NPASS Compound

Natural Product: NPC224517

Natural Product ID	NPC224517
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZVKXPPXCNUMUOR-VXUVUQTASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14034169
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001554] Tetraterpenoids [CHEMONTID:0001277] Carotenoids [CHEMONTID:0001410] Xanthophylls

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 100102 0 0 0 0 0 0 0 0999 V2000 -2.5455 -2.0150 0.4393 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8376 -0.7589 1.1542 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8029 -0.0166 1.5472 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4345 -0.4278 1.2834 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6055 0.2728 1.6517 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9941 -0.1015 1.4080 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0076 0.6370 1.7997 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7098 1.8863 2.5102 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3711 0.2250 1.5360 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4571 0.8667 1.8713 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8185 0.4074 1.5812 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8682 1.1120 1.9536 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6326 2.3863 2.6770 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2524 0.6963 1.6877 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3825 -0.5836 0.9585 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3034 -0.4369 0.0212 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8303 -1.3774 -0.9846 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6975 -2.4019 -0.2894 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7091 -2.1377 -1.6814 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6065 -0.6532 -2.0679 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9549 0.6615 -2.4241 C 0 0 1 0 0 0 0 0 0 0 0 0 10.7430 1.5655 -1.2659 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8140 0.9375 0.0883 C 0 0 2 0 0 0 0 0 0 0 0 0 12.1866 1.0485 0.7128 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9363 1.6393 0.9356 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6019 1.2785 -3.4953 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1891 -0.3193 1.4366 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2802 -0.9653 1.1001 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5921 -0.3938 1.4556 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6960 -1.0498 1.1135 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6115 -2.3230 0.3931 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9434 -0.4569 1.4777 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7620 -0.2211 0.4790 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4844 0.0079 -0.5795 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2802 1.2783 -1.2364 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4907 1.0157 -2.5256 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5061 2.2592 -0.4131 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6399 1.8212 -1.6553 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7617 1.0135 -1.0378 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.6793 -0.4480 -1.4357 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3895 -1.0779 -0.9280 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.7362 -1.9803 0.2347 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9196 -1.8832 -1.9821 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.7599 1.1946 0.3357 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8571 -1.7842 -0.4123 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4505 -2.5264 0.0768 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9894 -2.6668 1.1763 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0244 0.9207 2.0798 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2736 -1.3552 0.7606 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3926 1.2074 2.1806 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1967 -1.0234 0.8837 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3002 2.6503 1.7890 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5638 2.3819 2.9950 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9693 1.7267 3.3471 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5474 -0.7259 0.9969 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3573 1.8001 2.3979 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9497 -0.5324 1.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5925 2.8989 2.9267 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0305 2.1792 3.5854 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0056 3.0456 2.0208 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8134 0.5616 2.6550 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7963 -1.4655 1.1931 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7611 -2.0681 -0.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2797 -2.6378 0.7218 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7075 -3.3737 -0.8377 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8820 -1.4149 -1.8567 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3712 -3.0007 -1.0750 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1147 -2.4554 -2.6757 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6298 -0.4880 -1.7417 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6389 -1.3008 -2.9665 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9412 0.3729 -2.8331 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4699 2.4125 -1.3619 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7058 2.0097 -1.3655 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2128 2.0130 1.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0082 1.1205 -0.0185 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2920 0.2325 1.4427 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1782 0.5783 -3.9068 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3252 0.6254 1.9726 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2274 -1.8988 0.5728 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6360 0.5440 1.9853 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9780 -2.1760 -0.5107 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1153 -3.1319 0.9904 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6036 -2.6658 0.0444 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3380 -0.1678 2.4067 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7202 0.2385 -2.3645 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9452 1.9268 -2.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1741 0.6191 -3.3174 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8167 2.2642 0.6617 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4739 3.2682 -0.8459 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4361 1.9040 -0.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7334 1.9225 -2.7405 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7129 2.8480 -1.2110 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7134 1.4079 -1.4608 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5638 -0.9437 -0.9651 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7329 -0.4746 -2.5426 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8209 -1.9889 0.4316 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1417 -1.6425 1.1064 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4464 -3.0274 0.0181 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9595 -1.8232 -2.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6392 0.8973 0.6824 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 21 26 1 0 2 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 30 32 1 0 32 33 2 0 33 34 2 0 34 35 1 0 35 36 1 0 35 37 1 0 35 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 6 39 44 1 0 25 14 1 0 41 34 1 0 23 16 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 4 49 1 0 5 50 1 0 6 51 1 0 8 52 1 0 8 53 1 0 8 54 1 0 9 55 1 0 10 56 1 0 11 57 1 0 13 58 1 0 13 59 1 0 13 60 1 0 14 61 1 1 15 62 1 0 18 63 1 0 18 64 1 0 18 65 1 0 19 66 1 0 19 67 1 0 19 68 1 0 20 69 1 0 20 70 1 0 21 71 1 6 22 72 1 0 22 73 1 0 24 74 1 0 24 75 1 0 24 76 1 0 26 77 1 0 27 78 1 0 28 79 1 0 29 80 1 0 31 81 1 0 31 82 1 0 31 83 1 0 32 84 1 0 36 85 1 0 36 86 1 0 36 87 1 0 37 88 1 0 37 89 1 0 37 90 1 0 38 91 1 0 38 92 1 0 39 93 1 6 40 94 1 0 40 95 1 0 42 96 1 0 42 97 1 0 42 98 1 0 43 99 1 0 44100 1 0 M END

Standard InCHIKey	ZVKXPPXCNUMUOR-VXUVUQTASA-N
Standard InCHI	InChI=1S/C40H56O4/c1-28(17-13-18-30(3)21-22-35-37(5,6)24-32(41)26-39(35,9)43)15-11-12-16-29(2)19-14-20-31(4)34-23-36-38(7,8)25-33(42)27-40(36,10)44-34/h11-21,23,32-34,41-43H,24-27H2,1-10H3/b12-11+,17-13+,19-14+,28-15+,29-16+,30-18+,31-20+/t22?,32-,33-,34+,39+,40+/m0/s1
SMILES	C/C(=CC=CC=C(/C)C=CC=C(/C)[C@H]1C=C2C(C)(C)C[C@@H](C[C@@]2(C)O1)O)/C=C/C=C(C)/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	600.42	Volume:	683.523 ? Van der Waals volume.
Dense:	0.878	LogP:	4.267 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.709 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.573 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	25.0
TPSA:	69.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.148	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.603	Fsp³:	0.525
MCE-18:	70.82 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.875	Fluc inhibitor:	0.605 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.045 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.1 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.616	Promiscuous compounds:	0.326

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.031	MDCK Permeability:	-4.778
Pgp-inhibitor:	0.065	Pgp-substrate:	0.999
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):	0.0
20% Bioavailability (F20%):	0.973	30% Bioavailability (F30%):	0.876
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.684
Plasma Protein Binding (PPB):	91.762%	Volume Distribution (VD):	0.405
Fu:	8.144% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.04
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.854
CYP3A4-inhibitor:	0.02	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.108 ? 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):

7.672

Half-life (T1/2):

0.993

ADMET: Toxicity

hERG Blockers:	0.093	hERG Blockers (10um):	0.364
Human Hepatotoxicity (H-HT):	0.534	Drug-induced Liver Injury (DILI):	0.115
AMES Toxicity:	0.902	Rat Oral Acute Toxicity:	0.949
Maximum Recommended Daily Dose:	0.995	Skin Sensitization:	0.999
Carcinogencity:	0.873	Eye Corrosion:	0.0
Eye Irritation:	0.013	Respiratory Toxicity:	0.982
Drug-induced Neurotoxicity:	0.753	Ototoxicity:	0.902
Hematotoxicity:	0.068	Drug-induced Nephrotoxicity:	0.962
Genotoxicity:	0.768	RPMI-8226 Immunitoxicity:	0.426
A549 Cytotoxicity:	0.885	Hek293 Cytotoxicity:	0.898
BCF:	2.082 ? 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:	4.402 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.049 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.354 ? 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
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)88710-5]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096857]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15128261]
NPO24744	Chloranthus tianmushanensis	Species	Chloranthaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18357995]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19618898]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23186307]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23507152]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25919052]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31836445]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33321838]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34771092]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432812]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36987013]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37176852]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37751472]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836118]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836125]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38786901]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26042	Agnorhiza bolanderi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7552	Alligator mississippiensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18352	Anaxagorea clavata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25090	Araujia sericifera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24929	Aria pallescens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25144	Artemisia monogyna	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24556	Bassia butyracea	Species	Abylidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20833	Beyeria brevifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25529	Bursaria spinosa	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24744	Chloranthus tianmushanensis	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25471	Chromolaena pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25187	Cladonia evansii	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23567	Coccus fagi	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25326	Dendrosenecio kilimanjari	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24511	Dipterocarpus alatus	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24640	Echinops amplexicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25234	Epaltes gariepina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24383	Ficus formosana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24218	Fusarium gibbosum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25671	Gardenia fosbergii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1794	Ilex affinis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25291	Lactarius scrobiculatus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23963	Odixia angusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23453	Pheidole pallidula	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24830	Prosopis glandulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24068	Prunus laurocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7445	Pteris prolifera	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25390	Pterocarpus grandiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23691	Pyrosoma giganteum	Species	Pyrosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24675	Quercus aegilops	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24291	Rhizobium phaseoli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28665	Sesbania punicea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24987	Simira eliezeriana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20823	Stenostomum lucidum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24599	Streptomyces althioticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25699	Vitex madiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25045	Senecio squalidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20823	Stenostomum lucidum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24383	Ficus formosana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23567	Coccus fagi	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7552	Alligator mississippiensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23691	Pyrosoma giganteum	Species	Pyrosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7445	Pteris prolifera	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24929	Aria pallescens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22736	Drosera peltata	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24218	Fusarium gibbosum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24987	Simira eliezeriana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24511	Dipterocarpus alatus	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25529	Bursaria spinosa	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6714	Securidaca inappendiculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25291	Lactarius scrobiculatus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24744	Chloranthus tianmushanensis	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24068	Prunus laurocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25471	Chromolaena pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1794	Ilex affinis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25258	Seriphidium cinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24599	Streptomyces althioticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24291	Rhizobium phaseoli	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25415	Pseudopterogorgia kallos	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23453	Pheidole pallidula	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25144	Artemisia monogyna	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24556	Bassia butyracea	Species	Abylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25326	Dendrosenecio kilimanjari	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25187	Cladonia evansii	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25234	Epaltes gariepina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18352	Anaxagorea clavata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25671	Gardenia fosbergii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25699	Vitex madiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26042	Agnorhiza bolanderi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25623	Taxodium mucronatum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25390	Pterocarpus grandiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25090	Araujia sericifera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24640	Echinops amplexicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20833	Beyeria brevifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24830	Prosopis glandulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25359	Isodon kameba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28665	Sesbania punicea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24675	Quercus aegilops	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23963	Odixia angusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25045	Senecio squalidus	Species	Asteraceae	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 NPC224517 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	22733
0.1-0.2	26807
0.2-0.3	301
0.3-0.4	15
0.4-0.5	3
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC224517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7108
0.1-0.2	2023
0.2-0.3	17
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data