NPASS Compound

Natural Product: NPC476064

Natural Product ID	NPC476064
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Methyloximo-Olean-12-En-29-Oic Acid
IUPAC Name	(2R,4aS,6aR,6aS,6bR,8aR,10Z,12aR,14bR)-10-methoxyimino-2,4a,6a,6b,9,9,12a-heptamethyl-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL524160
PubChem CID	44566379
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 84 88 0 0 0 0 0 0 0 0999 V2000 8.1259 1.5231 0.0390 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2157 0.6014 -0.5325 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1730 1.0082 -1.3321 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9481 0.8853 -0.9752 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8838 1.3450 -1.8858 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9324 0.2274 -2.1371 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4314 -0.4516 -0.8694 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0738 0.1631 0.3424 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5478 0.3034 0.3187 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9157 1.3686 1.3664 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3012 -0.9434 0.6970 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5356 -0.4867 1.5848 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1089 -0.0083 1.7465 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3233 -0.4116 0.5473 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9601 -0.1516 -0.7799 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1217 -0.7677 -1.8449 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2989 -0.8865 -1.4823 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8744 -0.3896 -0.4046 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9981 0.3692 0.5429 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8361 1.7550 0.0220 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6142 0.4491 1.9153 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0693 0.7604 1.8642 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8091 -0.3478 1.1822 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3093 -0.5964 -0.1915 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0487 0.1696 -1.2617 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5271 -0.0346 -1.2460 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0008 -0.9421 -2.3619 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9759 -0.6495 0.0510 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2746 0.0765 1.1682 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2396 1.2647 -1.4300 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0267 1.6920 -0.5533 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0700 2.0502 -2.5580 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7512 -1.6193 2.0030 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0370 -1.8741 0.6932 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7594 -1.8965 -1.0131 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1286 1.4753 -0.4359 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7716 2.5750 -0.1355 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1433 1.3459 1.1258 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3885 2.2733 -1.5333 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3161 1.6185 -2.8876 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0863 0.6572 -2.7468 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4315 -0.4791 -2.8367 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6670 1.2228 0.3700 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7442 1.0154 2.0143 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1721 2.3403 0.8940 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0596 1.5490 2.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9301 -1.2918 -0.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0397 -0.7594 1.5336 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6375 -1.7449 1.1066 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5404 -1.5845 1.5798 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1525 -0.2087 2.4856 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6957 -0.5783 2.6224 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1517 1.0746 1.9338 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9009 0.9689 -0.9390 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1591 -0.1150 -2.7673 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4461 -1.7620 -2.1953 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9348 -1.4465 -2.1864 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6734 2.3744 0.4059 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9379 1.8253 -1.1009 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0802 2.2733 0.3832 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4190 -0.4173 2.5386 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1192 1.3400 2.4079 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3304 1.6940 1.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4447 0.9286 2.9106 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5083 -1.6868 -0.4182 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6446 -0.1783 -2.2384 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8163 1.2576 -1.2008 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5506 -1.9472 -2.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8735 -0.4532 -3.3582 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0961 -1.0675 -2.2324 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7831 -1.7349 0.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0770 -0.5021 0.1915 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3836 1.1587 1.0207 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7846 -0.1875 2.1171 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9608 3.0727 -2.4717 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7447 -1.8574 2.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4252 -2.4553 1.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0823 -1.5101 2.8951 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5300 -2.3481 1.5442 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1327 -2.4542 -0.2379 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1044 -2.0339 0.9447 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5220 -2.5540 -0.1907 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8791 -1.9556 -1.1554 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3912 -2.2822 -2.0093 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 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 9 11 1 0 8 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 2 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 26 28 1 0 28 29 1 0 26 30 1 0 30 31 2 0 30 32 1 0 23 33 1 1 14 34 1 1 7 35 1 6 9 4 1 0 19 14 1 0 29 23 1 0 15 7 1 0 24 18 1 0 1 36 1 0 1 37 1 0 1 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 8 43 1 1 10 44 1 0 10 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 15 54 1 6 16 55 1 0 16 56 1 0 17 57 1 0 20 58 1 0 20 59 1 0 20 60 1 0 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 24 65 1 6 25 66 1 0 25 67 1 0 27 68 1 0 27 69 1 0 27 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 32 75 1 0 33 76 1 0 33 77 1 0 33 78 1 0 34 79 1 0 34 80 1 0 34 81 1 0 35 82 1 0 35 83 1 0 35 84 1 0 M END

Standard InCHIKey	SAJCKHUHILYREB-VMJQRFLMSA-N
Standard InCHI	InChI=1S/C31H49NO3/c1-26(2)22-11-14-31(7)23(29(22,5)13-12-24(26)32-35-8)10-9-20-21-19-28(4,25(33)34)16-15-27(21,3)17-18-30(20,31)6/h9,21-23H,10-19H2,1-8H3,(H,33,34)/b32-24-/t21-,22-,23+,27+,28+,29-,30+,31+/m0/s1
SMILES	CO/N=C1/CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@@](C)(CC1)C(=O)O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	483.37	Volume:	531.408 ? Van der Waals volume.
Dense:	0.91	LogP:	3.429 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.14 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.898 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	58.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.321	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.905	Fsp³:	0.871
MCE-18:	103.552 ? 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:	0.935	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.159	Promiscuous compounds:	0.018

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.93	MDCK Permeability:	-4.861
Pgp-inhibitor:	0.997	Pgp-substrate:	0.0
PAMPA:	0.037 ? 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%):	0.286	30% Bioavailability (F30%):	0.021
50% Bioavailability (F50%):	0.556

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009	MRP1:	0.469
Plasma Protein Binding (PPB):	96.79%	Volume Distribution (VD):	-0.12
Fu:	3.619% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.98
OATP1B3 inhibitor:	0.7	BCRP inhibitor:	0.006
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.147	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.341	CYP2C19-substrate:	0.011
CYP2C9-inhibitor:	0.008	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.977
HLM stability:	0.043 ? 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):

1.729

Half-life (T1/2):

1.343

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.096
Human Hepatotoxicity (H-HT):	0.885	Drug-induced Liver Injury (DILI):	0.957
AMES Toxicity:	0.182	Rat Oral Acute Toxicity:	0.572
Maximum Recommended Daily Dose:	0.399	Skin Sensitization:	0.994
Carcinogencity:	0.815	Eye Corrosion:	0.019
Eye Irritation:	0.42	Respiratory Toxicity:	0.927
Drug-induced Neurotoxicity:	0.11	Ototoxicity:	0.624
Hematotoxicity:	0.547	Drug-induced Nephrotoxicity:	0.846
Genotoxicity:	0.779	RPMI-8226 Immunitoxicity:	0.01
A549 Cytotoxicity:	0.013	Hek293 Cytotoxicity:	0.165
BCF:	2.089 ? 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:	4.614 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.833 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.424 ? 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
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479314]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	stems	n.a.	n.a.	PMID[1517737]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22672802]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15299	Sandoricum koetjape	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15299	Sandoricum koetjape	Species	Meliaceae	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
IC50	1
Kii	2
Kis	2

Activity Type	# Activity
Individual protein	5

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	IC50	=	36000.0	nM	PMID[8377017]
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	Kii	=	35.0	uM	PMID[10479314]
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	Kis	=	9.1	uM	PMID[10479314]
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	Kis	=	73.0	uM	PMID[10479314]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC476064 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	30018
0.1-0.2	17285
0.2-0.3	1984
0.3-0.4	459
0.4-0.5	71
0.5-0.6	22
0.6-0.7	13
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8125	Intermediate Similarity	NPC263272
0.7838	Intermediate Similarity	NPC473938
0.75	Intermediate Similarity	NPC474964
0.6667	Remote Similarity	NPC46441
0.6571	Remote Similarity	NPC171203
0.6571	Remote Similarity	NPC307426
0.6571	Remote Similarity	NPC98442
0.6571	Remote Similarity	NPC242468
0.6301	Remote Similarity	NPC263393
0.6301	Remote Similarity	NPC474525
0.625	Remote Similarity	NPC474537
0.6197	Remote Similarity	NPC260385
0.6197	Remote Similarity	NPC110094
0.6164	Remote Similarity	NPC104545
0.6111	Remote Similarity	NPC96095
0.6	Remote Similarity	NPC474529
0.5946	Remote Similarity	NPC155120
0.5946	Remote Similarity	NPC288833
0.5921	Remote Similarity	NPC198818
0.5867	Remote Similarity	NPC281524
0.5867	Remote Similarity	NPC193750
0.5789	Remote Similarity	NPC78580
0.5652	Remote Similarity	NPC221647
0.557	Remote Similarity	NPC169343
0.5507	Remote Similarity	NPC142754
0.52	Remote Similarity	NPC274050
0.52	Remote Similarity	NPC162632
0.507	Remote Similarity	NPC82477
0.5065	Remote Similarity	NPC7260
0.5065	Remote Similarity	NPC210037
0.5065	Remote Similarity	NPC120968
0.5065	Remote Similarity	NPC227467
0.5065	Remote Similarity	NPC273621
0.5063	Remote Similarity	NPC4036
0.5063	Remote Similarity	NPC65120
0.5063	Remote Similarity	NPC145067
0.5063	Remote Similarity	NPC233455
0.5063	Remote Similarity	NPC158030

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476064 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6849
0.1-0.2	2277
0.2-0.3	15
0.3-0.4	6
0.4-0.5	2
0.5-0.6	1
0.6-0.7	0
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
0.5063	Remote Similarity	NPD7515	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