NPASS Compound

Natural Product: NPC277597

Natural Product ID	NPC277597
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DRAWQKGUORNASA-CLFAGFIQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5497165
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0003809] Diradylglycerols [CHEMONTID:0001129] Diacylglycerols [CHEMONTID:0001647] 1,3-diacylglycerols

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 116115 0 0 0 0 0 0 0 0999 V2000 12.8299 -0.0259 3.2168 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0760 1.0539 2.1964 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4083 0.4464 0.8275 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6405 1.5782 -0.1162 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9636 1.2657 -1.5046 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0866 0.5546 -2.4330 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7804 1.1035 -2.8332 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7078 1.1795 -1.7993 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2770 -0.1585 -1.3268 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0776 -0.6456 -1.3876 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9296 0.0646 -1.9452 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3835 -0.7373 -3.0918 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2217 -0.2376 -3.8090 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8985 -0.0238 -3.2192 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1608 -1.1676 -2.6370 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6707 -1.8095 -1.4127 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6149 -0.9125 -0.1902 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1845 -0.6078 0.1598 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7106 -1.4044 1.0394 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4745 0.4190 -0.4108 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1109 0.6455 0.0172 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1447 1.2284 1.3815 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1371 1.7129 1.9692 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0117 0.7233 2.2876 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7474 -0.0576 1.4531 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7227 0.0774 0.2166 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5991 -1.1024 2.0687 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0025 -0.5953 2.2123 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5644 -0.2714 0.8632 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9747 0.2188 1.0124 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8766 -0.7865 1.6465 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2991 -0.2131 1.7539 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1911 -1.2604 2.4279 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5673 -0.7915 2.5631 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6707 -1.3283 2.0705 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6365 -2.5501 1.2704 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1983 -2.4976 -0.1048 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5793 -1.5565 -1.0535 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6509 -0.0957 -0.7252 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0878 0.3761 -0.5925 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1803 1.8354 -0.2661 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.6705 2.1632 -0.1621 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.8204 3.6313 0.1714 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7295 0.3882 2.3224 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0810 0.2450 3.9748 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4973 -0.9723 2.7088 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7812 -0.2215 3.7741 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9079 1.6866 2.5585 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1742 1.6803 2.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3796 -0.1156 1.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7013 -0.3169 0.5388 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6295 2.0579 0.3032 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9534 2.4614 0.0545 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2014 2.2764 -2.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0163 0.8094 -1.5011 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6947 0.4151 -3.4000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9052 -0.5247 -2.1254 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3686 0.5213 -3.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9377 2.1456 -3.2880 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0899 1.6994 -0.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8769 1.8209 -2.1617 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0450 -0.7939 -0.9036 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8757 -1.6599 -1.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0464 1.1229 -2.1661 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1573 0.0363 -1.1295 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3870 -1.8175 -2.8183 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2494 -0.7122 -3.8629 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0729 -0.9211 -4.7088 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5167 0.7415 -4.3102 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2369 0.3670 -4.0625 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9169 0.8700 -2.5291 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0897 -0.8567 -2.4110 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0114 -1.9801 -3.4006 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6273 -2.3087 -1.4326 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9239 -2.6379 -1.1668 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1062 -1.4467 0.6361 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0795 0.0628 -0.3129 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6296 1.2359 -0.7532 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7352 -0.4416 0.0480 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8800 2.1249 1.3131 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6165 2.3505 1.1552 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0502 2.4365 2.8146 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6093 -1.9654 1.3677 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1700 -1.4191 3.0480 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6289 -1.2906 2.8082 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0253 0.3662 2.7993 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5686 -1.1355 0.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9783 0.5216 0.3406 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3518 0.5529 0.0356 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9302 1.1331 1.6514 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9293 -1.6806 0.9622 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5833 -1.1648 2.6214 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2755 0.6885 2.3941 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6877 0.0782 0.7682 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0066 -2.1977 1.9163 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7735 -1.4207 3.4790 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7144 0.1413 3.1590 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6528 -0.8274 2.2798 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5772 -2.8944 1.1621 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1998 -3.3428 1.8803 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0527 -3.5426 -0.5361 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3264 -2.4180 -0.0863 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0061 -1.6505 -2.0980 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4772 -1.8023 -1.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2819 0.4265 -1.6802 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9902 0.2622 0.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6308 0.2109 -1.5434 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6096 -0.1969 0.1877 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7384 2.4721 -1.0866 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6953 2.1282 0.6764 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.1592 1.5164 0.5858 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.1694 1.9603 -1.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3282 3.8342 1.1516 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2970 4.2348 -0.5904 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.9100 3.8257 0.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2252 0.9234 3.0209 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 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 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 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 22 44 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 2 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 10 63 1 0 11 64 1 0 11 65 1 0 12 66 1 0 12 67 1 0 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 0 15 73 1 0 16 74 1 0 16 75 1 0 17 76 1 0 17 77 1 0 21 78 1 0 21 79 1 0 22 80 1 0 23 81 1 0 23 82 1 0 27 83 1 0 27 84 1 0 28 85 1 0 28 86 1 0 29 87 1 0 29 88 1 0 30 89 1 0 30 90 1 0 31 91 1 0 31 92 1 0 32 93 1 0 32 94 1 0 33 95 1 0 33 96 1 0 34 97 1 0 35 98 1 0 36 99 1 0 36100 1 0 37101 1 0 37102 1 0 38103 1 0 38104 1 0 39105 1 0 39106 1 0 40107 1 0 40108 1 0 41109 1 0 41110 1 0 42111 1 0 42112 1 0 43113 1 0 43114 1 0 43115 1 0 44116 1 0 M END

Standard InCHIKey	DRAWQKGUORNASA-CLFAGFIQSA-N
Standard InCHI	InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-35-37(40)36-44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18-
SMILES	CCCCCCCC/C=CCCCCCCCC(=O)OCC(COC(=O)CCCCCCC/C=CCCCCCCCC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	620.54	Volume:	716.505 ? Van der Waals volume.
Dense:	0.866	LogP:	11.571 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.881 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-8.918 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	36.0	Rigid Bonds:	4.0
TPSA:	72.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.044	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.681	Fsp³:	0.846
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.641	Fluc inhibitor:	0.266 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.9	Promiscuous compounds:	0.133

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.084	MDCK Permeability:	-4.65
Pgp-inhibitor:	0.009	Pgp-substrate:	0.0
PAMPA:	0.0 ? 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):	0.013
20% Bioavailability (F20%):	0.982	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	99.416%	Volume Distribution (VD):	-0.278
Fu:	0.109% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.687
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.966
CYP2C9-inhibitor:	0.008	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.004 ? 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):

4.609

Half-life (T1/2):

1.323

ADMET: Toxicity

hERG Blockers:	0.772	hERG Blockers (10um):	0.926
Human Hepatotoxicity (H-HT):	0.123	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.225	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.234	Skin Sensitization:	1.0
Carcinogencity:	0.093	Eye Corrosion:	0.822
Eye Irritation:	0.69	Respiratory Toxicity:	0.312
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.422
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.818
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.971	Hek293 Cytotoxicity:	0.504
BCF:	-0.657 ? 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:	4.399 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.903 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	1.721 ? 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]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29873264]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
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]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
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]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26718	Chelidonura fulvipunctata	Species	Aglajidae	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]
NPO15520	Dracocephalum kotschyi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14948	Brucea javanica	Species	Simaroubaceae	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]
NPO211	Aplysina cauliformis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1641	Amycolatopsis azurea	Species	Pseudonocardiaceae	Bacteria	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]
NPO11873	Oecophylla smaragdina	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO211	Aplysina cauliformis	Species	Aplysinidae	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]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell line	5

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
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT2740	Cell line	Neutrophils	n.a.	IC50	>	10000.0	nM	PMID[28445049]

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 NPC277597 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	15815
0.1-0.2	29880
0.2-0.3	3486
0.3-0.4	505
0.4-0.5	107
0.5-0.6	34
0.6-0.7	20
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9118	High Similarity	NPC475443
0.9118	High Similarity	NPC473829
0.8	Intermediate Similarity	NPC104537
0.7368	Intermediate Similarity	NPC330426
0.7368	Intermediate Similarity	NPC127091
0.7368	Intermediate Similarity	NPC22101
0.7273	Intermediate Similarity	NPC128061
0.725	Intermediate Similarity	NPC473772
0.6667	Remote Similarity	NPC321919
0.6667	Remote Similarity	NPC223677
0.6667	Remote Similarity	NPC28779
0.6667	Remote Similarity	NPC476654
0.6667	Remote Similarity	NPC476655
0.6667	Remote Similarity	NPC476656
0.6596	Remote Similarity	NPC178758
0.6596	Remote Similarity	NPC192326
0.6596	Remote Similarity	NPC322769
0.65	Remote Similarity	NPC271921
0.6286	Remote Similarity	NPC488257
0.6286	Remote Similarity	NPC469937
0.6286	Remote Similarity	NPC94699
0.6286	Remote Similarity	NPC320588
0.6286	Remote Similarity	NPC53463
0.619	Remote Similarity	NPC48218
0.619	Remote Similarity	NPC141481
0.619	Remote Similarity	NPC464342
0.6176	Remote Similarity	NPC309606
0.6098	Remote Similarity	NPC209327
0.5952	Remote Similarity	NPC273508
0.5897	Remote Similarity	NPC148192
0.5789	Remote Similarity	NPC10316
0.5789	Remote Similarity	NPC200845
0.5778	Remote Similarity	NPC473559
0.5778	Remote Similarity	NPC324981
0.5745	Remote Similarity	NPC474321
0.5676	Remote Similarity	NPC71761
0.5676	Remote Similarity	NPC39633
0.5581	Remote Similarity	NPC54925
0.5556	Remote Similarity	NPC26253
0.5476	Remote Similarity	NPC143857
0.5476	Remote Similarity	NPC229252
0.5472	Remote Similarity	NPC317263
0.5455	Remote Similarity	NPC250028
0.5455	Remote Similarity	NPC236579
0.5455	Remote Similarity	NPC80234
0.5455	Remote Similarity	NPC203531
0.5455	Remote Similarity	NPC256163
0.5455	Remote Similarity	NPC40597
0.5405	Remote Similarity	NPC228473
0.5366	Remote Similarity	NPC485027
0.5366	Remote Similarity	NPC485028
0.5319	Remote Similarity	NPC170963
0.5319	Remote Similarity	NPC324165
0.5319	Remote Similarity	NPC114640
0.5319	Remote Similarity	NPC126366
0.5319	Remote Similarity	NPC608333
0.5278	Remote Similarity	NPC310746
0.5238	Remote Similarity	NPC476660
0.5208	Remote Similarity	NPC206601
0.5116	Remote Similarity	NPC473471
0.5102	Remote Similarity	NPC470268
0.5102	Remote Similarity	NPC321873

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC277597 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5996
0.1-0.2	2944
0.2-0.3	172
0.3-0.4	27
0.4-0.5	11
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