NPASS Compound

Natural Product: NPC152156

Natural Product ID	NPC152156
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CMAUMDKYDZZLTH-CATNFWIESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5321203
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 72 76 0 0 0 0 0 0 0 0999 V2000 7.1809 1.4002 -0.3868 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2593 -0.0258 -0.8072 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8418 -0.9202 0.2868 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5332 -2.3403 -0.1750 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0856 -2.6130 -0.1267 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3201 -1.3004 -0.5170 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1308 -1.6680 -1.0458 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9342 -1.5625 -0.5480 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2031 -0.2874 -0.3240 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9158 0.7910 0.3865 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9918 1.9754 0.6583 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6817 1.5051 1.1390 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1379 0.5398 0.0654 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1852 0.3434 0.3337 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3263 0.3749 -0.3801 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5042 0.1441 0.3471 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7526 0.1412 -0.2410 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8037 0.3784 -1.5991 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0368 0.3795 -2.2077 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0838 0.5913 -3.4308 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1525 0.1403 -1.4013 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0592 -0.0909 -0.0518 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2246 -0.3391 0.7910 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0602 -0.5301 2.1425 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1125 -0.7709 3.0201 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3935 -0.8192 2.4936 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5883 -0.6339 1.1577 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5015 -0.3911 0.2901 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4836 -1.0596 3.3428 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8425 -0.0779 0.4640 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6350 0.6105 -2.3357 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3950 0.6096 -1.7311 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2396 0.8441 -2.4870 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7283 0.8444 -3.6936 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9324 -0.6073 0.2578 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2753 2.5168 1.2398 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5857 2.7897 1.6428 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9252 1.2858 -0.4919 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1270 -0.5803 -1.3357 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6607 -2.9910 1.1595 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2996 -3.2586 0.5528 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2425 -0.7655 0.2332 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8204 1.5066 0.6550 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1894 1.9087 -0.4136 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5076 2.0084 -1.0268 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0286 -0.0414 -1.6513 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4284 -0.7459 1.2732 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8446 -2.3619 -1.2638 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7316 -3.3647 -0.8404 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1885 -0.7901 0.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2315 -2.1570 -1.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7889 -2.2408 0.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8793 0.1555 -1.3261 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3636 0.4989 1.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8159 2.5463 -0.2977 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7313 0.9950 2.1286 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4319 0.9376 -0.8977 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4793 -0.0436 1.4243 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1199 0.1467 -1.9061 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0545 -0.4905 2.5355 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0030 -0.9202 4.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5811 -0.6648 0.7087 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6783 -0.2507 -0.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4370 -0.9044 3.0808 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3125 1.1229 -3.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6591 0.0984 -4.3631 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8586 2.4024 2.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8561 3.6191 1.2080 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4197 1.9423 0.1097 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4817 -3.2185 1.6784 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2671 -3.1010 0.3221 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5723 -1.0524 -0.6726 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 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 26 29 1 0 22 30 1 0 18 31 1 0 31 32 2 0 32 33 1 0 31 34 1 0 13 35 1 0 12 36 1 0 11 37 1 0 10 38 1 0 6 39 1 0 5 40 1 0 4 41 1 0 3 42 1 0 39 2 1 0 35 9 1 0 32 15 1 0 30 17 1 0 28 23 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 6 3 47 1 1 4 48 1 6 5 49 1 6 6 50 1 1 8 51 1 0 8 52 1 0 9 53 1 6 10 54 1 1 11 55 1 6 12 56 1 1 13 57 1 6 16 58 1 0 21 59 1 0 24 60 1 0 25 61 1 0 27 62 1 0 28 63 1 0 29 64 1 0 33 65 1 0 34 66 1 0 36 67 1 0 37 68 1 0 38 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	CMAUMDKYDZZLTH-CATNFWIESA-N
Standard InCHI	InChI=1S/C27H30O15/c1-9-18(30)22(34)24(36)26(39-9)38-8-16-20(32)23(35)25(37)27(42-16)41-15-7-14-17(21(33)19(15)31)12(29)6-13(40-14)10-2-4-11(28)5-3-10/h2-7,9,16,18,20,22-28,30-37H,8H2,1H3/t9-,16+,18-,20+,22+,23-,24+,25+,26+,27+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3cc4c(c(=O)cc(c5ccc(cc5)O)o4)c(c3O)O)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	0.802 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.269 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.437 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.149	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.715	Fsp³:	0.444
MCE-18:	119.436 ? 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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.603	Fluc inhibitor:	0.304 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.866 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.617 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.128	Promiscuous compounds:	0.536

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.524	MDCK Permeability:	-5.052
Pgp-inhibitor:	0.0	Pgp-substrate:	0.9
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):	0.911
20% Bioavailability (F20%):	0.911	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.078
Plasma Protein Binding (PPB):	83.699%	Volume Distribution (VD):	0.052
Fu:	13.866% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.773
BSEP inhibitor:	0.001

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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.034
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.976
HLM stability:	0.011 ? 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):

1.463

Half-life (T1/2):

4.678

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.213
Human Hepatotoxicity (H-HT):	0.452	Drug-induced Liver Injury (DILI):	0.941
AMES Toxicity:	0.746	Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.08	Skin Sensitization:	0.962
Carcinogencity:	0.079	Eye Corrosion:	0.0
Eye Irritation:	0.669	Respiratory Toxicity:	0.014
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.836
Hematotoxicity:	0.07	Drug-induced Nephrotoxicity:	0.612
Genotoxicity:	0.845	RPMI-8226 Immunitoxicity:	0.193
A549 Cytotoxicity:	0.469	Hek293 Cytotoxicity:	0.458
BCF:	0.39 ? 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:	2.937 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.474 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.609 ? 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
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19948405]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23672042]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36483735]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5788	Millingtonia hortensis	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5788	Millingtonia hortensis	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5788	Millingtonia hortensis	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5788	Millingtonia hortensis	Species	Bignoniaceae	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 NPC152156 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	21044
0.1-0.2	25044
0.2-0.3	2783
0.3-0.4	614
0.4-0.5	256
0.5-0.6	80
0.6-0.7	27
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
0.7976	Intermediate Similarity	NPC44931
0.7195	Intermediate Similarity	NPC146792
0.7079	Intermediate Similarity	NPC210073
0.7059	Intermediate Similarity	NPC181616
0.6889	Remote Similarity	NPC22062
0.6889	Remote Similarity	NPC473634
0.6889	Remote Similarity	NPC138811
0.6848	Remote Similarity	NPC470443
0.6813	Remote Similarity	NPC204693
0.6629	Remote Similarity	NPC477848
0.6596	Remote Similarity	NPC209296
0.6562	Remote Similarity	NPC101636
0.6452	Remote Similarity	NPC186816
0.6444	Remote Similarity	NPC172807
0.6353	Remote Similarity	NPC331652
0.6344	Remote Similarity	NPC65563
0.6344	Remote Similarity	NPC470949
0.6322	Remote Similarity	NPC58716
0.6279	Remote Similarity	NPC45618
0.6237	Remote Similarity	NPC173582
0.6237	Remote Similarity	NPC265885
0.6237	Remote Similarity	NPC181465
0.6237	Remote Similarity	NPC215710
0.6237	Remote Similarity	NPC473438
0.6237	Remote Similarity	NPC253788
0.6224	Remote Similarity	NPC298171
0.617	Remote Similarity	NPC473512
0.617	Remote Similarity	NPC129827
0.6105	Remote Similarity	NPC473571
0.6105	Remote Similarity	NPC110941
0.6064	Remote Similarity	NPC67105
0.5934	Remote Similarity	NPC43211
0.5888	Remote Similarity	NPC298666
0.5876	Remote Similarity	NPC64051
0.5833	Remote Similarity	NPC203259
0.5833	Remote Similarity	NPC33054
0.5833	Remote Similarity	NPC176740
0.5833	Remote Similarity	NPC471725
0.5833	Remote Similarity	NPC303913
0.5833	Remote Similarity	NPC134532
0.5833	Remote Similarity	NPC602582
0.5778	Remote Similarity	NPC84265
0.5758	Remote Similarity	NPC473623
0.5728	Remote Similarity	NPC11468
0.5714	Remote Similarity	NPC475366
0.57	Remote Similarity	NPC270675
0.57	Remote Similarity	NPC488089
0.57	Remote Similarity	NPC195685
0.5684	Remote Similarity	NPC254540
0.567	Remote Similarity	NPC3583
0.5657	Remote Similarity	NPC65711
0.5644	Remote Similarity	NPC476472
0.5644	Remote Similarity	NPC294815
0.5644	Remote Similarity	NPC473073
0.5644	Remote Similarity	NPC16194
0.5625	Remote Similarity	NPC187379
0.56	Remote Similarity	NPC483707
0.5579	Remote Similarity	NPC211594
0.5577	Remote Similarity	NPC599948
0.5567	Remote Similarity	NPC227508
0.5566	Remote Similarity	NPC25523
0.5556	Remote Similarity	NPC39360
0.5556	Remote Similarity	NPC126784
0.5556	Remote Similarity	NPC241423
0.5556	Remote Similarity	NPC19709
0.5556	Remote Similarity	NPC29763
0.5556	Remote Similarity	NPC210003
0.5545	Remote Similarity	NPC142142
0.5543	Remote Similarity	NPC27942
0.5534	Remote Similarity	NPC472994
0.551	Remote Similarity	NPC65003
0.5495	Remote Similarity	NPC93337
0.5472	Remote Similarity	NPC472993
0.5446	Remote Similarity	NPC473327
0.5443	Remote Similarity	NPC198826
0.5435	Remote Similarity	NPC105025
0.5421	Remote Similarity	NPC473644
0.5408	Remote Similarity	NPC39834
0.537	Remote Similarity	NPC311850
0.5368	Remote Similarity	NPC99957
0.5347	Remote Similarity	NPC12013
0.5347	Remote Similarity	NPC11432
0.5347	Remote Similarity	NPC477613
0.5306	Remote Similarity	NPC295613
0.5306	Remote Similarity	NPC471079
0.5306	Remote Similarity	NPC473657
0.5294	Remote Similarity	NPC229409
0.5269	Remote Similarity	NPC245014
0.5253	Remote Similarity	NPC47923
0.5225	Remote Similarity	NPC68592
0.5217	Remote Similarity	NPC108831
0.5217	Remote Similarity	NPC182634
0.5189	Remote Similarity	NPC603856
0.5179	Remote Similarity	NPC198199
0.5158	Remote Similarity	NPC237435
0.5143	Remote Similarity	NPC221342
0.5143	Remote Similarity	NPC476470
0.5138	Remote Similarity	NPC480441
0.5109	Remote Similarity	NPC473043
0.5106	Remote Similarity	NPC46420
0.5098	Remote Similarity	NPC46202
0.5094	Remote Similarity	NPC602448
0.5093	Remote Similarity	NPC189564
0.5054	Remote Similarity	NPC249281
0.5054	Remote Similarity	NPC476405
0.5054	Remote Similarity	NPC83283
0.505	Remote Similarity	NPC479405
0.505	Remote Similarity	NPC156869
0.5048	Remote Similarity	NPC470447
0.5048	Remote Similarity	NPC477629
0.5043	Remote Similarity	NPC120952

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC152156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5520
0.1-0.2	3565
0.2-0.3	53
0.3-0.4	6
0.4-0.5	0
0.5-0.6	5
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
0.6596	Remote Similarity	NPD7054	Phase 4
0.5833	Remote Similarity	NPD6797	Phase 2
0.5728	Remote Similarity	NPD7472	Pre-clinical
0.5644	Remote Similarity	NPD7251	Phase 2
0.5158	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.514	Remote Similarity	NPD7808	Phase 3

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