NPASS Compound

Natural Product: NPC185977

Natural Product ID	NPC185977
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QUZHZFAQJATMCA-CVELTQQQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	91551905
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0000637] Glycosylglycerols [CHEMONTID:0003822] Glycosyldiradylglycerols [CHEMONTID:0003067] Glycosyldiacylglycerols [CHEMONTID:0003259] 1,2-diacyl-3-O-beta-D-galactosyl-sn-glycerols

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 129129 0 0 0 0 0 0 0 0999 V2000 30.8398 -9.2964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 29.4303 -8.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 28.0208 -8.2704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 26.8717 -9.2345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 25.4622 -8.7215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 24.0526 -8.2085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 23.7922 -6.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 22.3826 -6.2182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.9731 -5.7052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.8240 -6.6694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.4145 -6.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.0049 -5.6433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5954 -5.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1859 -4.6173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7763 -4.1042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3668 -3.5912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9572 -3.0782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5477 -2.5652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3986 -3.5293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2872 -1.0879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8777 -0.5749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4681 -0.0619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 1.8121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5691 2.3251 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9812 1.3477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0170 2.4967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1447 2.3429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5300 3.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0431 5.3158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5561 6.7253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0691 8.1349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5821 9.5444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0952 10.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6082 12.3635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1212 13.7730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5984 14.0335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1115 15.4430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6245 16.8526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6603 18.0017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1734 19.4112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6864 20.8207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1636 21.0812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6766 22.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1897 23.9003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 32.2494 -9.8095 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 30.3268 -10.7060 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 31.3529 -7.8869 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 29.9433 -7.3739 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 28.9173 -10.1929 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 27.7603 -6.7932 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 27.1322 -10.7118 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 25.9752 -7.3120 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 24.9491 -10.1311 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.9036 -9.1727 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 24.9412 -5.7671 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 21.8696 -7.6278 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.8956 -4.8087 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 20.7126 -4.2280 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 20.0845 -8.1466 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.9275 -4.7468 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.9014 -7.5659 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.4919 -7.0529 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.5180 -4.2338 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.1084 -3.7208 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0824 -6.5398 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6728 -6.0268 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6989 -3.2077 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2893 -2.6947 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2633 -5.5138 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8537 -5.0008 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8798 -2.1817 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4442 -4.4877 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4703 -1.6686 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3907 0.8346 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3647 -1.9844 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9551 -1.4714 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7212 -1.0104 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1511 1.3320 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3286 -0.8886 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 -2.7762 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -1.8121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1686 0.4341 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 2.7762 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6465 3.2216 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5215 1.1018 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8296 3.8023 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 -0.4512 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 -3.7404 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 -3.2893 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1205 4.4193 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9396 3.3932 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4526 4.8028 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6335 5.8288 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1465 7.2384 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9656 6.2123 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4787 7.6219 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6596 8.6479 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1726 10.0575 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9917 9.0314 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5047 10.4409 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6856 11.4670 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0177 11.8505 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1987 12.8765 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1571 14.9221 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5626 12.8844 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5210 14.9300 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7019 15.9561 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1017 17.1131 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1831 17.7412 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7638 19.9242 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5829 18.8982 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7222 21.9698 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1278 19.9321 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0862 21.9777 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2671 23.0038 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7027 25.3098 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7801 24.4133 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.5992 23.3873 0.0000 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 2 3 7 8 1 0 8 9 1 0 9 10 2 3 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 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 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 30 31 1 0 29 32 1 0 28 33 1 0 27 34 1 0 26 35 1 0 22 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 39 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 1 0 46 47 2 3 47 48 1 0 48 49 1 0 49 50 2 3 50 51 1 0 51 52 1 0 52 53 2 3 53 54 1 0 54 55 1 0 32 25 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 0 2 60 1 0 3 61 1 0 4 62 1 0 5 63 1 0 5 64 1 0 6 65 1 0 7 66 1 0 8 67 1 0 8 68 1 0 9 69 1 0 10 70 1 0 11 71 1 0 11 72 1 0 12 73 1 0 12 74 1 0 13 75 1 0 13 76 1 0 14 77 1 0 14 78 1 0 15 79 1 0 15 80 1 0 16 81 1 0 16 82 1 0 17 83 1 0 17 84 1 0 21 85 1 0 21 86 1 0 22 87 1 1 23 88 1 0 23 89 1 0 25 90 1 6 26 91 1 1 27 92 1 6 28 93 1 6 29 94 1 6 30 95 1 0 30 96 1 0 31 97 1 0 33 98 1 0 34 99 1 0 35100 1 0 39101 1 0 39102 1 0 40103 1 0 40104 1 0 41105 1 0 41106 1 0 42107 1 0 42108 1 0 43109 1 0 43110 1 0 44111 1 0 44112 1 0 45113 1 0 45114 1 0 46115 1 0 47116 1 0 48117 1 0 48118 1 0 49119 1 0 50120 1 0 51121 1 0 51122 1 0 52123 1 0 53124 1 0 54125 1 0 54126 1 0 55127 1 0 55128 1 0 55129 1 0 M END

Standard InCHIKey	QUZHZFAQJATMCA-CVELTQQQSA-N
Standard InCHI	InChI=1S/C45H74O10/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(47)52-36-38(37-53-45-44(51)43(50)42(49)39(35-46)55-45)54-41(48)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,38-39,42-46,49-51H,3-4,9-10,15-16,21-37H2,1-2H3/t38-,39-,42+,43+,44-,45-/m1/s1
SMILES	CCC=CCC=CCC=CCCCCCCCC(=O)OC[C@H](CO[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)OC(=O)CCCCCCCC=CCC=CCC=CCC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	774.53	Volume:	845.13 ? Van der Waals volume.
Dense:	0.916	LogP:	9.265 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.62 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.922 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	35.0	Rigid Bonds:	14.0
TPSA:	151.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	4.0	Rings:	1.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.029	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.973	Fsp³:	0.689
MCE-18:	23.447 ? 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:	0.716	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:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.585	Promiscuous compounds:	0.166

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.33	MDCK Permeability:	-5.049
Pgp-inhibitor:	0.142	Pgp-substrate:	0.116
PAMPA:	0.009 ? 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):	0.402
20% Bioavailability (F20%):	0.983	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.982
Plasma Protein Binding (PPB):	97.748%	Volume Distribution (VD):	-0.418
Fu:	1.456% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.158
OATP1B3 inhibitor:	0.737	BCRP inhibitor:	0.036
BSEP inhibitor:	0.851

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.026	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.017	CYP2C8-inhibitor:	1.0
HLM stability:	0.033 ? 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):

2.814

Half-life (T1/2):

0.98

ADMET: Toxicity

hERG Blockers:	0.087	hERG Blockers (10um):	0.079
Human Hepatotoxicity (H-HT):	0.026	Drug-induced Liver Injury (DILI):	0.002
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	1.0
Carcinogencity:	0.271	Eye Corrosion:	0.009
Eye Irritation:	0.627	Respiratory Toxicity:	0.346
Drug-induced Neurotoxicity:	0.031	Ototoxicity:	0.629
Hematotoxicity:	0.004	Drug-induced Nephrotoxicity:	0.801
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.081
A549 Cytotoxicity:	0.951	Hek293 Cytotoxicity:	0.163
BCF:	1.003 ? 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:	5.131 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.724 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.495 ? 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
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10757717]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[12943781]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951446]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	stems	Thailand	n.a.	PMID[14510595]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738381]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	Argentine	n.a.	PMID[14738381]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21905650]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697288]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32998509]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36031812]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36938717]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37533365]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[9599285]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15393	Eucalyptus flocktoniae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13548	Chrozophora obliqua	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16175	Trichia floriformis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16678	Flindersia brayleyana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13859	Senecio flavus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13710	Lyophyllum shimeji	Species	Lyophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3391	Jungermannia obovata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24732	Cereus weberi	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15138	Rheum webbianum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4267	Ceratocystis clavigera	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11194	Bombus hortorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5552	Solanum sisymbriifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16175	Trichia floriformis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13230	Pedicularis condensata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15272	Mascarenhasia arborescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5078	Turraeanthus mannii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4935	Dinemasporium strigosum	Species	Chaetosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15755	Thymbra spicata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5269	Coleus garckeanus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11881	Adenopeltis colliguaya	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16678	Flindersia brayleyana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12680	Perityle vaseyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15393	Eucalyptus flocktoniae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14218	Spodoptera littoralis	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13548	Chrozophora obliqua	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8499	Osmerus mordax	Species	Osmeridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14034	Salvia coulteri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15015	Meconopsis napaulensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23289	Heracleum sphondylium	Species	Apiaceae	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

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

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 NPC185977 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	18868
0.1-0.2	25152
0.2-0.3	5179
0.3-0.4	527
0.4-0.5	97
0.5-0.6	17
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	5
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC236649
0.931	High Similarity	NPC110813
0.9298	High Similarity	NPC21693
0.9167	High Similarity	NPC38295
0.8983	High Similarity	NPC133377
0.8871	High Similarity	NPC470313
0.8871	High Similarity	NPC473500
0.8871	High Similarity	NPC611497
0.8772	High Similarity	NPC488689
0.8065	Intermediate Similarity	NPC156089
0.7719	Intermediate Similarity	NPC488690
0.7183	Intermediate Similarity	NPC22558
0.7059	Intermediate Similarity	NPC488692
0.6857	Remote Similarity	NPC476612
0.6857	Remote Similarity	NPC476613
0.6618	Remote Similarity	NPC488694
0.64	Remote Similarity	NPC476611
0.6	Remote Similarity	NPC83839
0.5965	Remote Similarity	NPC54925
0.5821	Remote Similarity	NPC489083
0.5789	Remote Similarity	NPC271921
0.5735	Remote Similarity	NPC488693
0.5652	Remote Similarity	NPC331437
0.5574	Remote Similarity	NPC473559
0.5574	Remote Similarity	NPC324981
0.5397	Remote Similarity	NPC206601
0.5254	Remote Similarity	NPC330426
0.5254	Remote Similarity	NPC127091
0.5254	Remote Similarity	NPC22101
0.5152	Remote Similarity	NPC285003
0.5147	Remote Similarity	NPC469469
0.5128	Remote Similarity	NPC488691
0.5082	Remote Similarity	NPC48218
0.5082	Remote Similarity	NPC141481
0.5082	Remote Similarity	NPC464342

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC185977 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6647
0.1-0.2	2341
0.2-0.3	143
0.3-0.4	13
0.4-0.5	6
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