NPASS Compound

Natural Product: NPC32141

Natural Product ID	NPC32141
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KFPLVZLISLBBSJ-BUHFOSPRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5321100
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

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 57 56 0 0 0 0 0 0 0 0999 V2000 -3.3797 3.8256 0.4526 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4456 2.9543 -0.1693 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1855 1.4857 0.3057 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2587 0.6871 -0.3362 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3806 -0.7465 -0.0689 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3525 -1.7262 -0.3883 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0132 -1.6726 0.2496 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2391 -2.8926 -0.2957 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8774 -3.0261 0.2636 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0161 -1.8298 -0.0366 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4206 -2.2422 0.1791 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4197 -1.4082 -0.1465 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8436 -1.7471 0.0375 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4868 -0.8880 1.0820 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4397 0.5937 0.7523 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1362 0.9122 -0.5270 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0758 2.3813 -0.8367 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7470 3.2051 0.1756 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3528 2.6886 1.1330 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7126 4.5876 0.0741 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9807 -3.0707 0.4441 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3519 -0.7578 0.7451 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8086 -3.4026 1.6003 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4418 3.6546 -0.1244 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6782 4.8860 0.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2221 3.5262 1.5103 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3216 2.9340 -1.2716 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4683 3.2342 0.1352 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2516 1.4665 1.4058 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1703 1.2591 -0.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2250 0.9290 -1.4416 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2378 1.2043 -0.0315 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3432 -1.1300 -0.5864 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7193 -0.8761 1.0340 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1800 -1.6999 -1.5160 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7918 -2.7532 -0.1860 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0511 -1.7569 1.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4422 -0.7641 -0.0081 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2498 -2.7546 -1.3967 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8717 -3.8155 -0.1369 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4301 -3.9466 -0.2732 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1218 -1.5378 -1.1224 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6598 -3.2113 0.5975 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1041 -0.4567 -0.5593 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3356 -1.6635 -0.9512 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5717 -1.1628 1.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9823 -1.0549 2.0463 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3386 0.8283 0.6616 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8294 1.1103 1.6417 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2260 0.6660 -0.3979 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7241 0.2965 -1.3589 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0050 2.6896 -0.9103 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5788 2.5384 -1.8219 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7839 5.2038 0.8719 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3550 -3.1524 1.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0626 0.0942 0.3385 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5208 -2.6954 2.2025 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 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 13 21 1 0 10 22 1 0 9 23 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 0 2 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 5 33 1 0 5 34 1 0 6 35 1 0 6 36 1 0 7 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 10 42 1 0 11 43 1 0 12 44 1 0 13 45 1 0 14 46 1 0 14 47 1 0 15 48 1 0 15 49 1 0 16 50 1 0 16 51 1 0 17 52 1 0 17 53 1 0 20 54 1 0 21 55 1 0 22 56 1 0 23 57 1 0 M END

Standard InCHIKey	KFPLVZLISLBBSJ-BUHFOSPRSA-N
Standard InCHI	InChI=1S/C18H34O5/c1-2-3-4-5-6-7-11-16(20)17(21)14-13-15(19)10-8-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+
SMILES	CCCCCCCCC(C(/C=C/C(CCCCC(=O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	330.24	Volume:	358.562 ? Van der Waals volume.
Dense:	0.921	LogP:	3.283 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.56 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.173 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	2.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	0.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.273	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.415	Fsp³:	0.833
MCE-18:	4.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.008	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:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.677	Promiscuous compounds:	0.108

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.161	MDCK Permeability:	-4.659
Pgp-inhibitor:	0.0	Pgp-substrate:	0.013
PAMPA:	0.994 ? 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):	1.0
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.104
Plasma Protein Binding (PPB):	91.615%	Volume Distribution (VD):	0.107
Fu:	7.249% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.982
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.003
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.007	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.06
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.403
HLM stability:	0.0 ? 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):

5.028

Half-life (T1/2):

1.024

ADMET: Toxicity

hERG Blockers:	0.039	hERG Blockers (10um):	0.286
Human Hepatotoxicity (H-HT):	0.475	Drug-induced Liver Injury (DILI):	0.107
AMES Toxicity:	0.065	Rat Oral Acute Toxicity:	0.334
Maximum Recommended Daily Dose:	0.655	Skin Sensitization:	0.092
Carcinogencity:	0.187	Eye Corrosion:	0.0
Eye Irritation:	0.404	Respiratory Toxicity:	0.85
Drug-induced Neurotoxicity:	0.034	Ototoxicity:	0.971
Hematotoxicity:	0.125	Drug-induced Nephrotoxicity:	0.287
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.008	Hek293 Cytotoxicity:	0.05
BCF:	0.719 ? 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:	3.62 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.934 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.447 ? 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
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1042/BA20020118]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1556/abot.45.2003.3-4.15]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17366734]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37685099]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10246	Fumaria officinalis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13588	Sanguinaria canadensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13588	Sanguinaria canadensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10246	Fumaria officinalis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13588	Sanguinaria canadensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10246	Fumaria officinalis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17796	Lamprocapnos spectabilis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17796	Lamprocapnos spectabilis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18366	Papaver commutatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10246	Fumaria officinalis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13588	Sanguinaria canadensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17458	Sparganium stoloniferum	Species	Typhaceae	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 NPC32141 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	26562
0.1-0.2	21320
0.2-0.3	1689
0.3-0.4	162
0.4-0.5	78
0.5-0.6	16
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC99619
0.7111	Intermediate Similarity	NPC26500
0.7045	Intermediate Similarity	NPC325627
0.6444	Remote Similarity	NPC255863
0.6444	Remote Similarity	NPC136164
0.6444	Remote Similarity	NPC245947
0.617	Remote Similarity	NPC470320
0.5854	Remote Similarity	NPC324004
0.5854	Remote Similarity	NPC328497
0.5849	Remote Similarity	NPC192006
0.5556	Remote Similarity	NPC227396
0.551	Remote Similarity	NPC327112
0.5472	Remote Similarity	NPC88735
0.5455	Remote Similarity	NPC7414
0.5455	Remote Similarity	NPC279537
0.5417	Remote Similarity	NPC243532
0.5306	Remote Similarity	NPC321838
0.5217	Remote Similarity	NPC606120
0.5179	Remote Similarity	NPC47031
0.5179	Remote Similarity	NPC67076
0.5098	Remote Similarity	NPC323045
0.5098	Remote Similarity	NPC49863
0.5098	Remote Similarity	NPC317881

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC32141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5980
0.1-0.2	2921
0.2-0.3	210
0.3-0.4	17
0.4-0.5	13
0.5-0.6	4
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
0.551	Remote Similarity	NPD4246	Phase 2
0.5455	Remote Similarity	NPD4269	Phase 4
0.5455	Remote Similarity	NPD4270	Approved
0.5098	Remote Similarity	NPD4247	Clinical (unspecified phase)

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