NPASS Compound

Natural Product: NPC165550

Natural Product ID	NPC165550
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LDBQEVDAHSVWKL-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	130632
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 50 52 0 0 0 0 0 0 0 0999 V2000 -4.2241 1.7721 1.8581 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0135 1.3001 0.4375 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1744 2.4918 -0.4765 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6686 0.6837 0.3195 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5627 1.4373 -0.0187 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3022 0.8925 -0.1355 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1706 -0.4759 0.1033 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9779 -1.2379 0.0489 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2721 -0.8826 -0.3060 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1358 -2.0501 -0.5531 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3925 -1.8115 -0.9014 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9003 -0.4506 -1.0351 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9008 -0.2116 -1.7615 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1900 0.6172 -0.2848 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6578 1.9914 -0.6651 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5298 0.3870 1.1926 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7512 0.4043 -0.4315 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0156 1.5548 -0.6866 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6695 1.8093 -0.4818 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2630 2.9813 -0.6176 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2523 -1.2600 0.4431 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5166 -0.6691 0.5518 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5687 -1.4988 0.8951 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3638 -2.1867 -0.0601 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0393 -2.5926 0.6606 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1106 -3.6004 -0.3275 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3177 1.7473 2.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7037 1.1174 2.5821 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8716 2.8270 1.9055 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7737 0.5291 0.1968 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5514 3.3232 -0.1196 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2423 2.8105 -0.3908 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9338 2.2816 -1.5226 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6786 2.4953 -0.2009 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8662 -2.2911 0.3264 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7095 -3.0205 -0.4401 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0428 -2.6557 -1.0871 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2383 2.7110 0.0416 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7725 2.0001 -0.4814 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5273 2.2154 -1.7207 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6636 0.6866 1.8313 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7058 -0.6888 1.3948 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4254 0.9413 1.5001 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5901 2.3478 -1.1010 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0798 -1.9136 -1.0905 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4362 -1.8755 0.0490 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3580 -3.2820 0.1229 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1169 -4.0187 -0.3195 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7545 -3.2661 -1.3124 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4123 -4.4166 0.0054 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 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 14 16 1 0 14 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 7 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 21 25 1 0 25 26 1 0 22 4 1 0 19 6 1 0 17 9 1 0 1 27 1 0 1 28 1 0 1 29 1 0 2 30 1 0 3 31 1 0 3 32 1 0 3 33 1 0 5 34 1 0 8 35 1 0 10 36 1 0 11 37 1 0 15 38 1 0 15 39 1 0 15 40 1 0 16 41 1 0 16 42 1 0 16 43 1 0 18 44 1 0 24 45 1 0 24 46 1 0 24 47 1 0 26 48 1 0 26 49 1 0 26 50 1 0 M END

Standard InCHIKey	LDBQEVDAHSVWKL-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C22H24O4/c1-12(2)14-10-15-16(21(26-6)20(14)25-5)9-13-7-8-19(24)22(3,4)17(13)11-18(15)23/h7-12H,1-6H3
SMILES	CC(C)c1cc2c(cc3C=CC(=O)C(C)(C)c3cc2=O)c(c1OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	352.17	Volume:	377.468 ? Van der Waals volume.
Dense:	0.933	LogP:	3.764 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.382 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.981 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	19.0
TPSA:	52.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.83	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.989	Fsp³:	0.364
MCE-18:	45.467 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.877	Fluc inhibitor:	0.312 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.52 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.607 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.363	Promiscuous compounds:	0.017

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.659	MDCK Permeability:	-4.689
Pgp-inhibitor:	0.968	Pgp-substrate:	0.007
PAMPA:	0.06 ? 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):	0.007
20% Bioavailability (F20%):	0.123	30% Bioavailability (F30%):	0.225
50% Bioavailability (F50%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052	MRP1:	0.996
Plasma Protein Binding (PPB):	97.882%	Volume Distribution (VD):	0.256
Fu:	1.833% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.973
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.043
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.247	CYP1A2-substrate:	0.892
CYP2C19-inhibitor:	0.971	CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.737
CYP3A4-inhibitor:	0.983	CYP3A4-substrate:	0.908
CYP2B6-substrate:	0.241	CYP2C8-inhibitor:	1.0
HLM stability:	0.967 ? 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):

7.879

Half-life (T1/2):

0.581

ADMET: Toxicity

hERG Blockers:	0.158	hERG Blockers (10um):	0.445
Human Hepatotoxicity (H-HT):	0.639	Drug-induced Liver Injury (DILI):	0.625
AMES Toxicity:	0.577	Rat Oral Acute Toxicity:	0.644
Maximum Recommended Daily Dose:	0.897	Skin Sensitization:	0.136
Carcinogencity:	0.751	Eye Corrosion:	0.002
Eye Irritation:	0.633	Respiratory Toxicity:	0.85
Drug-induced Neurotoxicity:	0.866	Ototoxicity:	0.617
Hematotoxicity:	0.811	Drug-induced Nephrotoxicity:	0.925
Genotoxicity:	0.98	RPMI-8226 Immunitoxicity:	0.238
A549 Cytotoxicity:	0.313	Hek293 Cytotoxicity:	0.592
BCF:	2.19 ? 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:	4.385 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.717 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.347 ? 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
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 36006216]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[11473432]
NPO25366	Sapium indicum	Species	Euphorbiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[12713411]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124776]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17907781]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18804027]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[19646881]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20233596]
NPO25054	Phaleria macrocarpa	Species	Thymelaeaceae	Eukaryota	nut shell	n.a.	n.a.	PMID[23044367]
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24460410]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058711]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8557595]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[8991951]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644081]
NPO24461	Clusia sandiensis	Species	Clusiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24882	Erythrophleum chlorostachys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25492	Botryllus leachi	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25441	Desmodium pulchellu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18706	Anemone thalictroides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25389	Allium angulosum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28460	Achyrocline tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3721	Achyranthes obtusifolia	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23994	Ormosia macrophylla	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15482	Vanderbylia fraxinea	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22152	Tecoma undulata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25277	Seiridium cupressi	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25366	Sapium indicum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23894	Pulicaria insignis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22618	Psolus eximius	Species	Psolidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25054	Phaleria macrocarpa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14189	Osmundaria spiralis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24802	Diploprion bifasciatum	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20264	Moonia heterophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24566	Marasmiellus ramealis	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25466	Lecanora sulphurella	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24730	Lactarius deliciosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24607	Goniothalamus dolichocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27390	Vernonia brevifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30249	Taxus malrei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28460	Achyrocline tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20264	Moonia heterophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25277	Seiridium cupressi	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24730	Lactarius deliciosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25252	Nannocystis exedens	Species	Nannocystaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15482	Vanderbylia fraxinea	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24278	Pistacia chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25366	Sapium indicum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14189	Osmundaria spiralis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23894	Pulicaria insignis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18706	Anemone thalictroides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25492	Botryllus leachi	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25389	Allium angulosum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27390	Vernonia brevifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25054	Phaleria macrocarpa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24373	Lobelia inflata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25466	Lecanora sulphurella	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22152	Tecoma undulata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23788	Beauveria bassiana	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25441	Desmodium pulchellu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24802	Diploprion bifasciatum	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24566	Marasmiellus ramealis	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24882	Erythrophleum chlorostachys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3721	Achyranthes obtusifolia	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24607	Goniothalamus dolichocarpus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24461	Clusia sandiensis	Species	Clusiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22618	Psolus eximius	Species	Psolidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23994	Ormosia macrophylla	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22283	Alhagi maurorum	Species	Fabaceae	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 NPC165550 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	23990
0.1-0.2	24729
0.2-0.3	1137
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6575	Remote Similarity	NPC263212

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC165550 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4659
0.1-0.2	4475
0.2-0.3	16
0.3-0.4	0
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