NPASS Compound

Natural Product: NPC230047

Natural Product ID	NPC230047
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(+)-(5S,8R,9R,10S,13R)-8-Hydroxylabdan-15-Oic Acid
IUPAC Name	(3R)-5-[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3233988
PubChem CID	11868539
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 59 60 0 0 0 0 0 0 0 0999 V2000 3.7867 -1.7816 1.3749 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0534 -0.7451 0.5078 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1039 -1.5082 -0.3415 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2654 -0.7340 -1.2815 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3216 0.2725 -0.7409 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7467 -0.2360 0.1864 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9992 -1.7069 0.0579 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2914 0.0758 1.5988 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3783 0.6670 2.4673 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6170 -0.1199 2.2552 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1643 0.1979 0.8730 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8918 1.5482 1.0769 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2136 -0.8047 0.5873 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0961 0.4352 -0.1078 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4912 0.1196 -1.5194 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3724 0.3436 -2.4964 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2043 1.0661 -1.9185 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8313 1.1175 -3.0583 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4294 2.4076 -1.6292 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1303 -0.0238 -0.2620 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0328 0.6099 0.7352 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9212 -0.0364 1.3492 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9118 1.9649 1.0182 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6618 -2.1473 0.7694 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1791 -1.3501 2.2937 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1402 -2.6695 1.5116 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6199 -0.0259 1.2096 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5866 -2.2239 0.3212 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7492 -2.1806 -0.9922 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8146 -1.3746 -2.0973 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0152 -0.1255 -1.8889 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.0236 -0.1866 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5016 -2.1966 -0.7982 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7002 -2.2612 0.9679 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0861 -1.9676 -0.0891 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4943 0.8924 1.5909 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0941 -0.8314 2.1109 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0352 0.5408 3.5211 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4933 1.7547 2.3190 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3927 0.0449 3.0365 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3670 -1.1973 2.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4547 2.1192 1.9118 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9614 1.3605 1.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8274 2.1632 0.1653 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0460 -1.7321 1.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4668 -1.0187 -0.4415 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1831 -0.4196 1.0357 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8506 1.5189 -0.0778 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3002 0.8548 -1.8070 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8925 -0.8776 -1.6845 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9826 -0.6735 -2.7986 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7291 0.7803 -3.4570 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3203 1.7903 -3.8170 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7351 1.6592 -2.7847 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9452 0.1665 -3.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4152 2.9478 -1.7322 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7572 -0.7446 -0.8311 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7454 0.7919 -0.9056 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5636 2.4789 1.5916 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 1 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 11 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 1 2 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 17 5 1 0 14 6 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 1 3 28 1 0 3 29 1 0 4 30 1 0 4 31 1 0 5 32 1 1 7 33 1 0 7 34 1 0 7 35 1 0 8 36 1 0 8 37 1 0 9 38 1 0 9 39 1 0 10 40 1 0 10 41 1 0 12 42 1 0 12 43 1 0 12 44 1 0 13 45 1 0 13 46 1 0 13 47 1 0 14 48 1 6 15 49 1 0 15 50 1 0 16 51 1 0 16 52 1 0 18 53 1 0 18 54 1 0 18 55 1 0 19 56 1 0 20 57 1 0 20 58 1 0 23 59 1 0 M END

Standard InCHIKey	KHCCSRVJJDOANA-VQEGESQYSA-N
Standard InCHI	InChI=1S/C20H36O3/c1-14(13-17(21)22)7-8-16-19(4)11-6-10-18(2,3)15(19)9-12-20(16,5)23/h14-16,23H,6-13H2,1-5H3,(H,21,22)/t14-,15+,16-,19+,20-/m1/s1
SMILES	C[C@H](CC[C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC[C@@]1(C)O)CC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	324.27	Volume:	361.097 ? Van der Waals volume.
Dense:	0.898	LogP:	3.451 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.026 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.395 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	12.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.758	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.068	Fsp³:	0.95
MCE-18:	47.744 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.08	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.91	Promiscuous compounds:	0.646

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.005	MDCK Permeability:	-4.918
Pgp-inhibitor:	0.008	Pgp-substrate:	0.0
PAMPA:	0.982 ? 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%):	0.003	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.23

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047	MRP1:	0.735
Plasma Protein Binding (PPB):	97.276%	Volume Distribution (VD):	-0.513
Fu:	3.22% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.025
BSEP inhibitor:	0.927

ADMET: Metabolism

CYP1A2-inhibitor:	0.045	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.372	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.012	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.975	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.004
HLM stability:	0.142 ? 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):

3.668

Half-life (T1/2):

1.206

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.06
Human Hepatotoxicity (H-HT):	0.692	Drug-induced Liver Injury (DILI):	0.452
AMES Toxicity:	0.249	Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.348	Skin Sensitization:	0.965
Carcinogencity:	0.635	Eye Corrosion:	0.917
Eye Irritation:	0.928	Respiratory Toxicity:	0.869
Drug-induced Neurotoxicity:	0.135	Ototoxicity:	0.713
Hematotoxicity:	0.648	Drug-induced Nephrotoxicity:	0.894
Genotoxicity:	0.118	RPMI-8226 Immunitoxicity:	0.032
A549 Cytotoxicity:	0.091	Hek293 Cytotoxicity:	0.113
BCF:	0.631 ? 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:	3.361 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.916 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.065 ? 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
NPO4182	Hygrophorus chrysodon	Species	Hygrophoraceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[17253868]
NPO14064	Phaeodactylum tricornutum	Species	Phaeodactylaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18570469]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20045319]
NPO3829	Euphorbia myrsinites	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[22192329]
NPO33188	ageratina jocotepecana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24702233]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26341132]
NPO623	Amaranthus hypochondriacus	Species	Amaranthaceae	Eukaryota	Flowers	SÃƒÂ£o Paulo, Brazil.		PMID[32156350]
NPO4182	Hygrophorus chrysodon	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14064	Phaeodactylum tricornutum	Species	Phaeodactylaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5143	Millettia ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11973	Gymnothorax javanicus	Species	Muraenidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3829	Euphorbia myrsinites	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8478	Gnaphalium undulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1870	Polyporus dryadeus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO623	Amaranthus hypochondriacus	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4007	Vicia amurensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26520	Wyethia mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17959	Berberis repens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13431	Streptomyces amphibiosporus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14064	Phaeodactylum tricornutum	Species	Phaeodactylaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5918	Thermopsis dolichocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8478	Gnaphalium undulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2862	Dendrilla cavernosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17959	Berberis repens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2302	Sedum litoreum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1509	Hippeastrum papilio	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25934	Diphasiastrum thyoides	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26520	Wyethia mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6081	Limnocharis flava	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4007	Vicia amurensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3423	Teucrium asiaticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5481	Fomes robiniae	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO275	Amphilophis odorata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1870	Polyporus dryadeus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO780	Senecio viscosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14314	Olea cunninghamii	Species	Limapontiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5143	Millettia ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO623	Amaranthus hypochondriacus	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11973	Gymnothorax javanicus	Species	Muraenidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7932	Ips confusus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3829	Euphorbia myrsinites	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6480	Zanthoxylum fraxineum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8268	Croton laccifer	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4182	Hygrophorus chrysodon	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7057	Ptarmica ptarmicifolia	n.a.	n.a.	n.a.	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
MIC	2

Activity Type	# Activity
Organism	2

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
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	1560.0	ug.mL-1	PMID[24702233]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2340.0	ug.mL-1	PMID[24702233]

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 NPC230047 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	25633
0.1-0.2	21058
0.2-0.3	2951
0.3-0.4	172
0.4-0.5	28
0.5-0.6	13
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
0.7174	Intermediate Similarity	NPC19311
0.5745	Remote Similarity	NPC135438
0.5532	Remote Similarity	NPC88454
0.5532	Remote Similarity	NPC101307
0.5532	Remote Similarity	NPC117607
0.5472	Remote Similarity	NPC2524
0.54	Remote Similarity	NPC378624
0.5385	Remote Similarity	NPC41542
0.5306	Remote Similarity	NPC64123
0.5283	Remote Similarity	NPC160817
0.5185	Remote Similarity	NPC217714
0.5185	Remote Similarity	NPC485095
0.5098	Remote Similarity	NPC201048
0.5098	Remote Similarity	NPC476366

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC230047 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6275
0.1-0.2	2679
0.2-0.3	192
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