NPASS Compound

Natural Product: NPC205797

Natural Product ID	NPC205797
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(+)-Calanolide A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL267447
PubChem CID	64972
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

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 53 56 0 0 0 0 0 0 0 0999 V2000 -4.0460 -2.9239 -1.2744 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1357 -2.1993 0.0225 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1043 -1.0798 0.1750 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8130 -1.6335 0.1342 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5918 -2.9928 0.1663 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2955 -3.4943 0.1230 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1390 -4.7696 0.1546 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7533 -2.7139 0.0519 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5954 -1.4193 0.0202 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6624 -0.8500 0.0594 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7779 0.5109 0.0271 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3170 1.3761 -0.0459 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1408 2.8186 -0.0775 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0642 3.3345 -0.0376 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2747 2.4910 0.0398 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0702 2.7688 1.3051 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1020 2.8515 -1.1932 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9910 1.1081 0.0660 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5697 0.7727 -0.0849 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7307 -0.5902 -0.0540 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0307 -1.2761 -0.0979 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1874 -0.3457 -0.1394 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2775 -0.9512 0.7556 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8933 1.0166 0.4251 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0446 1.9363 0.1224 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7065 1.5678 -0.1572 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0604 -2.0299 -1.2905 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2375 -4.0169 -1.1983 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0975 -2.7114 -1.8112 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8507 -2.5704 -1.9902 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0946 -2.8833 0.9181 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1835 -1.7752 0.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2508 -0.5169 -0.8154 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5161 -0.4333 0.9018 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3674 -3.7096 0.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0351 3.4595 -0.1365 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2005 4.4137 -0.0618 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0129 3.2589 0.9936 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4950 3.3500 2.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3909 1.8296 1.8267 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5769 3.8284 -0.9675 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8672 2.0999 -1.4207 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3959 3.0227 -2.0350 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0843 -2.0256 0.7188 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6337 -0.2196 -1.1548 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1480 -0.5998 1.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1724 -2.0594 0.7971 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2836 -0.7393 0.3748 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7227 0.9550 1.5099 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9818 1.5723 0.6211 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1747 2.0607 -0.9686 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7686 2.9399 0.5297 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2931 -1.8133 -1.8738 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 2 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 12 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 24 26 1 0 21 27 1 0 10 4 1 0 18 11 1 0 26 19 1 0 20 9 1 0 1 28 1 0 1 29 1 0 1 30 1 0 2 31 1 0 2 32 1 0 3 33 1 0 3 34 1 0 5 35 1 0 13 36 1 0 14 37 1 0 16 38 1 0 16 39 1 0 16 40 1 0 17 41 1 0 17 42 1 0 17 43 1 0 21 44 1 1 22 45 1 6 23 46 1 0 23 47 1 0 23 48 1 0 24 49 1 1 25 50 1 0 25 51 1 0 25 52 1 0 27 53 1 0 M END

Standard InCHIKey	NIDRYBLTWYFCFV-FMTVUPSXSA-N
Standard InCHI	InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18+/m1/s1
SMILES	CCCc1cc(=O)oc2c1c1c(C=CC(C)(C)O1)c1c2[C@H]([C@H](C)[C@@H](C)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	370.18	Volume:	382.975 ? Van der Waals volume.
Dense:	0.967	LogP:	3.871 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.543 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.511 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	22.0
TPSA:	68.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.795	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.171	Fsp³:	0.5
MCE-18:	84.303 ? 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:	0.835	Fluc inhibitor:	0.01 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.92 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.57 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.079	Promiscuous compounds:	0.136

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.971	MDCK Permeability:	-4.697
Pgp-inhibitor:	0.933	Pgp-substrate:	0.005
PAMPA:	0.1 ? 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%):	0.812	30% Bioavailability (F30%):	0.958
50% Bioavailability (F50%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.534	MRP1:	0.993
Plasma Protein Binding (PPB):	98.661%	Volume Distribution (VD):	0.068
Fu:	1.147% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.977	BCRP inhibitor:	0.036
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.023	CYP1A2-substrate:	0.994
CYP2C19-inhibitor:	0.13	CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.427
CYP3A4-inhibitor:	0.008	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.676 ? 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):

5.795

Half-life (T1/2):

1.11

ADMET: Toxicity

hERG Blockers:	0.114	hERG Blockers (10um):	0.45
Human Hepatotoxicity (H-HT):	0.635	Drug-induced Liver Injury (DILI):	0.7
AMES Toxicity:	0.574	Rat Oral Acute Toxicity:	0.515
Maximum Recommended Daily Dose:	0.533	Skin Sensitization:	0.94
Carcinogencity:	0.746	Eye Corrosion:	0.038
Eye Irritation:	0.709	Respiratory Toxicity:	0.75
Drug-induced Neurotoxicity:	0.158	Ototoxicity:	0.383
Hematotoxicity:	0.542	Drug-induced Nephrotoxicity:	0.584
Genotoxicity:	0.561	RPMI-8226 Immunitoxicity:	0.143
A549 Cytotoxicity:	0.311	Hek293 Cytotoxicity:	0.402
BCF:	2.115 ? 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:	4.435 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.529 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.867 ? 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
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	Sarawak, Malaysia	n.a.	PMID[11430019]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[11908963]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662094]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1379639]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104480]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15340243]
NPO17406.1	Calophyllum lanigerum var. austrocoriaceum	Varieties	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[8792623]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792623]
NPO17406.1	Calophyllum lanigerum var. austrocoriaceum	Varieties	Calophyllaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9784162]
NPO17406.1	Calophyllum lanigerum var. austrocoriaceum	Varieties	Calophyllaceae	Eukaryota	n.a.	twig	n.a.	PMID[9784162]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	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	20
Inhibition	10
EC50	30
Max protection	1
TI	1
Activity	10
MIC	6
ED50	1
DOSE	4

Activity Type	# Activity
Individual protein	14
Cell line	29
Organism	31
Nucleic acid	3
Non-molecular	1
Others	5

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT317	Nucleic acid	Nucleic Acid	n.a.	Inhibition	=	22.9	%	PMID[8632437]
NPT317	Nucleic acid	Nucleic Acid	n.a.	IC50	=	205000.0	nM	PMID[8632437]
NPT317	Nucleic acid	Nucleic Acid	n.a.	Inhibition	=	62.0	%	PMID[8632437]
NPT609	Individual protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	IC50	=	380.0	nM	PMID[8632437]
NPT609	Individual protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	Inhibition	=	83.9	%	PMID[8632437]
NPT609	Individual protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	IC50	=	320.0	nM	PMID[8632437]
NPT609	Individual protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	Inhibition	=	97.4	%	PMID[8632437]
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	0.0	%	PMID[8632437]
NPT609	Individual protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	IC50	=	10100.0	nM	PMID[8632437]
NPT609	Individual protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	Inhibition	=	91.5	%	PMID[8632437]
NPT4638	Individual protein	DNA-directed RNA polymerase beta chain	Escherichia coli K-12	Inhibition	=	16.0	%	PMID[8632437]
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	EC50	=	320.0	nM	PMID[9083491]
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	EC50	=	970.0	nM	PMID[9083491]
NPT59	Individual protein	DNA polymerase beta	Homo sapiens	IC50	=	205000.0	nM	PMID[8864237]
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	320.0	nM	PMID[8864237]
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	1000.0	nM	PMID[7561895]
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	20000.0	nM	PMID[27484512]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT315	Cell line	CEM-SS	Homo sapiens	Max protection	=	100.0	%	PMID[1379639]
NPT315	Cell line	CEM-SS	Homo sapiens	EC50	=	100.0	nM	PMID[1379639]
NPT315	Cell line	CEM-SS	Homo sapiens	IC50	=	20000.0	nM	PMID[1379639]
NPT315	Cell line	CEM-SS	Homo sapiens	EC50	=	80.0	nM	PMID[1379639]
NPT315	Cell line	CEM-SS	Homo sapiens	EC50	=	270.0	nM	PMID[9083491]
NPT315	Cell line	CEM-SS	Homo sapiens	EC50	=	170.0	nM	PMID[9873509]
NPT315	Cell line	CEM-SS	Homo sapiens	EC50	=	140.0	nM	PMID[9873509]
NPT404	Cell line	CCRF-CEM	Homo sapiens	EC50	=	267.0	nM	PMID[8632437]
NPT404	Cell line	CCRF-CEM	Homo sapiens	IC50	=	22960.0	nM	PMID[8632437]
NPT460	Cell line	MT2	Homo sapiens	EC50	=	53.0	nM	PMID[8632437]
NPT460	Cell line	MT2	Homo sapiens	IC50	=	14800.0	nM	PMID[8632437]
NPT460	Cell line	MT2	Homo sapiens	EC50	=	107.0	nM	PMID[8632437]
NPT460	Cell line	MT2	Homo sapiens	IC50	=	7150.0	nM	PMID[8632437]
NPT460	Cell line	MT2	Homo sapiens	EC50	=	27.0	nM	PMID[8632437]
NPT460	Cell line	MT2	Homo sapiens	IC50	=	7170.0	nM	PMID[8632437]
NPT460	Cell line	MT2	Homo sapiens	EC50	=	427.0	nM	PMID[8632437]
NPT460	Cell line	MT2	Homo sapiens	IC50	=	6990.0	nM	PMID[8632437]
NPT315	Cell line	CEM-SS	Homo sapiens	EC50	=	180.0	nM	PMID[8893846]
NPT315	Cell line	CEM-SS	Homo sapiens	IC50	=	7300.0	nM	PMID[8893846]
NPT315	Cell line	CEM-SS	Homo sapiens	IC50	=	23000.0	nM	PMID[9083491]
NPT315	Cell line	CEM-SS	Homo sapiens	EC50	=	490.0	nM	PMID[9083491]
NPT189	Cell line	Vero	Chlorocebus aethiops	Activity	=	6.0	%	PMID[18155519]
NPT189	Cell line	Vero	Chlorocebus aethiops	Activity	=	1.0	%	PMID[18155519]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[12662094]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[12662094]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	TI	=	40.0	n.a.	PMID[8893846]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	3.13	ug.mL-1	PMID[21752642]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	3.1	ug.mL-1	PMID[24694175]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	16000.0	nM	PMID[1379639]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	200.0	nM	PMID[11430019]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	98.0	%	PMID[18155519]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	86.0	%	PMID[18155519]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	100.0	nM	PMID[19785437]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	<=	30.0	nM	PMID[11430019]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	<=	600.0	nM	PMID[11430019]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	70.0	nM	PMID[15217281]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	ED50	=	0.31	uM	PMID[15217281]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	11.4	nM	PMID[20050672]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	464.0	nM	PMID[20050672]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	10591.0	nM	PMID[20050672]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	7166.0	nM	PMID[20050672]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	159.4	nM	PMID[20050672]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	2.2	nM	PMID[20050672]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	2.85	nM	PMID[28850227]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	100.0	nM	PMID[27484512]
NPT1115	Organism	Avian myeloblastosis virus	Avian myeloblastosis virus	Inhibition	=	20.6	%	PMID[8632437]
NPT2	Others	Unspecified	n.a.	Activity	=	0.0	%	PMID[12662094]
NPT2	Others	Unspecified	n.a.	Activity	=	27.7	%	PMID[12662094]
NPT2	Others	Unspecified	n.a.	Activity	=	66.6	%	PMID[12662094]
NPT2	Others	Unspecified	n.a.	Activity	=	92.5	%	PMID[12662094]
NPT2	Others	Unspecified	n.a.	IC50	=	290.0	molar ratio	PMID[12662094]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	DOSE	=	150.0	mg.kg-1	PMID[10021914]
NPT32	Organism	Mus musculus	Mus musculus	DOSE	=	200.0	mg.kg-1	PMID[10021914]
NPT32	Organism	Mus musculus	Mus musculus	DOSE	=	100.0	mg.kg-1	PMID[10021914]

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 NPC205797 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	14005
0.1-0.2	34467
0.2-0.3	1278
0.3-0.4	70
0.4-0.5	19
0.5-0.6	2
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC141822
1.0	High Similarity	NPC1220
1.0	High Similarity	NPC142563
1.0	High Similarity	NPC241165
0.7941	Intermediate Similarity	NPC603144
0.6944	Remote Similarity	NPC469965
0.6933	Remote Similarity	NPC139595
0.6933	Remote Similarity	NPC60704
0.6892	Remote Similarity	NPC201820
0.6667	Remote Similarity	NPC293642
0.6282	Remote Similarity	NPC35501
0.6282	Remote Similarity	NPC137262
0.6282	Remote Similarity	NPC144512
0.6282	Remote Similarity	NPC278600
0.6282	Remote Similarity	NPC37428
0.6282	Remote Similarity	NPC47040
0.5974	Remote Similarity	NPC38153
0.5443	Remote Similarity	NPC291551

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC205797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3068
0.1-0.2	6058
0.2-0.3	22
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	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD5123	Phase 1
1.0	High Similarity	NPD5124	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