NPASS Compound

Natural Product: NPC248830

Natural Product ID	NPC248830
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	30-Hydroxylupeol
IUPAC Name	(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-(3-hydroxyprop-1-en-2-yl)-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-9-ol
Synonyms	30-Hydroxylupeol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL518390
PubChem CID	489919
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 82 86 0 0 0 0 0 0 0 0999 V2000 -5.9560 2.1735 -1.0946 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6916 2.2138 -1.6473 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2432 0.8468 -2.0190 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9636 0.6451 -3.3157 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0622 -0.2657 -1.0319 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3627 -0.5080 -0.3219 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1214 -0.0561 1.1321 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6976 -0.5420 1.2703 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1036 0.1504 0.0288 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7166 -0.3365 -0.0814 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1022 -0.1719 -1.4516 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2225 -0.9490 -1.3659 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0826 -0.1440 -0.4294 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5662 -0.3125 0.9551 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8683 0.1767 1.0360 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8329 1.6767 1.1748 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4834 -0.3456 2.3232 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9520 -0.0133 2.4378 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6211 -1.6934 1.5094 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4156 0.5602 1.8897 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8677 0.0691 1.8131 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3017 0.3775 0.4088 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5421 -0.3810 -0.6379 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8891 -1.7957 -0.8616 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9138 0.3647 -1.9371 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3595 0.2718 -2.2505 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2958 0.1002 -1.1087 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7767 0.4512 0.2371 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4518 -0.3897 1.3348 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2508 1.8798 0.5881 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9223 -1.1739 -1.1279 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7008 -2.0212 1.1250 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6281 2.4583 -1.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7199 2.8762 -2.5636 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9637 2.7271 -0.9827 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0764 1.4619 -3.9966 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6306 -0.3081 -3.6936 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7218 -1.1573 -1.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2390 -0.0153 -0.7059 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5666 -1.6214 -0.2350 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2329 1.0136 1.2737 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7548 -0.6043 1.8349 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2291 1.2307 0.1578 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7552 -1.4600 0.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7241 -0.7670 -2.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9258 0.8589 -1.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0700 -1.9313 -0.9170 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6520 -1.1326 -2.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9041 0.9406 -0.6993 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2911 2.1911 0.3810 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8293 2.1498 1.2794 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3748 1.8665 2.1937 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4203 -1.4487 2.4156 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9699 0.1017 3.1988 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3098 -0.5836 3.3469 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1630 1.0321 2.6386 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5996 -2.2062 1.3458 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1463 -2.3820 1.1303 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5900 -1.5877 2.6370 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0904 0.5297 2.9202 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4902 1.5921 1.4483 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9955 -0.9457 2.1346 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4371 0.7459 2.4867 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9214 1.4396 0.2392 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4941 -2.2971 -0.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9172 -2.3600 -1.0179 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4105 -1.9941 -1.8498 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5508 1.4293 -1.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3441 -0.0811 -2.7789 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5534 -0.5868 -2.9624 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6122 1.1774 -2.8815 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1807 0.7788 -1.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5529 -0.4653 1.1474 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3884 0.1851 2.3067 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9568 -1.3363 1.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5752 2.2383 1.3879 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0911 2.5187 -0.3188 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3104 1.8873 0.8516 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7986 -1.6720 -0.3082 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9465 -2.5710 1.6822 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6952 -2.4033 1.5034 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6539 -2.3705 0.0731 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 14 19 1 1 14 20 1 0 20 21 1 0 21 22 1 0 22 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 28 30 1 0 27 31 1 0 8 32 1 6 9 5 1 0 15 10 1 0 28 22 1 0 18 8 1 0 23 13 1 0 1 33 1 0 2 34 1 0 2 35 1 0 4 36 1 0 4 37 1 0 5 38 1 6 6 39 1 0 6 40 1 0 7 41 1 0 7 42 1 0 9 43 1 1 10 44 1 1 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 6 16 50 1 0 16 51 1 0 16 52 1 0 17 53 1 0 17 54 1 0 18 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 19 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 22 64 1 6 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 27 72 1 6 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 M END

Standard InCHIKey	ZNUAKACHFYTNFX-QGTGJCAVSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-19(18-31)20-10-13-27(4)16-17-29(6)21(25(20)27)8-9-23-28(5)14-12-24(32)26(2,3)22(28)11-15-30(23,29)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1
SMILES	OCC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	5.392 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.639 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.702 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	26.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.452	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.816	Fsp³:	0.933
MCE-18:	100.793 ? 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:	0.723	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.511	Promiscuous compounds:	0.209

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.089	MDCK Permeability:	-4.875
Pgp-inhibitor:	0.013	Pgp-substrate:	0.424
PAMPA:	0.871 ? 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%):	0.666	30% Bioavailability (F30%):	0.591
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.937	MRP1:	0.822
Plasma Protein Binding (PPB):	95.935%	Volume Distribution (VD):	0.067
Fu:	4.689% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.749
BSEP inhibitor:	0.345

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.914	CYP2C19-substrate:	0.289
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.944	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
HLM stability:	0.523 ? 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):

10.422

Half-life (T1/2):

0.489

ADMET: Toxicity

hERG Blockers:	0.103	hERG Blockers (10um):	0.236
Human Hepatotoxicity (H-HT):	0.631	Drug-induced Liver Injury (DILI):	0.268
AMES Toxicity:	0.392	Rat Oral Acute Toxicity:	0.229
Maximum Recommended Daily Dose:	0.475	Skin Sensitization:	0.964
Carcinogencity:	0.936	Eye Corrosion:	0.168
Eye Irritation:	0.846	Respiratory Toxicity:	0.865
Drug-induced Neurotoxicity:	0.068	Ototoxicity:	0.544
Hematotoxicity:	0.56	Drug-induced Nephrotoxicity:	0.701
Genotoxicity:	0.314	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.272	Hek293 Cytotoxicity:	0.467
BCF:	2.356 ? 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:	4.358 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.394 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.098 ? 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]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843583]
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]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[136119]
NPO16746	Lendenfeldia frondosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402955]
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]
NPO25743	Cassipourea madagascariensis	Species	Rhizophoraceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[16499334]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[16643054]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[17125218]
NPO25232	Peperomia heyneana	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17291043]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[17315960]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791477]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
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]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24680612]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697288]
NPO32825	cassine xylocarpa	Species	Celastraceae	Eukaryota	dried stems	Ahuachapan, El Salvado	n.a.	PMID[25927586]
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]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26370	Iryanthera juruensis	Species	Myristicaceae	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]
NPO2922	Botryosphaeria berengeriana	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14953	Thapsia transtagana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15430	Abutilon grandiflorum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29099	Sinocrassula indica	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19229	Aniba parviflora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14711.1	Arabidopsis lyrata subsp. lyrata	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6425	Betula davurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18497	Euphorbia aellenii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13673	Ipomoea muelleri	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11042	Lecanora sordida	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16746	Lendenfeldia frondosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19753	Liabum bourgeaui	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11777	Pluchea sericea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28174	Poterium sanguisorba	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16040	Pristimera indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19692	Quercus variabilis	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23370	Sticta mougeotiana	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17440	Thryptomene kochii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3022	Toxicopueraria peduncularis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19073	Uncaria lancifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18830	Valeriana cardamines	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18008	Viburnum rhytidophyllum	Species	Adoxaceae	Eukaryota	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]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	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]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25743	Cassipourea madagascariensis	Species	Rhizophoraceae	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]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16040	Pristimera indica	Species	Celastraceae	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]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19073	Uncaria lancifolia	Species	Rubiaceae	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]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
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]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3022	Toxicopueraria peduncularis	Species	Fabaceae	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]
NPO19073	Uncaria lancifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16040	Pristimera indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18659	Prunus japonica	Species	Rosaceae	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]
NPO11777	Pluchea sericea	Species	Asteraceae	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]
NPO18659	Prunus japonica	Species	Rosaceae	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]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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]
NPO11777	Pluchea sericea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11194	Bombus hortorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28174	Poterium sanguisorba	Species	Rosaceae	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]
NPO18008	Viburnum rhytidophyllum	Species	Adoxaceae	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]
NPO6425	Betula davurica	Species	Betulaceae	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]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	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]
NPO18497	Euphorbia aellenii	Species	Euphorbiaceae	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]
NPO22423	Microtropis fokienensis	Species	Celastraceae	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]
NPO14953	Thapsia transtagana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27395	Mandragora officinarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2922	Botryosphaeria berengeriana	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18830	Valeriana cardamines	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14711.1	Arabidopsis lyrata subsp. lyrata	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16040	Pristimera indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19073	Uncaria lancifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23370	Sticta mougeotiana	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29099	Sinocrassula indica	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19692	Quercus variabilis	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11042	Lecanora sordida	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18252	Cajanus cajan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27107	Coleus coerulescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16746	Lendenfeldia frondosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26370	Iryanthera juruensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24417	Centaurea hololeuca	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13673	Ipomoea muelleri	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3022	Toxicopueraria peduncularis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25232	Peperomia heyneana	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16903	Chisocheton siamensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25293	Beaumontia brevituba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19229	Aniba parviflora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15430	Abutilon grandiflorum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17440	Thryptomene kochii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26578	Astragalus pamirensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8818	Rohdea wattii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19753	Liabum bourgeaui	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25743	Cassipourea madagascariensis	Species	Rhizophoraceae	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	7
Inhibition	1

Activity Type	# Activity
Cell line	3
Organism	1
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	=	12.2	ug.mL-1	PMID[16499334]
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]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	<	50.0	%	PMID[25927586]

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 NPC248830 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	26571
0.1-0.2	19902
0.2-0.3	2766
0.3-0.4	459
0.4-0.5	79
0.5-0.6	45
0.6-0.7	21
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC212241
0.8542	High Similarity	NPC192638
0.8542	High Similarity	NPC25511
0.8542	High Similarity	NPC600137
0.8077	Intermediate Similarity	NPC119355
0.7736	Intermediate Similarity	NPC269396
0.7059	Intermediate Similarity	NPC142712
0.7037	Intermediate Similarity	NPC231256
0.7037	Intermediate Similarity	NPC178383
0.6923	Remote Similarity	NPC480925
0.6923	Remote Similarity	NPC48079
0.6852	Remote Similarity	NPC202540
0.6852	Remote Similarity	NPC301226
0.6667	Remote Similarity	NPC97534
0.6667	Remote Similarity	NPC195155
0.6667	Remote Similarity	NPC103754
0.6607	Remote Similarity	NPC93662
0.6545	Remote Similarity	NPC144075
0.6491	Remote Similarity	NPC246956
0.6491	Remote Similarity	NPC74595
0.6491	Remote Similarity	NPC264665
0.6271	Remote Similarity	NPC12774
0.625	Remote Similarity	NPC104387
0.625	Remote Similarity	NPC240235
0.625	Remote Similarity	NPC14112
0.6102	Remote Similarity	NPC298168
0.6102	Remote Similarity	NPC143133
0.6071	Remote Similarity	NPC185536
0.6071	Remote Similarity	NPC102708
0.6032	Remote Similarity	NPC16377
0.5968	Remote Similarity	NPC607755
0.5965	Remote Similarity	NPC78067
0.5965	Remote Similarity	NPC91573
0.5965	Remote Similarity	NPC278091
0.5893	Remote Similarity	NPC80297
0.5893	Remote Similarity	NPC475727
0.5893	Remote Similarity	NPC116119
0.5893	Remote Similarity	NPC606606
0.5862	Remote Similarity	NPC42853
0.5862	Remote Similarity	NPC237460
0.5763	Remote Similarity	NPC5767
0.5763	Remote Similarity	NPC296701
0.5763	Remote Similarity	NPC475742
0.5763	Remote Similarity	NPC218616
0.5714	Remote Similarity	NPC483720
0.5714	Remote Similarity	NPC35652
0.5556	Remote Similarity	NPC472738
0.5556	Remote Similarity	NPC232112
0.55	Remote Similarity	NPC211009
0.5469	Remote Similarity	NPC4643
0.5424	Remote Similarity	NPC245869
0.541	Remote Similarity	NPC13554
0.541	Remote Similarity	NPC57469
0.5397	Remote Similarity	NPC471900
0.5397	Remote Similarity	NPC477577
0.5323	Remote Similarity	NPC126993
0.5312	Remote Similarity	NPC264317
0.5312	Remote Similarity	NPC294438
0.5254	Remote Similarity	NPC43300
0.5238	Remote Similarity	NPC474484
0.5238	Remote Similarity	NPC49599
0.5238	Remote Similarity	NPC49627
0.5231	Remote Similarity	NPC292553
0.5231	Remote Similarity	NPC33768
0.5217	Remote Similarity	NPC475416
0.5161	Remote Similarity	NPC305835
0.5161	Remote Similarity	NPC86305
0.5161	Remote Similarity	NPC212879
0.5156	Remote Similarity	NPC477578
0.5152	Remote Similarity	NPC168231
0.5082	Remote Similarity	NPC58631
0.5082	Remote Similarity	NPC285761
0.5082	Remote Similarity	NPC34930
0.5077	Remote Similarity	NPC201406
0.5077	Remote Similarity	NPC289486

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC248830 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7664
0.1-0.2	1423
0.2-0.3	57
0.3-0.4	5
0.4-0.5	0
0.5-0.6	1
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
0.5312	Remote Similarity	NPD7520	Phase 1

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