NPASS Compound

Natural Product: NPC97534

Natural Product ID	NPC97534
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	30-Norlupan-3Beta-Ol-20-One
IUPAC Name	1-[(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-1-yl]ethanone
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3109322
PubChem CID	490365
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives

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 -4.5051 2.0321 -2.3879 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3422 0.5504 -2.3584 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2378 0.0134 -3.4500 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3097 -0.2222 -1.0702 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5999 -0.0307 -0.2976 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2087 0.3555 1.1190 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8165 -0.1644 1.2163 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8680 -1.6573 1.3784 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0060 0.3855 2.3388 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5650 -0.0079 2.1955 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0388 0.1845 0.8197 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9424 1.6810 0.5913 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9218 -0.3895 -0.2687 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3644 -0.1505 -1.6218 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0901 -0.3590 -1.7912 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9128 0.0553 -0.5957 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3760 -0.1640 -0.7884 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6124 -1.4437 -1.4939 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8702 0.9462 -1.7319 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0520 1.6705 -1.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1175 0.7952 -0.6088 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5633 -0.0709 0.4960 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0169 0.5753 1.8217 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1137 -1.4549 0.5005 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0833 0.0460 0.4938 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5175 -0.7162 1.6662 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1080 -0.2432 1.8818 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3149 -0.5056 0.6505 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0424 -1.9921 0.5731 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7867 0.0362 -1.5886 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2666 0.2577 -0.1353 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4864 2.2248 -2.9044 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4789 2.4873 -1.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7290 2.4287 -3.0761 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1584 -1.2842 -1.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0983 -1.0299 -0.2308 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2910 0.6716 -0.7644 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8327 -0.1383 1.8821 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2767 1.4605 1.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0595 -2.0504 2.0289 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8921 -2.2200 0.4515 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8225 -1.8924 1.9279 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3776 -0.1076 3.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1578 1.4701 2.5095 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4035 -0.9892 2.6490 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9901 0.7115 2.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7947 2.1621 1.1598 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0297 2.1182 1.0821 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0789 1.9872 -0.4428 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0739 -1.4842 -0.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6707 0.8586 -2.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8912 -0.8685 -2.3222 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2935 -1.3775 -2.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4307 0.3144 -2.6344 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7845 1.1786 -0.5297 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2811 -1.2856 -2.5675 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0946 -2.3203 -1.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6796 -1.7238 -1.6122 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1248 0.5624 -2.7302 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0678 1.7139 -1.9040 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5249 2.2111 -2.0610 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8106 2.4688 -0.4605 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9141 1.4872 -0.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0333 0.9799 1.6341 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2988 1.3261 2.1655 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1537 -0.2356 2.5921 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8448 -1.6416 1.3458 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7537 -1.6223 -0.4171 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3570 -2.2572 0.6219 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8782 1.1320 0.7659 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1040 -0.3629 2.5670 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6470 -1.7900 1.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1711 0.8471 2.1485 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6816 -0.8398 2.7157 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8115 -2.3060 1.2245 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9057 -2.6016 0.9488 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2028 -2.3510 -0.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4301 0.6055 -2.0663 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2425 1.3595 -0.1438 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 21 30 1 0 13 31 1 0 31 4 1 0 31 7 1 0 28 11 1 0 28 16 1 0 25 17 1 0 1 32 1 0 1 33 1 0 1 34 1 0 4 35 1 6 5 36 1 0 5 37 1 0 6 38 1 0 6 39 1 0 8 40 1 0 8 41 1 0 8 42 1 0 9 43 1 0 9 44 1 0 10 45 1 0 10 46 1 0 12 47 1 0 12 48 1 0 12 49 1 0 13 50 1 1 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 16 55 1 1 18 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 21 63 1 1 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 24 69 1 0 25 70 1 1 26 71 1 0 26 72 1 0 27 73 1 0 27 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 31 79 1 1 M END

Standard InCHIKey	RCXANGLYPFOYKX-XJJQXQETSA-N
Standard InCHI	InChI=1S/C29H48O2/c1-18(30)19-10-13-26(4)16-17-28(6)20(24(19)26)8-9-22-27(5)14-12-23(31)25(2,3)21(27)11-15-29(22,28)7/h19-24,31H,8-17H2,1-7H3/t19-,20+,21-,22+,23-,24+,26+,27-,28+,29+/m0/s1
SMILES	CC(=O)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	428.37	Volume:	482.302 ? Van der Waals volume.
Dense:	0.888	LogP:	5.237 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.488 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.877 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	26.0
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:	0.486	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.646	Fsp³:	0.966
MCE-18:	101.263 ? 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:	0.949	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.54	Promiscuous compounds:	0.375

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.378	MDCK Permeability:	-5.048
Pgp-inhibitor:	0.761	Pgp-substrate:	0.119
PAMPA:	0.475 ? 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%):	0.452	30% Bioavailability (F30%):	0.159
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.919	MRP1:	0.965
Plasma Protein Binding (PPB):	97.807%	Volume Distribution (VD):	-0.053
Fu:	2.964% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.435
BSEP inhibitor:	0.988

ADMET: Metabolism

CYP1A2-inhibitor:	0.009	CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.105
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.071	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.764	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.597
HLM stability:	0.762 ? 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):

11.835

Half-life (T1/2):

0.282

ADMET: Toxicity

hERG Blockers:	0.117	hERG Blockers (10um):	0.271
Human Hepatotoxicity (H-HT):	0.644	Drug-induced Liver Injury (DILI):	0.393
AMES Toxicity:	0.482	Rat Oral Acute Toxicity:	0.392
Maximum Recommended Daily Dose:	0.624	Skin Sensitization:	0.946
Carcinogencity:	0.928	Eye Corrosion:	0.303
Eye Irritation:	0.823	Respiratory Toxicity:	0.89
Drug-induced Neurotoxicity:	0.112	Ototoxicity:	0.388
Hematotoxicity:	0.611	Drug-induced Nephrotoxicity:	0.699
Genotoxicity:	0.635	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.336	Hek293 Cytotoxicity:	0.452
BCF:	2.494 ? 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:	4.357 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.199 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.973 ? 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
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10757717]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[12943781]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951446]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	stems	Thailand	n.a.	PMID[14510595]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738381]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	Argentine	n.a.	PMID[14738381]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21905650]
NPO33010	euonymus carnosus	Species	Celastraceae	Eukaryota	Plant	n.a.	n.a.	PMID[24467317]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697288]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32998509]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36031812]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36938717]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37533365]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[9599285]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15393	Eucalyptus flocktoniae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13548	Chrozophora obliqua	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16175	Trichia floriformis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16678	Flindersia brayleyana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13859	Senecio flavus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13710	Lyophyllum shimeji	Species	Lyophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3391	Jungermannia obovata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24732	Cereus weberi	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15138	Rheum webbianum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4267	Ceratocystis clavigera	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11194	Bombus hortorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5552	Solanum sisymbriifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16175	Trichia floriformis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13230	Pedicularis condensata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15272	Mascarenhasia arborescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5078	Turraeanthus mannii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4935	Dinemasporium strigosum	Species	Chaetosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15755	Thymbra spicata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5269	Coleus garckeanus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11881	Adenopeltis colliguaya	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16678	Flindersia brayleyana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12680	Perityle vaseyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15393	Eucalyptus flocktoniae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14218	Spodoptera littoralis	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13548	Chrozophora obliqua	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8499	Osmerus mordax	Species	Osmeridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14034	Salvia coulteri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15015	Meconopsis napaulensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23289	Heracleum sphondylium	Species	Apiaceae	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
IC50	6

Activity Type	# Activity
Cell line	2
Non-molecular	4

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
NPT179	Cell line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[24467317]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[24467317]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[24467317]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	6090.0	nM	PMID[24467317]

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 NPC97534 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	20697
0.1-0.2	24805
0.2-0.3	3636
0.3-0.4	544
0.4-0.5	111
0.5-0.6	35
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC195155
0.7843	Intermediate Similarity	NPC5767
0.7843	Intermediate Similarity	NPC475742
0.7826	Intermediate Similarity	NPC232112
0.7347	Intermediate Similarity	NPC142712
0.72	Intermediate Similarity	NPC480925
0.72	Intermediate Similarity	NPC48079
0.7143	Intermediate Similarity	NPC289486
0.7059	Intermediate Similarity	NPC192638
0.7059	Intermediate Similarity	NPC25511
0.7059	Intermediate Similarity	NPC600137
0.7037	Intermediate Similarity	NPC269396
0.6667	Remote Similarity	NPC248830
0.6667	Remote Similarity	NPC212241
0.6607	Remote Similarity	NPC298168
0.6607	Remote Similarity	NPC143133
0.6481	Remote Similarity	NPC301226
0.6182	Remote Similarity	NPC144075
0.614	Remote Similarity	NPC74595
0.614	Remote Similarity	NPC264665
0.6	Remote Similarity	NPC30583
0.5932	Remote Similarity	NPC12774
0.5902	Remote Similarity	NPC483720
0.5789	Remote Similarity	NPC231256
0.5789	Remote Similarity	NPC178383
0.569	Remote Similarity	NPC201725
0.5645	Remote Similarity	NPC481321
0.5645	Remote Similarity	NPC607755
0.5593	Remote Similarity	NPC246956
0.5593	Remote Similarity	NPC119355
0.5574	Remote Similarity	NPC477578
0.5574	Remote Similarity	NPC477577
0.5517	Remote Similarity	NPC58631
0.55	Remote Similarity	NPC126993
0.5424	Remote Similarity	NPC93662
0.5424	Remote Similarity	NPC602784
0.541	Remote Similarity	NPC603388
0.5345	Remote Similarity	NPC104387
0.5345	Remote Similarity	NPC202540
0.5263	Remote Similarity	NPC606606
0.5185	Remote Similarity	NPC11908
0.5172	Remote Similarity	NPC472741
0.5172	Remote Similarity	NPC185536
0.5167	Remote Similarity	NPC471737
0.5167	Remote Similarity	NPC211009
0.5161	Remote Similarity	NPC472608
0.5161	Remote Similarity	NPC477508
0.5085	Remote Similarity	NPC245869
0.5085	Remote Similarity	NPC91573
0.5085	Remote Similarity	NPC240235
0.5085	Remote Similarity	NPC14112
0.5082	Remote Similarity	NPC91387
0.5082	Remote Similarity	NPC231680
0.5082	Remote Similarity	NPC57469
0.5082	Remote Similarity	NPC270306
0.5079	Remote Similarity	NPC61107

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC97534 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6404
0.1-0.2	2652
0.2-0.3	89
0.3-0.4	4
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