NPASS Compound

Natural Product: NPC33913

Natural Product ID	NPC33913
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VMXMLOFNEQBYHM-INVHITAPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3356400
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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 71 74 0 0 0 0 0 0 0 0999 V2000 -5.9641 -0.7921 -1.6509 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8507 0.0495 -0.7853 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9882 -0.6260 0.5474 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3517 1.4467 -0.6587 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0503 2.4199 -1.0561 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0531 1.7609 -0.0794 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2209 0.8390 0.3790 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8829 1.1598 0.9758 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9612 0.8863 2.4374 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8574 0.5050 0.1885 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9520 1.0420 -1.2495 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5004 1.2835 -1.6763 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2106 0.3295 -0.8070 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6671 0.3234 -0.8170 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1216 -0.1497 -2.1859 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6054 -0.0854 -2.1935 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3019 -0.3605 -1.1218 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7801 -0.2849 -1.1714 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3666 -1.5789 -0.6537 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6823 -2.1090 0.5568 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1739 -2.1681 0.4342 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6618 -0.7461 0.1424 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2003 0.1737 1.2510 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1758 -0.7306 0.1559 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5950 -0.3917 1.5111 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0926 -0.5151 1.4100 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 0.6148 0.5608 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0256 1.9635 0.9843 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6969 -1.2972 -0.2993 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1211 -0.1719 -2.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5323 -1.1041 -2.5489 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6330 -1.7379 -1.1678 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8529 0.1025 -1.2523 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6751 0.0416 1.3967 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0569 -0.8428 0.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4673 -1.6094 0.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7280 2.7738 -0.0072 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5521 -0.1909 0.3059 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7932 2.2783 0.8734 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0173 0.9886 2.9850 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6770 1.5833 2.9497 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3467 -0.1297 2.6714 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0849 -0.5997 0.0848 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5263 1.9834 -1.2914 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3724 0.3225 -1.9467 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3662 1.0135 -2.7576 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2166 2.3320 -1.5746 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1544 -0.7033 -1.0641 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1914 1.2430 -0.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7433 0.5916 -2.9145 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7512 -1.1787 -2.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1158 0.2041 -3.1378 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1828 0.6018 -0.6550 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1252 -0.1984 -2.2361 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3416 -2.3155 -1.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0130 -3.1824 0.6725 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0023 -1.6178 1.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7798 -2.5609 1.3723 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9456 -2.7801 -0.4586 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0050 -0.2752 2.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2902 0.2728 1.1560 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7618 1.1691 1.1110 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7567 -1.7373 -0.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9197 -1.1462 2.2777 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9451 0.5867 1.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4001 -0.6609 2.3582 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0908 -1.4560 0.8092 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8100 2.7247 0.9515 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8190 2.4096 0.3473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4624 1.9726 2.0261 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0324 -1.9586 0.3793 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 8 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 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 19 29 1 0 27 10 1 0 27 13 1 0 24 14 1 0 22 17 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 0 3 34 1 0 3 35 1 0 3 36 1 0 6 37 1 0 7 38 1 0 8 39 1 1 9 40 1 0 9 41 1 0 9 42 1 0 10 43 1 6 11 44 1 0 11 45 1 0 12 46 1 0 12 47 1 0 13 48 1 6 14 49 1 1 15 50 1 0 15 51 1 0 16 52 1 0 18 53 1 0 18 54 1 0 19 55 1 6 20 56 1 0 20 57 1 0 21 58 1 0 21 59 1 0 23 60 1 0 23 61 1 0 23 62 1 0 24 63 1 6 25 64 1 0 25 65 1 0 26 66 1 0 26 67 1 0 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 M END

Standard InCHIKey	VMXMLOFNEQBYHM-INVHITAPSA-N
Standard InCHI	InChI=1S/C27H42O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h6-7,11,17-18,20-24,28H,8-10,12-16H2,1-5H3/b11-6+/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
SMILES	CC(C)C(=O)/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	398.32	Volume:	450.993 ? Van der Waals volume.
Dense:	0.883	LogP:	5.86 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.53 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.358 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	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:	0.443	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.483	Fsp³:	0.815
MCE-18:	70.531 ? 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:	0.966	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.524	Promiscuous compounds:	0.096

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.264	MDCK Permeability:	-4.914
Pgp-inhibitor:	0.743	Pgp-substrate:	0.007
PAMPA:	0.006 ? 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%):	0.133	30% Bioavailability (F30%):	0.892
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.089
Plasma Protein Binding (PPB):	96.771%	Volume Distribution (VD):	-0.062
Fu:	3.449% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.585
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.606
CYP2D6-inhibitor:	0.009	CYP2D6-substrate:	0.216
CYP3A4-inhibitor:	0.953	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.186 ? 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):

14.241

Half-life (T1/2):

0.708

ADMET: Toxicity

hERG Blockers:	0.248	hERG Blockers (10um):	0.273
Human Hepatotoxicity (H-HT):	0.674	Drug-induced Liver Injury (DILI):	0.386
AMES Toxicity:	0.106	Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.696	Skin Sensitization:	0.927
Carcinogencity:	0.802	Eye Corrosion:	0.13
Eye Irritation:	0.936	Respiratory Toxicity:	0.876
Drug-induced Neurotoxicity:	0.08	Ototoxicity:	0.564
Hematotoxicity:	0.383	Drug-induced Nephrotoxicity:	0.57
Genotoxicity:	0.064	RPMI-8226 Immunitoxicity:	0.067
A549 Cytotoxicity:	0.249	Hek293 Cytotoxicity:	0.799
BCF:	2.21 ? 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:	4.177 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.358 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.931 ? 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	%	Open TG-GATES in vivo data: Hematology
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	49970.0	nM	PMID[26331426]
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[1967654]
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	=	15.98	%	PMID[25497963]
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	DOI[10.6019/CHEMBL1201861]
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 NPC33913 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	16141
0.1-0.2	27286
0.2-0.3	5970
0.3-0.4	314
0.4-0.5	81
0.5-0.6	18
0.6-0.7	38
0.7-0.8	1
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
0.75	Intermediate Similarity	NPC59453
0.7407	Intermediate Similarity	NPC154330
0.7273	Intermediate Similarity	NPC113733
0.7222	Intermediate Similarity	NPC221758
0.6897	Remote Similarity	NPC472265
0.6842	Remote Similarity	NPC51014
0.6727	Remote Similarity	NPC162742
0.6727	Remote Similarity	NPC304309
0.6727	Remote Similarity	NPC470228
0.6667	Remote Similarity	NPC243985
0.6667	Remote Similarity	NPC280710
0.6667	Remote Similarity	NPC240650
0.6607	Remote Similarity	NPC22105
0.6607	Remote Similarity	NPC34019
0.6607	Remote Similarity	NPC107059
0.6607	Remote Similarity	NPC600590
0.6491	Remote Similarity	NPC136188
0.6491	Remote Similarity	NPC28657
0.6491	Remote Similarity	NPC474216
0.6491	Remote Similarity	NPC328313
0.6379	Remote Similarity	NPC230301
0.6379	Remote Similarity	NPC198968
0.6379	Remote Similarity	NPC285893
0.6379	Remote Similarity	NPC134847
0.6333	Remote Similarity	NPC318495
0.6316	Remote Similarity	NPC151519
0.6271	Remote Similarity	NPC241290
0.6271	Remote Similarity	NPC164840
0.6271	Remote Similarity	NPC484739
0.6271	Remote Similarity	NPC209944
0.6271	Remote Similarity	NPC264245
0.6271	Remote Similarity	NPC155986
0.625	Remote Similarity	NPC601043
0.625	Remote Similarity	NPC605412
0.623	Remote Similarity	NPC603646
0.6167	Remote Similarity	NPC328714
0.6167	Remote Similarity	NPC321381
0.6129	Remote Similarity	NPC473943
0.6129	Remote Similarity	NPC155011
0.6102	Remote Similarity	NPC76879
0.6032	Remote Similarity	NPC47761
0.6032	Remote Similarity	NPC488870
0.5968	Remote Similarity	NPC58063
0.5932	Remote Similarity	NPC20688
0.5781	Remote Similarity	NPC474164
0.5714	Remote Similarity	NPC96319
0.5469	Remote Similarity	NPC477522
0.5312	Remote Similarity	NPC1272
0.5312	Remote Similarity	NPC470614
0.5156	Remote Similarity	NPC31564
0.5156	Remote Similarity	NPC145879
0.5156	Remote Similarity	NPC26959
0.5147	Remote Similarity	NPC474349
0.5147	Remote Similarity	NPC474189
0.5139	Remote Similarity	NPC147835
0.5139	Remote Similarity	NPC253645
0.5139	Remote Similarity	NPC85001
0.5139	Remote Similarity	NPC95920
0.5077	Remote Similarity	NPC474778
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 NPC33913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6153
0.1-0.2	2693
0.2-0.3	265
0.3-0.4	31
0.4-0.5	3
0.5-0.6	1
0.6-0.7	3
0.7-0.8	1
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
0.6491	Remote Similarity	NPD6942	Phase 4
0.6379	Remote Similarity	NPD7339	Approved
0.6316	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