NPASS Compound

Natural Product: NPC602763

Natural Product ID	NPC602763
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LLOKIGWPNVSDGJ-AFBVCZJXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2000089
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

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 83 87 0 0 0 0 0 0 0 0999 V2000 -3.8263 2.4497 0.0696 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8372 1.8909 0.4338 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8606 0.5676 0.6108 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8134 -0.5466 0.4322 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6360 -0.2658 -0.8445 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5904 -1.3893 -1.0141 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8425 -1.3163 -0.4407 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7742 -2.3494 -0.5732 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4459 -3.4648 -1.2874 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2069 -3.5638 -1.8687 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2860 -2.5225 -1.7272 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9141 -1.6976 0.1874 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 -1.4740 -0.7802 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7186 -2.9474 0.6714 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3548 -3.9183 1.4090 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2114 -4.5001 2.2617 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1728 -4.6959 1.1743 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3292 -3.5409 0.2833 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4495 -2.4051 0.7594 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4525 -2.2141 1.9914 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3679 -1.5336 0.0509 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9209 -0.3452 0.7579 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3509 -0.1366 0.4920 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7329 0.0662 -0.9291 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2176 0.2846 -1.1176 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0447 -0.8540 -0.6451 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5051 -0.5727 -0.8606 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0469 0.5778 -0.1402 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4018 1.2407 0.6375 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4866 0.9640 -0.3750 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1097 1.8835 0.5892 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6150 2.4059 -0.6139 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0065 0.7517 0.2569 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3788 0.8652 -0.9157 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5278 1.7799 1.0812 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5646 2.6999 0.6916 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2726 3.6129 -0.4258 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0684 4.4436 -0.2628 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1345 4.0048 -0.7553 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3053 4.7513 -0.6214 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2343 5.9568 0.0239 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0298 6.4174 0.5279 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1279 5.6640 0.3877 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9811 0.1743 1.0790 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4717 -0.6121 1.2402 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1919 0.6732 -0.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9541 -0.2769 -1.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1544 -0.4731 0.1266 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7522 -2.2851 -0.1213 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1547 -4.2908 -1.4091 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9696 -4.4545 -2.4285 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3311 -2.6315 -2.1917 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1399 -3.4969 2.0896 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7847 -4.7733 0.8169 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5254 -5.4357 2.7194 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9399 -3.7192 2.9850 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1795 -4.7243 1.7057 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3346 -5.6885 0.7071 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3144 -3.6776 -0.7860 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6103 -1.6829 -0.8945 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7269 -0.4032 1.8452 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8866 -1.0595 0.8643 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7202 0.6753 1.1639 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4570 -0.8280 -1.5406 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1958 0.9263 -1.3497 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5628 1.2245 -0.6625 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4394 0.4029 -2.2198 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8781 -1.0687 0.4496 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8388 -1.7981 -1.2285 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7255 -0.4793 -1.9486 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1321 -1.4629 -0.5458 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0837 0.3685 -1.0816 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5518 2.0932 1.5129 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2193 1.8416 0.7020 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1096 1.8276 1.9943 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8595 3.2697 1.6273 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1703 4.2639 -0.6333 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1400 3.0544 -1.3974 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2237 3.0652 -1.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2616 4.4278 -0.9994 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1479 6.5593 0.1390 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0138 7.3873 1.0383 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0339 6.0624 0.7940 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 4 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 31 32 1 0 22 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 36 2 1 0 43 38 1 0 11 6 1 0 18 14 1 0 32 30 1 0 3 44 1 0 4 45 1 1 5 46 1 0 5 47 1 0 7 48 1 0 8 49 1 0 9 50 1 0 10 51 1 0 11 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 6 21 60 1 0 22 61 1 1 23 62 1 0 23 63 1 0 24 64 1 0 24 65 1 0 25 66 1 0 25 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 27 71 1 0 30 72 1 6 31 73 1 0 31 74 1 0 35 75 1 0 36 76 1 1 37 77 1 0 37 78 1 0 39 79 1 0 40 80 1 0 41 81 1 0 42 82 1 0 43 83 1 0 M END

Standard InCHIKey	LLOKIGWPNVSDGJ-AFBVCZJXSA-N
Standard InCHI	InChI=1S/C33H40N4O6/c38-28(29-21-43-29)17-9-3-8-15-24-30(39)35-25(19-22-11-4-1-5-12-22)31(40)36-26(20-23-13-6-2-7-14-23)33(42)37-18-10-16-27(37)32(41)34-24/h1-2,4-7,11-14,24-27,29H,3,8-10,15-21H2,(H,34,41)(H,35,39)(H,36,40)/t24-,25-,26-,27+,29-/m0/s1
SMILES	O=C1N[C@@H](Cc2ccccc2)C(=O)N2CCC[C@@H]2C(=O)N[C@@H](CCCCCC(=O)[C@@H]2CO2)C(=O)N[C@H]1Cc1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	588.29	Volume:	604.269 ? Van der Waals volume.
Dense:	0.974	LogP:	2.142 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.192 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.051 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	36.0
TPSA:	137.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.271	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.48	Fsp³:	0.485
MCE-18:	94.286 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.084	Fluc inhibitor:	0.029 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.773 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.192

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.481	MDCK Permeability:	-4.639
Pgp-inhibitor:	0.988	Pgp-substrate:	0.961
PAMPA:	0.348 ? 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):	0.803
20% Bioavailability (F20%):	0.957	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.41
Plasma Protein Binding (PPB):	92.48%	Volume Distribution (VD):	-0.562
Fu:	8.561% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.883
OATP1B3 inhibitor:	0.624	BCRP inhibitor:	0.711
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.411	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.877	CYP3A4-substrate:	0.132
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.017 ? 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):

3.22

Half-life (T1/2):

1.369

ADMET: Toxicity

hERG Blockers:	0.067	hERG Blockers (10um):	0.107
Human Hepatotoxicity (H-HT):	0.996	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.958	Rat Oral Acute Toxicity:	0.323
Maximum Recommended Daily Dose:	0.792	Skin Sensitization:	1.0
Carcinogencity:	0.237	Eye Corrosion:	0.0
Eye Irritation:	0.873	Respiratory Toxicity:	0.011
Drug-induced Neurotoxicity:	0.999	Ototoxicity:	0.178
Hematotoxicity:	0.516	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.671
A549 Cytotoxicity:	0.173	Hek293 Cytotoxicity:	0.302
BCF:	0.91 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.582 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.903 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.42 ? 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
NPO43645	Helicoma ambiens RF-1023	Genus	Tubeufiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
GI50	56
AC50	1

Activity Type	# Activity
Individual protein	4
Cell line	59
Protein family	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT684	Individual protein	Histone deacetylase 1	Homo sapiens	IC50	=	0.11	nM	PMID[19362838]
NPT5658	Individual protein	Histone deacetylase HD2	Zea mays	IC50	=	10.0	nM	PMID[15857140]
NPT5658	Individual protein	Histone deacetylase HD2	Zea mays	IC50	=	10.0	nM	PMID[11405644]
NPT5660	Individual protein	Histone deacetylase 1	Mus musculus	IC50	=	100.0	nM	PMID[15163181]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	2.089	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	0.4966	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	102.8	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	0.2118	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	0.5534	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	50.0	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	0.2118	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	0.52	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	47.53	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	0.6855	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	2.0	nM	PMID[11831887]
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	1.253	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	2.698	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	0.7129	nM	PubChem BioAssay data set
NPT2410	Cell line	NCI-H1299	Homo sapiens	IC50	=	4.0	nM	PMID[14521422]
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	221.82	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	161.44	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	0.2118	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	0.778	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	2.944	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	1.222	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	0.7345	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	2.0	nM	PMID[14521422]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	1.164	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	0.2564	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	5.741	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	0.2118	nM	PubChem BioAssay data set
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	10.38	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	1.242	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	0.2118	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	1.361	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	517.61	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	2.089	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	3.664	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	0.4721	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	43.15	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	3.681	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	0.5458	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	3.396	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	2.655	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	220.8	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	11.91	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	0.3319	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	0.4355	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	0.597	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	34.28	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	11.04	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	15.14	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	18.97	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	14.52	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	389.05	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	1.972	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	5.408	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	0.3048	nM	PubChem BioAssay data set
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	0.5117	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	1.57	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	0.2118	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	63.24	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	17.46	nM	PubChem BioAssay data set
NPT30138	Protein family	Histone deacetylase	Homo sapiens	AC50	=	10.0	nM	PMID[11831887]
NPT30138	Protein family	Histone deacetylase	Homo sapiens	IC50	=	4.0	nM	PMID[11831887]
NPT30138	Protein family	Histone deacetylase	Homo sapiens	IC50	<	5.0	nM	PMID[11831887]
NPT30138	Protein family	Histone deacetylase	Homo sapiens	IC50	<	5.0	nM	PMID[14521422]

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 NPC602763 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	23884
0.1-0.2	24701
0.2-0.3	1061
0.3-0.4	162
0.4-0.5	34
0.5-0.6	6
0.6-0.7	8
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
0.6757	Remote Similarity	NPC608835
0.6184	Remote Similarity	NPC604706
0.6125	Remote Similarity	NPC610311
0.6076	Remote Similarity	NPC611487
0.6049	Remote Similarity	NPC601881
0.6026	Remote Similarity	NPC600414
0.6	Remote Similarity	NPC603333
0.6	Remote Similarity	NPC604183
0.5867	Remote Similarity	NPC610520
0.5833	Remote Similarity	NPC606808
0.5714	Remote Similarity	NPC604624
0.5529	Remote Similarity	NPC606807
0.5465	Remote Similarity	NPC602956
0.5114	Remote Similarity	NPC607800

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC602763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3475
0.1-0.2	5495
0.2-0.3	176
0.3-0.4	4
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