NPASS Compound

Natural Product: NPC312131

Natural Product ID	NPC312131
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HCPRGPVRLFRENV-ZRGMOMPTSA-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] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 80 83 0 0 0 0 0 0 0 0999 V2000 2.5375 -0.6517 -0.9654 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3927 0.5759 -1.8515 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4400 1.5612 -1.4172 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9866 2.4483 -0.2882 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5911 2.9768 -0.6445 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7123 1.7407 -0.7558 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1234 1.0637 -1.8886 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5827 2.1662 -0.8832 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4306 1.7228 0.1577 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8850 2.8852 0.9837 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1893 2.5662 1.6354 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6721 3.6362 2.5784 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7080 3.7657 3.5772 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1093 2.3631 0.5815 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8745 1.0657 0.1337 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4936 0.8305 -0.3519 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1459 -0.5275 -0.1546 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8606 0.7200 -0.7881 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7020 -0.2897 -0.2993 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7625 -0.6581 -1.2925 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5972 -1.7261 -0.6885 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2774 -3.0768 -0.8629 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0411 -4.0732 -0.3091 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1401 -3.7770 0.4314 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4639 -2.4340 0.6088 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6984 -1.4194 0.0532 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5889 -2.1358 1.3670 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9232 -4.7646 0.9981 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0689 4.0025 0.1611 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6994 3.5424 -1.9052 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9880 1.8276 0.9368 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5986 0.8414 -1.1239 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8006 0.9701 -1.7847 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8759 1.7868 -2.7173 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9219 0.1463 -1.3605 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8170 -0.7116 -0.3701 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8996 -1.5512 0.0881 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6998 -2.4319 1.1407 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6859 -3.2586 1.6266 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9369 -3.2409 1.0718 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1612 -2.3816 0.0322 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1546 -1.5441 -0.4567 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4095 -2.3272 -0.5617 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9467 -4.0732 1.5537 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0594 -0.5063 0.0201 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6095 -0.8859 -0.8007 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0875 -1.5560 -1.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6656 0.2496 -2.8824 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6800 2.2438 -2.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6309 3.3503 -0.2408 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2065 3.6601 0.1197 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7891 1.1242 0.1711 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7532 1.1119 0.8265 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1342 3.1928 1.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0817 1.6207 2.1917 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5992 3.2729 3.0581 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8572 4.5928 2.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0602 3.5052 4.4634 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0477 0.4112 1.0263 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5137 0.9392 -1.4776 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3043 -0.7948 0.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1256 -1.1689 0.0517 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1962 0.1210 0.6242 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3824 0.2312 -1.5266 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3156 -0.9841 -2.2474 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3992 -3.2912 -1.4554 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7594 -5.0937 -0.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9911 -0.3792 0.2192 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4835 -2.4258 0.9839 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6952 -5.7242 0.8926 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3588 3.9556 -0.5467 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4735 2.9131 -2.6348 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6588 1.1251 1.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8548 0.2473 -1.8738 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8503 -0.8148 0.1606 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7149 -2.4758 1.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5176 -3.9475 2.4553 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3872 -0.8795 -1.2856 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8140 -1.3901 -0.6627 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8948 -3.7015 1.5938 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 11 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 24 28 1 0 10 29 1 0 5 30 1 0 4 31 1 0 3 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 2 3 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 41 43 1 0 40 44 1 0 7 2 1 0 16 9 1 0 26 21 1 0 42 37 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 6 3 49 1 6 4 50 1 1 5 51 1 1 6 52 1 1 9 53 1 1 10 54 1 1 11 55 1 1 12 56 1 0 12 57 1 0 13 58 1 0 15 59 1 1 16 60 1 6 17 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 22 66 1 0 23 67 1 0 26 68 1 0 27 69 1 0 28 70 1 0 29 71 1 0 30 72 1 0 31 73 1 0 35 74 1 0 36 75 1 0 38 76 1 0 39 77 1 0 42 78 1 0 43 79 1 0 44 80 1 0 M END

Standard InCHIKey	HCPRGPVRLFRENV-ZRGMOMPTSA-N
Standard InCHI	InChI=1S/C29H36O15/c1-13-26(43-21(35)7-4-14-2-5-16(31)18(33)10-14)23(37)24(38)29(41-13)44-27-22(36)20(12-30)42-28(25(27)39)40-9-8-15-3-6-17(32)19(34)11-15/h2-7,10-11,13,20,22-34,36-39H,8-9,12H2,1H3/t13-,20-,22+,23-,24-,25-,26+,27+,28-,29-/m1/s1
SMILES	C[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)O[C@H]1[C@H]([C@@H](CO)O[C@H]([C@@H]1O)OCCc1ccc(c(c1)O)O)O)O)O)OC(=O)C=Cc1ccc(c(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.21	Volume:	586.676 ? Van der Waals volume.
Dense:	1.064	LogP:	0.174 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.747 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.596 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	26.0
TPSA:	245.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	4.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.087	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.742	Fsp³:	0.483
MCE-18:	100.488 ? 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:	0.701	Fluc inhibitor:	0.664 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.118 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.611 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.273	Promiscuous compounds:	0.417

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.643	MDCK Permeability:	-5.15
Pgp-inhibitor:	0.0	Pgp-substrate:	0.288
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):	0.925
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.427
Plasma Protein Binding (PPB):	66.313%	Volume Distribution (VD):	-0.282
Fu:	30.776% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.983
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.06
BSEP inhibitor:	0.009

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:	0.016
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.933
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.526 ? 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):

4.585

Half-life (T1/2):

3.484

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.65
Human Hepatotoxicity (H-HT):	0.321	Drug-induced Liver Injury (DILI):	0.364
AMES Toxicity:	0.832	Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.053	Skin Sensitization:	1.0
Carcinogencity:	0.008	Eye Corrosion:	0.0
Eye Irritation:	0.179	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.995
Hematotoxicity:	0.042	Drug-induced Nephrotoxicity:	0.512
Genotoxicity:	0.236	RPMI-8226 Immunitoxicity:	0.031
A549 Cytotoxicity:	0.963	Hek293 Cytotoxicity:	0.393
BCF:	0.617 ? 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:	3.362 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.121 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.402 ? 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
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[19674905]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32044231]
NPO3751	Orthantha lutea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12083	Hydnellum zonatum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3751	Orthantha lutea	n.a.	n.a.	n.a.	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 NPC312131 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	13094
0.1-0.2	32689
0.2-0.3	3504
0.3-0.4	426
0.4-0.5	93
0.5-0.6	35
0.6-0.7	14
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
0.7949	Intermediate Similarity	NPC483705
0.7297	Intermediate Similarity	NPC886
0.6977	Remote Similarity	NPC269141
0.6951	Remote Similarity	NPC205195
0.6818	Remote Similarity	NPC296954
0.6548	Remote Similarity	NPC64141
0.6548	Remote Similarity	NPC483706
0.6471	Remote Similarity	NPC472350
0.6471	Remote Similarity	NPC197316
0.6471	Remote Similarity	NPC89105
0.6444	Remote Similarity	NPC112
0.631	Remote Similarity	NPC81515
0.6207	Remote Similarity	NPC68092
0.6154	Remote Similarity	NPC298257
0.6154	Remote Similarity	NPC175214
0.6118	Remote Similarity	NPC260425
0.5977	Remote Similarity	NPC328273
0.5976	Remote Similarity	NPC55608
0.5955	Remote Similarity	NPC76406
0.5921	Remote Similarity	NPC100558
0.5889	Remote Similarity	NPC611289
0.5882	Remote Similarity	NPC488390
0.5824	Remote Similarity	NPC263829
0.5638	Remote Similarity	NPC205864
0.5638	Remote Similarity	NPC247032
0.5638	Remote Similarity	NPC252292
0.5625	Remote Similarity	NPC96795
0.5625	Remote Similarity	NPC264632
0.5618	Remote Similarity	NPC171134
0.5612	Remote Similarity	NPC476384
0.561	Remote Similarity	NPC287597
0.5579	Remote Similarity	NPC476397
0.5567	Remote Similarity	NPC300894
0.5567	Remote Similarity	NPC23845
0.5521	Remote Similarity	NPC100998
0.5393	Remote Similarity	NPC235294
0.5392	Remote Similarity	NPC64195
0.5333	Remote Similarity	NPC46137
0.53	Remote Similarity	NPC106818
0.5294	Remote Similarity	NPC35731
0.5213	Remote Similarity	NPC476383
0.5196	Remote Similarity	NPC476380
0.5196	Remote Similarity	NPC476381
0.5161	Remote Similarity	NPC321184
0.5152	Remote Similarity	NPC610636
0.5116	Remote Similarity	NPC34293
0.5109	Remote Similarity	NPC40305
0.5102	Remote Similarity	NPC119537
0.5096	Remote Similarity	NPC87403
0.5067	Remote Similarity	NPC266045
0.5053	Remote Similarity	NPC476377

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC312131 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4571
0.1-0.2	4495
0.2-0.3	81
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
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
0.6471	Remote Similarity	NPD7266	Phase 2

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