NPASS Compound

Natural Product: NPC277477

Natural Product ID	NPC277477
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VJTBJVHQCFQKLQ-XTNHTTTKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102317132
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

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 76 79 0 0 0 0 0 0 0 0999 V2000 7.6857 1.4072 1.5905 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2302 0.5955 0.4302 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7646 -0.8215 0.5683 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2596 -0.8748 0.5686 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6248 -0.3408 -0.6837 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1194 -0.3922 -0.6802 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6583 -1.8003 -0.5378 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1716 -1.9158 -0.5411 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6649 -3.0424 -0.4301 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3322 -0.8344 -0.6612 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1030 -0.9682 -0.6621 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6067 -1.5758 0.5861 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0564 -1.3419 0.8809 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2093 -1.5191 2.4017 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5056 0.0643 0.5832 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1496 0.5467 -0.7991 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0965 2.0499 -0.7271 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8424 2.9369 -0.0825 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0030 2.6818 0.7970 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6408 1.4143 0.4134 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8950 0.2467 0.9919 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8491 -0.8413 0.8319 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0655 -0.3285 0.8662 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3308 -1.1096 0.7393 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9649 1.1424 1.0358 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7882 1.9148 1.5634 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8600 1.3398 -0.9546 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4818 4.3867 -0.2522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3727 4.4491 -1.1062 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 0.0528 -1.3264 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7241 -1.2916 -2.0008 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2705 -1.4477 -3.1626 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8861 -2.2143 -2.0957 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6957 0.8756 1.4284 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9070 0.9600 2.5697 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6227 1.6075 1.4430 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2134 2.3855 1.5578 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3473 0.6743 0.5292 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9141 1.0691 -0.5038 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1170 -1.4456 -0.2820 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0973 -1.2797 1.5311 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9957 -1.9666 0.6886 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9275 -0.3101 1.4726 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9715 -0.9416 -1.5707 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9988 0.6883 -0.8853 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7553 0.2526 0.1476 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7883 -0.0188 -1.6725 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0355 -2.3903 -1.3982 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0470 -2.2659 0.4131 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0154 -1.1769 1.4361 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4764 -2.6955 0.5033 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7071 -2.1284 0.4511 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8495 -2.5358 2.7000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2417 -1.3671 2.7358 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5501 -0.7861 2.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9174 0.2294 -1.5463 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2821 2.5010 -1.3251 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7356 3.5168 0.5855 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7884 2.7528 1.8681 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8851 0.4615 2.1135 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6878 -1.9150 0.7018 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2195 -0.4644 0.6112 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2855 -1.7546 -0.1849 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5259 -1.7242 1.6455 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8590 2.2605 -1.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1275 4.7232 0.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3372 4.9709 -0.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5522 4.7422 -0.6395 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2615 0.8405 -1.8960 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3428 -1.3086 -4.0866 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0113 -0.6469 -3.1322 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6963 -2.4709 -3.1715 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6493 -3.1123 -1.4525 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9652 -2.6711 -3.1271 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8638 -1.7765 -1.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1291 1.0724 2.2730 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 2 0 8 10 1 0 11 10 1 6 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 2 0 20 27 1 6 18 28 1 0 28 29 1 0 16 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 15 34 1 1 30 11 1 0 31 11 1 0 21 15 1 0 25 20 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 2 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 6 46 1 0 6 47 1 0 7 48 1 0 7 49 1 0 12 50 1 0 12 51 1 0 13 52 1 6 14 53 1 0 14 54 1 0 14 55 1 0 16 56 1 6 17 57 1 0 19 58 1 0 19 59 1 0 21 60 1 1 22 61 1 0 24 62 1 0 24 63 1 0 24 64 1 0 27 65 1 0 28 66 1 0 28 67 1 0 29 68 1 0 30 69 1 6 32 70 1 0 32 71 1 0 32 72 1 0 33 73 1 0 33 74 1 0 33 75 1 0 34 76 1 0 M END

Standard InCHIKey	VJTBJVHQCFQKLQ-XTNHTTTKSA-N
Standard InCHI	InChI=1S/C28H42O6/c1-6-7-8-9-10-11-22(30)34-27-14-18(3)28(33)20(23(27)25(27,4)5)13-19(16-29)15-26(32)21(28)12-17(2)24(26)31/h12-13,18,20-21,23,29,32-33H,6-11,14-16H2,1-5H3/t18-,20+,21-,23-,26-,27+,28-/m1/s1
SMILES	CCCCCCCC(=O)O[C@@]12C[C@@H](C)[C@]3([C@@H](C=C(C[C@]4([C@H]3C=C(C)C4=O)O)CO)[C@@H]1C2(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	474.3	Volume:	500.814 ? Van der Waals volume.
Dense:	0.947	LogP:	3.654 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.571 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.211 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	20.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.28	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.854	Fsp³:	0.786
MCE-18:	76.8 ? 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:	0.174	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.233	Promiscuous compounds:	0.712

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.987	MDCK Permeability:	-4.6
Pgp-inhibitor:	0.005	Pgp-substrate:	0.808
PAMPA:	0.882 ? 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):	0.038
20% Bioavailability (F20%):	0.851	30% Bioavailability (F30%):	0.912
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.986
Plasma Protein Binding (PPB):	90.847%	Volume Distribution (VD):	0.484
Fu:	12.015% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.942
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.026
BSEP inhibitor:	0.969

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.616
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.519	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.95
CYP3A4-inhibitor:	0.029	CYP3A4-substrate:	0.887
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.11 ? 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):

5.363

Half-life (T1/2):

0.799

ADMET: Toxicity

hERG Blockers:	0.16	hERG Blockers (10um):	0.397
Human Hepatotoxicity (H-HT):	0.635	Drug-induced Liver Injury (DILI):	0.266
AMES Toxicity:	0.226	Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.311	Skin Sensitization:	0.923
Carcinogencity:	0.544	Eye Corrosion:	0.102
Eye Irritation:	0.747	Respiratory Toxicity:	0.796
Drug-induced Neurotoxicity:	0.131	Ototoxicity:	0.512
Hematotoxicity:	0.552	Drug-induced Nephrotoxicity:	0.485
Genotoxicity:	0.022	RPMI-8226 Immunitoxicity:	0.075
A549 Cytotoxicity:	0.233	Hek293 Cytotoxicity:	0.181
BCF:	1.47 ? 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:	4.118 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.881 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.052 ? 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
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	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

Activity Type	# Activity
IC50	4
Activity	1

Activity Type	# Activity
Cell line	5

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
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT2740	Cell line	Neutrophils	n.a.	Activity	=	109.6	%	PMID[28445049]
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	2100.0	nM	PMID[28445049]

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 NPC277477 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	15530
0.1-0.2	32588
0.2-0.3	1568
0.3-0.4	70
0.4-0.5	31
0.5-0.6	31
0.6-0.7	15
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC485736
1.0	High Similarity	NPC479003
1.0	High Similarity	NPC485735
0.8889	High Similarity	NPC485732
0.8136	Intermediate Similarity	NPC153036
0.8095	Intermediate Similarity	NPC485733
0.7869	Intermediate Similarity	NPC158523
0.7846	Intermediate Similarity	NPC482454
0.7727	Intermediate Similarity	NPC17138
0.7727	Intermediate Similarity	NPC101825
0.7727	Intermediate Similarity	NPC215643
0.7727	Intermediate Similarity	NPC265499
0.7619	Intermediate Similarity	NPC71889
0.7619	Intermediate Similarity	NPC475937
0.7612	Intermediate Similarity	NPC221511
0.7286	Intermediate Similarity	NPC151216
0.7286	Intermediate Similarity	NPC89227
0.7246	Intermediate Similarity	NPC485731
0.7206	Intermediate Similarity	NPC170212
0.7123	Intermediate Similarity	NPC472760
0.7	Intermediate Similarity	NPC477091
0.6957	Remote Similarity	NPC275696
0.6957	Remote Similarity	NPC255081
0.6712	Remote Similarity	NPC479000
0.6667	Remote Similarity	NPC153651
0.662	Remote Similarity	NPC5991
0.662	Remote Similarity	NPC196500
0.662	Remote Similarity	NPC471108
0.662	Remote Similarity	NPC5989
0.6575	Remote Similarity	NPC22628
0.6575	Remote Similarity	NPC600005
0.6462	Remote Similarity	NPC91189
0.6269	Remote Similarity	NPC96739
0.6197	Remote Similarity	NPC609113
0.6143	Remote Similarity	NPC171905
0.6	Remote Similarity	NPC174471
0.5974	Remote Similarity	NPC609983
0.5946	Remote Similarity	NPC474872
0.5926	Remote Similarity	NPC180640
0.5867	Remote Similarity	NPC603912
0.5854	Remote Similarity	NPC185876
0.5854	Remote Similarity	NPC19336
0.5833	Remote Similarity	NPC474871
0.5833	Remote Similarity	NPC260786
0.5802	Remote Similarity	NPC138641
0.5802	Remote Similarity	NPC611243
0.5652	Remote Similarity	NPC156252
0.5641	Remote Similarity	NPC484333
0.5513	Remote Similarity	NPC183540
0.5479	Remote Similarity	NPC472397
0.5432	Remote Similarity	NPC159692
0.5333	Remote Similarity	NPC157252
0.5333	Remote Similarity	NPC472758
0.5309	Remote Similarity	NPC222307
0.5301	Remote Similarity	NPC469647
0.5301	Remote Similarity	NPC469648
0.527	Remote Similarity	NPC478681
0.5263	Remote Similarity	NPC471125
0.5195	Remote Similarity	NPC145182
0.5122	Remote Similarity	NPC602538
0.5119	Remote Similarity	NPC482199
0.5119	Remote Similarity	NPC482197
0.5116	Remote Similarity	NPC479001
0.5116	Remote Similarity	NPC479002
0.5114	Remote Similarity	NPC283875
0.5063	Remote Similarity	NPC471128
0.5063	Remote Similarity	NPC471126

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC277477 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6346
0.1-0.2	2759
0.2-0.3	45
0.3-0.4	0
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