NPASS Compound

Structure

NPC473633 OpenBabel07101718272D 58 65 0 0 1 0 0 0 0 0999 V2000 -2.4271 -2.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 -5.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 -6.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8966 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8200 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7045 -2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5521 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -2.1756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8200 -4.6910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2219 -6.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -3.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8200 2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3559 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2219 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5521 -1.6910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9540 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7226 -1.1810 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9540 -5.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6861 -2.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0880 -4.6910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8200 -1.6910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0880 -3.6910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8200 -0.6910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9540 -3.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0880 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3559 -6.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -4.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4181 -2.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6361 -0.7743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 -6.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 -3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0181 0.4013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -1.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8200 -3.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -5.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 -2.1910 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 1 17 2 0 0 0 0 2 18 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 8 9 1 0 0 0 0 8 22 2 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 40 1 0 0 0 0 12 22 1 0 0 0 0 12 23 1 0 0 0 0 13 23 1 0 0 0 0 13 29 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 52 1 0 0 0 0 16 27 1 0 0 0 0 16 51 1 0 0 0 0 17 31 1 0 0 0 0 18 30 1 0 0 0 0 18 42 1 6 0 0 0 19 3 1 1 0 0 0 19 32 1 0 0 0 0 19 53 1 0 0 0 0 20 43 2 0 0 0 0 20 54 1 0 0 0 0 21 44 2 0 0 0 0 21 55 1 0 0 0 0 22 41 1 0 0 0 0 23 45 1 1 0 0 0 24 9 1 6 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 25 41 1 1 0 0 0 26 40 1 1 0 0 0 27 33 1 0 0 0 0 27 46 1 6 0 0 0 28 14 1 1 0 0 0 28 30 1 0 0 0 0 28 58 1 0 0 0 0 29 41 1 1 0 0 0 29 56 1 0 0 0 0 30 40 1 1 0 0 0 31 37 1 0 0 0 0 31 47 1 6 0 0 0 32 34 1 0 0 0 0 32 48 1 6 0 0 0 33 35 1 0 0 0 0 33 49 1 6 0 0 0 34 36 1 0 0 0 0 34 54 1 1 0 0 0 35 38 1 0 0 0 0 35 57 1 1 0 0 0 36 39 1 0 0 0 0 36 55 1 1 0 0 0 37 42 1 6 0 0 0 37 50 1 0 0 0 0 38 51 1 0 0 0 0 38 56 1 6 0 0 0 39 53 1 0 0 0 0 39 57 1 6 0 0 0 40 6 1 1 0 0 0 41 7 1 1 0 0 0 42 52 1 6 0 0 0 42 58 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	822.4
Volume:	796.634
LogP:	2.181
LogD:	2.46
LogS:	-4.49
# Rotatable Bonds:	8
TPSA:	229.36
# H-Bond Aceptor:	16
# H-Bond Donor:	6
# Rings:	8
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.162
Synthetic Accessibility Score:	6.758
Fsp3:	0.857
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.109
MDCK Permeability:	0.00013894075527787209
Pgp-inhibitor:	0.631
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.83
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.106
Plasma Protein Binding (PPB):	32.69548416137695%
Volume Distribution (VD):	0.597
Pgp-substrate:	42.597354888916016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.135
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	0.9
Half-life (T1/2):	0.69

ADMET: Toxicity

hERG Blockers:	0.769
Human Hepatotoxicity (H-HT):	0.857
Drug-inuced Liver Injury (DILI):	0.752
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.437
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.176
Carcinogencity:	0.479
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC473633

Natural Product ID:	NPC473633
*Common Name:**	Draconin B
IUPAC Name:	n.a.
Synonyms:	draconin B
Standard InCHIKey:	RKZQYSQHBPDHHB-ASZZWXFMSA-N
Standard InCHI:	InChI=1S/C42H62O16/c1-17-15-52-42(37(50)31(17)47)18(2)30-28(58-42)14-26-24-9-8-22-12-23(45)13-29(41(22,7)25(24)10-11-40(26,30)6)56-38-35(33(49)27(46)16-51-38)57-39-36(55-21(5)44)34(54-20(4)43)32(48)19(3)53-39/h8,18-19,23-39,45-50H,1,9-16H2,2-7H3/t18-,19-,23+,24+,25-,26-,27-,28-,29+,30-,31-,32-,33-,34+,35+,36+,37-,38-,39-,40-,41-,42-/m0/s1
SMILES:	CC(=O)O[C@H]1[C@H](O[C@H]2[C@@H](OC[C@@H]([C@@H]2O)O)O[C@@H]2C[C@H](O)CC3=CC[C@@H]4[C@@H]([C@@]23C)CC[C@]2([C@H]4C[C@H]3[C@@H]2[C@H](C)[C@@]2(O3)OCC(=C)[C@@H]([C@@H]2O)O)C)O[C@H]([C@@H]([C@H]1OC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447737
PubChem CID:	10930857
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal 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
NPO3545	Dracaena draco	Species	Asparagaceae	Eukaryota	bark	n.a.	n.a.	PMID[12828464]
NPO3545	Dracaena draco	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3545	Dracaena draco	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3545	Dracaena draco	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3545	Dracaena draco	Species	Asparagaceae	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	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	39000.0	nM	PMID[460843]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	9.4	%	PMID[460843]

☑ 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 NPC473633 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	270
0.1-0.2	1903
0.2-0.3	5676
0.3-0.4	12948
0.4-0.5	9387
0.5-0.6	6412
0.6-0.7	3515
0.7-0.8	1641
0.8-0.85	642
0.85-0.9	197
0.9-0.95	85
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476085
0.9909	High Similarity	NPC50689
0.9908	High Similarity	NPC160888
0.9908	High Similarity	NPC475403
0.9818	High Similarity	NPC195560
0.9818	High Similarity	NPC229962
0.973	High Similarity	NPC233391
0.973	High Similarity	NPC207243
0.973	High Similarity	NPC198325
0.9646	High Similarity	NPC257207
0.9646	High Similarity	NPC295133
0.9558	High Similarity	NPC43842
0.9545	High Similarity	NPC63609
0.9541	High Similarity	NPC51154
0.9474	High Similarity	NPC202261
0.9474	High Similarity	NPC106589
0.9459	High Similarity	NPC477807
0.9455	High Similarity	NPC11548
0.945	High Similarity	NPC112274
0.9369	High Similarity	NPC477029
0.9369	High Similarity	NPC477030
0.9358	High Similarity	NPC13190
0.9279	High Similarity	NPC477808
0.9273	High Similarity	NPC42171
0.9204	High Similarity	NPC475357
0.9196	High Similarity	NPC477031
0.9196	High Similarity	NPC148965
0.9182	High Similarity	NPC470748
0.9182	High Similarity	NPC475247
0.9182	High Similarity	NPC294129
0.9174	High Similarity	NPC477026
0.9174	High Similarity	NPC306131
0.9174	High Similarity	NPC477027
0.9174	High Similarity	NPC475670
0.9174	High Similarity	NPC70204
0.9091	High Similarity	NPC141433
0.9083	High Similarity	NPC476541
0.9083	High Similarity	NPC476538
0.9083	High Similarity	NPC98696
0.9083	High Similarity	NPC476539
0.9083	High Similarity	NPC476540
0.9083	High Similarity	NPC295980
0.9027	High Similarity	NPC146652
0.9018	High Similarity	NPC144068
0.9009	High Similarity	NPC114188
0.9	High Similarity	NPC248746
0.9	High Similarity	NPC95051
0.9	High Similarity	NPC171073
0.9	High Similarity	NPC6806
0.9	High Similarity	NPC309278
0.9	High Similarity	NPC218571
0.9	High Similarity	NPC232054
0.9	High Similarity	NPC208383
0.9	High Similarity	NPC470433
0.9	High Similarity	NPC475333
0.9	High Similarity	NPC22779
0.9	High Similarity	NPC300557
0.9	High Similarity	NPC102016
0.9	High Similarity	NPC194207
0.9	High Similarity	NPC475550
0.9	High Similarity	NPC249265
0.9	High Similarity	NPC84956
0.9	High Similarity	NPC73243
0.9	High Similarity	NPC224098
0.9	High Similarity	NPC244086
0.9	High Similarity	NPC477809
0.9	High Similarity	NPC150372
0.9	High Similarity	NPC46190
0.8991	High Similarity	NPC470432
0.8991	High Similarity	NPC283829
0.8991	High Similarity	NPC305423
0.8991	High Similarity	NPC14704
0.8991	High Similarity	NPC230507
0.8991	High Similarity	NPC113044
0.8991	High Similarity	NPC161676
0.8974	High Similarity	NPC208193
0.8974	High Similarity	NPC117445
0.8974	High Similarity	NPC308262
0.8966	High Similarity	NPC120390
0.8966	High Similarity	NPC475419
0.8966	High Similarity	NPC173555
0.8966	High Similarity	NPC314535
0.8966	High Similarity	NPC474908
0.8966	High Similarity	NPC475590
0.8919	High Similarity	NPC477811
0.8919	High Similarity	NPC222202
0.8919	High Similarity	NPC269297
0.8919	High Similarity	NPC224314
0.8919	High Similarity	NPC87998
0.8919	High Similarity	NPC247037
0.8919	High Similarity	NPC23808
0.8899	High Similarity	NPC181845
0.8899	High Similarity	NPC473476
0.8899	High Similarity	NPC473923
0.8889	High Similarity	NPC474423
0.8889	High Similarity	NPC264336
0.8889	High Similarity	NPC193893
0.8889	High Similarity	NPC74259
0.8879	High Similarity	NPC72260
0.8879	High Similarity	NPC475629
0.8879	High Similarity	NPC475358
0.8879	High Similarity	NPC475556
0.8879	High Similarity	NPC107607
0.8879	High Similarity	NPC473566
0.887	High Similarity	NPC218093
0.886	High Similarity	NPC207637
0.885	High Similarity	NPC469347
0.885	High Similarity	NPC469348
0.8839	High Similarity	NPC124677
0.8839	High Similarity	NPC13193
0.8839	High Similarity	NPC477028
0.8839	High Similarity	NPC197231
0.8839	High Similarity	NPC477032
0.8839	High Similarity	NPC476547
0.8829	High Similarity	NPC157530
0.8829	High Similarity	NPC40440
0.8829	High Similarity	NPC42482
0.8829	High Similarity	NPC14630
0.8829	High Similarity	NPC250089
0.8818	High Similarity	NPC94272
0.8818	High Similarity	NPC226642
0.8803	High Similarity	NPC475219
0.8803	High Similarity	NPC231518
0.8803	High Similarity	NPC40749
0.8793	High Similarity	NPC236973
0.8793	High Similarity	NPC291820
0.8793	High Similarity	NPC469756
0.8793	High Similarity	NPC32177
0.8793	High Similarity	NPC292467
0.8793	High Similarity	NPC30483
0.8793	High Similarity	NPC81222
0.8793	High Similarity	NPC470897
0.8793	High Similarity	NPC55532
0.8783	High Similarity	NPC100048
0.8783	High Similarity	NPC203862
0.8783	High Similarity	NPC20979
0.8783	High Similarity	NPC476690
0.8772	High Similarity	NPC477810
0.8761	High Similarity	NPC244431
0.8761	High Similarity	NPC254255
0.8761	High Similarity	NPC32361
0.8761	High Similarity	NPC210569
0.8761	High Similarity	NPC31896
0.8761	High Similarity	NPC19888
0.8761	High Similarity	NPC263359
0.8727	High Similarity	NPC309448
0.8727	High Similarity	NPC242748
0.8718	High Similarity	NPC475136
0.8718	High Similarity	NPC474466
0.8707	High Similarity	NPC10366
0.8696	High Similarity	NPC212660
0.8684	High Similarity	NPC79900
0.8684	High Similarity	NPC307642
0.8684	High Similarity	NPC476693
0.8673	High Similarity	NPC65167
0.8655	High Similarity	NPC256983
0.8649	High Similarity	NPC234160
0.8649	High Similarity	NPC473469
0.8649	High Similarity	NPC190395
0.8636	High Similarity	NPC93352
0.8632	High Similarity	NPC329905
0.8632	High Similarity	NPC44899
0.8632	High Similarity	NPC304260
0.8632	High Similarity	NPC29639
0.8632	High Similarity	NPC5883
0.8621	High Similarity	NPC87250
0.8621	High Similarity	NPC471355
0.8621	High Similarity	NPC84987
0.8621	High Similarity	NPC309034
0.8621	High Similarity	NPC471354
0.8621	High Similarity	NPC34390
0.8621	High Similarity	NPC244402
0.8621	High Similarity	NPC196429
0.8621	High Similarity	NPC142066
0.8621	High Similarity	NPC474418
0.8621	High Similarity	NPC158344
0.8621	High Similarity	NPC471351
0.8621	High Similarity	NPC27507
0.8621	High Similarity	NPC93883
0.8621	High Similarity	NPC77319
0.8621	High Similarity	NPC157376
0.8621	High Similarity	NPC99728
0.8621	High Similarity	NPC50305
0.8621	High Similarity	NPC471353
0.8621	High Similarity	NPC473852
0.8621	High Similarity	NPC243196
0.8609	High Similarity	NPC32707
0.8609	High Similarity	NPC167183
0.8596	High Similarity	NPC216595
0.8596	High Similarity	NPC473567
0.8596	High Similarity	NPC308140
0.8584	High Similarity	NPC170974
0.8584	High Similarity	NPC65155
0.8584	High Similarity	NPC191439
0.8584	High Similarity	NPC103627
0.8571	High Similarity	NPC220427
0.8571	High Similarity	NPC472988
0.8571	High Similarity	NPC38217
0.8571	High Similarity	NPC49032
0.8571	High Similarity	NPC125324

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 NPC473633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	2054
0.2-0.3	4178
0.3-0.4	1812
0.4-0.5	462
0.5-0.6	294
0.6-0.7	81
0.7-0.8	21
0.8-0.85	3
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8966	High Similarity	NPD8335	Approved
0.8966	High Similarity	NPD8380	Approved
0.8966	High Similarity	NPD8379	Approved
0.8966	High Similarity	NPD8378	Approved
0.8966	High Similarity	NPD8296	Approved
0.8879	High Similarity	NPD8377	Approved
0.8879	High Similarity	NPD8294	Approved
0.8803	High Similarity	NPD8033	Approved
0.8547	High Similarity	NPD7327	Approved
0.8547	High Similarity	NPD7328	Approved
0.8475	Intermediate Similarity	NPD7516	Approved
0.8205	Intermediate Similarity	NPD8133	Approved
0.8182	Intermediate Similarity	NPD7503	Approved
0.792	Intermediate Similarity	NPD7507	Approved
0.7874	Intermediate Similarity	NPD7319	Approved
0.7692	Intermediate Similarity	NPD6412	Phase 2
0.7568	Intermediate Similarity	NPD8171	Discontinued
0.75	Intermediate Similarity	NPD8450	Suspended
0.7479	Intermediate Similarity	NPD6686	Approved
0.746	Intermediate Similarity	NPD8513	Phase 3
0.746	Intermediate Similarity	NPD8516	Approved
0.746	Intermediate Similarity	NPD8515	Approved
0.746	Intermediate Similarity	NPD8517	Approved
0.7424	Intermediate Similarity	NPD8449	Approved
0.7417	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7736	Approved
0.7344	Intermediate Similarity	NPD8328	Phase 3
0.7308	Intermediate Similarity	NPD8293	Discontinued
0.728	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7639	Approved
0.7179	Intermediate Similarity	NPD7640	Approved
0.7154	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6370	Approved
0.7094	Intermediate Similarity	NPD7638	Approved
0.7023	Intermediate Similarity	NPD7492	Approved
0.6993	Remote Similarity	NPD7625	Phase 1
0.6977	Remote Similarity	NPD6059	Approved
0.6977	Remote Similarity	NPD6054	Approved
0.697	Remote Similarity	NPD6616	Approved
0.6917	Remote Similarity	NPD7078	Approved
0.6875	Remote Similarity	NPD7115	Discovery
0.6825	Remote Similarity	NPD8297	Approved
0.6825	Remote Similarity	NPD6882	Approved
0.6818	Remote Similarity	NPD6067	Discontinued
0.6814	Remote Similarity	NPD7524	Approved
0.6807	Remote Similarity	NPD4225	Approved
0.6794	Remote Similarity	NPD6016	Approved
0.6794	Remote Similarity	NPD6015	Approved
0.6744	Remote Similarity	NPD6009	Approved
0.6742	Remote Similarity	NPD5988	Approved
0.6718	Remote Similarity	NPD6319	Approved
0.6696	Remote Similarity	NPD6051	Approved
0.6696	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6399	Phase 3
0.6641	Remote Similarity	NPD4632	Approved
0.664	Remote Similarity	NPD7320	Approved
0.6639	Remote Similarity	NPD7632	Discontinued
0.6613	Remote Similarity	NPD6008	Approved
0.6613	Remote Similarity	NPD6675	Approved
0.6613	Remote Similarity	NPD7128	Approved
0.6613	Remote Similarity	NPD6402	Approved
0.6613	Remote Similarity	NPD5739	Approved
0.6607	Remote Similarity	NPD6695	Phase 3
0.6587	Remote Similarity	NPD6372	Approved
0.6587	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6373	Approved
0.6581	Remote Similarity	NPD7637	Suspended
0.6562	Remote Similarity	NPD6053	Discontinued
0.6557	Remote Similarity	NPD5344	Discontinued
0.6544	Remote Similarity	NPD8074	Phase 3
0.6529	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7750	Discontinued
0.6508	Remote Similarity	NPD6899	Approved
0.6508	Remote Similarity	NPD6881	Approved
0.6496	Remote Similarity	NPD6033	Approved
0.6486	Remote Similarity	NPD6928	Phase 2
0.6484	Remote Similarity	NPD8130	Phase 1
0.6484	Remote Similarity	NPD6649	Approved
0.6484	Remote Similarity	NPD6650	Approved
0.6446	Remote Similarity	NPD6084	Phase 2
0.6446	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD5697	Approved
0.6422	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7102	Approved
0.6406	Remote Similarity	NPD6883	Approved
0.6406	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7290	Approved
0.6404	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6929	Approved
0.6378	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6847	Approved
0.6357	Remote Similarity	NPD6869	Approved
0.6357	Remote Similarity	NPD6617	Approved
0.6339	Remote Similarity	NPD7525	Registered
0.6339	Remote Similarity	NPD6931	Approved
0.6339	Remote Similarity	NPD6930	Phase 2
0.6333	Remote Similarity	NPD7748	Approved
0.633	Remote Similarity	NPD7339	Approved
0.633	Remote Similarity	NPD6942	Approved
0.6328	Remote Similarity	NPD6014	Approved
0.6328	Remote Similarity	NPD6012	Approved
0.6328	Remote Similarity	NPD6013	Approved
0.6324	Remote Similarity	NPD7604	Phase 2
0.6311	Remote Similarity	NPD7902	Approved
0.6303	Remote Similarity	NPD8034	Phase 2
0.6303	Remote Similarity	NPD8035	Phase 2
0.6299	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5983	Phase 2
0.629	Remote Similarity	NPD4159	Approved
0.6261	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD7645	Phase 2
0.624	Remote Similarity	NPD5211	Phase 2
0.6239	Remote Similarity	NPD4250	Approved
0.6239	Remote Similarity	NPD4251	Approved
0.6232	Remote Similarity	NPD6336	Discontinued
0.6231	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD46	Approved
0.6218	Remote Similarity	NPD6698	Approved
0.6218	Remote Similarity	NPD7838	Discovery
0.6216	Remote Similarity	NPD5776	Phase 2
0.6216	Remote Similarity	NPD6925	Approved
0.621	Remote Similarity	NPD6648	Approved
0.6186	Remote Similarity	NPD6903	Approved
0.6186	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD4755	Approved
0.6172	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.617	Remote Similarity	NPD5956	Approved
0.6167	Remote Similarity	NPD7515	Phase 2
0.6167	Remote Similarity	NPD7087	Discontinued
0.6161	Remote Similarity	NPD7145	Approved
0.6154	Remote Similarity	NPD7521	Approved
0.6154	Remote Similarity	NPD7334	Approved
0.6154	Remote Similarity	NPD6409	Approved
0.6154	Remote Similarity	NPD7146	Approved
0.6154	Remote Similarity	NPD6684	Approved
0.6154	Remote Similarity	NPD5330	Approved
0.6154	Remote Similarity	NPD6371	Approved
0.6154	Remote Similarity	NPD4634	Approved
0.6154	Remote Similarity	NPD4249	Approved
0.6148	Remote Similarity	NPD5695	Phase 3
0.6148	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD8336	Approved
0.6143	Remote Similarity	NPD8337	Approved
0.6142	Remote Similarity	NPD5141	Approved
0.6129	Remote Similarity	NPD5696	Approved
0.6121	Remote Similarity	NPD7799	Discontinued
0.6116	Remote Similarity	NPD4202	Approved
0.6087	Remote Similarity	NPD3667	Approved
0.608	Remote Similarity	NPD4700	Approved
0.608	Remote Similarity	NPD5286	Approved
0.608	Remote Similarity	NPD5285	Approved
0.608	Remote Similarity	NPD4696	Approved
0.6068	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6893	Approved
0.6068	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7900	Approved
0.6053	Remote Similarity	NPD7514	Phase 3
0.6045	Remote Similarity	NPD6274	Approved
0.6033	Remote Similarity	NPD5693	Phase 1
0.6029	Remote Similarity	NPD7101	Approved
0.6029	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD6902	Approved
0.5984	Remote Similarity	NPD5224	Approved
0.5984	Remote Similarity	NPD4633	Approved
0.5984	Remote Similarity	NPD5225	Approved
0.5984	Remote Similarity	NPD5226	Approved
0.5983	Remote Similarity	NPD3133	Approved
0.5983	Remote Similarity	NPD3665	Phase 1
0.5983	Remote Similarity	NPD3666	Approved
0.5982	Remote Similarity	NPD6933	Approved
0.5972	Remote Similarity	NPD8338	Approved
0.5969	Remote Similarity	NPD6640	Phase 3
0.5969	Remote Similarity	NPD4768	Approved
0.5969	Remote Similarity	NPD4767	Approved
0.5968	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD6335	Approved
0.5946	Remote Similarity	NPD4785	Approved
0.5946	Remote Similarity	NPD4784	Approved
0.5942	Remote Similarity	NPD6921	Approved
0.5942	Remote Similarity	NPD6908	Approved
0.5942	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD6909	Approved
0.5938	Remote Similarity	NPD5174	Approved
0.5938	Remote Similarity	NPD5175	Approved
0.5929	Remote Similarity	NPD6932	Approved
0.5917	Remote Similarity	NPD5737	Approved
0.5917	Remote Similarity	NPD6672	Approved
0.5913	Remote Similarity	NPD7332	Phase 2
0.5913	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4243	Approved
0.5906	Remote Similarity	NPD5223	Approved
0.5903	Remote Similarity	NPD7260	Phase 2
0.5902	Remote Similarity	NPD7983	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