NPASS Compound

Natural Product: NPC472949

Natural Product ID	NPC472949
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WJQOMUVKRDJBGZ-FLHQWXAYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3594169
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 122128 0 0 0 0 0 0 0 0999 V2000 -8.2988 0.4493 -3.5901 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6614 -0.4401 -2.5515 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5954 -0.4515 -1.3563 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2402 0.6587 -0.3573 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9826 0.2213 0.3780 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4079 1.3558 1.0919 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9518 1.3790 1.4369 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0798 0.9195 0.2352 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7516 -0.3366 -0.1223 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1936 -1.4749 0.1433 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8662 -1.5714 0.8161 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0608 -0.4993 0.1693 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6144 0.8425 0.5459 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8456 1.8060 -0.3904 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4532 1.3708 -0.7314 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1863 0.4784 0.2494 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6118 -0.7627 0.2975 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1714 -1.5285 1.5244 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9704 -0.8449 2.2515 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0999 -0.5320 1.3024 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6741 0.3596 0.1657 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2238 -0.0363 -1.1638 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1791 1.7903 0.4276 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2186 -0.0585 1.8662 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3558 -0.7951 1.8380 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4890 0.0338 1.3025 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6512 1.2414 2.1999 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7711 1.2543 3.3985 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5710 -0.0964 4.0308 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7596 -1.1450 3.1586 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4184 -0.2794 5.2298 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1577 -1.2840 5.3135 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4239 0.6294 6.2748 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4240 2.0493 4.3728 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0061 1.4050 2.5717 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2265 0.3525 -0.0038 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1420 -0.1125 -0.9094 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8832 1.0146 -1.6215 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1676 0.3519 -2.1392 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7550 -0.7948 -3.0080 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2964 -1.1022 -3.0130 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6600 -1.0379 -1.8036 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1678 -2.5537 -3.5008 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8580 -2.9388 -3.6471 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1030 -0.4399 -4.3329 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7539 -0.2154 -0.9822 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2549 1.9756 -0.7158 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2505 -1.6960 -0.8795 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2721 1.3086 1.9336 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0900 -0.3739 -0.7124 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3316 0.1708 -2.0514 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3170 2.0532 -0.7427 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3752 -0.8232 1.3592 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5692 -1.1675 1.4555 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4370 -1.4384 2.1865 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4557 -1.7858 -3.1573 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9668 -0.1394 -4.2294 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4967 0.9703 -4.1418 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8625 1.2543 -3.0509 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6342 -0.2368 -1.6826 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6147 -1.4377 -0.8571 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0908 0.6763 0.3706 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1317 1.5945 -0.9033 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7933 2.3146 0.6432 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9329 1.3880 2.1125 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7337 2.4431 1.6092 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8376 0.6956 2.2786 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6415 -2.4594 -0.1002 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9971 -1.4331 1.9106 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3774 -2.5346 0.6881 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3061 -0.5315 -0.9439 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7381 2.8040 0.1129 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3256 1.8681 -1.3912 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3832 0.8478 -1.7355 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1965 2.2632 -0.8631 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0819 0.9738 1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0130 -1.6901 2.2525 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1757 -2.5650 1.3048 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6745 -0.0336 2.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3863 -1.6407 2.9418 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3578 -1.5351 0.8444 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8481 -0.9638 -0.9916 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5083 -0.1384 -1.9776 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9900 0.6993 -1.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2668 2.3055 -0.5645 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1310 1.8048 0.9570 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4040 2.3944 0.9747 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3211 -1.7479 1.3242 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4161 -0.5770 1.4244 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4204 2.1404 1.5816 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7908 1.7689 3.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5022 -0.1625 4.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4391 0.2782 7.2450 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3734 3.0069 4.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2180 0.8992 3.3816 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9388 -0.6599 -0.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3341 1.3907 -2.4894 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8320 1.0797 -2.6172 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3559 -1.7073 -2.7983 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7328 -0.4921 -3.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5887 -3.1623 -2.6498 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8092 -2.7472 -4.3707 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7233 -3.4026 -4.5143 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1040 -0.4093 -4.4094 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2262 -1.0402 -1.2652 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1200 1.7541 -0.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7509 -2.0938 -0.8246 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5860 -1.2791 -1.8408 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9319 -2.5878 -0.7248 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8172 0.5390 2.5869 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1624 1.6175 2.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7010 2.2886 1.9431 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4658 -1.4497 -0.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5544 1.2488 -2.1384 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5689 -0.1830 -2.7518 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6743 2.9038 -0.4009 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3302 2.5388 -0.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2563 1.7969 -1.7892 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7846 -2.0438 2.9330 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2431 -1.6244 -4.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4197 -2.3348 -3.1451 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6088 -2.3598 -2.7567 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 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 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 2 0 31 33 1 0 28 34 1 0 27 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 41 43 1 0 43 44 1 0 40 45 1 0 39 46 1 0 38 47 1 0 17 48 1 0 13 49 1 0 9 50 1 0 50 51 1 0 8 52 1 0 5 53 1 0 53 54 2 0 53 55 1 0 2 56 1 0 51 2 1 0 50 5 1 0 13 8 1 0 17 12 1 0 21 16 1 0 30 25 1 0 42 37 1 0 1 57 1 0 1 58 1 0 1 59 1 0 3 60 1 0 3 61 1 0 4 62 1 0 4 63 1 0 6 64 1 0 6 65 1 0 7 66 1 0 7 67 1 0 10 68 1 0 11 69 1 0 11 70 1 0 12 71 1 0 14 72 1 0 14 73 1 0 15 74 1 0 15 75 1 0 16 76 1 0 18 77 1 0 18 78 1 0 19 79 1 0 19 80 1 0 20 81 1 0 22 82 1 0 22 83 1 0 22 84 1 0 23 85 1 0 23 86 1 0 23 87 1 0 25 88 1 0 26 89 1 0 27 90 1 0 28 91 1 0 29 92 1 0 33 93 1 0 34 94 1 0 35 95 1 0 37 96 1 0 38 97 1 0 39 98 1 0 40 99 1 0 41100 1 0 43101 1 0 43102 1 0 44103 1 0 45104 1 0 46105 1 0 47106 1 0 48107 1 0 48108 1 0 48109 1 0 49110 1 0 49111 1 0 49112 1 0 50113 1 0 51114 1 0 51115 1 0 52116 1 0 52117 1 0 52118 1 0 55119 1 0 56120 1 0 56121 1 0 56122 1 0 M END

Standard InCHIKey	WJQOMUVKRDJBGZ-FLHQWXAYSA-N
Standard InCHI	InChI=1S/C42H66O14/c1-37(2)14-16-42(36(51)52)17-15-40(6)20(21(42)18-37)8-9-24-39(5)12-11-25(38(3,4)23(39)10-13-41(24,40)7)54-35-32(29(47)28(46)31(55-35)33(49)50)56-34-30(48)27(45)26(44)22(19-43)53-34/h8,21-32,34-35,43-48H,9-19H2,1-7H3,(H,49,50)(H,51,52)/t21-,22+,23-,24+,25-,26+,27-,28-,29-,30+,31-,32+,34?,35+,39-,40+,41+,42-/m0/s1
SMILES	CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)O)OC7C(C(C(C(O7)CO)O)O)O)C)C)C2C1)C)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	794.45	Volume:	790.246 ? Van der Waals volume.
Dense:	1.005	LogP:	2.191 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.638 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.968 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	40.0
TPSA:	232.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.763	Fsp³:	0.905
MCE-18:	154.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.117	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.39 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.153	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.072	MDCK Permeability:	-5.013
Pgp-inhibitor:	0.0	Pgp-substrate:	0.008
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):	0.789
20% Bioavailability (F20%):	0.003	30% Bioavailability (F30%):	0.07
50% Bioavailability (F50%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	64.839%	Volume Distribution (VD):	-0.538
Fu:	26.282% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.02	BCRP inhibitor:	0.0
BSEP inhibitor:	0.013

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.251	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	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):

0.051

Half-life (T1/2):

2.978

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.019
Human Hepatotoxicity (H-HT):	0.421	Drug-induced Liver Injury (DILI):	0.379
AMES Toxicity:	0.027	Rat Oral Acute Toxicity:	0.141
Maximum Recommended Daily Dose:	0.345	Skin Sensitization:	0.022
Carcinogencity:	0.011	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.034
Drug-induced Neurotoxicity:	0.06	Ototoxicity:	0.999
Hematotoxicity:	0.044	Drug-induced Nephrotoxicity:	0.165
Genotoxicity:	0.007	RPMI-8226 Immunitoxicity:	0.025
A549 Cytotoxicity:	0.005	Hek293 Cytotoxicity:	0.096
BCF:	0.13 ? 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:	4.094 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.05 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.062 ? 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
NPO33325	silphium laciniatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26287548]
NPO33325	silphium laciniatum	Species	Asteraceae	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
IC50	1

Activity Type	# Activity
Cell line	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
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	7000.0	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 NPC472949 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	23406
0.1-0.2	22090
0.2-0.3	2989
0.3-0.4	748
0.4-0.5	381
0.5-0.6	118
0.6-0.7	57
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8523	High Similarity	NPC164194
0.8235	Intermediate Similarity	NPC606107
0.8172	Intermediate Similarity	NPC22956
0.8152	Intermediate Similarity	NPC127056
0.8043	Intermediate Similarity	NPC25605
0.7812	Intermediate Similarity	NPC114304
0.7684	Intermediate Similarity	NPC488561
0.764	Intermediate Similarity	NPC286347
0.7579	Intermediate Similarity	NPC109079
0.7576	Intermediate Similarity	NPC257468
0.75	Intermediate Similarity	NPC204407
0.7474	Intermediate Similarity	NPC59804
0.7368	Intermediate Similarity	NPC12288
0.7353	Intermediate Similarity	NPC324875
0.7353	Intermediate Similarity	NPC292677
0.7292	Intermediate Similarity	NPC56713
0.7282	Intermediate Similarity	NPC488564
0.72	Intermediate Similarity	NPC251768
0.7157	Intermediate Similarity	NPC79718
0.7157	Intermediate Similarity	NPC119794
0.7041	Intermediate Similarity	NPC114441
0.703	Intermediate Similarity	NPC180550
0.703	Intermediate Similarity	NPC35405
0.701	Intermediate Similarity	NPC136877
0.6979	Remote Similarity	NPC270667
0.6972	Remote Similarity	NPC166422
0.6972	Remote Similarity	NPC219180
0.6961	Remote Similarity	NPC139044
0.69	Remote Similarity	NPC80843
0.6882	Remote Similarity	NPC31839
0.6863	Remote Similarity	NPC104400
0.6863	Remote Similarity	NPC10320
0.6848	Remote Similarity	NPC283849
0.6832	Remote Similarity	NPC469945
0.6827	Remote Similarity	NPC64715
0.6822	Remote Similarity	NPC480939
0.6818	Remote Similarity	NPC251263
0.6771	Remote Similarity	NPC191410
0.6768	Remote Similarity	NPC174679
0.6768	Remote Similarity	NPC279554
0.6762	Remote Similarity	NPC276093
0.6698	Remote Similarity	NPC301449
0.6698	Remote Similarity	NPC323359
0.6698	Remote Similarity	NPC601290
0.6696	Remote Similarity	NPC54636
0.6667	Remote Similarity	NPC294112
0.6667	Remote Similarity	NPC62725
0.6634	Remote Similarity	NPC6377
0.6634	Remote Similarity	NPC208381
0.66	Remote Similarity	NPC309780
0.6571	Remote Similarity	NPC481082
0.6571	Remote Similarity	NPC164419
0.6476	Remote Similarity	NPC118440
0.6429	Remote Similarity	NPC323341
0.6364	Remote Similarity	NPC475472
0.6346	Remote Similarity	NPC192791
0.6321	Remote Similarity	NPC471383
0.6316	Remote Similarity	NPC28198
0.6316	Remote Similarity	NPC476123
0.6306	Remote Similarity	NPC288205
0.6306	Remote Similarity	NPC51465
0.6296	Remote Similarity	NPC114692
0.6283	Remote Similarity	NPC133818
0.6273	Remote Similarity	NPC475486
0.6262	Remote Similarity	NPC131469
0.6216	Remote Similarity	NPC280941
0.6216	Remote Similarity	NPC235772
0.6214	Remote Similarity	NPC482748
0.6204	Remote Similarity	NPC95437
0.6204	Remote Similarity	NPC302887
0.62	Remote Similarity	NPC480938
0.6182	Remote Similarity	NPC187618
0.6147	Remote Similarity	NPC236657
0.6134	Remote Similarity	NPC161717
0.6111	Remote Similarity	NPC73829
0.605	Remote Similarity	NPC258617
0.6036	Remote Similarity	NPC120116
0.6036	Remote Similarity	NPC160452
0.6	Remote Similarity	NPC471385
0.6	Remote Similarity	NPC284807
0.6	Remote Similarity	NPC157868
0.5979	Remote Similarity	NPC57362
0.596	Remote Similarity	NPC100383
0.5946	Remote Similarity	NPC23275
0.5926	Remote Similarity	NPC44716
0.5909	Remote Similarity	NPC488515
0.5893	Remote Similarity	NPC488209
0.5882	Remote Similarity	NPC470518
0.5877	Remote Similarity	NPC476992
0.5872	Remote Similarity	NPC475591
0.5872	Remote Similarity	NPC236870
0.5862	Remote Similarity	NPC471384
0.5842	Remote Similarity	NPC475633
0.5841	Remote Similarity	NPC469947
0.5841	Remote Similarity	NPC480948
0.5826	Remote Similarity	NPC313110
0.5804	Remote Similarity	NPC482737
0.5804	Remote Similarity	NPC477075
0.58	Remote Similarity	NPC242611
0.5798	Remote Similarity	NPC329923
0.5798	Remote Similarity	NPC475281
0.5778	Remote Similarity	NPC120840
0.5763	Remote Similarity	NPC470218
0.5702	Remote Similarity	NPC187290
0.5701	Remote Similarity	NPC488516
0.5691	Remote Similarity	NPC111466
0.5688	Remote Similarity	NPC605226
0.5673	Remote Similarity	NPC76999
0.5664	Remote Similarity	NPC218954
0.5664	Remote Similarity	NPC291903
0.5664	Remote Similarity	NPC477076
0.5664	Remote Similarity	NPC477079
0.5652	Remote Similarity	NPC480936
0.5636	Remote Similarity	NPC159309
0.5636	Remote Similarity	NPC473383
0.5636	Remote Similarity	NPC86222
0.563	Remote Similarity	NPC283417
0.563	Remote Similarity	NPC200049
0.5614	Remote Similarity	NPC477077
0.5614	Remote Similarity	NPC477078
0.5603	Remote Similarity	NPC475119
0.5596	Remote Similarity	NPC75417
0.5577	Remote Similarity	NPC473481
0.5565	Remote Similarity	NPC329657
0.5556	Remote Similarity	NPC473884
0.5556	Remote Similarity	NPC473824
0.5556	Remote Similarity	NPC603026
0.5534	Remote Similarity	NPC473538
0.5534	Remote Similarity	NPC480937
0.5495	Remote Similarity	NPC40775
0.547	Remote Similarity	NPC471962
0.5447	Remote Similarity	NPC265841
0.5447	Remote Similarity	NPC488308
0.5444	Remote Similarity	NPC480946
0.5444	Remote Similarity	NPC130577
0.5444	Remote Similarity	NPC142415
0.5444	Remote Similarity	NPC102683
0.5439	Remote Similarity	NPC247315
0.5439	Remote Similarity	NPC482728
0.5439	Remote Similarity	NPC114484
0.541	Remote Similarity	NPC181066
0.541	Remote Similarity	NPC82380
0.541	Remote Similarity	NPC244296
0.5403	Remote Similarity	NPC312650
0.5385	Remote Similarity	NPC270768
0.5385	Remote Similarity	NPC59263
0.5385	Remote Similarity	NPC210106
0.5378	Remote Similarity	NPC151543
0.5372	Remote Similarity	NPC475140
0.537	Remote Similarity	NPC108748
0.5366	Remote Similarity	NPC484061
0.5366	Remote Similarity	NPC484062
0.5364	Remote Similarity	NPC482747
0.5364	Remote Similarity	NPC202666
0.5364	Remote Similarity	NPC471961
0.5364	Remote Similarity	NPC242015
0.5364	Remote Similarity	NPC469946
0.5364	Remote Similarity	NPC482717
0.5351	Remote Similarity	NPC262199
0.5321	Remote Similarity	NPC275343
0.5315	Remote Similarity	NPC242840
0.5315	Remote Similarity	NPC112352
0.5312	Remote Similarity	NPC488309
0.531	Remote Similarity	NPC63159
0.5304	Remote Similarity	NPC281148
0.5289	Remote Similarity	NPC482736
0.5289	Remote Similarity	NPC482738
0.5285	Remote Similarity	NPC4749
0.5285	Remote Similarity	NPC71391
0.5285	Remote Similarity	NPC488211
0.528	Remote Similarity	NPC271610
0.5273	Remote Similarity	NPC470512
0.5273	Remote Similarity	NPC482751
0.5268	Remote Similarity	NPC471965
0.5268	Remote Similarity	NPC482749
0.5259	Remote Similarity	NPC75318
0.5242	Remote Similarity	NPC21691
0.5238	Remote Similarity	NPC484059
0.5238	Remote Similarity	NPC484060
0.5229	Remote Similarity	NPC482750
0.5225	Remote Similarity	NPC263756
0.5225	Remote Similarity	NPC213674
0.5225	Remote Similarity	NPC475171
0.5217	Remote Similarity	NPC275809
0.521	Remote Similarity	NPC25998
0.5203	Remote Similarity	NPC47995
0.5203	Remote Similarity	NPC277212
0.5203	Remote Similarity	NPC30279
0.5194	Remote Similarity	NPC484063
0.5194	Remote Similarity	NPC484064
0.5189	Remote Similarity	NPC480943
0.5185	Remote Similarity	NPC48499
0.5182	Remote Similarity	NPC480424
0.5182	Remote Similarity	NPC40085
0.5175	Remote Similarity	NPC258885
0.5175	Remote Similarity	NPC482722
0.5175	Remote Similarity	NPC471963
0.5167	Remote Similarity	NPC609119
0.5161	Remote Similarity	NPC158141

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6939
0.1-0.2	2146
0.2-0.3	56
0.3-0.4	7
0.4-0.5	1
0.5-0.6	1
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
0.5364	Remote Similarity	NPD8328	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data