NPASS Compound

Natural Product: NPC484212

Natural Product ID	NPC484212
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XAZFYXRTXXHUNA-SJNNCRIMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10460122
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 81 86 0 0 0 0 0 0 0 0999 V2000 6.7312 -1.5834 -1.3615 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9560 -0.3456 -1.8398 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5620 0.8824 -1.2582 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3883 0.9964 0.2309 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0705 0.3294 0.6658 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1872 0.3971 -0.5561 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6600 -0.5195 -1.4769 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8738 0.0539 -0.2978 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9345 1.0262 -0.5519 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9974 0.4253 -1.6177 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6971 -0.9522 -1.0600 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0578 -0.9403 0.2013 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0568 -2.3180 0.8122 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5340 -2.5406 1.8859 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5214 -0.7294 -0.0516 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1443 -1.4249 -1.1874 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5085 -0.7297 -1.3864 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3824 -0.8024 -0.1899 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5844 -1.6513 -0.5364 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8706 0.5185 0.3248 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5075 0.0976 1.6431 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6390 -1.0340 2.1601 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6992 -1.4093 1.0241 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3093 -1.0278 1.2154 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9837 0.1030 2.0946 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7631 0.5813 2.0592 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3573 0.0918 1.2038 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0547 1.2877 0.6314 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2696 -0.5138 2.0729 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7860 -2.7935 0.8676 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7868 1.2508 -0.5642 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5001 2.5096 -0.9449 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5494 3.0053 -1.8062 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6330 4.1520 -2.3665 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4679 2.0013 -1.9217 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0388 0.8910 -1.1972 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4758 0.4830 0.9031 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1535 1.4629 1.6368 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2034 2.0470 -1.9335 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1957 -1.4392 -0.3866 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0391 -2.4611 -1.3903 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5060 -1.7717 -2.1316 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0004 -0.3449 -2.9597 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6794 0.7866 -1.4221 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3468 2.0933 0.4649 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3232 -0.7106 0.9277 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6938 0.9298 1.5170 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1915 1.4375 -0.9333 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3119 1.9728 -0.9304 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0803 1.0036 -1.7313 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5797 0.2782 -2.5495 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2890 -1.5586 -1.8803 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7369 -1.3984 -0.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3239 -3.1557 0.2260 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6342 0.3806 -0.2462 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6350 -1.3276 -2.1702 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3349 -2.4855 -0.9227 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2536 0.3247 -1.6352 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0087 -1.1320 -2.3000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6198 -1.8703 -1.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5246 -1.3182 -0.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4126 -2.6783 -0.0862 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9867 1.1249 0.6270 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4672 0.9689 2.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5605 -0.1700 1.5658 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3529 -1.8821 2.3792 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1461 -0.8341 3.1082 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7575 -1.9132 1.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7091 0.5296 2.7423 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5467 1.4336 2.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2929 2.0442 0.3109 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6875 1.8159 1.3831 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7887 0.1627 2.5899 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1395 -3.2734 1.4624 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6267 3.1091 -0.6749 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8569 0.6337 -0.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9243 0.0710 -1.9719 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0096 1.0283 2.1545 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4948 2.2748 0.9476 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4192 1.9372 2.3216 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7250 2.1062 -2.7773 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 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 13 14 2 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 27 29 1 1 23 30 1 6 20 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 4 37 1 0 37 38 1 0 3 39 1 0 7 2 1 0 28 9 1 0 36 31 1 0 27 12 1 0 24 15 1 0 23 18 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 6 3 44 1 1 4 45 1 6 5 46 1 0 5 47 1 0 6 48 1 6 9 49 1 6 10 50 1 0 10 51 1 0 11 52 1 0 11 53 1 0 13 54 1 0 15 55 1 6 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 19 60 1 0 19 61 1 0 19 62 1 0 20 63 1 1 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 24 68 1 1 25 69 1 0 26 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 30 74 1 0 32 75 1 0 36 76 1 0 36 77 1 0 38 78 1 0 38 79 1 0 38 80 1 0 39 81 1 0 M END

Standard InCHIKey	XAZFYXRTXXHUNA-SJNNCRIMSA-N
Standard InCHI	InChI=1S/C30H42O9/c1-17-26(33)23(36-3)13-25(38-17)39-19-4-9-28(16-31)21-5-8-27(2)20(18-12-24(32)37-15-18)7-11-30(27,35)22(21)6-10-29(28,34)14-19/h6,10,12,16-17,19-23,25-26,33-35H,4-5,7-9,11,13-15H2,1-3H3/t17-,19+,20-,21+,22-,23-,25+,26-,27-,28+,29+,30+/m1/s1
SMILES	C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@H]1CC[C@]2(C=O)[C@H]3CC[C@]4(C)[C@H](CC[C@@]4([C@@H]3C=C[C@@]2(C1)O)O)C1=CC(=O)OC1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	546.28	Volume:	544.663 ? Van der Waals volume.
Dense:	1.003	LogP:	1.334 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.833 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.584 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	131.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.27	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.606	Fsp³:	0.8
MCE-18:	111.111 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.747	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.18	Promiscuous compounds:	0.44

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.52	MDCK Permeability:	-5.145
Pgp-inhibitor:	0.002	Pgp-substrate:	0.971
PAMPA:	0.992 ? 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):	0.009
20% Bioavailability (F20%):	0.219	30% Bioavailability (F30%):	0.515
50% Bioavailability (F50%):	0.925

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.519	MRP1:	0.61
Plasma Protein Binding (PPB):	67.774%	Volume Distribution (VD):	-0.18
Fu:	29.499% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.989
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.032
BSEP inhibitor:	0.47

ADMET: Metabolism

CYP1A2-inhibitor:	0.991	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.477	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.019	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.988	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.096
HLM stability:	0.948 ? 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):

3.849

Half-life (T1/2):

3.159

ADMET: Toxicity

hERG Blockers:	0.202	hERG Blockers (10um):	0.767
Human Hepatotoxicity (H-HT):	0.807	Drug-induced Liver Injury (DILI):	0.885
AMES Toxicity:	0.932	Rat Oral Acute Toxicity:	0.992
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.97	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.995
Drug-induced Neurotoxicity:	0.032	Ototoxicity:	0.627
Hematotoxicity:	0.41	Drug-induced Nephrotoxicity:	0.956
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.792
A549 Cytotoxicity:	0.842	Hek293 Cytotoxicity:	0.991
BCF:	0.572 ? 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:	3.36 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.993 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.333 ? 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
NPO3643	Nierembergia aristata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7673928]
NPO3643	Nierembergia aristata	Species	Solanaceae	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
ED50	12

Activity Type	# Activity
Cell line	8
Non-molecular	4

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
NPT2049	Cell line	HT	Homo sapiens	ED50	=	0.4	ug ml-1	PMID[7673928]
NPT1034	Cell line	Lu1	Homo sapiens	ED50	=	0.1	ug ml-1	PMID[7673928]
NPT147	Cell line	SK-MEL-2	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[7673928]
NPT1851	Cell line	Col2	Homo sapiens	ED50	=	0.9	ug ml-1	PMID[7673928]
NPT91	Cell line	KB	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[7673928]
NPT762	Cell line	A-431	Homo sapiens	ED50	=	0.7	ug ml-1	PMID[7673928]
NPT858	Cell line	LNCaP	Homo sapiens	ED50	=	0.5	ug ml-1	PMID[7673928]
NPT133	Cell line	ZR-75-1	Homo sapiens	ED50	=	0.2	ug ml-1	PMID[7673928]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.3	ug ml-1	PMID[7673928]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.5	ug ml-1	PMID[7673928]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.8	ug ml-1	PMID[7673928]

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 NPC484212 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	14666
0.1-0.2	31682
0.2-0.3	3211
0.3-0.4	132
0.4-0.5	119
0.5-0.6	22
0.6-0.7	11
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
0.7821	Intermediate Similarity	NPC484211
0.775	Intermediate Similarity	NPC180079
0.7073	Intermediate Similarity	NPC34390
0.6667	Remote Similarity	NPC484210
0.6588	Remote Similarity	NPC84949
0.6588	Remote Similarity	NPC480562
0.6588	Remote Similarity	NPC74945
0.6588	Remote Similarity	NPC31354
0.6588	Remote Similarity	NPC69576
0.6526	Remote Similarity	NPC329636
0.6437	Remote Similarity	NPC483822
0.6092	Remote Similarity	NPC6108
0.6092	Remote Similarity	NPC89514
0.6023	Remote Similarity	NPC152615
0.5667	Remote Similarity	NPC10823
0.5612	Remote Similarity	NPC146857
0.5556	Remote Similarity	NPC17896
0.5556	Remote Similarity	NPC469755
0.5556	Remote Similarity	NPC284406
0.5556	Remote Similarity	NPC99080
0.5556	Remote Similarity	NPC197707
0.5556	Remote Similarity	NPC251866
0.5393	Remote Similarity	NPC474418
0.5368	Remote Similarity	NPC103534
0.5368	Remote Similarity	NPC44899
0.5368	Remote Similarity	NPC304260
0.5368	Remote Similarity	NPC29639
0.5275	Remote Similarity	NPC219085
0.5269	Remote Similarity	NPC250556
0.5238	Remote Similarity	NPC329675
0.5238	Remote Similarity	NPC194716
0.5213	Remote Similarity	NPC484202
0.5204	Remote Similarity	NPC603096
0.52	Remote Similarity	NPC469749
0.5053	Remote Similarity	NPC93883
0.5051	Remote Similarity	NPC608063

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC484212 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6015
0.1-0.2	3017
0.2-0.3	104
0.3-0.4	5
0.4-0.5	5
0.5-0.6	3
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
0.6437	Remote Similarity	NPD7516	Pre-clinical
0.5556	Remote Similarity	NPD7319	Approved
0.5408	Remote Similarity	NPD8377	Phase 4
0.5269	Remote Similarity	NPD7507	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