NPASS Compound

Natural Product: NPC163003

Natural Product ID	NPC163003
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3Ar,6E,10E,14E,15As)-6,10,14-Trimethyl-3-Methylidene-3A,4,5,8,9,12,13,15A-Octahydrocyclotetradeca[B]Furan-2-One
IUPAC Name	(3aR,6E,10E,14E,15aS)-6,10,14-trimethyl-3-methylidene-3a,4,5,8,9,12,13,15a-octahydrocyclotetradeca[b]furan-2-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL485274
PubChem CID	10040485
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones [CHEMONTID:0002502] Cembranolides

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 50 51 0 0 0 0 0 0 0 0999 V2000 -0.8044 -3.4784 -0.7562 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1915 -2.4663 0.1440 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8889 -1.9861 1.1482 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3037 -2.4096 1.4182 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1721 -1.1569 1.4716 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9714 -0.2947 0.2835 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5877 0.9949 0.4213 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3630 1.9230 -0.6997 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3220 2.9418 -0.5433 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0795 2.6409 -0.3706 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7335 1.4816 -0.3510 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1757 1.3868 -0.1535 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6130 -0.1205 -0.2497 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7198 -0.9090 0.6268 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1392 -1.9875 -0.2308 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0127 0.0818 0.0727 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8849 -0.5721 0.8043 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3236 1.3388 -0.6803 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4770 1.7644 -0.8945 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0690 1.8990 -1.0701 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9358 3.9139 -0.1776 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1902 -0.7511 -1.1004 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3860 -4.2514 -0.2058 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4943 -2.9967 -1.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0298 -3.9636 -1.4094 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4912 -1.2664 1.8488 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4025 -2.9708 2.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7377 -3.0184 0.6031 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0698 -0.6217 2.4140 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2311 -1.5413 1.4441 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4344 1.3727 1.4297 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0819 1.2580 -1.5815 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3487 2.3704 -1.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6134 3.5438 0.4051 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4661 3.7819 -1.3285 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1723 0.5362 -0.4930 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5048 1.7409 0.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5367 -0.3553 -1.3323 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9782 -0.2821 1.1653 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3133 -1.4206 1.4384 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8475 -2.8548 -0.2196 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0905 -1.6770 -1.3002 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6199 -1.4653 1.3250 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8881 -0.1995 0.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9117 3.6298 0.2084 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0269 4.3154 -1.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3902 4.6463 0.4223 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2424 -0.7488 -1.6350 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9257 -0.0416 -1.5800 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6937 -1.7551 -1.1000 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 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 13 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 18 20 1 0 10 21 1 0 6 22 1 0 15 2 1 0 20 12 1 0 1 23 1 0 1 24 1 0 1 25 1 0 3 26 1 0 4 27 1 0 4 28 1 0 5 29 1 0 5 30 1 0 7 31 1 0 8 32 1 0 8 33 1 0 9 34 1 0 9 35 1 0 11 36 1 0 12 37 1 1 13 38 1 6 14 39 1 0 14 40 1 0 15 41 1 0 15 42 1 0 17 43 1 0 17 44 1 0 21 45 1 0 21 46 1 0 21 47 1 0 22 48 1 0 22 49 1 0 22 50 1 0 M END

Standard InCHIKey	RCAHBKAGTYTMES-ZEMHAMIXSA-N
Standard InCHI	InChI=1S/C20H28O2/c1-14-7-5-9-15(2)11-12-18-17(4)20(21)22-19(18)13-16(3)10-6-8-14/h8-9,13,18-19H,4-7,10-12H2,1-3H3/b14-8+,15-9+,16-13+/t18-,19+/m1/s1
SMILES	C/C/1=CCC/C(=C/CC/C(=C/[C@H]2[C@H](CC1)C(=C)C(=O)O2)/C)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	300.21	Volume:	341.761 ? Van der Waals volume.
Dense:	0.878	LogP:	3.766 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.425 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.926 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	20.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	2.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.346	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.316	Fsp³:	0.55
MCE-18:	32.71 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.694	Fluc inhibitor:	0.743 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.061 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.944	Promiscuous compounds:	0.146

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.762	MDCK Permeability:	-4.709
Pgp-inhibitor:	0.999	Pgp-substrate:	0.001
PAMPA:	0.002 ? 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):	0.013
20% Bioavailability (F20%):	0.038	30% Bioavailability (F30%):	0.647
50% Bioavailability (F50%):	0.645

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.847
Plasma Protein Binding (PPB):	95.379%	Volume Distribution (VD):	0.26
Fu:	5.141% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.001
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.011	CYP1A2-substrate:	0.482
CYP2C19-inhibitor:	0.913	CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.882	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.4	CYP2D6-substrate:	0.354
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.972
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.985
HLM stability:	0.871 ? 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):

11.595

Half-life (T1/2):

1.692

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.079
Human Hepatotoxicity (H-HT):	0.495	Drug-induced Liver Injury (DILI):	0.944
AMES Toxicity:	0.07	Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.33	Skin Sensitization:	0.894
Carcinogencity:	0.181	Eye Corrosion:	0.379
Eye Irritation:	0.982	Respiratory Toxicity:	0.06
Drug-induced Neurotoxicity:	0.764	Ototoxicity:	0.16
Hematotoxicity:	0.225	Drug-induced Nephrotoxicity:	0.532
Genotoxicity:	0.006	RPMI-8226 Immunitoxicity:	0.064
A549 Cytotoxicity:	0.093	Hek293 Cytotoxicity:	0.216
BCF:	2.67 ? 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:	4.777 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.343 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.292 ? 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
NPO15672	Clavularia koellikeri	Species	Clavulariidae	Eukaryota	n.a.	Okinawan soft coral	n.a.	PMID[11141107]
NPO15672	Clavularia koellikeri	Species	Clavulariidae	Eukaryota	n.a.	Okinawan soft coral	n.a.	PMID[12398540]
NPO15672	Clavularia koellikeri	Species	Clavulariidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[15104486]
NPO15672	Clavularia koellikeri	Species	Clavulariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30994348]
NPO15672	Clavularia koellikeri	Species	Clavulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15672	Clavularia koellikeri	Species	Clavulariidae	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	39

Activity Type	# Activity
Cell line	34
Non-molecular	5

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	0.9	ug.mL-1	PMID[23013356]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	4.5	ug.mL-1	PMID[23013356]
NPT370	Cell line	NCI-H23	Homo sapiens	IC50	=	3.6	ug.mL-1	PMID[17328523]
NPT405	Cell line	NCI-H226	Homo sapiens	IC50	=	1.14	ug.mL-1	PMID[23013356]
NPT455	Cell line	NCI-H522	Homo sapiens	IC50	=	0.66	ug.mL-1	PMID[23013356]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	3.3	ug.mL-1	PMID[23013356]
NPT81	Cell line	A549	Homo sapiens	IC50	=	1.26	ug.mL-1	PMID[25419616]
NPT572	Cell line	DMS-273	Homo sapiens	IC50	=	1.11	ug.mL-1	PMID[7901341]
NPT576	Cell line	DMS-114	Homo sapiens	IC50	=	3.6	ug.mL-1	PMID[22568524]
NPT390	Cell line	LOX IMVI	Homo sapiens	IC50	=	0.72	ug.mL-1	PMID[15974580]
NPT2722	Cell line	St-4	Homo sapiens	IC50	=	3.9	ug.mL-1	PMID[19805556]
NPT2398	Cell line	MKN-7	Homo sapiens	IC50	=	0.96	ug.mL-1	PMID[17850057]
NPT1179	Cell line	MKN-28	Homo sapiens	IC50	=	0.96	ug.mL-1	PMID[17850057]
NPT1097	Cell line	MKN-45	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[22014228]
NPT2723	Cell line	MKN-74	Homo sapiens	IC50	=	0.81	ug.mL-1	PMID[22014228]
NPT391	Cell line	HCC 2998	Homo sapiens	IC50	=	1.29	ug.mL-1	PMID[20815366]
NPT386	Cell line	KM12	Homo sapiens	IC50	=	1.32	ug.mL-1	PMID[22364815]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	1.47	ug.mL-1	PMID[20815366]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	2.01	ug.mL-1	PMID[20815366]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	1.17	ug.mL-1	PMID[12027739]
NPT369	Cell line	ACHN	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[10346943]
NPT377	Cell line	OVCAR-3	Homo sapiens	IC50	=	1.14	ug.mL-1	PMID[12027739]
NPT456	Cell line	OVCAR-4	Homo sapiens	IC50	=	2.25	ug.mL-1	PMID[22037378]
NPT382	Cell line	OVCAR-5	Homo sapiens	IC50	=	2.31	ug.mL-1	PMID[20815366]
NPT381	Cell line	OVCAR-8	Homo sapiens	IC50	=	0.93	ug.mL-1	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	6.6	ug.mL-1	PMID[18646829]
NPT380	Cell line	U-251	Homo sapiens	IC50	=	4.2	ug.mL-1	PMID[18161942]
NPT395	Cell line	SF-268	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[19496609]
NPT399	Cell line	SF-295	Homo sapiens	IC50	=	3.9	ug.mL-1	PMID[19689125]
NPT374	Cell line	SF-539	Homo sapiens	IC50	=	1.56	ug.mL-1	PMID[23376010]
NPT392	Cell line	SNB-75	Homo sapiens	IC50	=	3.3	ug.mL-1	PMID[23327668]
NPT578	Cell line	SNB-78	Homo sapiens	IC50	=	1.59	ug.mL-1	PMID[23327668]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	3.3	ug.mL-1	PMID[18289862]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	1.11	ug.mL-1	PMID[23327668]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1.62	ug.mL-1	PMID[12398540]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1.35	ug.mL-1	PMID[12398540]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	2.13	ug.mL-1	PMID[12398540]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1.2	ug.mL-1	PMID[12398540]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	4.8	ug.mL-1	PMID[12398540]

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 NPC163003 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	20432
0.1-0.2	25282
0.2-0.3	3456
0.3-0.4	559
0.4-0.5	73
0.5-0.6	27
0.6-0.7	18
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC58956
1.0	High Similarity	NPC295633
1.0	High Similarity	NPC269206
0.8333	Intermediate Similarity	NPC476355
0.814	Intermediate Similarity	NPC7563
0.7174	Intermediate Similarity	NPC123360
0.6977	Remote Similarity	NPC140287
0.6939	Remote Similarity	NPC93763
0.68	Remote Similarity	NPC108816
0.6739	Remote Similarity	NPC470256
0.6667	Remote Similarity	NPC601805
0.6531	Remote Similarity	NPC267231
0.6531	Remote Similarity	NPC250315
0.6512	Remote Similarity	NPC235906
0.6458	Remote Similarity	NPC194871
0.6444	Remote Similarity	NPC196653
0.6444	Remote Similarity	NPC603669
0.6304	Remote Similarity	NPC471465
0.6222	Remote Similarity	NPC171204
0.6222	Remote Similarity	NPC606745
0.6087	Remote Similarity	NPC611318
0.6078	Remote Similarity	NPC20713
0.6	Remote Similarity	NPC167881
0.6	Remote Similarity	NPC98557
0.5909	Remote Similarity	NPC129665
0.5833	Remote Similarity	NPC480697
0.551	Remote Similarity	NPC38468
0.551	Remote Similarity	NPC192678
0.551	Remote Similarity	NPC319795
0.551	Remote Similarity	NPC50362
0.551	Remote Similarity	NPC488056
0.551	Remote Similarity	NPC605079
0.5435	Remote Similarity	NPC65603
0.5349	Remote Similarity	NPC606552
0.5333	Remote Similarity	NPC306041
0.5306	Remote Similarity	NPC229825
0.5306	Remote Similarity	NPC473715
0.5306	Remote Similarity	NPC474760
0.5306	Remote Similarity	NPC59097
0.5306	Remote Similarity	NPC602858
0.5294	Remote Similarity	NPC165383
0.5283	Remote Similarity	NPC173609
0.5208	Remote Similarity	NPC155587
0.5208	Remote Similarity	NPC329852
0.5185	Remote Similarity	NPC470755
0.5185	Remote Similarity	NPC298801
0.5094	Remote Similarity	NPC481909
0.5094	Remote Similarity	NPC488117
0.5094	Remote Similarity	NPC473619
0.5094	Remote Similarity	NPC178702
0.5091	Remote Similarity	NPC284902

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC163003 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6977
0.1-0.2	2115
0.2-0.3	51
0.3-0.4	6
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
0.551	Remote Similarity	NPD1733	Clinical (unspecified phase)

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