NPASS Compound

Natural Product: NPC282616

Natural Product ID	NPC282616
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	gypsogenic acid
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	15560324
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 85 0 0 0 0 0 0 0 0999 V2000 -5.8743 -1.1971 0.7258 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1658 -1.1982 -0.6019 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7558 -2.2508 -1.4666 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4122 0.1680 -1.2559 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9446 1.1903 -0.2772 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4760 1.0877 0.0544 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7409 1.6536 -1.1566 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3076 1.8292 -0.7433 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 0.5113 -0.4943 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3921 -0.1081 -1.8684 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5424 -0.4551 0.2161 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9750 -1.5105 0.7696 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4575 -1.8258 0.7498 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2881 -0.7333 0.1992 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7381 -0.7534 0.6328 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9775 -0.7403 2.0858 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3030 -2.0690 0.0681 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7657 -2.2002 0.2800 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5608 -0.9456 0.2813 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8902 0.2648 -0.2545 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4515 1.4670 0.5240 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4235 0.3228 -0.1687 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8718 1.6941 0.2217 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4404 1.7223 -0.2762 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6199 0.5970 0.3110 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2669 0.9906 1.7269 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3431 0.5088 -1.6696 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1663 -0.2346 -2.2548 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8168 1.6043 -2.3335 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1683 -0.6864 1.5376 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0253 -0.2989 0.3427 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6826 -1.3531 -0.4797 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2620 2.0297 1.1839 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8566 1.6614 2.3159 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5423 3.3800 0.9139 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0926 -2.2305 1.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3354 -0.6734 1.5178 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8534 -0.6945 0.5861 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0217 -2.8709 -2.0133 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4848 -1.8428 -2.2076 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3604 -2.9739 -0.8456 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9002 0.2276 -2.2330 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4832 0.3219 -1.4356 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5764 1.1442 0.6233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0965 2.2212 -0.7047 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2009 2.6205 -1.4705 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9198 0.9546 -1.9709 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7215 2.3220 -1.5715 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2680 2.5541 0.0888 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5419 0.2738 -2.3189 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1878 0.1747 -2.5868 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4358 -1.2155 -1.8114 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6226 -2.2328 1.3003 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5746 -2.7370 0.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7485 -2.1878 1.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3684 -0.9246 -0.9199 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3833 0.1783 2.5190 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7126 -1.5478 2.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0809 -1.0052 2.7187 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1176 -2.0195 -1.0374 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7637 -2.9374 0.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1358 -2.9592 -0.4720 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9539 -2.7134 1.2684 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4654 -1.1466 -0.3735 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5034 2.3473 -0.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8894 1.6844 1.4285 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5185 1.2183 0.7903 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0226 0.1696 -1.2208 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8613 1.8597 1.2953 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4163 2.4743 -0.3381 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4404 1.7906 -1.3567 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9962 2.6730 0.1253 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4408 0.3371 2.2350 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2165 1.1626 2.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2126 2.0159 1.7309 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0394 1.8518 -3.2905 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1449 -1.5473 2.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2919 -0.5142 1.4202 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4906 -2.3463 -0.0082 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2699 -1.4303 -1.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5425 4.0509 1.6589 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 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 20 27 1 0 27 28 2 0 27 29 1 0 19 30 1 0 11 31 1 0 31 32 1 0 6 33 1 1 33 34 2 0 33 35 1 0 32 2 1 0 31 6 1 0 25 9 1 0 25 14 1 0 22 15 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 10 50 1 0 10 51 1 0 10 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 14 56 1 6 16 57 1 0 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 18 62 1 0 18 63 1 0 19 64 1 6 21 65 1 0 21 66 1 0 21 67 1 0 22 68 1 6 23 69 1 0 23 70 1 0 24 71 1 0 24 72 1 0 26 73 1 0 26 74 1 0 26 75 1 0 29 76 1 0 30 77 1 0 31 78 1 1 32 79 1 0 32 80 1 0 35 81 1 0 M END

Standard InCHIKey	PAIBKVQNJKUVCE-JUENUIDLSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-25(2)13-15-30(24(34)35)16-14-27(4)18(19(30)17-25)7-8-20-26(3)11-10-22(31)29(6,23(32)33)21(26)9-12-28(20,27)5/h7,19-22,31H,8-17H2,1-6H3,(H,32,33)(H,34,35)/t19-,20+,21+,22-,26+,27+,28+,29-,30-/m0/s1
SMILES	CC1(C)CC[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]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	3.455 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.892 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.558 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.398	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.774	Fsp³:	0.867
MCE-18:	108.571 ? 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:	0.806	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.094 ? 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:	0.415	Promiscuous compounds:	0.061

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.633	MDCK Permeability:	-5.194
Pgp-inhibitor:	0.001	Pgp-substrate:	0.001
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):	0.003
20% Bioavailability (F20%):	0.282	30% Bioavailability (F30%):	0.01
50% Bioavailability (F50%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039	MRP1:	0.984
Plasma Protein Binding (PPB):	94.067%	Volume Distribution (VD):	-0.547
Fu:	6.203% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.274	BCRP inhibitor:	0.003
BSEP inhibitor:	0.93

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.169
CYP2C9-inhibitor:	0.014	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.007	CYP3A4-substrate:	0.014
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.008
HLM stability:	0.046 ? 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):

0.767

Half-life (T1/2):

1.512

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.785	Drug-induced Liver Injury (DILI):	0.888
AMES Toxicity:	0.13	Rat Oral Acute Toxicity:	0.334
Maximum Recommended Daily Dose:	0.177	Skin Sensitization:	0.976
Carcinogencity:	0.918	Eye Corrosion:	0.069
Eye Irritation:	0.491	Respiratory Toxicity:	0.907
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.701
Hematotoxicity:	0.614	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	0.913	RPMI-8226 Immunitoxicity:	0.022
A549 Cytotoxicity:	0.04	Hek293 Cytotoxicity:	0.029
BCF:	0.768 ? 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:	3.785 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.377 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.571 ? 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
NPO41783	Schlegelella brevitalea DSM 7029 [n.a.]	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[29666226]
NPO41783	Schlegelella brevitalea DSM 7029 [n.a.]	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[29666226] PMID[34301933]
NPO41783	Schlegelella brevitalea DSM 7029 [n.a.]	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[31999442] PMID[32603592] PMID[34301933]
NPO41783	Schlegelella brevitalea DSM 7029 [n.a.]	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[34301933]

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
Inhibition	1

Activity Type	# Activity
Organism	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
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	0.0	%	PMID[23662817]

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 NPC282616 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	25008
0.1-0.2	21509
0.2-0.3	2606
0.3-0.4	428
0.4-0.5	172
0.5-0.6	76
0.6-0.7	29
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
0.7656	Intermediate Similarity	NPC106112
0.7656	Intermediate Similarity	NPC261935
0.7344	Intermediate Similarity	NPC480946
0.7344	Intermediate Similarity	NPC130577
0.7344	Intermediate Similarity	NPC142415
0.7344	Intermediate Similarity	NPC102683
0.7231	Intermediate Similarity	NPC270768
0.7231	Intermediate Similarity	NPC59263
0.7231	Intermediate Similarity	NPC210106
0.7231	Intermediate Similarity	NPC275809
0.7164	Intermediate Similarity	NPC132824
0.7015	Intermediate Similarity	NPC298554
0.697	Remote Similarity	NPC84319
0.697	Remote Similarity	NPC52021
0.697	Remote Similarity	NPC599947
0.6957	Remote Similarity	NPC174663
0.6866	Remote Similarity	NPC231063
0.6866	Remote Similarity	NPC282395
0.6866	Remote Similarity	NPC110308
0.6618	Remote Similarity	NPC481360
0.6567	Remote Similarity	NPC86372
0.6522	Remote Similarity	NPC155120
0.6522	Remote Similarity	NPC288833
0.6471	Remote Similarity	NPC182797
0.6471	Remote Similarity	NPC121798
0.6471	Remote Similarity	NPC64872
0.6471	Remote Similarity	NPC37038
0.6471	Remote Similarity	NPC25906
0.6471	Remote Similarity	NPC234346
0.6471	Remote Similarity	NPC52169
0.6471	Remote Similarity	NPC488562
0.6462	Remote Similarity	NPC604575
0.6377	Remote Similarity	NPC271614
0.6377	Remote Similarity	NPC130278
0.6377	Remote Similarity	NPC158141
0.6269	Remote Similarity	NPC280654
0.6143	Remote Similarity	NPC472149
0.6143	Remote Similarity	NPC609452
0.6087	Remote Similarity	NPC198664
0.6	Remote Similarity	NPC307282
0.6	Remote Similarity	NPC156981
0.5867	Remote Similarity	NPC474727
0.5833	Remote Similarity	NPC291028
0.5833	Remote Similarity	NPC200752
0.5833	Remote Similarity	NPC228784
0.5833	Remote Similarity	NPC324341
0.5833	Remote Similarity	NPC120840
0.5833	Remote Similarity	NPC601810
0.5753	Remote Similarity	NPC474963
0.575	Remote Similarity	NPC204407
0.5694	Remote Similarity	NPC88116
0.5694	Remote Similarity	NPC111214
0.5679	Remote Similarity	NPC283849
0.5679	Remote Similarity	NPC28198
0.5679	Remote Similarity	NPC476123
0.5679	Remote Similarity	NPC606107
0.5676	Remote Similarity	NPC130520
0.5634	Remote Similarity	NPC474806
0.5634	Remote Similarity	NPC133579
0.56	Remote Similarity	NPC296164
0.56	Remote Similarity	NPC222047
0.5556	Remote Similarity	NPC32118
0.5542	Remote Similarity	NPC286347
0.5541	Remote Similarity	NPC35239
0.5541	Remote Similarity	NPC201657
0.5526	Remote Similarity	NPC96580
0.5476	Remote Similarity	NPC100383
0.5417	Remote Similarity	NPC187722
0.5417	Remote Similarity	NPC172361
0.5405	Remote Similarity	NPC145667
0.5402	Remote Similarity	NPC171007
0.5402	Remote Similarity	NPC190849
0.5395	Remote Similarity	NPC324063
0.5349	Remote Similarity	NPC294112
0.5349	Remote Similarity	NPC284807
0.5342	Remote Similarity	NPC229281
0.5342	Remote Similarity	NPC51700
0.5342	Remote Similarity	NPC88716
0.5342	Remote Similarity	NPC306541
0.5342	Remote Similarity	NPC68160
0.5342	Remote Similarity	NPC606443
0.5333	Remote Similarity	NPC91010
0.5316	Remote Similarity	NPC188833
0.5316	Remote Similarity	NPC481362
0.5287	Remote Similarity	NPC191410
0.5281	Remote Similarity	NPC198621
0.5281	Remote Similarity	NPC216940
0.527	Remote Similarity	NPC61543
0.527	Remote Similarity	NPC293048
0.527	Remote Similarity	NPC225585
0.5263	Remote Similarity	NPC471588
0.5227	Remote Similarity	NPC475472
0.5222	Remote Similarity	NPC605663
0.52	Remote Similarity	NPC202728
0.52	Remote Similarity	NPC158059
0.52	Remote Similarity	NPC293564
0.52	Remote Similarity	NPC136697
0.52	Remote Similarity	NPC29765
0.519	Remote Similarity	NPC601365
0.5172	Remote Similarity	NPC473538
0.5169	Remote Similarity	NPC270667
0.5169	Remote Similarity	NPC164194
0.5139	Remote Similarity	NPC213832
0.5132	Remote Similarity	NPC191412
0.5132	Remote Similarity	NPC114159
0.5132	Remote Similarity	NPC6818
0.5067	Remote Similarity	NPC173744
0.5067	Remote Similarity	NPC204961
0.5067	Remote Similarity	NPC73004
0.5067	Remote Similarity	NPC71074
0.5067	Remote Similarity	NPC37221
0.5067	Remote Similarity	NPC481314
0.5067	Remote Similarity	NPC605937
0.5065	Remote Similarity	NPC127689
0.5065	Remote Similarity	NPC481316
0.5055	Remote Similarity	NPC136877
0.5055	Remote Similarity	NPC12288

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC282616 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6841
0.1-0.2	2264
0.2-0.3	41
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