NPASS Compound

Natural Product: NPC212768

Natural Product ID	NPC212768
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ICGBGSGMXXVFJP-DNLBTEDLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL262587
PubChem CID	44452031
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 86 91 0 0 0 0 0 0 0 0999 V2000 2.1119 -2.1419 -0.7210 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1397 -1.4532 -1.5931 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7900 -0.5422 -2.6147 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5106 0.8881 -2.4126 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2674 1.3466 -1.0072 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1743 0.5290 -0.2951 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6183 0.4428 1.1325 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1568 1.2476 -0.2519 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3404 0.3444 -0.0354 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2290 -1.0261 -0.6260 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9111 -1.6972 -0.3066 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0124 -0.7460 -1.0284 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7462 -0.3773 -2.1987 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0093 -0.8656 -2.1220 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2442 -2.1850 -2.8408 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9290 0.1325 -2.7787 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8491 -2.9784 -0.8435 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6100 -4.1101 -0.0661 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4539 -3.9505 1.1560 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5429 -5.4368 -0.6538 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6837 -5.6700 -2.0101 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6106 -6.9419 -2.5156 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3954 -8.0360 -1.7028 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2617 -7.7879 -0.3917 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3268 -6.5619 0.1391 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8253 0.3756 1.2729 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9971 0.8875 1.6894 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6878 1.3742 0.7853 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4851 0.9053 3.0837 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2569 2.2065 0.7958 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4052 3.5635 0.5661 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4422 3.9196 -0.6508 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5185 4.5700 1.6180 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5092 4.2909 2.9572 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6277 5.3026 3.8787 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7604 6.6388 3.5242 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7701 6.9266 2.1683 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6500 5.8939 1.2517 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2716 1.7086 -0.2565 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2193 2.1291 0.4721 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0362 3.4085 0.6875 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4016 1.5528 1.0933 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7862 0.2400 0.9592 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9050 -0.3039 1.5565 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7156 0.4939 2.3488 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3560 1.8153 2.5028 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2201 2.3342 1.8863 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9583 -1.9659 0.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0265 -3.2719 -0.8297 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1857 -2.0005 -1.0680 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6738 -2.2779 -2.2259 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4879 -0.8052 -3.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8882 -0.8211 -2.6077 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4062 1.4678 -2.7586 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6896 1.2199 -3.1032 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6965 2.3374 -1.1818 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0139 -0.1978 1.7807 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4611 1.4704 1.5835 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6474 0.1913 1.3056 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2131 1.8420 -1.1861 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1657 0.8267 -0.5860 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1107 -1.5934 -0.3558 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7155 -1.7808 0.7692 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3784 -2.6067 -3.3310 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7760 -2.8630 -2.1254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0063 -2.0748 -3.6740 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1534 -0.2768 -3.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4574 1.1044 -3.0220 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9342 0.1994 -2.3273 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8529 -4.8192 -2.6657 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7192 -7.1372 -3.5846 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3389 -9.0451 -2.1188 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2151 -6.3814 1.2139 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7071 1.2234 3.8069 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7053 -0.1609 3.3442 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4391 1.4390 3.1908 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4093 3.2769 3.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6266 5.1283 4.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8537 7.4489 4.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8704 7.9509 1.8406 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6621 6.1573 0.1900 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1671 -0.3973 0.3480 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1843 -1.3562 1.4278 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5977 0.0831 2.8253 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9954 2.4260 3.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9825 3.3830 2.0430 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 1 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 13 14 1 0 14 15 1 0 14 16 1 0 11 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 9 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 8 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 5 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 12 2 1 0 25 20 1 0 38 33 1 0 47 42 1 0 12 6 1 0 14 10 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 6 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 6 7 57 1 0 7 58 1 0 7 59 1 0 8 60 1 6 9 61 1 6 10 62 1 6 11 63 1 1 15 64 1 0 15 65 1 0 15 66 1 0 16 67 1 0 16 68 1 0 16 69 1 0 21 70 1 0 22 71 1 0 23 72 1 0 25 73 1 0 29 74 1 0 29 75 1 0 29 76 1 0 34 77 1 0 35 78 1 0 36 79 1 0 37 80 1 0 38 81 1 0 43 82 1 0 44 83 1 0 45 84 1 0 46 85 1 0 47 86 1 0 M END

Standard InCHIKey	ICGBGSGMXXVFJP-DNLBTEDLSA-N
Standard InCHI	InChI=1S/C37H39NO9/c1-22-18-19-27(44-32(40)24-13-8-6-9-14-24)36(5)31(46-33(41)25-15-10-7-11-16-25)29(43-23(2)39)28-30(37(22,36)47-35(28,3)4)45-34(42)26-17-12-20-38-21-26/h6-17,20-22,27-31H,18-19H2,1-5H3/t22-,27+,28-,29-,30-,31-,36+,37-/m1/s1
SMILES	C[C@@H]1CC[C@@H]([C@@]2(C)[C@@H]([C@@H]([C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)c1cccnc1)OC(=O)C)OC(=O)c1ccccc1)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	641.26	Volume:	653.004 ? Van der Waals volume.
Dense:	0.982	LogP:	4.165 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.562 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.929 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	36.0
TPSA:	127.32 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.238	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.671	Fsp³:	0.432
MCE-18:	176.604 ? 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:	0.712	Fluc inhibitor:	0.051 ? 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:	0.234 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.033	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.447	MDCK Permeability:	-4.954
Pgp-inhibitor:	1.0	Pgp-substrate:	0.068
PAMPA:	0.208 ? 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%):	0.094	30% Bioavailability (F30%):	0.42
50% Bioavailability (F50%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128	MRP1:	1.0
Plasma Protein Binding (PPB):	95.225%	Volume Distribution (VD):	-0.202
Fu:	4.868% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.576	BCRP inhibitor:	0.013
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.146	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

5.339

Half-life (T1/2):

0.526

ADMET: Toxicity

hERG Blockers:	0.094	hERG Blockers (10um):	0.584
Human Hepatotoxicity (H-HT):	0.047	Drug-induced Liver Injury (DILI):	0.921
AMES Toxicity:	0.321	Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.511	Skin Sensitization:	0.998
Carcinogencity:	0.876	Eye Corrosion:	0.0
Eye Irritation:	0.408	Respiratory Toxicity:	0.133
Drug-induced Neurotoxicity:	0.682	Ototoxicity:	0.145
Hematotoxicity:	0.017	Drug-induced Nephrotoxicity:	0.722
Genotoxicity:	0.413	RPMI-8226 Immunitoxicity:	0.076
A549 Cytotoxicity:	0.195	Hek293 Cytotoxicity:	0.444
BCF:	0.967 ? 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:	4.069 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.996 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.844 ? 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
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11112781]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	Tanzania	n.a.	PMID[11430019]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[12027753]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12502337]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[153409]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16557460]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	root	n.a.	PMID[17960072]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17960072]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21673922]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23265519]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23317005]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23488669]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26221771]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27524650]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29115831]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31287310]
NPO783	Pholiota squarrosa	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2642	Maytenus apurimacensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6076	Pentzia calva	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15601	Pyrus x bretschneideri	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20434	Tolypocladium ophioglossoides	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO783	Pholiota squarrosa	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15769	Solidago chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5923	Bidens cernua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3835	Reticulitermes flavipes	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2642	Maytenus apurimacensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6076	Pentzia calva	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1019	Citrus hybr	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3588	Crucianella maritima	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1358	Iris pallida	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8278	Perenniporia ochroleuca	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24527	Plazia daphnoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25151	Euphorbia cheiradenia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15601	Pyrus x bretschneideri	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20434	Tolypocladium ophioglossoides	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2309	Achillea micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6313	Phormidium sp	Species	Oscillatoriaceae	Bacteria	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
GI	8

Activity Type	# Activity
Organism	8

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
NPT3697	Organism	Leishmania tropica	Leishmania tropica	GI	=	2.3	%	PMID[18035546]
NPT3697	Organism	Leishmania tropica	Leishmania tropica	GI	=	96.1	%	PMID[18035546]
NPT3697	Organism	Leishmania tropica	Leishmania tropica	GI	=	0.8	%	PMID[18035546]
NPT3697	Organism	Leishmania tropica	Leishmania tropica	GI	=	59.2	%	PMID[18035546]
NPT3697	Organism	Leishmania tropica	Leishmania tropica	GI	=	0.0	%	PMID[18035546]
NPT3697	Organism	Leishmania tropica	Leishmania tropica	GI	=	21.2	%	PMID[18035546]
NPT3697	Organism	Leishmania tropica	Leishmania tropica	GI	=	8.6	%	PMID[18035546]

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 NPC212768 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	18723
0.1-0.2	29292
0.2-0.3	1390
0.3-0.4	263
0.4-0.5	130
0.5-0.6	36
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.942	High Similarity	NPC4421
0.7632	Intermediate Similarity	NPC608007
0.7536	Intermediate Similarity	NPC476094
0.7273	Intermediate Similarity	NPC483887
0.7273	Intermediate Similarity	NPC158020
0.7042	Intermediate Similarity	NPC475429
0.7042	Intermediate Similarity	NPC66761
0.7042	Intermediate Similarity	NPC483843
0.7037	Intermediate Similarity	NPC473115
0.7	Intermediate Similarity	NPC610927
0.6914	Remote Similarity	NPC301368
0.6914	Remote Similarity	NPC84815
0.6667	Remote Similarity	NPC488900
0.6575	Remote Similarity	NPC211137
0.6494	Remote Similarity	NPC473758
0.6463	Remote Similarity	NPC488899
0.6111	Remote Similarity	NPC488902
0.6111	Remote Similarity	NPC488903
0.593	Remote Similarity	NPC6576
0.5823	Remote Similarity	NPC90257
0.5823	Remote Similarity	NPC69357
0.5658	Remote Similarity	NPC183122
0.5632	Remote Similarity	NPC611111
0.5625	Remote Similarity	NPC246841
0.5542	Remote Similarity	NPC481059
0.5517	Remote Similarity	NPC483889
0.5513	Remote Similarity	NPC481047
0.5513	Remote Similarity	NPC481045
0.5506	Remote Similarity	NPC75600
0.5506	Remote Similarity	NPC483884
0.5476	Remote Similarity	NPC127720
0.5455	Remote Similarity	NPC283375
0.5432	Remote Similarity	NPC163719
0.5432	Remote Similarity	NPC483845
0.5432	Remote Similarity	NPC95810
0.5422	Remote Similarity	NPC483844
0.5375	Remote Similarity	NPC475759
0.5333	Remote Similarity	NPC127026
0.5333	Remote Similarity	NPC483890
0.5301	Remote Similarity	NPC66985
0.5287	Remote Similarity	NPC475039
0.5287	Remote Similarity	NPC476035
0.5281	Remote Similarity	NPC483881
0.5256	Remote Similarity	NPC474608
0.5233	Remote Similarity	NPC483848
0.5185	Remote Similarity	NPC90614
0.5165	Remote Similarity	NPC148896
0.5116	Remote Similarity	NPC481071
0.506	Remote Similarity	NPC200471
0.506	Remote Similarity	NPC472575
0.5056	Remote Similarity	NPC276735
0.5056	Remote Similarity	NPC603877
0.5055	Remote Similarity	NPC473089
0.5054	Remote Similarity	NPC253738

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC212768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3627
0.1-0.2	5388
0.2-0.3	133
0.3-0.4	2
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