NPASS Compound

Structure

NPC43976 OpenBabel07101719522D 57 62 0 0 1 0 0 0 0 0999 V2000 -3.0550 2.9209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4091 4.9206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9660 -2.4603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4091 -2.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5637 2.8942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6277 3.1983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0489 -2.3285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0648 -2.3285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 0.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4520 -0.4070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7046 -0.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7380 4.3836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4338 3.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3667 0.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8523 -1.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7006 4.5882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7882 0.1880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5568 0.4921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0924 2.7163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5568 4.4286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9660 -1.4762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2614 -2.4603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7882 1.7803 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8523 1.4762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8523 1.4762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4091 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7046 -0.9841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7046 4.9206 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8182 -0.9841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8523 4.4286 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8182 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8523 3.4444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9660 0.4921 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8523 0.4921 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4091 -0.9841 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7046 2.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1137 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3591 3.8568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5568 -1.4762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8523 0.4921 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1137 -2.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 5.9048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6705 -1.4762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.9206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6705 0.4921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9660 1.4762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3217 4.0614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5568 3.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1137 -0.9841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2614 -1.4762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 1.9683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2614 0.4921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 4 24 1 0 0 0 0 5 40 1 0 0 0 0 6 40 1 0 0 0 0 7 41 1 0 0 0 0 8 41 1 0 0 0 0 10 43 1 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 21 2 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 40 1 0 0 0 0 17 43 1 0 0 0 0 18 44 1 0 0 0 0 19 26 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 20 42 1 0 0 0 0 22 2 1 1 0 0 0 22 30 1 0 0 0 0 22 53 1 0 0 0 0 23 3 1 1 0 0 0 23 31 1 0 0 0 0 23 54 1 0 0 0 0 24 45 2 0 0 0 0 24 55 1 0 0 0 0 25 21 1 6 0 0 0 25 26 1 0 0 0 0 26 43 1 1 0 0 0 27 36 1 0 0 0 0 27 56 1 1 0 0 0 28 37 1 0 0 0 0 28 57 1 1 0 0 0 29 41 1 0 0 0 0 29 42 1 6 0 0 0 30 32 1 0 0 0 0 30 46 1 1 0 0 0 31 33 1 0 0 0 0 31 47 1 1 0 0 0 32 34 1 0 0 0 0 32 48 1 1 0 0 0 33 35 1 0 0 0 0 33 49 1 1 0 0 0 34 38 1 0 0 0 0 34 50 1 6 0 0 0 35 39 1 0 0 0 0 35 51 1 6 0 0 0 36 42 1 6 0 0 0 36 44 1 0 0 0 0 37 41 1 0 0 0 0 37 55 1 1 0 0 0 38 53 1 0 0 0 0 38 56 1 1 0 0 0 39 54 1 0 0 0 0 39 57 1 1 0 0 0 40 52 1 0 0 0 0 42 9 1 6 0 0 0 43 44 1 6 0 0 0 44 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	810.51
Volume:	827.241
LogP:	4.385
LogD:	4.164
LogS:	-3.935
# Rotatable Bonds:	10
TPSA:	204.83
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.101
Synthetic Accessibility Score:	6.108
Fsp3:	0.932
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:	-5.261
MDCK Permeability:	0.00011847657151520252
Pgp-inhibitor:	0.994
Pgp-substrate:	0.942
Human Intestinal Absorption (HIA):	0.83
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.835

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	87.01532745361328%
Volume Distribution (VD):	0.657
Pgp-substrate:	6.600650310516357%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.731
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.133
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	0.947
Half-life (T1/2):	0.457

ADMET: Toxicity

hERG Blockers:	0.261
Human Hepatotoxicity (H-HT):	0.161
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.787
Carcinogencity:	0.007
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.488

Download Data

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

Natural Product: NPC43976

Natural Product ID:	NPC43976
*Common Name:**	Combretaside C
IUPAC Name:	[(2R,3S,5R,8R,9R,10S,11R,13R,14R,17S)-17-[(E)-6-hydroxy-6-methylhept-2-en-2-yl]-4,4,8,10,14-pentamethyl-2,11-bis[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:
Standard InCHIKey:	KVVWOEVABSSLIR-REURVNLQSA-N
Standard InCHI:	InChI=1S/C44H74O13/c1-21(13-12-16-40(5,6)52)25-14-17-43(10)26(25)19-27(56-38-34(50)32(48)30(46)22(2)53-38)36-42(9)20-28(57-39-35(51)33(49)31(47)23(3)54-39)37(55-24(4)45)41(7,8)29(42)15-18-44(36,43)11/h13,22-23,25-39,46-52H,12,14-20H2,1-11H3/b21-13+/t22-,23-,25-,26-,27-,28-,29+,30+,31+,32+,33+,34-,35-,36-,37-,38+,39+,42+,43-,44-/m1/s1
SMILES:	C/C(=CCCC(C)(C)O)/[C@H]1CC[C@]2(C)[C@@H]1C[C@H]([C@@H]1[C@@]3(C)C[C@H]([C@H](C(C)(C)[C@@H]3CC[C@@]21C)OC(=O)C)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](C)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](C)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419359
PubChem CID:	73350747
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO32465	combretum inflatum	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23978065]

☑ 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	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	71.0	%	PMID[487590]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>=	30.0	ug.mL-1	PMID[487590]

☑ 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 NPC43976 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	243
0.1-0.2	1855
0.2-0.3	5851
0.3-0.4	13256
0.4-0.5	8960
0.5-0.6	5400
0.6-0.7	3958
0.7-0.8	1790
0.8-0.85	615
0.85-0.9	621
0.9-0.95	118
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC296761
1.0	High Similarity	NPC51925
1.0	High Similarity	NPC154085
1.0	High Similarity	NPC125361
0.99	High Similarity	NPC472988
0.99	High Similarity	NPC38217
0.9804	High Similarity	NPC65167
0.98	High Similarity	NPC234160
0.97	High Similarity	NPC473199
0.96	High Similarity	NPC165033
0.96	High Similarity	NPC273879
0.95	High Similarity	NPC155010
0.95	High Similarity	NPC473020
0.95	High Similarity	NPC286969
0.95	High Similarity	NPC114874
0.95	High Similarity	NPC16573
0.95	High Similarity	NPC472252
0.95	High Similarity	NPC16520
0.95	High Similarity	NPC131479
0.95	High Similarity	NPC211879
0.95	High Similarity	NPC8039
0.95	High Similarity	NPC157659
0.95	High Similarity	NPC31907
0.95	High Similarity	NPC120123
0.95	High Similarity	NPC245280
0.95	High Similarity	NPC189852
0.9423	High Similarity	NPC114188
0.9412	High Similarity	NPC181467
0.94	High Similarity	NPC159036
0.94	High Similarity	NPC288694
0.94	High Similarity	NPC312553
0.932	High Similarity	NPC180183
0.932	High Similarity	NPC246124
0.9314	High Similarity	NPC160816
0.9314	High Similarity	NPC208477
0.9314	High Similarity	NPC194842
0.9314	High Similarity	NPC69737
0.9314	High Similarity	NPC152584
0.9314	High Similarity	NPC269627
0.9314	High Similarity	NPC208594
0.9314	High Similarity	NPC127801
0.93	High Similarity	NPC4831
0.93	High Similarity	NPC47566
0.93	High Similarity	NPC472023
0.93	High Similarity	NPC129372
0.93	High Similarity	NPC160734
0.93	High Similarity	NPC88000
0.93	High Similarity	NPC309425
0.9245	High Similarity	NPC144068
0.9223	High Similarity	NPC231340
0.9223	High Similarity	NPC14946
0.9223	High Similarity	NPC208650
0.9223	High Similarity	NPC63368
0.9216	High Similarity	NPC173583
0.9216	High Similarity	NPC187400
0.9216	High Similarity	NPC470885
0.9216	High Similarity	NPC221562
0.9208	High Similarity	NPC136816
0.92	High Similarity	NPC7341
0.92	High Similarity	NPC473200
0.9135	High Similarity	NPC220427
0.9135	High Similarity	NPC159005
0.9135	High Similarity	NPC295980
0.9135	High Similarity	NPC6931
0.9118	High Similarity	NPC213190
0.91	High Similarity	NPC234287
0.91	High Similarity	NPC280825
0.9074	High Similarity	NPC146652
0.9057	High Similarity	NPC250481
0.9057	High Similarity	NPC285410
0.9057	High Similarity	NPC263827
0.9038	High Similarity	NPC190395
0.9038	High Similarity	NPC473469
0.9029	High Similarity	NPC31430
0.9029	High Similarity	NPC85593
0.902	High Similarity	NPC470053
0.901	High Similarity	NPC317019
0.9	High Similarity	NPC30483
0.9	High Similarity	NPC292467
0.9	High Similarity	NPC236973
0.9	High Similarity	NPC469756
0.9	High Similarity	NPC32177
0.9	High Similarity	NPC55532
0.9	High Similarity	NPC470897
0.9	High Similarity	NPC329905
0.8981	High Similarity	NPC473882
0.8962	High Similarity	NPC472717
0.8952	High Similarity	NPC472897
0.8952	High Similarity	NPC7213
0.8952	High Similarity	NPC472896
0.8942	High Similarity	NPC309448
0.8942	High Similarity	NPC472899
0.8942	High Similarity	NPC472898
0.8942	High Similarity	NPC242748
0.8942	High Similarity	NPC472900
0.8932	High Similarity	NPC473198
0.8922	High Similarity	NPC470054
0.8919	High Similarity	NPC135369
0.8919	High Similarity	NPC475629
0.8919	High Similarity	NPC474466
0.8919	High Similarity	NPC475556
0.8919	High Similarity	NPC475136
0.8919	High Similarity	NPC72260
0.8919	High Similarity	NPC473566
0.8919	High Similarity	NPC475358
0.8911	High Similarity	NPC157739
0.89	High Similarity	NPC472989
0.8899	High Similarity	NPC212660
0.8889	High Similarity	NPC251309
0.8879	High Similarity	NPC472715
0.8879	High Similarity	NPC470748
0.8879	High Similarity	NPC179434
0.8879	High Similarity	NPC473021
0.8879	High Similarity	NPC472987
0.8868	High Similarity	NPC302057
0.8868	High Similarity	NPC473844
0.8868	High Similarity	NPC240125
0.8868	High Similarity	NPC51947
0.8868	High Similarity	NPC91583
0.8846	High Similarity	NPC312774
0.8846	High Similarity	NPC470064
0.8846	High Similarity	NPC470059
0.8846	High Similarity	NPC470061
0.8846	High Similarity	NPC470060
0.8846	High Similarity	NPC470043
0.8846	High Similarity	NPC475521
0.8846	High Similarity	NPC470058
0.8846	High Similarity	NPC470062
0.8846	High Similarity	NPC470057
0.8839	High Similarity	NPC120390
0.8839	High Similarity	NPC474908
0.8839	High Similarity	NPC173555
0.8839	High Similarity	NPC40749
0.8839	High Similarity	NPC475590
0.8839	High Similarity	NPC475219
0.8839	High Similarity	NPC231518
0.8839	High Similarity	NPC314535
0.8839	High Similarity	NPC475419
0.8835	High Similarity	NPC272015
0.8835	High Similarity	NPC154452
0.8824	High Similarity	NPC282669
0.8818	High Similarity	NPC93883
0.8818	High Similarity	NPC152615
0.8812	High Similarity	NPC473555
0.8812	High Similarity	NPC278939
0.8812	High Similarity	NPC471770
0.88	High Similarity	NPC57964
0.88	High Similarity	NPC94582
0.8796	High Similarity	NPC475312
0.8796	High Similarity	NPC139894
0.8796	High Similarity	NPC472716
0.8796	High Similarity	NPC210420
0.8796	High Similarity	NPC233003
0.8796	High Similarity	NPC474265
0.8796	High Similarity	NPC473383
0.8785	High Similarity	NPC269095
0.8785	High Similarity	NPC59804
0.8785	High Similarity	NPC108709
0.8785	High Similarity	NPC110139
0.8785	High Similarity	NPC220984
0.8785	High Similarity	NPC475296
0.8785	High Similarity	NPC174679
0.8785	High Similarity	NPC199457
0.8785	High Similarity	NPC127056
0.8785	High Similarity	NPC56713
0.8785	High Similarity	NPC136877
0.8785	High Similarity	NPC75747
0.8785	High Similarity	NPC270667
0.8785	High Similarity	NPC474589
0.8785	High Similarity	NPC29069
0.8785	High Similarity	NPC68419
0.8785	High Similarity	NPC164194
0.8785	High Similarity	NPC78046
0.8785	High Similarity	NPC279554
0.8785	High Similarity	NPC90856
0.8785	High Similarity	NPC129340
0.8785	High Similarity	NPC7870
0.8785	High Similarity	NPC102914
0.8774	High Similarity	NPC88744
0.8774	High Similarity	NPC235824
0.8762	High Similarity	NPC470763
0.8762	High Similarity	NPC473476
0.8762	High Similarity	NPC470767
0.8762	High Similarity	NPC473923
0.8762	High Similarity	NPC165405
0.8762	High Similarity	NPC474569
0.8761	High Similarity	NPC264336
0.8761	High Similarity	NPC474423
0.8761	High Similarity	NPC193893
0.8761	High Similarity	NPC74259
0.8739	High Similarity	NPC472080
0.8739	High Similarity	NPC475899
0.8738	High Similarity	NPC263756
0.8738	High Similarity	NPC117714
0.8738	High Similarity	NPC121072
0.8738	High Similarity	NPC21064
0.8727	High Similarity	NPC99620
0.8727	High Similarity	NPC244127
0.8727	High Similarity	NPC193382
0.8727	High Similarity	NPC199428

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 NPC43976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	2062
0.2-0.3	4203
0.3-0.4	1781
0.4-0.5	448
0.5-0.6	277
0.6-0.7	131
0.7-0.8	25
0.8-0.85	2
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD8294	Approved
0.8919	High Similarity	NPD8377	Approved
0.8839	High Similarity	NPD8380	Approved
0.8839	High Similarity	NPD8379	Approved
0.8839	High Similarity	NPD8296	Approved
0.8839	High Similarity	NPD8378	Approved
0.8839	High Similarity	NPD8335	Approved
0.8839	High Similarity	NPD8033	Approved
0.8661	High Similarity	NPD7516	Approved
0.8571	High Similarity	NPD7328	Approved
0.8571	High Similarity	NPD7327	Approved
0.8378	Intermediate Similarity	NPD8133	Approved
0.819	Intermediate Similarity	NPD7503	Approved
0.8182	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD7507	Approved
0.7899	Intermediate Similarity	NPD8328	Phase 3
0.7869	Intermediate Similarity	NPD7319	Approved
0.7845	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6412	Phase 2
0.7714	Intermediate Similarity	NPD8171	Discontinued
0.7642	Intermediate Similarity	NPD7736	Approved
0.7611	Intermediate Similarity	NPD6686	Approved
0.7419	Intermediate Similarity	NPD8293	Discontinued
0.74	Intermediate Similarity	NPD7525	Registered
0.7364	Intermediate Similarity	NPD7638	Approved
0.7345	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7639	Approved
0.7297	Intermediate Similarity	NPD7640	Approved
0.7236	Intermediate Similarity	NPD6370	Approved
0.7206	Intermediate Similarity	NPD7625	Phase 1
0.7203	Intermediate Similarity	NPD6882	Approved
0.7203	Intermediate Similarity	NPD8297	Approved
0.7154	Intermediate Similarity	NPD8517	Approved
0.7154	Intermediate Similarity	NPD8515	Approved
0.7154	Intermediate Similarity	NPD8513	Phase 3
0.7154	Intermediate Similarity	NPD8516	Approved
0.713	Intermediate Similarity	NPD8034	Phase 2
0.713	Intermediate Similarity	NPD8035	Phase 2
0.712	Intermediate Similarity	NPD7492	Approved
0.7107	Intermediate Similarity	NPD6009	Approved
0.7075	Intermediate Similarity	NPD7524	Approved
0.7073	Intermediate Similarity	NPD6059	Approved
0.7073	Intermediate Similarity	NPD6319	Approved
0.7073	Intermediate Similarity	NPD6054	Approved
0.7063	Intermediate Similarity	NPD6616	Approved
0.7008	Intermediate Similarity	NPD7078	Approved
0.7	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD8449	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6983	Remote Similarity	NPD6675	Approved
0.6983	Remote Similarity	NPD7128	Approved
0.6983	Remote Similarity	NPD5739	Approved
0.6983	Remote Similarity	NPD6402	Approved
0.6964	Remote Similarity	NPD7902	Approved
0.6961	Remote Similarity	NPD7645	Phase 2
0.6949	Remote Similarity	NPD6372	Approved
0.6949	Remote Similarity	NPD6373	Approved
0.6947	Remote Similarity	NPD8450	Suspended
0.6909	Remote Similarity	NPD6399	Phase 3
0.6887	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6016	Approved
0.688	Remote Similarity	NPD6015	Approved
0.6864	Remote Similarity	NPD6899	Approved
0.6864	Remote Similarity	NPD6881	Approved
0.6864	Remote Similarity	NPD7320	Approved
0.6833	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8130	Phase 1
0.6833	Remote Similarity	NPD6650	Approved
0.6833	Remote Similarity	NPD6649	Approved
0.6829	Remote Similarity	NPD7115	Discovery
0.6825	Remote Similarity	NPD5988	Approved
0.6818	Remote Similarity	NPD7515	Phase 2
0.6807	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5697	Approved
0.678	Remote Similarity	NPD5701	Approved
0.6772	Remote Similarity	NPD6067	Discontinued
0.675	Remote Similarity	NPD6883	Approved
0.675	Remote Similarity	NPD7102	Approved
0.675	Remote Similarity	NPD7290	Approved
0.6731	Remote Similarity	NPD6928	Phase 2
0.6724	Remote Similarity	NPD7632	Discontinued
0.6723	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6695	Phase 3
0.6696	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7900	Approved
0.6694	Remote Similarity	NPD6847	Approved
0.6694	Remote Similarity	NPD6617	Approved
0.6694	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6641	Remote Similarity	NPD7604	Phase 2
0.6638	Remote Similarity	NPD5344	Discontinued
0.6614	Remote Similarity	NPD5983	Phase 2
0.6612	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4225	Approved
0.6606	Remote Similarity	NPD7750	Discontinued
0.6583	Remote Similarity	NPD6011	Approved
0.6569	Remote Similarity	NPD6942	Approved
0.6569	Remote Similarity	NPD7339	Approved
0.6565	Remote Similarity	NPD6033	Approved
0.6557	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6008	Approved
0.6542	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3669	Approved
0.6538	Remote Similarity	NPD6336	Discontinued
0.6522	Remote Similarity	NPD4755	Approved
0.6518	Remote Similarity	NPD7637	Suspended
0.6505	Remote Similarity	NPD6933	Approved
0.6486	Remote Similarity	NPD6051	Approved
0.6486	Remote Similarity	NPD5328	Approved
0.6481	Remote Similarity	NPD4786	Approved
0.648	Remote Similarity	NPD6940	Discontinued
0.6475	Remote Similarity	NPD4634	Approved
0.6466	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4202	Approved
0.6415	Remote Similarity	NPD6930	Phase 2
0.6415	Remote Similarity	NPD6931	Approved
0.641	Remote Similarity	NPD5285	Approved
0.641	Remote Similarity	NPD4696	Approved
0.641	Remote Similarity	NPD4700	Approved
0.641	Remote Similarity	NPD5286	Approved
0.64	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6115	Approved
0.6381	Remote Similarity	NPD6118	Approved
0.6381	Remote Similarity	NPD6114	Approved
0.6381	Remote Similarity	NPD6697	Approved
0.6372	Remote Similarity	NPD6079	Approved
0.6364	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8074	Phase 3
0.6364	Remote Similarity	NPD3618	Phase 1
0.6349	Remote Similarity	NPD6274	Approved
0.6348	Remote Similarity	NPD5695	Phase 3
0.6346	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7100	Approved
0.6328	Remote Similarity	NPD7101	Approved
0.6325	Remote Similarity	NPD5696	Approved
0.6321	Remote Similarity	NPD6929	Approved
0.6311	Remote Similarity	NPD6926	Approved
0.6311	Remote Similarity	NPD6924	Approved
0.6311	Remote Similarity	NPD1811	Approved
0.6311	Remote Similarity	NPD1810	Approved
0.6306	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5225	Approved
0.6303	Remote Similarity	NPD5226	Approved
0.6303	Remote Similarity	NPD4633	Approved
0.6303	Remote Similarity	NPD5224	Approved
0.6303	Remote Similarity	NPD5211	Phase 2
0.6296	Remote Similarity	NPD3667	Approved
0.6286	Remote Similarity	NPD6116	Phase 1
0.6286	Remote Similarity	NPD6932	Approved
0.6283	Remote Similarity	NPD3168	Discontinued
0.6281	Remote Similarity	NPD4767	Approved
0.6281	Remote Similarity	NPD4768	Approved
0.6271	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD6672	Approved
0.625	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD5175	Approved
0.6231	Remote Similarity	NPD6921	Approved
0.6231	Remote Similarity	NPD6909	Approved
0.6231	Remote Similarity	NPD6908	Approved
0.6228	Remote Similarity	NPD7087	Discontinued
0.6218	Remote Similarity	NPD5223	Approved
0.6216	Remote Similarity	NPD7334	Approved
0.6216	Remote Similarity	NPD6684	Approved
0.6216	Remote Similarity	NPD5330	Approved
0.6216	Remote Similarity	NPD6409	Approved
0.6216	Remote Similarity	NPD7521	Approved
0.6216	Remote Similarity	NPD7146	Approved
0.6207	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD5141	Approved
0.6195	Remote Similarity	NPD4753	Phase 2
0.6194	Remote Similarity	NPD8336	Approved
0.6194	Remote Similarity	NPD8337	Approved
0.619	Remote Similarity	NPD6117	Approved
0.6179	Remote Similarity	NPD4730	Approved
0.6179	Remote Similarity	NPD4729	Approved
0.6176	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6317	Approved
0.6168	Remote Similarity	NPD6683	Phase 2
0.6154	Remote Similarity	NPD5222	Approved
0.6154	Remote Similarity	NPD5221	Approved
0.6154	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4697	Phase 3
0.614	Remote Similarity	NPD6698	Approved
0.614	Remote Similarity	NPD46	Approved
0.614	Remote Similarity	NPD7838	Discovery
0.6132	Remote Similarity	NPD6925	Approved
0.6132	Remote Similarity	NPD5776	Phase 2
0.6131	Remote Similarity	NPD8338	Approved
0.6126	Remote Similarity	NPD6893	Approved
0.6124	Remote Similarity	NPD6314	Approved
0.6124	Remote Similarity	NPD6313	Approved
0.6117	Remote Similarity	NPD4243	Approved

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