NPASS Compound

Natural Product: NPC243893

Natural Product ID	NPC243893
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dichapetalin A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL453157
PubChem CID	5469156
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 91 98 0 0 0 0 0 0 0 0999 V2000 -9.7989 -0.1913 0.9956 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3528 0.6139 -0.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0854 0.9803 -0.2322 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1501 0.5859 0.8458 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2860 -0.5623 0.3748 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9304 -0.3781 1.0003 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8222 -0.4131 -0.0353 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7687 -1.7046 -0.7631 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3136 -2.0493 -0.8690 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5610 -1.1531 0.0815 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8988 -1.1443 1.4809 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4831 -0.1146 0.5363 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9369 1.2642 0.4905 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6359 1.5609 0.4221 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2912 0.4199 0.3915 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7259 0.8021 0.1646 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9800 1.7392 -0.9568 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1508 1.5400 1.4477 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6229 1.6064 1.5539 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4553 0.7717 0.9889 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9370 0.8998 1.1397 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5959 0.6027 -0.1806 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0404 0.3999 -0.0754 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7438 0.0010 -1.1915 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1133 -0.2103 -1.1616 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7926 -0.0167 0.0150 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1207 0.3829 1.1532 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7555 0.5844 1.0883 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0461 -0.4473 -0.8695 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6770 -0.2488 -1.1716 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9718 -0.3558 0.1603 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5230 -1.6322 0.8151 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5113 -0.4806 0.1056 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0327 -1.2880 -1.0683 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6532 -1.8135 -0.6988 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2590 -0.6262 -0.4933 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6287 -0.1231 -1.8787 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7482 -2.5551 0.4563 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0773 0.9522 1.6336 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3617 1.4873 2.5463 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1731 1.6074 1.0771 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3468 0.9878 -1.2356 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7536 1.7339 -2.2337 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1240 -1.0602 1.1796 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7529 0.4827 1.8838 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8063 -0.5881 0.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7580 1.5626 -1.0736 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6782 0.3299 1.7857 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7066 -1.5182 0.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2590 -0.5085 -0.7332 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7440 -1.1317 1.7927 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0665 0.3861 -0.7673 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2312 -1.6274 -1.7805 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3257 -2.5265 -0.2580 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1240 -3.1007 -0.5468 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0096 -1.8887 -1.9260 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3129 -0.8250 2.3376 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6356 -1.9433 1.8058 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6490 2.0852 0.5111 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3319 2.6066 0.3928 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2918 -0.0064 1.4410 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1380 2.4690 -1.0157 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8722 2.3885 -0.7012 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2416 1.2791 -1.9177 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6497 1.1456 2.3313 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7855 2.5892 1.3134 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0308 2.4141 2.1500 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2366 0.2205 1.9466 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2295 1.9314 1.4413 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4397 1.5212 -0.8184 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2139 -0.1528 -2.1217 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6752 -0.5187 -2.0161 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8616 -0.1600 0.1207 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6264 0.5461 2.1028 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2120 0.8942 1.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6267 0.7780 -1.5927 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3636 -1.0185 -1.8846 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3303 -2.4478 0.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8916 -1.8455 1.7052 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5924 -1.5481 1.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1940 -1.0624 1.0244 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7444 -2.1246 -1.2316 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9586 -0.7375 -2.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2325 -2.3878 -1.5519 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7118 0.1544 -1.9308 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0833 0.7732 -2.1827 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3955 -0.8961 -2.6695 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4297 -2.0585 1.2504 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1798 1.5866 -0.7991 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7341 0.0443 -1.7024 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1126 1.4794 -3.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 10 9 1 6 10 11 1 0 12 11 1 1 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 22 29 1 0 29 30 1 0 30 31 1 0 31 32 1 1 31 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 6 35 38 1 0 6 39 1 0 39 40 2 0 39 41 1 0 2 42 1 0 42 43 1 0 41 4 1 0 12 7 1 0 36 15 1 0 36 10 1 0 12 10 1 0 33 16 1 0 31 20 1 0 28 23 1 0 1 44 1 0 1 45 1 0 1 46 1 0 3 47 1 0 4 48 1 1 5 49 1 0 5 50 1 0 6 51 1 1 7 52 1 6 8 53 1 0 8 54 1 0 9 55 1 0 9 56 1 0 11 57 1 0 11 58 1 0 13 59 1 0 14 60 1 0 15 61 1 1 17 62 1 0 17 63 1 0 17 64 1 0 18 65 1 0 18 66 1 0 19 67 1 0 21 68 1 0 21 69 1 0 22 70 1 6 24 71 1 0 25 72 1 0 26 73 1 0 27 74 1 0 28 75 1 0 30 76 1 0 30 77 1 0 32 78 1 0 32 79 1 0 32 80 1 0 33 81 1 1 34 82 1 0 34 83 1 0 35 84 1 6 37 85 1 0 37 86 1 0 37 87 1 0 38 88 1 0 42 89 1 0 42 90 1 0 43 91 1 0 M END

Standard InCHIKey	LRJFCTOUXFAGON-NNLSLSRSSA-N
Standard InCHI	InChI=1S/C38H48O5/c1-23(20-39)16-26-18-27(33(41)43-26)28-11-15-38-21-37(28,38)14-12-30-34(2)13-10-25-17-29(24-8-6-5-7-9-24)42-22-35(25,3)31(34)19-32(40)36(30,38)4/h5-10,12,14,16,26-32,39-40H,11,13,15,17-22H2,1-4H3/b23-16+/t26-,27-,28-,29-,30+,31+,32+,34+,35-,36-,37+,38+/m0/s1
SMILES	C/C(=C[C@H]1C[C@@H]([C@@H]2CC[C@@]34C[C@]24C=C[C@@H]2[C@@]4(C)CC=C5C[C@@H](c6ccccc6)OC[C@]5(C)[C@@H]4C[C@H]([C@@]32C)O)C(=O)O1)/CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	584.35	Volume:	622.848 ? Van der Waals volume.
Dense:	0.938	LogP:	3.276 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.392 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.971 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	40.0
TPSA:	75.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	8.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.304	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.831	Fsp³:	0.658
MCE-18:	181.746 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.906	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.046	Promiscuous compounds:	0.191

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.972	MDCK Permeability:	-4.669
Pgp-inhibitor:	0.65	Pgp-substrate:	0.904
PAMPA:	0.525 ? 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%):	0.769	30% Bioavailability (F30%):	0.971
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.517	MRP1:	0.973
Plasma Protein Binding (PPB):	96.406%	Volume Distribution (VD):	0.11
Fu:	2.804% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.932
OATP1B3 inhibitor:	0.114	BCRP inhibitor:	0.043
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.93	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.116	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.035	CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.807	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.072
HLM stability:	0.666 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

7.137

Half-life (T1/2):

0.998

ADMET: Toxicity

hERG Blockers:	0.047	hERG Blockers (10um):	0.113
Human Hepatotoxicity (H-HT):	0.937	Drug-induced Liver Injury (DILI):	0.712
AMES Toxicity:	0.595	Rat Oral Acute Toxicity:	0.506
Maximum Recommended Daily Dose:	0.924	Skin Sensitization:	0.987
Carcinogencity:	0.608	Eye Corrosion:	0.0
Eye Irritation:	0.398	Respiratory Toxicity:	0.438
Drug-induced Neurotoxicity:	0.883	Ototoxicity:	0.479
Hematotoxicity:	0.127	Drug-induced Nephrotoxicity:	0.973
Genotoxicity:	0.988	RPMI-8226 Immunitoxicity:	0.136
A549 Cytotoxicity:	0.49	Hek293 Cytotoxicity:	0.371
BCF:	1.02 ? 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:	3.548 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.985 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.379 ? 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
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	stem bark	Philippines	n.a.	PMID[16562829]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597894]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Inhibition	1
EC90	3
ED50	11
GI50	60
EC50	3
IZ	2
IC50	6
Ratio IC50	1
mortality	1

Activity Type	# Activity
Individual protein	1
Cell line	82
Organism	3
Non-molecular	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	28.6	%	PMID[10757718]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell line	L1210	Mus musculus	EC90	<	0.0001	ug ml-1	PMID[14640532]
NPT1034	Cell line	Lu1	Homo sapiens	ED50	=	4.1	ug ml-1	PMID[24370010]
NPT1851	Cell line	Col2	Homo sapiens	ED50	=	6.1	ug ml-1	PMID[17970596]
NPT91	Cell line	KB	Homo sapiens	ED50	=	3.6	ug ml-1	PMID[20384296]
NPT91	Cell line	KB	Homo sapiens	ED50	=	11.6	ug ml-1	PMID[21155593]
NPT91	Cell line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[21155593]
NPT858	Cell line	LNCaP	Homo sapiens	ED50	=	7.0	ug ml-1	PMID[21155593]
NPT2345	Cell line	SW626	Homo sapiens	ED50	=	0.2	ug ml-1	PMID[20346682]
NPT136	Cell line	SK-N-SH	Homo sapiens	ED50	=	6.9	ug ml-1	PMID[21155593]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[21155593]
NPT737	Cell line	HUVEC	Homo sapiens	ED50	=	5.5	ug ml-1	PMID[21182258]
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	1914.26	nM	PMID[11277757]
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	1710.02	nM	PMID[24941130]
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	3334.26	nM	PMID[20524638]
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	1185.77	nM	DrugMatrix in vivo data: Pathology
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	2483.13	nM	PMID[18163588]
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	1196.74	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	1954.34	nM	Open TG-GATES in vivo data: Biochemistry
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	10209.39	nM	PMID[22209731]
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	5081.59	nM	PMID[24531199]
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	285.76	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	3564.51	nM	PMID[15808482]
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	436.52	nM	PMID[17524651]
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	553.35	nM	DOI[10.6019/CHEMBL3392926]
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	3515.6	nM	PMID[19581457]
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	1588.55	nM	DrugMatrix in vitro pharmacology data
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	3076.1	nM	PMID[24957203]
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	10185.91	nM	PMID[6292419]
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	1037.53	nM	PMID[19651906]
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	9817.48	nM	PMID[17524651]
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	4909.08	nM	PMID[18183025]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	5345.64	nM	PMID[19480409]
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	11803.21	nM	PMID[12488537]
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	10.0	nM	PMID[18183025]
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	2837.92	nM	PMID[22934671]
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	2716.44	nM	PMID[21625478]
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	2884.03	nM	PMID[16989518]
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	2449.06	nM	PMID[22168134]
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	2773.32	nM	PMID[18299417]
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	8279.42	nM	PMID[4851320]
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	623.73	nM	PMID[12762798]
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	3033.89	nM	PMID[21044847]
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	1517.05	nM	DrugMatrix in vivo data: Pathology
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	3775.72	nM	PMID[25442304]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	31405.09	nM	PMID[18341287]
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	5997.91	nM	PMID[18519719]
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	2786.12	nM	PMID[7807120]
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	3548.13	nM	PMID[18052029]
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	4375.22	nM	PMID[211235]
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	1142.88	nM	PMID[18183025]
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	6745.28	nM	DOI[10.6019/CHEMBL1201861]
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	2642.41	nM	PMID[12852754]
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	1506.61	nM	DrugMatrix in vitro pharmacology data
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	1782.38	nM	PMID[18458131]
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	36812.9	nM	PMID[18308563]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	721.11	nM	PMID[21872367]
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	2837.92	nM	PMID[20159656]
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	9015.71	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	2477.42	nM	PMID[20439614]
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	2084.49	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	2917.43	nM	PMID[15497961]
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	1342.76	nM	PMID[18715034]
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	4375.22	nM	PMID[18183025]
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	10864.26	nM	PMID[27177826]
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	1958.84	nM	PMID[15026054]
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	1037.53	nM	PMID[9461667]
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	14927.94	nM	PMID[21183354]
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	3741.11	nM	PMID[22951040]
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	2009.09	nM	PMID[25988923]
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	77803.66	nM	PMID[21146414]
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	2009.09	nM	PMID[21980963]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	20.0	nM	PMID[10757718]
NPT113	Cell line	RAW264.7	Mus musculus	Ratio IC50	=	20.0	n.a.	PMID[20515042]
NPT2345	Cell line	SW626	Homo sapiens	IC50	=	340.0	nM	PMID[33289552]
NPT137	Cell line	L1210	Mus musculus	EC90	<	0.17	nM	PMID[33289552]
NPT393	Cell line	HCT-116	Homo sapiens	EC50	=	250.0	nM	PMID[33289552]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	11000.0	nM	PMID[33289552]
NPT15	Cell line	Jurkat	Homo sapiens	IC50	=	3000.0	nM	PMID[33289552]
NPT404	Cell line	CCRF-CEM	Homo sapiens	IC50	=	9600.0	nM	PMID[33289552]
NPT858	Cell line	LNCaP	Homo sapiens	IC50	=	12000.0	nM	PMID[33289552]
NPT2779	Organism	Spodoptera exigua	Spodoptera exigua	EC50	=	3.1	microg/cm2	PMID[23046382]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	IZ	=	10.5	mm	PMID[23395661]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[16562829]
NPT610	Others	Molecular identity unknown	n.a.	IZ	=	12.8	mm	PMID[24597894]
NPT23813	Cell line	WM 266-4	Homo sapiens	EC50	=	17000.0	nM	PMID[33289552]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1272	Organism	Panagrellus redivivus	Panagrellus redivivus	mortality	=	15.3	%	PMID[24597894]

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 NPC243893 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	11488
0.1-0.2	35095
0.2-0.3	3236
0.3-0.4	8
0.4-0.5	17
0.5-0.6	6
0.6-0.7	2
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8764	High Similarity	NPC253591
0.8111	Intermediate Similarity	NPC262324
0.8	Intermediate Similarity	NPC79921
0.7826	Intermediate Similarity	NPC601361
0.7128	Intermediate Similarity	NPC471864
0.701	Intermediate Similarity	NPC261659
0.6809	Remote Similarity	NPC608970
0.6442	Remote Similarity	NPC600616
0.5948	Remote Similarity	NPC471861
0.5701	Remote Similarity	NPC471862
0.5392	Remote Similarity	NPC603083
0.5392	Remote Similarity	NPC606879
0.5192	Remote Similarity	NPC602510
0.5043	Remote Similarity	NPC471856

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC243893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3820
0.1-0.2	5271
0.2-0.3	59
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data