NPASS Compound

Natural Product: NPC205955

Natural Product ID	NPC205955
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QKJUIIHWGAGPPI-OCRPBTDZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10556620
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 93 98 0 0 0 0 0 0 0 0999 V2000 -6.2577 -2.7527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5298 -1.9578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3247 -3.2299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7349 -0.6857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2358 -0.7381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4410 0.5340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1452 1.8584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9419 0.4816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1470 1.7537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 -1.2135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3273 -0.2783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1683 -0.2563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5090 0.2098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9356 0.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6237 -0.7939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0503 -0.3303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4769 0.1332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7888 1.6004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2612 1.8866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6741 2.6041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8561 3.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2475 2.1406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1328 3.1443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7062 2.6807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4086 3.6844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8351 3.2209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9499 4.2246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5916 -0.8705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0182 -0.4070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2270 -1.8924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6177 -2.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7998 -1.5308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5910 -0.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0901 -0.0978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5892 -0.1501 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2002 0.5165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5040 -2.8552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8229 -3.7264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7279 -1.8400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5447 -2.7444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2742 -2.7784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2458 -1.6317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4547 -3.1171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6161 -1.0216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4391 0.6387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8916 -4.1122 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0597 -1.8501 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9857 -3.5476 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8019 -1.1629 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1590 -4.1739 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5968 -2.4350 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1196 -4.5020 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6983 -2.1385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5378 2.3156 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2143 -0.1736 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1147 1.2436 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2600 -1.1321 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4658 -3.1740 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6731 -1.7912 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7438 -1.2717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8817 -1.6109 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4259 -1.6968 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6762 -2.2929 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9196 -1.8246 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3112 4.0596 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9168 2.4670 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9326 4.7096 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0381 4.4511 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5593 3.6078 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5952 4.5447 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0562 4.3263 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8369 4.1750 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3140 0.9174 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9151 -3.3596 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7325 -3.4580 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2722 -1.2446 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9029 1.4218 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2209 -1.5920 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1424 1.4013 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3840 1.1220 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0030 -2.9076 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5271 -5.0508 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9330 -3.1121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5350 -3.8537 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7678 -2.6397 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5802 -2.1707 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7636 -0.0655 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1147 1.3429 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1433 1.9631 0.0000 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 21 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 36 41 1 0 35 42 1 0 34 43 1 0 16 44 1 0 15 45 1 0 14 46 1 1 46 47 2 0 46 48 1 0 4 49 1 0 30 9 1 0 40 33 1 0 14 10 1 0 26 18 1 0 28 11 1 0 17 11 1 0 1 50 1 0 1 51 1 0 1 52 1 0 2 53 1 0 3 54 1 0 3 55 1 0 3 56 1 0 5 57 1 0 9 58 1 6 10 59 1 1 12 60 1 0 12 61 1 0 15 62 1 1 16 63 1 1 17 64 1 6 19 65 1 0 19 66 1 0 19 67 1 0 20 68 1 0 24 69 1 1 25 70 1 0 25 71 1 0 25 72 1 0 26 73 1 6 27 74 1 0 27 75 1 0 28 76 1 1 33 77 1 1 34 78 1 6 35 79 1 1 36 80 1 6 37 81 1 1 38 82 1 0 38 83 1 0 39 84 1 0 41 85 1 0 42 86 1 0 43 87 1 0 44 88 1 0 45 89 1 0 48 90 1 0 49 91 1 0 49 92 1 0 49 93 1 0 M END

Standard InCHIKey	QKJUIIHWGAGPPI-OCRPBTDZSA-N
Standard InCHI	InChI=1S/C33H44O16/c1-11(2)12(3)6-18(35)49-24-26-32-10-45-33(26,30(43)44)27(41)23(40)25(32)31(5)8-15(19(36)13(4)14(31)7-17(32)48-28(24)42)46-29-22(39)21(38)20(37)16(9-34)47-29/h6,8,11,13-14,16-17,20-27,29,34,37-41H,7,9-10H2,1-5H3,(H,43,44)/b12-6+/t13-,14-,16+,17+,20+,21-,22+,23+,24+,25+,26+,27-,29+,31-,32+,33+/m0/s1
SMILES	CC(C)/C(=C/C(=O)O[C@@H]1[C@@H]2[C@]34CO[C@]2([C@H]([C@@H]([C@@H]4[C@@]2(C)C=C(C(=O)[C@@H](C)[C@@H]2C[C@H]3OC1=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)C(=O)O)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	696.26	Volume:	652.81 ? Van der Waals volume.
Dense:	1.067	LogP:	0.29 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.619 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.931 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	34.0
TPSA:	256.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.114	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.112	Fsp³:	0.758
MCE-18:	170.172 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.692	Fluc inhibitor:	0.008 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.08	Promiscuous compounds:	0.32

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.826	MDCK Permeability:	-5.333
Pgp-inhibitor:	0.001	Pgp-substrate:	0.395
PAMPA:	0.999 ? 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):	0.925
20% Bioavailability (F20%):	0.9	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.987
Plasma Protein Binding (PPB):	71.381%	Volume Distribution (VD):	-0.387
Fu:	24.892% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.147

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.992
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.003 ? 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):

1.033

Half-life (T1/2):

3.829

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.018
Human Hepatotoxicity (H-HT):	0.554	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.845	Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.122	Skin Sensitization:	1.0
Carcinogencity:	0.112	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.124
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.988
Hematotoxicity:	0.75	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.963	RPMI-8226 Immunitoxicity:	0.369
A549 Cytotoxicity:	0.055	Hek293 Cytotoxicity:	0.138
BCF:	0.435 ? 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:	3.207 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.956 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.097 ? 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 NPC205955 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	18024
0.1-0.2	28510
0.2-0.3	3241
0.3-0.4	59
0.4-0.5	9
0.5-0.6	6
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9432	High Similarity	NPC480789
0.8681	High Similarity	NPC295220
0.8646	High Similarity	NPC480790
0.7	Intermediate Similarity	NPC479019
0.6535	Remote Similarity	NPC190065
0.6408	Remote Similarity	NPC141215
0.6286	Remote Similarity	NPC295885
0.6226	Remote Similarity	NPC140045
0.6111	Remote Similarity	NPC471089
0.604	Remote Similarity	NPC475636
0.5962	Remote Similarity	NPC602216
0.5688	Remote Similarity	NPC54614
0.5545	Remote Similarity	NPC480779
0.5408	Remote Similarity	NPC299849
0.5304	Remote Similarity	NPC102465
0.5196	Remote Similarity	NPC312833

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC205955 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6038
0.1-0.2	3061
0.2-0.3	51
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