NPASS Compound

Natural Product: NPC263393

Natural Product ID	NPC263393
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta,23-Dihydroxyolean-12-En-29-Oic Acid
IUPAC Name	(2R,4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bR)-10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1079259
PubChem CID	21123690
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 82 86 0 0 0 0 0 0 0 0999 V2000 6.4099 -1.7116 -1.4760 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0730 -1.2916 -1.6706 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7383 -0.5006 -0.3939 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7025 0.6269 -0.3305 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0125 -1.4572 0.7378 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6562 -0.8493 1.8127 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6930 -2.0098 1.2345 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8631 -0.8889 1.8356 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6430 0.2450 0.8320 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3055 -0.1498 -0.4478 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0039 0.9005 -1.5253 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5299 0.7440 -1.8378 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6839 0.9993 -0.6013 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1511 0.2757 0.6080 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3714 0.7021 1.7990 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0792 0.5755 1.4901 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5914 0.4873 0.2706 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7046 0.5085 -0.9427 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7074 -0.8244 -1.6100 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4253 1.4808 -1.8832 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6688 0.7725 -2.3166 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6248 0.6024 -1.1856 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0673 0.3862 0.1626 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5708 -0.8921 0.7993 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0783 -0.9814 0.7456 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6539 -0.7437 -0.6031 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5536 -0.5489 -1.6174 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7247 -0.0667 1.7566 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4272 -2.3884 1.1496 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1394 -2.6478 2.1398 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9442 -3.4388 0.4007 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5409 1.8406 -1.2179 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6303 2.4955 -0.4391 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2013 1.4875 1.4508 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0397 -1.2561 -2.0883 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4670 -2.1965 -1.7585 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0958 -0.6561 -2.5641 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9739 0.9323 0.7016 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4310 1.4865 -0.9806 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6787 0.2485 -0.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6349 -2.3264 0.4409 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6073 -1.1548 1.8859 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9365 -2.6927 2.0748 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1521 -2.5946 0.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4299 -0.5440 2.7323 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9433 -1.3413 2.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7586 -1.0683 -0.8109 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5378 0.6308 -2.4555 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2500 1.9232 -1.1863 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3925 -0.2629 -2.2530 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2474 1.4889 -2.5961 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8783 -0.8144 0.4556 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5100 1.7609 2.0998 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6065 0.1068 2.7034 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7710 0.5547 2.3564 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1095 -1.5155 -1.2814 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5313 -0.7410 -2.7253 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6461 -1.3774 -1.4049 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7375 2.3463 -1.2622 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7876 1.7623 -2.7432 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4897 -0.1940 -2.8275 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1270 1.4197 -3.1236 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4896 1.1952 0.8387 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3355 -0.7847 1.9010 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1428 -1.8069 0.3942 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3479 0.1354 -0.5752 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2702 -1.5914 -0.9644 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0277 -0.2000 -2.5582 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0152 -1.4841 -1.7575 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3525 0.7171 1.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4101 -0.6103 2.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9883 0.4516 2.3781 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1325 -4.4189 0.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9762 2.7407 -1.5289 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8727 2.0190 -0.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3669 1.7120 -1.9132 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6695 2.9366 -0.3899 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2156 2.9112 -1.3928 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0081 2.8402 0.3704 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7823 1.2725 2.3983 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4440 2.2339 1.7666 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8672 2.0669 0.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 6 3 4 1 0 3 5 1 0 5 6 1 0 5 7 1 0 7 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 1 0 15 16 1 0 16 17 2 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 1 0 26 27 1 0 25 28 1 1 25 29 1 0 29 30 2 0 29 31 1 0 22 32 1 1 13 33 1 1 9 34 1 1 10 3 1 0 18 13 1 0 27 22 1 0 14 9 1 0 23 17 1 0 1 35 1 0 2 36 1 0 2 37 1 0 4 38 1 0 4 39 1 0 4 40 1 0 5 41 1 6 6 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 10 47 1 6 11 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 14 52 1 6 15 53 1 0 15 54 1 0 16 55 1 0 19 56 1 0 19 57 1 0 19 58 1 0 20 59 1 0 20 60 1 0 21 61 1 0 21 62 1 0 23 63 1 1 24 64 1 0 24 65 1 0 26 66 1 0 26 67 1 0 27 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 31 73 1 0 32 74 1 0 32 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	VVWRIMSHBALFKN-MXUJDEKRSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-25-13-14-26(2,24(33)34)17-20(25)19-7-8-22-27(3)11-10-23(32)28(4,18-31)21(27)9-12-30(22,6)29(19,5)16-15-25/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,25+,26+,27-,28-,29+,30+/m0/s1
SMILES	OC[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@](CC1)(C)C(=O)O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.409 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.05 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.485 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.418	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.847	Fsp³:	0.9
MCE-18:	105.368 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.863	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:	0.436	Promiscuous compounds:	0.079

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.517	MDCK Permeability:	-5.045
Pgp-inhibitor:	0.001	Pgp-substrate:	0.162
PAMPA:	1.0 ? 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%):	0.972	30% Bioavailability (F30%):	0.023
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.332	MRP1:	0.988
Plasma Protein Binding (PPB):	92.009%	Volume Distribution (VD):	-0.508
Fu:	8.023% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.97
OATP1B3 inhibitor:	0.0	BCRP inhibitor:	0.365
BSEP inhibitor:	0.953

ADMET: Metabolism

CYP1A2-inhibitor:	0.085	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.281	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.071	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.016	CYP3A4-substrate:	0.012
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.004 ? 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):

1.89

Half-life (T1/2):

1.316

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.014
Human Hepatotoxicity (H-HT):	0.638	Drug-induced Liver Injury (DILI):	0.39
AMES Toxicity:	0.161	Rat Oral Acute Toxicity:	0.289
Maximum Recommended Daily Dose:	0.252	Skin Sensitization:	0.996
Carcinogencity:	0.909	Eye Corrosion:	0.242
Eye Irritation:	0.82	Respiratory Toxicity:	0.796
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.534
Hematotoxicity:	0.605	Drug-induced Nephrotoxicity:	0.935
Genotoxicity:	0.495	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.327	Hek293 Cytotoxicity:	0.099
BCF:	1.027 ? 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:	3.716 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.402 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.606 ? 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
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19618898]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	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	2

Activity Type	# Activity
Cell line	1
Non-molecular	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
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	107220.0	nM	PMID[19743809]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	150000.0	nM	PMID[19618898]

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 NPC263393 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	24017
0.1-0.2	21619
0.2-0.3	3101
0.3-0.4	751
0.4-0.5	250
0.5-0.6	72
0.6-0.7	35
0.7-0.8	0
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8548	High Similarity	NPC171203
0.8548	High Similarity	NPC307426
0.8548	High Similarity	NPC98442
0.8548	High Similarity	NPC242468
0.7206	Intermediate Similarity	NPC155120
0.7206	Intermediate Similarity	NPC288833
0.6875	Remote Similarity	NPC196753
0.6857	Remote Similarity	NPC474525
0.6761	Remote Similarity	NPC46441
0.6667	Remote Similarity	NPC7260
0.6667	Remote Similarity	NPC270768
0.6667	Remote Similarity	NPC59263
0.6667	Remote Similarity	NPC210037
0.6667	Remote Similarity	NPC263272
0.6667	Remote Similarity	NPC210106
0.6667	Remote Similarity	NPC229281
0.6667	Remote Similarity	NPC120968
0.6667	Remote Similarity	NPC121798
0.6667	Remote Similarity	NPC234346
0.6667	Remote Similarity	NPC227467
0.6667	Remote Similarity	NPC273621
0.662	Remote Similarity	NPC474964
0.6571	Remote Similarity	NPC61543
0.6571	Remote Similarity	NPC293048
0.6571	Remote Similarity	NPC225585
0.6528	Remote Similarity	NPC127689
0.6528	Remote Similarity	NPC474529
0.6389	Remote Similarity	NPC191412
0.6389	Remote Similarity	NPC114159
0.6389	Remote Similarity	NPC6818
0.6301	Remote Similarity	NPC476064
0.6301	Remote Similarity	NPC130520
0.6286	Remote Similarity	NPC260385
0.6286	Remote Similarity	NPC110094
0.6216	Remote Similarity	NPC116457
0.6164	Remote Similarity	NPC4036
0.6164	Remote Similarity	NPC65120
0.6164	Remote Similarity	NPC145067
0.6164	Remote Similarity	NPC233455
0.6164	Remote Similarity	NPC158030
0.6027	Remote Similarity	NPC104545
0.5972	Remote Similarity	NPC182797
0.5972	Remote Similarity	NPC52169
0.5972	Remote Similarity	NPC488562
0.5942	Remote Similarity	NPC230295
0.5942	Remote Similarity	NPC98386
0.5915	Remote Similarity	NPC477872
0.589	Remote Similarity	NPC474537
0.589	Remote Similarity	NPC126369
0.589	Remote Similarity	NPC470589
0.589	Remote Similarity	NPC111110
0.5867	Remote Similarity	NPC78580
0.5833	Remote Similarity	NPC480946
0.5833	Remote Similarity	NPC187722
0.5833	Remote Similarity	NPC213412
0.5833	Remote Similarity	NPC130577
0.5833	Remote Similarity	NPC142415
0.5833	Remote Similarity	NPC102683
0.5811	Remote Similarity	NPC136697
0.5802	Remote Similarity	NPC476878
0.5778	Remote Similarity	NPC482748
0.5753	Remote Similarity	NPC51700
0.5753	Remote Similarity	NPC88716
0.5753	Remote Similarity	NPC68160
0.5735	Remote Similarity	NPC221647
0.5672	Remote Similarity	NPC290598
0.5672	Remote Similarity	NPC30590
0.56	Remote Similarity	NPC202728
0.56	Remote Similarity	NPC158059
0.56	Remote Similarity	NPC293564
0.5595	Remote Similarity	NPC473938
0.5541	Remote Similarity	NPC606443
0.5526	Remote Similarity	NPC193750
0.5495	Remote Similarity	NPC309780
0.5493	Remote Similarity	NPC253402
0.5479	Remote Similarity	NPC95246
0.5429	Remote Similarity	NPC101475
0.5405	Remote Similarity	NPC274330
0.5405	Remote Similarity	NPC198664
0.5405	Remote Similarity	NPC610937
0.5395	Remote Similarity	NPC298554
0.5341	Remote Similarity	NPC476887
0.5325	Remote Similarity	NPC281524
0.5278	Remote Similarity	NPC53744
0.5217	Remote Similarity	NPC27765
0.5217	Remote Similarity	NPC122418
0.5217	Remote Similarity	NPC491014
0.52	Remote Similarity	NPC86372
0.52	Remote Similarity	NPC172361
0.5195	Remote Similarity	NPC475921
0.5195	Remote Similarity	NPC228784
0.5195	Remote Similarity	NPC324341
0.5195	Remote Similarity	NPC474704
0.5195	Remote Similarity	NPC601810
0.519	Remote Similarity	NPC187933
0.5139	Remote Similarity	NPC235341
0.5139	Remote Similarity	NPC478657
0.5132	Remote Similarity	NPC112866
0.5106	Remote Similarity	NPC476881
0.5065	Remote Similarity	NPC231063
0.5065	Remote Similarity	NPC18872
0.5065	Remote Similarity	NPC282395
0.5065	Remote Similarity	NPC73489
0.5065	Remote Similarity	NPC130278
0.5065	Remote Similarity	NPC290614
0.5065	Remote Similarity	NPC173744
0.5065	Remote Similarity	NPC88116
0.5065	Remote Similarity	NPC204961
0.5065	Remote Similarity	NPC73004
0.5065	Remote Similarity	NPC609452
0.5063	Remote Similarity	NPC137072
0.5054	Remote Similarity	NPC476882
0.5053	Remote Similarity	NPC482751

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC263393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6790
0.1-0.2	2303
0.2-0.3	47
0.3-0.4	3
0.4-0.5	5
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
0.6164	Remote Similarity	NPD7515	Phase 2
0.5753	Remote Similarity	NPD7645	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