NPASS Compound

Natural Product: NPC61694

Natural Product ID	NPC61694
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZTCBOAIWPIKLEJ-DAMXAWHRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10030889
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

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 89 94 0 0 0 0 0 0 0 0999 V2000 -1.9361 4.7300 0.5268 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6391 3.6278 -0.1997 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4682 3.8634 -1.1033 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3664 2.3318 0.1350 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9763 1.1878 -0.4892 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8245 0.5145 0.5075 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2209 -0.8854 0.2660 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6680 -1.1814 0.2200 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5197 -0.3365 -0.6492 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1862 -0.9688 1.6592 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8322 -2.6422 -0.0021 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0036 -3.0842 -0.0742 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6455 -3.5051 -0.1277 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4733 -3.0377 -0.5170 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3875 -1.5992 -0.8278 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0552 -1.4519 -2.1664 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0396 -1.0446 -0.6894 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8389 -1.7727 -1.1328 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4025 -1.4256 -0.3263 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3969 0.0023 0.2313 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0147 -0.0614 1.6612 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7713 0.5523 0.0229 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5054 1.9834 -0.3382 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1529 1.9274 -0.9468 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5057 0.8176 -0.6466 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8719 0.3990 -1.0905 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9934 0.6059 -2.6130 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7338 0.5536 1.1319 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0851 1.2058 0.6754 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8685 0.8719 1.9289 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3315 1.1140 1.8437 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1642 1.2464 0.7069 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6681 0.9543 0.8834 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8041 1.5446 -0.7061 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7783 2.4287 1.5432 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5203 -0.4205 2.2411 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3469 -0.7437 1.5151 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7636 -1.4354 0.3394 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -2.7826 0.1916 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9110 -3.3863 1.1142 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9299 -3.5444 -1.0292 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8734 4.5198 0.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0178 5.6935 -0.0283 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4092 4.8104 1.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6715 1.6470 -1.2569 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3516 0.6963 1.5235 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7862 1.1070 0.6067 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8607 -1.4483 1.1955 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5242 -0.1366 -0.1642 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8144 -0.9467 -1.5538 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1254 0.6475 -0.8917 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4115 -1.2545 2.3873 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5294 0.0602 1.8120 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0659 -1.6338 1.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7366 -4.5691 0.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6543 -3.7018 -0.5921 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3813 -1.7665 -2.9608 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8974 -2.2132 -2.2333 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5906 -0.5050 -2.3148 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8803 -1.0155 0.4392 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9603 -2.8588 -0.9717 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6338 -1.6975 -2.2429 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5702 -2.1276 0.5108 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2455 -1.5577 -1.0339 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7453 0.3390 2.3898 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1451 -1.1163 2.0531 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9131 0.5778 1.9102 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2802 0.0843 -0.8711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2233 2.3127 -1.1096 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5223 2.6816 0.5026 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2552 2.7312 -1.5821 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6062 -0.2124 -3.2017 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9362 1.0660 -2.9138 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2435 1.4415 -2.8047 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4949 1.2188 1.9870 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0124 2.2742 0.5886 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5049 0.6269 -0.1443 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3988 1.5141 2.7291 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8585 0.7788 2.7974 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2487 1.4095 0.0807 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7487 -0.1564 0.7932 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9775 1.2199 1.9019 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0095 2.3173 -0.8374 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5497 0.6851 -1.3352 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6944 2.0156 -1.2362 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8075 -1.4295 2.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1836 -4.3338 -1.2711 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8679 -4.0748 -0.7573 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1523 -2.8730 -1.8669 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 8 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 6 22 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 30 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 26 5 1 0 37 28 1 0 15 7 1 0 26 17 1 0 35 31 1 0 25 20 1 0 1 42 1 0 1 43 1 0 1 44 1 0 5 45 1 6 6 46 1 0 6 47 1 0 7 48 1 1 9 49 1 0 9 50 1 0 9 51 1 0 10 52 1 0 10 53 1 0 10 54 1 0 13 55 1 0 14 56 1 0 16 57 1 0 16 58 1 0 16 59 1 0 17 60 1 1 18 61 1 0 18 62 1 0 19 63 1 0 19 64 1 0 21 65 1 0 21 66 1 0 21 67 1 0 22 68 1 6 23 69 1 0 23 70 1 0 24 71 1 0 27 72 1 0 27 73 1 0 27 74 1 0 28 75 1 1 29 76 1 0 29 77 1 0 30 78 1 1 31 79 1 1 33 80 1 0 33 81 1 0 33 82 1 0 34 83 1 0 34 84 1 0 34 85 1 0 37 86 1 1 41 87 1 0 41 88 1 0 41 89 1 0 M END

Standard InCHIKey	ZTCBOAIWPIKLEJ-DAMXAWHRSA-N
Standard InCHI	InChI=1S/C34H48O7/c1-18(35)38-27-17-25-30(3,4)26(37)13-15-33(25,8)24-12-14-32(7)21(10-11-23(32)34(24,27)9)20-16-22(28-31(5,6)41-28)40-29(20)39-19(2)36/h11,13,15,20-22,24-25,27-29H,10,12,14,16-17H2,1-9H3/t20-,21-,22+,24+,25-,27+,28-,29-,32-,33+,34-/m0/s1
SMILES	CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC=C3[C@]12C)[C@@H]1C[C@H]([C@H]2C(C)(C)O2)O[C@@H]1OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	568.34	Volume:	593.63 ? Van der Waals volume.
Dense:	0.957	LogP:	3.841 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.58 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.601 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	31.0
TPSA:	91.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.235	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.425	Fsp³:	0.794
MCE-18:	116.557 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.928	Fluc inhibitor:	0.016 ? 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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.336	Promiscuous compounds:	0.795

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.226	MDCK Permeability:	-4.916
Pgp-inhibitor:	0.999	Pgp-substrate:	0.038
PAMPA:	0.706 ? 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):	0.001
20% Bioavailability (F20%):	0.249	30% Bioavailability (F30%):	0.438
50% Bioavailability (F50%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.99
Plasma Protein Binding (PPB):	87.348%	Volume Distribution (VD):	-0.262
Fu:	11.705% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.942	BCRP inhibitor:	0.062
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.992	CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.009	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.009	CYP2C8-inhibitor:	0.954
HLM stability:	0.94 ? 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):

7.875

Half-life (T1/2):

0.391

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.088
Human Hepatotoxicity (H-HT):	0.544	Drug-induced Liver Injury (DILI):	0.799
AMES Toxicity:	0.727	Rat Oral Acute Toxicity:	0.828
Maximum Recommended Daily Dose:	0.794	Skin Sensitization:	0.979
Carcinogencity:	0.732	Eye Corrosion:	0.003
Eye Irritation:	0.253	Respiratory Toxicity:	0.689
Drug-induced Neurotoxicity:	0.099	Ototoxicity:	0.725
Hematotoxicity:	0.756	Drug-induced Nephrotoxicity:	0.952
Genotoxicity:	0.972	RPMI-8226 Immunitoxicity:	0.11
A549 Cytotoxicity:	0.204	Hek293 Cytotoxicity:	0.167
BCF:	0.906 ? 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:	4.013 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.866 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.228 ? 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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15949825]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18723353]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26522747]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29873264]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33172599]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36253818]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350091]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14150	Solanum jamaicense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12944	Sideritis tragoriganum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11637	Psilostrophe cooperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14528	Pneumatospora obcoronata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12717	Parmelia metastrigosa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11873	Oecophylla smaragdina	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14749	Lippia carviodora	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1641	Amycolatopsis azurea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26718	Chelidonura fulvipunctata	Species	Aglajidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14845	Ceratophyllum submersum	Species	Ceratophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9203	Cephalonomia gallicola	Species	Bethylidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11432	Centrolobium tomentosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5303	Castanea crenata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10818	Carpobrotus edulis	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11084	Asplenium normale	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3164	Yponomeuta malinellus	Species	Yponomeutidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15146	Myrica nana	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14749	Lippia carviodora	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11637	Psilostrophe cooperi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5303	Castanea crenata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14528	Pneumatospora obcoronata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14845	Ceratophyllum submersum	Species	Ceratophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1641	Amycolatopsis azurea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11873	Oecophylla smaragdina	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11432	Centrolobium tomentosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12717	Parmelia metastrigosa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9203	Cephalonomia gallicola	Species	Bethylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26718	Chelidonura fulvipunctata	Species	Aglajidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11084	Asplenium normale	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14150	Solanum jamaicense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12944	Sideritis tragoriganum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3164	Yponomeuta malinellus	Species	Yponomeutidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10818	Carpobrotus edulis	Species	Aizoaceae	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 NPC61694 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	21220
0.1-0.2	25268
0.2-0.3	3277
0.3-0.4	50
0.4-0.5	27
0.5-0.6	9
0.6-0.7	4
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
0.7534	Intermediate Similarity	NPC161065
0.7532	Intermediate Similarity	NPC204731
0.7324	Intermediate Similarity	NPC480954
0.7125	Intermediate Similarity	NPC243981
0.6579	Remote Similarity	NPC302471
0.6528	Remote Similarity	NPC292133
0.6234	Remote Similarity	NPC480952
0.6	Remote Similarity	NPC152117
0.5875	Remote Similarity	NPC5284
0.5802	Remote Similarity	NPC255017
0.573	Remote Similarity	NPC241192
0.5556	Remote Similarity	NPC79117
0.5256	Remote Similarity	NPC189616
0.5205	Remote Similarity	NPC38530
0.5205	Remote Similarity	NPC84335
0.5125	Remote Similarity	NPC469844
0.5111	Remote Similarity	NPC298841

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC61694 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7018
0.1-0.2	2012
0.2-0.3	120
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