75 ? 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:	0.178	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.209 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.106	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.649	MDCK Permeability:	-5.149
Pgp-inhibitor:	0.0	Pgp-substrate:	0.402
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):	0.998
20% Bioavailability (F20%):	0.887	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.389	MRP1:	0.999
Plasma Protein Binding (PPB):	58.033%	Volume Distribution (VD):	-0.284
Fu:	23.071% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.21	BCRP inhibitor:	0.0
BSEP inhibitor:	0.007

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.525
HLM stability:	0.001 ? 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):

0.474

Half-life (T1/2):

3.695

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.154
Human Hepatotoxicity (H-HT):	0.522	Drug-induced Liver Injury (DILI):	0.063
AMES Toxicity:	0.331	Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.307	Skin Sensitization:	0.054
Carcinogencity:	0.039	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.072	Ototoxicity:	1.0
Hematotoxicity:	0.013	Drug-induced Nephrotoxicity:	0.089
Genotoxicity:	0.036	RPMI-8226 Immunitoxicity:	0.069
A549 Cytotoxicity:	0.016	Hek293 Cytotoxicity:	0.468
BCF:	0.509 ? 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:	3.978 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.151 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.362 ? 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
NPO45587	Leucas nutans	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	58

Activity Type	# Activity
Cell line	58

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
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	38994.2	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	44771.33	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set

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 NPC604133 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	20857
0.1-0.2	23524
0.2-0.3	4372
0.3-0.4	842
0.4-0.5	169
0.5-0.6	68
0.6-0.7	17
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
0.7024	Intermediate Similarity	NPC199457
0.6941	Remote Similarity	NPC68419
0.6706	Remote Similarity	NPC237503
0.6667	Remote Similarity	NPC167383
0.6322	Remote Similarity	NPC116794
0.6292	Remote Similarity	NPC271138
0.625	Remote Similarity	NPC306746
0.6207	Remote Similarity	NPC605954
0.618	Remote Similarity	NPC310014
0.618	Remote Similarity	NPC269315
0.6146	Remote Similarity	NPC150400
0.6111	Remote Similarity	NPC102914
0.6111	Remote Similarity	NPC110139
0.6111	Remote Similarity	NPC108709
0.6064	Remote Similarity	NPC29069
0.6044	Remote Similarity	NPC220984
0.6	Remote Similarity	NPC7870
0.6	Remote Similarity	NPC75747
0.5957	Remote Similarity	NPC214484
0.5914	Remote Similarity	NPC209894
0.5833	Remote Similarity	NPC48499
0.5824	Remote Similarity	NPC48249
0.581	Remote Similarity	NPC96641
0.581	Remote Similarity	NPC163183
0.5758	Remote Similarity	NPC295371
0.5758	Remote Similarity	NPC473884
0.5758	Remote Similarity	NPC39211
0.5714	Remote Similarity	NPC235405
0.5714	Remote Similarity	NPC475516
0.5657	Remote Similarity	NPC249848
0.5657	Remote Similarity	NPC107966
0.5644	Remote Similarity	NPC223301
0.5644	Remote Similarity	NPC171544
0.56	Remote Similarity	NPC157868
0.5556	Remote Similarity	NPC139894
0.5545	Remote Similarity	NPC469946
0.5534	Remote Similarity	NPC10607
0.5534	Remote Similarity	NPC46665
0.5514	Remote Similarity	NPC481030
0.551	Remote Similarity	NPC475208
0.549	Remote Similarity	NPC192791
0.549	Remote Similarity	NPC242840
0.549	Remote Similarity	NPC112352
0.5481	Remote Similarity	NPC475591
0.5481	Remote Similarity	NPC236870
0.5481	Remote Similarity	NPC235438
0.5472	Remote Similarity	NPC104372
0.5464	Remote Similarity	NPC90856
0.5437	Remote Similarity	NPC30735
0.5429	Remote Similarity	NPC222580
0.5392	Remote Similarity	NPC473343
0.5385	Remote Similarity	NPC40775
0.5385	Remote Similarity	NPC251768
0.5385	Remote Similarity	NPC159309
0.5385	Remote Similarity	NPC86222
0.5376	Remote Similarity	NPC37739
0.537	Remote Similarity	NPC80986
0.5333	Remote Similarity	NPC191763
0.5333	Remote Similarity	NPC63159
0.5327	Remote Similarity	NPC281148
0.5326	Remote Similarity	NPC46388
0.5319	Remote Similarity	NPC212968
0.5301	Remote Similarity	NPC136313
0.5283	Remote Similarity	NPC297263
0.5238	Remote Similarity	NPC305267
0.5238	Remote Similarity	NPC473459
0.5213	Remote Similarity	NPC65590
0.5213	Remote Similarity	NPC125923
0.5196	Remote Similarity	NPC473373
0.5185	Remote Similarity	NPC114484
0.5182	Remote Similarity	NPC31838
0.5182	Remote Similarity	NPC187290
0.5158	Remote Similarity	NPC187056
0.5158	Remote Similarity	NPC137917
0.5158	Remote Similarity	NPC606216
0.5158	Remote Similarity	NPC607023
0.514	Remote Similarity	NPC609763
0.5138	Remote Similarity	NPC301449
0.5138	Remote Similarity	NPC601290
0.51	Remote Similarity	NPC1046
0.5094	Remote Similarity	NPC102439
0.5088	Remote Similarity	NPC475899
0.5088	Remote Similarity	NPC481031
0.505	Remote Similarity	NPC179434
0.5045	Remote Similarity	NPC481078
0.5042	Remote Similarity	NPC484942

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC604133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7265
0.1-0.2	1818
0.2-0.3	64
0.3-0.4	3
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data