NPASS Compound

Structure

NPC44261 OpenBabel07101718182D 26 27 0 0 1 0 0 0 0 0999 V2000 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 6 1 0 0 0 0 2 12 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 13 3 1 1 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 4 1 1 0 0 0 14 17 1 0 0 0 0 14 26 1 0 0 0 0 15 21 1 6 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 24 1 6 0 0 0 18 20 1 6 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 5 1 6 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.2
Volume:	379.559
LogP:	3.039
LogD:	2.98
LogS:	-3.93
# Rotatable Bonds:	8
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	4.417
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.729
MDCK Permeability:	1.950261867023073e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.329
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.925
Plasma Protein Binding (PPB):	73.0796890258789%
Volume Distribution (VD):	0.911
Pgp-substrate:	19.415477752685547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.297
CYP2C19-inhibitor:	0.517
CYP2C19-substrate:	0.581
CYP2C9-inhibitor:	0.663
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.2
CYP2D6-substrate:	0.147
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	9.18
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.737
Drug-inuced Liver Injury (DILI):	0.558
AMES Toxicity:	0.165
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.174
Skin Sensitization:	0.452
Carcinogencity:	0.254
Eye Corrosion:	0.233
Eye Irritation:	0.199
Respiratory Toxicity:	0.161

Download Data

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

Natural Product: NPC44261

Natural Product ID:	NPC44261
*Common Name:**	Botcinin D
IUPAC Name:	[(4aR,6S,7R,8R,8aS)-3,4a,6,8-tetramethyl-2-oxo-6,7,8,8a-tetrahydropyrano[3,2-b]pyran-7-yl] (E,4S)-4-hydroxyoct-2-enoate
Synonyms:	Botcinin D
Standard InCHIKey:	QJUKURZOKSVYNB-QMYRPDPQSA-N
Standard InCHI:	InChI=1S/C20H30O6/c1-6-7-8-15(21)9-10-16(22)24-17-13(3)18-20(5,26-14(17)4)11-12(2)19(23)25-18/h9-11,13-15,17-18,21H,6-8H2,1-5H3/b10-9+/t13-,14+,15+,17-,18+,20-/m1/s1
SMILES:	CCCC[C@@H](/C=C/C(=O)O[C@H]1[C@H](C)O[C@]2([C@H]([C@@H]1C)OC(=O)C(=C2)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522226
PubChem CID:	11646318
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	12500.0	nM	PMID[567185]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	12500.0	nM	PMID[567186]

☑ 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 NPC44261 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	163
0.1-0.2	1005
0.2-0.3	4320
0.3-0.4	9706
0.4-0.5	14428
0.5-0.6	7953
0.6-0.7	4290
0.7-0.8	813
0.8-0.85	17
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8506	High Similarity	NPC3952
0.8471	Intermediate Similarity	NPC311163
0.8391	Intermediate Similarity	NPC133450
0.8313	Intermediate Similarity	NPC112868
0.8312	Intermediate Similarity	NPC151481
0.8295	Intermediate Similarity	NPC177668
0.814	Intermediate Similarity	NPC471494
0.814	Intermediate Similarity	NPC11804
0.8118	Intermediate Similarity	NPC161045
0.8072	Intermediate Similarity	NPC139712
0.8049	Intermediate Similarity	NPC474278
0.8023	Intermediate Similarity	NPC243618
0.8023	Intermediate Similarity	NPC475035
0.8023	Intermediate Similarity	NPC70424
0.8022	Intermediate Similarity	NPC256368
0.8	Intermediate Similarity	NPC477749
0.7978	Intermediate Similarity	NPC212598
0.7957	Intermediate Similarity	NPC475332
0.7931	Intermediate Similarity	NPC475034
0.7912	Intermediate Similarity	NPC238090
0.7912	Intermediate Similarity	NPC472196
0.7912	Intermediate Similarity	NPC472195
0.7907	Intermediate Similarity	NPC474809
0.7901	Intermediate Similarity	NPC107654
0.7901	Intermediate Similarity	NPC474280
0.7901	Intermediate Similarity	NPC315843
0.7889	Intermediate Similarity	NPC475855
0.7889	Intermediate Similarity	NPC473448
0.7882	Intermediate Similarity	NPC325031
0.7882	Intermediate Similarity	NPC474894
0.7875	Intermediate Similarity	NPC316185
0.7872	Intermediate Similarity	NPC187761
0.7872	Intermediate Similarity	NPC83895
0.7872	Intermediate Similarity	NPC308567
0.7872	Intermediate Similarity	NPC261377
0.7872	Intermediate Similarity	NPC255592
0.7872	Intermediate Similarity	NPC475653
0.7857	Intermediate Similarity	NPC471537
0.7857	Intermediate Similarity	NPC475210
0.7849	Intermediate Similarity	NPC472995
0.7841	Intermediate Similarity	NPC475461
0.7841	Intermediate Similarity	NPC305475
0.7831	Intermediate Similarity	NPC475711
0.7831	Intermediate Similarity	NPC315394
0.7826	Intermediate Similarity	NPC71589
0.7826	Intermediate Similarity	NPC159698
0.7816	Intermediate Similarity	NPC266718
0.7816	Intermediate Similarity	NPC78673
0.7816	Intermediate Similarity	NPC160517
0.7816	Intermediate Similarity	NPC186155
0.7816	Intermediate Similarity	NPC9868
0.7805	Intermediate Similarity	NPC329852
0.7802	Intermediate Similarity	NPC470373
0.7802	Intermediate Similarity	NPC303697
0.7802	Intermediate Similarity	NPC470379
0.7802	Intermediate Similarity	NPC158061
0.7792	Intermediate Similarity	NPC96414
0.7791	Intermediate Similarity	NPC474291
0.7791	Intermediate Similarity	NPC474252
0.7789	Intermediate Similarity	NPC475053
0.7778	Intermediate Similarity	NPC477748
0.7766	Intermediate Similarity	NPC120299
0.7766	Intermediate Similarity	NPC40812
0.7753	Intermediate Similarity	NPC313658
0.7753	Intermediate Similarity	NPC316138
0.7753	Intermediate Similarity	NPC475037
0.7753	Intermediate Similarity	NPC199382
0.775	Intermediate Similarity	NPC473361
0.775	Intermediate Similarity	NPC329904
0.775	Intermediate Similarity	NPC4299
0.7742	Intermediate Similarity	NPC272050
0.7738	Intermediate Similarity	NPC279532
0.7738	Intermediate Similarity	NPC248775
0.7727	Intermediate Similarity	NPC261380
0.7727	Intermediate Similarity	NPC255307
0.7717	Intermediate Similarity	NPC109406
0.7717	Intermediate Similarity	NPC159092
0.7717	Intermediate Similarity	NPC476049
0.7717	Intermediate Similarity	NPC475912
0.7701	Intermediate Similarity	NPC473390
0.7701	Intermediate Similarity	NPC40746
0.7701	Intermediate Similarity	NPC169575
0.7701	Intermediate Similarity	NPC315559
0.7701	Intermediate Similarity	NPC16488
0.7701	Intermediate Similarity	NPC131669
0.7692	Intermediate Similarity	NPC202886
0.7692	Intermediate Similarity	NPC179394
0.7692	Intermediate Similarity	NPC201356
0.7692	Intermediate Similarity	NPC144133
0.7684	Intermediate Similarity	NPC203627
0.7674	Intermediate Similarity	NPC315731
0.7667	Intermediate Similarity	NPC260343
0.766	Intermediate Similarity	NPC173329
0.766	Intermediate Similarity	NPC288350
0.766	Intermediate Similarity	NPC255410
0.766	Intermediate Similarity	NPC279621
0.7647	Intermediate Similarity	NPC180725
0.7647	Intermediate Similarity	NPC469617
0.7647	Intermediate Similarity	NPC470148
0.7647	Intermediate Similarity	NPC470149
0.764	Intermediate Similarity	NPC186332
0.764	Intermediate Similarity	NPC316426
0.764	Intermediate Similarity	NPC47220
0.764	Intermediate Similarity	NPC116575
0.764	Intermediate Similarity	NPC61527
0.764	Intermediate Similarity	NPC315395
0.7634	Intermediate Similarity	NPC469491
0.7629	Intermediate Similarity	NPC13171
0.7629	Intermediate Similarity	NPC195510
0.7629	Intermediate Similarity	NPC473596
0.7629	Intermediate Similarity	NPC201191
0.7625	Intermediate Similarity	NPC101622
0.7619	Intermediate Similarity	NPC40049
0.7619	Intermediate Similarity	NPC474026
0.7614	Intermediate Similarity	NPC191476
0.7614	Intermediate Similarity	NPC476804
0.7614	Intermediate Similarity	NPC72464
0.7614	Intermediate Similarity	NPC114979
0.7609	Intermediate Similarity	NPC471324
0.7609	Intermediate Similarity	NPC476084
0.7609	Intermediate Similarity	NPC476075
0.7609	Intermediate Similarity	NPC114172
0.7609	Intermediate Similarity	NPC206679
0.7586	Intermediate Similarity	NPC229825
0.7586	Intermediate Similarity	NPC313677
0.7582	Intermediate Similarity	NPC471054
0.7582	Intermediate Similarity	NPC106040
0.7582	Intermediate Similarity	NPC115179
0.7579	Intermediate Similarity	NPC205143
0.7564	Intermediate Similarity	NPC19769
0.7564	Intermediate Similarity	NPC273600
0.7558	Intermediate Similarity	NPC233377
0.7558	Intermediate Similarity	NPC470147
0.7558	Intermediate Similarity	NPC133226
0.7556	Intermediate Similarity	NPC160138
0.7553	Intermediate Similarity	NPC14961
0.7553	Intermediate Similarity	NPC36954
0.7553	Intermediate Similarity	NPC300710
0.7553	Intermediate Similarity	NPC304886
0.7553	Intermediate Similarity	NPC270013
0.7551	Intermediate Similarity	NPC183570
0.7531	Intermediate Similarity	NPC202011
0.7531	Intermediate Similarity	NPC59558
0.7529	Intermediate Similarity	NPC209135
0.7529	Intermediate Similarity	NPC108816
0.7529	Intermediate Similarity	NPC127526
0.7529	Intermediate Similarity	NPC267231
0.7529	Intermediate Similarity	NPC474816
0.7529	Intermediate Similarity	NPC93763
0.7528	Intermediate Similarity	NPC242233
0.7528	Intermediate Similarity	NPC470124
0.7528	Intermediate Similarity	NPC67081
0.7528	Intermediate Similarity	NPC165162
0.7528	Intermediate Similarity	NPC470755
0.7528	Intermediate Similarity	NPC471223
0.7527	Intermediate Similarity	NPC475838
0.7527	Intermediate Similarity	NPC282644
0.7527	Intermediate Similarity	NPC125674
0.7527	Intermediate Similarity	NPC61201
0.7527	Intermediate Similarity	NPC205034
0.7527	Intermediate Similarity	NPC152778
0.7527	Intermediate Similarity	NPC162615
0.7527	Intermediate Similarity	NPC29798
0.7527	Intermediate Similarity	NPC469692
0.7527	Intermediate Similarity	NPC53555
0.7527	Intermediate Similarity	NPC469645
0.7527	Intermediate Similarity	NPC228451
0.7527	Intermediate Similarity	NPC59646
0.75	Intermediate Similarity	NPC474761
0.75	Intermediate Similarity	NPC231601
0.75	Intermediate Similarity	NPC159763
0.75	Intermediate Similarity	NPC476004
0.75	Intermediate Similarity	NPC301525
0.75	Intermediate Similarity	NPC475760
0.75	Intermediate Similarity	NPC182136
0.75	Intermediate Similarity	NPC265856
0.75	Intermediate Similarity	NPC187268
0.75	Intermediate Similarity	NPC49208
0.75	Intermediate Similarity	NPC250315
0.75	Intermediate Similarity	NPC311070
0.75	Intermediate Similarity	NPC278386
0.75	Intermediate Similarity	NPC310210
0.75	Intermediate Similarity	NPC65700
0.75	Intermediate Similarity	NPC23748
0.75	Intermediate Similarity	NPC203277
0.75	Intermediate Similarity	NPC469880
0.75	Intermediate Similarity	NPC116543
0.75	Intermediate Similarity	NPC170286
0.75	Intermediate Similarity	NPC68819
0.75	Intermediate Similarity	NPC316598
0.75	Intermediate Similarity	NPC469853
0.75	Intermediate Similarity	NPC124512
0.7474	Intermediate Similarity	NPC57664
0.7474	Intermediate Similarity	NPC473153
0.7474	Intermediate Similarity	NPC476315
0.7473	Intermediate Similarity	NPC106051
0.7473	Intermediate Similarity	NPC476805
0.7473	Intermediate Similarity	NPC153805
0.7473	Intermediate Similarity	NPC227379
0.7473	Intermediate Similarity	NPC474471

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 NPC44261 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1245
0.2-0.3	3737
0.3-0.4	2672
0.4-0.5	931
0.5-0.6	358
0.6-0.7	56
0.7-0.8	7
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
0.7889	Intermediate Similarity	NPD7838	Discovery
0.7872	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD46	Approved
0.7692	Intermediate Similarity	NPD6698	Approved
0.7526	Intermediate Similarity	NPD5344	Discontinued
0.75	Intermediate Similarity	NPD4225	Approved
0.7416	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6648	Approved
0.7125	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4819	Approved
0.6966	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4822	Approved
0.6966	Remote Similarity	NPD4821	Approved
0.6966	Remote Similarity	NPD4820	Approved
0.6923	Remote Similarity	NPD6686	Approved
0.6923	Remote Similarity	NPD7154	Phase 3
0.6881	Remote Similarity	NPD7115	Discovery
0.6875	Remote Similarity	NPD7983	Approved
0.6837	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5778	Approved
0.6804	Remote Similarity	NPD5779	Approved
0.6792	Remote Similarity	NPD6371	Approved
0.6771	Remote Similarity	NPD5785	Approved
0.6742	Remote Similarity	NPD4268	Approved
0.6742	Remote Similarity	NPD4271	Approved
0.6701	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5363	Approved
0.6569	Remote Similarity	NPD7639	Approved
0.6569	Remote Similarity	NPD7640	Approved
0.6559	Remote Similarity	NPD5362	Discontinued
0.6543	Remote Similarity	NPD368	Approved
0.6531	Remote Similarity	NPD6411	Approved
0.6526	Remote Similarity	NPD4249	Approved
0.6514	Remote Similarity	NPD6053	Discontinued
0.6491	Remote Similarity	NPD7503	Approved
0.6471	Remote Similarity	NPD7638	Approved
0.6458	Remote Similarity	NPD4251	Approved
0.6458	Remote Similarity	NPD4250	Approved
0.6452	Remote Similarity	NPD5209	Approved
0.6436	Remote Similarity	NPD7839	Suspended
0.6429	Remote Similarity	NPD7505	Discontinued
0.6421	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD1694	Approved
0.6383	Remote Similarity	NPD5332	Approved
0.6383	Remote Similarity	NPD5331	Approved
0.6374	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD8513	Phase 3
0.6344	Remote Similarity	NPD4790	Discontinued
0.6316	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7524	Approved
0.6277	Remote Similarity	NPD6435	Approved
0.6277	Remote Similarity	NPD4269	Approved
0.6277	Remote Similarity	NPD4270	Approved
0.6275	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5282	Discontinued
0.6237	Remote Similarity	NPD4252	Approved
0.6228	Remote Similarity	NPD7327	Approved
0.6228	Remote Similarity	NPD7328	Approved
0.622	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8297	Approved
0.6211	Remote Similarity	NPD6695	Phase 3
0.6211	Remote Similarity	NPD6110	Phase 1
0.6207	Remote Similarity	NPD8033	Approved
0.6207	Remote Similarity	NPD8517	Approved
0.6207	Remote Similarity	NPD8516	Approved
0.6207	Remote Similarity	NPD8515	Approved
0.6204	Remote Similarity	NPD5697	Approved
0.6186	Remote Similarity	NPD5786	Approved
0.6174	Remote Similarity	NPD7516	Approved
0.617	Remote Similarity	NPD5369	Approved
0.6162	Remote Similarity	NPD1695	Approved
0.6147	Remote Similarity	NPD6899	Approved
0.6147	Remote Similarity	NPD6881	Approved
0.6121	Remote Similarity	NPD8377	Approved
0.6121	Remote Similarity	NPD8294	Approved
0.6102	Remote Similarity	NPD7830	Approved
0.6102	Remote Similarity	NPD7829	Approved
0.6091	Remote Similarity	NPD6012	Approved
0.6091	Remote Similarity	NPD6014	Approved
0.6091	Remote Similarity	NPD6013	Approved
0.6087	Remote Similarity	NPD4756	Discovery
0.6068	Remote Similarity	NPD8378	Approved
0.6068	Remote Similarity	NPD8380	Approved
0.6068	Remote Similarity	NPD8335	Approved
0.6068	Remote Similarity	NPD8379	Approved
0.6068	Remote Similarity	NPD8296	Approved
0.6064	Remote Similarity	NPD7332	Phase 2
0.6064	Remote Similarity	NPD5368	Approved
0.6064	Remote Similarity	NPD7514	Phase 3
0.6058	Remote Similarity	NPD6083	Phase 2
0.6058	Remote Similarity	NPD6084	Phase 2
0.6044	Remote Similarity	NPD8264	Approved
0.6044	Remote Similarity	NPD8039	Approved
0.6036	Remote Similarity	NPD7102	Approved
0.6036	Remote Similarity	NPD6883	Approved
0.6036	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7290	Approved
0.6022	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD342	Phase 1
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD4732	Discontinued
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6051	Approved
0.5982	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD8130	Phase 1
0.5982	Remote Similarity	NPD6650	Approved
0.5982	Remote Similarity	NPD6617	Approved
0.5982	Remote Similarity	NPD6869	Approved
0.5982	Remote Similarity	NPD6847	Approved
0.5982	Remote Similarity	NPD6649	Approved
0.5981	Remote Similarity	NPD5211	Phase 2
0.5981	Remote Similarity	NPD7632	Discontinued
0.598	Remote Similarity	NPD6399	Phase 3
0.5977	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7642	Approved
0.5963	Remote Similarity	NPD6402	Approved
0.5963	Remote Similarity	NPD7128	Approved
0.5963	Remote Similarity	NPD6675	Approved
0.5963	Remote Similarity	NPD5739	Approved
0.596	Remote Similarity	NPD7750	Discontinued
0.5952	Remote Similarity	NPD4191	Approved
0.5952	Remote Similarity	NPD4193	Approved
0.5952	Remote Similarity	NPD4194	Approved
0.5952	Remote Similarity	NPD4192	Approved
0.595	Remote Similarity	NPD8074	Phase 3
0.5929	Remote Similarity	NPD6882	Approved
0.5926	Remote Similarity	NPD6647	Phase 2
0.5922	Remote Similarity	NPD7748	Approved
0.5909	Remote Similarity	NPD5701	Approved
0.5909	Remote Similarity	NPD6412	Phase 2
0.5905	Remote Similarity	NPD7902	Approved
0.5895	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6931	Approved
0.5895	Remote Similarity	NPD6930	Phase 2
0.5882	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7515	Phase 2
0.5877	Remote Similarity	NPD4632	Approved
0.5872	Remote Similarity	NPD5141	Approved
0.5868	Remote Similarity	NPD8451	Approved
0.5859	Remote Similarity	NPD6422	Discontinued
0.5856	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7320	Approved
0.5854	Remote Similarity	NPD7319	Approved
0.5851	Remote Similarity	NPD7145	Approved
0.5849	Remote Similarity	NPD5696	Approved
0.5847	Remote Similarity	NPD6319	Approved
0.5842	Remote Similarity	NPD5370	Suspended
0.5833	Remote Similarity	NPD6902	Approved
0.582	Remote Similarity	NPD8448	Approved
0.5818	Remote Similarity	NPD4211	Phase 1
0.5812	Remote Similarity	NPD7641	Discontinued
0.5806	Remote Similarity	NPD6933	Approved
0.5804	Remote Similarity	NPD6373	Approved
0.5804	Remote Similarity	NPD6372	Approved
0.58	Remote Similarity	NPD3573	Approved
0.5794	Remote Similarity	NPD5286	Approved
0.5794	Remote Similarity	NPD4696	Approved
0.5794	Remote Similarity	NPD5285	Approved
0.5789	Remote Similarity	NPD6929	Approved
0.5785	Remote Similarity	NPD8342	Approved
0.5785	Remote Similarity	NPD8341	Approved
0.5785	Remote Similarity	NPD8340	Approved
0.5785	Remote Similarity	NPD8299	Approved
0.5783	Remote Similarity	NPD9119	Approved
0.5783	Remote Similarity	NPD6109	Phase 1
0.5783	Remote Similarity	NPD69	Approved
0.5781	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD6926	Approved
0.5761	Remote Similarity	NPD6924	Approved
0.576	Remote Similarity	NPD7260	Phase 2
0.5752	Remote Similarity	NPD6421	Discontinued
0.5745	Remote Similarity	NPD6932	Approved
0.5745	Remote Similarity	NPD6925	Approved
0.5745	Remote Similarity	NPD5776	Phase 2
0.5729	Remote Similarity	NPD4695	Discontinued
0.5728	Remote Similarity	NPD5281	Approved
0.5728	Remote Similarity	NPD5693	Phase 1
0.5728	Remote Similarity	NPD7087	Discontinued
0.5728	Remote Similarity	NPD5284	Approved
0.5726	Remote Similarity	NPD6009	Approved
0.5726	Remote Similarity	NPD7500	Approved
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.57	Remote Similarity	NPD6684	Approved
0.57	Remote Similarity	NPD6409	Approved
0.57	Remote Similarity	NPD4519	Discontinued
0.57	Remote Similarity	NPD5330	Approved
0.57	Remote Similarity	NPD7334	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