NPASS Compound

Natural Product: NPC167116

Natural Product ID	NPC167116
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TWWDQMZTYKXKKW-SVBPBHIXSA-N
IUPAC Name	n.a.
Synonyms	(+)-Angchibangkine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL524668
PubChem CID	10602988
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related 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 76 83 0 0 0 0 0 0 0 0999 V2000 6.1558 -0.5349 1.9069 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6975 -0.4100 0.5608 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8652 -1.6377 -0.1820 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9199 -2.7040 0.2384 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5459 -2.1847 0.2187 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4992 -3.0953 0.1138 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1858 -2.6518 0.0997 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9185 -1.3003 0.1903 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9790 -0.4194 0.2959 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2986 -0.8509 0.3094 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4048 0.1680 0.4151 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4363 0.9786 -0.8743 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3731 2.0022 -0.8927 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4411 1.9623 -1.9006 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3680 2.8649 -1.9053 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2724 3.7851 -0.8838 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1955 3.8435 0.1263 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2287 2.9496 0.1011 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1680 4.6649 -0.9161 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9979 4.2367 -0.2543 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1184 2.9221 0.1395 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2328 2.4836 0.7806 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2396 3.3817 1.0286 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1381 4.6995 0.6429 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9878 5.1412 -0.0163 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8880 6.4789 -0.4063 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3926 1.0463 1.2146 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9920 0.2723 0.0938 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7549 -1.1658 0.0536 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7570 -2.0926 -0.0497 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1677 -1.6234 -0.0712 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2226 -0.3433 0.7353 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4040 0.6128 0.0462 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.8904 0.7871 -1.2993 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4981 -3.4370 -0.1341 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 -3.9088 -0.1182 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1889 -3.0005 -0.0147 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4425 -1.6491 0.0718 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3709 -0.7920 0.1769 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1101 -3.5281 -0.0041 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9440 -5.2632 -0.2040 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9824 -6.2269 -0.3121 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3422 -0.8420 2.5637 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9786 -1.2872 1.9272 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5446 0.4631 2.2278 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7877 -1.4829 -1.2753 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9048 -2.0065 0.0150 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2036 -3.0937 1.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0307 -3.5410 -0.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6546 -4.1588 0.0407 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7632 0.6220 0.4011 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2043 0.8253 1.2736 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4094 1.5016 -0.9804 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3513 0.2962 -1.7413 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5445 1.2303 -2.6870 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6548 2.8082 -2.7079 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0994 4.5682 0.9015 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9602 2.9842 0.8869 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3198 2.2222 -0.0604 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1595 3.1049 1.5361 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9198 5.4291 0.8271 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5453 6.7323 -1.3243 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4313 0.6956 1.5926 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1567 1.0601 2.0465 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5462 0.7113 -0.8541 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4109 -1.4170 -1.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8642 -2.3915 0.3139 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7799 -0.5921 1.7362 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2391 0.0629 0.8095 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8285 1.8623 -1.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9773 0.5365 -1.3734 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3435 0.1663 -2.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3231 -4.1652 -0.2165 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5971 -7.2543 -0.2976 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6796 -6.0811 0.5437 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5541 -6.0309 -1.2391 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 16 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 22 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 30 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 1 0 37 40 1 0 36 41 1 0 41 42 1 0 11 2 1 0 18 13 1 0 25 20 1 0 33 28 1 0 10 5 1 0 38 29 2 0 40 7 1 0 39 8 1 0 1 43 1 0 1 44 1 0 1 45 1 0 3 46 1 0 3 47 1 0 4 48 1 0 4 49 1 0 6 50 1 0 9 51 1 0 11 52 1 1 12 53 1 0 12 54 1 0 14 55 1 0 15 56 1 0 17 57 1 0 18 58 1 0 21 59 1 0 23 60 1 0 24 61 1 0 26 62 1 0 27 63 1 0 27 64 1 0 28 65 1 6 31 66 1 0 31 67 1 0 32 68 1 0 32 69 1 0 34 70 1 0 34 71 1 0 34 72 1 0 35 73 1 0 42 74 1 0 42 75 1 0 42 76 1 0 M END

Standard InCHIKey	TWWDQMZTYKXKKW-SVBPBHIXSA-N
Standard InCHI	InChI=1S/C35H34N2O5/c1-36-12-10-22-17-30-31-19-25(22)26(36)14-20-4-7-24(8-5-20)40-29-16-21(6-9-28(29)38)15-27-33-23(11-13-37(27)2)18-32(39-3)34(41-30)35(33)42-31/h4-9,16-19,26-27,38H,10-15H2,1-3H3/t26-,27-/m0/s1
SMILES	CN1CCc2cc3c4cc2[C@@H]1Cc1ccc(cc1)Oc1cc(ccc1O)C[C@H]1c2c(CCN1C)cc(c(c2O4)O3)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	562.25	Volume:	579.771 ? Van der Waals volume.
Dense:	0.97	LogP:	3.476 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.999 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.295 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	44.0
TPSA:	63.63 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	9.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.237	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.894	Fsp³:	0.314
MCE-18:	140.609 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.999	Fluc inhibitor:	0.022 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.922 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.991 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.179

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.131	MDCK Permeability:	-4.883
Pgp-inhibitor:	0.204	Pgp-substrate:	0.877
PAMPA:	0.012 ? 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%):	0.829	30% Bioavailability (F30%):	0.958
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.984	MRP1:	0.977
Plasma Protein Binding (PPB):	80.486%	Volume Distribution (VD):	0.333
Fu:	20.08% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.615
OATP1B3 inhibitor:	0.484	BCRP inhibitor:	0.548
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.99	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.996	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.939	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.197
CYP2B6-substrate:	0.276	CYP2C8-inhibitor:	0.045
HLM stability:	0.079 ? 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):

11.954

Half-life (T1/2):

2.675

ADMET: Toxicity

hERG Blockers:	0.882	hERG Blockers (10um):	0.852
Human Hepatotoxicity (H-HT):	0.592	Drug-induced Liver Injury (DILI):	0.017
AMES Toxicity:	0.741	Rat Oral Acute Toxicity:	0.916
Maximum Recommended Daily Dose:	0.987	Skin Sensitization:	0.609
Carcinogencity:	0.814	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.931
Drug-induced Neurotoxicity:	0.818	Ototoxicity:	0.372
Hematotoxicity:	0.058	Drug-induced Nephrotoxicity:	0.334
Genotoxicity:	0.952	RPMI-8226 Immunitoxicity:	0.085
A549 Cytotoxicity:	0.397	Hek293 Cytotoxicity:	0.705
BCF:	1.904 ? 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:	4.783 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.191 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.571 ? 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
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[9157192]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9157192]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	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	3

Activity Type	# Activity
Cell line	1
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
NPT91	Cell line	KB	Homo sapiens	IC50	=	12.0	ug.mL-1	PMID[21741249]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.306	ug.mL-1	PMID[21741249]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.265	ug.mL-1	PMID[21741249]

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 NPC167116 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	29301
0.1-0.2	19155
0.2-0.3	1135
0.3-0.4	130
0.4-0.5	38
0.5-0.6	34
0.6-0.7	31
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC274716
1.0	High Similarity	NPC609821
0.8267	Intermediate Similarity	NPC185639
0.8267	Intermediate Similarity	NPC251735
0.8267	Intermediate Similarity	NPC49075
0.8267	Intermediate Similarity	NPC599951
0.7838	Intermediate Similarity	NPC12424
0.7838	Intermediate Similarity	NPC129518
0.7838	Intermediate Similarity	NPC251580
0.7792	Intermediate Similarity	NPC223690
0.7792	Intermediate Similarity	NPC9532
0.7763	Intermediate Similarity	NPC608819
0.775	Intermediate Similarity	NPC24260
0.7606	Intermediate Similarity	NPC317272
0.7606	Intermediate Similarity	NPC268503
0.7595	Intermediate Similarity	NPC181796
0.7595	Intermediate Similarity	NPC54654
0.7595	Intermediate Similarity	NPC7715
0.7595	Intermediate Similarity	NPC328155
0.7595	Intermediate Similarity	NPC222661
0.7595	Intermediate Similarity	NPC285931
0.7442	Intermediate Similarity	NPC191132
0.7407	Intermediate Similarity	NPC212237
0.7375	Intermediate Similarity	NPC290005
0.7326	Intermediate Similarity	NPC85381
0.7317	Intermediate Similarity	NPC611658
0.7241	Intermediate Similarity	NPC60295
0.7195	Intermediate Similarity	NPC139783
0.7195	Intermediate Similarity	NPC65312
0.7195	Intermediate Similarity	NPC611798
0.6923	Remote Similarity	NPC240841
0.6914	Remote Similarity	NPC254441
0.6842	Remote Similarity	NPC256012
0.6842	Remote Similarity	NPC610965
0.6585	Remote Similarity	NPC311973
0.6538	Remote Similarity	NPC76682
0.6538	Remote Similarity	NPC10908
0.6538	Remote Similarity	NPC63646
0.6538	Remote Similarity	NPC317145
0.6538	Remote Similarity	NPC198498
0.6538	Remote Similarity	NPC115284
0.6512	Remote Similarity	NPC8836
0.6477	Remote Similarity	NPC480590
0.6456	Remote Similarity	NPC276890
0.6404	Remote Similarity	NPC254581
0.6386	Remote Similarity	NPC239824
0.6341	Remote Similarity	NPC290582
0.6341	Remote Similarity	NPC217748
0.6341	Remote Similarity	NPC182052
0.6341	Remote Similarity	NPC271013
0.6341	Remote Similarity	NPC42663
0.6341	Remote Similarity	NPC15414
0.6265	Remote Similarity	NPC279228
0.625	Remote Similarity	NPC41376
0.6222	Remote Similarity	NPC206900
0.6196	Remote Similarity	NPC41122
0.6196	Remote Similarity	NPC318805
0.6145	Remote Similarity	NPC73492
0.6145	Remote Similarity	NPC299990
0.6118	Remote Similarity	NPC116465
0.6098	Remote Similarity	NPC610959
0.5952	Remote Similarity	NPC480587
0.5934	Remote Similarity	NPC480586
0.5926	Remote Similarity	NPC480592
0.5909	Remote Similarity	NPC16357
0.5909	Remote Similarity	NPC302245
0.5833	Remote Similarity	NPC603853
0.5811	Remote Similarity	NPC317439
0.5789	Remote Similarity	NPC247639
0.5789	Remote Similarity	NPC25084
0.5783	Remote Similarity	NPC603603
0.5778	Remote Similarity	NPC249996
0.5747	Remote Similarity	NPC601503
0.5729	Remote Similarity	NPC175890
0.5729	Remote Similarity	NPC201508
0.5657	Remote Similarity	NPC256124
0.5652	Remote Similarity	NPC239584
0.5632	Remote Similarity	NPC600054
0.5632	Remote Similarity	NPC601504
0.5595	Remote Similarity	NPC227060
0.5584	Remote Similarity	NPC104196
0.5506	Remote Similarity	NPC229373
0.5446	Remote Similarity	NPC475654
0.5435	Remote Similarity	NPC275680
0.5435	Remote Similarity	NPC22115
0.5405	Remote Similarity	NPC185838
0.5326	Remote Similarity	NPC601489
0.5326	Remote Similarity	NPC604804
0.5287	Remote Similarity	NPC480591
0.5269	Remote Similarity	NPC605743
0.5195	Remote Similarity	NPC135538
0.5195	Remote Similarity	NPC24233
0.5146	Remote Similarity	NPC38964
0.5111	Remote Similarity	NPC286119
0.5068	Remote Similarity	NPC314682

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC167116 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4831
0.1-0.2	4222
0.2-0.3	88
0.3-0.4	3
0.4-0.5	0
0.5-0.6	3
0.6-0.7	2
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
0.6538	Remote Similarity	NPD8099	Discontinued
0.622	Remote Similarity	NPD8156	Discontinued
0.5789	Remote Similarity	NPD8053	Approved
0.5765	Remote Similarity	NPD8095	Phase 1
0.5567	Remote Similarity	NPD8054	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