NPASS Compound

Structure

NPC474816 OpenBabel07101719512D 32 33 0 0 1 0 0 0 0 0999 V2000 4.4347 5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5327 2.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0327 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2738 3.0485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 2.9945 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 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 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 19 2 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 22 2 0 0 0 0 13 24 1 0 0 0 0 15 27 1 0 0 0 0 16 23 2 0 0 0 0 16 26 1 0 0 0 0 17 23 1 0 0 0 0 17 28 1 0 0 0 0 18 22 1 0 0 0 0 18 31 1 0 0 0 0 20 24 2 0 0 0 0 21 29 2 0 0 0 0 21 31 1 0 0 0 0 23 25 1 0 0 0 0 24 27 1 0 0 0 0 25 14 1 1 0 0 0 25 32 1 0 0 0 0 26 30 2 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.29
Volume:	486.568
LogP:	4.967
LogD:	4.022
LogS:	-4.158
# Rotatable Bonds:	12
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.299
Synthetic Accessibility Score:	3.668
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:	-4.835
MDCK Permeability:	2.3624210371053778e-05
Pgp-inhibitor:	0.496
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.934
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.383
Plasma Protein Binding (PPB):	92.6029281616211%
Volume Distribution (VD):	2.743
Pgp-substrate:	1.8141331672668457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.13
CYP1A2-substrate:	0.148
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.197
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.655
CYP2D6-substrate:	0.813
CYP3A4-inhibitor:	0.357
CYP3A4-substrate:	0.24

ADMET: Excretion

Clearance (CL):	5.156
Half-life (T1/2):	0.912

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.318
Drug-inuced Liver Injury (DILI):	0.596
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.442
Carcinogencity:	0.198
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC474816

Natural Product ID:	NPC474816
*Common Name:**	Z-24-Acetoxyneomanoalide
IUPAC Name:	[(E,2Z)-2-[2-[(2R)-3-(hydroxymethyl)-5-oxo-2H-furan-2-yl]ethylidene]-6-methyl-8-(2,6,6-trimethylcyclohexen-1-yl)oct-5-enyl] acetate
Synonyms:	6Z-24-Acetoxyneomanoalide
Standard InCHIKey:	MRHKMIZTLJVJLS-CVSCDAIJSA-N
Standard InCHI:	InChI=1S/C27H40O5/c1-19(11-13-24-20(2)9-7-15-27(24,4)5)8-6-10-22(18-31-21(3)29)12-14-25-23(17-28)16-26(30)32-25/h8,12,16,25,28H,6-7,9-11,13-15,17-18H2,1-5H3/b19-8+,22-12-/t25-/m1/s1
SMILES:	OCC1=CC(=O)O[C@@H]1C/C=C(COC(=O)C)/CC/C=C(/CCC1=C(C)CCCC1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483832
PubChem CID:	44593600
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
NPO32622	luffariella sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1624940]
NPO32622	luffariella sp.	Species	Thorectidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[8482949]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	3.0	ug.mL-1	PMID[534614]
NPT91	Cell Line	KB	Homo sapiens	GI	=	44.8	%	PMID[534614]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	Activity	=	8.0	ug	PMID[534613]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Activity	=	2.0	ug	PMID[534613]

☑ 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 NPC474816 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	158
0.1-0.2	1162
0.2-0.3	5488
0.3-0.4	16045
0.4-0.5	9631
0.5-0.6	6463
0.6-0.7	3239
0.7-0.8	460
0.8-0.85	35
0.85-0.9	4
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC209135
0.9861	High Similarity	NPC262747
0.96	High Similarity	NPC475944
0.9474	High Similarity	NPC323251
0.9351	High Similarity	NPC474809
0.9306	High Similarity	NPC222244
0.9306	High Similarity	NPC16349
0.9231	High Similarity	NPC31086
0.9231	High Similarity	NPC474865
0.9231	High Similarity	NPC126518
0.9114	High Similarity	NPC163606
0.8974	High Similarity	NPC471298
0.8861	High Similarity	NPC471297
0.8861	High Similarity	NPC42476
0.8816	High Similarity	NPC473756
0.8734	High Similarity	NPC324170
0.8625	High Similarity	NPC472377
0.859	High Similarity	NPC471299
0.8554	High Similarity	NPC474629
0.8554	High Similarity	NPC472378
0.8519	High Similarity	NPC471301
0.8415	Intermediate Similarity	NPC474860
0.8415	Intermediate Similarity	NPC471300
0.8395	Intermediate Similarity	NPC311070
0.8353	Intermediate Similarity	NPC78973
0.8333	Intermediate Similarity	NPC282760
0.8293	Intermediate Similarity	NPC471302
0.8276	Intermediate Similarity	NPC104925
0.8276	Intermediate Similarity	NPC298973
0.8267	Intermediate Similarity	NPC4299
0.8235	Intermediate Similarity	NPC470734
0.8214	Intermediate Similarity	NPC312561
0.8205	Intermediate Similarity	NPC477202
0.8171	Intermediate Similarity	NPC474193
0.8171	Intermediate Similarity	NPC12283
0.8158	Intermediate Similarity	NPC257618
0.814	Intermediate Similarity	NPC232426
0.814	Intermediate Similarity	NPC281942
0.8133	Intermediate Similarity	NPC101622
0.8118	Intermediate Similarity	NPC472810
0.8118	Intermediate Similarity	NPC472809
0.8101	Intermediate Similarity	NPC477203
0.8095	Intermediate Similarity	NPC131813
0.8072	Intermediate Similarity	NPC186155
0.8072	Intermediate Similarity	NPC78673
0.8072	Intermediate Similarity	NPC160517
0.8068	Intermediate Similarity	NPC469697
0.8052	Intermediate Similarity	NPC476489
0.8052	Intermediate Similarity	NPC476490
0.8049	Intermediate Similarity	NPC471296
0.8049	Intermediate Similarity	NPC471218
0.8046	Intermediate Similarity	NPC141831
0.8026	Intermediate Similarity	NPC469660
0.7976	Intermediate Similarity	NPC471795
0.7975	Intermediate Similarity	NPC469880
0.7975	Intermediate Similarity	NPC27205
0.7955	Intermediate Similarity	NPC472812
0.7955	Intermediate Similarity	NPC53555
0.7952	Intermediate Similarity	NPC161045
0.7922	Intermediate Similarity	NPC472254
0.7922	Intermediate Similarity	NPC316185
0.7901	Intermediate Similarity	NPC139712
0.7901	Intermediate Similarity	NPC242767
0.7895	Intermediate Similarity	NPC151481
0.7889	Intermediate Similarity	NPC162346
0.7882	Intermediate Similarity	NPC61527
0.7882	Intermediate Similarity	NPC211892
0.7867	Intermediate Similarity	NPC472266
0.7841	Intermediate Similarity	NPC472811
0.7821	Intermediate Similarity	NPC477085
0.7802	Intermediate Similarity	NPC53844
0.7792	Intermediate Similarity	NPC473361
0.7792	Intermediate Similarity	NPC329904
0.7791	Intermediate Similarity	NPC199382
0.7791	Intermediate Similarity	NPC476600
0.7778	Intermediate Similarity	NPC276110
0.7765	Intermediate Similarity	NPC11804
0.7765	Intermediate Similarity	NPC35933
0.7765	Intermediate Similarity	NPC42586
0.7765	Intermediate Similarity	NPC473251
0.7753	Intermediate Similarity	NPC115021
0.7753	Intermediate Similarity	NPC472954
0.7753	Intermediate Similarity	NPC162615
0.7753	Intermediate Similarity	NPC152778
0.7753	Intermediate Similarity	NPC205034
0.7738	Intermediate Similarity	NPC23748
0.7733	Intermediate Similarity	NPC37382
0.7727	Intermediate Similarity	NPC182136
0.7727	Intermediate Similarity	NPC221111
0.7727	Intermediate Similarity	NPC280149
0.7722	Intermediate Similarity	NPC470686
0.7722	Intermediate Similarity	NPC315843
0.7711	Intermediate Similarity	NPC315731
0.7711	Intermediate Similarity	NPC112868
0.7692	Intermediate Similarity	NPC477087
0.7692	Intermediate Similarity	NPC16967
0.7692	Intermediate Similarity	NPC165632
0.7692	Intermediate Similarity	NPC477086
0.7683	Intermediate Similarity	NPC110373
0.7683	Intermediate Similarity	NPC5908
0.7683	Intermediate Similarity	NPC80471
0.7674	Intermediate Similarity	NPC471219
0.7667	Intermediate Similarity	NPC53685
0.7667	Intermediate Similarity	NPC470255
0.7654	Intermediate Similarity	NPC315394
0.7654	Intermediate Similarity	NPC84360
0.7647	Intermediate Similarity	NPC470800
0.764	Intermediate Similarity	NPC477122
0.764	Intermediate Similarity	NPC177037
0.764	Intermediate Similarity	NPC472814
0.764	Intermediate Similarity	NPC72845
0.764	Intermediate Similarity	NPC329842
0.7634	Intermediate Similarity	NPC38855
0.7625	Intermediate Similarity	NPC329852
0.7619	Intermediate Similarity	NPC256112
0.7614	Intermediate Similarity	NPC79027
0.7614	Intermediate Similarity	NPC5509
0.7614	Intermediate Similarity	NPC50488
0.7614	Intermediate Similarity	NPC474396
0.7614	Intermediate Similarity	NPC174342
0.7609	Intermediate Similarity	NPC205143
0.7609	Intermediate Similarity	NPC477719
0.7609	Intermediate Similarity	NPC477718
0.76	Intermediate Similarity	NPC470123
0.7586	Intermediate Similarity	NPC166857
0.7586	Intermediate Similarity	NPC471796
0.7561	Intermediate Similarity	NPC279532
0.7561	Intermediate Similarity	NPC471220
0.7561	Intermediate Similarity	NPC184737
0.7558	Intermediate Similarity	NPC30984
0.7558	Intermediate Similarity	NPC471494
0.7558	Intermediate Similarity	NPC329630
0.7556	Intermediate Similarity	NPC156553
0.7556	Intermediate Similarity	NPC139692
0.7532	Intermediate Similarity	NPC276290
0.7532	Intermediate Similarity	NPC474823
0.7529	Intermediate Similarity	NPC477124
0.7529	Intermediate Similarity	NPC44261
0.7529	Intermediate Similarity	NPC16488
0.7529	Intermediate Similarity	NPC193198
0.7529	Intermediate Similarity	NPC49208
0.7528	Intermediate Similarity	NPC220216
0.7528	Intermediate Similarity	NPC310479
0.7527	Intermediate Similarity	NPC325229
0.7527	Intermediate Similarity	NPC275086
0.75	Intermediate Similarity	NPC134072
0.75	Intermediate Similarity	NPC107654
0.75	Intermediate Similarity	NPC474758
0.75	Intermediate Similarity	NPC477204
0.75	Intermediate Similarity	NPC8538
0.75	Intermediate Similarity	NPC474280
0.75	Intermediate Similarity	NPC234993
0.75	Intermediate Similarity	NPC473153
0.75	Intermediate Similarity	NPC184208
0.75	Intermediate Similarity	NPC242848
0.75	Intermediate Similarity	NPC170303
0.75	Intermediate Similarity	NPC159148
0.75	Intermediate Similarity	NPC146811
0.7473	Intermediate Similarity	NPC469491
0.7473	Intermediate Similarity	NPC105490
0.7473	Intermediate Similarity	NPC57117
0.7473	Intermediate Similarity	NPC191521
0.7471	Intermediate Similarity	NPC311163
0.7471	Intermediate Similarity	NPC477668
0.7471	Intermediate Similarity	NPC475461
0.7471	Intermediate Similarity	NPC329692
0.7471	Intermediate Similarity	NPC315395
0.7471	Intermediate Similarity	NPC316426
0.7471	Intermediate Similarity	NPC305475
0.747	Intermediate Similarity	NPC471537
0.747	Intermediate Similarity	NPC325869
0.7467	Intermediate Similarity	NPC226066
0.7447	Intermediate Similarity	NPC477721
0.7447	Intermediate Similarity	NPC474012
0.7447	Intermediate Similarity	NPC477716
0.7447	Intermediate Similarity	NPC476299
0.7447	Intermediate Similarity	NPC227865
0.7444	Intermediate Similarity	NPC124374
0.7444	Intermediate Similarity	NPC2882
0.7444	Intermediate Similarity	NPC234335
0.7442	Intermediate Similarity	NPC96055
0.7439	Intermediate Similarity	NPC40049
0.7439	Intermediate Similarity	NPC474278
0.7436	Intermediate Similarity	NPC475004
0.7432	Intermediate Similarity	NPC55376
0.7419	Intermediate Similarity	NPC73911
0.7419	Intermediate Similarity	NPC51499
0.7419	Intermediate Similarity	NPC475709
0.7419	Intermediate Similarity	NPC208094
0.7416	Intermediate Similarity	NPC261320
0.7416	Intermediate Similarity	NPC246028
0.7416	Intermediate Similarity	NPC314727
0.7416	Intermediate Similarity	NPC133450
0.7416	Intermediate Similarity	NPC20946
0.7412	Intermediate Similarity	NPC474252
0.7403	Intermediate Similarity	NPC203335
0.7391	Intermediate Similarity	NPC472441
0.7386	Intermediate Similarity	NPC473891
0.7386	Intermediate Similarity	NPC316138
0.7386	Intermediate Similarity	NPC313658

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 NPC474816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	128
0.1-0.2	1654
0.2-0.3	4067
0.3-0.4	2447
0.4-0.5	542
0.5-0.6	244
0.6-0.7	60
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD6400	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4225	Approved
0.7253	Intermediate Similarity	NPD7637	Suspended
0.72	Intermediate Similarity	NPD4192	Approved
0.72	Intermediate Similarity	NPD4194	Approved
0.72	Intermediate Similarity	NPD4191	Approved
0.72	Intermediate Similarity	NPD4193	Approved
0.7143	Intermediate Similarity	NPD46	Approved
0.7143	Intermediate Similarity	NPD6698	Approved
0.7143	Intermediate Similarity	NPD5785	Approved
0.7126	Intermediate Similarity	NPD7154	Phase 3
0.7083	Intermediate Similarity	NPD7639	Approved
0.7083	Intermediate Similarity	NPD7640	Approved
0.7011	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD8039	Approved
0.6979	Remote Similarity	NPD7638	Approved
0.6977	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7838	Discovery
0.6941	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5344	Discontinued
0.6809	Remote Similarity	NPD5779	Approved
0.6809	Remote Similarity	NPD5778	Approved
0.6786	Remote Similarity	NPD8264	Approved
0.6782	Remote Similarity	NPD4820	Approved
0.6782	Remote Similarity	NPD4821	Approved
0.6782	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4819	Approved
0.6782	Remote Similarity	NPD4822	Approved
0.6778	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6686	Approved
0.6744	Remote Similarity	NPD4268	Approved
0.6744	Remote Similarity	NPD4271	Approved
0.6742	Remote Similarity	NPD5362	Discontinued
0.6742	Remote Similarity	NPD6695	Phase 3
0.6702	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6051	Approved
0.6633	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5209	Approved
0.6628	Remote Similarity	NPD6925	Approved
0.6628	Remote Similarity	NPD5776	Phase 2
0.6593	Remote Similarity	NPD5363	Approved
0.6591	Remote Similarity	NPD7514	Phase 3
0.6591	Remote Similarity	NPD7332	Phase 2
0.6574	Remote Similarity	NPD7115	Discovery
0.6566	Remote Similarity	NPD6648	Approved
0.6556	Remote Similarity	NPD5332	Approved
0.6556	Remote Similarity	NPD5331	Approved
0.6552	Remote Similarity	NPD7145	Approved
0.6552	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4219	Approved
0.6531	Remote Similarity	NPD6083	Phase 2
0.6531	Remote Similarity	NPD6084	Phase 2
0.6517	Remote Similarity	NPD6902	Approved
0.6517	Remote Similarity	NPD4790	Discontinued
0.6489	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6929	Approved
0.6476	Remote Similarity	NPD6371	Approved
0.6458	Remote Similarity	NPD6399	Phase 3
0.6452	Remote Similarity	NPD7750	Discontinued
0.6452	Remote Similarity	NPD7524	Approved
0.6452	Remote Similarity	NPD4251	Approved
0.6452	Remote Similarity	NPD4250	Approved
0.6444	Remote Similarity	NPD4269	Approved
0.6444	Remote Similarity	NPD4270	Approved
0.6436	Remote Similarity	NPD7632	Discontinued
0.6429	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD1694	Approved
0.6404	Remote Similarity	NPD6931	Approved
0.6404	Remote Similarity	NPD4252	Approved
0.6404	Remote Similarity	NPD6930	Phase 2
0.6392	Remote Similarity	NPD7748	Approved
0.6386	Remote Similarity	NPD6923	Approved
0.6386	Remote Similarity	NPD6922	Approved
0.6355	Remote Similarity	NPD6053	Discontinued
0.6354	Remote Similarity	NPD7983	Approved
0.6354	Remote Similarity	NPD7515	Phase 2
0.6344	Remote Similarity	NPD7334	Approved
0.6344	Remote Similarity	NPD7146	Approved
0.6344	Remote Similarity	NPD6684	Approved
0.6344	Remote Similarity	NPD5330	Approved
0.6344	Remote Similarity	NPD7521	Approved
0.6344	Remote Similarity	NPD5786	Approved
0.6344	Remote Similarity	NPD6409	Approved
0.6344	Remote Similarity	NPD4249	Approved
0.6333	Remote Similarity	NPD6898	Phase 1
0.6329	Remote Similarity	NPD368	Approved
0.6327	Remote Similarity	NPD5695	Phase 3
0.631	Remote Similarity	NPD7143	Approved
0.631	Remote Similarity	NPD7144	Approved
0.6279	Remote Similarity	NPD6926	Approved
0.6279	Remote Similarity	NPD6924	Approved
0.6264	Remote Similarity	NPD6435	Approved
0.6263	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD6932	Approved
0.625	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD5739	Approved
0.625	Remote Similarity	NPD7128	Approved
0.625	Remote Similarity	NPD4756	Discovery
0.6237	Remote Similarity	NPD1696	Phase 3
0.6235	Remote Similarity	NPD7150	Approved
0.6235	Remote Similarity	NPD7152	Approved
0.6235	Remote Similarity	NPD7151	Approved
0.6226	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7328	Approved
0.6216	Remote Similarity	NPD7327	Approved
0.6211	Remote Similarity	NPD6672	Approved
0.6211	Remote Similarity	NPD6903	Approved
0.6211	Remote Similarity	NPD5737	Approved
0.6211	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6942	Approved
0.6207	Remote Similarity	NPD7339	Approved
0.6203	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7902	Approved
0.6195	Remote Similarity	NPD8033	Approved
0.6186	Remote Similarity	NPD7087	Discontinued
0.6163	Remote Similarity	NPD4732	Discontinued
0.6161	Remote Similarity	NPD7516	Approved
0.6154	Remote Similarity	NPD5369	Approved
0.6139	Remote Similarity	NPD5696	Approved
0.6136	Remote Similarity	NPD6933	Approved
0.6136	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6881	Approved
0.6132	Remote Similarity	NPD7320	Approved
0.6132	Remote Similarity	NPD6899	Approved
0.6129	Remote Similarity	NPD3133	Approved
0.6129	Remote Similarity	NPD3666	Approved
0.6129	Remote Similarity	NPD3665	Phase 1
0.6129	Remote Similarity	NPD4786	Approved
0.6126	Remote Similarity	NPD7505	Discontinued
0.6111	Remote Similarity	NPD6683	Phase 2
0.6111	Remote Similarity	NPD7645	Phase 2
0.6106	Remote Similarity	NPD8377	Approved
0.6106	Remote Similarity	NPD8294	Approved
0.6087	Remote Similarity	NPD3667	Approved
0.6081	Remote Similarity	NPD6927	Phase 3
0.6075	Remote Similarity	NPD6372	Approved
0.6075	Remote Similarity	NPD6373	Approved
0.6064	Remote Similarity	NPD6893	Approved
0.6053	Remote Similarity	NPD8378	Approved
0.6053	Remote Similarity	NPD8335	Approved
0.6053	Remote Similarity	NPD8380	Approved
0.6053	Remote Similarity	NPD7503	Approved
0.6053	Remote Similarity	NPD8296	Approved
0.6053	Remote Similarity	NPD8379	Approved
0.6044	Remote Similarity	NPD5368	Approved
0.6038	Remote Similarity	NPD5701	Approved
0.6038	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5697	Approved
0.6024	Remote Similarity	NPD7331	Phase 2
0.6022	Remote Similarity	NPD6110	Phase 1
0.602	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5693	Phase 1
0.6019	Remote Similarity	NPD7102	Approved
0.6019	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7290	Approved
0.6019	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD3618	Phase 1
0.5979	Remote Similarity	NPD5328	Approved
0.5979	Remote Similarity	NPD5370	Suspended
0.5979	Remote Similarity	NPD4753	Phase 2
0.5974	Remote Similarity	NPD342	Phase 1
0.5963	Remote Similarity	NPD6617	Approved
0.5963	Remote Similarity	NPD6650	Approved
0.5963	Remote Similarity	NPD6847	Approved
0.5963	Remote Similarity	NPD6649	Approved
0.5963	Remote Similarity	NPD6869	Approved
0.5963	Remote Similarity	NPD8130	Phase 1
0.5963	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD9119	Approved
0.5949	Remote Similarity	NPD69	Approved
0.5943	Remote Similarity	NPD4211	Phase 1
0.5943	Remote Similarity	NPD6640	Phase 3
0.5938	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6014	Approved
0.5926	Remote Similarity	NPD6012	Approved
0.5926	Remote Similarity	NPD6013	Approved
0.5918	Remote Similarity	NPD7136	Phase 2
0.5909	Remote Similarity	NPD6882	Approved
0.5909	Remote Similarity	NPD8297	Approved
0.5905	Remote Similarity	NPD6647	Phase 2
0.59	Remote Similarity	NPD5282	Discontinued
0.59	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.59	Remote Similarity	NPD7900	Approved
0.5895	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6412	Phase 2
0.587	Remote Similarity	NPD7525	Registered
0.587	Remote Similarity	NPD7509	Discontinued
0.587	Remote Similarity	NPD4695	Discontinued
0.5859	Remote Similarity	NPD6079	Approved
0.5847	Remote Similarity	NPD7507	Approved
0.5833	Remote Similarity	NPD4265	Approved
0.5833	Remote Similarity	NPD6011	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