NPASS Compound

Structure

NPC262747 OpenBabel07101718332D 28 29 0 0 1 0 0 0 0 0999 V2000 6.2788 2.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2429 2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2429 2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6090 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7429 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 1.7976 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 10.6090 1.2976 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 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8769 0.2976 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 1.2976 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 9.7429 1.7976 0.0000 C 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 -1.4945 -0.9706 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 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 18 2 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 19 2 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 25 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 28 1 0 0 0 0 20 22 2 0 0 0 0 21 23 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 1 0 0 0 24 27 2 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.28
Volume:	437.032
LogP:	7.176
LogD:	5.481
LogS:	-3.898
# Rotatable Bonds:	10
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.332
Synthetic Accessibility Score:	3.827
Fsp3:	0.64
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.874
MDCK Permeability:	1.6020872863009572e-05
Pgp-inhibitor:	0.828
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.539
30% Bioavailability (F30%):	0.358

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	94.39102935791016%
Volume Distribution (VD):	3.865
Pgp-substrate:	0.9981072545051575%

ADMET: Metabolism

CYP1A2-inhibitor:	0.193
CYP1A2-substrate:	0.302
CYP2C19-inhibitor:	0.446
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.393
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.297
CYP2D6-substrate:	0.748
CYP3A4-inhibitor:	0.296
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	7.286
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.237
Maximum Recommended Daily Dose:	0.209
Skin Sensitization:	0.391
Carcinogencity:	0.048
Eye Corrosion:	0.04
Eye Irritation:	0.44
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC262747

Natural Product ID:	NPC262747
*Common Name:**	Thorectidaeolide E
IUPAC Name:	3-[(1R,3E,7E)-1-hydroxy-4,8-dimethyl-10-(2,6,6-trimethylcyclohexen-1-yl)deca-3,7-dienyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	JUAXVUXRHYSTHI-BUJWZSRDSA-N
Standard InCHI:	InChI=1S/C25H38O3/c1-18(11-13-22-20(3)10-7-15-25(22,4)5)8-6-9-19(2)12-14-23(26)21-16-24(27)28-17-21/h8,12,16,23,26H,6-7,9-11,13-15,17H2,1-5H3/b18-8+,19-12+/t23-/m1/s1
SMILES:	C/C(=CCC/C(=C/C[C@H](C1=CC(=O)OC1)O)/C)/CCC1=C(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409152
PubChem CID:	72189182
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
NPO33221	hyrtios communis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23944963]

☑ 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

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[543841]
NPT396	Cell Line	T47D	Homo sapiens	IC50	>	10000.0	nM	PMID[543841]

☑ 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 NPC262747 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	159
0.1-0.2	1164
0.2-0.3	5801
0.3-0.4	16530
0.4-0.5	9172
0.5-0.6	6376
0.6-0.7	3077
0.7-0.8	373
0.8-0.85	28
0.85-0.9	6
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC474816
0.9861	High Similarity	NPC209135
0.9467	High Similarity	NPC475944
0.9342	High Similarity	NPC323251
0.9221	High Similarity	NPC474809
0.9167	High Similarity	NPC222244
0.9167	High Similarity	NPC16349
0.9103	High Similarity	NPC126518
0.9103	High Similarity	NPC31086
0.9103	High Similarity	NPC474865
0.8987	High Similarity	NPC163606
0.8974	High Similarity	NPC42476
0.8933	High Similarity	NPC473756
0.8846	High Similarity	NPC471298
0.8734	High Similarity	NPC471297
0.8734	High Similarity	NPC472377
0.8608	High Similarity	NPC324170
0.85	High Similarity	NPC311070
0.8462	Intermediate Similarity	NPC471299
0.8434	Intermediate Similarity	NPC472378
0.8434	Intermediate Similarity	NPC474629
0.8395	Intermediate Similarity	NPC471301
0.8313	Intermediate Similarity	NPC312561
0.8293	Intermediate Similarity	NPC471300
0.8293	Intermediate Similarity	NPC474860
0.8267	Intermediate Similarity	NPC257618
0.8235	Intermediate Similarity	NPC78973
0.8194	Intermediate Similarity	NPC282760
0.8171	Intermediate Similarity	NPC471302
0.8161	Intermediate Similarity	NPC298973
0.8161	Intermediate Similarity	NPC104925
0.8158	Intermediate Similarity	NPC476490
0.8158	Intermediate Similarity	NPC476489
0.8133	Intermediate Similarity	NPC4299
0.8118	Intermediate Similarity	NPC470734
0.8077	Intermediate Similarity	NPC477202
0.8077	Intermediate Similarity	NPC27205
0.8072	Intermediate Similarity	NPC471795
0.8049	Intermediate Similarity	NPC12283
0.8049	Intermediate Similarity	NPC474193
0.8026	Intermediate Similarity	NPC472254
0.8023	Intermediate Similarity	NPC232426
0.8023	Intermediate Similarity	NPC281942
0.8	Intermediate Similarity	NPC101622
0.8	Intermediate Similarity	NPC242767
0.8	Intermediate Similarity	NPC472810
0.8	Intermediate Similarity	NPC472809
0.7976	Intermediate Similarity	NPC131813
0.7975	Intermediate Similarity	NPC477203
0.7973	Intermediate Similarity	NPC472266
0.7955	Intermediate Similarity	NPC469697
0.7952	Intermediate Similarity	NPC160517
0.7952	Intermediate Similarity	NPC186155
0.7952	Intermediate Similarity	NPC78673
0.7931	Intermediate Similarity	NPC141831
0.7927	Intermediate Similarity	NPC471218
0.7927	Intermediate Similarity	NPC471296
0.7895	Intermediate Similarity	NPC469660
0.7857	Intermediate Similarity	NPC473251
0.7857	Intermediate Similarity	NPC42586
0.7848	Intermediate Similarity	NPC469880
0.7841	Intermediate Similarity	NPC472812
0.7841	Intermediate Similarity	NPC53555
0.7841	Intermediate Similarity	NPC115021
0.7841	Intermediate Similarity	NPC472954
0.7838	Intermediate Similarity	NPC37382
0.7831	Intermediate Similarity	NPC161045
0.7816	Intermediate Similarity	NPC221111
0.7816	Intermediate Similarity	NPC280149
0.7816	Intermediate Similarity	NPC182136
0.7792	Intermediate Similarity	NPC316185
0.7778	Intermediate Similarity	NPC139712
0.7778	Intermediate Similarity	NPC110373
0.7778	Intermediate Similarity	NPC5908
0.7778	Intermediate Similarity	NPC162346
0.7778	Intermediate Similarity	NPC80471
0.7765	Intermediate Similarity	NPC211892
0.7765	Intermediate Similarity	NPC471219
0.7765	Intermediate Similarity	NPC61527
0.7763	Intermediate Similarity	NPC151481
0.7738	Intermediate Similarity	NPC470800
0.7727	Intermediate Similarity	NPC177037
0.7727	Intermediate Similarity	NPC472814
0.7727	Intermediate Similarity	NPC472811
0.7722	Intermediate Similarity	NPC329852
0.7701	Intermediate Similarity	NPC79027
0.7701	Intermediate Similarity	NPC50488
0.7701	Intermediate Similarity	NPC474396
0.7692	Intermediate Similarity	NPC53844
0.7692	Intermediate Similarity	NPC477085
0.7674	Intermediate Similarity	NPC471796
0.7674	Intermediate Similarity	NPC476600
0.7674	Intermediate Similarity	NPC199382
0.7667	Intermediate Similarity	NPC276110
0.7662	Intermediate Similarity	NPC329904
0.7662	Intermediate Similarity	NPC473361
0.7654	Intermediate Similarity	NPC184737
0.7654	Intermediate Similarity	NPC471220
0.7647	Intermediate Similarity	NPC329630
0.7647	Intermediate Similarity	NPC35933
0.7647	Intermediate Similarity	NPC11804
0.764	Intermediate Similarity	NPC205034
0.764	Intermediate Similarity	NPC162615
0.764	Intermediate Similarity	NPC152778
0.7632	Intermediate Similarity	NPC474823
0.7632	Intermediate Similarity	NPC276290
0.7619	Intermediate Similarity	NPC193198
0.7619	Intermediate Similarity	NPC23748
0.7614	Intermediate Similarity	NPC310479
0.7595	Intermediate Similarity	NPC470686
0.7595	Intermediate Similarity	NPC315843
0.759	Intermediate Similarity	NPC159148
0.759	Intermediate Similarity	NPC112868
0.759	Intermediate Similarity	NPC315731
0.7582	Intermediate Similarity	NPC16967
0.7582	Intermediate Similarity	NPC165632
0.7568	Intermediate Similarity	NPC226066
0.7564	Intermediate Similarity	NPC477087
0.7564	Intermediate Similarity	NPC477086
0.7558	Intermediate Similarity	NPC329692
0.7556	Intermediate Similarity	NPC53685
0.7556	Intermediate Similarity	NPC470255
0.7532	Intermediate Similarity	NPC475004
0.7531	Intermediate Similarity	NPC84360
0.7531	Intermediate Similarity	NPC315394
0.7529	Intermediate Similarity	NPC96055
0.7528	Intermediate Similarity	NPC2882
0.7528	Intermediate Similarity	NPC72845
0.7528	Intermediate Similarity	NPC477122
0.7528	Intermediate Similarity	NPC329842
0.7527	Intermediate Similarity	NPC38855
0.75	Intermediate Similarity	NPC477719
0.75	Intermediate Similarity	NPC205143
0.75	Intermediate Similarity	NPC174342
0.75	Intermediate Similarity	NPC477718
0.75	Intermediate Similarity	NPC5509
0.75	Intermediate Similarity	NPC256112
0.7471	Intermediate Similarity	NPC473891
0.7471	Intermediate Similarity	NPC166857
0.747	Intermediate Similarity	NPC281880
0.747	Intermediate Similarity	NPC268827
0.7467	Intermediate Similarity	NPC182794
0.7467	Intermediate Similarity	NPC470123
0.7444	Intermediate Similarity	NPC139692
0.7444	Intermediate Similarity	NPC156553
0.7442	Intermediate Similarity	NPC474694
0.7442	Intermediate Similarity	NPC471494
0.7442	Intermediate Similarity	NPC475860
0.7442	Intermediate Similarity	NPC86316
0.7442	Intermediate Similarity	NPC106416
0.7442	Intermediate Similarity	NPC473659
0.7442	Intermediate Similarity	NPC30984
0.7439	Intermediate Similarity	NPC279532
0.7419	Intermediate Similarity	NPC275086
0.7419	Intermediate Similarity	NPC325229
0.7416	Intermediate Similarity	NPC220216
0.7412	Intermediate Similarity	NPC16488
0.7412	Intermediate Similarity	NPC472473
0.7412	Intermediate Similarity	NPC477124
0.7412	Intermediate Similarity	NPC477667
0.7412	Intermediate Similarity	NPC49208
0.7412	Intermediate Similarity	NPC44261
0.7412	Intermediate Similarity	NPC321385
0.7391	Intermediate Similarity	NPC242848
0.7391	Intermediate Similarity	NPC134072
0.7391	Intermediate Similarity	NPC234993
0.7391	Intermediate Similarity	NPC473153
0.7381	Intermediate Similarity	NPC184208
0.7381	Intermediate Similarity	NPC170303
0.7381	Intermediate Similarity	NPC325031
0.7381	Intermediate Similarity	NPC8538
0.7375	Intermediate Similarity	NPC474758
0.7375	Intermediate Similarity	NPC477204
0.7375	Intermediate Similarity	NPC107654
0.7375	Intermediate Similarity	NPC474280
0.7368	Intermediate Similarity	NPC146811
0.7363	Intermediate Similarity	NPC105490
0.7363	Intermediate Similarity	NPC469491
0.7363	Intermediate Similarity	NPC191521
0.7363	Intermediate Similarity	NPC57117
0.7356	Intermediate Similarity	NPC475461
0.7356	Intermediate Similarity	NPC477668
0.7356	Intermediate Similarity	NPC315395
0.7356	Intermediate Similarity	NPC316426
0.7356	Intermediate Similarity	NPC311163
0.7356	Intermediate Similarity	NPC305475
0.7349	Intermediate Similarity	NPC100906
0.7349	Intermediate Similarity	NPC325869
0.7349	Intermediate Similarity	NPC471537
0.734	Intermediate Similarity	NPC477721
0.734	Intermediate Similarity	NPC476299
0.734	Intermediate Similarity	NPC477716
0.734	Intermediate Similarity	NPC474012
0.734	Intermediate Similarity	NPC227865
0.7333	Intermediate Similarity	NPC329698
0.7333	Intermediate Similarity	NPC124374
0.7333	Intermediate Similarity	NPC234335
0.7326	Intermediate Similarity	NPC82297
0.7326	Intermediate Similarity	NPC474693
0.7317	Intermediate Similarity	NPC125365

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 NPC262747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	1669
0.2-0.3	4142
0.3-0.4	2381
0.4-0.5	518
0.5-0.6	248
0.6-0.7	48
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
0.9103	High Similarity	NPD6400	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4191	Approved
0.7297	Intermediate Similarity	NPD4192	Approved
0.7297	Intermediate Similarity	NPD4193	Approved
0.7297	Intermediate Similarity	NPD4194	Approved
0.7234	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD7637	Suspended
0.7073	Intermediate Similarity	NPD8039	Approved
0.7033	Intermediate Similarity	NPD6698	Approved
0.7033	Intermediate Similarity	NPD5785	Approved
0.7033	Intermediate Similarity	NPD46	Approved
0.7011	Intermediate Similarity	NPD7154	Phase 3
0.6979	Remote Similarity	NPD7639	Approved
0.6979	Remote Similarity	NPD7640	Approved
0.6897	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7638	Approved
0.6867	Remote Similarity	NPD8264	Approved
0.686	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7838	Discovery
0.6824	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5344	Discontinued
0.6706	Remote Similarity	NPD5776	Phase 2
0.6706	Remote Similarity	NPD6925	Approved
0.6702	Remote Similarity	NPD5779	Approved
0.6702	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6629	Remote Similarity	NPD5362	Discontinued
0.6629	Remote Similarity	NPD6695	Phase 3
0.6628	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4268	Approved
0.6628	Remote Similarity	NPD7145	Approved
0.6628	Remote Similarity	NPD4271	Approved
0.6622	Remote Similarity	NPD4219	Approved
0.6596	Remote Similarity	NPD6411	Approved
0.6591	Remote Similarity	NPD6902	Approved
0.6562	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6051	Approved
0.6556	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6929	Approved
0.6531	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5209	Approved
0.6484	Remote Similarity	NPD5363	Approved
0.6484	Remote Similarity	NPD1694	Approved
0.6481	Remote Similarity	NPD7115	Discovery
0.6477	Remote Similarity	NPD6930	Phase 2
0.6477	Remote Similarity	NPD6931	Approved
0.6465	Remote Similarity	NPD6648	Approved
0.6463	Remote Similarity	NPD6922	Approved
0.6463	Remote Similarity	NPD6923	Approved
0.6444	Remote Similarity	NPD5331	Approved
0.6444	Remote Similarity	NPD5332	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6413	Remote Similarity	NPD7521	Approved
0.6413	Remote Similarity	NPD7334	Approved
0.6413	Remote Similarity	NPD6409	Approved
0.6413	Remote Similarity	NPD7146	Approved
0.6413	Remote Similarity	NPD5330	Approved
0.6413	Remote Similarity	NPD6684	Approved
0.641	Remote Similarity	NPD368	Approved
0.6404	Remote Similarity	NPD6898	Phase 1
0.6404	Remote Similarity	NPD4790	Discontinued
0.6386	Remote Similarity	NPD7144	Approved
0.6386	Remote Similarity	NPD7143	Approved
0.6383	Remote Similarity	NPD6101	Approved
0.6383	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6371	Approved
0.6354	Remote Similarity	NPD6399	Phase 3
0.6353	Remote Similarity	NPD6924	Approved
0.6353	Remote Similarity	NPD6926	Approved
0.6344	Remote Similarity	NPD7524	Approved
0.6344	Remote Similarity	NPD7750	Discontinued
0.6344	Remote Similarity	NPD4251	Approved
0.6344	Remote Similarity	NPD4250	Approved
0.6337	Remote Similarity	NPD7632	Discontinued
0.6333	Remote Similarity	NPD4270	Approved
0.6333	Remote Similarity	NPD4269	Approved
0.6327	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6932	Approved
0.631	Remote Similarity	NPD7150	Approved
0.631	Remote Similarity	NPD7151	Approved
0.631	Remote Similarity	NPD7152	Approved
0.6304	Remote Similarity	NPD1696	Phase 3
0.6292	Remote Similarity	NPD4252	Approved
0.6289	Remote Similarity	NPD7748	Approved
0.6282	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6942	Approved
0.6279	Remote Similarity	NPD7339	Approved
0.6277	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6903	Approved
0.6262	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD7983	Approved
0.625	Remote Similarity	NPD7515	Phase 2
0.6237	Remote Similarity	NPD4249	Approved
0.6237	Remote Similarity	NPD5786	Approved
0.6235	Remote Similarity	NPD4732	Discontinued
0.6224	Remote Similarity	NPD5695	Phase 3
0.6207	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6933	Approved
0.6196	Remote Similarity	NPD4786	Approved
0.6196	Remote Similarity	NPD3666	Approved
0.6196	Remote Similarity	NPD3665	Phase 1
0.6196	Remote Similarity	NPD3133	Approved
0.618	Remote Similarity	NPD7645	Phase 2
0.618	Remote Similarity	NPD6683	Phase 2
0.6164	Remote Similarity	NPD6927	Phase 3
0.6162	Remote Similarity	NPD7839	Suspended
0.6154	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD5739	Approved
0.6154	Remote Similarity	NPD3667	Approved
0.6154	Remote Similarity	NPD6435	Approved
0.6154	Remote Similarity	NPD7128	Approved
0.6154	Remote Similarity	NPD6675	Approved
0.6136	Remote Similarity	NPD4756	Discovery
0.6132	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6893	Approved
0.6126	Remote Similarity	NPD7327	Approved
0.6126	Remote Similarity	NPD7328	Approved
0.6106	Remote Similarity	NPD8033	Approved
0.6105	Remote Similarity	NPD6672	Approved
0.6105	Remote Similarity	NPD5737	Approved
0.61	Remote Similarity	NPD7902	Approved
0.6098	Remote Similarity	NPD7331	Phase 2
0.6082	Remote Similarity	NPD7087	Discontinued
0.6071	Remote Similarity	NPD7516	Approved
0.6064	Remote Similarity	NPD5279	Phase 3
0.6064	Remote Similarity	NPD3618	Phase 1
0.6053	Remote Similarity	NPD342	Phase 1
0.6044	Remote Similarity	NPD5369	Approved
0.6042	Remote Similarity	NPD5328	Approved
0.604	Remote Similarity	NPD5696	Approved
0.6038	Remote Similarity	NPD6881	Approved
0.6038	Remote Similarity	NPD6899	Approved
0.6038	Remote Similarity	NPD7320	Approved
0.6036	Remote Similarity	NPD7505	Discontinued
0.6018	Remote Similarity	NPD8294	Approved
0.6018	Remote Similarity	NPD8377	Approved
0.6	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6372	Approved
0.5981	Remote Similarity	NPD6373	Approved
0.5965	Remote Similarity	NPD8296	Approved
0.5965	Remote Similarity	NPD8335	Approved
0.5965	Remote Similarity	NPD7503	Approved
0.5965	Remote Similarity	NPD8380	Approved
0.5965	Remote Similarity	NPD8379	Approved
0.5965	Remote Similarity	NPD8378	Approved
0.5957	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5701	Approved
0.5943	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5697	Approved
0.5934	Remote Similarity	NPD5368	Approved
0.5934	Remote Similarity	NPD7509	Discontinued
0.5926	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7290	Approved
0.5926	Remote Similarity	NPD6883	Approved
0.5926	Remote Similarity	NPD7102	Approved
0.5918	Remote Similarity	NPD6079	Approved
0.5918	Remote Similarity	NPD5693	Phase 1
0.5918	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD4265	Approved
0.5914	Remote Similarity	NPD6110	Phase 1
0.5895	Remote Similarity	NPD4623	Approved
0.5895	Remote Similarity	NPD4519	Discontinued
0.5876	Remote Similarity	NPD5370	Suspended
0.5876	Remote Similarity	NPD4753	Phase 2
0.5872	Remote Similarity	NPD6650	Approved
0.5872	Remote Similarity	NPD8130	Phase 1
0.5872	Remote Similarity	NPD6847	Approved
0.5872	Remote Similarity	NPD6649	Approved
0.5872	Remote Similarity	NPD6869	Approved
0.5872	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6617	Approved
0.5849	Remote Similarity	NPD6640	Phase 3
0.5849	Remote Similarity	NPD4211	Phase 1
0.5833	Remote Similarity	NPD6013	Approved
0.5833	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6014	Approved
0.5824	Remote Similarity	NPD4195	Approved
0.5823	Remote Similarity	NPD9119	Approved
0.5823	Remote Similarity	NPD69	Approved
0.5818	Remote Similarity	NPD6882	Approved
0.5818	Remote Similarity	NPD8297	Approved
0.5816	Remote Similarity	NPD7136	Phase 2
0.581	Remote Similarity	NPD6647	Phase 2
0.58	Remote Similarity	NPD5282	Discontinued
0.58	Remote Similarity	NPD7900	Approved
0.58	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6412	Phase 2
0.5763	Remote Similarity	NPD7507	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