NPASS Compound

Natural Product: NPC36963

Natural Product ID	NPC36963
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OIAYHNBCCCYHLL-XKBWGFJCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21594182
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 87 91 0 0 0 0 0 0 0 0999 V2000 -5.7687 -0.8280 -1.6284 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3381 -0.0978 -0.3439 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1281 -0.7138 0.7654 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8682 -0.2649 -0.2509 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4215 -1.7107 -0.2707 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9713 -1.6959 -0.7093 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1113 -0.8035 0.1377 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6498 -1.5976 1.3334 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7165 0.5164 0.4676 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8253 1.2510 1.4051 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5962 0.9175 1.2032 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0879 0.1266 0.2641 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5729 -0.0807 0.2346 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1637 1.2451 -0.1257 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5951 1.2492 -0.4918 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7001 1.6051 -1.9815 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2082 -0.1220 -0.3020 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3989 -1.0568 -1.1741 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0027 -1.2336 -0.5617 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1139 -1.6190 -1.7018 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6727 -1.7343 -1.3496 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1470 -0.4946 -0.6920 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1614 0.4922 -1.8138 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1309 -2.4487 0.3189 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4612 -3.4944 0.1261 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0134 -2.4585 1.4000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1611 -3.5783 2.2476 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3500 2.2997 0.2398 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7192 3.0293 1.0473 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6994 2.5107 0.0762 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3352 3.5533 0.8315 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1713 0.4842 0.8504 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4712 -0.0121 2.2148 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6852 1.9289 0.7787 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4597 2.1853 -0.4866 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7067 1.3404 -0.5454 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6108 1.7890 0.4363 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6677 -0.3382 -2.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0298 -1.8812 -1.4080 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9219 -0.8179 -2.3577 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1939 -0.1269 1.6796 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8058 -1.7708 0.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1900 -0.8057 0.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4562 0.1697 -1.2143 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0009 -2.2751 -1.0215 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5020 -2.2274 0.6791 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9694 -1.4560 -1.7876 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5439 -2.7203 -0.6321 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3297 -2.0927 1.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5051 -0.9965 2.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3744 -2.4268 1.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7003 1.1146 -0.4963 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0486 1.1370 2.4706 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9076 2.3618 1.2053 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2989 1.3853 1.9175 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8532 -0.2711 1.3141 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5299 1.7181 -0.9182 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0305 1.9159 0.7717 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7385 2.7117 -2.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5774 1.1076 -2.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7475 1.3064 -2.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0939 -0.4371 0.7360 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2484 -0.1541 -0.6764 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9056 -2.0309 -1.2807 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3218 -0.6307 -2.1955 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4555 -2.6278 -2.0539 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3208 -0.9288 -2.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1093 -1.8529 -2.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4839 -2.6640 -0.7970 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0171 1.5409 -1.5067 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5868 0.3091 -2.6418 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1462 0.3235 -2.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2469 -3.8247 2.2548 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7930 -3.3033 3.2568 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6060 -4.4541 1.8677 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3665 3.7065 0.4866 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3290 3.3088 1.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7224 4.4972 0.7368 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2038 0.6549 2.7625 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6129 -0.0834 2.9097 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9606 -1.0163 2.2484 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3880 2.1447 1.6252 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8878 2.6635 0.8408 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8194 3.2503 -0.3974 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8551 2.1583 -1.3991 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2003 1.5490 -1.5164 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8853 2.7009 0.1414 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 19 24 1 1 24 25 2 0 24 26 1 0 26 27 1 0 15 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 9 32 1 0 32 33 1 1 32 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 2 1 0 32 4 1 0 22 7 1 0 22 12 1 0 19 13 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 3 42 1 0 3 43 1 0 4 44 1 6 5 45 1 0 5 46 1 0 6 47 1 0 6 48 1 0 8 49 1 0 8 50 1 0 8 51 1 0 9 52 1 6 10 53 1 0 10 54 1 0 11 55 1 0 13 56 1 1 14 57 1 0 14 58 1 0 16 59 1 0 16 60 1 0 16 61 1 0 17 62 1 0 17 63 1 0 18 64 1 0 18 65 1 0 20 66 1 0 20 67 1 0 21 68 1 0 21 69 1 0 23 70 1 0 23 71 1 0 23 72 1 0 27 73 1 0 27 74 1 0 27 75 1 0 31 76 1 0 31 77 1 0 31 78 1 0 33 79 1 0 33 80 1 0 33 81 1 0 34 82 1 0 34 83 1 0 35 84 1 0 35 85 1 0 36 86 1 6 37 87 1 0 M END

Standard InCHIKey	OIAYHNBCCCYHLL-XKBWGFJCSA-N
Standard InCHI	InChI=1S/C32H50O5/c1-27(2)22-11-14-31(6)23(29(22,4)13-12-24(27)33)10-9-20-21-19-28(3,25(34)36-7)15-17-32(21,26(35)37-8)18-16-30(20,31)5/h9,21-24,33H,10-19H2,1-8H3/t21-,22-,23+,24-,28-,29-,30+,31+,32-/m0/s1
SMILES	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC=C4[C@@H]5C[C@](C)(CC[C@@]5(CC[C@@]34C)C(=O)OC)C(=O)OC)[C@@]2(C)CC[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	514.37	Volume:	555.287 ? Van der Waals volume.
Dense:	0.926	LogP:	4.441 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.998 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.455 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	28.0
TPSA:	72.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.337	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.779	Fsp³:	0.875
MCE-18:	106.667 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.934	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.029 ? 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:	0.383	Promiscuous compounds:	0.167

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.38	MDCK Permeability:	-4.977
Pgp-inhibitor:	0.158	Pgp-substrate:	0.114
PAMPA:	0.994 ? 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%):	0.818	30% Bioavailability (F30%):	0.175
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.871	MRP1:	0.997
Plasma Protein Binding (PPB):	95.48%	Volume Distribution (VD):	-0.181
Fu:	5.143% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.699
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.987	CYP1A2-substrate:	0.267
CYP2C19-inhibitor:	0.611	CYP2C19-substrate:	0.643
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.128	CYP2D6-substrate:	0.51
CYP3A4-inhibitor:	0.859	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.989 ? 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):

8.449

Half-life (T1/2):

0.422

ADMET: Toxicity

hERG Blockers:	0.107	hERG Blockers (10um):	0.115
Human Hepatotoxicity (H-HT):	0.795	Drug-induced Liver Injury (DILI):	0.343
AMES Toxicity:	0.215	Rat Oral Acute Toxicity:	0.426
Maximum Recommended Daily Dose:	0.873	Skin Sensitization:	0.937
Carcinogencity:	0.934	Eye Corrosion:	0.007
Eye Irritation:	0.149	Respiratory Toxicity:	0.903
Drug-induced Neurotoxicity:	0.038	Ototoxicity:	0.498
Hematotoxicity:	0.352	Drug-induced Nephrotoxicity:	0.887
Genotoxicity:	0.859	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.456	Hek293 Cytotoxicity:	0.326
BCF:	1.255 ? 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:	3.828 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.531 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.748 ? 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
NPO2259	Tieghemella heckelii	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502347]
NPO2259	Tieghemella heckelii	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2259	Tieghemella heckelii	Species	Sapotaceae	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

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

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 NPC36963 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	18267
0.1-0.2	25824
0.2-0.3	4545
0.3-0.4	908
0.4-0.5	221
0.5-0.6	69
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8596	High Similarity	NPC246708
0.7097	Intermediate Similarity	NPC40552
0.6818	Remote Similarity	NPC49776
0.6818	Remote Similarity	NPC63118
0.6818	Remote Similarity	NPC474436
0.6615	Remote Similarity	NPC136313
0.6613	Remote Similarity	NPC235341
0.6515	Remote Similarity	NPC488519
0.6508	Remote Similarity	NPC470588
0.65	Remote Similarity	NPC290598
0.65	Remote Similarity	NPC30590
0.6364	Remote Similarity	NPC295643
0.6351	Remote Similarity	NPC167383
0.619	Remote Similarity	NPC101475
0.6119	Remote Similarity	NPC214756
0.5968	Remote Similarity	NPC27765
0.5968	Remote Similarity	NPC122418
0.5968	Remote Similarity	NPC491014
0.5915	Remote Similarity	NPC476879
0.5909	Remote Similarity	NPC267517
0.5857	Remote Similarity	NPC164349
0.5797	Remote Similarity	NPC7260
0.5797	Remote Similarity	NPC210037
0.5797	Remote Similarity	NPC120968
0.5797	Remote Similarity	NPC171203
0.5797	Remote Similarity	NPC307426
0.5797	Remote Similarity	NPC98442
0.5797	Remote Similarity	NPC242468
0.5797	Remote Similarity	NPC227467
0.5797	Remote Similarity	NPC273621
0.5797	Remote Similarity	NPC481361
0.5758	Remote Similarity	NPC95594
0.5735	Remote Similarity	NPC162107
0.5735	Remote Similarity	NPC46912
0.5714	Remote Similarity	NPC120098
0.5692	Remote Similarity	NPC311078
0.5692	Remote Similarity	NPC34177
0.5606	Remote Similarity	NPC253807
0.5606	Remote Similarity	NPC158662
0.5571	Remote Similarity	NPC307335
0.5571	Remote Similarity	NPC74855
0.557	Remote Similarity	NPC237503
0.5522	Remote Similarity	NPC159168
0.5507	Remote Similarity	NPC477579
0.5479	Remote Similarity	NPC294360
0.5455	Remote Similarity	NPC191763
0.5455	Remote Similarity	NPC196753
0.5429	Remote Similarity	NPC610937
0.5373	Remote Similarity	NPC40394
0.5352	Remote Similarity	NPC259788
0.5352	Remote Similarity	NPC255589
0.5303	Remote Similarity	NPC474989
0.5286	Remote Similarity	NPC477872
0.5281	Remote Similarity	NPC473373
0.5278	Remote Similarity	NPC18872
0.5278	Remote Similarity	NPC290614
0.5263	Remote Similarity	NPC283343
0.525	Remote Similarity	NPC46388
0.5211	Remote Similarity	NPC480946
0.5211	Remote Similarity	NPC272075
0.5211	Remote Similarity	NPC187722
0.5211	Remote Similarity	NPC213412
0.5211	Remote Similarity	NPC130577
0.5211	Remote Similarity	NPC142415
0.5211	Remote Similarity	NPC102683
0.5211	Remote Similarity	NPC2539
0.5195	Remote Similarity	NPC473160
0.5169	Remote Similarity	NPC139894
0.5147	Remote Similarity	NPC291379
0.5139	Remote Similarity	NPC182797
0.5139	Remote Similarity	NPC51700
0.5139	Remote Similarity	NPC88716
0.5139	Remote Similarity	NPC68160
0.5139	Remote Similarity	NPC52169
0.5139	Remote Similarity	NPC488562
0.5139	Remote Similarity	NPC112866
0.5139	Remote Similarity	NPC606443
0.5072	Remote Similarity	NPC230295
0.5072	Remote Similarity	NPC98386
0.5065	Remote Similarity	NPC471433
0.5065	Remote Similarity	NPC471432
0.5057	Remote Similarity	NPC214484
0.5054	Remote Similarity	NPC104071
0.5054	Remote Similarity	NPC309714

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC36963 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7006
0.1-0.2	2062
0.2-0.3	77
0.3-0.4	3
0.4-0.5	1
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
0.5352	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