NPASS Compound

Natural Product: NPC246445

Natural Product ID	NPC246445
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3,4-Seco-Lupan-20(30)-Ene-3,28-Dioic Acid
IUPAC Name	(3S,4S,5R,8R,9R,10R,13S,14R,15R)-4-(2-carboxyethyl)-4,9,10-trimethyl-3-propan-2-yl-15-prop-1-en-2-yl-2,3,5,6,7,8,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2063163
PubChem CID	70682277
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003364] Steroid acids [CHEMONTID:0003368] 3-carboxy steroids

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 82 85 0 0 0 0 0 0 0 0999 V2000 -3.9994 -1.8921 -2.8709 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1359 -0.6450 -2.4556 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2946 0.4340 -3.4381 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1246 -0.3712 -0.9994 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4398 0.2908 -0.5852 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0681 1.4217 0.3414 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7088 0.9576 0.8231 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8913 2.0899 1.3987 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5747 1.3869 1.7963 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8499 1.0130 0.4991 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6361 2.3131 -0.1998 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7231 0.0420 -0.2824 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9510 -0.2762 -1.5324 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2212 -1.1685 -1.0522 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1149 -0.2177 -0.2898 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5440 -0.6660 -0.1812 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5532 -2.1912 -0.2701 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1415 -0.2954 -1.5659 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5726 -0.6282 -1.7161 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9525 -0.2307 -3.1298 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1467 -0.4396 -3.4495 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0600 0.3230 -4.0150 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3655 -0.0633 0.8531 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6215 0.6665 1.9586 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 1.4121 1.4463 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4584 0.3255 0.9171 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1536 -0.5822 2.0375 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4219 -0.8695 1.5504 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0005 -2.0609 2.3164 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0672 0.0971 2.5704 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0992 0.5507 -0.4940 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9399 -0.1180 1.7815 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5424 -1.2832 1.7780 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7466 0.2269 2.8903 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8798 -2.7185 -2.1848 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0059 -2.1036 -3.9243 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6303 0.1761 -4.3136 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3267 0.4558 -3.8511 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9549 1.4260 -3.0773 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -1.3242 -0.4375 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9224 0.7455 -1.4765 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1422 -0.4229 -0.1351 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7312 1.4500 1.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0305 2.4016 -0.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3352 2.4940 2.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7021 2.7998 0.5932 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0297 2.1207 2.3850 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8438 0.5361 2.4135 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3087 2.4603 -0.7132 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4216 2.5209 -0.9796 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7207 3.2111 0.4876 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7983 -0.9047 0.2699 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4485 -0.8678 -2.2821 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4511 0.6350 -1.9551 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7173 -1.6145 -1.9113 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2731 -1.9131 -0.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1454 0.6868 -0.9921 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3977 -2.5404 -1.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5183 -2.6397 -0.0078 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7480 -2.6781 0.2679 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0005 0.7911 -1.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5660 -0.8783 -2.3106 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1753 0.1037 -1.1020 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8697 -1.6643 -1.6041 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2617 0.2465 -5.0031 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9766 0.7856 0.3923 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2489 1.4793 2.3989 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3605 0.0125 2.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9921 1.9604 2.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7766 2.0653 0.6320 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0508 0.0703 2.9604 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9007 -1.3195 2.3233 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8058 -1.1356 1.9930 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2978 -1.0848 0.8762 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1881 -1.9549 3.4335 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6272 -2.9788 2.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9466 -2.3574 2.2688 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3697 0.1554 3.4266 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2127 1.0955 2.1660 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9952 -0.3606 2.9771 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1413 1.4687 -1.1341 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0243 -0.4443 3.5816 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 16 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 23 28 1 0 28 29 1 0 28 30 1 0 12 31 1 0 7 32 1 1 32 33 2 0 32 34 1 0 31 4 1 0 31 7 1 0 26 10 1 0 26 15 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 1 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 8 45 1 0 8 46 1 0 9 47 1 0 9 48 1 0 11 49 1 0 11 50 1 0 11 51 1 0 12 52 1 1 13 53 1 0 13 54 1 0 14 55 1 0 14 56 1 0 15 57 1 6 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 0 19 64 1 0 22 65 1 0 23 66 1 6 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 30 79 1 0 30 80 1 0 31 81 1 6 34 82 1 0 M END

Standard InCHIKey	WIPYWDLXFRPWFA-RGAAFHQASA-N
Standard InCHI	InChI=1S/C30H48O4/c1-18(2)20-10-15-30(26(33)34)17-16-28(6)22(25(20)30)8-9-23-27(5,13-12-24(31)32)21(19(3)4)11-14-29(23,28)7/h19-23,25H,1,8-17H2,2-7H3,(H,31,32)(H,33,34)/t20-,21-,22+,23+,25+,27-,28+,29+,30-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@](C)(CCC(=O)O)[C@@H](CC[C@@]34C)C(C)C)[C@@H]12)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	520.462 ? Van der Waals volume.
Dense:	0.908	LogP:	4.931 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.67 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.608 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	23.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.394	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.737	Fsp³:	0.867
MCE-18:	86.036 ? 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:	0.795	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.44	Promiscuous compounds:	0.189

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.143	MDCK Permeability:	-5.008
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.922 ? 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%):	0.001	30% Bioavailability (F30%):	0.003
50% Bioavailability (F50%):	0.077

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058	MRP1:	0.992
Plasma Protein Binding (PPB):	97.515%	Volume Distribution (VD):	-0.425
Fu:	2.444% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.976	BCRP inhibitor:	0.003
BSEP inhibitor:	0.255

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.938	CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	0.765	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.67
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
HLM stability:	0.0 ? 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):

2.391

Half-life (T1/2):

1.073

ADMET: Toxicity

hERG Blockers:	0.037	hERG Blockers (10um):	0.046
Human Hepatotoxicity (H-HT):	0.656	Drug-induced Liver Injury (DILI):	0.511
AMES Toxicity:	0.075	Rat Oral Acute Toxicity:	0.238
Maximum Recommended Daily Dose:	0.504	Skin Sensitization:	0.574
Carcinogencity:	0.758	Eye Corrosion:	0.096
Eye Irritation:	0.857	Respiratory Toxicity:	0.937
Drug-induced Neurotoxicity:	0.053	Ototoxicity:	0.729
Hematotoxicity:	0.553	Drug-induced Nephrotoxicity:	0.677
Genotoxicity:	0.452	RPMI-8226 Immunitoxicity:	0.017
A549 Cytotoxicity:	0.007	Hek293 Cytotoxicity:	0.034
BCF:	0.632 ? 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:	3.578 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.062 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.256 ? 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
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	Fruits	n.a.	n.a.	PMID[22691179]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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	8

Activity Type	# Activity
Cell line	8

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
NPT393	Cell line	HCT-116	Homo sapiens	IC50	<	10000.0	nM	PMID[17665951]
NPT83	Cell line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[15568769]
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	<	10000.0	nM	DOI[10.6019/CHEMBL1201861]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[9868153]
NPT165	Cell line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PubChem BioAssay data set
NPT65	Cell line	HepG2	Homo sapiens	IC50	<	10000.0	nM	DOI[10.1039/C5MD00325C]
NPT373	Cell line	SK-MEL-5	Homo sapiens	IC50	<	10000.0	nM	PMID[23145884]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[19879150]

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 NPC246445 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	31375
0.1-0.2	16235
0.2-0.3	1981
0.3-0.4	155
0.4-0.5	74
0.5-0.6	22
0.6-0.7	15
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
0.6842	Remote Similarity	NPC68828
0.65	Remote Similarity	NPC192744
0.6393	Remote Similarity	NPC264317
0.6393	Remote Similarity	NPC294438
0.629	Remote Similarity	NPC488506
0.629	Remote Similarity	NPC488164
0.629	Remote Similarity	NPC220498
0.629	Remote Similarity	NPC213832
0.629	Remote Similarity	NPC264005
0.619	Remote Similarity	NPC271974
0.619	Remote Similarity	NPC247312
0.619	Remote Similarity	NPC201655
0.6129	Remote Similarity	NPC80590
0.6094	Remote Similarity	NPC4309
0.6032	Remote Similarity	NPC24772
0.5968	Remote Similarity	NPC119743
0.5909	Remote Similarity	NPC160506
0.5909	Remote Similarity	NPC486704
0.5821	Remote Similarity	NPC478841
0.5821	Remote Similarity	NPC488166
0.5781	Remote Similarity	NPC211162
0.5781	Remote Similarity	NPC183374
0.5781	Remote Similarity	NPC291373
0.5692	Remote Similarity	NPC277399
0.5692	Remote Similarity	NPC195395
0.5606	Remote Similarity	NPC16377
0.5522	Remote Similarity	NPC474719
0.5522	Remote Similarity	NPC475061
0.5522	Remote Similarity	NPC601275
0.5441	Remote Similarity	NPC488165
0.5373	Remote Similarity	NPC151191
0.5362	Remote Similarity	NPC608379
0.5294	Remote Similarity	NPC488213
0.5147	Remote Similarity	NPC2783
0.5075	Remote Similarity	NPC280654
0.5072	Remote Similarity	NPC269360
0.5065	Remote Similarity	NPC486709

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC246445 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6683
0.1-0.2	2380
0.2-0.3	79
0.3-0.4	5
0.4-0.5	1
0.5-0.6	1
0.6-0.7	1
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
0.6393	Remote Similarity	NPD7520	Phase 1
0.5909	Remote Similarity	NPD8035	Phase 2

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