NPASS Compound

Structure

NPC473707 OpenBabel07101719502D 42 44 0 0 1 0 0 0 0 0999 V2000 23.8834 0.6528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3247 -1.7522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 23.7529 1.6443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 22.8290 2.0270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 22.0356 1.4182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 21.1118 1.8009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.3184 1.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.3945 1.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.6012 0.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.6773 1.3487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.8839 0.7400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7530 1.6010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6769 1.2183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9597 0.9923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.9601 1.1227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1114 1.6705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4703 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0358 1.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1875 2.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.1667 0.5139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9047 2.2793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4151 1.1054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5616 1.4590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5514 -0.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3186 1.1489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5357 2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6088 -0.7934 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5252 0.5401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3942 1.4444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2425 0.7662 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.2428 0.8966 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8286 1.8966 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.5357 0.1895 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8286 0.8966 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5664 0.8241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5247 0.4530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3730 -0.2253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2326 1.7668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.2428 1.8966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5357 2.6037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5357 0.1895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 29 1 0 0 0 0 22 23 1 0 0 0 0 24 27 1 0 0 0 0 24 28 2 0 0 0 0 25 28 1 0 0 0 0 25 30 1 0 0 0 0 26 39 1 0 0 0 0 26 40 1 0 0 0 0 27 2 1 6 0 0 0 27 41 1 0 0 0 0 28 35 1 0 0 0 0 29 36 1 6 0 0 0 30 37 1 1 0 0 0 31 20 1 1 0 0 0 31 33 1 0 0 0 0 31 39 1 0 0 0 0 32 21 1 1 0 0 0 32 34 1 0 0 0 0 32 40 1 0 0 0 0 33 22 1 6 0 0 0 33 42 1 0 0 0 0 34 23 1 1 0 0 0 34 42 1 0 0 0 0 35 38 2 0 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.45
Volume:	644.505
LogP:	8.928
LogD:	4.979
LogS:	-6.797
# Rotatable Bonds:	23
TPSA:	101.52
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.11
Synthetic Accessibility Score:	5.345
Fsp3:	0.886
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.007
MDCK Permeability:	2.074582880595699e-05
Pgp-inhibitor:	0.115
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.489

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	97.30367279052734%
Volume Distribution (VD):	0.773
Pgp-substrate:	3.261343002319336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.427
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.208
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	7.626
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.982
Carcinogencity:	0.064
Eye Corrosion:	0.005
Eye Irritation:	0.052
Respiratory Toxicity:	0.727

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC473707

Natural Product ID:	NPC473707
*Common Name:**	Cis-Annonacin Formal
IUPAC Name:	(2S)-4-[(2R,8R)-11-[(1S,2S,6R,7S)-2-dodecyl-3,5,10-trioxabicyclo[5.2.1]decan-6-yl]-2,8-dihydroxyundecyl]-2-methyl-2H-furan-5-one
Synonyms:	Cis-Annonacin Formal
Standard InCHIKey:	CVTBDMFBFBIITE-RLWOUWICSA-N
Standard InCHI:	InChI=1S/C35H62O7/c1-3-4-5-6-7-8-9-10-11-15-20-31-33-22-23-34(42-33)32(40-26-39-31)21-16-19-29(36)17-13-12-14-18-30(37)25-28-24-27(2)41-35(28)38/h24,27,29-34,36-37H,3-23,25-26H2,1-2H3/t27-,29+,30+,31-,32+,33-,34-/m0/s1
SMILES:	CCCCCCCCCCCC[C@@H]1OCO[C@@H]([C@H]2O[C@H]1CC2)CCC[C@@H](CCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449783
PubChem CID:	44584240
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473425]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975482]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7494150]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673926]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673935]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673936]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[8946744]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8991944]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[9584396]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26234	Annona muricata	Species	Annonaceae	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	NP ID	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
Others	1

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.079	ug.mL-1	PMID[555905]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.6	ug.mL-1	PMID[555905]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2.1	ug.mL-1	PMID[555905]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	22.0	%	PMID[555905]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC473707 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	1696
0.2-0.3	6150
0.3-0.4	14740
0.4-0.5	10737
0.5-0.6	6725
0.6-0.7	2015
0.7-0.8	250
0.8-0.85	73
0.85-0.9	92
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9432	High Similarity	NPC473723
0.9432	High Similarity	NPC473561
0.9432	High Similarity	NPC473663
0.9432	High Similarity	NPC475173
0.9205	High Similarity	NPC473904
0.9186	High Similarity	NPC62118
0.9186	High Similarity	NPC231096
0.9186	High Similarity	NPC107717
0.9186	High Similarity	NPC232555
0.9186	High Similarity	NPC114694
0.9186	High Similarity	NPC142117
0.9186	High Similarity	NPC240695
0.9186	High Similarity	NPC475581
0.9186	High Similarity	NPC171174
0.9091	High Similarity	NPC139418
0.907	High Similarity	NPC110710
0.907	High Similarity	NPC132496
0.907	High Similarity	NPC1083
0.907	High Similarity	NPC231009
0.907	High Similarity	NPC283085
0.907	High Similarity	NPC286338
0.907	High Similarity	NPC223871
0.907	High Similarity	NPC473651
0.907	High Similarity	NPC103284
0.907	High Similarity	NPC473478
0.907	High Similarity	NPC107986
0.907	High Similarity	NPC473669
0.907	High Similarity	NPC66346
0.907	High Similarity	NPC82795
0.9	High Similarity	NPC473520
0.8977	High Similarity	NPC151403
0.8977	High Similarity	NPC191929
0.8977	High Similarity	NPC274446
0.8977	High Similarity	NPC171135
0.8977	High Similarity	NPC169511
0.8977	High Similarity	NPC242364
0.8977	High Similarity	NPC172821
0.8977	High Similarity	NPC133730
0.8977	High Similarity	NPC21208
0.8977	High Similarity	NPC39754
0.8977	High Similarity	NPC81045
0.8977	High Similarity	NPC40376
0.8977	High Similarity	NPC61257
0.8977	High Similarity	NPC280621
0.8977	High Similarity	NPC234077
0.8977	High Similarity	NPC233551
0.8977	High Similarity	NPC100454
0.8977	High Similarity	NPC261952
0.8977	High Similarity	NPC320569
0.8977	High Similarity	NPC48338
0.8977	High Similarity	NPC20339
0.8977	High Similarity	NPC287164
0.8966	High Similarity	NPC473687
0.8966	High Similarity	NPC103523
0.8966	High Similarity	NPC308412
0.8966	High Similarity	NPC134807
0.8966	High Similarity	NPC210218
0.8966	High Similarity	NPC204686
0.8966	High Similarity	NPC219498
0.8966	High Similarity	NPC279267
0.8966	High Similarity	NPC134885
0.8966	High Similarity	NPC69082
0.8966	High Similarity	NPC134865
0.8953	High Similarity	NPC156804
0.8876	High Similarity	NPC477011
0.8876	High Similarity	NPC81778
0.8876	High Similarity	NPC318963
0.8876	High Similarity	NPC93794
0.8876	High Similarity	NPC91067
0.8876	High Similarity	NPC40066
0.8876	High Similarity	NPC473504
0.8876	High Similarity	NPC20621
0.8876	High Similarity	NPC42598
0.8864	High Similarity	NPC178215
0.8851	High Similarity	NPC329615
0.8851	High Similarity	NPC120398
0.8851	High Similarity	NPC322529
0.8851	High Similarity	NPC471567
0.8851	High Similarity	NPC329838
0.8791	High Similarity	NPC11456
0.8778	High Similarity	NPC239517
0.875	High Similarity	NPC112685
0.875	High Similarity	NPC132940
0.875	High Similarity	NPC241360
0.875	High Similarity	NPC47937
0.875	High Similarity	NPC293136
0.8736	High Similarity	NPC163093
0.8721	High Similarity	NPC180363
0.8721	High Similarity	NPC94875
0.8721	High Similarity	NPC73310
0.8721	High Similarity	NPC473529
0.8721	High Similarity	NPC65930
0.8721	High Similarity	NPC145914
0.8721	High Similarity	NPC473780
0.8721	High Similarity	NPC131002
0.8721	High Similarity	NPC329829
0.8721	High Similarity	NPC475159
0.8721	High Similarity	NPC473712
0.8721	High Similarity	NPC11332
0.8667	High Similarity	NPC14901
0.8667	High Similarity	NPC130359
0.8652	High Similarity	NPC20533
0.8652	High Similarity	NPC476583
0.8652	High Similarity	NPC258068
0.8636	High Similarity	NPC319036
0.8636	High Similarity	NPC292809
0.8636	High Similarity	NPC39167
0.8636	High Similarity	NPC477013
0.8636	High Similarity	NPC202055
0.8636	High Similarity	NPC473156
0.8636	High Similarity	NPC470400
0.8636	High Similarity	NPC77871
0.8636	High Similarity	NPC9678
0.8636	High Similarity	NPC39279
0.8636	High Similarity	NPC477018
0.8636	High Similarity	NPC235809
0.8636	High Similarity	NPC100921
0.8636	High Similarity	NPC25764
0.8636	High Similarity	NPC182383
0.8636	High Similarity	NPC475268
0.8636	High Similarity	NPC477014
0.8636	High Similarity	NPC473671
0.8621	High Similarity	NPC144415
0.8621	High Similarity	NPC253801
0.8556	High Similarity	NPC89001
0.8556	High Similarity	NPC320458
0.8556	High Similarity	NPC473905
0.8539	High Similarity	NPC219652
0.8539	High Similarity	NPC309211
0.8539	High Similarity	NPC282815
0.8539	High Similarity	NPC473840
0.8539	High Similarity	NPC477010
0.8539	High Similarity	NPC477015
0.8539	High Similarity	NPC25703
0.8462	Intermediate Similarity	NPC280612
0.8462	Intermediate Similarity	NPC477017
0.8462	Intermediate Similarity	NPC477016
0.8444	Intermediate Similarity	NPC473995
0.8444	Intermediate Similarity	NPC473649
0.8444	Intermediate Similarity	NPC159750
0.8444	Intermediate Similarity	NPC154097
0.8444	Intermediate Similarity	NPC470401
0.8242	Intermediate Similarity	NPC477012
0.8111	Intermediate Similarity	NPC41856
0.8	Intermediate Similarity	NPC286770
0.8	Intermediate Similarity	NPC229799
0.8	Intermediate Similarity	NPC284472
0.798	Intermediate Similarity	NPC473332
0.7979	Intermediate Similarity	NPC80875
0.7959	Intermediate Similarity	NPC187268
0.7938	Intermediate Similarity	NPC306041
0.7912	Intermediate Similarity	NPC288471
0.7895	Intermediate Similarity	NPC30515
0.7889	Intermediate Similarity	NPC310450
0.7889	Intermediate Similarity	NPC475046
0.7889	Intermediate Similarity	NPC474959
0.7889	Intermediate Similarity	NPC11383
0.7872	Intermediate Similarity	NPC295312
0.7812	Intermediate Similarity	NPC81419
0.7812	Intermediate Similarity	NPC179746
0.7789	Intermediate Similarity	NPC473619
0.7789	Intermediate Similarity	NPC118078
0.7789	Intermediate Similarity	NPC474098
0.7789	Intermediate Similarity	NPC475995
0.7789	Intermediate Similarity	NPC51004
0.7778	Intermediate Similarity	NPC203627
0.7732	Intermediate Similarity	NPC474338
0.7708	Intermediate Similarity	NPC12172
0.7708	Intermediate Similarity	NPC473321
0.7708	Intermediate Similarity	NPC208886
0.7708	Intermediate Similarity	NPC184463
0.7684	Intermediate Similarity	NPC307411
0.7684	Intermediate Similarity	NPC474032
0.766	Intermediate Similarity	NPC160138
0.7653	Intermediate Similarity	NPC36954
0.7653	Intermediate Similarity	NPC471141
0.7634	Intermediate Similarity	NPC21469
0.7629	Intermediate Similarity	NPC288240
0.7629	Intermediate Similarity	NPC476300
0.7629	Intermediate Similarity	NPC273579
0.7629	Intermediate Similarity	NPC320089
0.7629	Intermediate Similarity	NPC295204
0.7629	Intermediate Similarity	NPC238090
0.7629	Intermediate Similarity	NPC472195
0.7629	Intermediate Similarity	NPC475912
0.7629	Intermediate Similarity	NPC472196
0.7629	Intermediate Similarity	NPC162205
0.7604	Intermediate Similarity	NPC476004
0.7604	Intermediate Similarity	NPC474761
0.76	Intermediate Similarity	NPC473326
0.76	Intermediate Similarity	NPC279561
0.7579	Intermediate Similarity	NPC202672
0.7576	Intermediate Similarity	NPC476315
0.7576	Intermediate Similarity	NPC54731
0.7576	Intermediate Similarity	NPC279621
0.7573	Intermediate Similarity	NPC474917
0.7558	Intermediate Similarity	NPC84038
0.7553	Intermediate Similarity	NPC469483
0.7553	Intermediate Similarity	NPC284902
0.7551	Intermediate Similarity	NPC81386

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473707 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	2429
0.2-0.3	3905
0.3-0.4	1846
0.4-0.5	561
0.5-0.6	185
0.6-0.7	27
0.7-0.8	1
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
0.7426	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD46	Approved
0.7423	Intermediate Similarity	NPD6698	Approved
0.7358	Intermediate Similarity	NPD6686	Approved
0.7264	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7838	Discovery
0.7	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7983	Approved
0.6757	Remote Similarity	NPD6371	Approved
0.6735	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.661	Remote Similarity	NPD8517	Approved
0.661	Remote Similarity	NPD8513	Phase 3
0.661	Remote Similarity	NPD8516	Approved
0.661	Remote Similarity	NPD8515	Approved
0.66	Remote Similarity	NPD4251	Approved
0.66	Remote Similarity	NPD4250	Approved
0.6569	Remote Similarity	NPD5785	Approved
0.65	Remote Similarity	NPD4249	Approved
0.6471	Remote Similarity	NPD1695	Approved
0.6465	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5363	Approved
0.64	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7507	Approved
0.6364	Remote Similarity	NPD7829	Approved
0.6364	Remote Similarity	NPD7154	Phase 3
0.6364	Remote Similarity	NPD7830	Approved
0.6364	Remote Similarity	NPD5362	Discontinued
0.6296	Remote Similarity	NPD4225	Approved
0.6262	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD4756	Discovery
0.624	Remote Similarity	NPD7319	Approved
0.623	Remote Similarity	NPD7642	Approved
0.6224	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7641	Discontinued
0.621	Remote Similarity	NPD8074	Phase 3
0.6207	Remote Similarity	NPD6053	Discontinued
0.6198	Remote Similarity	NPD8033	Approved
0.6195	Remote Similarity	NPD6412	Phase 2
0.6182	Remote Similarity	NPD5344	Discontinued
0.618	Remote Similarity	NPD3197	Phase 1
0.6154	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7638	Approved
0.6116	Remote Similarity	NPD8377	Approved
0.6116	Remote Similarity	NPD8294	Approved
0.61	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4269	Approved
0.61	Remote Similarity	NPD4270	Approved
0.6091	Remote Similarity	NPD7640	Approved
0.6091	Remote Similarity	NPD7639	Approved
0.6083	Remote Similarity	NPD7327	Approved
0.6083	Remote Similarity	NPD7328	Approved
0.6075	Remote Similarity	NPD5282	Discontinued
0.6066	Remote Similarity	NPD8379	Approved
0.6066	Remote Similarity	NPD8378	Approved
0.6066	Remote Similarity	NPD8296	Approved
0.6066	Remote Similarity	NPD8380	Approved
0.6066	Remote Similarity	NPD8335	Approved
0.6066	Remote Similarity	NPD8444	Approved
0.6061	Remote Similarity	NPD4252	Approved
0.6033	Remote Similarity	NPD7516	Approved
0.6032	Remote Similarity	NPD7736	Approved
0.6031	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4271	Approved
0.602	Remote Similarity	NPD4268	Approved
0.6019	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD5369	Approved
0.5981	Remote Similarity	NPD5779	Approved
0.5981	Remote Similarity	NPD5778	Approved
0.5952	Remote Similarity	NPD8448	Approved
0.5952	Remote Similarity	NPD8293	Discontinued
0.5948	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6648	Approved
0.5941	Remote Similarity	NPD6435	Approved
0.5922	Remote Similarity	NPD1694	Approved
0.592	Remote Similarity	NPD7492	Approved
0.59	Remote Similarity	NPD4820	Approved
0.59	Remote Similarity	NPD4821	Approved
0.59	Remote Similarity	NPD4819	Approved
0.59	Remote Similarity	NPD4822	Approved
0.5897	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD6370	Approved
0.5882	Remote Similarity	NPD5332	Approved
0.5882	Remote Similarity	NPD6110	Phase 1
0.5882	Remote Similarity	NPD8133	Approved
0.5882	Remote Similarity	NPD5331	Approved
0.5876	Remote Similarity	NPD8039	Approved
0.5873	Remote Similarity	NPD6616	Approved
0.5868	Remote Similarity	NPD7500	Approved
0.5868	Remote Similarity	NPD7115	Discovery
0.5859	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6054	Approved
0.5843	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4790	Discontinued
0.584	Remote Similarity	NPD8328	Phase 3
0.5827	Remote Similarity	NPD7078	Approved
0.5814	Remote Similarity	NPD8392	Approved
0.5814	Remote Similarity	NPD8390	Approved
0.5814	Remote Similarity	NPD8391	Approved
0.5812	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7503	Approved
0.5794	Remote Similarity	NPD8341	Approved
0.5794	Remote Similarity	NPD8340	Approved
0.5794	Remote Similarity	NPD8299	Approved
0.5794	Remote Similarity	NPD8342	Approved
0.5784	Remote Similarity	NPD5209	Approved
0.5761	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.576	Remote Similarity	NPD8080	Discontinued
0.5743	Remote Similarity	NPD5368	Approved
0.5738	Remote Similarity	NPD6009	Approved
0.5738	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6059	Approved
0.5714	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6067	Discontinued
0.5701	Remote Similarity	NPD5370	Suspended
0.5699	Remote Similarity	NPD3704	Approved
0.5698	Remote Similarity	NPD4266	Approved
0.5698	Remote Similarity	NPD3196	Approved
0.5698	Remote Similarity	NPD3194	Approved
0.5698	Remote Similarity	NPD3195	Phase 2
0.5688	Remote Similarity	NPD6399	Phase 3
0.568	Remote Similarity	NPD8269	Approved
0.568	Remote Similarity	NPD6015	Approved
0.568	Remote Similarity	NPD8267	Approved
0.568	Remote Similarity	NPD8266	Approved
0.568	Remote Similarity	NPD8268	Approved
0.568	Remote Similarity	NPD6016	Approved
0.5649	Remote Similarity	NPD7260	Phase 2
0.5648	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD5988	Approved
0.563	Remote Similarity	NPD2067	Discontinued
0.5625	Remote Similarity	NPD7902	Approved
0.561	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD6845	Suspended

Bioactivity similarity: Similar Natural Products in NPASS

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