NPASS Compound

Natural Product: NPC6597

Natural Product ID	NPC6597
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(+)-Curcuphenol
IUPAC Name	5-methyl-2-[(2S)-6-methylhept-5-en-2-yl]phenol
Synonyms	(+)-Curcuphenol; (1S)-(+)-Curcuphenol; (S)-(+)-Curcuphenol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL451860
PubChem CID	156118
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

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 38 38 0 0 0 0 0 0 0 0999 V2000 4.1788 -0.3127 1.6307 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9779 -0.0691 0.1974 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8761 -0.5547 -0.3996 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8609 -1.3268 0.3450 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5269 -0.7028 0.4310 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2237 -0.4174 -0.8055 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3637 0.5159 -1.7924 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6173 -0.0401 -0.4167 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9875 1.2721 -0.1788 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2830 1.6116 0.1813 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2511 0.6454 0.3149 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6488 0.9355 0.6949 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8904 -0.6581 0.0803 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 -1.0077 -0.2828 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2409 -2.3377 -0.5167 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9569 0.6921 -0.5874 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3097 0.0312 2.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2818 -1.4126 1.8376 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0856 0.1574 2.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7162 -0.4027 -1.4657 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2974 -1.5103 1.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8472 -2.3499 -0.1060 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1198 -1.4304 1.0252 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5845 0.1762 1.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3434 -1.4120 -1.3413 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7561 -0.0057 -2.6588 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5163 1.1292 -2.1946 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0814 1.2610 -1.3970 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2387 2.0346 -0.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5792 2.6382 0.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0046 1.9090 0.3061 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6706 1.0372 1.8148 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2985 0.0958 0.4501 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6107 -1.4445 0.1722 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1384 -2.9139 0.3275 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4299 1.3531 -1.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5217 -0.0398 -1.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5978 1.3492 0.0055 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 6 7 1 0 6 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 13 14 2 0 14 15 1 0 2 16 1 0 14 8 1 0 1 17 1 0 1 18 1 0 1 19 1 0 3 20 1 0 4 21 1 0 4 22 1 0 5 23 1 0 5 24 1 0 6 25 1 6 7 26 1 0 7 27 1 0 7 28 1 0 9 29 1 0 10 30 1 0 12 31 1 0 12 32 1 0 12 33 1 0 13 34 1 0 15 35 1 0 16 36 1 0 16 37 1 0 16 38 1 0 M END

Standard InCHIKey	BTXSROVNGICYFE-ZDUSSCGKSA-N
Standard InCHI	InChI=1S/C15H22O/c1-11(2)6-5-7-13(4)14-9-8-12(3)10-15(14)16/h6,8-10,13,16H,5,7H2,1-4H3/t13-/m0/s1
SMILES	CC(=CCC[C@H](C)c1ccc(C)cc1O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	218.17	Volume:	257.684 ? Van der Waals volume.
Dense:	0.847	LogP:	4.6 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.664 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.244 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	7.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	1.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.735	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.787	Fsp³:	0.467
MCE-18:	16.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.192	Fluc inhibitor:	0.101 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.066 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.099 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.987	Promiscuous compounds:	0.134

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.72	MDCK Permeability:	-4.642
Pgp-inhibitor:	0.499	Pgp-substrate:	0.136
PAMPA:	0.061 ? 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%):	0.047
50% Bioavailability (F50%):	0.433

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.74	MRP1:	0.98
Plasma Protein Binding (PPB):	94.565%	Volume Distribution (VD):	0.361
Fu:	5.998% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.929
OATP1B3 inhibitor:	0.812	BCRP inhibitor:	0.052
BSEP inhibitor:	0.901

ADMET: Metabolism

CYP1A2-inhibitor:	0.62	CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.935	CYP2C19-substrate:	0.605
CYP2C9-inhibitor:	0.74	CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.928	CYP2D6-substrate:	0.783
CYP3A4-inhibitor:	0.827	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.893
HLM stability:	0.984 ? 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):

8.342

Half-life (T1/2):

0.827

ADMET: Toxicity

hERG Blockers:	0.197	hERG Blockers (10um):	0.64
Human Hepatotoxicity (H-HT):	0.654	Drug-induced Liver Injury (DILI):	0.075
AMES Toxicity:	0.287	Rat Oral Acute Toxicity:	0.243
Maximum Recommended Daily Dose:	0.187	Skin Sensitization:	0.957
Carcinogencity:	0.187	Eye Corrosion:	0.934
Eye Irritation:	0.992	Respiratory Toxicity:	0.896
Drug-induced Neurotoxicity:	0.42	Ototoxicity:	0.257
Hematotoxicity:	0.162	Drug-induced Nephrotoxicity:	0.348
Genotoxicity:	0.02	RPMI-8226 Immunitoxicity:	0.082
A549 Cytotoxicity:	0.409	Hek293 Cytotoxicity:	0.13
BCF:	2.326 ? 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:	4.588 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.568 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.297 ? 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
NPO40764	Parahigginsia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10217711]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO26494	Didiscus oxeata	Species	Halichondriidae	Eukaryota	n.a.	Rio Bueno, Jamaica	n.a.	PMID[12444675]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO40764	Parahigginsia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26494	Didiscus oxeata	Species	Halichondriidae	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	10
MIC	12
MFC	2
MBC	2
GI	1
Activity	57

Activity Type	# Activity
Individual protein	1
Cell line	54
Organism	13
Non-molecular	16

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT36	Individual protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	=	35800.0	nM	DOI[10.1039/C2MD20185B]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell line	P388	Mus musculus	IC50	=	7.0	ug.mL-1	DOI[10.1021/np50053a042]
NPT81	Cell line	A549	Homo sapiens	MIC	=	10.0	ug.mL-1	DOI[10.1021/np50053a042]
NPT180	Cell line	HCT-8	Homo sapiens	MIC	=	0.1	ug.mL-1	DOI[10.1021/np50053a042]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	209000.0	nM	PMID[12762791]
NPT168	Cell line	P388	Mus musculus	IC50	=	0.1	ug.mL-1	PMID[10217711]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	8.1	ug.mL-1	PMID[10217711]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI	>	20.0	%	DOI[10.1039/C2MD20185B]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	20000.0	nM	DOI[10.1039/C2MD20185B]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	37200.0	nM	DOI[10.1039/C2MD20185B]
NPT784	Cell line	MDA-MB-468	Homo sapiens	Activity	=	95.65	%	DOI[10.1039/C2MD20185B]
NPT396	Cell line	T47D	Homo sapiens	Activity	=	110.61	%	DOI[10.1039/C2MD20185B]
NPT457	Cell line	BT-549	Homo sapiens	Activity	=	114.49	%	DOI[10.1039/C2MD20185B]
NPT82	Cell line	MDA-MB-231	Homo sapiens	Activity	=	97.07	%	DOI[10.1039/C2MD20185B]
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	97.84	%	DOI[10.1039/C2MD20185B]
NPT384	Cell line	TK-10	Homo sapiens	Activity	=	109.99	%	DOI[10.1039/C2MD20185B]
NPT368	Cell line	SN12C	Homo sapiens	Activity	=	104.83	%	DOI[10.1039/C2MD20185B]
NPT406	Cell line	RXF 393	Homo sapiens	Activity	=	103.08	%	DOI[10.1039/C2MD20185B]
NPT308	Cell line	CAKI-1	Homo sapiens	Activity	=	107.0	%	DOI[10.1039/C2MD20185B]
NPT369	Cell line	ACHN	Homo sapiens	Activity	=	109.35	%	DOI[10.1039/C2MD20185B]
NPT376	Cell line	A498	Homo sapiens	Activity	=	87.85	%	DOI[10.1039/C2MD20185B]
NPT401	Cell line	786-0	Homo sapiens	Activity	=	79.88	%	DOI[10.1039/C2MD20185B]
NPT458	Cell line	IGROV-1	Homo sapiens	Activity	=	97.76	%	DOI[10.1039/C2MD20185B]
NPT373	Cell line	SK-MEL-5	Homo sapiens	Activity	=	97.46	%	DOI[10.1039/C2MD20185B]
NPT170	Cell line	SK-MEL-28	Homo sapiens	Activity	=	119.18	%	DOI[10.1039/C2MD20185B]
NPT147	Cell line	SK-MEL-2	Homo sapiens	Activity	=	147.33	%	DOI[10.1039/C2MD20185B]
NPT400	Cell line	MDA-MB-435	Homo sapiens	Activity	=	100.32	%	DOI[10.1039/C2MD20185B]
NPT387	Cell line	M14	Homo sapiens	Activity	=	106.0	%	DOI[10.1039/C2MD20185B]
NPT375	Cell line	Malme-3M	Homo sapiens	Activity	=	114.51	%	DOI[10.1039/C2MD20185B]
NPT390	Cell line	LOX IMVI	Homo sapiens	Activity	=	107.4	%	DOI[10.1039/C2MD20185B]
NPT380	Cell line	U-251	Homo sapiens	Activity	=	102.89	%	DOI[10.1039/C2MD20185B]
NPT392	Cell line	SNB-75	Homo sapiens	Activity	=	94.35	%	DOI[10.1039/C2MD20185B]
NPT383	Cell line	SNB-19	Homo sapiens	Activity	=	98.46	%	DOI[10.1039/C2MD20185B]
NPT374	Cell line	SF-539	Homo sapiens	Activity	=	103.29	%	DOI[10.1039/C2MD20185B]
NPT399	Cell line	SF-295	Homo sapiens	Activity	=	106.62	%	DOI[10.1039/C2MD20185B]
NPT323	Cell line	SW-620	Homo sapiens	Activity	=	113.87	%	DOI[10.1039/C2MD20185B]
NPT386	Cell line	KM12	Homo sapiens	Activity	=	93.79	%	DOI[10.1039/C2MD20185B]
NPT139	Cell line	HT-29	Homo sapiens	Activity	=	102.73	%	DOI[10.1039/C2MD20185B]
NPT391	Cell line	HCC 2998	Homo sapiens	Activity	=	99.54	%	DOI[10.1039/C2MD20185B]
NPT407	Cell line	COLO 205	Homo sapiens	Activity	=	116.6	%	DOI[10.1039/C2MD20185B]
NPT455	Cell line	NCI-H522	Homo sapiens	Activity	=	100.89	%	DOI[10.1039/C2MD20185B]
NPT397	Cell line	NCI-H460	Homo sapiens	Activity	=	106.79	%	DOI[10.1039/C2MD20185B]
NPT388	Cell line	NCI-H322M	Homo sapiens	Activity	=	112.83	%	DOI[10.1039/C2MD20185B]
NPT370	Cell line	NCI-H23	Homo sapiens	Activity	=	94.86	%	DOI[10.1039/C2MD20185B]
NPT405	Cell line	NCI-H226	Homo sapiens	Activity	=	106.52	%	DOI[10.1039/C2MD20185B]
NPT372	Cell line	HOP-92	Homo sapiens	Activity	=	84.95	%	DOI[10.1039/C2MD20185B]
NPT379	Cell line	HOP-62	Homo sapiens	Activity	=	102.09	%	DOI[10.1039/C2MD20185B]
NPT81	Cell line	A549	Homo sapiens	Activity	=	92.59	%	DOI[10.1039/C2MD20185B]
NPT389	Cell line	RPMI-8226	Homo sapiens	Activity	=	99.89	%	DOI[10.1039/C2MD20185B]
NPT112	Cell line	MOLT-4	Homo sapiens	Activity	=	102.06	%	DOI[10.1039/C2MD20185B]
NPT111	Cell line	K562	Homo sapiens	Activity	=	93.03	%	DOI[10.1039/C2MD20185B]
NPT116	Cell line	HL-60	Homo sapiens	Activity	=	85.65	%	DOI[10.1039/C2MD20185B]
NPT404	Cell line	CCRF-CEM	Homo sapiens	Activity	=	104.92	%	DOI[10.1039/C2MD20185B]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	20000.0	nM	DOI[10.1039/C2MD20185B]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	DOI[10.1039/C2MD20185B]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	MIC	=	3.6	ug.mL-1	PMID[12444675]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	MIC	=	1.8	ug.mL-1	PMID[12444675]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	MIC	=	3.6	ug.mL-1	PMID[33038665]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	MIC	=	1.8	ug.mL-1	PMID[33038665]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	MIC	=	0.1	ug.mL-1	DOI[10.1021/np50053a042]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	8.0	ug.mL-1	DOI[10.1021/np50053a042]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	7.5	ug.mL-1	PMID[12444675]
NPT20	Organism	Candida albicans	Candida albicans	MFC	=	12.5	ug ml-1	PMID[12444675]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	8.3	ug.mL-1	PMID[10217711]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	114.35	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	80.0	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	83.0	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	118.93	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	98.97	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	108.08	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	100.35	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	96.28	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	99.98	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	107.12	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	109.18	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	97.29	%	DOI[10.1039/C2MD20185B]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	109.82	%	DOI[10.1039/C2MD20185B]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	7.5	ug.mL-1	PMID[12444675]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	7.5	ug.mL-1	PMID[12444675]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MFC	=	12.5	ug ml-1	PMID[12444675]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	12.5	ug ml-1	PMID[12444675]

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 NPC6597 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	24274
0.1-0.2	23439
0.2-0.3	2056
0.3-0.4	70
0.4-0.5	9
0.5-0.6	7
0.6-0.7	3
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
0.6923	Remote Similarity	NPC475225
0.6	Remote Similarity	NPC79241
0.6	Remote Similarity	NPC72729
0.5854	Remote Similarity	NPC602826
0.5854	Remote Similarity	NPC610248
0.5758	Remote Similarity	NPC259512
0.5714	Remote Similarity	NPC606473
0.5676	Remote Similarity	NPC198023
0.5476	Remote Similarity	NPC77492
0.5116	Remote Similarity	NPC489507

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC6597 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5569
0.1-0.2	3497
0.2-0.3	81
0.3-0.4	2
0.4-0.5	0
0.5-0.6	1
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
0.5758	Remote Similarity	NPD288	Phase 4

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