NPASS Compound

Natural Product: NPC474684

Natural Product ID	NPC474684
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Beta-Hydroxytirucalla-7,24-Dien-21-Oic Acid
IUPAC Name	(2S)-2-[(3S,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL479306
PubChem CID	10695137
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 81 84 0 0 0 0 0 0 0 0999 V2000 7.6029 1.8042 0.8645 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8495 0.4568 0.2762 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9618 -0.5093 0.3557 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6369 -0.3197 1.0460 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5769 -0.5707 0.0031 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1836 -0.3987 0.6214 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1214 -0.6501 -0.4232 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2460 0.3116 -1.5860 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8447 0.7914 -1.9227 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0079 -0.2642 -1.2602 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7447 -0.3883 0.0733 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7195 1.0082 0.6682 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1062 -1.4213 0.8957 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3525 -1.7049 0.6079 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0277 -0.4196 0.2703 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3564 0.2252 -0.8878 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9819 1.1927 -1.5160 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3371 1.7152 -1.1746 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9653 0.9336 -0.0495 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4781 -0.5099 -0.0459 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7235 -1.1297 -1.4125 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2848 -1.3070 0.9365 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9184 -0.4197 1.9990 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9509 0.4890 1.3471 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4256 1.1079 0.0759 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2562 0.6464 -1.0610 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6573 2.6230 0.2201 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1416 -0.2206 1.0943 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0326 -1.4942 -2.0841 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0698 -1.3303 1.7666 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8406 -0.8874 2.9284 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2061 -2.7068 1.6277 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1402 0.2094 -0.4177 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6507 1.7864 1.9771 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6302 2.2338 0.4989 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3769 2.5155 0.5152 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1745 -1.4749 -0.0830 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6318 0.7189 1.4283 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5867 -1.0665 1.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7304 0.1895 -0.7987 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6829 -1.6016 -0.3413 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1787 0.6310 1.0271 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2631 -1.6671 -0.7992 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6483 -0.2193 -2.4887 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8432 1.2036 -1.3348 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6689 1.8055 -1.5509 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6643 0.7335 -3.0281 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5772 1.6198 0.2644 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1846 1.5885 0.3179 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8132 0.9737 1.7560 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6300 -2.4072 0.7381 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2782 -1.1753 1.9781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7460 -2.0861 1.5989 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5302 -2.5163 -0.0954 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9416 0.2238 1.1978 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4843 1.6638 -2.3584 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9275 1.7374 -2.0918 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1770 2.7887 -0.8752 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5130 1.3689 0.8949 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 -1.9717 -1.6089 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6635 -0.4335 -2.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7493 -1.6062 -1.4376 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1617 -1.7936 0.4137 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7666 -2.1069 1.4550 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1830 0.1499 2.5645 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4549 -1.1037 2.6933 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2202 1.2408 2.1211 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1474 1.3182 -1.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7678 0.7009 -2.0547 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7203 -0.3692 -0.8811 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0403 2.9296 1.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7106 2.8367 0.4536 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2706 3.1533 -0.6603 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0097 -1.1771 1.0185 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4107 -2.9051 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9045 -1.7034 -2.6431 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3849 -2.4077 -1.5197 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6075 -3.2734 2.2483 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9603 0.4708 0.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2715 0.9332 -1.2713 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2327 -0.8066 -0.8020 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 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 0 11 12 1 1 11 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 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 24 28 1 0 10 29 1 6 6 30 1 0 30 31 2 0 30 32 1 0 2 33 1 0 11 7 1 0 20 15 1 0 16 10 1 0 25 19 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 6 42 1 1 7 43 1 6 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 12 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 15 55 1 1 17 56 1 0 18 57 1 0 18 58 1 0 19 59 1 1 21 60 1 0 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 24 67 1 1 26 68 1 0 26 69 1 0 26 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 32 78 1 0 33 79 1 0 33 80 1 0 33 81 1 0 M END

Standard InCHIKey	CGPBVNAIDFBRJG-ZRMZZLDZSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,11,20-22,24-25,31H,8,10,12-18H2,1-7H3,(H,32,33)/t20-,21-,22-,24-,25-,28+,29-,30+/m0/s1
SMILES	CC(=CCC[C@@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	511.671 ? Van der Waals volume.
Dense:	0.892	LogP:	5.39 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.847 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.235 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.424	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.717	Fsp³:	0.833
MCE-18:	81.455 ? 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:	0.695	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.54	Promiscuous compounds:	0.106

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.906	MDCK Permeability:	-4.738
Pgp-inhibitor:	0.016	Pgp-substrate:	0.016
PAMPA:	0.982 ? 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%):	0.025	30% Bioavailability (F30%):	0.004
50% Bioavailability (F50%):	0.871

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204	MRP1:	0.925
Plasma Protein Binding (PPB):	92.322%	Volume Distribution (VD):	-0.124
Fu:	7.465% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.26
BSEP inhibitor:	0.835

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.841	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.894	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.022
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):

7.924

Half-life (T1/2):

0.965

ADMET: Toxicity

hERG Blockers:	0.041	hERG Blockers (10um):	0.127
Human Hepatotoxicity (H-HT):	0.491	Drug-induced Liver Injury (DILI):	0.141
AMES Toxicity:	0.108	Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.432	Skin Sensitization:	0.869
Carcinogencity:	0.582	Eye Corrosion:	0.026
Eye Irritation:	0.62	Respiratory Toxicity:	0.836
Drug-induced Neurotoxicity:	0.037	Ototoxicity:	0.64
Hematotoxicity:	0.335	Drug-induced Nephrotoxicity:	0.527
Genotoxicity:	0.088	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.045	Hek293 Cytotoxicity:	0.115
BCF:	1.954 ? 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:	5.81 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.387 ? 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
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	wood	n.a.	n.a.	PMID[10691716]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	husks	Inner Mongolia, China	2004-SEP	PMID[18549275]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22801644]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23313635]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Inhibition	1

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual protein	Protease	Human immunodeficiency virus 1	IC50	=	100.0	ug.mL-1	PMID[24601675]
NPT202	Individual protein	Protease	Human immunodeficiency virus 1	Inhibition	=	50.0	%	DrugMatrix in vitro pharmacology data

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 NPC474684 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	21625
0.1-0.2	23300
0.2-0.3	4063
0.3-0.4	684
0.4-0.5	121
0.5-0.6	41
0.6-0.7	13
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC142361
0.8387	Intermediate Similarity	NPC475921
0.8387	Intermediate Similarity	NPC474704
0.7656	Intermediate Similarity	NPC470375
0.7656	Intermediate Similarity	NPC470376
0.7164	Intermediate Similarity	NPC96496
0.6818	Remote Similarity	NPC147066
0.6667	Remote Similarity	NPC471896
0.6418	Remote Similarity	NPC233836
0.6418	Remote Similarity	NPC159046
0.6418	Remote Similarity	NPC187376
0.6377	Remote Similarity	NPC472240
0.6377	Remote Similarity	NPC262858
0.6364	Remote Similarity	NPC478800
0.6324	Remote Similarity	NPC84271
0.6324	Remote Similarity	NPC102414
0.6301	Remote Similarity	NPC474570
0.6232	Remote Similarity	NPC478801
0.6056	Remote Similarity	NPC482518
0.5735	Remote Similarity	NPC328052
0.5694	Remote Similarity	NPC480720
0.5672	Remote Similarity	NPC1319
0.5616	Remote Similarity	NPC469406
0.5571	Remote Similarity	NPC470049
0.557	Remote Similarity	NPC609156
0.5556	Remote Similarity	NPC112866
0.5493	Remote Similarity	NPC486523
0.5429	Remote Similarity	NPC470224
0.5417	Remote Similarity	NPC610937
0.5373	Remote Similarity	NPC100334
0.5362	Remote Similarity	NPC30166
0.5352	Remote Similarity	NPC470077
0.5352	Remote Similarity	NPC125399
0.5352	Remote Similarity	NPC486522
0.5333	Remote Similarity	NPC484791
0.5333	Remote Similarity	NPC484790
0.527	Remote Similarity	NPC18872
0.527	Remote Similarity	NPC484789
0.527	Remote Similarity	NPC484801
0.527	Remote Similarity	NPC484786
0.527	Remote Similarity	NPC290614
0.527	Remote Similarity	NPC484787
0.527	Remote Similarity	NPC484788
0.5205	Remote Similarity	NPC173272
0.52	Remote Similarity	NPC471293
0.5135	Remote Similarity	NPC7260
0.5135	Remote Similarity	NPC210037
0.5135	Remote Similarity	NPC210268
0.5135	Remote Similarity	NPC120968
0.5135	Remote Similarity	NPC171203
0.5135	Remote Similarity	NPC307426
0.5135	Remote Similarity	NPC98442
0.5135	Remote Similarity	NPC242468
0.5135	Remote Similarity	NPC227467
0.5135	Remote Similarity	NPC273621
0.5135	Remote Similarity	NPC190604
0.5132	Remote Similarity	NPC5358
0.5132	Remote Similarity	NPC216260
0.5068	Remote Similarity	NPC477872
0.5067	Remote Similarity	NPC77168

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474684 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6398
0.1-0.2	2671
0.2-0.3	75
0.3-0.4	4
0.4-0.5	2
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