NPASS Compound

Natural Product: NPC92898

Natural Product ID	NPC92898
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DSTCZBGJCUOFLM-SXNKARFESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	124511085
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

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

Chemical Representations

RDKit 3D 100103 0 0 0 0 0 0 0 0999 V2000 11.8318 0.4965 -2.3570 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0532 1.7349 -1.5261 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7373 2.1957 -0.9080 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2172 1.0773 -0.0377 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9211 1.3897 0.6352 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8279 1.6836 -0.3713 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5937 0.5090 -1.2909 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1872 -0.7333 -0.5692 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8898 -0.4593 0.1718 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4396 -1.6842 0.9108 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1719 -1.4095 1.6443 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0944 -1.0126 0.6922 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7590 -0.7366 1.3811 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2713 -1.9507 2.1023 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0719 -1.6051 2.7520 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9917 -1.2190 1.6602 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0989 -0.0386 1.2954 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7398 -2.1978 1.0407 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6320 -1.8735 -0.0111 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6940 -0.9165 0.4460 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7396 0.2555 -0.1929 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6463 1.4473 -0.0176 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3277 1.8528 -1.2906 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7219 1.7031 -1.4725 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7338 1.4933 -0.4611 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8456 0.0801 0.1306 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6447 -0.7130 -0.8903 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4532 -0.3906 0.2887 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9931 -0.9084 -0.9897 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8768 -2.2527 -0.9000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4400 -3.2149 -1.9621 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2423 -2.7064 0.4596 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -1.4280 1.2334 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5906 -1.3254 1.5544 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3654 -0.5684 2.7068 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7748 -1.4352 2.4305 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4760 -3.2730 0.5605 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7446 0.8469 0.8064 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0899 1.2844 1.8404 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0479 3.1145 -1.4210 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9887 3.8524 -2.7699 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3751 3.9977 -0.2632 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7363 0.3250 -2.9915 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7082 -0.4026 -1.7452 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9421 0.5822 -3.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4681 2.5413 -2.1600 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7538 1.4994 -0.7054 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0451 2.4180 -1.7238 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9650 3.0694 -0.2971 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9579 0.8376 0.7763 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0770 0.1730 -0.6659 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6562 0.5428 1.2820 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0135 2.2818 1.2925 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8889 1.9801 0.1050 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1447 2.5372 -1.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4953 0.3434 -1.9342 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7321 0.8096 -1.9514 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9866 -1.0385 0.1246 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9581 -1.5097 -1.3209 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9550 0.3609 0.8838 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1478 -0.2112 -0.6379 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3186 -2.4931 0.1554 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2489 -1.9570 1.6221 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3650 -0.5326 2.3179 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8805 -2.2345 2.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8890 -1.8060 -0.0563 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3410 -0.0500 0.1766 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9118 0.1288 2.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0645 -0.4536 0.5635 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9460 -2.3015 2.8904 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1504 -2.7888 1.3871 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0321 -0.7897 3.4703 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4891 -2.4755 3.3070 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0854 -2.8120 -0.3474 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0956 -1.4168 -0.8446 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0114 0.3776 -0.9624 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1311 2.2674 0.5034 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6452 1.6277 -2.1668 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0772 1.4330 -2.5187 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7035 2.1724 0.4356 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7553 1.6978 -0.8927 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4327 0.1267 1.0512 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3148 -1.4687 -0.3950 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0039 -1.1703 -1.6601 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3412 -0.0286 -1.4242 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7381 -0.4687 -1.9494 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3343 -3.6773 -2.4583 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7872 -2.6973 -2.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8288 -3.9930 -1.4664 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4778 -3.4625 0.7706 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2526 -2.3656 1.8485 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4715 -0.7219 3.0821 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1768 -1.5239 3.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9374 -3.1444 1.4068 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9752 4.3229 -2.7944 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1437 3.1068 -3.5595 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7977 4.5877 -2.7571 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0375 5.0260 -0.5142 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8353 3.7388 0.6668 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4860 4.1183 -0.0972 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 1 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 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 28 29 1 6 29 30 2 0 30 31 1 0 30 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 1 32 37 1 0 28 38 1 0 38 39 2 0 24 40 1 0 40 41 1 0 40 42 1 0 34 20 1 0 38 22 1 0 40 23 1 0 33 28 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 6 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 10 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 19 74 1 0 19 75 1 0 21 76 1 0 22 77 1 1 23 78 1 6 24 79 1 6 25 80 1 0 25 81 1 0 26 82 1 1 27 83 1 0 27 84 1 0 27 85 1 0 29 86 1 0 31 87 1 0 31 88 1 0 31 89 1 0 32 90 1 1 34 91 1 1 35 92 1 0 36 93 1 0 37 94 1 0 41 95 1 0 41 96 1 0 41 97 1 0 42 98 1 0 42 99 1 0 42100 1 0 M END

Standard InCHIKey	DSTCZBGJCUOFLM-SXNKARFESA-N
Standard InCHI	InChI=1S/C36H58O6/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-29(37)42-23-26-21-27-30-28(34(30,4)5)20-25(3)35(33(27)40)22-24(2)31(38)36(35,41)32(26)39/h21-22,25,27-28,30-32,38-39,41H,6-20,23H2,1-5H3/t25-,27+,28-,30+,31+,32-,35+,36-/m1/s1
SMILES	CCCCCCCCCCCCCCCC(=O)OCC1=C[C@H]2[C@H]3[C@@H](C[C@@H](C)[C@@]4(C=C(C)[C@@H]([C@]4([C@@H]1O)O)O)C2=O)C3(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	586.42	Volume:	639.182 ? Van der Waals volume.
Dense:	0.917	LogP:	7.339 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.901 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.456 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	20.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.104	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.914	Fsp³:	0.833
MCE-18:	102.394 ? 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:	0.602	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? 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:	0.219	Promiscuous compounds:	0.411

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.147	MDCK Permeability:	-4.661
Pgp-inhibitor:	0.001	Pgp-substrate:	0.039
PAMPA:	0.02 ? 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):	0.732
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048	MRP1:	0.862
Plasma Protein Binding (PPB):	98.451%	Volume Distribution (VD):	0.731
Fu:	1.586% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.332
BSEP inhibitor:	0.945

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.171
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.143	CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.015 ? 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):

4.581

Half-life (T1/2):

1.567

ADMET: Toxicity

hERG Blockers:	0.184	hERG Blockers (10um):	0.547
Human Hepatotoxicity (H-HT):	0.637	Drug-induced Liver Injury (DILI):	0.459
AMES Toxicity:	0.299	Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.821	Skin Sensitization:	0.999
Carcinogencity:	0.795	Eye Corrosion:	0.0
Eye Irritation:	0.342	Respiratory Toxicity:	0.916
Drug-induced Neurotoxicity:	0.019	Ototoxicity:	0.525
Hematotoxicity:	0.333	Drug-induced Nephrotoxicity:	0.783
Genotoxicity:	0.007	RPMI-8226 Immunitoxicity:	0.208
A549 Cytotoxicity:	0.911	Hek293 Cytotoxicity:	0.375
BCF:	1.013 ? 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:	5.063 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.548 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.153 ? 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
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542364]
NPO3171	Menisporopsis theobromae	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[15104506]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15165157]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548580]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[21627109]
NPO5813	Ligularia songarica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23043462]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24195447]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	Gum resin	n.a.	n.a.	PMID[26457560]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30817151]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31095383]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14881	Senecio nemorensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10833	Heteromma simplicifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4494	Ecbolium linneanum	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3940	Erioderma chilense	Species	Pannariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO460	Alangium ridleyi	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28795	Retiboletus ornatipes	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO735	Pteraster multipes	Species	Pterasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3171	Menisporopsis theobromae	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5813	Ligularia songarica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO392	Laurencia composita	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3319	Helichrysum nitens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4658	Hedysarum denticulatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5007	Deltocyathus magnificus	Species	Caryophylliidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4783	Cyphus niveus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5571	Jacobaea arnautorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1000	Thymus transcaucasicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8283	Pseudophegopteris subaurita	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10733	Plantago uniflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10479	Ophiocoma echinata	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10959	Kalanchoe marmorata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14881	Senecio nemorensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14881	Senecio nemorensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14881	Senecio nemorensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8283	Pseudophegopteris subaurita	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4494	Ecbolium linneanum	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5571	Jacobaea arnautorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10833	Heteromma simplicifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4658	Hedysarum denticulatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO392	Laurencia composita	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5007	Deltocyathus magnificus	Species	Caryophylliidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5813	Ligularia songarica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3171	Menisporopsis theobromae	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1000	Thymus transcaucasicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO735	Pteraster multipes	Species	Pterasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10733	Plantago uniflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3319	Helichrysum nitens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10479	Ophiocoma echinata	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3940	Erioderma chilense	Species	Pannariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO460	Alangium ridleyi	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28795	Retiboletus ornatipes	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14881	Senecio nemorensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10959	Kalanchoe marmorata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4783	Cyphus niveus	n.a.	n.a.	n.a.	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	1
Ratio CC50/IC50	1
CC50	1

Activity Type	# Activity
Cell line	1
Organism	1
Others	1

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
NPT25	Cell line	MT4	Homo sapiens	CC50	>	1700.0	nM	PMID[31184480]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	1.1	nM	PMID[31184480]
NPT2	Others	Unspecified	n.a.	Ratio CC50/IC50	>	1538.5	n.a.	PMID[31184480]

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 NPC92898 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	17678
0.1-0.2	30018
0.2-0.3	2042
0.3-0.4	82
0.4-0.5	18
0.5-0.6	12
0.6-0.7	3
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC31883
1.0	High Similarity	NPC179891
0.8246	Intermediate Similarity	NPC604048
0.7313	Intermediate Similarity	NPC123855
0.7313	Intermediate Similarity	NPC76550
0.6491	Remote Similarity	NPC607158
0.6418	Remote Similarity	NPC473488
0.6066	Remote Similarity	NPC261341
0.5942	Remote Similarity	NPC267734
0.5942	Remote Similarity	NPC482241
0.5479	Remote Similarity	NPC475661
0.5278	Remote Similarity	NPC308191
0.5278	Remote Similarity	NPC38423
0.519	Remote Similarity	NPC67290
0.519	Remote Similarity	NPC133677
0.5139	Remote Similarity	NPC607683
0.5125	Remote Similarity	NPC75898
0.5125	Remote Similarity	NPC221349
0.5063	Remote Similarity	NPC482242
0.5063	Remote Similarity	NPC482243

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC92898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6494
0.1-0.2	2563
0.2-0.3	88
0.3-0.4	4
0.4-0.5	1
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