NPASS Compound

Structure

NPC146852 OpenBabel07101718302D 27 28 0 0 1 0 0 0 0 0999 V2000 -0.5878 4.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7782 2.9071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7782 3.9071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9122 3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4122 4.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0878 3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4122 4.2731 0.0000 C 0 0 2 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 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9122 3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9122 5.1391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4122 2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.1910 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 13 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 13 2 0 0 0 0 7 10 1 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 19 1 0 0 0 0 15 22 1 6 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 1 0 0 0 18 21 1 6 0 0 0 18 27 1 0 0 0 0 19 24 2 0 0 0 0 20 25 1 0 0 0 0 21 4 1 6 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.24
Volume:	399.491
LogP:	1.787
LogD:	1.488
LogS:	-3.667
# Rotatable Bonds:	8
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	4.703
Fsp3:	0.81
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.698
MDCK Permeability:	2.442794902890455e-05
Pgp-inhibitor:	0.926
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.159
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.769
Plasma Protein Binding (PPB):	75.14554595947266%
Volume Distribution (VD):	0.448
Pgp-substrate:	18.741884231567383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.581
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.296
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	6.788
Half-life (T1/2):	0.348

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.113
AMES Toxicity:	0.112
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.389
Carcinogencity:	0.109
Eye Corrosion:	0.004
Eye Irritation:	0.078
Respiratory Toxicity:	0.405

Download Data

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

Natural Product: NPC146852

Natural Product ID:	NPC146852
*Common Name:**	Bicycloalternarene B
IUPAC Name:	(2S,5R)-5-hydroxy-2-[(E,2S,9R)-2,9,10-trihydroxy-6,10-dimethylundec-5-en-2-yl]-3,5,6,7-tetrahydro-2H-1-benzofuran-4-one
Synonyms:
Standard InCHIKey:	GNNBTXNIZDKENT-YIVRKDDVSA-N
Standard InCHI:	InChI=1S/C21H34O6/c1-13(7-10-17(23)20(2,3)25)6-5-11-21(4,26)18-12-14-16(27-18)9-8-15(22)19(14)24/h6,15,17-18,22-23,25-26H,5,7-12H2,1-4H3/b13-6+/t15-,17-,18+,21+/m1/s1
SMILES:	C/C(=CCC[C@@]([C@H]1OC2=C(C1)C(=O)[C@@H](CC2)O)(O)C)/CC[C@H](C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431880
PubChem CID:	72704485
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32811	Alternaria sp. JJY-32	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24128115]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	70000.0	nM	PMID[498280]

☑ 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 NPC146852 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	198
0.1-0.2	1290
0.2-0.3	5070
0.3-0.4	9426
0.4-0.5	15625
0.5-0.6	7633
0.6-0.7	3041
0.7-0.8	396
0.8-0.85	14
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9884	High Similarity	NPC61275
0.913	High Similarity	NPC300584
0.8617	High Similarity	NPC20066
0.8317	Intermediate Similarity	NPC471400
0.8172	Intermediate Similarity	NPC469464
0.8172	Intermediate Similarity	NPC166554
0.8081	Intermediate Similarity	NPC70369
0.8043	Intermediate Similarity	NPC179659
0.798	Intermediate Similarity	NPC471401
0.7959	Intermediate Similarity	NPC35717
0.7938	Intermediate Similarity	NPC8803
0.7925	Intermediate Similarity	NPC247069
0.7917	Intermediate Similarity	NPC469819
0.7917	Intermediate Similarity	NPC114162
0.7865	Intermediate Similarity	NPC472948
0.7835	Intermediate Similarity	NPC91408
0.7835	Intermediate Similarity	NPC279313
0.7816	Intermediate Similarity	NPC477708
0.78	Intermediate Similarity	NPC181645
0.7789	Intermediate Similarity	NPC471399
0.7789	Intermediate Similarity	NPC265856
0.7778	Intermediate Similarity	NPC306908
0.7766	Intermediate Similarity	NPC472008
0.7766	Intermediate Similarity	NPC228415
0.7766	Intermediate Similarity	NPC476708
0.7766	Intermediate Similarity	NPC87189
0.7755	Intermediate Similarity	NPC135576
0.7755	Intermediate Similarity	NPC472734
0.7755	Intermediate Similarity	NPC93271
0.7755	Intermediate Similarity	NPC472733
0.7732	Intermediate Similarity	NPC477241
0.7708	Intermediate Similarity	NPC30515
0.7708	Intermediate Similarity	NPC184463
0.7684	Intermediate Similarity	NPC307411
0.7677	Intermediate Similarity	NPC473574
0.7677	Intermediate Similarity	NPC472731
0.7677	Intermediate Similarity	NPC20078
0.7677	Intermediate Similarity	NPC239895
0.7677	Intermediate Similarity	NPC472732
0.7677	Intermediate Similarity	NPC27105
0.767	Intermediate Similarity	NPC471332
0.767	Intermediate Similarity	NPC471333
0.7667	Intermediate Similarity	NPC470945
0.7667	Intermediate Similarity	NPC470946
0.7667	Intermediate Similarity	NPC470947
0.766	Intermediate Similarity	NPC472007
0.7624	Intermediate Similarity	NPC476270
0.7619	Intermediate Similarity	NPC38154
0.7604	Intermediate Similarity	NPC51004
0.76	Intermediate Similarity	NPC472730
0.76	Intermediate Similarity	NPC153776
0.76	Intermediate Similarity	NPC177680
0.76	Intermediate Similarity	NPC472687
0.76	Intermediate Similarity	NPC471330
0.76	Intermediate Similarity	NPC203388
0.76	Intermediate Similarity	NPC471331
0.76	Intermediate Similarity	NPC99657
0.76	Intermediate Similarity	NPC472729
0.7596	Intermediate Similarity	NPC144854
0.7596	Intermediate Similarity	NPC3316
0.7579	Intermediate Similarity	NPC202672
0.7579	Intermediate Similarity	NPC476707
0.7579	Intermediate Similarity	NPC476704
0.7579	Intermediate Similarity	NPC476706
0.7576	Intermediate Similarity	NPC279722
0.7573	Intermediate Similarity	NPC40170
0.757	Intermediate Similarity	NPC66108
0.7553	Intermediate Similarity	NPC472009
0.7549	Intermediate Similarity	NPC474747
0.7547	Intermediate Similarity	NPC99760
0.7526	Intermediate Similarity	NPC12172
0.7526	Intermediate Similarity	NPC111883
0.7526	Intermediate Similarity	NPC208886
0.7525	Intermediate Similarity	NPC472728
0.7525	Intermediate Similarity	NPC472727
0.7524	Intermediate Similarity	NPC154608
0.7524	Intermediate Similarity	NPC192813
0.7524	Intermediate Similarity	NPC277017
0.75	Intermediate Similarity	NPC236176
0.7476	Intermediate Similarity	NPC475945
0.7476	Intermediate Similarity	NPC472747
0.7476	Intermediate Similarity	NPC475871
0.7476	Intermediate Similarity	NPC472750
0.7475	Intermediate Similarity	NPC36954
0.7453	Intermediate Similarity	NPC77089
0.7453	Intermediate Similarity	NPC20192
0.7453	Intermediate Similarity	NPC101018
0.7451	Intermediate Similarity	NPC9878
0.7451	Intermediate Similarity	NPC47880
0.7451	Intermediate Similarity	NPC472753
0.7449	Intermediate Similarity	NPC179746
0.7449	Intermediate Similarity	NPC475912
0.7449	Intermediate Similarity	NPC81419
0.7449	Intermediate Similarity	NPC476300
0.7449	Intermediate Similarity	NPC212486
0.7423	Intermediate Similarity	NPC474761
0.7423	Intermediate Similarity	NPC478004
0.7423	Intermediate Similarity	NPC476004
0.7423	Intermediate Similarity	NPC478003
0.7423	Intermediate Similarity	NPC158388
0.7423	Intermediate Similarity	NPC477684
0.7419	Intermediate Similarity	NPC477786
0.7419	Intermediate Similarity	NPC477784
0.7419	Intermediate Similarity	NPC477785
0.7404	Intermediate Similarity	NPC472748
0.7396	Intermediate Similarity	NPC269677
0.7391	Intermediate Similarity	NPC67254
0.7383	Intermediate Similarity	NPC210005
0.7379	Intermediate Similarity	NPC39996
0.7379	Intermediate Similarity	NPC324017
0.7379	Intermediate Similarity	NPC320019
0.7379	Intermediate Similarity	NPC149371
0.7379	Intermediate Similarity	NPC472754
0.7374	Intermediate Similarity	NPC474035
0.7374	Intermediate Similarity	NPC81386
0.7368	Intermediate Similarity	NPC112685
0.7368	Intermediate Similarity	NPC47937
0.7364	Intermediate Similarity	NPC251236
0.7364	Intermediate Similarity	NPC40632
0.7364	Intermediate Similarity	NPC96312
0.7364	Intermediate Similarity	NPC328374
0.7347	Intermediate Similarity	NPC476705
0.7347	Intermediate Similarity	NPC475441
0.7347	Intermediate Similarity	NPC329952
0.7345	Intermediate Similarity	NPC472000
0.7345	Intermediate Similarity	NPC471999
0.7345	Intermediate Similarity	NPC472001
0.7339	Intermediate Similarity	NPC49451
0.7333	Intermediate Similarity	NPC472751
0.7333	Intermediate Similarity	NPC472749
0.7333	Intermediate Similarity	NPC102352
0.7327	Intermediate Similarity	NPC266842
0.732	Intermediate Similarity	NPC477011
0.7315	Intermediate Similarity	NPC476023
0.7308	Intermediate Similarity	NPC472755
0.7308	Intermediate Similarity	NPC320294
0.73	Intermediate Similarity	NPC14961
0.73	Intermediate Similarity	NPC270013
0.7297	Intermediate Similarity	NPC97908
0.7297	Intermediate Similarity	NPC474654
0.7297	Intermediate Similarity	NPC122033
0.7297	Intermediate Similarity	NPC287343
0.7297	Intermediate Similarity	NPC470854
0.7292	Intermediate Similarity	NPC471738
0.7292	Intermediate Similarity	NPC248602
0.729	Intermediate Similarity	NPC470257
0.729	Intermediate Similarity	NPC27814
0.7283	Intermediate Similarity	NPC162741
0.7283	Intermediate Similarity	NPC91332
0.7283	Intermediate Similarity	NPC103634
0.7282	Intermediate Similarity	NPC474742
0.7282	Intermediate Similarity	NPC15993
0.7273	Intermediate Similarity	NPC295204
0.7273	Intermediate Similarity	NPC473798
0.7273	Intermediate Similarity	NPC288240
0.7273	Intermediate Similarity	NPC273579
0.7273	Intermediate Similarity	NPC162205
0.7263	Intermediate Similarity	NPC475206
0.7263	Intermediate Similarity	NPC77971
0.7263	Intermediate Similarity	NPC182383
0.7257	Intermediate Similarity	NPC478051
0.7255	Intermediate Similarity	NPC473326
0.7255	Intermediate Similarity	NPC471144
0.7253	Intermediate Similarity	NPC231739
0.7248	Intermediate Similarity	NPC90769
0.7248	Intermediate Similarity	NPC474516
0.7245	Intermediate Similarity	NPC316228
0.7245	Intermediate Similarity	NPC473619
0.7238	Intermediate Similarity	NPC474741
0.7238	Intermediate Similarity	NPC472756
0.7234	Intermediate Similarity	NPC11620
0.7228	Intermediate Similarity	NPC91439
0.7228	Intermediate Similarity	NPC158416
0.7228	Intermediate Similarity	NPC39859
0.7228	Intermediate Similarity	NPC470883
0.7228	Intermediate Similarity	NPC476315
0.7228	Intermediate Similarity	NPC76862
0.7222	Intermediate Similarity	NPC5103
0.7216	Intermediate Similarity	NPC58219
0.7216	Intermediate Similarity	NPC177629
0.7212	Intermediate Similarity	NPC478176
0.7212	Intermediate Similarity	NPC197835
0.7212	Intermediate Similarity	NPC189609
0.7212	Intermediate Similarity	NPC291500
0.7212	Intermediate Similarity	NPC303653
0.7212	Intermediate Similarity	NPC140591
0.7207	Intermediate Similarity	NPC235539
0.7207	Intermediate Similarity	NPC207217
0.7207	Intermediate Similarity	NPC134869
0.7207	Intermediate Similarity	NPC152199
0.72	Intermediate Similarity	NPC14322
0.72	Intermediate Similarity	NPC196227
0.72	Intermediate Similarity	NPC71589
0.72	Intermediate Similarity	NPC190294
0.7196	Intermediate Similarity	NPC293850
0.7191	Intermediate Similarity	NPC160540
0.7188	Intermediate Similarity	NPC134885
0.7188	Intermediate Similarity	NPC475581
0.7188	Intermediate Similarity	NPC204686
0.7188	Intermediate Similarity	NPC231096

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 NPC146852 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1910
0.2-0.3	3866
0.3-0.4	2160
0.4-0.5	691
0.5-0.6	272
0.6-0.7	72
0.7-0.8	5
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
0.7609	Intermediate Similarity	NPD6110	Phase 1
0.7551	Intermediate Similarity	NPD5282	Discontinued
0.7245	Intermediate Similarity	NPD46	Approved
0.7245	Intermediate Similarity	NPD6698	Approved
0.7176	Intermediate Similarity	NPD7331	Phase 2
0.7	Intermediate Similarity	NPD7983	Approved
0.6977	Remote Similarity	NPD3704	Approved
0.6875	Remote Similarity	NPD4632	Approved
0.6789	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6675	Approved
0.6697	Remote Similarity	NPD7128	Approved
0.6697	Remote Similarity	NPD6402	Approved
0.6697	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6637	Remote Similarity	NPD6053	Discontinued
0.6637	Remote Similarity	NPD8297	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6628	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6371	Approved
0.6607	Remote Similarity	NPD4634	Approved
0.6602	Remote Similarity	NPD5778	Approved
0.6602	Remote Similarity	NPD5779	Approved
0.6598	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6435	Approved
0.6591	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6899	Approved
0.6577	Remote Similarity	NPD7320	Approved
0.6577	Remote Similarity	NPD6881	Approved
0.6571	Remote Similarity	NPD4697	Phase 3
0.6566	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD8080	Discontinued
0.6555	Remote Similarity	NPD6370	Approved
0.6552	Remote Similarity	NPD6009	Approved
0.6549	Remote Similarity	NPD6650	Approved
0.6549	Remote Similarity	NPD6649	Approved
0.6549	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4700	Approved
0.6542	Remote Similarity	NPD4696	Approved
0.6542	Remote Similarity	NPD5285	Approved
0.6542	Remote Similarity	NPD5286	Approved
0.6531	Remote Similarity	NPD7154	Phase 3
0.65	Remote Similarity	NPD8328	Phase 3
0.65	Remote Similarity	NPD7604	Phase 2
0.6495	Remote Similarity	NPD5369	Approved
0.6486	Remote Similarity	NPD5697	Approved
0.6486	Remote Similarity	NPD5701	Approved
0.6481	Remote Similarity	NPD5223	Approved
0.6471	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6101	Approved
0.6471	Remote Similarity	NPD6016	Approved
0.6471	Remote Similarity	NPD5328	Approved
0.6471	Remote Similarity	NPD5983	Phase 2
0.6471	Remote Similarity	NPD6015	Approved
0.646	Remote Similarity	NPD7290	Approved
0.646	Remote Similarity	NPD7102	Approved
0.646	Remote Similarity	NPD6883	Approved
0.6449	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7492	Approved
0.6429	Remote Similarity	NPD6011	Approved
0.6429	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6686	Approved
0.6422	Remote Similarity	NPD5224	Approved
0.6422	Remote Similarity	NPD5226	Approved
0.6422	Remote Similarity	NPD5211	Phase 2
0.6422	Remote Similarity	NPD4633	Approved
0.6422	Remote Similarity	NPD5225	Approved
0.6421	Remote Similarity	NPD4756	Discovery
0.6417	Remote Similarity	NPD5988	Approved
0.6415	Remote Similarity	NPD5222	Approved
0.6415	Remote Similarity	NPD5221	Approved
0.6415	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7838	Discovery
0.6404	Remote Similarity	NPD6617	Approved
0.6404	Remote Similarity	NPD8130	Phase 1
0.6404	Remote Similarity	NPD6847	Approved
0.6404	Remote Similarity	NPD6869	Approved
0.6404	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6008	Approved
0.6393	Remote Similarity	NPD6336	Discontinued
0.6393	Remote Similarity	NPD6616	Approved
0.6392	Remote Similarity	NPD5368	Approved
0.6392	Remote Similarity	NPD4695	Discontinued
0.6372	Remote Similarity	NPD6014	Approved
0.6372	Remote Similarity	NPD6012	Approved
0.6372	Remote Similarity	NPD6013	Approved
0.6372	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD4754	Approved
0.6364	Remote Similarity	NPD5174	Approved
0.6356	Remote Similarity	NPD7641	Discontinued
0.6355	Remote Similarity	NPD6083	Phase 2
0.6355	Remote Similarity	NPD6084	Phase 2
0.6355	Remote Similarity	NPD5173	Approved
0.6348	Remote Similarity	NPD6882	Approved
0.6346	Remote Similarity	NPD6411	Approved
0.6346	Remote Similarity	NPD6079	Approved
0.6341	Remote Similarity	NPD8293	Discontinued
0.6341	Remote Similarity	NPD7078	Approved
0.6337	Remote Similarity	NPD3618	Phase 1
0.6337	Remote Similarity	NPD5786	Approved
0.6337	Remote Similarity	NPD5279	Phase 3
0.6333	Remote Similarity	NPD8516	Approved
0.6333	Remote Similarity	NPD8517	Approved
0.6333	Remote Similarity	NPD8515	Approved
0.6333	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8513	Phase 3
0.633	Remote Similarity	NPD5344	Discontinued
0.6321	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4753	Phase 2
0.6306	Remote Similarity	NPD5141	Approved
0.629	Remote Similarity	NPD6033	Approved
0.629	Remote Similarity	NPD7736	Approved
0.6286	Remote Similarity	NPD6399	Phase 3
0.6275	Remote Similarity	NPD4250	Approved
0.6275	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD4768	Approved
0.6238	Remote Similarity	NPD5363	Approved
0.6238	Remote Similarity	NPD1696	Phase 3
0.6204	Remote Similarity	NPD7902	Approved
0.618	Remote Similarity	NPD3197	Phase 1
0.6176	Remote Similarity	NPD4249	Approved
0.6174	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4629	Approved
0.6168	Remote Similarity	NPD5210	Approved
0.6168	Remote Similarity	NPD5695	Phase 3
0.6147	Remote Similarity	NPD5696	Approved
0.6142	Remote Similarity	NPD7260	Phase 2
0.614	Remote Similarity	NPD4729	Approved
0.614	Remote Similarity	NPD5128	Approved
0.614	Remote Similarity	NPD4730	Approved
0.6139	Remote Similarity	NPD3665	Phase 1
0.6139	Remote Similarity	NPD3133	Approved
0.6139	Remote Similarity	NPD4786	Approved
0.6139	Remote Similarity	NPD3666	Approved
0.6134	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7115	Discovery
0.6134	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4202	Approved
0.6129	Remote Similarity	NPD7507	Approved
0.6111	Remote Similarity	NPD7839	Suspended
0.61	Remote Similarity	NPD4269	Approved
0.61	Remote Similarity	NPD3667	Approved
0.61	Remote Similarity	NPD4270	Approved
0.6095	Remote Similarity	NPD5785	Approved
0.6083	Remote Similarity	NPD6335	Approved
0.608	Remote Similarity	NPD8074	Phase 3
0.6078	Remote Similarity	NPD5329	Approved
0.6075	Remote Similarity	NPD7748	Approved
0.6058	Remote Similarity	NPD6672	Approved
0.6058	Remote Similarity	NPD5737	Approved
0.605	Remote Similarity	NPD6274	Approved
0.604	Remote Similarity	NPD5362	Discontinued
0.6038	Remote Similarity	NPD7515	Phase 2
0.6034	Remote Similarity	NPD5135	Approved
0.6034	Remote Similarity	NPD5169	Approved
0.6034	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD5248	Approved
0.6034	Remote Similarity	NPD5250	Approved
0.6034	Remote Similarity	NPD5247	Approved
0.6034	Remote Similarity	NPD5251	Approved
0.6034	Remote Similarity	NPD5249	Phase 3
0.6033	Remote Similarity	NPD7101	Approved
0.6033	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD4225	Approved
0.5984	Remote Similarity	NPD7319	Approved
0.5983	Remote Similarity	NPD5127	Approved
0.5983	Remote Similarity	NPD5215	Approved
0.5983	Remote Similarity	NPD5216	Approved
0.5983	Remote Similarity	NPD5217	Approved
0.598	Remote Similarity	NPD4197	Approved
0.5968	Remote Similarity	NPD7642	Approved
0.5962	Remote Similarity	NPD7524	Approved
0.595	Remote Similarity	NPD6313	Approved
0.595	Remote Similarity	NPD6314	Approved
0.5948	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6648	Approved
0.5946	Remote Similarity	NPD7639	Approved
0.5946	Remote Similarity	NPD7640	Approved
0.5935	Remote Similarity	NPD6909	Approved
0.5935	Remote Similarity	NPD6908	Approved
0.5935	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7900	Approved
0.5917	Remote Similarity	NPD6868	Approved
0.5913	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4820	Approved
0.59	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4819	Approved
0.59	Remote Similarity	NPD4821	Approved
0.59	Remote Similarity	NPD4822	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