NPASS Compound

Structure

NPC163606 OpenBabel07101718312D 33 35 0 0 1 0 0 0 0 0999 V2000 6.2788 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7429 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5623 -1.7484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3769 6.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8769 5.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6090 5.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6090 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7429 6.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7429 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5134 -1.4394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8769 4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 3.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8769 5.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2565 -2.1085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 4.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.7024 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 20 2 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 27 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 18 22 2 0 0 0 0 19 28 2 0 0 0 0 19 31 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 21 1 6 0 0 0 23 32 1 0 0 0 0 24 29 2 0 0 0 0 24 33 1 0 0 0 0 25 30 1 1 0 0 0 25 32 1 0 0 0 0 26 31 1 6 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.27
Volume:	486.801
LogP:	5.453
LogD:	4.008
LogS:	-3.875
# Rotatable Bonds:	9
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	4.585
Fsp3:	0.593
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:	-4.809
MDCK Permeability:	2.8250737159396522e-05
Pgp-inhibitor:	0.354
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.317
Plasma Protein Binding (PPB):	92.87448120117188%
Volume Distribution (VD):	1.666
Pgp-substrate:	2.8815407752990723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.332
CYP2C19-substrate:	0.426
CYP2C9-inhibitor:	0.423
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.18
CYP2D6-substrate:	0.754
CYP3A4-inhibitor:	0.242
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	2.869
Half-life (T1/2):	0.262

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.236
Drug-inuced Liver Injury (DILI):	0.362
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.838
Carcinogencity:	0.921
Eye Corrosion:	0.003
Eye Irritation:	0.055
Respiratory Toxicity:	0.848

Download Data

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

Natural Product: NPC163606

Natural Product ID:	NPC163606
*Common Name:**	Manoalide 25-Acetate
IUPAC Name:	[(2R)-3-[(2R,6R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2H-furan-2-yl] acetate
Synonyms:	Manoalide 25-Acetate
Standard InCHIKey:	IBDCHSSSHBQBDQ-RFUQPTSVSA-N
Standard InCHI:	InChI=1S/C27H38O6/c1-17(11-13-22-18(2)9-7-15-27(22,4)5)8-6-10-20-12-14-23(32-25(20)30)21-16-24(29)33-26(21)31-19(3)28/h8,12,16,23,25-26,30H,6-7,9-11,13-15H2,1-5H3/b17-8+/t23-,25-,26-/m1/s1
SMILES:	CC(=O)O[C@@H]1OC(=O)C=C1[C@H]1CC=C([C@@H](O1)O)CC/C=C(/CCC1=C(C)CCCC1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490765
PubChem CID:	44575737
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33331	brachiaster sp.	Species	n.a.	n.a.	n.a.	Thai	n.a.	PMID[15497961]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
MIC	1

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	260.0	nM	PMID[541501]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	760.0	nM	PMID[541501]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1680.0	nM	PMID[541501]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	630.0	nM	PMID[541501]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	7000.0	nM	PMID[541501]

☑ 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 NPC163606 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	182
0.1-0.2	1282
0.2-0.3	5704
0.3-0.4	15933
0.4-0.5	9428
0.5-0.6	7356
0.6-0.7	2544
0.7-0.8	231
0.8-0.85	22
0.85-0.9	8
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC126518
0.962	High Similarity	NPC323251
0.9136	High Similarity	NPC471298
0.9114	High Similarity	NPC474816
0.9114	High Similarity	NPC209135
0.9024	High Similarity	NPC471297
0.8987	High Similarity	NPC473756
0.8987	High Similarity	NPC262747
0.8941	High Similarity	NPC474629
0.8902	High Similarity	NPC324170
0.8864	High Similarity	NPC104925
0.8864	High Similarity	NPC298973
0.878	High Similarity	NPC475944
0.869	High Similarity	NPC471301
0.8652	High Similarity	NPC469697
0.8621	High Similarity	NPC470734
0.8588	High Similarity	NPC474860
0.8588	High Similarity	NPC471300
0.8571	High Similarity	NPC474809
0.8506	High Similarity	NPC472810
0.8506	High Similarity	NPC472378
0.8506	High Similarity	NPC472809
0.8481	Intermediate Similarity	NPC476489
0.8481	Intermediate Similarity	NPC16349
0.8481	Intermediate Similarity	NPC476490
0.8481	Intermediate Similarity	NPC222244
0.8471	Intermediate Similarity	NPC31086
0.8471	Intermediate Similarity	NPC471302
0.8471	Intermediate Similarity	NPC474865
0.8462	Intermediate Similarity	NPC162346
0.8353	Intermediate Similarity	NPC42476
0.8333	Intermediate Similarity	NPC472812
0.8235	Intermediate Similarity	NPC471296
0.8222	Intermediate Similarity	NPC472811
0.8161	Intermediate Similarity	NPC42586
0.8161	Intermediate Similarity	NPC473251
0.8068	Intermediate Similarity	NPC211892
0.8046	Intermediate Similarity	NPC470800
0.8043	Intermediate Similarity	NPC470255
0.8022	Intermediate Similarity	NPC141831
0.8022	Intermediate Similarity	NPC477122
0.8021	Intermediate Similarity	NPC201191
0.8	Intermediate Similarity	NPC477716
0.8	Intermediate Similarity	NPC477721
0.7979	Intermediate Similarity	NPC477719
0.7979	Intermediate Similarity	NPC477718
0.7955	Intermediate Similarity	NPC329630
0.7955	Intermediate Similarity	NPC472442
0.7931	Intermediate Similarity	NPC311070
0.7931	Intermediate Similarity	NPC472440
0.7931	Intermediate Similarity	NPC472377
0.7917	Intermediate Similarity	NPC477717
0.7912	Intermediate Similarity	NPC281942
0.7912	Intermediate Similarity	NPC232426
0.7912	Intermediate Similarity	NPC469403
0.7912	Intermediate Similarity	NPC78973
0.7895	Intermediate Similarity	NPC474440
0.7882	Intermediate Similarity	NPC471299
0.7849	Intermediate Similarity	NPC474554
0.7789	Intermediate Similarity	NPC475709
0.7789	Intermediate Similarity	NPC98112
0.7766	Intermediate Similarity	NPC472441
0.7742	Intermediate Similarity	NPC242069
0.7717	Intermediate Similarity	NPC477782
0.7717	Intermediate Similarity	NPC202886
0.7708	Intermediate Similarity	NPC473154
0.7684	Intermediate Similarity	NPC17578
0.7684	Intermediate Similarity	NPC165632
0.7684	Intermediate Similarity	NPC240673
0.7667	Intermediate Similarity	NPC131813
0.766	Intermediate Similarity	NPC324078
0.7634	Intermediate Similarity	NPC477783
0.7634	Intermediate Similarity	NPC329842
0.7629	Intermediate Similarity	NPC324841
0.7624	Intermediate Similarity	NPC470024
0.7614	Intermediate Similarity	NPC471218
0.7609	Intermediate Similarity	NPC477748
0.7595	Intermediate Similarity	NPC282760
0.7582	Intermediate Similarity	NPC316138
0.7582	Intermediate Similarity	NPC313658
0.7582	Intermediate Similarity	NPC312561
0.7576	Intermediate Similarity	NPC120009
0.7561	Intermediate Similarity	NPC4299
0.7556	Intermediate Similarity	NPC217394
0.7553	Intermediate Similarity	NPC156553
0.7553	Intermediate Similarity	NPC469939
0.7553	Intermediate Similarity	NPC53555
0.7553	Intermediate Similarity	NPC472196
0.7553	Intermediate Similarity	NPC238090
0.7553	Intermediate Similarity	NPC472195
0.7551	Intermediate Similarity	NPC198992
0.7549	Intermediate Similarity	NPC206618
0.7529	Intermediate Similarity	NPC477202
0.7528	Intermediate Similarity	NPC12283
0.7528	Intermediate Similarity	NPC474193
0.7525	Intermediate Similarity	NPC109376
0.7475	Intermediate Similarity	NPC238397
0.7475	Intermediate Similarity	NPC471363
0.7475	Intermediate Similarity	NPC472815
0.7474	Intermediate Similarity	NPC256368
0.7474	Intermediate Similarity	NPC477722
0.7474	Intermediate Similarity	NPC474555
0.7474	Intermediate Similarity	NPC475572
0.7474	Intermediate Similarity	NPC159698
0.7471	Intermediate Similarity	NPC139712
0.7471	Intermediate Similarity	NPC242767
0.747	Intermediate Similarity	NPC257618
0.7451	Intermediate Similarity	NPC38948
0.7451	Intermediate Similarity	NPC224660
0.7449	Intermediate Similarity	NPC477720
0.7447	Intermediate Similarity	NPC477749
0.7444	Intermediate Similarity	NPC186155
0.7444	Intermediate Similarity	NPC78673
0.7444	Intermediate Similarity	NPC160517
0.7442	Intermediate Similarity	NPC477203
0.7439	Intermediate Similarity	NPC101622
0.7439	Intermediate Similarity	NPC151481
0.7426	Intermediate Similarity	NPC172867
0.7426	Intermediate Similarity	NPC153095
0.7426	Intermediate Similarity	NPC82251
0.7426	Intermediate Similarity	NPC239961
0.7419	Intermediate Similarity	NPC251528
0.7419	Intermediate Similarity	NPC293044
0.7404	Intermediate Similarity	NPC17791
0.74	Intermediate Similarity	NPC127933
0.74	Intermediate Similarity	NPC134270
0.74	Intermediate Similarity	NPC475889
0.74	Intermediate Similarity	NPC45897
0.74	Intermediate Similarity	NPC7613
0.74	Intermediate Similarity	NPC7644
0.7396	Intermediate Similarity	NPC276110
0.7396	Intermediate Similarity	NPC476488
0.7396	Intermediate Similarity	NPC476487
0.7391	Intermediate Similarity	NPC199382
0.7374	Intermediate Similarity	NPC471075
0.7368	Intermediate Similarity	NPC115021
0.7368	Intermediate Similarity	NPC152778
0.7368	Intermediate Similarity	NPC162615
0.7368	Intermediate Similarity	NPC205034
0.7363	Intermediate Similarity	NPC471795
0.7363	Intermediate Similarity	NPC471494
0.7363	Intermediate Similarity	NPC35933
0.7356	Intermediate Similarity	NPC326753
0.7349	Intermediate Similarity	NPC469660
0.734	Intermediate Similarity	NPC182136
0.734	Intermediate Similarity	NPC470817
0.734	Intermediate Similarity	NPC280149
0.734	Intermediate Similarity	NPC221111
0.734	Intermediate Similarity	NPC253186
0.7333	Intermediate Similarity	NPC470025
0.7333	Intermediate Similarity	NPC317460
0.7333	Intermediate Similarity	NPC328074
0.7333	Intermediate Similarity	NPC161045
0.7333	Intermediate Similarity	NPC321272
0.7333	Intermediate Similarity	NPC469
0.7333	Intermediate Similarity	NPC44261
0.7327	Intermediate Similarity	NPC470321
0.7327	Intermediate Similarity	NPC201880
0.7327	Intermediate Similarity	NPC264867
0.7327	Intermediate Similarity	NPC473207
0.7327	Intermediate Similarity	NPC81567
0.7326	Intermediate Similarity	NPC27205
0.7326	Intermediate Similarity	NPC469880
0.732	Intermediate Similarity	NPC16967
0.732	Intermediate Similarity	NPC143446
0.732	Intermediate Similarity	NPC112654
0.7312	Intermediate Similarity	NPC106051
0.7312	Intermediate Similarity	NPC196407
0.7308	Intermediate Similarity	NPC316708
0.73	Intermediate Similarity	NPC121423
0.73	Intermediate Similarity	NPC134077
0.7283	Intermediate Similarity	NPC471219
0.7283	Intermediate Similarity	NPC311163
0.7283	Intermediate Similarity	NPC61527
0.7283	Intermediate Similarity	NPC474062
0.7282	Intermediate Similarity	NPC392
0.7282	Intermediate Similarity	NPC177524
0.7282	Intermediate Similarity	NPC219900
0.7273	Intermediate Similarity	NPC228251
0.7273	Intermediate Similarity	NPC161527
0.7273	Intermediate Similarity	NPC474012
0.7273	Intermediate Similarity	NPC20113
0.7273	Intermediate Similarity	NPC321728
0.7273	Intermediate Similarity	NPC477971
0.7273	Intermediate Similarity	NPC477968
0.7273	Intermediate Similarity	NPC227865
0.7273	Intermediate Similarity	NPC477972
0.7273	Intermediate Similarity	NPC476299
0.7273	Intermediate Similarity	NPC219285
0.7273	Intermediate Similarity	NPC472644
0.7273	Intermediate Similarity	NPC38855
0.7264	Intermediate Similarity	NPC470027
0.7263	Intermediate Similarity	NPC177037
0.7263	Intermediate Similarity	NPC72845
0.7263	Intermediate Similarity	NPC472814
0.7263	Intermediate Similarity	NPC179517
0.7263	Intermediate Similarity	NPC165904
0.7262	Intermediate Similarity	NPC316185
0.7262	Intermediate Similarity	NPC472254
0.7255	Intermediate Similarity	NPC252296

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 NPC163606 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1739
0.2-0.3	4157
0.3-0.4	2349
0.4-0.5	487
0.5-0.6	241
0.6-0.7	29
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9873	High Similarity	NPD6400	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6686	Approved
0.7	Intermediate Similarity	NPD4225	Approved
0.6907	Remote Similarity	NPD7637	Suspended
0.6832	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7640	Approved
0.6765	Remote Similarity	NPD7639	Approved
0.6747	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7328	Approved
0.6696	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7516	Approved
0.6633	Remote Similarity	NPD5785	Approved
0.6633	Remote Similarity	NPD46	Approved
0.6633	Remote Similarity	NPD6698	Approved
0.6596	Remote Similarity	NPD7154	Phase 3
0.6585	Remote Similarity	NPD4191	Approved
0.6585	Remote Similarity	NPD4194	Approved
0.6585	Remote Similarity	NPD4192	Approved
0.6585	Remote Similarity	NPD4193	Approved
0.6579	Remote Similarity	NPD8294	Approved
0.6579	Remote Similarity	NPD8377	Approved
0.6522	Remote Similarity	NPD8378	Approved
0.6522	Remote Similarity	NPD8379	Approved
0.6522	Remote Similarity	NPD8335	Approved
0.6522	Remote Similarity	NPD8380	Approved
0.6522	Remote Similarity	NPD8296	Approved
0.65	Remote Similarity	NPD5778	Approved
0.65	Remote Similarity	NPD5779	Approved
0.6465	Remote Similarity	NPD7838	Discovery
0.646	Remote Similarity	NPD7115	Discovery
0.6452	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD8039	Approved
0.6444	Remote Similarity	NPD8264	Approved
0.6421	Remote Similarity	NPD6695	Phase 3
0.6413	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6411	Approved
0.6389	Remote Similarity	NPD6412	Phase 2
0.6381	Remote Similarity	NPD5344	Discontinued
0.6364	Remote Similarity	NPD6051	Approved
0.6354	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5776	Phase 2
0.6304	Remote Similarity	NPD6925	Approved
0.6303	Remote Similarity	NPD7507	Approved
0.6289	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4819	Approved
0.6277	Remote Similarity	NPD4821	Approved
0.6277	Remote Similarity	NPD4822	Approved
0.6277	Remote Similarity	NPD4820	Approved
0.6277	Remote Similarity	NPD7332	Phase 2
0.6277	Remote Similarity	NPD7514	Phase 3
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD5362	Discontinued
0.6239	Remote Similarity	NPD8513	Phase 3
0.6237	Remote Similarity	NPD7145	Approved
0.6237	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4271	Approved
0.6237	Remote Similarity	NPD4268	Approved
0.6214	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6902	Approved
0.62	Remote Similarity	NPD6101	Approved
0.62	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6399	Phase 3
0.617	Remote Similarity	NPD6929	Approved
0.6168	Remote Similarity	NPD7632	Discontinued
0.6162	Remote Similarity	NPD7524	Approved
0.6162	Remote Similarity	NPD7750	Discontinued
0.6154	Remote Similarity	NPD7839	Suspended
0.6148	Remote Similarity	NPD7319	Approved
0.6146	Remote Similarity	NPD5209	Approved
0.6132	Remote Similarity	NPD6648	Approved
0.6122	Remote Similarity	NPD5363	Approved
0.6122	Remote Similarity	NPD1694	Approved
0.6117	Remote Similarity	NPD7748	Approved
0.6106	Remote Similarity	NPD6882	Approved
0.6105	Remote Similarity	NPD6931	Approved
0.6105	Remote Similarity	NPD6930	Phase 2
0.6102	Remote Similarity	NPD8515	Approved
0.6102	Remote Similarity	NPD8516	Approved
0.6102	Remote Similarity	NPD8517	Approved
0.6082	Remote Similarity	NPD5332	Approved
0.6082	Remote Similarity	NPD5331	Approved
0.6078	Remote Similarity	NPD7515	Phase 2
0.6071	Remote Similarity	NPD6371	Approved
0.6067	Remote Similarity	NPD6922	Approved
0.6067	Remote Similarity	NPD6923	Approved
0.6061	Remote Similarity	NPD7146	Approved
0.6061	Remote Similarity	NPD7521	Approved
0.6061	Remote Similarity	NPD5330	Approved
0.6061	Remote Similarity	NPD6409	Approved
0.6061	Remote Similarity	NPD6684	Approved
0.6061	Remote Similarity	NPD7334	Approved
0.6058	Remote Similarity	NPD5695	Phase 3
0.6042	Remote Similarity	NPD6898	Phase 1
0.6042	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD7144	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD7143	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD4251	Approved
0.5982	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4269	Approved
0.5979	Remote Similarity	NPD4270	Approved
0.5978	Remote Similarity	NPD6926	Approved
0.5978	Remote Similarity	NPD6924	Approved
0.5976	Remote Similarity	NPD4219	Approved
0.5957	Remote Similarity	NPD6932	Approved
0.5943	Remote Similarity	NPD7902	Approved
0.5941	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6672	Approved
0.5941	Remote Similarity	NPD5737	Approved
0.5941	Remote Similarity	NPD6903	Approved
0.5938	Remote Similarity	NPD4252	Approved
0.5934	Remote Similarity	NPD7152	Approved
0.5934	Remote Similarity	NPD7150	Approved
0.5934	Remote Similarity	NPD7151	Approved
0.5922	Remote Similarity	NPD7087	Discontinued
0.5922	Remote Similarity	NPD7983	Approved
0.5914	Remote Similarity	NPD7339	Approved
0.5914	Remote Similarity	NPD6942	Approved
0.59	Remote Similarity	NPD4249	Approved
0.59	Remote Similarity	NPD5786	Approved
0.5893	Remote Similarity	NPD7320	Approved
0.5893	Remote Similarity	NPD6899	Approved
0.5893	Remote Similarity	NPD6881	Approved
0.5888	Remote Similarity	NPD5696	Approved
0.5882	Remote Similarity	NPD689	Discontinued
0.5859	Remote Similarity	NPD3665	Phase 1
0.5859	Remote Similarity	NPD4786	Approved
0.5859	Remote Similarity	NPD3666	Approved
0.5859	Remote Similarity	NPD3133	Approved
0.5856	Remote Similarity	NPD4211	Phase 1
0.5851	Remote Similarity	NPD6933	Approved
0.5851	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6372	Approved
0.5841	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD7645	Phase 2
0.5833	Remote Similarity	NPD6683	Phase 2
0.5816	Remote Similarity	NPD6435	Approved
0.5816	Remote Similarity	NPD3667	Approved
0.5814	Remote Similarity	NPD368	Approved
0.5804	Remote Similarity	NPD5701	Approved
0.5804	Remote Similarity	NPD5697	Approved
0.58	Remote Similarity	NPD1696	Phase 3
0.58	Remote Similarity	NPD6893	Approved
0.5789	Remote Similarity	NPD6883	Approved
0.5789	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7290	Approved
0.5789	Remote Similarity	NPD4756	Discovery
0.5789	Remote Similarity	NPD7102	Approved
0.5776	Remote Similarity	NPD8133	Approved
0.5769	Remote Similarity	NPD5693	Phase 1
0.5763	Remote Similarity	NPD7505	Discontinued
0.5743	Remote Similarity	NPD3618	Phase 1
0.5743	Remote Similarity	NPD5279	Phase 3
0.5739	Remote Similarity	NPD6847	Approved
0.5739	Remote Similarity	NPD6650	Approved
0.5739	Remote Similarity	NPD6617	Approved
0.5739	Remote Similarity	NPD8130	Phase 1
0.5739	Remote Similarity	NPD6649	Approved
0.5739	Remote Similarity	NPD6869	Approved
0.5738	Remote Similarity	NPD7830	Approved
0.5738	Remote Similarity	NPD7829	Approved
0.5738	Remote Similarity	NPD8328	Phase 3
0.5728	Remote Similarity	NPD4753	Phase 2
0.5728	Remote Similarity	NPD5328	Approved
0.5726	Remote Similarity	NPD8293	Discontinued
0.5714	Remote Similarity	NPD6640	Phase 3
0.5714	Remote Similarity	NPD5369	Approved
0.5702	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD6012	Approved
0.5702	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6014	Approved
0.5699	Remote Similarity	NPD4732	Discontinued
0.5698	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.569	Remote Similarity	NPD8297	Approved
0.5686	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.568	Remote Similarity	NPD7736	Approved
0.5673	Remote Similarity	NPD7136	Phase 2
0.5664	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.566	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.566	Remote Similarity	NPD7900	Approved
0.5656	Remote Similarity	NPD6370	Approved
0.5619	Remote Similarity	NPD6079	Approved
0.5619	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6011	Approved
0.5612	Remote Similarity	NPD5368	Approved
0.5612	Remote Similarity	NPD7525	Registered

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