NPASS Compound

Natural Product: NPC280654

Natural Product ID	NPC280654
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-Olean-12-Ene-3,28-Dioic Acid
IUPAC Name	(1S,2S,4aR,4bS,6aS,10aS,12aR)-1-(2-carboxyethyl)-1,4a,4b,9,9-pentamethyl-2-propan-2-yl-3,4,5,6,7,8,10,10a,12,12a-decahydro-2H-chrysene-6a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL485790
PubChem CID	10719253
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 -5.2676 2.8307 1.4736 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1393 1.6082 2.1622 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1528 0.8781 2.1294 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8673 1.3188 2.8321 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7006 1.1009 2.0125 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5934 -0.0447 1.0228 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7792 -1.2474 1.9458 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5576 -0.0263 -0.0777 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8919 0.7683 -1.2307 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7336 -0.0112 -1.7961 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7404 -0.4232 -0.7600 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1434 0.0922 0.5689 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1656 -0.2124 1.6364 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1667 -0.6216 1.1402 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5933 -0.4372 -0.0868 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6430 0.2292 -1.0123 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6256 1.6968 -0.6693 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0581 0.1249 -2.4357 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4871 0.4743 -2.6526 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4575 0.0467 -1.6090 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9316 -0.8456 -0.5597 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9312 -1.0990 0.5390 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5853 0.1087 1.1105 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2313 0.2254 2.5725 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1172 0.0303 1.0637 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1847 1.3846 0.4088 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2366 1.2410 -1.0896 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4795 -0.7835 -2.3735 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6822 -1.9786 -2.1847 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2054 -0.1022 -3.3362 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5136 -1.9097 -0.7856 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1087 -1.2761 -0.6546 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0580 -0.8054 -1.7933 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0753 -2.0514 0.2372 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1326 3.1737 1.1352 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6744 2.2724 3.4420 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0068 0.5791 3.6753 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7809 1.0730 2.6955 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4926 2.0856 1.4590 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3299 -1.0575 2.9698 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8756 -1.1805 2.2342 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4768 -2.1940 1.5357 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4684 0.6190 0.0949 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5996 0.9568 -2.0561 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6160 1.7271 -0.7982 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3525 0.6232 -2.6143 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1199 -0.9180 -2.3043 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0441 1.2239 0.4201 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4720 -1.0152 2.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0587 0.6702 2.2981 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8091 -1.1021 1.8519 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8375 1.9168 0.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5043 2.1739 -1.2025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2409 2.2497 -1.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8354 -0.8285 -2.9193 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5085 0.9092 -3.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6096 1.5905 -2.7976 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7374 0.0947 -3.6926 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7983 -1.8603 -1.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7768 -1.6906 0.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5263 -1.8202 1.2759 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2234 0.6691 2.6992 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0042 0.7806 3.1462 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1444 -0.8361 2.9507 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5806 0.2179 2.0532 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5360 0.8246 0.3940 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4545 -0.9818 0.7543 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1993 1.7605 0.7414 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9335 2.1574 0.6803 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2898 1.1736 -1.4258 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8557 2.1849 -1.5308 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0781 -0.4705 -3.7290 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5115 -2.1687 -1.1694 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1647 -2.3308 -1.6083 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5908 -2.4265 0.1619 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4051 -1.9495 -1.1400 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6246 0.0940 -1.4843 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8118 -1.5988 -1.9758 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5126 -0.7107 -2.7447 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7448 -1.4229 0.8207 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5935 -2.8927 0.7736 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8100 -2.6291 -0.4321 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 6 5 1 1 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 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 23 26 1 0 26 27 1 0 20 28 1 6 28 29 2 0 28 30 1 0 11 31 1 1 8 32 1 0 32 33 1 0 32 34 1 0 12 6 1 0 21 15 1 0 16 11 1 0 27 20 1 0 1 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 5 39 1 0 7 40 1 0 7 41 1 0 7 42 1 0 8 43 1 1 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 12 48 1 6 13 49 1 0 13 50 1 0 14 51 1 0 17 52 1 0 17 53 1 0 17 54 1 0 18 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 21 59 1 6 22 60 1 0 22 61 1 0 24 62 1 0 24 63 1 0 24 64 1 0 25 65 1 0 25 66 1 0 25 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 27 71 1 0 30 72 1 0 31 73 1 0 31 74 1 0 31 75 1 0 32 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 M END

Standard InCHIKey	NQCJFEBTNHJJIB-NKQKOJDNSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-19(2)20-10-13-29(7)23(27(20,5)12-11-24(31)32)9-8-21-22-18-26(3,4)14-16-30(22,25(33)34)17-15-28(21,29)6/h8,19-20,22-23H,9-18H2,1-7H3,(H,31,32)(H,33,34)/t20-,22-,23+,27-,28+,29+,30-/m0/s1
SMILES	OC(=O)CC[C@@]1(C)[C@@H](CC[C@@]2([C@@H]1CC=C1[C@@]2(C)CC[C@@]2([C@H]1CC(C)(C)CC2)C(=O)O)C)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	520.462 ? Van der Waals volume.
Dense:	0.908	LogP:	4.92 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.616 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.563 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	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:	0.405	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.632	Fsp³:	0.867
MCE-18:	87.429 ? 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:	0.712	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.032 ? 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:	0.493	Promiscuous compounds:	0.079

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.233	MDCK Permeability:	-5.049
Pgp-inhibitor:	0.01	Pgp-substrate:	0.0
PAMPA:	0.997 ? 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%):	0.024	30% Bioavailability (F30%):	0.003
50% Bioavailability (F50%):	0.203

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.993
Plasma Protein Binding (PPB):	97.444%	Volume Distribution (VD):	-0.438
Fu:	2.783% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.912	BCRP inhibitor:	0.0
BSEP inhibitor:	0.947

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.978	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.016	CYP3A4-substrate:	0.008
CYP2B6-substrate:	0.009	CYP2C8-inhibitor:	0.006
HLM stability:	0.006 ? 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):

2.088

Half-life (T1/2):

1.029

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.044
Human Hepatotoxicity (H-HT):	0.596	Drug-induced Liver Injury (DILI):	0.351
AMES Toxicity:	0.067	Rat Oral Acute Toxicity:	0.452
Maximum Recommended Daily Dose:	0.483	Skin Sensitization:	0.569
Carcinogencity:	0.718	Eye Corrosion:	0.014
Eye Irritation:	0.486	Respiratory Toxicity:	0.936
Drug-induced Neurotoxicity:	0.093	Ototoxicity:	0.786
Hematotoxicity:	0.654	Drug-induced Nephrotoxicity:	0.872
Genotoxicity:	0.605	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.013	Hek293 Cytotoxicity:	0.047
BCF:	0.75 ? 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:	3.733 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.289 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.399 ? 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
NPO32595	junellia tridens	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141098]

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
MIC	1

Activity Type	# Activity
Organism	1

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
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	128.0	ug.mL-1	PubChem BioAssay data set

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 NPC280654 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	32057
0.1-0.2	15267
0.2-0.3	2013
0.3-0.4	277
0.4-0.5	178
0.5-0.6	34
0.6-0.7	26
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
0.7869	Intermediate Similarity	NPC37038
0.6774	Remote Similarity	NPC604575
0.6613	Remote Similarity	NPC471899
0.6364	Remote Similarity	NPC480946
0.6364	Remote Similarity	NPC130577
0.6364	Remote Similarity	NPC142415
0.6364	Remote Similarity	NPC102683
0.6269	Remote Similarity	NPC270768
0.6269	Remote Similarity	NPC59263
0.6269	Remote Similarity	NPC210106
0.6269	Remote Similarity	NPC282616
0.6269	Remote Similarity	NPC275809
0.6269	Remote Similarity	NPC84319
0.6269	Remote Similarity	NPC156981
0.6269	Remote Similarity	NPC52021
0.6269	Remote Similarity	NPC599947
0.6176	Remote Similarity	NPC106112
0.6176	Remote Similarity	NPC261935
0.6176	Remote Similarity	NPC231063
0.6176	Remote Similarity	NPC282395
0.6176	Remote Similarity	NPC158141
0.6176	Remote Similarity	NPC481360
0.6176	Remote Similarity	NPC110308
0.6094	Remote Similarity	NPC471897
0.6087	Remote Similarity	NPC200752
0.6087	Remote Similarity	NPC120840
0.6087	Remote Similarity	NPC298554
0.5833	Remote Similarity	NPC296164
0.5753	Remote Similarity	NPC96580
0.5571	Remote Similarity	NPC307282
0.5571	Remote Similarity	NPC64872
0.5571	Remote Similarity	NPC25906
0.5556	Remote Similarity	NPC474963
0.5526	Remote Similarity	NPC481362
0.5493	Remote Similarity	NPC130278
0.5417	Remote Similarity	NPC291028
0.5375	Remote Similarity	NPC204407
0.5352	Remote Similarity	NPC182797
0.5352	Remote Similarity	NPC121798
0.5352	Remote Similarity	NPC234346
0.5352	Remote Similarity	NPC52169
0.5352	Remote Similarity	NPC488562
0.5309	Remote Similarity	NPC606107
0.5278	Remote Similarity	NPC472149
0.5278	Remote Similarity	NPC609452
0.5263	Remote Similarity	NPC474727
0.5211	Remote Similarity	NPC474806
0.5211	Remote Similarity	NPC260385
0.5211	Remote Similarity	NPC110094
0.5211	Remote Similarity	NPC198664
0.5211	Remote Similarity	NPC133579
0.5143	Remote Similarity	NPC231431
0.5139	Remote Similarity	NPC32118
0.5135	Remote Similarity	NPC201657
0.5122	Remote Similarity	NPC283849
0.5122	Remote Similarity	NPC28198
0.5122	Remote Similarity	NPC476123
0.5075	Remote Similarity	NPC246445
0.5068	Remote Similarity	NPC271614
0.5068	Remote Similarity	NPC88116
0.5067	Remote Similarity	NPC471588

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC280654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7184
0.1-0.2	1911
0.2-0.3	50
0.3-0.4	5
0.4-0.5	0
0.5-0.6	0
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
		NPD

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