NPASS Compound

Natural Product: NPC51952

Natural Product ID	NPC51952
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VQWZLGYZILZLOV-JQMUJYSTSA-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: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 81 85 0 0 0 0 0 0 0 0999 V2000 -5.4740 1.8281 0.5979 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9966 0.7088 1.4702 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6039 0.9609 2.8582 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5933 -0.5813 0.9793 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5128 -1.5573 0.6981 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4637 -1.0580 -0.2959 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4949 -2.2065 -0.4329 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1378 -1.8443 -0.9274 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4726 -0.7923 -0.0438 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0732 -1.4581 1.2180 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4285 0.3016 0.2704 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8884 1.4647 0.6429 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5656 1.6454 0.7379 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9944 2.6253 1.3766 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4580 0.6973 0.1000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7604 1.1651 -0.4161 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6979 2.0891 -1.6253 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4380 2.0175 0.6452 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9120 2.2430 0.3788 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6761 1.0412 -0.0271 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8497 -0.2081 0.0159 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7084 -0.6557 1.4143 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6714 -1.2761 -0.7266 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -0.0359 -0.7851 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8297 -1.3322 -0.8215 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5372 -1.1018 -1.5329 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6282 -0.1492 -0.8448 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0820 0.7447 -1.8732 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3043 1.2047 -1.2812 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9015 0.2055 0.2251 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4921 0.6144 1.5824 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2196 -0.8556 -1.6089 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3840 -0.4135 -2.6215 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6966 2.3174 0.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2386 1.4590 -0.1489 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0462 2.5977 1.1796 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6037 2.0452 3.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6283 0.5458 2.9289 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9899 0.4258 3.6297 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2388 -1.0536 1.7853 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2411 -0.4718 0.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0204 -1.8606 1.6686 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9341 -2.5351 0.3192 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9458 -2.8790 -1.2163 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4549 -2.8162 0.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0728 -1.6101 -2.0003 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5209 -2.7820 -0.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2262 -0.7851 2.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0227 -1.9342 1.6164 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5995 -2.3228 1.0726 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4921 2.3250 0.8864 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7336 -0.0437 0.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4438 1.6016 -2.5597 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7885 2.3870 -1.7720 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2098 3.0479 -1.4053 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0176 3.0633 0.5107 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2233 1.7040 1.6643 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0911 3.0585 -0.3590 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3127 2.6642 1.3492 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5294 0.8841 0.6910 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7463 -1.0284 1.7464 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9947 0.1641 2.1395 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4506 -1.4715 1.6684 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2784 -2.2484 -0.4047 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7101 -1.1881 -0.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6034 -1.1328 -1.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9687 0.0929 -1.8497 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7431 -1.8127 0.1593 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4181 -2.0482 -1.4487 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0952 -2.0903 -1.7665 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7957 -0.6810 -2.5462 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2248 1.8087 -1.7640 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0437 0.3548 -2.9040 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1781 0.7794 -1.6988 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0724 0.5742 -1.3177 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2255 1.0293 -0.4782 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0553 1.5658 1.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2290 -0.1222 2.3686 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6747 -1.8098 -1.9505 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0611 -0.1571 -1.4560 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1605 -1.1426 -3.2399 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 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 20 29 1 0 11 30 1 0 30 31 1 0 6 32 1 6 32 33 1 0 31 2 1 0 30 6 1 0 27 9 1 0 27 15 1 0 24 16 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 7 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 10 48 1 0 10 49 1 0 10 50 1 0 12 51 1 0 15 52 1 1 17 53 1 0 17 54 1 0 17 55 1 0 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 20 60 1 1 22 61 1 0 22 62 1 0 22 63 1 0 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 6 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 30 76 1 6 31 77 1 0 31 78 1 0 32 79 1 0 32 80 1 0 33 81 1 0 M END

Standard InCHIKey	VQWZLGYZILZLOV-JQMUJYSTSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-25(2)12-14-30(18-31)15-13-28(6)19(20(30)17-25)16-21(32)24-27(5)10-9-23(33)26(3,4)22(27)8-11-29(24,28)7/h16,20,22-24,31,33H,8-15,17-18H2,1-7H3/t20-,22+,23-,24+,27-,28+,29+,30+/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC(=O)[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@H]5CC[C@@]34C)O)[C@@H]2C1)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	505.751 ? Van der Waals volume.
Dense:	0.902	LogP:	3.303 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.204 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.398 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.485	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.77	Fsp³:	0.9
MCE-18:	104.0 ? 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:	0.537	Fluc inhibitor:	0.013 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.087 ? 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:	0.328	Promiscuous compounds:	0.363

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.318	MDCK Permeability:	-4.919
Pgp-inhibitor:	0.313	Pgp-substrate:	0.033
PAMPA:	0.911 ? 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%):	0.846	30% Bioavailability (F30%):	0.351
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.998	MRP1:	0.858
Plasma Protein Binding (PPB):	97.197%	Volume Distribution (VD):	-0.176
Fu:	3.452% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.643	BCRP inhibitor:	0.673
BSEP inhibitor:	0.98

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.974	CYP2C19-substrate:	0.492
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.949	CYP3A4-substrate:	0.013
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.832
HLM stability:	0.527 ? 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):

10.316

Half-life (T1/2):

0.517

ADMET: Toxicity

hERG Blockers:	0.088	hERG Blockers (10um):	0.224
Human Hepatotoxicity (H-HT):	0.826	Drug-induced Liver Injury (DILI):	0.391
AMES Toxicity:	0.545	Rat Oral Acute Toxicity:	0.487
Maximum Recommended Daily Dose:	0.566	Skin Sensitization:	0.968
Carcinogencity:	0.936	Eye Corrosion:	0.007
Eye Irritation:	0.704	Respiratory Toxicity:	0.861
Drug-induced Neurotoxicity:	0.36	Ototoxicity:	0.57
Hematotoxicity:	0.644	Drug-induced Nephrotoxicity:	0.901
Genotoxicity:	0.747	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.521	Hek293 Cytotoxicity:	0.509
BCF:	2.271 ? 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:	4.351 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.705 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.203 ? 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
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)83457-3]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075772]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843567]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043405]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16155971]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125219]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17665952]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18345641]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19824618]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21667999]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27592135]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[324959]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33325237]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO2304	Byssovorax cruenta	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10806	Achillea roseoalba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1355	Urechis caupo	Species	Urechidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5319	Ulmus thomasii	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6310	Ruta bracteosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7766	Pericopsis schliebenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO276	Miscanthus sacchariflorus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25481	Lonchocarpus oaxacensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8103	Lecanora melanophthalma	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7060	Ficus ruficaulis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4516	Fasciospongia rimosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3830	Euplotes rariseta	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9903	Engelhardia spicata	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24370	Crassocephalum crepidioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15610	Citrus trifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2304	Byssovorax cruenta	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4516	Fasciospongia rimosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5319	Ulmus thomasii	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10806	Achillea roseoalba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO276	Miscanthus sacchariflorus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7060	Ficus ruficaulis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1355	Urechis caupo	Species	Urechidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7766	Pericopsis schliebenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8103	Lecanora melanophthalma	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9903	Engelhardia spicata	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25481	Lonchocarpus oaxacensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15610	Citrus trifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24370	Crassocephalum crepidioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3830	Euplotes rariseta	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6310	Ruta bracteosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	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 NPC51952 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	18709
0.1-0.2	25758
0.2-0.3	4587
0.3-0.4	675
0.4-0.5	102
0.5-0.6	14
0.6-0.7	10
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
0.7705	Intermediate Similarity	NPC214756
0.6984	Remote Similarity	NPC479748
0.6721	Remote Similarity	NPC101475
0.6615	Remote Similarity	NPC295643
0.6508	Remote Similarity	NPC602872
0.6232	Remote Similarity	NPC4036
0.6232	Remote Similarity	NPC65120
0.6232	Remote Similarity	NPC145067
0.6232	Remote Similarity	NPC233455
0.6232	Remote Similarity	NPC158030
0.6056	Remote Similarity	NPC471966
0.5882	Remote Similarity	NPC272075
0.5873	Remote Similarity	NPC190035
0.5775	Remote Similarity	NPC610635
0.5672	Remote Similarity	NPC480944
0.5606	Remote Similarity	NPC235341
0.5469	Remote Similarity	NPC290598
0.5469	Remote Similarity	NPC30590
0.5417	Remote Similarity	NPC98874
0.5362	Remote Similarity	NPC246708
0.5294	Remote Similarity	NPC3915
0.5147	Remote Similarity	NPC253807
0.5147	Remote Similarity	NPC158662
0.5147	Remote Similarity	NPC475862
0.5072	Remote Similarity	NPC470588

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC51952 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6823
0.1-0.2	2201
0.2-0.3	117
0.3-0.4	5
0.4-0.5	3
0.5-0.6	0
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	Drug ID	Developmental Stage
0.6232	Remote Similarity	NPD7515	Phase 2

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