NPASS Compound

Natural Product: NPC166709

Natural Product ID	NPC166709
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NSZFSZBDUJELCA-JBJYXYLFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101277261
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 79 83 0 0 0 0 0 0 0 0999 V2000 6.1718 0.6113 1.5235 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8516 1.0570 0.9379 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6445 2.5218 1.3724 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7406 0.1942 1.5182 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8857 -0.3467 0.4308 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5846 -0.2153 0.4532 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9011 0.4749 1.5690 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3842 0.7155 1.4608 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1498 0.3261 0.2856 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6440 0.3555 0.5735 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0089 -0.3271 1.8337 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9703 1.8477 0.7613 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4454 2.0632 0.8985 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2796 1.4393 -0.1546 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8426 0.1108 -0.6452 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5861 -0.9630 0.0718 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2752 0.0300 -2.1221 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3484 -0.0586 -0.6643 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9465 -1.4074 -1.1599 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4641 -1.2928 -1.5544 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6666 -0.9399 -0.3113 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7267 -2.1371 0.5941 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7875 -0.7601 -0.6827 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9709 0.1364 -1.8870 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4252 -2.0908 -1.0701 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7958 -1.7492 -1.6441 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6600 -1.0790 -0.6445 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7172 -0.2160 -1.2451 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8992 1.0860 -0.5501 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0733 2.1102 -1.0303 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3837 -2.1607 0.1325 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6304 -2.2432 0.1091 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6258 -3.0548 0.8690 O 0 0 0 0 0 1 0 0 0 0 0 0 -5.4092 2.3459 -1.2275 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4990 1.3449 2.2813 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0273 -0.3562 2.0594 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9473 0.4828 0.7363 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7941 2.9421 0.7913 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5008 2.5922 2.4617 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5464 3.0824 1.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2326 0.8053 2.2535 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1926 -0.6652 2.0935 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4406 0.7758 2.4782 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8412 1.2331 2.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0276 1.1373 -0.4939 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0506 -0.5219 2.4021 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6295 -1.2208 1.7522 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5743 0.3445 2.5490 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4792 2.2386 1.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6341 2.4044 -0.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8553 1.7845 1.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6010 3.1809 0.8312 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3312 1.3342 0.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1239 -1.9595 0.0307 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8712 -0.6590 1.1220 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5913 -1.0887 -0.4322 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2224 0.5907 -2.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5165 0.4685 -2.7838 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4501 -1.0327 -2.4148 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9951 0.6664 -1.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1347 -2.2367 -0.4808 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4738 -1.5554 -2.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4329 -0.4720 -2.3084 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1098 -2.2021 -2.0325 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4271 -3.0194 -0.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0487 -2.0972 1.3991 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7135 -2.4044 0.9666 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3356 1.0249 -1.9059 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8253 -0.5141 -2.7814 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0207 0.5084 -1.8566 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8699 -2.5533 -1.9078 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5774 -2.7660 -0.2315 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2575 -2.7490 -1.8927 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7184 -1.2359 -2.6164 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7130 -0.7335 -1.3012 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4765 0.0136 -2.3158 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9427 1.4417 -0.8172 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9610 2.0152 -1.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4424 3.2463 -0.8141 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 1 1 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 6 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 27 31 1 1 31 32 2 0 31 33 1 0 14 34 1 0 29 2 1 0 27 5 1 0 23 6 1 0 21 9 1 0 18 10 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 7 43 1 0 8 44 1 0 9 45 1 6 11 46 1 0 11 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 1 16 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 17 59 1 0 18 60 1 6 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 24 68 1 0 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 28 75 1 0 28 76 1 0 29 77 1 1 30 78 1 0 34 79 1 0 M CHG 1 33 -1 M END

Standard InCHIKey	NSZFSZBDUJELCA-JBJYXYLFSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-25(2)16-19-18-8-9-21-27(5)12-11-22(31)26(3,4)20(27)10-13-29(21,7)28(18,6)14-15-30(19,24(33)34)17-23(25)32/h8-9,20-23,31-32H,10-17H2,1-7H3,(H,33,34)/p-1/t20-,21+,22+,23+,27-,28+,29+,30+/m0/s1
SMILES	CC1(C)CC2=C3C=C[C@@H]4[C@@]5(C)CC[C@H](C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@]2(C[C@H]1O)C(=O)[O-])O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	2.687 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.544 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.841 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.431	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.049	Fsp³:	0.833
MCE-18:	106.182 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.622	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.135 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.399	Promiscuous compounds:	0.101

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.448	MDCK Permeability:	-5.011
Pgp-inhibitor:	0.001	Pgp-substrate:	0.867
PAMPA:	0.999 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.135	30% Bioavailability (F30%):	0.034
50% Bioavailability (F50%):	0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105	MRP1:	0.977
Plasma Protein Binding (PPB):	92.717%	Volume Distribution (VD):	-0.231
Fu:	6.523% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.319	BCRP inhibitor:	0.027
BSEP inhibitor:	0.95

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.875	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.044	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.549	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.017 ? 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):

6.481

Half-life (T1/2):

1.486

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.577	Drug-induced Liver Injury (DILI):	0.127
AMES Toxicity:	0.3	Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.63	Skin Sensitization:	0.951
Carcinogencity:	0.902	Eye Corrosion:	0.053
Eye Irritation:	0.849	Respiratory Toxicity:	0.862
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.722
Hematotoxicity:	0.314	Drug-induced Nephrotoxicity:	0.95
Genotoxicity:	0.252	RPMI-8226 Immunitoxicity:	0.06
A549 Cytotoxicity:	0.028	Hek293 Cytotoxicity:	0.033
BCF:	0.516 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.264 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.783 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.996 ? 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
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	antarctic	n.a.	PMID[15270575]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO26453	Prunus lusitanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37240175]
NPO25793	Gremmeniella abietina	Species	Helotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3346	Piper sanctum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26109	Pilocarpus spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25926	Tephrosia pumila	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26903	Plectranthus purpuratus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26213	Tephrosia vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26625	Stichopus chloronotus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24378	Osmanthus heterophyllus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26078	Mussaenda parviflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2344	Carlina acanthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18292	Guarea trichilioides	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26352	Heuchera cylindrica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26952	Cineraria geifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26719	Tetrapanax papyrifer	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24378	Osmanthus heterophyllus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26289	Lecidella chodati	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26952	Cineraria geifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11845	Petrorhagia dubia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26078	Mussaenda parviflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26135	Walsura tubulata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26719	Tetrapanax papyrifer	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25873	Thaminophyllum multiflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13781	Eremostachys moluccelloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26026	Vitis silvestris	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26563	Alectoria japonica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26453	Prunus lusitanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18292	Guarea trichilioides	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26535	Balanus glandula	Species	Balanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26352	Heuchera cylindrica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26625	Stichopus chloronotus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26754	Stevia connata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25952	Lastrea thelypteris	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26213	Tephrosia vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2344	Carlina acanthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26430	Aplysina laevis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25741	Aster ageratoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26884	Helichrysum davenportii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27377	Diaporthe helianthi	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25793	Gremmeniella abietina	Species	Helotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26053	Pluchea suaveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26109	Pilocarpus spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26980	Halocarpus biformis	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26903	Plectranthus purpuratus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7214	Bufotes viridis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26186	Stereocaulon leprocauloides	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26377	Amelanchier vulgaris	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26678	Calea pilosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25849	Streptomyces lomondensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3346	Piper sanctum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26408	Melanophryniscus moreirae	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26727	Eremocarpus setiger	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25926	Tephrosia pumila	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19823	Vicia benghalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25997	Senecio rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO137	Nepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26244	Panax papyrifer	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC166709 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	24539
0.1-0.2	22730
0.2-0.3	2216
0.3-0.4	333
0.4-0.5	36
0.5-0.6	3
0.6-0.7	1
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	Natural Product ID
0.6567	Remote Similarity	NPC301244
0.5616	Remote Similarity	NPC80365
0.5541	Remote Similarity	NPC21728
0.5067	Remote Similarity	NPC600164

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC166709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7430
0.1-0.2	1674
0.2-0.3	44
0.3-0.4	1
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