NPASS Compound

Natural Product: NPC32940

Natural Product ID	NPC32940
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MJIKFVGKCRVQNL-WQKFSZIYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10653411
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 -4.9690 3.4058 -4.9299 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8030 3.5007 -3.4118 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0401 4.9250 -2.9657 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0905 5.0127 -1.8926 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0413 3.9172 -0.8983 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5357 2.5905 -1.4731 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6854 2.6121 -2.8221 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1957 2.5021 -1.1454 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9223 1.5779 -0.1578 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9526 2.1304 0.8615 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6058 1.9800 0.0574 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2863 0.4805 0.0658 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2477 0.2265 1.1045 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0051 0.7170 0.7095 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9838 0.5425 1.7173 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0004 -0.4046 1.1644 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4987 0.1063 -0.1612 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5062 1.5922 -0.1435 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4471 2.2458 1.1870 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7820 2.3834 1.8791 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4824 1.7709 2.0499 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4529 2.0579 -0.9563 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8589 -0.3113 -0.2889 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3205 -1.1758 -1.2508 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5283 -1.6626 -2.0658 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7678 -1.4653 -1.2516 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5672 -0.9088 -0.3572 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9995 -1.1189 -0.2754 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7270 -1.8763 -1.1533 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0844 -1.9990 -0.9860 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7810 -1.3983 0.0310 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0635 -0.6397 0.9173 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7025 -0.5015 0.7682 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7784 -0.0352 1.9487 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2754 0.7775 2.9517 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1727 -1.5516 0.1561 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0196 -0.5687 2.1123 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4843 -0.1717 0.4487 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4783 0.2319 -0.5233 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4986 -0.7477 -0.4377 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2555 -2.0988 -0.5397 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0377 -2.6377 -1.8036 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0608 -1.9462 -2.8497 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7899 -3.9814 -1.8997 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5605 -4.6188 -3.0895 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3100 -5.9700 -3.1685 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2873 -6.7332 -2.0078 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5131 -6.1228 -0.8241 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7638 -4.7657 -0.7393 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9794 -4.1749 0.3711 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2331 -2.8742 0.5829 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4604 -2.4466 1.9513 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8874 -1.2192 2.3296 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1128 -0.8423 3.6571 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8937 -1.7594 4.6539 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4640 -3.0052 4.3000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2466 -3.3589 2.9905 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2521 -3.9139 5.3501 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1122 -1.4036 5.9934 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0297 -8.0945 -2.1571 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5886 -3.8475 -4.2467 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6790 2.6367 0.8115 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8399 1.3576 2.0052 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3293 3.6804 -0.3441 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3629 5.0155 -2.4905 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8731 5.5924 -2.6639 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5211 2.4954 -5.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5131 4.3362 -5.2549 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9620 3.4938 -5.3729 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7628 3.2305 -3.1823 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4771 5.4894 -3.8451 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9954 6.0232 -1.4274 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4119 4.2571 -0.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1359 1.7882 -0.9620 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9476 1.4087 0.3061 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0810 3.2035 1.0522 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7819 2.3002 -0.9586 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9630 0.1266 -0.9030 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0926 -0.8486 1.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5374 0.6792 2.1013 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5281 0.0628 2.5958 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5112 -1.4006 0.9713 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8854 -0.3045 -1.0018 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4349 1.9668 -0.6639 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1104 3.3114 0.9783 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0506 3.4581 2.0732 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5767 2.0081 1.1955 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7991 1.9231 2.8811 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6468 1.9175 -1.9212 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1906 -2.1316 -1.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0957 -0.2481 0.3596 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2083 -2.3750 -1.9810 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6492 -2.5980 -1.6944 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1282 0.0934 1.4580 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2028 0.9844 2.8616 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8350 1.7524 2.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4852 0.3532 3.9715 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7951 -0.9469 -0.3811 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0857 -1.5366 2.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8802 0.1823 -1.4425 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1319 -6.4373 -4.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4938 -6.7320 0.0876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1072 -0.4617 1.6181 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4581 0.1597 3.8979 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9082 -4.3555 2.7408 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9795 -4.0075 6.0783 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7180 -1.9840 6.7370 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7909 -8.7706 -2.2051 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4920 -3.5306 -4.5553 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0459 2.9413 0.2035 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4708 1.9558 2.7110 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2014 3.4482 0.5946 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2456 4.9709 -3.4601 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2502 5.1302 -2.0767 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 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 31 36 1 0 16 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 33 28 1 0 49 44 1 0 1 67 1 0 1 68 1 0 1 69 1 0 2 70 1 6 3 71 1 6 4 72 1 1 5 73 1 1 6 74 1 1 9 75 1 1 10 76 1 1 11 77 1 6 12 78 1 6 13 79 1 0 13 80 1 0 15 81 1 1 16 82 1 6 17 83 1 6 18 84 1 6 19 85 1 6 20 86 1 0 20 87 1 0 20 88 1 0 22 89 1 0 26 90 1 0 27 91 1 0 29 92 1 0 30 93 1 0 33 94 1 0 35 95 1 0 35 96 1 0 35 97 1 0 36 98 1 0 37 99 1 0 39100 1 6 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	MJIKFVGKCRVQNL-WQKFSZIYSA-N
Standard InCHI	InChI=1S/C43H48O23/c1-15-29(50)33(54)35(56)42(61-15)66-40-34(55)31(52)26(14-59-41-36(57)38(30(51)16(2)60-41)64-27(49)9-5-17-4-7-21(46)24(10-17)58-3)63-43(40)65-39-32(53)28-23(48)12-19(44)13-25(28)62-37(39)18-6-8-20(45)22(47)11-18/h4-13,15-16,26,29-31,33-36,38,40-48,50-52,54-57H,14H2,1-3H3/b9-5+/t15-,16-,26+,29-,30-,31-,33+,34-,35+,36+,38+,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)OC(=O)/C=C/c2ccc(c(c2)OC)O)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:	1.272 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.616 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.013 ? 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:	5.784	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:	0.73	Fluc inhibitor:	0.639 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.743 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.664 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.272	Promiscuous compounds:	0.511

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.444	MDCK Permeability:	-5.297
Pgp-inhibitor:	0.0	Pgp-substrate:	0.875
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):	0.026
20% Bioavailability (F20%):	0.844	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.002
Plasma Protein Binding (PPB):	84.065%	Volume Distribution (VD):	-0.041
Fu:	12.525% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.675
BSEP inhibitor:	0.597

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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.693 ? 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):

0.98

Half-life (T1/2):

6.036

ADMET: Toxicity

hERG Blockers:	0.015	hERG Blockers (10um):	0.409
Human Hepatotoxicity (H-HT):	0.191	Drug-induced Liver Injury (DILI):	0.775
AMES Toxicity:	0.658	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.111	Skin Sensitization:	0.999
Carcinogencity:	0.011	Eye Corrosion:	0.0
Eye Irritation:	0.126	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.979
Hematotoxicity:	0.009	Drug-induced Nephrotoxicity:	0.123
Genotoxicity:	0.351	RPMI-8226 Immunitoxicity:	0.113
A549 Cytotoxicity:	0.779	Hek293 Cytotoxicity:	0.695
BCF:	0.557 ? 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:	3.359 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.989 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.214 ? 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 NPC32940 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	17309
0.1-0.2	28466
0.2-0.3	3288
0.3-0.4	444
0.4-0.5	198
0.5-0.6	111
0.6-0.7	28
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8033	Intermediate Similarity	NPC487501
0.7851	Intermediate Similarity	NPC249560
0.7739	Intermediate Similarity	NPC162394
0.7381	Intermediate Similarity	NPC487500
0.7355	Intermediate Similarity	NPC21359
0.7355	Intermediate Similarity	NPC460984
0.7311	Intermediate Similarity	NPC241781
0.7236	Intermediate Similarity	NPC473554
0.72	Intermediate Similarity	NPC487502
0.7182	Intermediate Similarity	NPC122467
0.6984	Remote Similarity	NPC72554
0.6957	Remote Similarity	NPC89052
0.6903	Remote Similarity	NPC89127
0.6855	Remote Similarity	NPC25946
0.685	Remote Similarity	NPC30011
0.6769	Remote Similarity	NPC97817
0.6716	Remote Similarity	NPC33083
0.6695	Remote Similarity	NPC173837
0.6693	Remote Similarity	NPC275977
0.6637	Remote Similarity	NPC12013
0.6637	Remote Similarity	NPC11432
0.6637	Remote Similarity	NPC477613
0.65	Remote Similarity	NPC303694
0.6434	Remote Similarity	NPC231787
0.6356	Remote Similarity	NPC602448
0.632	Remote Similarity	NPC156785
0.6306	Remote Similarity	NPC95866
0.629	Remote Similarity	NPC474093
0.629	Remote Similarity	NPC104910
0.6271	Remote Similarity	NPC221342
0.6271	Remote Similarity	NPC476470
0.627	Remote Similarity	NPC480444
0.6231	Remote Similarity	NPC487499
0.6148	Remote Similarity	NPC292019
0.6148	Remote Similarity	NPC202908
0.6111	Remote Similarity	NPC470713
0.6087	Remote Similarity	NPC155877
0.6083	Remote Similarity	NPC218161
0.5948	Remote Similarity	NPC203259
0.5948	Remote Similarity	NPC33054
0.5948	Remote Similarity	NPC176740
0.5948	Remote Similarity	NPC471725
0.5948	Remote Similarity	NPC134532
0.5948	Remote Similarity	NPC602582
0.5938	Remote Similarity	NPC488740
0.5938	Remote Similarity	NPC488736
0.5938	Remote Similarity	NPC488733
0.5923	Remote Similarity	NPC192539
0.5917	Remote Similarity	NPC220173
0.5882	Remote Similarity	NPC473327
0.5859	Remote Similarity	NPC480445
0.5846	Remote Similarity	NPC488737
0.5833	Remote Similarity	NPC142142
0.582	Remote Similarity	NPC223426
0.5789	Remote Similarity	NPC476215
0.5785	Remote Similarity	NPC476472
0.5785	Remote Similarity	NPC294815
0.5785	Remote Similarity	NPC16194
0.5772	Remote Similarity	NPC483765
0.5772	Remote Similarity	NPC81042
0.5692	Remote Similarity	NPC474522
0.568	Remote Similarity	NPC189564
0.5645	Remote Similarity	NPC96605
0.5645	Remote Similarity	NPC280642
0.5625	Remote Similarity	NPC139571
0.5625	Remote Similarity	NPC470718
0.561	Remote Similarity	NPC292929
0.5603	Remote Similarity	NPC254855
0.5603	Remote Similarity	NPC94610
0.5593	Remote Similarity	NPC163242
0.5593	Remote Similarity	NPC272068
0.5591	Remote Similarity	NPC480441
0.5591	Remote Similarity	NPC217520
0.5574	Remote Similarity	NPC221288
0.5574	Remote Similarity	NPC194836
0.5574	Remote Similarity	NPC91493
0.5574	Remote Similarity	NPC605081
0.5565	Remote Similarity	NPC483767
0.5565	Remote Similarity	NPC483769
0.5565	Remote Similarity	NPC483768
0.5565	Remote Similarity	NPC483766
0.5538	Remote Similarity	NPC488734
0.5538	Remote Similarity	NPC488735
0.5538	Remote Similarity	NPC488739
0.5538	Remote Similarity	NPC488732
0.5538	Remote Similarity	NPC488738
0.5522	Remote Similarity	NPC480442
0.5522	Remote Similarity	NPC480472
0.5512	Remote Similarity	NPC477895
0.5493	Remote Similarity	NPC475179
0.5476	Remote Similarity	NPC203145
0.5462	Remote Similarity	NPC173582
0.5462	Remote Similarity	NPC265885
0.5462	Remote Similarity	NPC181465
0.5462	Remote Similarity	NPC215710
0.5462	Remote Similarity	NPC473438
0.5462	Remote Similarity	NPC253788
0.5447	Remote Similarity	NPC101399
0.5447	Remote Similarity	NPC217822
0.5447	Remote Similarity	NPC11847
0.5447	Remote Similarity	NPC198938
0.5403	Remote Similarity	NPC85751
0.5403	Remote Similarity	NPC19240
0.5397	Remote Similarity	NPC214621
0.5397	Remote Similarity	NPC34267
0.5372	Remote Similarity	NPC255157
0.5372	Remote Similarity	NPC259896
0.5349	Remote Similarity	NPC470712
0.5338	Remote Similarity	NPC470719
0.5338	Remote Similarity	NPC470717
0.5333	Remote Similarity	NPC67326
0.5333	Remote Similarity	NPC39834
0.5328	Remote Similarity	NPC126784
0.5328	Remote Similarity	NPC480470
0.5328	Remote Similarity	NPC241423
0.5323	Remote Similarity	NPC205824
0.5323	Remote Similarity	NPC97119
0.5312	Remote Similarity	NPC470416
0.5299	Remote Similarity	NPC470720
0.5289	Remote Similarity	NPC156869
0.5285	Remote Similarity	NPC245452
0.5259	Remote Similarity	NPC209550
0.5246	Remote Similarity	NPC35167
0.5242	Remote Similarity	NPC104883
0.5242	Remote Similarity	NPC488679
0.5231	Remote Similarity	NPC25523
0.521	Remote Similarity	NPC116864
0.521	Remote Similarity	NPC244776
0.5188	Remote Similarity	NPC295625
0.5185	Remote Similarity	NPC488078
0.5175	Remote Similarity	NPC127546
0.5175	Remote Similarity	NPC57625
0.5175	Remote Similarity	NPC173637
0.5175	Remote Similarity	NPC317489
0.5175	Remote Similarity	NPC223424
0.5175	Remote Similarity	NPC600591
0.5164	Remote Similarity	NPC605592
0.5159	Remote Similarity	NPC471669
0.5128	Remote Similarity	NPC219904
0.5126	Remote Similarity	NPC170052
0.5126	Remote Similarity	NPC135846
0.5109	Remote Similarity	NPC480443
0.5086	Remote Similarity	NPC52550
0.5081	Remote Similarity	NPC153755
0.5075	Remote Similarity	NPC488086
0.5068	Remote Similarity	NPC482521
0.5043	Remote Similarity	NPC216496
0.5042	Remote Similarity	NPC223747
0.504	Remote Similarity	NPC470443

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC32940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4967
0.1-0.2	4122
0.2-0.3	52
0.3-0.4	5
0.4-0.5	3
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
0.5948	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