NPASS Compound

Natural Product: NPC486577

Natural Product ID	NPC486577
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MHSLLESNBWNULL-GDDOJEIXSA-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]

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 71 75 0 0 0 0 0 0 0 0999 V2000 8.1671 -3.8123 0.5954 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0570 -4.4921 0.0399 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8552 -3.7983 -0.0252 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7647 -4.4677 -0.5726 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5713 -3.7838 -0.6399 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4428 -2.4919 -0.1894 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5034 -1.8074 0.3561 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7134 -2.5039 0.4226 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3795 -0.5907 0.7809 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2401 0.1134 0.7350 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2639 1.4761 1.2595 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5064 2.0964 1.4400 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6291 3.3523 1.9817 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5315 4.0831 2.3824 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3063 3.4890 2.2130 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1797 2.2025 1.6595 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1781 4.1861 2.6008 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6329 5.3510 2.9297 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1332 -0.4867 0.2020 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2339 -1.8012 -0.2616 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2792 -2.4384 -0.7566 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9085 0.1059 0.0726 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4837 0.8651 -1.0724 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3437 -0.0231 -1.9405 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3451 0.7761 -2.7238 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1096 1.7801 -1.8866 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5118 1.9770 -0.5732 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9347 1.1762 0.5909 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2805 0.9160 0.7810 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0368 0.0209 0.0826 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5198 -0.6852 -0.8126 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4830 -0.1541 0.3467 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1173 0.5629 1.3183 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4690 0.3893 1.5434 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2064 -0.5146 0.7879 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5661 -1.2321 -0.1861 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2207 -1.0498 -0.3994 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3008 -2.1391 -0.9455 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5664 -0.7126 0.9880 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1223 1.1042 2.5194 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1099 1.9958 -0.6166 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0993 3.0475 -2.5862 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1533 -0.0369 -3.4960 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5092 -0.5808 -2.9512 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4682 -4.4213 -1.1793 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3310 -2.8244 0.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0945 -4.4235 0.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9819 -3.5537 1.6738 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8558 -5.4851 -0.9299 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5466 -1.9775 0.8460 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4013 1.5425 1.1323 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5986 3.8217 2.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2136 1.7532 1.5778 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6989 4.8524 1.9992 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2675 6.1185 2.3526 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3840 1.1380 -1.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -0.8616 -1.4107 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7550 1.3899 -3.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1597 1.5339 -1.8725 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7476 3.0695 -0.2779 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5929 1.6814 1.5725 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3322 0.2100 0.6500 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5773 1.2743 1.9250 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7024 -1.6234 -1.1808 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0256 -1.8368 -1.5907 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1763 -0.9009 0.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8335 0.6008 3.0541 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5535 3.6910 -2.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0223 0.3794 -3.7332 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0170 -1.2737 -3.4592 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5276 -5.3388 -1.6159 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 14 18 1 0 10 19 2 0 19 20 1 0 20 21 2 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 36 38 1 0 35 39 1 0 34 40 1 0 27 41 1 0 26 42 1 0 25 43 1 0 24 44 1 0 5 45 1 0 8 3 1 0 16 11 1 0 41 23 1 0 20 6 1 0 37 32 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 8 50 1 0 12 51 1 0 13 52 1 0 16 53 1 0 17 54 1 0 18 55 1 0 23 56 1 6 24 57 1 1 25 58 1 6 26 59 1 1 27 60 1 1 28 61 1 0 28 62 1 0 33 63 1 0 37 64 1 0 38 65 1 0 39 66 1 0 40 67 1 0 42 68 1 0 43 69 1 0 44 70 1 0 45 71 1 0 M END

Standard InCHIKey	MHSLLESNBWNULL-GDDOJEIXSA-N
Standard InCHI	InChI=1S/C29H26O16/c1-41-12-7-15(32)20-18(8-12)43-26(10-2-3-13(30)14(31)4-10)27(23(20)37)45-29-25(39)24(38)22(36)19(44-29)9-42-28(40)11-5-16(33)21(35)17(34)6-11/h2-8,19,22,24-25,29-36,38-39H,9H2,1H3/t19-,22-,24+,25-,29+/m1/s1
SMILES	COc1cc(c2c(c1)oc(c1ccc(c(c1)O)O)c(c2=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c2cc(c(c(c2)O)O)O)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	630.12	Volume:	576.364 ? Van der Waals volume.
Dense:	1.093	LogP:	1.158 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.421 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.046 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	31.0
TPSA:	266.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.101	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.308	Fsp³:	0.241
MCE-18:	114.722 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.72	Fluc inhibitor:	0.287 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.942 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.784 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.071	Promiscuous compounds:	0.951

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.25	MDCK Permeability:	-5.126
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
PAMPA:	0.788 ? 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):	0.012
20% Bioavailability (F20%):	0.945	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.973
Plasma Protein Binding (PPB):	84.316%	Volume Distribution (VD):	-0.123
Fu:	14.271% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.984
BSEP inhibitor:	0.137

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.959
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.939
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.974 ? 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):

3.814

Half-life (T1/2):

3.835

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.773
Human Hepatotoxicity (H-HT):	0.124	Drug-induced Liver Injury (DILI):	0.987
AMES Toxicity:	0.83	Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.551	Skin Sensitization:	1.0
Carcinogencity:	0.247	Eye Corrosion:	0.0
Eye Irritation:	0.7	Respiratory Toxicity:	0.018
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.976
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.005
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.007
A549 Cytotoxicity:	0.993	Hek293 Cytotoxicity:	0.501
BCF:	0.624 ? 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:	3.522 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.641 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.214 ? 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
NPO40956	Woodfordia uniflora	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32639158]

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
MIC	2

Activity Type	# Activity
Organism	2

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
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	317400.0	nM	PMID[32639158]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	10000.0	nM	PMID[32639158]

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 NPC486577 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	19597
0.1-0.2	26225
0.2-0.3	3018
0.3-0.4	556
0.4-0.5	288
0.5-0.6	137
0.6-0.7	17
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.809	Intermediate Similarity	NPC37668
0.75	Intermediate Similarity	NPC270448
0.7473	Intermediate Similarity	NPC154741
0.7093	Intermediate Similarity	NPC271692
0.6915	Remote Similarity	NPC296018
0.6591	Remote Similarity	NPC158674
0.6591	Remote Similarity	NPC136042
0.6517	Remote Similarity	NPC84362
0.6465	Remote Similarity	NPC135831
0.6458	Remote Similarity	NPC129264
0.6373	Remote Similarity	NPC121703
0.6364	Remote Similarity	NPC97119
0.6354	Remote Similarity	NPC293626
0.6333	Remote Similarity	NPC46420
0.625	Remote Similarity	NPC267680
0.6237	Remote Similarity	NPC605784
0.6122	Remote Similarity	NPC186816
0.6105	Remote Similarity	NPC116864
0.6105	Remote Similarity	NPC244776
0.6022	Remote Similarity	NPC611303
0.6	Remote Similarity	NPC470443
0.5978	Remote Similarity	NPC27640
0.5934	Remote Similarity	NPC249281
0.5882	Remote Similarity	NPC603079
0.587	Remote Similarity	NPC297987
0.5833	Remote Similarity	NPC277532
0.581	Remote Similarity	NPC81042
0.5784	Remote Similarity	NPC229409
0.5761	Remote Similarity	NPC289667
0.5758	Remote Similarity	NPC67326
0.5743	Remote Similarity	NPC488073
0.5743	Remote Similarity	NPC126784
0.5743	Remote Similarity	NPC241423
0.5743	Remote Similarity	NPC488074
0.5714	Remote Similarity	NPC223426
0.57	Remote Similarity	NPC203259
0.57	Remote Similarity	NPC33054
0.57	Remote Similarity	NPC176740
0.57	Remote Similarity	NPC471725
0.57	Remote Similarity	NPC134532
0.57	Remote Similarity	NPC156869
0.57	Remote Similarity	NPC602582
0.5684	Remote Similarity	NPC488071
0.5682	Remote Similarity	NPC25389
0.5673	Remote Similarity	NPC473073
0.567	Remote Similarity	NPC276377
0.5619	Remote Similarity	NPC470445
0.56	Remote Similarity	NPC67105
0.5596	Remote Similarity	NPC480441
0.5579	Remote Similarity	NPC59534
0.5567	Remote Similarity	NPC116458
0.5567	Remote Similarity	NPC246943
0.5566	Remote Similarity	NPC470446
0.5545	Remote Similarity	NPC210073
0.5545	Remote Similarity	NPC150164
0.5534	Remote Similarity	NPC65711
0.5526	Remote Similarity	NPC488078
0.5521	Remote Similarity	NPC175107
0.55	Remote Similarity	NPC476773
0.549	Remote Similarity	NPC35167
0.549	Remote Similarity	NPC144097
0.5488	Remote Similarity	NPC188871
0.5481	Remote Similarity	NPC72016
0.5474	Remote Similarity	NPC305811
0.5455	Remote Similarity	NPC166277
0.5455	Remote Similarity	NPC265115
0.5437	Remote Similarity	NPC253521
0.5437	Remote Similarity	NPC153755
0.5437	Remote Similarity	NPC113836
0.5426	Remote Similarity	NPC127546
0.5426	Remote Similarity	NPC57625
0.5426	Remote Similarity	NPC173637
0.5426	Remote Similarity	NPC317489
0.5426	Remote Similarity	NPC238376
0.5426	Remote Similarity	NPC223424
0.5426	Remote Similarity	NPC600591
0.5417	Remote Similarity	NPC42773
0.5417	Remote Similarity	NPC45522
0.5413	Remote Similarity	NPC470451
0.54	Remote Similarity	NPC254540
0.54	Remote Similarity	NPC251417
0.5393	Remote Similarity	NPC472859
0.537	Remote Similarity	NPC214621
0.537	Remote Similarity	NPC34267
0.537	Remote Similarity	NPC14187
0.5368	Remote Similarity	NPC145038
0.5368	Remote Similarity	NPC56077
0.5368	Remote Similarity	NPC281131
0.5368	Remote Similarity	NPC253662
0.5368	Remote Similarity	NPC179950
0.5368	Remote Similarity	NPC277205
0.5368	Remote Similarity	NPC37919
0.5368	Remote Similarity	NPC88789
0.5368	Remote Similarity	NPC491374
0.5357	Remote Similarity	NPC139571
0.5333	Remote Similarity	NPC606657
0.5294	Remote Similarity	NPC39834
0.5294	Remote Similarity	NPC275454
0.5294	Remote Similarity	NPC227508
0.5288	Remote Similarity	NPC46202
0.5288	Remote Similarity	NPC64051
0.5283	Remote Similarity	NPC142142
0.5263	Remote Similarity	NPC19709
0.5258	Remote Similarity	NPC599850
0.5238	Remote Similarity	NPC483414
0.5238	Remote Similarity	NPC483415
0.5234	Remote Similarity	NPC85751
0.5234	Remote Similarity	NPC471669
0.5234	Remote Similarity	NPC19240
0.5208	Remote Similarity	NPC189142
0.5208	Remote Similarity	NPC77660
0.52	Remote Similarity	NPC190003
0.5196	Remote Similarity	NPC480466
0.5196	Remote Similarity	NPC471079
0.5196	Remote Similarity	NPC609888
0.5189	Remote Similarity	NPC483416
0.5189	Remote Similarity	NPC473327
0.5185	Remote Similarity	NPC36138
0.5179	Remote Similarity	NPC217520
0.5161	Remote Similarity	NPC160780
0.5155	Remote Similarity	NPC24043
0.5155	Remote Similarity	NPC349108
0.5146	Remote Similarity	NPC173582
0.5146	Remote Similarity	NPC265885
0.5146	Remote Similarity	NPC181465
0.5146	Remote Similarity	NPC215710
0.5146	Remote Similarity	NPC473438
0.5146	Remote Similarity	NPC253788
0.5143	Remote Similarity	NPC470125
0.5143	Remote Similarity	NPC64425
0.514	Remote Similarity	NPC270675
0.514	Remote Similarity	NPC195685
0.5138	Remote Similarity	NPC470450
0.5096	Remote Similarity	NPC233994
0.5096	Remote Similarity	NPC22062
0.5096	Remote Similarity	NPC65563
0.5096	Remote Similarity	NPC473634
0.5096	Remote Similarity	NPC470949
0.5096	Remote Similarity	NPC138811
0.5094	Remote Similarity	NPC488364
0.5093	Remote Similarity	NPC80068
0.5093	Remote Similarity	NPC476472
0.5093	Remote Similarity	NPC294815
0.5093	Remote Similarity	NPC16194
0.5089	Remote Similarity	NPC292019
0.5089	Remote Similarity	NPC202908
0.5089	Remote Similarity	NPC480796
0.5089	Remote Similarity	NPC472993
0.5089	Remote Similarity	NPC477895
0.5085	Remote Similarity	NPC209550
0.5056	Remote Similarity	NPC484156
0.5053	Remote Similarity	NPC67037
0.5053	Remote Similarity	NPC255615
0.505	Remote Similarity	NPC355481
0.5048	Remote Similarity	NPC473571
0.5048	Remote Similarity	NPC110941
0.5047	Remote Similarity	NPC209296
0.5044	Remote Similarity	NPC25523

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4378
0.1-0.2	4701
0.2-0.3	61
0.3-0.4	4
0.4-0.5	2
0.5-0.6	3
0.6-0.7	1
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
0.6465	Remote Similarity	NPD7251	Phase 2
0.57	Remote Similarity	NPD6797	Phase 2
0.5463	Remote Similarity	NPD7808	Phase 3
0.5047	Remote Similarity	NPD7054	Phase 4

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