NPASS Compound

Natural Product: NPC477522

Natural Product ID	NPC477522
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3S,8S,9S,10R,13S,14S,16R,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol
IUPAC Name	(3S,8S,9S,10R,13S,14S,16R,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	122177416
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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 76 79 0 0 0 0 0 0 0 0999 V2000 -2.5134 0.1149 1.6781 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4463 0.2270 0.1755 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6482 -0.5837 -0.3432 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9330 -0.0252 0.1767 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0535 -0.8465 -0.3550 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8824 -1.8927 -1.1490 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4237 -0.4452 0.0449 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6390 -0.5326 1.5400 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6451 0.9749 -0.4471 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2313 -0.4224 -0.4228 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3129 -0.2180 -1.9269 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0759 0.2979 -2.3337 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9130 -0.1885 -1.2395 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0763 0.1248 0.0129 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7423 -0.5942 1.1376 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0479 -1.2210 0.8583 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9499 -0.5526 -0.1064 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2162 0.4606 -1.0026 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0952 0.6576 -2.1896 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3933 1.1674 -1.6895 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8901 0.8767 -0.5215 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2148 0.0017 0.4435 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2140 -1.1501 0.7058 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5394 -0.6167 1.1727 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1439 0.3688 0.2071 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2005 1.4753 -0.1692 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2538 0.9535 0.8258 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0439 0.6529 1.7997 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0658 1.6080 0.2625 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5215 -1.4618 -2.5172 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2547 0.9010 2.0092 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9331 -0.8530 1.9781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5537 0.2779 2.1849 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6255 1.2584 -0.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4716 -1.6276 -0.0394 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6366 -0.5538 -1.4519 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9279 -0.0012 1.2864 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 1.0028 -0.2418 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8740 -2.1665 -1.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7322 -2.4423 -1.4976 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2024 -1.0723 -0.4393 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3821 -1.5346 1.8871 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7172 -0.3649 1.7280 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9892 0.1869 2.0843 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1184 1.7241 0.1527 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7225 1.2078 -0.4718 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2800 0.9955 -1.5091 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2750 -1.5005 -0.1583 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0898 0.5209 -2.2117 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3428 -0.2241 -3.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0785 1.3618 -2.5392 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9610 -1.2995 -1.2734 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0129 -1.3873 1.4830 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8324 0.0943 2.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6006 -1.3028 1.8422 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8590 -2.3082 0.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2572 -1.3403 -0.8640 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1694 1.3878 -0.3963 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5948 1.4117 -2.8588 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2428 -0.3063 -2.7225 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9201 1.8333 -2.4096 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8128 -1.7902 1.5179 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3118 -1.7423 -0.2028 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2298 -1.4848 1.2204 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4656 -0.2181 2.2055 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4847 -0.1679 -0.6957 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6600 1.9863 -1.0465 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1176 2.2591 0.6076 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8759 1.7028 1.3835 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0883 -0.1248 2.5712 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9267 1.3065 1.9564 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1535 1.2989 1.8564 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8089 1.8596 1.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9081 1.9877 0.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3185 2.2111 -0.6264 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2110 -2.1738 -1.8887 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 2 0 5 7 1 0 7 8 1 0 7 9 1 0 2 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 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 22 28 1 1 14 29 1 1 11 30 1 0 14 10 1 0 18 13 1 0 22 17 1 0 26 21 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 1 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 6 39 1 0 6 40 1 0 7 41 1 0 8 42 1 0 8 43 1 0 8 44 1 0 9 45 1 0 9 46 1 0 9 47 1 0 10 48 1 6 11 49 1 1 12 50 1 0 12 51 1 0 13 52 1 6 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 6 18 58 1 1 19 59 1 0 19 60 1 0 20 61 1 0 23 62 1 0 23 63 1 0 24 64 1 0 24 65 1 0 25 66 1 6 26 67 1 0 26 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 M END

Standard InCHIKey	VQIMWWKEEWJICR-LPUDQSKKSA-N
Standard InCHI	InChI=1S/C28H46O2/c1-17(2)18(3)7-8-19(4)26-25(30)16-24-22-10-9-20-15-21(29)11-13-27(20,5)23(22)12-14-28(24,26)6/h9,17,19,21-26,29-30H,3,7-8,10-16H2,1-2,4-6H3/t19-,21+,22-,23+,24+,25-,26+,27+,28+/m1/s1
SMILES	C[C@H](CCC(=C)C(C)C)[C@H]1[C@@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	414.35	Volume:	470.926 ? Van der Waals volume.
Dense:	0.88	LogP:	5.687 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.446 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.247 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.502	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.679	Fsp³:	0.857
MCE-18:	72.154 ? 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:	0.931	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? 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:	0.459	Promiscuous compounds:	0.058

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.238	MDCK Permeability:	-5.028
Pgp-inhibitor:	0.311	Pgp-substrate:	0.154
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%):	0.136	30% Bioavailability (F30%):	0.758
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051	MRP1:	0.837
Plasma Protein Binding (PPB):	93.689%	Volume Distribution (VD):	0.012
Fu:	8.924% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.951
BSEP inhibitor:	0.792

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.009
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.903	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.805 ? 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):

12.716

Half-life (T1/2):

0.96

ADMET: Toxicity

hERG Blockers:	0.09	hERG Blockers (10um):	0.382
Human Hepatotoxicity (H-HT):	0.533	Drug-induced Liver Injury (DILI):	0.114
AMES Toxicity:	0.186	Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.636	Skin Sensitization:	0.969
Carcinogencity:	0.786	Eye Corrosion:	0.191
Eye Irritation:	0.879	Respiratory Toxicity:	0.726
Drug-induced Neurotoxicity:	0.093	Ototoxicity:	0.571
Hematotoxicity:	0.315	Drug-induced Nephrotoxicity:	0.477
Genotoxicity:	0.043	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.311	Hek293 Cytotoxicity:	0.368
BCF:	2.146 ? 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:	3.99 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.159 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.714 ? 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
NPO32454	monanchora sp.	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640525]
NPO32454	monanchora sp.	Species	Crambeidae	Eukaryota	n.a.	Korean	n.a.	PMID[23360104]
NPO32454	monanchora sp.	Species	Crambeidae	Eukaryota	n.a.	at 1520 m depth off the shore of Gageo Island, southwestern Korea	2009-JUL	PMID[25455409]

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
IC50	1

Activity Type	# Activity
Cell line	2

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
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	67	%	PMID[25455409]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	5200	nM	PMID[25455409]

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 NPC477522 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	27296
0.1-0.2	19970
0.2-0.3	2283
0.3-0.4	191
0.4-0.5	62
0.5-0.6	36
0.6-0.7	18
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
0.7857	Intermediate Similarity	NPC19607
0.7778	Intermediate Similarity	NPC134847
0.6949	Remote Similarity	NPC26117
0.678	Remote Similarity	NPC1272
0.678	Remote Similarity	NPC470614
0.6406	Remote Similarity	NPC176012
0.6379	Remote Similarity	NPC328313
0.6316	Remote Similarity	NPC162742
0.6316	Remote Similarity	NPC304309
0.6316	Remote Similarity	NPC470228
0.6207	Remote Similarity	NPC22105
0.6207	Remote Similarity	NPC34019
0.6207	Remote Similarity	NPC107059
0.6102	Remote Similarity	NPC136188
0.6102	Remote Similarity	NPC28657
0.6102	Remote Similarity	NPC474216
0.6066	Remote Similarity	NPC87604
0.6	Remote Similarity	NPC230301
0.6	Remote Similarity	NPC198968
0.6	Remote Similarity	NPC285893
0.5968	Remote Similarity	NPC472265
0.5932	Remote Similarity	NPC600590
0.5902	Remote Similarity	NPC241290
0.5902	Remote Similarity	NPC164840
0.5902	Remote Similarity	NPC484739
0.5902	Remote Similarity	NPC209944
0.5902	Remote Similarity	NPC264245
0.5902	Remote Similarity	NPC155986
0.5833	Remote Similarity	NPC154330
0.5806	Remote Similarity	NPC321381
0.5738	Remote Similarity	NPC113733
0.5714	Remote Similarity	NPC59453
0.5692	Remote Similarity	NPC47761
0.5667	Remote Similarity	NPC221758
0.5625	Remote Similarity	NPC603646
0.5614	Remote Similarity	NPC96319
0.5538	Remote Similarity	NPC473943
0.5538	Remote Similarity	NPC155011
0.5484	Remote Similarity	NPC84694
0.5484	Remote Similarity	NPC143182
0.5469	Remote Similarity	NPC33913
0.5455	Remote Similarity	NPC474164
0.5455	Remote Similarity	NPC488870
0.5397	Remote Similarity	NPC51014
0.5385	Remote Similarity	NPC124172
0.5323	Remote Similarity	NPC20688
0.5312	Remote Similarity	NPC328714
0.5303	Remote Similarity	NPC243985
0.5303	Remote Similarity	NPC280710
0.5303	Remote Similarity	NPC240650
0.5238	Remote Similarity	NPC76879
0.5231	Remote Similarity	NPC318495
0.5217	Remote Similarity	NPC601043
0.5217	Remote Similarity	NPC605412
0.5161	Remote Similarity	NPC151519
0.507	Remote Similarity	NPC91604

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477522 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8126
0.1-0.2	886
0.2-0.3	124
0.3-0.4	7
0.4-0.5	2
0.5-0.6	3
0.6-0.7	2
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
0.6102	Remote Similarity	NPD6942	Phase 4
0.6	Remote Similarity	NPD7339	Approved
0.5667	Remote Similarity	NPD4786	Phase 1
0.5614	Remote Similarity	NPD3701	Pre-clinical
0.5161	Remote Similarity	NPD3667	Phase 4

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