NPASS Compound

Natural Product: NPC101786

Natural Product ID	NPC101786
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PGWFWMDCOBABRO-MNFWPPMYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane 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 95101 0 0 0 0 0 0 0 0999 V2000 11.2471 0.6079 1.2955 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7620 0.2506 1.2641 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0443 1.5073 0.7896 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5339 1.2556 0.7254 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9091 2.5358 0.2538 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4304 2.4483 0.1494 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8337 1.3305 0.4587 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3902 1.2272 0.3638 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7841 0.1064 0.6737 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3104 0.0133 0.5736 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8188 -0.6814 1.6534 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5383 -0.3746 1.5704 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0282 -1.3056 0.4405 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8885 -2.6718 0.9259 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6623 -3.7143 0.2515 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4156 -4.7299 1.0984 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0756 -6.0319 0.7855 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3347 -3.3868 -1.0222 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6367 -2.6508 -2.0562 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3835 -1.9363 -1.8038 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0980 -1.6117 -3.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3695 -2.5359 -3.9807 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1490 -2.6364 -5.4596 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1833 -3.4935 -3.2328 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4827 -4.6795 -3.4188 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3602 -0.8450 -0.7965 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0567 0.4259 -1.2112 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3179 1.2268 -2.2414 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3837 1.3370 -0.0295 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5146 1.0455 1.1592 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7648 2.0524 2.2047 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0574 1.7469 3.4335 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6738 3.4931 1.8302 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8049 1.2707 0.7593 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7710 1.3542 0.2285 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5984 2.4500 0.0493 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0458 3.4669 -0.3712 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0354 2.4147 0.3368 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6392 1.3515 0.7832 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0581 1.3462 1.0575 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6114 0.1802 1.5438 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9563 0.1074 1.8205 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7984 1.1843 1.6256 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2433 2.3501 1.1391 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8771 2.4260 0.8576 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9905 -0.5152 -0.6452 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5536 -1.7718 -2.6812 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5755 -2.7676 -0.7170 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2820 -3.7444 0.3607 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3795 1.4049 2.0478 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8497 -0.2776 1.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5098 0.9846 0.2956 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5577 -0.6005 0.5895 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4303 0.0677 2.2960 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2064 2.3211 1.5054 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4164 1.7329 -0.2100 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2210 0.9799 1.7464 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3145 0.3979 0.0512 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2867 2.8610 -0.7241 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1207 3.3104 1.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8816 3.3210 -0.1838 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4162 0.4880 0.7841 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7940 2.0780 0.0340 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3555 -0.7381 0.9981 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9846 -0.6433 2.5161 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1394 -1.1286 0.2898 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8810 -2.7822 2.0602 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4929 -4.5954 0.8808 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3039 -4.5080 2.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1660 -6.2481 1.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6644 -4.3790 -1.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4633 -2.6406 -1.4830 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7104 -0.8068 -3.4816 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9357 -2.6989 -5.6903 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7470 -3.4378 -5.8798 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5014 -1.6549 -5.8855 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0488 0.1972 -1.6602 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5675 2.3051 -2.0254 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7017 1.0935 -3.2714 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7823 1.1748 -2.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1603 2.3707 -0.3438 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1463 0.7602 3.8098 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2304 2.5756 4.1515 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2323 3.6769 0.8405 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0678 3.9301 2.5563 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6489 4.0069 1.9017 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5840 3.3204 0.1618 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0186 0.4667 0.9378 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0231 -0.7131 1.7265 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3799 -0.8076 2.1994 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8609 1.1073 1.8509 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9018 3.1913 0.9864 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5179 3.3773 0.4779 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1688 -2.2401 -3.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2627 -3.0293 -1.3562 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 2 0 7 8 1 0 8 9 2 0 10 9 1 1 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 16 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 2 0 20 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 30 31 1 1 31 32 2 0 31 33 1 0 30 34 1 0 29 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 26 46 1 1 19 47 1 6 18 48 1 0 15 49 1 0 34 10 1 0 45 40 1 0 46 10 1 0 30 12 1 0 26 13 1 0 49 14 1 0 24 19 1 0 1 50 1 0 1 51 1 0 1 52 1 0 2 53 1 0 2 54 1 0 3 55 1 0 3 56 1 0 4 57 1 0 4 58 1 0 5 59 1 0 5 60 1 0 6 61 1 0 7 62 1 0 8 63 1 0 9 64 1 0 12 65 1 1 13 66 1 6 14 67 1 1 16 68 1 0 16 69 1 0 17 70 1 0 18 71 1 6 20 72 1 1 21 73 1 0 23 74 1 0 23 75 1 0 23 76 1 0 27 77 1 6 28 78 1 0 28 79 1 0 28 80 1 0 29 81 1 6 32 82 1 0 32 83 1 0 33 84 1 0 33 85 1 0 33 86 1 0 38 87 1 0 39 88 1 0 41 89 1 0 42 90 1 0 43 91 1 0 44 92 1 0 45 93 1 0 47 94 1 0 48 95 1 0 M END

Standard InCHIKey	PGWFWMDCOBABRO-MNFWPPMYSA-N
Standard InCHI	InChI=1S/C39H46O10/c1-6-7-8-9-10-11-15-20-36-47-33-29-32-35(22-40,46-32)34(43)37(44)27(21-24(4)30(37)42)39(29,49-36)25(5)31(38(33,48-36)23(2)3)45-28(41)19-18-26-16-13-12-14-17-26/h10-21,25,27,29,31-34,40,43-44H,2,6-9,22H2,1,3-5H3/b11-10+,19-18+,20-15+/t25-,27-,29+,31-,32+,33-,34-,35+,36-,37-,38+,39+/m1/s1
SMILES	CCCCC/C=C/C=C/[C@@]12O[C@@H]3[C@@H]4[C@H]5[C@@](CO)([C@H]([C@]6([C@@H](C=C(C)C6=O)[C@]4([C@H](C)[C@H]([C@]3(C(=C)C)O1)OC(=O)/C=C/c1ccccc1)O2)O)O)O5

Calculated Properties

Physi-Chem Properties

Molecular Weight:	674.31	Volume:	684.742 ? Van der Waals volume.
Dense:	0.985	LogP:	4.647 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.17 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.4 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	36.0
TPSA:	144.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	7.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.078	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.781	Fsp³:	0.538
MCE-18:	163.2 ? 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:	0.853	Fluc inhibitor:	0.333 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.251 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.13	Promiscuous compounds:	0.277

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.317	MDCK Permeability:	-4.945
Pgp-inhibitor:	0.802	Pgp-substrate:	0.002
PAMPA:	0.031 ? 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):	0.002
20% Bioavailability (F20%):	0.355	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029	MRP1:	0.457
Plasma Protein Binding (PPB):	96.746%	Volume Distribution (VD):	-0.078
Fu:	2.152% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.023
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.991
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.97
CYP2C9-inhibitor:	0.269	CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.395	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.007 ? 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):

4.182

Half-life (T1/2):

1.072

ADMET: Toxicity

hERG Blockers:	0.143	hERG Blockers (10um):	0.421
Human Hepatotoxicity (H-HT):	0.587	Drug-induced Liver Injury (DILI):	0.463
AMES Toxicity:	0.918	Rat Oral Acute Toxicity:	0.575
Maximum Recommended Daily Dose:	0.81	Skin Sensitization:	1.0
Carcinogencity:	0.15	Eye Corrosion:	0.005
Eye Irritation:	0.383	Respiratory Toxicity:	0.831
Drug-induced Neurotoxicity:	0.387	Ototoxicity:	0.717
Hematotoxicity:	0.696	Drug-induced Nephrotoxicity:	0.689
Genotoxicity:	0.064	RPMI-8226 Immunitoxicity:	0.275
A549 Cytotoxicity:	0.839	Hek293 Cytotoxicity:	0.861
BCF:	1.361 ? 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:	4.709 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.163 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.673 ? 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
NPO19803	Oxytropis ochrocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22494026]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24156713]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32997496]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19479	Trametes feei	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18393	Eugenia sandwicensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19803	Oxytropis ochrocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16416	Serratula strangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17135	Mikania goyazensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18816	Lindera glauca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18816	Lindera glauca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16416	Serratula strangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18393	Eugenia sandwicensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18816	Lindera glauca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16416	Serratula strangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15287	Vernonia megapotamica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10882	Acer caudatifolium	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12444	Astragalus sinicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17558	Cynoglossum formosanum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7037	Rumohra adiantiformis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18393	Eugenia sandwicensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17135	Mikania goyazensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14508	Aconitum heterophyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19406	Chrysanthemum leptophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13505	Grateloupia livida	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19479	Trametes feei	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14015	Salacia cordata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10705	Marshallia graminifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12376	Baccharis macraei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19803	Oxytropis ochrocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18816	Lindera glauca	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19303	Auricularia auricula-judae	Species	Auriculariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18247	Globicephala melas	Species	Delphinidae	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
EC50	1
IC50	1

Activity Type	# Activity
Cell line	1
Organism	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	IC50	>	34.0	nM	PMID[32997496]
NPT1114	Organism	Human immunodeficiency virus	Human immunodeficiency virus	EC50	=	2.2	nM	PMID[32997496]

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 NPC101786 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	10254
0.1-0.2	37199
0.2-0.3	2221
0.3-0.4	112
0.4-0.5	20
0.5-0.6	10
0.6-0.7	11
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC130886
0.931	High Similarity	NPC486153
0.8901	High Similarity	NPC481773
0.828	Intermediate Similarity	NPC481774
0.8182	Intermediate Similarity	NPC69240
0.7816	Intermediate Similarity	NPC223356
0.7816	Intermediate Similarity	NPC298697
0.7816	Intermediate Similarity	NPC475500
0.7816	Intermediate Similarity	NPC100017
0.7816	Intermediate Similarity	NPC481742
0.7766	Intermediate Similarity	NPC92598
0.7766	Intermediate Similarity	NPC43304
0.7766	Intermediate Similarity	NPC481753
0.7766	Intermediate Similarity	NPC477188
0.7766	Intermediate Similarity	NPC477190
0.7727	Intermediate Similarity	NPC182266
0.7727	Intermediate Similarity	NPC475154
0.7727	Intermediate Similarity	NPC485700
0.7727	Intermediate Similarity	NPC75831
0.7727	Intermediate Similarity	NPC471137
0.764	Intermediate Similarity	NPC471136
0.764	Intermediate Similarity	NPC116727
0.764	Intermediate Similarity	NPC39509
0.7624	Intermediate Similarity	NPC191992
0.7556	Intermediate Similarity	NPC481744
0.7556	Intermediate Similarity	NPC481743
0.7191	Intermediate Similarity	NPC324104
0.7191	Intermediate Similarity	NPC473548
0.7188	Intermediate Similarity	NPC164150
0.7188	Intermediate Similarity	NPC481754
0.7111	Intermediate Similarity	NPC180902
0.6768	Remote Similarity	NPC486154
0.6522	Remote Similarity	NPC251564
0.6522	Remote Similarity	NPC477189
0.6452	Remote Similarity	NPC474508
0.6452	Remote Similarity	NPC473485
0.6452	Remote Similarity	NPC171411
0.6452	Remote Similarity	NPC485701
0.6277	Remote Similarity	NPC475314
0.6277	Remote Similarity	NPC102997
0.6211	Remote Similarity	NPC485693
0.6162	Remote Similarity	NPC275477
0.5962	Remote Similarity	NPC481745
0.5789	Remote Similarity	NPC162495
0.5769	Remote Similarity	NPC481776
0.5743	Remote Similarity	NPC605479
0.5729	Remote Similarity	NPC475606
0.5714	Remote Similarity	NPC156682
0.5714	Remote Similarity	NPC49297
0.5514	Remote Similarity	NPC68282
0.5146	Remote Similarity	NPC481750
0.505	Remote Similarity	NPC181924

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC101786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3854
0.1-0.2	5231
0.2-0.3	65
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