NPASS Compound

Natural Product: NPC172742

Natural Product ID	NPC172742
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YBMMGZNGDURMBM-VXLSRJMWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102588575
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

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 73 77 0 0 0 0 0 0 0 0999 V2000 4.3461 1.7147 -0.2438 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0207 1.2847 1.0505 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6878 2.4200 1.7567 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8895 0.6792 1.9225 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2037 -0.2566 0.9545 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8972 -0.2176 0.8677 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1398 0.6956 1.6911 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1287 0.9180 1.3873 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7045 0.2286 0.2353 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2004 0.4378 0.2643 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8268 0.1574 1.5755 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4306 1.9388 -0.0090 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8907 2.2707 -0.0074 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7994 1.1410 -0.3294 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2083 0.0872 -1.2132 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0548 -1.1838 -1.0554 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4240 0.5317 -2.6525 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7706 -0.2318 -0.9272 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4560 -1.6954 -0.9384 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9389 -1.7535 -1.1504 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2434 -1.1854 0.0692 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5310 -2.1026 1.1979 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2505 -1.1199 -0.1302 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6311 -0.6168 -1.4999 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9301 -2.4554 0.0644 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3831 -2.3724 -0.3790 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0609 -1.2021 0.1999 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3331 -1.0008 0.0902 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9321 0.1710 0.7185 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1617 0.2452 0.9717 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9043 1.6898 -1.0294 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7459 2.7288 -0.5388 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6156 1.0502 -1.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2480 1.7019 -0.1751 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0486 3.1354 0.9638 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5679 2.1495 2.3429 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9332 2.9843 2.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3207 0.1227 2.7753 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2952 1.5444 2.1897 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5640 1.2037 2.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6811 1.6101 2.0226 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3827 0.7597 -0.6885 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5271 -0.6814 1.5962 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9888 0.0415 2.3289 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3940 1.0352 2.0137 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9601 2.1876 -1.0046 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9285 2.5649 0.7533 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0284 3.1042 -0.7587 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2052 2.7467 0.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2863 0.6899 0.5858 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1165 -0.8285 -1.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7787 -1.7484 -0.1619 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9298 -1.7444 -2.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4208 0.8324 -3.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0572 1.4209 -2.7364 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7929 -0.2851 -3.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1915 0.1925 -1.8033 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8021 -2.2679 -0.0959 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9034 -2.1345 -1.8672 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7996 -1.0764 -2.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6912 -2.7915 -1.3582 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0801 -1.9072 2.1084 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2836 -3.1454 0.8304 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5676 -2.1744 1.5204 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3294 0.4359 -1.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1962 -1.2208 -2.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7162 -0.6377 -1.7106 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9647 -2.6753 1.1554 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4746 -3.2618 -0.5305 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5083 -2.4901 -1.4672 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9174 -3.2724 0.0557 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9936 -1.6852 -0.4647 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1577 2.5685 -0.6497 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 2 0 28 29 1 0 29 30 2 0 14 31 1 0 29 2 1 0 27 5 1 0 23 6 1 0 21 9 1 0 18 10 1 0 1 32 1 0 1 33 1 0 1 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 7 40 1 0 8 41 1 0 9 42 1 6 11 43 1 0 11 44 1 0 11 45 1 0 12 46 1 0 12 47 1 0 13 48 1 0 13 49 1 0 14 50 1 1 16 51 1 0 16 52 1 0 16 53 1 0 17 54 1 0 17 55 1 0 17 56 1 0 18 57 1 6 19 58 1 0 19 59 1 0 20 60 1 0 20 61 1 0 22 62 1 0 22 63 1 0 22 64 1 0 24 65 1 0 24 66 1 0 24 67 1 0 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 28 72 1 0 31 73 1 0 M END

Standard InCHIKey	YBMMGZNGDURMBM-VXLSRJMWSA-N
Standard InCHI	InChI=1S/C29H42O2/c1-25(2)17-19-18(16-24(25)31)10-14-28(6)20(19)8-9-22-27(5)13-12-23(30)26(3,4)21(27)11-15-29(22,28)7/h8-9,16,21-23,30H,10-15,17H2,1-7H3/t21-,22+,23+,27-,28+,29+/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)CCC2=CC1=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	422.32	Volume:	474.392 ? Van der Waals volume.
Dense:	0.89	LogP:	3.868 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.548 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.656 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	27.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.466	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.845	Fsp³:	0.759
MCE-18:	95.765 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.693	Fluc inhibitor:	0.011 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.478 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.451	Promiscuous compounds:	0.326

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.057	MDCK Permeability:	-4.852
Pgp-inhibitor:	0.991	Pgp-substrate:	0.038
PAMPA:	0.576 ? 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%):	0.593	30% Bioavailability (F30%):	0.443
50% Bioavailability (F50%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059	MRP1:	0.967
Plasma Protein Binding (PPB):	96.894%	Volume Distribution (VD):	-0.16
Fu:	2.584% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.973	BCRP inhibitor:	0.026
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.881	CYP1A2-substrate:	0.158
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.012	CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.406	CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.991	CYP3A4-substrate:	0.775
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.852
HLM stability:	0.812 ? 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):

11.662

Half-life (T1/2):

0.389

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.115
Human Hepatotoxicity (H-HT):	0.643	Drug-induced Liver Injury (DILI):	0.297
AMES Toxicity:	0.588	Rat Oral Acute Toxicity:	0.338
Maximum Recommended Daily Dose:	0.613	Skin Sensitization:	0.912
Carcinogencity:	0.892	Eye Corrosion:	0.051
Eye Irritation:	0.861	Respiratory Toxicity:	0.821
Drug-induced Neurotoxicity:	0.082	Ototoxicity:	0.452
Hematotoxicity:	0.512	Drug-induced Nephrotoxicity:	0.813
Genotoxicity:	0.622	RPMI-8226 Immunitoxicity:	0.123
A549 Cytotoxicity:	0.124	Hek293 Cytotoxicity:	0.241
BCF:	1.5 ? 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:	3.979 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.503 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.889 ? 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]
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]
NPO26952	Cineraria geifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26352	Heuchera cylindrica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2344	Carlina acanthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
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]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2039	Callerya cinerea	Species	Fabaceae	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]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26135	Walsura tubulata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26078	Mussaenda parviflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26952	Cineraria geifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26289	Lecidella chodati	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26109	Pilocarpus spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11845	Petrorhagia dubia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26678	Calea pilosa	Species	Asteraceae	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]
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]
NPO24378	Osmanthus heterophyllus	Species	Oleaceae	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 NPC172742 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	18124
0.1-0.2	26904
0.2-0.3	4365
0.3-0.4	450
0.4-0.5	14
0.5-0.6	2
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	Natural Product ID
0.5507	Remote Similarity	NPC480945
0.5278	Remote Similarity	NPC301244

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC172742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6637
0.1-0.2	2297
0.2-0.3	214
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data