NPASS Compound

Structure

NPC61275 OpenBabel07101718292D 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 0.9122 3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 4.4071 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 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 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 3.4071 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 -3.5878 2.5411 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 -3.0878 3.4071 0.0000 C 0 0 2 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 -4.5878 2.5411 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 -3.9538 3.9071 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 13 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 13 2 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 20 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 3 1 6 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:	2.244
LogD:	1.444
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:	4.88
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:	-4.655
MDCK Permeability:	8.647291906527244e-06
Pgp-inhibitor:	0.985
Pgp-substrate:	0.186
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.045

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.494
Plasma Protein Binding (PPB):	86.74613189697266%
Volume Distribution (VD):	0.634
Pgp-substrate:	12.77785587310791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.73
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	7.485
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.422
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.185
Skin Sensitization:	0.152
Carcinogencity:	0.433
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.432

Download Data

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

Natural Product: NPC61275

Natural Product ID:	NPC61275
*Common Name:**	Bicycloalternarene A
IUPAC Name:	(2S,5R)-5-hydroxy-2-[(2S,5R,6S)-2,5,6-trihydroxy-6,10-dimethylundec-9-en-2-yl]-3,5,6,7-tetrahydro-2H-1-benzofuran-4-one
Synonyms:
Standard InCHIKey:	AVLXNKGSFZAMJF-UTYXMITFSA-N
Standard InCHI:	InChI=1S/C21H34O6/c1-13(2)6-5-10-20(3,25)17(23)9-11-21(4,26)18-12-14-16(27-18)8-7-15(22)19(14)24/h6,15,17-18,22-23,25-26H,5,7-12H2,1-4H3/t15-,17-,18+,20+,21+/m1/s1
SMILES:	CC(=CCC[C@@](C)([C@@H](CC[C@@](C)([C@@H]1CC2=C(CC[C@H](C2=O)O)O1)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431879
PubChem CID:	72704484
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	=	62000.0	nM	PMID[478682]

☑ 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 NPC61275 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	205
0.1-0.2	1290
0.2-0.3	4930
0.3-0.4	8903
0.4-0.5	15828
0.5-0.6	7815
0.6-0.7	3299
0.7-0.8	406
0.8-0.85	17
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	NPC146852
0.9032	High Similarity	NPC300584
0.8526	High Similarity	NPC20066
0.8416	Intermediate Similarity	NPC471400
0.8182	Intermediate Similarity	NPC70369
0.8085	Intermediate Similarity	NPC469464
0.8085	Intermediate Similarity	NPC166554
0.8081	Intermediate Similarity	NPC471401
0.8041	Intermediate Similarity	NPC8803
0.8021	Intermediate Similarity	NPC114162
0.8021	Intermediate Similarity	NPC469819
0.8019	Intermediate Similarity	NPC247069
0.7978	Intermediate Similarity	NPC472948
0.7957	Intermediate Similarity	NPC179659
0.7938	Intermediate Similarity	NPC279313
0.7938	Intermediate Similarity	NPC91408
0.79	Intermediate Similarity	NPC181645
0.7879	Intermediate Similarity	NPC35717
0.7872	Intermediate Similarity	NPC476708
0.7872	Intermediate Similarity	NPC228415
0.7872	Intermediate Similarity	NPC87189
0.7857	Intermediate Similarity	NPC135576
0.7857	Intermediate Similarity	NPC93271
0.7857	Intermediate Similarity	NPC472734
0.7857	Intermediate Similarity	NPC472733
0.7835	Intermediate Similarity	NPC477241
0.7812	Intermediate Similarity	NPC30515
0.7812	Intermediate Similarity	NPC184463
0.7789	Intermediate Similarity	NPC307411
0.7778	Intermediate Similarity	NPC20078
0.7778	Intermediate Similarity	NPC27105
0.7778	Intermediate Similarity	NPC473574
0.7778	Intermediate Similarity	NPC472731
0.7778	Intermediate Similarity	NPC472732
0.7778	Intermediate Similarity	NPC239895
0.7767	Intermediate Similarity	NPC471333
0.7767	Intermediate Similarity	NPC471332
0.7727	Intermediate Similarity	NPC477708
0.7723	Intermediate Similarity	NPC476270
0.7714	Intermediate Similarity	NPC38154
0.7708	Intermediate Similarity	NPC265856
0.7708	Intermediate Similarity	NPC51004
0.7708	Intermediate Similarity	NPC471399
0.77	Intermediate Similarity	NPC472730
0.77	Intermediate Similarity	NPC153776
0.77	Intermediate Similarity	NPC177680
0.77	Intermediate Similarity	NPC472687
0.77	Intermediate Similarity	NPC471331
0.77	Intermediate Similarity	NPC471330
0.77	Intermediate Similarity	NPC203388
0.77	Intermediate Similarity	NPC306908
0.77	Intermediate Similarity	NPC99657
0.77	Intermediate Similarity	NPC472729
0.7692	Intermediate Similarity	NPC3316
0.7692	Intermediate Similarity	NPC144854
0.7684	Intermediate Similarity	NPC202672
0.7684	Intermediate Similarity	NPC472008
0.7684	Intermediate Similarity	NPC476707
0.7684	Intermediate Similarity	NPC476706
0.7684	Intermediate Similarity	NPC476704
0.7677	Intermediate Similarity	NPC279722
0.767	Intermediate Similarity	NPC40170
0.7647	Intermediate Similarity	NPC474747
0.7642	Intermediate Similarity	NPC99760
0.7629	Intermediate Similarity	NPC12172
0.7629	Intermediate Similarity	NPC111883
0.7629	Intermediate Similarity	NPC208886
0.7624	Intermediate Similarity	NPC472727
0.7624	Intermediate Similarity	NPC472728
0.7619	Intermediate Similarity	NPC277017
0.7619	Intermediate Similarity	NPC154608
0.7619	Intermediate Similarity	NPC192813
0.76	Intermediate Similarity	NPC236176
0.7582	Intermediate Similarity	NPC470946
0.7582	Intermediate Similarity	NPC470945
0.7582	Intermediate Similarity	NPC470947
0.7579	Intermediate Similarity	NPC472007
0.7576	Intermediate Similarity	NPC36954
0.7573	Intermediate Similarity	NPC475945
0.7573	Intermediate Similarity	NPC472747
0.7573	Intermediate Similarity	NPC475871
0.7573	Intermediate Similarity	NPC472750
0.7551	Intermediate Similarity	NPC212486
0.7551	Intermediate Similarity	NPC476300
0.7551	Intermediate Similarity	NPC179746
0.7551	Intermediate Similarity	NPC81419
0.7551	Intermediate Similarity	NPC475912
0.7549	Intermediate Similarity	NPC472753
0.7549	Intermediate Similarity	NPC47880
0.7549	Intermediate Similarity	NPC9878
0.7547	Intermediate Similarity	NPC20192
0.7547	Intermediate Similarity	NPC77089
0.7547	Intermediate Similarity	NPC101018
0.7526	Intermediate Similarity	NPC474761
0.7526	Intermediate Similarity	NPC476004
0.7526	Intermediate Similarity	NPC478004
0.7526	Intermediate Similarity	NPC158388
0.7526	Intermediate Similarity	NPC478003
0.75	Intermediate Similarity	NPC269677
0.75	Intermediate Similarity	NPC66108
0.75	Intermediate Similarity	NPC472748
0.7477	Intermediate Similarity	NPC210005
0.7476	Intermediate Similarity	NPC149371
0.7476	Intermediate Similarity	NPC320019
0.7476	Intermediate Similarity	NPC324017
0.7476	Intermediate Similarity	NPC472754
0.7476	Intermediate Similarity	NPC39996
0.7475	Intermediate Similarity	NPC474035
0.7475	Intermediate Similarity	NPC81386
0.7474	Intermediate Similarity	NPC472009
0.7455	Intermediate Similarity	NPC328374
0.7455	Intermediate Similarity	NPC251236
0.7455	Intermediate Similarity	NPC40632
0.7455	Intermediate Similarity	NPC96312
0.7449	Intermediate Similarity	NPC329952
0.7449	Intermediate Similarity	NPC475441
0.7449	Intermediate Similarity	NPC476705
0.7434	Intermediate Similarity	NPC472000
0.7434	Intermediate Similarity	NPC472001
0.7434	Intermediate Similarity	NPC471999
0.7431	Intermediate Similarity	NPC49451
0.7429	Intermediate Similarity	NPC472751
0.7429	Intermediate Similarity	NPC472749
0.7429	Intermediate Similarity	NPC102352
0.7407	Intermediate Similarity	NPC476023
0.7404	Intermediate Similarity	NPC320294
0.7404	Intermediate Similarity	NPC472755
0.74	Intermediate Similarity	NPC14961
0.74	Intermediate Similarity	NPC270013
0.7396	Intermediate Similarity	NPC248602
0.7391	Intermediate Similarity	NPC103634
0.7387	Intermediate Similarity	NPC470854
0.7387	Intermediate Similarity	NPC97908
0.7387	Intermediate Similarity	NPC122033
0.7387	Intermediate Similarity	NPC287343
0.7387	Intermediate Similarity	NPC474654
0.7383	Intermediate Similarity	NPC27814
0.7383	Intermediate Similarity	NPC470257
0.7379	Intermediate Similarity	NPC474742
0.7379	Intermediate Similarity	NPC15993
0.7364	Intermediate Similarity	NPC473798
0.7353	Intermediate Similarity	NPC473326
0.7353	Intermediate Similarity	NPC471144
0.7347	Intermediate Similarity	NPC477684
0.7345	Intermediate Similarity	NPC478051
0.734	Intermediate Similarity	NPC477784
0.734	Intermediate Similarity	NPC11620
0.734	Intermediate Similarity	NPC477785
0.734	Intermediate Similarity	NPC477786
0.7339	Intermediate Similarity	NPC474516
0.7339	Intermediate Similarity	NPC90769
0.7333	Intermediate Similarity	NPC474741
0.7333	Intermediate Similarity	NPC472756
0.7327	Intermediate Similarity	NPC470883
0.7327	Intermediate Similarity	NPC476315
0.7327	Intermediate Similarity	NPC158416
0.7327	Intermediate Similarity	NPC91439
0.7327	Intermediate Similarity	NPC76862
0.7327	Intermediate Similarity	NPC39859
0.732	Intermediate Similarity	NPC58219
0.732	Intermediate Similarity	NPC177629
0.7315	Intermediate Similarity	NPC5103
0.7312	Intermediate Similarity	NPC67254
0.7308	Intermediate Similarity	NPC291500
0.7308	Intermediate Similarity	NPC197835
0.7308	Intermediate Similarity	NPC478176
0.7308	Intermediate Similarity	NPC303653
0.7308	Intermediate Similarity	NPC140591
0.7308	Intermediate Similarity	NPC189609
0.73	Intermediate Similarity	NPC14322
0.73	Intermediate Similarity	NPC196227
0.73	Intermediate Similarity	NPC71589
0.73	Intermediate Similarity	NPC190294
0.7297	Intermediate Similarity	NPC134869
0.7297	Intermediate Similarity	NPC152199
0.7297	Intermediate Similarity	NPC235539
0.7297	Intermediate Similarity	NPC207217
0.7292	Intermediate Similarity	NPC262026
0.7292	Intermediate Similarity	NPC112685
0.7292	Intermediate Similarity	NPC47937
0.729	Intermediate Similarity	NPC293850
0.7282	Intermediate Similarity	NPC472972
0.7273	Intermediate Similarity	NPC7921
0.7273	Intermediate Similarity	NPC208998
0.7273	Intermediate Similarity	NPC469463
0.7273	Intermediate Similarity	NPC208839
0.7273	Intermediate Similarity	NPC194100
0.7273	Intermediate Similarity	NPC469496
0.7273	Intermediate Similarity	NPC469454
0.7264	Intermediate Similarity	NPC181357
0.7263	Intermediate Similarity	NPC151176
0.7263	Intermediate Similarity	NPC9868
0.7263	Intermediate Similarity	NPC3464
0.7263	Intermediate Similarity	NPC475963
0.7255	Intermediate Similarity	NPC134454
0.7255	Intermediate Similarity	NPC328562
0.7255	Intermediate Similarity	NPC273269
0.7255	Intermediate Similarity	NPC272451
0.7255	Intermediate Similarity	NPC323421
0.7255	Intermediate Similarity	NPC17326

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 NPC61275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1915
0.2-0.3	3823
0.3-0.4	2165
0.4-0.5	706
0.5-0.6	254
0.6-0.7	101
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
0.7653	Intermediate Similarity	NPD5282	Discontinued
0.7527	Intermediate Similarity	NPD6110	Phase 1
0.7172	Intermediate Similarity	NPD6698	Approved
0.7172	Intermediate Similarity	NPD46	Approved
0.7093	Intermediate Similarity	NPD7331	Phase 2
0.6964	Remote Similarity	NPD4632	Approved
0.6931	Remote Similarity	NPD7983	Approved
0.6897	Remote Similarity	NPD3704	Approved
0.6881	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5739	Approved
0.6789	Remote Similarity	NPD6675	Approved
0.6789	Remote Similarity	NPD7128	Approved
0.6789	Remote Similarity	NPD6402	Approved
0.6782	Remote Similarity	NPD7341	Phase 2
0.6762	Remote Similarity	NPD4755	Approved
0.6757	Remote Similarity	NPD6372	Approved
0.6757	Remote Similarity	NPD6373	Approved
0.6752	Remote Similarity	NPD6319	Approved
0.6752	Remote Similarity	NPD6059	Approved
0.6752	Remote Similarity	NPD6054	Approved
0.6727	Remote Similarity	NPD6412	Phase 2
0.6726	Remote Similarity	NPD8297	Approved
0.6726	Remote Similarity	NPD6053	Discontinued
0.6701	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5779	Approved
0.6699	Remote Similarity	NPD5778	Approved
0.6696	Remote Similarity	NPD6371	Approved
0.6696	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD8080	Discontinued
0.6638	Remote Similarity	NPD6009	Approved
0.6637	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6649	Approved
0.6637	Remote Similarity	NPD6650	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6583	Remote Similarity	NPD8328	Phase 3
0.6583	Remote Similarity	NPD7604	Phase 2
0.6577	Remote Similarity	NPD5697	Approved
0.6577	Remote Similarity	NPD5701	Approved
0.6574	Remote Similarity	NPD5223	Approved
0.6569	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5328	Approved
0.6569	Remote Similarity	NPD6101	Approved
0.6555	Remote Similarity	NPD5983	Phase 2
0.6555	Remote Similarity	NPD6016	Approved
0.6555	Remote Similarity	NPD6015	Approved
0.6552	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6883	Approved
0.6549	Remote Similarity	NPD7102	Approved
0.6549	Remote Similarity	NPD7290	Approved
0.6531	Remote Similarity	NPD6435	Approved
0.6529	Remote Similarity	NPD7492	Approved
0.6518	Remote Similarity	NPD6686	Approved
0.6518	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6011	Approved
0.6517	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5211	Phase 2
0.6514	Remote Similarity	NPD5225	Approved
0.6514	Remote Similarity	NPD5226	Approved
0.6514	Remote Similarity	NPD4633	Approved
0.6514	Remote Similarity	NPD5224	Approved
0.6509	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5222	Approved
0.6509	Remote Similarity	NPD5221	Approved
0.6505	Remote Similarity	NPD7838	Discovery
0.65	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5988	Approved
0.6495	Remote Similarity	NPD4695	Discontinued
0.6491	Remote Similarity	NPD6617	Approved
0.6491	Remote Similarity	NPD8130	Phase 1
0.6491	Remote Similarity	NPD6869	Approved
0.6491	Remote Similarity	NPD6847	Approved
0.6491	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6008	Approved
0.6475	Remote Similarity	NPD6336	Discontinued
0.6475	Remote Similarity	NPD6616	Approved
0.6465	Remote Similarity	NPD7154	Phase 3
0.646	Remote Similarity	NPD6013	Approved
0.646	Remote Similarity	NPD6012	Approved
0.646	Remote Similarity	NPD6014	Approved
0.646	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4754	Approved
0.6455	Remote Similarity	NPD5175	Approved
0.6455	Remote Similarity	NPD5174	Approved
0.6449	Remote Similarity	NPD5173	Approved
0.6449	Remote Similarity	NPD6084	Phase 2
0.6449	Remote Similarity	NPD6083	Phase 2
0.6442	Remote Similarity	NPD6411	Approved
0.6442	Remote Similarity	NPD6079	Approved
0.6436	Remote Similarity	NPD5279	Phase 3
0.6436	Remote Similarity	NPD3618	Phase 1
0.6435	Remote Similarity	NPD6882	Approved
0.6429	Remote Similarity	NPD5369	Approved
0.6423	Remote Similarity	NPD7078	Approved
0.6423	Remote Similarity	NPD8293	Discontinued
0.6422	Remote Similarity	NPD5344	Discontinued
0.6417	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4753	Phase 2
0.6396	Remote Similarity	NPD5141	Approved
0.6389	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6399	Phase 3
0.6371	Remote Similarity	NPD6033	Approved
0.6371	Remote Similarity	NPD7736	Approved
0.6354	Remote Similarity	NPD4756	Discovery
0.6339	Remote Similarity	NPD4768	Approved
0.6339	Remote Similarity	NPD4767	Approved
0.6327	Remote Similarity	NPD5368	Approved
0.6303	Remote Similarity	NPD7641	Discontinued
0.6296	Remote Similarity	NPD7902	Approved
0.6281	Remote Similarity	NPD8515	Approved
0.6281	Remote Similarity	NPD8517	Approved
0.6281	Remote Similarity	NPD8516	Approved
0.6281	Remote Similarity	NPD8513	Phase 3
0.6275	Remote Similarity	NPD5786	Approved
0.6262	Remote Similarity	NPD4629	Approved
0.6262	Remote Similarity	NPD5695	Phase 3
0.6262	Remote Similarity	NPD5210	Approved
0.6261	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5696	Approved
0.6238	Remote Similarity	NPD3665	Phase 1
0.6238	Remote Similarity	NPD3666	Approved
0.6238	Remote Similarity	NPD4786	Approved
0.6238	Remote Similarity	NPD3133	Approved
0.6228	Remote Similarity	NPD4729	Approved
0.6228	Remote Similarity	NPD5128	Approved
0.6228	Remote Similarity	NPD4730	Approved
0.6226	Remote Similarity	NPD4202	Approved
0.622	Remote Similarity	NPD7260	Phase 2
0.6218	Remote Similarity	NPD7115	Discovery
0.6218	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4251	Approved
0.6214	Remote Similarity	NPD4250	Approved
0.621	Remote Similarity	NPD7507	Approved
0.62	Remote Similarity	NPD3667	Approved
0.6176	Remote Similarity	NPD5329	Approved
0.6176	Remote Similarity	NPD5363	Approved
0.6176	Remote Similarity	NPD1696	Phase 3
0.6168	Remote Similarity	NPD7748	Approved
0.6167	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD5737	Approved
0.6154	Remote Similarity	NPD6672	Approved
0.6134	Remote Similarity	NPD6274	Approved
0.6132	Remote Similarity	NPD7515	Phase 2
0.6121	Remote Similarity	NPD5135	Approved
0.6121	Remote Similarity	NPD5247	Approved
0.6121	Remote Similarity	NPD5249	Phase 3
0.6121	Remote Similarity	NPD5250	Approved
0.6121	Remote Similarity	NPD5169	Approved
0.6121	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5248	Approved
0.6121	Remote Similarity	NPD5251	Approved
0.6117	Remote Similarity	NPD4249	Approved
0.6116	Remote Similarity	NPD7100	Approved
0.6116	Remote Similarity	NPD7101	Approved
0.6111	Remote Similarity	NPD3197	Phase 1
0.6091	Remote Similarity	NPD4225	Approved
0.6091	Remote Similarity	NPD7638	Approved
0.6083	Remote Similarity	NPD6317	Approved
0.6078	Remote Similarity	NPD4197	Approved
0.6068	Remote Similarity	NPD5215	Approved
0.6068	Remote Similarity	NPD5217	Approved
0.6068	Remote Similarity	NPD5127	Approved
0.6068	Remote Similarity	NPD5216	Approved
0.6063	Remote Similarity	NPD7319	Approved
0.6058	Remote Similarity	NPD7524	Approved
0.6055	Remote Similarity	NPD7839	Suspended
0.604	Remote Similarity	NPD4270	Approved
0.604	Remote Similarity	NPD4269	Approved
0.6038	Remote Similarity	NPD5785	Approved
0.6036	Remote Similarity	NPD7640	Approved
0.6036	Remote Similarity	NPD6648	Approved
0.6036	Remote Similarity	NPD7639	Approved
0.6034	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6314	Approved
0.6033	Remote Similarity	NPD6313	Approved
0.6032	Remote Similarity	NPD8074	Phase 3
0.6019	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7900	Approved
0.6016	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6909	Approved
0.6016	Remote Similarity	NPD6908	Approved
0.6	Remote Similarity	NPD6868	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5362	Discontinued
0.5962	Remote Similarity	NPD6684	Approved
0.5962	Remote Similarity	NPD7334	Approved
0.5962	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7521	Approved
0.5962	Remote Similarity	NPD5280	Approved
0.5962	Remote Similarity	NPD6409	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