NPASS Compound

Structure

NPC160888 OpenBabel07101718242D 55 62 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 4.2219 -6.1910 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 5.0880 -6.6910 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 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 1 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 5.9540 -5.1910 0.0000 C 0 0 1 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 -0.9135 -0.5933 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 6.8200 -0.6910 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 5.0880 -7.6910 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 7.6861 -3.1910 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 -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 5.9540 -6.1910 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 16 2 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 7 8 1 0 0 0 0 7 20 2 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 38 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 21 1 0 0 0 0 12 27 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 50 1 0 0 0 0 15 25 1 0 0 0 0 15 49 1 0 0 0 0 16 29 1 0 0 0 0 17 28 1 0 0 0 0 17 40 1 6 0 0 0 18 3 1 1 0 0 0 18 33 1 0 0 0 0 18 51 1 0 0 0 0 19 41 2 0 0 0 0 19 52 1 0 0 0 0 20 39 1 0 0 0 0 21 42 1 1 0 0 0 22 8 1 6 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 39 1 1 0 0 0 24 38 1 1 0 0 0 25 30 1 0 0 0 0 25 43 1 6 0 0 0 26 13 1 1 0 0 0 26 28 1 0 0 0 0 26 55 1 0 0 0 0 27 39 1 1 0 0 0 27 53 1 0 0 0 0 28 38 1 1 0 0 0 29 35 1 0 0 0 0 29 44 1 6 0 0 0 30 34 1 0 0 0 0 30 45 1 6 0 0 0 31 32 1 0 0 0 0 31 33 1 0 0 0 0 31 46 1 1 0 0 0 32 36 1 0 0 0 0 32 47 1 1 0 0 0 33 52 1 6 0 0 0 34 37 1 0 0 0 0 34 54 1 1 0 0 0 35 40 1 6 0 0 0 35 48 1 0 0 0 0 36 51 1 0 0 0 0 36 54 1 6 0 0 0 37 49 1 0 0 0 0 37 53 1 6 0 0 0 38 5 1 1 0 0 0 39 6 1 1 0 0 0 40 50 1 6 0 0 0 40 55 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	780.39
Volume:	755.888
LogP:	2.032
LogD:	2.414
LogS:	-4.352
# Rotatable Bonds:	6
TPSA:	223.29
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	8
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.149
Synthetic Accessibility Score:	6.698
Fsp3:	0.875
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:	-6.227
MDCK Permeability:	0.0001099620494642295
Pgp-inhibitor:	0.383
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.84
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	35.01226043701172%
Volume Distribution (VD):	0.471
Pgp-substrate:	41.0816535949707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.108
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.052
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	0.84
Half-life (T1/2):	0.668

ADMET: Toxicity

hERG Blockers:	0.64
Human Hepatotoxicity (H-HT):	0.395
Drug-inuced Liver Injury (DILI):	0.453
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.465
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.271
Carcinogencity:	0.663
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC160888

Natural Product ID:	NPC160888
*Common Name:**	TVRSJBQDPYIKKM-IVTAWANVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TVRSJBQDPYIKKM-IVTAWANVSA-N
Standard InCHI:	InChI=1S/C40H60O15/c1-16-14-50-40(35(48)29(16)44)17(2)28-26(55-40)13-24-22-8-7-20-11-21(42)12-27(39(20,6)23(22)9-10-38(24,28)5)53-37-34(30(45)25(43)15-49-37)54-36-32(47)31(46)33(18(3)51-36)52-19(4)41/h7,17-18,21-37,42-48H,1,8-15H2,2-6H3/t17-,18-,21+,22+,23-,24-,25-,26-,27+,28-,29-,30-,31-,32+,33-,34+,35-,36-,37-,38-,39-,40-/m0/s1
SMILES:	C=C1CO[C@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@H](C[C@H]([C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)OC(=O)C)O)O)O)O2)[C@H]([C@H]1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509755
PubChem CID:	10509454
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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[506898]

☑ 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 NPC160888 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	264
0.1-0.2	1881
0.2-0.3	5587
0.3-0.4	12830
0.4-0.5	9410
0.5-0.6	6435
0.6-0.7	3632
0.7-0.8	1732
0.8-0.85	606
0.85-0.9	221
0.9-0.95	83
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475403
0.9908	High Similarity	NPC476085
0.9908	High Similarity	NPC473633
0.9818	High Similarity	NPC50689
0.9727	High Similarity	NPC195560
0.9727	High Similarity	NPC229962
0.964	High Similarity	NPC207243
0.964	High Similarity	NPC198325
0.964	High Similarity	NPC233391
0.963	High Similarity	NPC51154
0.9558	High Similarity	NPC295133
0.9558	High Similarity	NPC257207
0.9537	High Similarity	NPC112274
0.9469	High Similarity	NPC43842
0.9455	High Similarity	NPC63609
0.9444	High Similarity	NPC13190
0.9386	High Similarity	NPC202261
0.9386	High Similarity	NPC106589
0.9369	High Similarity	NPC477807
0.9364	High Similarity	NPC11548
0.9279	High Similarity	NPC477030
0.9279	High Similarity	NPC477029
0.9259	High Similarity	NPC477027
0.9259	High Similarity	NPC475670
0.9259	High Similarity	NPC306131
0.9259	High Similarity	NPC70204
0.9259	High Similarity	NPC477026
0.9189	High Similarity	NPC477808
0.9182	High Similarity	NPC42171
0.9174	High Similarity	NPC141433
0.9167	High Similarity	NPC476541
0.9167	High Similarity	NPC295980
0.9167	High Similarity	NPC476540
0.9167	High Similarity	NPC476539
0.9167	High Similarity	NPC476538
0.9115	High Similarity	NPC475357
0.9107	High Similarity	NPC148965
0.9107	High Similarity	NPC477031
0.9099	High Similarity	NPC144068
0.9091	High Similarity	NPC475247
0.9091	High Similarity	NPC470748
0.9091	High Similarity	NPC294129
0.9091	High Similarity	NPC114188
0.9074	High Similarity	NPC14704
0.9074	High Similarity	NPC230507
0.9074	High Similarity	NPC113044
0.9074	High Similarity	NPC161676
0.9074	High Similarity	NPC283829
0.9074	High Similarity	NPC470432
0.9074	High Similarity	NPC305423
0.9043	High Similarity	NPC314535
0.9043	High Similarity	NPC173555
0.8991	High Similarity	NPC98696
0.8981	High Similarity	NPC473923
0.8981	High Similarity	NPC473476
0.8981	High Similarity	NPC181845
0.8966	High Similarity	NPC193893
0.8957	High Similarity	NPC475629
0.8957	High Similarity	NPC475556
0.8957	High Similarity	NPC72260
0.8957	High Similarity	NPC107607
0.8947	High Similarity	NPC218093
0.8938	High Similarity	NPC207637
0.8938	High Similarity	NPC146652
0.8919	High Similarity	NPC197231
0.8909	High Similarity	NPC248746
0.8909	High Similarity	NPC84956
0.8909	High Similarity	NPC194207
0.8909	High Similarity	NPC208383
0.8909	High Similarity	NPC232054
0.8909	High Similarity	NPC40440
0.8909	High Similarity	NPC475550
0.8909	High Similarity	NPC157530
0.8909	High Similarity	NPC42482
0.8909	High Similarity	NPC102016
0.8909	High Similarity	NPC475333
0.8909	High Similarity	NPC470433
0.8909	High Similarity	NPC73243
0.8909	High Similarity	NPC95051
0.8909	High Similarity	NPC300557
0.8909	High Similarity	NPC171073
0.8909	High Similarity	NPC309278
0.8909	High Similarity	NPC477809
0.8909	High Similarity	NPC250089
0.8909	High Similarity	NPC249265
0.8909	High Similarity	NPC244086
0.8909	High Similarity	NPC22779
0.8909	High Similarity	NPC46190
0.8909	High Similarity	NPC224098
0.8909	High Similarity	NPC150372
0.8909	High Similarity	NPC6806
0.8909	High Similarity	NPC218571
0.8909	High Similarity	NPC14630
0.8899	High Similarity	NPC226642
0.8889	High Similarity	NPC308262
0.8889	High Similarity	NPC208193
0.8889	High Similarity	NPC117445
0.8879	High Similarity	NPC474908
0.8879	High Similarity	NPC40749
0.8879	High Similarity	NPC120390
0.8879	High Similarity	NPC231518
0.8879	High Similarity	NPC475590
0.8879	High Similarity	NPC475219
0.8879	High Similarity	NPC475419
0.887	High Similarity	NPC32177
0.887	High Similarity	NPC291820
0.887	High Similarity	NPC236973
0.887	High Similarity	NPC55532
0.887	High Similarity	NPC30483
0.887	High Similarity	NPC470897
0.887	High Similarity	NPC292467
0.887	High Similarity	NPC469756
0.887	High Similarity	NPC81222
0.886	High Similarity	NPC203862
0.8839	High Similarity	NPC19888
0.8829	High Similarity	NPC224314
0.8829	High Similarity	NPC269297
0.8829	High Similarity	NPC247037
0.8829	High Similarity	NPC23808
0.8829	High Similarity	NPC477811
0.8829	High Similarity	NPC87998
0.8829	High Similarity	NPC222202
0.8807	High Similarity	NPC242748
0.8803	High Similarity	NPC474423
0.8803	High Similarity	NPC264336
0.8803	High Similarity	NPC74259
0.8793	High Similarity	NPC474466
0.8793	High Similarity	NPC473566
0.8793	High Similarity	NPC475358
0.8793	High Similarity	NPC475136
0.8772	High Similarity	NPC212660
0.8761	High Similarity	NPC469347
0.8761	High Similarity	NPC469348
0.875	High Similarity	NPC477028
0.875	High Similarity	NPC476547
0.875	High Similarity	NPC13193
0.875	High Similarity	NPC477032
0.875	High Similarity	NPC124677
0.8727	High Similarity	NPC94272
0.8727	High Similarity	NPC234160
0.8727	High Similarity	NPC473469
0.8716	High Similarity	NPC93352
0.8707	High Similarity	NPC29639
0.8707	High Similarity	NPC44899
0.8707	High Similarity	NPC5883
0.8707	High Similarity	NPC329905
0.8707	High Similarity	NPC304260
0.8696	High Similarity	NPC93883
0.8696	High Similarity	NPC20979
0.8696	High Similarity	NPC99728
0.8696	High Similarity	NPC50305
0.8696	High Similarity	NPC471353
0.8696	High Similarity	NPC471351
0.8696	High Similarity	NPC157376
0.8696	High Similarity	NPC471355
0.8696	High Similarity	NPC471354
0.8696	High Similarity	NPC473852
0.8696	High Similarity	NPC244402
0.8696	High Similarity	NPC309034
0.8696	High Similarity	NPC243196
0.8696	High Similarity	NPC476690
0.8696	High Similarity	NPC87250
0.8696	High Similarity	NPC142066
0.8696	High Similarity	NPC196429
0.8696	High Similarity	NPC27507
0.8696	High Similarity	NPC100048
0.8696	High Similarity	NPC84987
0.8696	High Similarity	NPC158344
0.8696	High Similarity	NPC34390
0.8696	High Similarity	NPC474418
0.8696	High Similarity	NPC77319
0.8684	High Similarity	NPC477810
0.8673	High Similarity	NPC31896
0.8673	High Similarity	NPC473567
0.8673	High Similarity	NPC263359
0.8673	High Similarity	NPC244431
0.8673	High Similarity	NPC254255
0.8673	High Similarity	NPC32361
0.8673	High Similarity	NPC210569
0.8673	High Similarity	NPC216595
0.8661	High Similarity	NPC191439
0.8661	High Similarity	NPC170974
0.8661	High Similarity	NPC103627
0.8661	High Similarity	NPC65155
0.8649	High Similarity	NPC38217
0.8649	High Similarity	NPC472988
0.8636	High Similarity	NPC309448
0.8636	High Similarity	NPC474569
0.8621	High Similarity	NPC10366
0.8621	High Similarity	NPC83287
0.8611	High Similarity	NPC176406
0.8609	High Similarity	NPC99620
0.8609	High Similarity	NPC193382
0.8609	High Similarity	NPC5311
0.8609	High Similarity	NPC199428
0.8609	High Similarity	NPC310341
0.8596	High Similarity	NPC476693
0.8596	High Similarity	NPC79900
0.8596	High Similarity	NPC307642
0.8584	High Similarity	NPC65167

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 NPC160888 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	2031
0.2-0.3	4161
0.3-0.4	1833
0.4-0.5	484
0.5-0.6	295
0.6-0.7	85
0.7-0.8	21
0.8-0.85	3
0.85-0.9	4
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9043	High Similarity	NPD8380	Approved
0.9043	High Similarity	NPD8379	Approved
0.9043	High Similarity	NPD8378	Approved
0.9043	High Similarity	NPD8335	Approved
0.9043	High Similarity	NPD8296	Approved
0.8957	High Similarity	NPD8294	Approved
0.8957	High Similarity	NPD8377	Approved
0.8879	High Similarity	NPD8033	Approved
0.8621	High Similarity	NPD7328	Approved
0.8621	High Similarity	NPD7327	Approved
0.8547	High Similarity	NPD7516	Approved
0.825	Intermediate Similarity	NPD7503	Approved
0.812	Intermediate Similarity	NPD8133	Approved
0.7984	Intermediate Similarity	NPD7507	Approved
0.7937	Intermediate Similarity	NPD7319	Approved
0.7759	Intermediate Similarity	NPD6412	Phase 2
0.7636	Intermediate Similarity	NPD8171	Discontinued
0.7542	Intermediate Similarity	NPD6686	Approved
0.752	Intermediate Similarity	NPD8516	Approved
0.752	Intermediate Similarity	NPD8513	Phase 3
0.752	Intermediate Similarity	NPD8515	Approved
0.752	Intermediate Similarity	NPD8517	Approved
0.7481	Intermediate Similarity	NPD8449	Approved
0.7479	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7736	Approved
0.7424	Intermediate Similarity	NPD8450	Suspended
0.7364	Intermediate Similarity	NPD8293	Discontinued
0.7339	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD8328	Phase 3
0.7241	Intermediate Similarity	NPD7640	Approved
0.7241	Intermediate Similarity	NPD7639	Approved
0.7213	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6370	Approved
0.7155	Intermediate Similarity	NPD7638	Approved
0.7077	Intermediate Similarity	NPD7492	Approved
0.7042	Intermediate Similarity	NPD7625	Phase 1
0.7031	Intermediate Similarity	NPD6059	Approved
0.7031	Intermediate Similarity	NPD6054	Approved
0.7023	Intermediate Similarity	NPD6616	Approved
0.697	Remote Similarity	NPD7078	Approved
0.6929	Remote Similarity	NPD7115	Discovery
0.688	Remote Similarity	NPD6882	Approved
0.688	Remote Similarity	NPD8297	Approved
0.6875	Remote Similarity	NPD7524	Approved
0.687	Remote Similarity	NPD6067	Discontinued
0.6864	Remote Similarity	NPD4225	Approved
0.6846	Remote Similarity	NPD6016	Approved
0.6846	Remote Similarity	NPD6015	Approved
0.6797	Remote Similarity	NPD6009	Approved
0.6794	Remote Similarity	NPD5988	Approved
0.6769	Remote Similarity	NPD6319	Approved
0.6757	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6051	Approved
0.6724	Remote Similarity	NPD6399	Phase 3
0.6694	Remote Similarity	NPD7320	Approved
0.6694	Remote Similarity	NPD7632	Discontinued
0.6693	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD6402	Approved
0.664	Remote Similarity	NPD6372	Approved
0.664	Remote Similarity	NPD6373	Approved
0.664	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7637	Suspended
0.6614	Remote Similarity	NPD6053	Discontinued
0.6612	Remote Similarity	NPD5344	Discontinued
0.6593	Remote Similarity	NPD8074	Phase 3
0.6583	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7750	Discontinued
0.656	Remote Similarity	NPD6881	Approved
0.656	Remote Similarity	NPD6899	Approved
0.6545	Remote Similarity	NPD6928	Phase 2
0.6544	Remote Similarity	NPD6033	Approved
0.6535	Remote Similarity	NPD8130	Phase 1
0.6535	Remote Similarity	NPD6650	Approved
0.6535	Remote Similarity	NPD6649	Approved
0.65	Remote Similarity	NPD6083	Phase 2
0.65	Remote Similarity	NPD6084	Phase 2
0.6481	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5701	Approved
0.648	Remote Similarity	NPD5697	Approved
0.646	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7290	Approved
0.6457	Remote Similarity	NPD6883	Approved
0.6457	Remote Similarity	NPD7102	Approved
0.6457	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6929	Approved
0.6429	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6617	Approved
0.6406	Remote Similarity	NPD6847	Approved
0.6406	Remote Similarity	NPD6869	Approved
0.6396	Remote Similarity	NPD6931	Approved
0.6396	Remote Similarity	NPD6930	Phase 2
0.6396	Remote Similarity	NPD7525	Registered
0.6389	Remote Similarity	NPD7339	Approved
0.6389	Remote Similarity	NPD6942	Approved
0.6387	Remote Similarity	NPD7748	Approved
0.6378	Remote Similarity	NPD6014	Approved
0.6378	Remote Similarity	NPD6012	Approved
0.6378	Remote Similarity	NPD6013	Approved
0.637	Remote Similarity	NPD7604	Phase 2
0.6364	Remote Similarity	NPD7902	Approved
0.6356	Remote Similarity	NPD8035	Phase 2
0.6356	Remote Similarity	NPD8034	Phase 2
0.6349	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5983	Phase 2
0.6341	Remote Similarity	NPD4159	Approved
0.6316	Remote Similarity	NPD4786	Approved
0.6306	Remote Similarity	NPD7645	Phase 2
0.6299	Remote Similarity	NPD6011	Approved
0.6293	Remote Similarity	NPD4251	Approved
0.6293	Remote Similarity	NPD4250	Approved
0.629	Remote Similarity	NPD5211	Phase 2
0.6279	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6336	Discontinued
0.6273	Remote Similarity	NPD5776	Phase 2
0.6273	Remote Similarity	NPD6925	Approved
0.6271	Remote Similarity	NPD6698	Approved
0.6271	Remote Similarity	NPD46	Approved
0.6271	Remote Similarity	NPD7838	Discovery
0.626	Remote Similarity	NPD6648	Approved
0.6239	Remote Similarity	NPD6903	Approved
0.6239	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.623	Remote Similarity	NPD4755	Approved
0.622	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7087	Discontinued
0.6218	Remote Similarity	NPD7515	Phase 2
0.6216	Remote Similarity	NPD7145	Approved
0.6214	Remote Similarity	NPD5956	Approved
0.6207	Remote Similarity	NPD5330	Approved
0.6207	Remote Similarity	NPD6409	Approved
0.6207	Remote Similarity	NPD7146	Approved
0.6207	Remote Similarity	NPD6684	Approved
0.6207	Remote Similarity	NPD4249	Approved
0.6207	Remote Similarity	NPD7521	Approved
0.6207	Remote Similarity	NPD7334	Approved
0.6202	Remote Similarity	NPD4634	Approved
0.6202	Remote Similarity	NPD6371	Approved
0.6198	Remote Similarity	NPD5695	Phase 3
0.6198	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5141	Approved
0.6187	Remote Similarity	NPD8337	Approved
0.6187	Remote Similarity	NPD8336	Approved
0.6179	Remote Similarity	NPD5696	Approved
0.6167	Remote Similarity	NPD4202	Approved
0.6159	Remote Similarity	NPD7799	Discontinued
0.614	Remote Similarity	NPD3667	Approved
0.6129	Remote Similarity	NPD4696	Approved
0.6129	Remote Similarity	NPD5285	Approved
0.6129	Remote Similarity	NPD5286	Approved
0.6129	Remote Similarity	NPD4700	Approved
0.6121	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6893	Approved
0.6121	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7900	Approved
0.6116	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7514	Phase 3
0.609	Remote Similarity	NPD6274	Approved
0.6083	Remote Similarity	NPD5693	Phase 1
0.6074	Remote Similarity	NPD7101	Approved
0.6074	Remote Similarity	NPD7100	Approved
0.6053	Remote Similarity	NPD6902	Approved
0.605	Remote Similarity	NPD4753	Phase 2
0.605	Remote Similarity	NPD5328	Approved
0.6036	Remote Similarity	NPD6933	Approved
0.6034	Remote Similarity	NPD3666	Approved
0.6034	Remote Similarity	NPD3665	Phase 1
0.6034	Remote Similarity	NPD3133	Approved
0.6032	Remote Similarity	NPD5224	Approved
0.6032	Remote Similarity	NPD5226	Approved
0.6032	Remote Similarity	NPD4633	Approved
0.6032	Remote Similarity	NPD5225	Approved
0.6016	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6640	Phase 3
0.6016	Remote Similarity	NPD4767	Approved
0.6016	Remote Similarity	NPD4768	Approved
0.6014	Remote Similarity	NPD8338	Approved
0.6	Remote Similarity	NPD4784	Approved
0.6	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD4785	Approved
0.5985	Remote Similarity	NPD6909	Approved
0.5985	Remote Similarity	NPD6908	Approved
0.5985	Remote Similarity	NPD6921	Approved
0.5985	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD5174	Approved
0.5984	Remote Similarity	NPD5175	Approved
0.5982	Remote Similarity	NPD6932	Approved
0.5966	Remote Similarity	NPD5737	Approved
0.5966	Remote Similarity	NPD6672	Approved
0.5965	Remote Similarity	NPD7332	Phase 2
0.5965	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4243	Approved
0.5952	Remote Similarity	NPD5223	Approved
0.595	Remote Similarity	NPD7983	Approved
0.595	Remote Similarity	NPD6079	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