NPASS Compound

Natural Product: NPC472265

Natural Product ID	NPC472265
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FVDBETHWYUBTJW-FONZPGPPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3356399
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

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 77 80 0 0 0 0 0 0 0 0999 V2000 -8.2007 0.4616 -0.8730 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1032 0.7175 -0.0460 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6151 -0.5028 0.6561 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1699 -0.3588 1.0836 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3522 -0.3855 -0.1896 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7736 0.8106 -0.9701 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9322 1.3228 -1.8604 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5950 0.7858 -2.1351 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0213 -0.0764 -1.0683 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9237 -0.1893 0.1719 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3284 -1.2812 0.9889 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9337 -0.9010 1.4729 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0204 -0.5736 0.3561 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7364 0.4172 -0.5515 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3394 0.6457 -1.5644 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5083 0.9482 -0.6023 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1922 0.2515 0.7019 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3378 -0.4745 1.2850 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5557 0.3103 1.6430 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2426 1.0298 0.5708 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4176 0.7186 0.0807 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0279 1.5251 -1.0139 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1557 1.2137 -1.4709 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2604 2.6812 -1.5233 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1567 -0.4599 0.5935 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5501 -0.0067 1.0062 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3479 -1.3655 -0.6377 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8569 -1.1833 2.5640 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4494 -1.7848 -0.4006 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0895 1.4806 -0.8169 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6412 -1.6560 -0.9185 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9681 -0.0216 -1.6841 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5106 1.4027 0.7561 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7538 -1.3718 -0.0426 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2631 -0.7400 1.5325 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9270 -1.1937 1.7688 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0637 0.6343 1.5603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2248 2.2113 -2.4513 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8791 1.6218 -2.3250 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6532 0.2525 -3.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9920 -1.1183 -1.4710 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8377 0.7566 0.7438 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9148 -1.4936 1.9163 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2849 -2.2535 0.4360 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5725 -1.8263 1.9904 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0613 -0.1033 2.2025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9028 1.3319 0.0422 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1405 1.5828 -2.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5393 -0.2259 -2.1852 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3847 0.5854 -1.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5812 2.0400 -0.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8157 1.0489 1.4051 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6847 -1.3354 0.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2029 1.1026 2.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2157 -0.3072 2.2839 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8059 1.9385 0.1102 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2945 2.3538 -1.9545 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1128 3.4245 -0.6992 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8873 3.1989 -2.2890 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6661 -1.0419 1.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3406 -0.4367 0.3763 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6356 1.0982 0.9392 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6923 -0.3279 2.0594 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3067 -1.0716 -1.0962 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5494 -1.1832 -1.3858 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3349 -2.4309 -0.3305 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7519 -1.1218 3.2720 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0856 -0.6009 3.0928 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6612 -2.2446 2.4167 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2848 -2.1603 -1.1395 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4144 -1.6051 -0.9167 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6129 -2.6121 0.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9227 2.5064 -0.3930 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4432 1.6797 -1.8722 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8066 -2.0469 -1.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9131 -2.4852 -0.2023 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4988 -1.5320 -1.6428 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 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 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 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 21 25 1 0 25 26 1 0 25 27 1 0 18 28 1 0 13 29 1 6 6 30 1 0 5 31 1 6 30 2 1 0 10 5 1 0 17 13 1 0 14 9 1 0 1 32 1 0 2 33 1 1 3 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 9 41 1 6 10 42 1 1 11 43 1 0 11 44 1 0 12 45 1 0 12 46 1 0 14 47 1 1 15 48 1 0 15 49 1 0 16 50 1 0 16 51 1 0 17 52 1 1 18 53 1 6 19 54 1 0 19 55 1 0 20 56 1 0 24 57 1 0 24 58 1 0 24 59 1 0 25 60 1 0 26 61 1 0 26 62 1 0 26 63 1 0 27 64 1 0 27 65 1 0 27 66 1 0 28 67 1 0 28 68 1 0 28 69 1 0 29 70 1 0 29 71 1 0 29 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 M END

Standard InCHIKey	FVDBETHWYUBTJW-FONZPGPPSA-N
Standard InCHI	InChI=1S/C29H46O2/c1-18(2)23(20(4)30)9-7-19(3)25-11-12-26-24-10-8-21-17-22(31)13-15-28(21,5)27(24)14-16-29(25,26)6/h8-9,18-19,22,24-27,31H,7,10-17H2,1-6H3/b23-9+/t19-,22+,24+,25-,26+,27+,28+,29-/m1/s1
SMILES	O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](C/C=C(/C(=O)C)C(C)C)C)C)C1)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	426.35	Volume:	485.585 ? Van der Waals volume.
Dense:	0.878	LogP:	6.778 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.01 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.144 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.375	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.635	Fsp³:	0.828
MCE-18:	71.849 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.966	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.546	Promiscuous compounds:	0.15

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.001	MDCK Permeability:	-4.834
Pgp-inhibitor:	0.102	Pgp-substrate:	0.085
PAMPA:	0.015 ? 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%):	0.002	30% Bioavailability (F30%):	0.052
50% Bioavailability (F50%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068	MRP1:	0.093
Plasma Protein Binding (PPB):	78.025%	Volume Distribution (VD):	0.022
Fu:	20.224% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.853
BSEP inhibitor:	0.556

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.044	CYP2C19-substrate:	0.024
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.923	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.909
HLM stability:	0.912 ? 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):

12.096

Half-life (T1/2):

0.514

ADMET: Toxicity

hERG Blockers:	0.099	hERG Blockers (10um):	0.254
Human Hepatotoxicity (H-HT):	0.753	Drug-induced Liver Injury (DILI):	0.588
AMES Toxicity:	0.16	Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.692	Skin Sensitization:	0.936
Carcinogencity:	0.913	Eye Corrosion:	0.093
Eye Irritation:	0.865	Respiratory Toxicity:	0.822
Drug-induced Neurotoxicity:	0.058	Ototoxicity:	0.542
Hematotoxicity:	0.445	Drug-induced Nephrotoxicity:	0.656
Genotoxicity:	0.109	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.293	Hek293 Cytotoxicity:	0.691
BCF:	2.666 ? 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:	4.475 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.467 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.202 ? 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
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23548547]
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25497963]
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22674	Caulerpa racemosa	Species	Caulerpaceae	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	5
IC50	3
Activity	1

Activity Type	# Activity
Individual protein	6
Cell line	2
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1210	Individual protein	T-cell protein-tyrosine phosphatase	Homo sapiens	Inhibition	<	50.0	%	PMID[12444694]
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	3800.0	nM	PMID[17850214]
NPT205	Individual protein	Protein-tyrosine phosphatase 1C	Homo sapiens	Inhibition	<	50.0	%	PMID[20547801]
NPT206	Individual protein	Protein-tyrosine phosphatase 2C	Homo sapiens	Inhibition	<	50.0	%	PMID[15497938]
NPT1870	Individual protein	Receptor-type tyrosine-protein phosphatase F (LAR)	Homo sapiens	Inhibition	<	50.0	%	PMID[11277766]
NPT911	Individual protein	Dual specificity phosphatase Cdc25B	Homo sapiens	Inhibition	<	50.0	%	PMID[25798528]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	11.31	%	PMID[25497963]
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[21146414]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[25497963]

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 NPC472265 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	17964
0.1-0.2	25334
0.2-0.3	6113
0.3-0.4	301
0.4-0.5	80
0.5-0.6	19
0.6-0.7	26
0.7-0.8	2
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
0.7547	Intermediate Similarity	NPC107059
0.75	Intermediate Similarity	NPC59453
0.7358	Intermediate Similarity	NPC162742
0.7358	Intermediate Similarity	NPC304309
0.7358	Intermediate Similarity	NPC470228
0.7273	Intermediate Similarity	NPC134847
0.7222	Intermediate Similarity	NPC22105
0.7222	Intermediate Similarity	NPC221758
0.7222	Intermediate Similarity	NPC34019
0.7143	Intermediate Similarity	NPC264245
0.7091	Intermediate Similarity	NPC136188
0.7091	Intermediate Similarity	NPC28657
0.7091	Intermediate Similarity	NPC474216
0.6964	Remote Similarity	NPC230301
0.6964	Remote Similarity	NPC198968
0.6964	Remote Similarity	NPC285893
0.6897	Remote Similarity	NPC33913
0.6842	Remote Similarity	NPC241290
0.6842	Remote Similarity	NPC164840
0.6842	Remote Similarity	NPC51014
0.6842	Remote Similarity	NPC484739
0.6842	Remote Similarity	NPC209944
0.6842	Remote Similarity	NPC155986
0.6833	Remote Similarity	NPC47761
0.678	Remote Similarity	NPC603646
0.6724	Remote Similarity	NPC321381
0.6667	Remote Similarity	NPC473943
0.6667	Remote Similarity	NPC155011
0.6607	Remote Similarity	NPC600590
0.6557	Remote Similarity	NPC488870
0.6491	Remote Similarity	NPC328313
0.6491	Remote Similarity	NPC154330
0.6393	Remote Similarity	NPC243985
0.6393	Remote Similarity	NPC280710
0.6393	Remote Similarity	NPC240650
0.6379	Remote Similarity	NPC113733
0.625	Remote Similarity	NPC601043
0.625	Remote Similarity	NPC605412
0.6034	Remote Similarity	NPC151519
0.5968	Remote Similarity	NPC477522
0.5932	Remote Similarity	NPC20688
0.5902	Remote Similarity	NPC328714
0.5833	Remote Similarity	NPC76879
0.5806	Remote Similarity	NPC318495
0.5781	Remote Similarity	NPC474164
0.5714	Remote Similarity	NPC96319
0.5645	Remote Similarity	NPC87604
0.5397	Remote Similarity	NPC31564
0.5397	Remote Similarity	NPC145879
0.5397	Remote Similarity	NPC26959
0.5312	Remote Similarity	NPC1272
0.5312	Remote Similarity	NPC470614
0.5294	Remote Similarity	NPC599942
0.5152	Remote Similarity	NPC268406
0.5147	Remote Similarity	NPC474970
0.5077	Remote Similarity	NPC474778
0.5077	Remote Similarity	NPC153987
0.5077	Remote Similarity	NPC474733

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6506
0.1-0.2	2390
0.2-0.3	217
0.3-0.4	29
0.4-0.5	3
0.5-0.6	1
0.6-0.7	2
0.7-0.8	2
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
0.7222	Intermediate Similarity	NPD4786	Phase 1
0.7091	Intermediate Similarity	NPD6942	Phase 4
0.6964	Remote Similarity	NPD7339	Approved
0.6034	Remote Similarity	NPD3667	Phase 4
0.5714	Remote Similarity	NPD3701	Pre-clinical

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