NPASS Compound

Natural Product: NPC203596

Natural Product ID	NPC203596
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FVWJYYTZTCVBKE-JRYMWQMJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 -5.6173 -1.3730 -1.6997 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4535 -1.6604 -1.0921 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6020 -2.5645 -1.9167 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0978 -1.2389 0.2178 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3115 -0.4776 0.8243 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1106 0.9324 0.3956 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5910 1.0992 0.5031 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0515 1.8597 -0.6339 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5666 1.9579 -0.5386 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9753 0.5641 -0.6094 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1701 0.2121 -2.0871 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6131 -0.4267 0.3200 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0234 -1.7575 -0.0554 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4234 -1.8231 0.4232 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1820 -0.5641 0.2226 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5348 -0.9356 -0.4148 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2786 -1.7580 -1.6923 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1820 -1.9148 0.5359 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1670 -1.3263 1.4937 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2520 -0.7037 0.6553 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6022 0.5169 0.0220 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6892 1.0509 -0.9395 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5305 1.5474 1.0965 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4056 0.2086 -0.7699 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6557 1.4641 -1.1563 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2444 1.2059 -1.5447 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5135 0.6239 -0.3210 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6403 1.8082 0.6753 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3641 -0.3299 1.3826 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0240 -0.3220 0.6066 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3799 1.9070 1.7639 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9110 1.2226 2.8829 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8125 -1.8172 -2.7019 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3697 -0.7490 -1.2922 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8684 -2.0796 -2.5443 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2809 -3.2424 -2.5126 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1014 -3.2904 -1.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1006 -2.1799 0.9185 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1317 -0.5055 1.9466 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2463 -0.9478 0.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6525 1.5706 1.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4890 1.2421 -0.5666 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4365 1.5772 -1.6282 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4295 2.9226 -0.5082 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3183 2.5543 0.3221 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2447 2.4755 -1.5019 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7971 1.1254 -2.6550 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5928 -0.6086 -2.4532 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2165 0.1354 -2.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0479 -0.2656 1.3296 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0184 -2.0098 -1.1070 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6424 -2.5235 0.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8397 -2.7273 -0.0692 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3513 -2.1081 1.4937 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5442 -0.2781 1.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6892 -1.2102 -2.5920 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8363 -2.7177 -1.6956 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2458 -1.9767 -1.8913 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4377 -2.5132 1.0948 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7555 -2.6434 -0.0761 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6461 -2.1990 2.0064 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7457 -0.7000 2.2708 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5022 -1.4051 -0.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4634 2.1348 -1.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6908 0.9584 -0.4761 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6080 0.5746 -1.9275 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8615 1.2871 1.9408 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2794 2.5674 0.7809 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5364 1.6747 1.6108 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8597 -0.1039 -1.7842 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1266 1.9678 -2.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6850 2.2658 -0.3991 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1138 0.5815 -2.4344 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7557 2.1790 -1.7480 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6489 2.7729 0.2040 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0399 1.7558 1.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6581 1.6016 1.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2217 -0.6138 0.9625 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1078 -0.4263 1.7724 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3331 2.1543 1.9215 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9381 2.8621 1.7416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0537 1.8967 3.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 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 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 20 29 1 0 12 30 1 0 7 31 1 1 31 32 1 0 30 4 1 0 30 7 1 0 27 10 1 0 27 15 1 0 24 16 1 0 1 33 1 0 1 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 4 38 1 1 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 8 43 1 0 8 44 1 0 9 45 1 0 9 46 1 0 11 47 1 0 11 48 1 0 11 49 1 0 12 50 1 1 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 15 55 1 1 17 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 20 63 1 6 22 64 1 0 22 65 1 0 22 66 1 0 23 67 1 0 23 68 1 0 23 69 1 0 24 70 1 6 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 28 75 1 0 28 76 1 0 28 77 1 0 29 78 1 0 30 79 1 1 31 80 1 0 31 81 1 0 32 82 1 0 M END

Standard InCHIKey	FVWJYYTZTCVBKE-JRYMWQMJSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23-,24-,25-,27+,28+,29+,30+/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@H]4[C@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@H]12)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	4.502 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.005 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.077 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	26.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.452	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.761	Fsp³:	0.933
MCE-18:	100.793 ? 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:	0.854	Fluc inhibitor:	0.004 ? 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:	0.462	Promiscuous compounds:	0.321

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.84	MDCK Permeability:	-4.715
Pgp-inhibitor:	0.01	Pgp-substrate:	0.049
PAMPA:	0.111 ? 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%):	0.979	30% Bioavailability (F30%):	0.756
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992	MRP1:	0.993
Plasma Protein Binding (PPB):	90.994%	Volume Distribution (VD):	-0.045
Fu:	8.62% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.951
OATP1B3 inhibitor:	0.017	BCRP inhibitor:	0.07
BSEP inhibitor:	0.784

ADMET: Metabolism

CYP1A2-inhibitor:	0.49	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.025
CYP2C9-inhibitor:	0.729	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.16	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.014	CYP3A4-substrate:	0.951
CYP2B6-substrate:	0.029	CYP2C8-inhibitor:	0.667
HLM stability:	0.239 ? 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):

10.812

Half-life (T1/2):

0.634

ADMET: Toxicity

hERG Blockers:	0.118	hERG Blockers (10um):	0.382
Human Hepatotoxicity (H-HT):	0.621	Drug-induced Liver Injury (DILI):	0.119
AMES Toxicity:	0.355	Rat Oral Acute Toxicity:	0.481
Maximum Recommended Daily Dose:	0.591	Skin Sensitization:	0.993
Carcinogencity:	0.946	Eye Corrosion:	0.062
Eye Irritation:	0.823	Respiratory Toxicity:	0.882
Drug-induced Neurotoxicity:	0.373	Ototoxicity:	0.505
Hematotoxicity:	0.411	Drug-induced Nephrotoxicity:	0.609
Genotoxicity:	0.586	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.83	Hek293 Cytotoxicity:	0.692
BCF:	2.132 ? 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:	3.938 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.995 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.626 ? 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
NPO22129	Dracocephalum peregrinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18958424]
NPO12408	Jacaranda glabra	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20307077]
NPO21511	Gutierrezia texana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12408	Jacaranda glabra	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22129	Dracocephalum peregrinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21511	Gutierrezia texana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20540	Berrya mollis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12408	Jacaranda glabra	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16151	Inga oerstediana	Species	Fabaceae	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 NPC203596 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	27572
0.1-0.2	19171
0.2-0.3	2499
0.3-0.4	454
0.4-0.5	77
0.5-0.6	46
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC231256
1.0	High Similarity	NPC178383
0.88	High Similarity	NPC119355
0.8571	High Similarity	NPC78067
0.8571	High Similarity	NPC278091
0.78	Intermediate Similarity	NPC192638
0.78	Intermediate Similarity	NPC25511
0.78	Intermediate Similarity	NPC600137
0.7407	Intermediate Similarity	NPC86305
0.7407	Intermediate Similarity	NPC212879
0.7222	Intermediate Similarity	NPC5767
0.7222	Intermediate Similarity	NPC475742
0.7222	Intermediate Similarity	NPC93662
0.7091	Intermediate Similarity	NPC246956
0.7091	Intermediate Similarity	NPC74595
0.7091	Intermediate Similarity	NPC264665
0.7037	Intermediate Similarity	NPC248830
0.7037	Intermediate Similarity	NPC212241
0.7037	Intermediate Similarity	NPC472742
0.6852	Remote Similarity	NPC104387
0.6842	Remote Similarity	NPC12774
0.6545	Remote Similarity	NPC202540
0.65	Remote Similarity	NPC607755
0.6491	Remote Similarity	NPC201459
0.6491	Remote Similarity	NPC269396
0.6333	Remote Similarity	NPC5280
0.6271	Remote Similarity	NPC474233
0.625	Remote Similarity	NPC144075
0.625	Remote Similarity	NPC301226
0.614	Remote Similarity	NPC42853
0.6111	Remote Similarity	NPC142712
0.6071	Remote Similarity	NPC185536
0.6	Remote Similarity	NPC480925
0.6	Remote Similarity	NPC48079
0.5968	Remote Similarity	NPC33768
0.5965	Remote Similarity	NPC91573
0.5893	Remote Similarity	NPC606606
0.5862	Remote Similarity	NPC237460
0.5789	Remote Similarity	NPC97534
0.5789	Remote Similarity	NPC195155
0.5763	Remote Similarity	NPC296701
0.5763	Remote Similarity	NPC218616
0.5738	Remote Similarity	NPC474484
0.5714	Remote Similarity	NPC483720
0.569	Remote Similarity	NPC245869
0.569	Remote Similarity	NPC240235
0.569	Remote Similarity	NPC14112
0.5658	Remote Similarity	NPC478270
0.5658	Remote Similarity	NPC478271
0.5645	Remote Similarity	NPC175410
0.5625	Remote Similarity	NPC168231
0.5556	Remote Similarity	NPC264317
0.5556	Remote Similarity	NPC294438
0.5556	Remote Similarity	NPC232112
0.5517	Remote Similarity	NPC102708
0.55	Remote Similarity	NPC211009
0.5484	Remote Similarity	NPC49599
0.5484	Remote Similarity	NPC49627
0.5484	Remote Similarity	NPC93778
0.541	Remote Similarity	NPC13554
0.5397	Remote Similarity	NPC474482
0.5345	Remote Similarity	NPC80297
0.5345	Remote Similarity	NPC475727
0.5345	Remote Similarity	NPC116119
0.5323	Remote Similarity	NPC298168
0.5323	Remote Similarity	NPC143133
0.5323	Remote Similarity	NPC126993
0.5303	Remote Similarity	NPC16377
0.5172	Remote Similarity	NPC35652
0.5156	Remote Similarity	NPC477578
0.5156	Remote Similarity	NPC477577
0.5143	Remote Similarity	NPC471902
0.5119	Remote Similarity	NPC478272
0.5082	Remote Similarity	NPC58631
0.5082	Remote Similarity	NPC285761
0.5082	Remote Similarity	NPC34930
0.5082	Remote Similarity	NPC99168
0.5077	Remote Similarity	NPC201406
0.5077	Remote Similarity	NPC289486
0.5075	Remote Similarity	NPC151191

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC203596 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7996
0.1-0.2	1100
0.2-0.3	48
0.3-0.4	4
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
0.5556	Remote Similarity	NPD7520	Phase 1

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