NPASS Compound

Natural Product: NPC209528

Natural Product ID	NPC209528
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XQSMSRSJNXQHLT-ABYIYZCWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11803929
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 114120 0 0 0 0 0 0 0 0999 V2000 -7.2900 -3.0042 -2.8548 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5425 -2.9276 -1.5119 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1104 -4.0191 -0.6699 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2366 -4.4556 0.4762 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8489 -4.6466 -0.1016 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4045 -3.3229 -0.6853 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2023 -3.0128 -1.7870 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3498 -2.3150 0.2611 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0875 -1.8193 0.3491 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4219 -2.1066 1.7139 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9302 -1.9065 1.4166 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6824 -0.5897 0.7804 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7454 -0.5758 0.2439 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6516 -0.9279 1.2089 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9804 -0.8765 0.7210 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7846 -0.0236 1.6615 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3195 -0.9697 2.7713 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4223 -1.7500 2.0501 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7888 -2.3544 0.8403 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4665 -1.9663 -0.4549 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4319 -2.1908 0.8172 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9773 -2.6928 2.8818 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8860 -0.2305 3.7780 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9324 0.5628 1.1173 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2633 1.8974 1.3084 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4852 2.5839 1.9953 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4710 2.4821 0.7371 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3199 1.8334 -0.0011 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5228 2.4230 -0.5639 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9403 3.7159 -0.3674 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0983 4.2461 -0.9095 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8821 3.4422 -1.6907 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5215 2.1269 -1.9323 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3546 1.6472 -1.3662 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3493 1.3650 -2.7290 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1331 0.0352 -3.0909 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0562 3.9552 -2.2485 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5169 -0.2515 -0.2752 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8856 -0.3640 0.1487 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6285 0.2775 -0.8365 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6042 1.6833 -0.8058 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5893 2.3270 -1.5305 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7553 1.6512 -2.1761 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5127 3.6975 -1.5295 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5297 4.3743 -2.2306 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4935 5.7274 -2.2024 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4149 6.4572 -1.4893 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3959 5.7978 -0.7888 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4478 4.4051 -0.8074 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3781 3.7685 -0.1461 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5020 2.4349 -0.1119 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5996 1.9118 0.6788 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2342 2.7758 1.5685 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2982 2.4212 2.3465 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7656 1.1253 2.2359 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1851 0.2291 1.3787 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1116 0.6375 0.6132 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6710 -1.0491 1.2918 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8580 0.7198 3.0174 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4043 7.8572 -1.4406 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5988 3.6234 -2.9531 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6047 -2.9239 0.5039 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6967 -3.3617 2.1789 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9827 -5.5377 -1.1855 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6957 -5.6602 0.9891 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3784 -3.6255 -0.2410 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3337 -2.0291 -3.3585 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3288 -3.4036 -2.6651 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7917 -3.7846 -3.4578 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8038 -1.9026 -1.1301 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2850 -4.9209 -1.3064 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1963 -3.6700 1.2632 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1173 -5.0654 0.5784 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3882 -3.4717 -1.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4016 -2.3558 -0.3951 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7392 -1.3432 2.4531 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3324 -1.9703 2.3457 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7605 0.1924 1.5983 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7870 -1.3573 -0.5713 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9714 0.3824 -0.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9685 -0.5279 -0.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1676 0.7221 2.2090 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4770 -1.6152 3.0593 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1619 -0.9744 1.7153 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9516 -3.4756 0.9377 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7942 -1.2594 -0.9919 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5355 -2.8642 -1.1254 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4579 -1.5262 -0.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7542 -3.6235 2.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7229 -0.6784 4.0526 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6874 3.5468 0.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0919 0.7720 -0.2008 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3452 4.3712 0.2430 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3930 5.2774 -0.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0843 0.6177 -1.5643 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0966 -0.4286 -3.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6729 -0.5080 -2.2432 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4253 0.0458 -3.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0389 4.1113 -3.2492 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8939 0.1913 1.1294 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7293 6.2716 -2.7463 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1499 6.3168 -0.2054 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8669 3.7970 1.6584 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7827 3.1116 3.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6827 -0.0634 -0.0859 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6674 -1.2775 1.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2167 1.3365 3.7054 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1989 8.3990 -1.7158 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1013 4.0736 -3.7310 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0973 -3.4885 0.9243 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8849 -3.8115 2.5237 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1782 -6.4144 -0.7657 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9779 -6.1919 1.4178 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8120 -4.2948 0.3372 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 6 8 1 0 8 9 1 0 9 10 1 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 19 21 1 0 18 22 1 0 17 23 1 0 16 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 32 37 1 0 12 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 2 0 53 54 1 0 54 55 2 0 55 56 1 0 56 57 2 0 56 58 1 0 55 59 1 0 47 60 1 0 45 61 1 0 11 62 1 0 10 63 1 0 5 64 1 0 4 65 1 0 3 66 1 0 7 2 1 0 39 9 1 0 51 41 2 0 57 52 1 0 21 15 1 0 34 29 1 0 49 44 1 0 1 67 1 0 1 68 1 0 1 69 1 0 2 70 1 1 3 71 1 6 4 72 1 1 5 73 1 1 6 74 1 6 9 75 1 6 10 76 1 1 11 77 1 1 12 78 1 1 13 79 1 0 13 80 1 0 15 81 1 6 16 82 1 1 17 83 1 1 18 84 1 6 19 85 1 1 20 86 1 0 20 87 1 0 20 88 1 0 22 89 1 0 23 90 1 0 27 91 1 0 28 92 1 0 30 93 1 0 31 94 1 0 34 95 1 0 36 96 1 0 36 97 1 0 36 98 1 0 37 99 1 0 39100 1 1 46101 1 0 48102 1 0 53103 1 0 54104 1 0 57105 1 0 58106 1 0 59107 1 0 60108 1 0 61109 1 0 62110 1 0 63111 1 0 64112 1 0 65113 1 0 66114 1 0 M END

Standard InCHIKey	XQSMSRSJNXQHLT-ABYIYZCWSA-N
Standard InCHI	InChI=1S/C43H48O23/c1-15-29(50)33(54)36(57)41(60-15)66-40-35(56)31(52)26(14-59-42-39(34(55)30(51)16(2)61-42)64-27(49)9-5-17-4-7-21(46)24(10-17)58-3)63-43(40)65-38-32(53)28-23(48)12-19(44)13-25(28)62-37(38)18-6-8-20(45)22(47)11-18/h4-13,15-16,26,29-31,33-36,39-48,50-52,54-57H,14H2,1-3H3/b9-5+/t15-,16-,26+,29-,30-,31-,33+,34+,35-,36+,39+,40+,41-,42+,43-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H]([C@@H](CO[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)OC(=O)/C=C/c2ccc(c(c2)OC)O)O[C@H]1Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	932.26	Volume:	860.29 ? Van der Waals volume.
Dense:	1.084	LogP:	0.518 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.778 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.3 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	44.0
TPSA:	363.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	12.0	Rings:	7.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.047	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.776	Fsp³:	0.442
MCE-18:	174.194 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.721	Fluc inhibitor:	0.636 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.738 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.663 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.296	Promiscuous compounds:	0.518

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.333	MDCK Permeability:	-5.231
Pgp-inhibitor:	0.0	Pgp-substrate:	0.929
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):	0.004
20% Bioavailability (F20%):	0.695	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.003
Plasma Protein Binding (PPB):	84.225%	Volume Distribution (VD):	-0.051
Fu:	13.363% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.382
BSEP inhibitor:	0.635

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.015
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.064 ? 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):

1.076

Half-life (T1/2):

5.533

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.343
Human Hepatotoxicity (H-HT):	0.212	Drug-induced Liver Injury (DILI):	0.784
AMES Toxicity:	0.758	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.085	Skin Sensitization:	1.0
Carcinogencity:	0.006	Eye Corrosion:	0.0
Eye Irritation:	0.062	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.986
Hematotoxicity:	0.012	Drug-induced Nephrotoxicity:	0.095
Genotoxicity:	0.535	RPMI-8226 Immunitoxicity:	0.122
A549 Cytotoxicity:	0.889	Hek293 Cytotoxicity:	0.758
BCF:	0.601 ? 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:	3.46 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.94 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.285 ? 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
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	bud covers	n.a.	n.a.	PMID[11975520]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[12662107]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16643051]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[16989517]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3839140]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7684040]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9868153]
NPO10892	Xanthorrhoea resinosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5380	Eucalyptus australiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10594	Centaurea solstitialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14075	Streptomyces viridogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12726	Piptostigma fugax	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO875	Cryptocarya oblata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7608	Phelline lucida	Species	Phellinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13192	Chara ceratophylla	Species	Characeae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16013	Inga velutina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12726	Piptostigma fugax	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12035	Rhododendron ungerni	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20585	Urochloa decumbens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16306	Curcuma caesia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13683	Cosmos diversifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9342	Solenopsis punctaticeps	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO206	Ormosia nobilis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1398	Trichodesma incanum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11046	Ocimum pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10892	Xanthorrhoea resinosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10594	Centaurea solstitialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5380	Eucalyptus australiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12207	Lagochilus leiacanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14075	Streptomyces viridogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10928	Xenia obscuronata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3059	Erythrina pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2046	Cathormion altissimum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12557	Strychnos tricalysioides	Species	Loganiaceae	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 NPC209528 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	16957
0.1-0.2	28379
0.2-0.3	3652
0.3-0.4	504
0.4-0.5	199
0.5-0.6	115
0.6-0.7	35
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8018	Intermediate Similarity	NPC162394
0.8	Intermediate Similarity	NPC487501
0.7607	Intermediate Similarity	NPC21359
0.7607	Intermediate Similarity	NPC460984
0.7339	Intermediate Similarity	NPC487500
0.7333	Intermediate Similarity	NPC473554
0.729	Intermediate Similarity	NPC122467
0.7154	Intermediate Similarity	NPC487502
0.7097	Intermediate Similarity	NPC249560
0.7083	Intermediate Similarity	NPC25946
0.7054	Intermediate Similarity	NPC89052
0.7	Intermediate Similarity	NPC89127
0.68	Remote Similarity	NPC72554
0.6783	Remote Similarity	NPC173837
0.6727	Remote Similarity	NPC12013
0.6727	Remote Similarity	NPC11432
0.6727	Remote Similarity	NPC477613
0.6698	Remote Similarity	NPC95866
0.6667	Remote Similarity	NPC30011
0.664	Remote Similarity	NPC275977
0.6589	Remote Similarity	NPC97817
0.6581	Remote Similarity	NPC303694
0.6557	Remote Similarity	NPC241781
0.6475	Remote Similarity	NPC480444
0.6446	Remote Similarity	NPC470713
0.6435	Remote Similarity	NPC218161
0.6435	Remote Similarity	NPC602448
0.6393	Remote Similarity	NPC156785
0.6393	Remote Similarity	NPC488736
0.6393	Remote Similarity	NPC488733
0.6348	Remote Similarity	NPC221342
0.6348	Remote Similarity	NPC476470
0.6306	Remote Similarity	NPC155877
0.6299	Remote Similarity	NPC487499
0.629	Remote Similarity	NPC488737
0.626	Remote Similarity	NPC488740
0.625	Remote Similarity	NPC231787
0.6147	Remote Similarity	NPC476215
0.6121	Remote Similarity	NPC220173
0.6048	Remote Similarity	NPC480445
0.6018	Remote Similarity	NPC203259
0.6018	Remote Similarity	NPC33054
0.6018	Remote Similarity	NPC176740
0.6018	Remote Similarity	NPC471725
0.6018	Remote Similarity	NPC134532
0.6018	Remote Similarity	NPC602582
0.6017	Remote Similarity	NPC223426
0.5984	Remote Similarity	NPC192539
0.5968	Remote Similarity	NPC488734
0.5968	Remote Similarity	NPC488735
0.5968	Remote Similarity	NPC488732
0.5968	Remote Similarity	NPC488738
0.5966	Remote Similarity	NPC483765
0.5966	Remote Similarity	NPC81042
0.5948	Remote Similarity	NPC473327
0.5942	Remote Similarity	NPC33083
0.5935	Remote Similarity	NPC470718
0.5897	Remote Similarity	NPC142142
0.5847	Remote Similarity	NPC476472
0.5847	Remote Similarity	NPC294815
0.5847	Remote Similarity	NPC16194
0.584	Remote Similarity	NPC488739
0.5806	Remote Similarity	NPC139571
0.5804	Remote Similarity	NPC254855
0.5804	Remote Similarity	NPC94610
0.5798	Remote Similarity	NPC470445
0.5789	Remote Similarity	NPC163242
0.5789	Remote Similarity	NPC272068
0.5772	Remote Similarity	NPC217520
0.5763	Remote Similarity	NPC221288
0.5763	Remote Similarity	NPC194836
0.5763	Remote Similarity	NPC91493
0.5763	Remote Similarity	NPC605081
0.575	Remote Similarity	NPC483767
0.575	Remote Similarity	NPC483769
0.575	Remote Similarity	NPC483768
0.575	Remote Similarity	NPC483766
0.5748	Remote Similarity	NPC474522
0.5725	Remote Similarity	NPC480470
0.5714	Remote Similarity	NPC474093
0.5714	Remote Similarity	NPC104910
0.5692	Remote Similarity	NPC480472
0.5667	Remote Similarity	NPC292929
0.5645	Remote Similarity	NPC470712
0.5645	Remote Similarity	NPC480441
0.5625	Remote Similarity	NPC470719
0.5625	Remote Similarity	NPC470717
0.5583	Remote Similarity	NPC85751
0.5583	Remote Similarity	NPC19240
0.5581	Remote Similarity	NPC470720
0.5574	Remote Similarity	NPC214621
0.5574	Remote Similarity	NPC34267
0.5573	Remote Similarity	NPC480442
0.5565	Remote Similarity	NPC477895
0.5556	Remote Similarity	NPC255157
0.5556	Remote Similarity	NPC35167
0.5556	Remote Similarity	NPC259896
0.5517	Remote Similarity	NPC173582
0.5517	Remote Similarity	NPC265885
0.5517	Remote Similarity	NPC181465
0.5517	Remote Similarity	NPC215710
0.5517	Remote Similarity	NPC473438
0.5517	Remote Similarity	NPC253788
0.55	Remote Similarity	NPC97119
0.5484	Remote Similarity	NPC470416
0.5469	Remote Similarity	NPC295625
0.542	Remote Similarity	NPC209550
0.5391	Remote Similarity	NPC116864
0.5391	Remote Similarity	NPC244776
0.5385	Remote Similarity	NPC67326
0.5385	Remote Similarity	NPC39834
0.5378	Remote Similarity	NPC126784
0.5378	Remote Similarity	NPC241423
0.5372	Remote Similarity	NPC101399
0.5372	Remote Similarity	NPC217822
0.5372	Remote Similarity	NPC11847
0.5372	Remote Similarity	NPC198938
0.5364	Remote Similarity	NPC127546
0.5364	Remote Similarity	NPC57625
0.5364	Remote Similarity	NPC173637
0.5364	Remote Similarity	NPC317489
0.5364	Remote Similarity	NPC223424
0.5364	Remote Similarity	NPC600591
0.5357	Remote Similarity	NPC216496
0.5344	Remote Similarity	NPC488078
0.5339	Remote Similarity	NPC156869
0.5339	Remote Similarity	NPC605592
0.5328	Remote Similarity	NPC470447
0.5328	Remote Similarity	NPC471669
0.5317	Remote Similarity	NPC292019
0.5317	Remote Similarity	NPC202908
0.531	Remote Similarity	NPC219904
0.5304	Remote Similarity	NPC170052
0.5304	Remote Similarity	NPC135846
0.5289	Remote Similarity	NPC104883
0.5289	Remote Similarity	NPC488679
0.5285	Remote Similarity	NPC260504
0.5285	Remote Similarity	NPC89809
0.5276	Remote Similarity	NPC25523
0.525	Remote Similarity	NPC153755
0.5217	Remote Similarity	NPC223747
0.5175	Remote Similarity	NPC175107
0.5167	Remote Similarity	NPC470444
0.5149	Remote Similarity	NPC480443
0.5126	Remote Similarity	NPC470405
0.5124	Remote Similarity	NPC240306
0.5122	Remote Similarity	NPC603079
0.5103	Remote Similarity	NPC482521
0.5083	Remote Similarity	NPC304741
0.5082	Remote Similarity	NPC470443
0.5079	Remote Similarity	NPC478277
0.5079	Remote Similarity	NPC96605
0.5079	Remote Similarity	NPC280642
0.5079	Remote Similarity	NPC478276
0.5079	Remote Similarity	NPC478275
0.5079	Remote Similarity	NPC92815
0.5078	Remote Similarity	NPC219043
0.5042	Remote Similarity	NPC258044
0.5042	Remote Similarity	NPC217387
0.5041	Remote Similarity	NPC37668
0.504	Remote Similarity	NPC287889
0.5039	Remote Similarity	NPC203145

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC209528 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4776
0.1-0.2	4317
0.2-0.3	47
0.3-0.4	6
0.4-0.5	3
0.5-0.6	0
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	Drug ID	Developmental Stage
0.6018	Remote Similarity	NPD6797	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