NPASS Compound

Natural Product: NPC183993

Natural Product ID	NPC183993
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IFYMEZNJCAQUME-BDLHTDMPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10257732
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 99101 0 0 0 0 0 0 0 0999 V2000 3.8094 -1.6288 0.0030 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8163 -0.5506 -0.2462 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5407 -0.8549 -0.2792 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5603 0.1829 -0.5213 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7487 -0.1564 -0.5505 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7554 0.8665 -0.7936 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0229 0.4978 -0.8235 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0625 1.5544 -1.0746 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4428 -0.8744 -0.6320 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7582 -1.1759 -0.6831 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2091 -2.5245 -0.4979 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4365 -2.9040 -0.5273 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6857 -4.3928 -0.3118 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5796 -2.0304 -0.7700 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6732 -2.3073 0.2413 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2123 -1.1368 0.5277 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3225 -0.6960 1.4349 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7258 -1.8522 2.3569 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5368 -0.3593 0.6020 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8909 0.4438 2.3146 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2377 1.5586 1.5515 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1825 1.1407 0.5883 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5118 -0.0788 -0.2333 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1973 0.3130 -1.5150 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3278 -0.7244 -0.5524 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1324 2.4128 0.9317 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2796 0.8072 -0.4430 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6079 1.0920 -0.4061 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0602 2.4454 -0.6019 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3440 2.7603 -0.5760 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6977 4.2088 -0.7927 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3341 1.7304 -0.3431 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6368 1.9653 -0.3087 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6611 0.9457 -0.0754 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9288 1.3983 -0.0768 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2216 2.8403 -0.3041 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0909 0.5001 0.1575 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5695 -0.5516 1.1530 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5553 -1.3452 0.3790 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3315 -0.4829 0.1443 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4959 -1.0776 -0.9697 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5119 -0.5654 1.4244 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6112 -1.3608 1.6164 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2973 -2.6109 0.0953 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4880 -1.7351 -0.8972 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3918 -1.4765 0.9301 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2136 -1.9026 -0.1234 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7851 1.2184 -0.6823 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9647 -1.1866 -0.3870 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5210 1.8990 -0.9471 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8179 1.5401 -0.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6017 1.3490 -2.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5710 2.5302 -1.1569 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7925 -1.6931 -0.4500 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4335 -0.3674 -0.8830 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4064 -3.2804 -0.3166 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8366 -4.5483 0.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5647 -4.6272 -0.9481 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8034 -4.9228 -0.7048 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9868 -2.1575 -1.8014 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9702 -3.2605 0.6593 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7549 -1.6588 2.7199 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0153 -1.9789 3.1967 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7879 -2.7488 1.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4319 -0.5484 1.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5851 0.7048 0.2927 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5263 -0.9654 -0.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2002 0.0561 3.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7933 0.8480 2.8167 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7144 2.1853 2.3362 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1696 1.0677 1.0668 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0660 1.9949 -0.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8629 1.2048 -1.3570 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6846 -0.5071 -2.0425 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3969 0.7016 -2.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7632 2.8636 1.5275 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6576 1.6643 -0.6256 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2197 0.2328 -0.2226 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3118 3.2286 -0.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8687 4.7717 -0.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6670 4.4566 -0.3452 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5939 4.4924 -1.8537 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0403 0.6988 -0.1784 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9114 3.0067 -0.4796 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3086 3.0384 -0.2759 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7970 3.4641 0.5368 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8586 3.1957 -1.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4192 0.0025 -0.7675 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9017 1.0248 0.6847 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0691 -0.0112 1.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9769 -1.6261 -0.6146 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2429 -2.2680 0.9230 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3370 -0.3887 -1.8230 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5779 -1.5643 -0.6005 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1117 -1.9196 -1.4117 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2637 0.4539 1.8329 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0825 -1.0607 2.2508 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5503 -1.0891 1.2908 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0673 -1.8240 0.8883 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 6 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 1 0 34 35 2 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 40 42 1 0 38 43 1 0 25 14 1 0 40 34 1 0 23 16 1 0 1 44 1 0 1 45 1 0 1 46 1 0 3 47 1 0 4 48 1 0 5 49 1 0 6 50 1 0 8 51 1 0 8 52 1 0 8 53 1 0 9 54 1 0 10 55 1 0 11 56 1 0 13 57 1 0 13 58 1 0 13 59 1 0 14 60 1 6 15 61 1 0 18 62 1 0 18 63 1 0 18 64 1 0 19 65 1 0 19 66 1 0 19 67 1 0 20 68 1 0 20 69 1 0 21 70 1 1 22 71 1 0 22 72 1 0 24 73 1 0 24 74 1 0 24 75 1 0 26 76 1 0 27 77 1 0 28 78 1 0 29 79 1 0 31 80 1 0 31 81 1 0 31 82 1 0 32 83 1 0 33 84 1 0 36 85 1 0 36 86 1 0 36 87 1 0 37 88 1 0 37 89 1 0 38 90 1 1 39 91 1 0 39 92 1 0 41 93 1 0 41 94 1 0 41 95 1 0 42 96 1 0 42 97 1 0 42 98 1 0 43 99 1 0 M END

Standard InCHIKey	IFYMEZNJCAQUME-BDLHTDMPSA-N
Standard InCHI	InChI=1S/C40H56O3/c1-28(17-13-18-30(3)21-22-35-32(5)23-33(41)25-38(35,6)7)15-11-12-16-29(2)19-14-20-31(4)36-24-37-39(8,9)26-34(42)27-40(37,10)43-36/h11-22,24,33-34,36,41-42H,23,25-27H2,1-10H3/b12-11+,17-13+,19-14+,22-21+,28-15-,29-16-,30-18-,31-20-/t33-,34-,36+,40+/m0/s1
SMILES	C/C(=C/C=C/C=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=CC1=C(C)C[C@@H](CC1(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	584.42	Volume:	674.733 ? Van der Waals volume.
Dense:	0.866	LogP:	7.789 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.289 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.8 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	24.0
TPSA:	49.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.209	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.265	Fsp³:	0.5
MCE-18:	65.333 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.999	Fluc inhibitor:	0.61 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.218 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.032 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.624	Promiscuous compounds:	0.314

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.957	MDCK Permeability:	-4.749
Pgp-inhibitor:	0.315	Pgp-substrate:	0.998
PAMPA:	0.92 ? 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%):	0.887	30% Bioavailability (F30%):	0.81
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.995
Plasma Protein Binding (PPB):	92.628%	Volume Distribution (VD):	0.183
Fu:	7.931% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.982	BCRP inhibitor:	0.067
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.176
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.256	CYP3A4-substrate:	0.994
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.368 ? 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):

10.29

Half-life (T1/2):

0.695

ADMET: Toxicity

hERG Blockers:	0.519	hERG Blockers (10um):	0.502
Human Hepatotoxicity (H-HT):	0.487	Drug-induced Liver Injury (DILI):	0.643
AMES Toxicity:	0.872	Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	1.0
Carcinogencity:	0.658	Eye Corrosion:	0.0
Eye Irritation:	0.005	Respiratory Toxicity:	0.687
Drug-induced Neurotoxicity:	0.537	Ototoxicity:	0.843
Hematotoxicity:	0.399	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.869	RPMI-8226 Immunitoxicity:	0.438
A549 Cytotoxicity:	0.613	Hek293 Cytotoxicity:	0.911
BCF:	2.502 ? 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:	4.545 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.313 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.702 ? 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
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 16712885]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.foodchem.2013.08.121]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[10670815]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[12232058]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[16180814]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	seeds	Shizuoka prefecture, Japan	n.a.	PMID[16499314]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	Malatya Fruit Research Institute	between the first and third weeks of 2005-Jul.	PMID[18038980]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21434603]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21648406]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	flower	n.a.	PMID[21922925]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[21925888]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22377672]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265489]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaves	Bandung, West Java, Indonesia		PMID[23621359]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235013]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36675004]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37255739]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37759401]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38279238]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39181940]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39409699]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39716808]
NPO11322	Acacia dealbata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8083	Medicago falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18591	Senecio vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18591	Senecio vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3009	Rosa sp.	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8083	Medicago falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18591	Senecio vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15375	Narcissus sp.	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11322	Acacia dealbata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26059	Chrysanthemum sp.	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18591	Senecio vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18591	Senecio vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2379	Senecio oryzetorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11322	Acacia dealbata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8083	Medicago falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28919	Calendula officinalis	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 NPC183993 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	25088
0.1-0.2	24559
0.2-0.3	178
0.3-0.4	25
0.4-0.5	2
0.5-0.6	6
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	Natural Product ID
0.6078	Remote Similarity	NPC45782
0.5536	Remote Similarity	NPC606837
0.5246	Remote Similarity	NPC607338
0.5161	Remote Similarity	NPC171148
0.5161	Remote Similarity	NPC313179
0.5161	Remote Similarity	NPC69383
0.5161	Remote Similarity	NPC183736

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC183993 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7519
0.1-0.2	1618
0.2-0.3	3
0.3-0.4	8
0.4-0.5	1
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5161	Remote Similarity	NPD8264	Approved

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