NPASS Compound

Structure

NPC204556 OpenBabel07101719152D 29 31 0 0 1 0 0 0 0 0999 V2000 -0.0000 -4.8438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -4.8438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 -4.3594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0013 0.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4856 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9213 -0.2994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 -4.3594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 -3.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8390 -1.4531 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8390 -3.3906 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9213 1.2681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5169 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 -0.4844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6779 -2.9063 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3558 -2.9063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2207 2.1894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -3.3906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3940 -0.8850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4908 0.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 11 28 1 0 0 0 0 13 23 2 3 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 1 0 0 0 16 21 1 6 0 0 0 16 29 1 0 0 0 0 17 12 1 1 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 25 2 0 0 0 0 18 28 1 0 0 0 0 19 26 2 0 0 0 0 19 29 1 0 0 0 0 21 22 1 6 0 0 0 22 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	407.23
Volume:	416.591
LogP:	3.007
LogD:	1.942
LogS:	-4.094
# Rotatable Bonds:	6
TPSA:	101.93
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	4.771
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.88
MDCK Permeability:	2.2759537387173623e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.888
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.676
Plasma Protein Binding (PPB):	25.25641632080078%
Volume Distribution (VD):	0.883
Pgp-substrate:	57.09978485107422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.35
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.401
CYP3A4-substrate:	0.318

ADMET: Excretion

Clearance (CL):	3.737
Half-life (T1/2):	0.148

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.329
Drug-inuced Liver Injury (DILI):	0.198
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.434
Skin Sensitization:	0.11
Carcinogencity:	0.093
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.791

Download Data

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

Natural Product: NPC204556

Natural Product ID:	NPC204556
*Common Name:**	Rel-Berkedrimane B
IUPAC Name:	[(5aS,9S,9aR,9bS)-9b-hydroxy-6,6,9a-trimethyl-3-oxo-1,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-9-yl] (2S)-2-acetamido-3-methylbutanoate
Synonyms:	Rel-Berkedrimane B
Standard InCHIKey:	DFGYGTWTXGTQIC-FIOCPMRGSA-N
Standard InCHI:	InChI=1S/C22H33NO6/c1-12(2)17(23-13(3)24)19(26)29-16-9-10-20(4,5)15-8-7-14-18(25)28-11-22(14,27)21(15,16)6/h7,12,15-17,27H,8-11H2,1-6H3,(H,23,24)/t15-,16-,17-,21+,22+/m0/s1
SMILES:	CC(C)[C@@H](C(=O)O[C@H]1CCC(C)(C)[C@@H]2CC=C3C(=O)OC[C@@]3([C@@]12C)O)N=C(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011680
PubChem CID:	51723030
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO17955	Penicillium solitum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932120]
NPO17955	Penicillium solitum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276851]
NPO17955	Penicillium solitum	Species	Aspergillaceae	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	2
Others	1

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT277	Individual Protein	Caspase-1	Homo sapiens	IC50	=	90000.0	nM	PMID[510234]
NPT979	Individual Protein	Caspase-3	Homo sapiens	IC50	=	50000.0	nM	PMID[510234]
NPT979	Individual Protein	Caspase-3	Homo sapiens	IC25	=	10.0	uM	PMID[510234]

☑ 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 NPC204556 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	121
0.1-0.2	718
0.2-0.3	2958
0.3-0.4	8600
0.4-0.5	15656
0.5-0.6	9143
0.6-0.7	4992
0.7-0.8	504
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9145	High Similarity	NPC9714
0.8559	High Similarity	NPC269530
0.8276	Intermediate Similarity	NPC146731
0.812	Intermediate Similarity	NPC296950
0.7934	Intermediate Similarity	NPC235014
0.7934	Intermediate Similarity	NPC5103
0.7886	Intermediate Similarity	NPC469463
0.7886	Intermediate Similarity	NPC469454
0.7886	Intermediate Similarity	NPC469496
0.7881	Intermediate Similarity	NPC159533
0.7869	Intermediate Similarity	NPC304180
0.7869	Intermediate Similarity	NPC179798
0.784	Intermediate Similarity	NPC469684
0.7797	Intermediate Similarity	NPC295791
0.7778	Intermediate Similarity	NPC187497
0.7778	Intermediate Similarity	NPC471121
0.7778	Intermediate Similarity	NPC113620
0.7778	Intermediate Similarity	NPC100612
0.7778	Intermediate Similarity	NPC475599
0.7778	Intermediate Similarity	NPC471118
0.7778	Intermediate Similarity	NPC174336
0.7752	Intermediate Similarity	NPC469789
0.7752	Intermediate Similarity	NPC67251
0.7744	Intermediate Similarity	NPC90814
0.7744	Intermediate Similarity	NPC189393
0.7742	Intermediate Similarity	NPC56448
0.7742	Intermediate Similarity	NPC25909
0.7708	Intermediate Similarity	NPC265699
0.7708	Intermediate Similarity	NPC475527
0.7698	Intermediate Similarity	NPC473968
0.7698	Intermediate Similarity	NPC53396
0.7698	Intermediate Similarity	NPC471120
0.7698	Intermediate Similarity	NPC58662
0.7698	Intermediate Similarity	NPC98249
0.7698	Intermediate Similarity	NPC23046
0.7698	Intermediate Similarity	NPC471117
0.7692	Intermediate Similarity	NPC8369
0.7692	Intermediate Similarity	NPC470922
0.7687	Intermediate Similarity	NPC476111
0.7686	Intermediate Similarity	NPC187435
0.7686	Intermediate Similarity	NPC67321
0.7686	Intermediate Similarity	NPC112780
0.7667	Intermediate Similarity	NPC258532
0.7661	Intermediate Similarity	NPC472002
0.7661	Intermediate Similarity	NPC476801
0.7643	Intermediate Similarity	NPC193753
0.7643	Intermediate Similarity	NPC160222
0.7638	Intermediate Similarity	NPC284707
0.7634	Intermediate Similarity	NPC293112
0.7623	Intermediate Similarity	NPC151393
0.7623	Intermediate Similarity	NPC275539
0.7623	Intermediate Similarity	NPC189075
0.76	Intermediate Similarity	NPC477126
0.76	Intermediate Similarity	NPC471204
0.7597	Intermediate Similarity	NPC67569
0.7597	Intermediate Similarity	NPC46570
0.7583	Intermediate Similarity	NPC99510
0.7581	Intermediate Similarity	NPC317107
0.7581	Intermediate Similarity	NPC469656
0.7581	Intermediate Similarity	NPC469655
0.7581	Intermediate Similarity	NPC474846
0.7578	Intermediate Similarity	NPC473636
0.7578	Intermediate Similarity	NPC77689
0.7561	Intermediate Similarity	NPC474243
0.7559	Intermediate Similarity	NPC473656
0.7559	Intermediate Similarity	NPC134430
0.7557	Intermediate Similarity	NPC81736
0.7557	Intermediate Similarity	NPC476729
0.7557	Intermediate Similarity	NPC172154
0.7557	Intermediate Similarity	NPC24651
0.7541	Intermediate Similarity	NPC110496
0.754	Intermediate Similarity	NPC117712
0.7538	Intermediate Similarity	NPC170538
0.7538	Intermediate Similarity	NPC23786
0.7538	Intermediate Similarity	NPC107493
0.7538	Intermediate Similarity	NPC470265
0.7538	Intermediate Similarity	NPC269642
0.752	Intermediate Similarity	NPC90952
0.752	Intermediate Similarity	NPC317687
0.752	Intermediate Similarity	NPC277769
0.7518	Intermediate Similarity	NPC243902
0.75	Intermediate Similarity	NPC478211
0.75	Intermediate Similarity	NPC183571
0.75	Intermediate Similarity	NPC475372
0.75	Intermediate Similarity	NPC253906
0.75	Intermediate Similarity	NPC478206
0.75	Intermediate Similarity	NPC162973
0.75	Intermediate Similarity	NPC473635
0.75	Intermediate Similarity	NPC108581
0.75	Intermediate Similarity	NPC478205
0.7481	Intermediate Similarity	NPC265557
0.7481	Intermediate Similarity	NPC105926
0.7481	Intermediate Similarity	NPC18945
0.7481	Intermediate Similarity	NPC91693
0.7481	Intermediate Similarity	NPC11895
0.748	Intermediate Similarity	NPC306265
0.748	Intermediate Similarity	NPC176840
0.748	Intermediate Similarity	NPC37628
0.748	Intermediate Similarity	NPC94377
0.748	Intermediate Similarity	NPC270478
0.748	Intermediate Similarity	NPC89171
0.748	Intermediate Similarity	NPC476802
0.7479	Intermediate Similarity	NPC471413
0.7464	Intermediate Similarity	NPC246209
0.746	Intermediate Similarity	NPC478212
0.7459	Intermediate Similarity	NPC1679
0.7459	Intermediate Similarity	NPC477125
0.7459	Intermediate Similarity	NPC469607
0.7442	Intermediate Similarity	NPC268958
0.7442	Intermediate Similarity	NPC473839
0.7442	Intermediate Similarity	NPC475041
0.7442	Intermediate Similarity	NPC312536
0.7442	Intermediate Similarity	NPC476529
0.7442	Intermediate Similarity	NPC230513
0.7442	Intermediate Similarity	NPC211093
0.7442	Intermediate Similarity	NPC475775
0.744	Intermediate Similarity	NPC132790
0.744	Intermediate Similarity	NPC188738
0.744	Intermediate Similarity	NPC100329
0.744	Intermediate Similarity	NPC97939
0.744	Intermediate Similarity	NPC247031
0.7438	Intermediate Similarity	NPC474165
0.7438	Intermediate Similarity	NPC69171
0.7438	Intermediate Similarity	NPC254202
0.7438	Intermediate Similarity	NPC72842
0.7438	Intermediate Similarity	NPC99266
0.7422	Intermediate Similarity	NPC470775
0.7422	Intermediate Similarity	NPC13713
0.7422	Intermediate Similarity	NPC478204
0.7422	Intermediate Similarity	NPC176513
0.7422	Intermediate Similarity	NPC475323
0.7422	Intermediate Similarity	NPC475809
0.7422	Intermediate Similarity	NPC473590
0.7422	Intermediate Similarity	NPC476190
0.7419	Intermediate Similarity	NPC42662
0.7419	Intermediate Similarity	NPC469370
0.7417	Intermediate Similarity	NPC308824
0.7417	Intermediate Similarity	NPC471412
0.7405	Intermediate Similarity	NPC312833
0.7398	Intermediate Similarity	NPC78966
0.7398	Intermediate Similarity	NPC230541
0.7398	Intermediate Similarity	NPC143609
0.7398	Intermediate Similarity	NPC180744
0.7398	Intermediate Similarity	NPC284732
0.7395	Intermediate Similarity	NPC278386
0.7395	Intermediate Similarity	NPC159763
0.7395	Intermediate Similarity	NPC216478
0.7395	Intermediate Similarity	NPC23364
0.7395	Intermediate Similarity	NPC124512
0.7385	Intermediate Similarity	NPC109607
0.7385	Intermediate Similarity	NPC107338
0.7385	Intermediate Similarity	NPC154491
0.7385	Intermediate Similarity	NPC476961
0.7385	Intermediate Similarity	NPC474585
0.7385	Intermediate Similarity	NPC268530
0.7385	Intermediate Similarity	NPC48692
0.7381	Intermediate Similarity	NPC265391
0.7381	Intermediate Similarity	NPC12046
0.7381	Intermediate Similarity	NPC4573
0.7381	Intermediate Similarity	NPC194951
0.7377	Intermediate Similarity	NPC283850
0.7364	Intermediate Similarity	NPC470276
0.7364	Intermediate Similarity	NPC153440
0.7364	Intermediate Similarity	NPC50774
0.7364	Intermediate Similarity	NPC470776
0.7364	Intermediate Similarity	NPC709
0.7364	Intermediate Similarity	NPC251310
0.7364	Intermediate Similarity	NPC186525
0.736	Intermediate Similarity	NPC478209
0.736	Intermediate Similarity	NPC474567
0.7355	Intermediate Similarity	NPC476081
0.7355	Intermediate Similarity	NPC164551
0.7355	Intermediate Similarity	NPC472552
0.7355	Intermediate Similarity	NPC137430
0.7355	Intermediate Similarity	NPC58329
0.7348	Intermediate Similarity	NPC472399
0.7348	Intermediate Similarity	NPC120724
0.7344	Intermediate Similarity	NPC471127
0.7344	Intermediate Similarity	NPC234858
0.7344	Intermediate Similarity	NPC154363
0.7344	Intermediate Similarity	NPC207217
0.7344	Intermediate Similarity	NPC64318
0.7344	Intermediate Similarity	NPC474734
0.7344	Intermediate Similarity	NPC190286
0.7344	Intermediate Similarity	NPC471816
0.7339	Intermediate Similarity	NPC469916
0.7339	Intermediate Similarity	NPC322903
0.7339	Intermediate Similarity	NPC472439
0.7333	Intermediate Similarity	NPC47024
0.7333	Intermediate Similarity	NPC473593
0.7333	Intermediate Similarity	NPC231529
0.7328	Intermediate Similarity	NPC470779
0.7328	Intermediate Similarity	NPC159456
0.7328	Intermediate Similarity	NPC4021
0.7323	Intermediate Similarity	NPC475966
0.7323	Intermediate Similarity	NPC157441
0.7323	Intermediate Similarity	NPC470120
0.7323	Intermediate Similarity	NPC264153
0.7317	Intermediate Similarity	NPC127609
0.7317	Intermediate Similarity	NPC102352

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 NPC204556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	99
0.1-0.2	699
0.2-0.3	2906
0.3-0.4	3460
0.4-0.5	1422
0.5-0.6	415
0.6-0.7	146
0.7-0.8	3
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
0.7444	Intermediate Similarity	NPD8074	Phase 3
0.7395	Intermediate Similarity	NPD4225	Approved
0.7287	Intermediate Similarity	NPD7115	Discovery
0.7068	Intermediate Similarity	NPD6921	Approved
0.7029	Intermediate Similarity	NPD6914	Discontinued
0.7008	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7260	Phase 2
0.6953	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6908	Approved
0.694	Remote Similarity	NPD6909	Approved
0.6929	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6845	Suspended
0.6923	Remote Similarity	NPD6334	Approved
0.6923	Remote Similarity	NPD6333	Approved
0.6866	Remote Similarity	NPD6319	Approved
0.6838	Remote Similarity	NPD7642	Approved
0.6835	Remote Similarity	NPD7319	Approved
0.6822	Remote Similarity	NPD6371	Approved
0.6822	Remote Similarity	NPD6421	Discontinued
0.6815	Remote Similarity	NPD8516	Approved
0.6815	Remote Similarity	NPD8515	Approved
0.6815	Remote Similarity	NPD8513	Phase 3
0.6815	Remote Similarity	NPD8517	Approved
0.6797	Remote Similarity	NPD6686	Approved
0.6788	Remote Similarity	NPD7492	Approved
0.6774	Remote Similarity	NPD7639	Approved
0.6774	Remote Similarity	NPD7640	Approved
0.6741	Remote Similarity	NPD6054	Approved
0.6739	Remote Similarity	NPD8451	Approved
0.6739	Remote Similarity	NPD7507	Approved
0.6739	Remote Similarity	NPD6616	Approved
0.6719	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7604	Phase 2
0.6694	Remote Similarity	NPD7638	Approved
0.6691	Remote Similarity	NPD7078	Approved
0.6691	Remote Similarity	NPD8448	Approved
0.6667	Remote Similarity	NPD8342	Approved
0.6667	Remote Similarity	NPD8340	Approved
0.6667	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD8341	Approved
0.6667	Remote Similarity	NPD8299	Approved
0.6643	Remote Similarity	NPD7736	Approved
0.6642	Remote Similarity	NPD6370	Approved
0.6641	Remote Similarity	NPD6008	Approved
0.6618	Remote Similarity	NPD6059	Approved
0.6594	Remote Similarity	NPD8328	Phase 3
0.6594	Remote Similarity	NPD7830	Approved
0.6594	Remote Similarity	NPD7829	Approved
0.6591	Remote Similarity	NPD8297	Approved
0.6587	Remote Similarity	NPD5344	Discontinued
0.6571	Remote Similarity	NPD8293	Discontinued
0.6569	Remote Similarity	NPD6015	Approved
0.6569	Remote Similarity	NPD6016	Approved
0.6568	Remote Similarity	NPD8407	Phase 2
0.6557	Remote Similarity	NPD5778	Approved
0.6557	Remote Similarity	NPD5779	Approved
0.6549	Remote Similarity	NPD8392	Approved
0.6549	Remote Similarity	NPD8391	Approved
0.6549	Remote Similarity	NPD8390	Approved
0.6538	Remote Similarity	NPD6899	Approved
0.6538	Remote Similarity	NPD6881	Approved
0.6525	Remote Similarity	NPD1694	Approved
0.6522	Remote Similarity	NPD5988	Approved
0.6519	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6649	Approved
0.6515	Remote Similarity	NPD6650	Approved
0.6512	Remote Similarity	NPD6675	Approved
0.6512	Remote Similarity	NPD5739	Approved
0.6512	Remote Similarity	NPD6402	Approved
0.6512	Remote Similarity	NPD7128	Approved
0.6508	Remote Similarity	NPD6404	Discontinued
0.6489	Remote Similarity	NPD6373	Approved
0.6489	Remote Similarity	NPD6372	Approved
0.6488	Remote Similarity	NPD8368	Discontinued
0.6483	Remote Similarity	NPD8415	Approved
0.6466	Remote Similarity	NPD6053	Discontinued
0.6462	Remote Similarity	NPD5697	Approved
0.6452	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD7102	Approved
0.6439	Remote Similarity	NPD6883	Approved
0.6439	Remote Similarity	NPD4634	Approved
0.6439	Remote Similarity	NPD7290	Approved
0.6412	Remote Similarity	NPD7320	Approved
0.6408	Remote Similarity	NPD8337	Approved
0.6408	Remote Similarity	NPD8336	Approved
0.6406	Remote Similarity	NPD7632	Discontinued
0.6405	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD8080	Discontinued
0.6397	Remote Similarity	NPD7500	Approved
0.6397	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6009	Approved
0.6393	Remote Similarity	NPD46	Approved
0.6393	Remote Similarity	NPD6698	Approved
0.6391	Remote Similarity	NPD8130	Phase 1
0.6391	Remote Similarity	NPD6869	Approved
0.6391	Remote Similarity	NPD6617	Approved
0.6391	Remote Similarity	NPD6847	Approved
0.6391	Remote Similarity	NPD2204	Approved
0.6385	Remote Similarity	NPD5357	Phase 1
0.6378	Remote Similarity	NPD6648	Approved
0.6364	Remote Similarity	NPD6413	Approved
0.6364	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD6012	Approved
0.6364	Remote Similarity	NPD6014	Approved
0.635	Remote Similarity	NPD7641	Discontinued
0.6349	Remote Similarity	NPD7902	Approved
0.6345	Remote Similarity	NPD8338	Approved
0.6343	Remote Similarity	NPD6882	Approved
0.6341	Remote Similarity	NPD7983	Approved
0.6336	Remote Similarity	NPD5701	Approved
0.6331	Remote Similarity	NPD5983	Phase 2
0.6322	Remote Similarity	NPD8360	Approved
0.6322	Remote Similarity	NPD8361	Approved
0.629	Remote Similarity	NPD6399	Phase 3
0.6288	Remote Similarity	NPD6011	Approved
0.6279	Remote Similarity	NPD5211	Phase 2
0.6268	Remote Similarity	NPD6336	Discontinued
0.6268	Remote Similarity	NPD8273	Phase 1
0.626	Remote Similarity	NPD6640	Phase 3
0.6241	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.624	Remote Similarity	NPD7748	Approved
0.6234	Remote Similarity	NPD7625	Phase 1
0.6232	Remote Similarity	NPD7327	Approved
0.6232	Remote Similarity	NPD7328	Approved
0.6229	Remote Similarity	NPD8435	Approved
0.6214	Remote Similarity	NPD7503	Approved
0.6214	Remote Similarity	NPD8033	Approved
0.6214	Remote Similarity	NPD8444	Approved
0.6214	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD6412	Phase 2
0.621	Remote Similarity	NPD6411	Approved
0.6201	Remote Similarity	NPD8485	Approved
0.6187	Remote Similarity	NPD7516	Approved
0.6183	Remote Similarity	NPD5141	Approved
0.6181	Remote Similarity	NPD6033	Approved
0.6148	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD1719	Phase 1
0.6148	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD8294	Approved
0.6143	Remote Similarity	NPD8377	Approved
0.6134	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5785	Approved
0.6124	Remote Similarity	NPD4696	Approved
0.6124	Remote Similarity	NPD5285	Approved
0.6124	Remote Similarity	NPD5286	Approved
0.6118	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5282	Discontinued
0.6111	Remote Similarity	NPD7900	Approved
0.6111	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD8380	Approved
0.6099	Remote Similarity	NPD8296	Approved
0.6099	Remote Similarity	NPD8379	Approved
0.6099	Remote Similarity	NPD8335	Approved
0.6099	Remote Similarity	NPD8378	Approved
0.6099	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD4755	Approved
0.6087	Remote Similarity	NPD6274	Approved
0.608	Remote Similarity	NPD6079	Approved
0.608	Remote Similarity	NPD7515	Phase 2
0.6074	Remote Similarity	NPD6420	Discontinued
0.6071	Remote Similarity	NPD7101	Approved
0.6071	Remote Similarity	NPD7100	Approved
0.6066	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD8133	Approved
0.6048	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5328	Approved
0.6048	Remote Similarity	NPD6101	Approved
0.6047	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD5224	Approved
0.6031	Remote Similarity	NPD5226	Approved
0.6031	Remote Similarity	NPD4633	Approved
0.6031	Remote Similarity	NPD5225	Approved
0.6029	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7839	Suspended
0.6016	Remote Similarity	NPD3573	Approved
0.6013	Remote Similarity	NPD8384	Approved
0.6	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD7838	Discovery
0.5986	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD5175	Approved
0.5985	Remote Similarity	NPD5174	Approved
0.5969	Remote Similarity	NPD6083	Phase 2
0.5969	Remote Similarity	NPD6084	Phase 2
0.596	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD5223	Approved
0.5952	Remote Similarity	NPD7637	Suspended
0.5938	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5695	Phase 3
0.5935	Remote Similarity	NPD3618	Phase 1
0.5929	Remote Similarity	NPD7505	Discontinued
0.5929	Remote Similarity	NPD6317	Approved
0.5923	Remote Similarity	NPD5696	Approved
0.5909	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5903	Remote Similarity	NPD7122	Discontinued

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