NPASS Compound

Structure

NPC475860 OpenBabel07101718242D 25 27 0 0 1 0 0 0 0 0999 V2000 5.7938 -5.9018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7208 -3.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0809 -4.7428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7134 -0.8192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1246 -5.1586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0735 -2.5134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7645 -3.4644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0195 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0250 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4118 -3.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4044 -1.7702 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4336 -4.2076 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4263 -1.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 0.6045 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 14 1 0 0 0 0 3 14 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 15 4 1 6 0 0 0 15 17 1 0 0 0 0 16 6 1 1 0 0 0 17 21 1 1 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 2 0 0 0 0 20 25 1 0 0 0 0 21 5 1 1 0 0 0 22 24 1 6 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.25
Volume:	381.86
LogP:	4.703
LogD:	4.623
LogS:	-5.481
# Rotatable Bonds:	5
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.562
Synthetic Accessibility Score:	4.878
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.656
MDCK Permeability:	3.13267191813793e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.095

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	83.75798797607422%
Volume Distribution (VD):	1.102
Pgp-substrate:	1.8514107465744019%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.335
CYP2C19-inhibitor:	0.227
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.379
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.865
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	4.878
Half-life (T1/2):	0.103

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.262
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.53
Carcinogencity:	0.034
Eye Corrosion:	0.09
Eye Irritation:	0.337
Respiratory Toxicity:	0.675

Download Data

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

Natural Product: NPC475860

Natural Product ID:	NPC475860
*Common Name:**	Demethylincisterol A4
IUPAC Name:	(3aS,5aR,6R)-6-[(E,2R,5R)-5-ethyl-6-methylhept-3-en-2-yl]-3a-hydroxy-5a-methyl-4,5,6,7,8,8a-hexahydrocyclopenta[e][1]benzofuran-2-one
Synonyms:	Demethylincisterol A4
Standard InCHIKey:	BQOIBIMGHAKGTD-OGHANNSPSA-N
Standard InCHI:	InChI=1S/C22H34O3/c1-6-16(14(2)3)8-7-15(4)17-9-10-18-19-13-20(23)25-22(19,24)12-11-21(17,18)5/h7-8,13-18,24H,6,9-12H2,1-5H3/b8-7+/t15-,16+,17-,18?,21-,22+/m1/s1
SMILES:	CC[C@H](C(C)C)/C=C/[C@H]([C@H]1CCC2[C@]1(C)CC[C@]1(C2=CC(=O)O1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517527
PubChem CID:	11268011
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO33129	hominaxella sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15787431]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.92	ug ml-1	PMID[525189]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	0.79	ug ml-1	PMID[525189]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	0.55	ug ml-1	PMID[525189]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	0.68	ug ml-1	PMID[525189]
NPT393	Cell Line	HCT-116	Homo sapiens	ED50	=	0.65	ug ml-1	PMID[525189]

☑ 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 NPC475860 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	142
0.1-0.2	1129
0.2-0.3	4948
0.3-0.4	14911
0.4-0.5	9438
0.5-0.6	7746
0.6-0.7	3816
0.7-0.8	555
0.8-0.85	7
0.85-0.9	0
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474694
1.0	High Similarity	NPC473659
0.9873	High Similarity	NPC474693
0.9259	High Similarity	NPC30502
0.8659	High Similarity	NPC10636
0.8222	Intermediate Similarity	NPC329842
0.8191	Intermediate Similarity	NPC472826
0.8046	Intermediate Similarity	NPC471302
0.8046	Intermediate Similarity	NPC471301
0.8043	Intermediate Similarity	NPC201725
0.8043	Intermediate Similarity	NPC470255
0.8022	Intermediate Similarity	NPC289479
0.8022	Intermediate Similarity	NPC472811
0.7979	Intermediate Similarity	NPC476253
0.7955	Intermediate Similarity	NPC473251
0.7955	Intermediate Similarity	NPC42586
0.7935	Intermediate Similarity	NPC472303
0.7935	Intermediate Similarity	NPC472812
0.7931	Intermediate Similarity	NPC321385
0.7931	Intermediate Similarity	NPC311070
0.7912	Intermediate Similarity	NPC182136
0.7912	Intermediate Similarity	NPC78973
0.7889	Intermediate Similarity	NPC472809
0.7889	Intermediate Similarity	NPC472810
0.7865	Intermediate Similarity	NPC131813
0.7857	Intermediate Similarity	NPC472819
0.7857	Intermediate Similarity	NPC476439
0.7841	Intermediate Similarity	NPC96055
0.7816	Intermediate Similarity	NPC471298
0.7812	Intermediate Similarity	NPC201406
0.7802	Intermediate Similarity	NPC470734
0.7789	Intermediate Similarity	NPC231751
0.7778	Intermediate Similarity	NPC472818
0.7766	Intermediate Similarity	NPC472441
0.7765	Intermediate Similarity	NPC184737
0.7753	Intermediate Similarity	NPC146850
0.7753	Intermediate Similarity	NPC287015
0.7753	Intermediate Similarity	NPC253604
0.7753	Intermediate Similarity	NPC471795
0.7742	Intermediate Similarity	NPC53555
0.7742	Intermediate Similarity	NPC38232
0.7738	Intermediate Similarity	NPC476317
0.7732	Intermediate Similarity	NPC295110
0.7732	Intermediate Similarity	NPC222875
0.7732	Intermediate Similarity	NPC25177
0.7732	Intermediate Similarity	NPC268829
0.7732	Intermediate Similarity	NPC247701
0.7727	Intermediate Similarity	NPC471297
0.7727	Intermediate Similarity	NPC476927
0.7727	Intermediate Similarity	NPC474809
0.7717	Intermediate Similarity	NPC302280
0.7717	Intermediate Similarity	NPC310479
0.7701	Intermediate Similarity	NPC170303
0.77	Intermediate Similarity	NPC472820
0.7692	Intermediate Similarity	NPC472378
0.7684	Intermediate Similarity	NPC470801
0.7667	Intermediate Similarity	NPC471219
0.766	Intermediate Similarity	NPC298973
0.766	Intermediate Similarity	NPC469697
0.766	Intermediate Similarity	NPC104925
0.7647	Intermediate Similarity	NPC189206
0.7647	Intermediate Similarity	NPC132542
0.7647	Intermediate Similarity	NPC473756
0.7634	Intermediate Similarity	NPC477122
0.7634	Intermediate Similarity	NPC177641
0.7634	Intermediate Similarity	NPC2882
0.7629	Intermediate Similarity	NPC324841
0.7614	Intermediate Similarity	NPC256112
0.7614	Intermediate Similarity	NPC471218
0.7609	Intermediate Similarity	NPC474396
0.7609	Intermediate Similarity	NPC472240
0.7609	Intermediate Similarity	NPC262858
0.7609	Intermediate Similarity	NPC50488
0.7586	Intermediate Similarity	NPC281880
0.7586	Intermediate Similarity	NPC268827
0.7582	Intermediate Similarity	NPC471657
0.7582	Intermediate Similarity	NPC471796
0.7582	Intermediate Similarity	NPC45957
0.7579	Intermediate Similarity	NPC293052
0.7576	Intermediate Similarity	NPC196471
0.7576	Intermediate Similarity	NPC10232
0.7576	Intermediate Similarity	NPC187302
0.7576	Intermediate Similarity	NPC97487
0.7576	Intermediate Similarity	NPC112009
0.7576	Intermediate Similarity	NPC160583
0.7576	Intermediate Similarity	NPC180204
0.7576	Intermediate Similarity	NPC189588
0.7556	Intermediate Similarity	NPC472442
0.7556	Intermediate Similarity	NPC30984
0.7556	Intermediate Similarity	NPC474013
0.7553	Intermediate Similarity	NPC205034
0.7553	Intermediate Similarity	NPC162615
0.7553	Intermediate Similarity	NPC7349
0.7553	Intermediate Similarity	NPC472871
0.7553	Intermediate Similarity	NPC472954
0.7553	Intermediate Similarity	NPC152778
0.7549	Intermediate Similarity	NPC475030
0.7528	Intermediate Similarity	NPC472377
0.7528	Intermediate Similarity	NPC472473
0.7528	Intermediate Similarity	NPC42476
0.7528	Intermediate Similarity	NPC472440
0.7527	Intermediate Similarity	NPC281942
0.7527	Intermediate Similarity	NPC232426
0.7527	Intermediate Similarity	NPC221111
0.7527	Intermediate Similarity	NPC477782
0.7527	Intermediate Similarity	NPC280149
0.7526	Intermediate Similarity	NPC474440
0.75	Intermediate Similarity	NPC165632
0.75	Intermediate Similarity	NPC242448
0.75	Intermediate Similarity	NPC78677
0.75	Intermediate Similarity	NPC473153
0.75	Intermediate Similarity	NPC162346
0.75	Intermediate Similarity	NPC474629
0.75	Intermediate Similarity	NPC59994
0.75	Intermediate Similarity	NPC16967
0.75	Intermediate Similarity	NPC475944
0.75	Intermediate Similarity	NPC472471
0.75	Intermediate Similarity	NPC190713
0.75	Intermediate Similarity	NPC159148
0.7475	Intermediate Similarity	NPC472815
0.7474	Intermediate Similarity	NPC324078
0.7474	Intermediate Similarity	NPC105490
0.7473	Intermediate Similarity	NPC329692
0.7471	Intermediate Similarity	NPC242767
0.7449	Intermediate Similarity	NPC251680
0.7449	Intermediate Similarity	NPC16601
0.7449	Intermediate Similarity	NPC476767
0.7447	Intermediate Similarity	NPC141831
0.7447	Intermediate Similarity	NPC212948
0.7447	Intermediate Similarity	NPC110923
0.7447	Intermediate Similarity	NPC234335
0.7447	Intermediate Similarity	NPC74296
0.7447	Intermediate Similarity	NPC477783
0.7444	Intermediate Similarity	NPC164577
0.7444	Intermediate Similarity	NPC475100
0.7444	Intermediate Similarity	NPC306951
0.7442	Intermediate Similarity	NPC54996
0.7442	Intermediate Similarity	NPC262747
0.7426	Intermediate Similarity	NPC239961
0.7426	Intermediate Similarity	NPC220217
0.7426	Intermediate Similarity	NPC85670
0.7426	Intermediate Similarity	NPC186668
0.7426	Intermediate Similarity	NPC119855
0.7423	Intermediate Similarity	NPC141401
0.7423	Intermediate Similarity	NPC253826
0.7423	Intermediate Similarity	NPC477719
0.7423	Intermediate Similarity	NPC477718
0.7419	Intermediate Similarity	NPC251528
0.7419	Intermediate Similarity	NPC285982
0.7419	Intermediate Similarity	NPC177141
0.7419	Intermediate Similarity	NPC146554
0.7419	Intermediate Similarity	NPC66344
0.7416	Intermediate Similarity	NPC324170
0.7416	Intermediate Similarity	NPC323251
0.7416	Intermediate Similarity	NPC2524
0.7412	Intermediate Similarity	NPC113639
0.7412	Intermediate Similarity	NPC85831
0.7412	Intermediate Similarity	NPC265921
0.7412	Intermediate Similarity	NPC215215
0.74	Intermediate Similarity	NPC120009
0.74	Intermediate Similarity	NPC476237
0.74	Intermediate Similarity	NPC297617
0.74	Intermediate Similarity	NPC472821
0.7396	Intermediate Similarity	NPC276110
0.7396	Intermediate Similarity	NPC476488
0.7396	Intermediate Similarity	NPC476487
0.7396	Intermediate Similarity	NPC171395
0.7391	Intermediate Similarity	NPC128644
0.7391	Intermediate Similarity	NPC474832
0.7391	Intermediate Similarity	NPC166857
0.7391	Intermediate Similarity	NPC236618
0.7391	Intermediate Similarity	NPC312561
0.7391	Intermediate Similarity	NPC473891
0.7374	Intermediate Similarity	NPC476240
0.7374	Intermediate Similarity	NPC472643
0.7374	Intermediate Similarity	NPC198992
0.7374	Intermediate Similarity	NPC476223
0.7374	Intermediate Similarity	NPC224720
0.7368	Intermediate Similarity	NPC472640
0.7368	Intermediate Similarity	NPC472641
0.7368	Intermediate Similarity	NPC214697
0.7368	Intermediate Similarity	NPC139692
0.7368	Intermediate Similarity	NPC476304
0.7363	Intermediate Similarity	NPC86316
0.7363	Intermediate Similarity	NPC269638
0.7363	Intermediate Similarity	NPC329630
0.7363	Intermediate Similarity	NPC106416
0.7363	Intermediate Similarity	NPC109528
0.7363	Intermediate Similarity	NPC65661
0.7356	Intermediate Similarity	NPC209135
0.7356	Intermediate Similarity	NPC474816
0.7347	Intermediate Similarity	NPC181147
0.7347	Intermediate Similarity	NPC275086
0.7347	Intermediate Similarity	NPC218107
0.7347	Intermediate Similarity	NPC473154
0.7347	Intermediate Similarity	NPC108368
0.7347	Intermediate Similarity	NPC57079
0.7347	Intermediate Similarity	NPC325229
0.7347	Intermediate Similarity	NPC92275
0.7347	Intermediate Similarity	NPC471610

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 NPC475860 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1366
0.2-0.3	4133
0.3-0.4	2514
0.4-0.5	592
0.5-0.6	228
0.6-0.7	174
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7449	Intermediate Similarity	NPD7639	Approved
0.7449	Intermediate Similarity	NPD7640	Approved
0.7347	Intermediate Similarity	NPD7638	Approved
0.7253	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD7328	Approved
0.7	Intermediate Similarity	NPD4225	Approved
0.6937	Remote Similarity	NPD7516	Approved
0.6907	Remote Similarity	NPD7637	Suspended
0.6889	Remote Similarity	NPD4195	Approved
0.6875	Remote Similarity	NPD8377	Approved
0.6875	Remote Similarity	NPD8294	Approved
0.6875	Remote Similarity	NPD6051	Approved
0.6814	Remote Similarity	NPD8380	Approved
0.6814	Remote Similarity	NPD8378	Approved
0.6814	Remote Similarity	NPD8379	Approved
0.6814	Remote Similarity	NPD8296	Approved
0.6814	Remote Similarity	NPD8335	Approved
0.6814	Remote Similarity	NPD8033	Approved
0.6809	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5785	Approved
0.6796	Remote Similarity	NPD7632	Discontinued
0.6778	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5362	Discontinued
0.6757	Remote Similarity	NPD7115	Discovery
0.6735	Remote Similarity	NPD5693	Phase 1
0.6699	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6399	Phase 3
0.6636	Remote Similarity	NPD6686	Approved
0.6633	Remote Similarity	NPD5207	Approved
0.6632	Remote Similarity	NPD1694	Approved
0.6602	Remote Similarity	NPD6648	Approved
0.6598	Remote Similarity	NPD5737	Approved
0.6598	Remote Similarity	NPD6672	Approved
0.6598	Remote Similarity	NPD6903	Approved
0.6596	Remote Similarity	NPD5332	Approved
0.6596	Remote Similarity	NPD5331	Approved
0.6596	Remote Similarity	NPD6695	Phase 3
0.6585	Remote Similarity	NPD4193	Approved
0.6585	Remote Similarity	NPD4194	Approved
0.6585	Remote Similarity	NPD4192	Approved
0.6585	Remote Similarity	NPD4191	Approved
0.6581	Remote Similarity	NPD7507	Approved
0.6569	Remote Similarity	NPD6084	Phase 2
0.6569	Remote Similarity	NPD6083	Phase 2
0.6566	Remote Similarity	NPD5281	Approved
0.6566	Remote Similarity	NPD6079	Approved
0.6566	Remote Similarity	NPD5284	Approved
0.6562	Remote Similarity	NPD6409	Approved
0.6562	Remote Similarity	NPD7334	Approved
0.6562	Remote Similarity	NPD6684	Approved
0.6562	Remote Similarity	NPD7146	Approved
0.6562	Remote Similarity	NPD5330	Approved
0.6562	Remote Similarity	NPD7521	Approved
0.6559	Remote Similarity	NPD4790	Discontinued
0.6545	Remote Similarity	NPD6882	Approved
0.6535	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5695	Phase 3
0.6531	Remote Similarity	NPD6904	Approved
0.6531	Remote Similarity	NPD6673	Approved
0.6531	Remote Similarity	NPD6080	Approved
0.6531	Remote Similarity	NPD5328	Approved
0.6526	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6929	Approved
0.6522	Remote Similarity	NPD7503	Approved
0.6517	Remote Similarity	NPD6926	Approved
0.6517	Remote Similarity	NPD4785	Approved
0.6517	Remote Similarity	NPD4784	Approved
0.6517	Remote Similarity	NPD6924	Approved
0.6489	Remote Similarity	NPD4221	Approved
0.6489	Remote Similarity	NPD4223	Phase 3
0.6481	Remote Similarity	NPD6899	Approved
0.6481	Remote Similarity	NPD6881	Approved
0.6481	Remote Similarity	NPD7320	Approved
0.6477	Remote Similarity	NPD7150	Approved
0.6477	Remote Similarity	NPD4243	Approved
0.6477	Remote Similarity	NPD7151	Approved
0.6477	Remote Similarity	NPD7152	Approved
0.6458	Remote Similarity	NPD5329	Approved
0.6452	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6930	Phase 2
0.6452	Remote Similarity	NPD6931	Approved
0.6452	Remote Similarity	NPD7514	Phase 3
0.6452	Remote Similarity	NPD7525	Registered
0.6449	Remote Similarity	NPD6675	Approved
0.6449	Remote Similarity	NPD6402	Approved
0.6449	Remote Similarity	NPD7128	Approved
0.6449	Remote Similarity	NPD5739	Approved
0.6444	Remote Similarity	NPD7339	Approved
0.6444	Remote Similarity	NPD8039	Approved
0.6444	Remote Similarity	NPD6942	Approved
0.6442	Remote Similarity	NPD6404	Discontinued
0.6436	Remote Similarity	NPD7748	Approved
0.6436	Remote Similarity	NPD6001	Approved
0.6429	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5208	Approved
0.6417	Remote Similarity	NPD7319	Approved
0.6413	Remote Similarity	NPD7145	Approved
0.6413	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6050	Approved
0.64	Remote Similarity	NPD5694	Approved
0.6392	Remote Similarity	NPD4623	Approved
0.6392	Remote Similarity	NPD5690	Phase 2
0.6392	Remote Similarity	NPD4519	Discontinued
0.6392	Remote Similarity	NPD3618	Phase 1
0.6392	Remote Similarity	NPD6098	Approved
0.6389	Remote Similarity	NPD5697	Approved
0.6383	Remote Similarity	NPD6902	Approved
0.6374	Remote Similarity	NPD6933	Approved
0.6364	Remote Similarity	NPD7143	Approved
0.6364	Remote Similarity	NPD7144	Approved
0.6364	Remote Similarity	NPD7290	Approved
0.6364	Remote Similarity	NPD7102	Approved
0.6364	Remote Similarity	NPD6883	Approved
0.6354	Remote Similarity	NPD4786	Approved
0.6354	Remote Similarity	NPD4197	Approved
0.6353	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5696	Approved
0.633	Remote Similarity	NPD6011	Approved
0.6327	Remote Similarity	NPD7524	Approved
0.6327	Remote Similarity	NPD3573	Approved
0.6327	Remote Similarity	NPD7750	Discontinued
0.6311	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6650	Approved
0.6306	Remote Similarity	NPD8130	Phase 1
0.6306	Remote Similarity	NPD6847	Approved
0.6306	Remote Similarity	NPD6649	Approved
0.6306	Remote Similarity	NPD6869	Approved
0.6306	Remote Similarity	NPD6617	Approved
0.6304	Remote Similarity	NPD5776	Phase 2
0.6304	Remote Similarity	NPD6925	Approved
0.63	Remote Similarity	NPD5692	Phase 3
0.6289	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5363	Approved
0.6277	Remote Similarity	NPD7332	Phase 2
0.6277	Remote Similarity	NPD4821	Approved
0.6277	Remote Similarity	NPD4822	Approved
0.6277	Remote Similarity	NPD4820	Approved
0.6277	Remote Similarity	NPD4819	Approved
0.6273	Remote Similarity	NPD6012	Approved
0.6273	Remote Similarity	NPD6373	Approved
0.6273	Remote Similarity	NPD6014	Approved
0.6273	Remote Similarity	NPD6013	Approved
0.6273	Remote Similarity	NPD6372	Approved
0.6264	Remote Similarity	NPD8264	Approved
0.625	Remote Similarity	NPD6923	Approved
0.625	Remote Similarity	NPD6922	Approved
0.625	Remote Similarity	NPD7902	Approved
0.625	Remote Similarity	NPD7154	Phase 3
0.625	Remote Similarity	NPD8297	Approved
0.6239	Remote Similarity	NPD5701	Approved
0.6238	Remote Similarity	NPD8035	Phase 2
0.6238	Remote Similarity	NPD7515	Phase 2
0.6238	Remote Similarity	NPD8034	Phase 2
0.6237	Remote Similarity	NPD4268	Approved
0.6237	Remote Similarity	NPD4271	Approved
0.6224	Remote Similarity	NPD4689	Approved
0.6224	Remote Similarity	NPD4694	Approved
0.6224	Remote Similarity	NPD5280	Approved
0.6224	Remote Similarity	NPD4138	Approved
0.6224	Remote Similarity	NPD5279	Phase 3
0.6224	Remote Similarity	NPD4693	Phase 3
0.6224	Remote Similarity	NPD4688	Approved
0.6224	Remote Similarity	NPD4690	Approved
0.6224	Remote Similarity	NPD5205	Approved
0.6214	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD3666	Approved
0.6186	Remote Similarity	NPD3665	Phase 1
0.6186	Remote Similarity	NPD3133	Approved
0.6176	Remote Similarity	NPD5778	Approved
0.6176	Remote Similarity	NPD5779	Approved
0.6176	Remote Similarity	NPD4202	Approved
0.6168	Remote Similarity	NPD5211	Phase 2
0.6162	Remote Similarity	NPD4251	Approved
0.6162	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4250	Approved
0.6161	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5222	Approved
0.6154	Remote Similarity	NPD5221	Approved
0.6154	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4269	Approved
0.6146	Remote Similarity	NPD3667	Approved
0.6146	Remote Similarity	NPD5209	Approved
0.6146	Remote Similarity	NPD4270	Approved
0.6139	Remote Similarity	NPD7838	Discovery
0.6129	Remote Similarity	NPD6932	Approved
0.6122	Remote Similarity	NPD6893	Approved
0.6106	Remote Similarity	NPD6053	Discontinued
0.6105	Remote Similarity	NPD7509	Discontinued
0.61	Remote Similarity	NPD4518	Approved
0.6095	Remote Similarity	NPD5173	Approved
0.6087	Remote Similarity	NPD5275	Approved
0.6087	Remote Similarity	NPD4190	Phase 3
0.6087	Remote Similarity	NPD6868	Approved
0.6083	Remote Similarity	NPD7492	Approved
0.6078	Remote Similarity	NPD6411	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