NPASS Compound

Natural Product: NPC261946

Natural Product ID	NPC261946
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JESPWQGCCOLVKQ-AVFWISQGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	442671
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 66 71 0 0 0 0 0 0 0 0999 V2000 3.5310 1.0065 0.5469 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3651 2.0246 1.0210 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5972 2.1778 2.3709 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0064 1.3242 3.2771 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1727 0.3068 2.8007 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9299 0.1392 1.4570 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0397 -0.9582 1.0246 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8555 -2.1504 0.5785 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2782 -2.0512 -0.8552 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1393 -1.7364 -1.7598 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1323 -2.1898 -3.0702 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0510 -1.8675 -3.8624 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0184 -1.1130 -3.3387 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0249 -0.6620 -2.0358 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1164 0.1337 -1.5572 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7841 1.4514 -1.0271 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3405 2.1178 -1.4072 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6102 3.3543 -0.8799 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2027 3.9749 0.0280 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3473 3.2981 0.4154 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6352 2.0420 -0.1108 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7929 1.4251 0.3194 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1059 0.1332 -0.1737 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1530 -0.5083 0.6113 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3290 0.1871 0.8026 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3749 -0.3428 1.5517 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2224 -1.5986 2.1146 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0540 -2.2654 1.9126 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9881 -1.7456 1.1596 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2844 -2.0981 2.8557 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8659 -0.6209 -0.4326 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0776 -1.9377 -0.8501 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0709 5.2296 0.5632 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2218 1.5349 -2.3403 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1091 -0.9889 -1.2523 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1198 -0.5443 0.0384 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0455 -0.8181 -4.1821 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2105 -2.9481 -3.5323 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 -3.3501 0.8586 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4331 3.2044 2.7848 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3296 0.8600 -0.4983 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8310 2.6960 0.3245 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1981 1.4578 4.3285 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7068 -0.3656 3.5058 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4349 -1.2728 1.8980 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8042 -2.1242 1.1914 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1136 -1.3473 -1.0264 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6360 -3.0652 -1.1612 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0380 -2.2210 -4.8958 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8809 0.2387 -2.3553 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5200 3.8843 -1.1926 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0027 3.7678 1.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5836 0.3535 -1.1908 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5042 1.1736 0.3858 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2960 0.2063 1.6993 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9420 -3.2334 2.3493 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1123 -2.3701 1.0818 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1233 -2.3522 2.3133 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1780 -0.6083 0.4356 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2190 -2.4409 -0.7300 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6851 5.7587 0.9931 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2594 1.9829 -3.2335 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0541 -0.0263 -4.8073 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3839 -3.8187 -3.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2032 -3.4468 1.8516 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0049 3.7432 2.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 27 30 1 0 23 31 1 0 31 32 1 0 19 33 1 0 17 34 1 0 14 35 2 0 35 36 1 0 13 37 1 0 11 38 1 0 8 39 1 0 3 40 1 0 6 1 1 0 36 7 1 0 35 10 1 0 31 15 1 0 21 16 1 0 29 24 1 0 1 41 1 0 2 42 1 0 4 43 1 0 5 44 1 0 7 45 1 1 8 46 1 1 9 47 1 0 9 48 1 0 12 49 1 0 15 50 1 6 18 51 1 0 20 52 1 0 23 53 1 6 25 54 1 0 26 55 1 0 28 56 1 0 29 57 1 0 30 58 1 0 31 59 1 1 32 60 1 0 33 61 1 0 34 62 1 0 37 63 1 0 38 64 1 0 39 65 1 0 40 66 1 0 M END

Standard InCHIKey	JESPWQGCCOLVKQ-AVFWISQGSA-N
Standard InCHI	InChI=1S/C30H26O10/c31-15-5-1-13(2-6-15)28-22(37)11-18-19(34)12-21(36)25(30(18)40-28)26-24-20(35)9-17(33)10-23(24)39-29(27(26)38)14-3-7-16(32)8-4-14/h1-10,12,22,26-29,31-38H,11H2/t22-,26-,27-,28+,29+/m0/s1
SMILES	c1cc(ccc1[C@@H]1[C@H](Cc2c(cc(c([C@@H]3c4c(cc(cc4O[C@H](c4ccc(cc4)O)[C@H]3O)O)O)c2O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	546.15	Volume:	532.362 ? Van der Waals volume.
Dense:	1.026	LogP:	1.737 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.92 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.871 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	34.0
TPSA:	180.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.189	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.326	Fsp³:	0.2
MCE-18:	120.0 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.739	Fluc inhibitor:	0.273 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.279 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.43 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.513	Promiscuous compounds:	0.17

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.904	MDCK Permeability:	-5.014
Pgp-inhibitor:	0.001	Pgp-substrate:	0.647
PAMPA:	0.078 ? 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%):	0.209	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.832
Plasma Protein Binding (PPB):	92.917%	Volume Distribution (VD):	0.522
Fu:	9.935% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.18
BSEP inhibitor:	0.234

ADMET: Metabolism

CYP1A2-inhibitor:	0.493	CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.961	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

5.272

Half-life (T1/2):

3.359

ADMET: Toxicity

hERG Blockers:	0.103	hERG Blockers (10um):	0.646
Human Hepatotoxicity (H-HT):	0.847	Drug-induced Liver Injury (DILI):	0.098
AMES Toxicity:	0.414	Rat Oral Acute Toxicity:	0.411
Maximum Recommended Daily Dose:	0.957	Skin Sensitization:	0.964
Carcinogencity:	0.035	Eye Corrosion:	0.0
Eye Irritation:	0.951	Respiratory Toxicity:	0.792
Drug-induced Neurotoxicity:	0.281	Ototoxicity:	0.62
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.409
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.162
A549 Cytotoxicity:	0.904	Hek293 Cytotoxicity:	0.984
BCF:	1.182 ? 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:	3.654 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.541 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.132 ? 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
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17944538]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22823026]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	leaves and stems	Ha Long, Quang Ninh province, Vietnam	2014-Jul	PMID[25769817]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29792702]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14254	Kandelia candel	Species	Rhizophoraceae	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 NPC261946 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	24348
0.1-0.2	22131
0.2-0.3	2952
0.3-0.4	285
0.4-0.5	51
0.5-0.6	41
0.6-0.7	22
0.7-0.8	0
0.8-0.85	6
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8689	High Similarity	NPC211561
0.8621	High Similarity	NPC58190
0.8621	High Similarity	NPC108811
0.8621	High Similarity	NPC170103
0.8621	High Similarity	NPC236202
0.8621	High Similarity	NPC262911
0.8621	High Similarity	NPC202742
0.8475	Intermediate Similarity	NPC246202
0.8475	Intermediate Similarity	NPC224161
0.8475	Intermediate Similarity	NPC46335
0.8475	Intermediate Similarity	NPC279406
0.8475	Intermediate Similarity	NPC486519
0.8305	Intermediate Similarity	NPC601999
0.7966	Intermediate Similarity	NPC96576
0.7656	Intermediate Similarity	NPC70409
0.7656	Intermediate Similarity	NPC204770
0.7656	Intermediate Similarity	NPC600551
0.7656	Intermediate Similarity	NPC601980
0.7656	Intermediate Similarity	NPC602065
0.7656	Intermediate Similarity	NPC611024
0.7576	Intermediate Similarity	NPC278548
0.7538	Intermediate Similarity	NPC601997
0.7538	Intermediate Similarity	NPC609211
0.7538	Intermediate Similarity	NPC610665
0.7344	Intermediate Similarity	NPC313116
0.7344	Intermediate Similarity	NPC603340
0.7143	Intermediate Similarity	NPC277331
0.7143	Intermediate Similarity	NPC100482
0.7015	Intermediate Similarity	NPC226809
0.6912	Remote Similarity	NPC600630
0.6912	Remote Similarity	NPC607896
0.6912	Remote Similarity	NPC611369
0.6909	Remote Similarity	NPC207179
0.6909	Remote Similarity	NPC167571
0.6909	Remote Similarity	NPC278552
0.6667	Remote Similarity	NPC86630
0.6622	Remote Similarity	NPC147743
0.6622	Remote Similarity	NPC4809
0.6622	Remote Similarity	NPC73517
0.6579	Remote Similarity	NPC106601
0.6579	Remote Similarity	NPC151474
0.6515	Remote Similarity	NPC294558
0.6515	Remote Similarity	NPC18185
0.6515	Remote Similarity	NPC263940
0.6494	Remote Similarity	NPC212614
0.6494	Remote Similarity	NPC205613
0.6471	Remote Similarity	NPC155564
0.625	Remote Similarity	NPC159526
0.6129	Remote Similarity	NPC178054
0.6111	Remote Similarity	NPC134911
0.6081	Remote Similarity	NPC306267
0.5921	Remote Similarity	NPC471404
0.589	Remote Similarity	NPC46283
0.589	Remote Similarity	NPC469944
0.589	Remote Similarity	NPC302549
0.5833	Remote Similarity	NPC261619
0.5833	Remote Similarity	NPC61477
0.5833	Remote Similarity	NPC78770
0.5833	Remote Similarity	NPC219876
0.5833	Remote Similarity	NPC126029
0.5833	Remote Similarity	NPC15658
0.575	Remote Similarity	NPC78074
0.5733	Remote Similarity	NPC20050
0.5714	Remote Similarity	NPC184245
0.5714	Remote Similarity	NPC187801
0.5714	Remote Similarity	NPC610920
0.5676	Remote Similarity	NPC65333
0.5625	Remote Similarity	NPC171932
0.5584	Remote Similarity	NPC135021
0.557	Remote Similarity	NPC9309
0.5556	Remote Similarity	NPC478340
0.5541	Remote Similarity	NPC272552
0.5541	Remote Similarity	NPC226108
0.5541	Remote Similarity	NPC322899
0.5488	Remote Similarity	NPC478337
0.5488	Remote Similarity	NPC478338
0.5455	Remote Similarity	NPC478616
0.5455	Remote Similarity	NPC478339
0.5395	Remote Similarity	NPC44192
0.5385	Remote Similarity	NPC16435
0.5349	Remote Similarity	NPC478617
0.5333	Remote Similarity	NPC482472
0.5246	Remote Similarity	NPC268266
0.5246	Remote Similarity	NPC42760
0.5246	Remote Similarity	NPC220825
0.5246	Remote Similarity	NPC268342
0.5211	Remote Similarity	NPC82917
0.5132	Remote Similarity	NPC186228
0.5079	Remote Similarity	NPC47398
0.5079	Remote Similarity	NPC234333
0.5079	Remote Similarity	NPC260898
0.5077	Remote Similarity	NPC61946

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC261946 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4912
0.1-0.2	4165
0.2-0.3	62
0.3-0.4	8
0.4-0.5	1
0.5-0.6	2
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
0.5833	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1613	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