NPASS Compound

Natural Product: NPC202768

Natural Product ID	NPC202768
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FPJQGFLUORYYPE-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1197637
PubChem CID	160876
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 43 47 0 0 0 0 0 0 0 0999 V2000 -5.7069 -0.1311 2.5422 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2642 -0.1212 1.1972 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8876 -0.1219 0.8979 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9373 -0.1324 1.8830 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5728 -0.1335 1.6402 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5941 -0.0389 2.7244 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7008 -0.6553 2.3967 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1590 -0.3841 1.0596 N 0 0 0 0 0 4 0 0 0 0 0 0 2.5085 -0.3760 0.8363 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9575 -0.2336 -0.4488 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0927 -0.0987 -1.5185 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5750 0.0409 -2.7923 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9217 0.0519 -3.0509 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7867 -0.0819 -1.9899 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3124 -0.2226 -0.7077 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4087 -0.3350 0.1396 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6145 -0.1705 -0.5871 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1773 -0.1089 -1.9217 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7344 -0.1086 -1.2594 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2955 -0.2513 0.0438 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1561 -0.1273 0.3260 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0694 -0.1146 -0.7040 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4359 -0.1121 -0.3959 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3338 -0.0993 -1.4328 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9669 -0.0883 -2.7958 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7466 0.1829 2.6433 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1012 0.6397 3.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4804 -1.0935 3.0568 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2271 -0.1406 2.9230 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0005 -0.4675 3.6843 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4327 1.0807 2.8786 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6320 -1.7983 2.4597 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5043 -0.3781 3.1483 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1717 -0.4833 1.6908 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8972 0.1468 -3.6333 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3073 0.1647 -4.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0488 0.8011 -0.2342 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3165 -1.0130 -0.4188 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0405 -0.0051 -2.0610 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7861 -0.1088 -1.7319 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4983 -1.0671 -3.0521 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1731 0.6881 -2.9954 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7919 0.1504 -3.4647 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 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 11 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 23 3 1 0 21 5 2 0 20 8 1 0 15 10 1 0 18 14 1 0 1 26 1 0 1 27 1 0 1 28 1 0 4 29 1 0 6 30 1 0 6 31 1 0 7 32 1 0 7 33 1 0 9 34 1 0 12 35 1 0 13 36 1 0 17 37 1 0 17 38 1 0 19 39 1 0 22 40 1 0 25 41 1 0 25 42 1 0 25 43 1 0 M CHG 1 8 1 M END

Standard InCHIKey	FPJQGFLUORYYPE-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C20H18NO4/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
SMILES	COc1cc2CC[n+]3cc4c(ccc5c4OCO5)cc3-c2cc1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	336.12	Volume:	338.078 ? Van der Waals volume.
Dense:	0.994	LogP:	3.107 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.201 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.095 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	25.0
TPSA:	40.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.674	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.842	Fsp³:	0.25
MCE-18:	56.0 ? 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:	0.815	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.768 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.522 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.016	Promiscuous compounds:	0.782

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.005	MDCK Permeability:	-4.688
Pgp-inhibitor:	0.025	Pgp-substrate:	1.0
PAMPA:	0.097 ? 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):	0.144
20% Bioavailability (F20%):	0.95	30% Bioavailability (F30%):	0.306
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.667
Plasma Protein Binding (PPB):	70.987%	Volume Distribution (VD):	0.043
Fu:	35.461% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.792
OATP1B3 inhibitor:	0.87	BCRP inhibitor:	0.949
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.982	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.228	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.988	CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.009	CYP3A4-substrate:	0.64
CYP2B6-substrate:	0.94	CYP2C8-inhibitor:	0.0
HLM stability:	0.936 ? 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):

5.935

Half-life (T1/2):

1.265

ADMET: Toxicity

hERG Blockers:	0.273	hERG Blockers (10um):	0.457
Human Hepatotoxicity (H-HT):	0.134	Drug-induced Liver Injury (DILI):	0.134
AMES Toxicity:	0.35	Rat Oral Acute Toxicity:	0.884
Maximum Recommended Daily Dose:	0.916	Skin Sensitization:	0.967
Carcinogencity:	0.748	Eye Corrosion:	0.027
Eye Irritation:	0.975	Respiratory Toxicity:	0.92
Drug-induced Neurotoxicity:	0.073	Ototoxicity:	0.064
Hematotoxicity:	0.066	Drug-induced Nephrotoxicity:	0.081
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.118
A549 Cytotoxicity:	0.005	Hek293 Cytotoxicity:	0.537
BCF:	2.054 ? 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:	4.336 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.844 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.071 ? 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
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[11000020]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21401114]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24897106]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25277281]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	tuber	n.a.	PMID[25670016]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28627	Coptis trifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26538	Phellodendron chinese	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28627	Coptis trifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7001	Berberis floribunda	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7001	Berberis floribunda	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28627	Coptis trifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26538	Phellodendron chinese	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28410	Nandina domestica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28627	Coptis trifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7001	Berberis floribunda	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	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
Potency	31
AC50	2
IC50	7
Inhibition	4

Activity Type	# Activity
Individual protein	32
Nucleic acid	1
Protein complex	2
Organism	2
Protein-protein interaction	1
Single protein	5
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT151	Individual protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT1416	Individual protein	Neuropeptide S receptor	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT1005	Individual protein	Tumor susceptibility gene 101 protein	Homo sapiens	Potency	n.a.	56234.1	nM	PubChem BioAssay data set
NPT2971	Individual protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	326.4	nM	PubChem BioAssay data set
NPT1474	Individual protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT11	Individual protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	19952.6	nM	PubChem BioAssay data set
NPT1005	Individual protein	Tumor susceptibility gene 101 protein	Homo sapiens	Potency	n.a.	12981.9	nM	PubChem BioAssay data set
NPT105	Individual protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT11	Individual protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT161	Individual protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	125892.5	nM	PubChem BioAssay data set
NPT261	Individual protein	Monoamine oxidase A	Homo sapiens	Inhibition	<	30.0	%	PMID[33619958]
NPT261	Individual protein	Monoamine oxidase A	Homo sapiens	Inhibition	=	70.0	%	PMID[35101649]
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	10000.0	nM	PubChem BioAssay data set
NPT55	Individual protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	1990.5	nM	PubChem BioAssay data set
NPT5135	Nucleic acid	Salmon testes DNA	Oncorhynchus gorbuscha	AC50	=	32234.0	nM	PubChem BioAssay data set
NPT4214	Protein complex	SUMO-activating enzyme	Homo sapiens	IC50	=	8680.0	nM	PubChem BioAssay data set
NPT4214	Protein complex	SUMO-activating enzyme	Homo sapiens	IC50	=	4170.0	nM	PubChem BioAssay data set
NPT803	Individual protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	19952.6	nM	PubChem BioAssay data set
NPT9	Individual protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT582	Individual protein	Monoamine oxidase B	Homo sapiens	Inhibition	=	40.0	%	PMID[35101649]
NPT582	Individual protein	Monoamine oxidase B	Homo sapiens	Inhibition	<	30.0	%	PMID[33619958]
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT484	Individual protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	16944.1	nM	PubChem BioAssay data set
NPT444	Individual protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	25118.9	nM	PubChem BioAssay data set
NPT446	Individual protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	112201.8	nM	PubChem BioAssay data set
NPT831	Individual protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	8436.8	nM	PubChem BioAssay data set
NPT21762	Single protein	Lysine-specific histone demethylase 1	Homo sapiens	IC50	=	140.0	nM	PMID[35101649]
NPT21762	Single protein	Lysine-specific histone demethylase 1	Homo sapiens	IC50	=	140.0	nM	PMID[33945992]
NPT21762	Single protein	Lysine-specific histone demethylase 1	Homo sapiens	IC50	=	140.0	nM	PMID[33619958]
NPT21762	Single protein	Lysine-specific histone demethylase 1	Homo sapiens	IC50	=	140.0	nM	PMID[33581557]
NPT21762	Single protein	Lysine-specific histone demethylase 1	Homo sapiens	IC50	=	140.0	nM	PMID[35820351]
NPT93	Individual protein	Survival motor neuron protein	Homo sapiens	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT59	Individual protein	DNA polymerase beta	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	14125.4	nM	PubChem BioAssay data set
NPT755	Individual protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT3816	Individual protein	ORF 73	Human herpesvirus 8	AC50	=	20451.0	nM	PubChem BioAssay data set
NPT5	Individual protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	70794.6	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	147.2	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1041.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11582.1	nM	PubChem BioAssay data set

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 NPC202768 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	34708
0.1-0.2	14266
0.2-0.3	852
0.3-0.4	17
0.4-0.5	1
0.5-0.6	2
0.6-0.7	6
0.7-0.8	0
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8983	High Similarity	NPC171409
0.8833	High Similarity	NPC96405
0.8525	High Similarity	NPC53069
0.8387	Intermediate Similarity	NPC296482
0.8305	Intermediate Similarity	NPC16452
0.8167	Intermediate Similarity	NPC36229
0.6812	Remote Similarity	NPC481435
0.6471	Remote Similarity	NPC202605
0.6418	Remote Similarity	NPC313189
0.625	Remote Similarity	NPC4071
0.6154	Remote Similarity	NPC607600
0.6119	Remote Similarity	NPC135549
0.5571	Remote Similarity	NPC31930
0.5342	Remote Similarity	NPC112206

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC202768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6795
0.1-0.2	2324
0.2-0.3	28
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8525	High Similarity	NPD3816	Phase 3
0.8387	Intermediate Similarity	NPD3815	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