NPASS Compound

Structure

NPC100921 OpenBabel07101718312D 43 44 0 0 1 0 0 0 0 0999 V2000 2.3859 7.2000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0550 6.4569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0331 6.6648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7023 5.9217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6804 6.1296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3496 5.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3277 5.5943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5336 0.2297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7246 -0.3581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9968 4.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4472 -0.1771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8111 0.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9750 5.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2562 0.4107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0020 -0.5392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6441 4.3160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1697 0.0040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0885 -0.1324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6223 4.5239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9787 0.5918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2795 -0.7202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2914 3.7807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8923 0.1850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3479 1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2614 0.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9332 3.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3399 2.4365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3659 -0.3135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.2695 3.9886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7013 0.7728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.9387 3.2455 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.5968 1.7673 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5569 -0.9013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5786 4.9397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.6149 0.3661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 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 12.7308 2.2673 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 11 1 0 0 0 0 9 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 34 1 0 0 0 0 25 26 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 27 28 1 0 0 0 0 27 35 1 0 0 0 0 28 36 1 0 0 0 0 29 30 1 0 0 0 0 29 31 2 0 0 0 0 30 2 1 6 0 0 0 30 42 1 0 0 0 0 31 37 1 0 0 0 0 32 38 1 6 0 0 0 33 39 1 1 0 0 0 34 40 1 6 0 0 0 35 33 1 1 0 0 0 35 43 1 0 0 0 0 36 34 1 6 0 0 0 36 43 1 0 0 0 0 37 41 2 0 0 0 0 37 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.5
Volume:	678.863
LogP:	10.021
LogD:	4.989
LogS:	-6.333
# Rotatable Bonds:	28
TPSA:	103.29
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.071
Synthetic Accessibility Score:	4.325
Fsp3:	0.892
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:	-5.258
MDCK Permeability:	1.2410249837557785e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.949
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	98.48542022705078%
Volume Distribution (VD):	1.254
Pgp-substrate:	1.9363950490951538%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.184
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.981
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.132
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	4.69
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.324
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.489
Skin Sensitization:	0.971
Carcinogencity:	0.022
Eye Corrosion:	0.004
Eye Irritation:	0.051
Respiratory Toxicity:	0.381

Download Data

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

Natural Product: NPC100921

Natural Product ID:	NPC100921
*Common Name:**	Tonkinecin
IUPAC Name:	(2S)-4-[(3S,15R)-3,15-dihydroxy-15-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-2-methyl-2H-furan-5-one
Synonyms:	Tonkinecin
Standard InCHIKey:	BJNHGCXQPCYJLU-CXPQHEJVSA-N
Standard InCHI:	InChI=1S/C37H68O6/c1-3-4-5-6-7-8-11-14-17-20-23-33(39)35-27-28-36(43-35)34(40)24-21-18-15-12-9-10-13-16-19-22-32(38)26-25-31-29-30(2)42-37(31)41/h29-30,32-36,38-40H,3-28H2,1-2H3/t30-,32-,33+,34+,35+,36+/m0/s1
SMILES:	CCCCCCCCCCCC[C@H]([C@H]1CC[C@H]([C@@H](CCCCCCCCCCC[C@@H](CCC2=C[C@H](C)OC2=O)O)O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443402
PubChem CID:	177289
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
NPO32912	uvaria tonkinesis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778240]

☑ 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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	520.0	nM	PMID[484948]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	380.0	nM	PMID[484948]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	1500.0	nM	PMID[484948]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5100.0	nM	PMID[484948]

☑ 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 NPC100921 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	179
0.1-0.2	1450
0.2-0.3	5780
0.3-0.4	13329
0.4-0.5	11733
0.5-0.6	6812
0.6-0.7	2665
0.7-0.8	546
0.8-0.85	40
0.85-0.9	42
0.9-0.95	96
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477018
0.9875	High Similarity	NPC309211
0.9875	High Similarity	NPC477010
0.9753	High Similarity	NPC470401
0.9753	High Similarity	NPC159750
0.9753	High Similarity	NPC473649
0.9753	High Similarity	NPC154097
0.9634	High Similarity	NPC89001
0.9625	High Similarity	NPC156804
0.962	High Similarity	NPC11332
0.962	High Similarity	NPC131002
0.962	High Similarity	NPC65930
0.962	High Similarity	NPC145914
0.962	High Similarity	NPC94875
0.962	High Similarity	NPC475159
0.962	High Similarity	NPC473712
0.962	High Similarity	NPC473780
0.962	High Similarity	NPC180363
0.962	High Similarity	NPC329829
0.962	High Similarity	NPC473529
0.962	High Similarity	NPC73310
0.9518	High Similarity	NPC477016
0.9518	High Similarity	NPC477011
0.9518	High Similarity	NPC477017
0.9506	High Similarity	NPC77871
0.9506	High Similarity	NPC39279
0.9506	High Similarity	NPC9678
0.9506	High Similarity	NPC25764
0.9506	High Similarity	NPC319036
0.9506	High Similarity	NPC329838
0.9506	High Similarity	NPC329615
0.9506	High Similarity	NPC475268
0.9506	High Similarity	NPC292809
0.9506	High Similarity	NPC470400
0.9506	High Similarity	NPC471567
0.9506	High Similarity	NPC473671
0.9506	High Similarity	NPC235809
0.9506	High Similarity	NPC120398
0.9506	High Similarity	NPC322529
0.9506	High Similarity	NPC202055
0.9506	High Similarity	NPC39167
0.9506	High Similarity	NPC473156
0.95	High Similarity	NPC253801
0.95	High Similarity	NPC144415
0.939	High Similarity	NPC231096
0.939	High Similarity	NPC240695
0.939	High Similarity	NPC142117
0.939	High Similarity	NPC232555
0.939	High Similarity	NPC473840
0.939	High Similarity	NPC475581
0.939	High Similarity	NPC25703
0.939	High Similarity	NPC62118
0.939	High Similarity	NPC293136
0.939	High Similarity	NPC241360
0.939	High Similarity	NPC114694
0.939	High Similarity	NPC282815
0.939	High Similarity	NPC219652
0.939	High Similarity	NPC171174
0.939	High Similarity	NPC107717
0.939	High Similarity	NPC112685
0.939	High Similarity	NPC132940
0.9383	High Similarity	NPC163093
0.9286	High Similarity	NPC280612
0.9277	High Similarity	NPC476583
0.9277	High Similarity	NPC258068
0.9277	High Similarity	NPC473995
0.9277	High Similarity	NPC477012
0.9277	High Similarity	NPC20533
0.9268	High Similarity	NPC66346
0.9268	High Similarity	NPC473669
0.9268	High Similarity	NPC110710
0.9268	High Similarity	NPC82795
0.9268	High Similarity	NPC286338
0.9268	High Similarity	NPC132496
0.9268	High Similarity	NPC103284
0.9268	High Similarity	NPC1083
0.9268	High Similarity	NPC107986
0.9268	High Similarity	NPC223871
0.9268	High Similarity	NPC283085
0.9268	High Similarity	NPC473478
0.9268	High Similarity	NPC473651
0.9268	High Similarity	NPC231009
0.9268	High Similarity	NPC477013
0.9268	High Similarity	NPC477014
0.9167	High Similarity	NPC191929
0.9167	High Similarity	NPC274446
0.9167	High Similarity	NPC151403
0.9167	High Similarity	NPC20339
0.9167	High Similarity	NPC171135
0.9167	High Similarity	NPC473905
0.9167	High Similarity	NPC21208
0.9167	High Similarity	NPC169511
0.9167	High Similarity	NPC233551
0.9167	High Similarity	NPC234077
0.9167	High Similarity	NPC81045
0.9167	High Similarity	NPC40376
0.9167	High Similarity	NPC39754
0.9167	High Similarity	NPC320458
0.9167	High Similarity	NPC100454
0.9167	High Similarity	NPC261952
0.9167	High Similarity	NPC280621
0.9167	High Similarity	NPC133730
0.9167	High Similarity	NPC172821
0.9167	High Similarity	NPC242364
0.9167	High Similarity	NPC287164
0.9167	High Similarity	NPC61257
0.9167	High Similarity	NPC48338
0.9167	High Similarity	NPC320569
0.9157	High Similarity	NPC134807
0.9157	High Similarity	NPC473687
0.9157	High Similarity	NPC308412
0.9157	High Similarity	NPC210218
0.9157	High Similarity	NPC103523
0.9157	High Similarity	NPC477015
0.9157	High Similarity	NPC219498
0.9157	High Similarity	NPC279267
0.9157	High Similarity	NPC134885
0.9157	High Similarity	NPC204686
0.9157	High Similarity	NPC134865
0.9157	High Similarity	NPC69082
0.9059	High Similarity	NPC318963
0.9059	High Similarity	NPC91067
0.9059	High Similarity	NPC473504
0.9059	High Similarity	NPC20621
0.9059	High Similarity	NPC40066
0.9059	High Similarity	NPC93794
0.9059	High Similarity	NPC42598
0.9059	High Similarity	NPC81778
0.9048	High Similarity	NPC178215
0.8966	High Similarity	NPC11456
0.8953	High Similarity	NPC239517
0.8953	High Similarity	NPC473904
0.8929	High Similarity	NPC47937
0.8837	High Similarity	NPC14901
0.8837	High Similarity	NPC139418
0.8837	High Similarity	NPC130359
0.881	High Similarity	NPC182383
0.875	High Similarity	NPC473561
0.875	High Similarity	NPC473663
0.875	High Similarity	NPC473520
0.875	High Similarity	NPC475173
0.875	High Similarity	NPC473723
0.8636	High Similarity	NPC473707
0.8523	High Similarity	NPC474761
0.8523	High Similarity	NPC476004
0.8427	Intermediate Similarity	NPC30515
0.8409	Intermediate Similarity	NPC295312
0.8372	Intermediate Similarity	NPC21469
0.8333	Intermediate Similarity	NPC81419
0.8333	Intermediate Similarity	NPC179746
0.8315	Intermediate Similarity	NPC51004
0.8315	Intermediate Similarity	NPC473619
0.8276	Intermediate Similarity	NPC164393
0.8222	Intermediate Similarity	NPC208886
0.8222	Intermediate Similarity	NPC473321
0.8222	Intermediate Similarity	NPC184463
0.8222	Intermediate Similarity	NPC12172
0.8202	Intermediate Similarity	NPC474032
0.8202	Intermediate Similarity	NPC307411
0.8182	Intermediate Similarity	NPC248602
0.8161	Intermediate Similarity	NPC137033
0.8152	Intermediate Similarity	NPC36954
0.814	Intermediate Similarity	NPC11620
0.8132	Intermediate Similarity	NPC295204
0.8132	Intermediate Similarity	NPC476300
0.8132	Intermediate Similarity	NPC475912
0.8132	Intermediate Similarity	NPC162205
0.8132	Intermediate Similarity	NPC288240
0.8132	Intermediate Similarity	NPC273579
0.8125	Intermediate Similarity	NPC84038
0.809	Intermediate Similarity	NPC202672
0.809	Intermediate Similarity	NPC153805
0.809	Intermediate Similarity	NPC474471
0.809	Intermediate Similarity	NPC227379
0.8085	Intermediate Similarity	NPC473326
0.8068	Intermediate Similarity	NPC284902
0.8046	Intermediate Similarity	NPC474780
0.8046	Intermediate Similarity	NPC474251
0.8043	Intermediate Similarity	NPC81386
0.8043	Intermediate Similarity	NPC474035
0.8025	Intermediate Similarity	NPC474705
0.7957	Intermediate Similarity	NPC14961
0.7957	Intermediate Similarity	NPC270013
0.7955	Intermediate Similarity	NPC329749
0.7935	Intermediate Similarity	NPC212486
0.7912	Intermediate Similarity	NPC473448
0.7889	Intermediate Similarity	NPC177629
0.7889	Intermediate Similarity	NPC473715
0.7889	Intermediate Similarity	NPC58219
0.7889	Intermediate Similarity	NPC281516
0.7872	Intermediate Similarity	NPC477921
0.7872	Intermediate Similarity	NPC476315
0.7865	Intermediate Similarity	NPC474949
0.7865	Intermediate Similarity	NPC475019
0.7857	Intermediate Similarity	NPC475711
0.7841	Intermediate Similarity	NPC243618
0.7841	Intermediate Similarity	NPC9868
0.7841	Intermediate Similarity	NPC70424
0.7802	Intermediate Similarity	NPC92974
0.7791	Intermediate Similarity	NPC47653

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 NPC100921 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	2232
0.2-0.3	3887
0.3-0.4	1989
0.4-0.5	586
0.5-0.6	242
0.6-0.7	48
0.7-0.8	4
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
0.7717	Intermediate Similarity	NPD46	Approved
0.7717	Intermediate Similarity	NPD6698	Approved
0.7447	Intermediate Similarity	NPD7983	Approved
0.7353	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7838	Discovery
0.7174	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6686	Approved
0.6869	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3197	Phase 1
0.6822	Remote Similarity	NPD6371	Approved
0.6786	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6633	Remote Similarity	NPD5785	Approved
0.6606	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5362	Discontinued
0.6596	Remote Similarity	NPD7154	Phase 3
0.6562	Remote Similarity	NPD4249	Approved
0.6545	Remote Similarity	NPD6053	Discontinued
0.6505	Remote Similarity	NPD7638	Approved
0.6505	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD5778	Approved
0.65	Remote Similarity	NPD5779	Approved
0.6489	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6435	Approved
0.6484	Remote Similarity	NPD4756	Discovery
0.6471	Remote Similarity	NPD7839	Suspended
0.6458	Remote Similarity	NPD5363	Approved
0.6458	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7640	Approved
0.6442	Remote Similarity	NPD7639	Approved
0.6441	Remote Similarity	NPD7507	Approved
0.6421	Remote Similarity	NPD6110	Phase 1
0.6392	Remote Similarity	NPD5786	Approved
0.6381	Remote Similarity	NPD5344	Discontinued
0.6379	Remote Similarity	NPD8516	Approved
0.6379	Remote Similarity	NPD8513	Phase 3
0.6379	Remote Similarity	NPD8517	Approved
0.6379	Remote Similarity	NPD8515	Approved
0.6364	Remote Similarity	NPD1695	Approved
0.6281	Remote Similarity	NPD7319	Approved
0.6277	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5368	Approved
0.6273	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7829	Approved
0.6271	Remote Similarity	NPD7830	Approved
0.6265	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8039	Approved
0.6237	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4269	Approved
0.6146	Remote Similarity	NPD4270	Approved
0.6146	Remote Similarity	NPD5209	Approved
0.6125	Remote Similarity	NPD4266	Approved
0.6125	Remote Similarity	NPD3728	Approved
0.6125	Remote Similarity	NPD3730	Approved
0.6125	Remote Similarity	NPD3194	Approved
0.6125	Remote Similarity	NPD3195	Phase 2
0.6125	Remote Similarity	NPD3196	Approved
0.6122	Remote Similarity	NPD1694	Approved
0.6116	Remote Similarity	NPD8074	Phase 3
0.6105	Remote Similarity	NPD4252	Approved
0.6092	Remote Similarity	NPD7331	Phase 2
0.6082	Remote Similarity	NPD5332	Approved
0.6082	Remote Similarity	NPD5331	Approved
0.6064	Remote Similarity	NPD4271	Approved
0.6064	Remote Similarity	NPD4268	Approved
0.6063	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4632	Approved
0.6042	Remote Similarity	NPD5369	Approved
0.6042	Remote Similarity	NPD4790	Discontinued
0.604	Remote Similarity	NPD6101	Approved
0.604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7115	Discovery
0.6024	Remote Similarity	NPD6109	Phase 1
0.6	Remote Similarity	NPD3172	Approved
0.6	Remote Similarity	NPD7642	Approved
0.5983	Remote Similarity	NPD7641	Discontinued
0.5981	Remote Similarity	NPD6648	Approved
0.5966	Remote Similarity	NPD8444	Approved
0.5965	Remote Similarity	NPD8297	Approved
0.5962	Remote Similarity	NPD5282	Discontinued
0.595	Remote Similarity	NPD7492	Approved
0.5949	Remote Similarity	NPD6927	Phase 3
0.5946	Remote Similarity	NPD6412	Phase 2
0.5938	Remote Similarity	NPD4819	Approved
0.5938	Remote Similarity	NPD4821	Approved
0.5938	Remote Similarity	NPD4820	Approved
0.5938	Remote Similarity	NPD4822	Approved
0.5935	Remote Similarity	NPD7736	Approved
0.593	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6411	Approved
0.5909	Remote Similarity	NPD3704	Approved
0.5902	Remote Similarity	NPD6616	Approved
0.59	Remote Similarity	NPD6422	Discontinued
0.5882	Remote Similarity	NPD8294	Approved
0.5882	Remote Similarity	NPD6319	Approved
0.5882	Remote Similarity	NPD6054	Approved
0.5882	Remote Similarity	NPD8377	Approved
0.5872	Remote Similarity	NPD7632	Discontinued
0.5854	Remote Similarity	NPD8293	Discontinued
0.5854	Remote Similarity	NPD7078	Approved
0.5847	Remote Similarity	NPD7327	Approved
0.5847	Remote Similarity	NPD7328	Approved
0.5833	Remote Similarity	NPD8378	Approved
0.5833	Remote Similarity	NPD8379	Approved
0.5833	Remote Similarity	NPD8380	Approved
0.5833	Remote Similarity	NPD8033	Approved
0.5833	Remote Similarity	NPD8296	Approved
0.5833	Remote Similarity	NPD8335	Approved
0.581	Remote Similarity	NPD7748	Approved
0.5798	Remote Similarity	NPD7516	Approved
0.5794	Remote Similarity	NPD7260	Phase 2
0.5785	Remote Similarity	NPD6370	Approved
0.5772	Remote Similarity	NPD8451	Approved
0.5769	Remote Similarity	NPD7637	Suspended
0.5763	Remote Similarity	NPD6009	Approved
0.5752	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7320	Approved
0.5752	Remote Similarity	NPD6899	Approved
0.5752	Remote Similarity	NPD6881	Approved
0.575	Remote Similarity	NPD29	Approved
0.575	Remote Similarity	NPD6059	Approved
0.575	Remote Similarity	NPD28	Approved
0.5748	Remote Similarity	NPD6845	Suspended
0.5739	Remote Similarity	NPD2204	Approved
0.5739	Remote Similarity	NPD8130	Phase 1
0.5739	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD8328	Phase 3
0.5738	Remote Similarity	NPD7604	Phase 2
0.573	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5370	Suspended
0.5726	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD6008	Approved
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD6402	Approved
0.5702	Remote Similarity	NPD5983	Phase 2
0.5702	Remote Similarity	NPD6015	Approved
0.5702	Remote Similarity	NPD6016	Approved
0.5701	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD7909	Approved
0.5676	Remote Similarity	NPD6647	Phase 2
0.5664	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD5697	Approved
0.5657	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD5988	Approved
0.5656	Remote Similarity	NPD8080	Discontinued
0.5652	Remote Similarity	NPD6421	Discontinued
0.5652	Remote Similarity	NPD7290	Approved
0.5652	Remote Similarity	NPD6883	Approved
0.5652	Remote Similarity	NPD7102	Approved
0.5648	Remote Similarity	NPD6083	Phase 2
0.5648	Remote Similarity	NPD6084	Phase 2
0.5648	Remote Similarity	NPD7902	Approved
0.5647	Remote Similarity	NPD9119	Approved
0.5647	Remote Similarity	NPD69	Approved
0.5645	Remote Similarity	NPD6336	Discontinued
0.5645	Remote Similarity	NPD8273	Phase 1
0.5641	Remote Similarity	NPD8133	Approved
0.5631	Remote Similarity	NPD6903	Approved
0.563	Remote Similarity	NPD7500	Approved
0.563	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6079	Approved
0.5619	Remote Similarity	NPD7515	Phase 2
0.5619	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD7341	Phase 2
0.5614	Remote Similarity	NPD6011	Approved
0.5603	Remote Similarity	NPD6650	Approved
0.5603	Remote Similarity	NPD6649	Approved
0.5603	Remote Similarity	NPD6617	Approved
0.5603	Remote Similarity	NPD6869	Approved
0.5603	Remote Similarity	NPD6847	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