NPASS Compound

Natural Product: NPC238176

Natural Product ID	NPC238176
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S)-2,8-Dimethyl-2-[(4S,8S)-4,8,12-Trimethyltridecyl]-3,4-Dihydrochromen-6-Ol
IUPAC Name	(2S)-2,8-dimethyl-2-[(4S,8S)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1734310
PubChem CID	12444418
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0001546] Vitamin E compounds [CHEMONTID:0000201] Tocopherols

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 75 76 0 0 0 0 0 0 0 0999 V2000 8.0690 -0.9000 0.4993 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4099 -0.4702 -0.7677 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6412 1.0135 -0.9640 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8822 -0.7353 -0.7096 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3287 -0.2722 -2.0201 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8953 -0.4410 -2.2763 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8764 0.1732 -1.4233 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9134 1.6693 -1.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5216 -0.5442 -0.1578 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4307 0.2403 0.6124 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1369 -0.5382 1.8556 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0956 0.1582 2.6767 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1616 -0.6725 3.9154 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1768 0.3881 1.8675 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7154 -0.9101 1.4157 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9358 -0.9204 0.5820 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1512 -0.3323 1.2246 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4245 -1.0791 2.5145 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0844 1.1334 1.3328 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3371 1.8673 0.8482 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6281 1.4236 -0.5359 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9125 2.2878 -1.5752 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1847 1.7965 -2.8378 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1601 0.4289 -3.0102 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8735 -0.4537 -1.9663 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8566 -1.9218 -2.1828 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6046 0.0391 -0.7188 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3062 -0.7180 0.3952 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4718 2.6657 -3.8868 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4575 -1.9480 0.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3753 -0.8841 1.3755 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9759 -0.2867 0.7251 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7946 -0.9934 -1.6657 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7720 1.6160 -0.6481 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5083 1.3149 -0.3645 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9240 1.2274 -2.0315 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7494 -1.8105 -0.6109 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5253 -0.1415 0.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 0.7506 -2.2954 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8580 -0.9199 -2.7967 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7272 -0.2149 -3.3695 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6979 -1.5665 -2.2484 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8917 0.0385 -2.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9002 2.0224 -0.9920 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1716 2.1774 -2.2262 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5980 2.0163 -0.4840 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0297 -1.5305 -0.3542 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3502 -0.6234 0.5403 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8573 1.2201 0.8803 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5672 0.4126 -0.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1056 -0.5669 2.4298 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8858 -1.5997 1.6778 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4385 1.1529 3.0305 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0058 -1.7435 3.6798 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5656 -0.3805 4.6794 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1807 -0.4682 4.2572 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9322 1.0869 1.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8599 0.8899 2.6114 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8391 -1.5549 2.3487 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8998 -1.3988 0.7912 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7512 -0.3315 -0.3622 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1554 -1.9593 0.1781 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1553 -2.1398 2.4524 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5009 -1.0281 2.8062 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8621 -0.5495 3.3315 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2220 1.6191 0.8774 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0670 1.3858 2.4388 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0855 2.9413 0.8619 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1604 1.6184 1.5337 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9189 3.3670 -1.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3709 0.0227 -3.9932 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9050 -2.2911 -2.5778 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1094 -2.4075 -1.2167 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7167 -2.1440 -2.8602 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9769 3.5519 -3.9255 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 17 16 1 6 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 25 27 2 0 27 28 1 0 23 29 1 0 28 17 1 0 27 21 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 0 3 34 1 0 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 7 43 1 6 8 44 1 0 8 45 1 0 8 46 1 0 9 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 12 53 1 1 13 54 1 0 13 55 1 0 13 56 1 0 14 57 1 0 14 58 1 0 15 59 1 0 15 60 1 0 16 61 1 0 16 62 1 0 18 63 1 0 18 64 1 0 18 65 1 0 19 66 1 0 19 67 1 0 20 68 1 0 20 69 1 0 22 70 1 0 24 71 1 0 26 72 1 0 26 73 1 0 26 74 1 0 29 75 1 0 M END

Standard InCHIKey	GZIFEOYASATJEH-BERHBOFZSA-N
Standard InCHI	InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m0/s1
SMILES	CC(C)CCC[C@H](C)CCC[C@H](C)CCC[C@@]1(C)CCc2cc(cc(C)c2O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	402.35	Volume:	468.106 ? Van der Waals volume.
Dense:	0.86	LogP:	8.49 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.331 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.989 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	11.0
TPSA:	29.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.381	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.74	Fsp³:	0.778
MCE-18:	50.0 ? 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:	0.871	Fluc inhibitor:	0.151 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.107 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.515	Promiscuous compounds:	0.022

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.999	MDCK Permeability:	-4.775
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
PAMPA:	0.133 ? 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%):	0.001	30% Bioavailability (F30%):	0.628
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994	MRP1:	0.172
Plasma Protein Binding (PPB):	90.388%	Volume Distribution (VD):	0.253
Fu:	10.146% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.018
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.011	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.989	CYP2C19-substrate:	0.999
CYP2C9-inhibitor:	0.293	CYP2C9-substrate:	0.583
CYP2D6-inhibitor:	0.025	CYP2D6-substrate:	0.757
CYP3A4-inhibitor:	0.947	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.046	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

5.723

Half-life (T1/2):

0.436

ADMET: Toxicity

hERG Blockers:	0.276	hERG Blockers (10um):	0.652
Human Hepatotoxicity (H-HT):	0.674	Drug-induced Liver Injury (DILI):	0.044
AMES Toxicity:	0.399	Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.156	Skin Sensitization:	0.997
Carcinogencity:	0.765	Eye Corrosion:	0.661
Eye Irritation:	0.989	Respiratory Toxicity:	0.635
Drug-induced Neurotoxicity:	0.02	Ototoxicity:	0.396
Hematotoxicity:	0.216	Drug-induced Nephrotoxicity:	0.241
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.093
A549 Cytotoxicity:	0.623	Hek293 Cytotoxicity:	0.304
BCF:	2.455 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.56 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.645 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.999 ? 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
NPO1482	Gossypium barbadense	Species	Malvaceae	Eukaryota	n.a.	Zambia; France; West Africa; USA; South Africa	n.a.	DOI[10.1002/jsfa.2731]
NPO1482	Gossypium barbadense	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ie801365k]
NPO6363	Conyza filaginoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374974]
NPO7436	Annona foetida	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499336]
NPO997	Peltodon longipes	Species	Lamiaceae	Eukaryota	roots	Santa Maria, South Brazil	2007-Dec	PMID[21775156]
NPO1482	Gossypium barbadense	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO6621	Salvadora persica	Species	Salvadoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36514376]
NPO6621	Salvadora persica	Species	Salvadoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36854946]
NPO2853	Eschweilera coriacea	Species	Lecythidaceae	Eukaryota	bark	Suriname rainforest	n.a.	PMID[9677272]
NPO6363	Conyza filaginoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4134	Campanula persicifolia	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7436	Annona foetida	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6621	Salvadora persica	Species	Salvadoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1920	Podocarpus elongata	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO997	Peltodon longipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3809	Eucalyptus cladocalyx	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2853	Eschweilera coriacea	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23741	Aspergillus violaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1709	Pyrola virens	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10260	Tubifera dimorphotheca	Species	Reticulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3899	Spodoptera frugiperda	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7852	Senecio mairetianus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5502	Rhaponticum repens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10007	Desmostachya bipinnata	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9875	Primula spectabilis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8491	Piper montealegreanum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8652	Onychium japonicum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13596	Lambertella corni-maris	Species	Rutstroemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5615	Dipteryx alata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1482	Gossypium barbadense	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9493	Lactuca virosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8957	Mananthes patentiflora	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9493	Lactuca virosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5502	Rhaponticum repens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8652	Onychium japonicum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9493	Lactuca virosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3809	Eucalyptus cladocalyx	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4301	Wedelia triloba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3899	Spodoptera frugiperda	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1920	Podocarpus elongata	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6621	Salvadora persica	Species	Salvadoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8491	Piper montealegreanum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2853	Eschweilera coriacea	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1482	Gossypium barbadense	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO997	Peltodon longipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5615	Dipteryx alata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1709	Pyrola virens	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8957	Mananthes patentiflora	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9493	Lactuca virosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13596	Lambertella corni-maris	Species	Rutstroemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10007	Desmostachya bipinnata	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21060	Hydnocarpus annamensis	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21275	Phoenix paludosa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7852	Senecio mairetianus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6363	Conyza filaginoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8652	Onychium japonicum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3809	Eucalyptus cladocalyx	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10260	Tubifera dimorphotheca	Species	Reticulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5502	Rhaponticum repens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4134	Campanula persicifolia	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9875	Primula spectabilis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19467	Aeglopsis chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8860	Hippospongia equina	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23741	Aspergillus violaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7436	Annona foetida	Species	Annonaceae	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

Activity Type	# Activity
Potency	6
Inhibition	2

Activity Type	# Activity
Individual protein	6
Organism	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT161	Individual protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	7079.5	nM	PubChem BioAssay data set
NPT446	Individual protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	-3.19	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	6.32	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT532	Individual protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	100000.0	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	39810.7	nM	PubChem BioAssay data set

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 NPC238176 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	22280
0.1-0.2	26097
0.2-0.3	1389
0.3-0.4	46
0.4-0.5	20
0.5-0.6	17
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC187993
0.7222	Intermediate Similarity	NPC48623
0.7222	Intermediate Similarity	NPC168707
0.6071	Remote Similarity	NPC126759
0.6071	Remote Similarity	NPC242580
0.6071	Remote Similarity	NPC236070
0.5833	Remote Similarity	NPC69539
0.5571	Remote Similarity	NPC474246
0.5469	Remote Similarity	NPC32152
0.5469	Remote Similarity	NPC147896
0.5469	Remote Similarity	NPC606596
0.5441	Remote Similarity	NPC609807
0.5345	Remote Similarity	NPC238075
0.5294	Remote Similarity	NPC276962
0.5294	Remote Similarity	NPC190086
0.5278	Remote Similarity	NPC474143
0.5224	Remote Similarity	NPC610467
0.5217	Remote Similarity	NPC474131
0.5143	Remote Similarity	NPC601388
0.5139	Remote Similarity	NPC475880
0.5072	Remote Similarity	NPC232295
0.5072	Remote Similarity	NPC611336
0.507	Remote Similarity	NPC196621

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC238176 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4433
0.1-0.2	4665
0.2-0.3	47
0.3-0.4	2
0.4-0.5	1
0.5-0.6	1
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
0.6071	Remote Similarity	NPD7340	Approved
0.5345	Remote Similarity	NPD7644	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