NPASS Compound

Natural Product: NPC132824

Natural Product ID	NPC132824
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Diospyric Acid B
IUPAC Name	(3R,4R,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-3,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
Synonyms	diospyric acid B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL492457
PubChem CID	13857523
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 4.1634 -2.7562 0.0516 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5018 -1.5638 -0.8104 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5545 -0.6762 -0.2061 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0916 0.0629 0.9983 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7661 0.7540 0.8465 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0069 0.5605 2.1144 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5632 1.0391 2.0616 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8339 0.3132 0.9215 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8703 -1.1297 1.2858 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5729 0.6897 -0.3067 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9724 1.2331 -1.3619 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4847 1.5286 -1.4469 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1300 0.5869 -0.4699 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6079 0.5508 -0.6986 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2397 1.9055 -0.7910 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7825 -0.0751 -2.0941 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8182 -1.1414 -2.1377 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0533 -0.8484 -1.3500 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6217 -0.7764 0.1092 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7297 -2.2424 0.5917 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2119 -0.3740 0.2948 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9205 0.1835 1.6671 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4158 -0.0406 1.8635 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6023 0.7850 0.8862 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6030 2.1925 1.4172 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6178 -0.0382 0.9123 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1735 -0.5458 1.9078 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9711 1.2509 0.5829 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9273 -1.9455 -1.5404 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0613 0.5023 -0.4303 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3583 -0.7236 -1.2228 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5801 -0.4006 -2.7234 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 -1.5959 -1.3152 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1314 2.2296 0.8693 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7112 3.0280 1.7301 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9775 2.7486 -0.1082 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8769 -3.5933 -0.0873 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1201 -3.1020 -0.0990 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2452 -2.4389 1.1115 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9903 -2.0197 -1.7166 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4251 -1.3139 0.0493 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8953 0.0182 -1.0019 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9134 0.7356 1.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0306 -0.7012 1.8307 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4899 1.2154 2.9037 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1084 -0.4454 2.5612 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5994 2.1132 1.9011 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0977 0.7171 3.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5332 -1.1759 2.3703 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9102 -1.5469 1.3715 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3226 -1.8085 0.6381 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5443 1.5046 -2.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5834 2.5926 -1.1480 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8491 1.3230 -2.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7708 -0.4423 -0.7925 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5955 2.6224 -1.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5352 2.3524 0.1770 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1842 1.8931 -1.4027 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0564 0.6916 -2.8568 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8377 -0.5220 -2.4701 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4292 -2.1296 -1.8158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1270 -1.2627 -3.2036 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6265 0.0183 -1.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5860 -2.2642 1.6860 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7276 -2.5805 0.3157 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9653 -2.8318 0.0447 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5894 -1.3220 0.2356 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2240 1.2095 1.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4213 -0.4547 2.4105 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3245 -1.1439 1.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1509 0.1994 2.8913 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0354 2.8862 0.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5986 2.6664 1.4820 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3214 2.0951 2.5111 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5282 1.8010 1.2176 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8130 -1.6414 -1.1752 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4363 1.3319 -1.1246 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1404 -1.2610 -3.1414 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1958 0.4953 -2.8095 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6260 -0.3557 -3.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4262 -2.2477 -2.0368 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8387 3.6751 -0.5066 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 7 8 1 0 8 9 1 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 19 26 1 0 26 27 2 0 26 28 1 0 18 29 1 0 10 30 1 0 30 31 1 0 31 32 1 0 31 33 1 6 5 34 1 6 34 35 2 0 34 36 1 0 31 2 1 0 30 5 1 0 24 8 1 0 24 13 1 0 21 14 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 6 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 6 45 1 0 6 46 1 0 7 47 1 0 7 48 1 0 9 49 1 0 9 50 1 0 9 51 1 0 11 52 1 0 12 53 1 0 12 54 1 0 13 55 1 6 15 56 1 0 15 57 1 0 15 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 6 20 64 1 0 20 65 1 0 20 66 1 0 21 67 1 1 22 68 1 0 22 69 1 0 23 70 1 0 23 71 1 0 25 72 1 0 25 73 1 0 25 74 1 0 28 75 1 0 29 76 1 0 30 77 1 6 32 78 1 0 32 79 1 0 32 80 1 0 33 81 1 0 36 82 1 0 M END

Standard InCHIKey	UIEGOKVPCRANSU-NASGHRROSA-N
Standard InCHI	InChI=1S/C30H46O6/c1-17-9-14-30(24(34)35)16-15-26(3)18(22(30)29(17,6)36)7-8-19-25(2)12-11-21(31)28(5,23(32)33)20(25)10-13-27(19,26)4/h7,17,19-22,31,36H,8-16H2,1-6H3,(H,32,33)(H,34,35)/t17-,19-,20-,21-,22-,25-,26-,27-,28-,29-,30+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H]([C@@](C)([C@@H]5CC[C@@]34C)C(=O)O)O)[C@@H]2[C@]1(C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	502.33	Volume:	529.486 ? Van der Waals volume.
Dense:	0.949	LogP:	2.72 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.499 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.884 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	115.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.383	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.031	Fsp³:	0.867
MCE-18:	111.286 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.619	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.088 ? 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:	0.332	Promiscuous compounds:	0.071

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.456	MDCK Permeability:	-5.088
Pgp-inhibitor:	0.0	Pgp-substrate:	0.004
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):	0.001
20% Bioavailability (F20%):	0.071	30% Bioavailability (F30%):	0.007
50% Bioavailability (F50%):	0.432

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.999
Plasma Protein Binding (PPB):	87.096%	Volume Distribution (VD):	-0.597
Fu:	10.821% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.77	BCRP inhibitor:	0.0
BSEP inhibitor:	0.837

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.814	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.712	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.005
HLM stability:	0.0 ? 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):

1.763

Half-life (T1/2):

1.74

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.012
Human Hepatotoxicity (H-HT):	0.772	Drug-induced Liver Injury (DILI):	0.736
AMES Toxicity:	0.161	Rat Oral Acute Toxicity:	0.375
Maximum Recommended Daily Dose:	0.356	Skin Sensitization:	0.972
Carcinogencity:	0.977	Eye Corrosion:	0.033
Eye Irritation:	0.718	Respiratory Toxicity:	0.953
Drug-induced Neurotoxicity:	0.02	Ototoxicity:	0.675
Hematotoxicity:	0.311	Drug-induced Nephrotoxicity:	0.985
Genotoxicity:	0.915	RPMI-8226 Immunitoxicity:	0.026
A549 Cytotoxicity:	0.06	Hek293 Cytotoxicity:	0.08
BCF:	0.469 ? 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:	3.356 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.835 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.064 ? 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
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18798681]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[3430165]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]

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

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	30000.0	nM	PMID[25420212]

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 NPC132824 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	24327
0.1-0.2	22109
0.2-0.3	2768
0.3-0.4	438
0.4-0.5	127
0.5-0.6	56
0.6-0.7	16
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
0.7879	Intermediate Similarity	NPC35239
0.7647	Intermediate Similarity	NPC174663
0.7463	Intermediate Similarity	NPC202728
0.7463	Intermediate Similarity	NPC158059
0.7463	Intermediate Similarity	NPC136697
0.7353	Intermediate Similarity	NPC191412
0.7353	Intermediate Similarity	NPC114159
0.7353	Intermediate Similarity	NPC6818
0.7206	Intermediate Similarity	NPC259733
0.7206	Intermediate Similarity	NPC158371
0.7206	Intermediate Similarity	NPC207922
0.7164	Intermediate Similarity	NPC282616
0.7143	Intermediate Similarity	NPC187933
0.7101	Intermediate Similarity	NPC247139
0.7	Intermediate Similarity	NPC62516
0.6857	Remote Similarity	NPC118519
0.6761	Remote Similarity	NPC137072
0.6757	Remote Similarity	NPC96693
0.6667	Remote Similarity	NPC157113
0.6533	Remote Similarity	NPC233012
0.6528	Remote Similarity	NPC148964
0.6479	Remote Similarity	NPC256247
0.6338	Remote Similarity	NPC235053
0.6316	Remote Similarity	NPC54909
0.6301	Remote Similarity	NPC118964
0.6286	Remote Similarity	NPC86372
0.6267	Remote Similarity	NPC603658
0.625	Remote Similarity	NPC155120
0.625	Remote Similarity	NPC288833
0.6216	Remote Similarity	NPC284865
0.6	Remote Similarity	NPC147232
0.5897	Remote Similarity	NPC327179
0.5676	Remote Similarity	NPC106112
0.5676	Remote Similarity	NPC261935
0.5676	Remote Similarity	NPC111214
0.5584	Remote Similarity	NPC116457
0.5495	Remote Similarity	NPC25491
0.5488	Remote Similarity	NPC600756
0.5435	Remote Similarity	NPC482049
0.5435	Remote Similarity	NPC482050
0.5376	Remote Similarity	NPC482051
0.5333	Remote Similarity	NPC182797
0.5333	Remote Similarity	NPC275809
0.5333	Remote Similarity	NPC51700
0.5333	Remote Similarity	NPC121798
0.5333	Remote Similarity	NPC88716
0.5333	Remote Similarity	NPC234346
0.5333	Remote Similarity	NPC68160
0.5333	Remote Similarity	NPC52169
0.5333	Remote Similarity	NPC488562
0.5325	Remote Similarity	NPC9613
0.5263	Remote Similarity	NPC61543
0.5263	Remote Similarity	NPC293048
0.5263	Remote Similarity	NPC225585
0.5263	Remote Similarity	NPC88116
0.5263	Remote Similarity	NPC472149
0.5263	Remote Similarity	NPC71074
0.5263	Remote Similarity	NPC37221
0.5263	Remote Similarity	NPC605937
0.5263	Remote Similarity	NPC609452
0.5217	Remote Similarity	NPC482052
0.52	Remote Similarity	NPC480946
0.52	Remote Similarity	NPC187722
0.52	Remote Similarity	NPC130577
0.52	Remote Similarity	NPC142415
0.52	Remote Similarity	NPC102683
0.5195	Remote Similarity	NPC32407
0.5195	Remote Similarity	NPC293564
0.5195	Remote Similarity	NPC263548
0.5195	Remote Similarity	NPC606320
0.5135	Remote Similarity	NPC213832
0.5132	Remote Similarity	NPC270768
0.5132	Remote Similarity	NPC59263
0.5132	Remote Similarity	NPC210106
0.5132	Remote Similarity	NPC229281
0.5132	Remote Similarity	NPC84319
0.5132	Remote Similarity	NPC52021
0.5132	Remote Similarity	NPC599947
0.5102	Remote Similarity	NPC481234
0.5102	Remote Similarity	NPC479431
0.5065	Remote Similarity	NPC231063
0.5065	Remote Similarity	NPC282395
0.5065	Remote Similarity	NPC173744
0.5065	Remote Similarity	NPC204961
0.5065	Remote Similarity	NPC73004
0.5065	Remote Similarity	NPC481360
0.5065	Remote Similarity	NPC110308

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC132824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6819
0.1-0.2	2283
0.2-0.3	44
0.3-0.4	4
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