NPASS Compound

Natural Product: NPC302044

Natural Product ID	NPC302044
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RALMOKVINHMHFN-OGHRFRAUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

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 94 97 0 0 0 0 0 0 0 0999 V2000 -3.2226 -3.4999 -3.5457 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6844 -3.7003 -2.1612 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0073 -3.0738 -1.1768 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8492 -2.2170 -1.4389 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9275 -0.7697 -1.1847 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5728 -0.1193 -1.5423 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4064 -0.1742 -0.4076 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6154 -0.9846 -0.8148 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9342 -0.5044 -0.3627 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9903 -1.2432 -1.1506 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0224 -2.7179 -0.9880 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3819 -3.2381 0.3454 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5151 -3.9736 0.4279 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6372 -3.0646 1.6015 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1301 0.9884 -0.5166 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4198 1.3616 -1.9553 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3401 1.4117 0.3225 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0520 1.6966 -0.0483 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7923 1.1720 0.0715 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1439 1.9222 0.6652 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3254 3.3209 0.4348 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1814 3.9120 1.2219 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3266 4.1327 -0.5616 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9688 3.6984 -1.6937 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6501 4.5525 -2.5508 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6928 5.8886 -2.2752 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0450 6.3306 -1.1380 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3747 5.5101 -0.2867 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1053 7.7055 -0.8830 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3760 6.7646 -3.1300 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1100 1.2153 1.5607 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5364 1.7750 2.5749 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5581 -0.1746 1.2167 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9337 -0.9036 2.4570 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9770 -0.3080 3.2922 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7282 -0.0355 4.5568 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4083 -0.3260 5.1413 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7794 0.5684 5.4037 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2729 -0.8337 0.7420 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1591 -1.8172 1.2635 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5047 -0.2308 0.0654 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8495 1.2668 -0.2653 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8469 -0.8291 0.3748 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8556 -4.5689 -1.9287 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2139 -3.8598 -3.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9094 -3.9766 -4.2830 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2643 -2.4040 -3.7595 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3944 -3.2967 -0.1890 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6357 -2.3194 -2.5663 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9390 -2.7089 -1.0028 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5966 -0.3587 -2.0254 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7038 0.8476 -2.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1867 -0.7865 -2.3788 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4588 -2.0215 -0.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6388 -1.1094 -1.9337 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0665 -0.7323 0.6959 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8816 -1.0292 -2.2591 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0134 -0.8618 -0.9206 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0042 -3.1539 -1.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7175 -3.1910 -1.7407 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7930 -4.3610 1.3916 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1153 -4.1644 -0.4360 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0663 -2.2128 2.1959 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7560 -4.0181 2.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5629 -2.8919 1.4977 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3850 0.9303 -2.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5845 1.1107 -2.6321 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5586 2.4612 -1.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1936 1.1052 1.3646 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2833 1.0518 -0.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3641 2.5206 0.3042 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8731 2.6392 -1.9483 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1298 4.1249 -3.4185 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1148 5.9104 0.5914 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9489 8.0637 -0.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7604 7.3390 -3.7248 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1591 -1.9709 2.1875 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9951 -0.9892 3.0657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9794 -0.0578 2.9465 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1788 -1.4235 5.0215 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4101 -0.1424 6.2452 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6250 0.2245 4.6244 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4226 1.4421 5.9742 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1691 -0.2142 6.1146 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6736 0.8788 4.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8835 1.8315 0.6686 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8654 1.2659 -0.7053 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1800 1.6592 -1.0251 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8725 -1.5616 1.1740 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3011 -1.1601 -0.5987 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5771 -0.0221 0.7006 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0061 -4.7607 -0.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8116 -5.5256 -2.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7473 -4.0063 -2.3337 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 7 6 1 6 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 9 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 26 30 1 0 20 31 1 0 31 32 2 0 31 33 1 0 33 34 1 1 34 35 1 0 35 36 2 3 36 37 1 0 36 38 1 0 33 39 1 0 39 40 2 0 33 41 1 0 41 42 1 0 41 43 1 0 2 44 1 0 41 5 1 0 19 7 1 0 28 23 1 0 39 7 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 5 51 1 6 6 52 1 0 6 53 1 0 8 54 1 0 8 55 1 0 9 56 1 1 10 57 1 0 10 58 1 0 11 59 1 0 11 60 1 0 13 61 1 0 13 62 1 0 14 63 1 0 14 64 1 0 14 65 1 0 16 66 1 0 16 67 1 0 16 68 1 0 17 69 1 0 17 70 1 0 17 71 1 0 24 72 1 0 25 73 1 0 28 74 1 0 29 75 1 0 30 76 1 0 34 77 1 0 34 78 1 0 35 79 1 0 37 80 1 0 37 81 1 0 37 82 1 0 38 83 1 0 38 84 1 0 38 85 1 0 42 86 1 0 42 87 1 0 42 88 1 0 43 89 1 0 43 90 1 0 43 91 1 0 44 92 1 0 44 93 1 0 44 94 1 0 M END

Standard InCHIKey	RALMOKVINHMHFN-OGHRFRAUSA-N
Standard InCHI	InChI=1S/C38H50O6/c1-22(2)11-14-26-20-37-21-27(15-12-23(3)4)36(9,10)44-33(37)30(31(41)25-13-16-28(39)29(40)19-25)32(42)38(34(37)43,35(26,7)8)18-17-24(5)6/h11,13,16-17,19,26-27,39-40H,3,12,14-15,18,20-21H2,1-2,4-10H3/t26-,27-,37-,38-/m1/s1
SMILES	CC(=CC[C@@H]1C[C@@]23C[C@@H](CCC(=C)C)C(C)(C)OC2=C(C(=O)c2ccc(c(c2)O)O)C(=O)[C@](CC=C(C)C)(C3=O)C1(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.36	Volume:	657.955 ? Van der Waals volume.
Dense:	0.916	LogP:	6.31 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.807 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.711 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	27.0
TPSA:	100.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.097	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.142	Fsp³:	0.553
MCE-18:	158.034 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.917	Fluc inhibitor:	0.058 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.032 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.466 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.515	Promiscuous compounds:	0.123

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.847	MDCK Permeability:	-4.682
Pgp-inhibitor:	0.001	Pgp-substrate:	0.0
PAMPA:	0.573 ? 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%):	0.038	30% Bioavailability (F30%):	0.023
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027	MRP1:	0.952
Plasma Protein Binding (PPB):	89.703%	Volume Distribution (VD):	0.233
Fu:	11.473% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.889	BCRP inhibitor:	0.002
BSEP inhibitor:	0.118

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.288
CYP2C19-inhibitor:	0.98	CYP2C19-substrate:	0.198
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.411
CYP3A4-inhibitor:	0.967	CYP3A4-substrate:	0.752
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

7.146

Half-life (T1/2):

1.106

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.397
Human Hepatotoxicity (H-HT):	0.608	Drug-induced Liver Injury (DILI):	0.668
AMES Toxicity:	0.382	Rat Oral Acute Toxicity:	0.694
Maximum Recommended Daily Dose:	0.333	Skin Sensitization:	0.999
Carcinogencity:	0.689	Eye Corrosion:	0.0
Eye Irritation:	0.082	Respiratory Toxicity:	0.868
Drug-induced Neurotoxicity:	0.66	Ototoxicity:	0.916
Hematotoxicity:	0.328	Drug-induced Nephrotoxicity:	0.984
Genotoxicity:	0.98	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.74	Hek293 Cytotoxicity:	0.254
BCF:	2.044 ? 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:	5.611 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	8.098 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.841 ? 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
NPO6502	Moronobea coccinea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23245650]
NPO4624	Agathosma dielsiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3715	Helianthus rigidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6502	Moronobea coccinea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4624	Agathosma dielsiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6502	Moronobea coccinea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3715	Helianthus rigidus	Species	Asteraceae	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
Inhibition	2
Activity	26
IC50	6

Activity Type	# Activity
Individual protein	2
Cell line	32

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT38	Individual protein	Signal transducer and activator of transcription 3	Homo sapiens	Inhibition	n.a.	n.a.	%	PMID[36461923]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	11.09	%	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	11.75	%	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	4.17	%	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	IC50	=	9300.0	nM	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	80.82	%	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	80.26	%	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	3.01	%	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	5.65	%	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	6.37	%	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	2.09	%	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	5.35	%	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	11.74	%	PMID[36461923]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	11300.0	nM	PMID[36461923]
NPT1229	Cell line	Huh-7	Homo sapiens	Activity	=	77.7	%	PMID[36461923]
NPT20904	Cell line	Hep 3B2	Homo sapiens	IC50	=	17100.0	nM	PMID[36461923]

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 NPC302044 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	8782
0.1-0.2	40064
0.2-0.3	881
0.3-0.4	56
0.4-0.5	46
0.5-0.6	10
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	7
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC294679
1.0	High Similarity	NPC145301
1.0	High Similarity	NPC600911
0.8857	High Similarity	NPC8493
0.8857	High Similarity	NPC469375
0.8857	High Similarity	NPC110855
0.8857	High Similarity	NPC144247
0.8649	High Similarity	NPC606227
0.8649	High Similarity	NPC610595
0.8514	High Similarity	NPC231479
0.7895	Intermediate Similarity	NPC606237
0.75	Intermediate Similarity	NPC479152
0.6951	Remote Similarity	NPC305710
0.6933	Remote Similarity	NPC268930
0.6875	Remote Similarity	NPC264229
0.6875	Remote Similarity	NPC46549
0.6875	Remote Similarity	NPC606601
0.593	Remote Similarity	NPC602531
0.5529	Remote Similarity	NPC469857
0.5529	Remote Similarity	NPC245760
0.5309	Remote Similarity	NPC149773
0.5301	Remote Similarity	NPC483069
0.5294	Remote Similarity	NPC297797
0.5227	Remote Similarity	NPC471968
0.5176	Remote Similarity	NPC46242
0.5176	Remote Similarity	NPC91887
0.5176	Remote Similarity	NPC93556

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC302044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3592
0.1-0.2	5534
0.2-0.3	24
0.3-0.4	0
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